公开(公告)号：DK119161B

公开(公告)日：1970-11-23

申请号：DK558065

申请日：1965-10-29

Applicant: HOECHST AG

Inventor： PESCHKE W

IPC: A61K31/64 ,  C07C311/54 ,  C07D209/48 ,  C07D333/34 ,  C07D27/52 ,  C07D27/28 ,  C07C143/78

Abstract: Novel compounds of the formula X-Y-phenylene-SO2-NH-CO-NHR and their salts, wherein X is a phthalimide group which may be wholly or partly hydrogenated and/or may be mono- or di-substituted by one or two halogen, lower alkyl or lower alkoxy substituents, or is a tetrahydro- or hexahydro - endomethylene - or endoethylene - phthalimide group or a napthalimide, napththalene - 1, 2 - dicarbonimide or naphthalene - 2, 3 - dicarbonimide group; Y is a branched or unbranched C1- 4 hydrocarbon group; the "phenylene" group is an unsubstituted or halogen, C1- 4 alkyl or C1- 4 alkoxy substituted phenylene radical and R is a C2- 8 alkyl, alkenyl or mercapto alkyl group, a C4- 8 alkoxyalkyl or alkylmercaptoalkyl group (having at least two carbon atom in the alkylene portion), a phenyl lower alkyl or phenylcyclopropyl group, a cyclohexyl-lower alkyl, cycloheptylmethyl, cycloheptylethyl or cyclo-octylmethyl group, an endoalkylene - cyclohexyl, - cyclohexenyl, -cyclohexylmethyl or cyclohexenylmethyl group, a lower alkyl or lower alkoxycyclohexyl group, a C5- 8 cycloalkyl group, a cyclohexenyl or cyclohexenylmethyl group or a heterocyclic group having 4 or 5 carbon atoms and an oxygen or sulphur atom which may have one or two ethylenic double bonds and is attached to the N-atom directly or through a methylene group, are made by the usual sulphonyl urea syntheses, i.e. reaction of the appropriate benzenesulphonyl urea with an isocyanate RNCO or an equivalent carbamic ester or halide, thiocarbamic ester or urea derivative, or conversely reacting an amine R-NH2 or its salt with an X-Y-substituted benzenesulphonyl isocyanate or its equivalent; reacting a sulphonyl chloride of the formula X-Y-phenylene -SO2Cl with an R-substituted urea, isourea ether, isothiourea ether or parabanic acid and, if required, hydrolysing the product; replacing sulphur by oxygen in the corresponding benzenesulphonyl thiourea, or oxidizing a corresponding benzenesulphenyl or benzenesulphonyl urea; and also by converting a corresponding benzenesulphonyl urea of the formula Z-Y-phenylene-SO2-NH-CO-NHR, in which Z is a phthalic acid mono-amide group which may be partially hydrogenated and/or substituted into the corresponding phthalimide compound by cyclization. Pharmaceutical preparations having hypoglaycaemic comprise the above compounds of the invention in admixture or conjunction with a carrier, preferably in a form adapted to oral administration.

公开(公告)号：SE307350B

公开(公告)日：1969-01-07

申请号：SE264864

申请日：1964-03-04

Applicant: HOECHST AG

Inventor： KORGER G ,  AUMUELLER W ,  HAACK E ,  PESCHKE W

IPC: C07C311/54 ,  C07C143/833

公开(公告)号：FI45331B

公开(公告)日：1972-01-31

申请号：FI255965

申请日：1965-10-26

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  MUTH K ,  PESCHKE W ,  WEYER R ,  WEBER H

