NZ561210A - Spiro-oxindole compounds and their uses as therapeutic agents - Google Patents
Spiro-oxindole compounds and their uses as therapeutic agentsInfo
- Publication number
- NZ561210A NZ561210A NZ561210A NZ56121006A NZ561210A NZ 561210 A NZ561210 A NZ 561210A NZ 561210 A NZ561210 A NZ 561210A NZ 56121006 A NZ56121006 A NZ 56121006A NZ 561210 A NZ561210 A NZ 561210A
- Authority
- NZ
- New Zealand
- Prior art keywords
- indol
- benzodioxole
- furo
- oxospiro
- methyl
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 16
- 229940124597 therapeutic agent Drugs 0.000 title description 3
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 494
- 125000003118 aryl group Chemical group 0.000 claims description 485
- 125000000623 heterocyclic group Chemical group 0.000 claims description 481
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 401
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- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 258
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 258
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 147
- 125000003342 alkenyl group Chemical group 0.000 claims description 146
- 125000000304 alkynyl group Chemical group 0.000 claims description 131
- 125000001424 substituent group Chemical group 0.000 claims description 102
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 247
- 125000003003 spiro group Chemical group 0.000 claims 198
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 166
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 9
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- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
- RNOVGJWJVRESAA-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)phenol Chemical group OC1=CC=C(F)C=C1C(F)(F)F RNOVGJWJVRESAA-UHFFFAOYSA-N 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
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- AHFINSWGYAZBOZ-UHFFFAOYSA-N 4-chloro-2-(trifluoromethyl)benzaldehyde Chemical group FC(F)(F)C1=CC(Cl)=CC=C1C=O AHFINSWGYAZBOZ-UHFFFAOYSA-N 0.000 claims 3
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- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 3
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- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67089605P | 2005-04-11 | 2005-04-11 | |
| PCT/US2006/014352 WO2006110917A2 (en) | 2005-04-11 | 2006-04-11 | Spiro-oxindole compounds and their uses as therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ561210A true NZ561210A (en) | 2011-03-31 |
Family
ID=36952847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ561210A NZ561210A (en) | 2005-04-11 | 2006-04-11 | Spiro-oxindole compounds and their uses as therapeutic agents |
Country Status (30)
| Country | Link |
|---|---|
| US (4) | US7700641B2 (enExample) |
| EP (4) | EP2752417B1 (enExample) |
| JP (4) | JP5118627B2 (enExample) |
| KR (5) | KR20140063803A (enExample) |
| CN (2) | CN102153562B (enExample) |
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Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9278088B2 (en) | 2002-02-19 | 2016-03-08 | Xenon Pharmaceuticals Inc. | Methods for identifying analgesic agents |
| MY145694A (en) | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| MY158766A (en) | 2005-04-11 | 2016-11-15 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| TW200833698A (en) * | 2006-10-12 | 2008-08-16 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| WO2008046087A2 (en) * | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro compounds and their uses as therapeutic agents |
