WO2003045369A3 - Utilisation des isomeres l de derives aminoacides de l'hydroxyguanidine pour la protection localisee de no - Google Patents

Utilisation des isomeres l de derives aminoacides de l'hydroxyguanidine pour la protection localisee de no Download PDF

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Publication number
WO2003045369A3
WO2003045369A3 PCT/FR2002/004117 FR0204117W WO03045369A3 WO 2003045369 A3 WO2003045369 A3 WO 2003045369A3 FR 0204117 W FR0204117 W FR 0204117W WO 03045369 A3 WO03045369 A3 WO 03045369A3
Authority
WO
WIPO (PCT)
Prior art keywords
producing
nitrogen monoxide
hydroxyguanidine
isomers
amino acid
Prior art date
Application number
PCT/FR2002/004117
Other languages
English (en)
Other versions
WO2003045369A9 (fr
WO2003045369A2 (fr
Inventor
Petra Beranova
Andrei Klechtchev
Bernard Muller
Christa Schott
Jean-Claude Stoclet
Sylvie Dijols
Jean-Luc Boucher
Daniel Mansuy
Original Assignee
Universte Louis Pasteur Etabli
Centre Nat Rech Scient
Univ Paris Descartes
Petra Beranova
Andrei Klechtchev
Bernard Muller
Christa Schott
Jean-Claude Stoclet
Sylvie Dijols
Jean-Luc Boucher
Daniel Mansuy
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 Universte Louis Pasteur Etabli, Centre Nat Rech Scient, Univ Paris Descartes, Petra Beranova, Andrei Klechtchev, Bernard Muller, Christa Schott, Jean-Claude Stoclet, Sylvie Dijols, Jean-Luc Boucher, Daniel Mansuy filed Critical Universte Louis Pasteur Etabli
Priority to AU2002364804A priority Critical patent/AU2002364804A1/en
Publication of WO2003045369A2 publication Critical patent/WO2003045369A2/fr
Publication of WO2003045369A3 publication Critical patent/WO2003045369A3/fr
Publication of WO2003045369A9 publication Critical patent/WO2003045369A9/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Utilisation des isomères L de dérivés aminoacides de l'hydroxyguanidine pour la production de NO, compositions pharmaceutiques les contenant et utilisations pharmaceutiques La présente invention concerne le domaine de la chimie organique de synthèse appliquée au domaine pharmaceutique et a pour objet l'utilisation de l'isomère L d'un composé de formule générale (I) où m est un entier compris entre 0 et 4 (bornes incluses) pour la production localisée, in situ et in vivo dans les tuniques des vaisseaux sanguins chez l'homme ou chez l'animal, de monoxyde d'azote (NO) sous la forme de NO+ (ion nitrosonium), NO- (ion nitroxyle) ou NO* (NO radicalaire), d'un précurseur de monoxyde d'azote ou d'un dérivé résultant de l'interaction dudit monoxyde d'azote avec ses cibles biologiques. L'invention est particulièrement applicable pour l'obtention de nouveaux médicaments, notamment pour l'obtention d'un médicament destiné à prévenir ou à traiter une déficience, lésion ou absence de l'endothélium vasculaire.
PCT/FR2002/004117 2001-11-29 2002-11-29 Utilisation des isomeres l de derives aminoacides de l'hydroxyguanidine pour la protection localisee de no WO2003045369A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2002364804A AU2002364804A1 (en) 2001-11-29 2002-11-29 Use of l isomers of amino acid derivatives of hydroxyguanidine for producing no, pharmaceutical compositions containing same and pharmaceutical uses

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0115457A FR2832634A1 (fr) 2001-11-29 2001-11-29 Utilisation des isomeres l de derives aminoacides de l'hydroxyguanidine pour la production de no, compositions pharmaceutiques les contenant et utilisations pharmaceutiques
FR0115457 2001-11-29

Publications (3)

