JP2021507912A5 - - Google Patents
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- Publication number
- JP2021507912A5 JP2021507912A5 JP2020534474A JP2020534474A JP2021507912A5 JP 2021507912 A5 JP2021507912 A5 JP 2021507912A5 JP 2020534474 A JP2020534474 A JP 2020534474A JP 2020534474 A JP2020534474 A JP 2020534474A JP 2021507912 A5 JP2021507912 A5 JP 2021507912A5
- Authority
- JP
- Japan
- Prior art keywords
- isopropyl
- pyridine
- pyrrolo
- triazolo
- pyridin
- 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.)
- Granted
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- -1 [1,2,4] Triazolo [1,5-a] Pyridinyl Chemical group 0.000 claims 504
- 125000000217 alkyl group Chemical group 0.000 claims 100
- 125000003386 piperidinyl group Chemical group 0.000 claims 65
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 56
- 125000002757 morpholinyl group Chemical group 0.000 claims 46
- 125000004193 piperazinyl group Chemical group 0.000 claims 43
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 42
- 125000004076 pyridyl group Chemical group 0.000 claims 40
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 38
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 37
- 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 37
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 33
- 125000002393 azetidinyl group Chemical group 0.000 claims 29
- 125000000168 pyrrolyl group Chemical group 0.000 claims 28
- 125000001424 substituent group Chemical group 0.000 claims 28
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 24
- 125000003566 oxetanyl group Chemical group 0.000 claims 22
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 21
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 21
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 19
- 125000005959 diazepanyl group Chemical group 0.000 claims 18
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 18
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 17
- 229910052799 carbon Inorganic materials 0.000 claims 15
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000002883 imidazolyl group Chemical group 0.000 claims 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims 11
- AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 claims 11
- OJEOJUQOECNDND-UHFFFAOYSA-N oxetan-3-amine Chemical compound NC1COC1 OJEOJUQOECNDND-UHFFFAOYSA-N 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 8
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 8
- 125000001425 triazolyl group Chemical group 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 7
- 125000003725 azepanyl group Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 7
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 7
- 125000000335 thiazolyl group Chemical group 0.000 claims 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000003944 tolyl group Chemical group 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 4
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- AQWOIRBQLOOZGX-UHFFFAOYSA-N triazolo[1,5-a]pyridine Chemical compound C1=CC=CC2=CN=NN21 AQWOIRBQLOOZGX-UHFFFAOYSA-N 0.000 claims 4
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000005605 benzo group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 125000005879 dioxolanyl group Chemical group 0.000 claims 3
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 3
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 3
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 3
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 2
- OXVLCHLNJKLRGV-UHFFFAOYSA-N 1-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-methyl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-[(3-methyloxetan-3-yl)methyl]piperidin-4-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=C(N1)C=NC(N1CCC(CC1)NCC1(C)COC1)=C2C OXVLCHLNJKLRGV-UHFFFAOYSA-N 0.000 claims 2
- MJCZGYYLRRBGHK-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-(2-methoxyethyl)piperidin-4-amine Chemical compound FC1=C2C(=CN=C1N1CCC(CC1)NCCOC)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC MJCZGYYLRRBGHK-UHFFFAOYSA-N 0.000 claims 2
- MVTKXXYOCZHIPB-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-(oxetan-3-yl)piperidin-4-amine Chemical compound COC1=CC(=CN2N=CN=C12)C1=C(C(C)C)C2=C(N1)C=NC(N1CCC(CC1)NC1COC1)=C2F MVTKXXYOCZHIPB-UHFFFAOYSA-N 0.000 claims 2
- FKYPTBFYBRLEEE-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-(3-methyloxetan-3-yl)piperidin-4-amine Chemical compound CC(C)C1=C(NC2=C1C(F)=C(N=C2)N1CCC(CC1)NC1(C)COC1)C1=CN2N=CN=C2C(C)=C1 FKYPTBFYBRLEEE-UHFFFAOYSA-N 0.000 claims 2
- NUICZGVMGSDMBU-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-(oxan-4-yl)piperidin-4-amine Chemical compound FC1=C2C(=CN=C1N1CCC(CC1)NC1CCOCC1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)C NUICZGVMGSDMBU-UHFFFAOYSA-N 0.000 claims 2
- UMVOFFBBJCKIKE-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-[(3-methyloxetan-3-yl)methyl]piperidin-4-amine Chemical compound CC(C)C1=C(NC2=C1C(F)=C(N=C2)N1CCC(CC1)NCC1(C)COC1)C1=CN2N=CN=C2C(C)=C1 UMVOFFBBJCKIKE-UHFFFAOYSA-N 0.000 claims 2
- FLIXGHJCPMLVIL-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-methyl-N-(oxetan-3-yl)piperidin-4-amine Chemical compound CC(C)C1=C(NC2=C1C(F)=C(N=C2)N1CCC(CC1)N(C)C1COC1)C1=CN2N=CN=C2C(C)=C1 FLIXGHJCPMLVIL-UHFFFAOYSA-N 0.000 claims 2
- ASWGWYRZQPZRAR-UHFFFAOYSA-N 1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-methylpiperidin-4-amine Chemical compound CNC1CCN(CC1)C1=C(F)C2=C(NC(=C2C(C)C)C2=CN3N=CN=C3C(C)=C2)C=N1 ASWGWYRZQPZRAR-UHFFFAOYSA-N 0.000 claims 2
- PZNGKNHECKULKI-UHFFFAOYSA-N 1-[4-methyl-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-(oxan-4-yl)piperidin-4-amine Chemical compound C(C)(C)C1=C(NC2=CN=C(C(=C21)C)N1CCC(CC1)NC1CCOCC1)C=1C=C(C=2N(C=1)N=CN=2)C PZNGKNHECKULKI-UHFFFAOYSA-N 0.000 claims 2
- VLFHHCPZQFIQFY-UHFFFAOYSA-N 1-[4-methyl-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]-N-[(3-methyloxetan-3-yl)methyl]piperidin-4-amine Chemical compound C(C)(C)C1=C(NC2=CN=C(C(=C21)C)N1CCC(CC1)NCC1(COC1)C)C=1C=C(C=2N(C=1)N=CN=2)C VLFHHCPZQFIQFY-UHFFFAOYSA-N 0.000 claims 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 2
- LDJRVKDGDAMNRD-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-4-fluoro-5-[1-(2-methoxyethyl)piperidin-4-yl]-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridine Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCN(CC2)CCOC)N1)C(C)C)C LDJRVKDGDAMNRD-UHFFFAOYSA-N 0.000 claims 2
- NQINQUJFTLUOFU-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-4-fluoro-5-[1-(oxetan-3-yl)piperidin-4-yl]-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridine Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCN(CC2)C2COC2)N1)C(C)C)C NQINQUJFTLUOFU-UHFFFAOYSA-N 0.000 claims 2
