NO329682B1 - N-fenylarylsulfonamidforbindelse, og antagonist av EP1 reseptor og farmasoytisk preparat omfattende forbindelsen som aktiv bestanddel - Google Patents
N-fenylarylsulfonamidforbindelse, og antagonist av EP1 reseptor og farmasoytisk preparat omfattende forbindelsen som aktiv bestanddel Download PDFInfo
- Publication number
- NO329682B1 NO329682B1 NO20034007A NO20034007A NO329682B1 NO 329682 B1 NO329682 B1 NO 329682B1 NO 20034007 A NO20034007 A NO 20034007A NO 20034007 A NO20034007 A NO 20034007A NO 329682 B1 NO329682 B1 NO 329682B1
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- Norway
- Prior art keywords
- methyl
- amino
- isobutyl
- acid
- isopropyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 139
- 239000005557 antagonist Substances 0.000 title claims description 18
- 239000004480 active ingredient Substances 0.000 title claims description 8
- 101150058615 Ptger1 gene Proteins 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 5-methyl-2-furyl Chemical group 0.000 claims abstract description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 102000005962 receptors Human genes 0.000 claims abstract description 15
- 108020003175 receptors Proteins 0.000 claims abstract description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 11
- 230000027939 micturition Effects 0.000 claims abstract description 11
- 206010036018 Pollakiuria Diseases 0.000 claims abstract description 7
- 102000008866 Prostaglandin E receptors Human genes 0.000 claims abstract description 7
- 108010088540 Prostaglandin E receptors Proteins 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 208000011580 syndromic disease Diseases 0.000 claims abstract description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 220
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 153
- 229940124530 sulfonamide Drugs 0.000 claims description 118
- 239000002253 acid Substances 0.000 claims description 97
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 96
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 90
- 239000005711 Benzoic acid Substances 0.000 claims description 59
- 235000010233 benzoic acid Nutrition 0.000 claims description 45
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 39
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims description 39
- 229930016911 cinnamic acid Natural products 0.000 claims description 39
- 235000013985 cinnamic acid Nutrition 0.000 claims description 39
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 16
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 11
- 231100000252 nontoxic Toxicity 0.000 claims description 10
- 230000003000 nontoxic effect Effects 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 206010037660 Pyrexia Diseases 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 6
- 230000006698 induction Effects 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 230000027950 fever generation Effects 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- VBPYYHZBHWQNKY-UHFFFAOYSA-N 3-[3-methyl-4-[[2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-5-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC=C(C(F)(F)F)C=C1OCC1=CC=C(C=CC(O)=O)C=C1C VBPYYHZBHWQNKY-UHFFFAOYSA-N 0.000 claims description 3
- KCZHYRSBYSISRU-UHFFFAOYSA-N 3-[3-methyl-4-[[3-[(5-methylfuran-2-yl)sulfonyl-(2-methylpropyl)amino]naphthalen-2-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(CC(C)C)C1=CC2=CC=CC=C2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C KCZHYRSBYSISRU-UHFFFAOYSA-N 0.000 claims description 3