| ATE545416T1 (de) * | 2006-10-12 | 2012-03-15 | Xenon Pharmaceuticals Inc | Verwendung von spiro-oxindol-verbindungen als therapeutika |
| CL2007002953A1 (es) * | 2006-10-12 | 2008-02-01 | Xenon Pharmaceuticals Inc | Compuestos derivados de espiro-oxindol; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto en el tratamiento del dolor, cancer, prurito, hiperplasia prostatica benigna, hipercolesterolemia. |
| JP2010522690A (ja) * | 2006-10-12 | 2010-07-08 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 三環式スピロオキシインドール誘導体および治療薬としてのその使用 |
| US7553833B2 (en) * | 2007-05-17 | 2009-06-30 | Hoffmann-La Roche Inc. | 3,3-spiroindolinone derivatives |
| MX2010002938A (es) | 2007-09-24 | 2010-04-01 | Comentis Inc | Derivados de (3-hidroxi-4-amino-butan-2-il)-3-(2-tiazol-2-il-pirro lidin-1-carbonil)benzamida y compuestos relacionados como inhibidores de beta-secretasa para tratar enfermedad de alzheimer. |
| JP2010540628A (ja) * | 2007-10-04 | 2010-12-24 | メルク・シャープ・エンド・ドーム・コーポレイション | カルシウムチャネル遮断薬としてのｎ−置換されたオキシインドリン誘導体 |
| US8273749B2 (en) * | 2007-10-04 | 2012-09-25 | Merck Sharp & Dohme Corp. | N-substituted oxindoline derivatives as calcium channel blockers |
| HRP20150882T1 (hr) | 2008-10-17 | 2015-09-25 | Xenon Pharmaceuticals Inc. | Spirooksindolski spojevi i njihova upotreba kao terapijska sredstva |
| AU2014265116B2 (en) * | 2008-10-17 | 2017-02-02 | Xenon Pharmaceuticals Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| WO2010045197A1 (en) * | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| US20110269788A1 (en) | 2008-12-29 | 2011-11-03 | Xenon Pharmaceuticals Inc. | Spiro-oxindole-derivatives as sodium channel blockers |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| AU2015224493B2 (en) * | 2009-06-29 | 2017-06-15 | Xenon Pharmaceuticals Inc. | Enantiomers of spiro-oxindole compounds and their uses as therapeutic agents |
| MY165579A (en) * | 2009-10-14 | 2018-04-05 | Xenon Pharmaceuticals Inc | Synthetic methods for spiro-oxindole compounds |
| US20110086899A1 (en) * | 2009-10-14 | 2011-04-14 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
| JP2013521232A (ja) * | 2010-02-26 | 2013-06-10 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 局所投与のためのスピロオキシインドール化合物の医薬組成物および治療剤としてのその使用 |
| EP2593434A1 (en) | 2010-07-16 | 2013-05-22 | Purdue Pharma LP | Pyridine compounds as sodium channel blockers |
| WO2012049555A1 (en) | 2010-10-13 | 2012-04-19 | Lupin Limited | Spirocyclic compounds as voltage-gated sodium channel modulators |
| ES2583061T3 (es) | 2010-12-21 | 2016-09-16 | Bayer Intellectual Property Gmbh | Método para la producción de oxindoles sustituidos en el N con sulfonilo |
| HRP20161412T1 (hr) | 2011-06-27 | 2016-12-02 | Newron Pharmaceuticals S.P.A. | Fluorirani derivati arilalkilaminokarboksamida |
| EP2753317B1 (en) * | 2011-09-06 | 2020-02-26 | CuRNA, Inc. | TREATMENT OF DISEASES RELATED TO ALPHA SUBUNITS OF SODIUM CHANNELS, VOLTAGE-GATED (SCNxA) WITH SMALL MOLECULES |
| AU2013203824A1 (en) | 2012-03-16 | 2013-10-03 | Purdue Pharma L.P. | Substituted pyridines and pryimidines as sodium channel blockers |
| HK1205113A1 (en) | 2012-04-12 | 2015-12-11 | Xenon Pharmaceuticals Inc. | Asymmetric syntheses for spiro-oxindole compounds useful as therapeutic agents |
| KR101719893B1 (ko) * | 2012-05-22 | 2017-03-24 | 제넨테크, 인크. | Ｎ-치환된 벤즈아미드 및 통증의 치료에서 이들의 용도 |
