FI81796C - Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne. - Google Patents

Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne. Download PDF

Info

Publication number: FI81796C
Authority: FI; Finland
Prior art keywords: formula; thienyl; phenyl; furyl; oxindole
Prior art date: 1984-02-07

Application number

FI850491A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI850491A0 (fi

FI850491L (fi

FI81796B (fi

Inventor

Saul Bernard Kadin

Original Assignee

Pfizer

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.)

1984-02-07

Filing date

1985-02-06

Publication date

1990-12-10

1985-02-06 Application filed by Pfizer filed Critical Pfizer

1985-02-06 Publication of FI850491A0 publication Critical patent/FI850491A0/fi

1985-08-08 Publication of FI850491L publication Critical patent/FI850491L/fi

1989-09-15 Priority to FI894363A priority Critical patent/FI82448C/fi

1990-08-31 Publication of FI81796B publication Critical patent/FI81796B/fi

1990-12-10 Application granted granted Critical

1990-12-10 Publication of FI81796C publication Critical patent/FI81796C/fi

Links

-1 1,3-disubstituted 2-oxindol compound Chemical class 0.000 title claims description 190
238000000034 method Methods 0.000 title claims description 39
238000002360 preparation method Methods 0.000 title claims description 22
230000000202 analgesic effect Effects 0.000 title description 16
239000002260 anti-inflammatory agent Substances 0.000 title description 5
229940121363 anti-inflammatory agent Drugs 0.000 title description 5
239000000730 antalgic agent Substances 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 82
150000003839 salts Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000012948 isocyanate Substances 0.000 claims description 9
239000012442 inert solvent Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052770 Uranium Inorganic materials 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
239000000243 solution Substances 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
238000001914 filtration Methods 0.000 description 24
239000007787 solid Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
238000002844 melting Methods 0.000 description 10
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
208000002193 Pain Diseases 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
230000008018 melting Effects 0.000 description 9
239000002904 solvent Substances 0.000 description 9
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 8
241000699670 Mus sp. Species 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000002002 slurry Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 6
NFPZMLAKARIPMY-UHFFFAOYSA-N n-benzoyl-3-(furan-2-carbonyl)-2-oxo-3h-indole-1-carboxamide Chemical compound O=C1C(C(=O)C=2OC=CC=2)C2=CC=CC=C2N1C(=O)NC(=O)C1=CC=CC=C1 NFPZMLAKARIPMY-UHFFFAOYSA-N 0.000 description 6
150000005623 oxindoles Chemical class 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229940086542 triethylamine Drugs 0.000 description 6
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 5
HSYFISNDMZKGRS-UHFFFAOYSA-N 4-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)C(=O)N2 HSYFISNDMZKGRS-UHFFFAOYSA-N 0.000 description 5
208000004998 Abdominal Pain Diseases 0.000 description 5
208000002881 Colic Diseases 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 5
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 5
230000003110 anti-inflammatory effect Effects 0.000 description 5
239000003814 drug Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
125000003944 tolyl group Chemical group 0.000 description 5
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
LURYMYITPCOQAU-UHFFFAOYSA-N benzoyl isocyanate Chemical compound O=C=NC(=O)C1=CC=CC=C1 LURYMYITPCOQAU-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000010410 layer Substances 0.000 description 4
239000002609 medium Substances 0.000 description 4
239000000376 reactant Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
230000004044 response Effects 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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 description 3
JUPOEJXDARZUBY-UHFFFAOYSA-N 3-(thiophene-2-carbonyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)C1=CC=CS1 JUPOEJXDARZUBY-UHFFFAOYSA-N 0.000 description 3
XNSPDJAXCBZCRV-UHFFFAOYSA-N 4-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1CC(=O)N2 XNSPDJAXCBZCRV-UHFFFAOYSA-N 0.000 description 3
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 3
CENVPIZOTHULGJ-UHFFFAOYSA-N 6-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2CC(=O)NC2=C1 CENVPIZOTHULGJ-UHFFFAOYSA-N 0.000 description 3
RVXLBLSGEPQBIO-UHFFFAOYSA-N 6-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=C2C(=O)C(=O)NC2=C1 RVXLBLSGEPQBIO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000000679 carrageenan Substances 0.000 description 3
229920001525 carrageenan Polymers 0.000 description 3
235000010418 carrageenan Nutrition 0.000 description 3
229940113118 carrageenan Drugs 0.000 description 3
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
230000007774 longterm Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
IOMSWISKMUXPLV-UHFFFAOYSA-N n-benzoyl-2-oxo-3h-indole-1-carboxamide Chemical compound O=C1CC2=CC=CC=C2N1C(=O)NC(=O)C1=CC=CC=C1 IOMSWISKMUXPLV-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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 3
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 2
OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 2
XWLIAACTIOFOOA-UHFFFAOYSA-N 3-(2-thiophen-2-ylacetyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)CC1=CC=CS1 XWLIAACTIOFOOA-UHFFFAOYSA-N 0.000 description 2
MVZPGVKQORMMNZ-UHFFFAOYSA-N 3-(furan-2-carbonyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)C1=CC=CO1 MVZPGVKQORMMNZ-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
WPXZFSQTAFULLU-UHFFFAOYSA-N 4-chloro-3-hydrazinylindol-2-one Chemical compound C1=CC(Cl)=C2C(=NN)C(=O)NC2=C1 WPXZFSQTAFULLU-UHFFFAOYSA-N 0.000 description 2
WIEJKTTWCGNQHH-UHFFFAOYSA-N 5-butyl-1h-indole-2,3-dione Chemical compound CCCCC1=CC=C2NC(=O)C(=O)C2=C1 WIEJKTTWCGNQHH-UHFFFAOYSA-N 0.000 description 2
DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 2
FIWADZAJMKCAHJ-UHFFFAOYSA-N 5-fluoro-3-methyl-1,3-dihydroindole-2-thione Chemical compound C1=C(F)C=C2C(C)C(=S)NC2=C1 FIWADZAJMKCAHJ-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
208000017667 Chronic Disease Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
MDIAKIHKBBNYHF-UHFFFAOYSA-N Ethyl 2-(methylthio)acetate Chemical compound CCOC(=O)CSC MDIAKIHKBBNYHF-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
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 2
102000003820 Lipoxygenases Human genes 0.000 description 2
108090000128 Lipoxygenases Proteins 0.000 description 2
229920005479 Lucite® Polymers 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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150000008065 acid anhydrides Chemical class 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000002411 adverse Effects 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 2
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Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

