FR2424269A2 - 4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate - Google Patents

4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate

Info

Publication number
FR2424269A2
FR2424269A2 FR7812185A FR7812185A FR2424269A2 FR 2424269 A2 FR2424269 A2 FR 2424269A2 FR 7812185 A FR7812185 A FR 7812185A FR 7812185 A FR7812185 A FR 7812185A FR 2424269 A2 FR2424269 A2 FR 2424269A2
Authority
FR
France
Prior art keywords
alkyl
hydroxy
halo
pyridyl
alkoxycarbonyl
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
FR7812185A
Other languages
French (fr)
Other versions
FR2424269B2 (en
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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7812185A priority Critical patent/FR2424269A2/en
Priority to OA56480BISA priority patent/OA05950A/en
Priority to BE187744A priority patent/BE867128A/en
Priority to SE7805589A priority patent/SE7805589L/en
Priority to IL54735A priority patent/IL54735A0/en
Priority to AU36137/78A priority patent/AU3613778A/en
Priority to ES469883A priority patent/ES469883A1/en
Priority to GB19926/78A priority patent/GB1586917A/en
Priority to IT23473/78A priority patent/IT1096219B/en
Priority to PT197868047A priority patent/PT68047B/en
Priority to LU79663A priority patent/LU79663A1/en
Priority to IE983/78A priority patent/IE46829B1/en
Priority to DK214078A priority patent/DK214078A/en
Priority to NZ187290A priority patent/NZ187290A/en
Priority to DE19782821555 priority patent/DE2821555A1/en
Priority to AT356778A priority patent/ATA356778A/en
Priority to SU782615706A priority patent/SU852171A3/en
Priority to CA303,554A priority patent/CA1093078A/en
Publication of FR2424269A2 publication Critical patent/FR2424269A2/en
Application granted granted Critical
Publication of FR2424269B2 publication Critical patent/FR2424269B2/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