| US9714252B2 (en) | 2012-12-20 | 2017-07-25 | Purdue Pharma L.P. | Cyclic sulfonamides as sodium channel blockers |
| CN103554119B (zh) * | 2013-10-15 | 2015-09-16 | 华东师范大学 | 四氢呋喃并苯并二氢吡喃多环化合物的制备方法 |
| CN103554118B (zh) * | 2013-10-15 | 2015-08-19 | 华东师范大学 | 四氢呋喃并苯并二氢吡喃多环化合物及其应用 |
| CN103554120B (zh) * | 2013-10-16 | 2015-06-24 | 华东师范大学 | 3,3-螺(2-四氢呋喃)氧化吲哚多环状化合物的制备方法 |
| CN103554121B (zh) * | 2013-10-16 | 2015-06-24 | 华东师范大学 | 3,3-螺(2-四氢呋喃)氧化吲哚多环状化合物及其应用 |
| TW201623264A (zh) | 2014-03-29 | 2016-07-01 | 魯賓有限公司 | 作為電位閘控鈉通道調節劑之磺胺化合物 |
| US10730866B2 (en) | 2014-04-07 | 2020-08-04 | Purdue Pharma L.P. | Indole derivatives and use thereof |
| MX2016016363A (es) | 2014-06-12 | 2017-04-06 | Adamed Sp Zoo | Compuestos que comprenden un sistema de 1,1',2,5'-tetrahidroespiro [indol-3,2'-pirrol]-2,5'-diona como inhibidores de la interaccion de proteina-proteina p53-mdm2. |
| WO2016109795A1 (en) | 2014-12-31 | 2016-07-07 | Concert Pharmaceuticals, Inc. | Deuterated funapide and difluorofunapide |
| 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 |
| US9840513B2 (en) * | 2015-07-16 | 2017-12-12 | Abbvie S.Á.R.L. | Substituted tricyclics and method of use |
| TW201722938A (zh) | 2015-09-04 | 2017-07-01 | 魯賓有限公司 | 作為電位閘控鈉通道調節子之磺醯胺化合物 |
| CN108699015A (zh) | 2015-12-18 | 2018-10-23 | 默沙东公司 | 对电压门控性钠通道具有选择性活性的羟基烷基胺-和羟基环烷基胺-取代的二胺-芳基磺胺化合物 |
| WO2017127409A1 (en) | 2016-01-20 | 2017-07-27 | Chemocentryx, Inc. | 2-oxindole compounds |
| US10118932B2 (en) | 2016-06-16 | 2018-11-06 | Xenon Pharmaceuticals Inc. | Solid state forms of spiro-oxindole compounds |
| WO2017218920A1 (en) | 2016-06-16 | 2017-12-21 | Teva Pharmaceuticals International Gmbh | Asymmetric synthesis of funapide |
| WO2018163077A1 (en) | 2017-03-08 | 2018-09-13 | Lupin Limited | Indanyl compounds as voltage gated sodium channel modulators |
| EP3592747A1 (en) | 2017-03-10 | 2020-01-15 | Council of Scientific and Industrial Research | Spirooxindole compounds as gsk3 inhibitors and process for preparation thereof |
| US10513515B2 (en) | 2017-08-25 | 2019-12-24 | Biotheryx, Inc. | Ether compounds and uses thereof |
| KR101857408B1 (ko) * | 2018-02-28 | 2018-05-14 | 경북대학교 산학협력단 | 탈모 예방 또는 치료용 조성물 |
| EP3830093A1 (en) | 2018-07-27 | 2021-06-09 | Biotheryx, Inc. | Bifunctional compounds as cdk modulators |
| CN108976243B (zh) * | 2018-08-23 | 2020-03-03 | 青岛农业大学 | 通过二甲基呋喃与含氧化吲哚邻羟基苄醇合成螺-色满-4,3′-氧化吲哚的合成方法 |
| US11897930B2 (en) | 2020-04-28 | 2024-02-13 | Anwita Biosciences, Inc. | Interleukin-2 polypeptides and fusion proteins thereof, and their pharmaceutical compositions and therapeutic applications |
| KR102662391B1 (ko) | 2021-12-10 | 2024-05-03 | 원광대학교산학협력단 | 벤자제피노인돌 유도체 및 이의 제조 방법 |
| CN116173015B (zh) * | 2022-05-19 | 2024-09-20 | 四川大学 | 一种环己烯基异硫氰酸酯类化合物在制备Caspase-1抑制剂中的用途 |
| CN115160331B (zh) * | 2022-08-04 | 2023-06-02 | 青岛农业大学 | 一种氧化吲哚螺烯丙基取代色满骨架及其制备方法 |
| CN116554185B (zh) * | 2023-01-03 | 2025-07-08 | 中国科学技术大学 | 一种手性螺环氧化吲哚类化合物及其制备方法 |
| CN119823139A (zh) * | 2024-12-12 | 2025-04-15 | 武汉光化学技术研究院 | 一种手性螺环氧化吲哚类化合物及其合成方法 |
Family Cites Families (138)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3189617A (en) * | 1961-02-03 | 1965-06-15 | Sterling Drug Inc | 1-aryloxindoles and their preparation |
| DE1956237A1 (de) | 1969-11-08 | 1971-05-13 | Basf Ag | Spiro-pyrrolizidon-oxindole |
| DE2113343A1 (de) | 1971-03-19 | 1972-09-21 | Thiemann Chem Pharm Fab | Indolo[2,3-b] chinolone und Verfahren zu ihrer Herstellung |
