AR091192A1 - MULTICOMPONENT PROCEDURE FOR THE PREPARATION OF BICYCLE COMPOUNDS - Google Patents

MULTICOMPONENT PROCEDURE FOR THE PREPARATION OF BICYCLE COMPOUNDS

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Publication number
AR091192A1
AR091192A1 ARP130101870A AR091192A1 AR 091192 A1 AR091192 A1 AR 091192A1 AR P130101870 A ARP130101870 A AR P130101870A AR 091192 A1 AR091192 A1 AR 091192A1
Authority
AR
Argentina
Prior art keywords
formula
branched
linear
group
alkyl
Prior art date
Application number
Other languages
Spanish (es)
Inventor
Rasparini Marcello
Riva Renata
Moni Lisa
Banfi Luca
Minelli Cosima
Venegoni Serena
Carcone Luca
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 AR091192A1 publication Critical patent/AR091192A1/en

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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

Abstract

Se describe un procedimiento general, junto con sus posibles variantes, para la producción de los compuestos Telaprevir y Boceprevir. Reivindicación 1: Procedimiento para la preparación de N-acil prolinamidas bicíclicas de fórmula general (1), o sus sales, donde, si n = 0, entonces R⁸ y R⁹ son CH₃, y si n = 1, entonces R⁸ y R⁹ son hidrógeno; comprendiendo dicho procedimiento las siguientes operaciones: a) preparar una d-acilamino-a-hidroxiamida de fórmula (2); b) ciclar una d-acilamino-a-hidroxiamida de fórmula (2) para proporcionar una N-acil prolinamida bicíclica de fórmula (1) de acuerdo con las siguientes etapas: b.1) preparar, partiendo de un compuesto de fórmula (2), una a-activada-d-acilaminoamida de fórmula (3); b.2) ciclar la a-activada-d-acilaminoamida de fórmula (3) para producir la prolinamida de fórmula (1), donde: R² es un resto de fórmula (4); R³ es un resto de fórmula (5), (6) ó (7); R⁵ es alquilo C₁₋₆ lineal o ramificado o un alquilo C₁₋₆ lineal o ramificado sustituido con un alquilo C₁₋₆ cíclico; R¹⁰ es ciclopropilo, o uno de los grupos eliminables del isocianuro convertible; R¹¹ es un grupo saliente capaz de experimentar una sustitución nucleófila; R¹³ es NH₂; NH-Pg; NH-R¹⁴; o un resto de fórmula (8); R¹⁴ es un resto de fórmula (9); R¹⁵ es NH₂; NH-Pg; o NH-R¹⁸; R¹⁶ es OH; OPg; R¹⁷ es hidrógeno o ciclopropilo; R¹⁸ es un resto de fórmula (10); R¹⁹ es OH; un alcoxi C₁₋₆ lineal o ramificado; un alcoxi C₁₋₆ lineal o ramificado sustituido con un arilo C₆₋₁₀; NH-R¹⁰; o NH-R¹⁷; R²⁰ es hidrógeno; un alquilo C₁₋₆ lineal o ramificado; o un alquilo C₁₋₆ lineal o ramificado sustituido con un grupo arilo C₆₋₁₀; y Pg es un grupo protector; en el grupo -OPg en R¹⁶, es un grupo protector alcohol, mientras que en el grupo -NH-Pg en R¹³ o en R¹⁵ es un grupo protector de nitrógeno.A general procedure is described, together with its possible variants, for the production of the Telaprevir and Boceprevir compounds. Claim 1: Process for the preparation of bicyclic N-acyl prolinamides of general formula (1), or its salts, where, if n = 0, then R⁸ and R⁹ are CH₃, and if n = 1, then R⁸ and R⁹ are hydrogen ; said process comprising the following operations: a) preparing a d-acylamino-a-hydroxyamide of formula (2); b) cycling a d-acylamino-a-hydroxyamide of formula (2) to provide a bicyclic N-acyl prolinamide of formula (1) according to the following steps: b.1) preparing, starting from a compound of formula (2 ), an a-activated-d-acylaminoamide of formula (3); b.2) cycling the a-activated-d-acylaminoamide of formula (3) to produce the prolinamide of formula (1), where: R² is a moiety of formula (4); R³ is a residue of formula (5), (6) or (7); R⁵ is linear or branched C₁₋₆ alkyl or a linear or branched C₁₋₆ alkyl substituted with a cyclic C₁₋₆ alkyl; R¹⁰ is cyclopropyl, or one of the removable groups of the convertible isocyanide; R¹¹ is a leaving group capable of undergoing a nucleophilic substitution; R¹³ is NH₂; NH-Pg; NH-R¹⁴; or a remainder of formula (8); R¹⁴ is a remainder of formula (9); R¹⁵ is NH₂; NH-Pg; or NH-R¹⁸; R¹⁶ is OH; OPg; R¹⁷ is hydrogen or cyclopropyl; R¹⁸ is a remainder of formula (10); R¹⁹ is OH; a linear or branched C₁₋₆ alkoxy; a linear or branched C₁₋₆ alkoxy substituted with a C₆₋₁₀ aryl; NH-R¹⁰; or NH-R¹⁷; R²⁰ is hydrogen; a linear or branched C₁₋₆ alkyl; or a linear or branched C₁₋₆ alkyl substituted with a C₆₋₁₀ aryl group; and Pg is a protective group; in the -OPg group in R¹⁶, it is an alcohol protecting group, while in the -NH-Pg group in R¹³ or in R¹⁵ it is a nitrogen protecting group.

ARP130101870 2012-05-30 2013-05-29 MULTICOMPONENT PROCEDURE FOR THE PREPARATION OF BICYCLE COMPOUNDS AR091192A1 (en)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number Publication Date
AR091192A1 true AR091192A1 (en) 2015-01-21

Family

ID=48576982

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP130101870 AR091192A1 (en) 2012-05-30 2013-05-29 MULTICOMPONENT PROCEDURE FOR THE PREPARATION OF BICYCLE COMPOUNDS

Country Status (2)

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

Family Cites Families (11)

* 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
AU2001276988B2 (en) * 2000-07-21 2007-01-25 Dendreon Corporation Peptides as NS3-serine protease inhibitors of hepatitis C virus
SV2003000617A (en) 2000-08-31 2003-01-13 Lilly Co Eli INHIBITORS OF PROTEASA PEPTIDOMIMETICA REF. X-14912M
EP1633711B1 (en) 2003-06-17 2010-11-24 Schering Corporation Process and intermediates for the preparation of (1r,2s,5s)-6,6-dimethyl-3-azabicyclo[3,1,0]hexane-2-carboxylates or salts thereof
TW200518746A (en) 2003-12-11 2005-06-16 Schering Corp Novel inhibitors of hepatitis C virus NS3/NS4A serine protease
WO2005087730A1 (en) 2004-02-27 2005-09-22 Schering Corporation 3,4-(cyclopentyl)-fused proline compounds as inhibitors of hepatitis c virus ns3 serine protease
EP2364970A1 (en) 2005-08-19 2011-09-14 Vertex Pharmaceuticals Incorporated Processes and intermediates
US7723531B2 (en) 2005-12-22 2010-05-25 Schering Corporation Process for the preparation of 6,6-dimethyl-3-azabicyclo-[3.1.0]-hexane compounds and enantiomeric salts thereof
JP2011503231A (en) * 2007-11-20 2011-01-27 コンサート ファーマシューティカルズ インコーポレイテッド Peptides for treatment of HCV infection
WO2010008828A2 (en) 2008-06-24 2010-01-21 Codexis, Inc. Biocatalytic processes for the preparation of substantially stereomerically pure fused bicyclic proline compounds
BR112012021556A2 (en) 2010-02-25 2017-03-21 Ver Voor Christelijk Hoger Onderwijs Wetenschappelijk Onderzoek En Patiëntenzorg process for the preparation of substituted prolyl peptides and similar peptidomimetics

Also Published As

Publication number Publication date
WO2013178682A3 (en) 2014-03-13
WO2013178682A2 (en) 2013-12-05

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