JP2010539083A5 - - Google Patents
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- Publication number
- JP2010539083A5 JP2010539083A5 JP2010524085A JP2010524085A JP2010539083A5 JP 2010539083 A5 JP2010539083 A5 JP 2010539083A5 JP 2010524085 A JP2010524085 A JP 2010524085A JP 2010524085 A JP2010524085 A JP 2010524085A JP 2010539083 A5 JP2010539083 A5 JP 2010539083A5
- Authority
- JP
- Japan
- Prior art keywords
- thiophene
- carboxylic acid
- chlorophenyl
- bromophenyl
- fluorobenzamido
- 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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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 150000001875 compounds Chemical class 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- -1 4-chlorobenzamido Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000000651 prodrug Substances 0.000 claims 4
- 229940002612 prodrug Drugs 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 4
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
- DBPKFTINUNROTG-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(3-chlorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC(Cl)=C1 DBPKFTINUNROTG-UHFFFAOYSA-N 0.000 claims 2
- BTRWFHPWJJOKAL-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(3-fluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC(F)=C1 BTRWFHPWJJOKAL-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims 2
- SEMSENMTSCLCPW-UHFFFAOYSA-N 2-[(2-chloro-4-fluorobenzoyl)amino]-4-(4-chlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1Cl SEMSENMTSCLCPW-UHFFFAOYSA-N 0.000 claims 1
- RQGJBOGLIDKSLE-UHFFFAOYSA-N 2-[(3-fluorobenzoyl)amino]-4-(4-methylphenyl)thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)C=2C=C(F)C=CC=2)=C1C(O)=O RQGJBOGLIDKSLE-UHFFFAOYSA-N 0.000 claims 1
- WAUUGGMBUBUANN-UHFFFAOYSA-N 2-[(3-fluorobenzoyl)amino]-4-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 WAUUGGMBUBUANN-UHFFFAOYSA-N 0.000 claims 1
- BDBMXORBWMDZNN-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(2-bromophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Br)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 BDBMXORBWMDZNN-UHFFFAOYSA-N 0.000 claims 1
- HOKFGURHEXPDOX-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(3,4-dichlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 HOKFGURHEXPDOX-UHFFFAOYSA-N 0.000 claims 1
- VNJWGWLHJCVWII-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(3,5-dichlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=C(Cl)C=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 VNJWGWLHJCVWII-UHFFFAOYSA-N 0.000 claims 1
- XKADKRFWPHOYIH-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(3-chlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 XKADKRFWPHOYIH-UHFFFAOYSA-N 0.000 claims 1
- XJTBNLJGGPCAAN-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(4-bromophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 XJTBNLJGGPCAAN-UHFFFAOYSA-N 0.000 claims 1
- OKFFDBYTPKPSOR-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(4-chlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 OKFFDBYTPKPSOR-UHFFFAOYSA-N 0.000 claims 1
- YXIUASJWPWREKH-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(4-methylphenyl)thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(Br)=CC=2)=C1C(O)=O YXIUASJWPWREKH-UHFFFAOYSA-N 0.000 claims 1
- DANJEEZQZPBEJT-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)O)=C1NC(=O)C1=CC=C(Br)C=C1 DANJEEZQZPBEJT-UHFFFAOYSA-N 0.000 claims 1
- UDIWZNZAHJYFMW-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(3,4-dichlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 UDIWZNZAHJYFMW-UHFFFAOYSA-N 0.000 claims 1
- XHXKJTDAYTWDOP-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(3-chlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 XHXKJTDAYTWDOP-UHFFFAOYSA-N 0.000 claims 1
- NUTHQSADGDMPOK-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(4-chlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 NUTHQSADGDMPOK-UHFFFAOYSA-N 0.000 claims 1
- YTQXMVLXSXPAFM-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(4-fluorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(F)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 YTQXMVLXSXPAFM-UHFFFAOYSA-N 0.000 claims 1
