JP2016540022A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361915582P | 2013-12-13 | 2013-12-13 | |
| US61/915,582 | 2013-12-13 | ||
| PCT/EP2014/077124 WO2015086642A1 (en) | 2013-12-13 | 2014-12-10 | Inhibitors of bruton's tyrosine kinase |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016540022A JP2016540022A (ja) | 2016-12-22 |
| JP2016540022A5 true JP2016540022A5 (enExample) | 2017-09-28 |
| JP6219523B2 JP6219523B2 (ja) | 2017-10-25 |
Family
ID=52016584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016539166A Expired - Fee Related JP6219523B2 (ja) | 2013-12-13 | 2014-12-10 | ブルトンチロシンキナーゼの阻害剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9556150B2 (enExample) |
| EP (1) | EP3080099B1 (enExample) |
| JP (1) | JP6219523B2 (enExample) |
| KR (1) | KR101768402B1 (enExample) |
| CN (1) | CN105793252B (enExample) |
| CA (1) | CA2931189C (enExample) |
| MX (1) | MX374758B (enExample) |
| RU (1) | RU2648236C2 (enExample) |
| TW (1) | TW201534600A (enExample) |
| WO (1) | WO2015086642A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9624201B2 (en) * | 2013-12-13 | 2017-04-18 | Hoffmann-La Roche Inc. | Inhibitors of bruton's tyrosine kinase |
| WO2015099127A1 (ja) | 2013-12-27 | 2015-07-02 | 中外製薬株式会社 | Ｆｇｆｒゲートキーパー変異遺伝子およびそれを標的とする医薬 |
| JP6762300B2 (ja) | 2015-06-17 | 2020-09-30 | 中外製薬株式会社 | アミノピラゾール誘導体 |
| IL293821A (en) | 2015-07-02 | 2022-08-01 | Acerta Pharma Bv | Solid forms and formulations of (S)-4-(8-amino-3-(1-(but-2-aminoyl)pyrrolidine-2-yl)imidazo[5,1-yl]pyrazin-1-yl)-en- (pyridine-2-yl)benzamide |
| 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 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN1934074A (zh) | 2003-06-24 | 2007-03-21 | 尤尼罗亚尔化学公司 | 杀真菌的苯氧基苯肼衍生物 |
| JP4705630B2 (ja) | 2004-03-26 | 2011-06-22 | エフ．ホフマン−ラ ロシュ アーゲー | テトラヒドロカルバゾール及び誘導体 |
| WO2006072828A2 (en) | 2005-01-07 | 2006-07-13 | Pfizer Products Inc. | Heteroaromatic quinoline compounds and their use as pde10 inhibitors |
| US8957070B2 (en) | 2005-04-20 | 2015-02-17 | Takeda Pharmaceutical Company Limited | Glucokinase activator compounds, methods of activating glucokinase and methods of treating diabetes and obesity |
| FR2892416B1 (fr) | 2005-10-20 | 2008-06-27 | Sanofi Aventis Sa | Derives de 6-heteroarylpyridoindolone, leur preparation et leur application en therapeutique |
| US8629147B2 (en) | 2005-11-03 | 2014-01-14 | Chembridge Corporation | Heterocyclic compounds useful in the treatment of neoplastic diseases, inflammatory disorders and immunomodulatory disorders |
| 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 |
| CN101679408B (zh) | 2006-12-22 | 2016-04-27 | Astex治疗学有限公司 | 作为fgfr抑制剂的双环杂环化合物 |
| AU2008235455A1 (en) | 2007-04-06 | 2008-10-16 | Novartis Ag | 2, 6-naphthyridine derivatives as protein kinase modulators |
| EP2164840A2 (en) | 2007-05-09 | 2010-03-24 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
| 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 |
| PE20100851A1 (es) * | 2008-06-24 | 2011-01-31 | Hoffmann La Roche | PIRIDIN-2-ONAS Y PIRIDAZIN-3-ONAS SUSTITUIDAS COMO INHIBIDORES DE Btk |
| HRP20151258T1 (hr) * | 2009-08-07 | 2016-02-26 | Chugai Seiyaku Kabushiki Kaisha | Derivat aminopirazola |
| 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 |
-
2014
- 2014-12-10 JP JP2016539166A patent/JP6219523B2/ja not_active Expired - Fee Related
- 2014-12-10 RU RU2016126176A patent/RU2648236C2/ru active
- 2014-12-10 EP EP14809645.6A patent/EP3080099B1/en active Active
- 2014-12-10 KR KR1020167018757A patent/KR101768402B1/ko not_active Expired - Fee Related
- 2014-12-10 MX MX2016006744A patent/MX374758B/es active IP Right Grant
- 2014-12-10 WO PCT/EP2014/077124 patent/WO2015086642A1/en not_active Ceased
- 2014-12-10 CN CN201480066841.0A patent/CN105793252B/zh not_active Expired - Fee Related
- 2014-12-10 CA CA2931189A patent/CA2931189C/en active Active
- 2014-12-10 US US15/102,832 patent/US9556150B2/en not_active Expired - Fee Related
- 2014-12-11 TW TW103143358A patent/TW201534600A/zh unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014531449A5 (enExample) | ||
| US9833455B2 (en) | Preparation and methods of use for ortho-aryl 5-membered heteroaryl-carboxamide containing multi-targeted kinase inhibitors | |
| TWI455939B (zh) | ｃＭＥＴ抑制劑 | |
| JP2024540445A5 (enExample) | ||
| JP2015527401A5 (enExample) | ||
| JP2010533160A5 (enExample) | ||
| JP2016510035A5 (enExample) | ||
| JP2017504635A5 (enExample) | ||
| JP2007519694A5 (enExample) | ||
| HRP20210454T1 (hr) | 3-supstituirani 5-amino-6h-tiazolo[4,5-d]pirimidin-2,7-dion spojevi za liječenje i profilaksu virusne infekcije | |
| IL273000B2 (en) | Compounds that inhibit lysophosphatidic acid receptor 1 (lpar1) | |
| JP2010513283A (ja) | 新規なオキサジアゾール化合物 | |
| JP2013518129A5 (enExample) | ||
| JP2012522847A5 (enExample) | ||
| RU2009142431A (ru) | Производные триазолопиридинкарбоксамидов и триазолопиримидинкарбоксамидов, их получение и их применение в терапии | |
| NZ601077A (en) | Use of an adrenal hormone-modifying agent | |
| JP2013543896A5 (enExample) | ||
| SI3106463T1 (en) | Substituted pyrazolo(1,5-)pyrimidine compounds as trk kinase inhibitors | |
| JP2015519401A5 (enExample) | ||
| US8563562B2 (en) | Compounds having antiviral properties | |
| EA201650029A1 (ru) | Пиразолопиридины и пиразолопиримидины | |
| RU2009142434A (ru) | Производные триазолопиридин-карбоксамидов и триазолопиримидин-карбоксамидов, их получение и их применение в терапии | |
| JP2016532715A5 (enExample) | ||
| PE20141700A1 (es) | Compuestos de 2-(2,4,5-anilino sustituido) pirimidina | |
| JP2019504901A5 (enExample) |