NO325249B1 - Substituerte benzopyranderivater som antiinflammatoriske, farmasoytiske midler, samt fremgangsmater for fremstilling derav - Google Patents
Substituerte benzopyranderivater som antiinflammatoriske, farmasoytiske midler, samt fremgangsmater for fremstilling derav Download PDFInfo
- Publication number
- NO325249B1 NO325249B1 NO19995113A NO995113A NO325249B1 NO 325249 B1 NO325249 B1 NO 325249B1 NO 19995113 A NO19995113 A NO 19995113A NO 995113 A NO995113 A NO 995113A NO 325249 B1 NO325249 B1 NO 325249B1
- Authority
- NO
- Norway
- Prior art keywords
- trifluoromethyl
- benzopyran
- carboxylic acid
- acid
- chloro
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 149
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 94
- 150000001562 benzopyrans Chemical class 0.000 title description 5
- 230000003110 anti-inflammatory effect Effects 0.000 title description 2
- 239000008177 pharmaceutical agent Substances 0.000 title description 2
- -1 trifluoromethoxy, trifluoromethylthio, amino Chemical group 0.000 claims description 459
- 150000001875 compounds Chemical class 0.000 claims description 240
- 239000002253 acid Substances 0.000 claims description 151
- 150000003254 radicals Chemical class 0.000 claims description 97
- 239000000460 chlorine Substances 0.000 claims description 91
- 229910052736 halogen Inorganic materials 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
- 150000002367 halogens Chemical class 0.000 claims description 81
- 239000001257 hydrogen Substances 0.000 claims description 81
- 150000002148 esters Chemical class 0.000 claims description 67
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 63
- 150000002431 hydrogen Chemical class 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 62
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 55
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 53
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 51
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 42
- SMQUZDBALVYZAC-UHFFFAOYSA-N ortho-hydroxybenzaldehyde Natural products OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 42
- 229910052801 chlorine Inorganic materials 0.000 claims description 41
- 239000002585 base Substances 0.000 claims description 37
- 125000001544 thienyl group Chemical group 0.000 claims description 35
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- DEBZQUFVQZPPLC-UHFFFAOYSA-N 2h-chromene-3-carboxylic acid Chemical class C1=CC=C2OCC(C(=O)O)=CC2=C1 DEBZQUFVQZPPLC-UHFFFAOYSA-N 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 23
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000006413 ring segment Chemical group 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 230000004054 inflammatory process Effects 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 15
- 108010037462 Cyclooxygenase 2 Proteins 0.000 claims description 15
- 206010061218 Inflammation Diseases 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 15
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical class C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 12
- QGCKNIAMHUUUDI-UHFFFAOYSA-N 7-tert-butyl-6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=C1C=C(C(C)(C)C)C(Cl)=C2 QGCKNIAMHUUUDI-UHFFFAOYSA-N 0.000 claims description 11
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- NDCFBPDNHOZORS-UHFFFAOYSA-N 1,2-dihydroquinoline-3-carboxylic acid Chemical compound C1=CC=C2NCC(C(=O)O)=CC2=C1 NDCFBPDNHOZORS-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- QSLSQLYQCKEGMS-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QSLSQLYQCKEGMS-UHFFFAOYSA-N 0.000 claims description 9
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 8
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 7
- VEENGDJNDWZTOU-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 VEENGDJNDWZTOU-UHFFFAOYSA-N 0.000 claims description 7
- UNQDVTXJGNPKAY-UHFFFAOYSA-N 8-ethyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=CC=C2CC UNQDVTXJGNPKAY-UHFFFAOYSA-N 0.000 claims description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- IWTSTYWGRNOWJQ-UHFFFAOYSA-N 2-(trifluoromethyl)-3h-benzo[f]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(C=C(C(C(=O)O)O3)C(F)(F)F)C3=CC=C21 IWTSTYWGRNOWJQ-UHFFFAOYSA-N 0.000 claims description 6
