WO1999047497A3 - Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement - Google Patents

Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement Download PDF

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Publication number
WO1999047497A3
WO1999047497A3 PCT/CA1999/000212 CA9900212W WO9947497A3 WO 1999047497 A3 WO1999047497 A3 WO 1999047497A3 CA 9900212 W CA9900212 W CA 9900212W WO 9947497 A3 WO9947497 A3 WO 9947497A3
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WO
WIPO (PCT)
Prior art keywords
compounds
treatment
methods
compositions containing
acylsulfonamides
Prior art date
Application number
PCT/CA1999/000212
Other languages
English (en)
Other versions
WO1999047497A2 (fr
Inventor
Yves Gareau
Marc Labelle
Helene Juteau
Michel Gallant
Nicolas Lachance
Michel Belley
Original Assignee
Merck Frosst Canada Inc
Yves Gareau
Marc Labelle
Helene Juteau
Michel Gallant
Nicolas Lachance
Michel Belley
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from GBGB9815856.1A external-priority patent/GB9815856D0/en
Application filed by Merck Frosst Canada Inc, Yves Gareau, Marc Labelle, Helene Juteau, Michel Gallant, Nicolas Lachance, Michel Belley filed Critical Merck Frosst Canada Inc
Priority to JP2000536694A priority Critical patent/JP2002506851A/ja
Priority to EP99907214A priority patent/EP1071648A2/fr
Priority to AU27086/99A priority patent/AU756333B2/en
Priority to CA002322742A priority patent/CA2322742A1/fr
Publication of WO1999047497A2 publication Critical patent/WO1999047497A2/fr
Publication of WO1999047497A3 publication Critical patent/WO1999047497A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/64—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne des composés représentés par la formule (I), ainsi que des sels, des hydrates et des esters de ceux-ci qui sont acceptables d'un point de vue pharmaceutique. Les composés sont utiles pour traiter ou prévenir des maladies dans lesquelles intervient la prostaglandine. L'invention concerne également des compositions pharmaceutiques contenant ces composés et des méthodes de traitement.
PCT/CA1999/000212 1998-03-13 1999-03-12 Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement WO1999047497A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2000536694A JP2002506851A (ja) 1998-03-13 1999-03-12 カルボン酸類およびアシルスルホンアミド類、そのような化合物を含む組成物ならびに治療方法
EP99907214A EP1071648A2 (fr) 1998-03-13 1999-03-12 Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement
AU27086/99A AU756333B2 (en) 1998-03-13 1999-03-12 Carboxylic acids and acylsulfonamides, compositions containing such compounds and methods of treatment
CA002322742A CA2322742A1 (fr) 1998-03-13 1999-03-12 Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US7799098P 1998-03-13 1998-03-13
US60/077,990 1998-03-13
GBGB9815856.1A GB9815856D0 (en) 1998-07-21 1998-07-21 Carboxylic acids and acylsulfonamides compositions containing such compounds and methods of treatment
GB9815856.1 1998-07-21

Publications (2)

Publication Number Publication Date
WO1999047497A2 WO1999047497A2 (fr) 1999-09-23
WO1999047497A3 true WO1999047497A3 (fr) 1999-10-28

Family

ID=26314084

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1999/000212 WO1999047497A2 (fr) 1998-03-13 1999-03-12 Acides carboxyliques et acylsulfonamides, compositions contenant ces composes et methodes de traitement

Country Status (2)

Country Link
EP (1) EP1071648A2 (fr)
WO (1) WO1999047497A2 (fr)

Cited By (3)

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USRE43372E1 (en) 1999-03-05 2012-05-08 Duke University C16 unsaturated FP-selective prostaglandins analogs
US8906962B2 (en) 2000-03-31 2014-12-09 Duke University Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
US9346837B2 (en) 2000-03-31 2016-05-24 Duke University Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives

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US6521619B2 (en) 2000-06-29 2003-02-18 Icos Corporation Aryl phenylcyclopropyl sulfide derivatives and their use as cell adhesion inhibiting anti-inflammatory and immune suppressive agents
CA2414464A1 (fr) * 2000-06-29 2002-01-10 Abbott Laboratories Derives de sulfure d'aryle phenycyclopropyle et leur utilisation en tant que composes anti-inflammatoires inhibant l'adhesion cellulaire et agents immunosuppresseurs
AP2001002265A0 (en) * 2000-08-31 2001-09-30 Pfizer Phenoxybenzylamine derivatives as SSRIs.
US6610747B2 (en) 2000-08-31 2003-08-26 Pfizer Inc. Phenoxybenzylamine derivatives as SSRIs
HN2001000224A (es) 2000-10-19 2002-06-13 Pfizer Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos.
KR100637564B1 (ko) 2001-01-26 2006-10-20 추가이 세이야쿠 가부시키가이샤 대사 조절자로서 유용한 말로닐-코에이 데카르복실라제억제제
ATE359773T1 (de) 2001-01-26 2007-05-15 Chugai Pharmaceutical Co Ltd Verfahren zur behandlung von erkrankungen mit malonyl coa-decarboxylase-inhibitoren
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US7709510B2 (en) 2001-02-20 2010-05-04 Chugai Seiyaku Kabushiki Kaisha Azoles as malonyl-CoA decarboxylase inhibitors useful as metabolic modulators
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MXPA04009960A (es) 2002-04-12 2004-12-13 Pfizer Compuestos de pirazol como agentes anti-inflamatorios y analgesicos.
CA2533747C (fr) 2003-08-01 2012-11-13 Chugai Seiyaku Kabushiki Kaisha Composes heterocycliques utiles comme inhibiteurs de la malonyl-coa decarboxylase
ES2378418T3 (es) 2003-08-01 2012-04-12 Chugai Seiyaku Kabushiki Kaisha Compuestos de azol basados en cianoguanidina útiles como inhibidores de malonil-coadescarboxilasa
WO2005011812A1 (fr) 2003-08-01 2005-02-10 Chugai Seiyaku Kabushiki Kaisha Composes de cyanoamide utiles en tant qu'inhibiteurs de malonyl-coa decarboxylase
WO2005011693A1 (fr) 2003-08-01 2005-02-10 Chugai Seiyaku Kabushiki Kaisha Composes de piperidine utiles en tant qu'inhibiteurs de malonyl-coa decarboxylase
RU2008108984A (ru) * 2005-08-10 2009-09-20 Такеда Фармасьютикал Компани Лимитед (Jp) Терапевтический агент от диабета
US20080200568A1 (en) * 2005-08-30 2008-08-21 Stephanie Chissoe Genes Associated With Type ll Diabetes Mellitus
JP5147401B2 (ja) 2005-09-06 2013-02-20 塩野義製薬株式会社 Ｐｇｄ２受容体アンタゴニスト活性を有するインドールカルボン酸誘導体
TW200824692A (en) 2006-08-21 2008-06-16 Arqule Inc Novel lapachone compounds and methods of use thereof
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EP2257536A4 (fr) 2008-02-14 2011-03-23 Amira Pharmaceuticals Inc Composés diaryliques cycliques en tant qu'antagonistes de récepteurs de prostaglandine d2
JP2011518130A (ja) 2008-04-02 2011-06-23 アミラ ファーマシューティカルズ，インク． プロスタグランジンｄ２受容体のアミノアルキルフェニルアンタゴニスト
WO2010057118A2 (fr) 2008-11-17 2010-05-20 Amira Pharmaceuticals, Inc. Antagonistes hétérocycliques des récepteurs de la prostaglandine d2
CN102838515A (zh) * 2011-06-23 2012-12-26 南京大学 肉桂酰磺酰胺类化合物的制备及其在抗癌治疗药物中的应用
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CN107628981B (zh) * 2017-10-31 2019-07-30 威海市妇女儿童医院 一种肉桂酰基吲哚啉化合物及其制备青光眼药物的应用
CN117164462A (zh) * 2023-04-24 2023-12-05 江西师范大学 一种二芳基甲烷类化合物及其制备方法和应用

