KR102742178B1 - Tlr 억제제로서 유용한 치환된 인돌 화합물 - Google Patents
Tlr 억제제로서 유용한 치환된 인돌 화합물 Download PDFInfo
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- KR102742178B1 KR102742178B1 KR1020207020558A KR20207020558A KR102742178B1 KR 102742178 B1 KR102742178 B1 KR 102742178B1 KR 1020207020558 A KR1020207020558 A KR 1020207020558A KR 20207020558 A KR20207020558 A KR 20207020558A KR 102742178 B1 KR102742178 B1 KR 102742178B1
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- KR
- South Korea
- Prior art keywords
- isopropyl
- indol
- triazolo
- pyridin
- methoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003112 inhibitor Substances 0.000 title abstract description 10
- 150000002475 indoles Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 246
- 150000003839 salts Chemical class 0.000 claims abstract description 43
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 22
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
- 201000006417 multiple sclerosis Diseases 0.000 claims description 163
- -1 diazaspiro[4.5]decanonyl Chemical group 0.000 claims description 89
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 125000003386 piperidinyl group Chemical group 0.000 claims description 71
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 38
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 36
- 125000002393 azetidinyl group Chemical group 0.000 claims description 35
- 125000002757 morpholinyl group Chemical group 0.000 claims description 33
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 32
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004193 piperazinyl group Chemical group 0.000 claims description 22
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 22
- 125000004122 cyclic group Chemical group 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003725 azepanyl group Chemical group 0.000 claims description 16
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 125000003566 oxetanyl group Chemical group 0.000 claims description 14
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 13
- QBZLCMRAAJXEFT-UHFFFAOYSA-N 2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNCCO1)C1=CN2N=CN=C2C(C)=C1 QBZLCMRAAJXEFT-UHFFFAOYSA-N 0.000 claims description 12
- VYIOQCZAMSOEJW-UHFFFAOYSA-N 8-methoxy-6-(5-piperidin-3-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCNC1 VYIOQCZAMSOEJW-UHFFFAOYSA-N 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- GLGFHSIRUSWQOP-UHFFFAOYSA-N 4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)=O)C GLGFHSIRUSWQOP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 8
- 125000001425 triazolyl group Chemical group 0.000 claims description 8
- OJFNIVDLRWXLNX-UHFFFAOYSA-N 1-[3-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]-7-azabicyclo[4.1.1]octan-7-yl]-2-(dimethylamino)ethanone Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CC2N(C(CC1)C2)C(CN(C)C)=O OJFNIVDLRWXLNX-UHFFFAOYSA-N 0.000 claims description 7
- SODPIVPXQHNCES-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-[(5-propan-2-yl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl)methyl]-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)CN1CC2CN(CC2C1)C(C)C SODPIVPXQHNCES-UHFFFAOYSA-N 0.000 claims description 7
- HVDBIFIEJUXPSR-UHFFFAOYSA-N 4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(N)CC1 HVDBIFIEJUXPSR-UHFFFAOYSA-N 0.000 claims description 7
- DGKAGVRKCVOGBW-UHFFFAOYSA-N 5,5-dimethyl-2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNC(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 DGKAGVRKCVOGBW-UHFFFAOYSA-N 0.000 claims description 7
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 7
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 7
- IMAZOLGGKPXBIM-UHFFFAOYSA-N 1-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound CNCC(=O)N1CCCC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(OC)=C1 IMAZOLGGKPXBIM-UHFFFAOYSA-N 0.000 claims description 6
- VKSJLYFHMRBKKQ-UHFFFAOYSA-N 2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-4-(oxetan-3-yl)morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CCO1)C1COC1)C1=CN2N=CN=C2C(C)=C1 VKSJLYFHMRBKKQ-UHFFFAOYSA-N 0.000 claims description 6
- RKTLDPZHUMZVDO-UHFFFAOYSA-N 2-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCN(CC(=O)N(C)C)C1 RKTLDPZHUMZVDO-UHFFFAOYSA-N 0.000 claims description 6
- WAEBXNAPLHRSNV-UHFFFAOYSA-N 4-(2-methylsulfonylethyl)-2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CCS(C)(=O)=O)CCO1)C1=CN2N=CN=C2C(C)=C1 WAEBXNAPLHRSNV-UHFFFAOYSA-N 0.000 claims description 6
- QCQIHBWIQLVLJN-UHFFFAOYSA-N 6-[5-(azetidin-3-yl)-3-propan-2-yl-1H-indol-2-yl]-8-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNC1)C1=CN2N=CN=C2C(C)=C1 QCQIHBWIQLVLJN-UHFFFAOYSA-N 0.000 claims description 6
- PFQJZYIDNFIHJW-UHFFFAOYSA-N 6-[5-(azetidin-3-ylmethyl)-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(CC3CNC3)C=C12)C1=CN2N=CN=C2C(C)=C1C PFQJZYIDNFIHJW-UHFFFAOYSA-N 0.000 claims description 6
- LYJCBZCXKWXEIP-UHFFFAOYSA-N 6-[5-[(1-benzylpyrrolidin-2-yl)methyl]-3-propan-2-yl-1H-indol-2-yl]-8-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C1=CC=CC=C1)N1C(CCC1)CC=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C LYJCBZCXKWXEIP-UHFFFAOYSA-N 0.000 claims description 6
- NPFYDNNXAYWGAG-UHFFFAOYSA-N 8-methoxy-6-[3-propan-2-yl-5-(1-propan-2-ylpiperidin-3-yl)-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCN(C1)C(C)C NPFYDNNXAYWGAG-UHFFFAOYSA-N 0.000 claims description 6
- QGJGTRNASJZNRX-UHFFFAOYSA-N 8-methoxy-6-[5-[1-(2-methoxyethyl)piperidin-3-yl]-3-propan-2-yl-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(CCC1)CCOC)C=1C=C(C=2N(C=1)N=CN=2)OC QGJGTRNASJZNRX-UHFFFAOYSA-N 0.000 claims description 6
- WKNWULRFPOTOTI-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC(C)(C)O)CCO1)C1=CN2N=CN=C2C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC(C)(C)O)CCO1)C1=CN2N=CN=C2C(C)=C1 WKNWULRFPOTOTI-UHFFFAOYSA-N 0.000 claims description 6
- CUOXGAGUXSMPEU-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CCO1)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CCO1)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1 CUOXGAGUXSMPEU-UHFFFAOYSA-N 0.000 claims description 6
- JZKLZCUVYRRZMR-UHFFFAOYSA-N CNCC(=O)N1CCOC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1 Chemical compound CNCC(=O)N1CCOC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1 JZKLZCUVYRRZMR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- WHRHTSKMHVTWSL-UHFFFAOYSA-N 4,5,5-trimethyl-2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(C)C(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 WHRHTSKMHVTWSL-UHFFFAOYSA-N 0.000 claims description 5
