JP2016540022A5 - - Google Patents
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- Publication number
- JP2016540022A5 JP2016540022A5 JP2016539166A JP2016539166A JP2016540022A5 JP 2016540022 A5 JP2016540022 A5 JP 2016540022A5 JP 2016539166 A JP2016539166 A JP 2016539166A JP 2016539166 A JP2016539166 A JP 2016539166A JP 2016540022 A5 JP2016540022 A5 JP 2016540022A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- amino
- phenoxy
- indole
- pyrazol
- 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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- 150000003839 salts Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000001475 halogen functional group Chemical group 0.000 claims description 17
- -1 {5-Amino-1- [4- (2,3-difluoro-phenoxy) -2-methyl-phenyl] -1H-pyrazol-4-carbonyl} -1H-indol-5-yl Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 25
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 230000001363 autoimmune Effects 0.000 claims 3
- 230000002757 inflammatory effect Effects 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- FMESQYIRJMDGKN-UHFFFAOYSA-N 2-[4-[5-amino-4-(1H-indole-2-carbonyl)pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C=CC=C1)C(N(C)C)=O)Cl)C(=O)C=1NC2=CC=CC=C2C=1 FMESQYIRJMDGKN-UHFFFAOYSA-N 0.000 claims 1
- ASSSZLFXMYRUEW-UHFFFAOYSA-N 2-[4-[5-amino-4-[5-(4-methylpiperazine-1-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound NC1=C(C=NN1C1=C(C=C(OC2=C(C(=O)N(C)C)C=CC=C2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCN(CC1)C ASSSZLFXMYRUEW-UHFFFAOYSA-N 0.000 claims 1
- KPDJKSBPXDTOOL-UHFFFAOYSA-N 2-[4-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound NC1=C(C=NN1C1=C(C=C(OC2=C(C(=O)N(C)C)C=CC=C2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 KPDJKSBPXDTOOL-UHFFFAOYSA-N 0.000 claims 1
- FCBLVBCCQAQQIX-UHFFFAOYSA-N 2-[4-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-methylphenoxy]benzonitrile Chemical compound NC1=C(C=NN1C1=C(C=C(OC2=C(C#N)C=CC=C2)C=C1)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 FCBLVBCCQAQQIX-UHFFFAOYSA-N 0.000 claims 1
- XQOYEPRCBNYBFM-UHFFFAOYSA-N 2-[4-[5-amino-4-[5-[4-(methylamino)piperidine-1-carbonyl]-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound NC1=C(C=NN1C1=C(C=C(OC2=C(C(=O)N(C)C)C=CC=C2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCC(CC1)NC XQOYEPRCBNYBFM-UHFFFAOYSA-N 0.000 claims 1
- QYGROOKKWZGHEY-UHFFFAOYSA-N 2-[5-amino-1-[2-chloro-4-(3-cyano-2-fluorophenoxy)phenyl]pyrazole-4-carbonyl]-1H-indole-5-carboxylic acid Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C(=CC=C1)C#N)F)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)O QYGROOKKWZGHEY-UHFFFAOYSA-N 0.000 claims 1
- ULFBTRQJBNUGPM-UHFFFAOYSA-N 2-[5-amino-1-[2-chloro-4-(3-cyanophenoxy)phenyl]pyrazole-4-carbonyl]-1H-indole-5-carboxylic acid Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC(=CC=C1)C#N)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)O ULFBTRQJBNUGPM-UHFFFAOYSA-N 0.000 claims 1
- ISPUCYKAHULRLP-UHFFFAOYSA-N 2-[5-amino-1-[2-chloro-4-[2-(dimethylcarbamoyl)phenoxy]phenyl]pyrazole-4-carbonyl]-N-[2-(dimethylamino)ethyl]-1H-indole-5-carboxamide Chemical compound CN(CCNC(=O)C=1C=C2C=C(NC2=CC1)C(=O)C=1C=NN(C1N)C1=C(C=C(C=C1)OC1=C(C=CC=C1)C(N(C)C)=O)Cl)C ISPUCYKAHULRLP-UHFFFAOYSA-N 0.000 claims 1
