EP1133508A2 - Benzylglycosylamides utilises comme inhibiteurs de proliferation des cellules du muscle lisse - Google Patents

Benzylglycosylamides utilises comme inhibiteurs de proliferation des cellules du muscle lisse

Info

Publication number
EP1133508A2
EP1133508A2 EP99960570A EP99960570A EP1133508A2 EP 1133508 A2 EP1133508 A2 EP 1133508A2 EP 99960570 A EP99960570 A EP 99960570A EP 99960570 A EP99960570 A EP 99960570A EP 1133508 A2 EP1133508 A2 EP 1133508A2
Authority
EP
European Patent Office
Prior art keywords
carbon atoms
substituted
hydrogen
independently
alkyl
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.)
Withdrawn
Application number
EP99960570A
Other languages
German (de)
English (en)
Inventor
Robert Emmett Mcdevitt
Folake Oluwemimo Adebayo
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.)
Wyeth LLC
Original Assignee
American Home Products Corp
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 American Home Products Corp filed Critical American Home Products Corp
Publication of EP1133508A2 publication Critical patent/EP1133508A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • 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
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • 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
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • 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
    • A61P9/08—Vasodilators for multiple indications
    • 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
    • A61P9/12—Antihypertensives
    • 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
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

Definitions

  • heparin, heparin fragments, chemically modified heparin, low molecular weight heparins, and other heparin mimicking anionic polysaccharides may be compromised due to other pharmacological liabilities (excessive bleeding arising from anticoagulation effects, in particular) coupled with heterogeneity of the various preparations (Borman, S. Chemical and Engineering News, 1993, June 28, 27).
  • WO 96/14325 discloses acylated benzylglycosides as smooth muscle cell proliferation inhibitors.
  • the compounds of the present invention differ in that (a) the carbohydrate posesses an anomeric amide, (b) the substituents on the carbohydrate backbone are substantially different and, (c) the activity against smooth muscle cell proliferation is greater.
  • R 3 is hydrogen, acylamide of 2 to 6 carbon atoms or alkoxy of 1 to 6 carbon atoms;
  • R 4 , R 5 , R 6 , R 7 , and R 8 are each, independently, hydrogen, acyl of 1 to 6 carbon atoms, benzyl substituted with R 1 , and R 2 ; or benzoyl substituted with R 1 and R 2 ;
  • Alkyl includes both straight chain as well as branched moieties.
  • Halogen means bromine, chlorine, fluorine, and iodine.
  • Y is nitrogen, it is preferred that the pyridine carboxamide is pyridine 3-carboxamide.
  • the creams and ointments may be viscous liquid or semisolid emulsions of either the oil-in-water or water-in-oil type.
  • Pastes comprised of absorptive powders dispersed in petroleum or hydrophilic petroleum containing the active ingredient may also be suitable.
  • a variety of occlusive devices may be used to release the active ingredient into the blood stream such as a semipermeable membrane covering a reservoir containing the active ingredient with or without a carrier, or a matrix containing the active ingredient. Other occlusive devices are known in the literature.
  • the dosage requirements vary with the particular compositions employed, the route of administration, the severity of the symptoms presented and the particular subject being treated.

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pulmonology (AREA)
  • Pain & Pain Management (AREA)
  • Vascular Medicine (AREA)
  • Rheumatology (AREA)
  • Hospice & Palliative Care (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Cette invention concerne des inhibiteurs de prolifération des cellules du muscle lisse, ou un sel pharmaceutiquement acceptable desdits inhibiteurs, qui présentent une structure de la formule (I) dans laquelle Y est C ou N; n est compris entre 0 et 3; X est représenté par la formule (A); R1 et R2 sont chacun, indépendamment de l'autre, hydrogène, un alkyle comprenant 1 à 6 atomes de carbone, halo, acétyle, phényle, CF¿3?, CN, OH, NO2, NH2, un alcoxy comprenant 1 à 6 atomes de carbone, ou un alcoxynitrile comprenant 1 à 6 atomes de carbone; R?3¿ est hydrogène, un acylamide comprenant 2 à 6 atomes de carbone ou un alcoxy comprenant 1 à 6 atomes de carbone; R?4, R5, R6, R7 et R8¿ sont chacun, indépendamment des autres, hydrogène, un acyle comprenant 1 à 6 atomes de carbone, benzyle substitué par R1 et R2, ou benzoyle substitué par R?1 et R2; R9 et R10¿ sont chacun, indépendamment de l'autre, un acyle comprenant 1 à 6 atomes de carbone, ou les groupes R?9 et R10¿ aux positions 4' et 6' du maltose peuvent être pris ensemble pour former un acétal cyclique pouvant être substitué par un alkyle comprenant 1 à 6 atomes de carbone, deux groupes alkyle ayant chacun entre 1 et 6 atomes de carbone, pyridine substitué par R1, phényle substitué par R1, benzyle substitué par R1, 2-phényléthyle substitué par R1, ou 3-phénylpropyle substitué par R1.
EP99960570A 1998-11-24 1999-11-23 Benzylglycosylamides utilises comme inhibiteurs de proliferation des cellules du muscle lisse Withdrawn EP1133508A2 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US19843298A 1998-11-24 1998-11-24
US198432 1998-11-24
PCT/US1999/027780 WO2000031093A2 (fr) 1998-11-24 1999-11-23 Benzylglycosylamides utilises comme inhibiteurs de proliferation des cellules du muscle lisse

Publications (1)

Publication Number Publication Date
EP1133508A2 true EP1133508A2 (fr) 2001-09-19

Family

ID=22733358

Family Applications (1)

Application Number Title Priority Date Filing Date
EP99960570A Withdrawn EP1133508A2 (fr) 1998-11-24 1999-11-23 Benzylglycosylamides utilises comme inhibiteurs de proliferation des cellules du muscle lisse

Country Status (7)

Country Link
EP (1) EP1133508A2 (fr)
JP (1) JP2002530418A (fr)
CN (1) CN1333781A (fr)
AU (1) AU1743700A (fr)
BR (1) BR9915612A (fr)
CA (1) CA2350758A1 (fr)
WO (1) WO2000031093A2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2350755A1 (fr) * 1998-11-24 2000-06-02 Robert Emmett Mcdevitt Benzylglycosylamides utilises comme inhibiteurs de la proliferation cellulaire des muscles lisses

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3655327B2 (ja) * 1994-05-09 2005-06-02 三井化学株式会社 オリゴ糖鎖を有するスチレン誘導体およびその製造方法
DE4436164A1 (de) * 1994-10-10 1996-04-11 Hoechst Ag Neue Kohlenhydratkonjugate als Inhibitoren der Zelladhäsion
CA2350755A1 (fr) * 1998-11-24 2000-06-02 Robert Emmett Mcdevitt Benzylglycosylamides utilises comme inhibiteurs de la proliferation cellulaire des muscles lisses

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0031093A2 *

Also Published As

Publication number Publication date
WO2000031093A2 (fr) 2000-06-02
WO2000031093A3 (fr) 2000-12-28
CA2350758A1 (fr) 2000-06-02
BR9915612A (pt) 2001-08-14
CN1333781A (zh) 2002-01-30
JP2002530418A (ja) 2002-09-17
AU1743700A (en) 2000-06-13

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