HRP20100297T1 - Derivati n-(heteroaril)-1h-indol-2-karboksamida i njihova upotreba kao ligandi vaniloidnog receptora trpv1 - Google Patents
Derivati n-(heteroaril)-1h-indol-2-karboksamida i njihova upotreba kao ligandi vaniloidnog receptora trpv1 Download PDFInfo
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- HRP20100297T1 HRP20100297T1 HR20100297T HRP20100297T HRP20100297T1 HR P20100297 T1 HRP20100297 T1 HR P20100297T1 HR 20100297 T HR20100297 T HR 20100297T HR P20100297 T HRP20100297 T HR P20100297T HR P20100297 T1 HRP20100297 T1 HR P20100297T1
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- Prior art keywords
- indole
- carboxamide
- methyl
- fluorophenyl
- cycloalkyl
- Prior art date
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- 108010025083 TRPV1 receptor Proteins 0.000 title claims 2
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- -1 C1-C6-fluoroalkoxy Chemical group 0.000 claims abstract 26
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 24
- 125000003118 aryl group Chemical group 0.000 claims abstract 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 12
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 10
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 239000012453 solvate Substances 0.000 claims abstract 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000002253 acid Substances 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 4
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims abstract 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 125000001041 indolyl group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 125000004149 thio group Chemical group *S* 0.000 claims abstract 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims abstract 2
- 208000002193 Pain Diseases 0.000 claims 5
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- 210000000278 spinal cord Anatomy 0.000 claims 3
- 206010020853 Hypertonic bladder Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 210000004556 brain Anatomy 0.000 claims 2
- 125000005434 dihydrobenzoxazinyl group Chemical group O1N(CCC2=C1C=CC=C2)* 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000005493 quinolyl group Chemical group 0.000 claims 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 2
- 238000010992 reflux Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 208000014001 urinary system disease Diseases 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- PKTVXRVTARBIEP-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(1,2,3,4-tetrahydroquinolin-7-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3NCCCC3=CC=2)C(F)(F)F)=C1 PKTVXRVTARBIEP-UHFFFAOYSA-N 0.000 claims 1
- YHZXCLSRWNHIQL-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(1-methyl-3,4-dihydro-2h-quinolin-7-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C1=C2N(C)CCCC2=CC=C1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 YHZXCLSRWNHIQL-UHFFFAOYSA-N 0.000 claims 1
- KNIPJAJCTMPHJK-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(1-methylbenzimidazol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2N(C)C=NC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 KNIPJAJCTMPHJK-UHFFFAOYSA-N 0.000 claims 1
- UPUYSHGQTIWVQR-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(1-methylindazol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 UPUYSHGQTIWVQR-UHFFFAOYSA-N 0.000 claims 1
- QZJKKKZIUXOYJJ-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(1-methylsulfonyl-2,3-dihydroindol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2N(S(=O)(=O)C)CCC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 QZJKKKZIUXOYJJ-UHFFFAOYSA-N 0.000 claims 1
- LOYDYOADOAOHON-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(2-methyl-1,3-benzothiazol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 LOYDYOADOAOHON-UHFFFAOYSA-N 0.000 claims 1
- PNTBVZDVNSUOCY-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(2-methyl-1,3-benzoxazol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2OC(C)=NC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 PNTBVZDVNSUOCY-UHFFFAOYSA-N 0.000 claims 1
- LASLMYWQAXQRKI-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(2-oxo-1,3-dihydroindol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3CC(=O)NC3=CC=2)C(F)(F)F)=C1 LASLMYWQAXQRKI-UHFFFAOYSA-N 0.000 claims 1
- LRJIWCORZWGFKK-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(2-oxo-3,4-dihydro-1h-quinolin-7-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3NC(=O)CCC3=CC=2)C(F)(F)F)=C1 LRJIWCORZWGFKK-UHFFFAOYSA-N 0.000 claims 1
- OTDYJCLPYGVKCH-UHFFFAOYSA-N 1-[(3-fluorophenyl)methyl]-n-(2-phenyl-1,3-benzoxazol-5-yl)-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3N=C(OC3=CC=2)C=2C=CC=CC=2)C(F)(F)F)=C1 OTDYJCLPYGVKCH-UHFFFAOYSA-N 0.000 claims 1
- FFQAAFSSHWHTPG-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-6-methoxy-n-(2-oxo-3,4-dihydro-1h-quinolin-7-yl)indole-2-carboxamide Chemical compound C12=CC(OC)=CC=C2C=C(C(=O)NC=2C=C3NC(=O)CCC3=CC=2)N1CC1=CC=C(F)C=C1 FFQAAFSSHWHTPG-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- SKUBEBDZVXNHGO-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1,2,3,4-tetrahydroquinolin-7-yl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3NCCCC3=CC=2)=C1 SKUBEBDZVXNHGO-UHFFFAOYSA-N 0.000 claims 1
- BCGWWDBCBPVAFE-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methyl-2,3-dihydroindol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2N(C)CCC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 BCGWWDBCBPVAFE-UHFFFAOYSA-N 0.000 claims 1
- KVHSBECCXMNHDG-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methyl-3,4-dihydro-2h-quinolin-7-yl)indole-2-carboxamide Chemical compound C1=C2N(C)CCCC2=CC=C1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 KVHSBECCXMNHDG-UHFFFAOYSA-N 0.000 claims 1
- IWPXZDKDXNRUKF-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methylbenzimidazol-4-yl)indole-2-carboxamide Chemical compound C1=CC=C2N(C)C=NC2=C1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 IWPXZDKDXNRUKF-UHFFFAOYSA-N 0.000 claims 1
- YFIWGWQFZWMCNH-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methylbenzimidazol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2N(C)C=NC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 YFIWGWQFZWMCNH-UHFFFAOYSA-N 0.000 claims 1
- QIEMLIYGKUSJPQ-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methylindazol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2N(C)N=CC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 QIEMLIYGKUSJPQ-UHFFFAOYSA-N 0.000 claims 1
- ZMZNZKIJBLYCOI-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(1-methylsulfonyl-2,3-dihydroindol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2N(S(=O)(=O)C)CCC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 ZMZNZKIJBLYCOI-UHFFFAOYSA-N 0.000 claims 1
- WYYNNFBSXVXTEV-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(2-methyl-1,3-benzothiazol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2SC(C)=NC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 WYYNNFBSXVXTEV-UHFFFAOYSA-N 0.000 claims 1
- CQVQOEOAYMDMSO-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(2-methyl-1,3-benzoxazol-5-yl)indole-2-carboxamide Chemical compound C=1C=C2OC(C)=NC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 CQVQOEOAYMDMSO-UHFFFAOYSA-N 0.000 claims 1
- ANMMGLXFKACBNC-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(2-methyl-3h-benzimidazol-5-yl)indole-2-carboxamide Chemical compound C1=C2NC(C)=NC2=CC=C1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 ANMMGLXFKACBNC-UHFFFAOYSA-N 0.000 claims 1
- DWFGZKZPINRQST-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(2-oxo-1,3-dihydroindol-5-yl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3CC(=O)NC3=CC=2)=C1 DWFGZKZPINRQST-UHFFFAOYSA-N 0.000 claims 1