- XNDJOBNKFLWXMK-UHFFFAOYSA-N 2-[5-amino-1-[4-(2,3-difluorophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-1H-indole-5-carboxylic acid Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C(=CC=C1)F)F)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)O XNDJOBNKFLWXMK-UHFFFAOYSA-N 0.000 claims 1
- FAIWGSNGZQGHPB-UHFFFAOYSA-N 2-[5-amino-1-[4-(2,3-difluorophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-N-(2-methoxyethyl)-1H-indole-5-carboxamide Chemical compound COCCNC(=O)C=1C=C2C=C(NC2=CC1)C(=O)C=1C=NN(C1N)C1=C(C=C(C=C1)OC1=C(C(=CC=C1)F)F)C FAIWGSNGZQGHPB-UHFFFAOYSA-N 0.000 claims 1
- NXRYPTQXZOJNOC-UHFFFAOYSA-N 2-[5-amino-1-[4-(3-cyanophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-1H-indole-5-carboxylic acid Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC(=CC=C1)C#N)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)O NXRYPTQXZOJNOC-UHFFFAOYSA-N 0.000 claims 1
- FHYSSWICUKGRGR-UHFFFAOYSA-N 2-[5-amino-1-[4-(3-cyanophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-3H-benzimidazole-5-carboxylic acid Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC(=CC=C1)C#N)C)C(=O)C1=NC2=C(N1)C=CC(=C2)C(=O)O FHYSSWICUKGRGR-UHFFFAOYSA-N 0.000 claims 1
- NFYJJGQALFAWCQ-UHFFFAOYSA-N 2-[5-amino-1-[4-(3-cyanophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-N-(2-aminoethyl)-1H-indole-5-carboxamide Chemical compound NCCNC(=O)C=1C=C2C=C(NC2=CC1)C(=O)C=1C=NN(C1N)C1=C(C=C(C=C1)OC1=CC(=CC=C1)C#N)C NFYJJGQALFAWCQ-UHFFFAOYSA-N 0.000 claims 1
- OSNCYTRHOZBIJO-UHFFFAOYSA-N 2-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-5-(2,3-difluorophenoxy)benzonitrile Chemical compound NC1=C(C=NN1C1=C(C#N)C=C(C=C1)OC1=C(C(=CC=C1)F)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 OSNCYTRHOZBIJO-UHFFFAOYSA-N 0.000 claims 1
- OXGSVMFOSTVUKX-UHFFFAOYSA-N 3-[4-[5-amino-4-(5-bromo-1H-indole-2-carbonyl)pyrazol-1-yl]-3-chlorophenoxy]benzonitrile Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C#N)C=CC2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)Br OXGSVMFOSTVUKX-UHFFFAOYSA-N 0.000 claims 1
- BVMIGWDBNPVZDE-UHFFFAOYSA-N 3-[4-[5-amino-4-[5-(4-methylpiperazine-1-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C(=O)N(C)C)C=CC2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCN(CC1)C BVMIGWDBNPVZDE-UHFFFAOYSA-N 0.000 claims 1
- GICYIHRZQFIHTG-UHFFFAOYSA-N 3-[4-[5-amino-4-[5-(4-methylpiperazine-1-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]benzonitrile hydrochloride Chemical compound Cl.CN1CCN(CC1)C(=O)C1=CC=C2NC(=CC2=C1)C(=O)C1=C(N)N(N=C1)C1=C(Cl)C=C(OC2=CC=CC(=C2)C#N)C=C1 GICYIHRZQFIHTG-UHFFFAOYSA-N 0.000 claims 1
- QARVIPGXIAPCCM-UHFFFAOYSA-N 3-[4-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]benzamide Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C(=O)N)C=CC2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 QARVIPGXIAPCCM-UHFFFAOYSA-N 0.000 claims 1
- SHEGNVHCEQJQOS-UHFFFAOYSA-N 3-[4-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]benzonitrile Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C#N)C=CC2)C=C1)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 SHEGNVHCEQJQOS-UHFFFAOYSA-N 0.000 claims 1
