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

Info

Publication number
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
Authority
JP
Japan
Prior art keywords
compound
formula
acyl
protecting group
oxygen protecting
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.)
Active
Application number
JP2008517192A
Other languages
English (en)
Japanese (ja)
Other versions
JP2008543874A (ja
JP2008543874A5 (https=
Inventor
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,
Original Assignee
カーディオム ファーマ コーポレイション
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 カーディオム ファーマ コーポレイション filed Critical カーディオム ファーマ コーポレイション
Publication of JP2008543874A publication Critical patent/JP2008543874A/ja
Publication of JP2008543874A5 publication Critical patent/JP2008543874A5/ja
Application granted granted Critical
Publication of JP5159616B2 publication Critical patent/JP5159616B2/ja
Anticipated expiration legal-status Critical
Active legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/04Heterocyclic 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
    • C07D207/10Heterocyclic 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
    • C07D207/12Oxygen or sulfur atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/06Antiarrhythmics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02Carboxylic 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
    • C07C235/04Carboxylic 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
    • C07C235/14Carboxylic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic 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
    • C07D207/30Heterocyclic 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
    • C07D207/34Heterocyclic 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
    • C07D207/36Oxygen or sulfur atoms
    • C07D207/402,5-Pyrrolidine-diones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/12Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14The 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)
  • 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

Family

ID=37395936

Family Applications (1)

Application Number Title Priority Date Filing Date
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) MX2007016248A (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
MXPA06011420A (es) * 2004-04-01 2007-04-20 Cardiome Pharma Corp Compuestos pegilados de modulacion de canal de iones.
US7705036B2 (en) * 2004-04-01 2010-04-27 Cardiome Pharma Corp. Deuterated aminocyclohexyl ether compounds and processes for preparing same
MX2007016248A (es) 2005-06-15 2008-03-07 Cardiome Pharma Corp Procedimiento sintetico para la preparacion de compuestos de eter aminociclohexilico.
EA200971025A1 (ru) * 2007-05-04 2010-04-30 Кардиом Фарма Корп. Пероральные композиции с регулируемым высвобождением соединений, модулирующих ионные каналы, и связанные с ними способы предупреждения аритмии
WO2010151551A1 (en) * 2009-06-23 2010-12-29 Medicinova, Inc. ENANTIOMERIC COMPOSITIONS OF 2-AMINO-1-(2-ISOPROPYLPYRAZOLO[1,5-a]PYRIDIN-3-YL)PROPAN-1-ONE AND RELATED METHODS
US9006460B2 (en) 2010-08-16 2015-04-14 Cardiome International Ag Process for preparing aminocyclohexyl ether compounds
EP2606139B1 (en) 2010-08-16 2015-07-15 Codexis, Inc. Biocatalysts and methods for the synthesis of (1r,2r)-2-(3,4-dimethoxyphenethoxy)cyclohexanamine
EP2804602B1 (en) 2012-01-20 2024-12-04 Del Mar Pharmaceuticals Use of substituted hexitols including dianhydrogalactitol and analogs to treat neoplastic disease and cancer stem cells including glioblastoma multforme and medulloblastoma
CA2868302A1 (en) 2012-03-23 2013-09-26 Dennis M. 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
KR20160061911A (ko) 2013-04-08 2016-06-01 데니스 엠. 브라운 최적하 투여된 화학 화합물의 치료 효과
SG11201608303QA (en) 2014-04-04 2016-11-29 Del Mar Pharmaceuticals Use of dianhydrogalactitol and analogs or derivatives thereof to treat non-small-cell carcinoma of the lung and ovarian cancer
IL314380A (en) 2016-10-06 2024-09-01 Orbus Therapeutics Inc Preparations for administration of aflornithine
AU2018260628A1 (en) 2017-04-25 2019-12-12 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
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
US4684728A (en) 1979-01-12 1987-08-04 Bayer Aktiengesellschaft Solubilizing biologically active compounds with reactive hydrogen atoms
EP0317780B1 (en) 1987-11-25 1992-05-20 American Cyanamid Company Sustained (controlled) release delivery system for substituted dihydropyridine calcium channel blockers
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
ES2293638T3 (es) 1994-03-25 2008-03-16 Isotechnika, Inc. Mejora de la eficacia de farmacos por deuteracion.
CN1087348C (zh) 1995-02-03 2002-07-10 巴斯福股份公司 通过酶催化酰化拆分杂原子取代的伯胺和仲胺的外消旋体
DE19523868A1 (de) 1995-06-30 1997-01-02 Huels Chemische Werke Ag Verfahren zur Herstellung von Cyclopropanamin
CN1304058C (zh) 1996-03-12 2007-03-14 Pg-Txl有限公司 水溶性紫杉醇产品
US6441025B2 (en) 1996-03-12 2002-08-27 Pg-Txl Company, L.P. Water soluble paclitaxel derivatives
US6342507B1 (en) 1997-09-05 2002-01-29 Isotechnika, Inc. Deuterated rapamycin compounds, method and uses thereof
AU750245B2 (en) 1997-10-08 2002-07-11 Aurinia Phamaceuticals Inc. Deuterated cyclosporine analogs and their use as immunomodulating agents
DK1087934T3 (da) 1998-04-01 2004-06-28 Cardiome Pharma Corp Aminocyclohexyletherforbindelser og anvendelser deraf
EP1143896B1 (en) 1998-10-20 2006-12-13 The University of North Carolina at Chapel Hill Methods of hydrating the nasal mucosal surface
US7053087B1 (en) 1999-03-04 2006-05-30 Cardiome Pharma Corp. Aminocycloalkyl cinnamide compounds for arrhythmia and 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
WO2003105756A2 (en) 2002-06-14 2003-12-24 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
CA2524034A1 (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
WO2005097087A2 (en) 2004-04-01 2005-10-20 Cardiome Pharma Corp. Merged ion channel modulating compounds and uses thereof
MXPA06011420A (es) * 2004-04-01 2007-04-20 Cardiome Pharma Corp Compuestos pegilados de modulacion de canal de iones.
US7705036B2 (en) 2004-04-01 2010-04-27 Cardiome Pharma Corp. Deuterated aminocyclohexyl ether compounds and processes for preparing same
CA2561819A1 (en) * 2004-04-01 2005-12-01 Cardiome Pharma Corp. Prodrugs of ion channel modulating compounds and uses thereof
US8692002B2 (en) * 2004-11-18 2014-04-08 Cardiome Pharma Corp. Synthetic process for aminocyclohexyl ether compounds
MX2007016248A (es) 2005-06-15 2008-03-07 Cardiome Pharma Corp Procedimiento sintetico para la preparacion de compuestos de eter aminociclohexilico.
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
MX346530B (es) 2017-03-22
EP1915340B1 (en) 2013-08-07
US8080673B2 (en) 2011-12-20
US20120065408A1 (en) 2012-03-15
US7754897B2 (en) 2010-07-13
WO2006138673A3 (en) 2007-03-22
US20100217014A1 (en) 2010-08-26
US20070015924A1 (en) 2007-01-18
BRPI0612138A2 (pt) 2010-10-19
US20120271057A9 (en) 2012-10-25
CA2612375A1 (en) 2006-12-28
BRPI0612138B8 (pt) 2021-05-25
WO2006138673A2 (en) 2006-12-28
EP1915340A2 (en) 2008-04-30
US8618311B2 (en) 2013-12-31
CA2612375C (en) 2013-08-06
JP2008543874A (ja) 2008-12-04
BRPI0612138B1 (pt) 2021-03-16
MX2007016248A (es) 2008-03-07
US20130090483A1 (en) 2013-04-11
US8344162B2 (en) 2013-01-01