| US3723459A (en) * | 1971-04-23 | 1973-03-27 | Mc Neil Labor Inc | 2-oxospiro (indoline -3,4{40 -thiochroman) derivatives |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| SE400966B (sv) * | 1975-08-13 | 1978-04-17 | Robins Co Inc A H | Forfarande for framstellning av 2-amino-3-(eller 5-)bensoyl-fenylettiksyror |
| US4670566A (en) * | 1979-07-12 | 1987-06-02 | A. H. Robins Company, Incorporated | 3-methyl-hio-4-(5-, 6-, or 7-)phenylindolindolin-2-ones |
| DE3019562A1 (de) * | 1980-05-22 | 1981-11-26 | Daimler-Benz Ag, 7000 Stuttgart | Vorrichtung zum steuern einer brennkraftmaschine |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US4440785A (en) * | 1980-10-30 | 1984-04-03 | A. H. Robins Company, Inc. | Methods of using 2-aminobiphenylacetic acids, esters, and metal salts thereof to treat inflammation |
| US4438130A (en) * | 1981-11-12 | 1984-03-20 | The Upjohn Company | Analgesic 1-oxa-, aza- and thia-spirocyclic compounds |
| JPS60142984A (ja) | 1983-12-28 | 1985-07-29 | Kyorin Pharmaceut Co Ltd | 新規なスピロピロリジン−２，５−ジオン誘導体およびその製造法 |
| US4569942A (en) | 1984-05-04 | 1986-02-11 | Pfizer Inc. | N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents |
| JPS6130554A (ja) | 1984-07-23 | 1986-02-12 | Ono Pharmaceut Co Ltd | プロスタグランジン類似化合物のある特定の立体配置を有する異性体及びそれらを有効成分として含有する治療剤 |
| US4690943A (en) | 1984-09-19 | 1987-09-01 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| US4721721A (en) | 1984-12-18 | 1988-01-26 | Rorer Pharmaceutical Corporation | 6-(4-thiazole) compounds, cardiotonic compositions including the same, and their uses |
| JPS62194907A (ja) * | 1986-02-21 | 1987-08-27 | Bridgestone Corp | 外観の改良された低転り抵抗ラジアルタイヤ |
| DE3608088C2 (de) * | 1986-03-07 | 1995-11-16 | Schering Ag | Pharmazeutische Präparate, enthaltend Cyclodextrinclathrate von Carbacyclinderivaten |
| WO1993012786A1 (en) | 1986-07-10 | 1993-07-08 | Howard Harry R Jr | Indolinone derivatives |
| GB2205103A (en) * | 1987-05-21 | 1988-11-30 | Shell Int Research | Modified block copolymers and process for the preparation thereof |
| IL87116A (en) * | 1987-07-17 | 1993-03-15 | Schering Ag | 9-halogen-(z)-prostaglandin derivatives and pharmaceutical compositions containing the same |
| US5182289A (en) * | 1988-06-14 | 1993-01-26 | Schering Corporation | Heterobicyclic compounds having antiinflammatory activity |
| KR930011300B1 (ko) | 1989-07-25 | 1993-11-29 | 다이호오 야꾸힌 고오교오 가부시끼가이샤 | 옥시인돌유도체 |
| DE3932953A1 (de) | 1989-10-03 | 1991-04-11 | Boehringer Mannheim Gmbh | Neue 2-bicyclo-benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3935514A1 (de) | 1989-10-25 | 1991-05-02 | Boehringer Mannheim Gmbh | Neue bicyclo-imidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5023265A (en) * | 1990-06-01 | 1991-06-11 | Schering Corporation | Substituted 1-H-pyrrolopyridine-3-carboxamides |
| US5484778C1 (en) | 1990-07-17 | 2001-05-08 | Univ Cleveland Hospitals | Phthalocynine photosensitizers for photodynamic therapy and methods for their use |
| AU648359B2 (en) | 1990-11-22 | 1994-04-21 | Janssen Pharmaceutica N.V. | Isonicotinic acid derivatives |
| US5116854A (en) * | 1991-06-28 | 1992-05-26 | Pfizer Inc. | Anti-inflammatory 1-heteroaryl-3-acyl-2-oxindoles |
| 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 |
| US5849780A (en) * | 1992-01-30 | 1998-12-15 | Sanofi | 1-benzenesulfonyl-1-1,3-dihydroindol-2-one derivatives, their preparation and pharmaceutical compositions in which they are present |
