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WO2007090733A1 - Dérivés nitrooxy utilisables comme agonistes des récepteurs alpha 2 adrénergiques - Google Patents

Dérivés nitrooxy utilisables comme agonistes des récepteurs alpha 2 adrénergiques Download PDF

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Publication number
WO2007090733A1
WO2007090733A1 PCT/EP2007/050627 EP2007050627W WO2007090733A1 WO 2007090733 A1 WO2007090733 A1 WO 2007090733A1 EP 2007050627 W EP2007050627 W EP 2007050627W WO 2007090733 A1 WO2007090733 A1 WO 2007090733A1
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WO
WIPO (PCT)
Prior art keywords
compound
group
integer
formula
ono
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/EP2007/050627
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English (en)
Inventor
Nicoletta Almirante
Angela Monopoli
Stefano Biondi
Ennio Ongini
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.)
Nicox SA
Original Assignee
Nicox 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 Nicox SA filed Critical Nicox SA
Publication of WO2007090733A1 publication Critical patent/WO2007090733A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D233/44—Nitrogen atoms not forming part of a nitro radical
    • C07D233/50—Nitrogen atoms not forming part of a nitro radical with carbocyclic radicals directly attached to said nitrogen atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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

Definitions

  • the present invention relates to ⁇ 2 adrenergic receptor agonist derivatives. More particularly, the present invention relates to nitrooxy derivatives of ⁇ 2 adrenergic receptor agonists, pharmaceutical compositions containing them and their use for the treatment of cardiovascular, renal and chronic liver diseases, inflammatory processes and metabolic syndromes.
  • n 5 is as defined a ove
  • Y 2 is an heterocyclic saturated, unsaturated or aromatic 5 or 6 members ring, containing one or more heteroatoms selected from nitrogen, oxygen, sulfur, and is selected from
  • C1-C20 alkylene refers to branched or straight chain C1-C20 hydrocarbon, preferably having from 1 to 10 carbon atoms such as methylene, ethylene, propylene, isopropylene, n-butylene, pentylene, n-hexylene and the like.
  • Ci-Ci 0 alkyl refers to branched or straight chain alkyl groups comprising one to ten carbon atoms, including methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, pentyl, hexyl, octyl and the like.
  • X3 is -O- or -S-, n 3 is 1 and R 2 is H;
  • Compound of formula B wherein B is equal to A when A is (Id) wherein N ia is -NH 2 is a known compound named guanabenz and can be prepared as described in GB1019120.
  • Compound of formula B wherein B is equal to A when A is (Ie) wherein Ni is -NH- is a known compound named tiamenidine and can be prepared as described in US 3,758,476.
  • Ni is -N-, Ni a is -NH and N 2 is -OH, can be obtained by a process comprising:

Landscapes

  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des dérivés nitrooxy agonistes alpha 2 adrénergiques de formule (I) : A-(X0-ONO2)s (I) et leurs énantiomères, leurs diastéréoisomères et leurs sels pharmaceutiquement acceptables, où s est un nombre entier égal à 1, 2 ou 3 ; A est un précurseur d'un agoniste des récepteurs alpha 2 adrénergiques ayant une activité pharmacologique étendue et une tolérabilité améliorée. Ces composés peuvent être employés pour le traitement de maladies cardiovasculaires, en particulier l'hypertension systémique, de maladies rénales et hépatiques chroniques, de processus inflammatoires et de syndromes métaboliques.
PCT/EP2007/050627 2006-02-06 2007-01-23 Dérivés nitrooxy utilisables comme agonistes des récepteurs alpha 2 adrénergiques Ceased WO2007090733A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US76515906P 2006-02-06 2006-02-06
US60/765,159 2006-02-06

Publications (1)

Publication Number Publication Date
WO2007090733A1 true WO2007090733A1 (fr) 2007-08-16