- DXKVGAPNDQXAPY-UHFFFAOYSA-N 3-[4-[5-amino-4-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-methylphenoxy]benzonitrile Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C#N)C=CC2)C=C1)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 DXKVGAPNDQXAPY-UHFFFAOYSA-N 0.000 claims 1
- IFRBUGHFMWMQIE-UHFFFAOYSA-N 3-[4-[5-amino-4-[6-(morpholine-4-carbonyl)-1H-benzimidazole-2-carbonyl]pyrazol-1-yl]-3-methylphenoxy]benzonitrile Chemical compound NC1=C(C=NN1C1=C(C=C(OC=2C=C(C#N)C=CC2)C=C1)C)C(=O)C1=NC2=C(N1)C=CC(=C2)C(=O)N2CCOCC2 IFRBUGHFMWMQIE-UHFFFAOYSA-N 0.000 claims 1
- MDTRISVNYSVZMG-UHFFFAOYSA-N 7-(2,3-difluorophenoxy)-3-[5-(morpholine-4-carbonyl)-1H-indole-2-carbonyl]-4H-pyrazolo[1,5-a]quinazolin-5-one Chemical compound FC1=CC=CC(OC2=CC=C3N4N=CC(C(=O)C5=CC6=CC(=CC=C6N5)C(=O)N5CCOCC5)=C4NC(=O)C3=C2)=C1F MDTRISVNYSVZMG-UHFFFAOYSA-N 0.000 claims 1
- XAPUMHZHAVBSGG-UHFFFAOYSA-N CC(O)=O.CN(C)C(=O)C1=C(OC2=CC(Cl)=C(C=C2)N2N=C(C=C2N)C(=O)C2=CC3=CC(=CC=C3N2)C(=O)NC2CCN(C)C2)C=CC=C1 Chemical compound CC(O)=O.CN(C)C(=O)C1=C(OC2=CC(Cl)=C(C=C2)N2N=C(C=C2N)C(=O)C2=CC3=CC(=CC=C3N2)C(=O)NC2CCN(C)C2)C=CC=C1 XAPUMHZHAVBSGG-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- XRMDUUNRWNFGCZ-UHFFFAOYSA-N [2-[5-amino-1-(2-chloro-4-phenoxyphenyl)pyrazole-4-carbonyl]-1h-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C(=O)C=2NC3=CC=C(C=C3C=2)C(=O)N2CCOCC2)C=NN1C(C(=C1)Cl)=CC=C1OC1=CC=CC=C1 XRMDUUNRWNFGCZ-UHFFFAOYSA-N 0.000 claims 1
- ALZXLQMBUNQGFN-UHFFFAOYSA-N [2-[5-amino-1-(2-fluoro-4-phenoxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC=CC=C1)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 ALZXLQMBUNQGFN-UHFFFAOYSA-N 0.000 claims 1
- YGRJCUYPHRTGLV-UHFFFAOYSA-N [2-[5-amino-1-(2-methyl-4-phenoxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC=CC=C1)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 YGRJCUYPHRTGLV-UHFFFAOYSA-N 0.000 claims 1
- SCSXQTADRPKLIC-UHFFFAOYSA-N [2-[5-amino-1-(2-methyl-4-pyridin-2-yloxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=NC=CC=C1)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 SCSXQTADRPKLIC-UHFFFAOYSA-N 0.000 claims 1
- NSEDUGIZFVIBTI-UHFFFAOYSA-N [2-[5-amino-1-(3-fluoro-4-phenoxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=CC(=C(C=C1)OC1=CC=CC=C1)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 NSEDUGIZFVIBTI-UHFFFAOYSA-N 0.000 claims 1
- RVTLUXZXCDOXEX-UHFFFAOYSA-N [2-[5-amino-1-(4-methoxy-2-methylphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 RVTLUXZXCDOXEX-UHFFFAOYSA-N 0.000 claims 1
- CWOQLWVUANQSDC-UHFFFAOYSA-N [2-[5-amino-1-(4-methyl-6-phenoxypyridin-3-yl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C=1C=NC(=CC1C)OC1=CC=CC=C1)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 CWOQLWVUANQSDC-UHFFFAOYSA-N 0.000 claims 1
- GKEJAWPZSHGAMG-UHFFFAOYSA-N [2-[5-amino-1-(4-phenoxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=CC=C(C=C1)OC1=CC=CC=C1)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 GKEJAWPZSHGAMG-UHFFFAOYSA-N 0.000 claims 1
- PYSRXXMVFHPFEL-UHFFFAOYSA-N [2-[5-amino-1-(5-fluoro-2-methyl-4-phenoxyphenyl)pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C(=C1)F)OC1=CC=CC=C1)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 PYSRXXMVFHPFEL-UHFFFAOYSA-N 0.000 claims 1