| EP0654024A1 (en) | 1992-08-06 | 1995-05-24 | Warner-Lambert Company | 2-thioindoles (selenoindoles) and related disulfides (selenides) which inhibit protein tyrosine kinases and which have antitumor properties |
| US5278162A (en) * | 1992-09-18 | 1994-01-11 | The Du Pont Merck Pharmaceutical Company | 3,3'-disubstituted-1,3-dihydro-2H-pyrrolo[2,3-b]heterocyclic-2-one useful in the treatment of cognitive disorders of man |
| US5296478A (en) * | 1992-10-07 | 1994-03-22 | The Dupont Merck Pharmaceutical Co. | 1-substituted oxindoles as cognition enhancers |
| US5776936A (en) * | 1992-11-13 | 1998-07-07 | Pharmacia & Upjohn Company | Marcfortine/paraherquamide derivatives useful as antiparasitic agents |
| DE4242451A1 (de) | 1992-12-16 | 1994-06-23 | Basf Ag | Verfahren zur Herstellung von 5-Ringheterocyclen |
| US5298522A (en) | 1993-01-22 | 1994-03-29 | Pfizer Inc. | 6-chloro-5-fluoro-3-(2-thenoyl)-2-oxindole-1-carboxamide as an analgesic and anti-inflammatory agent while maintaining a normal urine protein/creatinine ratio |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| US5502072A (en) | 1993-11-26 | 1996-03-26 | Pfizer Inc. | Substituted oxindoles |
| AT400950B (de) * | 1994-02-04 | 1996-04-25 | Immodal Pharmaka Gmbh | Verfahren zur technischen herstellung definierter isomerengemische aus verbindungen mit spirozyklischen - aminocarboxyl- und/oder spirozyklischen - aminocarbonyl-systemen |
| CN1047386C (zh) * | 1994-04-07 | 1999-12-15 | 西玛夫公司 | 新型褪黑激素拮抗物螺旋[吲哚吡咯烷丁]衍生物,其制备方法及其作为药物产品的用途 |
| FR2722195B1 (fr) | 1994-07-07 | 1996-08-23 | Adir | Nouveaux derives de 1,3-dihydro-2h-pyrrolo(2,3-b) pyridin-2-ones et oxazolo(4,5-b) pyridin-2(3h)-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5618819A (en) * | 1994-07-07 | 1997-04-08 | Adir Et Compagnie | 1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one and oxazolo[4,5-b]pyridin-2-(3H)-one compounds |
| CA2235686C (en) | 1995-10-24 | 2007-06-26 | Sanofi | Indolin-2-one derivatives, process for their production and the pharmaceutical compositions containing them |
| FR2740136B1 (fr) * | 1995-10-24 | 1998-01-09 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant |
| HUP9600855A3 (en) | 1996-04-03 | 1998-04-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing tenidap |
| JPH1095766A (ja) | 1996-09-19 | 1998-04-14 | Sanwa Kagaku Kenkyusho Co Ltd | アセトアミド誘導体、及びその用途 |
| FR2757157B1 (fr) | 1996-12-13 | 1999-12-31 | Sanofi Sa | Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant |
| EP0989856B1 (de) * | 1997-01-20 | 2010-05-12 | IMMODAL PHARMAKA GESELLSCHAFT m.b.H. | Verfahren und stoffe zur freisetzung eines wachstumsfaktors aus endothelzellen, und nach dem verfahren freigesetzter wachstumsfaktor sowie seine verwendung |
| NO317155B1 (no) * | 1997-02-04 | 2004-08-30 | Ono Pharmaceutical Co | <omega>-cykloalkyl-prostagladin-E<N>2</N>-derivater |
| PT1008588E (pt) * | 1997-02-10 | 2003-09-30 | Ono Pharmaceutical Co | Derivados da 11,15-o-diaklquil-prostaglandina e processo de producao dos mesmos e farmaco que os contem como ingrediente activo |
| NZ501236A (en) | 1997-05-07 | 2002-02-01 | Galen Chemicals Ltd | Intravaginal drug delivery devices for the administration of testosterone and testosterone precursors in a polymer matrix and surrounded by a sheath |
| WO1999033794A1 (en) * | 1997-12-25 | 1999-07-08 | Ono Pharmaceutical Co., Ltd. | φ-CYCLOALKYL-PROSTAGLANDIN E2 DERIVATIVES |
| JP4087938B2 (ja) * | 1998-02-04 | 2008-05-21 | 高砂香料工業株式会社 | ヒノキチオ−ル類の分岐サイクロデキストリン包接化合物からなる抗菌剤およびそれを含有する組成物 |
