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US 2026/0007680 A1Published application
Compounds and Their Use as PDE4 Activators
AssigneeMironid Limited
InventorsJulia Mary Adam, David Roger Adams
Life of this patent
Estimating the term…
Abstract
The present invention relates to compounds of Formulas I to IV, their use as activators of long form cyclic nucleotide phosphodiesterase-4 (PDE4) enzymes (isoforms) and to these compounds for use in a method for the treatment or prevention of disorders requiring a reduction of second messenger responses mediated by cyclic 3′,5′-adenosine monophosphate (cAMP).
Claims42
A compound of Formula I
- or a pharmaceutically acceptable salt or derivative thereof, wherein:
- one of X1 and X2 is N and the other is N or CR3a, one of Y1 and Y2 is N and the other is C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b;
- or
- one of X1 and X2 is N and the other is NR3c or O, Y1 and Y2 are each C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b;
- or
- one of X1 and X2 is S and the other is N or CR3a, Y1 and Y2 are each C, and one of Z1, Z2 and Z3 is N and the others are each CR3b;
- R1 is a 4- to 10-membered monocyclic, bridged or bicyclic ring containing at least 1 ring N heteroatom and optionally a ring O heteroatom, and wherein R1 is optionally substituted with 1 or more R4;
- R2 is
- (v) (C5-7)cycloalkyl, fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vi) a 5- to 7-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vii) CH2Ar, where Ar is a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- or
- (viii) a (C3-8)alkyl group that may be straight chain, branched or cyclic, or a combination thereof;
- and wherein R2 is optionally substituted with 1 or more R5;
- each R3a is independently H or (C1-6)alkyl, the (C1-6)alkyl being optionally substituted by 1 or more halogen;
- each R3b is independently H, (C1-6)alkyl, (C1-6)alkoxy, CN or halogen, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen;
- each R3c is independently H or (C1-6)alkyl, the (C1-6)alkyl being optionally substituted by 1 or more halogen;
- each R4 is independently halogen, CN, OH, (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl and —(C1-6)alkylene-(C1-6)alkoxy being optionally substituted with 1 or more substituents independently selected from halogen, OH and (C1-6)alkoxy;
- and
- each R5 is independently halogen, OH, CN, (C1-6)alkyl, (C1-6)alkoxy or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen or OH;
- for use in the treatment or prevention of a disease or disorder that can be ameliorated by activation of long isoforms of PDE4 or a disease or disorder mediated by excessive intracellular cyclic AMP signalling.
18 more elements
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein R2 is:
- (i) (C5-7)cycloalkyl, fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms, wherein the (C5-7)cycloalkyl is optionally substituted with 1 to 3 substituents independently selected from OH, halogen, (C1-4)alkyl and (C1-4)alkoxy, the (C1-4)alkyl and (C1-4)alkoxy groups being optionally substituted with one or more fluoro, and the 6-membered aromatic or heteroaromatic ring is optionally substituted with 1 to 3 substituents independently selected from (C1-4)alkyl, (C1-4)alkoxy, CN and halogen, the (C1-4)alkyl and (C1-4)alkoxy groups being optionally substituted with one or more fluoro;
- (ii) a 5- to 7-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms, wherein the 5- to 7-membered non-aromatic heterocycle is optionally substituted with 1 to 3 substituents on one or more ring carbon atoms independently selected from OH, halogen, (C1-4)alkyl and (C1-4)alkoxy, the (C1-4)alkyl and (C1-4)alkoxy groups being optionally substituted with one or more fluoro, and the 6-membered aromatic or heteroaromatic ring is optionally substituted with 1 to 3 substituents independently selected from (C1-4)alkyl, (C1-4)alkoxy, CN and halogen, the (C1-4)alkyl and (C1-4)alkoxy groups being optionally substituted with one or more fluoro;
- (iii) CH2Ar, wherein the Ar is optionally substituted with 1 to 3 substituents selected from halogen, CN, (C1-4)alkyl, (C1-4)alkoxy and the CH2 is optionally substituted with (C1-4)alkyl the (C1-4)alkyl group being optionally substituted with OH or (C1-4)alkyloxy;
- or
- (iv) a (C3-8)alkyl group that may be straight chain, branched or cyclic or a combination thereof, optionally substituted with 1 or more halogen, (C1-4)alkoxy or OH.