IPC: A61K31/64 ,  C07C311/54 ,  C07D209/48 ,  C07D333/34 ,  C07D27/52

Abstract: Novel compounds of the formula X-Y-phenylene-SO2-NH-CO-NHR and their salts, wherein X is a phthalimide group which may be wholly or partly hydrogenated and/or may be mono- or di-substituted by one or two halogen, lower alkyl or lower alkoxy substituents, or is a tetrahydro- or hexahydro - endomethylene - or endoethylene - phthalimide group or a napthalimide, napththalene - 1, 2 - dicarbonimide or naphthalene - 2, 3 - dicarbonimide group; Y is a branched or unbranched C1- 4 hydrocarbon group; the "phenylene" group is an unsubstituted or halogen, C1- 4 alkyl or C1- 4 alkoxy substituted phenylene radical and R is a C2- 8 alkyl, alkenyl or mercapto alkyl group, a C4- 8 alkoxyalkyl or alkylmercaptoalkyl group (having at least two carbon atom in the alkylene portion), a phenyl lower alkyl or phenylcyclopropyl group, a cyclohexyl-lower alkyl, cycloheptylmethyl, cycloheptylethyl or cyclo-octylmethyl group, an endoalkylene - cyclohexyl, - cyclohexenyl, -cyclohexylmethyl or cyclohexenylmethyl group, a lower alkyl or lower alkoxycyclohexyl group, a C5- 8 cycloalkyl group, a cyclohexenyl or cyclohexenylmethyl group or a heterocyclic group having 4 or 5 carbon atoms and an oxygen or sulphur atom which may have one or two ethylenic double bonds and is attached to the N-atom directly or through a methylene group, are made by the usual sulphonyl urea syntheses, i.e. reaction of the appropriate benzenesulphonyl urea with an isocyanate RNCO or an equivalent carbamic ester or halide, thiocarbamic ester or urea derivative, or conversely reacting an amine R-NH2 or its salt with an X-Y-substituted benzenesulphonyl isocyanate or its equivalent; reacting a sulphonyl chloride of the formula X-Y-phenylene -SO2Cl with an R-substituted urea, isourea ether, isothiourea ether or parabanic acid and, if required, hydrolysing the product; replacing sulphur by oxygen in the corresponding benzenesulphonyl thiourea, or oxidizing a corresponding benzenesulphenyl or benzenesulphonyl urea; and also by converting a corresponding benzenesulphonyl urea of the formula Z-Y-phenylene-SO2-NH-CO-NHR, in which Z is a phthalic acid mono-amide group which may be partially hydrogenated and/or substituted into the corresponding phthalimide compound by cyclization. Pharmaceutical preparations having hypoglaycaemic comprise the above compounds of the invention in admixture or conjunction with a carrier, preferably in a form adapted to oral administration.

公开(公告)号：DK118661B

公开(公告)日：1970-09-21

申请号：DK468966

申请日：1966-09-12

Applicant: HOECHST AG

Inventor： PESCHKE W

IPC: A61K31/64 ,  C07D209/46 ,  C07D335/02 ,  C07D27/50 ,  C07D27/56

Abstract: Novel benzenesulphonyl ureas of the Formula I and their physiologically tolerable salts wherein R is H or CH3, Z and Z1 are H or halogen atoms or C1- 4 alkyl or alkoxy groups, Y is a straight or branched chain hydrocarbon group of 1-4 carbon atoms and R1 is (a) a 3 or 4 carbon atom alkyl group; (b) a cyclohexylmethyl group; (c) a C1- 3-alkyl-cyclohexyl or C1- 3 alkoxy-cyclohexyl group; (d) a C5- 8 cycloalkyl group; (e) a cyclohexenyl or cyclohexenylmethyl group; or (f) an endoalkylenecyclohexyl, - cyclohexenyl, - cyclohexylmethyl or -cyclohexenylmethyl group each containing 1 or 2 endoalkylene carbon atoms, are made by (a) reacting an appropriately substituted benzenesulphonyl isocyanate, carbamic ester, thiocarbamic ester, carbamic halide or urea with an amine R1NH2; (b) reacting an R1 substituted isocyanate, carbamic or thiocarbamic ester, carbamic halide or urea with the appropriately substituted benzenesulphonamide; (c) hydrolysing the corresponding isourea or isothiourea ether or parabanic acid compound; (d) replacing the sulphur atom in a corresponding benzenesulphonylthiourea by oxygen by known methods; (e) oxidizing a benzenesulphuryl or benzenesulphenyl urea; or (f) subjecting a compound of the Formula III or IV to ring closure Phthalimidinoalkyl - benzenesulphonamides 4-(b - Phthalimidinoethyl) - benzenesulphonamide is made by reacting phthalide with 4-(b -aminoethyl) - benzenesulphonamide and subjecting the resulting 4-(b -o-hydroxymethyl-benzamidoethyl) - benzenesulphonamide to ring closure. 4 - (b - Phthalimidino - a - methylethyl)- benzenesulphonamide is made by reacting 4-a -methyl - b - aminoethyl) benzenesulphonamide with phthalic anhydride and reducing the resulting 4 - (b - phthalimido - a - methylethyl)-benzenesulphonamide with tin and HCl. 4-(b - 5 - Chlorophthalimidoethyl) - benzenesulphonamide is made by reducing the corresponding phthalimide derivative. 4 - Phthalimidinomethyl - benzenesulphonamide and 4 - (b - 3 ethyl - phthalimidinoethyl)-benzenesulphonamide are made by chlorosulphonating the corresponding phthalimidinoalkyl benzenes and treating the resulting sulphonyl chlorides with ammonia. 4 - (b - o - Hydroxymethylbenzamidoethyl)-benzenesulphonamide is prepared by reaction of 4 - (b - aminoethyl) - benzenesulphonamide with phthalide. N - [4 - (b - Phthalimidino - ethyl) - benzenesulphonyl] - N1 - cyclohexyl - isourea methyl ether is formed by treating the corresponding thiourea compound with mercury oxide in methanol. N - [4 - (b - Phthalimidinoethyl) - benzenesulphonyl]-carbamic acid methyl ester is obtained by the action of methyl chloroformate on the corresponding sulphonamide. Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier preferably in a form adapted to oral administration such as tablets.

