ES2540232T3 - Análogos de TOFA útiles en el tratamiento de trastornos o afecciones dermatológicas - Google Patents
Análogos de TOFA útiles en el tratamiento de trastornos o afecciones dermatológicas Download PDFInfo
- Publication number
- ES2540232T3 ES2540232T3 ES13163877.7T ES13163877T ES2540232T3 ES 2540232 T3 ES2540232 T3 ES 2540232T3 ES 13163877 T ES13163877 T ES 13163877T ES 2540232 T3 ES2540232 T3 ES 2540232T3
- Authority
- ES
- Spain
- Prior art keywords
- optionally substituted
- tetradecyloxy
- furan
- mmol
- carboxylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Landscapes
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Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010270797B2 (en) * | 2009-07-08 | 2015-03-19 | Dermira (Canada), Inc. | TOFA analogs useful in treating dermatological disorders or conditions |
| US8927679B2 (en) * | 2013-01-15 | 2015-01-06 | Xerox Corporation | Tuning toner gloss with bio-based stabilizers |
| US20160220557A1 (en) | 2013-09-12 | 2016-08-04 | Pfizer Inc. | Use of acetyl-coa carboxylase inhibitors for treating acne vulgaris |
| CN107567441A (zh) * | 2015-02-05 | 2018-01-09 | 德米拉公司 | 用于制备2‑糠酸衍生物的合成方法 |
| CN107406400B (zh) | 2015-02-05 | 2020-08-04 | 德米拉公司 | 用于制备(5-十四烷氧基)呋喃-2-甲酸2-((2-乙氧基-2-氧代乙基)(甲基)氨基)-2-氧代乙酯的合成方法 |
| CA3031815A1 (en) | 2016-07-26 | 2018-02-01 | Dermira Inc. | Dermatological formulations of 2-(2-ethoxy-2-oxoethyl)(methyl)amino-2-oxoethyl 5-(tetradecyloxy)furan-2-carboxylate |
| WO2018170316A1 (en) * | 2017-03-16 | 2018-09-20 | The Board Of Trustees Of The Leland Stanford Junior University | Methods of identifying myc-driven and lipogenesis-dependent neoplasms and methods of treating the same |
| US11129818B2 (en) | 2017-06-07 | 2021-09-28 | Arcutis Biotherapeutics, Inc. | Topical roflumilast formulation having improved delivery and plasma half life |
| US9895359B1 (en) | 2017-06-07 | 2018-02-20 | Arcutis, Inc. | Inhibition of crystal growth of roflumilast |
| US12011437B1 (en) | 2017-06-07 | 2024-06-18 | Arcutis Biotherapeutics, Inc. | Roflumilast formulations with an improved pharmacokinetic profile |
| US20210161870A1 (en) | 2017-06-07 | 2021-06-03 | Arcutis Biotherapeutics, Inc. | Roflumilast formulations with an improved pharmacokinetic profile |
| CN110799187B (zh) | 2017-06-30 | 2023-10-03 | 汇科锦公司 | 螺内酯化合物 |
| WO2019072478A1 (en) | 2017-10-10 | 2019-04-18 | Galderma Research & Development | SPECIFIC ACETYL-COA CARBOXYLASE INHIBITORS FOR USE IN THE TREATMENT AND / OR PREVENTION OF ACNE |
| JP6950524B2 (ja) * | 2017-12-28 | 2021-10-13 | トヨタ自動車株式会社 | ハイブリッド車両の制御装置 |
| EP3801461A2 (en) | 2018-06-04 | 2021-04-14 | Arcutis, Inc. | Method and formulation for improving roflumilast skin penetration lag time |
| RU2678307C1 (ru) * | 2018-11-13 | 2019-01-25 | Индивидуальный предприниматель Талагаева Елена Владимировна | Активная против акне добавка к парфюмерно-косметическим продуктам |
| CN109608415B (zh) * | 2019-01-21 | 2020-12-01 | 暨南大学 | 噻唑甲酰胺类化合物及其合成和应用 |
| US20200330429A1 (en) * | 2019-04-22 | 2020-10-22 | Nestlé Skin Health Sa | Method of treating truncal acne with trifarotene |
| WO2021226370A1 (en) * | 2020-05-07 | 2021-11-11 | Arcutis Biotherapeutics, Inc. | Treatment of skin conditions using high krafft temperature anionic surfactants |
| US11707454B2 (en) | 2020-12-04 | 2023-07-25 | Arcutis Biotherapeutics, Inc. | Topical roflumilast formulation having antifungal properties |
| CN114767665B (zh) * | 2021-06-11 | 2023-10-10 | 同济大学 | 5-十四烷氧基-2-呋喃甲酸在制备用于治疗银屑病样皮炎的药物中的用途 |
| CN117881649A (zh) * | 2021-07-02 | 2024-04-12 | 安基生技新药股份有限公司 | 二甲基姜黄素的外用调配物 |
