NO314184B1 - Substituert benzensulfonamid derivater, fremgangsmåte for fremstilling av samme, farmasöytisk sammensetning innbefattende samme og anvendelseav samme forfremstilling av medikament - Google Patents
Substituert benzensulfonamid derivater, fremgangsmåte for fremstilling av samme, farmasöytisk sammensetning innbefattende samme og anvendelseav samme forfremstilling av medikament Download PDFInfo
- Publication number
- NO314184B1 NO314184B1 NO19984727A NO984727A NO314184B1 NO 314184 B1 NO314184 B1 NO 314184B1 NO 19984727 A NO19984727 A NO 19984727A NO 984727 A NO984727 A NO 984727A NO 314184 B1 NO314184 B1 NO 314184B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- sulfonyl
- methyl
- phenylisoxazol
- acetamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 69
- 238000002360 preparation method Methods 0.000 title claims description 35
- 230000008569 process Effects 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title claims description 6
- 229940079593 drug Drugs 0.000 title description 3
- 150000008331 benzenesulfonamides Chemical class 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 191
- 159000000000 sodium salts Chemical class 0.000 claims description 154
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 149
- 150000001875 compounds Chemical class 0.000 claims description 133
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 128
- -1 methylcarbonyloxymethyl Chemical group 0.000 claims description 85
- 150000003254 radicals Chemical class 0.000 claims description 71
- 150000003839 salts Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 229940124530 sulfonamide Drugs 0.000 claims description 32
- 150000003456 sulfonamides Chemical class 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 30
- 239000002585 base Substances 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- HJZVHUQSQGITAM-UHFFFAOYSA-N butanamide Chemical compound CC[CH]C(N)=O HJZVHUQSQGITAM-UHFFFAOYSA-N 0.000 claims description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 24
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 17
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 16
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 125000002541 furyl group Chemical group 0.000 claims description 15
- 230000004054 inflammatory process Effects 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 14
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 14
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
- 125000002971 oxazolyl group Chemical group 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- TZRHLKRLEZJVIJ-UHFFFAOYSA-N parecoxib Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 TZRHLKRLEZJVIJ-UHFFFAOYSA-N 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 14
- 239000011734 sodium Substances 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UMBILIGVYYXBRD-UHFFFAOYSA-N n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 UMBILIGVYYXBRD-UHFFFAOYSA-N 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
- BOVVAGCRFBVSMH-UHFFFAOYSA-N 2-[[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]acetic acid Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(=O)(=O)NCC(O)=O)C=C1 BOVVAGCRFBVSMH-UHFFFAOYSA-N 0.000 claims description 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 150000002460 imidazoles Chemical class 0.000 claims description 10
- DABKXKAHZRINCJ-UHFFFAOYSA-N n-[4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C(=NC=CC=2)C)=NC(C(F)(F)F)=C1 DABKXKAHZRINCJ-UHFFFAOYSA-N 0.000 claims description 10
- XLANJOIUYYCBSJ-UHFFFAOYSA-N n-[4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 XLANJOIUYYCBSJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 8
- SEVVOVNLQZXWRO-UHFFFAOYSA-N [4-[4-(acetylsulfamoyl)phenyl]-3-phenyl-1,2-oxazol-5-yl]methyl acetate Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(COC(C)=O)ON=C1C1=CC=CC=C1 SEVVOVNLQZXWRO-UHFFFAOYSA-N 0.000 claims description 8
- 150000008064 anhydrides Chemical group 0.000 claims description 8
- IVQPYWFNIZDTFB-UHFFFAOYSA-N n-[4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C=C(C)C=NC=2)=NC(C(F)(F)F)=C1 IVQPYWFNIZDTFB-UHFFFAOYSA-N 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 7
- GXLPXTQMKIFHNL-UHFFFAOYSA-N 2-amino-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylacetamide Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(=O)(=O)NC(=O)CN)C=C1 GXLPXTQMKIFHNL-UHFFFAOYSA-N 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- AROIRVNGHKAPEJ-UHFFFAOYSA-N n-[4-[2-(5-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylbutanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CCC)=CC=C1N1C(C=2C=C(C)C=NC=2)=NC(C(F)(F)F)=C1 AROIRVNGHKAPEJ-UHFFFAOYSA-N 0.000 claims description 7
