GB1022045A - Substituted 4-thiazolidinones and preparation thereof - Google Patents

Substituted 4-thiazolidinones and preparation thereof

Info

Publication number
GB1022045A
GB1022045A GB44348/62A GB4434862A GB1022045A GB 1022045 A GB1022045 A GB 1022045A GB 44348/62 A GB44348/62 A GB 44348/62A GB 4434862 A GB4434862 A GB 4434862A GB 1022045 A GB1022045 A GB 1022045A
Authority
GB
United Kingdom
Prior art keywords
lower alkyl
aryl
reacting
thiazolidinones
acyl radical
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.)
Expired
Application number
GB44348/62A
Inventor
Gerhard Satzinger
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.)
Warner Lambert Co LLC
Original Assignee
Warner Lambert Pharmaceutical Co
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 Warner Lambert Pharmaceutical Co filed Critical Warner Lambert Pharmaceutical Co
Priority to GB44348/62A priority Critical patent/GB1022045A/en
Publication of GB1022045A publication Critical patent/GB1022045A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/34—Oxygen atoms

Landscapes

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

Abstract

The invention comprises thiazolidinones of the formula <FORM:1022045/C2/1> wherein R1 is hydrogen, lower alkyl or aryl; R2 is cyano, -CO.R5 in which R5 is lower alkoxy or aryl, or SO2R6 wherein R6 is lower alkyl or aryl; R3 is hydrogen or lower alkyl; and R4 is lower alkyl, alkenyl or alkynyl, the acyl radical of a C1-6 aliphatic carboxylic acid or -(CH2)n-R7 wherein n is 1-3 and R7 is halogen, hydroxyl, aryl, the acyl radical of a lower alkyl carboxylic acid, carbalkoxy in which the alkyl portion is lower alkyl, or <FORM:1022045/C2/2> wherein R8 is a lower alkyl radical or together with the nitrogen atom forms a piperidino, morpholino or pyrrolidino group (the word "lower" indicating a group of 1-6 carbon atoms); and their preparation by (a) reacting a compound of the formula <FORM:1022045/C2/3> wherein M is an alkali metal, with a compound R4X wherein X is a halogen atom; (b) when R4 is lower alkyl, reacting the alkali metal derivative II with a dialkyl sulphate R4.OSO2O.R4 or (c) when R4 is a carboxylic acyl radical reacting the 3-unsubstituted thiazolidinone with an acid anhydride R4-O-R4. Specified products include 2-cyanomethylene-, carbethoxymethylene-, benzoylmethylene-, phenylsulphonylmethylene and a - carbethoxybenzylidene-, 4 - thiazolidinones, 3 - substituted by methyl, dimethylaminoethyl, dimethylaminopropyl, diethylaminoethyl, diethylaminopropyl, benzyl, allyl, carbethoxymethyl, b -acetylethyl, b -hydroxyethyl, b -bromoethyl, propargyl, acetyl and piperidinoethyl groups. Pharmaceutical preparations having analgesic, sedative and anti-inflammatory activity comprise the above compounds together with a pharmaceutical carrier, suitably in the form of tablets, capsules, solutions, suspensions or suppositories.
GB44348/62A 1962-11-23 1962-11-23 Substituted 4-thiazolidinones and preparation thereof Expired GB1022045A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB44348/62A GB1022045A (en) 1962-11-23 1962-11-23 Substituted 4-thiazolidinones and preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB44348/62A GB1022045A (en) 1962-11-23 1962-11-23 Substituted 4-thiazolidinones and preparation thereof

Publications (1)

Publication Number Publication Date
GB1022045A true GB1022045A (en) 1966-03-09

Family

ID=10432852

Family Applications (1)

Application Number Title Priority Date Filing Date
GB44348/62A Expired GB1022045A (en) 1962-11-23 1962-11-23 Substituted 4-thiazolidinones and preparation thereof

Country Status (1)

Country Link
GB (1) GB1022045A (en)

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