WO1998054211A3 - Cyclodepsipeptides and pharmaceutical compositions containing them - Google Patents

Cyclodepsipeptides and pharmaceutical compositions containing them Download PDF

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Publication number
WO1998054211A3
WO1998054211A3 PCT/JP1998/002380 JP9802380W WO9854211A3 WO 1998054211 A3 WO1998054211 A3 WO 1998054211A3 JP 9802380 W JP9802380 W JP 9802380W WO 9854211 A3 WO9854211 A3 WO 9854211A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
lower alkyl
alkyl group
cyclodepsipeptides
hydrogen atom
Prior art date
Application number
PCT/JP1998/002380
Other languages
French (fr)
Other versions
WO1998054211A2 (en
Inventor
Akinobu Tsunoo
Masayuki Kamijo
Original Assignee
Meiji Milk Prod Co Ltd
Akinobu Tsunoo
Masayuki Kamijo
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 Meiji Milk Prod Co Ltd, Akinobu Tsunoo, Masayuki Kamijo filed Critical Meiji Milk Prod Co Ltd
Publication of WO1998054211A2 publication Critical patent/WO1998054211A2/en
Publication of WO1998054211A3 publication Critical patent/WO1998054211A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
    • 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
    • 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
    • A61P9/06—Antiarrhythmics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K11/00—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K11/02—Depsipeptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof cyclic, e.g. valinomycins ; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Cardiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Hospice & Palliative Care (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

This invention relates to the cyclodepsipeptide represented by formula (1), wherein R?1a, R1b and R1c¿ are a hydrogen atom or a methyl group, R?2 and R4¿ lower alkyl groups, and R3 a lower alkyl group or an aralkyl group. R?5 and R6¿ are a hydrogen, an alkyl group of 1 to 8 carbons or an aralkyl group (but not R5=R6=H), A and B are individually an ethylene group or a methylene group that is substituted by a lower alkyl group, X and Y represent -O- and -N(R1d)- in which R1d is a hydrogen atom or a methyl group, R?2 and R1d¿ of X, and/or R?4 and R1c¿ being capable of forming a nitrogen-containing ring together with the contiguous carbon and nitrogen atoms. This invention also provides a medicine containing this compound as an effective ingredient. These compounds have strong cardiotonic, antiarrhythnic and vasodilating effects without an arrhythmic side effect.
PCT/JP1998/002380 1997-05-29 1998-05-29 Cyclodepsipeptides and pharmaceutical compositions containing them WO1998054211A2 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP9/140111 1997-05-29
JP14011197 1997-05-29
JP9/276114 1997-10-08
JP27611497 1997-10-08
JP9308589A JPH11171897A (en) 1997-05-29 1997-11-11 Cyclic depsipeptide and medicine containing the same as active ingedient
JP9/308589 1997-11-11

Publications (2)

Publication Number Publication Date
WO1998054211A2 WO1998054211A2 (en) 1998-12-03
WO1998054211A3 true WO1998054211A3 (en) 1999-03-04

Family

ID=27318000

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1998/002380 WO1998054211A2 (en) 1997-05-29 1998-05-29 Cyclodepsipeptides and pharmaceutical compositions containing them

Country Status (2)

Country Link
JP (1) JPH11171897A (en)
WO (1) WO1998054211A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004518716A (en) * 2001-02-14 2004-06-24 ドン ワ ファーマシューティカル インダストリアル カンパニー リミテッド Pharmaceutical composition for prevention and treatment of osteoporosis
JP6024880B2 (en) * 2012-09-03 2016-11-16 国立大学法人東北大学 Novel usage of cyclic depsipeptide

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03251597A (en) * 1990-02-27 1991-11-11 Mitsubishi Kasei Corp Versaferrocide-based compound
JPH04321698A (en) * 1991-04-17 1992-11-11 Asahi Chem Ind Co Ltd Physiologically active substance m6124 and production thereof
JPH07138290A (en) * 1993-11-22 1995-05-30 Meiji Milk Prod Co Ltd Cardiotonic agent
JPH07188286A (en) * 1993-09-30 1995-07-25 Meiji Milk Prod Co Ltd Cyclic depsipeptide and cardiotonic agent containing the same
JPH09315996A (en) * 1996-05-27 1997-12-09 Meiji Milk Prod Co Ltd Cardiotonic agent and its production

