MX2009001687A - Inhibidores del tipo i de 11-beta hidroxiesteroide deshidrogenasa ciclicos. - Google Patents
Inhibidores del tipo i de 11-beta hidroxiesteroide deshidrogenasa ciclicos.Info
- Publication number
- MX2009001687A MX2009001687A MX2009001687A MX2009001687A MX2009001687A MX 2009001687 A MX2009001687 A MX 2009001687A MX 2009001687 A MX2009001687 A MX 2009001687A MX 2009001687 A MX2009001687 A MX 2009001687A MX 2009001687 A MX2009001687 A MX 2009001687A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- aryl
- heterocyclyl
- cycloalkyl
- arylalkyl
- Prior art date
Links
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| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
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| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
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| JP6033791B2 (ja) | 2011-12-23 | 2016-11-30 | Meiji Seikaファルマ株式会社 | 新規s1p受容体調整薬 |
| US9580422B2 (en) | 2013-10-22 | 2017-02-28 | Bristol-Myers Squibb Company | Isotopically labeled triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
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Family Cites Families (89)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL99113C (enExample) | 1956-06-16 | |||
| US3674836A (en) | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
| US4027009A (en) | 1973-06-11 | 1977-05-31 | Merck & Co., Inc. | Compositions and methods for depressing blood serum cholesterol |
| JPS5612114B2 (enExample) | 1974-06-07 | 1981-03-18 | ||
| US4231938A (en) | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| DK149080C (da) | 1980-06-06 | 1986-07-28 | Sankyo Co | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| US4450171A (en) | 1980-08-05 | 1984-05-22 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| US4448784A (en) | 1982-04-12 | 1984-05-15 | Hoechst-Roussel Pharmaceuticals, Inc. | 1-(Aminoalkylphenyl and aminoalkylbenzyl)-indoles and indolines and analgesic method of use thereof |
| US5354772A (en) | 1982-11-22 | 1994-10-11 | Sandoz Pharm. Corp. | Indole analogs of mevalonolactone and derivatives thereof |
| FR2547814B1 (fr) | 1983-06-22 | 1985-10-18 | Sanofi Sa | Derives de l'acide bicyclo (3.2.1.) octane carboxylique, leur procede de preparation et leur application therapeutique |
| US4691051A (en) | 1985-01-04 | 1987-09-01 | Pennwalt Corporation | Adamantyl phenyl β-alanines |
| US4681893A (en) | 1986-05-30 | 1987-07-21 | Warner-Lambert Company | Trans-6-[2-(3- or 4-carboxamido-substituted pyrrol-1-yl)alkyl]-4-hydroxypyran-2-one inhibitors of cholesterol synthesis |
| US4759923A (en) | 1987-06-25 | 1988-07-26 | Hercules Incorporated | Process for lowering serum cholesterol using poly(diallylmethylamine) derivatives |
| JP2569746B2 (ja) | 1987-08-20 | 1997-01-08 | 日産化学工業株式会社 | キノリン系メバロノラクトン類 |
| NO177005C (no) | 1988-01-20 | 1995-07-05 | Bayer Ag | Analogifremgangsmåte for fremstilling av substituerte pyridiner, samt mellomprodukter til bruk ved fremstillingen |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5177080A (en) | 1990-12-14 | 1993-01-05 | Bayer Aktiengesellschaft | Substituted pyridyl-dihydroxy-heptenoic acid and its salts |
| WO1992018132A1 (en) | 1991-04-17 | 1992-10-29 | Merck & Co., Inc. | Pharmaceutical combination for the treatment of benign prostatic hyperplasia comtaining a 5 alpha-reductase inhibitor |
| JP2648897B2 (ja) | 1991-07-01 | 1997-09-03 | 塩野義製薬株式会社 | ピリミジン誘導体 |
| US5595872A (en) | 1992-03-06 | 1997-01-21 | Bristol-Myers Squibb Company | Nucleic acids encoding microsomal trigyceride transfer protein |
