US 11,440,913 B2Granted

Aminoimidazopyridazines as kinase inhibitors

AssigneeBristol-Myers Squibb Company

InventorsMichael E. Mertzman, Carolyn Diane Dzierba, Jason M. Guernon, Amy C. Hart, Guanglin Luo, John E. Macor, William J. Pitts, Jianliang Shi, Steven H. Spergel

Life of this patent

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Abstract

Compounds having formula (I), and enantiomers, and diastereomers, stereoisomers, pharmaceutically-acceptable salts thereof, (I) are useful as kinase modulators, including RIPK1 modulation. All the variables are as defined herein.

Claims14

Dependent claims

A compound having formula (I):

or pharmaceutically acceptable salt thereof,
wherein:
X is CR7 or N;
(i) L is —C(O)NRa— or
and
A is C1-4 alkyl, C1-4 deuteroalkyl, C1-3 alkyl-C3-6 cycloalkyl, C0-3 alkyl-heterocyclyl, C1-4 alkoxy, or C3-6 cycloalkyl-C1-3 alkyl;
wherein the C1-4 alkyl, C1-4 deuteroalkyl, or C1-4 alkoxy is substituted with 0-1 OH substituent;
wherein the alkyl of the C0-3 alkyl-heterocyclyl is substituted with 0-1 OH substituent;
wherein the heterocyclyl of the C0-3 alkyl-heterocyclyl is a 3-6 membered ring containing 1-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the heterocyclyl of the C0-3 alkyl-heterocyclyl is substituted with 0-2 substituents independently selected from the group consisting of halo, C1-3 alkyl, and OH;
or
(ii) L is —CH2—;
and
A is —NRaC(O)—;
Ra is H, C1-4 alkyl, C1-4 deuteroalkyl, ((phosphonooxy)alkylcarbonyloxy)alkyl, ((amino)alkylcarbonyloxy)alkyl, ((amino)cycloalkylcarbonyloxy)alkyl, ((((phosphonooxy)alkyl)carbonyloxy)alkyl)oxycarbonyl, ((((phosphonooxy)cycloalkyl)carbonyloxy)alkyl)oxycarbonyl, ((((amino)alkyl)carbonyloxy)alkyl)oxycarbonyl, ((((amino)cycloalkyl)carbonyloxy)alkyl)oxycarbonyl, or ((((phosphonooxy)(alkoxy)benzoyl)alkyloxycarbonyl;
R1 is H, halo, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R2 is H, halo, CN, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, NH2, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R3 is phenyl, pyrrolyl, or pyridinyl, wherein the phenyl, pyrrolyl, or pyridinyl is substituted with 0-3 independently selected R3a substituents;
each R3a is independently halo, C1-6 alkyl, C1-6 deuteroalkyl, C1-6 haloalkyl, C1-3 alkyl-C1-6 alkoxy, C1-3 alkyl-C3-6 cycloalkoxy, CH2-heterocyclyl, C(O)NRcRd, C(O)heterocyclyl, C1-6 alkoxy, hydroxy-C1-6 alkoxy, C1-6 deuteroalkoxy, C1-6 haloalkoxy, C1-3 alkoxy-C3-6 cycloalkyl, C1-3 deuteroalkoxy-C3-6 cycloalkyl, C1-3 haloalkoxy-C3-6 cycloalkyl, OP(O)(OH)2, Oheterocyclyl, OC6-10 aryl, SC6-10 aryl, S(O)2C1-4 alkyl, S(O)2C3-6 cycloalkyl, C3-6 cycloalkyl, C3-6 halocycloalkyl, C3-6 cycloalkoxy, heterocyclyl, or aryl;
wherein each heterocyclyl is independently a 4-6 membered ring containing 1-2 heteroatoms independently selected from the group consisting of N and O;
and
wherein each alkyl, cycloalkyl, heterocyclyl, and aryl is independently substituted with 0-2 independently selected Rb substituents;
or
two R3a on adjacent atoms join to form —OCH2CH2—, —OCH2CH2CH2—, —OCH2O—, or —OCH2CH2O—;
each Rb is independently halo, C1-3 alkyl, C1-3 haloalkyl, hydroxy-C1-3 alkyl, OH, C1-3 alkoxy, ═O, or C3-6 cycloalkyl;
each Rc is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
each Rd is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
each Rc and Rd, taken together with the nitrogen atom to which they are attached, independently forms a 4-6 membered heterocyclyl;
wherein each 4-6 membered heterocyclyl independently contains 0-1 additional heteroatom selected from the group consisting of N, O, and S;
and
wherein each 4-6 membered heterocyclyl is independently substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
R4 is H, F, Cl, Br, C1-4 alkyl, C1-4 deuteroalkyl, C1-4 haloalkyl, NReRf, C1-4 alkoxy, C1-4 deuteroalkoxy, or cyclopropyl;
Re is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rf is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
Re and Rf, taken together with the nitrogen atom to which they are attached, form a 4-6 membered heterocyclyl, wherein the heterocyclyl is substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
(iii) R5 is H, CN, C(O)CHR8NH2, NRgRh, OH, C1-3 alkoxy, OC(O)C1-3 alkyl, or OP(O)(OH)2;
R5a is H or C1-3 alkyl;
and
R5b is H or C1-3 alkyl;
or
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-2 substituents independently selected from the group consisting of F, C1-3 alkyl, and C1-3 haloalkyl;
or
(iv) R5 is absent;
and
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-1 substituent selected from the group consisting of F and C1-3 alkyl;
Rg is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rh is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
Rg and R1, taken together with the nitrogen atom to which they are attached, form azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl, or morpholin-4-yl, wherein the azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl, or morpholin-4-yl is substituted with 0-3 independently selected Ri substituents;
each Ri is independently halo, C1-3 alkyl, or C1-3 haloalkyl;
each Rj is independently halo or OH;
R6 is H or C1-3 alkyl;
R7 is H, halo, CN, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, or C1-3 haloalkoxy;
R8 is H, C1-3 alkyl, or C1-3 alkyl-C1-3 alkoxy;
and
n is 0, 1, or 2.