2 more elements
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein R2 is:
- (i) (C5-6)cycloalkyl, optionally fused to a phenyl ring;
- (ii) a 5- to 6-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a phenyl ring;
- wherein R2 is optionally substituted with 1 or more R5.
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein R2 is a group of formula
- wherein A is O or CH2;
- p is 1, 2 or 3;
- Ph is an optionally present, fused phenyl ring, and wherein R2 is optionally substituted with 1 or more R5;
- optionally wherein A is O or C(R5)2 (for example, CF2).
1 more element
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein:
- a) each R3a is independently —H or CH3;
- b) each R3b is independently —H, —CH3, —OCH3, halo, CN or cyclopropyl;
- and/or
- c) each R3c is independently —H or CH3.
1 more element
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein the bicyclic heteroaromatic ring system containing X1, X2, Y1, Y2, Z1, Z2 and Z3 is selected from:
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein one of X1 and X2 is N and the other is N or CR3a, one of Y1 and Y2 is N and the other is C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b.
The compound, or a pharmaceutically acceptable salt or derivative thereof, for use of any preceding claim, wherein
- R1 is a 6-membered saturated
- monocyclic ring containing 1 or 2 ring N heteroatoms, wherein at least 1 ring N heteroatom is not at the point of attachment of R1, or a 7- to 8-membered saturated, bridged ring system containing 2 ring N heteroatoms, and wherein R1 is optionally substituted with 1 R4;
- R2 is
- (i) (C5-6)cycloalkyl, optionally fused to a phenyl ring;
- or
- (ii) a 5- to 6-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a phenyl ring;
- and wherein R2 is optionally substituted with 1 or more R5;
- R3a, R3b and R3c, where present, are each independently H or methyl (optionally wherein 0 or 1 of R3a, R3b and R3c is methyl and the others are H);
- R4, where present, is (C1-6)alkyl optionally substituted with OH;
- and
- R5, where present, is OH.
8 more elements
A compound of Formula II
- or a pharmaceutically acceptable salt or derivative thereof, wherein:
- one of X1 and X2 is N and the other is N or CR3a, one of Y1 and Y2 is N and the other is C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b;
- or
- one of X1 and X2 is S and the other is N or CR3a, Y1 and Y2 are each C, and one of Z1, Z2 and Z3 is N and the others are each CR3b;
- R1a is a 4- to 10-membered non-aromatic ring that can be monocyclic, bridged or bicyclic containing at least 1 ring N heteroatom and optionally a ring O heteroatom, wherein at least 1 ring N heteroatom is not at the point of attachment of R1a, and wherein R1a is optionally substituted with 1 or more R4;
- R2 is
- (v) (C5-7)cycloalkyl, fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vi) a 5- to 7-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vii) CH2Ar, where Ar is a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- or
- (viii) a (C3-8)alkyl group that may be straight chain, branched or cyclic, or a combination thereof;
- and wherein R2 is optionally substituted with 1 or more R5;
- each R3a is independently H or (C1-6)alkyl, the (C1-6)alkyl being optionally substituted by 1 or more halogen;
- each R3b is independently H, (C1-6)alkyl, (C1-6)alkoxy, CN or halogen, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen;
- each R4 is independently halogen, CN, OH, (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl and —(C1-6)alkylene-(C1-6)alkoxy being optionally substituted with 1 or more substituents independently selected from halogen, OH and (C1-6)alkoxy;
- and
- each R5 is independently halogen, OH, CN, (C1-6)alkyl, (C1-6)alkoxy or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen or OH.
