NO310974B1 - Indolin-2-on-derivater, anvendelse derav, fremgangsmate for fremstilling av dem og farmasoytiske preparater inneholdende dem - Google Patents
Indolin-2-on-derivater, anvendelse derav, fremgangsmate for fremstilling av dem og farmasoytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO310974B1 NO310974B1 NO19981817A NO981817A NO310974B1 NO 310974 B1 NO310974 B1 NO 310974B1 NO 19981817 A NO19981817 A NO 19981817A NO 981817 A NO981817 A NO 981817A NO 310974 B1 NO310974 B1 NO 310974B1
- Authority
- NO
- Norway
- Prior art keywords
- spiro
- indolin
- compound
- ethoxy
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 51
- 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 194
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 146
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 72
- 239000002904 solvent Substances 0.000 claims description 58
- -1 benzyloxycarbonylamino Chemical group 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 42
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- 150000004677 hydrates Chemical class 0.000 claims description 27
- 239000012453 solvate Substances 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
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- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 21
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
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- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 125000003277 amino group Chemical group 0.000 claims description 4
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- 229960002198 irbesartan Drugs 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- 230000009471 action Effects 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- ODFOZFFJBAJZQG-UHFFFAOYSA-M sodium;1,4-dioxaspiro[4.5]decane-8-carboxylate Chemical compound [Na+].C1CC(C(=O)[O-])CCC21OCCO2 ODFOZFFJBAJZQG-UHFFFAOYSA-M 0.000 description 1
- BLXAGSNYHSQSRC-UHFFFAOYSA-M sodium;2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=CC=CC=C1S([O-])(=O)=O BLXAGSNYHSQSRC-UHFFFAOYSA-M 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- 238000012453 sprague-dawley rat model Methods 0.000 description 1
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- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000002536 vasopressin receptor antagonist Substances 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9512533A FR2740136B1 (fr) | 1995-10-24 | 1995-10-24 | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| PCT/FR1996/001666 WO1997015556A1 (fr) | 1995-10-24 | 1996-10-24 | Derives 3-spiro-indolin-2-one comme ligands des recepteurs de la vasopressine et/ou de l'ocytocine |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981817L NO981817L (no) | 1998-04-23 |
| NO981817D0 NO981817D0 (no) | 1998-04-23 |
| NO310974B1 true NO310974B1 (no) | 2001-09-24 |
Family
ID=9483867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981817A NO310974B1 (no) | 1995-10-24 | 1998-04-23 | Indolin-2-on-derivater, anvendelse derav, fremgangsmate for fremstilling av dem og farmasoytiske preparater inneholdende dem |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US5994350A (cs) |
| EP (1) | EP0873309B1 (cs) |
| JP (2) | JP3274471B2 (cs) |
| KR (1) | KR100298925B1 (cs) |
| CN (1) | CN1106384C (cs) |
| AR (1) | AR004225A1 (cs) |
| AT (1) | ATE229940T1 (cs) |
| AU (1) | AU715841B2 (cs) |
| BR (1) | BR9611198A (cs) |
| CZ (1) | CZ295585B6 (cs) |
| DE (1) | DE69625517T2 (cs) |
| DK (1) | DK0873309T3 (cs) |
| EE (1) | EE04433B1 (cs) |
| ES (1) | ES2191769T3 (cs) |
| FR (1) | FR2740136B1 (cs) |
| HU (1) | HUP9900331A3 (cs) |
| IL (1) | IL124002A (cs) |
| IN (1) | IN185328B (cs) |
| IS (1) | IS1949B (cs) |
| MY (1) | MY115864A (cs) |
| NO (1) | NO310974B1 (cs) |
| NZ (1) | NZ320352A (cs) |
| PL (1) | PL187093B1 (cs) |
| RU (1) | RU2167864C2 (cs) |
| SK (1) | SK284546B6 (cs) |
| TR (1) | TR199800719T2 (cs) |
| TW (1) | TW474917B (cs) |
| UA (1) | UA59345C2 (cs) |
| WO (1) | WO1997015556A1 (cs) |
| ZA (1) | ZA968945B (cs) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2757157B1 (fr) * | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2775598A1 (fr) | 1998-03-06 | 1999-09-10 | Sanofi Sa | Compositions pharmaceutiques contenant en association un antagoniste selectif des recepteurs v1a de l'arginine-vasopressine et un antagoniste selectif des recepteur v2 de l'arginine-vasopressine |
| FR2778103A1 (fr) * | 1998-04-29 | 1999-11-05 | Sanofi Sa | Compositions pharmaceutiques contenant en association un antagoniste v1a de l'arginine-vasopressine et un antagoniste des recepteurs at1 de l'angiotensine ii |
| HU225703B1 (en) * | 1999-07-15 | 2007-06-28 | Sanofi Aventis | Process for producing spiro[cis-4-(betha-hydroxy-ethyloxi)-cyclohexane-[3h]indole]-2'[1'h]-one derivatives |
| HU225150B1 (en) * | 1999-07-15 | 2006-07-28 | Sanofi Aventis | Novel process for producing 2-methoxy-4-(t-butylaminocarbonyl)-benzenesulfonyl chloride |
| HUP9902374A3 (en) | 1999-07-15 | 2002-11-28 | Sanofi Aventis | Process for producing spiro[(4-cyclohexanone)-[3h]indol-2'[1'h]-on derivatives and intermediates |
| HUP9902376A3 (en) * | 1999-07-15 | 2002-11-28 | Sanofi Aventis | Process for producing n-(1,1-dimethyl)-4-[[s'-ethoxi-4-cis-[2-(4-morpholino)-ethoxi]-2'-oxospiro[cyclohexane-1,3'-[3h]indole]-1'(2'h)yl]-sulfonyl]-3-methoxybenzamide and its salts |
| US20030103983A1 (en) * | 2002-05-09 | 2003-06-05 | Pressler Milton Lethan | Ace inhibitor-vasopressin antagonist combinations |
| WO2002044179A1 (fr) * | 2000-11-28 | 2002-06-06 | Yamanouchi Pharmaceutical Co., Ltd. | Dérivés de 1,4,5,6-tétrahydroimidazo[4,5-d]diazépine ou sels de ces derniers |
| AU2002231098A1 (en) * | 2000-12-15 | 2002-06-24 | Emory University | Nonpeptide agonists and antagonists of vasopressin receptors |
| WO2002064022A2 (en) * | 2001-02-14 | 2002-08-22 | Duke University | Therapy for cerebral vasospasm |
| DE60204154T2 (de) | 2001-07-31 | 2006-01-19 | Sanofi-Aventis | Verfahren zur herstellung von 3 spiro'cyclohexan-1,3'-'3h!indolin-2'-on!derivaten |
| US7414052B2 (en) | 2004-03-30 | 2008-08-19 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| US7517899B2 (en) | 2004-03-30 | 2009-04-14 | Wyeth | Phenylaminopropanol derivatives and methods of their use |
| DE602005025755D1 (de) | 2004-06-04 | 2011-02-17 | Teva Pharma | Irbesartan enthaltende pharmazeutische zusammensetzung |
| FR2874920B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one comme ligand des recepteurs de la vasopressine |
| FR2874921B1 (fr) * | 2004-09-09 | 2006-10-20 | Sanofi Aventis Sa | Derives de 3-spiro-indolin-2-one, leur preparation et leur application en therapeutique |
| EP1836183A2 (en) * | 2004-12-13 | 2007-09-26 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| WO2006072458A2 (de) * | 2004-12-31 | 2006-07-13 | Abbott Gmbh & Co. Kg | Substituierte oxindol-derivate, diese enthaltende arzneimittel und deren verwendung |