62 more elements

A compound having formula (I):

or pharmaceutically acceptable salt thereof,
wherein:
X is CR7 or N;
(i) L is —C(O)NRa— or —NRaC(O)—;
and
A is C1-4 alkyl, C1-4 deuteroalkyl, C1-3 alkyl-C3-6 cycloalkyl, or C3-6 cycloalkyl-C1-3 alkyl, wherein the C1-4 alkyl or C1-4 deuteroalkyl is substituted with 0-1 OH substituent;
or
(ii) L is —CH2—;
and
A is —NRaC(O)—;
Ra is H, C1-4 alkyl, or C1-4 deuteroalkyl;
R1 is H, halo, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R2 is H, halo, CN, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, NH2, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R3 is phenyl, pyrrolyl, or pyridinyl, wherein the phenyl, pyrrolyl, or pyridinyl is substituted with 0-3 independently selected R3a substituents;
each R3a is independently halo, C1-6 alkyl, C1-6 deuteroalkyl, C1-6 haloalkyl, C1-3 alkyl-C1-6 alkoxy, C1-3 alkyl-C3-6 cycloalkoxy, CH2-heterocyclyl, C(O)NRcRd, C1-6 alkoxy, hydroxy-C1-6 alkoxy, C1-6 deuteroalkoxy, C1-6 haloalkoxy, C1-3 alkoxy-C3-6 cycloalkyl, C1-3 deuteroalkoxy-C3-6 cycloalkyl, C1-3 haloalkoxy-C3-6 cycloalkyl, Oheterocyclyl, SC6-10 aryl, S(O)2C1-4 alkyl, S(O)2C3-6 cycloalkyl, C3-6 cycloalkyl, C3-6 halocycloalkyl, C3-6 cycloalkoxy, or heterocyclyl;
wherein each heterocyclyl is independently a 4-6 membered ring containing 1-2 heteroatoms independently selected from the group consisting of N and O;
and
wherein each alkyl, cycloalkyl, and heterocyclyl is independently substituted with 0-2 independently selected Rb substituents;
each Rb is independently halo, C1-3 alkyl, C1-3 haloalkyl, or =0;
each Rc is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
each Rd is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
each Rc and Rd, taken together with the nitrogen atom to which they are attached, independently forms a 4-6 membered heterocyclyl;
wherein each 4-6 membered heterocyclyl independently contains 0-1 additional heteroatom selected from the group consisting of N, O, and S;
and
wherein each 4-6 membered heterocyclyl is independently substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
R4 is H, F, Cl, Br, C1-4 alkyl, C1-4 deuteroalkyl, C1-4 haloalkyl, NReRf C1-4 alkoxy, C1-4 deuteroalkoxy, or cyclopropyl;
Re is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rf is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
Re and Rf, taken together with the nitrogen atom to which they are attached, form a 4-6 membered heterocyclyl, wherein the heterocyclyl is substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
(iii) R5 is H, CN, C(O)CHRgNH2, NRgRh, OH, C1-3 alkoxy, OC(O)C1-3 alkyl, or OP(O)(OH)2;
R5a is H or C1-3 alkyl;
and
R5b is H or C1-3 alkyl;
or
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-1 substituent selected from the group consisting of F and C1-3 alkyl;
or
(iv) R5 is absent;
and
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-1 substituent selected from the group consisting of F and C1-3 alkyl;
Rg is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rh is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
R6 is H or C1-3 alkyl;
R7 is H, halo, CN, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, or C1-3 haloalkoxy;
and
R8 is H, C1-3 alkyl, or C1-3 alkyl-C1-3 alkoxy.

