WO2014083575A3 - Improved process for the preparation of boceprevir intermediate - Google Patents

Improved process for the preparation of boceprevir intermediate Download PDF

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Publication number
WO2014083575A3
WO2014083575A3 PCT/IN2013/000697 IN2013000697W WO2014083575A3 WO 2014083575 A3 WO2014083575 A3 WO 2014083575A3 IN 2013000697 W IN2013000697 W IN 2013000697W WO 2014083575 A3 WO2014083575 A3 WO 2014083575A3
Authority
WO
WIPO (PCT)
Prior art keywords
boceprevir
preparation
improved process
hydroxypropionamide
cyclobutylmethyl
Prior art date
Application number
PCT/IN2013/000697
Other languages
French (fr)
Other versions
WO2014083575A2 (en
Inventor
Shankar Rama
Sarat Chandra Srikanth Gorantla
Raja Reddy ANUPATI
Hima Prasad Naidu
Suresh Reddy SABBELLA
Original Assignee
Mylan Laboratories 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 Mylan Laboratories Ltd filed Critical Mylan Laboratories Ltd
Publication of WO2014083575A2 publication Critical patent/WO2014083575A2/en
Publication of WO2014083575A3 publication Critical patent/WO2014083575A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to the process for the preparation of 3-amino-3- cyclobutylmethyl-2-hydroxypropionamide or an acid addition salt thereof and its further conversion into Boceprevir.
PCT/IN2013/000697 2012-11-29 2013-11-14 Improved process for the preparation of boceprevir intermediate WO2014083575A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN4980/CHE/2012 2012-11-29
IN4980CH2012 2012-11-29

Publications (2)

Publication Number Publication Date
WO2014083575A2 WO2014083575A2 (en) 2014-06-05
WO2014083575A3 true WO2014083575A3 (en) 2016-06-02

Family

ID=49956289

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2013/000697 WO2014083575A2 (en) 2012-11-29 2013-11-14 Improved process for the preparation of boceprevir intermediate

Country Status (1)

Country Link
WO (1) WO2014083575A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104744291B (en) * 2015-02-13 2017-01-11 宁波九胜创新医药科技有限公司 N-benzyl-4-cyclobutyl-2-hydroxy-3-nitrobutyrylamide and use thereof
CN112094204B (en) * 2019-06-18 2022-06-21 成都郑源生化科技有限公司 Method for preparing Fmoc-Tyr (tBu) -OH

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050249702A1 (en) * 2004-05-06 2005-11-10 Schering Corporation (1R,2S,5S)-N-[(1S)-3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide as inhibitor of hepatitis C virus NS3/NS4a serine protease
US6992220B2 (en) * 2003-06-17 2006-01-31 Schering Corporation Process and intermediates for the preparation of 3-(amino)-3-cyclobutylmethyl-2-hydroxy-propionamide or salts thereof
US20110034705A1 (en) * 2007-12-21 2011-02-10 Schering-Plough Corporation Process For the Synthesis of 3- Amino-3-Cyclobuthylmethyl-2-Hydroxypropionamide or Salts Thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102372764A (en) 2000-07-21 2012-03-14 先灵公司 Novel peptides as NS3-serine protease inhibitors of hepatitis c virus
JP4955779B2 (en) 2006-12-20 2012-06-20 シェーリング コーポレイション (1R, 2S, 5S) -N-[(1S) -3-Amino-1- (cyclobutylmethyl) -2,3-dioxopropyl] -3-[(2S) -2-[[[(1 , 1-dimethylethyl) amino] carbonyl] -amino] -3,3-dimethyl-1-oxobutyl] -6,6-dimethyl-3-azabicyclo [3.1.0] hexane-2-carboxamide the method of

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6992220B2 (en) * 2003-06-17 2006-01-31 Schering Corporation Process and intermediates for the preparation of 3-(amino)-3-cyclobutylmethyl-2-hydroxy-propionamide or salts thereof
US20050249702A1 (en) * 2004-05-06 2005-11-10 Schering Corporation (1R,2S,5S)-N-[(1S)-3-amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]-3-[(2S)-2-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]-6,6-dimethyl-3-azabicyclo[3.1.0]hexane-2-carboxamide as inhibitor of hepatitis C virus NS3/NS4a serine protease
US20110034705A1 (en) * 2007-12-21 2011-02-10 Schering-Plough Corporation Process For the Synthesis of 3- Amino-3-Cyclobuthylmethyl-2-Hydroxypropionamide or Salts Thereof

Also Published As

Publication number Publication date
WO2014083575A2 (en) 2014-06-05

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