- IWIGQJKWMNVSOD-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(4-methylphenyl)thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(Cl)=CC=2)=C1C(O)=O IWIGQJKWMNVSOD-UHFFFAOYSA-N 0.000 claims 1
- WCTIULSZBBTXSV-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(=CC=2)C(F)(F)F)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 WCTIULSZBBTXSV-UHFFFAOYSA-N 0.000 claims 1
- ZPOMRVLYWGBIKB-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-4-(4-methylphenyl)thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(F)=CC=2)=C1C(O)=O ZPOMRVLYWGBIKB-UHFFFAOYSA-N 0.000 claims 1
- DRGPXTMDFBWKEG-UHFFFAOYSA-N 2-[(4-fluorobenzoyl)amino]-4-phenylthiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 DRGPXTMDFBWKEG-UHFFFAOYSA-N 0.000 claims 1
- QZIXZOVENYVEQN-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC(Cl)=CC=2)Cl)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 QZIXZOVENYVEQN-UHFFFAOYSA-N 0.000 claims 1
- SNQDCURCBCFYFO-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC(Cl)=CC=2)Cl)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 SNQDCURCBCFYFO-UHFFFAOYSA-N 0.000 claims 1
- FSXGQBATJXQKBL-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC(Cl)=CC=2)Cl)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 FSXGQBATJXQKBL-UHFFFAOYSA-N 0.000 claims 1
- PGGDTXCRWWNYBP-UHFFFAOYSA-N 4-(2-bromophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Br)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 PGGDTXCRWWNYBP-UHFFFAOYSA-N 0.000 claims 1
- SZKNPSNBPOAFTK-UHFFFAOYSA-N 4-(2-bromophenyl)-2-[(4-chlorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Br)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 SZKNPSNBPOAFTK-UHFFFAOYSA-N 0.000 claims 1
- CKJGQFCTHZEGID-UHFFFAOYSA-N 4-(2-bromophenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Br)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 CKJGQFCTHZEGID-UHFFFAOYSA-N 0.000 claims 1
- CREAZSCUZDDGET-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Cl)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 CREAZSCUZDDGET-UHFFFAOYSA-N 0.000 claims 1
- IQLVGIVWXXJUMN-UHFFFAOYSA-N 4-(2-chlorophenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC=CC=2)Cl)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 IQLVGIVWXXJUMN-UHFFFAOYSA-N 0.000 claims 1
- ZWISNYQPSINYDS-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 ZWISNYQPSINYDS-UHFFFAOYSA-N 0.000 claims 1
- MALAFHOJEGPMEA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 MALAFHOJEGPMEA-UHFFFAOYSA-N 0.000 claims 1
- POQKFHHGFKGEGF-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 POQKFHHGFKGEGF-UHFFFAOYSA-N 0.000 claims 1
- RQFBTIOQAZQHGT-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(NC(=O)C=2C=C(F)C=CC=2)=C1C(O)=O RQFBTIOQAZQHGT-UHFFFAOYSA-N 0.000 claims 1
- RNCPDPBDTAYEGB-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(F)=CC=2)=C1C(O)=O RNCPDPBDTAYEGB-UHFFFAOYSA-N 0.000 claims 1
- KNKGXYKGEYCWLF-UHFFFAOYSA-N 4-(3,5-dichlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=C(Cl)C=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 KNKGXYKGEYCWLF-UHFFFAOYSA-N 0.000 claims 1
- RTUFBIHOJZLUBJ-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 RTUFBIHOJZLUBJ-UHFFFAOYSA-N 0.000 claims 1
- BQNPNOGZPYQDTP-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=C(Cl)C=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 BQNPNOGZPYQDTP-UHFFFAOYSA-N 0.000 claims 1
- DCHPIQBGCGQKCM-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(2-chloro-4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1Cl DCHPIQBGCGQKCM-UHFFFAOYSA-N 0.000 claims 1
- QNXRDAVIADLKCK-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(2-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=CC=C1F QNXRDAVIADLKCK-UHFFFAOYSA-N 0.000 claims 1
- NRVKDCQHKRCBLD-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(3,4-difluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C(F)=C1 NRVKDCQHKRCBLD-UHFFFAOYSA-N 0.000 claims 1
- DRQNMCYZPREQRJ-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(3-fluoro-4-methoxybenzoyl)amino]thiophene-3-carboxylic acid Chemical compound C1=C(F)C(OC)=CC=C1C(=O)NC1=C(C(O)=O)C(C=2C=CC(Br)=CC=2)=CS1 DRQNMCYZPREQRJ-UHFFFAOYSA-N 0.000 claims 1