50 more elements

A compound selected from the group consisting of:

N-[(5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridin-3-yl)methyl]-2-fluoro-5-(trifluoromethoxy)benzamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl](D2)methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxypyridine-3-carboxamide;
2-methoxy-5-[2-(2-methoxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-2-methoxy-5-[2-(2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-[2-(2-cyanoacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-[2-(2-cyano-2,2-dimethylacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-5-[2-(2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxy-6-methyl-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxy-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3-fluorophenyl]methyl}-5-[2-(2-hydroxy-2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-({2-[(1-hydroxypropan-2-yl)oxy]phenyl}methyl)-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-(trifluoromethyl)pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[2-(propan-2-yloxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-[3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
2-fluoro-N-(6-{3-[(3-phenylbutyl)carbamoyl]phenyl}imidazo[1,2-b]pyridazin-2-yl)pyridine-4-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-(3-phenylbutyl)pyridine-3-carboxamide;
5-[2-(2-cyano-2,2-dimethylacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-[(2-{[2-(hydroxymethyl)phenyl]sulfanyl}phenyl)methyl]-2-methylpyridine-3-carboxamide;
5-[2-(2-cyano-2,2-dimethylacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
5-[2-(2-cyano-2,2-dimethylacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-[2-(2-cyano-2,2-dimethylacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-(trifluoromethyl)pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,6-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(trifluoromethyl)pyridine-3-carboxamide;
5-[2-(2-cyanoacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxy-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-[2-(2-cyanoacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxypyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxypyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-5-[2-(2-hydroxy-2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]-2-methoxypyridine-3-carboxamide;
5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-N-(2-fluoro-5-methoxybenzyl)-2,6-dimethylnicotinamide;
N-(2-fluoro-5-(trifluoromethoxy)benzyl)-5-(2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl)-2,6-dimethylnicotinamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(2-fluoro-5-methoxyphenyl)methyl]-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3R)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl](deutero)methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-(D3)methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxetan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxy-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(D3)methoxy-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-(D3)methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3R)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(2-methyloxan-4-yl)oxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-[(2-{[(2R,6S)-2,6-dimethyloxan-4-yl]oxy}-3-fluorophenyl)methyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-({2-[(2,6-dimethyloxan-4-yl)oxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[3-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}pyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl](deutero)methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl](2,2,2-deutero)ethyl]-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[2-(2,2,2-trifluoroethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]methyl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[3-(2,2,2-trifluoroethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[3-(trifluoromethyl)phenyl](deutero)methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl](deutero)methyl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2,6-dimethylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxetan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2,6-dimethylpyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)pyridin-3-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)pyridin-3-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2,6-dimethylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2,6-dimethylpyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethyl)phenyl](deutero)methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2,6-dimethylpyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2,6-dimethylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2,6-dimethylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(2-methyloxan-4-yl)oxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(2-fluoro-5-methoxyphenyl)methyl]-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[3-(2,2,2-trifluoroethoxy)pyridin-2-yl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-({2-[(2,6-dimethyloxan-4-yl)oxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-[(1R)-1-[2-(trifluoromethyl)phenyl]ethyl]pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1S)-1-[2-fluoro-5-(trifluoromethyl)phenyl](2,2,2-deutero)ethyl]-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl](2,2,2-deutero)ethyl]-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(2,2,2-trifluoroethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[3-(trifluoromethyl)phenyl](deutero)methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl](deutero)methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-[(1R)-1-[3-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-({2-[(morpholin-4-yl)methyl]phenyl}methyl)pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-({2-[(propan-2-yloxy)methyl]phenyl}methyl)pyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxetan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(2-methylpropoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(2-methylpropoxy)phenyl]methyl}pyridine-3-carboxamide;
