JP2011518196A5 - - Google Patents
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- JP2011518196A5 JP2011518196A5 JP2011505265A JP2011505265A JP2011518196A5 JP 2011518196 A5 JP2011518196 A5 JP 2011518196A5 JP 2011505265 A JP2011505265 A JP 2011505265A JP 2011505265 A JP2011505265 A JP 2011505265A JP 2011518196 A5 JP2011518196 A5 JP 2011518196A5
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Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7565145B2 (en) | 2002-10-18 | 2009-07-21 | Kineto Wireless, Inc. | Handover messaging in an unlicensed mobile access telecommunications system |
| US7940746B2 (en) | 2004-08-24 | 2011-05-10 | Comcast Cable Holdings, Llc | Method and system for locating a voice over internet protocol (VoIP) device connected to a network |
| US20090175973A1 (en) * | 2007-09-05 | 2009-07-09 | Nina Vikhrieva | Coffee cherry compositions and methods for their use in the treatment of diabetes and diabetes related disorders |
| EP2282735B1 (en) | 2008-04-21 | 2019-01-16 | Signum Biosciences, Inc. | Pp2a modulators for treating alzheimer, parkinson, diabetes |
| DE102008025893B4 (de) * | 2008-05-26 | 2014-09-18 | Technische Universität Dresden | Verfahren zur Herstellung von Fettsäureamiden mit gesättigten, ungesättigten oder Hydroxy-Fettsäuren |
| FR2942625B1 (fr) * | 2009-03-02 | 2013-11-22 | Centre Nat Rech Scient | Derives indoliques pour le traitement de maladies neurodegeneratives |
| US9073851B2 (en) | 2011-10-28 | 2015-07-07 | Board Of Regents, The University Of Texas System | Compositions and methods for treating cancer |
| CN103086948A (zh) * | 2011-11-02 | 2013-05-08 | 上海朴颐化学科技有限公司 | (s,s,s)-2-氮杂双环[3,3,0]辛烷-3-羧酸的制备方法 |
| CA2877167A1 (en) | 2012-06-29 | 2014-01-03 | Lixte Biotechnology, Inc. | Oxabicycloheptanes and oxabicycloheptenes for the treatment of diabetes |
| US20170224757A1 (en) | 2014-07-22 | 2017-08-10 | Signum Nutralogix, Inc. | Natural extracts for modulating pp2a methylation, and providing antioxidant and anti inflammatory activity |
| MX395174B (es) * | 2014-10-15 | 2025-03-21 | Signum Biosciences Inc | Composiciones de triptamina y metodos de uso. |
| US20160201009A1 (en) * | 2015-01-10 | 2016-07-14 | Aurelio Lopez | Integrated oil extraction apparatus |
| KR101874594B1 (ko) * | 2016-12-07 | 2018-07-05 | 한국한의학연구원 | 아떼모야 잎 추출물 또는 이의 분획물을 포함하는 인지기능 장애의 예방 또는 치료용 조성물 |
| WO2020092930A1 (en) * | 2018-11-02 | 2020-05-07 | Rutgers, The State University Of New Jersey | Synergistic composition having neuroprotective properties and methods of use thereof |
| EP4003363A4 (en) * | 2019-07-25 | 2023-08-16 | North Carolina State University | CROSS-LINKING COMPOUNDS AND METHODS OF USE |
| JP2021028325A (ja) * | 2019-08-09 | 2021-02-25 | 株式会社ACrux | 中枢機能改善剤および中枢機能改善用飲食品 |
| EP4334285A4 (en) * | 2021-05-05 | 2025-07-30 | Kare Chemical Tech Inc | CATALYTIC TRYPTAMINE PROCESSES AND PRECURSORS |
| WO2023019368A1 (en) * | 2021-08-20 | 2023-02-23 | Mindset Pharma Inc. | 3-cycloamino-indole compounds as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (191)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2852520A (en) | 1957-01-08 | 1958-09-16 | Searle & Co | Trialkoxybenzoyloxyalkyl derivatives related to norharman |
| DE2856856A1 (de) * | 1978-01-09 | 1979-07-12 | Sandoz Ag | Fettsaeure-amid-und-hydracid derivate, ihre herstellung und ihre verwendung als pharmazeutika |
| US4448785A (en) * | 1978-01-09 | 1984-05-15 | Sandoz, Inc. | N-Unsaturated fatty acid amides of tryptophan ester homologues and anti-cholesteric use thereof |