- RRPAVYZAEYJLIV-UHFFFAOYSA-N n-[4-[3-(3-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(C)ON=C1C1=CC=CC(F)=C1 RRPAVYZAEYJLIV-UHFFFAOYSA-N 0.000 claims description 7
- SHEZNOJEXCHKRT-UHFFFAOYSA-N 2-methyl-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C(C)C)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 SHEZNOJEXCHKRT-UHFFFAOYSA-N 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- OBNHDXLHPUVWBZ-UHFFFAOYSA-N methyl 3-[[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]-3-oxopropanoate Chemical compound C1=CC(S(=O)(=O)NC(=O)CC(=O)OC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 OBNHDXLHPUVWBZ-UHFFFAOYSA-N 0.000 claims description 6
- CQWCMDRFKCDDBE-UHFFFAOYSA-N n-[4-(4,5-dimethyl-2-phenylpyrazol-3-yl)phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(C)C(C)=NN1C1=CC=CC=C1 CQWCMDRFKCDDBE-UHFFFAOYSA-N 0.000 claims description 6
- HBJRELCEAUESDU-UHFFFAOYSA-N n-[4-[2-(3-chloro-5-methylphenyl)-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C=C(Cl)C=C(C)C=2)=NC(C(F)(F)F)=C1 HBJRELCEAUESDU-UHFFFAOYSA-N 0.000 claims description 6
- UFLSIWXZTLGQBO-UHFFFAOYSA-N n-[4-[2-pyridin-3-yl-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1N1C(C=2C=NC=CC=2)=NC(C(F)(F)F)=C1 UFLSIWXZTLGQBO-UHFFFAOYSA-N 0.000 claims description 6
- JEFLFHUNDHMHBS-UHFFFAOYSA-N n-[4-[5-(difluoromethyl)-3-phenyl-1,2-oxazol-4-yl]phenyl]sulfonylbutanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CCC)=CC=C1C1=C(C(F)F)ON=C1C1=CC=CC=C1 JEFLFHUNDHMHBS-UHFFFAOYSA-N 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 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 description 5
- FEAXYAGGPKJWNP-UHFFFAOYSA-N 2-acetamido-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CNC(=O)C)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 FEAXYAGGPKJWNP-UHFFFAOYSA-N 0.000 claims description 5
- VKAMRRXGHIGUOC-UHFFFAOYSA-N 3-methoxy-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CCOC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 VKAMRRXGHIGUOC-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- UUYJQYHQMGMJNE-UHFFFAOYSA-N n-[4-[2-(2-methylpyridin-3-yl)-4-(trifluoromethyl)imidazol-1-yl]phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1N1C(C=2C(=NC=CC=2)C)=NC(C(F)(F)F)=C1 UUYJQYHQMGMJNE-UHFFFAOYSA-N 0.000 claims description 5
- RNIVHFUBFIQAKR-UHFFFAOYSA-N n-[4-[5-(4-chlorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1N1C(C=2C=CC(Cl)=CC=2)=CC(C(F)(F)F)=N1 RNIVHFUBFIQAKR-UHFFFAOYSA-N 0.000 claims description 5
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 5
- QWTFAROZGRGVKP-UHFFFAOYSA-N tert-butyl n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylcarbamate Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(=O)(=O)NC(=O)OC(C)(C)C)C=C1 QWTFAROZGRGVKP-UHFFFAOYSA-N 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- UOJZXAVHVOSLBY-UHFFFAOYSA-N 2,2-dimethyl-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpropanamide Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(=O)(=O)NC(=O)C(C)(C)C)C=C1 UOJZXAVHVOSLBY-UHFFFAOYSA-N 0.000 claims description 4
- UPCOALQBVSRRJH-UHFFFAOYSA-N 2-ethoxy-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)COCC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 UPCOALQBVSRRJH-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical group CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012346 acetyl chloride Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- OEHMOWQXDQWJOK-UHFFFAOYSA-N methyl 4-[[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]-4-oxobutanoate Chemical compound C1=CC(S(=O)(=O)NC(=O)CCC(=O)OC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 OEHMOWQXDQWJOK-UHFFFAOYSA-N 0.000 claims description 4
- XZOXXAKVMYDPGI-UHFFFAOYSA-N n-[4-(2-oxo-3-phenyl-3h-furan-4-yl)phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=COC(=O)C1C1=CC=CC=C1 XZOXXAKVMYDPGI-UHFFFAOYSA-N 0.000 claims description 4
- JEKRFLTZIYZCFN-UHFFFAOYSA-N n-[4-[2-(3-chloro-4-fluorophenyl)cyclopenten-1-yl]phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(C=2C=C(Cl)C(F)=CC=2)CCC1 JEKRFLTZIYZCFN-UHFFFAOYSA-N 0.000 claims description 4
- QYTCSNACICVAQU-UHFFFAOYSA-N n-[4-[3-(difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)pyrazol-1-yl]phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1N1C(C=2C=C(F)C(OC)=CC=2)=CC(C(F)F)=N1 QYTCSNACICVAQU-UHFFFAOYSA-N 0.000 claims description 4
- RYKTYZGWZMSGIT-UHFFFAOYSA-N n-[4-[5-(hydroxymethyl)-3-phenyl-1,2-oxazol-4-yl]phenyl]sulfonylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CC)=CC=C1C1=C(CO)ON=C1C1=CC=CC=C1 RYKTYZGWZMSGIT-UHFFFAOYSA-N 0.000 claims description 4