| DE102005014936A1 (de) * | 2005-03-24 | 2006-12-14 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
| MY145694A (en) | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| MY144968A (en) | 2005-04-11 | 2011-11-30 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| US7351706B2 (en) * | 2006-01-05 | 2008-04-01 | Hoffmann-La Roche Inc. | Indol-3-yl-carbonyl-spiro-piperidine derivatives |
| AR063280A1 (es) | 2006-10-12 | 2009-01-21 | Xenon Pharmaceuticals Inc | Uso de compuestos de espiro-oxindol como agentes terapeuticos |
| AU2007307635A1 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Tricyclic spiro-oxindole derivatives and their uses as therapeutic agents |
| AR063278A1 (es) * | 2006-10-12 | 2009-01-14 | Xenon Pharmaceuticals Inc | Compuestos de espiro-oxindol, una composicion farmaceutica que los comprende y su uso para el tratamiento de enfermedades o condiciones mediadas por los canales de sodio. |
| FR2927625B1 (fr) | 2008-02-19 | 2010-03-12 | Sanofi Aventis | Nouveaux derives de 3-aminoalkyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique |
| US7723372B2 (en) * | 2008-03-19 | 2010-05-25 | Hoffman-La Roche Inc. | Spiroindolinone derivatives |
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| JP5570172B2 (ja) * | 2008-10-08 | 2014-08-13 | 持田製薬株式会社 | 喫煙による循環機能不全の予防／改善または治療剤 |
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| WO2011047173A2 (en) * | 2009-10-14 | 2011-04-21 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
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| CN105726531A (zh) | 2010-02-26 | 2016-07-06 | 泽农医药公司 | 用于局部给药的螺-羟吲哚化合物的药物组合物及其作为治疗剂的用途 |
| US8217044B2 (en) | 2010-04-28 | 2012-07-10 | Hoffmann-La Roche Inc. | Spiroindolinone pyrrolidines |
| MD4202C1 (ro) * | 2012-03-21 | 2013-09-30 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a derivaţilor carbometoxi ai spiro[ciclopropan-oxindolilor] |
| MD4201C1 (ro) * | 2012-03-21 | 2013-09-30 | Институт Химии Академии Наук Молдовы | Procedeu de obţinere a derivaţilor carbonitrilici ai spiro[ciclopropan-oxindolilor] |
| CA2904079C (en) * | 2013-03-08 | 2017-09-19 | Wockhardt Limited | A process for preparation of (2s,5r)-7-oxo-6-sulphooxy-2-[((3r)-piperidine-3-carbonyl)-hydrazino carbonyl]-1,6-diaza-bicyclo-[3.2.1]-octane |
| TW201636017A (zh) | 2015-02-05 | 2016-10-16 | 梯瓦製藥國際有限責任公司 | 以螺吲哚酮化合物之局部調配物治療帶狀疱疹後遺神經痛之方法 |
| TW201938171A (zh) | 2017-12-15 | 2019-10-01 | 匈牙利商羅特格登公司 | 作為血管升壓素Ｖ１ａ受體拮抗劑之三環化合物 |
| HU231206B1 (hu) | 2017-12-15 | 2021-10-28 | Richter Gedeon Nyrt. | Triazolobenzazepinek |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3818830A1 (de) * | 1988-06-03 | 1989-12-14 | Boehringer Mannheim Gmbh | Bicyclische carboxamide, verfahren zu ihrer herstellung, deren vorstufen, und diese verbindungen enthaltende arzneimittel |
| FR2686878B1 (fr) * | 1992-01-30 | 1995-06-30 | Sanofi Elf | Derives du n-sulfonyl oxo-2 indole, leur preparation, les compositions pharmaceutiques en contenant. |
| US5663431A (en) * | 1992-01-30 | 1997-09-02 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708605A1 (fr) * | 1993-07-30 | 1995-02-10 | Sanofi Sa | Dérivés du N-sulfonylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| US5686624A (en) * | 1992-01-30 | 1997-11-11 | Sanofi | 1-benzenesulfonyl-1,3-dihydro-indol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
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