CA2383298A1 - Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent - Google Patents

Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Download PDF

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Publication number
CA2383298A1
CA2383298A1 CA002383298A CA2383298A CA2383298A1 CA 2383298 A1 CA2383298 A1 CA 2383298A1 CA 002383298 A CA002383298 A CA 002383298A CA 2383298 A CA2383298 A CA 2383298A CA 2383298 A1 CA2383298 A1 CA 2383298A1
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CA
Canada
Prior art keywords
group
amino acids
nitro
formula
contain
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Granted
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CA002383298A
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English (en)
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CA2383298C (fr
Inventor
Guillaume De Nanteuil
Bernard Portevin
Alain Benoist
Nigel Levens
Olivier Nosjean
Bernadette Husson-Robert
Michelle Boulanger
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Laboratoires Servier SAS
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Laboratoires Servier SAS
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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
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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

Abstract

L'invention concerne de nouveaux composés répondant à la formule (I) (voir formule I) dans laquelle (voir formule II) représente un hétérocycle à 5 chaînons; Ak représente une chaîne alkylène ; X représente une liaison simple ou un groupement phényl~;ne ; R1 et R2, identiques ou différents, représentent chacun un atome d'hydrogène ou un groupement alkyle ; Y représente un groupement CHNO2 ou NR4 dans lequel R4 représente un atome d'hydrogène ou un groupement alkyle ; et R1 représente soit un groupement alkyle, nitro ou cyano, lorsque Y représente CHNO2, soit un groupement nitro ou cyano, lorsque Y représente NR4 ; sous réserve que , lorsque (voir formule III) représente un hétérocycl e azoté à 5 chaînons non substitués, Ak représente un groupement -(CH2)3-, X représente une liaison simple et Y représente NH, R3 ne peut représenter un groupement nitro. L'invention vise également des tautomères et isomères optiques des composés de formule (I), ainsi que leurs sels d'addition à un acide pharmaceutiquement acceptable. Les composés selon l'invention sont utiles en tant qu'inhibiteurs de dipeptidyl-peptidase IV, dans le traitement de l'intolérance au glucose et des maladies associées à l'hyperglycémie.
CA002383298A 2001-05-15 2002-05-10 Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent Expired - Fee Related CA2383298C (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0106375A FR2824825B1 (fr) 2001-05-15 2001-05-15 Nouveaux derives d'alpha-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR01.06375 2001-05-15

Publications (2)

Publication Number Publication Date
CA2383298A1 true CA2383298A1 (fr) 2002-11-15
CA2383298C CA2383298C (fr) 2008-01-29

Family

ID=8863284

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002383298A Expired - Fee Related CA2383298C (fr) 2001-05-15 2002-05-10 Nouveaux derives d'.alpha.-amino-acides, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Country Status (25)

Country Link
US (1) US6706742B2 (fr)
EP (1) EP1258476B1 (fr)
JP (1) JP3798337B2 (fr)
KR (1) KR100460782B1 (fr)
CN (1) CN1164573C (fr)
AR (1) AR033735A1 (fr)
AT (1) ATE331705T1 (fr)
AU (1) AU780480B2 (fr)
BR (1) BR0201697A (fr)
CA (1) CA2383298C (fr)
CY (1) CY1105385T1 (fr)
DE (1) DE60212759T2 (fr)
DK (1) DK1258476T3 (fr)
EA (1) EA004865B1 (fr)
ES (1) ES2266422T3 (fr)
FR (1) FR2824825B1 (fr)
HK (1) HK1050526A1 (fr)
HU (1) HUP0201646A3 (fr)
MX (1) MXPA02004642A (fr)
NO (1) NO322569B1 (fr)
NZ (1) NZ518948A (fr)
PL (1) PL353910A1 (fr)
PT (1) PT1258476E (fr)
SI (1) SI1258476T1 (fr)
ZA (1) ZA200203867B (fr)

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