| US4185118A (en) | 1978-01-09 | 1980-01-22 | Sandoz, Inc. | Benzocycloalkylamides |
| US4194002A (en) | 1978-03-29 | 1980-03-18 | Sandoz, Inc. | Cholesterol ester-reducing amides of hexahydroindolinols |
| US4229463A (en) | 1978-02-27 | 1980-10-21 | Sandoz, Inc. | Unsaturated fatty acid hydrazides |
| US4201785A (en) | 1978-02-27 | 1980-05-06 | Sandoz Inc. | Cyclopropanyl-bearing hydrazides |
| US4248893A (en) | 1978-12-30 | 1981-02-03 | Sandoz, Inc. | Arterial wall cholesterol ester reducing cyclopropanyl-bearing amides |
| DE3105850A1 (de) | 1981-02-18 | 1982-08-19 | Horst, Hans Jörg, Priv.Doz.Dr., 2057 Reinbek | Mittel zum behandeln von tumoren |
| CA1280414C (en) | 1985-03-15 | 1991-02-19 | Saichi Matsumoto | Isoprenoidamine derivatives and antiulcer agents |
| US4709094A (en) | 1986-07-10 | 1987-11-24 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | Sigma brain receptor ligands and their use |
| US4906779A (en) | 1986-07-10 | 1990-03-06 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US5093525A (en) | 1986-07-10 | 1992-03-03 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| US5190976A (en) | 1986-07-10 | 1993-03-02 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And University Of Oregon | N,N'-disubstituted guanidines and their use as excitatory amino acid antagonists |
| JPH0752542Y2 (ja) | 1988-02-26 | 1995-11-29 | 東芝設備機器株式会社 | 冷却器 |
| US4933324A (en) | 1988-02-26 | 1990-06-12 | Shashoua Victor E | Fatty acid-neuroactive drug conjugate as a prodrug |
| US5284876A (en) | 1988-02-26 | 1994-02-08 | Neuromedica, Inc. | Method of treating tardive dyskinesia using dopaminergic agents of prodrugs of therapeutic agents |
| US4939174A (en) | 1988-02-26 | 1990-07-03 | Shashoua Victor E | Appetite suppression with dopamine-fatty acid conjugates |
| US5994392A (en) | 1988-02-26 | 1999-11-30 | Neuromedica, Inc. | Antipsychotic prodrugs comprising an antipsychotic agent coupled to an unsaturated fatty acid |
| US6107499A (en) | 1988-02-26 | 2000-08-22 | Neuromedica, Inc. | Dopamine analog amide |
| US4935422A (en) | 1988-12-15 | 1990-06-19 | E. I. Du Pont De Nemours And Company | Acyloxypropanolamines |
| US5175183A (en) | 1989-02-01 | 1992-12-29 | Abbott Laboratories | Lipoxygenase inhibiting compounds |
| IE68593B1 (en) | 1989-12-06 | 1996-06-26 | Sanofi Sa | Heterocyclic substituted acylaminothiazoles their preparation and pharmaceutical compositions containing them |
| JPH0625276Y2 (ja) | 1989-12-29 | 1994-07-06 | 株式会社ワコール | 硬質線状体の押込み手作業用プロテクタ |
| IT1243846B (it) | 1990-10-17 | 1994-06-28 | Pulitzer Italiana | Derivato della melatonina ad attivita' terapeutica in dermatologia. |
| EP0590009B1 (en) | 1991-06-19 | 1998-03-18 | PHARMACIA & UPJOHN COMPANY | Dialkyl (dialkoxyphosphinyl)methyl phosphates as anti-inflammatory agents |
| GB9218541D0 (en) | 1991-09-30 | 1992-10-14 | Ici Plc | Fungicides |
| FR2706456B1 (fr) | 1993-06-18 | 1996-06-28 | Rhone Poulenc Agrochimie | Dérivés optiquement actifs de 2-imidazoline-5-ones et 2-imidazoline-5-thiones fongicides. |
| US5322858A (en) | 1992-02-14 | 1994-06-21 | Jacobus Pharmaceutical Co. Inc. | N,N'-substituted imidodicarbonimidic diamides derived from hydroxylamines |
| JPH0625276A (ja) | 1992-05-13 | 1994-02-01 | Tanabe Seiyaku Co Ltd | アシルアミノ糖誘導体及びその製法 |
| US5585358A (en) | 1993-07-06 | 1996-12-17 | Yissum Research Development Corporation Of The Hebrew University Of Jerusalem | Derivatives of valproic acid amides and 2-valproenoic acid amides, method of making and use thereof as anticonvulsant agents |
