AU567543B2 - 1,2-dithiol-3-one derivatives - Google Patents

1,2-dithiol-3-one derivatives

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Publication number
AU567543B2
AU567543B2 AU24856/84A AU2485684A AU567543B2 AU 567543 B2 AU567543 B2 AU 567543B2 AU 24856/84 A AU24856/84 A AU 24856/84A AU 2485684 A AU2485684 A AU 2485684A AU 567543 B2 AU567543 B2 AU 567543B2
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AU
Australia
Prior art keywords
radical
denotes
general formula
product
substituted
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Ceased
Application number
AU24856/84A
Other versions
AU2485684A (en
Inventor
Jean-Dominique Bourzat
Claude Cotrel
Daniel Farge
Jean-Marc Paris
Gerard Taurand
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Rhone Poulenc Sante SA
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Rhone Poulenc Sante SA
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Application filed by Rhone Poulenc Sante SA filed Critical Rhone Poulenc Sante SA
Publication of AU2485684A publication Critical patent/AU2485684A/en
Application granted granted Critical
Publication of AU567543B2 publication Critical patent/AU567543B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D339/00Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02Five-membered rings
    • C07D339/04Five-membered rings having the hetero atoms in positions 1 and 2, e.g. lipoic acid
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Rheumatology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Pain & Pain Management (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Saccharide Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

For the Contracting States : BE, CH, DE, FR, GB, IT, LI, LU, NL, SE 1. 1,2-Dithiol-3-one derivative, characterized in that it corresponds to the general formula : see diagramm : EP0119895,P26,F1 in which - either R denotes a hydrogen or chlorine atom, A denotes an oxygen atom or an imino, alkylimino, alkylcarbonylimino or formylimino radical and Ar denotes a phenyl radical substituted by a cycloalkyl radical in which the alkyl part contains 3 to 7 carbon atoms, an alkenyl radical containing 2 to 4 carbon atoms as a straight or branched chain, an anilino, formyl, semicarbazonomethyl, 1,3-dithiolan-2-yl, 1,3-dioxolan-2-yl, dialkylaminomethyleneamino, trifluoromethylthio or alkylcarbonyloxy radical or an alkyl radical substituted by a hydroxy, alkoxy, carboxy, amino, alkylcarbonylamino, alkoxycarbonylamino, dialkylaminomethyleneamino, formamido, alkylureido, phenylsulphonyl, carbamoyl, alkylcarbamoyl, dialklylcarbamoyl, formul, semicarbazonomethyl, 1,3-dithiolan-2-yl or 1,3-dioxolan-2-yl radical or Ar denotes a pyridyl, quinolyl, isoquinolyl, indanyl or quinoxalinyl radical, - or R denotes a hydrogen atom, A denotes an oxygen atom or an amino, alkylimino, alkylcarbonylimino or formylimino radical and Ar denotes a phenyl radical substituted by an alkyl radical, - or R denotes a chlorine atom, A denotes an oxygen atom or an alkylcarbonylimino or formylimino radical and Ar denotes a phenyol radical substituted by an alkyl radical, it being understood that, unless specially mentioned, all the alkyl radicals and alkyl moieties contain 1 to 4 carbon atoms as a straight or branched chain, as well as, where these exist, its salts of addition with acids, its metal salts and its salts of addition with organic bases. For the Contracting State : AT 1. Process for the preparation of 1,2-dithiol-3-one derivative, of general formula : see diagramm : EP0119895,P28,F1 in which - either R denotes a hydrogen or chlorine atom, A denotes an oxygen atom or an imino, alkylimino, alkylcarbonylimino or formylimino radical and Ar denotes a phenyl radical substituted by a cycloalkyl radical in which the alkyl part contains 3 to 7 carbon atoms, an alkenyl radical containing 2 to 4 carbon atoms as a straight or branched chain, an anilino, formyl, semicarbazonomethyl, 1,3-dithiolan-2-yl, 1,3-dioxolan-2-yl, dialkylaminomethyleneamino, trifluoromethylthio or alkylcarbonyloxy radical or an alkyl radical substituted by a hydroxy, alkoxy, carboxy, amino, alkylcarbonylamino, alkoxycarbonylamino, dialkylaminomethyleneamino, formamido, alkylureido, phenylsulphonyl, carbamoyl, alkylcarbamoyl, dialklylcarbamoyl, formyl, semicarbazonomethyl, 1,3-dithiolan-2-yl or 1,3-dioxolan-2-yl radical or Ar denotes a pyridyl, quinolyl, isoquinolyl, indanyl or quinoxalinyl radical, - or R denotes a hydrogen atom, A denotes an oxygen atom or an amino, alkylimino, alkylcarbonylimino or formylimino radical and Ar denotes a phenyl radical substituted by an alkyl radical, - or R denotes a chlorine atom, A denotes an oxygen atom or an alkylcarbonylimino or formylimino radical and Ar denotes a phenyol radical substituted by an alkyl radical, it being understood that, unless specially mentioned, all the alkyl radicals and alkyl moieties contain 1 to 4 carbon atoms as a straight or branched chain, as well as, where these exist, its salts of addition with acids, its metal salts and its salts of addition with organic bases, characterized in that a) for the preparation of a product of general formula (I) in which A denotes an oxygen atom or an imino or alkylimino radical, R denotes a chlorine atom and Ar is defined as above except for denoting a phenyl radical substituted by a dialkylamino-methyleneamino radical or an alkyl radical substituted by a dialkylaminomethyleneamino radical, a product of general formula : Ar-A-H in which Ar and A have the corresponding definition, is reacted with 4,5-dichloro-1,2-dithiol-3-one of formula : see diagramm : EP0119895,P28,F2 and the product obtained is then isolated and converted, if appropriate, into a salt of addition with an acid, into a metal salt or into a salt of addition with a nitrogenous base, or in that b) for the preparation of a product of general formula (I) in which A denotes an alkylimino radical and the other symbols are defined as above, a product of general formula : R1 X in which R1 denotes an alkyl radical and X denotes a halogen atom or a reactive ester residue such as mesyloxy or tosyloxy, is reacted with a product of general formula (I), in which A denotes an imino radical and the other symbols are defined as above, that is to say a product of general formula : see diagramm : EP0119895,P29,F3 and the product obtained is then isolated and is converted, if appropriate, into a salt of addition with an acid, into a metal salt or into a salt of addition with an organic base, or in that c) for the preparation of a product of general formula (I) in which A denotes an alkylcarbonylimino or formylimino radical and the other symbols are defined as above, a mixed anhydride of general formula : R2 COOCOCH3 in which R2 denotes a hydrogen atom or an alkyl radical, is reacted with a product of general formula (I) in which A denotes an imino radical and the other symbols are defined as above, that is to say a product of general formula : see diagramm : EP0119895,P29,F4 and the product obtained is then isolated and is converted, if appropriate, into a salt of addition with an acid, into a metal salt or into a salt of addition with a nitrogenous base, or in that d) for the preparation of a product of general formula (I) in which R denotes a hydrogen atom and the other symbols are defined as above, a product of general formula (I) in which R denotes a chlorine atom and the other symbols are defined as above, that is to say a product of general formula : see diagramm : EP0119895,P29,F5 is dechlorinated and the product obtained is then isolated and is converted, if appropriate, into a salt of addition with an acid, into a metal salt or into a salt of addition with a nitrogenous base, or in that e) for the preparation of a product of general formula (I), in which Ar denotes a phenyl radical substituted by a 1,3-dithiolan-2-yl or 1,3-dioxolan-2-yl radical or an alkyl radical substituted by a 1,3-dithiolan-2-yl or 1,3-dioxolan-2-yl radical and the other symbols are defined as above, a product of general formula : H-Y(CH2 )2 -Y-H in which the symbols Y both denotes a sulphur or oxygen atom, is reacted with a product of general formula (I), in which Ar denotes a phenyl radical substituted by a formyl radical or by an alkyl radical substituted by a formyl radical, that is to say a product of general formula : see diagramm : EP0119895,P29,F6 in which Q denotes a valency bond or an alkylene radical containing 1 to 4 carbon atoms as a straight or branched chain, and the other symbols are defined as above, and the product obtained is then isolated, or in that f) for the preparation of a product of general formula (I), in which Ar denotes a phenyl radical substituted by a dialkylaminomethyleneamino radical or by an alkyl radical substituted by a dialkylaminomethyleneamino radical and the other symbols are defined as above, a product of general formula : see diagramm : EP0119895,P29,F7 in which the radicals R3 , R4 , R5 and R6 denote alkyl radicals is reacted with a product of general formula (I), in which Ar denotes a phenyl radical substituted by an amino radical or by an alkyl radical substituted by amino radical, that is to say a product of general formula : see diagramm : EP0119895,P29,F8 in which Q denotes a valency bond or an alkylene radical containing 1 to 4 carbon atoms as a straight or branched chain and the other symbols are defined as above, and the product obtained is then isolated and is converted, if appropriate, into a salt of addition with an acid, or in that g) for the preparation of a product of general formula (I), in which Ar denotes a phenyl radical substituted by an alkyl radical which is itself substituted by an alkylcarbonylamino or alkoxycarbonylamino radical and the other symbols are defined as above, a product of general formula : R7 X1 in which R7 denotes an alkylcarbonyl or alkoxycarbonyl radical and X1 denotes a halogen atom, is reacted with a product of general formula (I), in which A denotes a phenyl radical substituted by an alkyl radical substituted by an amino radical and the other symbols are defined as above, that is to say a product of general formula : see diagramm : EP0119895,P30,F9 in which Q' denotes an alkylene radical containing 1 to 4 carbon atoms as a straight or branched chain and the other symbols are defined as above, and the product obtained is then isolated, or in that h) for the preparation of a product of general formula (I), in which Ar denotes a phenyl radical substituted by an alkyl radical substituted by a formamido radical and the other symbols are defined as above, an alkyl formate of general formula : HCOOR8 in which R8 denotes an alkyl radical, is reacted with a product of general formula (I), in which Ar denotes a phenyl radical substituted by an alkyl radical which is itself substituted by an amino radical, that is to say a product of general formula : see diagramm : EP0119895,P30,F10 in which Q' denotes an alkylene radical containing 1 to 4 carbon atoms as a straight or branched chain and the other symbols are defined as above, and the product obtained is then isolated, or in that i) for the preparation of a product of general formula (I), in which Ar denotes a phenyl radical which is itself substituted by an alkyl radical substituted by a ureido radical and the other symbols are defined as above, an isocyanate of general formula : OCNR9 in which R9 denotes an alkyl radical, is reacted with a product of general formula (I), in which Ar denotes a phenyl radical substituted by an alkyl radical which is itself subst
AU24856/84A 1983-02-24 1984-02-23 1,2-dithiol-3-one derivatives Ceased AU567543B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8303004 1983-02-24
FR8303004A FR2541679B1 (en) 1983-02-24 1983-02-24 NOVEL DITHIOLE-1,2 ONE-3 DERIVATIVES, THEIR PREPARATION AND THE MEDICINAL COMPOSITIONS CONTAINING THEM