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical class NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims description 6
- KSDMMCFWQWBVBW-UHFFFAOYSA-N 2-sulfanylbenzaldehyde Chemical class SC1=CC=CC=C1C=O KSDMMCFWQWBVBW-UHFFFAOYSA-N 0.000 claims description 6
- ZFKBWSREWJOSSJ-UHFFFAOYSA-N 6,8-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=CC(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ZFKBWSREWJOSSJ-UHFFFAOYSA-N 0.000 claims description 6
- CSOISVJKLBMNCK-UHFFFAOYSA-N 6-(trifluoromethoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)OC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 CSOISVJKLBMNCK-UHFFFAOYSA-N 0.000 claims description 6
- XCTHXVRBSIHBAC-UHFFFAOYSA-N 6-chloro-2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound ClC1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 XCTHXVRBSIHBAC-UHFFFAOYSA-N 0.000 claims description 6
- DEIAIXWIMOETNX-UHFFFAOYSA-N 6-formyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O=CC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 DEIAIXWIMOETNX-UHFFFAOYSA-N 0.000 claims description 6
- ABNPGORLVYQTCX-UHFFFAOYSA-N 7-phenyl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=C1C1=CC=CC=C1 ABNPGORLVYQTCX-UHFFFAOYSA-N 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- JDAUSBADDDDUKJ-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)C1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 JDAUSBADDDDUKJ-UHFFFAOYSA-N 0.000 claims description 5
- ICNSSUXDLAOCAM-UHFFFAOYSA-N 2-(trifluoromethyl)-6-(trifluoromethylsulfanyl)-2h-chromene-3-carboxylic acid Chemical compound FC(F)(F)SC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 ICNSSUXDLAOCAM-UHFFFAOYSA-N 0.000 claims description 5
- XSKBUYZVRRYHKJ-UHFFFAOYSA-N 6-(4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1OC1=CC=C(OC(C(=C2)C(O)=O)C(F)(F)F)C2=C1 XSKBUYZVRRYHKJ-UHFFFAOYSA-N 0.000 claims description 5
- YHQKTWYBVAMUJX-UHFFFAOYSA-N 6-(benzylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 YHQKTWYBVAMUJX-UHFFFAOYSA-N 0.000 claims description 5
- NENVFGXZTXDKIF-UHFFFAOYSA-N 6-chloro-8-(4-chlorophenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=C(Cl)C=C1 NENVFGXZTXDKIF-UHFFFAOYSA-N 0.000 claims description 5
- CBMIVBLNFVXYHN-UHFFFAOYSA-N 6-chloro-8-propan-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2C(C)C CBMIVBLNFVXYHN-UHFFFAOYSA-N 0.000 claims description 5
- YSZVXNMIWQLFDC-UHFFFAOYSA-N 6-chloro-8-thiophen-2-yl-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C1=CC=CS1 YSZVXNMIWQLFDC-UHFFFAOYSA-N 0.000 claims description 5
- YKJCXFQLAGEPJU-UHFFFAOYSA-N 6-iodo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound IC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 YKJCXFQLAGEPJU-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- PCPVDBRLCKJFCI-UHFFFAOYSA-N ethyl 6-amino-2-(trifluoromethyl)-2h-chromene-3-carboxylate Chemical compound NC1=CC=C2OC(C(F)(F)F)C(C(=O)OCC)=CC2=C1 PCPVDBRLCKJFCI-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- AKYBWCBXYSTSIR-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-benzo[h]chromene-3-carboxylic acid Chemical compound C1=CC=CC2=C(OC(C(C(=O)O)=C3)C(F)(F)F)C3=CC=C21 AKYBWCBXYSTSIR-UHFFFAOYSA-N 0.000 claims description 4
- ASSYTOFEDCYDMO-UHFFFAOYSA-N 2-(trifluoromethyl)-2h-thiochromene-3-carboxylic acid Chemical compound C1=CC=C2SC(C(F)(F)F)C(C(=O)O)=CC2=C1 ASSYTOFEDCYDMO-UHFFFAOYSA-N 0.000 claims description 4
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical class CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 claims description 4
- YWZLKGBSKMLBMS-UHFFFAOYSA-N 3-(trifluoromethyl)-3h-[1]benzofuro[3,2-f]chromene-2-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC1=C2C=C(C(=O)O)C(C(F)(F)F)O1 YWZLKGBSKMLBMS-UHFFFAOYSA-N 0.000 claims description 4
- KJOSDRUNXOPTEP-UHFFFAOYSA-N 5,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1Cl KJOSDRUNXOPTEP-UHFFFAOYSA-N 0.000 claims description 4