- KSSLQILEPYSNIO-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-4-fluoro-5-[1-[(3-methyloxetan-3-yl)methyl]piperidin-4-yl]-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridine Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCN(CC2)CC2(COC2)C)N1)C(C)C)C KSSLQILEPYSNIO-UHFFFAOYSA-N 0.000 claims 2
- KDAWIPDYRZISKF-UHFFFAOYSA-N 2-(2,6-dimethylpyridin-4-yl)-4-fluoro-5-piperidin-4-yl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridine Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCNCC2)N1)C(C)C)C KDAWIPDYRZISKF-UHFFFAOYSA-N 0.000 claims 2
- YLHNIRTVNRZMRQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-3-methyl-5-[1-[1-(2-methylpropyl)piperidin-4-yl]piperidin-4-yl]-1H-pyrrolo[2,3-c]pyridine Chemical compound COC=1C=C(C=CC=1OC)C1=C(C=2C(=CN=C(C=2)C2CCN(CC2)C2CCN(CC2)CC(C)C)N1)C YLHNIRTVNRZMRQ-UHFFFAOYSA-N 0.000 claims 2
- ASZRRJZLIVDLMX-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=CN=1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC)C ASZRRJZLIVDLMX-UHFFFAOYSA-N 0.000 claims 2
- RREMYPFRNNURHL-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-4-methyl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C(=C2C(=CN=1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC)C)C RREMYPFRNNURHL-UHFFFAOYSA-N 0.000 claims 2
- OBZZYDGPMBDCOP-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCC(CC1)C=1C=C2C(=CN=1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)C)C OBZZYDGPMBDCOP-UHFFFAOYSA-N 0.000 claims 2
- WJDSZSRPWLNMED-UHFFFAOYSA-N 2-(dimethylamino)-1-[4-[4-fluoro-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperazin-1-yl]ethanone Chemical compound CN(CC(=O)N1CCN(CC1)C=1C(=C2C(=CN=1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC)F)C WJDSZSRPWLNMED-UHFFFAOYSA-N 0.000 claims 2
- MJADZBZRKJWBEF-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-4-fluoro-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]-N,N-dimethylacetamide Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCN(CC2)CC(=O)N(C)C)N1)C(C)C)C MJADZBZRKJWBEF-UHFFFAOYSA-N 0.000 claims 2
- GEHFIYMAZMNWBK-UHFFFAOYSA-N 2-[4-[2-(2,6-dimethylpyridin-4-yl)-4-fluoro-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound CC1=NC(=CC(=C1)C1=C(C=2C(=CN=C(C=2F)C2CCN(CC2)CC(=O)NC)N1)C(C)C)C GEHFIYMAZMNWBK-UHFFFAOYSA-N 0.000 claims 2
- CGWGARBIMIYUDY-UHFFFAOYSA-N 2-[4-[2-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]-N-methylethanamine Chemical compound COC=1C=C(C=CC=1OC)C1=C(C=2C(=CN=C(C=2)C2CCN(CC2)CCNC)N1)C CGWGARBIMIYUDY-UHFFFAOYSA-N 0.000 claims 2
- WXLXJXKZNANEJV-UHFFFAOYSA-N 2-[4-[2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-1-yl]-N-methylacetamide Chemical compound C(C)(C)C1=C(NC2=CN=C(C=C21)C1CCN(CC1)CC(=O)NC)C=1C=C(C=2N(C=1)N=CN=2)OC WXLXJXKZNANEJV-UHFFFAOYSA-N 0.000 claims 2
- LQULLAIGCDLIEJ-UHFFFAOYSA-N 2-[[1-[4-fluoro-2-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-4-yl]-methylamino]-N,N-dimethylacetamide Chemical compound FC1=C2C(=CN=C1N1CCC(CC1)N(CC(=O)N(C)C)C)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC LQULLAIGCDLIEJ-UHFFFAOYSA-N 0.000 claims 2