| EP0634402A1 (en) | 1993-07-14 | 1995-01-18 | Takeda Chemical Industries, Ltd. | Isochinolinone derivatives, their production and use |
| JP3268073B2 (ja) | 1993-08-17 | 2002-03-25 | 三菱製紙株式会社 | 可逆性感熱記録材料 |
| US6869957B1 (en) | 1993-11-17 | 2005-03-22 | Eli Lilly And Company | Non-peptide tachykinin receptor antagonists |
| US6403577B1 (en) | 1993-11-17 | 2002-06-11 | Eli Lilly And Company | Hexamethyleneiminyl tachykinin receptor antagonists |
| ATE346595T1 (de) * | 1994-02-08 | 2006-12-15 | Nps Pharma Inc | An einer neuen stelle von rezeptorabhängigen kalziumkanälen wirkende verbindungen zur behandlung von neurologischen erkrankungen |
| DE69519963T2 (de) * | 1994-07-23 | 2001-06-21 | Societe Des Produits Nestle S.A., Vevey | Antioxidantzusammensetzung und Verfahren zu ihrer Herstellung |
| FR2724384B1 (fr) | 1994-09-14 | 1999-04-16 | Cemaf | Nouveaux derives de la 3,4-dihydro beta-carboline agonistes de la melatonine, leur procede de preparation et leur utilisation a titre de medicament |
| JP3795093B2 (ja) | 1994-11-25 | 2006-07-12 | キッセイ薬品工業株式会社 | 1−ヒドロキシインドール誘導体 |
| JPH08157816A (ja) | 1994-12-02 | 1996-06-18 | Oriza Yuka Kk | 天然抗酸化剤およびその製造方法 |
| GB9426102D0 (en) | 1994-12-23 | 1995-02-22 | Merck Sharp & Dohme | Pharmacuetical compositions |
| HUP9702388A3 (en) | 1995-01-27 | 1999-01-28 | Novo Nordisk As | Compounds with growth hormone releasing properties and pharmaceuticals contg. them |
| FR2734814B1 (fr) | 1995-05-31 | 1997-07-04 | Adir | Nouveaux composes alkoxy-aryles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| GB9513972D0 (en) | 1995-07-08 | 1995-09-06 | Merck Sharp & Dohme | Pharmaceutical compositions |
| CA2203424A1 (en) | 1995-08-21 | 1997-02-27 | Eli Lilly And Company | 2-acylaminopropanamines as growth hormone secretagogues |
| US5821261A (en) | 1995-12-08 | 1998-10-13 | Merck & Co., Inc. | Substituted saturated aza heterocycles as inhibitors of nitric oxide synthase |
| US5849764A (en) * | 1995-12-14 | 1998-12-15 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| JPH09301954A (ja) | 1996-05-14 | 1997-11-25 | Kumiai Chem Ind Co Ltd | N−(縮合ヘテロアリールアルキル)アルカン酸アミド誘導体及び農園芸用殺菌剤 |
| US5795877A (en) | 1996-12-31 | 1998-08-18 | Guilford Pharmaceuticals Inc. | Inhibitors of NAALADase enzyme activity |
| US5902817A (en) | 1997-04-09 | 1999-05-11 | Guilford Pharmaceuticals Inc. | Certain sulfoxide and sulfone derivatives |
| US5977090A (en) | 1996-09-27 | 1999-11-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating compulsive disorders using NAALADase inhibitors |
| US5824662A (en) | 1996-09-27 | 1998-10-20 | Guilford Pharmaceuticals Inc. | Treatment of global and focal ischemia using naaladase inhibitors |
| US6025344A (en) | 1996-06-17 | 2000-02-15 | Guilford Pharmaceuticals Inc. | Certain dioic acid derivatives useful as NAALADase inhibitors |
| US6054444A (en) | 1997-04-24 | 2000-04-25 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US6017903A (en) | 1996-09-27 | 2000-01-25 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors |
| US5863536A (en) | 1996-12-31 | 1999-01-26 | Guilford Pharmaceuticals Inc. | Phosphoramidate derivatives |
| US6071965A (en) | 1996-06-17 | 2000-06-06 | Guilford Pharmaceuticals Inc. | Phosphinic alkanoic acid derivatives |
| US6046180A (en) | 1996-06-17 | 2000-04-04 | Guilford Pharmaceuticals Inc. | NAALADase inhibitors |
| US5700821A (en) | 1996-07-30 | 1997-12-23 | University Of Pittsburgh | Phosphatase inhibitors and methods of use thereof |