| DE102022201276A1 (de) | 2022-02-08 | 2023-08-10 | Beiersdorf Aktiengesellschaft | Neue TOFA-Analoga, Zubereitungen zur Sebumreduktion mit einem Gehalt an solchen Analoga und die kosmetische und/oder therapeutische Verwendung solcher Analoga als wirksames Prinzip zur Sebumreduktion oder -verhinderung |
| DE102022201277A1 (de) | 2022-02-08 | 2023-08-10 | Beiersdorf Aktiengesellschaft | Neue TOFA-Analoga, Zubereitungen zur Sebumreduktion mit einem Gehalt an solchen Analoga und die kosmetische und/oder therapeutische Verwendung solcher Analoga als wirksames Prinzip zur Sebumreduktion oder -verhinderung |
| WO2024058848A1 (en) | 2022-09-15 | 2024-03-21 | Arcutis Biotherapeutics, Inc. | Pharmaceutical compositions of roflumilast and solvents capable of dissolving high amounts of the drug |
| WO2025160513A1 (en) * | 2024-01-26 | 2025-07-31 | Rerx Therapeutics, Inc. | Crystalline forms of 5-(tetradecyloxy)furan-2-carboxylic acid and salts thereof |
| WO2025165758A1 (en) * | 2024-01-31 | 2025-08-07 | The Regents Of The University Of California | Combination formulations and methods for treating severe metabolic disorders or diseases |
Family Cites Families (192)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS502373B1 (enExample) | 1969-08-18 | 1975-01-25 | ||
| US4110351A (en) | 1973-04-02 | 1978-08-29 | Richardson-Merrell Inc. | Hypolipidemic agents RO- or RS- substituted furoic acids, esters and salts |
| US4602099A (en) | 1973-04-02 | 1986-07-22 | Merrell Dow Pharmaceuticals Inc. | Antirhinovirus agents |
| US4093622A (en) | 1975-05-19 | 1978-06-06 | Zoecon Corporation | Pyridine esters of cyclopropane-carboxylic acid |
| SU689180A1 (ru) * | 1978-02-20 | 2006-12-27 | Пермский ордена Трудового Красного Знамени государственный университет им. А.М.Горького | β-(5-Бромфуроил)-β-фенилгидразиды диалкилгликолевых кислот, проявляющие противовоспалительную активность |
| US4935421A (en) | 1981-11-12 | 1990-06-19 | E. I. Du Pont De Nemours And Company | 2-hydroxypropylamine aryl ester derivatives and pharmaceutical use |
| IT1140323B (it) | 1981-12-09 | 1986-09-24 | Montedison Spa | Processo per la preparazione di composti carbossilati aromatici o etero-aromatici |
| US5087240A (en) | 1983-08-18 | 1992-02-11 | Drug Delivery Systems Inc. | Transdermal drug patch with conductive fibers |
| US4921475A (en) | 1983-08-18 | 1990-05-01 | Drug Delivery Systems Inc. | Transdermal drug patch with microtubes |
| US5163899A (en) | 1987-03-20 | 1992-11-17 | Drug Delivery Systems Inc. | Transdermal drug delivery system |
| US5312325A (en) | 1987-05-28 | 1994-05-17 | Drug Delivery Systems Inc | Pulsating transdermal drug delivery system |
| US5151424A (en) | 1987-07-01 | 1992-09-29 | Janssen Pharmaceutica N.V. | Pharmacologically active (Bicyclic heterocyclyl)methyl and -hetero) substituted hexahydro-1H-azepines and pyrrolidines |
| US5710100A (en) | 1987-08-13 | 1998-01-20 | Monsanto Company | Safening imidazolinone herbicides |
| US5256625A (en) | 1987-08-13 | 1993-10-26 | Monsanto Company | Safening imidazolinone herbicides |
| GB8804164D0 (en) | 1988-02-23 | 1988-03-23 | Tucker J M | Bandage for administering physiologically active compound |
| WO1989011535A1 (en) | 1988-05-25 | 1989-11-30 | The Queen's University Of Belfast | Methylation of organic compounds |
| DE3829450A1 (de) | 1988-08-31 | 1990-03-01 | Hoechst Ag | Nigericinderivate, verfahren zu deren herstellung, diese enthaltende mittel und verwendung derselben |
| DE3830509A1 (de) | 1988-09-08 | 1990-03-22 | Hoechst Ag | Arzneimittel mit synergistischer antimykotischer und antiviraler wirksamkeit |
| US5008110A (en) | 1988-11-10 | 1991-04-16 | The Procter & Gamble Company | Storage-stable transdermal patch |
| US5088977A (en) | 1988-12-21 | 1992-02-18 | Drug Delivery Systems Inc. | Electrical transdermal drug applicator with counteractor and method of drug delivery |
