CA2526635C - Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof - Google Patents

Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof Download PDF

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Publication number
CA2526635C
CA2526635C CA2526635A CA2526635A CA2526635C CA 2526635 C CA2526635 C CA 2526635C CA 2526635 A CA2526635 A CA 2526635A CA 2526635 A CA2526635 A CA 2526635A CA 2526635 C CA2526635 C CA 2526635C
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compound
formula
group
process according
salt
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Expired - Fee Related
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CA2526635A
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English (en)
French (fr)
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CA2526635A1 (en
Inventor
Jeonghan Park
Anantha Sudhakar
George S. Wong
Minzhang Chen
Juergen Weber
Xiaojing Yang
Daw-Iong Kwok
Ingyu Jeon
Ramani R. Raghavan
Maria Tamarez
Weidong Tong
Eugene J. Vater
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Merck Sharp and Dohme LLC
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Schering Corp
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Publication of CA2526635C publication Critical patent/CA2526635C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/20—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated the carbon skeleton being saturated and containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/18—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by doubly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA2526635A 2003-06-17 2004-06-15 Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof Expired - Fee Related CA2526635C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US47951603P 2003-06-17 2003-06-17
US60/479,516 2003-06-17
PCT/US2004/019135 WO2004113295A1 (en) 2003-06-17 2004-06-15 Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof

Publications (2)

Publication Number Publication Date
CA2526635A1 CA2526635A1 (en) 2004-12-29
CA2526635C true CA2526635C (en) 2012-06-05

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CA2526635A Expired - Fee Related CA2526635C (en) 2003-06-17 2004-06-15 Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof

Country Status (12)

Country Link
US (3) US7309717B2 (enExample)
EP (1) EP1633711B1 (enExample)
JP (1) JP4825129B2 (enExample)
CN (2) CN101823965B (enExample)
AT (1) ATE489365T1 (enExample)
CA (1) CA2526635C (enExample)
DE (1) DE602004030239D1 (enExample)
ES (1) ES2354817T3 (enExample)
MX (1) MXPA05013752A (enExample)
SG (1) SG180022A1 (enExample)
WO (1) WO2004113295A1 (enExample)
ZA (1) ZA201006378B (enExample)