- YRELYMJXQXTQJY-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(2-oxo-3,4-dihydro-1h-quinolin-7-yl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3NC(=O)CCC3=CC=2)=C1 YRELYMJXQXTQJY-UHFFFAOYSA-N 0.000 claims 1
- WQXUXIAZFFVURE-UHFFFAOYSA-N 5-fluoro-1-[(3-fluorophenyl)methyl]-n-(3-methylbenzimidazol-5-yl)indole-2-carboxamide Chemical compound C1=C2N(C)C=NC2=CC=C1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 WQXUXIAZFFVURE-UHFFFAOYSA-N 0.000 claims 1
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- QVKZVBUGTJUXEZ-UHFFFAOYSA-N n-(1,2,3,4-tetrahydroquinolin-7-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3NCCCC3=CC=2)=C1 QVKZVBUGTJUXEZ-UHFFFAOYSA-N 0.000 claims 1
- SSPLBGRGFOMDTI-UHFFFAOYSA-N n-(1,2,3,4-tetrahydroquinolin-8-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=3NCCCC=3C=CC=2)=C1 SSPLBGRGFOMDTI-UHFFFAOYSA-N 0.000 claims 1
- APWLFRWRGUPKLP-UHFFFAOYSA-N n-(1,2-dimethylbenzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound C=1C=C2N(C)C(C)=NC2=CC=1NC(=O)C1=CC2=CC(F)=CC=C2N1CC1=CC=CC(F)=C1 APWLFRWRGUPKLP-UHFFFAOYSA-N 0.000 claims 1
- VKKYTNPZCZTWKG-UHFFFAOYSA-N n-(1,3-benzothiazol-6-yl)-1-[(3-fluorophenyl)methyl]-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3SC=NC3=CC=2)C(F)(F)F)=C1 VKKYTNPZCZTWKG-UHFFFAOYSA-N 0.000 claims 1
- HHWCKXOPWGRBBD-UHFFFAOYSA-N n-(1,3-benzothiazol-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3SC=NC3=CC=2)=C1 HHWCKXOPWGRBBD-UHFFFAOYSA-N 0.000 claims 1
- JTGULXJXNPJQTN-UHFFFAOYSA-N n-(1,3-benzoxazol-5-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3N=COC3=CC=2)=C1 JTGULXJXNPJQTN-UHFFFAOYSA-N 0.000 claims 1
- PLMLCZNZBAGCPU-UHFFFAOYSA-N n-(1-benzofuran-5-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3C=COC3=CC=2)=C1 PLMLCZNZBAGCPU-UHFFFAOYSA-N 0.000 claims 1
- MYBMLGBSCSGNRT-UHFFFAOYSA-N n-(1-benzofuran-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3C=COC3=CC=2)=C1 MYBMLGBSCSGNRT-UHFFFAOYSA-N 0.000 claims 1
- BDLZNYYUEFSOHW-UHFFFAOYSA-N n-(1-methyl-2,3-dihydroindol-5-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound C=1C=C2N(C)CCC2=CC=1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(C(F)(F)F)=C1 BDLZNYYUEFSOHW-UHFFFAOYSA-N 0.000 claims 1
- LIFUXCTWVXFXOP-UHFFFAOYSA-N n-(1-methyl-3,4-dihydro-2h-quinolin-7-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound C1=C2N(C)CCCC2=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(C(F)(F)F)=C1 LIFUXCTWVXFXOP-UHFFFAOYSA-N 0.000 claims 1
- OGRMTXIJQFZQRX-UHFFFAOYSA-N n-(2-ethyl-1,3-benzoxazol-5-yl)-1-[(3-fluorophenyl)methyl]-5-(trifluoromethyl)indole-2-carboxamide Chemical compound C=1C=C2OC(CC)=NC2=CC=1NC(=O)C1=CC2=CC(C(F)(F)F)=CC=C2N1CC1=CC=CC(F)=C1 OGRMTXIJQFZQRX-UHFFFAOYSA-N 0.000 claims 1
- RYMKAPFJXKYNKN-UHFFFAOYSA-N n-(2-methyl-1,3-benzoxazol-5-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound C=1C=C2OC(C)=NC2=CC=1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(C(F)(F)F)=C1 RYMKAPFJXKYNKN-UHFFFAOYSA-N 0.000 claims 1
- GPQAUCAYFVRDRE-UHFFFAOYSA-N n-(2-oxo-3,4-dihydro-1h-quinolin-7-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3NC(=O)CCC3=CC=2)=C1 GPQAUCAYFVRDRE-UHFFFAOYSA-N 0.000 claims 1
- LKKIJJCLXBJABH-UHFFFAOYSA-N n-(2h-benzotriazol-5-yl)-1-[(3-fluorophenyl)methyl]-5-(trifluoromethyl)indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=C2C(=O)NC=2C=C3N=NNC3=CC=2)C(F)(F)F)=C1 LKKIJJCLXBJABH-UHFFFAOYSA-N 0.000 claims 1
- GODINVZOTFPFLA-UHFFFAOYSA-N n-(2h-benzotriazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3N=NNC3=CC=2)=C1 GODINVZOTFPFLA-UHFFFAOYSA-N 0.000 claims 1
- FPGZVBQUTNPHDD-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,2-benzoxazin-6-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3CCNOC3=CC=2)=C1 FPGZVBQUTNPHDD-UHFFFAOYSA-N 0.000 claims 1
- ATXITNOOWRUDFS-UHFFFAOYSA-N n-(3,4-dihydro-2h-1,2-benzoxazin-6-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3CCNOC3=CC=2)=C1 ATXITNOOWRUDFS-UHFFFAOYSA-N 0.000 claims 1