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03251597A (en) * 1990-02-27 1991-11-11 Mitsubishi Kasei Corp Versaferrocide-based compound
JPH04321698A (en) * 1991-04-17 1992-11-11 Asahi Chem Ind Co Ltd Physiologically active substance m6124 and production thereof
JPH07188286A (en) * 1993-09-30 1995-07-25 Meiji Milk Prod Co Ltd Cyclic depsipeptide and cardiotonic agent containing the same
JPH07138290A (en) * 1993-11-22 1995-05-30 Meiji Milk Prod Co Ltd Cardiotonic agent
JPH09315996A (en) * 1996-05-27 1997-12-09 Meiji Milk Prod Co Ltd Cardiotonic agent and its production

Non-Patent Citations (20)

* Cited by examiner, † Cited by third party
Title
BIOORG KHIM, vol. 1, no. 1, 1975, pages 25 - 32 *
BIOORG KHIM, vol. 2, no. 12, 1976, pages 1597 - 1605 *
CHEMICAL ABSTRACTS, vol. 83, no. 13, 29 September 1975, Columbus, Ohio, US; abstract no. 114870, IVANOV E.A.: "Conformational states of cyclopeptide systems XII" page 606; column 2; XP002085052 *
CHEMICAL ABSTRACTS, vol. 83, no. 9, 1 September 1975, Columbus, Ohio, US; abstract no. 79585q, IVANOV E.A.: "Conformations of cyclopeptide systems IX" page 698; column 1; XP002085053 *
CHEMICAL ABSTRACTS, vol. 86, no. 17, 25 April 1977, Columbus, Ohio, US; abstract no. 121764m, SHISHOVA E.A.: "Molecular and crxstal structure of a cyclic hexadepsipeptide" page 586; column 2; XP002085054 *
DAS E.A.: "The identification of depsipeptides by chemical ionisation mass spectroscopy", J.ANTIBIOT., vol. XXXII, no. 6, June 1979 (1979-06-01), pages 569 - 574, XP002085049 *
DATABASE WPI Section Ch Week 9151, Derwent World Patents Index; Class C02, AN 91-373598, XP002075565 *
DATABASE WPI Section Ch Week 9252, Derwent World Patents Index; Class B03, AN 92-427199, XP002075567 *
DATABASE WPI Section Ch Week 9534, Derwent World Patents Index; Class B04, AN 95-256991, XP002075564 *
DATABASE WPI Section Ch Week 9538, Derwent World Patents Index; Class B04, AN 95-290422, XP002075563 *
DATABASE WPI Section Ch Week 9808, Derwent World Patents Index; Class B03, AN 98-082574, XP002075566 *
GILLIS E.A.: "Isolation and structure of sporidesmolide V from cultures of P.chartarum", CAN.J.CHEM., vol. 68, 1990, pages 19 - 21, XP002085050 *
GIRALT E.A.: "peptides 90, proceedings 21st EPS", ESCOM, LEIDEN, XP002075562 *
KHIM.PRIR. SOEDIN, vol. 11, no. 1, 1975, pages 63 - 69 *
KRASNOFF E.A.: "New destruxins from the entomopathogenic fungus Aschersonia sp.", J.NAT.PROD., vol. 59, no. 5, May 1996 (1996-05-01), pages 485 - 489, XP002075558 *
LOSSE E.A.: "Synthese von Enniatin-B-analogen mit D-valin anstelle von D-Alpha-hydroxyvaleriansäure", TETRAHEDRON, vol. 25, 1969, pages 2677 - 2685, XP002075560 *
LOUTELIER E.A.: "Studies on the dynamics of the production of destruxins by M.anisopliae", J.CHROM. A, vol. 738, 1996, pages 181 - 189, XP002075557 *
TSUNOO E.A.: "Roseocardin, a novel cardiotonic cyclodepsipeptide from T.roseum TT103", J.ANTIBIOT., vol. 50, no. 12, December 1997 (1997-12-01), pages 1007 - 1013, XP002075561 *
YEH E.A.: "Study of structure-activity corelation in destruxins, a class of cyclodepsipeptides possessing suppressive effect on the generation of Hepatitis B virus surface antigen in human hepatoma cells", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 229, no. 1, 1996, ORLANDO, FL US, pages 65-72, XP002075559 *
ZERVAS: "Peptides, proc.6th EPS, Athens, September 1963", 1966, PERGAMON PRESS, OXFORD, XP002085051 *

Also Published As

Publication number Publication date
JPH11171897A (en) 1999-06-29
WO1998054211A2 (en) 1998-12-03

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