- DDECXYJJPKIXEY-UHFFFAOYSA-N 3-[3-methyl-4-[[6-[propan-2-yl(1,3-thiazol-2-ylsulfonyl)amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C=CSC=1S(=O)(=O)N(C(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C DDECXYJJPKIXEY-UHFFFAOYSA-N 0.000 claims description 3
- SLHKHBZSGXVQFX-UHFFFAOYSA-N 3-[4-[[2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-5-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC=C(C(F)(F)F)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 SLHKHBZSGXVQFX-UHFFFAOYSA-N 0.000 claims description 3
- LGSYGWHHUFLCLI-UHFFFAOYSA-N 3-[4-[[6-[(4-methyl-1,3-thiazol-2-yl)sulfonyl-propan-2-ylamino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(C(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1 LGSYGWHHUFLCLI-UHFFFAOYSA-N 0.000 claims description 3
- LPJLBUOIRQJTAH-UHFFFAOYSA-N 3-chloro-4-[[4-chloro-5-methyl-2-[propan-2-yl(pyridin-2-ylsulfonyl)amino]phenoxy]methyl]benzoic acid Chemical compound C=1C=CC=NC=1S(=O)(=O)N(C(C)C)C1=CC(Cl)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1Cl LPJLBUOIRQJTAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- PAUAESUQPKSFEF-UHFFFAOYSA-N 4-[[2-[propan-2-yl(1,3-thiazol-2-ylsulfonyl)amino]-5-(trifluoromethyl)phenoxy]methyl]benzoic acid Chemical compound N=1C=CSC=1S(=O)(=O)N(C(C)C)C1=CC=C(C(F)(F)F)C=C1OCC1=CC=C(C(O)=O)C=C1 PAUAESUQPKSFEF-UHFFFAOYSA-N 0.000 claims description 3
- JQCOUWNBDQATQD-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[(4-methyl-1,3-thiazol-2-yl)sulfonyl-propylamino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CCC)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C JQCOUWNBDQATQD-UHFFFAOYSA-N 0.000 claims description 3
- HKYZMEKVLDVTFB-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[(5-methylfuran-2-yl)sulfonyl-prop-2-enylamino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound O1C(C)=CC=C1S(=O)(=O)N(CC=C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C HKYZMEKVLDVTFB-UHFFFAOYSA-N 0.000 claims description 3
- AEANKAMGBZVZMQ-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[2-methylpropyl(pyridin-2-ylsulfonyl)amino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound C=1C=CC=NC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C AEANKAMGBZVZMQ-UHFFFAOYSA-N 0.000 claims description 3
- TWMVCGIHQSAHEM-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[2-methylpropyl(pyridin-3-ylsulfonyl)amino]phenoxy]methyl]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1COC1=CC(C)=C(C)C=C1N(CC(C)C)S(=O)(=O)C1=CC=CN=C1 TWMVCGIHQSAHEM-UHFFFAOYSA-N 0.000 claims description 3
- HUSKYHHXCMIKGS-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C HUSKYHHXCMIKGS-UHFFFAOYSA-N 0.000 claims description 3
- PDIHXAWISZWDRS-UHFFFAOYSA-N 4-[[4,5-dimethyl-2-[methyl-(5-methylfuran-2-yl)sulfonylamino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C PDIHXAWISZWDRS-UHFFFAOYSA-N 0.000 claims description 3
- BIPADBRDQDDYLO-UHFFFAOYSA-N 4-[[4-chloro-5-methyl-2-[2-methylprop-2-enyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]phenoxy]methyl]-3-methylbenzoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(=C)C)C1=CC(Cl)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1C BIPADBRDQDDYLO-UHFFFAOYSA-N 0.000 claims description 3
- KBPARJNQCKKDJC-UHFFFAOYSA-N 4-[[6-[(2-hydroxy-2-methylpropyl)-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]benzoic acid Chemical compound CC1=CSC(S(=O)(=O)N(CC(C)(C)O)C=2C(=CC=3CCCC=3C=2)OCC=2C=CC(=CC=2)C(O)=O)=N1 KBPARJNQCKKDJC-UHFFFAOYSA-N 0.000 claims description 3
- ZZQVRLPENZFYLY-UHFFFAOYSA-N 4-[[6-[(5-methylfuran-2-yl)sulfonyl-propan-2-ylamino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]benzoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(C(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C(O)=O)C=C1 ZZQVRLPENZFYLY-UHFFFAOYSA-N 0.000 claims description 3
- CUYJEGYERUEYMP-UHFFFAOYSA-N 4-[[6-[methyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]benzoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C(O)=O)C=C1 CUYJEGYERUEYMP-UHFFFAOYSA-N 0.000 claims description 3
- 241001237754 Algia Species 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- MQSJQFQDEHNUMO-UHFFFAOYSA-N 3-[3-methyl-4-[[6-[(4-methyl-1,3-thiazol-2-yl)sulfonyl-propylamino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CCC)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C MQSJQFQDEHNUMO-UHFFFAOYSA-N 0.000 claims description 2
- NARMEKHGSVNOBX-UHFFFAOYSA-N 3-[3-methyl-4-[[6-[2-methylprop-2-enyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(=C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C NARMEKHGSVNOBX-UHFFFAOYSA-N 0.000 claims description 2
- TXABTIGJIGZLCS-UHFFFAOYSA-N 3-[3-methyl-4-[[6-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C TXABTIGJIGZLCS-UHFFFAOYSA-N 0.000 claims description 2
- AYYHDPOKMMBQEM-UHFFFAOYSA-N 3-[3-methyl-4-[[6-[methyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1C AYYHDPOKMMBQEM-UHFFFAOYSA-N 0.000 claims description 2
- POUBSLPBNFGQAO-UHFFFAOYSA-N 3-[4-[[2-[2-methylpropyl(pyridin-2-ylsulfonyl)amino]-5-(trifluoromethyl)phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound C=1C=CC=NC=1S(=O)(=O)N(CC(C)C)C1=CC=C(C(F)(F)F)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 POUBSLPBNFGQAO-UHFFFAOYSA-N 0.000 claims description 2
- LBWJZHUGNUPISB-UHFFFAOYSA-N 3-[4-[[3-[(4-methyl-1,3-thiazol-2-yl)sulfonyl-propan-2-ylamino]naphthalen-2-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(C(C)C)C1=CC2=CC=CC=C2C=C1OCC1=CC=C(C=CC(O)=O)C=C1 LBWJZHUGNUPISB-UHFFFAOYSA-N 0.000 claims description 2
- OOKCHIGXDLJTJK-UHFFFAOYSA-N 3-[4-[[3-[(5-methylfuran-2-yl)sulfonyl-propan-2-ylamino]naphthalen-2-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(C(C)C)C1=CC2=CC=CC=C2C=C1OCC1=CC=C(C=CC(O)=O)C=C1 OOKCHIGXDLJTJK-UHFFFAOYSA-N 0.000 claims description 2
- MAGNVKOIELHLCE-UHFFFAOYSA-N 3-[4-[[4,5-dimethyl-2-[(5-methylfuran-2-yl)sulfonyl-(2-methylpropyl)amino]phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 MAGNVKOIELHLCE-UHFFFAOYSA-N 0.000 claims description 2
- STDLEQZHOPZMTF-UHFFFAOYSA-N 3-[4-[[4,5-dimethyl-2-[2-methylpropyl(pyridin-2-ylsulfonyl)amino]phenoxy]methyl]-3-methylphenyl]prop-2-enoic acid Chemical compound C=1C=CC=NC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C=CC(O)=O)C=C1C STDLEQZHOPZMTF-UHFFFAOYSA-N 0.000 claims description 2
- ILTMQNRYNXMLNS-UHFFFAOYSA-N 3-[4-[[4,5-dimethyl-2-[2-methylpropyl(pyridin-3-ylsulfonyl)amino]phenoxy]methyl]-3-methylphenyl]prop-2-enoic acid Chemical compound C=1C=CN=CC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C=CC(O)=O)C=C1C ILTMQNRYNXMLNS-UHFFFAOYSA-N 0.000 claims description 2
- XYDIYHFBOGBMQA-UHFFFAOYSA-N 3-[4-[[4,5-dimethyl-2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]phenoxy]methyl]-3-methoxyphenyl]prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1COC1=CC(C)=C(C)C=C1N(CC(C)C)S(=O)(=O)C1=NC(C)=CS1 XYDIYHFBOGBMQA-UHFFFAOYSA-N 0.000 claims description 2