公开(公告)号：FI45330B

公开(公告)日：1972-01-31

申请号：FI180365

申请日：1965-07-26

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  MUTH K ,  PESCHKE W ,  WEBER H ,  WEYER R

IPC: A61K31/64 ,  C07D209/46 ,  C07D335/02 ,  C07D27/50

Abstract: Novel benzenesulphonyl ureas of the Formula I and their physiologically tolerable salts wherein R is H or CH3, Z and Z1 are H or halogen atoms or C1- 4 alkyl or alkoxy groups, Y is a straight or branched chain hydrocarbon group of 1-4 carbon atoms and R1 is (a) a 3 or 4 carbon atom alkyl group; (b) a cyclohexylmethyl group; (c) a C1- 3-alkyl-cyclohexyl or C1- 3 alkoxy-cyclohexyl group; (d) a C5- 8 cycloalkyl group; (e) a cyclohexenyl or cyclohexenylmethyl group; or (f) an endoalkylenecyclohexyl, - cyclohexenyl, - cyclohexylmethyl or -cyclohexenylmethyl group each containing 1 or 2 endoalkylene carbon atoms, are made by (a) reacting an appropriately substituted benzenesulphonyl isocyanate, carbamic ester, thiocarbamic ester, carbamic halide or urea with an amine R1NH2; (b) reacting an R1 substituted isocyanate, carbamic or thiocarbamic ester, carbamic halide or urea with the appropriately substituted benzenesulphonamide; (c) hydrolysing the corresponding isourea or isothiourea ether or parabanic acid compound; (d) replacing the sulphur atom in a corresponding benzenesulphonylthiourea by oxygen by known methods; (e) oxidizing a benzenesulphuryl or benzenesulphenyl urea; or (f) subjecting a compound of the Formula III or IV to ring closure Phthalimidinoalkyl - benzenesulphonamides 4-(b - Phthalimidinoethyl) - benzenesulphonamide is made by reacting phthalide with 4-(b -aminoethyl) - benzenesulphonamide and subjecting the resulting 4-(b -o-hydroxymethyl-benzamidoethyl) - benzenesulphonamide to ring closure. 4 - (b - Phthalimidino - a - methylethyl)- benzenesulphonamide is made by reacting 4-a -methyl - b - aminoethyl) benzenesulphonamide with phthalic anhydride and reducing the resulting 4 - (b - phthalimido - a - methylethyl)-benzenesulphonamide with tin and HCl. 4-(b - 5 - Chlorophthalimidoethyl) - benzenesulphonamide is made by reducing the corresponding phthalimide derivative. 4 - Phthalimidinomethyl - benzenesulphonamide and 4 - (b - 3 ethyl - phthalimidinoethyl)-benzenesulphonamide are made by chlorosulphonating the corresponding phthalimidinoalkyl benzenes and treating the resulting sulphonyl chlorides with ammonia. 4 - (b - o - Hydroxymethylbenzamidoethyl)-benzenesulphonamide is prepared by reaction of 4 - (b - aminoethyl) - benzenesulphonamide with phthalide. N - [4 - (b - Phthalimidino - ethyl) - benzenesulphonyl] - N1 - cyclohexyl - isourea methyl ether is formed by treating the corresponding thiourea compound with mercury oxide in methanol. N - [4 - (b - Phthalimidinoethyl) - benzenesulphonyl]-carbamic acid methyl ester is obtained by the action of methyl chloroformate on the corresponding sulphonamide. Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier preferably in a form adapted to oral administration such as tablets.