14 more elements
A compound of Formula III
- or a pharmaceutically acceptable salt or derivative thereof, wherein:
- one of X1 and X2 is N and the other is N or CR3a, one of Y1 and Y2 is N and the other is C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b;
- or
- one of X1 and X2 is S and the other is N or CR3a, Y1 and Y2 are each C, and one of Z1, Z2 and Z3 is N and the others are each CR3b;
- R1 is a 4- to 10-membered monocyclic, bridged or bicyclic ring containing at least 1 ring N heteroatom and optionally a ring O heteroatom, and wherein R1 is optionally substituted with 1 or more R4;
- R2a is
- (iii) (C5-7)cycloalkyl fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (35) a 5- to 7-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- or
- (iv) a (C5-6)cycloalkyl group;
- and wherein R2a is optionally substituted with 1 or more R5;
- each R3a is independently H or (C1-6)alkyl, the (C1-6)alkyl being optionally substituted by 1 or more halogen;
- each R3b is independently —H, (C1-6)alkyl, (C1-6)alkoxy, CN or halogen, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen;
- each R4 is independently halogen, CN, OH, (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl and —(C1-6)alkylene-(C1-6)alkoxy being optionally substituted with 1 or more substituents independently selected from halogen, OH and (C1-6)alkoxy;
- and
- each R5 is independently halogen, OH, CN, (C1-6)alkyl, (C1-6)alkoxy or —(C1-6)alkylene-(C1-6)alkoxy the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen or OH;
- and wherein when one of X1 and X2 is S and the other is N, Y1 and Y2 are each C, one of Z1, Z2 and Z3 is N and R2a is (iv) a (C5-6)cycloalkyl group, R2a is substituted by at least 2 R5.
14 more elements
A compound of Formula IV
- or a pharmaceutically acceptable salt or derivative thereof, wherein:
- one of X1 and X2 is N and the other is N or CR3a, one of Y1 and Y2 is N and the other is C, and one of Z1, Z2 and Z3 is N or CR3b and the others are each CR3b;
- or
- one of X1 and X2 is S and the other is N or CR3a, Y1 and Y2 are each C, and one of Z1, Z2 and Z3 is N and the others are each CR3b;
- R1 is a 4- to 10-membered monocyclic, bridged or bicyclic ring containing at least 1 ring N heteroatom and optionally a ring O heteroatom, and wherein R1 is optionally substituted with 1 or more R4;
- R2 is
- (v) (C5-7)cycloalkyl, fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vi) a 5- to 7-membered non-aromatic heterocycle containing one ring O heteroatom, optionally fused to a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- (vii) CH2Ar, where Ar is a 6-membered aromatic or heteroaromatic ring that contains 0, 1 or 2 ring N atoms;
- or
- (viii) a (C3-8)alkyl group that may be straight chain, branched or cyclic, or a combination thereof;
- and wherein R2 is optionally substituted with 1 or more R5;
- each R3a is independently H or (C1-6)alkyl, the (C1-6)alkyl being optionally substituted by 1 or more halogen;
- each R3b is independently H, (C1-6)alkyl, (C1-6)alkoxy, CN or halogen, the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen, wherein at least 1 R3b is other than H;
- each R4 is independently halogen, CN, OH, (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl or —(C1-6)alkylene-(C1-6)alkoxy, the (C1-6)alkyl, (C1-6)alkoxy, (C3-7)cycloalkyl and (C1-6)alkylene-(C1-6)alkoxy being optionally substituted with 1 or more substituents independently selected from halogen, OH and (C1-6)alkoxy;
- and
- each R5 is independently halogen, OH, CN, (C1-6)alkyl, (C1-6)alkoxy or —(C1-6)alkylene-(C1-6)alkoxy the (C1-6)alkyl and (C1-6)alkoxy being optionally substituted by 1 or more halogen or OH.
