DE69429836T2 - Tricyclische,substituierte Pyrazolyl- benzolsulfonamide und ihre Verwendung als Cyclooxygenase II Inhibitoren - Google Patents
Tricyclische,substituierte Pyrazolyl- benzolsulfonamide und ihre Verwendung als Cyclooxygenase II InhibitorenInfo
- Publication number
- DE69429836T2 DE69429836T2 DE69429836T DE69429836T DE69429836T2 DE 69429836 T2 DE69429836 T2 DE 69429836T2 DE 69429836 T DE69429836 T DE 69429836T DE 69429836 T DE69429836 T DE 69429836T DE 69429836 T2 DE69429836 T2 DE 69429836T2
- Authority
- DE
- Germany
- Prior art keywords
- radicals
- dihydro
- benzenesulfonamide
- indazol
- trifluoromethyl
- 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.)
- Expired - Lifetime
Links
- 108010037462 Cyclooxygenase 2 Proteins 0.000 title description 6
- HMDUADNDMXESSJ-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=NN1 HMDUADNDMXESSJ-UHFFFAOYSA-N 0.000 title description 2
- 102000010907 Cyclooxygenase 2 Human genes 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- -1 cyano, carboxyl Chemical group 0.000 claims description 232
- 150000003254 radicals Chemical class 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 5
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 5
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 5
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 5
- 125000006001 difluoroethyl group Chemical group 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 5
- 125000006343 heptafluoro propyl group Chemical group 0.000 claims description 5
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 5
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- LTAXFLQWGJQFJX-UHFFFAOYSA-N 4-[3-(trifluoromethyl)-4,5-dihydrobenzo[g]indazol-1-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1C(C2=CC=CC=C2CC2)=C2C(C(F)(F)F)=N1 LTAXFLQWGJQFJX-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 3
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- BYJVPJTWOSYORV-UHFFFAOYSA-N methyl 7-methoxy-1-(4-sulfamoylphenyl)-4,5-dihydrobenzo[g]indazole-3-carboxylate Chemical compound C1CC2=CC(OC)=CC=C2C2=C1C(C(=O)OC)=NN2C1=CC=C(S(N)(=O)=O)C=C1 BYJVPJTWOSYORV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
- YIJVXISJMKGULJ-UHFFFAOYSA-N 4-[3-(difluoromethyl)-7-methoxy-4,5-dihydrobenzo[g]indazol-1-yl]benzenesulfonamide Chemical compound C1CC2=CC(OC)=CC=C2C2=C1C(C(F)F)=NN2C1=CC=C(S(N)(=O)=O)C=C1 YIJVXISJMKGULJ-UHFFFAOYSA-N 0.000 claims description 2
- JCOIFYCOGNRBBZ-UHFFFAOYSA-N 4-[3-(difluoromethyl)-7-methyl-4,5-dihydrobenzo[g]indazol-1-yl]benzenesulfonamide Chemical compound C1CC2=CC(C)=CC=C2C2=C1C(C(F)F)=NN2C1=CC=C(S(N)(=O)=O)C=C1 JCOIFYCOGNRBBZ-UHFFFAOYSA-N 0.000 claims description 2
- ZKWXOBYASCSKBJ-UHFFFAOYSA-N 4-[7-methoxy-3-(trifluoromethyl)-4,5-dihydrobenzo[g]indazol-1-yl]benzenesulfonamide Chemical compound C1CC2=CC(OC)=CC=C2C2=C1C(C(F)(F)F)=NN2C1=CC=C(S(N)(=O)=O)C=C1 ZKWXOBYASCSKBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 abstract description 13
- 206010061218 Inflammation Diseases 0.000 abstract description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
- 208000035475 disorder Diseases 0.000 abstract description 3
- IGCQXMQOKRXHHN-UHFFFAOYSA-N n-(1h-pyrazol-5-yl)benzenesulfonamide Chemical class C=1C=CC=CC=1S(=O)(=O)NC=1C=CNN=1 IGCQXMQOKRXHHN-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 235000002639 sodium chloride Nutrition 0.000 description 16
- 238000000034 method Methods 0.000 description 15
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000005840 aryl radicals Chemical class 0.000 description 12
- 150000003217 pyrazoles Chemical class 0.000 description 11
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 10
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 235000010418 carrageenan Nutrition 0.000 description 8
- 239000000679 carrageenan Substances 0.000 description 8
- 229920001525 carrageenan Polymers 0.000 description 8
- 229940113118 carrageenan Drugs 0.000 description 8
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 8
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 8