Family

ID=37807832

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/050627 Ceased WO2007090733A1 (fr) 2006-02-06 2007-01-23 Dérivés nitrooxy utilisables comme agonistes des récepteurs alpha 2 adrénergiques

Country Status (1)

Country Link
WO (1) WO2007090733A1 (fr)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008014299A3 (fr) * 2006-07-27 2008-04-24 Allergan Inc Méthodes et compositions utiles pour le traitement de l'hyperlipidémie
US20120065152A1 (en) * 2010-09-15 2012-03-15 Shire Llc Prodrugs of guanfacine
EP2398761A4 (fr) * 2009-02-18 2015-11-04 Bezwada Biomedical Llc Libération contrôlée d'oxyde nitrique et de médicaments à parti de macromères et d'oligomères fonctionnalisés
US11845736B2 (en) 2021-10-01 2023-12-19 Empathbio, Inc. Prodrugs of MDMA, MDA, and derivatives thereof
US11912680B2 (en) * 2021-12-28 2024-02-27 Empathbio, Inc. Nitric oxide releasing prodrugs of MDA and MDMA
US11993577B2 (en) 2021-09-01 2024-05-28 Empathbio, Inc. Synthesis of MDMA or its optically active (R)- or (S)-MDMA isomers
US12492178B2 (en) 2021-09-01 2025-12-09 Empathbio, Inc. Stable polymorph of R-MDMA HCl

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4312878A (en) * 1979-04-27 1982-01-26 Boehringer Ingelheim International Gmbh Method of eliminating opiate withdrawal symptoms with clonidine in humans
WO2005053685A1 (fr) * 2003-12-02 2005-06-16 Nicox S.A. Derives nitrooxy de carvedilol et d'autres beta-bloquants utilises comme medicaments antihypertenseurs
WO2005054218A1 (fr) * 2003-12-02 2005-06-16 Nicox S.A. Nitro-oxyderives de medicaments contre l'hypertension

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4312878A (en) * 1979-04-27 1982-01-26 Boehringer Ingelheim International Gmbh Method of eliminating opiate withdrawal symptoms with clonidine in humans
WO2005053685A1 (fr) * 2003-12-02 2005-06-16 Nicox S.A. Derives nitrooxy de carvedilol et d'autres beta-bloquants utilises comme medicaments antihypertenseurs
WO2005054218A1 (fr) * 2003-12-02 2005-06-16 Nicox S.A. Nitro-oxyderives de medicaments contre l'hypertension

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008014299A3 (fr) * 2006-07-27 2008-04-24 Allergan Inc Méthodes et compositions utiles pour le traitement de l'hyperlipidémie
EP2398761A4 (fr) * 2009-02-18 2015-11-04 Bezwada Biomedical Llc Libération contrôlée d'oxyde nitrique et de médicaments à parti de macromères et d'oligomères fonctionnalisés
US20120065152A1 (en) * 2010-09-15 2012-03-15 Shire Llc Prodrugs of guanfacine
WO2012035346A1 (fr) * 2010-09-15 2012-03-22 Shire, Llc Promédicaments de guanfacine
US11993577B2 (en) 2021-09-01 2024-05-28 Empathbio, Inc. Synthesis of MDMA or its optically active (R)- or (S)-MDMA isomers
US12492178B2 (en) 2021-09-01 2025-12-09 Empathbio, Inc. Stable polymorph of R-MDMA HCl
US11845736B2 (en) 2021-10-01 2023-12-19 Empathbio, Inc. Prodrugs of MDMA, MDA, and derivatives thereof
US11912680B2 (en) * 2021-12-28 2024-02-27 Empathbio, Inc. Nitric oxide releasing prodrugs of MDA and MDMA
US20240400532A1 (en) * 2021-12-28 2024-12-05 Empathbio, Inc. Nitric oxide releasing prodrugs of mda and mdma
US12454516B2 (en) * 2021-12-28 2025-10-28 Empathbio, Inc. Nitric oxide releasing prodrugs of MDA and MDMA

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