N-[(2-cyclopropoxy-3,5-difluorophenyl)methyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[4-fluoro-2-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{1-[2-(cyclopropylmethoxy)-6-fluorophenyl]ethyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{1-[3-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
N-{1-[2-(cyclopropylmethoxy)-6-fluorophenyl]ethyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{1-[3-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,6-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(oxan-4-yloxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{1-[2-(cyclopropylmethoxy)-3,5-difluorophenyl]ethyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{1-[2-(cyclopropylmethoxy)-3,5-difluorophenyl]ethyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[3-(1-cyclopropylethoxy)pyridin-2-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
N-{[3-(cyclopropylmethoxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-[(3,6-difluoro-2-methoxyphenyl)methyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[3-(cyclopropylmethoxy)-4-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-methyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-{[2-chloro-5-(trifluoromethyl)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(1-cyclopropylethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-4,6-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[4-fluoro-2-(oxan-4-yloxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-N-((3,5-difluoro-2-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)methyl-d2)-2-methoxynicotinamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropanesulfonyl)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(1H-pyrrol-1-yl)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[(1S,2S)-2-(4-fluorophenyl)cyclopropyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(morpholin-4-yl)phenyl]methyl}pyridine-3-carboxamide;
N-{[3-(cyclopentyloxy)pyridin-2-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(propan-2-yloxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-({2-[(2,6-dimethyloxan-4-yl)oxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-[(2-{[(2R,6S)-2,6-dimethyloxan-4-yl]oxy}-3-fluorophenyl)methyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3R)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(2-methyloxan-4-yl)oxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-(deutero)methoxy-6-methylpyridine-3-carboxamide;
N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl](deutero)methyl}-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-5-[2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl]-2-methylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-3-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(3S)-oxolan-3-yloxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-({3,5-difluoro-2-[(2-methyloxan-4-yl)oxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-({2-[(2,6-dimethyloxan-4-yl)oxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[4-(trifluoromethyl)pyridin-2-yl]methyl}pyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl](deutero)methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[2-(2,2,2-trifluoroethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[3-(2,2,2-trifluoroethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(2,2,2-trifluoroethoxy)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1S)-1-[2-fluoro-5-(trifluoromethyl)phenyl](2,2,2-deutero)ethyl]-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl](2,2,2-deutero)ethyl]-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl](deutero)methyl}-2-methylpyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)pyridin-3-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[2-(oxolan-3-yloxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl](2,2,2-deutero)ethyl]-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-6-methyl-N-(3-phenylbutyl)pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-6-methyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-(3-phenylbutyl)pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[3-(cyclopentyloxy)pyridin-2-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-(cyclopentyloxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-2-methoxy-5-{2-propanamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-2-methyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methylpyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-N-{[4-fluoro-3-(trifluoromethoxy)phenyl]methyl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-(3-phenylbutyl)pyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-5-{2-acetamido-3-methylimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-2-methoxy-5-[2-(2-methoxyacetamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-2-methoxy-5-[2-(2-methoxyacetamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-5-[2-(2-methoxyacetamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
2-methoxy-5-[2-(2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-2-methoxy-5-[2-(2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
N-{[3,5-difluoro-2-(oxan-4-yloxy)phenyl]methyl}-2-methoxy-5-[2-(2-methylpropanamido)imidazo[1,2-b]pyridazin-6-yl]pyridine-3-carboxamide;
2-chloro-N-({2-[cyclopropyl(deutero)methoxy]-3,5-difluorophenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
2-chloro-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
2-chloro-N-{[2-(1-cyclobutylethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