- NUDZXOZPZDHDEZ-UHFFFAOYSA-N 4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-(2-methoxyethyl)-N-methylcyclohexan-1-amine Chemical compound COCCN(C)C1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1C NUDZXOZPZDHDEZ-UHFFFAOYSA-N 0.000 claims description 5
- UVXQKXGFQKIFIN-UHFFFAOYSA-N 4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methylcyclohexan-1-amine Chemical compound CNC1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(OC)=C1 UVXQKXGFQKIFIN-UHFFFAOYSA-N 0.000 claims description 5
- YFFRSVFAPFSHAS-UHFFFAOYSA-N C(C)(C)C1=C(NC2=CC=C(C=C12)C1OCCN(C1)CC(=O)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)C Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1OCCN(C1)CC(=O)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)C YFFRSVFAPFSHAS-UHFFFAOYSA-N 0.000 claims description 5
- VQVFBJWATNYZNT-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CN(C(=O)CN(C)C)C(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(C(=O)CN(C)C)C(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 VQVFBJWATNYZNT-UHFFFAOYSA-N 0.000 claims description 5
- XBXDYVKEHPNBMA-UHFFFAOYSA-N CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC(=O)N(C)C)C(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC(=O)N(C)C)C(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1 XBXDYVKEHPNBMA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- ALSPNHUQMRLLPD-UHFFFAOYSA-N 1-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCN(CC(C)(C)O)C1 ALSPNHUQMRLLPD-UHFFFAOYSA-N 0.000 claims description 4
- RNXRXOVQESUXEA-UHFFFAOYSA-N 1-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-N,N-dimethylmethanamine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC(CN(C)C)CC1)C1=CC(C)=NC(C)=C1 RNXRXOVQESUXEA-UHFFFAOYSA-N 0.000 claims description 4
- XUIRREMJZHMORH-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCN(C1)C(=O)CN(C)C XUIRREMJZHMORH-UHFFFAOYSA-N 0.000 claims description 4
- CUNFXLDCFONNDL-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]ethanone Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(C1)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1 CUNFXLDCFONNDL-UHFFFAOYSA-N 0.000 claims description 4
- FVGRSNHGNJEETA-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-1-methylcyclohexyl]acetamide Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(C)(CC1)NC(=O)CN(C)C FVGRSNHGNJEETA-UHFFFAOYSA-N 0.000 claims description 4
- JYSITAWXDOJNFJ-UHFFFAOYSA-N 2-(methylamino)-1-[3-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]ethanone Chemical compound CNCC(=O)N1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1 JYSITAWXDOJNFJ-UHFFFAOYSA-N 0.000 claims description 4
- YIVWVEHXSPYPHT-UHFFFAOYSA-N 2-[3-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)CCNC YIVWVEHXSPYPHT-UHFFFAOYSA-N 0.000 claims description 4
- IDSKCFSCVBCTSK-UHFFFAOYSA-N 2-[3-[[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]methyl]azetidin-1-yl]-N,N-dimethylacetamide Chemical compound CC(C)C1=C(NC2=CC=C(CC3CN(CC(=O)N(C)C)C3)C=C12)C1=CN2N=CN=C2C(C)=C1C IDSKCFSCVBCTSK-UHFFFAOYSA-N 0.000 claims description 4
- OOBKGONBXIJPIV-UHFFFAOYSA-N 3,3,3-trifluoro-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]propanamide Chemical compound FC(CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)(F)F OOBKGONBXIJPIV-UHFFFAOYSA-N 0.000 claims description 4
- ULUKBDNFVKOOTE-UHFFFAOYSA-N 3-(dimethylamino)-N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]propanamide Chemical compound CN(CCC(=O)NCC=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)CC)C ULUKBDNFVKOOTE-UHFFFAOYSA-N 0.000 claims description 4
- KETXJLUIWNSGDJ-UHFFFAOYSA-N 4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]-1-(trifluoromethyl)cyclohexan-1-ol Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)(O)C(F)(F)F)C KETXJLUIWNSGDJ-UHFFFAOYSA-N 0.000 claims description 4
- SDCIULZNONADQG-UHFFFAOYSA-N 4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methyl-N-(2-methylsulfonylethyl)cyclohexan-1-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)N(C)CCS(C)(=O)=O SDCIULZNONADQG-UHFFFAOYSA-N 0.000 claims description 4
- YOOGDLWVSZPXAN-UHFFFAOYSA-N 4-[2-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]ethyl]morpholine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)CCN1CCOCC1)C YOOGDLWVSZPXAN-UHFFFAOYSA-N 0.000 claims description 4
- XUUYWERTMXUPNC-UHFFFAOYSA-N 6-[5-(4-methoxycyclohexyl)-3-propan-2-yl-1H-indol-2-yl]-8-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)OC)C=1C=C(C=2N(C=1)N=CN=2)C XUUYWERTMXUPNC-UHFFFAOYSA-N 0.000 claims description 4
- CRYQGXSDULVWEI-UHFFFAOYSA-N 8-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]-1,3-diazaspiro[4.5]decane-2,4-dione Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC2(CC1)NC(=O)NC2=O)C1=CC(C)=NC(C)=C1 CRYQGXSDULVWEI-UHFFFAOYSA-N 0.000 claims description 4
- KULAXBLYDWZLHN-UHFFFAOYSA-N 8-methyl-6-[3-propan-2-yl-5-(pyrrolidin-2-ylmethyl)-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(CC3CCCN3)C=C12)C1=CN2N=CN=C2C(C)=C1 KULAXBLYDWZLHN-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
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- QJJZAYWNSXDWJI-UHFFFAOYSA-N 1,3-dimethyl-5-[5-(2-piperidin-1-ylethyl)-3-propan-2-yl-1H-indol-2-yl]pyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CCCCC3)C=C12)C1=CN(C)C(=O)C(C)=C1 QJJZAYWNSXDWJI-UHFFFAOYSA-N 0.000 claims 2
- UHQVMXQKQIMQLP-UHFFFAOYSA-N 1-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCN(C1)C(=O)C(C)(C)C)C1=CC(C)=NC(C)=C1 UHQVMXQKQIMQLP-UHFFFAOYSA-N 0.000 claims 2
- HVNKTMKSIYIGRR-UHFFFAOYSA-N 1-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCCC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CC(C)=NC(C)=C1 HVNKTMKSIYIGRR-UHFFFAOYSA-N 0.000 claims 2
- DAYASGQXGZKJMZ-UHFFFAOYSA-N 1-[3-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(dimethylamino)ethanone Chemical compound COC1=C(OC)C=C(C=C1)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCCN(C1)C(=O)CN(C)C DAYASGQXGZKJMZ-UHFFFAOYSA-N 0.000 claims 2
- VNTWGQWGNHBFOW-UHFFFAOYSA-N 1-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC(C)(C)O)C1)C1=CN2N=CN=C2C(C)=C1C VNTWGQWGNHBFOW-UHFFFAOYSA-N 0.000 claims 2
- XTPZRSQZNNBEKR-UHFFFAOYSA-N 1-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)ethanone Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CN(CCC1)C(CNC)=O)N=CN=2)C XTPZRSQZNNBEKR-UHFFFAOYSA-N 0.000 claims 2
- YIWCWEBEKKVRJX-UHFFFAOYSA-N 1-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCN(CC(C)(C)O)C1)C1=CN2N=CN=C2C(C)=C1C YIWCWEBEKKVRJX-UHFFFAOYSA-N 0.000 claims 2
- VHHCEVDIQDTRFW-UHFFFAOYSA-N 1-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]-2-(methylamino)ethanone Chemical compound CNCC(=O)N1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(OC)=C1 VHHCEVDIQDTRFW-UHFFFAOYSA-N 0.000 claims 2
