US 2026/0217672 A1Published application

Benzamide compounds for treatment of bacterial infections

AssigneeHoffmann-La Roche Inc.

InventorsFabian Dey, Xiao Ding, Houguang Shi, Xuefei Tan, Jun Wu, Jiamin Zheng, Mingwei Zhou

Life of this patent

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Abstract

The present invention relates to compounds of formula (I), wherein R1 to R8, Y, A, Q, X and M are as described herein, and their pharmaceutically acceptable salt thereof, and compositions including the compounds and methods of using the compounds.

Claims38

Dependent claims

A compound of formula (I),

wherein
R1 is COR9;
wherein R9 is selected from the group consisting of
((hydroxyC1-6alkyl)amino)C1-6alkyl,
1-oxa-2,9-diazaspiro[4.5]dec-2-enyl,
4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazinyl,
4,6-dihydropyrrolo[3,4-c]pyrazolyl substituted by C1-6alkyl,
6,7-dihydro-5H-pyrrolo[3,4-b]pyridinyl,
indanyl substituted by amino or aminoC1-6alkylamino,
isoindolinyl,
piperazinylC1-6alkyl,
pyrazolo[1,5-a]pyrimidinyl,
pyrazolyl substituted once or twice by the substituents independently selected from aminoC1-6alkyl, azetidinyl, C1-6alkyl and carboxy,
pyridinyl substituted by (aminoC1-6alkylamino)C1-6alkyl, and
phenyl substituted once or twice by the substituents independently selected from ((amino(carboxy)C1-6alkyl)amino)C1-6alkyl, ((aminoC1-6alkyl)-3-azabicyclo[3.1.0]hexanyl)C1-6alkyl, ((aminoC1-6alkyl)pyrrolidinyl)C1-6alkyl, ((aminoC3-7 cycloalkyl)C1-6alkylamino)C1-6alkyl, ((aminoC3-7cycloalkyl)pyrrolidinyl)C1-6alkyl, ((oxooxazolidinyl)C1-6alkylamino)C1-6alkyl, ((oxopyrrolidinyl)C1-6alkylamino)C1-6alkyl, ((piperidinyl)C1-6alkylamino)C1-6alkyl, (3,3a,4,5,6,6a-hexahydro-2H-pyrrolo[3,4-b]pyrrolyl)C1-6alkyl, (3,6-diazabicyclo[3.1.1]heptanyl)C1-6alkyl, (amino-2-azaspiro[3.3]heptanyl)C1-6alkyl, (amino-5-azaspiro[2.4]heptanyl)C1-6alkyl, (aminoC1-6alkyl)piperazinyl, (aminoC1-6alkyl)pyrrolidinyl, (aminoC1-6alkylamino)C1-6alkyl, (aminopyrrolidinyl)C1-6alkyl, (C1-6alkyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrolyl)C1-6alkyl, (diaminoC1-6alkylcarbonyl)amino, (morpholinylC1-6alkylamino)C1-6alkyl, (piperazinylC1-6alkylamino)C1-6alkyl, (piperidinylC1-6alkylamino)C1-6alkyl, [((C1-6alkyl)2aminocarbonylC1-6alkyl)amino]C1-6alkyl, [((hydroxyC1-6alkyl)2amino)C1-6alkylamino]C1-6alkyl, 2,5-diazabicyclo[2.2.1]heptanyl, 3,6-diazabicyclo[3.2.0]heptanyl, aminoC1-6alkoxy, aminoC1-6alkyl, aminopyrrolidinyl, azetidinylC1-6alkoxy, azetidinylC1-6alkylamino, C1-6alkylcarbonyloxy, C1-6alkoxy, carboxy, hydroxy and piperazinyl;
R2 is H;
R3 is H, hydroxy or C1-6alkoxy, or
R2 and R3 together with the atoms they are attached to form a pyrrolidinyl;
R4 is H, hydroxy or C1-6alkoxy;
R5 is H or C1-6alkyl,
R6 is H or C1-6alkyl, or
R5 and R6 together with the atoms they are attached to form a C3-7cycloalkyl;
R7 is halogen, cyano, haloC1-6alkyl or C1-6alkoxycarbonyl;
R8 is H, halogen, cyano, amino, C3-7cycloalkoxy, C1-6alkyl, C1-6alkoxy or haloC1-6alkyl;
Y is CH or N;
A is O, N(CN), or N(C1-6alkyl),
Q is CH or N;
X is CH or N;
and
M is N or CR10;
wherein R10 is H, halogen, C1-6alkyl or C3-7cycloalkyl;
with the proviso that Q, X and M are not N simultaneously;
or a pharmaceutically acceptable salt thereof.

