JP2010539083A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 1
- 201000002481 Myositis Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010046914 Vaginal infection Diseases 0.000 claims 1
- 201000008100 Vaginitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 201000001981 dermatomyositis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 125000004404 heteroalkyl group Chemical group 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 206010028417 myasthenia gravis Diseases 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 206010043778 thyroiditis Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97116107P | 2007-09-10 | 2007-09-10 | |
| US60/971,161 | 2007-09-10 | ||
| PCT/US2008/073392 WO2009035818A1 (en) | 2007-09-10 | 2008-08-15 | Compounds that modulate intracellular calcium |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010539083A JP2010539083A (ja) | 2010-12-16 |
| JP2010539083A5 true JP2010539083A5 (enExample) | 2011-09-29 |
| JP5411141B2 JP5411141B2 (ja) | 2014-02-12 |
Family
ID=40452397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010524085A Expired - Fee Related JP5411141B2 (ja) | 2007-09-10 | 2008-08-15 | 細胞内カルシウムを調節する化合物 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8263641B2 (enExample) |
| EP (1) | EP2200607A4 (enExample) |
| JP (1) | JP5411141B2 (enExample) |
| KR (1) | KR101257550B1 (enExample) |
| CN (1) | CN101854933A (enExample) |
| AU (1) | AU2008299220B2 (enExample) |
| BR (1) | BRPI0816326A2 (enExample) |
| CA (1) | CA2699157A1 (enExample) |
| MX (1) | MX2010002712A (enExample) |
| RU (1) | RU2465272C2 (enExample) |
| WO (1) | WO2009035818A1 (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ580195A (en) * | 2007-03-05 | 2012-03-30 | Univ Queensland | Targeting crac for breast cancer therapy and/or diagnosis |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8389567B2 (en) * | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| TWI392673B (zh) | 2008-08-27 | 2013-04-11 | Calcimedica Inc | 調控細胞內鈣離子濃度之化合物 |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| US8143269B2 (en) * | 2008-10-03 | 2012-03-27 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
| EP2477982A4 (en) * | 2009-09-16 | 2013-04-03 | Calcimedica Inc | COMPOUNDS THAT MODULATE INTRACELLULAR CALCIUM |
| US8377970B2 (en) | 2009-10-08 | 2013-02-19 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel |
| US8993612B2 (en) | 2009-10-08 | 2015-03-31 | Rhizen Pharmaceuticals Sa | Modulators of calcium release-activated calcium channel and methods for treatment of non-small cell lung cancer |
| CN102574843B (zh) | 2009-10-22 | 2015-06-17 | 法博太科制药有限公司 | 抗纤维化剂的稠环类似物 |
| US20120231006A1 (en) | 2009-11-20 | 2012-09-13 | Amgen Inc. | Anti-orai1 antigen binding proteins and uses thereof |
| US10703722B2 (en) | 2010-04-27 | 2020-07-07 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| KR101799304B1 (ko) | 2010-05-12 | 2017-11-20 | 렘펙스 파머수티클스 인코퍼레이티드 | 테트라사이클린 조성물 |
| EP2609095A4 (en) | 2010-08-27 | 2014-06-18 | Calcimedica Inc | COMPOUNDS MODULATING INTRACELLULAR CALCIUM |
| AU2011322068B2 (en) | 2010-10-30 | 2015-11-05 | Lupin Limited | Oxazoline and isoxazoline derivatives as CRAC modulators |