公开(公告)号：NO120317B

公开(公告)日：1970-10-05

申请号：NO16023365

申请日：1965-10-27

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  WEBER H ,  PESCHKE W ,  WEYER R ,  MUTH K

IPC: A61K31/64 ,  C07C311/54 ,  C07D209/48 ,  C07D333/34

Abstract: Novel compounds of the formula X-Y-phenylene-SO2-NH-CO-NHR and their salts, wherein X is a phthalimide group which may be wholly or partly hydrogenated and/or may be mono- or di-substituted by one or two halogen, lower alkyl or lower alkoxy substituents, or is a tetrahydro- or hexahydro - endomethylene - or endoethylene - phthalimide group or a napthalimide, napththalene - 1, 2 - dicarbonimide or naphthalene - 2, 3 - dicarbonimide group; Y is a branched or unbranched C1- 4 hydrocarbon group; the "phenylene" group is an unsubstituted or halogen, C1- 4 alkyl or C1- 4 alkoxy substituted phenylene radical and R is a C2- 8 alkyl, alkenyl or mercapto alkyl group, a C4- 8 alkoxyalkyl or alkylmercaptoalkyl group (having at least two carbon atom in the alkylene portion), a phenyl lower alkyl or phenylcyclopropyl group, a cyclohexyl-lower alkyl, cycloheptylmethyl, cycloheptylethyl or cyclo-octylmethyl group, an endoalkylene - cyclohexyl, - cyclohexenyl, -cyclohexylmethyl or cyclohexenylmethyl group, a lower alkyl or lower alkoxycyclohexyl group, a C5- 8 cycloalkyl group, a cyclohexenyl or cyclohexenylmethyl group or a heterocyclic group having 4 or 5 carbon atoms and an oxygen or sulphur atom which may have one or two ethylenic double bonds and is attached to the N-atom directly or through a methylene group, are made by the usual sulphonyl urea syntheses, i.e. reaction of the appropriate benzenesulphonyl urea with an isocyanate RNCO or an equivalent carbamic ester or halide, thiocarbamic ester or urea derivative, or conversely reacting an amine R-NH2 or its salt with an X-Y-substituted benzenesulphonyl isocyanate or its equivalent; reacting a sulphonyl chloride of the formula X-Y-phenylene -SO2Cl with an R-substituted urea, isourea ether, isothiourea ether or parabanic acid and, if required, hydrolysing the product; replacing sulphur by oxygen in the corresponding benzenesulphonyl thiourea, or oxidizing a corresponding benzenesulphenyl or benzenesulphonyl urea; and also by converting a corresponding benzenesulphonyl urea of the formula Z-Y-phenylene-SO2-NH-CO-NHR, in which Z is a phthalic acid mono-amide group which may be partially hydrogenated and/or substituted into the corresponding phthalimide compound by cyclization. Pharmaceutical preparations having hypoglaycaemic comprise the above compounds of the invention in admixture or conjunction with a carrier, preferably in a form adapted to oral administration.

公开(公告)号：SE314072B

公开(公告)日：1969-09-01

申请号：SE1390965

申请日：1965-10-28

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  WEYER R ,  PESCHKE W ,  WEBER H ,  MUTH K