| AU6824396A (en) | 1996-08-09 | 1998-03-06 | Sederma Sa | Melatonin derivatives and their use in cosmetic or dermopharmaceutical compositions |
| JPH1077229A (ja) | 1996-09-03 | 1998-03-24 | Sagami Chem Res Center | 自発運動抑制剤 |
| JPH1077267A (ja) | 1996-09-03 | 1998-03-24 | Sagami Chem Res Center | 5−メトキシトリプタミン誘導体 |
| US5962521A (en) | 1997-04-04 | 1999-10-05 | Guilford Pharmaceuticals Inc. | Hydroxamic acid derivatives |
| GB9620777D0 (en) | 1996-10-07 | 1996-11-20 | Merck Sharp & Dohme | Therapeutic use |
| AT2009U1 (de) | 1997-01-24 | 1998-03-25 | Trodat Werke Walter Just Gmbh | Einrichtung zur ablage von handstempeln und anderen büroutensilien |
| RU2141483C1 (ru) | 1997-07-04 | 1999-11-20 | Небольсин Владимир Евгеньевич | Производные пептидов или их фармацевтически приемлемые соли, способ их получения, применение и фармацевтическая композиция |
| CA2295697A1 (en) | 1997-07-10 | 1999-01-21 | Jason Scott Sawyer | Inhibitors of neutrophil mediated oxidant production |
| CN1067527C (zh) | 1997-07-13 | 2001-06-27 | 赵宁斌 | 柿叶茶的制备方法 |
| AP9801302A0 (en) | 1997-07-23 | 2000-01-23 | Pfizer | Indole compounds as anti-inflammatory/analgesic agents.. |
| US7041702B1 (en) | 1997-10-21 | 2006-05-09 | Scion Pharmaceuticals, Inc. | Pharmaceutically active compounds and methods of use |
| HU227568B1 (en) | 1997-12-24 | 2011-08-29 | Sanofi Aventis Deutschland | Indole derivatives, as inhibitors os factor xa |
| GB9804343D0 (en) | 1998-02-27 | 1998-04-22 | Univ Cardiff | Chemical compounds |
| WO1999054442A1 (en) | 1998-04-17 | 1999-10-28 | Emory University | Protein phosphatase methylesterase dna |
| FR2778671B1 (fr) | 1998-05-14 | 2002-07-05 | Rhone Poulenc Agrochimie | Nouveau procede de preparation d'intermediaires de synthese |
| GB9812083D0 (en) | 1998-06-05 | 1998-08-05 | Ici Plc | Removal of water |
| WO2000012045A2 (en) | 1998-08-26 | 2000-03-09 | St. Elizabeth's Medical Center Of Boston, Inc. | Method for treating neurodegenerative disorders |
| DE19842416A1 (de) * | 1998-09-16 | 2000-04-13 | Max Planck Gesellschaft | Sekundäre Amine zur Prävention und Therapie von Erkrankungen, die durch Oxidationsprozesse verursacht oder verstärkt werden |
| IL145771A0 (en) | 1999-04-09 | 2002-07-25 | Basf Ag | Low-molecular inhibitors of complement proteases |
| US6503949B1 (en) | 1999-05-17 | 2003-01-07 | Noro Nordisk A/S | Glucagon antagonists/inverse agonists |
| WO2001021606A1 (en) | 1999-09-21 | 2001-03-29 | Qinetiq Limited | Liquid crystal compounds |
| AU7832000A (en) | 1999-09-23 | 2001-04-24 | Washington University | Compounds directed against pilus biogenesis and activity in pathogenic bacteria;methods and compositions for synthesis thereof |
| US20030036070A1 (en) | 1999-10-21 | 2003-02-20 | Shukti Chakravarti | Gene expression profiling of inflammatory bowel disease |
| FR2802206B1 (fr) | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | Derives de 4-aminopiperidine et leur utilisation en tant que medicament |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| US6372752B1 (en) | 2000-02-07 | 2002-04-16 | Genzyme Corporation | Inha inhibitors and methods of use thereof |
| US6653304B2 (en) | 2000-02-11 | 2003-11-25 | Bristol-Myers Squibb Co. | Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators for treating respiratory and non-respiratory diseases |
| JP2001247539A (ja) | 2000-03-03 | 2001-09-11 | Hunan Research Inst Of Chemical Industry | 殺生物性のアルキル置換された(ヘテロ)アリール‐ケトキシム‐o‐エーテルおよびその製造方法 |