30 more elements

A compound selected from:

4-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[5-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[3-chloro-5-(trifluoromethyl) phenyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[2-chloro-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[2-amino-6-(trifluoromethyl)pyrimidin-4-yl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-(4-bromo-6-chloro-2-pyridyl)piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[5-cyclopropyl-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-(cyclopropoxy)-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-ethoxy-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-ethyl-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[4-(trifluoromethyl)pyrimidin-2-yl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopropylamino)ethyl]-N-[4-[4-[5-methyl-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopropylamino)ethyl]-N-[4-[4-(4,5-dichloro-2-pyridyl)piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopropylamino)ethyl]-N-[4-[4-[4-cyano-6-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopropylamino)ethyl]-N-[4-[4-[6-cyano-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopropylamino)ethyl]-N-[4-[4-[6-chloro-4-(1,1-difluoroethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-methyl-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
Methyl 2-[4-[4-[[3-[(3-aminopropylamino)methyl]benzoyl]amino]phenyl]sulfonylpiperazin-1-yl]-6-chloro-pyridine-4-carboxylate;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-(6-chloro-4-cyano-2-pyridyl)piperazin-1-yl]sulfonylphenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]-2-methyl-piperazin-1-yl]sulfonylphenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]-3-methyl-piperazin-1-yl]sulfonylphenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[[5-[6-chloro-4-(trifluoromethyl)-2-pyridyl]-2,5-diazabicyclo[4.2.0]octan-2-yl]sulfonyl]phenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[2-(3-Aminopropylamino)ethyl]-N-[4-[S-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]-N-cyano-sulfonimidoyl]phenyl]benzamide;
3-[(3-aminopropylamino)methyl]-N-[4-[S-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]-N-methyl-sulfonimidoyl]phenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonyl-3-methoxy-phenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonyl-3-hydroxy-phenyl]benzamide;
4-[(3-Aminopropylamino)methyl]-N-[5-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonyl-2-pyridyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonyl-2-methoxy-phenyl]benzamide;
3-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonyl-2-hydroxy-phenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-methyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-1-methyl-4,6-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide;
[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]-pyrazolo[1,5-a]pyrimidin-3-yl-methanone;
4-[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindoline-1-carbonyl]-2-methyl-pyrazole-3-carboxylic acid;
[1-(Azetidin-3-yl)pyrazol-4-yl]-[5-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]methanone;
[1-(3-Aminopropyl)pyrazol-4-yl]-[5-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]methanone;
[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]-(4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-3-yl)methanone;
[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]-(1-oxa-2,9-diazaspiro[4.5]dec-2-en-3-yl)methanone;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-piperazin-1-yl-acetamide;
1-[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindolin-1-yl]-2-(2-hydroxyethylamino)ethanone;
2-[5-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindoline-1-carbonyl]benzoic acid;
[2-Acetoxy-4-[5-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylindoline-1-carbonyl]phenyl]acetate;
N-[4-[4-[4-methyl-6-(trifluoromethyl)pyrimidin-2-yl]piperazin-1-yl]sulfonylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxamide;