- ACRRKHDCOYVBNO-UHFFFAOYSA-N 3-[4-[[4,5-dimethyl-2-[propan-2-yl(1,3-thiazol-2-ylsulfonyl)amino]phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound N=1C=CSC=1S(=O)(=O)N(C(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 ACRRKHDCOYVBNO-UHFFFAOYSA-N 0.000 claims description 2
- YVBMIUFKFRJIKX-UHFFFAOYSA-N 3-[4-[[4-chloro-5-methyl-2-[2-methylpropyl(pyridin-3-ylsulfonyl)amino]phenoxy]methyl]-3-methylphenyl]prop-2-enoic acid Chemical compound C=1C=CN=CC=1S(=O)(=O)N(CC(C)C)C1=CC(Cl)=C(C)C=C1OCC1=CC=C(C=CC(O)=O)C=C1C YVBMIUFKFRJIKX-UHFFFAOYSA-N 0.000 claims description 2
- QLYHJUNLCINBQT-UHFFFAOYSA-N 3-[4-[[5-chloro-4-methyl-2-[(5-methylfuran-2-yl)sulfonyl-(2-methylpropyl)amino]phenoxy]methyl]-3-methylphenyl]prop-2-enoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(Cl)C=C1OCC1=CC=C(C=CC(O)=O)C=C1C QLYHJUNLCINBQT-UHFFFAOYSA-N 0.000 claims description 2
- MOIRWZLTLCHZFQ-UHFFFAOYSA-N 3-[4-[[5-chloro-4-methyl-2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(Cl)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 MOIRWZLTLCHZFQ-UHFFFAOYSA-N 0.000 claims description 2
- BHVSBVVACASXJO-UHFFFAOYSA-N 3-[4-[[5-chloro-4-methyl-2-[propan-2-yl(pyridin-2-ylsulfonyl)amino]phenoxy]methyl]phenyl]prop-2-enoic acid Chemical compound C=1C=CC=NC=1S(=O)(=O)N(C(C)C)C1=CC(C)=C(Cl)C=C1OCC1=CC=C(C=CC(O)=O)C=C1 BHVSBVVACASXJO-UHFFFAOYSA-N 0.000 claims description 2
- YLXSHCBLGREHCG-UHFFFAOYSA-N 3-[4-[[6-[propan-2-yl(1,3-thiazol-2-ylsulfonyl)amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoic acid Chemical compound N=1C=CSC=1S(=O)(=O)N(C(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC(O)=O)C=C1 YLXSHCBLGREHCG-UHFFFAOYSA-N 0.000 claims description 2
- WTCCEWIQTAHILZ-UHFFFAOYSA-N 3-chloro-4-[[4,5-dimethyl-2-[(5-methylfuran-2-yl)sulfonyl-propan-2-ylamino]phenoxy]methyl]benzoic acid Chemical compound C=1C=C(C)OC=1S(=O)(=O)N(C(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C(O)=O)C=C1Cl WTCCEWIQTAHILZ-UHFFFAOYSA-N 0.000 claims description 2
- RCLVSQKFUQWWTO-UHFFFAOYSA-N 3-chloro-4-[[5-chloro-4-methyl-2-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]phenoxy]methyl]benzoic acid Chemical compound N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(Cl)C=C1OCC1=CC=C(C(O)=O)C=C1Cl RCLVSQKFUQWWTO-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- ARRNBPCNZJXHRJ-UHFFFAOYSA-M hydron;tetrabutylazanium;phosphate Chemical compound OP(O)([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC ARRNBPCNZJXHRJ-UHFFFAOYSA-M 0.000 description 1
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- 239000011777 magnesium Substances 0.000 description 1
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- PMGPSOBNHFIPAR-UHFFFAOYSA-N methyl 3-methyl-4-(methylsulfonyloxymethyl)benzoate Chemical compound COC(=O)C1=CC=C(COS(C)(=O)=O)C(C)=C1 PMGPSOBNHFIPAR-UHFFFAOYSA-N 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- MDNASDRVZCHFNG-UHFFFAOYSA-N n-(2-methylpropyl)-n-[2-[[4-(2h-tetrazol-5-yl)phenyl]methoxy]-4-(trifluoromethyl)phenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC=NC=1S(=O)(=O)N(CC(C)C)C1=CC=C(C(F)(F)F)C=C1OCC(C=C1)=CC=C1C=1N=NNN=1 MDNASDRVZCHFNG-UHFFFAOYSA-N 0.000 description 1
- FZYUIJASXBXSOZ-UHFFFAOYSA-N n-(2-methylpropyl)pyridine-2-sulfonamide Chemical compound CC(C)CNS(=O)(=O)C1=CC=CC=N1 FZYUIJASXBXSOZ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- PULGYDLMFSFVBL-SMFNREODSA-N nociceptin Chemical compound C([C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)[C@@H](C)O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 PULGYDLMFSFVBL-SMFNREODSA-N 0.000 description 1