2-chloro-N-{[2-chloro-5-(trifluoromethyl)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N,6-dimethyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl](deutero)methyl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-N,6-dimethyl-N-{[2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-4,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-[(3,6-difluoro-2-methoxyphenyl)methyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,4-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl](deutero)methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{1-[3-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{1-[2-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{1-[3-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[3-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[2-(trifluoromethoxy)phenyl](deutero)methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-4,6-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(1-cyclopentylethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(1-cyclopentylethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{2-[3-(trifluoromethoxy)phenyl]ethyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[3-(trifluoromethyl)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[2-(oxolan-3-yloxy)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[2-(oxolan-3-yloxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)-4,6-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[3-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-({2-[(4,4-difluorocyclohexyl)methoxy]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[3-(cyclopentylmethoxy)pyridin-2-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)pyridin-3-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclobutylmethoxy)pyridin-3-yl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopentylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)-4-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxy-6-methyl-N-{[3-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
2-((6-(5-((2-fluoro-5-(trifluoromethoxy)benzyl)carbamoyl)-2,6-dimethylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl)amino)-2-oxoethyl dihydrogen phosphate;
6-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
6-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(trifluoromethoxy)phenyl]methyl}pyridine-3-carboxamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-3,5-difluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methoxypyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(2,2,2-trifluoroethoxy)phenyl]methyl}-2,6-dimethylpyridine-3-carboxamide;
N-{[5-(cyclopropylmethoxy)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-dimethylpyridine-3-carboxamide;
({6-[5-({[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}carbamoyl)-2,6-dimethylpyridin-3-yl]imidazo[1,2-b]pyridazin-2-yl}carbamoyl)methyl acetate;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-ethyl-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-ethyl-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}pyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-N,2-dimethylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-2-methyl-5-(2-{2-[4-(trifluoromethyl)piperidin-1-yl]acetamido}imidazo[1,2-b]pyridazin-6-yl)pyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-2-methyl-5-{2-[2-(4-methylpiperazin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]-2-methyl-5-{2-[2-(pyrrolidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
5-{2-[2-(4,4-difluoropiperidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
5-{2-[2-(3,3-difluoroazetidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methyl-5-{2-[2-(4-methylpiperazin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methyl-5-{2-[2-(morpholin-4-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
5-{2-[2-(dimethylamino)acetamido]imidazo[1,2-b]pyridazin-6-yl}-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
N—((R)-1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl)-5-(2-((S)-2-hydroxypropanamido)imidazo[1,2-b]pyridazin-6-yl)-2-methylnicotinamide;
N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methyl-5-{2-[2-(methylamino)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
5-[2-(2-aminoacetamido)imidazo[1,2-b]pyridazin-6-yl]-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylpyridine-3-carboxamide;
{[6-(5-{[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]carbamoyl}-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]carbamoyl}methyl acetate;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-[2-(4,4-difluoropiperidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-[2-(3,3-difluoroazetidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-methyl-5-{2-[2-(morpholin-4-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-methyl-5-{2-[2-(morpholin-4-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}pyridine-3-carboxamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-[2-(dimethylamino)acetamido]imidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[1-(4-fluorophenyl)ethyl]-1H-pyrazol-4-yl}-2-methylpyridine-3-carboxamide;
N-{1-[(4-chlorophenyl)methyl]-1H-imidazol-4-yl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{1-[(4-fluorophenyl)methyl]-1H-imidazol-4-yl}-2-methylpyridine-3-carboxamide;
N-(1-benzyl-1H-imidazol-4-yl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylpyridine-3-carboxamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}-2-methylpyridine-3-carboxamide;
N-[6-(5-{3-[(4-fluorophenyl)(hydroxy)methyl]piperidine-1-carbonyl}-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-[3-(4-fluorophenyl)-2-hydroxy-2-methylpropyl]-2-methylpyridine-3-carboxamide;
N-[6-(5-{3-[(4-fluorophenyl)methyl]-3-hydroxypiperidine-1-carbonyl}-6-methylpyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]acetamide;
5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-3-fluoro-N-(2-fluoro-5-(1-methyl-1H-pyrazol-4-yl)benzyl)-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-N-{[2-fluoro-3-(trifluoromethoxy)phenyl]methyl}-2-methylbenzamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-[2-(dimethylamino)acetamido]imidazo[1,2-b]pyridazin-6-yl}-3-fluoro-2-methylbenzamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-fluoro-2-methyl-5-{2-[2-(methylamino)acetamido]imidazo[1,2-b]pyridazin-6-yl}benzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-2-methyl-N-[(2-phenoxyphenyl)methyl]benzamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-6-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,3-difluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,3-difluoro-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]benzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4,5-trifluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4,5-trifluoro-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}benzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-5-fluorobenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-3-fluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxybenzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-5-fluoro-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-4-methylbenzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-5-fluoro-4-methylbenzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methoxybenzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]-6-methoxybenzamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-5-fluorophenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methoxybenzamide;