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- DLZQFPWULWNSFC-UHFFFAOYSA-N 2-[acetyl-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]acetic acid Chemical compound C1=CC(S(=O)(=O)N(CC(O)=O)C(=O)C)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 DLZQFPWULWNSFC-UHFFFAOYSA-N 0.000 claims description 3
- WZCCGMXSPZYGDX-UHFFFAOYSA-N 2-methoxy-n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)COC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 WZCCGMXSPZYGDX-UHFFFAOYSA-N 0.000 claims description 3
- IJTOZRCITTULPA-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)pyrrol-1-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC=C1 IJTOZRCITTULPA-UHFFFAOYSA-N 0.000 claims description 3
- DMYSIIFBWILMSH-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-(trifluoromethyl)pyrazol-1-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1N1C(C=2C=CC(F)=CC=2)=CC(C(F)(F)F)=N1 DMYSIIFBWILMSH-UHFFFAOYSA-N 0.000 claims description 3
- KYFKXZLWTIWCBK-UHFFFAOYSA-N 4-[[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]-4-oxobutanoic acid Chemical compound CC=1ON=C(C=2C=CC=CC=2)C=1C1=CC=C(S(=O)(=O)NC(=O)CCC(O)=O)C=C1 KYFKXZLWTIWCBK-UHFFFAOYSA-N 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- CXDHGRAOXJEMOO-UHFFFAOYSA-N methyl 2-[[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylamino]-2-oxoacetate Chemical compound C1=CC(S(=O)(=O)NC(=O)C(=O)OC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 CXDHGRAOXJEMOO-UHFFFAOYSA-N 0.000 claims description 3
- IRIHYRQDKBVTRJ-UHFFFAOYSA-N n-[4-(2-methyl-4-phenyl-1,3-oxazol-5-yl)phenyl]sulfonylacetamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1C1=C(C=2C=CC=CC=2)N=C(C)O1 IRIHYRQDKBVTRJ-UHFFFAOYSA-N 0.000 claims description 3
- WCNGJPSUNBDLGE-UHFFFAOYSA-N n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylhexanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CCCCC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 WCNGJPSUNBDLGE-UHFFFAOYSA-N 0.000 claims description 3
- LSFPSLNEPSCUPY-UHFFFAOYSA-N n-[4-(5-methyl-3-phenyl-1,2-oxazol-4-yl)phenyl]sulfonylpentanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)CCCC)=CC=C1C1=C(C)ON=C1C1=CC=CC=C1 LSFPSLNEPSCUPY-UHFFFAOYSA-N 0.000 claims description 3
- WTWBDSYHGPGDBG-UHFFFAOYSA-N n-[4-[3-(difluoromethyl)-5-(3-fluoro-4-methoxyphenyl)pyrazol-1-yl]phenyl]sulfonylacetamide Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C(F)F)=NN1C1=CC=C(S(=O)(=O)NC(C)=O)C=C1 WTWBDSYHGPGDBG-UHFFFAOYSA-N 0.000 claims description 3
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- 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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- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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Applications Claiming Priority (2)
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US63151496A | 1996-04-12 | 1996-04-12 | |
PCT/US1997/005497 WO1997038986A1 (en) | 1996-04-12 | 1997-04-11 | Substituted benzenesulfonamide derivatives as prodrugs of cox-2 inhibitors |
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NO984727D0 NO984727D0 (no) | 1998-10-09 |
NO984727L NO984727L (no) | 1998-12-14 |
NO314184B1 true NO314184B1 (no) | 2003-02-10 |
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NO19984727A NO314184B1 (no) | 1996-04-12 | 1998-10-09 | Substituert benzensulfonamid derivater, fremgangsmåte for fremstilling av samme, farmasöytisk sammensetning innbefattende samme og anvendelseav samme forfremstilling av medikament |
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EP (2) | EP1288206B1 (he) |
JP (2) | JP3382624B2 (he) |
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CN (1) | CN1098256C (he) |
AP (1) | AP1009A (he) |
AT (2) | ATE233743T1 (he) |
AU (1) | AU734275C (he) |
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BR (2) | BR9708574A (he) |
CA (1) | CA2249009C (he) |
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CZ (1) | CZ297430B6 (he) |
DE (2) | DE69719496T2 (he) |
DK (2) | DK0892791T3 (he) |
EA (1) | EA003319B1 (he) |
EE (1) | EE03685B1 (he) |
ES (2) | ES2311571T3 (he) |
GE (1) | GEP20032998B (he) |
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IL (3) | IL153738A (he) |
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ME (1) | ME00768B (he) |
NO (1) | NO314184B1 (he) |
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OA (1) | OA11015A (he) |
PL (1) | PL195955B1 (he) |
PT (2) | PT1288206E (he) |
RO (1) | RO121338B1 (he) |
RS (1) | RS50019B (he) |
SI (2) | SI22713B (he) |
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UA (1) | UA47475C2 (he) |
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