NO790821L - Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-2-(substituerte-thio)pyrroler og deres tilsvarende sulfoxyder og sulfoner - Google Patents

Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-2-(substituerte-thio)pyrroler og deres tilsvarende sulfoxyder og sulfoner

Info

Publication number: NO790821L
Authority: NO; Norway
Prior art keywords: compound according; product; methyl; mixture; alkyl
Prior art date: 1978-03-13

Application number

NO790821A

Other languages

English (en)

Norwegian (no)

Inventor

Saul Carl Cherkofsky

Original Assignee

Du Pont

Priority date (The priority date 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 date listed.)

1978-03-13

Filing date

1979-03-12

Publication date

1979-09-14

1979-03-12 Application filed by Du Pont filed Critical Du Pont

1979-09-14 Publication of NO790821L publication Critical patent/NO790821L/no

Links

-1 SUBSTITUTED-THIO Chemical class 0.000 title claims description 22
238000000034 method Methods 0.000 title abstract description 37
238000002360 preparation method Methods 0.000 title abstract description 11
230000003110 anti-inflammatory effect Effects 0.000 title abstract description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 15
150000001875 compounds Chemical class 0.000 claims description 44
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 7
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
150000001336 alkenes Chemical class 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
150000007529 inorganic bases Chemical class 0.000 claims 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims 1
150000003457 sulfones Chemical class 0.000 abstract description 4
150000003462 sulfoxides Chemical class 0.000 abstract description 4
230000008569 process Effects 0.000 abstract description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000000203 mixture Substances 0.000 description 44
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
238000004458 analytical method Methods 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
239000013078 crystal Substances 0.000 description 10
238000012360 testing method Methods 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 9
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
206010003246 arthritis Diseases 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
VNMNSTIGSQBDPI-UHFFFAOYSA-N 2,3-diphenyl-1h-pyrrole Chemical class N1C=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VNMNSTIGSQBDPI-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000000463 material Substances 0.000 description 6
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000003826 tablet Substances 0.000 description 6
208000002193 Pain Diseases 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
210000002683 foot Anatomy 0.000 description 5
150000003233 pyrroles Chemical class 0.000 description 5
IPYGWVOVGORWKF-UHFFFAOYSA-N 2,3-bis(4-fluorophenyl)-5-(trifluoromethylsulfanyl)-1h-pyrrole Chemical class C1=CC(F)=CC=C1C1=C(C=2C=CC(F)=CC=2)NC(SC(F)(F)F)=C1 IPYGWVOVGORWKF-UHFFFAOYSA-N 0.000 description 4
WGVQZBURQZKDBN-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC=C1 WGVQZBURQZKDBN-UHFFFAOYSA-N 0.000 description 4
GVJWJQJTASSMOL-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)-5-(trifluoromethylsulfanyl)-1h-pyrrole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(SC(F)(F)F)=C1 GVJWJQJTASSMOL-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
239000002260 anti-inflammatory agent Substances 0.000 description 4
229940121363 anti-inflammatory agent Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
235000011089 carbon dioxide Nutrition 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000007789 gas Substances 0.000 description 4
239000005457 ice water Substances 0.000 description 4
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
238000002390 rotary evaporation Methods 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
WJYMBVJBSFMDLE-UHFFFAOYSA-N 2-(dimethylhydrazinylidene)acetaldehyde Chemical compound CN(C)N=CC=O WJYMBVJBSFMDLE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000007903 gelatin capsule Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
LXCFILQKKLGQFO-UHFFFAOYSA-N p-hydroxybenzoic acid methyl ester Natural products COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
OTKCEEWUXHVZQI-UHFFFAOYSA-N 1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(=O)CC1=CC=CC=C1 OTKCEEWUXHVZQI-UHFFFAOYSA-N 0.000 description 2
BULRPSMQHLOYEZ-UHFFFAOYSA-N 1-[4,5-bis(4-methoxyphenyl)-1h-pyrrol-2-yl]-2,2,2-trifluoroethanone Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C(=O)C(F)(F)F)=C1 BULRPSMQHLOYEZ-UHFFFAOYSA-N 0.000 description 2
OHOSQDJLNADBBF-UHFFFAOYSA-N 2,3-bis(4-chlorophenyl)-4-propyl-1h-pyrrole Chemical compound CCCC1=CNC(C=2C=CC(Cl)=CC=2)=C1C1=CC=C(Cl)C=C1 OHOSQDJLNADBBF-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
XAAUTNQRSSJJGO-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1h-pyrrole-2-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C=O)=C1 XAAUTNQRSSJJGO-UHFFFAOYSA-N 0.000 description 2
BRNDHRUVIBSOAO-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-1h-pyrrole-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)NC(C(O)=O)=C1 BRNDHRUVIBSOAO-UHFFFAOYSA-N 0.000 description 2