N-{[2-(cyclopropylmethoxy)phenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methoxybenzamide;
(R)-3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)-6-methoxybenzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-difluoro-N-[(1S)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]benzamide;
(R)-3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2,6-difluoro-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)benzamide;
N-{[2-(4,4-difluoropiperidine-1-carbonyl)-5-fluorophenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,6-difluorobenzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4-dimethylbenzamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4-dimethylbenzamide;
N-{[3-chloro-2-fluoro-5-(trifluoromethyl)phenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4-dimethylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethyl)phenyl]methyl}-2-(trifluoromethyl)benzamide;
2-chloro-N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}benzamide;
2-chloro-N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}benzamide;
6-chloro-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]benzamide;
6-chloro-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-{[2-fluoro-5-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}benzamide;
6-chloro-N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluorobenzamide;
6-chloro-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-{[4-(trifluoromethoxy)phenyl]methyl}benzamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-N-[(1R)-1-[2-fluoro-5-(trifluoromethoxy)phenyl]ethyl]benzamide;
2-chloro-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-4-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methylbenzamide;
(S)—N-(2-fluoro-5-(trifluoromethoxy)benzyl)-5-(2-(2-hydroxypropanamido)imidazo[1,2-b]pyridazin-6-yl)-2-methylbenzamide;
(R)-5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl)-2-methylbenzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
N-[(3S)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
N-(1-benzyl-1H-pyrazol-4-yl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-(2-hydroxy-3-phenoxypropyl)-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[(1S,2S)-2-(4-fluorophenyl)cyclopropyl]methyl}-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-6-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}-2-methylbenzamide;
N-{[5-(3,3-difluoroazetidine-1-carbonyl)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-4-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
N-{[5-(3,3-dimethylpyrrolidine-1-carbonyl)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
N-({3,5-difluoro-2-[(3S)-3-hydroxypyrrolidine-1-carbonyl]phenyl}methyl)-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[5-fluoro-2-(piperidine-1-carbonyl)phenyl]methyl}-2-methylbenzamide;
N-{[5-(1-cyclopropyl-1H-pyrazol-4-yl)-2-fluorophenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methylbenzamide;
N-{[2-(1-cyclopropyl-1H-pyrazol-4-yl)-5-fluorophenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methylbenzamide;
N-{[2-(3,3-difluoropyrrolidine-1-carbonyl)-3,4-difluorophenyl]methyl}-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methylbenzamide;
(R)-3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)-6-methylbenzamide;
(R)-3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-(1-(2-fluoro-5-(trifluoromethyl)phenyl)ethyl-2,2,2-d3)-6-methylbenzamide;
N-[(3,5-difluoro-2-methoxyphenyl)methyl]-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-6-methylbenzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-2-methylbenzamide;
N-{[5-(2,2-dimethylpyrrolidine-1-carbonyl)-2-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-2-methylbenzamide;
5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-N-(2-fluoro-5-(trifluoromethoxy)benzyl)-2-(methoxy-d3)-4-methylbenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxybenzamide;
N-{[2-(2,2-dimethylpyrrolidine-1-carbonyl)-5-fluorophenyl]methyl}-5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-2-methoxybenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-N-[(2-fluoro-6-methoxyphenyl)methyl]-2-methoxybenzamide;
5-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-2-methoxy-4-methylbenzamide;
N-(2-fluoro-5-(trifluoromethoxy)benzyl)-5-(2-(2-hydroxyacetamido)imidazo[1,2-b]pyridazin-6-yl)-2-methoxy-4-methylbenzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2,4-difluoro-N-[(1R)-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethyl]benzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-N-(5-(2,2-dimethylazetidine-1-carbonyl)-2-fluorobenzyl)-2-fluorobenzamide;
3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-((2-fluoro-5-(trifluoromethoxy)phenyl)methyl-d2)benzamide;
3-{2-[2-(4,4-difluoropiperidin-1-yl)acetamido]imidazo[1,2-b]pyridazin-6-yl}-2-fluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
N-[(3R)-3-(4-chlorophenyl)-3-hydroxypropyl]-2-fluoro-3-(2-{2-[4-(trifluoromethyl)piperidin-1-yl]acetamido}imidazo[1,2-b]pyridazin-6-yl)benzamide;
(S)-3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl-2,2,2-d3)-4-methylbenzamide;
3-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-fluoro-N-((2-fluoro-5-(trifluoromethoxy)phenyl)methyl-d2)-4-methylbenzamide;
4-chloro-3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-4-fluoro-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}benzamide;
3-{2-acetamidoimidazo[1,2-b]pyridazin-6-yl}-N-{[2-fluoro-5-(trifluoromethoxy)phenyl]methyl}-4-methylbenzamide;
and
(R)-(((5-(2-acetamidoimidazo[1,2-b]pyridazin-6-yl)-2-methylnicotinoyl)(1-(2-fluoro-5-(trifluoromethoxy)phenyl)ethyl)carbamoyl)oxy)methyl 3-methoxy-4-(phosphonooxy)benzoate, or pharmaceutically acceptable salt thereof.