- 125000004430 oxygen atom Chemical group O* 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 150000003180 prostaglandins Chemical class 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000701447 unidentified baculovirus Species 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 125000005594 diketone group Chemical group 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 125000004434 sulfur atom Chemical group 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
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- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
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- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
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- 241000238631 Hexapoda Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
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- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
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- 239000003472 antidiabetic agent Substances 0.000 description 4
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- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
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- IBLXSXYZUJVQNK-UHFFFAOYSA-N 4-[7-methyl-3-(trifluoromethyl)-4,5-dihydrobenzo[g]indazol-1-yl]benzenesulfonamide Chemical compound C1CC2=CC(C)=CC=C2C2=C1C(C(F)(F)F)=NN2C1=CC=C(S(N)(=O)=O)C=C1 IBLXSXYZUJVQNK-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- A—HUMAN NECESSITIES
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- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/16—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/160,594 US5466823A (en) | 1993-11-30 | 1993-11-30 | Substituted pyrazolyl benzenesulfonamides |
| US08/223,629 US5521207A (en) | 1993-11-30 | 1994-04-06 | Substituted pyrazolyl benzenesulfonamide for the treatment of inflammation |
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| DE69429836D1 DE69429836D1 (de) | 2002-03-21 |
| DE69429836T2 true DE69429836T2 (de) | 2002-07-18 |
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| DE69429836T Expired - Lifetime DE69429836T2 (de) | 1993-11-30 | 1994-11-14 | Tricyclische,substituierte Pyrazolyl- benzolsulfonamide und ihre Verwendung als Cyclooxygenase II Inhibitoren |
| DE69432193T Expired - Lifetime DE69432193T2 (de) | 1993-11-30 | 1994-11-14 | Substituierte Pyrazolyl-benzolsulfonamide und ihre Verwendung als CyclooxygenaseII Inhibitoren |
| DE69422306A Expired - Lifetime DE69422306D1 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
| DE69430930T Expired - Lifetime DE69430930T2 (de) | 1993-11-30 | 1994-11-14 | Substitutierte Pyrazolyl-Benzolsulfonamide zur Verwendung in der Behandlung von Entzündungen |
| DE2000175033 Active DE10075033I2 (de) | 1993-11-30 | 1994-11-14 | substituierte Pyrazolyl-benzolsulfonamide zur Behandlung von Entzündungen. |
| DE69422306T Expired - Lifetime DE69422306T4 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
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| DE69432193T Expired - Lifetime DE69432193T2 (de) | 1993-11-30 | 1994-11-14 | Substituierte Pyrazolyl-benzolsulfonamide und ihre Verwendung als CyclooxygenaseII Inhibitoren |
| DE69422306A Expired - Lifetime DE69422306D1 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
| DE69430930T Expired - Lifetime DE69430930T2 (de) | 1993-11-30 | 1994-11-14 | Substitutierte Pyrazolyl-Benzolsulfonamide zur Verwendung in der Behandlung von Entzündungen |
| DE2000175033 Active DE10075033I2 (de) | 1993-11-30 | 1994-11-14 | substituierte Pyrazolyl-benzolsulfonamide zur Behandlung von Entzündungen. |
| DE69422306T Expired - Lifetime DE69422306T4 (de) | 1993-11-30 | 1994-11-14 | Substituierte pyrazolyl-benzolsulfonamide zur behandlung von entzündungen |
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| EP (1) | EP0731795B1 (OSRAM) |
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| CN (4) | CN1268614C (OSRAM) |
| AT (4) | ATE233245T1 (OSRAM) |
| CA (4) | CA2277954A1 (OSRAM) |