IBGBVQURUWBTKN-UHFFFAOYSA-N 4,5-diphenyl-1h-pyrrole-2,3-dicarboxylic acid Chemical compound OC(=O)C1=C(C(=O)O)NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IBGBVQURUWBTKN-UHFFFAOYSA-N 0.000 description 2
NIUHOLQUENISHN-UHFFFAOYSA-N 4-methyl-2,3-diphenyl-1h-pyrrole Chemical compound CC1=CNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NIUHOLQUENISHN-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000124008 Mammalia Species 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
230000009471 action Effects 0.000 description 2
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000006114 decarboxylation reaction Methods 0.000 description 2
VQMOVERDZSFLOQ-UHFFFAOYSA-N dimethyl 4,5-diphenyl-1h-pyrrole-2,3-dicarboxylate Chemical compound COC(=O)C1=C(C(=O)OC)NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 VQMOVERDZSFLOQ-UHFFFAOYSA-N 0.000 description 2
VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
HTSROGFJSMXEFJ-UHFFFAOYSA-N ethyl 4,5-diphenyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=CNC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 HTSROGFJSMXEFJ-UHFFFAOYSA-N 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
238000013265 extended release Methods 0.000 description 2
210000000548 hind-foot Anatomy 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 2
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 2
229960002216 methylparaben Drugs 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
239000003182 parenteral nutrition solution Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000010998 test method Methods 0.000 description 2
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
238000001665 trituration Methods 0.000 description 2
XDIYNQZUNSSENW-UUBOPVPUSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XDIYNQZUNSSENW-UUBOPVPUSA-N 0.000 description 1
GJJYFCVVBKFNBF-UHFFFAOYSA-N (4,5-diphenyl-1h-pyrrol-2-yl) thiocyanate Chemical compound N1C(SC#N)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GJJYFCVVBKFNBF-UHFFFAOYSA-N 0.000 description 1
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IAISXHNMHVYJBM-UHFFFAOYSA-N 2,3-diphenyl-5-(trifluoromethylsulfanyl)-1h-pyrrole Chemical compound N1C(SC(F)(F)F)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 IAISXHNMHVYJBM-UHFFFAOYSA-N 0.000 description 1
ZVAKZVDJIUFFFP-UHFFFAOYSA-N 2-chlorooxolane Chemical compound ClC1CCCO1 ZVAKZVDJIUFFFP-UHFFFAOYSA-N 0.000 description 1
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
NVBQXVCAUWQLSD-UHFFFAOYSA-N 5-methylsulfanyl-2,3-diphenyl-1h-pyrrole Chemical compound N1C(SC)=CC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 NVBQXVCAUWQLSD-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
235000006491 Acacia senegal Nutrition 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
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HUUSTUALCPTCGJ-UHFFFAOYSA-N n,n-diethylcarbamothioyl chloride Chemical compound CCN(CC)C(Cl)=S HUUSTUALCPTCGJ-UHFFFAOYSA-N 0.000 description 1
OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000001151 other effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
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239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
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159000000000 sodium salts Chemical class 0.000 description 1
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239000003549 soybean oil Substances 0.000 description 1
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125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
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208000024891 symptom Diseases 0.000 description 1
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239000000454 talc Substances 0.000 description 1
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
238000006055 thio-Claisen rearrangement reaction Methods 0.000 description 1
DTMHTVJOHYTUHE-UHFFFAOYSA-N thiocyanogen Chemical compound N#CSSC#N DTMHTVJOHYTUHE-UHFFFAOYSA-N 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000008736 traumatic injury Effects 0.000 description 1
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238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/323—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atoms
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/36—Oxygen or sulfur atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Rheumatology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

NO790821A 1978-03-13 1979-03-12 Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-2-(substituerte-thio)pyrroler og deres tilsvarende sulfoxyder og sulfoner NO790821L (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date
US88633778A	1978-03-13	1978-03-13
US97220178A	1978-12-28	1978-12-28
US1025979A	1979-02-08	1979-02-08

Publications (1)

Publication Number	Publication Date
NO790821L true NO790821L (no)	1979-09-14

Family

ID=27359191

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO790821A NO790821L (no)	1978-03-13	1979-03-12	Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-2-(substituerte-thio)pyrroler og deres tilsvarende sulfoxyder og sulfoner

