AU2008299220B2 - Compounds that modulate intracellular calcium - Google Patents
Compounds that modulate intracellular calcium Download PDFInfo
- Publication number
- AU2008299220B2 AU2008299220B2 AU2008299220A AU2008299220A AU2008299220B2 AU 2008299220 B2 AU2008299220 B2 AU 2008299220B2 AU 2008299220 A AU2008299220 A AU 2008299220A AU 2008299220 A AU2008299220 A AU 2008299220A AU 2008299220 B2 AU2008299220 B2 AU 2008299220B2
- Authority
- AU
- Australia
- Prior art keywords
- thiophene
- carboxylic acid
- chlorophenyl
- calcium
- bromophenyl
- 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.)
- Ceased
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- 150000001875 compounds Chemical class 0.000 title claims abstract 18
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052791 calcium Inorganic materials 0.000 title abstract 2
- 239000011575 calcium Substances 0.000 title abstract 2
- 230000003834 intracellular effect Effects 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 17
- 201000010099 disease Diseases 0.000 claims abstract 9
- 238000000034 method Methods 0.000 claims abstract 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims 6
- YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- -1 C -C 6 heteroalkyl Chemical group 0.000 claims 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 3
- 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
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims 1
- 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
- IFUQFGLMSDXWSZ-UHFFFAOYSA-N 2-[(3-methylbenzoyl)amino]-4-(4-methylphenyl)thiophene-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CSC(NC(=O)C=2C=C(C)C=CC=2)=C1C(O)=O IFUQFGLMSDXWSZ-UHFFFAOYSA-N 0.000 claims 1
- LWUNRVPXCBAAPY-UHFFFAOYSA-N 2-[(3-methylbenzoyl)amino]-4-[4-(trifluoromethyl)phenyl]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C=CC(=CC=2)C(F)(F)F)C(O)=O)=C1 LWUNRVPXCBAAPY-UHFFFAOYSA-N 0.000 claims 1
- FNQXPIAFGXVYBW-UHFFFAOYSA-N 2-[(3-methylbenzoyl)amino]-4-phenylthiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C=CC=CC=2)C(O)=O)=C1 FNQXPIAFGXVYBW-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
- RTVOTROUINYISJ-UHFFFAOYSA-N 2-[(4-bromobenzoyl)amino]-4-(3,4-dimethylphenyl)thiophene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(Br)=CC=2)=C1C(O)=O RTVOTROUINYISJ-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
- 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
- ZFSAIEBONYFRBD-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(2,4-dichlorophenyl)thiophene-3-carboxylic acid Chemical compound S1C=C(C=2C(=CC(Cl)=CC=2)Cl)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 ZFSAIEBONYFRBD-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
- FAPAAQCHSJJJIV-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-(3,4-dimethylphenyl)thiophene-3-carboxylic acid Chemical compound C1=C(C)C(C)=CC=C1C1=CSC(NC(=O)C=2C=CC(Cl)=CC=2)=C1C(O)=O FAPAAQCHSJJJIV-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
- PKAQUCGJDWSTGF-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]-4-phenylthiophene-3-carboxylic acid Chemical compound S1C=C(C=2C=CC=CC=2)C(C(=O)O)=C1NC(=O)C1=CC=C(Cl)C=C1 PKAQUCGJDWSTGF-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
- JQQKIAGSXSVGJF-UHFFFAOYSA-N 2-[(4-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=C(F)C=C1 JQQKIAGSXSVGJF-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
- IYBDBXSVHLLBGP-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[(3-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C(=CC(Cl)=CC=2)Cl)C(O)=O)=C1 IYBDBXSVHLLBGP-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
- AEWSOHDSAUPSPG-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-2-[(4-iodobenzoyl)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(I)C=C1 AEWSOHDSAUPSPG-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
