WO2005000281A2 - Derives de pyrazolidinedione - Google Patents

Derives de pyrazolidinedione Download PDF

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Publication number
WO2005000281A2
WO2005000281A2 PCT/EP2004/006471 EP2004006471W WO2005000281A2 WO 2005000281 A2 WO2005000281 A2 WO 2005000281A2 EP 2004006471 W EP2004006471 W EP 2004006471W WO 2005000281 A2 WO2005000281 A2 WO 2005000281A2
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
propoxy
dione
pyrazolidine
methyl
Prior art date
Application number
PCT/EP2004/006471
Other languages
English (en)
Other versions
WO2005000281A3 (fr
Inventor
Olivier Houille
Heinz Fretz
Kurt Hilpert
Markus Riederer
Thomas Giller
Oliver Valdenaire
Original Assignee
Actelion Pharmaceuticals Ltd.
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
Application filed by Actelion Pharmaceuticals Ltd. filed Critical Actelion Pharmaceuticals Ltd.
Priority to CA002529436A priority Critical patent/CA2529436A1/fr
Priority to JP2006515947A priority patent/JP2007506661A/ja
Priority to US10/562,623 priority patent/US20070037846A1/en
Priority to EP04739938A priority patent/EP1638540A2/fr
Publication of WO2005000281A2 publication Critical patent/WO2005000281A2/fr
Publication of WO2005000281A3 publication Critical patent/WO2005000281A3/fr

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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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4152—1,2-Diazoles having oxo groups directly attached to the heterocyclic ring, e.g. antipyrine, phenylbutazone, sulfinpyrazone
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
    • C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/542—Alkylated benzaldehydes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/548—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
    • C07C47/565—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups all hydroxy groups bound to the ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • 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
    • C07D231/14—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 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
    • C07D231/28—Two oxygen or sulfur atoms
    • C07D231/30—Two oxygen or sulfur atoms attached in positions 3 and 5
    • C07D231/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne des dérivés de pyrazolidinédione de formule générale (I), dans laquelle R1 désigne un hydrogène, un alkyle éventuellement substitué, un cycloalkyle, un aryle, un arylalkyle, un hétéroaryle, un hétéroarylalkyle ou un alkanoyle; et R2 représente un aryle ou un hétéroaryle; des tautomères de ceux-ci; des isomères géométriques de ceux-ci et des tautomères de ces isomères géométriques, notamment des mélanges de composés individuels de formule (I), ou des tautomères de ceux-ci, et des isomères géométriques de ceux-ci ou des tautomères de ceux-ci, des sels d'ajout acides acceptables sur le plan pharmaceutique des composés qui sont basiques; des sels acceptables sur le plan pharmaceutique de composés renfermant des groupes acides avec des bases; des esters acceptables sur le plan pharmaceutique des composés renfermant des groupes hydroxy ou carboxy; des promédicaments de composés dans lesquels un groupe formant un promédicament est présent; ainsi que des hydrates ou solvates de ceux-ci; lesdits dérivés sont actifs comme antagonistes du récepteur de l'adénosine diphosphate des plaquettes et peuvent être utilisés pour la prévention et/ou le traitement de maladies vasculaires périphériques, vasculaires viscérales, hépatiques et rénales, cardio-vasculaires et cérébro-vasculaires ou d'états associés à l'agrégation plaquettaire, notamment la thrombose et, respectivement, pour la fabrication des médicaments correspondants. Quelques composés, mais pas tous, de la formule (I) susmentionnée sont nouveaux.
PCT/EP2004/006471 2003-06-24 2004-06-16 Derives de pyrazolidinedione WO2005000281A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CA002529436A CA2529436A1 (fr) 2003-06-24 2004-06-16 Derives de pyrazolidinedione
JP2006515947A JP2007506661A (ja) 2003-06-24 2004-06-16 ピラゾリジンジオン誘導体
US10/562,623 US20070037846A1 (en) 2003-06-24 2004-06-16 Pyrazolidinedione derivatives
EP04739938A EP1638540A2 (fr) 2003-06-24 2004-06-16 Dérivés de pyrazolidinedione et leur utilisation comme inhibiteurs d'agrégation plaquettaire