| CZ302147B6 (cs) | 1998-04-01 | 2010-11-18 | Nortran Pharmaceuticals Inc. | Aminocyklohexyletherová sloucenina, použití této slouceniny pri výrobe léciva, farmaceutická kompozice tuto slouceninu obsahující a tato sloucenina a kompozice pro použití pri lécení |
| US20040038970A1 (en) * | 1998-06-12 | 2004-02-26 | Societe De Conseils De Recherches Etd' Application Scientifiques, S.A.S. A Paris, France Corp. | Beta-carboline compounds |
| CN1169808C (zh) * | 1998-06-12 | 2004-10-06 | 研究及应用科学协会股份有限公司 | β-咔啉化合物 |
| US6235780B1 (en) * | 1998-07-21 | 2001-05-22 | Ono Pharmaceutical Co., Ltd. | ω-cycloalkyl-prostaglandin E1 derivatives |
| AU5227999A (en) | 1998-07-27 | 2000-02-21 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| US6407101B1 (en) * | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| US6355648B1 (en) * | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| WO2000071129A1 (en) | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
| ES2306665T3 (es) * | 1999-07-21 | 2008-11-16 | Boehringer Ingelheim Pharmaceuticals Inc. | Pequeñas moleculas utiles en el tratamiento de la enfermedad inflamatoria. |
| US6566372B1 (en) * | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| WO2001038564A2 (en) | 1999-11-26 | 2001-05-31 | Mcgill University | Loci for idiopathic generalized epilepsy, mutations thereof and method using same to assess, diagnose, prognose or treat epilepsy |
| FR2807038B1 (fr) | 2000-04-03 | 2002-08-16 | Sanofi Synthelabo | Nouveaux derives d'indolin-2-one, leur preparation et les compositions pharmaceutiques les contenant |
| US20020045566A1 (en) | 2000-10-13 | 2002-04-18 | Gribkoff Valentin K. | Selective maxi-K potassium channel openers functional under conditions of high intracellular calcium concentration, methods and uses thereof |
| CA2421594A1 (en) | 2000-11-10 | 2002-05-16 | John Arnold Werner | 3-substituted oxindole beta 3 agonists |
| US6670357B2 (en) * | 2000-11-17 | 2003-12-30 | Bristol-Myers Squibb Company | Methods of treating p38 kinase-associated conditions and pyrrolotriazine compounds useful as kinase inhibitors |
| RU2233082C2 (ru) * | 2001-06-26 | 2004-07-27 | Институт животноводства УААН | Регулятор вакуума доильного агрегата |
| US20030078278A1 (en) | 2001-06-26 | 2003-04-24 | Pfizer Inc. | Spiropiperidine compounds as ligands for ORL-1 receptor |
| ES2262817T3 (es) * | 2001-08-14 | 2006-12-01 | Eli Lilly And Company | Agonistas beta-3 oxindol 3-sustituidos. |
| US7244744B2 (en) | 2001-11-01 | 2007-07-17 | Icagen, Inc. | Piperidines |
| ATE455104T1 (de) | 2001-11-01 | 2010-01-15 | Icagen Inc | Pyrazolamide zur anwendung in der behandlung von schmerz |
| US7205407B2 (en) * | 2001-11-20 | 2007-04-17 | Eli Lilly And Company | 3-Substituted oxindole β3 agonists |
| SE0104341D0 (sv) * | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New use |
| WO2003064425A1 (en) | 2002-01-28 | 2003-08-07 | Pfizer Japan Inc. | N-substituted spiropiperidine compounds as ligands for orl-1 receptor |
| US6995144B2 (en) * | 2002-03-14 | 2006-02-07 | Eisai Co., Ltd. | Nitrogen containing heterocyclic compounds and medicines containing the same |
| US7250442B2 (en) | 2002-03-15 | 2007-07-31 | Eli Lilly And Company | Dihydroindol-2-one derivatives as steroid hormone nuclear receptor modulators |
| GB0213715D0 (en) | 2002-06-14 | 2002-07-24 | Syngenta Ltd | Chemical compounds |
| CN1662206A (zh) | 2002-06-25 | 2005-08-31 | 惠氏公司 | 硫代－2－羟基吲哚衍生物在治疗皮肤病中的用途 |
