CN103189337A - 氨基二氢化茚衍生物、包含所述氨基二氢化茚衍生物的药物组合物及其在治疗中的用途 - Google Patents
氨基二氢化茚衍生物、包含所述氨基二氢化茚衍生物的药物组合物及其在治疗中的用途 Download PDFInfo
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- CN103189337A CN103189337A CN2011800397167A CN201180039716A CN103189337A CN 103189337 A CN103189337 A CN 103189337A CN 2011800397167 A CN2011800397167 A CN 2011800397167A CN 201180039716 A CN201180039716 A CN 201180039716A CN 103189337 A CN103189337 A CN 103189337A
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- Prior art keywords
- dihydro
- indenes
- methyl
- azetidine
- alkyl
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 title abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 title description 5
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/10—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
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- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
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- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
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- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings 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
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- 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
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- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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| PCT/EP2011/063973 WO2012020131A2 (en) | 2010-08-13 | 2011-08-12 | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
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Cited By (2)
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| CN114276243A (zh) * | 2021-12-13 | 2022-04-05 | 浙江九洲药业股份有限公司 | 一种洛索洛芬及其类似物的合成方法 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009121872A2 (en) | 2008-04-01 | 2009-10-08 | Abbott Gmbh & Co. Kg | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
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| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
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| JP2014521682A (ja) | 2011-08-05 | 2014-08-28 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン、アミノチオクロマンおよびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、ならびに治療におけるこれらの使用 |
| CN104011028A (zh) | 2011-11-18 | 2014-08-27 | 艾伯维德国有限责任两合公司 | N-取代的氨基苯并环庚烯、氨基四氢化萘、氨基茚满和苯烷基胺衍生物、包含所述衍生物的药物组合物及其在治疗中的用途 |
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| US9227901B2 (en) | 2012-07-05 | 2016-01-05 | Abbvie Inc. | Process for preparing bicyclic amine derivatives |
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| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| CN105992764A (zh) | 2013-10-17 | 2016-10-05 | 艾伯维德国有限责任两合公司 | 氨基色满、氨基硫代色满及氨基-1,2,3,4-四氢喹啉衍生物，包含其的药物组合物及其在治疗中的用途 |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US10421756B2 (en) | 2015-07-06 | 2019-09-24 | Rodin Therapeutics, Inc. | Heterobicyclic N-aminophenyl-amides as inhibitors of histone deacetylase |
| RS62639B1 (sr) | 2015-07-06 | 2021-12-31 | Alkermes Inc | Hetero-halo inhibitori histonskih deacetilaza |
| MD3570834T2 (ro) | 2017-01-11 | 2022-04-30 | Alkermes Inc | Inhibitori biciclici ai histon deacetilazei |
| JP7152471B2 (ja) | 2017-08-07 | 2022-10-12 | ロダン・セラピューティクス，インコーポレーテッド | ヒストン脱アセチル化酵素の二環阻害剤 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998004521A1 (en) * | 1996-07-26 | 1998-02-05 | Icagen, Inc. | Potassium channel inhibitors |
| CN1309631A (zh) * | 1998-07-31 | 2001-08-22 | 阿克佐诺贝尔公司 | 氨甲基羧酸衍生物 |
| WO2003045924A1 (en) * | 2001-11-21 | 2003-06-05 | Pharmacia & Upjohn Company | Substituted aryl 1,4-pyrazine derivatives |
| WO2009121872A2 (en) * | 2008-04-01 | 2009-10-08 | Abbott Gmbh & Co. Kg | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
