CA2299308C - Cyclohexenone long-chain alcohol and medicament containing same - Google Patents

Cyclohexenone long-chain alcohol and medicament containing same Download PDF

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Publication number
CA2299308C
CA2299308C CA002299308A CA2299308A CA2299308C CA 2299308 C CA2299308 C CA 2299308C CA 002299308 A CA002299308 A CA 002299308A CA 2299308 A CA2299308 A CA 2299308A CA 2299308 C CA2299308 C CA 2299308C
Authority
CA
Canada
Prior art keywords
compound
hexane
solution
nmr
mhz
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.)
Expired - Lifetime
Application number
CA002299308A
Other languages
English (en)
French (fr)
Other versions
CA2299308A1 (en
Inventor
Bang Luu
Gaby Schmitt
Florence Keyling
Celine Junges-Girlanda
Masashi Yamada
Yukie Suma
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Centre National de la Recherche Scientifique CNRS
Universite de Strasbourg
Meiji Co Ltd
Original Assignee
Meiji Milk Products Co 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 Meiji Milk Products Co Ltd filed Critical Meiji Milk Products Co Ltd
Publication of CA2299308A1 publication Critical patent/CA2299308A1/en
Application granted granted Critical
Publication of CA2299308C publication Critical patent/CA2299308C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • 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
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • 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
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • 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
    • C07C45/676—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 by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/713—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA002299308A 1997-08-13 1998-08-11 Cyclohexenone long-chain alcohol and medicament containing same Expired - Lifetime CA2299308C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP9/218474 1997-08-13
JP21847497 1997-08-13
PCT/JP1998/003560 WO1999008987A1 (en) 1997-08-13 1998-08-11 Cyclohexenone long-chain alcohol and medicament containing same

Publications (2)

Publication Number Publication Date
CA2299308A1 CA2299308A1 (en) 1999-02-25
CA2299308C true CA2299308C (en) 2008-03-25

Family

ID=16720502

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002299308A Expired - Lifetime CA2299308C (en) 1997-08-13 1998-08-11 Cyclohexenone long-chain alcohol and medicament containing same

Country Status (7)

Country Link
US (1) US6228893B1 (enExample)
EP (1) EP1003706B1 (enExample)
JP (1) JP3766591B2 (enExample)
AT (1) ATE233724T1 (enExample)
CA (1) CA2299308C (enExample)
DE (1) DE69811905T2 (enExample)
WO (1) WO1999008987A1 (enExample)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4469441B2 (ja) 1999-02-10 2010-05-26 明治乳業株式会社 神経変性疾患の予防又は治療薬
JP4490536B2 (ja) * 2000-01-31 2010-06-30 明治乳業株式会社 脳血管障害に基づく疾患の予防又は治療薬
JP2002068973A (ja) * 2000-06-16 2002-03-08 Meiji Milk Prod Co Ltd 幹細胞分化誘導促進剤
US20040115810A1 (en) * 2000-10-04 2004-06-17 Bang Luu Stem cell differentiation-inducing promoter
JP4250882B2 (ja) * 2000-10-18 2009-04-08 住友化学株式会社 スルホン誘導体およびその製造方法
JP4861560B2 (ja) * 2001-02-19 2012-01-25 株式会社明治 糖尿病合併症治療剤
JP3836684B2 (ja) * 2001-02-19 2006-10-25 明治乳業株式会社 排尿障害治療剤
WO2002094252A1 (en) * 2001-05-24 2002-11-28 Meiji Dairies Corporation Preventive or remedy for diseases caused by cerebrovascular disturbances
JP2005518403A (ja) * 2002-01-09 2005-06-23 トリデント サイエンシーズ エルエルシー アンドロゲンレセプターをブロックする化合物
JP4035332B2 (ja) * 2002-01-22 2008-01-23 明治乳業株式会社 シクロヘキセノン長鎖アルコールの製造法
US7307098B2 (en) 2002-07-19 2007-12-11 Meiji Dairies Corporation Indole derivatives and drugs containing the same
CA2519178C (en) 2003-03-28 2010-01-12 Meiji Dairies Corporation Process for producing cyclohexenone long-chain alcohols
CA2583699C (en) * 2004-10-13 2012-11-20 Meiji Dairies Corporation Stat3 phosphorylation inhibitor and notch1 expression inhibitor
CN101180041B (zh) * 2005-01-18 2011-04-13 明治乳业株式会社 感觉障碍治疗剂
EP1854777A4 (en) * 2005-02-28 2010-07-07 Meiji Dairies Corp LONG-CHAINED HYDROCHINONE DERIVATIVE AND / OR LONG-CHAINED PHENOXY DERIVATIVE AND PHARMACEUTICAL PREPARATION CONTAINING THEREOF
US20080312336A1 (en) * 2005-05-26 2008-12-18 Keisuke Satoh Preventive and/or Therapeutic Agent for Diabetic Vascular Disorder and Respiratory Disorder
WO2013147072A1 (ja) * 2012-03-29 2013-10-03 大鵬薬品工業株式会社 3-(15-ヒドロキシペンタデシル)-2,4,4-トリメチル-2-シクロヘキセン-1-オンの共結晶
JP5566521B1 (ja) 2013-09-27 2014-08-06 大鵬薬品工業株式会社 膀胱・尿道協調不全改善剤
US20170035705A1 (en) * 2015-08-04 2017-02-09 Taiho Pharmaceutical Co., Ltd. Detrusor hyperactivity with impaired contractility ameliorating agent
BR112018014841B1 (pt) 2016-01-22 2022-03-03 Taiho Pharmaceutical Co., Ltd. Álcoois de cadeia longa cicloexenona, seus usos e métodos para a produção dos mesmos com alta pureza
JP2022013721A (ja) 2020-07-03 2022-01-18 大鵬薬品工業株式会社 排尿症状治療剤
US20230295068A1 (en) * 2020-08-07 2023-09-21 Taiho Pharmaceutical Co., Ltd. Novel cycloalkenone compound or salt thereof
US20250178998A1 (en) 2022-02-09 2025-06-05 Taiho Pharmaceutical Co., Ltd. Crystal form of cyclohexenone compound

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0448697B1 (fr) * 1989-10-13 1996-04-10 Neurofit Analogues de la vitamine a, leurs applications, notamment en tant que molecules cytotrophiques et cytoprotectrices, et compositions pharmaceutiques les contenant
ATE105282T1 (de) * 1992-11-18 1994-05-15 Medafor Langkettige fettalkohole mit neurotropischer und gedaechtnissfoerdernder wirkung.

Also Published As

Publication number Publication date
JP3766591B2 (ja) 2006-04-12
DE69811905T2 (de) 2003-11-06
WO1999008987A1 (en) 1999-02-25
EP1003706A1 (en) 2000-05-31
DE69811905D1 (de) 2003-04-10
ATE233724T1 (de) 2003-03-15
US6228893B1 (en) 2001-05-08
JP2001515058A (ja) 2001-09-18
EP1003706B1 (en) 2003-03-05
CA2299308A1 (en) 1999-02-25

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Effective date: 20180813