MX2009011600A - Antagonistas de trpvi y usos de los mismos. - Google Patents
Antagonistas de trpvi y usos de los mismos.Info
- Publication number
- MX2009011600A MX2009011600A MX2009011600A MX2009011600A MX2009011600A MX 2009011600 A MX2009011600 A MX 2009011600A MX 2009011600 A MX2009011600 A MX 2009011600A MX 2009011600 A MX2009011600 A MX 2009011600A MX 2009011600 A MX2009011600 A MX 2009011600A
- Authority
- MX
- Mexico
- Prior art keywords
- halo
- alkyl
- another formulation
- formula
- independently
- Prior art date
Links
- 101150016206 Trpv1 gene Proteins 0.000 title claims description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 127
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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| US10954567B2 (en) | 2012-07-24 | 2021-03-23 | Pharmacyclics Llc | Mutations associated with resistance to inhibitors of Bruton's Tyrosine Kinase (BTK) |
| JP6249517B2 (ja) * | 2012-11-08 | 2017-12-20 | 花王株式会社 | 体感温度低減用外用剤 |
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| JP6308881B2 (ja) * | 2014-06-11 | 2018-04-11 | 保土谷化学工業株式会社 | 電荷制御剤およびそれを用いたトナー |
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Family Cites Families (149)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536809A (en) | 1969-02-17 | 1970-10-27 | Alza Corp | Medication method |
| US3598123A (en) | 1969-04-01 | 1971-08-10 | Alza Corp | Bandage for administering drugs |
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| US4409229A (en) | 1977-12-02 | 1983-10-11 | Hoechst-Roussel Pharmaceuticals, Inc. | Antidepressive and tranquilizing substituted 1,3-dihydrospiro[benzo(c)thiophene]s |
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| JPH0680054B2 (ja) | 1985-06-19 | 1994-10-12 | 吉富製薬株式会社 | ピペリジン誘導体 |
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| US5120548A (en) | 1989-11-07 | 1992-06-09 | Merck & Co., Inc. | Swelling modulated polymeric drug delivery device |
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| JP3191429B2 (ja) | 1992-09-02 | 2001-07-23 | 富士通テン株式会社 | 電子機器の挿排装置 |
| JP2789134B2 (ja) | 1992-09-28 | 1998-08-20 | ファイザー・インク. | 糖尿病の合併症を制御する置換ピリミジン類 |
| DE4234295A1 (de) * | 1992-10-12 | 1994-04-14 | Thomae Gmbh Dr K | Carbonsäurederivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5591767A (en) * | 1993-01-25 | 1997-01-07 | Pharmetrix Corporation | Liquid reservoir transdermal patch for the administration of ketorolac |
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| IT1270594B (it) | 1994-07-07 | 1997-05-07 | Recordati Chem Pharm | Composizione farmaceutica a rilascio controllato di moguisteina in sospensione liquida |
| DE19514313A1 (de) | 1994-08-03 | 1996-02-08 | Bayer Ag | Benzoxazolyl- und Benzothiazolyloxazolidinone |
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| KR100384979B1 (ko) * | 1995-09-07 | 2003-10-17 | 에프. 호프만-라 로슈 아게 | 심부전증및신부전증치료용의신규한4-(옥시알콕시페닐)-3-옥시-피페리딘 |
| EP0861075A1 (en) | 1995-11-13 | 1998-09-02 | Albany Medical College | Analgesic compounds and uses thereof |
| FR2744448B1 (fr) | 1996-02-02 | 1998-04-24 | Pf Medicament | Nouvelles piperidines derivees d'aryl piperazine, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| WO1997038665A2 (en) | 1996-04-03 | 1997-10-23 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5891889A (en) | 1996-04-03 | 1999-04-06 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US5948786A (en) * | 1996-04-12 | 1999-09-07 | Sumitomo Pharmaceuticals Company, Limited | Piperidinylpyrimidine derivatives |