430 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/758,892Filed 29 Oct 2018 · us provisional application
Priority: 30 Oct 2017
Published: US 2020/0277296 A13 Sep 2020
Granted: 13 Sep 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07F 9/6561
Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom: containing systems of two or more relevant hetero rings condensed among…

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Application62/578,607Us provisional application · filed 30 Oct 2017
Application62/626,853Us provisional application · filed 6 Feb 2018
US 2020/0277296 A1Pre-grant publication · published 3 Sep 2020
US 11,440,913 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound having formula (I):

or pharmaceutically acceptable salt thereof,
wherein:
X is CR7 or N;
(i) L is —C(O)NRa— or
and
A is C1-4 alkyl, C1-4 deuteroalkyl, C1-3 alkyl-C3-6 cycloalkyl, C0-3 alkyl-heterocyclyl, C1-4 alkoxy, or C3-6 cycloalkyl-C1-3 alkyl;
wherein the C1-4 alkyl, C1-4 deuteroalkyl, or C1-4 alkoxy is substituted with 0-1 OH substituent;
wherein the alkyl of the C0-3 alkyl-heterocyclyl is substituted with 0-1 OH substituent;
wherein the heterocyclyl of the C0-3 alkyl-heterocyclyl is a 3-6 membered ring containing 1-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the heterocyclyl of the C0-3 alkyl-heterocyclyl is substituted with 0-2 substituents independently selected from the group consisting of halo, C1-3 alkyl, and OH;
or
(ii) L is —CH2—;
and
A is —NRaC(O)—;
Ra is H, C1-4 alkyl, C1-4 deuteroalkyl, ((phosphonooxy)alkylcarbonyloxy)alkyl, ((amino)alkylcarbonyloxy)alkyl, ((amino)cycloalkylcarbonyloxy)alkyl, ((((phosphonooxy)alkyl)carbonyloxy)alkyl)oxycarbonyl, ((((phosphonooxy)cycloalkyl)carbonyloxy)alkyl)oxycarbonyl, ((((amino)alkyl)carbonyloxy)alkyl)oxycarbonyl, ((((amino)cycloalkyl)carbonyloxy)alkyl)oxycarbonyl, or ((((phosphonooxy)(alkoxy)benzoyl)alkyloxycarbonyl;
R1 is H, halo, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R2 is H, halo, CN, C1-3 alkyl, C1-3 deuteroalkyl, C1-3 haloalkyl, NH2, C1-3 alkoxy, C1-3 deuteroalkoxy, or C1-3 haloalkoxy;
R3 is phenyl, pyrrolyl, or pyridinyl, wherein the phenyl, pyrrolyl, or pyridinyl is substituted with 0-3 independently selected R3a substituents;
each R3a is independently halo, C1-6 alkyl, C1-6 deuteroalkyl, C1-6 haloalkyl, C1-3 alkyl-C1-6 alkoxy, C1-3 alkyl-C3-6 cycloalkoxy, CH2-heterocyclyl, C(O)NRcRd, C(O)heterocyclyl, C1-6 alkoxy, hydroxy-C1-6 alkoxy, C1-6 deuteroalkoxy, C1-6 haloalkoxy, C1-3 alkoxy-C3-6 cycloalkyl, C1-3 deuteroalkoxy-C3-6 cycloalkyl, C1-3 haloalkoxy-C3-6 cycloalkyl, OP(O)(OH)2, Oheterocyclyl, OC6-10 aryl, SC6-10 aryl, S(O)2C1-4 alkyl, S(O)2C3-6 cycloalkyl, C3-6 cycloalkyl, C3-6 halocycloalkyl, C3-6 cycloalkoxy, heterocyclyl, or aryl;
wherein each heterocyclyl is independently a 4-6 membered ring containing 1-2 heteroatoms independently selected from the group consisting of N and O;
and
wherein each alkyl, cycloalkyl, heterocyclyl, and aryl is independently substituted with 0-2 independently selected Rb substituents;
or
two R3a on adjacent atoms join to form —OCH2CH2—, —OCH2CH2CH2—, —OCH2O—, or —OCH2CH2O—;