- SXSJTNFDQNFKJG-UHFFFAOYSA-N 1-[3-[2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]ethyl]azetidin-1-yl]-2-methylpropan-2-ol Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CCC1CN(C1)CC(C)(O)C)C=1C=C(C=2N(C=1)N=CN=2)OC SXSJTNFDQNFKJG-UHFFFAOYSA-N 0.000 claims 2
- YBHKHDNPCSSSIM-UHFFFAOYSA-N 1-[[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]amino]-2-methylpropan-2-ol Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NCC(C)(C)O YBHKHDNPCSSSIM-UHFFFAOYSA-N 0.000 claims 2
- NFVBGVCUBPWBGR-LIKPIUCQSA-N 2,3,3a,4,6,6a-hexahydro-1H-pyrrolo[3,4-c]pyrrol-5-yl-[(1R,2S)-2-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclopropyl]methanone Chemical compound C1N(CC2C1CNC2)C(=O)[C@H]1[C@H](C1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C NFVBGVCUBPWBGR-LIKPIUCQSA-N 0.000 claims 2
- WFGGXUPXRQEXAN-TZWRJOPASA-N 2,5-diazabicyclo[2.2.1]heptan-2-yl-[(1R,2S)-2-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclopropyl]methanone Chemical compound C12N(CC(NC1)C2)C(=O)[C@H]1[C@H](C1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC=C1)C)C(C)C WFGGXUPXRQEXAN-TZWRJOPASA-N 0.000 claims 2
- KRVDQEBMDKQSPQ-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-[1-(1-propan-2-ylpiperidin-4-yl)piperidin-3-yl]-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)C1CCN(CC1)C(C)C)C KRVDQEBMDKQSPQ-UHFFFAOYSA-N 0.000 claims 2
- MUPANLIKWABJHF-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-5-pyrrolidin-3-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CNCC1)C MUPANLIKWABJHF-UHFFFAOYSA-N 0.000 claims 2
- UVWOHXLOQZSQBT-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[1-[(2-methyl-1H-imidazol-5-yl)methyl]piperidin-3-yl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)CC=1N=C(NC=1)C)C UVWOHXLOQZSQBT-UHFFFAOYSA-N 0.000 claims 2
- FTTGBFKIKPBRMQ-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-[4-(4-methylpiperazin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)N1CCN(CC1)C)C FTTGBFKIKPBRMQ-UHFFFAOYSA-N 0.000 claims 2
- INHPLFJOPMVAFV-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-5-piperidin-3-yl-3-propan-2-yl-1H-indole Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CNCCC1)C INHPLFJOPMVAFV-UHFFFAOYSA-N 0.000 claims 2
- NIAVPSJBCJWMFR-SFTDATJTSA-N 2-(2-methylpyridin-4-yl)-3-propan-2-yl-5-[(1R,2R)-2-(pyrrolidin-1-ylmethyl)cyclopropyl]-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)[C@H]1[C@@H](C1)CN1CCCC1)C1=CC(=NC=C1)C NIAVPSJBCJWMFR-SFTDATJTSA-N 0.000 claims 2
- WZWQUOYRGVIDGL-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-(4-piperidin-4-yloxycyclohexyl)-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)OC1CCNCC1)C1=CC(=NC=C1)C WZWQUOYRGVIDGL-UHFFFAOYSA-N 0.000 claims 2
- JSEWNOGKPSBKHQ-UHFFFAOYSA-N 2-(2-methylpyridin-4-yl)-5-piperidin-3-yl-3-propan-2-yl-1H-indole Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CNCCC1)C1=CC(=NC=C1)C JSEWNOGKPSBKHQ-UHFFFAOYSA-N 0.000 claims 2
- AHUPVZJVRLAAOJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-ethyl-5-(pyrrolidin-2-ylmethyl)-1H-indole Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1CC)CC1NCCC1 AHUPVZJVRLAAOJ-UHFFFAOYSA-N 0.000 claims 2
- SYVFYOWXQVYSFH-UHFFFAOYSA-N 2-(diethylamino)-N-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound C(C)N(CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C)CC SYVFYOWXQVYSFH-UHFFFAOYSA-N 0.000 claims 2
- MSTINECIUDWUAV-UHFFFAOYSA-N 2-(dimethylamino)-1-[2-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]morpholin-4-yl]ethanone Chemical compound CN(CC(=O)N1CC(OCC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C MSTINECIUDWUAV-UHFFFAOYSA-N 0.000 claims 2
- STNRNSHLNYITKN-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]pyrrolidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C STNRNSHLNYITKN-UHFFFAOYSA-N 0.000 claims 2
- BRLWUBRWCRIGCO-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]ethanone Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(C1)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1C BRLWUBRWCRIGCO-UHFFFAOYSA-N 0.000 claims 2
- MZHJOWNENJPQDO-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanone Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCN(C1)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1C MZHJOWNENJPQDO-UHFFFAOYSA-N 0.000 claims 2
- NWYKBUFFXYAEFC-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]ethyl]azetidin-1-yl]ethanone Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(CCC3CN(C3)C(=O)CN(C)C)=CC=C2N1 NWYKBUFFXYAEFC-UHFFFAOYSA-N 0.000 claims 2
- AAOPGPOQVRRSPR-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]methyl]azetidin-1-yl]ethanone Chemical compound CC(C)C1=C(NC2=CC=C(CC3CN(C3)C(=O)CN(C)C)C=C12)C1=CN2N=CN=C2C(C)=C1C AAOPGPOQVRRSPR-UHFFFAOYSA-N 0.000 claims 2
- KWXIMPCQXZOLOT-UHFFFAOYSA-N 2-(dimethylamino)-1-[3-[[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]methyl]azetidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CC(C1)CC=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C KWXIMPCQXZOLOT-UHFFFAOYSA-N 0.000 claims 2
- AYEXYFZEHSEWSK-UHFFFAOYSA-N 2-(dimethylamino)-1-[5-[2-(7,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]ethanone Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CC3C(CN(C3)C(CN(C)C)=O)C1)C=NN=2)C AYEXYFZEHSEWSK-UHFFFAOYSA-N 0.000 claims 2
- KFOOCACNNUWHPS-UHFFFAOYSA-N 2-(dimethylamino)-N-[3-[3-propan-2-yl-2-(1,4,5-trimethyl-6-oxopyridin-3-yl)-1H-indol-5-yl]cyclobutyl]acetamide Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC(C1)NC(=O)CN(C)C)C1=CN(C)C(=O)C(C)=C1C KFOOCACNNUWHPS-UHFFFAOYSA-N 0.000 claims 2
- IHBJXUCYOJAMPS-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CN(CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C)C IHBJXUCYOJAMPS-UHFFFAOYSA-N 0.000 claims 2
- JHRJBIKXULFXSG-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1C JHRJBIKXULFXSG-UHFFFAOYSA-N 0.000 claims 2
- YLPMRAGBHSRIAU-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CN(CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C)C YLPMRAGBHSRIAU-UHFFFAOYSA-N 0.000 claims 2
- FOMMVYRLQUAVAQ-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[3-propan-2-yl-2-(1,4,5-trimethyl-6-oxopyridin-3-yl)-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CN(CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C1=CN(C(C(=C1C)C)=O)C)C(C)C)C FOMMVYRLQUAVAQ-UHFFFAOYSA-N 0.000 claims 2
- JHKJGHOEPBGNLL-UHFFFAOYSA-N 2-(dimethylamino)-N-methyl-N-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CN(CC(=O)N(C)C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C)C JHKJGHOEPBGNLL-UHFFFAOYSA-N 0.000 claims 2
- OAOLBQWDKLYCGK-UHFFFAOYSA-N 2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methylamino]-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound CC1(OCC(O1)CNCC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C OAOLBQWDKLYCGK-UHFFFAOYSA-N 0.000 claims 2