| US5594016A (en) | 1992-12-28 | 1997-01-14 | Mitsubishi Chemical Corporation | Naphthalene derivatives |
| SG45369A1 (en) | 1993-01-19 | 1998-10-16 | Warner Lambert Co | Stable oral ci-981 formulation and process of preparing same |
| US5739135A (en) | 1993-09-03 | 1998-04-14 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| IL111175A0 (en) | 1993-10-07 | 1994-12-29 | Du Pont Merck Pharma | Electrophilic peptide analogs as inhibitors of trypsin-like serine proteases and pharmaceutical compositions containing them |
| US5776983A (en) | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5488064A (en) | 1994-05-02 | 1996-01-30 | Bristol-Myers Squibb Company | Benzo 1,3 dioxole derivatives |
| US5385929A (en) | 1994-05-04 | 1995-01-31 | Warner-Lambert Company | [(Hydroxyphenylamino) carbonyl] pyrroles |
| FR2723317B1 (fr) | 1994-08-04 | 1996-10-31 | Sanofi Sa | Utilisation d'antagonistes de la neurotensine pour la preparation de medicaments diuretiques |
| US5612359A (en) | 1994-08-26 | 1997-03-18 | Bristol-Myers Squibb Company | Substituted biphenyl isoxazole sulfonamides |
| US5491134A (en) | 1994-09-16 | 1996-02-13 | Bristol-Myers Squibb Company | Sulfonic, phosphonic or phosphiniic acid β3 agonist derivatives |
| US5541204A (en) | 1994-12-02 | 1996-07-30 | Bristol-Myers Squibb Company | Aryloxypropanolamine β 3 adrenergic agonists |
| US5620997A (en) | 1995-05-31 | 1997-04-15 | Warner-Lambert Company | Isothiazolones |
| WO1997012613A1 (en) | 1995-10-05 | 1997-04-10 | Warner-Lambert Company | Method for treating and preventing inflammation and atherosclerosis |
| EP0873361B1 (en) | 1995-12-13 | 2006-11-02 | The Regents Of The University Of California | Crystals of the ligand-binding domain of the thyroid hormone receptor complexed to a ligand |
| KR100487032B1 (ko) | 1996-03-14 | 2005-12-21 | 워너-램버트 캄파니 엘엘씨 | 약제로서신규한브리지된시클릭아미노산 |
| US5770615A (en) | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
| US5962440A (en) | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
| US5885983A (en) | 1996-05-10 | 1999-03-23 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| US5827875A (en) | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
| DZ2285A1 (fr) | 1996-08-08 | 2002-12-25 | Smithkline Beecham Corp | Inhibiteurs de protéase de la cystéine. |
| GB9624611D0 (en) | 1996-11-26 | 1997-01-15 | Zeneca Ltd | Bicyclic amine compounds |
| US5760246A (en) | 1996-12-17 | 1998-06-02 | Biller; Scott A. | Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method |
| TW536540B (en) | 1997-01-30 | 2003-06-11 | Bristol Myers Squibb Co | Endothelin antagonists: N-[[2'-[[(4,5-dimethyl-3-isoxazolyl)amino]sulfonyl]-4-(2-oxazolyl)[1,1'-biphenyl]-2-yl]methyl]-N,3,3-trimethylbutanamide and N-(4,5-dimethyl-3-isoxazolyl)-2'-[(3,3-dimethyl-2-oxo-1-pyrrolidinyl)methyl]-4'-(2-oxazolyl)[1,1'-biphe |
| AU6843498A (en) | 1997-03-28 | 1998-10-22 | Zeneca Limited | Process for the preparation of n-(3-hydroxy-succinyl)-amino acid derivatives |
| GB9713739D0 (en) | 1997-06-27 | 1997-09-03 | Karobio Ab | Thyroid receptor ligands |
| EP1009405A4 (en) | 1997-08-28 | 2001-05-09 | Merck & Co Inc | PAYRROLIDINE AND PIPERIDINE MODULATORS OF CHEMOKINE RECEPTOR ACTIVITY |
| UA57811C2 (uk) | 1997-11-21 | 2003-07-15 | Пфайзер Продактс Інк. | Фармацевтична композиція, що містить інгібітор альдозоредуктази та інгібітор глікогенфосфорилази (варіанти), комплект, який її включає, та способи лікування ссавців зі станом інсулінорезистентності |
| TR200001795T2 (tr) | 1997-12-16 | 2000-11-21 | Warner-Lambert Company | 1-İkameli-1-Aminometil-sikloalkan türevleri (=Gabapentin analogları), bunların hazırlanması ve nörolojik bozuklukların tedavisinde kullanımı. |