| US5854245A (en) * | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| US5990107A (en) * | 1996-06-28 | 1999-11-23 | Merck & Co., Inc. | Fibrinogen receptor antagonist prodrugs |
| US5798360A (en) | 1996-08-01 | 1998-08-25 | Isis Pharmaceuticals, Inc. | N-(aminoalkyl)- and/or N-(amidoalkyl)- dinitrogen heterocyclic compositions |
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| FR2758328B1 (fr) | 1997-01-15 | 1999-04-02 | Pf Medicament | Nouvelles amines aromatiques derivees d'amines cycliques utiles comme medicaments |
| DE69819345T2 (de) | 1997-08-20 | 2004-07-15 | The Regents Of The University Of California, Oakland | Für den capsaicin rezeptor kodierende nukleinsäuresequenzen und dem capsaicin rezeptor ähnliche polypeptide und ihre verwendung |
| JPH11199573A (ja) | 1998-01-07 | 1999-07-27 | Yamanouchi Pharmaceut Co Ltd | 5ht3受容体作動薬及び新規ベンゾチアゾール誘導体 |
| IL137517A0 (en) | 1998-01-27 | 2001-07-24 | Aventis Pharm Prod Inc | Substituted oxoazaheterocyclyl factor xa inhibitors |
| EP0943683A1 (en) | 1998-03-10 | 1999-09-22 | Smithkline Beecham Plc | Human vanilloid receptor homologue Vanilrep1 |
| WO1999065896A1 (en) | 1998-06-19 | 1999-12-23 | Eli Lilly And Company | Preparation of heteroaryl compounds |
| WO2000001688A1 (en) | 1998-07-02 | 2000-01-13 | Sankyo Company, Limited | Five-membered heteroaryl compounds |
| BR9914018A (pt) | 1998-09-22 | 2001-07-03 | Yamanouchi Pharmaceuticals Co | Derivado de cianofenila |
| AU3215500A (en) | 1999-01-25 | 2000-08-07 | Smithkline Beecham Corporation | Compounds and methods |
| GB9907097D0 (en) | 1999-03-26 | 1999-05-19 | Novartis Ag | Organic compounds |
| TR200102810T2 (tr) * | 1999-04-01 | 2002-01-21 | Pfizer Products Inc. | Sorbitol dehidrojenaz inhibitörleri olarak aminopirimidinler |
| AU4797400A (en) | 1999-05-17 | 2000-12-05 | Eli Lilly And Company | Metabotropic glutamate receptor antagonists |
| GB9912411D0 (en) | 1999-05-28 | 1999-07-28 | Pfizer Ltd | Compounds useful in therapy |
| DE19934799B4 (de) | 1999-07-28 | 2008-01-24 | Az Electronic Materials (Germany) Gmbh | Chiral-smektische Flüssigkristallmischung und ihre Verwendung in Aktivmatrix-Displays mit hohen Kontrastwerten |
| US7343017B2 (en) * | 1999-08-26 | 2008-03-11 | American Technology Corporation | System for playback of pre-encoded signals through a parametric loudspeaker system |
| AU7514700A (en) | 1999-09-07 | 2001-04-10 | Syngenta Participations Ag | Cyanopiperidines |
| US6887870B1 (en) | 1999-10-12 | 2005-05-03 | Bristol-Myers Squibb Company | Heterocyclic sodium/proton exchange inhibitors and method |
| US7091227B2 (en) | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| EP1276736A2 (en) | 2000-04-25 | 2003-01-22 | Pharmacia Corporation | Regioselective synthesis of 3,4-di(carbocyclyl or heterocyclyl)thiophenes |
| BR0112395A (pt) | 2000-06-21 | 2003-07-08 | Hoffmann La Roche | Derivados de benzotiazol |
| AR028782A1 (es) | 2000-07-05 | 2003-05-21 | Taisho Pharmaceutical Co Ltd | Derivados heterociclicos tetrahidropiridino o piperidino |
| EP1299334B1 (en) | 2000-07-13 | 2008-01-16 | MERCK PATENT GmbH | Chiral compounds i |
| KR20030024799A (ko) * | 2000-07-20 | 2003-03-26 | 뉴로젠 코포레이션 | 캡사이신 수용체 리간드 |
| CA2426592A1 (en) | 2000-10-18 | 2002-04-25 | Pfizer Products Inc. | Combination of statins and sorbitol dehydrogenase inhibitors |
| EP1337271B1 (en) | 2000-11-30 | 2004-11-03 | Pfizer Products Inc. | Combination of gaba agonists and sorbitol dehydrogenase inhibitors |