- XJAUFLRBJQVPJI-UHFFFAOYSA-N [2-[5-amino-1-[2-bromo-4-(2,3-difluorophenoxy)phenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C(=CC=C1)F)F)Br)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 XJAUFLRBJQVPJI-UHFFFAOYSA-N 0.000 claims 1
- PFPXJKXLIAEWJP-UHFFFAOYSA-N [2-[5-amino-1-[2-chloro-4-(2-fluorophenoxy)phenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C=CC=C1)F)Cl)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 PFPXJKXLIAEWJP-UHFFFAOYSA-N 0.000 claims 1
- DCAYNDKXJSYVKI-UHFFFAOYSA-N [2-[5-amino-1-[4-(2,3-difluorophenoxy)-2,6-dimethylphenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1C)OC1=C(C(=CC=C1)F)F)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 DCAYNDKXJSYVKI-UHFFFAOYSA-N 0.000 claims 1
- QTLQGIGMWIPTAG-UHFFFAOYSA-N [2-[5-amino-1-[4-(2,3-difluorophenoxy)-2-hydroxyphenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C(=CC=C1)F)F)O)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 QTLQGIGMWIPTAG-UHFFFAOYSA-N 0.000 claims 1
- MPUWAWPEWIXDBP-UHFFFAOYSA-N [2-[5-amino-1-[4-(2,3-difluorophenoxy)phenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=CC=C(C=C1)OC1=C(C(=CC=C1)F)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 MPUWAWPEWIXDBP-UHFFFAOYSA-N 0.000 claims 1
- LQGGDBKEHYSZCN-UHFFFAOYSA-N [2-[5-amino-1-[4-(2-fluorophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=C(C=CC=C1)F)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 LQGGDBKEHYSZCN-UHFFFAOYSA-N 0.000 claims 1
- UVLGBWNEBAXSLR-UHFFFAOYSA-N [2-[5-amino-1-[4-(3-tert-butylphenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OC1=CC(=CC=C1)C(C)(C)C)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 UVLGBWNEBAXSLR-UHFFFAOYSA-N 0.000 claims 1
- HJOAIDTZUYOTOL-UHFFFAOYSA-N [2-[5-amino-1-[4-[(4-chlorophenyl)methoxy]-2-methylphenyl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C1=C(C=C(C=C1)OCC1=CC=C(C=C1)Cl)C)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 HJOAIDTZUYOTOL-UHFFFAOYSA-N 0.000 claims 1
- VXSCQLSRUAXZGX-UHFFFAOYSA-N [2-[5-amino-1-[6-(2,3-difluorophenoxy)-2-methoxypyridin-3-yl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C=1C(=NC(=CC1)OC1=C(C(=CC=C1)F)F)OC)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 VXSCQLSRUAXZGX-UHFFFAOYSA-N 0.000 claims 1
- VDYYFVZNNGUYBP-UHFFFAOYSA-N [2-[5-amino-1-[6-(2,3-difluorophenoxy)pyridin-3-yl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C=1C=NC(=CC1)OC1=C(C(=CC=C1)F)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 VDYYFVZNNGUYBP-UHFFFAOYSA-N 0.000 claims 1
- FZRBKJQDEBZBSU-UHFFFAOYSA-N [2-[5-amino-1-[6-(2,5-difluorophenoxy)pyridin-3-yl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C=1C=NC(=CC1)OC1=C(C=CC(=C1)F)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 FZRBKJQDEBZBSU-UHFFFAOYSA-N 0.000 claims 1
- PYMNBPDGSGXXQN-UHFFFAOYSA-N [2-[5-amino-1-[6-(2-fluorophenoxy)pyridin-3-yl]pyrazole-4-carbonyl]-1H-indol-5-yl]-morpholin-4-ylmethanone Chemical compound NC1=C(C=NN1C=1C=NC(=CC1)OC1=C(C=CC=C1)F)C(=O)C=1NC2=CC=C(C=C2C1)C(=O)N1CCOCC1 PYMNBPDGSGXXQN-UHFFFAOYSA-N 0.000 claims 1
- LGLRZFPDQWCOHF-UHFFFAOYSA-N acetic acid 2-[4-[5-amino-4-[5-(piperazine-1-carbonyl)-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound CC(O)=O.CN(C)C(=O)C1=C(OC2=CC(Cl)=C(C=C2)N2N=CC(C(=O)C3=CC4=CC(=CC=C4N3)C(=O)N3CCNCC3)=C2N)C=CC=C1 LGLRZFPDQWCOHF-UHFFFAOYSA-N 0.000 claims 1
- OTUBHVRSOISFNP-UHFFFAOYSA-N acetic acid 2-[4-[5-amino-4-[5-[3-(dimethylamino)pyrrolidine-1-carbonyl]-1H-indole-2-carbonyl]pyrazol-1-yl]-3-chlorophenoxy]-N,N-dimethylbenzamide Chemical compound CC(O)=O.CN(C)C1CCN(C1)C(=O)c1ccc2[nH]c(cc2c1)C(=O)c1cnn(c1N)-c1ccc(Oc2ccccc2C(=O)N(C)C)cc1Cl OTUBHVRSOISFNP-UHFFFAOYSA-N 0.000 claims 1
- VNLHXAABUFWCRS-UHFFFAOYSA-N acetic acid 2-[5-amino-1-[2-chloro-4-[2-(dimethylcarbamoyl)phenoxy]phenyl]pyrazole-4-carbonyl]-N-[2-(methylamino)ethyl]-1H-indole-5-carboxamide Chemical compound CC(O)=O.CNCCNC(=O)C1=CC=C2NC(=CC2=C1)C(=O)C1=C(N)N(N=C1)C1=C(Cl)C=C(OC2=C(C=CC=C2)C(=O)N(C)C)C=C1 VNLHXAABUFWCRS-UHFFFAOYSA-N 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- DLTBAYKGXREKMW-UHFFFAOYSA-N cyclopropanesulfonic acid Chemical compound OS(=O)(=O)C1CC1 DLTBAYKGXREKMW-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004968 inflammatory condition Effects 0.000 claims 1
- IKUGZZGMNVPMDO-UHFFFAOYSA-N methyl 2-[5-amino-1-[4-(3-cyanophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-1H-indole-5-carboxylate Chemical compound COC(=O)C=1C=C2C=C(NC2=CC1)C(=O)C=1C=NN(C1N)C1=C(C=C(C=C1)OC1=CC(=CC=C1)C#N)C IKUGZZGMNVPMDO-UHFFFAOYSA-N 0.000 claims 1
- FCFRJNBOCYYBBJ-UHFFFAOYSA-N methyl 2-[5-amino-1-[4-(3-cyanophenoxy)-2-methylphenyl]pyrazole-4-carbonyl]-3H-benzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC2=C(NC(=N2)C(=O)C=2C=NN(C2N)C2=C(C=C(C=C2)OC2=CC(=CC=C2)C#N)C)C=C1 FCFRJNBOCYYBBJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- NDODNIYYGCXIGS-UHFFFAOYSA-N tert-butyl N-[1-[2-[5-amino-1-[2-chloro-4-[2-(dimethylcarbamoyl)phenoxy]phenyl]pyrazole-4-carbonyl]-1H-indole-5-carbonyl]pyrrolidin-3-yl]-N-methylcarbamate Chemical compound CN(C)C(=O)C1=C(OC2=CC(Cl)=C(C=C2)N2N=CC(C(=O)C3=CC4=CC(=CC=C4N3)C(=O)N3CCC(C3)N(C)C(=O)OC(C)(C)C)=C2N)C=CC=C1 NDODNIYYGCXIGS-UHFFFAOYSA-N 0.000 claims 1
- WSEZKXVAOZHMQE-UHFFFAOYSA-N tert-butyl N-[2-[[2-[5-amino-1-[2-chloro-4-[2-(dimethylcarbamoyl)phenoxy]phenyl]pyrazole-4-carbonyl]-1H-indole-5-carbonyl]amino]ethyl]-N-methylcarbamate Chemical compound C(C)(C)(C)OC(N(C)CCNC(=O)C=1C=C2C=C(NC2=CC1)C(=O)C=1C=NN(C1N)C1=C(C=C(C=C1)OC1=C(C=CC=C1)C(N(C)C)=O)Cl)=O WSEZKXVAOZHMQE-UHFFFAOYSA-N 0.000 claims 1
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| BR112016013540B1 (pt) | 2013-12-13 | 2021-03-02 | F. Hoffmann-La Roche Ag | inibidores de tirosina quinase de bruton |
| US10391081B2 (en) | 2013-12-27 | 2019-08-27 | Chugai Seiyaku Kabushiki Kaisha | FGFR gatekeeper mutant gene and drug targeting same |
| EP3312172B1 (en) | 2015-06-17 | 2020-05-06 | Chugai Seiyaku Kabushiki Kaisha | Aminopyrazole derivatives useful as src kinase inhibitors |
| PL3954690T3 (pl) | 2015-07-02 | 2023-08-14 | Acerta Pharma B.V. | Postacie stałe i formulacje (s)-4-(8-amino-3-(1-(but-2-ynoilo)pirolidyn-2-ylo)imidazo[1,5-a]-pirazyn-1-ylo)-n-(pirydyn-2-ylo)benzamidu |
| WO2018152434A1 (en) * | 2017-02-17 | 2018-08-23 | The Regents Of The University Of California | Systems and methods for making assignments in isotope-labelled proteins using nuclear magnetic resonance data |
