Patent ID: 11912703
Assignee: BRISTOL-MYERS SQUIBB COMPANY
Field: Organic fine chemistry (Chemistry)
Classification: CPC C  A | IPC C

Claim 0:
1. A compound of Formula (I), N-oxide, or a salt thereof, wherein:
G is:
(i), or
(ii), A is:
(i) —O-L1-R6;
(ii) —NR7R8;
(iii) -L2-C(O)NR9R10;
(iv) —CHRxR11, —CH2CH2R11, —CH2NH2, —CH2NHC(O)R11, —CH2NHC(O)CH2CH2(piperidinyl), —CH2NHC(O)OCH2(piperidinyl), or —CH2NHC(O)CH2CH2N(CH3)2;
(v) —CHR12R13, wherein R12 and R13 together with the carbon atom to which they are attached form a cyclic group selected from azabicyclo[4.1.1]octanyl, azepanyl, azetidinyl, C3-6 cycloalkyl, diazaspiro[4.5]decanonyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperidinyl, pyrrolidinyl, and quinuclidinyl, each substituted with zero to 3 R12a;
(vi) —CH═CH(piperidinyl); or
(vii) an aromatic group selected from [1,2,4]triazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridinyl, imidazolyl, indazolyl, isoquinolinyl, oxadiazolyl, oxazolyl, phenyl, pyrazinyl, pyrazolo[3,4-b]pyridinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, quinolinonyl, quinolinyl, quinoxalinyl, tetrahydro-[1,2,4]triazolo[1,5-a]pyrazinyl, tetrahydroimidazo[1,2-a]pyrazinyl, tetrahydroisoquinolinyl, tetrahydrothiazolo[5,4-c]pyridinyl, tetrahydrothieno[2,3-c]pyridinyl, thiadiazolyl, thiazolyl, thiooxadiazolyl, and triazolyl, each substituted with zero to 2 R14a and zero to 3 R14b;
L1 is bond, —CH2—, —CH2CH2—, —CH2C(O)—, —CH2C(O)NH—, —CH2C(O)N(CH3)—, —CH2C(O)NHCH2—, or —CH2C(O)NHCH2CH2—;
L2 is a bond, —CH(CH3)—, —C(CH3)2—, or —CH2CH2—;
R1 is H, Cl, —CN, C1-4 alkyl, C1-2 fluoroalkyl, C1-2 hydroxyalkyl, or —C(O)O(C1-2 alkyl);
each R2 is independently F, Cl, —CN, —OH, C1-3 alkyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, C1-3 hydroxyalkyl, C1-2 aminoalkyl, —(CH2)0-2O(C1-3 alkyl), C3-6 cycloalkyl, —NRxRx, —(CH2)0-2C(O)NRxRx, —(CH2)0-2S(O)2(C1-3 alkyl), —CH2(C3-6 cycloalkyl), —CH2(phenyl), or phenyl;
each R5 is independently F, Cl, —CN, C1-2 alkyl, or —OCH3;
R6 is:
(i) —CH2C(O)NHCH2C(CH3)2OH, —CH2C(O)NHCH2CH2C(CH3)2OH, —CH2C(O)NHCH2CH2NH2, or —CH2C(O)NHCH2CHFC(CH3)2OH; or
(ii) azabicyclo[3.2.1]octanyl, azaspiro[5.5]undecanyl, azetidinyl, cyclohexyl, diazabicyclo[2.2.1]heptanyl, diazaspiro[3.5]nonanyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, piperazinyl, piperidinyl, pyrrolidinyl, or quinuclidinyl, each substituted with zero to 2 R6a;

each R6a is independently F, —OH, —CH3, —CH2CH2CH3, —C(CH3)2, —CH2CH(CH3)2, —CH2CH2CH2CF3, —CH2CH2OH, —CH2CH2CH2OH, —CH2CH(CH3)OH, —CH2C(CH3)2OH, —CH2CH2OCH3, —NH2, —N(CH3)2, —CH2NH2, —CH2CH2NH2, —CH2CH2S(O)2CH3, —CH2C(O)N(CH3)2, —C(O)CH2N(CH3)2, oxetanyl, tetrahydropyranyl, piperidinyl, isobutylpiperidinyl, or —O(piperidinyl);
R7 is:
(i) —CH2(isopropyl azaspiro[3.5]nonanyl), —CH2(methylpyrrolidinyl), —C(O)(CH2)1-3NH2, —C(O)CH(NH2)CH2CH2CH3, —C(O)CH(NH2)CH2CH(CH3)2, —C(O)CH(NH2)CH(CH3)CH2CH3, —C(O)CH(NH2)CH2CH2C(O)OH, —C(O)CH(NH2)(CH2)3-4NH2, —C(O)CH(NH2)(CH2)1-2C(O)NH2, —C(O)CH(NH2)(cyclohexyl), —C(O)CH(NH2)(phenyl), —C(O)(aminocyclohexyl), —C(O)(morpholinyl), —C(O)(pyrrolidinyl), pentamethylpiperidinyl, methylpiperidinyl-piperidinyl, methylpyrrolidinyl-pyrrolidinyl, or phenyl substituted with —OCH2CH2(pyrrolidinyl) or —OCH2CH2NHCH2CH3; or
(ii) cyclohexyl substituted with —NRx(CH2)2-3N(CH3)2, —NHCH2CH2NHCH3, —NH(methylpiperidinyl), —NH(CH2)2-3(morpholinyl), dimethylamino piperidinyl, or piperazinyl substituted with —CH3, —CH2CH3, —C(CH3)3, —CH2CH(CH3)2, —C(O)CH3, —CH2CH2OCH3, —CH2(methylphenyl), —(CH2)2-3(pyrrolidinyl), cyclopentyl, pyridinyl, or methylpiperidinyl;

R7b is:
(i) C1-4 alkyl, C1-2 fluoroalkyl, C1-2 cyanoalkyl, C3-4 hydroxyalkyl, —CH2CH2CH2C≡CH, —CH2CH2OCH3, —CH2CH2S(O)2CH3, —(CH2)1-2NRxRx, —CH2C(O)NRxRx, —NRxRy, —NRx(C1-4 hydroxyalkyl), —NRx(CH2CRxRxOCH3), —NRy(C1-2 cyanoalkyl), —NRx(C1-2 fluoroalkyl), —NRx(C2-5 hydroxyfluoroalkyl), —NRx(CH2)1-2C(O)NRxRx, —NRx(CH2)1-3NRxRx, —NRxCH2CH2N(CH3)2, —NRxC(O)(CH2)1-2NRxRx, —OCH2CH2N(CH3)2, —C(O)(C1-3 alkyl), —C(O)CH2NRxRx, —S(O)2CH3, —(CH2)1-2R7d, —CH2C(O)R7d, —C(O)CH2R7d, —NHR7d, —NH(CH2)1-2R7d, or —OR7d; or
(ii) azepanyl, azetidinyl, bicyclo[1.1.1]pentanyl, C4-6 cycloalkyl, diazepanyl, dioxothiomorpholinyl, morpholinyl, oxaazaspiro[3.3]heptanyl, oxetanyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, or tetrahydropyranyl, each substituted with zero to 1 R8a and zero to 3 R8b;

each R7c is independently —CH3 or —CH2CN;
R7d is azaspiro[3.5]nonanyl, bicyclo[1.1.1]pentanyl, C3-6 cycloalkyl, morpholinyl, oxetanyl, phenyl, piperidinyl, pyrazolyl, pyrrolidinyl, tetrahydrofuranyl, or tetrahydropyranyl, each substituted with zero to 1 substituent selected from C1-3 alkyl, —NH2, —C(O)CH3, methylpiperidinyl, methylpyrrolidinyl, tetramethylpiperidinyl, —OCH2CH2(pyrrolidinyl), and —OCH2CH2NHCH2CH3; and zero to 4 substituents selected from —CH3;
R8 is H, —CH3, or —CH2CH3;
or R7 and R8 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azetidinyl, diazepanonyl, diazepanyl, diazaspiro[3.3]heptanyl, diazaspiro[3.3]heptanyl, diazaspiro[3.5]nonanyl, diazaspiro[5.5]undecanyl, imidazolidinonyl, octahydro-1H-pyrrolo[3,4-b]pyridinyl, piperazinyl, piperidinyl, pyrrolidinonyl, and pyrrolidinyl, wherein said heterocyclic ring is substituted with zero to 1 R7b and zero to 2 R7c;
R8a is —OH, —CH3, —CH2CH3, —CH(CH3)2, —C(CH3)3, —CH2CH(CH3)2, —CH2CH2OCH3, —CH2CH2CF3, —C(O)CH3, —CH2(cyclopropyl), —CH2(methyl phenyl), —(CH2)2-3(pyrrolidinyl), —CH2(methylpyrazolyl), —CH2(thiophenyl), —NRxRx, cyclopentyl, methylpiperidinyl, or pyridinyl;
each R8b is —CH3;
R9 is —CH3, —CH2CH2OH, —CH2C(CH3)2OH, —CH2C(CH3)2CH2OH, —CH2CHFC(CH3)2OH, —CH2CH2C(CH3)2OH, —CH(CH2OH)2, —CH2CH2OCH3, —CH2CH2NH2, —CH2CH2N(CH3)2, —CH2CH2CH2N(CH3)2, —CH2CH2C(O)NH2, —CH2S(O)2OH, —CH2CH2C(CH3)2NHS(O)2CH3, or —(CH2)0-3R9a;
R9a is cyclohexyl, cycloheptyl, furanyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinyl, quinuclidinyl, thiazolyl, or octahydrocyclopenta[c]pyrrolyl, each substituted with zero to 2 substituents independently selected from —OH, C1-3 alkyl, —NH2, —N(CH3)2, oxetanyl, phenyl, piperazinyl, piperidinyl, and pyrrolidinyl;
R10 is H, —CH3, —CH2CH3, —CH2CH2OCH3, or cyclopropyl;
or R9 and R10 together with the nitrogen atom to which they are attached form a heterocyclic ring selected from azabicyclo[3.1.1]heptanyl, azaspiro[5.5]undecanyl, diazabicyclo[2.2.1]heptanyl, diazabicyclo[3.1.1]heptanyl, diazabicyclo[3.2.0]heptanyl, diazaspiro[3.5]nonanyl, diazaspiro[4.4]nonanyl, diazaspiro[4.5]decanyl, diazepanyl, indolinyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, piperazinonyl, piperazinyl, piperidinyl, and pyrrolidinyl, each substituted with zero to 2 R10a;
each R10a is independently —CH3, —CH2CH3, —CH(CH3)2, —CH2OH, —CH2CH2OH, —CH2OCH3, —CH2CH2OCH3, —CH2NH2, —CH2CH2NH2, —CH2CH2NH(CH3), —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2(methyltriazolyl), —CH2CH2(phenyl), —CH2CH2(morpholinyl), —C(O)CH3, —C(O)NH2, —C(O)N(CH2CH3)2, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —NH2, —N(CH3)2, —NHC(O)CH3, —C(O)(furanyl), —O(piperidinyl), —C(O)CH2(diethylcarbamoylpiperidinyl), methylpiperazinyl, piperidinyl, methylpiperidinyl, diethylcarbamoylpiperidinyl, isopropylpiperidinyl, pyridinyl, trifluoromethylpyridinyl, pyrimidinyl, or dihydrobenzo[d]imidazolonyl;