- CECWKNBPRACUNP-UHFFFAOYSA-N 2-[[1-[4-fluoro-2-(8-methyl-[1,2,4]triazolo[1,5-a]pyridin-6-yl)-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-5-yl]piperidin-4-yl]-methylamino]-N,N-dimethylacetamide Chemical compound CC(C)C1=C(NC2=C1C(F)=C(N=C2)N1CCC(CC1)N(C)CC(=O)N(C)C)C1=CN2N=CN=C2C(C)=C1 CECWKNBPRACUNP-UHFFFAOYSA-N 0.000 claims 2
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 2
- RXVAFWJQQROKCM-UHFFFAOYSA-N 6-(4-chloro-5-piperazin-1-yl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-2-yl)-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound ClC1=C2C(=CN=C1N1CCNCC1)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC RXVAFWJQQROKCM-UHFFFAOYSA-N 0.000 claims 2
- MDYDLMNKQRJUAG-UHFFFAOYSA-N 6-(4-fluoro-5-piperazin-1-yl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-2-yl)-7,8-dimethyl-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1(NC2=C(C=1C(C)C)C(=C(N=C2)N1CCNCC1)F)C1=CN2C(C(=C1C)C)=NC=N2 MDYDLMNKQRJUAG-UHFFFAOYSA-N 0.000 claims 2
- DBUNODZFUPCWFG-UHFFFAOYSA-N 6-(4-fluoro-5-piperidin-4-yl-3-propan-2-yl-1H-pyrrolo[2,3-c]pyridin-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=C(N1)C=NC(C1CCNCC1)=C2F DBUNODZFUPCWFG-UHFFFAOYSA-N 0.000 claims 2
- BSMAGMDGOUHGLS-UHFFFAOYSA-N 6-[4-fluoro-3-propan-2-yl-5-(4-propan-2-ylpiperazin-1-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1=C2C(=CN=C1N1CCN(CC1)C(C)C)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC BSMAGMDGOUHGLS-UHFFFAOYSA-N 0.000 claims 2
- OQKBWRFKNVOQRD-UHFFFAOYSA-N 6-[4-fluoro-3-propan-2-yl-5-(6-propyl-2,6-diazaspiro[3.3]heptan-2-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl]-8-methoxy-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC1=C2C(=CN=C1N1CC3(C1)CN(C3)CCC)NC(=C2C(C)C)C=1C=C(C=2N(C=1)N=CN=2)OC OQKBWRFKNVOQRD-UHFFFAOYSA-N 0.000 claims 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762607507P | 2017-12-19 | 2017-12-19 | |
| US62/607,507 | 2017-12-19 | ||
| PCT/US2018/066107 WO2019126082A1 (en) | 2017-12-19 | 2018-12-18 | 6-azaindole compounds |
Publications (3)
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Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| ES2904773T3 (es) * | 2017-12-20 | 2022-04-06 | Bristol Myers Squibb Co | Compuestos de diazaindol |
| 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 |
| GB201913752D0 (en) | 2019-09-24 | 2019-11-06 | Syngenta Crop Protection Ag | Herbicidal compounds |
| GB201914277D0 (en) | 2019-10-03 | 2019-11-20 | Syngenta Crop Protection Ag | Herbicidal 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 |
| GB201917898D0 (en) | 2019-12-06 | 2020-01-22 | Syngenta Crop Protection Ag | Herbicidal compounds |
| JP7462772B2 (ja) | 2020-08-13 | 2024-04-05 | エルジー エナジー ソリューション リミテッド | 改善された電極リード接続構造を有するバッテリーモジュール、それを含むバッテリーパック及び自動車 |
| 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 |
| CA3189816A1 (en) * | 2020-08-19 | 2022-02-24 | Chunjian Liu | Substituted heteroaryl compounds useful as inhibitors of tlr9 |
| AU2021328577A1 (en) * | 2020-08-19 | 2023-03-23 | Bristol-Myers Squibb Company | 1H-pyrrolo[3,2-c]pyridine and 1H-pyrrolo[2,3-c]pyridine derivatives as TLR9 inhibitors for the treatment of fibrosis |
| 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 |
| JP7588224B2 (ja) | 2020-10-05 | 2024-11-21 | エンライブン インコーポレイテッド | Ｂｃｒ－ａｂｌチロシンキナーゼの阻害のための５－及び６－アザインドール化合物 |
| 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 |