| US20240100172A1 (en) | 2020-12-21 | 2024-03-28 | Hangzhou Jijing Pharmaceutical Technology Limited | Methods and compounds for targeted autophagy |
| WO2025175249A1 (en) | 2024-02-14 | 2025-08-21 | Olema Pharmaceuticals, Inc. | Estrogen receptor modulators and uses thereof |
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| US5527819A (en) | 1991-09-06 | 1996-06-18 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| FR2772763B1 (fr) | 1997-12-24 | 2004-01-23 | Sod Conseils Rech Applic | Nouveaux analogues tetracycliques de camptothecines, leurs procedes de preparation, leur application comme medicaments et les compositions pharmaceutiques les contenant |
| US6316466B1 (en) * | 1998-05-05 | 2001-11-13 | Syntex (U.S.A.) Llc | Pyrazole derivatives P-38 MAP kinase inhibitors |
| US20030236288A1 (en) | 2002-02-28 | 2003-12-25 | Karl Schoenafinger | Use of substituted 3-phenyl-5-alkoxy-3H-(1,3,4)-oxadizol-2-ones for inhibiting pancreatic lipase |
| UA79804C2 (en) | 2002-07-03 | 2007-07-25 | Janssen Pharmaceutica Nv | Cck-1 receptor modulators |
| EA011609B1 (ru) | 2003-06-24 | 2009-04-28 | Юнироял Кемикал Компани, Инк. | Фунгицидные феноксифенилгидразиновые производные |
| PT1732892E (pt) | 2004-03-26 | 2008-12-22 | Hoffmann La Roche | Tetra-hidrocarbazóis e os seus derivados |
| UA86283C2 (uk) | 2005-01-07 | 2009-04-10 | Пфайзер Продактс Инк. | Гетероароматичні сполуки хіноліну і їх застосування як інгібіторів pde10 |
| EP2308839B1 (en) | 2005-04-20 | 2017-03-01 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compounds |
| FR2892416B1 (fr) | 2005-10-20 | 2008-06-27 | Sanofi Aventis Sa | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
| EP1960382A1 (en) | 2005-11-03 | 2008-08-27 | ChemBridge Research Laboratories, Inc. | Heterocyclic compounds as tyrosine kinase modulators |
| JP2009516702A (ja) | 2005-11-18 | 2009-04-23 | スミスクライン・ビーチャム・コーポレイション | 化合物 |
| US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
| WO2008078091A1 (en) | 2006-12-22 | 2008-07-03 | Astex Therapeutics Limited | Bicyclic heterocyclic compounds as fgfr inhibitors |
| MX2009010696A (es) | 2007-04-06 | 2009-10-20 | Novartis Ag | Derivados de 2,6-naftiridina como moduladores de cinasa de proteina. |
| CN104447716A (zh) | 2007-05-09 | 2015-03-25 | 沃泰克斯药物股份有限公司 | Cftr调节剂 |
| US8026257B2 (en) | 2007-07-11 | 2011-09-27 | Bristol-Myers Squibb Company | Substituted heterocyclic ethers and their use in CNS disorders |
| TW200920369A (en) | 2007-10-26 | 2009-05-16 | Amira Pharmaceuticals Inc | 5-lipoxygenase activating protein (flap) inhibitor |
| ES2552320T3 (es) * | 2008-06-24 | 2015-11-27 | F. Hoffmann-La Roche Ag | Nuevas piridín-2-onas y piridazín-3-onas sustituidas |
| PH12012500252A1 (en) * | 2009-08-07 | 2015-06-26 | Chugai Pharmaceutical Co Ltd | Aminopyrazole derivative |
| US9840515B2 (en) | 2010-12-09 | 2017-12-12 | University of Pittsburgh—of the Commonwealth System of Higher Education | Protein kinase D inhibitors |
| JP5620417B2 (ja) | 2011-02-07 | 2014-11-05 | 中外製薬株式会社 | アミノピラゾール誘導体を含む医薬 |
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