| CN104878098A (zh) * | 2011-12-19 | 2015-09-02 | 上海吉凯基因化学技术有限公司 | 人stim1基因的用途及其相关药物 |
| WO2013164773A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyrazole compounds as crac modulators |
| CA2871270A1 (en) | 2012-05-02 | 2013-11-07 | Lupin Limited | Substituted pyridine compounds as crac modulators |
| US9512116B2 (en) | 2012-10-12 | 2016-12-06 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| WO2014203217A1 (en) | 2013-06-21 | 2014-12-24 | Lupin Limited | Substituted heterocyclic compounds as crac modulators |
| WO2014207648A1 (en) | 2013-06-24 | 2014-12-31 | Lupin Limited | Chromane and chromene derivatives and their use as crac modulators |
| EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| JP6399874B2 (ja) * | 2013-09-20 | 2018-10-03 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 化合物の抗炎症効果または免疫抑制効果を予測する方法 |
| PL2982982T3 (pl) * | 2014-08-06 | 2018-03-30 | Centre Hospitalier Regional Et Univ De Brest | Sposób badania przesiewowego związków przy użyciu błonowego STIM1 |
| EP3778595B1 (en) | 2015-02-27 | 2021-08-25 | Calcimedica, Inc. | Pancreatitis treatment |
| CA2995094A1 (en) | 2015-08-07 | 2017-02-16 | Calcimedica, Inc. | Use of crac channel inhibitors for the treatment of stroke and traumatic brain injury |
| JP7185631B2 (ja) | 2017-02-03 | 2022-12-07 | サータ セラピューティクス プロプライエタリー リミテッド | 抗線維化化合物 |
| CN108938625B (zh) * | 2017-05-27 | 2021-06-29 | 北京大学 | 2-芳甲酰胺基噻吩-3-羧酸类衍生物作为ano1蛋白抑制剂的用途及制备方法 |
| CN107496420B (zh) * | 2017-08-25 | 2020-07-07 | 中国科学院微生物研究所 | 环匹阿尼酸类生物碱化合物的用途 |
| CA3087830A1 (en) * | 2018-02-08 | 2019-08-15 | Enyo Pharma | Non-fused thiophene derivatives and their uses |
| WO2020053834A1 (en) | 2018-09-14 | 2020-03-19 | Rhizen Pharmaceuticals Sa | Compositions comprising a crac inhibitor and a corticosteroid and methods of use thereof |
| CN109081824A (zh) * | 2018-10-08 | 2018-12-25 | 浙江工业大学上虞研究院有限公司 | 2-氨基噻吩类化合物的制备方法 |
| JP2023528537A (ja) | 2020-03-20 | 2023-07-04 | カルシメディカ，インク． | 急性肺傷害及び急性呼吸窮迫症候群を処置するための方法及び組成物 |
| CA3198798A1 (en) | 2020-11-13 | 2022-05-19 | Kenneth Stauderman | Improved synthesis of crac channel inhibitors |
| CN116444481B (zh) * | 2022-01-05 | 2025-07-25 | 北京大学 | 作为ano1蛋白抑制剂的4-芳基噻吩甲酸类化合物 |
| CN114948923A (zh) * | 2022-06-02 | 2022-08-30 | 南京中医药大学 | 奥替溴铵及其盐在制备治疗周围神经病变以及肺纤维化药物中的应用 |
Family Cites Families (140)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3472802A (en) | 1966-11-23 | 1969-10-14 | Inter Chem Corp | Novel nitrocellulose flexographic printing inks |
| US3598122A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| US3993073A (en) | 1969-04-01 | 1976-11-23 | Alza Corporation | Novel drug delivery device |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
| ES371373A1 (es) * | 1969-09-10 | 1972-04-01 | Patronato De Investigacion Cie | Procedimiento para la obtencion de derivados de 4-oxo-3- amino-3,4 - dihidrotieno (3,2-d) pirimidina sustituidos. |
| US3710795A (en) | 1970-09-29 | 1973-01-16 | Alza Corp | Drug-delivery device with stretched, rate-controlling membrane |
| US4069307A (en) | 1970-10-01 | 1978-01-17 | Alza Corporation | Drug-delivery device comprising certain polymeric materials for controlled release of drug |