| CA2431616C (en) | 2000-12-15 | 2010-02-09 | Japan Science And Technology Corporation | Arylbis(perfluoroalkylsulfonyl)methane and metallic salt thereof, and methods for producing the same |
| US7193113B2 (en) | 2000-12-15 | 2007-03-20 | Japan Science And Technology Corporation | Arylbis(perfluoroalkylsulfonyl) methane and metallic salt thereof, and methods for producing the same |
| US20030232996A1 (en) | 2001-04-20 | 2003-12-18 | Brown David L | Regioselective synthesis of 3,4-di{(carboclyl or heterocyclyl)thiophenes |
| DE60229059D1 (de) * | 2001-05-08 | 2008-11-06 | Univ Yale | Proteomimetische verbindungen und verfahren |
| US20040038982A1 (en) | 2001-07-13 | 2004-02-26 | Bondinell William E. | Compounds and methods |
| JP2003095951A (ja) | 2001-09-25 | 2003-04-03 | Sumitomo Pharmaceut Co Ltd | 慢性関節リウマチ治療剤 |
| EP1437344A4 (en) | 2001-09-28 | 2006-09-20 | Takeda Pharmaceutical | BENZENE DERIVATIVES AND PROCESS FOR THE PREPARATION AND USE THEREOF |
| JP2005516950A (ja) | 2001-12-19 | 2005-06-09 | メルク エンド カムパニー インコーポレーテッド | 代謝型グルタミン酸受容体−5のヘテロアリール置換イミダゾールモジュレータ |
| US7390813B1 (en) * | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| JP2003192673A (ja) | 2001-12-27 | 2003-07-09 | Bayer Ag | ピペラジンカルボキシアミド誘導体 |
| ATE465993T1 (de) | 2002-02-01 | 2010-05-15 | Euro Celtique Sa | 2-piperazinpyridine für die schmerzbehandlung |
| JP2005526723A (ja) * | 2002-02-15 | 2005-09-08 | グラクソ グループ リミテッド | バニロイド受容体モジュレーター |
| US6974818B2 (en) | 2002-03-01 | 2005-12-13 | Euro-Celtique S.A. | 1,2,5-thiadiazol-3-YL-piperazine therapeutic agents useful for treating pain |
| WO2003076400A1 (en) * | 2002-03-13 | 2003-09-18 | Janssen Pharmaceutica N.V. | New inhibitors of histone deacetylase |
| GB0209715D0 (en) | 2002-04-27 | 2002-06-05 | Astrazeneca Ab | Chemical compounds |
| CN1150176C (zh) | 2002-05-22 | 2004-05-19 | 上海医药工业研究院 | 芳烷酮哌嗪衍生物及其应用 |
| WO2003099266A2 (en) * | 2002-05-23 | 2003-12-04 | Abbott Laboratories | Acetamides and benzamides that are useful in treating sexual dysfunction |
| AU2003248245A1 (en) | 2002-06-26 | 2004-01-19 | Ono Pharmaceutical Co., Ltd. | Remedies for diseases caused by vascular contraction or dilation |
| BR0312322A (pt) * | 2002-06-28 | 2005-04-12 | Euro Celtique Sa | Compostos, composições, métodos para o tratamento da dor em um animal, da incontinência urinária em um animal, de uma úlcera em um animal, de sìndrome de intestino irritável em um animal, da doença inflamatória do intestino em um animal, métodos para a inibição da função de vr1 em uma célula, kits e métodos para a preparação de uma composição |
| EP1388538B1 (en) | 2002-07-09 | 2010-09-01 | Merck Patent GmbH | Polymerisation Initiator |
| US7262194B2 (en) * | 2002-07-26 | 2007-08-28 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| AU2003256922A1 (en) | 2002-07-31 | 2004-02-16 | Smithkline Beecham Corporation | Substituted heterocyclic compounds as modulators of the ccr5 receptor |
| US7157462B2 (en) | 2002-09-24 | 2007-01-02 | Euro-Celtique S.A. | Therapeutic agents useful for treating pain |
| NZ539064A (en) | 2002-09-27 | 2007-09-28 | Dainippon Sumitomo Pharma Co | Novel adenine compound and use thereof |
| US7582761B2 (en) | 2002-10-17 | 2009-09-01 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US7582635B2 (en) * | 2002-12-24 | 2009-09-01 | Purdue Pharma, L.P. | Therapeutic agents useful for treating pain |
| US7223788B2 (en) | 2003-02-14 | 2007-05-29 | Sanofi-Aventis Deutschland Gmbh | Substituted N-aryl heterocycles, process for their preparation and their use as medicaments |