| CN1289341A (zh) | 1998-01-26 | 2001-03-28 | Basf公司 | 凝血酶抑制剂 |
| TR200002480T2 (tr) | 1998-02-27 | 2000-12-21 | Pfizer Products Inc. | İzaşemi tedavisi için guanidin türevleri |
| IL140622A0 (en) | 1998-07-06 | 2002-02-10 | Bristol Myers Squibb Co | Biphenyl sufonamide derivatives, pharmaceutical compositions containing the same and methods for the preparation thereof |
| GB9828442D0 (en) | 1998-12-24 | 1999-02-17 | Karobio Ab | Novel thyroid receptor ligands and method II |
| HUP9900445A2 (hu) * | 1999-02-24 | 2001-06-28 | EGIS Gyógyszergyár Rt. | Eljárás (1R,2S,4R)-(-)-N,N-(dimetilamino-etoxi)-2-fenil-1,7,7-trimetil-biciklo[2.2.1]heptán előállítására és ennek köztiterméke |
| US6548529B1 (en) | 1999-04-05 | 2003-04-15 | Bristol-Myers Squibb Company | Heterocyclic containing biphenyl aP2 inhibitors and method |
| TW200514783A (en) | 1999-09-22 | 2005-05-01 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| PH12000002657B1 (en) | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| WO2001060818A1 (en) | 2000-02-14 | 2001-08-23 | Tularik Inc. | Lxr modulators |
| US6620829B2 (en) * | 2000-10-17 | 2003-09-16 | Warner-Lambert Company | Method of treating noninflammatory cartilage damage |
| US7112593B2 (en) | 2001-03-27 | 2006-09-26 | Eisai Co., Ltd. | N-aryl-substituted cyclic amine derivative and medicine containing the same as active ingredient |
| JP4776810B2 (ja) | 2001-05-30 | 2011-09-21 | 日本曹達株式会社 | α位トリ置換酢酸の製造方法 |
| DK1404324T4 (da) * | 2001-06-11 | 2011-07-11 | Xenoport Inc | Prolægemidler af GABA analoger, sammensætninger og anvendelser deraf |
| US20030114460A1 (en) | 2001-12-14 | 2003-06-19 | Allergan Sales, Inc. | Pharmaceutical conjugates with enhanced pharmacokinetic characteristics |
| KR20040081478A (ko) | 2002-01-31 | 2004-09-21 | 워너-램버트 캄파니 엘엘씨 | 이명을 치료하기 위한 알파 2 델타 리간드 |
| DE60317631T2 (de) | 2002-02-01 | 2008-09-25 | Merck & Co., Inc. | 11-beta-hydroxysteroid-dehydrogenase-1-hemmer zur behandlung von diabetes, adipositas und dyslipidämie |
| TW200401635A (en) * | 2002-07-23 | 2004-02-01 | Yamanouchi Pharma Co Ltd | 2-Cyano-4-fluoropyrrolidine derivative or salt thereof |
| JP4012016B2 (ja) * | 2002-08-29 | 2007-11-21 | キヤノン株式会社 | 画像処理装置、画像処理方法、記憶媒体、及びプログラム |
| US20040209858A1 (en) | 2002-10-22 | 2004-10-21 | Bennani Youssef L. | Cycloalkylamides and their therapeutic applications |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| TW200503994A (en) | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| US7135575B2 (en) * | 2003-03-03 | 2006-11-14 | Array Biopharma, Inc. | P38 inhibitors and methods of use thereof |
| JP2006522744A (ja) | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | グルココルチコイド受容体アゴニスト療法に伴う副作用を最小化するための、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤およびグルココルチコイド受容体アゴニストを使用する併用療法 |
| US20060094699A1 (en) | 2003-04-11 | 2006-05-04 | Kampen Gita Camilla T | Combination therapy using an 11beta-hydroxysteroid dehydrogenase type 1 inhibitor and a glucocorticoid receptor agonist to minimize the side effects associated with glucocorticoid receptor agonist therapy |
| JP2006522750A (ja) | 2003-04-11 | 2006-10-05 | ノボ ノルディスク アクティーゼルスカブ | 代謝性症候群ならびに関連の疾患および障害を治療するために、11β−ヒドロキシステロイドデヒドロゲナーゼ1型阻害剤および抗高血圧剤を使用する併用療法 |
| US7700583B2 (en) | 2003-04-11 | 2010-04-20 | High Point Pharmaceuticals, Llc | 11β-hydroxysteroid dehydrogenase type 1 active compounds |
| US7501405B2 (en) | 2003-04-11 | 2009-03-10 | High Point Pharmaceuticals, Llc | Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders |
| EP1615698B1 (en) | 2003-04-11 | 2010-09-29 | High Point Pharmaceuticals, LLC | New amide derivatives and pharmaceutical use thereof |
| TW200528440A (en) * | 2003-10-31 | 2005-09-01 | Fujisawa Pharmaceutical Co | 2-cyanopyrrolidinecarboxamide compound |
| US20080096922A1 (en) * | 2004-04-06 | 2008-04-24 | Dainippon Sumitomo Pharma Co., Ltd. | Novel Sulfonamide derivative |
| US7880001B2 (en) | 2004-04-29 | 2011-02-01 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase Type 1 enzyme |
| EP1841723A1 (en) | 2004-12-31 | 2007-10-10 | Universität Dortmund | Decaline derived compounds as pharmaceutically active agents |
| US7217838B2 (en) | 2005-01-05 | 2007-05-15 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| US20060148871A1 (en) | 2005-01-05 | 2006-07-06 | Rohde Jeffrey J | Metabolic stabilization of substituted adamantane |
| US7511175B2 (en) | 2005-01-05 | 2009-03-31 | Abbott Laboratories | Inhibitors of the 11-beta-hydroxysteroid dehydrogenase type 1 enzyme |
| WO2007038452A1 (en) | 2005-09-28 | 2007-04-05 | Merck & Co., Inc. | Process for synthesizing 1,2,4-triazoles |
| NI200800069A (es) | 2005-10-20 | 2008-06-25 | Merck & Co Inc | Derivados de triazol como inhibidores de 11-beta-hidroxiesteroide-deshidrogenasa-1 |
| EP1801098A1 (en) | 2005-12-16 | 2007-06-27 | Merck Sante | 2-Adamantylurea derivatives as selective 11B-HSD1 inhibitors |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| US7727978B2 (en) * | 2006-08-24 | 2010-06-01 | Bristol-Myers Squibb Company | Cyclic 11-beta hydroxysteroid dehydrogenase type I inhibitors |
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2007
- 2007-08-22 US US11/843,015 patent/US7727978B2/en active Active
- 2007-08-23 KR KR1020097005903A patent/KR20090057038A/ko not_active Withdrawn
- 2007-08-23 CN CN201410057480.5A patent/CN103833544A/zh active Pending
- 2007-08-23 EP EP20120181050 patent/EP2527317A1/en not_active Withdrawn
- 2007-08-23 JP JP2009525773A patent/JP5268912B2/ja not_active Expired - Fee Related
- 2007-08-23 CA CA002661401A patent/CA2661401A1/en not_active Abandoned
- 2007-08-23 BR BRPI0715839-4A patent/BRPI0715839A2/pt not_active IP Right Cessation
- 2007-08-23 EA EA200900344A patent/EA200900344A1/ru unknown
- 2007-08-23 EP EP07814376.5A patent/EP2054368B1/en active Active
- 2007-08-23 MX MX2009001687A patent/MX2009001687A/es active IP Right Grant
- 2007-08-23 AU AU2007286629A patent/AU2007286629A1/en not_active Abandoned
- 2007-08-23 WO PCT/US2007/076593 patent/WO2008024892A2/en not_active Ceased
- 2007-08-24 TW TW096131558A patent/TW200817353A/zh unknown
- 2007-08-24 AR ARP070103783A patent/AR062533A1/es not_active Application Discontinuation
- 2007-08-24 CL CL2007002492A patent/CL2007002492A1/es unknown
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| WO2008024892A3 (en) | 2008-12-11 |
| IL196989A0 (en) | 2009-11-18 |
| BRPI0715839A2 (pt) | 2013-07-23 |
| EP2054368B1 (en) | 2015-09-16 |
| JP2010501589A (ja) | 2010-01-21 |
| AR062533A1 (es) | 2008-11-12 |
| US7727978B2 (en) | 2010-06-01 |
| WO2008024892A2 (en) | 2008-02-28 |
| CA2661401A1 (en) | 2008-02-28 |
| EP2527317A1 (en) | 2012-11-28 |
| NO20090445L (no) | 2009-02-26 |
| JP2013173783A (ja) | 2013-09-05 |
| CN103833544A (zh) | 2014-06-04 |
| US20080234249A1 (en) | 2008-09-25 |
| KR20090057038A (ko) | 2009-06-03 |
| JP5268912B2 (ja) | 2013-08-21 |
| US8299054B2 (en) | 2012-10-30 |
| EA200900344A1 (ru) | 2009-10-30 |
| US20100204199A1 (en) | 2010-08-12 |
| CL2007002492A1 (es) | 2008-01-11 |
| TW200817353A (en) | 2008-04-16 |
| EP2054368A2 (en) | 2009-05-06 |
| AU2007286629A1 (en) | 2008-02-28 |
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