N-[4-[4-[6-methyl-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-6,7-dihydro-5H-pyrrolo[3,4-b]pyridine-3-carboxamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]isoindoline-5-carboxamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-(2,5-diazabicyclo[2.2.1]heptan-2-yl)benzamide;
3-(2-Aminoethoxy)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-(Azetidin-3-ylmethylamino)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-(Azetidin-3-ylmethoxy)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[(3R)-3-aminopyrrolidin-1-yl]benzamide;
N-[4-[4-[6-Chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[3,6-diazabicyclo[3.2.0]heptan-3-yl]benzamide;
3-(2-Aminoethyl)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-piperazin-1-yl-benzamide;
2-Amino-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]indane-5-carboxamide;
5-(Aminomethyl)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-hydroxy-benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-(2,4-diaminobutanoylamino)benzamide;
4-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]pyridine-2-carboxamide;
6-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]pyridine-2-carboxamide;
5-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]pyridine-3-carboxamide;
2-(3-Aminopropylamino)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]indane-5-carboxamide;
3-(3-Aminopropylamino)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]indane-5-carboxamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-methoxy-5-[(5-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-1-yl)methyl]benzamide;
1-(3-Aminopropylamino)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]indane-5-carboxamide;
3,4-bis(3-Aminopropoxy)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[1-(3-Aminopropyl)pyrrolidin-2-yl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[1-(3-Aminopropyl)pyrrolidin-3-yl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[4-(3-Aminopropyl)piperazin-1-yl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(3-Aminopyrrolidin-1-yl)ethyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
4-[2-(7-Amino-2-azaspiro[3.3]heptan-2-yl)ethyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-4-[2-(5-methyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrol-1-yl)ethyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-4-[[(2S)-2-(2-aminoethyl)pyrrolidin-1-yl]methyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-4-[2-(3-morpholinopropylamino)ethyl]benzamide;
4-[2-(2-Amino-5-azaspiro[2.4]heptan-5-yl)ethyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-4-[2-(3,6-diazabicyclo[3.1.1]heptan-6-yl)ethyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[(4-piperidylmethylamino)methyl]benzamide;
3-[[(3-Aminocyclobutyl)methylamino]methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[(3-piperazin-1-ylpropylamino)methyl]benzamide;
3-[[3-(1-Aminocyclopropyl)pyrrolidin-1-yl]methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
3-[[3-[Bis(2-hydroxyethyl)amino]propylamino]methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-methoxy-5-[[3-(4-piperidyl)propylamino]methyl]benzamide;
3-[[1-(Aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
(2R)-2-Amino-4-[[3-[[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]carbamoyl]phenyl]methylamino]butanoic acid;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[[(2-oxooxazolidin-4-yl)methylamino]methyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[[(5-oxopyrrolidin-3-yl)methylamino]methyl]benzamide;
N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-3-[[[3-(dimethylamino)-3-oxo-propyl]amino]methyl]benzamide;
5-(3,3a,4,5,6,6a-Hexahydro-2H-pyrrolo[3,4-b]pyrrol-1-ylmethyl)-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]-2-methoxy-benzamide;
and
2-[(3-Aminopropylamino)methyl]-N-[4-[4-[6-chloro-4-(trifluoromethyl)-2-pyridyl]piperazin-1-yl]sulfonylphenyl]benzamide;
or a pharmaceutically acceptable salt thereof.