FI850491A 1984-02-07 1985-02-06 Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne. FI81796C (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
FI894363A FI82448C (fi)	1984-02-07	1989-09-15	2-oxindolderivat.

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US57790384A	1984-02-07	1984-02-07
US57790384		1984-02-07
US61986184A	1984-06-12	1984-06-12
US61986184		1984-06-12

Publications (4)

Publication Number	Publication Date
FI850491A0 FI850491A0 (fi)	1985-02-06
FI850491L FI850491L (fi)	1985-08-08
FI81796B FI81796B (fi)	1990-08-31
FI81796C true FI81796C (fi)	1990-12-10

Family

ID=27077370

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI850491A FI81796C (fi)	1984-02-07	1985-02-06	Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne.

Country Status (12)

Country	Link
AU (1)	AU552760B2 (pt)
CA (1)	CA1255657A (pt)
EG (1)	EG17329A (pt)
ES (3)	ES8605232A1 (pt)
FI (1)	FI81796C (pt)
HU (2)	HU193942B (pt)
IL (1)	IL74251A (pt)
NO (1)	NO165798C (pt)
NZ (1)	NZ211052A (pt)
PH (2)	PH20395A (pt)
PT (1)	PT79926B (pt)
ZW (1)	ZW1585A1 (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PH23498A (en) *	1984-08-06	1989-08-16	Sterling Drug Inc	3-carbonyl-1-aminoalkyl-1h-indoles,composition and use thereof

1985
- 1985-02-05 ZW ZW1585A patent/ZW1585A1/xx unknown
- 1985-02-05 PT PT7992685A patent/PT79926B/pt unknown
- 1985-02-05 CA CA000473576A patent/CA1255657A/en not_active Expired
- 1985-02-05 PH PH31819A patent/PH20395A/en unknown
- 1985-02-05 NZ NZ21105285A patent/NZ211052A/xx unknown
- 1985-02-05 ES ES540133A patent/ES8605232A1/es not_active Expired
- 1985-02-05 IL IL74251A patent/IL74251A/xx not_active IP Right Cessation
- 1985-02-06 AU AU38467/85A patent/AU552760B2/en not_active Expired
- 1985-02-06 NO NO850443A patent/NO165798C/no not_active IP Right Cessation
- 1985-02-06 HU HU45285A patent/HU193942B/hu unknown
- 1985-02-06 EG EG7185A patent/EG17329A/xx active
- 1985-02-06 FI FI850491A patent/FI81796C/fi not_active IP Right Cessation
- 1985-02-06 HU HU45285D patent/HUT39159A/hu unknown
- 1985-11-15 ES ES548944A patent/ES8605776A1/es not_active Expired
- 1985-11-15 ES ES548943A patent/ES8606273A1/es not_active Expired
1986
- 1986-07-01 PH PH33969A patent/PH23393A/en unknown