- HMBUMPBGRPVQME-UHFFFAOYSA-N 6,7-dichloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound ClC1=C(Cl)C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 HMBUMPBGRPVQME-UHFFFAOYSA-N 0.000 claims description 4
- QOQKUIZOHDRLNJ-UHFFFAOYSA-N 6,8-dibromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC(Br)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 QOQKUIZOHDRLNJ-UHFFFAOYSA-N 0.000 claims description 4
- XUSRBZSQUXSUFO-UHFFFAOYSA-N 6-(3-chloro-4-methoxyphenoxy)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1OC1=CC=C(OC(C(=C2)C(O)=O)C(F)(F)F)C2=C1 XUSRBZSQUXSUFO-UHFFFAOYSA-N 0.000 claims description 4
- XRCIFEVLZNDSDG-UHFFFAOYSA-N 6-(4-hydroxybenzoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1C(=O)C1=CC=C(O)C=C1 XRCIFEVLZNDSDG-UHFFFAOYSA-N 0.000 claims description 4
- LJAIXLITIWWLMU-UHFFFAOYSA-N 6-(benzylsulfamoyl)-8-chloro-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C(Cl)=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CC=C1 LJAIXLITIWWLMU-UHFFFAOYSA-N 0.000 claims description 4
- WRWBASOXAVOXNF-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)N(C)C)=CC=C21 WRWBASOXAVOXNF-UHFFFAOYSA-N 0.000 claims description 4
- DBRFBZFRUCUHKM-UHFFFAOYSA-N 6-(furan-2-ylmethylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=1C=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC=1S(=O)(=O)NCC1=CC=CO1 DBRFBZFRUCUHKM-UHFFFAOYSA-N 0.000 claims description 4
- MQSZXCIMIPOLLQ-UHFFFAOYSA-N 6-(tert-butylsulfamoyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound O1C(C(F)(F)F)C(C(O)=O)=CC2=CC(S(=O)(=O)NC(C)(C)C)=CC=C21 MQSZXCIMIPOLLQ-UHFFFAOYSA-N 0.000 claims description 4
- NFSQSAYXIRPZAG-UHFFFAOYSA-N 6-(trifluoromethyl)-6h-[1,3]dioxolo[4,5-g]chromene-7-carboxylic acid Chemical compound C1=C2OC(C(F)(F)F)C(C(=O)O)=CC2=CC2=C1OCO2 NFSQSAYXIRPZAG-UHFFFAOYSA-N 0.000 claims description 4
- OODLETPYKNYFPC-UHFFFAOYSA-N 6-bromo-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound BrC1=CC=C2OC(C(F)(F)F)C(C(=O)O)=CC2=C1 OODLETPYKNYFPC-UHFFFAOYSA-N 0.000 claims description 4
- OPSPKIBCFWXEJT-UHFFFAOYSA-N 6-chloro-8-(2-phenylethynyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C=12OC(C(F)(F)F)C(C(=O)O)=CC2=CC(Cl)=CC=1C#CC1=CC=CC=C1 OPSPKIBCFWXEJT-UHFFFAOYSA-N 0.000 claims description 4
- UURZIRMVOPZSTF-UHFFFAOYSA-N 6-chloro-8-(3-methoxyphenyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound COC1=CC=CC(C=2C=3OC(C(=CC=3C=C(Cl)C=2)C(O)=O)C(F)(F)F)=C1 UURZIRMVOPZSTF-UHFFFAOYSA-N 0.000 claims description 4
- QJXCLFOKEYXFMB-UHFFFAOYSA-N 6-chloro-8-(methoxymethyl)-2-(trifluoromethyl)-2h-chromene-3-carboxylic acid Chemical compound C1=C(C(O)=O)C(C(F)(F)F)OC2=C1C=C(Cl)C=C2COC QJXCLFOKEYXFMB-UHFFFAOYSA-N 0.000 claims description 4
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US4448597P | 1997-04-21 | 1997-04-21 | |
PCT/US1998/007677 WO1998047890A1 (en) | 1997-04-21 | 1998-04-18 | Substituted benzopyran derivatives for the treatment of inflammation |
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NO995113D0 NO995113D0 (no) | 1999-10-20 |
NO995113L NO995113L (no) | 1999-12-21 |
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NO19995113A NO325249B1 (no) | 1997-04-21 | 1999-10-20 | Substituerte benzopyranderivater som antiinflammatoriske, farmasoytiske midler, samt fremgangsmater for fremstilling derav |
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US (3) | US6034256A (hu) |
EP (1) | EP0977748B1 (hu) |
JP (1) | JP4577534B2 (hu) |
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CN (2) | CN1196692C (hu) |
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AT (1) | ATE235481T1 (hu) |
AU (1) | AU742033B2 (hu) |
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BR (1) | BR9808953A (hu) |
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ES (1) | ES2194314T3 (hu) |
GE (1) | GEP20022739B (hu) |
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IL (2) | IL132296A0 (hu) |
IS (1) | IS1976B (hu) |
NO (1) | NO325249B1 (hu) |
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OA (1) | OA11302A (hu) |
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UA (1) | UA64746C2 (hu) |
WO (1) | WO1998047890A1 (hu) |
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