4-Hydroxy-thiazolidine-2-thione derivs. of formula (I) and their salts (when R2 = carboxyalkyl) are new: In the formulae, R1 = H or halo in position 4,5 or 6; R2=H, 1-8C alkyl, 1-4C alkyl (substd. by 1-3 halo atoms or by a phenyl, hydroxy, alkoxy, alkylthio, carboxy, alkoxycarbonyl, alkoxycarbonylalkoxy, alkoxycarbonyl-alkylthio; acyloxy, acyloxy-alkoxy or acyloxy-alkylthio), 3-6C cycloalkyl, cyclohexenyl, phenyl (opt. substd. by halo, alkyl, alkoxy, hydroxy or nitro), 2-thienyl or alkoxycarbonyl; R3 = H, alkyl, acyloxyalkyl, alkoxycarbonylalkyl or alkoxycarbonyl or together with R2 forms a 3-4C alkylene chain which with the 2-C atoms to which R2 and R3 are attached may form a benzene ring and R4 = H or alkyl. The alkyl and acyl radicals may be opt. branched and unless otherwise stated contain 1-4C atoms. (I) are anthelmintics having broad activity. Some cpds. are active against (a) Nematosperoides dubius in mice orally at 5-200 mg/kg (b) Litomosoides carinii filiariosis in rats at 25-100 mg/kg when administered orally for 5 days, (c) Ankylostome carinium and Uncinaria stenocephale in dogs orally at 10-50 mg/kg and Toxocara canis and Toxascaris leonina orally at 5-50 mg/kg.
FR7812185A 1977-05-17 1978-04-25 4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate Granted FR2424269A2 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
FR7812185A FR2424269A2 (en) 1978-04-25 1978-04-25 4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate
OA56480BISA OA05950A (en) 1977-05-17 1978-04-27 New derivatives of 4-hydroxy thiazolidinethione-2 and their preparation.
IE983/78A IE46829B1 (en) 1977-05-17 1978-05-16 4-hydroxythiazolidine-2-thione derivatives
IL54735A IL54735A0 (en) 1977-05-17 1978-05-16 4-hydroxythiazolidine-2-thione derivatives, a process for their preparation and pharmaceutical compositions containing them
AU36137/78A AU3613778A (en) 1977-05-17 1978-05-16 4-hydroxythiazolidine-2-thione derivatives
ES469883A ES469883A1 (en) 1977-05-17 1978-05-16 4-hydroxythiazolidine-2-thione derivatives
GB19926/78A GB1586917A (en) 1977-05-17 1978-05-16 4-hydroxythiazolidine-2-thione derivatives
IT23473/78A IT1096219B (en) 1977-05-17 1978-05-16 DERIVATIVES OF HYDROXY-4 THIAZOLIDINTION-2, THEIR PREPARATION AND COMPOSITIONS CONTAINING THEM
BE187744A BE867128A (en) 1977-05-17 1978-05-16 NEW DERIVATIVES OF HYDROXY-4 THIAZOLIDINETHIONE-2, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
LU79663A LU79663A1 (en) 1977-05-17 1978-05-16 NEW DERIVATIVES OF HYDROXY-4 THIAZOLIDINETHIONE-2, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
SE7805589A SE7805589L (en) 1977-05-17 1978-05-16 PROCEDURE FOR THE PREPARATION OF NEW 4-HYDROXITIAZOLIDIN-2-THION DERIVATIVES
DK214078A DK214078A (en) 1977-05-17 1978-05-16 PROCEDURE FOR THE PREPARATION OF 4-HYDROXYTHIAZOLIDIN-2-THION DERIVATIVES
NZ187290A NZ187290A (en) 1977-05-17 1978-05-16 4-hydroxy-3-(pyrid-2-yl)-thiazolidine-2-thione derivatives and pharmaceutical or veterinary compositions
PT197868047A PT68047B (en) 1977-05-17 1978-05-16 NOVEL DERIVATIVES OF HYDROXY-4 THIAZOLIDINETHIONE-2 PREPARATION THEREOF AND THE COMPOSITIONS CONTAINING THEM
DE19782821555 DE2821555A1 (en) 1977-05-17 1978-05-17 4-HYDROXI-THIAZOLIDINE-2-THIONE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND COMPOSITIONS OF THESE
AT356778A ATA356778A (en) 1977-05-17 1978-05-17 METHOD FOR PRODUCING NEW 4-HYDROXY-THIAZOLIDIN-2-THION DERIVATIVES AND THEIR SALTS
SU782615706A SU852171A3 (en) 1977-05-17 1978-05-17 Method of preparing derivatives of 4-oxythiazolidinthioketene-2 and their salts
CA303,554A CA1093078A (en) 1977-05-17 1978-05-17 No translation available

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7812185A FR2424269A2 (en) 1978-04-25 1978-04-25 4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate

Publications (2)

Publication Number Publication Date
FR2424269A2 true FR2424269A2 (en) 1979-11-23
FR2424269B2 FR2424269B2 (en) 1980-09-19

Family

ID=9207548

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7812185A Granted FR2424269A2 (en) 1977-05-17 1978-04-25 4-Hydroxy-3-pyridyl-thiazolidine-2-thione derivs. - are anthelmintics prepd. by reacting an alpha-halo-ketone with a pyridyl-di:thiocarbamate

Country Status (1)

Country Link
FR (1) FR2424269A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725422A (en) * 1971-09-07 1973-04-03 Parke Davis & Co New organic sulfur compounds and methods for their production
US3726880A (en) * 1971-09-07 1973-04-10 Parke Davis & Co Organic amides and methods for their production
US3761485A (en) * 1971-09-07 1973-09-25 Parke Davis & Co 3-(5-chloro-2-pyridyl)rhodanine and 3-(5-chloro-2-pyridyl)-5-(lower alkyl)rhodanines

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3725422A (en) * 1971-09-07 1973-04-03 Parke Davis & Co New organic sulfur compounds and methods for their production
US3726880A (en) * 1971-09-07 1973-04-10 Parke Davis & Co Organic amides and methods for their production
US3761485A (en) * 1971-09-07 1973-09-25 Parke Davis & Co 3-(5-chloro-2-pyridyl)rhodanine and 3-(5-chloro-2-pyridyl)-5-(lower alkyl)rhodanines

Also Published As

Publication number Publication date
FR2424269B2 (en) 1980-09-19

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