CA2384525A1 - Thienylhydrazon with digitalis-like properties (positive inotropic effects) - Google Patents

Thienylhydrazon with digitalis-like properties (positive inotropic effects) Download PDF

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Publication number
CA2384525A1
CA2384525A1 CA002384525A CA2384525A CA2384525A1 CA 2384525 A1 CA2384525 A1 CA 2384525A1 CA 002384525 A CA002384525 A CA 002384525A CA 2384525 A CA2384525 A CA 2384525A CA 2384525 A1 CA2384525 A1 CA 2384525A1
Authority
CA
Canada
Prior art keywords
digitalis
properties
positive inotropic
thienylhydrazon
lassbio
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.)
Granted
Application number
CA002384525A
Other languages
French (fr)
Other versions
CA2384525C (en
Inventor
Eliezer J. De Barreiro
Roberto Takashi Sudo
Edson X. Albuquerque
Yasco Aracava
Paulo De Assis Melo
Gisele Zapata Sudo
Newton Goncalves De Castro
Carlos Alberto Manssour Fraga
Wagner Monteiro Cintra
Francois Germain Noel
Claudia Lucia Martins Da Silva
Patricia Dias Fernandes
Ana Luisa Palhares De Miranda
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.)
Universidade Federal do Rio de Janeiro UFRJ
University of Maryland at Baltimore
Original Assignee
University Of Maryland, Baltimore
Eliezer J. De Barreiro
Roberto Takashi Sudo
Edson X. Albuquerque
Yasco Aracava
Paulo De Assis Melo
Gisele Zapata Sudo
Newton Goncalves De Castro
Carlos Alberto Manssour Fraga
Wagner Monteiro Cintra
Francois Germain Noel
Claudia Lucia Martins Da Silva
Patricia Dias Fernandes
Ana Luisa Palhares De Miranda
Universidade Federal Do Rio De Janeiro
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 University Of Maryland, Baltimore, Eliezer J. De Barreiro, Roberto Takashi Sudo, Edson X. Albuquerque, Yasco Aracava, Paulo De Assis Melo, Gisele Zapata Sudo, Newton Goncalves De Castro, Carlos Alberto Manssour Fraga, Wagner Monteiro Cintra, Francois Germain Noel, Claudia Lucia Martins Da Silva, Patricia Dias Fernandes, Ana Luisa Palhares De Miranda, Universidade Federal Do Rio De Janeiro filed Critical University Of Maryland, Baltimore
Publication of CA2384525A1 publication Critical patent/CA2384525A1/en
Application granted granted Critical
Publication of CA2384525C publication Critical patent/CA2384525C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

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

Abstract

The invention discloses a compound having the formula (I) wherein R1 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, unsubstituted phenyl, and substituted phenyl; R2 is selected from the group consisting of H, alkene, un-substituted phenol, and substituted phenyl;
and pharmaceutically acceptable salts thereof, having digitalis-like properties. The invention further discloses a novel method to synthesize 3,4-methylenedioxyben-zoyl-2-thienylhydrazone (LASSBio-294). LASSBio-294 produces positive inotropic effect on cardiac and skeletal muscle. The invention is useful for the treatment of congestive heart failure and muscle fatigue. It lacks toxic effects seen in digitalis glycosides.
CA002384525A 1999-06-21 2000-06-21 Thienylhydrazon with digitalis-like properties (positive inotropic effects) Expired - Fee Related CA2384525C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US14035299P 1999-06-21 1999-06-21
US60/140,352 1999-06-21
PCT/US2000/017024 WO2000078754A1 (en) 1999-06-21 2000-06-21 Thienylhydrazon with digitalis-like properties (positive inotropic effects)

Publications (2)

Publication Number Publication Date
CA2384525A1 true CA2384525A1 (en) 2000-12-28
CA2384525C CA2384525C (en) 2007-03-06

Family

ID=22490853

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002384525A Expired - Fee Related CA2384525C (en) 1999-06-21 2000-06-21 Thienylhydrazon with digitalis-like properties (positive inotropic effects)

Country Status (4)

Country Link
EP (1) EP1532140A1 (en)
AU (1) AU5628700A (en)
CA (1) CA2384525C (en)
WO (1) WO2000078754A1 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0403363A (en) * 2004-08-20 2006-05-02 Univ Rio De Janeiro selective muscle relaxants and pharmaceutical compositions
BRPI0601885A (en) * 2006-05-15 2008-03-25 Univ Rio De Janeiro antiinflammatory and analgesic pharmaceutical composition containing n-acylhydrazenic derivatives of safrol, use, and process for their preparation
ATE554759T1 (en) * 2007-01-31 2012-05-15 Guangzhou Zhongwei Biotechnology Ltd HYDROHYDROLOAD FREEZE-DRIED PIPERPHENTONAMINE POWDER FOR PREPARATION OF A SOLUTION FOR INJECTION, PRODUCTION METHOD AND USES
CN103304561B (en) * 2013-06-21 2016-06-01 天津药物研究院 One class has the compound of anti thrombotic action

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4410540A (en) * 1981-11-04 1983-10-18 Merrell Dow Pharmaceuticals Inc. Cardiotonic 4-aroylimidazolidin-2-ones
CA1266268C (en) * 1985-10-15 1990-02-27 Cardiotonic aroylthiazolones

Also Published As

Publication number Publication date
EP1532140A1 (en) 2005-05-25
CA2384525C (en) 2007-03-06
WO2000078754A1 (en) 2000-12-28
AU5628700A (en) 2001-01-09

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