| AU779041B2 (en) | 2000-05-02 | 2005-01-06 | Meiji Seika Kaisha Ltd. | Novel indole derivatives exhibiting chymase-inhibitory activities and process for preparation thereof |
| US20020034524A1 (en) | 2000-06-19 | 2002-03-21 | Poret Jacques Louis | Cosmetic compositions containing keratinization modulators and methods for improving keratinous surfaces |
| US6562807B2 (en) | 2000-06-23 | 2003-05-13 | Novo Nordisk A/S | Glucagon antagonists/inverse agonists |
| CA2321348A1 (en) | 2000-09-27 | 2002-03-27 | Blaise Magloire N'zemba | Aromatic derivatives with hiv integrase inhibitory properties |
| US20040053963A1 (en) | 2000-12-11 | 2004-03-18 | Dashyant Dhanak | Urotensin-II receptor antagonists |
| JP2002193923A (ja) | 2000-12-26 | 2002-07-10 | Taisho Pharmaceut Co Ltd | アミノ安息香酸誘導体 |
| WO2003080556A1 (en) | 2001-01-19 | 2003-10-02 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. | Amine derivative with potassium channel regulatory function, its preparation and use |
| JP2004524295A (ja) | 2001-01-26 | 2004-08-12 | スミスクライン・ビーチャム・コーポレイション | ウロテンシン−ii受容体アンタゴニスト |
| US7173027B2 (en) | 2001-01-29 | 2007-02-06 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
| US7820144B2 (en) | 2001-01-29 | 2010-10-26 | University Of Connecticut | Receptor selective cannabimimetic aminoalkylindoles |
| AUPR392301A0 (en) | 2001-03-23 | 2001-04-26 | University Of Newcastle Research Associates Limited, The | Protein phosphatase inhibitors |
| US20040138224A1 (en) | 2002-03-28 | 2004-07-15 | Dashyant Dhanak | Pyrrolidine sulfonamides |
| WO2002079155A1 (en) | 2001-03-29 | 2002-10-10 | Smithkline Beecham Corporation | Pyrrolidine sulfonamides |
| EP1392639B1 (en) | 2001-05-03 | 2008-09-17 | Galileo Laboratories, Inc. | Pyruvate derivatives |
| US6608196B2 (en) | 2001-05-03 | 2003-08-19 | Galileo Pharmaceuticals, Inc. | Process for solid supported synthesis of pyruvate-derived compounds |
| SE0101978D0 (sv) | 2001-06-01 | 2001-06-01 | Astrazeneca Ab | New compounds |
| WO2003008632A1 (en) | 2001-07-16 | 2003-01-30 | Hoegestaett Edward | Fatty acid conjugation as a method for screening of potentially bioactive substances |
| US7262268B2 (en) * | 2001-08-06 | 2007-08-28 | Cubist Pharmaceuticals, Inc. | Lipopeptide stereoisomers, methods for preparing same, and useful intermediates |
| AU2002324666B2 (en) | 2001-08-10 | 2007-10-11 | The Rockefeller University | Compostions and methods for modulation of DARPP-32 phosphorylation |
| AU2002336532C1 (en) | 2001-09-14 | 2008-10-16 | Amgen, Inc | Linked biaryl compounds |
| US20030215456A1 (en) | 2001-10-02 | 2003-11-20 | Sui-Long Yao | Method of treating cancer |
| AU2002342859B2 (en) | 2001-10-30 | 2007-07-26 | Merck Serono Sa | Oxindole hydrazide modulators of protein tyrosine phosphatases (PTPS) |
| JP4156825B2 (ja) | 2001-11-01 | 2008-09-24 | 株式会社ロッテ | 抗鬱・抗ストレス剤及びそれを含有する組成物 |
| AU2002363177B2 (en) | 2001-11-01 | 2008-09-18 | Janssen Pharmaceutica N.V. | Aminobenzamide derivatives as glycogen synthase kinase 3Beta inhibitors |
| CN1205175C (zh) | 2001-11-02 | 2005-06-08 | 中国人民解放军军事医学科学院毒物药物研究所 | 胺衍生物在制备具有抗肺动脉高压作用的药物中用途 |
| US20030171411A1 (en) | 2001-12-21 | 2003-09-11 | Kodra Janos Tibor | Amide derivatives as therapeutic agents |
| US7794965B2 (en) | 2002-03-13 | 2010-09-14 | Signum Biosciences, Inc. | Method of identifying modulators of PP2A methylase |
| US20040138238A1 (en) | 2002-08-08 | 2004-07-15 | Dhanoa Dale S. | Substituted aminopyrimidine compounds as neurokinin antagonists |