Family Cites Families (124)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867391A (en) | 1973-08-09 | 1975-02-18 | Pfizer | Cyclic n-substituted derivatives of 1,4-benzene disulphonamide |
| SE8004002L (sv) | 1980-05-29 | 1981-11-30 | Arvidsson Folke Lars Erik | Terapeutiskt anvendbara tetralinderivat |
| ATE39483T1 (de) | 1982-04-02 | 1989-01-15 | Takeda Chemical Industries Ltd | Kondensierte pyrrolinon-derivate, und ihre herstellung. |
| US4789678A (en) | 1986-08-25 | 1988-12-06 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing α-alkyl-4-amino-3-quinolinemethanols and 1-(4-aralkylamino-3-quinolinyl)alkanones and related compounds |
| US4927838A (en) | 1987-07-10 | 1990-05-22 | Hoffman-La Roche Inc. | Pyridine compounds which are useful in treating a disease state characterized by an excess of platelet activating factors |
| CA1327795C (en) | 1987-08-14 | 1994-03-15 | Jules Freedman | Antidepressants which are aryloxy inadanamines |
| US5300523A (en) | 1988-07-28 | 1994-04-05 | Bayer Aktiengesellschaft | Substituted aminomethyltetralins and their heterocyclic analogues |
| US5545755A (en) | 1989-05-31 | 1996-08-13 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| KR100195656B1 (ko) | 1989-05-31 | 1999-06-15 | 로버트 에이.아미테이지 | 치료학적으로 유용한 2-아미노테트랄린 유도체 |
| US5071875A (en) | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| KR100207876B1 (ko) | 1990-10-12 | 1999-07-15 | 로버트 에이. 아미테이지 | 치료학적으로 유용한 2-아미노테트랄린 유도체 |
| AU1915192A (en) | 1991-04-26 | 1992-12-21 | Upjohn Company, The | Method of treating/preventing substance abuse using 1-alkyl-5(substituted oxy)-2-aminotetralins |
| JPH05213884A (ja) | 1991-06-14 | 1993-08-24 | Upjohn Co:The | 新規な４−アミノキノリン類およびこれを有効成分とする高血圧・鬱血性心不全の予防・治療剤 |
| GB9127306D0 (en) | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| DK1019385T3 (da) | 1995-09-15 | 2004-05-24 | Upjohn Co | Aminoaryloxazolidinon-N-oxider |
| CN1327383A (zh) | 1996-05-31 | 2001-12-19 | 阿列里克斯神经科学公司 | 治疗神经和神经精神障碍的药物 |
| US6057357A (en) * | 1997-04-30 | 2000-05-02 | Warner-Lambert Company | Peripherally selective kappa opioid agonists |
| AU7552198A (en) | 1997-06-11 | 1998-12-30 | Sankyo Company Limited | Benzylamine derivatives |
| US6060491A (en) | 1997-06-19 | 2000-05-09 | Dupont Pharmaceuticals | 6-membered aromatics as factor Xa inhibitors |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| US6197798B1 (en) | 1998-07-21 | 2001-03-06 | Novartis Ag | Amino-benzocycloalkane derivatives |
| PT1119543E (pt) | 1998-10-07 | 2005-03-31 | Ortho Mcneil Pharm Inc | N-aralquilaminotetralinas como ligandos para o receptor y5 do neuropeptido y |
| DE60024631T2 (de) | 1999-07-26 | 2006-06-14 | Banyu Pharma Co Ltd | Biaryl-harnstoff-derivate |
| NZ516782A (en) | 1999-07-28 | 2004-12-24 | Ortho Mcneil Pharm Inc | Amine and amide derivatives as ligands for the neuropeptide Y Y5 receptor useful in the treatment of obesity and other disorders |
| GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| US6426364B1 (en) | 1999-11-01 | 2002-07-30 | Nps Allelix Corp. | Diaryl-enynes |
| EP1240147A1 (en) | 1999-12-21 | 2002-09-18 | Icagen, Inc. | Potassium channel inhibitors |
| JP4850332B2 (ja) | 2000-10-18 | 2012-01-11 | 東京エレクトロン株式会社 | デュアルダマシン構造のエッチング方法 |
| JP2004529132A (ja) | 2001-03-27 | 2004-09-24 | アクテリオン ファマシューティカルズ リミテッド | １，２，３，４−テトラヒドロイソキノリン誘導体 |
| AU2756602A (en) | 2001-04-25 | 2002-10-31 | Pfizer Products Inc. | Methods and kits for treating depression or preventing deterioration of cognitive function |
| US6831193B2 (en) | 2001-05-18 | 2004-12-14 | Abbott Laboratories | Trisubstituted-N-[(1S)-1,2,3,4-Tetrahydro-1-naphthalenyl]benzamides which inhibit P2X3 and P2X2/3 containing receptors |