| US3731683A (en) | 1971-06-04 | 1973-05-08 | Alza Corp | Bandage for the controlled metering of topical drugs to the skin |
| US3996934A (en) | 1971-08-09 | 1976-12-14 | Alza Corporation | Medical bandage |
| US3742951A (en) | 1971-08-09 | 1973-07-03 | Alza Corp | Bandage for controlled release of vasodilators |
| BE795384A (fr) | 1972-02-14 | 1973-08-13 | Ici Ltd | Pansements |
| GB1419074A (en) | 1972-06-09 | 1975-12-24 | Ici Ltd | Process for manufacturing substituted thiophene compounds |
| US3921636A (en) | 1973-01-15 | 1975-11-25 | Alza Corp | Novel drug delivery device |
| US3993072A (en) | 1974-08-28 | 1976-11-23 | Alza Corporation | Microporous drug delivery device |
| US4151273A (en) | 1974-10-31 | 1979-04-24 | The Regents Of The University Of California | Increasing the absorption rate of insoluble drugs |
| US3972995A (en) | 1975-04-14 | 1976-08-03 | American Home Products Corporation | Dosage form |
| GB1548398A (en) * | 1975-06-05 | 1979-07-11 | Lilly Industries Ltd | Acylamino pyrroles furans and thiophenes |
| US4077407A (en) | 1975-11-24 | 1978-03-07 | Alza Corporation | Osmotic devices having composite walls |
| US4031894A (en) | 1975-12-08 | 1977-06-28 | Alza Corporation | Bandage for transdermally administering scopolamine to prevent nausea |
| US4060084A (en) | 1976-09-07 | 1977-11-29 | Alza Corporation | Method and therapeutic system for providing chemotherapy transdermally |
| US4201211A (en) | 1977-07-12 | 1980-05-06 | Alza Corporation | Therapeutic system for administering clonidine transdermally |
| JPS5562012A (en) | 1978-11-06 | 1980-05-10 | Teijin Ltd | Slow-releasing preparation |
| US4230105A (en) | 1978-11-13 | 1980-10-28 | Merck & Co., Inc. | Transdermal delivery of drugs |
| US4229447A (en) | 1979-06-04 | 1980-10-21 | American Home Products Corporation | Intraoral methods of using benzodiazepines |
| CA1146866A (en) | 1979-07-05 | 1983-05-24 | Yamanouchi Pharmaceutical Co. Ltd. | Process for the production of sustained release pharmaceutical composition of solid medical material |
| US4291015A (en) | 1979-08-14 | 1981-09-22 | Key Pharmaceuticals, Inc. | Polymeric diffusion matrix containing a vasodilator |
| US4327725A (en) | 1980-11-25 | 1982-05-04 | Alza Corporation | Osmotic device with hydrogel driving member |
| US4476116A (en) | 1982-12-10 | 1984-10-09 | Syntex (U.S.A.) Inc. | Polypeptides/chelating agent nasal compositions having enhanced peptide absorption |
| US5116817A (en) | 1982-12-10 | 1992-05-26 | Syntex (U.S.A.) Inc. | LHRH preparations for intranasal administration |
| US4596795A (en) | 1984-04-25 | 1986-06-24 | The United States Of America As Represented By The Secretary, Dept. Of Health & Human Services | Administration of sex hormones in the form of hydrophilic cyclodextrin derivatives |
| US4624848A (en) | 1984-05-10 | 1986-11-25 | Ciba-Geigy Corporation | Active agent containing hydrogel devices wherein the active agent concentration profile contains a sigmoidal concentration gradient for improved constant release, their manufacture and use |