| 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 |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5468757A (en) * | 1994-01-31 | 1995-11-21 | Eli Lilly And Company | 6-azaindole thromboxane synthase inhibitors |
| US6187777B1 (en) | 1998-02-06 | 2001-02-13 | Amgen Inc. | Compounds and methods which modulate feeding behavior and related diseases |
| JP2002532479A (ja) | 1998-12-18 | 2002-10-02 | アクシス・ファーマシューティカルズ・インコーポレイテッド | プロテアーゼインヒビター |
| WO2000038683A1 (en) * | 1998-12-23 | 2000-07-06 | Du Pont Pharmaceuticals Company | THROMBIN OR FACTOR Xa INHIBITORS |
| GEP20053530B (en) | 1999-10-19 | 2005-05-25 | Merck & Co Inc | Tyrosine Kinase Inhibitors, Pharmaceutical Compositions Containing Them and Use Thereof |
| ES2262996T3 (es) | 2002-01-07 | 2006-12-01 | Eisai Co., Ltd. | Deazapurinas y sus usos. |
| BRPI0411514A (pt) | 2003-06-20 | 2006-08-01 | Coley Pharm Gmbh | antagonistas de receptor toll-like de molécula pequena |
| US20060235037A1 (en) | 2005-04-15 | 2006-10-19 | Purandare Ashok V | Heterocyclic inhibitors of protein arginine methyl transferases |
| EP2010187A4 (en) | 2006-04-04 | 2010-11-17 | Myriad Genetics Inc | CONNECTIONS FOR DISEASES AND FUNCTIONAL DISORDERS |
| DE102006033109A1 (de) | 2006-07-18 | 2008-01-31 | Grünenthal GmbH | Substituierte Heteroaryl-Derivate |
| US8027888B2 (en) | 2006-08-31 | 2011-09-27 | Experian Interactive Innovation Center, Llc | Online credit card prescreen systems and methods |
| DE602007012133D1 (de) | 2006-12-01 | 2011-03-03 | Andrew Burritt | Triazolopyridinverbindungen zur behandlung von degenerations- und entzündungskrankheiten |
| WO2008152471A1 (en) | 2007-06-12 | 2008-12-18 | Coley Pharmaceutical Group, Inc. | Quinazoline derivative useful as toll-like receptor antagonist |
| WO2009030996A1 (en) | 2007-09-05 | 2009-03-12 | Coley Pharmaceutical Group, Inc. | Triazole compounds as toll-like receptor (tlr) agonists |
| EP2205085A1 (en) | 2007-09-25 | 2010-07-14 | Merck Sharp & Dohme Corp. | 2-aryl or heteroaryl indole derivatives |
| FR2930249B1 (fr) | 2008-04-21 | 2010-05-14 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique. |
| WO2010036905A1 (en) | 2008-09-26 | 2010-04-01 | Eisai R & D Management Co., Ltd. | Benzoxazole compounds and methods of use |
| US20110183975A1 (en) | 2008-10-07 | 2011-07-28 | Yasuhiro Goto | Novel 6-azaindole aminopyrimidine derivatives having nik inhibitory activity |
| US8785489B2 (en) | 2008-10-17 | 2014-07-22 | Boehringer Ingelheim International Gmbh | Heteroaryl substituted indole compounds useful as MMP-13 inhibitors |
| TWI462920B (zh) | 2009-06-26 | 2014-12-01 | 葛萊伯格有限公司 | 用於治療退化性及發炎疾病之新穎化合物 |
| NO2453895T3 (enExample) | 2009-07-16 | 2018-10-20 | ||
| CA2771026A1 (en) | 2009-09-24 | 2011-03-31 | F. Hoffmann-La Roche Ag | Indole derivatives as crac modulators |
| AU2010310449A1 (en) | 2009-10-22 | 2012-05-03 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| WO2012054862A2 (en) | 2010-10-21 | 2012-04-26 | The Brigham And Women's Hospital, Inc. | Agents, compositions, and methods for treating pruritis and related skin conditions |
| US9718796B2 (en) | 2011-01-12 | 2017-08-01 | Ventirx Pharmaceuticals, Inc. | Substituted benzoazepines as toll-like receptor modulators |
| BR112013017947A2 (pt) | 2011-01-12 | 2018-12-18 | Array Biopharma Inc | benzoazepinas substituídas como moduladores de receptor toll-like |