| US4980371A (en) | 1988-12-21 | 1990-12-25 | Merrell Dow Pharmaceuticals | Antiretroviral furan ketones |
| DE3907784A1 (de) | 1989-03-10 | 1990-09-13 | Hoechst Ag | Heteroaryl-aryl-buten- und -butanderivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als schaedlingsbekaempfungsmittel |
| FR2648140B1 (fr) | 1989-06-08 | 1991-05-03 | Centre Nat Rech Scient | Procede de preparation d'oligomeres d'heterocycles aromatiques par couplage oxydant d'oligomeres inferieurs |
| DE3927786A1 (de) | 1989-08-23 | 1991-02-28 | Bayer Ag | Verfahren zur herstellung von aldehyden |
| JPH03101679A (ja) | 1989-09-14 | 1991-04-26 | Sankyo Co Ltd | リゾキシン誘導体 |
| DK0431519T3 (da) | 1989-12-04 | 1994-07-04 | Searle & Co | System til transdermal indgivelse af albuterol |
| EP0434517A3 (en) | 1989-12-20 | 1991-10-16 | Rhone-Poulenc Chimie | Process for the preparation of mono- or poly-alkoxylated aromatic compounds |
| JPH03197441A (ja) | 1989-12-26 | 1991-08-28 | Sagami Chem Res Center | カルボン酸類の製造方法 |
| DE4005648A1 (de) | 1990-02-22 | 1991-08-29 | Wacker Chemie Gmbh | Heteroarylenmethine und daraus hergestellte polymere |
| EP0446899A1 (en) | 1990-03-16 | 1991-09-18 | Konica Corporation | Silver halide photographic material |
| JP2916700B2 (ja) | 1990-07-05 | 1999-07-05 | コニカ株式会社 | ハロゲン化銀写真感光材料 |
| JP2916694B2 (ja) | 1990-03-16 | 1999-07-05 | コニカ株式会社 | ハロゲン化銀写真感光材料及びその製造方法 |
| JPH0429969A (ja) | 1990-05-28 | 1992-01-31 | Nippon Oil & Fats Co Ltd | ポリフルオロアルキル基含有ヘテロ芳香族誘導体及びその製造方法 |
| US5034385A (en) | 1990-06-26 | 1991-07-23 | Merck & Co., Inc. | 2-(heteroarylsubstituted)phenyl carbapenem antibacterial agents |
| MY107955A (en) | 1990-07-27 | 1996-07-15 | Ici Plc | Fungicides. |
| LU87821A1 (fr) | 1990-10-12 | 1992-05-25 | Cird Galderma | Composes bi-aromatiques,et leur utilisation en medecine humaine et veterinaire et en cosmetique |
| DE4033563A1 (de) * | 1990-10-22 | 1992-04-23 | Henkel Kgaa | Antiseborrhoische zubereitungen |
| US5354858A (en) | 1991-03-28 | 1994-10-11 | The University Of Toledo | Production and use of Diels Alder adducts of vinyl porphyrins and of compositions containing such adducts |
| TW279162B (enExample) | 1991-09-26 | 1996-06-21 | Mitsubishi Chem Corp | |
| US5352456A (en) | 1991-10-10 | 1994-10-04 | Cygnus Therapeutic Systems | Device for administering drug transdermally which provides an initial pulse of drug |
| DE4138026A1 (de) | 1991-11-19 | 1993-06-03 | Bayer Ag | Substituierte pyridin-4-carbonsaeureamide |
| DE69228827T2 (de) | 1991-12-18 | 1999-10-21 | Minnesota Mining And Mfg. Co., Saint Paul | Mehrschichtige sperrstrukturen |
| FR2686162B1 (fr) | 1992-01-13 | 1995-09-22 | Commissariat Energie Atomique | Modulateur spatial de lumiere a adressage optique. |
| ATE132381T1 (de) | 1992-01-29 | 1996-01-15 | Voelkl Franz Ski | Ballspielschläger, insbesondere tennisschläger |
| US5334389A (en) | 1992-10-15 | 1994-08-02 | Duke University | Antifouling coating and method for using same |
| US6190894B1 (en) | 1993-03-19 | 2001-02-20 | The Regents Of The University Of California | Method and compositions for disrupting the epithelial barrier function |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| DE69416057T2 (de) | 1993-08-31 | 1999-07-01 | Canon K.K., Tokio/Tokyo | Mesomorphe Verbindung, eine diese enthaltene Flüssigkristallzusammensetzung, eine diese Zusammensetzung verwendende Flüssigkristallvorrichtung, Flüssigkristallapparat und Anzeigeverfahren |
| JP3015998B2 (ja) | 1993-08-31 | 2000-03-06 | キヤノン株式会社 | 液晶性化合物、それを含む液晶組成物、該液晶組成物を用いた液晶素子、液晶装置、並びに表示方法 |
| US5569675A (en) | 1994-03-07 | 1996-10-29 | Bar Ilan University | Methods of using carboxylic acid esters to increase fetal-hemoglobin levels |