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- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
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- 235000011009 potassium phosphates Nutrition 0.000 description 1
- ZAKWLULNQIXBNT-UHFFFAOYSA-M potassium;3-[4-[[6-[(4-methyl-1,3-thiazol-2-yl)sulfonyl-propan-2-ylamino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]phenyl]prop-2-enoate Chemical compound [K+].N=1C(C)=CSC=1S(=O)(=O)N(C(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C=CC([O-])=O)C=C1 ZAKWLULNQIXBNT-UHFFFAOYSA-M 0.000 description 1
- LDFSIKKPLWOEMQ-UHFFFAOYSA-M potassium;4-[[4,5-dimethyl-2-[2-methylpropyl(1,3-thiazol-2-ylsulfonyl)amino]phenoxy]methyl]benzoate Chemical compound [K+].N=1C=CSC=1S(=O)(=O)N(CC(C)C)C1=CC(C)=C(C)C=C1OCC1=CC=C(C([O-])=O)C=C1 LDFSIKKPLWOEMQ-UHFFFAOYSA-M 0.000 description 1
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- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
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- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- DSDNAKHZNJAGHN-UHFFFAOYSA-N resinferatoxin Natural products C1=C(O)C(OC)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-UHFFFAOYSA-N 0.000 description 1
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- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- DXIHILNWDOYYCH-UHDJGPCESA-M sodium;(e)-3-phenylprop-2-enoate Chemical compound [Na+].[O-]C(=O)\C=C\C1=CC=CC=C1 DXIHILNWDOYYCH-UHDJGPCESA-M 0.000 description 1
- ZNJHFNUEQDVFCJ-UHFFFAOYSA-M sodium;2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid;hydroxide Chemical compound [OH-].[Na+].OCCN1CCN(CCS(O)(=O)=O)CC1 ZNJHFNUEQDVFCJ-UHFFFAOYSA-M 0.000 description 1
- HIHFEVWQBIGCIR-UHFFFAOYSA-M sodium;2-methylbenzoate Chemical compound [Na+].CC1=CC=CC=C1C([O-])=O HIHFEVWQBIGCIR-UHFFFAOYSA-M 0.000 description 1
- HKWRZSXEWPTLQS-UHFFFAOYSA-M sodium;4-[[6-[2-methylpropyl-[(4-methyl-1,3-thiazol-2-yl)sulfonyl]amino]-2,3-dihydro-1h-inden-5-yl]oxymethyl]benzoate Chemical compound [Na+].N=1C(C)=CSC=1S(=O)(=O)N(CC(C)C)C1=CC=2CCCC=2C=C1OCC1=CC=C(C([O-])=O)C=C1 HKWRZSXEWPTLQS-UHFFFAOYSA-M 0.000 description 1
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- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
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- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- BXVYJQULAWJPSR-UHFFFAOYSA-N thiadiazepine Chemical compound S1C=CC=CN=N1 BXVYJQULAWJPSR-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 1
- 125000000034 thioazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
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- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/64—Sulfur atoms
-
- 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
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2001068498 | 2001-03-12 | ||
JP2001281569 | 2001-09-17 | ||
JP2002007760 | 2002-01-16 | ||
PCT/JP2002/002245 WO2002072564A1 (fr) | 2001-03-12 | 2002-03-11 | Compose de n-phenylarylsulfonamide, medicament contenant le compose en tant que principe actif, intermediaire pour le compose et ses procedes de production |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20034007D0 NO20034007D0 (no) | 2003-09-10 |
NO20034007L NO20034007L (no) | 2003-11-12 |
NO329682B1 true NO329682B1 (no) | 2010-11-29 |
Family
ID=27346214
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20034007A NO329682B1 (no) | 2001-03-12 | 2003-09-10 | N-fenylarylsulfonamidforbindelse, og antagonist av EP1 reseptor og farmasoytisk preparat omfattende forbindelsen som aktiv bestanddel |
