CA2612375C - Synthetic processes for the preparation of aminocyclohexyl ether compounds - Google Patents

Synthetic processes for the preparation of aminocyclohexyl ether compounds Download PDF

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Publication number
CA2612375C
CA2612375C CA2612375A CA2612375A CA2612375C CA 2612375 C CA2612375 C CA 2612375C CA 2612375 A CA2612375 A CA 2612375A CA 2612375 A CA2612375 A CA 2612375A CA 2612375 C CA2612375 C CA 2612375C
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CA
Canada
Prior art keywords
formula
compound
oxygen
hydrogen
group
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
CA2612375A
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English (en)
French (fr)
Other versions
CA2612375A1 (en
Inventor
Bertrand M. C. Plouvier
Doug Ta Hung Chou
Grace Jung
James Gee Ken Yee
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.)
Cipher Pharmaceuticals Inc
Original Assignee
Cardiome Pharma Corp
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 Cardiome Pharma Corp filed Critical Cardiome Pharma Corp
Publication of CA2612375A1 publication Critical patent/CA2612375A1/en
Application granted granted Critical
Publication of CA2612375C publication Critical patent/CA2612375C/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
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/12—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/14—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • 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
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrrole Compounds (AREA)
CA2612375A 2005-06-15 2006-06-15 Synthetic processes for the preparation of aminocyclohexyl ether compounds Expired - Lifetime CA2612375C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US69098905P 2005-06-15 2005-06-15
US60/690,989 2005-06-15
US74824805P 2005-12-07 2005-12-07
US60/748,248 2005-12-07
PCT/US2006/023668 WO2006138673A2 (en) 2005-06-15 2006-06-15 Synthetic processes for the preparation of aminocyclohexyl ether compounds

Publications (2)

Publication Number Publication Date
CA2612375A1 CA2612375A1 (en) 2006-12-28
CA2612375C true CA2612375C (en) 2013-08-06

Family

ID=37395936

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2612375A Expired - Lifetime CA2612375C (en) 2005-06-15 2006-06-15 Synthetic processes for the preparation of aminocyclohexyl ether compounds

Country Status (7)

Country Link
US (4) US7754897B2 (enExample)
EP (1) EP1915340B1 (enExample)
JP (1) JP5159616B2 (enExample)
BR (1) BRPI0612138B8 (enExample)
CA (1) CA2612375C (enExample)
MX (2) MX2007016248A (enExample)
WO (1) WO2006138673A2 (enExample)

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US7705036B2 (en) * 2004-04-01 2010-04-27 Cardiome Pharma Corp. Deuterated aminocyclohexyl ether compounds and processes for preparing same
CA2561733A1 (en) * 2004-04-01 2005-10-13 Cardiome Pharma Corp. Pegylated ion channel modulating compounds
US8692002B2 (en) 2004-11-18 2014-04-08 Cardiome Pharma Corp. Synthetic process for aminocyclohexyl ether compounds
JP5159616B2 (ja) 2005-06-15 2013-03-06 カーディオム ファーマ コーポレイション アミノシクロヘキシルエーテル化合物の調製のための合成プロセス
US20080312309A1 (en) * 2007-05-04 2008-12-18 Cardiome Pharma Corp. Controlled release oral formulations of ion channel modulating compounds and related methods for preventing arrhythmia
EP2445504A4 (en) 2009-06-23 2012-11-14 Medicinova Inc 2-AMINO-1- (2-ISOPROPYLPYRAZOLO [1,5-A] PYRIDINE-3-YL) PROPAN-1-ONE ENANTIOMER COMPOSITIONS AND METHODS THEREOF
US8932836B2 (en) 2010-08-16 2015-01-13 Codexis, Inc. Biocatalysts and methods for the synthesis of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine
WO2012024100A2 (en) 2010-08-16 2012-02-23 Merck Sharp & Dohme Corp. Process for preparing aminocyclohexyl ether compounds
CN115778934A (zh) 2012-01-20 2023-03-14 德玛公司 经取代的己糖醇类用于治疗恶性肿瘤的用途
WO2013142817A2 (en) 2012-03-23 2013-09-26 Dennis Brown Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo
US20150182490A1 (en) 2012-06-26 2015-07-02 Del Mar Pharmaceuticals Methods for treating tyrosine-kinase-inhibitor-resistant malignancies in patients with genetic polymorphisms or ahi1 dysregulations or mutations employing dianhydrogalactitol, diacetyldianhydrogalactitol, dibromodulcitol, or analogs or derivatives thereof
CN105492011A (zh) 2013-04-08 2016-04-13 丹尼斯·M·布朗 不理想给药化学化合物的治疗增效
KR102359214B1 (ko) 2014-04-04 2022-02-07 델 마 파마슈티컬스 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체
NZ792518A (en) 2016-10-06 2023-04-28 Orbus Therapeutics Inc Formulations for administration of eflornithine
WO2018200381A1 (en) 2017-04-25 2018-11-01 Temple Otorongo Llc Pharmaceutical composition comprising tryptophan and phyllokinin derivative for use in treating psychiatric and psychological conditions
US12605349B2 (en) 2024-09-05 2026-04-21 Orbus Therapeutics, Inc. Methods of treating grade 3 astrocytoma

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CA710830A (en) 1965-06-01 Moser Paul Disodium and calcium salt of the calcium complex of 2-aminocyclohexyl 2'-aminoethyl ether-n,n,n',n'-tetraacetic acid
DE2860703D1 (en) 1977-12-01 1981-08-20 Bayer Ag Benzyl ethers of cyclic 1,2-diols, methods for their preparation and their use as herbicides
DE2753556A1 (de) 1977-12-01 1979-06-07 Bayer Ag Benzylaether von cyclischen 1,2-diolen, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide
US4684728A (en) 1979-01-12 1987-08-04 Bayer Aktiengesellschaft Solubilizing biologically active compounds with reactive hydrogen atoms
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CA2561733A1 (en) * 2004-04-01 2005-10-13 Cardiome Pharma Corp. Pegylated ion channel modulating compounds
US8692002B2 (en) * 2004-11-18 2014-04-08 Cardiome Pharma Corp. Synthetic process for aminocyclohexyl ether compounds
JP5159616B2 (ja) 2005-06-15 2013-03-06 カーディオム ファーマ コーポレイション アミノシクロヘキシルエーテル化合物の調製のための合成プロセス
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Also Published As

Publication number Publication date
BRPI0612138B1 (pt) 2021-03-16
US8344162B2 (en) 2013-01-01
BRPI0612138A2 (pt) 2010-10-19
MX346530B (es) 2017-03-22
JP5159616B2 (ja) 2013-03-06
JP2008543874A (ja) 2008-12-04
EP1915340B1 (en) 2013-08-07
US20070015924A1 (en) 2007-01-18
US8618311B2 (en) 2013-12-31
EP1915340A2 (en) 2008-04-30
WO2006138673A3 (en) 2007-03-22
US20120271057A9 (en) 2012-10-25
CA2612375A1 (en) 2006-12-28
MX2007016248A (es) 2008-03-07
US20130090483A1 (en) 2013-04-11
BRPI0612138B8 (pt) 2021-05-25
US20120065408A1 (en) 2012-03-15
WO2006138673A2 (en) 2006-12-28
US8080673B2 (en) 2011-12-20
US7754897B2 (en) 2010-07-13
US20100217014A1 (en) 2010-08-26

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