| ES2248493T3 (es) | 2001-08-16 | 2006-03-16 | Pfizer Products Inc. | Difluorometilen-eteres aromaticos y su uso como inhibidores del transportador de glicina tipo 1. |
| DE10149370A1 (de) | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| CA2467118A1 (en) | 2001-12-20 | 2003-07-03 | H. Lundbeck A/S | Aryloxyphenyl and arylsulfanylphenyl derivatives |
| GB0130696D0 (en) | 2001-12-21 | 2002-02-06 | Smithkline Beecham Plc | Chemical Compounds |
| AU2003208711A1 (en) | 2002-02-12 | 2003-09-04 | Akzo Nobel N.V. | 1-arylsulfonyl-3-substituted indole and indoline derivatives useful in the treatment of central nervous system disorders |
| DE10210779A1 (de) | 2002-03-12 | 2003-10-09 | Merck Patent Gmbh | Cyclische Amide |
| DE10217006A1 (de) | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| FR2838739B1 (fr) | 2002-04-19 | 2004-05-28 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl)benzamide, leur preparation et leur application en therapeutique |
| EP1506166B1 (en) | 2002-05-17 | 2011-11-16 | Janssen Pharmaceutica NV | Aminotetralin-derived urea modulators of vanilloid vr1 receptor |
| JP4530852B2 (ja) | 2002-07-15 | 2010-08-25 | メルク・シャープ・エンド・ドーム・コーポレイション | 糖尿病治療のためのピペリジノピリミジンジペプチジルペプチダーゼ阻害剤 |
| FR2842805A1 (fr) | 2002-07-29 | 2004-01-30 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide,leur preparation et leur application et therapeutique |
| FR2842804B1 (fr) | 2002-07-29 | 2004-09-03 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| US20040152741A1 (en) | 2002-09-09 | 2004-08-05 | Nps Allelix Corporation | Arylglycine derivatives and their use as glycine transport inhibitors |
| US7084154B2 (en) | 2003-02-11 | 2006-08-01 | Pharmacopeia Drug Disclovery, Inc. | 2-(aminomethyl) arylamide analgesics |
| JP4368375B2 (ja) | 2003-02-17 | 2009-11-18 | エフ．ホフマン−ラ ロシュ アーゲー | ピペリジン−ベンゼンスルホンアミド誘導体 |
| CA2518194A1 (en) | 2003-03-07 | 2004-09-23 | Eli Lilly And Company | 6-substituted nicotinamide derivatives as opioid receptor antagonists |
| DE10315570A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Triazolderivate |
| MXPA05011198A (es) | 2003-04-30 | 2005-12-14 | Lundbeck & Co As H | Derivados de oxifenilo aromaticos y de sulfanilfenilo aromaticos. |
| JP2004359633A (ja) | 2003-06-06 | 2004-12-24 | Bayer Cropscience Ag | イソインドリノン誘導体の殺虫剤としての利用 |
| GB0314476D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314478D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| GB0314479D0 (en) | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Compounds |
| JP2006528186A (ja) | 2003-07-23 | 2006-12-14 | ワイス | ５−ヒドロキシトリプタミン−６リガンドとしてのスルホニルジヒドロベンゾイミダゾロン化合物 |
| WO2005014563A1 (en) | 2003-08-11 | 2005-02-17 | F. Hoffmann-La Roche Ag | Piperazine with or-substituted phenyl group and their use as glyt1 inhibitors |
| RU2355683C2 (ru) | 2003-09-09 | 2009-05-20 | Ф.Хоффманн-Ля Рош Аг | Производные 1-бензоилпиперазина в качестве ингибиторов поглощения глицина для лечения психозов |
| EP1663232B1 (en) | 2003-09-09 | 2007-10-03 | F. Hoffmann-La Roche Ag | 1-(2-amino-benzoyl)-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses |
| FR2861076B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
| FR2861071B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
| FR2861070B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861074B1 (fr) | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861073B1 (fr) | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| DE602004010419T2 (de) | 2003-10-23 | 2008-10-09 | F. Hoffmann-La Roche Ag | Triazaspiropiperidinderivate zur verwendung als glyt-1-inhibitoren bei der behandlung von neurologischen und neuropsychiatrischen erkrankungen |
| US20070105902A1 (en) | 2003-11-12 | 2007-05-10 | Lindsley Craig W | 4-Phenyl piperdine sulfonyl glycine transporter inhibitors |
| GB0326840D0 (en) | 2003-11-18 | 2003-12-24 | Glaxo Group Ltd | Compounds |