Country Status (24)
Country | Link |
---|---|
US (3) | US7235667B2 (pl) |
EP (2) | EP1612208B1 (pl) |
JP (3) | JP3555620B2 (pl) |
KR (1) | KR100886854B1 (pl) |
CN (1) | CN1294126C (pl) |
AT (2) | ATE522513T1 (pl) |
AU (1) | AU2002238855B2 (pl) |
BR (1) | BR0208027A (pl) |
CA (1) | CA2439604C (pl) |
CZ (1) | CZ304035B6 (pl) |
DE (1) | DE60220255T2 (pl) |
DK (2) | DK1612208T3 (pl) |
ES (1) | ES2286230T3 (pl) |
HU (1) | HU230056B1 (pl) |
IL (2) | IL157701A0 (pl) |
MX (1) | MXPA03008134A (pl) |
NO (1) | NO329682B1 (pl) |
NZ (1) | NZ528120A (pl) |
PL (1) | PL218750B1 (pl) |
PT (2) | PT1369419E (pl) |
RU (1) | RU2299202C2 (pl) |
TW (1) | TWI317359B (pl) |
WO (1) | WO2002072564A1 (pl) |
ZA (1) | ZA200306884B (pl) |
Families Citing this family (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2003264388A1 (en) * | 2002-09-09 | 2004-03-29 | Ono Pharmaceutical Co., Ltd. | Process for producing 4-methyl-1,3-thiazol-2-ylsulfonyl halide |
AU2004207675B2 (en) * | 2003-01-29 | 2010-05-20 | Asterand Uk Acquisition Limited | EP4 receptor antagonists |
GB0317500D0 (en) * | 2003-07-25 | 2003-08-27 | Pfizer Ltd | Treatment of bph |
JPWO2005000356A1 (ja) * | 2003-06-27 | 2006-08-03 | 小野薬品工業株式会社 | 尿路疾患治療剤 |
GB0401334D0 (en) * | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
EP1767208A4 (en) * | 2004-07-05 | 2007-12-05 | Chugai Pharmaceutical Co Ltd | REMEDY FOR HYPERACTIVE BLADDER |
JP2008189549A (ja) * | 2005-05-12 | 2008-08-21 | Astellas Pharma Inc | カルボン酸誘導体またはその塩 |
JP2009057282A (ja) * | 2005-12-19 | 2009-03-19 | Astellas Pharma Inc | カルボン酸誘導体又はその塩 |
TW200817319A (en) * | 2006-08-10 | 2008-04-16 | Astellas Pharma Inc | Sulfonamide compound or salt thereof |
BRPI0807942A2 (pt) * | 2007-02-16 | 2014-07-01 | Ono Pharmaceutical Co | Agente terapêutico para distúrbio de excreção urinária |
DK2177512T3 (da) * | 2007-08-01 | 2012-06-18 | Taisho Pharmaceutical Co Ltd | S1P1-bindingshæmmer |
EP2116618A1 (en) | 2008-05-09 | 2009-11-11 | Agency for Science, Technology And Research | Diagnosis and treatment of Kawasaki disease |
AU2009263457B2 (en) * | 2008-06-23 | 2013-05-16 | Astellas Pharma Inc. | Sulfonamide compounds or salts thereof |
TW201107309A (en) * | 2009-07-27 | 2011-03-01 | Kissei Pharmaceutical | Indole derivatives, or the pharmaceutically acceptable salts |
JP2013532688A (ja) * | 2010-07-26 | 2013-08-19 | ブリストル−マイヤーズ スクイブ カンパニー | Cyp17阻害剤として有用なスルホンアミド化合物 |
JP5363636B2 (ja) * | 2011-10-21 | 2013-12-11 | ファイザー・リミテッド | 新規な塩および医学的使用 |
US20140039004A1 (en) * | 2012-07-31 | 2014-02-06 | Ono Pharmaceutical Co., Ltd. | Method of treating of gastroesophageal reflux disease |
JP6103893B2 (ja) * | 2012-11-15 | 2017-03-29 | サントリー食品インターナショナル株式会社 | コーヒーオイルの製造方法 |
ES2709005T3 (es) * | 2014-04-30 | 2019-04-12 | Ind Penalver Sl | Cabezal concéntrico programable para la aplicación líquida en tapas multiformato |
RS60927B1 (sr) * | 2015-11-13 | 2020-11-30 | Daewoong Pharmaceutical Co Ltd | Blokator natrijumovih kanala |
RU2659955C1 (ru) * | 2017-10-26 | 2018-07-04 | Галина Ильхамовна Лукина | Способ диагностики высоких гастроэзофагеальных рефлюксов |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2419923A1 (de) * | 1973-04-28 | 1974-11-28 | Fujisawa Pharmaceutical Co | Sulfonsaeureester, verfahren zu deren herstellung und verwendung derselben als kondensationsmittel |
JPS5748534B2 (pl) | 1974-03-04 | 1982-10-16 | ||
