JP5159616B2 - 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 - Google Patents

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 Download PDF

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JP5159616B2
JP5159616B2 JP2008517192A JP2008517192A JP5159616B2 JP 5159616 B2 JP5159616 B2 JP 5159616B2 JP 2008517192 A JP2008517192 A JP 2008517192A JP 2008517192 A JP2008517192 A JP 2008517192A JP 5159616 B2 JP5159616 B2 JP 5159616B2
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compound
formula
acyl
protecting group
oxygen protecting
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JP2008543874A5 (https=
JP2008543874A (ja
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グレース ユング，
ジェームス ギー ケン イー，
ダグ タ ハン チョウ，
バートランド エム． シー． プルービエ，
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カーディオム ファーマ コーポレイション
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    • 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

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  • 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)
  • Pyrrole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2008517192A 2005-06-15 2006-06-15 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 Active JP5159616B2 (ja)

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 (3)

Publication Number Publication Date
JP2008543874A JP2008543874A (ja) 2008-12-04
JP2008543874A5 JP2008543874A5 (https=) 2012-02-23
JP5159616B2 true JP5159616B2 (ja) 2013-03-06

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JP2008517192A Active JP5159616B2 (ja) 2005-06-15 2006-06-15 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

Country Status (7)

Country Link
US (4) US7754897B2 (https=)
EP (1) EP1915340B1 (https=)
JP (1) JP5159616B2 (https=)
BR (1) BRPI0612138B8 (https=)
CA (1) CA2612375C (https=)
MX (2) MX346530B (https=)
WO (1) WO2006138673A2 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013032392A (ja) * 2004-11-18 2013-02-14 Cardiome Pharma Corp アミノシクロヘキシルエーテル化合物の合成方法

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7705036B2 (en) 2004-04-01 2010-04-27 Cardiome Pharma Corp. Deuterated aminocyclohexyl ether compounds and processes for preparing same
JP4991037B2 (ja) * 2004-04-01 2012-08-01 カーディオム ファーマ コーポレイション イオンチャネル調節化合物を含む薬物結合体
US7754897B2 (en) 2005-06-15 2010-07-13 Cardiome Pharma Corp. Synthetic processes for the preparation of aminocyclohexyl ether compounds
WO2008137778A2 (en) * 2007-05-04 2008-11-13 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
WO2012024100A2 (en) 2010-08-16 2012-02-23 Merck Sharp & Dohme Corp. Process for preparing aminocyclohexyl ether compounds
US8932836B2 (en) 2010-08-16 2015-01-13 Codexis, Inc. Biocatalysts and methods for the synthesis of (1R,2R)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine
BR112014017833A2 (pt) 2012-01-20 2021-03-23 Dennis Brown Uso de hexitóis substituídos incluindo dianidrogalactitol e análogos para tratar doença neoplástica e células-tronco de câncer incluindo glioblastoma multiforme e meduloblastoma
US20150087687A1 (en) 2012-03-23 2015-03-26 Dennis Brown Compositions and methods to improve the therapeutic benefit of indirubin and analogs thereof, including meisoindigo
JP6280546B2 (ja) 2012-06-26 2018-02-14 デル マー ファーマシューティカルズ ジアンヒドロガラクチトール、ジアセチルジアンヒドロガラクチトール、ジブロモズルシトール、又はこれらの類似体若しくは誘導体を用いた、遺伝子多型又はａｈｉ１の調節不全若しくは変異を有する患者におけるチロシンキナーゼインヒビター抵抗性悪性腫瘍を処置するための方法
EP2983674A4 (en) 2013-04-08 2017-05-10 Dennis M. Brown Therapeutic benefit of suboptimally administered chemical compounds
KR102359214B1 (ko) 2014-04-04 2022-02-07 델 마 파마슈티컬스 폐의 비소세포 암종 및 난소암을 치료하기 위한 디안하이드로갈락티톨 및 이의 유사체 또는 유도체
JP7262118B2 (ja) 2016-10-06 2023-04-21 オーバス セラピューティクス インコーポレイテッド 医薬組成物およびその使用
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