- FGHCFDMIAZXTCF-UHFFFAOYSA-N 2-[(2-hydroxy-2-methylpropyl)amino]-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NC(=O)CNCC(C)(C)O FGHCFDMIAZXTCF-UHFFFAOYSA-N 0.000 claims 2
- CSFIZLJOLBBTOQ-UHFFFAOYSA-N 2-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]-4-(oxetan-3-yl)morpholine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCO1)C1COC1)C CSFIZLJOLBBTOQ-UHFFFAOYSA-N 0.000 claims 2
- UEUBCIVNFDKRLR-UHFFFAOYSA-N 2-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-4-(2-methylsulfonylethyl)morpholine Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CN(CCO1)CCS(=O)(=O)C)N=CN=2)C UEUBCIVNFDKRLR-UHFFFAOYSA-N 0.000 claims 2
- NVMASXPSNIEBSK-UHFFFAOYSA-N 2-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-5,5-dimethylmorpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNC(C)(C)CO1)C1=CN2N=CN=C2C(C)=C1C NVMASXPSNIEBSK-UHFFFAOYSA-N 0.000 claims 2
- QRUJQICFUNAZLI-UHFFFAOYSA-N 2-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CNCCO1)N=CN=2)C QRUJQICFUNAZLI-UHFFFAOYSA-N 0.000 claims 2
- RVOBUITVERWCNF-UHFFFAOYSA-N 2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-4,5,5-trimethylmorpholine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CN(C)C(C)(C)CO1 RVOBUITVERWCNF-UHFFFAOYSA-N 0.000 claims 2
- MCWMHEYQHCAUNQ-UHFFFAOYSA-N 2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-5,5-dimethyl-4-(oxetan-3-yl)morpholine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CN(C2COC2)C(C)(C)CO1 MCWMHEYQHCAUNQ-UHFFFAOYSA-N 0.000 claims 2
- WCAFZXNQMVYVOD-UHFFFAOYSA-N 2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-5,5-dimethylmorpholine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CNC(C)(C)CO1 WCAFZXNQMVYVOD-UHFFFAOYSA-N 0.000 claims 2
- ZTOSNNMVMUFYOH-UHFFFAOYSA-N 2-[3,3-bis(hydroxymethyl)azetidin-1-yl]-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound OCC1(CN(C1)CC(=O)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)CO ZTOSNNMVMUFYOH-UHFFFAOYSA-N 0.000 claims 2
- BUHVCIYLAOXRKS-UHFFFAOYSA-N 2-[3-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)CC(=O)N(C)C BUHVCIYLAOXRKS-UHFFFAOYSA-N 0.000 claims 2
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- MGMICNHCPVHNMX-UHFFFAOYSA-N 2-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]-N-methylacetamide Chemical compound CNC(=O)CN1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1C MGMICNHCPVHNMX-UHFFFAOYSA-N 0.000 claims 2
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- MGYLVKOMFUMQBE-UHFFFAOYSA-N 3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-(2-methylsulfonylethyl)cyclobutan-1-amine Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CC(C1)NCCS(=O)(=O)C)N=CN=2)C MGYLVKOMFUMQBE-UHFFFAOYSA-N 0.000 claims 2
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- GIYFRWSZZSTBPD-UHFFFAOYSA-N 3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N,N-dimethylcyclobutan-1-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CC(C1)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC GIYFRWSZZSTBPD-UHFFFAOYSA-N 0.000 claims 2
- XYDBUGBRQFMWTA-UHFFFAOYSA-N 3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-(2-methylsulfonylethyl)cyclobutan-1-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CC(C1)NCCS(C)(=O)=O XYDBUGBRQFMWTA-UHFFFAOYSA-N 0.000 claims 2
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- UVXIBASXINBGMX-UHFFFAOYSA-N 3-chloro-1,4-dimethyl-5-[3-propan-2-yl-5-(1-propylazetidin-3-yl)-1H-indol-2-yl]pyridin-2-one Chemical compound ClC=1C(N(C=C(C=1C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(C1)CCC)C)=O UVXIBASXINBGMX-UHFFFAOYSA-N 0.000 claims 2
- UESVQISBAQJRPZ-UHFFFAOYSA-N 3-chloro-1,4-dimethyl-5-[5-[1-(oxolan-3-ylmethyl)azetidin-3-yl]-3-propan-2-yl-1H-indol-2-yl]pyridin-2-one Chemical compound ClC=1C(N(C=C(C=1C)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(C1)CC1COCC1)C)=O UESVQISBAQJRPZ-UHFFFAOYSA-N 0.000 claims 2
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- HWIWCCDFYCWEGD-UHFFFAOYSA-N 3-methyl-N-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]oxetan-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC1(COC1)C)C=1C=C(C=2N(C=1)N=CN=2)C HWIWCCDFYCWEGD-UHFFFAOYSA-N 0.000 claims 2
- CESKXUSPVJAMTF-UHFFFAOYSA-N 4-(2-methoxyethyl)-2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound COCCN1CCOC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(OC)=C1 CESKXUSPVJAMTF-UHFFFAOYSA-N 0.000 claims 2
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- JFFYCHIIOJWMQG-UHFFFAOYSA-N 4-(2-methoxyethyl)-5,5-dimethyl-2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(C(CO1)(C)C)CCOC)C=1C=C(C=2N(C=1)N=CN=2)C JFFYCHIIOJWMQG-UHFFFAOYSA-N 0.000 claims 2
- WTHLNDJNMQTZOQ-UHFFFAOYSA-N 4-[(3-methyloxetan-3-yl)methyl]-2-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN(CC2(C)COC2)CCO1)C1=CN2N=CN=C2C(C)=C1 WTHLNDJNMQTZOQ-UHFFFAOYSA-N 0.000 claims 2
- WDLVKCLQVOZKQV-UHFFFAOYSA-N 4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]-N-[(4-methoxyphenyl)methyl]cyclohexan-1-amine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)NCC1=CC=C(C=C1)OC)C WDLVKCLQVOZKQV-UHFFFAOYSA-N 0.000 claims 2
- IDZSYRSXOGPDKA-UHFFFAOYSA-N 4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methylcyclohexan-1-amine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)NC)C IDZSYRSXOGPDKA-UHFFFAOYSA-N 0.000 claims 2
- OWQALSHFGFHWNT-UHFFFAOYSA-N 4-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-ol Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)O)C1=CC(=NC=C1)C OWQALSHFGFHWNT-UHFFFAOYSA-N 0.000 claims 2
- PIZQRKXUPBZLSG-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)N PIZQRKXUPBZLSG-UHFFFAOYSA-N 0.000 claims 2
- ZIBKTCVZFPGFOL-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyphenyl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-ol Chemical compound COC=1C=C(C=CC=1OC)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)O ZIBKTCVZFPGFOL-UHFFFAOYSA-N 0.000 claims 2
- KPLMFWXPXBJEAG-UHFFFAOYSA-N 4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-ethyl-N-methylcyclohexan-1-amine Chemical compound CCN(C)C1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1C KPLMFWXPXBJEAG-UHFFFAOYSA-N 0.000 claims 2
- YAFWDGHOQFGZJU-UHFFFAOYSA-N 4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methyl-N-(2-methylsulfonylethyl)cyclohexan-1-amine Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CCC(CC1)N(CCS(=O)(=O)C)C)N=CN=2)C YAFWDGHOQFGZJU-UHFFFAOYSA-N 0.000 claims 2
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- KTRGIAGCHXDPRA-UHFFFAOYSA-N 4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-(1-methylcyclopropyl)cyclohexan-1-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC1(CC1)C)C=1C=C(C=2N(C=1)N=CN=2)OC KTRGIAGCHXDPRA-UHFFFAOYSA-N 0.000 claims 2