| DE10311065A1 (de) * | 2003-03-13 | 2004-09-23 | Abbott Gmbh & Co. Kg | Pyrimidin-2-on-Verbindungen und ihre therapeutische Verwendung |
| ATE556067T1 (de) * | 2003-05-20 | 2012-05-15 | Ajinomoto Kk | Modulatoren des vanilloid rezeptors |
| AR044688A1 (es) | 2003-06-12 | 2005-09-21 | Euro Celtique Sa | Agentes terapeuticos utiles para el tratamiento del dolor |
| US20050009841A1 (en) * | 2003-07-11 | 2005-01-13 | Zheng Guo Zhu | Novel amides useful for treating pain |
| US7129235B2 (en) * | 2003-07-11 | 2006-10-31 | Abbott Laboratories | Amides useful for treating pain |
| DE602004021206D1 (de) | 2003-07-24 | 2009-07-02 | Euro Celtique Sa | Zur Behandlung oder Vorbeugung von Schmerzen geeignete Heteroaryl-Tetrahydropiperidyl-Verbindungen |
| DE602004020994D1 (de) * | 2003-07-24 | 2009-06-18 | Euro Celtique Sa | Piperidinverbindungen und pharmazeutische zusammensetzungen, die diese enthalten |
| PL1867644T3 (pl) | 2003-07-24 | 2009-10-30 | Euro Celtique Sa | Związki heteroarylo-tetrahydropiperydylowe przydatne w leczeniu lub zapobieganiu bólu |
| CA2533898A1 (en) * | 2003-07-29 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
| EP1651620B1 (en) * | 2003-07-30 | 2011-11-09 | Xenon Pharmaceuticals Inc. | Piperazine derivatives and their use as therapeutic agents |
| US7759348B2 (en) * | 2003-07-30 | 2010-07-20 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| JP4831577B2 (ja) * | 2003-07-30 | 2011-12-07 | 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 | ピリダジン誘導体および治療剤としての用途 |
| AU2004261267B9 (en) * | 2003-07-30 | 2009-04-09 | Xenon Pharmaceuticals Inc. | Pyridyl derivatives and their use as therapeutic agents |
| US7754711B2 (en) * | 2003-07-30 | 2010-07-13 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| CA2533899C (en) | 2003-07-30 | 2011-01-04 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| US7632950B2 (en) * | 2003-08-18 | 2009-12-15 | Fujifilm Finechemicals Co., Ltd | Pyridyltetrahydropyridines and pyridylpiperidines and method of manufacturing them |
| WO2005037284A1 (en) | 2003-10-15 | 2005-04-28 | Pfizer Products Inc. | Sorbitol dehydrogenase inhibitor and hypertensive agent combinations |
| US20050130974A1 (en) * | 2003-10-17 | 2005-06-16 | Rigel Pharmaceuticals, Inc. | Benzothiazole compositions and their use as ubiquitin ligase inhibitors |
| GB0325287D0 (en) | 2003-10-29 | 2003-12-03 | Merck Sharp & Dohme | Therapeutic agents |
| MY145822A (en) * | 2004-08-13 | 2012-04-30 | Neurogen Corp | Substituted biaryl piperazinyl-pyridine analogues |
| DE102004039789A1 (de) | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2006101521A2 (en) | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| AU2005286647A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515499A (pt) | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de piridina para a inibição de estearoil-coa-desaturase humana |
| AU2005286846A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| US20060116368A1 (en) | 2004-11-29 | 2006-06-01 | Calvo Raul R | 4-Piperidinecarboxamide modulators of vanilloid VR1 receptor |
| GT200600046A (es) | 2005-02-09 | 2006-09-25 | Terapia de combinacion | |
| US7893267B2 (en) * | 2005-03-14 | 2011-02-22 | High Point Pharmaceuticals, Llc | Benzazole derivatives, compositions, and methods of use as β-secretase inhibitors |
| DE102005014904A1 (de) | 2005-03-26 | 2007-02-01 | Abbott Gmbh & Co. Kg | Substituierte Oxindol-Derivate, diese enthaltende Arzneimittel und deren Verwendung |
