GB604259A - Manufacture of 4-aminobenzenesulphonyl-ureas - Google Patents

Manufacture of 4-aminobenzenesulphonyl-ureas

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Publication number
GB604259A
GB604259A GB34855/45A GB3485545A GB604259A GB 604259 A GB604259 A GB 604259A GB 34855/45 A GB34855/45 A GB 34855/45A GB 3485545 A GB3485545 A GB 3485545A GB 604259 A GB604259 A GB 604259A
Authority
GB
United Kingdom
Prior art keywords
sulphonamide
aminobenzenesulphonyl
benzylamine
urea
formula
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
GB34855/45A
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.)
Novartis AG
Original Assignee
JR Geigy 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 JR Geigy AG filed Critical JR Geigy AG
Publication of GB604259A publication Critical patent/GB604259A/en
Expired legal-status Critical Current

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Abstract

4 - Aminobenzene - sulphonyl ureas of the general formula <FORM:0604259/IV(b)/1> (in which Ar represents a substituted or unsubstituted phenyl group) are prepared by the following processes: (a) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/2> (in which R represents a substituent convertible into an amino group and X represents hydrogen or a metal) with a benzyl derivative of the formula Y-CH2-Ar (in which Y is an isocyano group, an acid-azide group or an acid-halogenamide group), and subsequently converting R into an amino group; (b) treating a benzene sulphonamide as in (a) with a benzyl derivative of the general formula Z-CO-NH-CH2-Ar (in which Z is a halogen atom, an alkoxy or thioalkoxy group) and subsequently converting R into an amino group; (c) treating a benzene sulphonamide of formula <FORM:0604259/IV(b)/3> with a benzyl derivative of the formula Alkoxy -CO-NH-CH2-Ar; (d) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/4> (in which R1 is an amino group or a substituent convertible into an amino group) with a benzyl derivative of the formula NH2-CO-NH-CH2 -Ar and, when necessary, subsequently converting the convertible group into an amino group; (e) treating a benzene sulphonyl halide with a benzylisourea-O-alkyl ether of the formula <FORM:0604259/IV(b)/5> NH2-C(O Alkyl)=N-CH2-Ar, hydrolysing the product and converting R into an amino group; (f) treating a benzene sulphonamide as in (a) with a benzyl isothiocyanate, exchanging the sulphur atom in the thiourea derivative for oxygen by means of a desulphurizing agent, e.g. an alcoholic solution of silver nitrate, and subsequently converting R into an amino group; (g) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/6> with a benzylamine and subsequently converting the R into an amino group; (h) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/7> with a benzylamine and, when necessary, converting R1 into an amino group; (i) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/8> with a benzylamine of the formula U-NH-CH2-Ar (in which U represents H or alkyl) or with a salt of such amine with an inorganic acid, and when necessary, converting R1 into an amino group, and (j) treating a benzene sulphonamide of the formula <FORM:0604259/IV(b)/9> with a benzylamine or with a salt of such amine with an inorganic acid, exchanging the sulphur atom in the product for oxygen by means of a desulphurizing agent, and subsequently converting the R into an amino group. Salts of N-(4-aminobenzenesulphonyl)-N1-benzylurea are made by treating with a base, e.g. alkalis, alkali carbonates and bicarbonates, magnesium hydroxide, alkaline earth metal hydroxides, diethylamine, morpholine, aminoethanol and ethylene diamine. In examples: (1) N-(4-aminobenzenesulphonyl) - N1 - benzylurea (and similarly N - (4 - aminobenzenesulphonyl) - N1 - (31,41 - dimethylbenzyl) - urea) is obtained from 4-acetylaminobenzenesulphonamide and benzyl isocyanate; (2), (3) and (4) the sodium, ethylenediamine and calcium salts are prepared from N - (4 - aminobenzenesulphonyl) - N1 - benzylurea; N - (4-aminobenzenesulphonyl) - N1 - benzylurea is made from (5) sodium 4-carbomethoxyaminobenzene sulphonamide and benzyl isocyanate; (6) sodium 4-nitrobenzene sulphonamide and benzyl isocyanate; (7) 4-nitrobenzene sulphonamide, benzylamine and phosgene; (8) potassium 4-aminobenzene sulphonamide and benzylaminocarbonic acid methyl ester; (9) 4-acetylaminobenzene sulphochloride and benzyl isourea-O-methyl ether methyl sulphate; (10) 4 - acetylaminobenzene sulphonamide and benzylurea; (11) 4-aminobenzene sulphonamide and benzylurea; (12) sodium 4-nitrobenzene sulphonamide, phenylacetic acid chloride and sodium azide; (13) sodium 4-acetylaminobenzene sulphonamide and N-bromophenylacetamide and (14) sodium 4-acetylamino benzene sulphonamide and benzyl isothiocyanate; (15) N-(4-aminobenzenesulphonyl)-N1-(31, 41-dimethylbenzyl)-urea is made from sodium 4-nitrobenzene sulphonamide and 3,4-dimethylbenzyl isocyanate; (16) N-(4-aminobenzenesulphonyl) - N1 - (41 - methylbenzyl) - urea is made from 4-acetylaminobenzene sulphonamide and 4-methylbenzyl isocyanate; N-(4-aminobenzenesulphonyl) - N1 - benzyl urea is made from (17) 4-nitrobenzene sulphochloride, silver cyanate and benzylamine; (18) 4-acetylaminobenzene sulphonamidocarbonic acid methyl ester and benzylamine; (19) 4-acetylaminobenzenesulphonyl urea and benzylamine; (20) 4-nitrobenzenesulphonyl urea and benzylamine; (21) 4-aminobenzenesulphonyl urea and benzylamine; (22) 4-acetylaminobenzenesulphonyl urea and benzyl-methylamine hydrochloride; (23) sodium 4-nitrobenzenesulphonyl urea and benzylamine, and (24) 4-acetylaminobenzenesulphonyl thiourea and benzylamine, using silver nitrate to desulphurize the intermediate product. Specification 538,884 is referred to. The Specification as open to inspection under Sect. 91 relates also to the preparation of compounds <FORM:0604259/IV(b)/100> in which R may be alkyl or cycloalkyl groups and includes also examples in which N-aminobenzenesulphonyl)-N1-benzylurea is made from (a) 4-nitrobenzene sulphenic acid chloride and benzylurea; (b) 4-nitrobenzene sulphenamide and benzyl isocyanate; and (c) N-(4-nitrobenzenesulphinyl)-urea and benzylamine; (d) N-(4-aminobenzenesulphonyl) - N1 - (a - methylbenzyl) - urea is made from 4 - acetylamino - benzene sulphonamide and a -methylbenzyl isocyanate; (e) N-(4-aminobenzenesulphonyl)-N1-(a -ethylbenzyl)-urea is made from sodium 4-nitrobenzene sulphonamide and a -ethylbenzyl isocyanate; and (f) N-(4-aminobenzenesulphonyl)-N1-[a -(n-propyl)-31, 41-dimethylbenzyl]-urea is made from 4-nitrobenzene sulphonamide and a -(n-propyl)-3,4-dimethylbenzyl isocyanate. This subject-matter does not appear in the Specification as accepted.
GB34855/45A 1944-12-28 1945-12-22 Manufacture of 4-aminobenzenesulphonyl-ureas Expired GB604259A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH604259X 1944-12-28