| GB8518301D0 (en) | 1985-07-19 | 1985-08-29 | Fujisawa Pharmaceutical Co | Hydrodynamically explosive systems |
| US5011692A (en) | 1985-12-28 | 1991-04-30 | Sumitomo Pharmaceuticals Company, Limited | Sustained pulsewise release pharmaceutical preparation |
| US4755386A (en) | 1986-01-22 | 1988-07-05 | Schering Corporation | Buccal formulation |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| US4968509A (en) | 1987-07-27 | 1990-11-06 | Mcneilab, Inc. | Oral sustained release acetaminophen formulation and process |
| US5052558A (en) | 1987-12-23 | 1991-10-01 | Entravision, Inc. | Packaged pharmaceutical product |
| US5033252A (en) | 1987-12-23 | 1991-07-23 | Entravision, Inc. | Method of packaging and sterilizing a pharmaceutical product |
| IL92966A (en) | 1989-01-12 | 1995-07-31 | Pfizer | Dispensing devices powered by hydrogel |
| PH27357A (en) | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
| US5739136A (en) | 1989-10-17 | 1998-04-14 | Ellinwood, Jr.; Everett H. | Intraoral dosing method of administering medicaments |
| US5017381A (en) | 1990-05-02 | 1991-05-21 | Alza Corporation | Multi-unit pulsatile delivery system |
| US5633009A (en) | 1990-11-28 | 1997-05-27 | Sano Corporation | Transdermal administration of azapirones |
| WO1992018106A1 (fr) | 1991-04-16 | 1992-10-29 | Nippon Shinyaku Co., Ltd. | Procede de production d'une dispersion solide |
| US5229135A (en) | 1991-11-22 | 1993-07-20 | Prographarm Laboratories | Sustained release diltiazem formulation |
| HU227530B1 (en) | 1991-11-22 | 2011-07-28 | Warner Chilcott Company | Delayed-release compositions containing risedronate and process for their production |
| US5340591A (en) | 1992-01-24 | 1994-08-23 | Fujisawa Pharmaceutical Co., Ltd. | Method of producing a solid dispersion of the sparingly water-soluble drug, nilvadipine |
| US5461140A (en) | 1992-04-30 | 1995-10-24 | Pharmaceutical Delivery Systems | Bioerodible polymers for solid controlled release pharmaceutical compositions |
| US5260068A (en) | 1992-05-04 | 1993-11-09 | Anda Sr Pharmaceuticals Inc. | Multiparticulate pulsatile drug delivery system |
| US5281420A (en) | 1992-05-19 | 1994-01-25 | The Procter & Gamble Company | Solid dispersion compositions of tebufelone |
| US5323907A (en) | 1992-06-23 | 1994-06-28 | Multi-Comp, Inc. | Child resistant package assembly for dispensing pharmaceutical medications |
| AU4198793A (en) | 1992-07-24 | 1994-01-27 | Takeda Chemical Industries Ltd. | Microparticle preparation and production thereof |
| US5700485A (en) | 1992-09-10 | 1997-12-23 | Children's Medical Center Corporation | Prolonged nerve blockade by the combination of local anesthetic and glucocorticoid |
| JP2616252B2 (ja) | 1992-10-16 | 1997-06-04 | 日本新薬株式会社 | ワックスマトリックスの製法 |
| DE69306595T2 (de) * | 1992-11-23 | 1997-04-03 | Pfizer | Regioselektive synthese von 4-chlor-2-thiophencarbonsäure |
| US5260069A (en) | 1992-11-27 | 1993-11-09 | Anda Sr Pharmaceuticals Inc. | Pulsatile particles drug delivery system |
| US5604260A (en) | 1992-12-11 | 1997-02-18 | Merck Frosst Canada Inc. | 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2 |