Similar Documents

Publication Publication Date Title
US8344162B2 (en) Synthetic processes for the preparation of aminocyclohexyl ether compounds
EP2534140B1 (en) Efficient methods for z- or cis-selective cross-metathesis
WO2002085850A1 (en) Cyclic amidine derivative
EA020815B1 (ru) Ингибиторы вируса гепатита с
JP2009502939A (ja) 新規1−アリール−3−アザビシクロ[3.1.0]ヘキサン:調製および神経精神障害の処理への使用
EP2468724B1 (en) Synthesis of pyrrolidine compounds
EP0486386B1 (fr) Nouveaux dérivés de la N-benzoyl proline, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
WO2003066040A1 (en) Medicinal compositions containing gabapentin or pregabalin and n-type calcium channel antagonist
WO2013160273A1 (en) (3,4-dichloro-phenyl)-((s)-3-propyl-pyrrolidin-3-yl)-methanone hydrochloride and manufacturing processes
CN101277931B (zh) 用于制备氨基环己基醚化合物的合成方法
EP0869952B1 (fr) Derives de 5-naphtalen-1-y1-1,3-dioxanes, leur preparation et leur application en therapeutique
JPH0128019B2 (https=)
EP1076646B1 (de) Verfahren zur stereochemisch kontrollierten herstellung isomerenreiner hochsubstituierter azacyclischer verbindungen
US20070191614A1 (en) Process for producing nitrogenous 5-membered cyclic compound
RU2776802C2 (ru) Способ получения производных 7h-пирроло[2,3-d]пиримидина и промежуточных продуктов для их синтеза
WO2000000458A1 (en) Substituted propionyl derivatives and intermediates thereof
WO2003106423A1 (ja) 環状アミン類およびそれを含む医薬組成物
KR20010013342A (ko) 키랄 3,4-데히드로프롤린의 제조 방법
HK1200818B (en) (3,4-dichloro-phenyl)-((s)-3-propyl-pyrrolidin-3-yl)-methanone hydrochloride and manufacturing processes
HK1172030B (en) Synthesis of pyrrolidine compounds
HK1172030A1 (en) Synthesis of pyrrolidine compounds

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20090602

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20090602

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20090604

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20111228

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20120516

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120814

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120821

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20120824

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20120831

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20121115

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20121129

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20121211

R150 Certificate of patent or registration of utility model

Ref document number: 5159616

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

FPAY Renewal fee payment (event date is renewal date of database)

Free format text: PAYMENT UNTIL: 20151221

Year of fee payment: 3

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

S111 Request for change of ownership or part of ownership

Free format text: JAPANESE INTERMEDIATE CODE: R313113

S531 Written request for registration of change of domicile

Free format text: JAPANESE INTERMEDIATE CODE: R313531

R350 Written notification of registration of transfer

Free format text: JAPANESE INTERMEDIATE CODE: R350

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250

R250 Receipt of annual fees

Free format text: JAPANESE INTERMEDIATE CODE: R250