Publications (2)

Publication Number Publication Date
AU2485684A AU2485684A (en) 1984-08-30
AU567543B2 true AU567543B2 (en) 1987-11-26

Family

ID=9286217

Family Applications (1)

Application Number Title Priority Date Filing Date
AU24856/84A Ceased AU567543B2 (en) 1983-02-24 1984-02-23 1,2-dithiol-3-one derivatives

Country Status (17)

Country Link
EP (1) EP0119895B1 (en)
JP (1) JPS59163384A (en)
KR (1) KR840008011A (en)
AT (1) ATE25253T1 (en)
AU (1) AU567543B2 (en)
CA (1) CA1227208A (en)
DE (1) DE3462260D1 (en)
DK (1) DK158734C (en)
ES (1) ES8500930A1 (en)
FR (1) FR2541679B1 (en)
GR (1) GR79526B (en)
HU (1) HU199820B (en)
IE (1) IE56921B1 (en)
NO (1) NO169488C (en)
NZ (1) NZ207245A (en)
SU (2) SU1480769A3 (en)
ZA (1) ZA841275B (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1528170A (en) * 1965-06-18 1968-06-07 Agripat Sa 3-oxo-1, 2-dithioles, their preparation and application as agents for combating microorganisms

Also Published As

Publication number Publication date
NZ207245A (en) 1986-12-05
DK93784D0 (en) 1984-02-23
ES529985A0 (en) 1984-11-01
DK93784A (en) 1984-08-25
EP0119895A1 (en) 1984-09-26
NO169488B (en) 1992-03-23
SU1480769A3 (en) 1989-05-15
NO840697L (en) 1984-08-27
HUT35664A (en) 1985-07-29
FR2541679B1 (en) 1985-06-14
ZA841275B (en) 1984-09-26
NO169488C (en) 1992-07-01
DK158734C (en) 1990-11-19
CA1227208A (en) 1987-09-22
IE56921B1 (en) 1992-01-29
KR840008011A (en) 1984-12-12
EP0119895B1 (en) 1987-01-28
FR2541679A1 (en) 1984-08-31
HU199820B (en) 1990-03-28
ATE25253T1 (en) 1987-02-15
DK158734B (en) 1990-07-09
IE840419L (en) 1984-08-24
ES8500930A1 (en) 1984-11-01
JPS59163384A (en) 1984-09-14
GR79526B (en) 1984-10-30
AU2485684A (en) 1984-08-30
DE3462260D1 (en) 1987-03-05
SU1286107A3 (en) 1987-01-23

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