| DE4412334A1 (de) | 1994-04-11 | 1995-10-19 | Hoechst Ag | Substituierte N-Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| FR2720393B1 (fr) | 1994-05-27 | 1996-10-25 | Rhone Poulenc Chimie | Réactif utile pour et procédé pour la synthèse d'ester et xanthate transestérifiable. |
| DE4425146A1 (de) | 1994-07-15 | 1996-01-18 | Basf Ag | Verwendung heterocyclischer Verbindungen |
| JPH0859611A (ja) | 1994-08-26 | 1996-03-05 | Nippon Soda Co Ltd | ヘテロ環誘導体の製造法 |
| US5512596A (en) | 1994-09-02 | 1996-04-30 | Gilead Sciences, Inc. | Aromatic compounds |
| US5597826A (en) | 1994-09-14 | 1997-01-28 | Pfizer Inc. | Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist |
| TW307746B (enExample) | 1994-10-14 | 1997-06-11 | Sumitomo Chemical Co | |
| US5702637A (en) | 1995-04-19 | 1997-12-30 | Minnesota Mining And Manufacturing Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| US5993690A (en) | 1995-07-27 | 1999-11-30 | Chisso Corporation | Organosilicon compound, liquid crystal composition, and liquid-crystal display element |
| US6756053B2 (en) | 1995-07-28 | 2004-06-29 | Zars, Inc. | Controlled heat induced rapid delivery of pharmaceuticals from skin depot |
| JP2000513373A (ja) | 1996-07-02 | 2000-10-10 | ジュウ,サング,スプ | オキシランカルボキシル酸誘導体及びその製造方法 |
| GB9620061D0 (en) | 1996-09-26 | 1996-11-13 | Secr Defence | Liquid crystalline (e,e)-butadiene compounds and mixtures and devices containing such compounds |
| WO1998017253A1 (en) | 1996-10-23 | 1998-04-30 | The Regents Of The University Of California | Method and compositions for disrupting the epithelial barrier function |
| US6444194B1 (en) | 1997-02-14 | 2002-09-03 | Miravant Pharmaceuticals, Inc. | Indium photosensitizers for PDT |
| US6541472B1 (en) | 1997-02-21 | 2003-04-01 | Viropharma Incorporated | Compounds, compositions and methods for preventing and treating pestivirus infection and associated diseases |
| JPH10287654A (ja) | 1997-04-11 | 1998-10-27 | Nissan Chem Ind Ltd | ピラゾロン誘導体及び除草剤 |
| DE19717898A1 (de) | 1997-04-28 | 1998-10-29 | Agfa Gevaert Ag | Farbfotografisches Aufzeichnungsmaterial |
| DE19718742A1 (de) | 1997-05-02 | 1998-11-05 | Hoechst Ag | Verfahren zur Herstellung von aromatischen Aldehyden durch katalytische Gasphasenhydrierung der Carbonsäuren |
| CZ294715B6 (cs) | 1997-05-07 | 2005-02-16 | Qlt Inc. | Ethylenglykol estery monohydrobenzoporfyrinových derivátů jako fotoaktivní činidla |
| JPH1143792A (ja) | 1997-07-23 | 1999-02-16 | Asahi Kagaku Kogyo Co Ltd | 酸洗促進剤、酸洗促進剤を含んだ酸洗液組成物およびこれを用いる酸洗方法 |
| US5851952A (en) | 1997-11-07 | 1998-12-22 | American Cyanamid Company | Herbicidal thienyloxyazines |
| US5869426A (en) | 1997-11-07 | 1999-02-09 | American Cyanamid Company | Herbicidal 6-thienyloxypyrid-2-carboxamides |
| JP2001522848A (ja) | 1997-11-07 | 2001-11-20 | アメリカン・サイアナミド・カンパニー | 除草性フラニル−およびチエニルオキシアジン |
| US6309561B1 (en) | 1997-12-24 | 2001-10-30 | 3M Innovative Properties Company | Liquid crystal compounds having a chiral fluorinated terminal portion |
| WO1999040088A1 (en) | 1998-02-09 | 1999-08-12 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines as protease inhibitors, in particular as urokinase inhibitors |
| WO1999048371A1 (en) | 1998-03-27 | 1999-09-30 | The Regents Of The University Of California | Novel hiv integrase inhibitors and hiv therapy based on drug combinations including integrase inhibitors |
| JP4048645B2 (ja) | 1998-04-10 | 2008-02-20 | 東レ株式会社 | 発光素子 |
| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
| SE9802793D0 (sv) | 1998-08-21 | 1998-08-21 | Astra Ab | New compounds |
| US6139924A (en) | 1998-11-20 | 2000-10-31 | 3M Innovative Properties Company | Chiral liquid crystal compounds having a fluorinated terminal portion |