each Rb is independently halo, C1-3 alkyl, C1-3 haloalkyl, hydroxy-C1-3 alkyl, OH, C1-3 alkoxy, ═O, or C3-6 cycloalkyl;
each Rc is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
each Rd is independently H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
each Rc and Rd, taken together with the nitrogen atom to which they are attached, independently forms a 4-6 membered heterocyclyl;
wherein each 4-6 membered heterocyclyl independently contains 0-1 additional heteroatom selected from the group consisting of N, O, and S;
and
wherein each 4-6 membered heterocyclyl is independently substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
R4 is H, F, Cl, Br, C1-4 alkyl, C1-4 deuteroalkyl, C1-4 haloalkyl, NReRf, C1-4 alkoxy, C1-4 deuteroalkoxy, or cyclopropyl;
Re is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rf is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
Re and Rf, taken together with the nitrogen atom to which they are attached, form a 4-6 membered heterocyclyl, wherein the heterocyclyl is substituted with 0-4 substituents independently selected from the group consisting of deuterium and halo;
(iii) R5 is H, CN, C(O)CHR8NH2, NRgRh, OH, C1-3 alkoxy, OC(O)C1-3 alkyl, or OP(O)(OH)2;
R5a is H or C1-3 alkyl;
and
R5b is H or C1-3 alkyl;
or
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-2 substituents independently selected from the group consisting of F, C1-3 alkyl, and C1-3 haloalkyl;
or
(iv) R5 is absent;
and
R5a and R5b, taken together with the carbon atom to which they are attached, form a 3-6 membered carbocyclyl or 3-6 membered heterocyclyl;
wherein the 3-6 membered heterocyclyl contains 0-2 heteroatoms independently selected from the group consisting of N, O, and S;
and
wherein the 3-6 membered carbocyclyl or 3-6 membered heterocyclyl is substituted with 0-1 substituent selected from the group consisting of F and C1-3 alkyl;
Rg is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
Rh is H, C1-3 alkyl, C1-3 deuteroalkyl, or C3-6 cycloalkyl;
or
Rg and R1, taken together with the nitrogen atom to which they are attached, form azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl, or morpholin-4-yl, wherein the azetidin-1-yl, pyrrolidin-1-yl, piperidin-1-yl, piperazin-1-yl, or morpholin-4-yl is substituted with 0-3 independently selected Ri substituents;
each Ri is independently halo, C1-3 alkyl, or C1-3 haloalkyl;
each Rj is independently halo or OH;
R6 is H or C1-3 alkyl;
R7 is H, halo, CN, C1-3 alkyl, C1-3 haloalkyl, C1-3 alkoxy, or C1-3 haloalkoxy;
R8 is H, C1-3 alkyl, or C1-3 alkyl-C1-3 alkoxy;
and
n is 0, 1, or 2.

62 more elements

Facts

Application

16/758,892Filed 29 Oct 2018 · us provisional application

Priority

30 Oct 2017

Published

US 2020/0277296 A13 Sep 2020

Granted

13 Sep 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification7 codes

A61P 29/00
Non-central analgesic, antipyretic or antiinflammatory agents
C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07F 9/6561
Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom: containing systems of two or more relevant hetero rings condensed among…