| AU2003245637A1 (en) | 2002-06-25 | 2004-01-06 | Wyeth | Use of thio-oxindole derivatives in treatment of hormone-related conditions |
| US7256218B2 (en) | 2002-11-22 | 2007-08-14 | Jacobus Pharmaceutical Company, Inc. | Biguanide and dihydrotriazine derivatives |
| EP1626722A1 (en) * | 2003-05-16 | 2006-02-22 | Pfizer Products Inc. | Method for enhancing cognition using ziprasidone |
| CA2525868A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Anxiety treatments with ziprasidone |
| WO2004100954A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Treatment of psychotic and depressive disorders |
| CA2525326A1 (en) * | 2003-05-16 | 2004-11-25 | Pfizer Products Inc. | Treatment of bipolar disorders and associated symptoms |
| CN101693697A (zh) | 2003-07-30 | 2010-04-14 | 泽农医药公司 | 哌嗪衍生物和它们作为治疗剂的用途 |
| DE10337184A1 (de) | 2003-08-13 | 2005-03-10 | Gruenenthal Gmbh | Substituierte 3-Pyrrolidin-Indol-Derivate |
| WO2005016913A1 (en) * | 2003-08-19 | 2005-02-24 | Pfizer Japan, Inc. | Tetrahydroisoquinoline or isochroman compounds as orl-1 receptor ligands for the treatment of pain and cns disorders |
| JPWO2005035498A1 (ja) * | 2003-10-08 | 2006-12-21 | 住友製薬株式会社 | 含窒素二環性化合物の摂食調節剤としての用途 |
| EP1557166A1 (en) | 2004-01-21 | 2005-07-27 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders |
| US7507760B2 (en) * | 2004-01-22 | 2009-03-24 | Neuromed Pharmaceuticals Ltd. | N-type calcium channel blockers |
| GB0406867D0 (en) | 2004-03-26 | 2004-04-28 | F2G Ltd | Antifungal agents |
| BRPI0509377A (pt) | 2004-03-29 | 2007-09-11 | Pfizer | compostos de ácido alfa arila ou heteroaril metil beta piperidino propanóico como antagonistas do receptor orl1 |
| WO2005099689A1 (en) | 2004-04-01 | 2005-10-27 | Case Western Reserve University | Topical delivery of phthalocyanines |
| GT200500063A (es) | 2004-04-01 | 2005-10-14 | Metodo para tratar la esquizofrenia y/o anormalidades glucoregulatorias | |
| US20070299102A1 (en) * | 2004-04-08 | 2007-12-27 | Topo Target A/S | Diphenyl Ox-Indol-2-One Compounds and Their Use in the Treatment of Cancer |
| AU2005237520B2 (en) | 2004-04-27 | 2012-01-19 | Wyeth | Purification of progesterone receptor modulators |
| EP1742920A2 (en) | 2004-05-05 | 2007-01-17 | Unibioscreen S.A. | Naphthalimide derivatives for the treatment of cancer |
| TWI350168B (en) | 2004-05-07 | 2011-10-11 | Incyte Corp | Amido compounds and their use as pharmaceuticals |
| JP2007537235A (ja) | 2004-05-14 | 2007-12-20 | ファイザー・プロダクツ・インク | 異常細胞増殖の治療用ピリミジン誘導体 |
| MXPA06014573A (es) | 2004-06-24 | 2007-03-12 | Incyte Corp | Compuestos amido y su uso como farmaceuticos. |
| GT200500186A (es) | 2004-07-07 | 2006-03-02 | Regimenes anticonceptivos con antagonistas del receptor de progesterona y kits | |
| GT200500185A (es) | 2004-08-09 | 2006-04-10 | Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos | |
| GT200500183A (es) | 2004-08-09 | 2006-04-10 | Moduladores del receptor de progesterona que comprenden derivados de pirrol-oxindol y sus usos | |
| JP4677323B2 (ja) | 2004-11-01 | 2011-04-27 | キヤノン株式会社 | 画像処理装置及び画像処理方法 |
| CA2587153A1 (en) | 2004-11-18 | 2006-05-26 | Incyte Corporation | Inhibitors of 11-.beta. hydroxyl steroid dehydrogenase type 1 and methods of using the same |
| DE102005007694A1 (de) | 2005-02-18 | 2006-09-21 | Henkel Kgaa | Mittel zum Färben von keratinhaltigen Fasern |
| KR100944301B1 (ko) | 2005-02-22 | 2010-02-24 | 더 리젠츠 오브 더 유니버시티 오브 미시간 | Ｍｄｍ２의 소분자 억제제 및 이의 용도 |