| EP0679157B1 (en) | 1993-01-15 | 1997-11-19 | G.D. Searle & Co. | Novel 3,4-diaryl thiophenes and analogs thereof having use as antiinflammatory agents |
| US5686105A (en) | 1993-10-19 | 1997-11-11 | The Procter & Gamble Company | Pharmaceutical dosage form with multiple enteric polymer coatings for colonic delivery |
| US5409944A (en) | 1993-03-12 | 1995-04-25 | Merck Frosst Canada, Inc. | Alkanesulfonamido-1-indanone derivatives as inhibitors of cyclooxygenase |
| US5380738A (en) | 1993-05-21 | 1995-01-10 | Monsanto Company | 2-substituted oxazoles further substituted by 4-fluorophenyl and 4-methylsulfonylphenyl as antiinflammatory agents |
| US5436265A (en) | 1993-11-12 | 1995-07-25 | Merck Frosst Canada, Inc. | 1-aroyl-3-indolyl alkanoic acids and derivatives thereof useful as anti-inflammatory agents |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| GB9602877D0 (en) | 1996-02-13 | 1996-04-10 | Merck Frosst Canada Inc | 3,4-Diaryl-2-hydroxy-2,5- dihydrofurans as prodrugs to cox-2 inhibitors |
| US5344991A (en) | 1993-10-29 | 1994-09-06 | G.D. Searle & Co. | 1,2 diarylcyclopentenyl compounds for the treatment of inflammation |
| US5466823A (en) | 1993-11-30 | 1995-11-14 | G.D. Searle & Co. | Substituted pyrazolyl benzenesulfonamides |
| US5393790A (en) | 1994-02-10 | 1995-02-28 | G.D. Searle & Co. | Substituted spiro compounds for the treatment of inflammation |
| US5665378A (en) | 1994-09-30 | 1997-09-09 | Davis; Roosevelt | Transdermal therapeutic formulation |
| US5633272A (en) | 1995-02-13 | 1997-05-27 | Talley; John J. | Substituted isoxazoles for the treatment of inflammation |
| US5567441A (en) | 1995-03-24 | 1996-10-22 | Andrx Pharmaceuticals Inc. | Diltiazem controlled release formulation |
| JPH11505258A (ja) | 1995-05-17 | 1999-05-18 | セダーシナイ メディカル センター | 小腸における消化および吸収を改善させる脂肪酸を含む組成物 |
| SE9502244D0 (sv) | 1995-06-20 | 1995-06-20 | Bioglan Ab | A composition and a process for the preparation thereof |
| US6020343A (en) | 1995-10-13 | 2000-02-01 | Merck Frosst Canada, Inc. | (Methylsulfonyl)phenyl-2-(5H)-furanones as COX-2 inhibitors |
| GB9523946D0 (en) | 1995-11-23 | 1996-01-24 | Bayer Ag | Leukotriene antagonistic benzoic acid derivatives |
| US5837284A (en) | 1995-12-04 | 1998-11-17 | Mehta; Atul M. | Delivery of multiple doses of medications |
| US6323227B1 (en) | 1996-01-02 | 2001-11-27 | Aventis Pharmaceuticals Products Inc. | Substituted N-[(aminoiminomethyl or aminomethyl)phenyl]propyl amides |
| US5858401A (en) | 1996-01-22 | 1999-01-12 | Sidmak Laboratories, Inc. | Pharmaceutical composition for cyclosporines |
| US6929801B2 (en) | 1996-02-19 | 2005-08-16 | Acrux Dds Pty Ltd | Transdermal delivery of antiparkinson agents |
| US6923983B2 (en) | 1996-02-19 | 2005-08-02 | Acrux Dds Pty Ltd | Transdermal delivery of hormones |
| ATE233743T1 (de) | 1996-04-12 | 2003-03-15 | Searle & Co | N-((4-(5-methyl-3-phenylisoxazol-4- yl)phenyl)sulphonylpropylamid und sein natriumsalz als pro-pharmakon von cox-2 inhibitoren |
| US5861419A (en) | 1996-07-18 | 1999-01-19 | Merck Frosst Canad, Inc. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| US6458373B1 (en) | 1997-01-07 | 2002-10-01 | Sonus Pharmaceuticals, Inc. | Emulsion vehicle for poorly soluble drugs |