Publication Number Publication Date
WO2003045369A2 WO2003045369A2 (fr) 2003-06-05
WO2003045369A3 true WO2003045369A3 (fr) 2004-06-03
WO2003045369A9 WO2003045369A9 (fr) 2004-07-01

Family

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PCT/FR2002/004117 WO2003045369A2 (fr) 2001-11-29 2002-11-29 Utilisation des isomeres l de derives aminoacides de l'hydroxyguanidine pour la protection localisee de no

Country Status (3)

Country Link
AU (1) AU2002364804A1 (fr)
FR (1) FR2832634A1 (fr)
WO (1) WO2003045369A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2424515B1 (fr) 2009-01-09 2017-03-22 Christian-Albrechts-Universität zu Kiel Dérivés de n omega-hydroxy-l-arginine pour le traitement de maladies
US20110160200A1 (en) * 2009-11-23 2011-06-30 Cardioxyl Pharmaceuticals, Inc. Nitroxyl Progenitors for the Treatment of Pulmonary Hypertension
AU2010328230B2 (en) 2009-12-07 2016-06-02 Cardioxyl Pharmaceuticals, Inc. Bis-acylated hydroxylamine derivatives

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998058633A2 (fr) * 1997-06-23 1998-12-30 Queen's University At Kingston Traitement par administration de microdoses
WO2001032167A1 (fr) * 1999-10-26 2001-05-10 Nitromed, Inc. Synthese de l'acide nitrique endogene dans des conditions de basse tension en oxygene
AU1439301A (en) * 1999-10-29 2001-05-30 Nitromed, Inc. Methods of treating vascular diseases characterized by nitric oxide insufficiency
WO2001078717A1 (fr) * 2000-04-12 2001-10-25 Cornell Research Foundation, Inc. Pharmacotherapie pour dysfonction vasculaire associee a la bioactivite deficiente de l'oxyde nitrique
WO2001089519A1 (fr) * 2000-05-22 2001-11-29 Nitromed, Inc. Inhibiteurs de thromboxane, compositions, procedes d'utilisation et applications correspondantes
WO2002034303A1 (fr) * 2000-10-27 2002-05-02 Nitromed, Inc. Methodes de traitement de maladies vasculaires caracterisees par une insuffisance en monoxyde d'azote

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998058633A2 (fr) * 1997-06-23 1998-12-30 Queen's University At Kingston Traitement par administration de microdoses
WO2001032167A1 (fr) * 1999-10-26 2001-05-10 Nitromed, Inc. Synthese de l'acide nitrique endogene dans des conditions de basse tension en oxygene
AU1439301A (en) * 1999-10-29 2001-05-30 Nitromed, Inc. Methods of treating vascular diseases characterized by nitric oxide insufficiency
WO2001078717A1 (fr) * 2000-04-12 2001-10-25 Cornell Research Foundation, Inc. Pharmacotherapie pour dysfonction vasculaire associee a la bioactivite deficiente de l'oxyde nitrique
WO2001089519A1 (fr) * 2000-05-22 2001-11-29 Nitromed, Inc. Inhibiteurs de thromboxane, compositions, procedes d'utilisation et applications correspondantes
WO2002034303A1 (fr) * 2000-10-27 2002-05-02 Nitromed, Inc. Methodes de traitement de maladies vasculaires caracterisees par une insuffisance en monoxyde d'azote

Non-Patent Citations (26)

