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

Info

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
Authority
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.)
Filing date
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

Links

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

Landscapes

  • 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)
  • Wood Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Microbiology (AREA)
  • Genetics & Genomics (AREA)
  • General Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (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
DE10343798.3 2003-09-22
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

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
NL76833C (en) * 1951-05-28 1954-12-15
JPS298279B1 (en) * 1949-09-01 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

Similar Documents

Publication Publication Date Title
WO2006100082A3 (en) Substituted oxindol derivatives, drugs containing said derivatives and the use thereof
WO2004074244A3 (en) Pyrimidine compounds
AU2003228770A1 (en) Substituted pyrazolopyrimidines
TW200726753A (en) 2,4-diamino-pyrimidines as aurora inhibitors
MX2007005221A (en) Ascomycin crystalline forms and preparation thereof.
TNSN05007A1 (en) Novel thiophenylglycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof.
TW200801003A (en) Novel compounds
WO2008012532A3 (en) : pyridine-3-carboxamide compounds and their use for inhibiting 11-beta-hydroxysteroid dehydrogenase
MX2009004707A (en) Chemical compounds.
MX2007010045A (en) Pyrazolopyrimidines.
DE602004024213D1 (en) Aminopropanolderivate
WO2005037198A3 (en) Preparation of 1,7-disubstituted azabenzimidazoles as kinase inhibitors
MXPA06000921A (en) N-methyl-substituted benzamidzoles.
WO2006125555A3 (en) Quinazolinones
PT1753712E (en) Amino-propanol derivatives
MY140739A (en) 2, 6-quinolinyl derivatives, processes for preparing them and their uses
WO2007065595A3 (en) Xanthine derivatives, processes for preparing them and their uses
WO2007065684A3 (en) Bicyclic heteroyclic compounds as antiinflammatory or antiallergic agents
TW200508197A (en) Indolone-acetamide derivatives, processes for preparing them and their uses
IL183636A0 (en) Quinoline derivative, use and production thereof, and drug containing the same
TW200503619A (en) Use of isoindolinone derivatives as insecticides
WO2006074940A3 (en) Macrocyclic compounds and compositions useful as bace inhibitors
WO2006052886A8 (en) Metabolites of certain [1,4]diazepino[6,7,1-ij]quinoline derivatives and methods of preparation and use thereof
WO2007068473A3 (en) Organic compounds
WO2008102888A1 (en) Novel pseudoglycolipid and use thereof

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase