AR044018A1 - Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril - Google Patents

Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril

Info

Publication number
AR044018A1
AR044018A1 ARP040101247A ARP040101247A AR044018A1 AR 044018 A1 AR044018 A1 AR 044018A1 AR P040101247 A ARP040101247 A AR P040101247A AR P040101247 A ARP040101247 A AR P040101247A AR 044018 A1 AR044018 A1 AR 044018A1
Authority
AR
Argentina
Prior art keywords
formula
compound
synthesis
defined above
linear
Prior art date
Application number
ARP040101247A
Other languages
English (en)
Inventor
Thierry Dubuffet
Pascal Langlois
Original Assignee
Servier Lab
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 Servier Lab filed Critical Servier Lab
Publication of AR044018A1 publication Critical patent/AR044018A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/022—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2
    • C07K5/0222—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -X-C(=O)-(C)n-N-C-C(=O)-Y-; X and Y being heteroatoms; n being 1 or 2 with the first amino acid being heterocyclic, e.g. Pro, Trp
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/20—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/22—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated the carbon skeleton being further substituted by oxygen atoms
    • 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
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cardiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Heart & Thoracic Surgery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

Procedimiento para la síntesis de compuestos, aplicables en la síntesis de perindopril y sales farmacéuticamente aceptables del mismo. Reivindicación 1: Procedimiento para la síntesis de compuestos de fórmula (1), donde R representa un átomo de hidrógeno o un grupo bencilo o alquilo (C1-6) lineal o ramificado, caracterizado porque la (L)-serina protegida de fórmula (2), donde R1 representa un grupo bencilo o alquilo (C1-6) lineal o ramificado, se condensa con un compuesto de fórmula (3), donde Ar representa un grupo fenilo opcionalmente sustituido por uno o más grupos alquilo (C1-6) lineal o ramificado o un grupo naftilo, para obtener un compuesto de fórmula (4), donde Ar y R1 son tal como se han definido anteriormente, que se somete a reducción diastereoselectiva para obtener un compuesto de fórmula (5), donde Ar y R1 son tal como se han definido anteriormente, que se condensa con ciclohexanona para obtener un compuesto de fórmula (6), donde Ar y R1 son tal como se han definido anteriormente, que se convierte por halogenación en un compuesto de fórmula (7), donde Ar y R1 son tal como se han definido anteriormente y X representa un átomo de cloro, bromo o yodo, que se somete a ciclización de radicales libres por tratamiento con hidruro de n-tributilestaño, en presencia de un iniciador de radicales libres, para obtener un compuesto de fórmula (8), donde Ar y R1 son tal como se han definido anteriormente, la función amina y, si se desea, la función ácido del mismo se desprotegen para obtener el compuesto de fórmula (1).
ARP040101247A 2003-04-15 2004-04-14 Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril AR044018A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP03290931A EP1354874B1 (fr) 2003-04-15 2003-04-15 Nouveau procédé de synthèse de l'acide (2s, 3aS, 7aS)-perhydroindole-2-carboxylique et de ses esters, et application a la synthèse du perindopril

Publications (1)

Publication Number Publication Date
AR044018A1 true AR044018A1 (es) 2005-08-24

Family

ID=28459640

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP040101247A AR044018A1 (es) 2003-04-15 2004-04-14 Procedimiento para la sintesis del acido (2s,3as,7as)-perhidroindol-2-carboxilico y esteres del mismo, y aplicacion en la sintesis de perindopril

Country Status (10)

Country Link
EP (1) EP1354874B1 (es)
AR (1) AR044018A1 (es)
AT (1) ATE283257T1 (es)
DE (1) DE60300166T2 (es)
DK (1) DK1354874T3 (es)
ES (1) ES2233913T3 (es)
MY (1) MY136549A (es)
PT (1) PT1354874E (es)
SI (1) SI1354874T1 (es)
WO (1) WO2004092133A1 (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100391945C (zh) * 2005-05-31 2008-06-04 浙江大学 一种s-(-)-吲哚啉-2-羧酸的合成方法
RU2012103753A (ru) * 2009-07-16 2013-08-27 Эбботт Лабораториз Способ синтеза (2s, 3ar, 7as)-октагидро-1н-индол-карбоновой кислоты в качестве промежуточного соединения для получения трандолаприла

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ202903A (en) * 1981-12-29 1988-01-08 Hoechst Ag 1-- pe pyrrol-2-yl-carboxylic acid derivatives and pharmaceutical compositions
FR2620703B1 (fr) * 1987-09-17 1991-10-04 Adir Procede de synthese industrielle de l'acide perhydroindole carboxylique - 2(2s, 3as, 7as). application a la synthese de carboxyalkyl dipeptides

Also Published As

Publication number Publication date
EP1354874B1 (fr) 2004-11-24
PT1354874E (pt) 2005-03-31
ES2233913T3 (es) 2005-06-16
EP1354874A1 (fr) 2003-10-22
SI1354874T1 (en) 2005-04-30
ATE283257T1 (de) 2004-12-15
MY136549A (en) 2008-10-31
DE60300166D1 (de) 2004-12-30
DK1354874T3 (da) 2005-03-14
DE60300166T2 (de) 2005-12-01
WO2004092133A1 (fr) 2004-10-28

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