- XKKJDZPKODPJLA-UHFFFAOYSA-N 4-(2-bromophenyl)-2-[(3-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C(=CC=CC=2)Br)C(O)=O)=C1 XKKJDZPKODPJLA-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
- OWQMPUDJVKTRBK-UHFFFAOYSA-N 4-(3,4-dimethylphenyl)-2-[(3-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C=C(C)C(C)=CC=2)C(O)=O)=C1 OWQMPUDJVKTRBK-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
- IUPFXQQDEUYVIH-UHFFFAOYSA-N 4-(3-chlorophenyl)-2-[(3-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C=C(Cl)C=CC=2)C(O)=O)=C1 IUPFXQQDEUYVIH-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
- OAIYXBQEALWRIL-UHFFFAOYSA-N 4-(4-bromophenyl)-2-[(3-methylbenzoyl)amino]thiophene-3-carboxylic acid Chemical compound CC1=CC=CC(C(=O)NC2=C(C(=CS2)C=2C=CC(Br)=CC=2)C(O)=O)=C1 OAIYXBQEALWRIL-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
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| US97116107P | 2007-09-10 | 2007-09-10 | |
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| PCT/US2008/073392 WO2009035818A1 (en) | 2007-09-10 | 2008-08-15 | Compounds that modulate intracellular calcium |
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| AU2008299220A1 AU2008299220A1 (en) | 2009-03-19 |
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|---|---|---|---|---|
| WO2008106731A1 (en) | 2007-03-05 | 2008-09-12 | The University Of Queensland | A target for breast cancer therapy and/or diagnosis |
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| 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 |
| US20090069288A1 (en) * | 2007-07-16 | 2009-03-12 | Breinlinger Eric C | Novel therapeutic compounds |
| CN101854933A (zh) | 2007-09-10 | 2010-10-06 | 钙医学公司 | 调节细胞内钙的化合物 |
| US8389567B2 (en) | 2007-12-12 | 2013-03-05 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| AU2009288245B2 (en) | 2008-08-27 | 2012-12-20 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| 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 |
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2008
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- 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 WO PCT/US2008/073392 patent/WO2009035818A1/en not_active Ceased
- 2008-08-15 CA CA2699157A patent/CA2699157A1/en not_active Abandoned
- 2008-08-15 EP EP08798036A patent/EP2200607A4/en not_active Withdrawn
- 2008-08-15 AU AU2008299220A patent/AU2008299220B2/en not_active Ceased
- 2008-08-15 US US12/192,812 patent/US8263641B2/en not_active Expired - Fee Related
- 2008-08-15 RU RU2010112967/04A patent/RU2465272C2/ru not_active IP Right Cessation
- 2008-08-15 JP JP2010524085A patent/JP5411141B2/ja not_active Expired - Fee Related
- 2008-08-15 MX MX2010002712A patent/MX2010002712A/es not_active Application Discontinuation
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO1998054116A1 (en) * | 1997-05-28 | 1998-12-03 | Cadus Pharmaceutical Corporation | Synthesis and use of thiophene- and pyrrole-based heteroaromatic compounds |
| US20040068120A1 (en) * | 2000-12-12 | 2004-04-08 | Stefan Peukert | Arylated furan- and thiophenecarboxamides, processes for their preparation, their use as medicaments, and pharmaceutical preparations comprising them |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090137659A1 (en) | 2009-05-28 |
| KR101257550B1 (ko) | 2013-04-24 |
| US8524765B2 (en) | 2013-09-03 |
| CA2699157A1 (en) | 2009-03-19 |
| US20120289587A1 (en) | 2012-11-15 |
| EP2200607A4 (en) | 2012-02-22 |
| AU2008299220A1 (en) | 2009-03-19 |
| JP2010539083A (ja) | 2010-12-16 |
| WO2009035818A8 (en) | 2009-05-14 |
| RU2465272C2 (ru) | 2012-10-27 |
| EP2200607A1 (en) | 2010-06-30 |
| KR20100061836A (ko) | 2010-06-09 |
| CN101854933A (zh) | 2010-10-06 |
| BRPI0816326A2 (pt) | 2015-03-24 |
| WO2009035818A1 (en) | 2009-03-19 |
| US8263641B2 (en) | 2012-09-11 |
| RU2010112967A (ru) | 2011-10-20 |
| MX2010002712A (es) | 2010-06-09 |
| JP5411141B2 (ja) | 2014-02-12 |
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