| MY158766A (en) | 2005-04-11 | 2016-11-15 | Xenon Pharmaceuticals Inc | Spiro-oxindole compounds and their uses as therapeutic agents |
| MY145694A (en) * | 2005-04-11 | 2012-03-30 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| AR053713A1 (es) | 2005-04-20 | 2007-05-16 | Xenon Pharmaceuticals Inc | Compuestos heterociclicos y sus usos como agentes terapeuticos |
| AR056317A1 (es) * | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| CN101166722A (zh) * | 2005-04-29 | 2008-04-23 | 惠氏公司 | 制备3,3-二取代的羟吲哚和硫代羟吲哚的方法 |
| WO2006125048A2 (en) * | 2005-05-16 | 2006-11-23 | Gilead Sciences, Inc. | Hiv-integrase inhibitor compounds |
| PL1924264T3 (pl) * | 2005-09-01 | 2014-03-31 | Hoffmann La Roche | Diaminopirymidyny jako modulatory P2X<sub>3</sub> I P2X<sub>2/3</sub> |
| TW200833698A (en) | 2006-10-12 | 2008-08-16 | Xenon Pharmaceuticals Inc | Spiroheterocyclic compounds and their uses as therapeutic agents |
| WO2008046082A2 (en) | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Use of heterocyclic compounds as therapeutic agents |
| JP2010522690A (ja) | 2006-10-12 | 2010-07-08 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 三環式スピロオキシインドール誘導体および治療薬としてのその使用 |
| WO2008046087A2 (en) | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiro compounds and their uses as therapeutic agents |
| CL2007002953A1 (es) | 2006-10-12 | 2008-02-01 | Xenon Pharmaceuticals Inc | Compuestos derivados de espiro-oxindol; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto en el tratamiento del dolor, cancer, prurito, hiperplasia prostatica benigna, hipercolesterolemia. |
| WO2008046084A2 (en) | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Spiroheterocyclic compounds and their uses as therapeutic agents |
| ATE545416T1 (de) * | 2006-10-12 | 2012-03-15 | Xenon Pharmaceuticals Inc | Verwendung von spiro-oxindol-verbindungen als therapeutika |
| WO2008046083A2 (en) | 2006-10-12 | 2008-04-17 | Xenon Pharmaceuticals Inc. | Use of oxindole compounds as therapeutic agents |
| WO2008117050A1 (en) | 2007-03-27 | 2008-10-02 | Astrazeneca Ab | Pyrazolyl-amino-substituted pyrazines and their use for the treatment of cancer |
| WO2010045197A1 (en) | 2008-10-17 | 2010-04-22 | Xenon Pharmaceuticals, Inc. | Spiro-oxindole compounds and their use as therapeutic agents |
| HRP20150882T1 (hr) | 2008-10-17 | 2015-09-25 | Xenon Pharmaceuticals Inc. | Spirooksindolski spojevi i njihova upotreba kao terapijska sredstva |
| WO2010053998A1 (en) | 2008-11-05 | 2010-05-14 | Xenon Pharmaceuticals, Inc. | Spiro-condensed indole derivatives as sodium channel inhibitors |
| US20110269788A1 (en) | 2008-12-29 | 2011-11-03 | Xenon Pharmaceuticals Inc. | Spiro-oxindole-derivatives as sodium channel blockers |
| WO2010132352A2 (en) | 2009-05-11 | 2010-11-18 | Xenon Pharmaceuticals Inc. | Spiro compounds and their use as therapeutic agents |
| AR077252A1 (es) | 2009-06-29 | 2011-08-10 | Xenon Pharmaceuticals Inc | Enantiomeros de compuestos de espirooxindol y sus usos como agentes terapeuticos |
| US20110086899A1 (en) * | 2009-10-14 | 2011-04-14 | Xenon Pharmaceuticals Inc. | Pharmaceutical compositions for oral administration |
| MY165579A (en) * | 2009-10-14 | 2018-04-05 | Xenon Pharmaceuticals Inc | Synthetic methods for spiro-oxindole compounds |
| JP2013521232A (ja) | 2010-02-26 | 2013-06-10 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 局所投与のためのスピロオキシインドール化合物の医薬組成物および治療剤としてのその使用 |
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