14 more elements
A compound selected from:
- (S)—N-(chroman-4-yl)-2-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(6-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(2-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(5-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)-2-(pyridin-3-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)-2-(pyridin-3-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)—N-(chroman-4-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)—N-(2,3-dihydro-1H-inden-1-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)—N-(6-chlorochroman-4-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(6-chlorochroman-4-yl)-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)-2-(1-methylpiperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)-2-(1-methylpiperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (R)—N-(6-chlorochroman-4-yl)-2-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(6-chlorochroman-4-yl)-2-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-methylpiperidin-4-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(6-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(2-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(4-methylpyridin-3-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(6-methylpyridin-3-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(2-methylpyridin-3-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(5-methylpyridin-3-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(pyridin-3-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)-1-methyl-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)-1-methyl-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-1-methyl-2-(piperazin-1-yl)-1H-benzo[d]imidazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(pyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(6-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(5-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(2-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(2,6-dimethylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-morpholino-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)-2-(4-(tert-butyl)piperazin-1-yl)-N-(chroman-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-isopropylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (R)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-methylpiperidin-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-ethylpiperidin-4-yl)-[1,2,4]triazolo[1, 5-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(2-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-hydroxypiperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-morpholino-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)-2-(4-(tert-butyl)piperazin-1-yl)-N-(chroman-4-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperidin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-isopropylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (R)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(4-ethylpiperazin-1-yl)-[1,2,4]triazolo[1,5-a]pyridine-7-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-(4,4-difluorocyclohexyl)imidazo[1,2-a]pyridine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-cyclopentylimidazo[1,2-a]pyridine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclopentyl-2-(4-ethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclohexyl-2-(4-ethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(4-ethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(4-ethylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclopentyl-2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclohexyl-2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-cyclopentylpyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclopentyl-2-(3-methyl-3,8-diazabicyclo[3.2.1]octan-8-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(2,3-dihydro-1H-inden-1-yl)-2-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-ethylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclopentyl-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclohexyl-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4-fluorobenzyl)-2-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-7-methyl-2-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-7-methyl-2-(piperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-ethylpiperidin-4-yl)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(1-ethylpiperidin-4-yl)-7-methylpyrazolo[1,5-a]pyrimidine-6-carboxamide;
- (S)—N-(chroman-4-yl)-7-methyl-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-(4,4-difluorocyclohexyl)-7-methyl-2-(1-methylpiperidin-4-yl)pyrazolo[1,5-a]pyrimidine-6-carboxamide;
- N-cyclopentyl-2-(piperidin-4-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(1-methylpiperidin-4-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(1-ethylpiperidin-4-yl)benzo[d]oxazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(piperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(piperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-ethylpiperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(4-ethylpiperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-methylpiperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(4-methylpiperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- (S)—N-(chroman-4-yl)-2-(4-(2-hydroxyethyl)piperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(4-(2-hydroxyethyl)piperazin-1-yl)benzo[d]oxazole-5-carboxamide;
- N-cyclopentyl-2-(4-ethylpiperazin-1-yl)benzo[d]oxazole-6-carboxamide;
- N-cyclopentyl-2-(piperazin-1-yl)benzo[d]oxazole-6-carboxamide;
- (S)—N-(chroman-4-yl)-2-(1-methyl-1H-pyrazol-4-yl)benzo[d]oxazole-6-carboxamide;
- N-cyclopentyl-2-(piperidin-4-yl)thiazolo[5,4-b]pyridine-5-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(piperidin-4-yl)thiazolo[5,4-b]pyridine-5-carboxamide;
- N-cyclopentyl-2-(1-methylpiperidin-4-yl)thiazolo[5,4-b]pyridine-5-carboxamide;
- N-(4,4-difluorocyclohexyl)-2-(1-methylpiperidin-4-yl)thiazolo[5,4-b]pyridine-5-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-cyclopentylthiazolo[5,4-b]pyridine-5-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-(4,4-difluorocyclohexyl)thiazolo[5,4-b]pyridine-5-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-(4,4-difluorocyclohexyl)thiazolo[4,5-b]pyridine-6-carboxamide;
- N-cyclopentyl-2-(piperidin-4-yl)thiazolo[4,5-b]pyridine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-cyclopentylthiazolo[4,5-c]pyridine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-(4,4-difluorocyclohexyl)thiazolo[4,5-c]pyridine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-cyclopentylthieno[3,2-b]pyridine-6-carboxamide;
- 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)-N-(4,4-difluorocyclohexyl)thieno[3,2-b]pyridine-6-carboxamide;
- or a pharmaceutically acceptable salt or derivative thereof.
120 more elements
Dependencies are inferred from the claim text.