| JP6093759B2 (ja) | 2011-06-01 | 2017-03-08 | ジャナス バイオセラピューティクス，インク． | 新規の免疫系調節剤 |
| EP2713737B1 (en) | 2011-06-01 | 2016-04-20 | Janus Biotherapeutics, Inc. | Novel immune system modulators |
| EA031618B1 (ru) | 2011-06-09 | 2019-01-31 | Ризен Фармасьютикалз Са | Соединения-модуляторы gpr-119 |
| EA023045B1 (ru) | 2011-07-15 | 2016-04-29 | Янссен Фармасьютикалз, Инк. | Новые замещенные производные индола в качестве модуляторов гамма-секретазы |
| DE102011111400A1 (de) * | 2011-08-23 | 2013-02-28 | Merck Patent Gmbh | Bicyclische heteroaromatische Verbindungen |
| US9873694B2 (en) | 2011-10-04 | 2018-01-23 | Janus Biotherapeutics, Inc. | Imidazole quinoline-based immune system modulators |
| MY178053A (en) | 2012-05-18 | 2020-09-30 | Sumitomo Dainippon Pharma Co Ltd | Carboxylic acid compounds |
| JO3407B1 (ar) * | 2012-05-31 | 2019-10-20 | Eisai R&D Man Co Ltd | مركبات رباعي هيدرو بيرازولو بيريميدين |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| MD4635C1 (ro) | 2013-10-14 | 2020-01-31 | Eisai R&D Management Co., Ltd. | Compuşi de chinolină substituiţi selectiv |
| WO2015088045A1 (en) | 2013-12-13 | 2015-06-18 | Takeda Pharmaceutical Company Limited | Pyrrolo[3,2-c]pyridine derivatives as tlr inhibitors |
| SI3190113T1 (sl) | 2014-08-15 | 2021-09-30 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pirolopirimidinske spojine, ki se uporabljajo kot agonist TLR7 |
| US20170275287A1 (en) | 2014-08-22 | 2017-09-28 | Janus Biotherapeutics, Inc. | Novel n2, n4, n7, 6-tetrasubstituted pteridine-2,4,7-triamine and 2, 4, 6, 7-tetrasubstituted pteridine compounds and methods of synthesis and use thereof |
| US10071079B2 (en) | 2016-06-29 | 2018-09-11 | Bristol-Myers Squibb Company | [1,2,4]triazolo[1,5-a]pyridinyl substituted indole compounds |
| CA3031675A1 (en) | 2016-07-30 | 2018-02-08 | Bristol-Myers Squibb Company | Dimethoxyphenyl substituted indole compounds as tlr7, tlr8 or tlr9 inhibitors |
| WO2018049089A1 (en) | 2016-09-09 | 2018-03-15 | Bristol-Myers Squibb Company | Pyridyl substituted indole compounds |
| AU2018390820A1 (en) * | 2017-12-19 | 2020-08-06 | Bristol-Myers Squibb Company | Substituted indole compounds useful as TLR inhibitors |
-
2018
- 2018-12-18 SG SG11202005704RA patent/SG11202005704RA/en unknown
- 2018-12-18 US US16/955,089 patent/US11427580B2/en active Active
- 2018-12-18 AU AU2018390543A patent/AU2018390543A1/en not_active Abandoned
- 2018-12-18 CA CA3085761A patent/CA3085761A1/en active Pending
- 2018-12-18 CN CN201880089130.3A patent/CN111699185B/zh active Active
- 2018-12-18 EA EA202091508A patent/EA202091508A1/ru unknown
- 2018-12-18 JP JP2020534474A patent/JP7304352B2/ja active Active
- 2018-12-18 WO PCT/US2018/066107 patent/WO2019126082A1/en not_active Ceased
- 2018-12-18 BR BR112020011788-9A patent/BR112020011788A2/pt not_active Application Discontinuation
- 2018-12-18 KR KR1020207020877A patent/KR102742181B1/ko active Active
- 2018-12-18 ES ES18830673T patent/ES2977657T3/es active Active
- 2018-12-18 MX MX2020005873A patent/MX2020005873A/es unknown
- 2018-12-18 EP EP18830673.2A patent/EP3728253B1/en active Active
-
2020
- 2020-06-14 IL IL275365A patent/IL275365A/en unknown
-
2022
- 2022-06-30 US US17/854,089 patent/US11912703B2/en active Active
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