| WO2000033836A1 (en) | 1998-12-04 | 2000-06-15 | Ontogen Corporation | 5-membered heterocycles for the treatment of human diseases involving modulators of selectins |
| US6183773B1 (en) | 1999-01-04 | 2001-02-06 | The General Hospital Corporation | Targeting of sebaceous follicles as a treatment of sebaceous gland disorders |
| DE19904389A1 (de) | 1999-02-04 | 2000-08-10 | Bayer Ag | Verwendung von substituierten Isoxazolcarbonsäuren und Derivate und neue Stoffe |
| KR20010098982A (ko) | 1999-02-09 | 2001-11-08 | 3-디멘져널 파마슈티칼즈 인코오포레이티드 | 프로테아제 억제제로서의 헤테로아릴 아미딘, 메틸아미딘및 구아니딘 |
| GB9906168D0 (en) | 1999-03-17 | 1999-05-12 | Rolic Ag | Liquid crystal compounds |
| FR2793791B1 (fr) | 1999-05-19 | 2002-01-25 | Univ Paris 7 Denis Diderot | Nouveaux composes inhibiteurs specifiques de phospholipases a2 |
| CN1073571C (zh) | 1999-06-02 | 2001-10-24 | 山西大学 | 单核芳香族、杂环类单酰异羟肟酸二烃基锡化合物及其合成 |
| TR200202129T2 (tr) | 1999-06-02 | 2003-03-21 | Shionogi & Co., Ltd. | Yeni ikameli propenon türevlerinin hazırlanması için prosesler. |
| DE19929783A1 (de) | 1999-06-29 | 2001-01-04 | Bayer Ag | Substituierte 6-[4-(Oxymethyl)-phenyl]-dihydropyridazinone und ihre Verwendung |
| JP2002060658A (ja) | 2000-08-11 | 2002-02-26 | Fuji Photo Film Co Ltd | インクジェット用インク及びインクジェット記録方法 |
| AU2002213467A8 (en) | 2000-10-11 | 2009-07-30 | Chemocentryx Inc | Modulation of ccr4 function |
| US20050049242A1 (en) | 2000-12-21 | 2005-03-03 | W. Edward Robinson | Novel HIV integrase inhibitors and HIV therapy based on drug combinations including integrase inhibitors |
| DE10104231A1 (de) | 2001-01-31 | 2002-08-08 | Consortium Elektrochem Ind | Verfahren zur enzymatischen Herstellung von enantiomerenreinen 1,3-Dioxolan-4-on-Derivaten |
| US7709677B2 (en) | 2001-01-31 | 2010-05-04 | Glaxosmithkline Llc | Process of preparing arylethanoldiamines |
| WO2002068397A1 (en) | 2001-02-28 | 2002-09-06 | Melacure Therapeutics Ab | Diaminoquinazoline esters for use as dihydrofolate reductade inhibitors |
| JP2002363123A (ja) | 2001-03-29 | 2002-12-18 | Kansai Research Institute | 光活性化合物および感光性樹脂組成物 |
| WO2002079131A1 (en) | 2001-03-29 | 2002-10-10 | Kansai Research Institute, Inc. | Optically active compound and photosensitive resin composition |
| ATE427948T1 (de) | 2001-04-24 | 2009-04-15 | Purdue Research Foundation | Folat-mimetika und deren folatrezeptorbindende konjugate |
| DE10125145A1 (de) | 2001-05-22 | 2002-11-28 | Gruenenthal Gmbh | Substituierte C-Furan-2-yl-methylamin- und C-Thiophen-2-yl-methylamin-Derivate |
| EP1270535A3 (de) | 2001-06-20 | 2004-02-18 | Clariant GmbH | Verfahren zur Herstellung von substituierten aromatischen Verbindungen |
| EP1275301A1 (en) | 2001-07-10 | 2003-01-15 | Bayer CropScience S.A. | Trisubstituted heterocyclic compounds and their use as fungicides |
| JP2003055367A (ja) | 2001-08-15 | 2003-02-26 | Kuraray Co Ltd | 3−ホルミルフラン類の製造方法 |
| JP2005194190A (ja) | 2001-10-05 | 2005-07-21 | Fumie Satou | 19−ノル−ビタミンd誘導体の製造法 |
| BR0213562A (pt) | 2001-10-26 | 2004-08-31 | Aventis Pharma Inc | Benzimidazóis e análogos e seu uso como inibidores de cinases de proteìna |
| US6897208B2 (en) | 2001-10-26 | 2005-05-24 | Aventis Pharmaceuticals Inc. | Benzimidazoles |
| FR2831537B1 (fr) | 2001-10-26 | 2008-02-29 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation |
| AUPR970701A0 (en) | 2001-12-21 | 2002-01-24 | Fujisawa Pharmaceutical Co., Ltd. | Benzhydryl derivatives |
| US7160921B2 (en) | 2002-01-29 | 2007-01-09 | The Gillette Company | Reduction of hair growth |
| JP4157765B2 (ja) | 2002-02-18 | 2008-10-01 | 花王株式会社 | 粉末油脂 |
| US7122296B2 (en) | 2002-03-05 | 2006-10-17 | Brewer Science Inc. | Lithography pattern shrink process and articles |