- GPCNHCRJKLJCEL-UHFFFAOYSA-N n-(3-oxo-4h-1,2-benzoxazin-7-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(N2C3=CC=CC=C3C=C2C(=O)NC=2C=C3ONC(=O)CC3=CC=2)=C1 GPCNHCRJKLJCEL-UHFFFAOYSA-N 0.000 claims 1
- KPJQIABFPZABTN-UHFFFAOYSA-N n-(3h-benzimidazol-5-yl)-5-fluoro-1-[(3-fluorophenyl)methyl]indole-2-carboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(F)C=C3C=C2C(=O)NC=2C=C3NC=NC3=CC=2)=C1 KPJQIABFPZABTN-UHFFFAOYSA-N 0.000 claims 1
- BZZRHPSCFUOADT-UHFFFAOYSA-N n-(4-methyl-3-oxo-4h-1,2-benzoxazin-6-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound C1=C2C(C)C(=O)NOC2=CC=C1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(C(F)(F)F)=C1 BZZRHPSCFUOADT-UHFFFAOYSA-N 0.000 claims 1
- CZEMZMXRUSSLSH-UHFFFAOYSA-N n-(4-methyl-3-oxo-4h-1,2-benzoxazin-7-yl)-1-[3-(trifluoromethyl)phenyl]indole-2-carboxamide Chemical compound C=1C=C2C(C)C(=O)NOC2=CC=1NC(=O)C1=CC2=CC=CC=C2N1C1=CC=CC(C(F)(F)F)=C1 CZEMZMXRUSSLSH-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 230000002981 neuropathic effect Effects 0.000 claims 1
- 208000020629 overactive bladder Diseases 0.000 claims 1
- 230000001575 pathological effect Effects 0.000 claims 1
- 210000004197 pelvis Anatomy 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 230000000552 rheumatic effect Effects 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 208000004371 toothache Diseases 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 claims 1
- 210000003905 vulva Anatomy 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Virology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Biotechnology (AREA)
- Ophthalmology & Optometry (AREA)
- Rheumatology (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0550068A FR2880625B1 (fr) | 2005-01-07 | 2005-01-07 | Derives de n-(heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
PCT/FR2006/000008 WO2006072736A1 (fr) | 2005-01-07 | 2006-01-04 | DERIVES DE N- (HETEROARYL) -1H-IND0LE-2-CARB0XAMIDΞS ET LEUR UTILISATION COMME LIGANDS DU RECEPTEUR VANILLOIDE TRPVl |
Publications (1)
Publication Number | Publication Date |
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HRP20100297T1 true HRP20100297T1 (hr) | 2010-07-31 |
Family
ID=34955041
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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HR20100297T HRP20100297T1 (hr) | 2005-01-07 | 2010-05-26 | Derivati n-(heteroaril)-1h-indol-2-karboksamida i njihova upotreba kao ligandi vaniloidnog receptora trpv1 |
Country Status (36)
Country | Link |
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US (2) | US7407950B2 (pt) |
EP (1) | EP1841737B1 (pt) |
JP (1) | JP5242167B2 (pt) |
KR (1) | KR101288698B1 (pt) |
CN (1) | CN101115718B (pt) |
AR (1) | AR052450A1 (pt) |
AT (1) | ATE460397T1 (pt) |
AU (1) | AU2006204405B2 (pt) |
BR (1) | BRPI0606472A2 (pt) |
CA (1) | CA2594418C (pt) |
CR (1) | CR9210A (pt) |
CY (1) | CY1110647T1 (pt) |
DE (1) | DE602006012802D1 (pt) |
DK (1) | DK1841737T3 (pt) |
EA (1) | EA013264B1 (pt) |
ES (1) | ES2342318T3 (pt) |
FR (1) | FR2880625B1 (pt) |
HK (1) | HK1117506A1 (pt) |
HR (1) | HRP20100297T1 (pt) |
IL (1) | IL184268A (pt) |
MA (1) | MA29239B1 (pt) |
MX (1) | MX2007008308A (pt) |
MY (1) | MY145932A (pt) |
NO (1) | NO20073811L (pt) |
NZ (1) | NZ556318A (pt) |
PE (1) | PE20061019A1 (pt) |
PL (1) | PL1841737T3 (pt) |
PT (1) | PT1841737E (pt) |
RS (1) | RS51358B (pt) |
SI (1) | SI1841737T1 (pt) |
TN (1) | TNSN07253A1 (pt) |
TW (1) | TWI367879B (pt) |
UA (1) | UA93668C2 (pt) |
UY (1) | UY29327A1 (pt) |
WO (1) | WO2006072736A1 (pt) |
ZA (1) | ZA200705548B (pt) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2874015B1 (fr) * | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
FR2888847B1 (fr) | 2005-07-22 | 2007-08-31 | Sanofi Aventis Sa | Derives de n-(heteriaryl)-1-heteorarylalkyl-1h-indole-2- carboxamides, leur preparation et application en therapeutique |