IPC: A61K31/64 ,  C07C311/54 ,  C07D209/48 ,  C07D333/34 ,  C07C143/833

Abstract: Novel compounds of the formula X-Y-phenylene-SO2-NH-CO-NHR and their salts, wherein X is a phthalimide group which may be wholly or partly hydrogenated and/or may be mono- or di-substituted by one or two halogen, lower alkyl or lower alkoxy substituents, or is a tetrahydro- or hexahydro - endomethylene - or endoethylene - phthalimide group or a napthalimide, napththalene - 1, 2 - dicarbonimide or naphthalene - 2, 3 - dicarbonimide group; Y is a branched or unbranched C1- 4 hydrocarbon group; the "phenylene" group is an unsubstituted or halogen, C1- 4 alkyl or C1- 4 alkoxy substituted phenylene radical and R is a C2- 8 alkyl, alkenyl or mercapto alkyl group, a C4- 8 alkoxyalkyl or alkylmercaptoalkyl group (having at least two carbon atom in the alkylene portion), a phenyl lower alkyl or phenylcyclopropyl group, a cyclohexyl-lower alkyl, cycloheptylmethyl, cycloheptylethyl or cyclo-octylmethyl group, an endoalkylene - cyclohexyl, - cyclohexenyl, -cyclohexylmethyl or cyclohexenylmethyl group, a lower alkyl or lower alkoxycyclohexyl group, a C5- 8 cycloalkyl group, a cyclohexenyl or cyclohexenylmethyl group or a heterocyclic group having 4 or 5 carbon atoms and an oxygen or sulphur atom which may have one or two ethylenic double bonds and is attached to the N-atom directly or through a methylene group, are made by the usual sulphonyl urea syntheses, i.e. reaction of the appropriate benzenesulphonyl urea with an isocyanate RNCO or an equivalent carbamic ester or halide, thiocarbamic ester or urea derivative, or conversely reacting an amine R-NH2 or its salt with an X-Y-substituted benzenesulphonyl isocyanate or its equivalent; reacting a sulphonyl chloride of the formula X-Y-phenylene -SO2Cl with an R-substituted urea, isourea ether, isothiourea ether or parabanic acid and, if required, hydrolysing the product; replacing sulphur by oxygen in the corresponding benzenesulphonyl thiourea, or oxidizing a corresponding benzenesulphenyl or benzenesulphonyl urea; and also by converting a corresponding benzenesulphonyl urea of the formula Z-Y-phenylene-SO2-NH-CO-NHR, in which Z is a phthalic acid mono-amide group which may be partially hydrogenated and/or substituted into the corresponding phthalimide compound by cyclization. Pharmaceutical preparations having hypoglaycaemic comprise the above compounds of the invention in admixture or conjunction with a carrier, preferably in a form adapted to oral administration.

公开(公告)号：DK123869B

公开(公告)日：1972-08-14

申请号：DK469266

申请日：1966-09-12

Applicant: HOECHST AG

Inventor： PESCHKE W

IPC: A61K31/64 ,  C07D209/46 ,  C07D335/02 ,  C07D27/56

Abstract: Novel benzenesulphonyl ureas of the Formula I and their physiologically tolerable salts wherein R is H or CH3, Z and Z1 are H or halogen atoms or C1- 4 alkyl or alkoxy groups, Y is a straight or branched chain hydrocarbon group of 1-4 carbon atoms and R1 is (a) a 3 or 4 carbon atom alkyl group; (b) a cyclohexylmethyl group; (c) a C1- 3-alkyl-cyclohexyl or C1- 3 alkoxy-cyclohexyl group; (d) a C5- 8 cycloalkyl group; (e) a cyclohexenyl or cyclohexenylmethyl group; or (f) an endoalkylenecyclohexyl, - cyclohexenyl, - cyclohexylmethyl or -cyclohexenylmethyl group each containing 1 or 2 endoalkylene carbon atoms, are made by (a) reacting an appropriately substituted benzenesulphonyl isocyanate, carbamic ester, thiocarbamic ester, carbamic halide or urea with an amine R1NH2; (b) reacting an R1 substituted isocyanate, carbamic or thiocarbamic ester, carbamic halide or urea with the appropriately substituted benzenesulphonamide; (c) hydrolysing the corresponding isourea or isothiourea ether or parabanic acid compound; (d) replacing the sulphur atom in a corresponding benzenesulphonylthiourea by oxygen by known methods; (e) oxidizing a benzenesulphuryl or benzenesulphenyl urea; or (f) subjecting a compound of the Formula III or IV to ring closure Phthalimidinoalkyl - benzenesulphonamides 4-(b - Phthalimidinoethyl) - benzenesulphonamide is made by reacting phthalide with 4-(b -aminoethyl) - benzenesulphonamide and subjecting the resulting 4-(b -o-hydroxymethyl-benzamidoethyl) - benzenesulphonamide to ring closure. 4 - (b - Phthalimidino - a - methylethyl)- benzenesulphonamide is made by reacting 4-a -methyl - b - aminoethyl) benzenesulphonamide with phthalic anhydride and reducing the resulting 4 - (b - phthalimido - a - methylethyl)-benzenesulphonamide with tin and HCl. 4-(b - 5 - Chlorophthalimidoethyl) - benzenesulphonamide is made by reducing the corresponding phthalimide derivative. 4 - Phthalimidinomethyl - benzenesulphonamide and 4 - (b - 3 ethyl - phthalimidinoethyl)-benzenesulphonamide are made by chlorosulphonating the corresponding phthalimidinoalkyl benzenes and treating the resulting sulphonyl chlorides with ammonia. 4 - (b - o - Hydroxymethylbenzamidoethyl)-benzenesulphonamide is prepared by reaction of 4 - (b - aminoethyl) - benzenesulphonamide with phthalide. N - [4 - (b - Phthalimidino - ethyl) - benzenesulphonyl] - N1 - cyclohexyl - isourea methyl ether is formed by treating the corresponding thiourea compound with mercury oxide in methanol. N - [4 - (b - Phthalimidinoethyl) - benzenesulphonyl]-carbamic acid methyl ester is obtained by the action of methyl chloroformate on the corresponding sulphonamide. Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier preferably in a form adapted to oral administration such as tablets.