R11 is azetidinyl, azaspiro[3.5]nonanyl, dioxidothiomorpholinyl, hexahydropyrrolo[3,4-c]pyrrolyl, morpholinyl, piperazinyl, piperidinyl, or pyrrolidinyl, each substituted with zero to 2 substituents independently selected from F, —CH3, —CH(CH3)2, —CH2CN, —CH2(phenyl), —C(O)CH2N(CH3)2, —CH2C(CH3)2OH, —CH2C(O)N(CH3)2, —CH2CH2S(O)2CH3, —CH2CH2S(O)CH3, oxetanyl, and tetrahydropyranyl;
each R12a is independently —OH, —CH3, —CH2CH2CH3, —CH(CH3)2, —CH2CH(CH3)2, —CF3, —CH2CF3, —CH2CH2CH2CF3, —CH2CN, —CH2C(CH3)2OH, —CH2CH2OCH3, —CH2C(O)NH(CH3), —CH2C(O)N(CH3)2, —CH2C(O)NH2, —CH2CH2S(O)2CH3, —CH2CH2NHS(O)2CH3, —CH2NRxRx, —CH2CH2NH(CH3), —OCH3, —NRxRy, —NRx(C2-4 fluoroalkyl), —NRx(CH2CHFC(CH3)2OH), —NRx(CH2CRxRxOCH3), —NH(CH2CN), —N(CH3)CH2N(CH3)2, —NRx(CH2CHFC(CH3)2OH), —NH(CH2CH2OCH3), —NH(CH2C(CH3)2OH), —NRx(CH2C(O)NRxRx), —N(CH3)(OCH3), —NRxCH2CH2S(O)2CH3, —NHC(O)CH3, —NHC(O)CH2CF3, —NHC(O)CHRxNH(CH3), —NRxC(O)CH2N(CH3)2, —NHC(O)CH2N(CH3)(CH2CH3), —NHC(O)CH2N(CH2CH3)2, —NHC(O)CH2NH(CH2C(CH3)2OH), —NHCH2C(O)NRx(CH3), —NHS(O)2CH3, —C(O)C(CH3)3, —C(O)CH(CH2CH3)2, —C(O)CH2OCH3, —C(O)CH2CH2OCH3, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —C(O)CH(CH3)NH(CH3), —C(O)CH2N(CH3)(CH2CH3), —C(O)CH2N(CH2CH3)2, R12b, —CH2R12b, —C(O)R12b, —C(O)CH2R12b, —C(O)CH2NHR12b, —C(O)NRxR12b, —NRxC(O)CH2R12b, —NRxR12b, —N(CH2CN)R12b, —NRxCH2R12b, —N(CH2CN)R12b, —NHC(O)CH2NRxR12b, —NHC(O)CH2NRxCH2R12b, —NHCH2C(O)NHR12b, or —OR12b; or two R12a and the carbon atom to which they are attached form C═O;
R12b is azetidinyl, bicyclo[1.1.1]pentanyl, cyclopropyl, diazabicyclo[2.2.1]heptanyl, dioxolanyl, dioxidotetrahydrothiopyranyl, dioxidothiomorpholinyl, imidazolyl, morpholinyl, octahydrocyclopenta[c]pyrrolyl, octahydropyrrolo[3,4-c]pyrrolyl, oxaazaspiro[3.3]heptanyl, oxetanyl, phenyl, piperazinyl, piperazinonyl, piperidinyl, pyridinyl, pyrrolidinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydropyranyl, or triazolyl, each substituted with zero to 4 substituents independently selected from F, —OH, —CH3, —CH(CH3)2, —CH2OH, —OCH3, —CH2CH2OCH3, —NRxRx, —C(O)NH2, and —CH2S(O)2CH3;
each R14a is independently:
(i) H, F, Cl, —OH, —CH3, —CH(CH3)2, —CH(CH3)(CH2CH3), —CH2CH2CH2C(CH3)2, —CF3, —CH2CF3, —CH2OH, —OCH3, —CH2CH2OCH3, —CHRxNRx(CH3), —CH2N(CH3)(CH(CH3)2), —CH2NH(CH2C(CH3)3), —CH2NH(CH2CN), —CH2N(CH3)(CH2CH2OCH3), —CH2N(CH2CH2OCH3)2, —CH2NRx(CH2C≡CH), —CH2NHCH2CH2N(CH3)2, —CH2CH2NRx(CH3), —CH2CRx(CH3)NH2, —CH2CH2CH2N(CH3)2, —CH2CH2CH2CH2NH2, —CH(NH2)(CH2)3-4NH2, —CH2NHCH2CH2O(C1-3 alkyl), —CH2NHCH2CH2OCH2CH2OH, —CH2NHCH2CH2S(O)2OH, —CH2C(O)NRx(CH3), —NRxRx, —NH(CH(CH3)2), —NHCH2CH2NH(CH3), —NHCH2CH2CH2N(CH3)2, —NHC(O)CH3, —NHC(O)CF3, —NHC(O)OC(CH3)3, —NHC(O)CH2N(CH3)2, —NHC(O)CH2CH2N(CH3)2, —NHCH2C(O)CH2NH(CH3), —C(O)CH3, —C(O)CH2CH(CH3)OH, —C(O)CH2NRx(CH3), —C(O)NRxRx, —C(O)NH(CH2CN), —C(O)NHCH2CH2CH2NRxRx, —C(O)NHCH2CH(CH3)CH2NH2, —C(O)NHCH2C(O)NH2, —C(O)N(CH3)CH2CH2CH2N(CH3)2, —C(O)N(CH2CH3)CH2CH2N(CH3)2, —OCH2CH2CH2N(CH3)2, —C(O)NHCH2CH2NHC(O)CH3, —S(O)2NH2, or —C(O)CH2S(O)2CH3;
(ii) 8-azabicyclo[3.2.1]octanyl, azaspiro[3.5]nonanyl, azetidinyl, benzo[c][1,2,5]oxadiazolyl, cyclopentyl, cyclohexyl, diazepanyl, morpholinyl, phenyl, piperazinyl, piperidinyl, pyrazolyl, pyridinyl, pyrrolidinonyl, quinolinyl, quinuclidinyl, tetrahydroisoquinolinyl, tetrahydropyridinyl, or thiazolidinyl, each substituted with zero to 2 substituents independently selected from —CH3, —CH(CH3)2, —CH2CH(CH3)2, —CF3, —CH2CH2CF3, —CH2CH2OH, —CH2CH2CH(CH3)OH, —NH2, —CH2N(CH3)2, —CH2CH2NH(CH3), —C(O)CH3, —C(O)CH2NH(CH3), —C(O)CH2N(CH3)2, —C(O)O(C(CH3)3), —CH2C(O)NRx(CH3), cyclobutyl, cyclopentyl, —CH2(phenyl), —CH2(pyrrolyl), —CH2(morpholinyl), —CH2(methylpiperazinyl), —CH2(thiophenyl), methylpiperidinyl, isobutylpiperidinyl, and pyridinyl; or
(iii) -L3-R14c;
each R14b is —CH3;

L3 is —(CH2)1-3—, —CH(CH3)—, —CH(NH2)—, —CH2NH—, —C(O)—, —C(O)NH(CH2)0-4—, —C(O)N(CH3)CH2CH2—, —NH—, —NHC(O)—, —NHCH2—, —NHCH2C(O)—, —O—, or —OCH2CH2—;
R14c is adamantanyl, azetidinyl, cyclopropyl, cyclohexyl, diazepanyl, imidazolyl, indolyl, morpholinyl, octahydropyrrolo[3,4-c]pyrrolyl, phenyl, piperazinonyl, piperazinyl, piperidinyl, pyridinyl, pyrrolidinonyl, pyrrolidinyl, or tetrazolyl, each substituted with zero to 1 substituent selected from —OH, —CH3, —CH(CH3)2, —CH2CH(CH3)2, —C(CH3)2OH, —NH2, —N(CH3)2, —NH(C(CH3)2, —NHC(O)CH3, —C(O)CH3, —C(O)NH2, —C(O)N(CH2CH3)2, —C(O)(tetrahydrofuranyl), —C(O)OCH2CH3, —CH2C(O)NH(CH(CH3)2, morpholinyl, methylpiperidinyl, pyrazinyl, pyridinyl, and pyrrolidinyl;
each Rx is independently H or —CH3;
each Ry is independently H or C1-6 alkyl;
n is zero or 1; and
p is zero, 1, 2, or 3.