| US5840329A (en) | 1997-05-15 | 1998-11-24 | Bioadvances Llc | Pulsatile drug delivery system |
| US6037340A (en) | 1997-05-28 | 2000-03-14 | Cadus Pharmaceutical Corporation | Synthesis and use of thiophene- and pyrrole-based heteroaromatic compounds |
| US6391452B1 (en) | 1997-07-18 | 2002-05-21 | Bayer Corporation | Compositions for nasal drug delivery, methods of making same, and methods of removing residual solvent from pharmaceutical preparations |
| US5869090A (en) | 1998-01-20 | 1999-02-09 | Rosenbaum; Jerry | Transdermal delivery of dehydroepiandrosterone |
| US6946144B1 (en) | 1998-07-08 | 2005-09-20 | Oryxe | Transdermal delivery system |
| ATE400252T1 (de) | 1999-02-10 | 2008-07-15 | Pfizer Prod Inc | Pharmazeutische feste dispersionen |
| US6395300B1 (en) | 1999-05-27 | 2002-05-28 | Acusphere, Inc. | Porous drug matrices and methods of manufacture thereof |
| US6803375B1 (en) | 2000-01-06 | 2004-10-12 | The Regents Of The University Of California | Non-peptide inhibition of T-lymphocyte activation and therapies related thereto |
| US6313138B1 (en) | 2000-02-25 | 2001-11-06 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
| EP1324993A2 (en) | 2000-04-18 | 2003-07-09 | Cytovia, Inc. | Substituted 1,4-thiazepine and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| WO2002030976A1 (en) | 2000-10-11 | 2002-04-18 | The University Of Melbourne | Cell control nucleic acids and proteins |
| DE10061876A1 (de) * | 2000-12-12 | 2002-06-20 | Aventis Pharma Gmbh | Arylierte Furan- und Thiophencarbonsäureamide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament sowie sie enthaltende pharmazeutische Zubereitungen |
| US6465014B1 (en) | 2001-03-21 | 2002-10-15 | Isp Investments Inc. | pH-dependent sustained release, drug-delivery composition |
| AU2002342607B2 (en) | 2001-08-06 | 2006-10-19 | Pharmacia Italia S.P.A. | Aminoisoxazole derivatives active as kinase inhibitors |
| US6960563B2 (en) | 2001-08-31 | 2005-11-01 | Morton Grove Pharmaceuticals, Inc. | Spontaneous emulsions containing cyclosporine |
| CA2466375A1 (en) | 2001-11-08 | 2003-05-15 | Pharmacia & Upjohn Company | Azabicyclic-substituted-heteroaryl compounds for the treatment of disease |
| AR040123A1 (es) | 2002-05-31 | 2005-03-16 | Upjohn Co | Compuestos tiofeno, antihelminticos e insecticidas |
| WO2004002977A1 (en) | 2002-07-01 | 2004-01-08 | Pharmacia & Upjohn Company Llc | Inhibitors of hcv ns5b polymerase |
| JP4818726B2 (ja) | 2002-10-16 | 2011-11-16 | プロミクス・プロプライエタリー・リミテッド | 炎症性腸疾患の治療 |
| AR043057A1 (es) | 2002-10-30 | 2005-07-13 | Vertex Pharma | Compuestos derivados de piridintiazoles como inhibidores de la quinasa rock y otras proteinas quinasa |
| US7645588B2 (en) | 2003-03-04 | 2010-01-12 | Calcimedica, Inc. | Composition comprising a cell comprising a STIM1 protein and an agent that modulates intracellular calcium and methods of use |
| MXPA05012459A (es) | 2003-05-19 | 2006-02-22 | Irm Llc | Compuestos y composiciones inmunosupresoras. |
| AU2003902851A0 (en) | 2003-06-06 | 2003-06-26 | Australian Ballet School | Ballet shoe insert |