| AU2003251942A1 (en) | 2002-07-17 | 2004-02-02 | Titan Pharmaceuticals, Inc. | Combination of chemotherapeutic drugs for increasing antitumor activity |
| JP2004107271A (ja) | 2002-07-22 | 2004-04-08 | Mitsubishi Rayon Co Ltd | 水溶性アルキルホスフィン誘導体とその製造方法、ホスフィン配位子錯体並びにビアリール誘導体の製造方法 |
| US7847101B2 (en) | 2002-07-24 | 2010-12-07 | Valocor Therapeutics, Inc. | Pyrazolylbenzothiazole derivatives and their use as therapeutic agents |
| DE10240262A1 (de) | 2002-08-31 | 2004-03-11 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Aryllithium-Basen |
| DE10240261A1 (de) | 2002-08-31 | 2004-03-11 | Clariant Gmbh | Verfahren zur metallorganischen Herstellung organischer Zwischenprodukte über Halogen-Metall-Austauschreaktionen |
| WO2004043457A1 (en) | 2002-11-06 | 2004-05-27 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| TW585898B (en) | 2002-12-26 | 2004-05-01 | Ind Tech Res Inst | Liquid crystal compounds with optical activities having high helical twisting power, method for preparing the same, and liquid crystal composition containing the compounds |
| US7445926B2 (en) | 2002-12-30 | 2008-11-04 | The Regents Of The University Of California | Fluid control structures in microfluidic devices |
| DE10300097A1 (de) | 2003-01-07 | 2004-07-22 | Bayer Ag | Kupfer-Komplexe und ihre Verwendung |
| JP4083028B2 (ja) | 2003-02-04 | 2008-04-30 | 広栄化学工業株式会社 | アリールボラン化合物の製造方法 |
| EP1606289B1 (en) | 2003-02-14 | 2009-12-02 | Glaxo Group Limited | Carboxamide derivatives |
| US7029729B2 (en) | 2003-02-24 | 2006-04-18 | 3M Innovative Properties Company | Cholesteric liquid crystal additives |
| JP4715992B2 (ja) | 2003-03-28 | 2011-07-06 | 日産化学工業株式会社 | アクリロニトリル化合物の製造方法 |
| BRPI0409529B1 (pt) | 2003-03-28 | 2015-03-03 | Nissan Chemical Ind Ltd | Processo para a produção de um composto de acrilonitrila |
| AU2004248187A1 (en) | 2003-06-12 | 2004-12-23 | University Of Colorado System Technology | Systems and methods for treating human inflammatory and proliferative diseases and wounds, with fatty acid metabolism inhibitors and/or glycolytic inhibitors |
| WO2004113258A1 (ja) | 2003-06-20 | 2004-12-29 | Shionogi & Co., Ltd. | 炭素−炭素結合生成反応 |
| ITMI20031941A1 (it) * | 2003-10-09 | 2005-04-10 | Sinclair Pharmaceuticals Ltd | Composizioni farmaceutiche topiche per il trattamento delle dermatiti |
| JP2007515429A (ja) | 2003-12-19 | 2007-06-14 | エリクシアー ファーマシューティカルズ, インコーポレイテッド | 障害を治療する方法 |
| WO2005066152A1 (en) | 2003-12-30 | 2005-07-21 | The Brigham And Women's Hospital, Inc. | Thiophene derivatives for up-regulating hla-dm activity |
| US7510710B2 (en) | 2004-01-08 | 2009-03-31 | The Regents Of The University Of Colorado | Compositions of UCP inhibitors, Fas antibody, a fatty acid metabolism inhibitor and/or a glucose metabolism inhibitor |
| CA2553670A1 (en) | 2004-01-29 | 2005-08-11 | Elixir Pharmaceuticals, Inc. | Anti-viral therapeutics |
| US7297168B2 (en) | 2004-02-02 | 2007-11-20 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| CA2457214A1 (en) | 2004-02-06 | 2005-08-06 | Qlt Inc. | Photodynamic therapy for the treatment of acne |
| JP2007534735A (ja) | 2004-04-28 | 2007-11-29 | アロウ セラピューティクス リミテッド | 抗ウイルス剤として使用するためのモルホリニルアニリノキナゾリン誘導体 |
| US7582365B2 (en) | 2005-01-10 | 2009-09-01 | Universal Display Corporation | Reversibly reducible metal complexes as electron transporting materials for OLEDs |
| US7601436B2 (en) | 2004-05-18 | 2009-10-13 | The University Of Southern California | Carbene metal complexes as OLED materials |
| US7279704B2 (en) | 2004-05-18 | 2007-10-09 | The University Of Southern California | Complexes with tridentate ligands |