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EP0157420A2 (fr) * 1984-04-04 1985-10-09 TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION Dérivés d'amide et inhibiteurs de 5-lipoxygénase les contenant comme substance active
EP0223593A2 (fr) * 1985-11-19 1987-05-27 Glaxo Group Limited Acides et esters phénoxyalcoylcarboxyliques, leur préparation ainsi que leur formule pharmaceutique
US4996214A (en) * 1990-06-28 1991-02-26 Smithkline Beecham Corporation Quinolinyl substituted phenyl/thioalkanoic acid substituted propionic acids and leucotriene antagonist use thereof
EP0459243A2 (fr) * 1990-05-30 1991-12-04 Bayer Ag Azines substituées
WO1992002495A1 (fr) * 1990-07-27 1992-02-20 Schering Aktiengesellschaft Berlin/Bergkamen Derives de cyclopentane, procede pour leur fabrication, ainsi que leur utilisation pharmaceutique
JPH0578230A (ja) * 1991-09-18 1993-03-30 Kanebo Ltd 美白化粧料
EP0536713A1 (fr) * 1991-10-07 1993-04-14 E.R. SQUIBB & SONS, INC. Oxazoles et imidazoles comme analogues de prostaglandines
EP0560080A1 (fr) * 1992-03-03 1993-09-15 Hodogaya Chemical Co., Ltd. Toner électrophotographique
WO1996011902A1 (fr) * 1994-10-12 1996-04-25 Zeneca Limited Composes aromatiques substitues pharmaceutiquement actifs
WO1996031505A1 (fr) * 1995-04-07 1996-10-10 Pharmacopeia, Inc. Composes tricycliques utiles pour l'inhibition de la fonction de la proteine-g et le traitement des maladies proliferatives
WO1997008934A2 (fr) * 1995-06-19 1997-03-13 Ontogen Corporation Derives d'acide aryl-acrylique convenant comme inhibiteurs de proteine-tyrosine-phosphatase
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WO1997025328A1 (fr) * 1996-01-10 1997-07-17 Rhone-Poulenc Rorer S.A. DERIVES DE 5H,10H-IMIDAZO(1,2-a)INDENO(1,2-e)PYRAZINE-4-ONE, LEUR PREPARATION, LEURS INTERMEDIAIRES ET LES MEDICAMENTS LES CONTENANT______________________________________________________________

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Publication number Priority date Publication date Assignee Title
EP0028063A1 (fr) * 1979-09-05 1981-05-06 Glaxo Group Limited Dérivés de phénol, procédés pour leur préparation et composés pharmaceutiques les contenant
EP0157420A2 (fr) * 1984-04-04 1985-10-09 TERUMO KABUSHIKI KAISHA trading as TERUMO CORPORATION Dérivés d'amide et inhibiteurs de 5-lipoxygénase les contenant comme substance active
EP0223593A2 (fr) * 1985-11-19 1987-05-27 Glaxo Group Limited Acides et esters phénoxyalcoylcarboxyliques, leur préparation ainsi que leur formule pharmaceutique
EP0459243A2 (fr) * 1990-05-30 1991-12-04 Bayer Ag Azines substituées
US4996214A (en) * 1990-06-28 1991-02-26 Smithkline Beecham Corporation Quinolinyl substituted phenyl/thioalkanoic acid substituted propionic acids and leucotriene antagonist use thereof
WO1992002495A1 (fr) * 1990-07-27 1992-02-20 Schering Aktiengesellschaft Berlin/Bergkamen Derives de cyclopentane, procede pour leur fabrication, ainsi que leur utilisation pharmaceutique
JPH0578230A (ja) * 1991-09-18 1993-03-30 Kanebo Ltd 美白化粧料
EP0536713A1 (fr) * 1991-10-07 1993-04-14 E.R. SQUIBB & SONS, INC. Oxazoles et imidazoles comme analogues de prostaglandines
EP0560080A1 (fr) * 1992-03-03 1993-09-15 Hodogaya Chemical Co., Ltd. Toner électrophotographique
WO1996011902A1 (fr) * 1994-10-12 1996-04-25 Zeneca Limited Composes aromatiques substitues pharmaceutiquement actifs
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USRE43372E1 (en) 1999-03-05 2012-05-08 Duke University C16 unsaturated FP-selective prostaglandins analogs
US8906962B2 (en) 2000-03-31 2014-12-09 Duke University Compositions and methods for treating hair loss using non-naturally occurring prostaglandins
US9346837B2 (en) 2000-03-31 2016-05-24 Duke University Cosmetic and pharmaceutical compositions and methods using 2-decarboxy-2-phosphinico derivatives
US9579270B2 (en) 2000-03-31 2017-02-28 Duke University Compositions and methods for treating hair loss using non-naturally occurring prostaglandins

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