| TWI376370B (en) | 2003-07-23 | 2012-11-11 | Synta Pharmaceuticals Corp | Compounds for inflammation and immune-related uses |
| US20050085531A1 (en) | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| WO2005048942A2 (en) | 2003-11-13 | 2005-06-02 | Pharmacia Corporation | Combination therapy comprising a cox-2 inhibitor and an antineoplastic agent |
| WO2006093518A2 (en) | 2004-06-25 | 2006-09-08 | Apath, Llc | Thienyl compounds for treating virus-related conditions |
| US20060223812A1 (en) * | 2004-07-17 | 2006-10-05 | Max-Planck-Gesellschaft Zur Forderungder Wissenschaften, E.V. | Treating neurodegenerative conditions |
| WO2006007864A1 (en) * | 2004-07-17 | 2006-01-26 | Max Planck Geselllschaft Zur Förderung Der Wissenschaft | Treating neurodegenerative conditions |
| CA2573426C (en) | 2004-07-30 | 2015-11-17 | Exelixis, Inc. | Pyrrole derivatives as pharmaceutical agents |
| KR20070057965A (ko) | 2004-09-21 | 2007-06-07 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| KR20140018997A (ko) | 2005-01-07 | 2014-02-13 | 신타 파마슈티칼스 코프. | 염증 및 면역 관련 용도를 위한 화합물 |
| PL1848435T3 (pl) | 2005-01-25 | 2016-08-31 | Synta Pharmaceuticals Corp | Związki przeciwko zapaleniom i zastosowania związane z odpornością |
| EP1846388A4 (en) | 2005-01-25 | 2011-12-07 | Synta Pharmaceuticals Corp | THIOPHEN COMPOUNDS FOR IGNITIONS AND THE IMMUNE SYSTEM APPLICATIONS |
| MX2007009888A (es) | 2005-02-17 | 2007-10-16 | Synta Pharmaceuticals Corp | Compuestos para el tratamiento de trastornos proliferativos. |
| US7563813B2 (en) | 2005-05-13 | 2009-07-21 | Wyeth | Iminothiazolidinone derivatives as SFRP-1 antagonists |
| GB0516379D0 (en) | 2005-08-09 | 2005-09-14 | Glaxo Group Ltd | Compounds |
| EP1754483A1 (en) | 2005-08-18 | 2007-02-21 | Merck Sante | Use of thienopyridone derivatives as AMPK activators and pharmaceutical compositions containing them |
| JP5881270B2 (ja) | 2006-01-05 | 2016-03-09 | チルドレンズ メディカル センター コーポレーション | Ｎｆａｔの制御因子 |
| WO2007083689A1 (ja) | 2006-01-19 | 2007-07-26 | Renascience Co., Ltd. | プラスミノーゲンアクチベーターインヒビター－１阻害剤 |
| TW200806641A (en) | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted aromatic compounds for inflammation and immune-related uses |
| TW200806290A (en) | 2006-01-25 | 2008-02-01 | Synta Pharmaceuticals Corp | Substituted biaryl compounds for inflammation and immune-related uses |
| US8455658B2 (en) | 2006-01-25 | 2013-06-04 | Synta Pharmaceuticals Corp. | Thiazole and thiadiazole compounds for inflammation and immune-related uses |
| US7816535B2 (en) | 2006-01-25 | 2010-10-19 | Synta Pharmaceuticals Corp. | Vinyl-phenyl derivatives for inflammation and immune-related uses |
| WO2007087429A2 (en) | 2006-01-25 | 2007-08-02 | Synta Pharmaceuticals Corp. | Phenyl and pyridyl compounds for inflammation and immune-related uses |
| US20070254926A1 (en) | 2006-01-31 | 2007-11-01 | Jun Jiang | Pyridylphenyl compounds for inflammation and immune-related uses |
| AU2007227210A1 (en) | 2006-03-20 | 2007-09-27 | Synta Pharmaceuticals Corp. | Benzoimidazolyl-parazine compounds for inflammation and immune-related uses |
