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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| JP2021507912A5 true JP2021507912A5 (https=) | 2022-01-04 |
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| JP (1) | JP7304352B2 (https=) |
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| SG11202005733QA (en) * | 2017-12-20 | 2020-07-29 | Bristol Myers Squibb Co | Diazaindole compounds |
| EP3728218B1 (en) * | 2017-12-20 | 2021-12-01 | Bristol-Myers Squibb Company | Amino indole compounds useful as tlr inhibitors |
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| EP3807270B1 (en) | 2018-06-12 | 2023-09-13 | F. Hoffmann-La Roche AG | Novel heteroaryl heterocyclyl compounds for the treatment of autoimmune disease |
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| EP3847169A1 (en) | 2018-09-04 | 2021-07-14 | 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 |
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2018
- 2018-12-18 JP JP2020534474A patent/JP7304352B2/ja active Active
- 2018-12-18 SG SG11202005704RA patent/SG11202005704RA/en unknown
- 2018-12-18 KR KR1020207020877A patent/KR102742181B1/ko active Active
- 2018-12-18 AU AU2018390543A patent/AU2018390543A1/en not_active Abandoned
- 2018-12-18 US US16/955,089 patent/US11427580B2/en active Active
- 2018-12-18 BR BR112020011788-9A patent/BR112020011788A2/pt not_active Application Discontinuation
- 2018-12-18 CN CN201880089130.3A patent/CN111699185B/zh active Active
- 2018-12-18 ES ES18830673T patent/ES2977657T3/es active Active
- 2018-12-18 WO PCT/US2018/066107 patent/WO2019126082A1/en not_active Ceased
- 2018-12-18 EP EP18830673.2A patent/EP3728253B1/en active Active
- 2018-12-18 EA EA202091508A patent/EA202091508A1/ru unknown
- 2018-12-18 MX MX2020005873A patent/MX2020005873A/es unknown
- 2018-12-18 CA CA3085761A patent/CA3085761A1/en active Pending
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2020
- 2020-06-14 IL IL275365A patent/IL275365A/en unknown
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2022
- 2022-06-30 US US17/854,089 patent/US11912703B2/en active Active
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