| WO2004031177A1 (ja) | 2002-09-30 | 2004-04-15 | Banyu Pharmaceutical Co., Ltd. | 2−アミノベンズイミダゾール誘導体 |
| DE10253426B4 (de) | 2002-11-15 | 2005-09-22 | Elbion Ag | Neue Hydroxyindole, deren Verwendung als Inhibitoren der Phosphodiesterase 4 und Verfahren zu deren Herstellung |
| DE10300099A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Indol-Phenylsulfonamid-Derivate |
| WO2004063147A1 (en) | 2003-01-10 | 2004-07-29 | Novo Nordisk A/S | Salts and solvates of glucagon antagonists |
| JP5208411B2 (ja) | 2003-02-06 | 2013-06-12 | ドムペ・ファ.ル.マ・ソチエタ・ペル・アツィオーニ | 2−アリール−酢酸、その誘導体、及びそれらを含有する医薬組成物 |
| JP4421832B2 (ja) | 2003-03-27 | 2010-02-24 | 株式会社常磐植物化学研究所 | 記憶促進剤 |
| AU2004236247B2 (en) | 2003-04-30 | 2008-11-06 | The Institutes For Pharmaceutical Discovery, Llc | Substituted amino carboxylic acids as inhibitors of protein tyrosine phosphatase-1 B |
| WO2005001041A2 (en) | 2003-05-28 | 2005-01-06 | Paul Anziano | Compositions and methods for inhibiting an isoform of human manganese superoxide dismutase |
| NZ545747A (en) | 2003-08-06 | 2010-06-25 | Senomyx Inc | T1R hetero-oligomeric taste receptors, cell lines that express said receptors, and taste compounds |
| WO2005014532A1 (en) | 2003-08-08 | 2005-02-17 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds, compositions and methods of use |
| WO2005019168A2 (en) | 2003-08-20 | 2005-03-03 | Pfizer Products Inc. | Fluorinated lysine derivatives as dipeptidyl peptidase iv inhibitors |
| US7282593B2 (en) | 2003-09-11 | 2007-10-16 | Board Of Trustees Of Michigan State University | Withanamide and withanolide compositions and method of use thereof |
| FR2860793A1 (fr) | 2003-10-14 | 2005-04-15 | Entomed | Composes derives de norcantharidine, leurs procedes de preparation, les compositions les contenant et leurs utilisations |
| DE602004011985T2 (de) | 2003-11-25 | 2009-03-05 | Eli Lilly And Co., Indianapolis | Modulatoren des peroxisomproliferatoraktivierten rezeptors |
| CA2548281C (en) | 2003-12-09 | 2013-11-12 | Medcrystalforms, Llc | Method of preparation of mixed phase co-crystals with active agents |
| WO2005071101A1 (en) | 2004-01-23 | 2005-08-04 | University Hospital Of Basel | Treatment of hepatitis c infection by increasing stat1 methylation |
| EP1711495A2 (en) | 2004-01-23 | 2006-10-18 | Amgen Inc. | Quinoline, quinazoline, pyridine and pyrimidine counds and their use in the treatment of inflammation, angiogenesis and cancer |
| US8053462B2 (en) | 2004-03-08 | 2011-11-08 | Masanori Somei | Indole derivative and application thereof |
| EP1744751A4 (en) | 2004-03-18 | 2010-03-10 | Brigham & Womens Hospital | METHOD FOR THE TREATMENT OF SYNUCLEINOPATHIES |
| AU2006230674A1 (en) | 2004-03-18 | 2006-11-16 | The Brigham And Women's Hospital, Inc. | Methods for the Treatment of Synucleinopathies |
| CA2561801A1 (en) | 2004-04-02 | 2005-10-20 | Elixir Pharmaceuticals, Inc. | Sulfonamides and uses thereof |
| CN101031289A (zh) | 2004-04-26 | 2007-09-05 | 范德比尔特大学 | 作为具有降低胃肠毒性的治疗剂的吲哚乙酸和茚乙酸衍生物 |
| US20050250819A1 (en) | 2004-05-07 | 2005-11-10 | Xiaobing Li | Inhibitors of bacterial type III protein secretion systems |
| FR2872704B1 (fr) | 2004-07-12 | 2007-11-02 | Laurent Schwartz | Pluritherapie contre le cancer |
| US20060045953A1 (en) | 2004-08-06 | 2006-03-02 | Catherine Tachdjian | Aromatic amides and ureas and their uses as sweet and/or umami flavor modifiers, tastants and taste enhancers |
| EP1790640A4 (en) | 2004-09-09 | 2009-07-29 | Chugai Pharmaceutical Co Ltd | NEW IMIDAZOLIDINE DERIVATIVE AND APPLICATION THEREOF |