| GB0329362D0 (en) | 2003-12-18 | 2004-01-21 | Glaxo Group Ltd | Compounds |
| WO2005058317A1 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Glycine transporter-1 inhibirors |
| WO2005058885A2 (en) | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Piperidine derivatives and their use as glycine transporter inhibitors |
| WO2005099353A2 (en) | 2004-04-19 | 2005-10-27 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| DE102004030099A1 (de) | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| PL1768967T3 (pl) | 2004-07-20 | 2009-09-30 | Symed Labs Ltd | Nowe związki pośrednie do wytwarzania linezolidu oraz związki pokrewne |
| WO2006025308A1 (ja) | 2004-08-31 | 2006-03-09 | Matsushita Electric Industrial Co., Ltd. | コンテンツ購入処理端末とその方法、及びプログラム |
| US20060074105A1 (en) | 2004-09-20 | 2006-04-06 | Serenex, Inc. | Substituted quinoline and quinazoline inhibitors of quinone reductase 2 |
| JP2008514702A (ja) | 2004-09-29 | 2008-05-08 | エーエムアール テクノロジー インコーポレイテッド | 新規シクロスポリン類似体およびそれらの薬学的使用 |
| WO2006040177A1 (en) | 2004-10-14 | 2006-04-20 | Abbott Gmbh & Co.Kg | 6-amino(aza)indane compounds suitable for treating disorders that respond to modulation of the dopamine d3 recptor |
| ES2338139T3 (es) | 2004-12-15 | 2010-05-04 | F. Hoffmann-La Roche Ag | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador de la glicina i (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| DE102005000666B3 (de) | 2005-01-04 | 2006-10-05 | Sanofi-Aventis Deutschland Gmbh | Sulfonylpyrrolidine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DK1848694T3 (da) | 2005-02-07 | 2010-01-25 | Hoffmann La Roche | Heterocykliske substituerede phenylmethanoner som inhibitorer af glycintransporter |
| EP1863804A1 (en) | 2005-04-01 | 2007-12-12 | Methylgene, Inc. | Inhibitors of histone deacetylase |
| WO2006121767A2 (en) | 2005-05-06 | 2006-11-16 | Apath, Llc | 4-aminoquinoline compounds for treating virus-related conditions |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| UA95454C2 (uk) | 2005-07-15 | 2011-08-10 | Амр Текнолоджи, Інк. | Арил- і гетероарилзаміщені тетрагідробензазепіни і їх застосування для блокування зворотного захоплення норепінефрину, допаміну і серотоніну |
| US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| US7732609B2 (en) | 2005-12-01 | 2010-06-08 | Elan Pharmaceuticals, Inc. | 5-(arylsulfonyl)-pyrazolopiperidines |
| US7592461B2 (en) | 2005-12-21 | 2009-09-22 | Bristol-Myers Squibb Company | Indane modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| WO2007143823A1 (en) | 2006-06-12 | 2007-12-21 | Merck Frosst Canada Ltd. | Azetidine derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| GB0619176D0 (en) | 2006-09-29 | 2006-11-08 | Lectus Therapeutics Ltd | Ion channel modulators & uses thereof |
| WO2008038841A1 (en) | 2006-09-30 | 2008-04-03 | Japan Tobacco Inc. | Thiadiazolone derivative and use thereof |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| MX2009008465A (es) | 2007-02-15 | 2009-08-20 | Hoffmann La Roche | Nuevas 2-aminooxazolinas como ligandos de taar1. |
| CA2686545C (en) | 2007-04-19 | 2010-11-02 | Concert Pharmaceuticals Inc. | Deuterated morpholinyl compounds |
| US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| EP2150538B1 (en) | 2007-06-06 | 2012-03-28 | DSM Sinochem Pharmaceuticals Netherlands B.V. | Novel 5-substituted hydantoins |
| US8420670B2 (en) | 2007-08-22 | 2013-04-16 | Abbott Laboratories | 4-benzylaminoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| WO2009035598A1 (en) | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| US20090137457A1 (en) | 2007-10-02 | 2009-05-28 | Concert Pharmaceuticals, Inc. | Pyrimidinedione derivatives |