| WO2005113704A2 (en) | 2004-05-18 | 2005-12-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7598388B2 (en) | 2004-05-18 | 2009-10-06 | The University Of Southern California | Carbene containing metal complexes as OLEDs |
| US7445855B2 (en) | 2004-05-18 | 2008-11-04 | The University Of Southern California | Cationic metal-carbene complexes |
| US7655323B2 (en) | 2004-05-18 | 2010-02-02 | The University Of Southern California | OLEDs utilizing macrocyclic ligand systems |
| US7393599B2 (en) | 2004-05-18 | 2008-07-01 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7534505B2 (en) | 2004-05-18 | 2009-05-19 | The University Of Southern California | Organometallic compounds for use in electroluminescent devices |
| US7491823B2 (en) | 2004-05-18 | 2009-02-17 | The University Of Southern California | Luminescent compounds with carbene ligands |
| US7154114B2 (en) | 2004-05-18 | 2006-12-26 | Universal Display Corporation | Cyclometallated iridium carbene complexes for use as hosts |
| JP2005350527A (ja) | 2004-06-09 | 2005-12-22 | Kyowa Hakko Chemical Co Ltd | 環状保護基で置換された単量体および重合体 |
| WO2005123667A1 (en) | 2004-06-22 | 2005-12-29 | Syngenta Participations Ag | Substituted bicyclooctenes and their use as herbicides |
| ES2285972T1 (es) | 2004-08-23 | 2007-12-01 | Sun Pharmaceutical Industries Limited | Procedimiento de fabricacion de citalopram y enantiomeros. |
| RU2007117147A (ru) | 2004-10-08 | 2008-11-20 | Юнилевер Н.В. (Nl) | Комплекс железа |
| KR100784337B1 (ko) | 2004-11-12 | 2007-12-13 | 한국생명공학연구원 | 신규한 o-아실옥심 유도체, 그의 제조방법 및 이를유효성분으로 하는 심장순환계 질환의 예방 및 치료용약학 조성물 |
| US6987207B1 (en) | 2005-03-03 | 2006-01-17 | Alan Jeffrey Ronyak | Hydrocarbonaceous composition |
| WO2006092059A1 (en) | 2005-03-04 | 2006-09-08 | Fan Wu | Design and synthesis of novel antimicrobials |
| GB0505861D0 (en) | 2005-03-22 | 2005-04-27 | Univ Cardiff | Methods for the synthesis of heteroaromatic compounds |
| JP5154406B2 (ja) | 2005-04-13 | 2013-02-27 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| WO2006127569A2 (en) | 2005-05-25 | 2006-11-30 | The Board Of Governors For Higher Education, Stat E Of Rhode Island And Providence Plantations | Thermochromic and thermoflourescent pigments: enhancing color and flourescence with additives |
| US7816524B2 (en) | 2005-08-05 | 2010-10-19 | Cylene Pharmaceuticals, Inc. | Methods of preparing quinolone analogs |
| DE102005045132A1 (de) | 2005-09-22 | 2007-03-29 | Archimica Gmbh | Verfahren zur Herstellung von 2-Arylcarbonylverbindungen, 2-Arylestern und 2-Arylnitrilen sowie ihrer heteroaromatischen Analoga |
| EP1787981A1 (en) | 2005-11-22 | 2007-05-23 | Bayer CropScience S.A. | New N-phenethylcarboxamide derivatives |
| WO2007064861A2 (en) | 2005-12-02 | 2007-06-07 | Brandeis University | Asymmetric friedel-crafts alkylations catalyzed by byfunctional cinchona alkaloids |
| US20070203236A1 (en) | 2006-01-11 | 2007-08-30 | Smith Jeffrey W | Novel antagonists of the human fatty acid synthase thioesterase |
| JP4895267B2 (ja) | 2006-02-21 | 2012-03-14 | 三菱レイヨン株式会社 | 3,6−エポキシ−1,2,3,6−テトラヒドロフタル酸無水物誘導体の製造方法 |
| EP1840188B1 (en) | 2006-03-31 | 2011-09-07 | Sony Deutschland GmbH | A composition comprising at least one type of liquid crystal |
| DE602006007804D1 (de) | 2006-03-31 | 2009-08-27 | Sony Deutschland Gmbh | Zusammensetzung die mindestens eine Art von Flüssigkristall enthält |
| US20080027044A1 (en) | 2006-06-13 | 2008-01-31 | Kim Lewis | Prodrug antibiotic screens |
| WO2008003746A1 (en) | 2006-07-06 | 2008-01-10 | Bayer Cropscience Sa | N-(4-pyridin-2-ylbutyl) carboxamide derivatives, their process of preparation and their use as fungicides |
| CA2659956C (en) | 2006-08-04 | 2016-01-05 | Lewis C. Cantley | Inhibitors of pyruvate kinase and methods of treating disease |