- PXGYUBINGLWGPU-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 PXGYUBINGLWGPU-UHFFFAOYSA-N 0.000 claims 1
- LMBFGEPCZOHWGY-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(4-chlorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 LMBFGEPCZOHWGY-UHFFFAOYSA-N 0.000 claims 1
- BQURYOHDRQHPEV-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(4-cyanobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(C#N)C=C1 BQURYOHDRQHPEV-UHFFFAOYSA-N 0.000 claims 1
- VHZIYRHPROFEMO-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[3-(2,4-difluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C=C1F VHZIYRHPROFEMO-UHFFFAOYSA-N 0.000 claims 1
- YBRIENQMGZJMLX-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[3-(3,4-difluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C(F)=C1 YBRIENQMGZJMLX-UHFFFAOYSA-N 0.000 claims 1
- FGGKIYANINBSQV-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[3-(3-fluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC(F)=C1 FGGKIYANINBSQV-UHFFFAOYSA-N 0.000 claims 1
- CZJLFEYYSLDZFS-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[3-(4-fluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Br)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C=C1 CZJLFEYYSLDZFS-UHFFFAOYSA-N 0.000 claims 1
- DZOVNYIHSJWERL-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(3-phenylpropanoylamino)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=CC=C1 DZOVNYIHSJWERL-UHFFFAOYSA-N 0.000 claims 1
- PUCHNSSEKHJLCL-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[(3-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=CC(F)=C1 PUCHNSSEKHJLCL-UHFFFAOYSA-N 0.000 claims 1
- XSERXLGNPCOWGA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[(4-ethylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C(=O)NC1=C(C(O)=O)C(C=2C=CC(Cl)=CC=2)=CS1 XSERXLGNPCOWGA-UHFFFAOYSA-N 0.000 claims 1
- UAQFVJIIXIDYBM-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[(4-fluorobenzoyl)amino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(F)C=C1 UAQFVJIIXIDYBM-UHFFFAOYSA-N 0.000 claims 1
- XXRBXQCBRPYVKA-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[(4-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C(=O)NC1=C(C(O)=O)C(C=2C=CC(Cl)=CC=2)=CS1 XXRBXQCBRPYVKA-UHFFFAOYSA-N 0.000 claims 1
- ASQBCIOXNPNBKP-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(2,4-difluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C=C1F ASQBCIOXNPNBKP-UHFFFAOYSA-N 0.000 claims 1
- ZGDHPHJEJUVNKJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(3,4-difluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C(F)=C1 ZGDHPHJEJUVNKJ-UHFFFAOYSA-N 0.000 claims 1
- YWMBSLLFFXFKBF-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(4-chlorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(Cl)C=C1 YWMBSLLFFXFKBF-UHFFFAOYSA-N 0.000 claims 1
- FPUHHWYMUBTYKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[3-(4-fluorophenyl)propanoylamino]thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC(Cl)=CC=2)C(C(=O)O)=C1NC(=O)CCC1=CC=C(F)C=C1 FPUHHWYMUBTYKQ-UHFFFAOYSA-N 0.000 claims 1
- 206010071198 Allergic hepatitis Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
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-
2008
- 2008-08-15 AU AU2008299220A patent/AU2008299220B2/en not_active Ceased
- 2008-08-15 MX MX2010002712A patent/MX2010002712A/es not_active Application Discontinuation
- 2008-08-15 BR BRPI0816326 patent/BRPI0816326A2/pt not_active IP Right Cessation
- 2008-08-15 CN CN200880115726A patent/CN101854933A/zh active Pending
- 2008-08-15 WO PCT/US2008/073392 patent/WO2009035818A1/en not_active Ceased
- 2008-08-15 JP JP2010524085A patent/JP5411141B2/ja not_active Expired - Fee Related
- 2008-08-15 KR KR1020107007759A patent/KR101257550B1/ko not_active Expired - Fee Related
- 2008-08-15 US US12/192,812 patent/US8263641B2/en not_active Expired - Fee Related
- 2008-08-15 EP EP08798036A patent/EP2200607A4/en not_active Withdrawn
- 2008-08-15 CA CA2699157A patent/CA2699157A1/en not_active Abandoned
- 2008-08-15 RU RU2010112967/04A patent/RU2465272C2/ru not_active IP Right Cessation
-
2012
- 2012-07-19 US US13/553,726 patent/US8524765B2/en active Active
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