GB953097A - New benzenesulphonyl ureas and process for their manufacture - Google Patents

New benzenesulphonyl ureas and process for their manufacture

Info

Publication number
GB953097A
GB953097A GB24183/62A GB2418362A GB953097A GB 953097 A GB953097 A GB 953097A GB 24183/62 A GB24183/62 A GB 24183/62A GB 2418362 A GB2418362 A GB 2418362A GB 953097 A GB953097 A GB 953097A
Authority
GB
United Kingdom
Prior art keywords
benzenesulphonyl
urea
trifluoromethoxy
benzenesulphony
ester
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
GB24183/62A
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.)
Hoechst AG
Original Assignee
Hoechst AG
Farbwerke Hoechst AG
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 Hoechst AG, Farbwerke Hoechst AG filed Critical Hoechst AG
Publication of GB953097A publication Critical patent/GB953097A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/50Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52Y being a hetero atom
    • C07C311/54Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises compounds of the formula: <FORM:0953097/C2/1> in which X is oxygen or sulphur and R1 is a saturated or unsaturated aliphatic or alicyclic hydrocarbon radical of 2 to 8 carbon atoms, with the exception of n-propyl and n-butyl, or is an alkyl or cycloalkyl radical of 4-8 carbon atoms, interrupted by an oxygen and/or sulphur atom or is a benyyl or b -phenethyl radical, and salts of these compounds with physiologically tolerable bases. The compound are made by standard methods for the preparation of sulphonyl ureas e.g. by reacting a benzenesulphonyl isocyanate, carbamic ester, carbamic halide or mono-thiocarbamic ester or a benzenusulphonyl urea, N1-acyl urea or bis benzenesulphonyl urea with an amine R1-NH2 or conversely by reaction of a benzenesulphonamide with an isocyanate R1NCO, a carbamic ester R1-NH-COOR2, wherein R2 is alkyl or phenyl, or a carbamic halide. The sulphonyl ureas may also be made by forming a benzenesulphonyl isourea ether, benzenesulphonyl guanidine, benzenesulphonyl parabamic acid or benzenesulphony thiourea and converting these by known means such as hydrolysis or oxidation into the desired sulphonyl urea. Products are specified in which R1 is a cycloheptyl, isobutyl, cyclooctyl or cyclohexyl group. N-(4-Trifluoromethoxy - benzenesulphony)-N1-cyclohepty thiourea is made by reaction of 4-trifluoromethoxy - benzenesulphonamide with cycloheptyl mustard oil. 4-Tribluoromethylthio - benzenesulphonamide is made by diazotising trifluoromethyl 4-aminophenyl sulphide and reacting the product with sulphur dioxide and cuprous chloride in glacial acetic acid to give trifluoromethylthio - benzenesulphonyl chloride which is then treated with ammonia. Methyltrifluoroemthoxy-benzenesulphony -urethane is prepared by reaction of 4-trifluoromethoxy-benzensulphonamide and chloroformic ester. N-Trifluoromethoxy - benzenesulphony - N1-acetyl urea is made by the action of acetic anhydride on trifluoromethoxy-benzenesulphonyl urea. N,N-diphenyl-N1-cycloheptyl urea is prepared from dephenyl carbamoyl chloride and cycloheptylamine. Pharmaceutical preparations for oral treatment of diabetes mellitus comprise the above compounds of the invention in admixture or conjunction with a carrier, preferably in the form of a tablet.
GB24183/62A 1961-06-22 1962-06-22 New benzenesulphonyl ureas and process for their manufacture Expired GB953097A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF0034239 1961-06-22

Publications (1)

Publication Number Publication Date
GB953097A true GB953097A (en) 1964-03-25

Family

ID=7095468

Family Applications (1)

Application Number Title Priority Date Filing Date
GB24183/62A Expired GB953097A (en) 1961-06-22 1962-06-22 New benzenesulphonyl ureas and process for their manufacture

Country Status (5)

Country Link
BE (1) BE619289A (en)
CH (3) CH448056A (en)
DK (2) DK103072C (en)
FR (1) FR2022M (en)
GB (1) GB953097A (en)

Also Published As

Publication number Publication date
BE619289A (en) 1962-12-24
CH419090A (en) 1966-08-31
FR2022M (en) 1963-09-16
CH448056A (en) 1967-12-15
DK103072C (en) 1965-11-15
DK109745C (en) 1968-06-24
CH448055A (en) 1967-12-15

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