| JP3964417B2 (ja) | 2004-09-27 | 2007-08-22 | 国立大学法人金沢大学 | インドール誘導体を有効成分とするα2受容体遮断剤及び血管拡張剤 |
| CA2585934C (en) | 2004-10-29 | 2013-09-10 | Abbott Laboratories | Novel pyrazolopyridine urea kinase inhibitors |
| ES2321858T3 (es) | 2004-11-11 | 2009-06-12 | Ferrer Internacional, S.A. | Compuestos de imidazo(1,2-a)piridina, composiciones, usos y metodos relacionados. |
| US20060160109A1 (en) | 2004-11-22 | 2006-07-20 | Odyssey Thera, Inc. | Harnessing network biology to improve drug discovery |
| US20070212677A1 (en) | 2004-11-22 | 2007-09-13 | Odyssey Thera, Inc. | Identifying off-target effects and hidden phenotypes of drugs in human cells |
| CA2587664A1 (en) | 2004-12-21 | 2006-06-29 | Devgen N.V. | Compounds with kv4 ion channel activity |
| FR2879601B1 (fr) | 2004-12-22 | 2007-01-19 | Galderma Res & Dev | Nouveaux composes derives d'acide phenyl-boronique et leur procede de preparation |
| EP1676842A1 (en) | 2004-12-30 | 2006-07-05 | Laboratorios Del Dr. Esteve, S.A. | Nitro-substituted phenyl-piperazine compounds, their preparation and use in medicaments |
| US20070161644A1 (en) | 2005-01-25 | 2007-07-12 | Stockwell Brent R | Erastin analogs and uses thereof |
| AU2006209245A1 (en) | 2005-01-28 | 2006-08-03 | Irm Llc | Phenyl-substituted pyrrolidones |
| US8221804B2 (en) * | 2005-02-03 | 2012-07-17 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| EP1853590A1 (en) | 2005-03-03 | 2007-11-14 | Sirtris Pharmaceuticals, Inc. | Fused heterocyclic compounds and their use as sirtuin modulators |
| WO2006101456A1 (en) | 2005-03-21 | 2006-09-28 | S*Bio Pte Ltd | Bicyclic heterocycles hydroxamate compounds useful as histone deacetylase (hdac) inhibitors |
| JP2008534593A (ja) | 2005-03-30 | 2008-08-28 | メルク エンド カムパニー インコーポレーテッド | グルカゴン受容体アンタゴニスト化合物、そのような化合物を含む組成物、及びその使用方法 |
| CN1304396C (zh) | 2005-04-08 | 2007-03-14 | 中山大学 | 斑蝥素衍生物及其制备方法 |
| TW200738677A (en) | 2005-06-27 | 2007-10-16 | Elbion Ag | Nitro-substituted hydroxyindoles, their use as inhibitors of phosphodiesterase 4, and processes for preparing them |
| WO2007008514A2 (en) | 2005-07-07 | 2007-01-18 | Georgetown University | Inhibitors of glycogen synthase kinase 3 |
| WO2007015866A2 (en) | 2005-07-20 | 2007-02-08 | Kalypsys, Inc. | Inhibitors of p38 kinase and methods of treating inflammatory disorders |
| JP2009504712A (ja) | 2005-08-17 | 2009-02-05 | ゾルファイ ファーマスーティカルズ ゲゼルシャフト ミット ベシュレンクテル ハフツング | カリウムチャンネル阻害化合物の使用方法 |
| EP1931632A4 (en) | 2005-08-18 | 2011-05-11 | Microbia Inc | USEFUL INDOOR CONNECTIONS |
| AU2006302371A1 (en) | 2005-10-06 | 2007-04-19 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding cassette transporters |
| US20080021198A1 (en) | 2005-10-12 | 2008-01-24 | Yigong Shi | Modulators of protein phosphatase 2A and PP2A methyl esterase |
| US7902251B2 (en) | 2005-10-19 | 2011-03-08 | Allergan, Inc. | Method for treating pain |
| US20070105940A1 (en) | 2005-10-19 | 2007-05-10 | Allergan, Inc. | Method for treating pain |
| US20070259945A1 (en) | 2005-10-19 | 2007-11-08 | Allergan, Inc. | Method for treating pain |
| JP4993900B2 (ja) | 2005-11-28 | 2012-08-08 | 国立大学法人 東京医科歯科大学 | 記憶障害抑制剤 |
| CN1974545B (zh) * | 2005-11-29 | 2010-05-26 | 上海第二医科大学 | 长链脂肪酰胺类化合物及其应用 |
| DE102005061428A1 (de) | 2005-12-22 | 2007-08-16 | Grünenthal GmbH | Substituierte Cyclohexylmethyl-Derivate |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| GB0611417D0 (en) | 2006-06-09 | 2006-07-19 | Leuven K U Res & Dev | Treatment of cndaria intoxication |