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EPPCT/EP03/006616 2003-06-24
PCT/EP2003/006616 WO2005002574A1 (fr) 2003-06-24 2003-06-24 Derives de pyrazolidinedione et leur utilisation en tant qu'inhibiteurs de l'agregation des plaquettes

Publications (2)

Publication Number Publication Date
WO2005000281A2 true WO2005000281A2 (fr) 2005-01-06
WO2005000281A3 WO2005000281A3 (fr) 2005-04-14

Family

ID=33547562

Family Applications (2)

Application Number Title Priority Date Filing Date
PCT/EP2003/006616 WO2005002574A1 (fr) 2003-06-24 2003-06-24 Derives de pyrazolidinedione et leur utilisation en tant qu'inhibiteurs de l'agregation des plaquettes
PCT/EP2004/006471 WO2005000281A2 (fr) 2003-06-24 2004-06-16 Derives de pyrazolidinedione

Family Applications Before (1)

Application Number Title Priority Date Filing Date
PCT/EP2003/006616 WO2005002574A1 (fr) 2003-06-24 2003-06-24 Derives de pyrazolidinedione et leur utilisation en tant qu'inhibiteurs de l'agregation des plaquettes

Country Status (6)

Country Link
EP (1) EP1638540A2 (fr)
JP (1) JP2007506661A (fr)
CN (1) CN1812782A (fr)
AU (1) AU2003249865A1 (fr)
CA (1) CA2529436A1 (fr)
WO (2) WO2005002574A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1666469A1 (fr) * 2003-09-11 2006-06-07 Institute of Medicinal Molecular Design, Inc. Inhibiteur d'inhibiteur-1 activateur de plasmogene
WO2007020935A1 (fr) * 2005-08-17 2007-02-22 Ono Pharmaceutical Co., Ltd. Agent thérapeutique pour soulager la douleur, comprenant un récepteur p2y12 et/ou un bloqueur de récepteur p2y14
WO2007105751A1 (fr) 2006-03-16 2007-09-20 Astellas Pharma Inc. Derive de quinolone ou sel pharmaceutiquement acceptable de celui-ci
WO2009080227A2 (fr) 2007-12-26 2009-07-02 Sanofi-Aventis Dérivés de pyrazole-carboxamide utiles en tant qu'antagonistes de p2y12
US8426420B2 (en) 2007-12-26 2013-04-23 Sanofi Heterocyclic pyrazole-carboxamidesas P2Y12 antagonists
WO2017038650A1 (fr) * 2015-08-28 2017-03-09 積水メディカル株式会社 Composé benzyle
US11179390B2 (en) * 2017-03-15 2021-11-23 Idorsia Pharmaceuticals Ltd Subcutaneous administration of a P2Y12 receptor antagonist
US11584710B2 (en) 2017-07-31 2023-02-21 Horitzonts Tecnologics Hungary Korlátolt Felelosségu Társaság Compounds for treating infections

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6016788B2 (ja) * 2011-05-16 2016-10-26 国立大学法人九州大学 ＤＯＣＫ−Ａサブファミリー分子によるＲａｃ活性化を制御する低分子化合物及びその用途
WO2017131149A1 (fr) * 2016-01-29 2017-08-03 小野薬品工業株式会社 Dérivé de tétrahydronaphtalène

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2012634A1 (fr) * 1990-03-20 1991-09-20 Hassan Salari Tyrphostines pour le traitement des allergies et des affections inflammatoires et cardiovasculaires
WO2001009121A2 (fr) * 1999-07-30 2001-02-08 Basf Aktiengesellschaft 2-pyrazolin-5-ones
WO2002102359A2 (fr) * 2001-06-18 2002-12-27 Applied Research Systems Ars Holding N.V. Derives d'alkylidene pyrazolidinedione
WO2003074550A2 (fr) * 2002-03-01 2003-09-12 Pintex Pharmaceuticals, Inc. Composes de modulation de pin1 et procedes d'utilisation correspondant