FR2903985B1 (fr) | 2006-07-24 | 2008-09-05 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
FR2904316B1 (fr) * | 2006-07-31 | 2008-09-05 | Sanofi Aventis Sa | Derives de n-(amino-heteroaryl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique. |
JP5746471B2 (ja) * | 2006-12-15 | 2015-07-08 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプJanssen Pharmaceutica Naamloze Vennootschap | ベンゾイミダゾール系trpv1阻害剤 |
FR2911604B1 (fr) | 2007-01-19 | 2009-04-17 | Sanofi Aventis Sa | Derives de n-(heteroaryl-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
EA020332B1 (ru) * | 2007-08-10 | 2014-10-30 | Х. Лундбекк А/С | Аналоги гетероариламидов |
JP2011509296A (ja) * | 2008-01-09 | 2011-03-24 | レノビス, インコーポレイテッド | イオンチャネルリガンドとしてのアミド誘導体およびそれを使用する薬学的組成物および方法 |
FR2926554B1 (fr) * | 2008-01-22 | 2010-03-12 | Sanofi Aventis | Derives de carboxamides azabicycliques, leur preparation et leur application en therapeutique |
FR2926555B1 (fr) | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives bicycliques de carboxamides azabicycliques, leur preparation et leur application en therapeutique |
FR2926556B1 (fr) * | 2008-01-22 | 2010-02-19 | Sanofi Aventis | Derives de carboxamides n-azabicycliques, leur preparation et leur application en therapeutique |
EP3295794A1 (en) | 2010-07-27 | 2018-03-21 | Flex Pharma, Inc. | Methods and compositions for preventing and relieving muscle cramps and for recovery from neuromuscular irritability and fatigue following exercise |
KR101293384B1 (ko) * | 2010-10-13 | 2013-08-05 | 주식회사 대웅제약 | 신규 피리딜 벤조옥사진 유도체, 이를 포함하는 약학 조성물 및 이의 용도 |
EP3570861A4 (en) | 2017-01-23 | 2020-11-18 | Flex Pharma, Inc. | COMPOSITIONS AND PROCEDURES EFFECTING SPORTING PERFORMANCE |
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US5846990A (en) * | 1995-07-24 | 1998-12-08 | Bristol-Myers Squibb Co. | Substituted biphenyl isoxazole sulfonamides |
CA2245587C (en) * | 1996-02-13 | 2008-12-30 | Abbott Laboratories | Novel benzo-1,3-dioxolyl- and benzofuranyl substituted pyrrolidine derivatives as endothelin antagonists |
SK281737B6 (sk) * | 1996-04-19 | 2001-07-10 | American Home Products Corporation | 2-fenylindolové zlúčeniny, farmaceutický prostriedok s ich obsahom a ich použitie |
TR200000993T2 (tr) * | 1997-08-04 | 2000-12-21 | Abbott Laboratories | Endotelin antagonistleri. |
UA68365C2 (en) * | 1997-11-06 | 2004-08-16 | Wyeth Corp | Peroral contraception by combination of anti-estrogen and progestin |
DK1042287T3 (da) * | 1997-12-24 | 2005-08-15 | Aventis Pharma Gmbh | Indolderivater som inhibitorer af faktor Xa |
BR9911040A (pt) * | 1998-05-15 | 2001-02-13 | American Home Prod | 2-fenil-1-[4-(2-aminoetóxi)-benzil]-indol em combinação com estrogêneos |
CO5180550A1 (es) * | 1999-04-19 | 2002-07-30 | Smithkline Beecham Corp | Inhibidores de fab i |
AR030064A1 (es) * | 2000-07-06 | 2003-08-13 | Wyeth Corp | Metodos para inhibir los efectos uterotroficos de los agentes estrogenicos |
EP1314733A1 (en) * | 2001-11-22 | 2003-05-28 | Aventis Pharma Deutschland GmbH | Indole-2-carboxamides as factor Xa inhibitors |
ES2316777T3 (es) * | 2002-02-15 | 2009-04-16 | Glaxo Group Limited | Moduladores de receptores vainilloides. |
CA2510811A1 (en) * | 2002-12-20 | 2004-07-08 | Bayer Healthcare Ag | Use of substituted 2,5-diamidoindoles for the treatment of urological diseases |
ATE450533T1 (de) * | 2003-02-14 | 2009-12-15 | Glaxo Group Ltd | Carboxamidderivate |
AR045979A1 (es) * | 2003-04-28 | 2005-11-23 | Astrazeneca Ab | Amidas heterociclicas |
EP1628661A2 (en) * | 2003-06-05 | 2006-03-01 | Vertex Pharmaceuticals Incorporated | Modulators of vr1 receptor |
US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
FR2874015B1 (fr) * | 2004-08-05 | 2006-09-15 | Sanofi Synthelabo | Derives de n-(1h-indolyl)-1h-indole-2-carboxamides, leur preparation et leur application en therapeutique |
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