WO2013178682A3 - Procédé à multicomposants pour la préparation de composés bicycliques - Google Patents

Procédé à multicomposants pour la préparation de composés bicycliques Download PDF

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Publication number
WO2013178682A3
WO2013178682A3 PCT/EP2013/061073 EP2013061073W WO2013178682A3 WO 2013178682 A3 WO2013178682 A3 WO 2013178682A3 EP 2013061073 W EP2013061073 W EP 2013061073W WO 2013178682 A3 WO2013178682 A3 WO 2013178682A3
Authority
WO
WIPO (PCT)
Prior art keywords
preparation
bicyclic compounds
multicomponent process
multicomponent
compounds
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.)
Ceased
Application number
PCT/EP2013/061073
Other languages
English (en)
Other versions
WO2013178682A2 (fr
Inventor
Renata Riva
Lisa MONI
Luca Banfi
Marcello Rasparini
Luca Carcone
Cosima MINELLI
Serena Venegoni
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.)
Chemo Iberica SA
Original Assignee
Chemo Iberica SA
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 Chemo Iberica SA filed Critical Chemo Iberica SA
Publication of WO2013178682A2 publication Critical patent/WO2013178682A2/fr
Publication of WO2013178682A3 publication Critical patent/WO2013178682A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C247/00—Compounds containing azido groups
    • C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C247/12—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • C07C271/22—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 carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C291/00—Compounds containing carbon and nitrogen and having functional groups not covered by groups C07C201/00 - C07C281/00
    • C07C291/10—Isocyanides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • 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
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Genetics & Genomics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biophysics (AREA)
  • Toxicology (AREA)
  • Biochemistry (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

La présente invention concerne un procédé général, ainsi que ses variantes possibles, pour la production des composés Télaprévir (I) et Bocéprevir (II).
PCT/EP2013/061073 2012-05-30 2013-05-29 Procédé à multicomposants pour la préparation de composés bicycliques Ceased WO2013178682A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12382216 2012-05-30
EP12382216.5 2012-05-30

Publications (2)

Publication Number Publication Date
WO2013178682A2 WO2013178682A2 (fr) 2013-12-05
WO2013178682A3 true WO2013178682A3 (fr) 2014-03-13

Family

ID=48576982

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2013/061073 Ceased WO2013178682A2 (fr) 2012-05-30 2013-05-29 Procédé à multicomposants pour la préparation de composés bicycliques

Country Status (2)

Country Link
AR (1) AR091192A1 (fr)
WO (1) WO2013178682A2 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002008244A2 (fr) * 2000-07-21 2002-01-31 Schering Corporation Nouveau peptide sous forme d'inhibiteurs de protease a serine ns3 d'hepatite virale c
WO2004113295A1 (fr) * 2003-06-17 2004-12-29 Schering Corporation Procede et intermediaires de preparation de (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates ou sels de ces derniers
WO2007022459A2 (fr) * 2005-08-19 2007-02-22 Vertex Pharmaceuticals Incorporated Procedes et intermediaires
WO2009067225A2 (fr) * 2007-11-20 2009-05-28 Concert Pharmaceuticals, Inc. Peptides pour le traitement d'infections par le vhc

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7244721B2 (en) 2000-07-21 2007-07-17 Schering Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
SV2003000617A (es) 2000-08-31 2003-01-13 Lilly Co Eli Inhibidores de la proteasa peptidomimetica ref. x-14912m
WO2005058821A1 (fr) 2003-12-11 2005-06-30 Schering Corporation Inhibiteurs de la protease serine ns3/ns4a du virus de l'hepatite c (hcv)
EP1737821B1 (fr) 2004-02-27 2009-08-05 Schering Corporation Composes de proline fusionnes a 3,4-(cyclopentyl) en tant qu'inhibiteurs de la protease serine ns3 du virus de l'hepatite c
WO2007075790A1 (fr) 2005-12-22 2007-07-05 Schering Corporation Procede pour la preparation de composes 6, 6-dimethyl-3-azabicyclo-[3.1.0]-hexane et leurs sels enantiomeriques
MX2010014500A (es) 2008-06-24 2011-05-30 Codexis Inc Procedimientos biocataliticos para la preparacion de compuestos de prolina biciclica fusionada sustancialmente estereomericamente puros.
US8686145B2 (en) 2010-02-25 2014-04-01 Vereniging Voor Christelijk Hoger Onderwijs, Wetenschappelijk Onderzoek en Patientenzorg C/O Technology Transfer Officer VU & Vumc Process for the preparation of α-acyloxy β-formamido amides

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002008244A2 (fr) * 2000-07-21 2002-01-31 Schering Corporation Nouveau peptide sous forme d'inhibiteurs de protease a serine ns3 d'hepatite virale c
WO2004113295A1 (fr) * 2003-06-17 2004-12-29 Schering Corporation Procede et intermediaires de preparation de (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates ou sels de ces derniers
WO2007022459A2 (fr) * 2005-08-19 2007-02-22 Vertex Pharmaceuticals Incorporated Procedes et intermediaires
WO2009067225A2 (fr) * 2007-11-20 2009-05-28 Concert Pharmaceuticals, Inc. Peptides pour le traitement d'infections par le vhc

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ANASS ZNABET ET AL: "A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions", CHEMICAL COMMUNICATIONS, vol. 46, no. 42, 1 January 2010 (2010-01-01), pages 7918, XP055027224, ISSN: 1359-7345, DOI: 10.1039/c0cc02823a *
TAO LI ET AL: "Efficient, Chemoenzymatic Process for Manufacture of the Boceprevir Bicyclic [3.1.0]Proline Intermediate Based on Amine Oxidase-Catalyzed Desymmetrization", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 134, no. 14, 11 April 2012 (2012-04-11), pages 6467 - 6472, XP055027044, ISSN: 0002-7863, DOI: 10.1021/ja3010495 *

Also Published As

Publication number Publication date
AR091192A1 (es) 2015-01-21
WO2013178682A2 (fr) 2013-12-05

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