* Cited by examiner, † Cited by third party
Title
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BOTTING ET AL.: "The many function sof nitric oxide", DRUG NEWS PERSPECTIVES, vol. 1993, no. 6, 1910, pages 733 - 736, XP008016959 *
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DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; February 2000 (2000-02-01), MULLER B ET AL: "Inducible NO synthase activity in blood vessels and heart: New insight into cell origin and consequences.", XP002211487, Database accession no. PREV200000164530 *
DATABASE BIOSIS [online] BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US; July 1998 (1998-07-01), STOCLET J -C ET AL: "Overproduction of nitric oxide in pathophysiology of blood vessels.", XP002211485, Database accession no. PREV199800492352 *
DATABASE MEDLINE [online] June 1998 (1998-06-01), KLESCHYOV A L ET AL: "Role of adventitial nitric oxide in vascular hyporeactivity induced by lipopolysaccharide in rat aorta.", XP002211484, Database accession no. NLM9690852 *
GARLICHS C D ET AL: "DECREASED PLASMA CONCENTRATIONS OF L-HYDROXY-ARGININE AS A MARKER OF REDUCED NO FORMATION IN PATIENTS WITH COMBINED CARDIOVASCULAR RISK FACTORS", JOURNAL OF LABORATORY AND CLINICAL MEDICINE, ST. LOUIS, MO, US, vol. 5, no. 135, May 2000 (2000-05-01), pages 419 - 425, XP008004793, ISSN: 0022-2143 *
HECKER M ET AL: "NG-HYDROXY-L-ARGININE: A NITRIC OXIDE SYNTHASE-INDEPENDENT VASODILATOR AND POTENTIAL INTERCELLULAR NITRIC OXIDE CARRIER", BIOLOGY OF NITRIC OXIDE, XX, XX, no. 2, 1992, pages 128 - 130, XP008004749 *
KERWIN J F ET AL: "NITRIC OXIDE: A NEW PARADIGM FOR SECOND MESSENGERS", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 22, no. 38, 27 October 1995 (1995-10-27), pages 4343 - 4362, XP001073968, ISSN: 0022-2623 *
MOALI ET AL.: "OXIDATIONS OF NG-HYDROXYARGININE ANALOGUES AND VARIOUS N-HYDROXYGUANIDINES NY NO-SYNTHASE II: KEY ROLE OF TETRAHYDROBIOPTERIN IN THE REACTION MECHANISM AND SUSTRATE SELECTIVITY", CHEM. RES. TOXICOL., vol. 14, no. 2, February 2001 (2001-02-01), pages 202 - 210, XP002211483 *
MODOLELL M ET AL: "OXIDATION OF NG-HYDROXYL-L-ARGININE TO NITRIC OXIDE MEDIATED BY RESPIRATORY BURST: AN ALTERNATIVE PATHWAY TO NO SYNTHESIS", FEBS LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 2/3, no. 401, 1997, pages 123 - 126, XP001073975, ISSN: 0014-5793 *
PHYSIOLOGICAL RESEARCH., vol. 49, no. 1, February 2000 (2000-02-01), pages 19 - 26, ISSN: 0862-8408 *
SAKAMAKI T ET AL: "SYNTHETIC NOMEGA-HYDROXY-L-ARGININE CAUSES ENDOTHELIUM-DEPENDENT VASCULAR RELAXATION BOTH IN VITRO AND IN VIVO", JOURNAL OF SMOOTH MUSCLE RESEARCH, NIHON HEIKATSUKIN GAKKAI, HIROSAKI,, JP, vol. 6, no. 31, December 1995 (1995-12-01), pages 439 - 443, XP008004798, ISSN: 0916-8737 *