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1404682B1 (fr) * 2001-06-29 2005-09-14 Novo Nordisk A/S Procede permettant d'inhiber ptp1b et / ou ptp de lymphocyteet et / ou d'autres ptpases a reste asp en position 48

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2012634A1 (fr) * 1990-03-20 1991-09-20 Hassan Salari Tyrphostines pour le traitement des allergies et des affections inflammatoires et cardiovasculaires
WO2001009121A2 (fr) * 1999-07-30 2001-02-08 Basf Aktiengesellschaft 2-pyrazolin-5-ones
WO2002102359A2 (fr) * 2001-06-18 2002-12-27 Applied Research Systems Ars Holding N.V. Derives d'alkylidene pyrazolidinedione
WO2003074550A2 (fr) * 2002-03-01 2003-09-12 Pintex Pharmaceuticals, Inc. Composes de modulation de pin1 et procedes d'utilisation correspondant

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1666469A4 (fr) * 2003-09-11 2008-12-03 Inst Med Molecular Design Inc Inhibiteur d'inhibiteur-1 activateur de plasmogene
EP1666469A1 (fr) * 2003-09-11 2006-06-07 Institute of Medicinal Molecular Design, Inc. Inhibiteur d'inhibiteur-1 activateur de plasmogene
WO2007020935A1 (fr) * 2005-08-17 2007-02-22 Ono Pharmaceutical Co., Ltd. Agent thérapeutique pour soulager la douleur, comprenant un récepteur p2y12 et/ou un bloqueur de récepteur p2y14
US8629126B2 (en) 2006-03-16 2014-01-14 Astellas Pharma Inc. Quinolone derivative or pharmaceutically acceptable salt thereof
WO2007105751A1 (fr) 2006-03-16 2007-09-20 Astellas Pharma Inc. Derive de quinolone ou sel pharmaceutiquement acceptable de celui-ci
US8133882B2 (en) 2006-03-16 2012-03-13 Astellas Pharma Inc Quinolone derivative or pharmaceutically acceptable salt thereof
WO2009080227A2 (fr) 2007-12-26 2009-07-02 Sanofi-Aventis Dérivés de pyrazole-carboxamide utiles en tant qu'antagonistes de p2y12
US8598179B2 (en) 2007-12-26 2013-12-03 Sanofi Pyrazole-carboxamide derivatives as P2Y12 antagonists
US8426420B2 (en) 2007-12-26 2013-04-23 Sanofi Heterocyclic pyrazole-carboxamidesas P2Y12 antagonists
WO2017038650A1 (fr) * 2015-08-28 2017-03-09 積水メディカル株式会社 Composé benzyle
JP6201076B1 (ja) * 2015-08-28 2017-09-20 積水メディカル株式会社 ベンジル化合物
JP2018002700A (ja) * 2015-08-28 2018-01-11 積水メディカル株式会社 ベンジル化合物
CN108026116A (zh) * 2015-08-28 2018-05-11 积水医疗株式会社 苄基化合物
US10822357B2 (en) 2015-08-28 2020-11-03 Sekisui Medical Co., Ltd. Benzyl compound
US11591351B2 (en) 2015-08-28 2023-02-28 Sekisui Medical Co., Ltd. Benzyl compound
US11179390B2 (en) * 2017-03-15 2021-11-23 Idorsia Pharmaceuticals Ltd Subcutaneous administration of a P2Y12 receptor antagonist
US11584710B2 (en) 2017-07-31 2023-02-21 Horitzonts Tecnologics Hungary Korlátolt Felelosségu Társaság Compounds for treating infections

Also Published As

Publication number Publication date
AU2003249865A1 (en) 2005-01-21
JP2007506661A (ja) 2007-03-22
CN1812782A (zh) 2006-08-02
CA2529436A1 (fr) 2005-01-16
WO2005000281A3 (fr) 2005-04-14
EP1638540A2 (fr) 2006-03-29
WO2005002574A1 (fr) 2005-01-13

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