| FR2884516B1 (fr) | 2005-04-15 | 2007-06-22 | Cerep Sa | Antagonistes npy, preparation et utilisations |
| US8193206B2 (en) * | 2005-06-14 | 2012-06-05 | Taigen Biotechnology Co., Ltd. | Pyrimidine compounds |
| JP4324221B2 (ja) | 2005-08-26 | 2009-09-02 | 株式会社医薬分子設計研究所 | Pparアゴニスト活性を有する誘導体 |
| EP1939175B1 (en) | 2005-09-27 | 2017-03-01 | Shionogi&Co., Ltd. | Sulfonamide derivative having pgd2 receptor antagonistic activity |
| US20070155707A1 (en) | 2005-12-29 | 2007-07-05 | Kadmus Pharmaceuticals, Inc. | Ionizable inhibitors of fatty acid amide hydrolase |
| JP2009523747A (ja) | 2006-01-18 | 2009-06-25 | シエナ ビオテク ソシエタ ペル アチオニ | α7ニコチン性アセチルコリン受容体のモジュレーターおよびその治療上の使用 |
| NZ570844A (en) | 2006-02-28 | 2011-11-25 | Helicon Therapeutics Inc | Therapeutic piperazines as PDE4 inhibitors |
| US20070208001A1 (en) | 2006-03-03 | 2007-09-06 | Jincong Zhuo | Modulators of 11- beta hydroxyl steroid dehydrogenase type 1, pharmaceutical compositions thereof, and methods of using the same |
| TW200815426A (en) * | 2006-06-28 | 2008-04-01 | Astrazeneca Ab | New pyridine analogues II 333 |
| WO2008005368A2 (en) * | 2006-06-30 | 2008-01-10 | Abbott Laboratories | Piperazines as p2x7 antagonists |
| WO2008013622A2 (en) | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| AU2007323193A1 (en) | 2006-11-20 | 2008-05-29 | Glenmark Pharmaceuticals S.A. | Acetylene derivatives as Stearoyl CoA Desaturase inhibitors |
| DE102006060598A1 (de) * | 2006-12-21 | 2008-06-26 | Merck Patent Gmbh | Tetrahydrobenzoisoxazole |
| US7998966B2 (en) | 2007-04-13 | 2011-08-16 | Supergen, Inc. | Axl kinase inhibitors |
| CA2685266C (en) | 2007-04-27 | 2014-01-28 | Purdue Pharma L.P. | Trpv1 antagonists and uses thereof for the treatment of prevention of pain, ui and ulcer, ibd, or ibs in an animal |
| JP5372913B2 (ja) * | 2007-04-27 | 2013-12-18 | パーデュー、ファーマ、リミテッド、パートナーシップ | 疼痛治療に有効な治療薬 |
| WO2008147864A2 (en) | 2007-05-22 | 2008-12-04 | Xenon Pharmaceuticals Inc. | Methods of using piperazine compounds in treating sodium channel-mediated diseases or conditions |
| US8058299B2 (en) | 2007-05-22 | 2011-11-15 | Via Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| IN2009KN04568A (enExample) | 2007-06-01 | 2015-08-28 | Univ Princeton | |
| MX2009013686A (es) | 2007-06-13 | 2010-01-27 | Univ Northeastern | Compuestos antibioticos. |
| US20100249144A1 (en) | 2007-06-28 | 2010-09-30 | Demong Duane Eugene | Substituted piperazines as cb1 antagonists |
| CN101815518B (zh) | 2007-06-29 | 2013-01-09 | 埃莫里大学 | 用于神经保护的nmda受体拮抗剂 |
| CA2708320A1 (en) | 2007-08-09 | 2009-02-19 | Abbott Laboratories | Amide derivatives as trpv1 antagonists |
| US7994174B2 (en) | 2007-09-19 | 2011-08-09 | Vertex Pharmaceuticals Incorporated | Pyridyl sulfonamides as modulators of ion channels |
| US8138168B1 (en) | 2007-09-26 | 2012-03-20 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| CA2700974A1 (en) | 2007-10-04 | 2009-04-09 | Merck Sharp & Dohme Corp. | Substituted aryl sulfone derivatives as calcium channel blockers |
| CA2708364A1 (en) | 2007-12-11 | 2009-06-18 | Efrat Ben-Zeev | Carboxamide compounds and their use as chemokine receptor agonists |
| JP2009249346A (ja) | 2008-04-08 | 2009-10-29 | Fujifilm Corp | ピリジン骨格を有する血液脳関門透過性化合物 |
| NZ590416A (en) | 2008-07-21 | 2012-10-26 | Purdue Pharma Lp | Substituted-quinoxaline-type bridged-piperidine compounds and the uses thereof |
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