WO2005042442A3 - 2-methylthio-1,4-naphthoquinone derivatives, methods for the production thereof, pharmaceutical compositions containing the same, and use thereof - Google Patents

2-methylthio-1,4-naphthoquinone derivatives, methods for the production thereof, pharmaceutical compositions containing the same, and use thereof Download PDF

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Publication number
WO2005042442A3
WO2005042442A3 PCT/EP2004/010465 EP2004010465W WO2005042442A3 WO 2005042442 A3 WO2005042442 A3 WO 2005042442A3 EP 2004010465 W EP2004010465 W EP 2004010465W WO 2005042442 A3 WO2005042442 A3 WO 2005042442A3
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WO
WIPO (PCT)
Prior art keywords
methylthio
production
methods
pharmaceutical compositions
same
Prior art date
Application number
PCT/EP2004/010465
Other languages
German (de)
French (fr)
Other versions
WO2005042442A2 (en
Inventor
Werner E G Mueller
Narshinh L Thakur
Arachana N Thakur
Heinz C Schroeder
Gerhard Lang
Hideyuki Tsuruta
Gerhard Bringmann
Original Assignee
Univ Mainz Johannes Gutenberg
Univ Wuerzburg J Maximilians
Werner E G Mueller
Narshinh L Thakur
Arachana N Thakur
Heinz C Schroeder
Gerhard Lang
Hideyuki Tsuruta
Gerhard Bringmann
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.)
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Publication date
Application filed by Univ Mainz Johannes Gutenberg, Univ Wuerzburg J Maximilians, Werner E G Mueller, Narshinh L Thakur, Arachana N Thakur, Heinz C Schroeder, Gerhard Lang, Hideyuki Tsuruta, Gerhard Bringmann filed Critical Univ Mainz Johannes Gutenberg
Publication of WO2005042442A2 publication Critical patent/WO2005042442A2/en
Publication of WO2005042442A3 publication Critical patent/WO2005042442A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P11/00—Preparation of sulfur-containing organic compounds

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Wood Science & Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Microbiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Disclosed are the compounds 2-methylthio-1,4-naphthoquinone (MTN) and MTN derivatives of general formula (2) as well as methods for the production or isolation thereof. MTN and MTN derivatives have antitumor properties, especially antiangiogenetic properties in cell culture models while being provided with characteristics preventing/inhibiting neointimal proliferation.
PCT/EP2004/010465 2003-09-22 2004-09-17 2-methylthio-1,4-naphthoquinone derivatives, methods for the production thereof, pharmaceutical compositions containing the same, and use thereof WO2005042442A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10343798A DE10343798A1 (en) 2003-09-22 2003-09-22 New 2-thio-1,4-naphthoquinone derivatives, obtained by culturing alpha-Proteobacterium MBIC3368, are angiogenesis inhibitors useful e.g. for combating tumor diseases and neointimal hyperplasia
DE10343798.3 2003-09-22

Publications (2)

Publication Number Publication Date
WO2005042442A2 WO2005042442A2 (en) 2005-05-12
WO2005042442A3 true WO2005042442A3 (en) 2005-07-07

Family

ID=34306014

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2004/010465 WO2005042442A2 (en) 2003-09-22 2004-09-17 2-methylthio-1,4-naphthoquinone derivatives, methods for the production thereof, pharmaceutical compositions containing the same, and use thereof

Country Status (2)

Country Link
DE (1) DE10343798A1 (en)
WO (1) WO2005042442A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107879958B (en) * 2017-10-30 2019-07-19 黑龙江八一农垦大学 2- (4- methoxybenzene sulfydryl) -5,8- dimethoxy -1,4- naphthoquinones and preparation method thereof and drug containing it

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2691661A (en) * 1951-08-15 1954-10-12 Shell Dev Manufacture of organomercaptosubstituted quinones
JPS298279B1 (en) * 1949-09-01 1954-12-15
NL76833C (en) * 1951-05-28 1954-12-15
DE955597C (en) * 1955-02-04 1957-01-03 Bayer Ag Process for the preparation of alkyleneiminoquinones
EP0863442A2 (en) * 1997-03-06 1998-09-09 Mita Industrial Co. Ltd. Naphthoquinone derivative and electrophotosensitive material using the same
WO2001004130A1 (en) * 1999-07-14 2001-01-18 Purdue Research Foundation Phosphoramide compounds

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS298279B1 (en) * 1949-09-01 1954-12-15
NL76833C (en) * 1951-05-28 1954-12-15
US2691661A (en) * 1951-08-15 1954-10-12 Shell Dev Manufacture of organomercaptosubstituted quinones
DE955597C (en) * 1955-02-04 1957-01-03 Bayer Ag Process for the preparation of alkyleneiminoquinones
EP0863442A2 (en) * 1997-03-06 1998-09-09 Mita Industrial Co. Ltd. Naphthoquinone derivative and electrophotosensitive material using the same
WO2001004130A1 (en) * 1999-07-14 2001-01-18 Purdue Research Foundation Phosphoramide compounds

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TJEPKEMA, JACOBUS J. ET AL: "Fungicidal preparations", XP002325222, retrieved from STN Database accession no. 1955:62269 *
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MIZUNO, DAIJI: "2,3-Dialkylthio-1,4-naphthoquinone from 2-alkylthio-1,4-naphthoquinone", XP002325221, retrieved from STN Database accession no. 1956:74214 *
FIESER, LOUIS F. ET AL: "Synthesis of naphthoquinones for studies of the inhibition of enzyme systems", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 71, 1949, pages 3609 - 3614, XP002325220 *
GERSHON, HERMAN ET AL: "Fungitoxicity of 1,4-naphthoquinones to Candida albicans and Trichophyton mentagrophytes", CANADIAN JOURNAL OF MICROBIOLOGY, vol. 21, no. 9, 1975, pages 1317 - 1321, XP009046007 *
HORI, MITSUO ET AL: "Antibacterial effects of naphthoquinone derivatives on tubercle bacteria . I. Bacteriostatic action of naphthoquinone derivatives in vitro", OSAKA DAIGAKU IGAKU ZASSHI, 13, 1961, pages 147 - 156, XP009045998 *
IKEDA, NISABURO: "Antibacterial properties of 2- and 2,3-substituted 1,4-naphthoquinones. V. Antibacterial effects of arylthio-1,4-naphthoquinones and related compounds", YAKUGAKU ZASSHI, 75, 1955, pages 645 - 648, XP009046010 *
MIYAKI, KOMEI ET AL: "Tumor -inhibiting activities of arylnaphthoquinones", PHARM. BULL. (TOKYO), 4, 1956, pages 417 - 419, XP009046012 *
NESNOW, STEPHEN ET AL: "Inhibition of microsomal metabolism and chemical oncogenesis in culture by naphthalene quinones", JOURNAL OF ENVIRONMENTAL PATHOLOGY AND TOXICOLOGY, vol. 4, no. 5-6, 1980, pages 17 - 30, XP009046026 *
PRAKASH, GOPALAKRISHNAN ET AL: "Discriminant analysis and structure-activity relationships. 1. Naphthoquinones", JOURNAL OF MEDICINAL CHEMISTRY, vol. 21, no. 4, 1978, pages 369 - 374, XP002325218 *
TAKANO, KOUICHI ET AL: "Anticancer effects of naphthoquinone derivatives tested by a screening with Ehrlich ascites cells in mice", JAPAN. J. MED. SCI. & BIOL. , 12, 1959, pages 473 - 478, XP009046030 *

Also Published As

Publication number Publication date
WO2005042442A2 (en) 2005-05-12
DE10343798A1 (en) 2005-04-14

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