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    1.
    发明专利
    未知

    公开(公告)号：SE310494B

    公开(公告)日：1969-05-05

    申请号：SE464265

    申请日：1965-04-09

    Applicant: HOECHST AG

    Inventor： WEYER R ,  KORGER G ,  AUMUELLER W ,  WEBER H

    IPC: C07C311/54 ,  C07C311/59 ,  C07C143/833

    Abstract: Novel sulphonyl ureas of the formula and physiologically tolerable salts thereof, wherein R and R1 are each hydrogen or halogen or a C1- 6 alkyl or alkoxy group or, when R1 is hydrogen, R may also be azido, trifluoromethyl, or C1- 7 acyl group, and R2 is a C2- 4 alkyl group, are made by reacting an R,R1-substituted benzenesulphonyl isocyanate or a compound which reacts as an isocyanate such as the corresponding benzenesulphonyl carbamic ester, carbamic halide or thiocarbamic ester or the reaction product of a benzenesulphonyl isocyanate and an acid amide, e.g. caprolactam or butyrolactam, or a weakly basic amine, e.g. carbazole, with an R2-substituted cyclohexylamine or its acyl derivative, or conversely, reacting an R2-substituted cyclohexyl isocyanate, or a compound which behaves as a cyclohexyl isocyanate such as the carbamic ester or halide, with the corresponding benzenesulphonamide. Alternatively, a benzenesulphonyl urea, benzenesulphonyl-N1-acyl-urea or bis-benzenesulphonyl urea is reacted with a cyclohexylamine, or a cyclohexyl urea, N1-acyl-cyclohexyl urea, N1,N1-diphenyl cyclohexyl urea or N,N1-bis-cyclohexyl urea is reacted with a benzenesulphonamide. Further processes include reacting a cyclohexyl isourea ether, isothiourea ether or guanidine or the tertiary amine salt of a cyclohexyl-substituted parabanic acid with the appropriate benzenesulphonyl halide and converting the resulting benzeneslphonyl isourea ether, isothiourea ether, guanidine or parabanic acid to the desired benzenesulphonyl urea. 4-Isopropyl-cyclohexyl urea is made by reacting 4 - isopropylcyclohexylamine hydrochloride with potassium cyanate. 4-Isopropyl-cyclohexyl isocyanate is made by the action of phosgene on cyclohexylamine hydrochloride. Pharmaceutical preparations for oral treatment of diabetes mellitus comprise the above compounds of the invention in admixture or conjunction with a carrier suitably in the form of tablets.

    3.
    发明专利
    未知

    公开(公告)号：SE310492B

    公开(公告)日：1969-05-05

    申请号：SE464065

    申请日：1965-04-09

    Applicant: HOECHST AG

    Inventor： WEYER R ,  AUMUELLER W ,  WEBER H ,  KORGER G

    IPC: C07C311/54 ,  C07C311/59 ,  C07C143/833

    Abstract: Novel sulphonyl ureas of the formula and physiologically tolerable salts thereof, wherein R and R1 are each hydrogen or halogen or a C1- 6 alkyl or alkoxy group or, when R1 is hydrogen, R may also be azido, trifluoromethyl, or C1- 7 acyl group, and R2 is a C2- 4 alkyl group, are made by reacting an R,R1-substituted benzenesulphonyl isocyanate or a compound which reacts as an isocyanate such as the corresponding benzenesulphonyl carbamic ester, carbamic halide or thiocarbamic ester or the reaction product of a benzenesulphonyl isocyanate and an acid amide, e.g. caprolactam or butyrolactam, or a weakly basic amine, e.g. carbazole, with an R2-substituted cyclohexylamine or its acyl derivative, or conversely, reacting an R2-substituted cyclohexyl isocyanate, or a compound which behaves as a cyclohexyl isocyanate such as the carbamic ester or halide, with the corresponding benzenesulphonamide. Alternatively, a benzenesulphonyl urea, benzenesulphonyl-N1-acyl-urea or bis-benzenesulphonyl urea is reacted with a cyclohexylamine, or a cyclohexyl urea, N1-acyl-cyclohexyl urea, N1,N1-diphenyl cyclohexyl urea or N,N1-bis-cyclohexyl urea is reacted with a benzenesulphonamide. Further processes include reacting a cyclohexyl isourea ether, isothiourea ether or guanidine or the tertiary amine salt of a cyclohexyl-substituted parabanic acid with the appropriate benzenesulphonyl halide and converting the resulting benzeneslphonyl isourea ether, isothiourea ether, guanidine or parabanic acid to the desired benzenesulphonyl urea. 4-Isopropyl-cyclohexyl urea is made by reacting 4 - isopropylcyclohexylamine hydrochloride with potassium cyanate. 4-Isopropyl-cyclohexyl isocyanate is made by the action of phosgene on cyclohexylamine hydrochloride. Pharmaceutical preparations for oral treatment of diabetes mellitus comprise the above compounds of the invention in admixture or conjunction with a carrier suitably in the form of tablets.

    5.
    发明专利
    未知

    公开(公告)号：SE315877B

    公开(公告)日：1969-10-13

    申请号：SE1161265

    申请日：1965-09-06

    Applicant: HOECHST AG

    Inventor： AUMUELLER W ,  KORGER G

    IPC: C07C303/36 ,  C07C303/40 ,  C07C311/54 ,  C07C311/57 ,  C07C311/59 ,  C07C143/833

    Abstract: The invention comprises sulphonyl ureas of the formula and salts thereof with physiologically tolerable bases, wherein R is a C1- 6 alkyl group, X is a C2- 3 alkylene group and R1 is (a) a saturated or unsaturated aliphatic hydrocarbon radical of 2-8 carbon atoms which, when it contains 3-8 carbon atoms may be interrupted by an oxygen and/or sulphur atom, (b) an alicyclic hydrocarbon radical of 3-8 carbon atoms which may be interrupted by oxygen and/or sulphur, (c) a benzyl radical or (d) a b -phenethyl radical. The compounds are prepared by (a) reacting an appropriately substituted benzenesulphonyl isocyanate or a compound which during the reaction forms or behaves as an isocyanate, e.g. a benzenesulphonyl carbamic ester, thiocarbamic ester or carbamic halide or a benzenesulphonyl urea, N1-acyl urea or bis-benzenesulphonyl urea, with an amine R1NH2, (b) reacting an isocyanate of the formula R1NCO or a compound which forms or behaves as an isocyanate, e.g. a carbamic ester, thiocarbamic ester or carbamic halide, with a benzenesulphonamide; (c) reacting a guanidine, isourea ether, or a tertiary amine salt of a mono R1 substituted parabanic acid, with a benzenesulphonyl halide and converting the sulphonyl-isourea ether or sulphonyl-parabanic acid formed into a benzenesulphonyl urea, by hydrolysis; (d) treating a benzene sulphonyl-thiourea to replace the sulphur by an oxygen atom, e.g. by reaction with oxides of heavy metals or oxidizing agents; or (e) oxidizing the corresponding sulphenyl or sulphinyl ureas. 4 - (b - Methoxyethoxy) - benzenesulphonamide and 4 - (b - ethoxyethoxy) - benzenesulphonamide are made by reacting the appropriate b -alkoxyethoxybenzene with amidosulphonic acid, converting the resulting benzenesulphonic acid to the sulphonyl chloride by reaction with phosphorus pentachloride and reacting with ammonia. Pharmaceutical preparations for the oral treatment of diabetes comprise the above sulphonyl ureas or their salts with bases, e.g. alkali or alkaline earth metals in admixture or conjunction with a carrier, preferably in the form of tablets.

    7.
    发明专利
    未知

    公开(公告)号：SE309583B

    公开(公告)日：1969-03-31

    申请号：SE825562

    申请日：1962-07-26

    Applicant: HOECHST AG

    Inventor： AUMUELLER W ,  KORGER G

    IPC: C07C303/36 ,  C07C303/40 ,  C07C311/54 ,  C07C311/57 ,  C07C311/59 ,  C07C143/833

    Abstract: The invention comprises sulphonyl ureas of the formula and salts thereof with physiologically tolerable bases, wherein R is a C1- 6 alkyl group, X is a C2- 3 alkylene group and R1 is (a) a saturated or unsaturated aliphatic hydrocarbon radical of 2-8 carbon atoms which, when it contains 3-8 carbon atoms may be interrupted by an oxygen and/or sulphur atom, (b) an alicyclic hydrocarbon radical of 3-8 carbon atoms which may be interrupted by oxygen and/or sulphur, (c) a benzyl radical or (d) a b -phenethyl radical. The compounds are prepared by (a) reacting an appropriately substituted benzenesulphonyl isocyanate or a compound which during the reaction forms or behaves as an isocyanate, e.g. a benzenesulphonyl carbamic ester, thiocarbamic ester or carbamic halide or a benzenesulphonyl urea, N1-acyl urea or bis-benzenesulphonyl urea, with an amine R1NH2, (b) reacting an isocyanate of the formula R1NCO or a compound which forms or behaves as an isocyanate, e.g. a carbamic ester, thiocarbamic ester or carbamic halide, with a benzenesulphonamide; (c) reacting a guanidine, isourea ether, or a tertiary amine salt of a mono R1 substituted parabanic acid, with a benzenesulphonyl halide and converting the sulphonyl-isourea ether or sulphonyl-parabanic acid formed into a benzenesulphonyl urea, by hydrolysis; (d) treating a benzene sulphonyl-thiourea to replace the sulphur by an oxygen atom, e.g. by reaction with oxides of heavy metals or oxidizing agents; or (e) oxidizing the corresponding sulphenyl or sulphinyl ureas. 4 - (b - Methoxyethoxy) - benzenesulphonamide and 4 - (b - ethoxyethoxy) - benzenesulphonamide are made by reacting the appropriate b -alkoxyethoxybenzene with amidosulphonic acid, converting the resulting benzenesulphonic acid to the sulphonyl chloride by reaction with phosphorus pentachloride and reacting with ammonia. Pharmaceutical preparations for the oral treatment of diabetes comprise the above sulphonyl ureas or their salts with bases, e.g. alkali or alkaline earth metals in admixture or conjunction with a carrier, preferably in the form of tablets.

    10.
    发明专利
    未知

    公开(公告)号：SE315878B

    公开(公告)日：1969-10-13

    申请号：SE1161365

    申请日：1965-09-06

    Applicant: HOECHST AG

    Inventor： AUMUELLER W ,  KORGER G

    IPC: C07C303/36 ,  C07C303/40 ,  C07C311/54 ,  C07C311/57 ,  C07C311/59 ,  C07C143/833

    Abstract: The invention comprises sulphonyl ureas of the formula and salts thereof with physiologically tolerable bases, wherein R is a C1- 6 alkyl group, X is a C2- 3 alkylene group and R1 is (a) a saturated or unsaturated aliphatic hydrocarbon radical of 2-8 carbon atoms which, when it contains 3-8 carbon atoms may be interrupted by an oxygen and/or sulphur atom, (b) an alicyclic hydrocarbon radical of 3-8 carbon atoms which may be interrupted by oxygen and/or sulphur, (c) a benzyl radical or (d) a b -phenethyl radical. The compounds are prepared by (a) reacting an appropriately substituted benzenesulphonyl isocyanate or a compound which during the reaction forms or behaves as an isocyanate, e.g. a benzenesulphonyl carbamic ester, thiocarbamic ester or carbamic halide or a benzenesulphonyl urea, N1-acyl urea or bis-benzenesulphonyl urea, with an amine R1NH2, (b) reacting an isocyanate of the formula R1NCO or a compound which forms or behaves as an isocyanate, e.g. a carbamic ester, thiocarbamic ester or carbamic halide, with a benzenesulphonamide; (c) reacting a guanidine, isourea ether, or a tertiary amine salt of a mono R1 substituted parabanic acid, with a benzenesulphonyl halide and converting the sulphonyl-isourea ether or sulphonyl-parabanic acid formed into a benzenesulphonyl urea, by hydrolysis; (d) treating a benzene sulphonyl-thiourea to replace the sulphur by an oxygen atom, e.g. by reaction with oxides of heavy metals or oxidizing agents; or (e) oxidizing the corresponding sulphenyl or sulphinyl ureas. 4 - (b - Methoxyethoxy) - benzenesulphonamide and 4 - (b - ethoxyethoxy) - benzenesulphonamide are made by reacting the appropriate b -alkoxyethoxybenzene with amidosulphonic acid, converting the resulting benzenesulphonic acid to the sulphonyl chloride by reaction with phosphorus pentachloride and reacting with ammonia. Pharmaceutical preparations for the oral treatment of diabetes comprise the above sulphonyl ureas or their salts with bases, e.g. alkali or alkaline earth metals in admixture or conjunction with a carrier, preferably in the form of tablets.

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