Publications (1)

Publication Number Publication Date
GB604259A true GB604259A (en) 1948-06-30

Family

ID=4522932

Family Applications (1)

Application Number Title Priority Date Filing Date
GB34855/45A Expired GB604259A (en) 1944-12-28 1945-12-22 Manufacture of 4-aminobenzenesulphonyl-ureas

Country Status (1)

Country Link
GB (1) GB604259A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2666073A (en) * 1951-01-19 1954-01-12 Chemie Linz Ag Process for the manufacture of n1-acylated aminoarylsulfonamides
DE974062C (en) * 1955-08-09 1960-09-01 Hoechst Ag Process for the preparation of new benzenesulfonylureas
DE1114804B (en) * 1959-04-07 1961-10-12 Cilag Chemie Process for the preparation of N-arylsulfonyl-N'-alkyl-ureas
US3005022A (en) * 1958-01-28 1961-10-17 Pfizer & Co C Process for the production of sulfonylureas
US3013072A (en) * 1958-09-02 1961-12-12 Pfizer & Co C Novel process for the production of sulfonylureas
US3069466A (en) * 1959-04-21 1962-12-18 Anton Von Waldheim New n1-halogenoalkyl-phenyl-sulfonyl-n2-substituted ureas, and the corresponding cyclohexyl compounds
US3075012A (en) * 1959-04-07 1963-01-22 Cilag Chemie Process for the production of n1-arylsulfonyl-n2-alkyl ureas
US3097241A (en) * 1956-08-10 1963-07-09 Hoechst Ag Nu-cyclohexane-sulphonyl-n'-(beta-phenylethyl)-urea
US3121102A (en) * 1959-01-26 1964-02-11 Merck & Co Inc Process for preparing sulfonylureas
US3832397A (en) * 1970-03-19 1974-08-27 Hoffmann La Roche Process for substituted sulfonylureas
WO2008147797A3 (en) * 2007-05-25 2009-07-09 Vertex Pharma Ion channel modulators and methods of use

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2666073A (en) * 1951-01-19 1954-01-12 Chemie Linz Ag Process for the manufacture of n1-acylated aminoarylsulfonamides
DE974062C (en) * 1955-08-09 1960-09-01 Hoechst Ag Process for the preparation of new benzenesulfonylureas
US3097241A (en) * 1956-08-10 1963-07-09 Hoechst Ag Nu-cyclohexane-sulphonyl-n'-(beta-phenylethyl)-urea
US3005022A (en) * 1958-01-28 1961-10-17 Pfizer & Co C Process for the production of sulfonylureas
US3013072A (en) * 1958-09-02 1961-12-12 Pfizer & Co C Novel process for the production of sulfonylureas
US3121102A (en) * 1959-01-26 1964-02-11 Merck & Co Inc Process for preparing sulfonylureas
DE1114804B (en) * 1959-04-07 1961-10-12 Cilag Chemie Process for the preparation of N-arylsulfonyl-N'-alkyl-ureas
US3075012A (en) * 1959-04-07 1963-01-22 Cilag Chemie Process for the production of n1-arylsulfonyl-n2-alkyl ureas
US3069466A (en) * 1959-04-21 1962-12-18 Anton Von Waldheim New n1-halogenoalkyl-phenyl-sulfonyl-n2-substituted ureas, and the corresponding cyclohexyl compounds
US3832397A (en) * 1970-03-19 1974-08-27 Hoffmann La Roche Process for substituted sulfonylureas
WO2008147797A3 (en) * 2007-05-25 2009-07-09 Vertex Pharma Ion channel modulators and methods of use
US8193194B2 (en) 2007-05-25 2012-06-05 Vertex Pharmaceuticals Incorporated Ion channel modulators and methods of use

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