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US20060276407A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis C virus
US20070237818A1 (en) * 2005-06-02 2007-10-11 Malcolm Bruce A Controlled-release formulation of HCV protease inhibitor and methods using the same
EP1898941A2 (en) * 2005-06-02 2008-03-19 Schering Corporation Controlled-release formulation useful for treating disorders associated with hepatitis c virus
US20060281689A1 (en) * 2005-06-02 2006-12-14 Schering Corporation Method for modulating activity of HCV protease through use of a novel HCV protease inhibitor to reduce duration of treatment period
US8119602B2 (en) 2005-06-02 2012-02-21 Schering Corporation Administration of HCV protease inhibitors in combination with food to improve bioavailability
ES2572980T3 (es) * 2005-06-02 2016-06-03 Merck Sharp & Dohme Corp. Combinación de inhibidores de la proteasa del VHC con un tensioactivo
WO2006130666A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Medicaments and methods combining a hcv protease inhibitor and an akr competitor
WO2006130687A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Liver/plasma concentration ratio for dosing hepatitis c virus protease inhibitor
WO2006130552A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis c virus
AR056805A1 (es) * 2005-11-14 2007-10-24 Schering Corp Un proceso para oxidacion para la preparcion de n- (3- amino-1- ( ciclobutilmetil) -2,3- dioxopropil ) -3-(n-(( ter-butilamino) carbonil )-3- metil- l- valil) -6,6- dimetil-3- azabiciclo (3.1.0) hexano -2- carboxamida y compuestos ralacionados
WO2007075790A1 (en) * 2005-12-22 2007-07-05 Schering Corporation Process for the preparation of 6, 6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof
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WO2007122744A1 (ja) 2006-04-17 2007-11-01 Sumitomo Chemical Company, Limited 多環式プロリン誘導体又はその酸付加塩の製造方法
CN101415676A (zh) 2006-04-17 2009-04-22 住友化学株式会社 N-叔丁氧基羰基-2-吡咯烷酮类及其制造方法
JP5272324B2 (ja) * 2006-04-17 2013-08-28 住友化学株式会社 Ｎ−ｔｅｒｔ−ブトキシカルボニル−２−ピロリジノン類およびその製造方法
JP5272325B2 (ja) * 2006-04-17 2013-08-28 住友化学株式会社 多環式プロリン誘導体またはその酸付加塩の製造方法
SG160363A1 (en) 2006-04-17 2010-04-29 Sumitomo Chemical Company Limt Ester of cyclic carboxylic acid
JP2010513492A (ja) * 2006-12-19 2010-04-30 シェーリング コーポレイション ３−（アミノ）−３−（シクロブチルメチル）−２−（ヒドロキシ）−プロピオンアミド塩酸塩の調製
JP5095824B2 (ja) 2007-10-10 2012-12-12 ノバルティス アーゲー スピロピロリジン類およびｈｃｖおよびｈｉｖ感染に対するその使用
WO2009073380A1 (en) * 2007-11-28 2009-06-11 Schering Corporation Dehydrohalogenation process for the preparation of intermediates useful in providing 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds
US20110137046A1 (en) * 2008-06-05 2011-06-09 Fen-Er Chen Preparation method of (4s,5r)-semiester
CN102816106A (zh) 2008-06-24 2012-12-12 默沙东公司 用于制备基本上立体异构纯的稠合二环脯氨酸化合物的生物催化方法
US8188137B2 (en) 2008-08-15 2012-05-29 Avila Therapeutics, Inc. HCV protease inhibitors and uses thereof
JP5613168B2 (ja) * 2008-11-17 2014-10-22 アナディス ファーマシューティカルズ インク デオキシリボフラノース化合物の製造方法
US8512690B2 (en) 2009-04-10 2013-08-20 Novartis Ag Derivatised proline containing peptide compounds as protease inhibitors
CN101863866B (zh) * 2009-04-16 2012-07-04 上海联友制药技术有限公司 3,3-二甲基环丙烷-1,2-二甲酸酐的合成方法
WO2011014494A1 (en) 2009-07-29 2011-02-03 Schering Corporation ENANTIO- AND STEREO-SPECIFIC SYNTHESES OF β-AMINO-α- HYDROXY AMIDES
CN102070575B (zh) * 2010-12-28 2012-10-17 上海北卡医药技术有限公司 卡隆酸酐的合成方法
CN102127040B (zh) * 2010-12-30 2013-05-01 西安彩晶光电科技股份有限公司 6,6-二甲基-3-氧杂双环[3.1.0]己烷-2,4-二酮的制备方法
FR2972453B1 (fr) * 2011-03-09 2013-11-29 Minakem Nouveau procede de synthese du (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxylate de methyle ou de l'un de ses sels
JP2013010738A (ja) * 2011-05-31 2013-01-17 Sumitomo Chemical Co Ltd エステル化合物の製造方法
JP2013010732A (ja) * 2011-06-03 2013-01-17 Sumitomo Chemical Co Ltd プロリン化合物の製造方法
JP2013010733A (ja) * 2011-06-03 2013-01-17 Sumitomo Chemical Co Ltd ヘミアミナール化合物の製造方法及びシアノアミン化合物の製造方法
JP2013010734A (ja) * 2011-06-03 2013-01-17 Sumitomo Chemical Co Ltd Ｎ−置換ラクタム化合物の製造方法
WO2013178682A2 (en) 2012-05-30 2013-12-05 Chemo Ibérica, S.A. Multicomponent process for the preparation of bicyclic compounds
CN103435532B (zh) * 2013-09-02 2015-07-08 苏州永健生物医药有限公司 波普瑞韦中间体的合成方法
CN104151279A (zh) * 2014-08-26 2014-11-19 广西梧松林化集团有限公司 卡龙酸酐的合成方法
CN114539125B (zh) * 2022-03-07 2024-02-09 杭州国瑞生物科技有限公司 一种帕西洛韦中间体的合成方法
CN114478690B (zh) * 2022-03-08 2024-01-02 新发药业有限公司 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷衍生物的制备方法
WO2023175526A1 (en) * 2022-03-16 2023-09-21 Laurus Labs Limited Process for preparation of azabicyclo [3.1.0] hexane intermediates
CN114605309B (zh) * 2022-03-23 2023-07-21 浙江新和成股份有限公司 一种氮杂双环衍生物的合成方法
CN114989067B (zh) * 2022-07-18 2022-10-28 苏州奥普拓新材料有限公司 一种帕罗韦德中间体的合成方法
CN115947679B (zh) * 2022-12-16 2024-06-07 杭州澳赛诺生物科技有限公司 一种6,6-二甲基-3-杂氮-双环[3.1.0]己烷-2-羧酸甲酯的合成方法

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Also Published As

Publication number Publication date
US7728165B2 (en) 2010-06-01
US20050059648A1 (en) 2005-03-17
CN1805931A (zh) 2006-07-19
MXPA05013752A (es) 2006-03-08
CN101823965B (zh) 2012-12-19
EP1633711A1 (en) 2006-03-15
EP1633711B1 (en) 2010-11-24
HK1081199A1 (en) 2006-05-12
JP4825129B2 (ja) 2011-11-30
WO2004113295A1 (en) 2004-12-29
ES2354817T3 (es) 2011-03-18
CN1805931B (zh) 2010-06-23
US7309717B2 (en) 2007-12-18
CA2526635A1 (en) 2004-12-29
US20080114179A1 (en) 2008-05-15
SG180022A1 (en) 2012-05-30
US20090247784A1 (en) 2009-10-01
DE602004030239D1 (de) 2011-01-05
CN101823965A (zh) 2010-09-08
JP2007520434A (ja) 2007-07-26
ATE489365T1 (de) 2010-12-15
US7569705B2 (en) 2009-08-04
ZA201006378B (en) 2011-05-25

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