公开(公告)号：DK119007B

公开(公告)日：1970-11-02

申请号：DK469066

申请日：1966-09-12

Applicant: HOECHST AG

Inventor： PESCHKE W

IPC: A61K31/64 ,  C07D209/46 ,  C07D335/02 ,  C07D27/50 ,  C07D27/56

Abstract: Novel benzenesulphonyl ureas of the Formula I and their physiologically tolerable salts wherein R is H or CH3, Z and Z1 are H or halogen atoms or C1- 4 alkyl or alkoxy groups, Y is a straight or branched chain hydrocarbon group of 1-4 carbon atoms and R1 is (a) a 3 or 4 carbon atom alkyl group; (b) a cyclohexylmethyl group; (c) a C1- 3-alkyl-cyclohexyl or C1- 3 alkoxy-cyclohexyl group; (d) a C5- 8 cycloalkyl group; (e) a cyclohexenyl or cyclohexenylmethyl group; or (f) an endoalkylenecyclohexyl, - cyclohexenyl, - cyclohexylmethyl or -cyclohexenylmethyl group each containing 1 or 2 endoalkylene carbon atoms, are made by (a) reacting an appropriately substituted benzenesulphonyl isocyanate, carbamic ester, thiocarbamic ester, carbamic halide or urea with an amine R1NH2; (b) reacting an R1 substituted isocyanate, carbamic or thiocarbamic ester, carbamic halide or urea with the appropriately substituted benzenesulphonamide; (c) hydrolysing the corresponding isourea or isothiourea ether or parabanic acid compound; (d) replacing the sulphur atom in a corresponding benzenesulphonylthiourea by oxygen by known methods; (e) oxidizing a benzenesulphuryl or benzenesulphenyl urea; or (f) subjecting a compound of the Formula III or IV to ring closure Phthalimidinoalkyl - benzenesulphonamides 4-(b - Phthalimidinoethyl) - benzenesulphonamide is made by reacting phthalide with 4-(b -aminoethyl) - benzenesulphonamide and subjecting the resulting 4-(b -o-hydroxymethyl-benzamidoethyl) - benzenesulphonamide to ring closure. 4 - (b - Phthalimidino - a - methylethyl)- benzenesulphonamide is made by reacting 4-a -methyl - b - aminoethyl) benzenesulphonamide with phthalic anhydride and reducing the resulting 4 - (b - phthalimido - a - methylethyl)-benzenesulphonamide with tin and HCl. 4-(b - 5 - Chlorophthalimidoethyl) - benzenesulphonamide is made by reducing the corresponding phthalimide derivative. 4 - Phthalimidinomethyl - benzenesulphonamide and 4 - (b - 3 ethyl - phthalimidinoethyl)-benzenesulphonamide are made by chlorosulphonating the corresponding phthalimidinoalkyl benzenes and treating the resulting sulphonyl chlorides with ammonia. 4 - (b - o - Hydroxymethylbenzamidoethyl)-benzenesulphonamide is prepared by reaction of 4 - (b - aminoethyl) - benzenesulphonamide with phthalide. N - [4 - (b - Phthalimidino - ethyl) - benzenesulphonyl] - N1 - cyclohexyl - isourea methyl ether is formed by treating the corresponding thiourea compound with mercury oxide in methanol. N - [4 - (b - Phthalimidinoethyl) - benzenesulphonyl]-carbamic acid methyl ester is obtained by the action of methyl chloroformate on the corresponding sulphonamide. Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier preferably in a form adapted to oral administration such as tablets.