- NRIRKYMRBOSKMQ-UHFFFAOYSA-N 4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-(1-propan-2-ylpiperidin-4-yl)cyclohexane-1-carboxamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)C(=O)NC1CCN(CC1)C(C)C)C=1C=C(C=2N(C=1)N=CN=2)C NRIRKYMRBOSKMQ-UHFFFAOYSA-N 0.000 claims 2
- BLAQBNDCAHEFPU-UHFFFAOYSA-N 4-[2-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]ethyl]-1,4-thiazinane 1,1-dioxide Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CCS(=O)(=O)CC3)C=C12)C1=CC(C)=NC(C)=C1 BLAQBNDCAHEFPU-UHFFFAOYSA-N 0.000 claims 2
- BPSIMNFOBXYYBO-UHFFFAOYSA-N 4-[2-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]ethyl]morpholine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CCN1CCOCC1)C=1C=C(C=2N(C=1)N=CN=2)OC BPSIMNFOBXYYBO-UHFFFAOYSA-N 0.000 claims 2
- SFWLZPPPTRPMNY-UHFFFAOYSA-N 4-[3-propan-2-yl-5-(4-pyridin-4-yloxycyclohexyl)-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)OC1=CC=NC=C1)C1=C2C(=NC=C1)NN=C2 SFWLZPPPTRPMNY-UHFFFAOYSA-N 0.000 claims 2
- YMVZQNLNFNTFRA-UHFFFAOYSA-N 4-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]morpholine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N1CCOCC1)C1=CN2N=CN=C2C(C)=C1C YMVZQNLNFNTFRA-UHFFFAOYSA-N 0.000 claims 2
- TTWKBAJROXFJBP-UHFFFAOYSA-N 4-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-2,6-dimethylmorpholine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)N1CC(C)OC(C)C1 TTWKBAJROXFJBP-UHFFFAOYSA-N 0.000 claims 2
- LAEIJNFHMHEJSR-UHFFFAOYSA-N 4-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]morpholine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N1CCOCC1)C=1C=C(C=2N(C=1)N=CN=2)C LAEIJNFHMHEJSR-UHFFFAOYSA-N 0.000 claims 2
- CWLKUMPMVPDZTE-UHFFFAOYSA-N 4-[5-(1-piperidin-4-ylethyl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C(C)C1CCNCC1)C1=C2C(=NC=C1)NN=C2 CWLKUMPMVPDZTE-UHFFFAOYSA-N 0.000 claims 2
- RMZJXKGMOLQTHX-UHFFFAOYSA-N 4-[5-(2-piperidin-4-ylethyl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CCC1CCNCC1)C1=C2C(=NC=C1)NN=C2 RMZJXKGMOLQTHX-UHFFFAOYSA-N 0.000 claims 2
- PWIOUQALWAWEIL-UHFFFAOYSA-N 4-[5-(4-piperidin-4-yloxycyclohexyl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)OC1CCNCC1)C1=C2C(=NC=C1)NN=C2 PWIOUQALWAWEIL-UHFFFAOYSA-N 0.000 claims 2
- HOVIACXZDVHHMR-UHFFFAOYSA-N 4-[5-(azepan-4-yl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound N1CCC(CCC1)C=1C=C2C(=C(NC2=CC=1)C1=C2C(=NC=C1)NN=C2)C(C)C HOVIACXZDVHHMR-UHFFFAOYSA-N 0.000 claims 2
- IBTFDGFDHMDFRO-UHFFFAOYSA-N 4-[5-(piperidin-1-ylmethyl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CN1CCCCC1)C1=C2C(=NC=C1)NN=C2 IBTFDGFDHMDFRO-UHFFFAOYSA-N 0.000 claims 2
- LIKAZLPRJOLYRJ-UHFFFAOYSA-N 4-[5-(piperidin-4-ylmethyl)-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CC1CCNCC1)C1=C2C(=NC=C1)NN=C2 LIKAZLPRJOLYRJ-UHFFFAOYSA-N 0.000 claims 2
- HWHYRVJPBKIIGZ-UHFFFAOYSA-N 4-[5-[(4-methylpiperazin-1-yl)methyl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CN1CCN(CC1)C)C1=C2C(=NC=C1)NN=C2 HWHYRVJPBKIIGZ-UHFFFAOYSA-N 0.000 claims 2
- FMACPBCZPANKIB-ONEGZZNKSA-N 4-[5-[(E)-2-piperidin-4-ylethenyl]-3-propan-2-yl-1H-indol-2-yl]-1H-pyrazolo[3,4-b]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)\C=C\C1CCNCC1)C1=C2C(=NC=C1)NN=C2 FMACPBCZPANKIB-ONEGZZNKSA-N 0.000 claims 2
- ZXJWXWVCAMVTQB-UHFFFAOYSA-N 5-(5-cyclohexyl-3-propan-2-yl-1H-indol-2-yl)-1,3-dimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCCC1)C1=CN(C)C(=O)C(C)=C1 ZXJWXWVCAMVTQB-UHFFFAOYSA-N 0.000 claims 2
- RSKUHVQQCIUZIL-UHFFFAOYSA-N 5-(azetidin-3-yl)-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNC1)C1=CC(C)=NC(C)=C1 RSKUHVQQCIUZIL-UHFFFAOYSA-N 0.000 claims 2
- JCWSUPGAFPKNRI-UHFFFAOYSA-N 5-[5-(3-aminocyclobutyl)-3-propan-2-yl-1H-indol-2-yl]-1,3,4-trimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC(N)C1)C1=CN(C)C(=O)C(C)=C1C JCWSUPGAFPKNRI-UHFFFAOYSA-N 0.000 claims 2
- PQYPJWXEFIQVEP-UHFFFAOYSA-N 5-[5-(azetidin-3-yl)-3-propan-2-yl-1H-indol-2-yl]-1,3,4-trimethylpyridin-2-one Chemical compound N1CC(C1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C(N(C=1)C)=O)C)C)C(C)C PQYPJWXEFIQVEP-UHFFFAOYSA-N 0.000 claims 2
- IBWZUUUPFSDXKE-UHFFFAOYSA-N 5-[5-(azetidin-3-ylmethyl)-3-propan-2-yl-1H-indol-2-yl]-1,3,4-trimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CC3CNC3)C=C12)C1=CN(C)C(=O)C(C)=C1C IBWZUUUPFSDXKE-UHFFFAOYSA-N 0.000 claims 2
- IUJVIBSJKDJMEI-UHFFFAOYSA-N 5-[5-[1-(2-methoxyethyl)azetidin-3-yl]-3-propan-2-yl-1H-indol-2-yl]-1,3,4-trimethylpyridin-2-one Chemical compound COCCN1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN(C)C(=O)C(C)=C1C IUJVIBSJKDJMEI-UHFFFAOYSA-N 0.000 claims 2
- JUUFYCBATDXZKT-UHFFFAOYSA-N 5-[5-[2-(3,3-difluoropiperidin-1-yl)ethyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CCCC(F)(F)C3)C=C12)C1=CN(C)C(=O)C(C)=C1 JUUFYCBATDXZKT-UHFFFAOYSA-N 0.000 claims 2
- RSXMXMFCDLGBCJ-UHFFFAOYSA-N 5-[5-[2-(3-fluoropiperidin-1-yl)ethyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CCCC(F)C3)C=C12)C1=CN(C)C(=O)C(C)=C1 RSXMXMFCDLGBCJ-UHFFFAOYSA-N 0.000 claims 2
- RSIOCNAXSDNODZ-UHFFFAOYSA-N 5-[5-[2-(4-fluoropiperidin-1-yl)ethyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CCC(F)CC3)C=C12)C1=CN(C)C(=O)C(C)=C1 RSIOCNAXSDNODZ-UHFFFAOYSA-N 0.000 claims 2
- WSSXFHSXPMGWHK-LJQANCHMSA-N 5-[5-[2-[(3R)-3-fluoropyrrolidin-1-yl]ethyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(CCN3CC[C@@H](F)C3)C=C12)C1=CN(C)C(=O)C(C)=C1 WSSXFHSXPMGWHK-LJQANCHMSA-N 0.000 claims 2
- DHVAQOUMEPMNLZ-UHFFFAOYSA-N 5-[5-[4-(3,3-difluoropiperidin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound FC1(CN(CCC1)C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C)C(C)C)F DHVAQOUMEPMNLZ-UHFFFAOYSA-N 0.000 claims 2
- CYVUTDJAPMGNEE-UHFFFAOYSA-N 5-[5-[4-(4,4-difluoropiperidin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-1,3-dimethylpyridin-2-one Chemical compound FC1(CCN(CC1)C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C(N(C=1)C)=O)C)C(C)C)F CYVUTDJAPMGNEE-UHFFFAOYSA-N 0.000 claims 2
- DXWOCIUJWHLJQS-UHFFFAOYSA-N 5-[5-[4-(dimethylamino)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-1,3,4-trimethylpyridin-2-one Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N(C)C)C1=CN(C)C(=O)C(C)=C1C DXWOCIUJWHLJQS-UHFFFAOYSA-N 0.000 claims 2
- OBEZRBVTUUJMRA-UHFFFAOYSA-N 5-cyclohexyl-2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indole Chemical compound C1(CCCCC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C OBEZRBVTUUJMRA-UHFFFAOYSA-N 0.000 claims 2
- YJHCVPGBDBXGBB-UHFFFAOYSA-N 5-methyl-6-(5-piperidin-3-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCNC1)C1=C(C)N2N=CN=C2C=C1 YJHCVPGBDBXGBB-UHFFFAOYSA-N 0.000 claims 2
- KAGHIIOPKAISMU-UHFFFAOYSA-N 6-[5-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-yl)-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC2CNCC2C1)C1=CN2N=CN=C2C(C)=C1C KAGHIIOPKAISMU-UHFFFAOYSA-N 0.000 claims 2