DE2555048A1 (de) * | 1975-12-06 | 1977-06-30 | Pfersee Chem Fab | Verfahren und vorrichtung zur herstellung bestaendiger, waessriger emulsionen wasserunloeslicher substanzen |
JPS5293469A (en) | 1976-02-02 | 1977-08-05 | Fuji Photo Film Co Ltd | Method of curing gelatin |
JPH05293469A (ja) | 1992-04-17 | 1993-11-09 | Toda Constr Co Ltd | 滅菌精製水の製造方法およびその装置 |
TW523506B (en) * | 1996-12-18 | 2003-03-11 | Ono Pharmaceutical Co | Sulfonamide or carbamide derivatives and drugs containing the same as active ingredients |
WO2000069465A1 (fr) * | 1999-05-12 | 2000-11-23 | Ono Pharmaceutical Co., Ltd. | Agents anticancereux contenant des antagonistes de ep1 en tant que principe actif |
EP1201238A4 (en) | 1999-07-29 | 2003-01-15 | Ono Pharmaceutical Co | SULPHONAMIDE DERIVATIVES AND HEALING AGENTS FOR ALLODYNIA |
WO2002072145A1 (fr) * | 2001-03-14 | 2002-09-19 | Ono Pharmaceutical Co., Ltd. | Remedes antidepresseurs contenant un antagoniste ep1 en tant que principe actif |
-
2002
- 2002-03-11 AT AT05109059T patent/ATE522513T1/de active
- 2002-03-11 CN CNB028097904A patent/CN1294126C/zh not_active Expired - Fee Related
- 2002-03-11 EP EP05109059A patent/EP1612208B1/en not_active Expired - Lifetime
- 2002-03-11 IL IL15770102A patent/IL157701A0/xx unknown
- 2002-03-11 WO PCT/JP2002/002245 patent/WO2002072564A1/ja active IP Right Grant
- 2002-03-11 DK DK05109059.5T patent/DK1612208T3/da active
- 2002-03-11 JP JP2002571480A patent/JP3555620B2/ja not_active Expired - Fee Related
- 2002-03-11 PT PT02705096T patent/PT1369419E/pt unknown
- 2002-03-11 EP EP02705096A patent/EP1369419B1/en not_active Expired - Lifetime
- 2002-03-11 TW TW091104451A patent/TWI317359B/zh not_active IP Right Cessation
- 2002-03-11 DE DE60220255T patent/DE60220255T2/de not_active Expired - Lifetime
- 2002-03-11 BR BR0208027-3A patent/BR0208027A/pt not_active IP Right Cessation
- 2002-03-11 HU HU0400155A patent/HU230056B1/hu not_active IP Right Cessation
- 2002-03-11 MX MXPA03008134A patent/MXPA03008134A/es active IP Right Grant
- 2002-03-11 PL PL365100A patent/PL218750B1/pl unknown
- 2002-03-11 PT PT05109059T patent/PT1612208E/pt unknown
- 2002-03-11 CZ CZ20032452A patent/CZ304035B6/cs not_active IP Right Cessation
- 2002-03-11 CA CA2439604A patent/CA2439604C/en not_active Expired - Fee Related
- 2002-03-11 US US10/471,673 patent/US7235667B2/en not_active Expired - Fee Related
- 2002-03-11 DK DK02705096T patent/DK1369419T3/da active
- 2002-03-11 AT AT02705096T patent/ATE362924T1/de active
- 2002-03-11 ES ES02705096T patent/ES2286230T3/es not_active Expired - Lifetime
- 2002-03-11 RU RU2003127677/04A patent/RU2299202C2/ru not_active IP Right Cessation
- 2002-03-11 AU AU2002238855A patent/AU2002238855B2/en not_active Ceased
- 2002-03-11 KR KR1020037011921A patent/KR100886854B1/ko not_active IP Right Cessation
- 2002-03-11 NZ NZ528120A patent/NZ528120A/en not_active IP Right Cessation
-
2003
- 2003-09-02 IL IL157701A patent/IL157701A/en not_active IP Right Cessation
- 2003-09-03 ZA ZA2003/06884A patent/ZA200306884B/en unknown
- 2003-09-10 NO NO20034007A patent/NO329682B1/no not_active IP Right Cessation
- 2003-12-24 JP JP2003427226A patent/JP3741120B2/ja not_active Expired - Fee Related
-
2005
- 2005-08-26 JP JP2005245763A patent/JP4432051B2/ja not_active Expired - Fee Related
- 2005-09-30 US US11/239,406 patent/US7629369B2/en not_active Expired - Fee Related
-
2009
- 2009-10-21 US US12/603,194 patent/US8088802B2/en not_active Expired - Fee Related
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