Also Published As

Publication number	Publication date
AU552760B2 (en)	1986-06-19
ES540133A0 (es)	1986-03-16
PT79926A (en)	1985-03-01
ZW1585A1 (en)	1985-06-19
AU3846785A (en)	1985-08-15
NO165798C (no)	1991-04-10
ES8605776A1 (es)	1986-04-01
PH20395A (en)	1986-12-12
IL74251A0 (en)	1985-05-31
HUT39159A (en)	1986-08-28
PH23393A (en)	1989-07-26
ES8605232A1 (es)	1986-03-16
ES548943A0 (es)	1986-04-16
ES8606273A1 (es)	1986-04-16
NO165798B (no)	1991-01-02
NO850443L (no)	1985-08-08
CA1255657A (en)	1989-06-13
HU193942B (en)	1987-12-28
HUT37753A (en)	1986-02-28
NZ211052A (en)	1988-08-30
EG17329A (en)	1991-11-30
FI850491A0 (fi)	1985-02-06
FI850491L (fi)	1985-08-08
IL74251A (en)	1990-01-18
FI81796B (fi)	1990-08-31
PT79926B (en)	1987-02-05
ES548944A0 (es)	1986-04-01

Publication	Publication Date	Title
KR860001873B1 (ko)	1986-10-24	3-치환된 2-옥신돌-1-카르복스아미드의 제조방법
US7022708B2 (en)	2006-04-04	4-piperazinyl benzenesulfonyl indoles and uses thereof
EP0175551B1 (en)	1989-05-10	Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4721712A (en)	1988-01-26	1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
HUT71553A (en)	1995-12-28	2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties
IL109234A (en)	1998-04-05	Indole derivatives, their preparation and pharmaceutical compositions containing them
US4658037A (en)	1987-04-14	Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
EP0153818B1 (en)	1989-03-15	1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
KR860001874B1 (ko)	1986-10-24	2-옥스인돌-1-카복스 아미드의 제조방법
FI81796C (fi)	1990-12-10	Foerfarande foer framstaellning av en 1,3-disubstituerad 2-oxindolfoerening som fungerar som ett analgetiskt och anti-inflammatoriskt aemne.
FI80270C (fi)	1990-05-10	Foerfarande foer framstaellning av analgetiska och anti-inflammatoriska 1,3-diacyl-2-oxoindol-foereningar och mellanprodukter.
US4665194A (en)	1987-05-12	Process for making 2-oxindole-1-carboxamides and intermediates therefor
JPH0437076B2 (pt)	1992-06-18
FI80016C (fi)	1990-04-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara 2-oxindol-1-karboxiamidderivat.
FI92827B (fi)	1994-09-30	Menetelmä terapeuttisesti käyttökelpoisten 1-heteroaryyli-3-asyyli-2-oksindolijohdannaisten valmistamiseksi
CA1289556C (en)	1991-09-24	1- or 3-monosubstituted 2-oxindole compound intermediates useful for the production of analgesic and anti-inflammatory agents
IE57689B1 (en)	1993-02-24	1,3-disubstituted oxindoles as analgesic and antiinflammatory agents
CS252498B2 (cs)	1987-09-17	Způsob výroby 1,3-disubstituovaných 2-oxindoiů
HK1135986A1 (en)	2010-06-18	4-(heterocyclyl)alkyl-n-(arylsulfonyl) indole compounds and their use as 5-ht6 ligands
HK1135986B (en)	2013-02-08	4-(heterocyclyl)alkyl-n-(arylsulfonyl) indole compounds and their use as 5-ht6 ligands
CS252847B2 (cs)	1987-10-15	Způsob výroby N,3-disubstituovaných 2-oxindol-1-karboxamidů
CZ418791A3 (en)	1993-05-12	2-oxo-indole-1-carboxamides substituted in position 3 as analgesic and antiphlogistic agents

Legal Events

Date	Code	Title	Description
2004-08-31	FG	Patent granted	Owner name: PFIZER INC.
2005-03-02	MA	Patent expired