- SVXWCDAAJIYENY-UHFFFAOYSA-N 6-[5-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-yl)-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC2CNCC2C1)C1=CN2C=NN=C2C(C)=C1C SVXWCDAAJIYENY-UHFFFAOYSA-N 0.000 claims 2
- AUBPUXFXUJUHEN-UHFFFAOYSA-N 6-[5-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-5-yl)-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CC2CNCC2C1 AUBPUXFXUJUHEN-UHFFFAOYSA-N 0.000 claims 2
- BGZOKTGEBPJSRN-UHFFFAOYSA-N 6-[5-(1-azabicyclo[2.2.2]octan-3-yl)-3-propan-2-yl-1H-indol-2-yl]-8-methyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CN2CCC1CC2)C1=CN2N=CN=C2C(C)=C1 BGZOKTGEBPJSRN-UHFFFAOYSA-N 0.000 claims 2
- OSZVKTTZYHKEEW-UHFFFAOYSA-N 6-[5-(azetidin-3-yl)-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CNC1)C1=CN2N=CN=C2C(C)=C1C OSZVKTTZYHKEEW-UHFFFAOYSA-N 0.000 claims 2
- ANCAXXFEXAQKFO-UHFFFAOYSA-N 6-[5-(azetidin-3-yl)-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound N1CC(C1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C=2N(C=1)C=NN=2)C)C)C(C)C ANCAXXFEXAQKFO-UHFFFAOYSA-N 0.000 claims 2
- RYAJEHZWCYBXBY-UHFFFAOYSA-N 6-[5-(azetidin-3-yl)-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1CC(C1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C RYAJEHZWCYBXBY-UHFFFAOYSA-N 0.000 claims 2
- AGKHSGMNWYDDQR-UHFFFAOYSA-N 6-[5-(azetidin-3-ylmethyl)-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1CC(C1)CC=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C AGKHSGMNWYDDQR-UHFFFAOYSA-N 0.000 claims 2
- KOFBUIBBMPIXPE-UHFFFAOYSA-N 6-[5-[1-(2-methoxyethyl)azetidin-3-yl]-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridine Chemical compound COCCN1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2C=NN=C2C(C)=C1C KOFBUIBBMPIXPE-UHFFFAOYSA-N 0.000 claims 2
- GCBUDTVJQWRUPH-UHFFFAOYSA-N 6-[5-[2-(azetidin-3-yl)ethyl]-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1CC(C1)CCC=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C GCBUDTVJQWRUPH-UHFFFAOYSA-N 0.000 claims 2
- MDNRXDVMSIQSPD-UHFFFAOYSA-N 6-[5-[4-(3,3-difluoroazetidin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1(CN(C1)C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C)F MDNRXDVMSIQSPD-UHFFFAOYSA-N 0.000 claims 2
- DKAOGLNGQHRWQE-UHFFFAOYSA-N 6-[5-[4-(3,3-difluoroazetidin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1(CN(C1)C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)F DKAOGLNGQHRWQE-UHFFFAOYSA-N 0.000 claims 2
- MXMYYQVBJDAYLO-UHFFFAOYSA-N 6-[5-[4-(3,3-difluoropiperidin-1-yl)cyclohexyl]-3-propan-2-yl-1H-indol-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)N1CCCC(F)(F)C1 MXMYYQVBJDAYLO-UHFFFAOYSA-N 0.000 claims 2
- QMYQVLQALQONMY-UHFFFAOYSA-N 7,8-dimethyl-6-(5-piperidin-3-yl-3-propan-2-yl-1H-indol-2-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CNCCC1)C=1C(=C(C=2N(C=1)N=CN=2)C)C QMYQVLQALQONMY-UHFFFAOYSA-N 0.000 claims 2
- PSIMWZHQEVCNLM-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-(1-propan-2-ylazetidin-3-yl)-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound CC(C)N1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1C PSIMWZHQEVCNLM-UHFFFAOYSA-N 0.000 claims 2
- KBUOAUXJZYFMGI-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-(1-propan-2-ylazetidin-3-yl)-1H-indol-2-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound CC(C)N1CC(C1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2C=NN=C2C(C)=C1C KBUOAUXJZYFMGI-UHFFFAOYSA-N 0.000 claims 2
- UJYUURHFJGMVRS-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-(1-propylazetidin-3-yl)-1H-indol-2-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(C1)CCC)C=1C(=C(C=2N(C=1)C=NN=2)C)C UJYUURHFJGMVRS-UHFFFAOYSA-N 0.000 claims 2
- GQSGCGWXRRLELF-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-(2-propan-2-yl-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-5-yl)-1H-indol-2-yl]-[1,2,4]triazolo[4,3-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CC2C(CN(C2)C(C)C)C1)C=1C(=C(C=2N(C=1)C=NN=2)C)C GQSGCGWXRRLELF-UHFFFAOYSA-N 0.000 claims 2
- CTKHYSJEADBPLC-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-[(1-propan-2-ylazetidin-3-yl)methyl]-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)CC1CN(C1)C(C)C)C=1C(=C(C=2N(C=1)N=CN=2)C)C CTKHYSJEADBPLC-UHFFFAOYSA-N 0.000 claims 2
- FCVDSQFKSQSPHR-UHFFFAOYSA-N 7,8-dimethyl-6-[3-propan-2-yl-5-[1-(2H-triazol-4-ylmethyl)azetidin-3-yl]-1H-indol-2-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound N1N=NC(=C1)CN1CC(C1)C=1C=C2C(=C(NC2=CC=1)C=1C(=C(C=2N(C=1)N=CN=2)C)C)C(C)C FCVDSQFKSQSPHR-UHFFFAOYSA-N 0.000 claims 2
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- WDSGXGPCIDPXSS-UHFFFAOYSA-N N,N-dimethyl-2-[2-[[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]methyl]pyrrolidin-1-yl]acetamide Chemical compound CC(C)C1=C(NC2=CC=C(CC3CCCN3CC(=O)N(C)C)C=C12)C1=CN2N=CN=C2C(C)=C1 WDSGXGPCIDPXSS-UHFFFAOYSA-N 0.000 claims 2
- XEHMJUCBVALWSI-UHFFFAOYSA-N N,N-dimethyl-2-[3-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]acetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(C1)CC(=O)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)C XEHMJUCBVALWSI-UHFFFAOYSA-N 0.000 claims 2
- MUAPSYZVMLHDCK-UHFFFAOYSA-N N,N-dimethyl-2-[3-[3-propan-2-yl-2-(1,4,5-trimethyl-6-oxopyridin-3-yl)-1H-indol-5-yl]azetidin-1-yl]acetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(C1)CC(=O)N(C)C)C1=CN(C(C(=C1C)C)=O)C MUAPSYZVMLHDCK-UHFFFAOYSA-N 0.000 claims 2
- WCBOLDXKGHCHAL-UHFFFAOYSA-N N-(2,2-difluoroethyl)-4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NCC(F)F WCBOLDXKGHCHAL-UHFFFAOYSA-N 0.000 claims 2
- SLAJUHJIBKPGTF-UHFFFAOYSA-N N-[2-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]azetidin-1-yl]ethyl]methanesulfonamide Chemical compound CC1=C(C=2N(C=C1C=1NC3=CC=C(C=C3C=1C(C)C)C1CN(C1)CCNS(=O)(=O)C)N=CN=2)C SLAJUHJIBKPGTF-UHFFFAOYSA-N 0.000 claims 2
- RMONMJQVIKJDNK-UHFFFAOYSA-N N-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclobutyl]oxetan-3-amine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CC(C1)NC1COC1)C1=CN2N=CN=C2C(C)=C1C RMONMJQVIKJDNK-UHFFFAOYSA-N 0.000 claims 2
- JBYMFLNXHARTEP-UHFFFAOYSA-N N-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclobutyl]oxetan-3-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CC(C1)NC1COC1 JBYMFLNXHARTEP-UHFFFAOYSA-N 0.000 claims 2
- YMVVEUWBIMWUQN-UHFFFAOYSA-N N-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-2-(methylamino)acetamide Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)NC(CNC)=O)C YMVVEUWBIMWUQN-UHFFFAOYSA-N 0.000 claims 2
- JJHJWGYRXRLUHT-UHFFFAOYSA-N N-[4-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]oxetan-3-amine Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CCC(CC1)NC1COC1)C JJHJWGYRXRLUHT-UHFFFAOYSA-N 0.000 claims 2
- IXFHLYLKYCVIGJ-UHFFFAOYSA-N N-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-3-methyloxetan-3-amine Chemical compound CC1=C(C2=NC=NN2C=C1C3=C(C4=C(N3)C=CC(=C4)C5CCC(CC5)NC6(COC6)C)C(C)C)C IXFHLYLKYCVIGJ-UHFFFAOYSA-N 0.000 claims 2
- GIGHRBHIDNJOMT-UHFFFAOYSA-N N-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]oxetan-3-amine Chemical compound CC1=C(C2=NC=NN2C=C1C3=C(C4=C(N3)C=CC(=C4)C5CCC(CC5)NC6COC6)C(C)C)C GIGHRBHIDNJOMT-UHFFFAOYSA-N 0.000 claims 2
- RXPRNGLGXPRLSJ-UHFFFAOYSA-N N-[4-[2-(7,8-dimethyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]oxetan-3-amine Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC1COC1)C1=CN2C=NN=C2C(C)=C1C RXPRNGLGXPRLSJ-UHFFFAOYSA-N 0.000 claims 2
- RZVKLHDVWVJCLG-UHFFFAOYSA-N N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-2-(2-oxa-6-azaspiro[3.3]heptan-6-yl)acetamide Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NC(=O)CN1CC2(COC2)C1 RZVKLHDVWVJCLG-UHFFFAOYSA-N 0.000 claims 2
- WVOBYQWVJOXABY-UHFFFAOYSA-N N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-2-[(3-methyloxetan-3-yl)amino]acetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC(CNC1(COC1)C)=O)C=1C=C(C=2N(C=1)N=CN=2)OC WVOBYQWVJOXABY-UHFFFAOYSA-N 0.000 claims 2
- MPALSODRRDFPOY-UHFFFAOYSA-N N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-2-pyrrolidin-1-ylacetamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)NC(CN1CCCC1)=O)C=1C=C(C=2N(C=1)N=CN=2)OC MPALSODRRDFPOY-UHFFFAOYSA-N 0.000 claims 2
- FUMHLBATCPKOLW-UHFFFAOYSA-N N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-3-methyloxetan-3-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NC1(C)COC1 FUMHLBATCPKOLW-UHFFFAOYSA-N 0.000 claims 2
- XQHSHJAACRBZCF-UHFFFAOYSA-N N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]-1-methylpiperidine-4-carboxamide Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(=O)C1CCN(CC1)C)C1=CC(=NC=C1)C XQHSHJAACRBZCF-UHFFFAOYSA-N 0.000 claims 2
- BMVWRNVGOIWPBV-UHFFFAOYSA-N N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]-3-piperidin-4-ylpropanamide Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(CCC1CCNCC1)=O)C1=CC(=NC=C1)C BMVWRNVGOIWPBV-UHFFFAOYSA-N 0.000 claims 2
- SRYSYFRCBDMYCZ-UHFFFAOYSA-N N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]-4-methylpiperazine-1-carboxamide Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(=O)N1CCN(CC1)C)C1=CC(=NC=C1)C SRYSYFRCBDMYCZ-UHFFFAOYSA-N 0.000 claims 2
- JSRVJFUWYJHQSD-UHFFFAOYSA-N N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]-7-azaspiro[3.5]nonane-2-carboxamide Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(=O)C1CC2(C1)CCNCC2)C1=CC(=NC=C1)C JSRVJFUWYJHQSD-UHFFFAOYSA-N 0.000 claims 2
- OXWNDNNYYYOWBS-UHFFFAOYSA-N N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]pyrrolidine-3-carboxamide Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(=O)C1CNCC1)C1=CC(=NC=C1)C OXWNDNNYYYOWBS-UHFFFAOYSA-N 0.000 claims 2
- DFZACIAVORBTPM-UHFFFAOYSA-N N-cyclopropyl-4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methylcyclohexan-1-amine Chemical compound C1(CC1)N(C1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C DFZACIAVORBTPM-UHFFFAOYSA-N 0.000 claims 2
- RIBSXSIVMFKYLZ-UHFFFAOYSA-N N-cyclopropyl-4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NC1CC1 RIBSXSIVMFKYLZ-UHFFFAOYSA-N 0.000 claims 2
- DVCXFVLWQWYRKT-UHFFFAOYSA-N N-cyclopropyl-4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound C1(CC1)NC1CCC(CC1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)C)C(C)C DVCXFVLWQWYRKT-UHFFFAOYSA-N 0.000 claims 2
- ITACBXSUSSJVQJ-UHFFFAOYSA-N N-ethyl-4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methylcyclohexan-1-amine Chemical compound CCN(C)C1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(OC)=C1 ITACBXSUSSJVQJ-UHFFFAOYSA-N 0.000 claims 2
- OHNMYUQTAZKOIO-UHFFFAOYSA-N N-ethyl-N-methyl-4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexan-1-amine Chemical compound CCN(C)C1CCC(CC1)C1=CC=C2NC(=C(C(C)C)C2=C1)C1=CN2N=CN=C2C(C)=C1 OHNMYUQTAZKOIO-UHFFFAOYSA-N 0.000 claims 2
- SHZTZCOOAYCZBA-UHFFFAOYSA-N N-methoxy-4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]-N-methylcyclohexan-1-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N(OC)C)C=1C=C(C=2N(C=1)N=CN=2)OC SHZTZCOOAYCZBA-UHFFFAOYSA-N 0.000 claims 2
- DKZLQBMOQNFVSX-UHFFFAOYSA-N N-methyl-2-[3-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]ethanamine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(CCC1)CCNC)C1=CC(=NC=C1)C DKZLQBMOQNFVSX-UHFFFAOYSA-N 0.000 claims 2
- RZWBYPDJOBNQCN-UHFFFAOYSA-N [3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-(3-methyloxetan-3-yl)methanone Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)C(=O)C1(COC1)C)C RZWBYPDJOBNQCN-UHFFFAOYSA-N 0.000 claims 2
- OFOHBBDOSCGXFL-UHFFFAOYSA-N [3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-(1-methylpiperidin-4-yl)methanone Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CN(CCC1)C(=O)C1CCN(CC1)C)C=1C=C(C=2N(C=1)N=CN=2)OC OFOHBBDOSCGXFL-UHFFFAOYSA-N 0.000 claims 2
- HNINYOGGWLGUOE-UHFFFAOYSA-N [4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-piperidin-1-ylmethanone Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)C(=O)N1CCCCC1)C=1C=C(C=2N(C=1)N=CN=2)C HNINYOGGWLGUOE-UHFFFAOYSA-N 0.000 claims 2
- YFGFNHOHRYLFMS-UHFFFAOYSA-N azetidin-3-yl-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]methanone Chemical compound N1CC(C1)C(=O)N1CC(CCC1)C=1C=C2C(=C(NC2=CC=1)C1=CC(=NC(=C1)C)C)C(C)C YFGFNHOHRYLFMS-UHFFFAOYSA-N 0.000 claims 2
- YAEGPBYHTNIDKX-UHFFFAOYSA-N piperidin-4-ylmethyl N-[[3-ethyl-2-(2-methylpyridin-4-yl)-1H-indol-5-yl]methyl]carbamate Chemical compound C(C)C1=C(NC2=CC=C(C=C12)CNC(OCC1CCNCC1)=O)C1=CC(=NC=C1)C YAEGPBYHTNIDKX-UHFFFAOYSA-N 0.000 claims 2
- JIIUBDHYJYDTQM-MXKXXCEUSA-N (1R,2R)-N-(1-azabicyclo[2.2.2]octan-2-yl)-N-methyl-2-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclopropane-1-carboxamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)[C@H]1[C@@H](C1)C(=O)N(C1N2CCC(C1)CC2)C)C1=CC(=NC=C1)C JIIUBDHYJYDTQM-MXKXXCEUSA-N 0.000 claims 1
- BWVFLQHTPHMRQE-AUAZYCQOSA-N (1R,2S)-N-(1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrol-4-yl)-2-[2-(2-methylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]cyclopropane-1-carboxamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)[C@@H]1[C@@H](C1)C(=O)NC1CCC2CNCC21)C1=CC(=NC=C1)C BWVFLQHTPHMRQE-AUAZYCQOSA-N 0.000 claims 1
- WAMIMFBUKQWNAN-YMBRHYMPSA-N (2R)-1-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)propan-1-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)C([C@@H](C)NC)=O)C WAMIMFBUKQWNAN-YMBRHYMPSA-N 0.000 claims 1
- WAMIMFBUKQWNAN-ZQRQZVKFSA-N (2S)-1-[3-[2-(2,6-dimethylpyridin-4-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-2-(methylamino)propan-1-one Chemical compound CC1=NC(=CC(=C1)C=1NC2=CC=C(C=C2C=1C(C)C)C1CN(CCC1)C([C@H](C)NC)=O)C WAMIMFBUKQWNAN-ZQRQZVKFSA-N 0.000 claims 1