| CA2657093A1 (en) | 2006-07-07 | 2008-01-10 | Steven P. Govek | Bicyclic heteroaryl inhibitors of pde4 |
| WO2008007123A2 (en) | 2006-07-14 | 2008-01-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
| AU2007281747B2 (en) | 2006-08-07 | 2013-11-07 | Ironwood Pharmaceuticals, Inc. | Indole compounds |
| RU2446157C2 (ru) | 2006-09-13 | 2012-03-27 | Санофи-Авентис | Изосериновые производные для применения в качестве ингибиторов фактора свертывания крови ixa |
| EP2068869A4 (en) | 2006-10-06 | 2011-05-25 | Abbott Lab | NEW IMIDAZOTHIAZOLE AND IMIDAZOXAZOLE |
| US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| EP2076513A1 (en) | 2006-10-20 | 2009-07-08 | Irm Llc | Compositions and methods for modulating c-kit and pdgfr receptors |
| GB0623258D0 (en) | 2006-11-22 | 2007-01-03 | Remynd Nv | Thiadiazole derivatives for the treatment of neuro-degenerative diseases |
| JP4771975B2 (ja) | 2007-02-27 | 2011-09-14 | 三菱製紙株式会社 | 可逆性感熱記録材料 |
| US20100184803A1 (en) | 2007-03-09 | 2010-07-22 | Link Medicine Corporation | Treatment of Lysosomal Storage Diseases |
| EA200970841A1 (ru) | 2007-03-09 | 2010-04-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Фармацевтическое применение замещенных амидов |
| DE102007012284A1 (de) | 2007-03-16 | 2008-09-18 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue substituierte Arylsulfonylglycine, deren Herstellung und deren Verwendung als Arzneimittel |
| WO2008141013A1 (en) | 2007-05-08 | 2008-11-20 | Allergan, Inc. | S1p3 receptor inhibitors for treating pain |
| EP1992621A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide-substituted pyrimidone derivatives for the treatment of neurodegenerative diseases |
| EP1992624A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
| US20110236953A1 (en) | 2007-08-03 | 2011-09-29 | Beth Israel Deaconness Medical Center | EMBRYONIC CEREBROSPINAL FLUID (e-CSF), PROTEINS FROM e-CSF, AND RELATED METHODS AND COMPOSITIONS |
| EP2282735B1 (en) | 2008-04-21 | 2019-01-16 | Signum Biosciences, Inc. | Pp2a modulators for treating alzheimer, parkinson, diabetes |
| JP4842996B2 (ja) | 2008-06-09 | 2011-12-21 | 株式会社ロッテ | 抗鬱・抗ストレス組成物 |
| CN115941304B (zh) | 2022-11-29 | 2025-10-03 | 深圳云里物里科技股份有限公司 | 数据的加密方法、装置、终端设备和计算机可读存储介质 |
-
2009
- 2009-04-21 EP EP09734282.8A patent/EP2282735B1/en not_active Not-in-force
- 2009-04-21 WO PCT/US2009/041321 patent/WO2009132051A1/en not_active Ceased
- 2009-04-21 US US12/427,743 patent/US9486441B2/en not_active Expired - Fee Related
- 2009-04-21 CA CA2758424A patent/CA2758424C/en active Active
- 2009-04-21 JP JP2011505265A patent/JP5607025B2/ja not_active Expired - Fee Related
- 2009-04-21 AU AU2009239430A patent/AU2009239430B2/en not_active Ceased
- 2009-04-21 CN CN200980114132.4A patent/CN102014897B/zh not_active Expired - Fee Related
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2012
- 2012-03-30 JP JP2012082834A patent/JP2012126753A/ja not_active Withdrawn
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2014
- 2014-08-07 JP JP2014161026A patent/JP2014208706A/ja active Pending
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- 2015-04-22 AU AU2015202037A patent/AU2015202037A1/en not_active Abandoned
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- 2016-04-25 JP JP2016086767A patent/JP2016135809A/ja active Pending
- 2016-11-08 US US15/346,636 patent/US10583119B2/en not_active Expired - Fee Related
- 2016-12-15 AU AU2016273941A patent/AU2016273941B2/en not_active Ceased
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