公开(公告)号：NO122923B

公开(公告)日：1971-09-06

申请号：NO15913665

申请日：1965-07-29

Applicant: HOECHST AG

Inventor： AUMUELLER W ,  MUTH K ,  PESCHKE W ,  WEBER H ,  WEYER R

IPC: A61K31/64 ,  C07D209/46 ,  C07D335/02

Abstract: Novel benzenesulphonyl ureas of the Formula I and their physiologically tolerable salts wherein R is H or CH3, Z and Z1 are H or halogen atoms or C1- 4 alkyl or alkoxy groups, Y is a straight or branched chain hydrocarbon group of 1-4 carbon atoms and R1 is (a) a 3 or 4 carbon atom alkyl group; (b) a cyclohexylmethyl group; (c) a C1- 3-alkyl-cyclohexyl or C1- 3 alkoxy-cyclohexyl group; (d) a C5- 8 cycloalkyl group; (e) a cyclohexenyl or cyclohexenylmethyl group; or (f) an endoalkylenecyclohexyl, - cyclohexenyl, - cyclohexylmethyl or -cyclohexenylmethyl group each containing 1 or 2 endoalkylene carbon atoms, are made by (a) reacting an appropriately substituted benzenesulphonyl isocyanate, carbamic ester, thiocarbamic ester, carbamic halide or urea with an amine R1NH2; (b) reacting an R1 substituted isocyanate, carbamic or thiocarbamic ester, carbamic halide or urea with the appropriately substituted benzenesulphonamide; (c) hydrolysing the corresponding isourea or isothiourea ether or parabanic acid compound; (d) replacing the sulphur atom in a corresponding benzenesulphonylthiourea by oxygen by known methods; (e) oxidizing a benzenesulphuryl or benzenesulphenyl urea; or (f) subjecting a compound of the Formula III or IV to ring closure Phthalimidinoalkyl - benzenesulphonamides 4-(b - Phthalimidinoethyl) - benzenesulphonamide is made by reacting phthalide with 4-(b -aminoethyl) - benzenesulphonamide and subjecting the resulting 4-(b -o-hydroxymethyl-benzamidoethyl) - benzenesulphonamide to ring closure. 4 - (b - Phthalimidino - a - methylethyl)- benzenesulphonamide is made by reacting 4-a -methyl - b - aminoethyl) benzenesulphonamide with phthalic anhydride and reducing the resulting 4 - (b - phthalimido - a - methylethyl)-benzenesulphonamide with tin and HCl. 4-(b - 5 - Chlorophthalimidoethyl) - benzenesulphonamide is made by reducing the corresponding phthalimide derivative. 4 - Phthalimidinomethyl - benzenesulphonamide and 4 - (b - 3 ethyl - phthalimidinoethyl)-benzenesulphonamide are made by chlorosulphonating the corresponding phthalimidinoalkyl benzenes and treating the resulting sulphonyl chlorides with ammonia. 4 - (b - o - Hydroxymethylbenzamidoethyl)-benzenesulphonamide is prepared by reaction of 4 - (b - aminoethyl) - benzenesulphonamide with phthalide. N - [4 - (b - Phthalimidino - ethyl) - benzenesulphonyl] - N1 - cyclohexyl - isourea methyl ether is formed by treating the corresponding thiourea compound with mercury oxide in methanol. N - [4 - (b - Phthalimidinoethyl) - benzenesulphonyl]-carbamic acid methyl ester is obtained by the action of methyl chloroformate on the corresponding sulphonamide. Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier preferably in a form adapted to oral administration such as tablets.