Country Status (17)

Country	Link
EP (1)	EP0005156B1 (da)
JP (1)	JPS54141766A (da)
AR (2)	AR225739A1 (da)
AU (1)	AU527243B2 (da)
CA (1)	CA1126275A (da)
DE (1)	DE2963707D1 (da)
DK (1)	DK75779A (da)
ES (2)	ES478556A1 (da)
FI (1)	FI790852A7 (da)
GR (1)	GR66513B (da)
IL (1)	IL56856A (da)
MX (1)	MX5685E (da)
NO (1)	NO790821L (da)
NZ (1)	NZ189881A (da)
PH (1)	PH14378A (da)
PT (1)	PT69336A (da)
YU (1)	YU58979A (da)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4267184A (en) *	1979-02-08	1981-05-12	E. I. Du Pont De Nemours And Company	Antiinflammatory 4,5-diaryl-2-(substituted-thio)pyrroles and their corresponding sulfoxides and sulfones
DK350280A (da) *	1979-08-27	1981-02-28	Du Pont	Fremgangsmaade til fremstilling af 4,5-diaryl-alfapolyfluoralkyl-1h-pyrrol-2-methanoler og 1-(4,5-diaryl-1h-pyrrol-2-yl)-polyfluoralkanoner
US4267190A (en) *	1980-04-18	1981-05-12	E. I. Du Pont De Nemours And Company	Antiinflammatory 4,5-diaryl-α,α-bis(polyfluoromethyl)-1H-pyrrole-2-methanethiols
EP0044485A1 (en) *	1980-07-21	1982-01-27	E.I. Du Pont De Nemours And Company	Antiinflammatory 2,3-diaryl-5(2,2,2-trifluoro-1-(trifluoromethyl)-ethyl)-1H-pyrroles
DE3317653A1 (de) *	1983-05-14	1984-11-15	Gödecke AG, 1000 Berlin	2-alkylthio-1-aminoalkyl-2-pyrrolin-3-carbonitrile, verfahren zu deren herstellung sowie deren verwendung bei der prophylaxe und therapie thrombotischer zustaende
US5306827A (en) *	1991-12-04	1994-04-26	American Cyanamid Company	Haloalkylthio, -sulfinyl and -sulfonyl arylpyrrole insecticidal and acaricidal agents
US5492925A (en) *	1993-08-31	1996-02-20	American Cyanamid Company	Thienyl-and furylpyrrole insecticidal and acaricidal agents
FR2874012B1 (fr) *	2004-08-09	2008-08-22	Sanofi Synthelabo	Derives de pyrrole, leur preparation et leur utlisation en therapeutique
MY210229A (en)	2009-02-25	2025-09-04	Takeda Pharmaceuticals Co	Process for producing pyrrole compound

1979
- 1979-02-21 DK DK75779A patent/DK75779A/da not_active Application Discontinuation
- 1979-03-09 PH PH22271A patent/PH14378A/en unknown
- 1979-03-12 EP EP79100736A patent/EP0005156B1/en not_active Expired
- 1979-03-12 NO NO790821A patent/NO790821L/no unknown
- 1979-03-12 CA CA323,172A patent/CA1126275A/en not_active Expired
- 1979-03-12 DE DE7979100736T patent/DE2963707D1/de not_active Expired
- 1979-03-12 NZ NZ189881A patent/NZ189881A/xx unknown
- 1979-03-12 IL IL56856A patent/IL56856A/xx unknown
- 1979-03-12 MX MX797806U patent/MX5685E/es unknown
- 1979-03-12 ES ES478556A patent/ES478556A1/es not_active Expired
- 1979-03-12 YU YU00589/79A patent/YU58979A/xx unknown
- 1979-03-12 PT PT69336A patent/PT69336A/pt unknown
- 1979-03-12 GR GR58568A patent/GR66513B/el unknown
- 1979-03-13 FI FI790852A patent/FI790852A7/fi not_active Application Discontinuation
- 1979-03-13 AR AR275794A patent/AR225739A1/es active
- 1979-03-13 JP JP2926779A patent/JPS54141766A/ja active Pending
- 1979-03-13 AU AU45040/79A patent/AU527243B2/en not_active Ceased
- 1979-09-14 ES ES484196A patent/ES484196A1/es not_active Expired
1980
- 1980-10-16 AR AR282895A patent/AR224276A1/es active