SCHOTT C A ET AL: "EXOGENOUS NG-HYDROXY-L-ARGININE CAUSES NITRITE PRODUCTION IN VASCULAR SMOOTH MUSCLE CELLS IN THE ABSENCE OF NITRIC OXIDE SYNTHASE ACTIVITY", FEBS LETTERS, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 2/3, no. 341, 21 March 1994 (1994-03-21), pages 203 - 207, XP001073964, ISSN: 0014-5793 *
STOCLET ET AL.: "THE INDUCIBLE NITRIC OXIDE SYNTHASE IN VASCULAR AND CARDIAC TISSUE", EUR. J. PHARMACOL., vol. 375, no. 1-3, 30 June 1999 (1999-06-30), pages 139 - 155, XP001104514 *
SWIERKOSZ T A ET AL: "NG-HYDROXY-L-ARGININE RELEASES FROM ENDOTHELIAL CELLS NITRIC OXIDE WHICH INCREASES CGMP IN RFL-6 FIBROBLASTS", ENDOTHELIUM, HARWOOD ACADEMIC PUBLISHERS, CH, vol. 2, no. 3, 1995, pages 121 - 129, XP008004795, ISSN: 1062-3329 *
SWIERKOSZ T A ET AL: "THE NATURE OF ENDOTHELIAL CELL-DEPENDENT VASORELAXATIONS INDUCED BY NG-HYDROXY-L-ARGININE", BRITISH JOURNAL OF PHARMACOLOGY, BASINGSTOKE, HANTS, GB, vol. SUPPL, no. 107, October 1992 (1992-10-01), pages 80P, XP008004739, ISSN: 0007-1188 *
VETROVSKY P ET AL: "NITROGEN(II) OXIDE (NITRIC OXIDE, NO): ITS ORIGIN, FATE AND PHYSIOLOGICAL SIGNIFICANCE. A REVIEW", COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, ACADEMIC PRESS, LONDON, GB, vol. 9, no. 62, 1997, pages 1355 - 1383, XP001073967, ISSN: 0010-0765 *
WALDER C E ET AL: "NG-HYDROXY-L-ARGININE PREVENTS THE HAEMODYNAMIC EFFECTS OF NITRIC OXIDE SYNTHESIS INHIBITION IN THE ANAESTHETIZED RAT", BRITISH JOURNAL OF PHARMACOLOGY, BASINGSTOKE, HANTS, GB, vol. 2, no. 107, October 1992 (1992-10-01), pages 476 - 480, XP008004742, ISSN: 0007-1188 *
WALLACE G C ET AL: "NOMEGA-HYDROXY-L-ARGININE: A NOVEL ARGININE ANALOG CAPABLE OF CAUSING VASORELAXATION IN BOVINE INTRAPULMONARY ARTERY", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, ACADEMIC PRESS INC. ORLANDO, FL, US, vol. 1, no. 176, 15 April 1991 (1991-04-15), pages 528 - 534, XP001073965, ISSN: 0006-291X *
ZEMBOWICZ A ET AL: "MECHANISMS OF THE ENDOTHELIUM-DEPENDENT RELAXATION INDUCED BY NG-HYDROXY-L-ARGININE", JOURNAL OF CARDIOVASCULAR PHARMACOLOGY, NEW YORK, NY, US, vol. SUPPL. 12, no. 20, 1992, pages S57 - S59, XP008004799, ISSN: 0160-2446 *
ZEMBOWICZ A ET AL: "NITRIC OXIDE AND ANOTHER POTENT VASODILARTOR ARE FORMED FROM NG-HYDROXY-L-ARGININE BY CULTURED ENDOTHELIAL CELLS", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF USA, NATIONAL ACADEMY OF SCIENCE. WASHINGTON, US, vol. 88, December 1991 (1991-12-01), pages 11172 - 11176, XP002939261, ISSN: 0027-8424 *
ZEMBOWICZ ET AL.: "NG-HYDROXY-L-ARGININE AND HYDROXYGUANIDINE POTENTIATE THE BIOLOGICAL ACTIVITY OF ENDOTHELIUM-DERIVED RELAXING FACTOR RELEASED BY RABBIT AORTA", BIOCEHM. BIOPHYS. RES. COMMUN., vol. 189, no. 2, 15 December 1992 (1992-12-15), pages 711 - 716, XP001073971 *

Also Published As

Publication number Publication date
AU2002364804A1 (en) 2003-06-10
WO2003045369A9 (fr) 2004-07-01
WO2003045369A2 (fr) 2003-06-05
FR2832634A1 (fr) 2003-05-30
AU2002364804A8 (en) 2003-06-10

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