87 more elements

Dependencies are inferred from the claim text.

Facts

Application: 18/823,634Filed 2 Mar 2023
Priority: WO PCT/CN2022/0793264 Mar 2022
Published: 30 Jul 2026
Term ends: Not estimatedThe source records don’t support an estimate.

Classification24 codes

C07D 213/72
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/496
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: non-condensed piperazines…
A61K 31/4985
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyrazines or piperazines…

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Abstract

A compound of formula (I),

wherein
R1 is COR9;
wherein R9 is selected from the group consisting of
((hydroxyC1-6alkyl)amino)C1-6alkyl,
1-oxa-2,9-diazaspiro[4.5]dec-2-enyl,
4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazinyl,
4,6-dihydropyrrolo[3,4-c]pyrazolyl substituted by C1-6alkyl,
6,7-dihydro-5H-pyrrolo[3,4-b]pyridinyl,
indanyl substituted by amino or aminoC1-6alkylamino,
isoindolinyl,
piperazinylC1-6alkyl,
pyrazolo[1,5-a]pyrimidinyl,
pyrazolyl substituted once or twice by the substituents independently selected from aminoC1-6alkyl, azetidinyl, C1-6alkyl and carboxy,
pyridinyl substituted by (aminoC1-6alkylamino)C1-6alkyl, and
phenyl substituted once or twice by the substituents independently selected from ((amino(carboxy)C1-6alkyl)amino)C1-6alkyl, ((aminoC1-6alkyl)-3-azabicyclo[3.1.0]hexanyl)C1-6alkyl, ((aminoC1-6alkyl)pyrrolidinyl)C1-6alkyl, ((aminoC3-7 cycloalkyl)C1-6alkylamino)C1-6alkyl, ((aminoC3-7cycloalkyl)pyrrolidinyl)C1-6alkyl, ((oxooxazolidinyl)C1-6alkylamino)C1-6alkyl, ((oxopyrrolidinyl)C1-6alkylamino)C1-6alkyl, ((piperidinyl)C1-6alkylamino)C1-6alkyl, (3,3a,4,5,6,6a-hexahydro-2H-pyrrolo[3,4-b]pyrrolyl)C1-6alkyl, (3,6-diazabicyclo[3.1.1]heptanyl)C1-6alkyl, (amino-2-azaspiro[3.3]heptanyl)C1-6alkyl, (amino-5-azaspiro[2.4]heptanyl)C1-6alkyl, (aminoC1-6alkyl)piperazinyl, (aminoC1-6alkyl)pyrrolidinyl, (aminoC1-6alkylamino)C1-6alkyl, (aminopyrrolidinyl)C1-6alkyl, (C1-6alkyl-2,3,3a,4,6,6a-hexahydropyrrolo[2,3-c]pyrrolyl)C1-6alkyl, (diaminoC1-6alkylcarbonyl)amino, (morpholinylC1-6alkylamino)C1-6alkyl, (piperazinylC1-6alkylamino)C1-6alkyl, (piperidinylC1-6alkylamino)C1-6alkyl, [((C1-6alkyl)2aminocarbonylC1-6alkyl)amino]C1-6alkyl, [((hydroxyC1-6alkyl)2amino)C1-6alkylamino]C1-6alkyl, 2,5-diazabicyclo[2.2.1]heptanyl, 3,6-diazabicyclo[3.2.0]heptanyl, aminoC1-6alkoxy, aminoC1-6alkyl, aminopyrrolidinyl, azetidinylC1-6alkoxy, azetidinylC1-6alkylamino, C1-6alkylcarbonyloxy, C1-6alkoxy, carboxy, hydroxy and piperazinyl;
R2 is H;
R3 is H, hydroxy or C1-6alkoxy, or
R2 and R3 together with the atoms they are attached to form a pyrrolidinyl;
R4 is H, hydroxy or C1-6alkoxy;
R5 is H or C1-6alkyl,
R6 is H or C1-6alkyl, or
R5 and R6 together with the atoms they are attached to form a C3-7cycloalkyl;
R7 is halogen, cyano, haloC1-6alkyl or C1-6alkoxycarbonyl;
R8 is H, halogen, cyano, amino, C3-7cycloalkoxy, C1-6alkyl, C1-6alkoxy or haloC1-6alkyl;
Y is CH or N;
A is O, N(CN), or N(C1-6alkyl),
Q is CH or N;
X is CH or N;
and
M is N or CR10;
wherein R10 is H, halogen, C1-6alkyl or C3-7cycloalkyl;
with the proviso that Q, X and M are not N simultaneously;
or a pharmaceutically acceptable salt thereof.

30 more elements

Facts

Application

18/823,634Filed 2 Mar 2023

Priority

WO PCT/CN2022/0793264 Mar 2022

Published

30 Jul 2026

Term ends

Not estimatedThe source records don’t support an estimate.

Classification24 codes

C07D 213/72
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
A61K 31/496
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: non-condensed piperazines…
A61K 31/4985
Having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines: pyrazines or piperazines…