Also Published As

Publication number	Publication date
ES484196A1 (es)	1980-05-16
MX5685E (es)	1983-12-09
NZ189881A (en)	1981-02-11
AR224276A1 (es)	1981-11-13
AU527243B2 (en)	1983-02-24
ES478556A1 (es)	1979-12-16
DE2963707D1 (en)	1982-11-04
EP0005156A1 (en)	1979-11-14
IL56856A (en)	1982-09-30
CA1126275A (en)	1982-06-22
FI790852A7 (fi)	1979-09-14
AU4504079A (en)	1979-09-20
IL56856A0 (en)	1979-05-31
DK75779A (da)	1979-09-14
AR225739A1 (es)	1982-04-30
PT69336A (en)	1979-04-01
EP0005156B1 (en)	1982-09-22
PH14378A (en)	1981-06-17
GR66513B (da)	1981-03-24
JPS54141766A (en)	1979-11-05
YU58979A (en)	1983-04-30

Publication	Publication Date	Title
US4267184A (en)	1981-05-12	Antiinflammatory 4,5-diaryl-2-(substituted-thio)pyrroles and their corresponding sulfoxides and sulfones
US4302461A (en)	1981-11-24	Antiinflammatory 5-substituted-2,3-diarylthiophenes
DE69115134T2 (de)	1996-06-13	Pyranderivate zur Verwendung als 5-Lipoxygenasehemmer.
US4198421A (en)	1980-04-15	Antiinflammatory 2-substituted-dibenzo[2,3:6,7]oxepino[4,5-d]imidazoles
JPS6089474A (ja)	1985-05-20	モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤
GB1587373A (en)	1981-04-01	Anti-inflammatory 1-substituted - 4,5-diaryl-2-(substituted thio) imidazoles and their corresponding sulphoxides and sulphones
US4438117A (en)	1984-03-20	2-Substituted thio-4,5-diarylpyrimidines
EP0181136B1 (en)	1992-03-25	Oxindole antiinflammatory agents
NO790821L (no)	1979-09-14	Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-2-(substituerte-thio)pyrroler og deres tilsvarende sulfoxyder og sulfoner
US4159338A (en)	1979-06-26	Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones
US4652582A (en)	1987-03-24	Antiinflammatory-2-halo-4,5-diarylpyrroles
US4820827A (en)	1989-04-11	2,3-diaryl-5-bromothiophene compounds of use for the treatment of inflammaton and dysmenorrhea
FI80032B (fi)	1989-12-29	Foer behandling av oegats inre tryck an- vaendbara 2-sulfamoylbenzo/b/tiofenderivat.
EP0087629B1 (en)	1986-01-15	Antiinflammatory and/or analgesic 2,3-diaryl-5-halo thiophenes
JP2707936B2 (ja)	1998-02-04	β−オキソ−β−ベンゼンプロパンチオアミド誘導体
NO811321L (no)	1981-10-19	Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-alfa-(polyfluoralkyl)-1h-pyrrol-2-methanaminer
NO802528L (no)	1981-03-02	Fremgangsmaate ved fremstilling av antiinflammatorisk aktive 4,5-diaryl-alfa-polyfluoralkyl-1h pyrrol-2-methanoler og 1-(4,5-diaryl-1h-pyrrol-2-yl)polyfluoralkanoner
DE60129445T2 (de)	2008-04-24	Quinolin-derivate als antientzündungsmittel
GB1564184A (en)	1980-04-02	Antiinflammatory 4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulphoxides and sulphones
KR960012367B1 (ko)	1996-09-20	2-알킬설피닐-4(3h)-퀴나졸리논 유도체, 이의 제조방법 및 약제학적 조성물
JPS597168A (ja)	1984-01-14	カルボスチリル誘導体
FI89802C (fi)	1993-11-25	Foerfarande foer framstaellning av terapeutiskt aktiva 3,4-dihydro-2-alkyl-3-oxo-n-aryl-2h-/1/bensotieno/3,2-e/-1,2-tiazin-4-karboxiamid-1,1-dioxiderivat och 3,4-dihydro-2-alkyl-3-oxo-2h-/1/bensotieno/3,2-e/-1,2-tiazin-1,1-dioxifoereningar
EP0011115B1 (en)	1982-01-20	Antiinflammatory 2-substituted-1h-phenanthro(9,10-d)imidazoles, their preparation and pharmaceutical compositions containing them
US4215135A (en)	1980-07-29	Antiinflammatory 2-substituted-1H-phenanthro[9,10-d]imidazoles
US4256753A (en)	1981-03-17	4-(2-Pyridylamino)phenylacetic acid derivatives