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
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
EP0002214B1 (de) 1977-12-01 1981-05-13 Bayer Ag Benzyläther 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
ATE76292T1 (de) 1987-11-25 1992-06-15 American Cyanamid Co System fuer die verzoegerte (kontrollierte) freisetzung von substituierten dihydropyridincalciumantagonisten.
DE3836917A1 (de) * 1988-10-29 1990-05-17 Bayer Ag Verfahren zur herstellung von cyclopropylamin
US5215919A (en) * 1991-02-25 1993-06-01 Takeda Chemical Industries, Ltd. Process for producing optically active 2-hydroxycycloalkanecarboxylic acid esters using microbially derived reductase
CN1087725C (zh) * 1994-03-25 2002-07-17 同位素技术有限公司 用氘代方法增强药物效果
US6214608B1 (en) 1995-02-03 2001-04-10 Basf Aktiengesellschaft Resolution of racemates of primary and secondary heteroatom-substitued amines by enzyme-catalyzed acylation
DE19523868A1 (de) * 1995-06-30 1997-01-02 Huels Chemische Werke Ag Verfahren zur Herstellung von Cyclopropanamin
US6441025B2 (en) * 1996-03-12 2002-08-27 Pg-Txl Company, L.P. Water soluble paclitaxel derivatives
DE69735057T2 (de) 1996-03-12 2006-08-31 PG-TXL Co., L.P., Houston Wasserlösliche paclitaxel-prodrogen
US6342507B1 (en) * 1997-09-05 2002-01-29 Isotechnika, Inc. Deuterated rapamycin compounds, method and uses thereof
EP0991660B8 (en) * 1997-10-08 2006-04-05 Isotechnika,Inc. DEUTERATED and undeuterated CYCLOSPORINE ANALOGS AND THEIR USE AS IMMUNOMODULATING AGENTS
CA2326777C (en) 1998-04-01 2011-12-20 Nortran Pharmaceuticals Inc. Aminocyclohexyl ether compounds and uses thereof
EP1143896B1 (en) 1998-10-20 2006-12-13 The University of North Carolina at Chapel Hill Methods of hydrating the nasal mucosal surface
AU2899400A (en) * 1999-03-04 2000-09-21 Nortran Pharmaceuticals Inc. Aminocycloalkyl cinnamide compounds for arrhythmia and as analgesics and anesthetics
CA2311483A1 (en) 2000-06-12 2001-12-12 Gregory N Beatch IMIDAZO [1,2-A] PYRIDINIC ETHERS AND USES THEREOF
JP2004501191A (ja) * 2000-06-28 2004-01-15 テバ　ファーマシューティカル　インダストリーズ　リミティド カルベジロール
US7524879B2 (en) 2000-10-06 2009-04-28 Cardiome Pharma Corp. Ion channel modulating compounds and uses thereof
US7057053B2 (en) 2000-10-06 2006-06-06 Cardiome Pharma Corp. Ion channel modulating compounds and uses thereof
EP1291336A3 (en) * 2001-09-05 2003-10-08 Solvias AG Preparation of optically active alpha-hydroxyethers
JP2003250577A (ja) * 2001-12-27 2003-09-09 Sumitomo Chem Co Ltd ２‐ヒドロキシシクロアルカンカルボン酸エステルの製造方法
US20040049049A1 (en) 2002-06-14 2004-03-11 Johnson Matthey Pharmaceutical Materials, Inc. Stereoselective synthesis of 1,2-disubstituted cycloalkyls
WO2004014973A2 (en) 2002-08-13 2004-02-19 Sirus Pharmaceuticals Ltd Biodegradable polymer
US7056540B2 (en) * 2002-10-29 2006-06-06 Council Of Scientific And Industrial Research Enzymatic process for the preparation of optically active alcohols from ketones using tuberous root Daucus carota
WO2004098525A2 (en) 2003-05-02 2004-11-18 Cardiome Pharma Corp. Uses of ion channel modulating compounds
CA2524323C (en) 2003-05-02 2012-05-15 Cardiome Pharma Corp. Aminocyclohexyl ether compounds and uses thereof
WO2005016242A2 (en) 2003-06-04 2005-02-24 Cardiome Pharma Corp. Synthetic process for trans-aminocyclohexyl ether compounds
US7345087B2 (en) * 2003-10-31 2008-03-18 Cardiome Pharma Corp. Aminocyclohexyl ether compounds and uses thereof
US7754897B2 (en) * 2005-06-15 2010-07-13 Cardiome Pharma Corp. Synthetic processes for the preparation of aminocyclohexyl ether compounds
MXPA06011419A (es) * 2004-04-01 2007-04-20 Cardiome Pharma Corp Profarmacos de compuestos moduladores de canales ionicos y usos de los mismos.
WO2005097087A2 (en) 2004-04-01 2005-10-20 Cardiome Pharma Corp. Merged ion channel modulating compounds and uses thereof
JP4991037B2 (ja) * 2004-04-01 2012-08-01 カーディオム ファーマ コーポレイション イオンチャネル調節化合物を含む薬物結合体
US7705036B2 (en) * 2004-04-01 2010-04-27 Cardiome Pharma Corp. Deuterated aminocyclohexyl ether compounds and processes for preparing same
EP1828099B1 (en) 2004-11-18 2020-01-22 Correvio International Sàrl Synthetic process for aminocyclohexyl ether compounds
US20090069404A1 (en) * 2007-09-09 2009-03-12 Protia, Llc Deuterium-enriched vernakalant

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013032392A (ja) * 2004-11-18 2013-02-14 Cardiome Pharma Corp アミノシクロヘキシルエーテル化合物の合成方法

Also Published As

Publication number Publication date
EP1915340B1 (en) 2013-08-07
US8080673B2 (en) 2011-12-20
BRPI0612138A2 (pt) 2010-10-19
US20120065408A1 (en) 2012-03-15
US8618311B2 (en) 2013-12-31
US20120271057A9 (en) 2012-10-25
BRPI0612138B1 (pt) 2021-03-16
CA2612375A1 (en) 2006-12-28
WO2006138673A3 (en) 2007-03-22
US7754897B2 (en) 2010-07-13
MX2007016248A (es) 2008-03-07
US20130090483A1 (en) 2013-04-11
EP1915340A2 (en) 2008-04-30
BRPI0612138B8 (pt) 2021-05-25
US8344162B2 (en) 2013-01-01
WO2006138673A2 (en) 2006-12-28
MX346530B (es) 2017-03-22
JP2008543874A (ja) 2008-12-04
US20100217014A1 (en) 2010-08-26
CA2612375C (en) 2013-08-06
US20070015924A1 (en) 2007-01-18

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