- MHUKJALTLUOOSF-DLUKIOLESA-N (2S)-1-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]pyrrolidine-2-carboxamide Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N1[C@@H](CCC1)C(=O)N)C=1C=C(C=2N(C=1)N=CN=2)OC MHUKJALTLUOOSF-DLUKIOLESA-N 0.000 claims 1
- JJDZZJFIIYQFRO-VZYOYLOZSA-N (3R)-1-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]-N,N-dimethylpyrrolidin-3-amine Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N1C[C@@H](CC1)N(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC JJDZZJFIIYQFRO-VZYOYLOZSA-N 0.000 claims 1
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- FKOCCMCOCAWYFP-UHFFFAOYSA-N 1-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]azetidin-3-ol Chemical compound C(C)(C)C1=C(NC2=CC=C(C=C12)C1CCC(CC1)N1CC(C1)O)C=1C=C(C=2N(C=1)N=CN=2)OC FKOCCMCOCAWYFP-UHFFFAOYSA-N 0.000 claims 1
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- NETIQPLZIFLUGN-UHFFFAOYSA-N 2-(dimethylamino)-N-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclobutyl]-N-methylacetamide Chemical compound CC(C)C1=C(NC2=C1C=C(C=C2)C1CC(C1)N(C)C(=O)CN(C)C)C1=CN2N=CN=C2C(C)=C1C NETIQPLZIFLUGN-UHFFFAOYSA-N 0.000 claims 1
- BRUBXXCAHDRVEN-UHFFFAOYSA-N 2-(dimethylamino)-N-[3-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclobutyl]-N-methylacetamide Chemical compound CN(CC(=O)N(C)C1CC(C1)C=1C=C2C(=C(NC2=CC=1)C=1C=C(C=2N(C=1)N=CN=2)OC)C(C)C)C BRUBXXCAHDRVEN-UHFFFAOYSA-N 0.000 claims 1
- ZBUOUZIZINRRGR-UHFFFAOYSA-N 2-(dimethylamino)-N-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]cyclohexyl]acetamide Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=CC(=CC=C2N1)C1CCC(CC1)NC(=O)CN(C)C ZBUOUZIZINRRGR-UHFFFAOYSA-N 0.000 claims 1
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- UGNCNQLNUYIDEF-UHFFFAOYSA-N 2-[3-[2-(7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-indol-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC(C)C1=C(NC2=CC=C(C=C12)C1CCCN(CC(=O)N(C)C)C1)C1=CN2N=CN=C2C(C)=C1C UGNCNQLNUYIDEF-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
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- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- C—CHEMISTRY; METALLURGY
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| SG11202005704RA (en) * | 2017-12-19 | 2020-07-29 | Bristol Myers Squibb Co | 6-azaindole compounds |
| KR102730859B1 (ko) * | 2017-12-20 | 2024-11-15 | 브리스톨-마이어스 스큅 컴퍼니 | 아릴 및 헤테로아릴 치환된 인돌 화합물 |
| BR112020011984A2 (pt) * | 2017-12-20 | 2020-11-17 | Bristol-Myers Squibb Company | compostos de amino indol úteis como inibidores de tlr |
| JP7328977B2 (ja) | 2018-02-12 | 2023-08-17 | エフ. ホフマン-ラ ロシュ アーゲー | ウイルス感染の処置および予防のための新規のスルホン化合物および誘導体 |
| PE20210131A1 (es) | 2018-06-05 | 2021-01-19 | Hoffmann La Roche | COMPUESTOS TETRAHIDRO-1H-PIRAZINO[2,1-a]ISOINDOLILQUINOLINA PARA EL TRATAMIENTO DE ENFERMEDADES AUTOINMUNES |
| EP3807270B1 (en) | 2018-06-12 | 2023-09-13 | F. Hoffmann-La Roche AG | Novel heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
| EP3826724B1 (en) | 2018-07-23 | 2022-10-05 | F. Hoffmann-La Roche AG | Novel piperazine compounds for the treatment of autoimmune disease |
| WO2020048583A1 (en) | 2018-09-04 | 2020-03-12 | F. Hoffmann-La Roche Ag | Benzothiazole compounds for the treatment of autoimmune diseases |
| EP3847173B1 (en) | 2018-09-06 | 2023-04-12 | F. Hoffmann-La Roche AG | Novel pyrazolopyridine compounds for the treatment of autoimmune disease |
| US11548884B2 (en) | 2018-09-06 | 2023-01-10 | Hoffmann-La Roche Inc. | Cyclic amidine compounds for the treatment of autoimmune disease |
| CN112955450A (zh) | 2018-10-24 | 2021-06-11 | 百时美施贵宝公司 | 经取代的吲哚和吲唑化合物 |
| KR20210080462A (ko) * | 2018-10-24 | 2021-06-30 | 브리스톨-마이어스 스큅 컴퍼니 | 치환된 인돌 이량체 화합물 |
| WO2020227484A1 (en) * | 2019-05-09 | 2020-11-12 | Bristol-Myers Squibb Company | Substituted benzimidazolone compounds |
| EP4038059B1 (en) * | 2019-10-04 | 2023-09-20 | Bristol-Myers Squibb Company | Substituted carbazole compounds |
| EP4051387B1 (en) | 2019-10-31 | 2025-02-19 | F. Hoffmann-La Roche AG | Hydropyrazino[1,2-d][1,4]diazepine compounds for the treatment of autoimmune disease |
| US12486273B2 (en) | 2019-11-19 | 2025-12-02 | Hoffmann-La Roche Inc. | Hydro-1H-pyrrolo[1,2-a]pyrazine compounds for the treatment of autoimmune disease |
| WO2021099406A1 (en) | 2019-11-20 | 2021-05-27 | F. Hoffmann-La Roche Ag | Spiro(isobenzofuranazetidine) compounds for the treatment of autoimmune disease |
| US20230116201A1 (en) * | 2020-01-30 | 2023-04-13 | Anima Biotech Inc. | Collagen 1 translation inhibitors and methods of use thereof |
| JP2023538619A (ja) | 2020-08-19 | 2023-09-08 | ブリストル-マイヤーズ スクイブ カンパニー | 線維症の処置のためのtlr9阻害剤としての1h-ベンゾ[d]イミダゾール誘導体 |
| IL300727A (en) | 2020-08-19 | 2023-04-01 | Bristol Myers Squibb Co | Imidazo[1,2-a]pyridine and [1,2,4]triazolo[1,5-a]pyridine derivatives as tlr9 inhibitors for the treatment of fibrosis |
| WO2022140325A1 (en) * | 2020-12-22 | 2022-06-30 | Gilead Sciences, Inc. | 6-substituted indole compounds |
| CN116783202A (zh) * | 2021-02-09 | 2023-09-19 | 吉利德科学公司 | 噻吩并吡咯化合物 |
| TWI861488B (zh) | 2021-04-16 | 2024-11-11 | 美商基利科學股份有限公司 | 噻吩并吡咯化合物 |
| KR20240056747A (ko) | 2021-09-10 | 2024-04-30 | 길리애드 사이언시즈, 인코포레이티드 | 티에노피롤 화합물 |
| EP4479135A1 (en) * | 2022-02-18 | 2024-12-25 | Bristol-Myers Squibb Company | Substituted imidazopyridinyl compounds useful as inhibitors of tlr9 |
| CN114591339B (zh) * | 2022-05-10 | 2022-08-02 | 上海维申医药有限公司 | 一类Toll样受体抑制剂及其制备和应用 |
| WO2025147320A1 (en) * | 2024-01-03 | 2025-07-10 | Kymera Therapeutics, Inc. | Stat6 inhibitors and uses thereof |
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| GEP20053530B (en) | 1999-10-19 | 2005-05-25 | Merck & Co Inc | Tyrosine Kinase Inhibitors, Pharmaceutical Compositions Containing Them and Use Thereof |
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- 2018-12-18 MX MX2020005462A patent/MX2020005462A/es unknown
- 2018-12-18 KR KR1020207020558A patent/KR102742178B1/ko active Active
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| JP2021506889A (ja) | 2021-02-22 |
| IL275356A (en) | 2020-07-30 |
| CA3085590A1 (en) | 2019-06-27 |
| EP3728225B1 (en) | 2022-11-09 |
| MX2020005462A (es) | 2020-09-07 |
| US11878975B2 (en) | 2024-01-23 |
| WO2019126113A1 (en) | 2019-06-27 |
| CN111491930B (zh) | 2023-09-26 |
| KR20200101402A (ko) | 2020-08-27 |
| JP7291145B2 (ja) | 2023-06-14 |
| SG11202005696YA (en) | 2020-07-29 |
| BR112020012084A2 (pt) | 2020-11-24 |
| EP3728225A1 (en) | 2020-10-28 |
| ES2932361T3 (es) | 2023-01-18 |
| EA202091474A1 (ru) | 2020-11-18 |
| AU2018390820A1 (en) | 2020-08-06 |
| US20200308172A1 (en) | 2020-10-01 |
| CN111491930A (zh) | 2020-08-04 |
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