| CY (2) | CY2237B1 (OSRAM) |
| CZ (1) | CZ294630B6 (OSRAM) |
| DE (6) | DE69429836T2 (OSRAM) |
| DK (3) | DK0924201T3 (OSRAM) |
| ES (4) | ES2172959T3 (OSRAM) |
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| FR (1) | FR09C0007I2 (OSRAM) |
| GR (1) | GR3032696T3 (OSRAM) |
| HU (1) | HU223824B1 (OSRAM) |
| LU (2) | LU90698I2 (OSRAM) |
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| NO (1) | NO306460B1 (OSRAM) |
| NZ (3) | NZ276885A (OSRAM) |
| PL (1) | PL180717B1 (OSRAM) |
| PT (3) | PT923933E (OSRAM) |
| RO (1) | RO118291B1 (OSRAM) |
| RU (1) | RU2139281C1 (OSRAM) |
| WO (1) | WO1995015316A1 (OSRAM) |
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1994
- 1994-11-14 KR KR1019997003745A patent/KR100263817B1/ko not_active Expired - Lifetime
- 1994-11-14 PT PT99101697T patent/PT923933E/pt unknown
- 1994-11-14 JP JP7515611A patent/JP3025017B2/ja not_active Expired - Lifetime
- 1994-11-14 HU HU9601455A patent/HU223824B1/hu active Protection Beyond IP Right Term
- 1994-11-14 EP EP95902444A patent/EP0731795B1/en not_active Expired - Lifetime
- 1994-11-14 KR KR1019960702677A patent/KR100229343B1/ko not_active Expired - Lifetime
- 1994-11-14 US US08/648,113 patent/US5760068A/en not_active Ceased
- 1994-11-14 CN CNB2003101142478A patent/CN1268614C/zh not_active Expired - Lifetime
- 1994-11-14 ES ES99101677T patent/ES2172959T3/es not_active Expired - Lifetime
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- 1994-11-14 CA CA002277954A patent/CA2277954A1/en not_active Abandoned
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- 1994-11-14 DK DK99101677T patent/DK0924201T3/da active
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- 1994-11-14 DE DE69429836T patent/DE69429836T2/de not_active Expired - Lifetime
- 1994-11-14 DE DE69432193T patent/DE69432193T2/de not_active Expired - Lifetime
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- 1994-11-14 AT AT99101687T patent/ATE233245T1/de active
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- 1994-11-14 DK DK95902444T patent/DK0731795T3/da active
- 1994-11-14 CA CA002276945A patent/CA2276945C/en not_active Expired - Lifetime
- 1994-11-14 AT AT95902444T patent/ATE187965T1/de active
- 1994-11-14 PT PT99101677T patent/PT924201E/pt unknown
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- 1994-11-14 AT AT99101697T patent/ATE219937T1/de active
- 1994-11-14 DE DE69430930T patent/DE69430930T2/de not_active Expired - Lifetime
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- 1994-11-14 ES ES99101687T patent/ES2193609T3/es not_active Expired - Lifetime
- 1994-11-14 AT AT99101677T patent/ATE212985T1/de active
- 1994-11-14 WO PCT/US1994/012720 patent/WO1995015316A1/en not_active Ceased
- 1994-11-14 DE DE2000175033 patent/DE10075033I2/de active Active
- 1994-11-14 PT PT95902444T patent/PT731795E/pt unknown
- 1994-11-14 DK DK99101697T patent/DK0923933T3/da active
- 1994-11-14 RU RU96115039A patent/RU2139281C1/ru active
- 1994-11-14 RO RO96-01100A patent/RO118291B1/ro unknown
- 1994-11-14 CA CA002276946A patent/CA2276946A1/en not_active Abandoned
- 1994-11-14 PL PL94314695A patent/PL180717B1/pl unknown
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1995
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1996
- 1996-05-29 FI FI962249A patent/FI115053B/fi not_active IP Right Cessation
- 1996-05-29 NO NO962184A patent/NO306460B1/no not_active IP Right Cessation
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1999
- 1999-04-28 KR KR1019997003746A patent/KR100261669B1/ko not_active Expired - Lifetime
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2000
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- 2000-12-13 LU LU90698C patent/LU90698I2/fr unknown
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2001
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2003
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2009
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- 2009-03-09 CY CY200900003C patent/CY2009003I1/el unknown
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