| DE102006037399A1 (de) | 2006-08-10 | 2008-02-14 | Archimica Gmbh | Verfahren zur Herstellung von Arylaminen |
| US7858126B2 (en) | 2006-08-31 | 2010-12-28 | Trinity Laboratories Inc. | Derivatives of sandalwood oil and santalols for treating cold sores and herpes |
| WO2008033466A2 (en) | 2006-09-14 | 2008-03-20 | Combinatorx (Singapore) Pre. Ltd. | Compositions and methods for treatment of viral diseases |
| US20100204317A1 (en) | 2006-11-03 | 2010-08-12 | Qlt Inc. | Methods of treating dermatological disorders or conditions |
| RU2319694C1 (ru) | 2007-01-19 | 2008-03-20 | Михаил Иванович Власов | Способ получения производных 3-гидроксипиридина |
| CL2008000512A1 (es) | 2007-02-22 | 2008-08-29 | Bayer Cropscience Sa | Compuestos derivados de n-(3-fenilpropil)carboxamida; procedimiento de preparacion de dichos compuestos; composicion fungicida; y metodo para combatir de forma preventiva o curativa los hongos fitopatogenos de cultivos. |
| WO2008131258A2 (en) | 2007-04-19 | 2008-10-30 | State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State University | Pactamycin biosynthetic gene cluster |
| EP2581081A3 (en) * | 2007-06-01 | 2013-07-31 | The Trustees Of Princeton University | Treatment of viral infections by modulation of host cell metabolic pathways |
| HUP0700395A2 (en) | 2007-06-07 | 2009-03-02 | Sanofi Aventis | Substituted [1,2,4] triazolo [1,5-a] quinolines, process for their preparation, pharmaceutical compositions thereof, and intermediates |
| WO2008156610A2 (en) | 2007-06-13 | 2008-12-24 | Northeastern University | Antibiotic compounds |
| EP2003125A1 (en) | 2007-06-14 | 2008-12-17 | Total Petrochemicals Research Feluy | New tridentate ligand compounds with imino furan units, method for manufacturing said compounds, and their use in the preparation of catalysts for the homopolymerisation and copolymerisation of ethylene and alpha-olefins |
| GB0715454D0 (en) | 2007-08-08 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| GB0715576D0 (en) | 2007-08-09 | 2007-09-19 | Syngenta Ltd | Novel herbicides |
| CN101801940B (zh) | 2007-09-10 | 2013-04-10 | 日产化学工业株式会社 | 取代异*唑啉化合物和有害生物防除剂 |
| CN101918389A (zh) | 2007-11-02 | 2010-12-15 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| US10047066B2 (en) | 2007-11-30 | 2018-08-14 | Newlink Genetics Corporation | IDO inhibitors |
| PT2303270T (pt) | 2008-05-05 | 2017-08-25 | Sanofi Sa | Derivados fundidos do ácido ciclopentanocarboxílico substituídos por acilamino e sua utilização como produtos farmacêuticos |
| JP2010235590A (ja) | 2009-03-09 | 2010-10-21 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
| CN101857622B (zh) | 2009-04-07 | 2014-12-03 | 中国医学科学院药物研究所 | 一种腺苷衍生物及其制备方法和应用 |
| AU2010270797B2 (en) * | 2009-07-08 | 2015-03-19 | Dermira (Canada), Inc. | TOFA analogs useful in treating dermatological disorders or conditions |
| CN101704700B (zh) | 2009-10-28 | 2012-04-11 | 东北师范大学 | 一种氢溴酸(溴化氢)催化芳烃的傅-克反应方法 |
| AR079022A1 (es) | 2009-11-02 | 2011-12-21 | Sanofi Aventis | Derivados de acido carboxilico ciclico sustituidos con acilamino, su uso como productos farmaceuticos, composicion farmaceutica y metodo de preparacion |
| US8920681B2 (en) | 2009-12-30 | 2014-12-30 | Korea University Research And Business Foundation | Electrically conductive polymers with enhanced conductivity |
| TWI532725B (zh) | 2010-01-26 | 2016-05-11 | 賽諾菲阿凡提斯公司 | 經氧取代之3-雜芳醯基胺基-丙酸衍生物及其作為藥物之用途 |
| CN102134180A (zh) | 2011-01-06 | 2011-07-27 | 华东理工大学 | 一种呋喃衍生物的开环加氢反应新方法 |
| BR112013017953A2 (pt) | 2011-01-13 | 2017-08-29 | Quadra Logic Tech Inc | Composição farmacêutica, formulação tópica, método, e, composição fotossensibilizadora |
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