| US8410124B2 (en) | 2007-10-18 | 2013-04-02 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| SA08290668B1 (ar) * | 2007-10-25 | 2012-02-12 | شيونوجي آند كو.، ليمتد | مشتقات أمين لها نشاط مضاد لمستقبل npy y5 واستخداماتها |
| WO2009055006A1 (en) | 2007-10-26 | 2009-04-30 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| WO2010020548A1 (en) | 2008-08-20 | 2010-02-25 | F. Hoffmann-La Roche Ag | Glyt1 receptor antagonists |
| AU2009289846B2 (en) | 2008-09-02 | 2014-10-16 | Sanofi-Aventis | Substituted aminoindanes and analogs thereof, and the pharmaceutical use thereof |
| DE102008047162A1 (de) | 2008-09-15 | 2010-03-25 | Institut Für Solarenergieforschung Gmbh | Rückkontaktsolarzelle mit integrierter Bypass-Diode sowie Herstellungsverfahren hierfür |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| EP2246331A1 (en) | 2009-04-24 | 2010-11-03 | Westfälische Wilhelms-Universität Münster | NR2B-selective NMDA-receptor antagonists |
| WO2010138901A1 (en) | 2009-05-29 | 2010-12-02 | Biogen Idec Ma Inc | Carboxylic acid-containing compounds, derivatives thereof, and related methods of use |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| JP2014521682A (ja) | 2011-08-05 | 2014-08-28 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン、アミノチオクロマンおよびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、ならびに治療におけるこれらの使用 |
| CN104011028A (zh) | 2011-11-18 | 2014-08-27 | 艾伯维德国有限责任两合公司 | N-取代的氨基苯并环庚烯、氨基四氢化萘、氨基茚满和苯烷基胺衍生物、包含所述衍生物的药物组合物及其在治疗中的用途 |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2016004934A (es) | 2013-10-17 | 2016-12-20 | Abbvie Deutschland | Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia. |
| CN105992764A (zh) | 2013-10-17 | 2016-10-05 | 艾伯维德国有限责任两合公司 | 氨基色满、氨基硫代色满及氨基-1,2,3,4-四氢喹啉衍生物，包含其的药物组合物及其在治疗中的用途 |
-
2011
- 2011-08-10 US US13/207,030 patent/US8846743B2/en active Active
- 2011-08-11 TW TW100128729A patent/TW201211030A/zh unknown
- 2011-08-12 JP JP2013523639A patent/JP2013538801A/ja active Pending
- 2011-08-12 MX MX2013001789A patent/MX2013001789A/es not_active Application Discontinuation
- 2011-08-12 CN CN2011800397167A patent/CN103189337A/zh active Pending
- 2011-08-12 EP EP11757790.8A patent/EP2603481B1/en not_active Not-in-force
- 2011-08-12 WO PCT/EP2011/063973 patent/WO2012020131A2/en not_active Ceased
- 2011-08-12 ES ES11757790.8T patent/ES2526074T3/es active Active
- 2011-08-12 CA CA2806644A patent/CA2806644A1/en not_active Abandoned
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2014
- 2014-06-27 US US14/317,104 patent/US9227930B2/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998004521A1 (en) * | 1996-07-26 | 1998-02-05 | Icagen, Inc. | Potassium channel inhibitors |
| CN1309631A (zh) * | 1998-07-31 | 2001-08-22 | 阿克佐诺贝尔公司 | 氨甲基羧酸衍生物 |
| WO2003045924A1 (en) * | 2001-11-21 | 2003-06-05 | Pharmacia & Upjohn Company | Substituted aryl 1,4-pyrazine derivatives |
| WO2009121872A2 (en) * | 2008-04-01 | 2009-10-08 | Abbott Gmbh & Co. Kg | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104418775A (zh) * | 2013-09-05 | 2015-03-18 | 中国科学院大连化学物理研究所 | 一种钯催化氨基醇的不对称氢解合成手性胺的方法 |
| CN104418775B (zh) * | 2013-09-05 | 2017-01-18 | 中国科学院大连化学物理研究所 | 一种钯催化氨基醇的不对称氢解合成手性胺的方法 |
| CN114276243A (zh) * | 2021-12-13 | 2022-04-05 | 浙江九洲药业股份有限公司 | 一种洛索洛芬及其类似物的合成方法 |
Also Published As
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| CA2806644A1 (en) | 2012-02-16 |
| MX2013001789A (es) | 2013-09-02 |
| TW201211030A (en) | 2012-03-16 |
| ES2526074T3 (es) | 2015-01-05 |
| WO2012020131A2 (en) | 2012-02-16 |
| EP2603481B1 (en) | 2014-09-17 |
| JP2013538801A (ja) | 2013-10-17 |
| US20140309206A1 (en) | 2014-10-16 |
| EP2603481A2 (en) | 2013-06-19 |
| US20120040948A1 (en) | 2012-02-16 |
| WO2012020131A3 (en) | 2012-04-05 |
| US9227930B2 (en) | 2016-01-05 |
| US8846743B2 (en) | 2014-09-30 |
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