| AU2007230911A1 (en) | 2006-03-23 | 2007-10-04 | Synta Pharmaceuticals Corp. | Benzimidazolyl-pyridine compounds for inflammation and immune-related uses |
| US20080207641A1 (en) | 2006-11-13 | 2008-08-28 | Synta Pharmaceuticals Corp. | Cyclohexenyl-aryl compounds for inflammation and immune-related uses |
| WO2008122038A1 (en) | 2007-04-02 | 2008-10-09 | President And Fellows Of Harvard College | Regulating autophagy |
| CA2688417C (en) * | 2007-05-24 | 2017-04-25 | Calcimedica, Inc. | Calcium channel proteins and uses thereof |
| WO2009001214A2 (en) * | 2007-06-28 | 2008-12-31 | Pfizer Products Inc. | Thieno[2,3-d]pyrimidin-4(3h)-one, isoxazolo[5,4-d]pyrimidin-4(5h)-one and isothiazolo[5,4-d]pyrimidin-4(5h)-one derivatives as calcium receptor antagonists |
| WO2009011850A2 (en) * | 2007-07-16 | 2009-01-22 | Abbott Laboratories | Novel therapeutic compounds |
| US8263641B2 (en) | 2007-09-10 | 2012-09-11 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| TWI392673B (zh) | 2008-08-27 | 2013-04-11 | Calcimedica Inc | 調控細胞內鈣離子濃度之化合物 |
| JP4879240B2 (ja) | 2008-09-16 | 2012-02-22 | 株式会社リコー | 発振回路、ｄｃ−ｄｃコンバータ及び半導体装置 |
| US8524763B2 (en) | 2008-09-22 | 2013-09-03 | Calcimedica, Inc. | Inhibitors of store operated calcium release |
-
2008
- 2008-08-15 US US12/192,812 patent/US8263641B2/en not_active Expired - Fee Related
- 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 KR KR1020107007759A patent/KR101257550B1/ko not_active Expired - Fee Related
- 2008-08-15 AU AU2008299220A patent/AU2008299220B2/en not_active Ceased
- 2008-08-15 RU RU2010112967/04A patent/RU2465272C2/ru not_active IP Right Cessation
- 2008-08-15 CA CA2699157A patent/CA2699157A1/en not_active Abandoned
- 2008-08-15 JP JP2010524085A patent/JP5411141B2/ja not_active Expired - Fee Related
- 2008-08-15 WO PCT/US2008/073392 patent/WO2009035818A1/en not_active Ceased
- 2008-08-15 EP EP08798036A patent/EP2200607A4/en not_active Withdrawn
- 2008-08-15 CN CN200880115726A patent/CN101854933A/zh active Pending
-
2012
- 2012-07-19 US US13/553,726 patent/US8524765B2/en active Active
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010539083A5 (enExample) | ||
| RU2010112967A (ru) | Соединения, моделирующие внутриклеточный кальций | |
| JP2013536259A5 (enExample) | ||
| JP2013525448A5 (enExample) | ||
| JP2013525433A5 (enExample) | ||
| JP2018520161A5 (enExample) | ||
| JP2009507846A5 (enExample) | ||
| CA2797533A1 (en) | Compounds that modulate intracellular calcium | |
| JP2009530283A5 (enExample) | ||
| JP2024529839A5 (enExample) | ||
| JP2013518881A5 (enExample) | ||
| CA2797663A1 (en) | Compounds that modulate intracellular calcium | |
| JP2015514780A5 (enExample) | ||
| JP2009531292A5 (enExample) | ||
| JP2011500693A5 (enExample) | ||
| JP2008521829A5 (enExample) | ||
| JP2010513435A5 (enExample) | ||
| JP2015501847A5 (enExample) | ||
| JP2012532112A5 (enExample) | ||
| JP2017523192A5 (enExample) | ||
| RU2011108969A (ru) | Соединения, модулирующие внутриклеточный кальций | |
| JP2009084270A5 (enExample) | ||
| JP2010540602A5 (enExample) | ||
| EP0731793A1 (en) | 1,5-diphenyl pyrazole compounds for treatment of inflammation | |
| JP2006510676A5 (enExample) |