GB791923A - New sulphonamides - Google Patents

New sulphonamides

Info

Publication number
GB791923A
GB791923A GB22803/55A GB2280355A GB791923A GB 791923 A GB791923 A GB 791923A GB 22803/55 A GB22803/55 A GB 22803/55A GB 2280355 A GB2280355 A GB 2280355A GB 791923 A GB791923 A GB 791923A
Authority
GB
United Kingdom
Prior art keywords
substituted
chloro
methyl
ethyl
amino
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
GB22803/55A
Inventor
Francis Leslie Rose
Alfred Spinks
Charles Henry Vasey
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB22803/55A priority Critical patent/GB791923A/en
Publication of GB791923A publication Critical patent/GB791923A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C315/00Preparation of sulfones; Preparation of sulfoxides
    • C07C315/02Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00Preparation of carboxylic acid amides
    • C07C231/12Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention comprises sulphonamides of the general formula <FORM:0791923/IV (b)/1> wherein R is a hydrocarbon radical which may be substituted, x is 1 or 2, R1 is hydrogen or an alkyl radical of 1-4 carbon atoms, and the nucleus A may be further substituted, otherwise than by amino groups, with the proviso that when R is a methyl, a p-nitro- or p-aminophenyl radical R1 does not stand for hydrogen; and the manufacture thereof by (1) oxidation of compounds of the general formula <FORM:0791923/IV (b)/2> (e.g. with hydrogen peroxide), or (2) interaction of compounds of the general formula <FORM:0791923/IV (b)/3> wherein X is a halogen atom, with a compound of the formula NH2.R1 (both processes (1) and (2) may take place in the presence of an inert solvent and the reaction may be assisted and/or completed by the application of heat); also pharmaceutical compositions containing these products (see Group VI). In examples, sulphonamides of the general formula, where x= 2, R1=H and R=ethyl-, n-propyl-, isopropyl-, n-butyl-, cyclohexyl-, 4-nitrobenzyl-, phenyl-, 4-chlorophenyl-, and 4-bromophenyl-; where x=2, R1=H, R=ethyl-, and the ring A is substituted as follows: 3-chloro-, 3-bromo-, 3 : 5-dibromo-, 3-methyl-, 3-bromo-5-methyl-, 3 : 5-dichloro-, 3 : 6-dichloro-; where x=2, R1=methyl, R=ethyl, and the ring A is substituted by 3-chloro-; and where x=2, R1=H, R=phenyl and A is substituted by 2-chloro-, are formed by oxidation of the corresponding thio-compounds as in process (1). Similarly, examples are given of the preparation of compounds wherein x=1, R1=H, and R=isopropyl or n-propyl by the same process except that the heating period is shortened or the reaction takes place at 20-25 DEG C. In further examples, using process (2), sulphonamides wherein x=2, R1=H and R=isopropyl, or R=ethyl, with A substituted by 2-chloro-, are prepared by converting the corresponding sulphonylbenzene sulphonic acid to the acid chloride and reacting this with ammonia. The Provisional Specification also refers to the preparation of compounds wherein x=2 by oxidation of corresponding compounds wherein x=1, by hydrogen peroxide. Starting materials. 4 - R - Thiobenzenesulphonamides (wherein R=ethyl, n-propyl, isopropyl, n-butyl, cyclohexyl and 4-nitrobenzyl) are prepared by reacting diazotized 4-aminobenzene-sulphonic acid with potassium ethyl xanthate, alkylating or aralkylating the resulting mercapto benzene sulphonate, and converting this into the acid chloride and thence into the amide. 4 - Ethylthiobenzenesulphonamides (wherein the ring A is substituted by halogen and/or methyl) are prepared in a similar manner to that above but using the appropriately substituted 4-amino benzene sulphonic acid. 4 : 21 - Dichlorodiphenylsulphide - 41 - sulphonamide, as above, using 4-amino-3-chlorobenzenesulphonic acid and 4-nitrochlorobenzene, in place of the alkylating agent, and with subsequent reduction of the nitro group. 4-Chloro- and 4-bromo-diphenylsulphide-41-sulphonamides are prepared by reduction of 4-nitro-diphenylsulphide - 41 - sulphonamide, diazotization and replacement of the amino group by -Cl or -Br. 4 - n - and iso - propylsulphonylbenzene sulphonic acids, from the corresponding thiosulphonic acids, by oxidation with hydrogen peroxide. 2 - Chloro - 4 - ethylsulphonylbenzene sulphonic acid is prepared from ethyl-4-chlorophenyl-sulphone by nitration to give 2-chloro-5-ethylsulphonyl-1-nitrobenzene, converting this to sodium 4 - ethylsulphonyl - 2 - nitrobenzene sulphonate, with sodium sulphite, reducing this to the amino compound, diazotizing and replacing the amino group by Cl.ALSO:Pharmaceutical compositions (e.g. tablets, pills and dispersions) comprise, as active ingredients, one or more sulphonamides of the general formula <FORM:0791923/VI/1> (wherein R is a hydrocarbon radical which may be substituted, x is 1 or 2, R1 is hydrogen or an alkyl radical of one to four carbon atoms, and the nucleus A may be further substituted, otherwise than by amino groups, with the proviso that when R is a methyl, a p-nitro- or p-amino-phenyl radical R1 does not stand for hydrogen), mixed with one or more pharmaceutical excipients. Tablets and pills may contain 5-90 per cent by weight of active ingredient or ingredients together with a diluent (e.g. calcium carbonate or lactose), a disintegrating agent (e.g. maize starch), a lubricating agent (e.g. stearic acid or magnesium stearate) and/or a granulating or binding agent (e.g. starch paste, gelatin solution or gum acacia), and aqueous dispersions may contain not less than 0.5-50 per cent by weight of active ingredient or ingredients in an aqueous medium together with a suspending or dispersing agent (e.g. sodium carboxymethyl cellulose) and/or a wetting agent (e.g. a polyethyleneoxycetanol). In examples: 3 - chloro - 4 - ethylsulphonylsulphonamide is mixed with maize starch and/or calcium carbonate and granulated by admixture with an aqueous solution of acacia, followed by compression into tablet form; 4-chloro-diphenyl-41-sulphonamide is ball milled with a pharmaceutical base comprising icing sugar, sodium carboxymethylcellulose solution, heptadecaethylene-oxycetanol and methyl- and propyl-p-hydroxybenzoates.
GB22803/55A 1955-08-08 1955-08-08 New sulphonamides Expired GB791923A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB22803/55A GB791923A (en) 1955-08-08 1955-08-08 New sulphonamides

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB22803/55A GB791923A (en) 1955-08-08 1955-08-08 New sulphonamides

Publications (1)

Publication Number Publication Date
GB791923A true GB791923A (en) 1958-03-12

Family

ID=10185309

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22803/55A Expired GB791923A (en) 1955-08-08 1955-08-08 New sulphonamides

Country Status (1)

Country Link
GB (1) GB791923A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4476321A (en) * 1980-07-17 1984-10-09 Ciba-Geigy Corporation O-Substituted phenylsulfonamides
US4678855A (en) * 1985-10-09 1987-07-07 Merck & Co., Inc. Substituted benzenesulfonamides

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4476321A (en) * 1980-07-17 1984-10-09 Ciba-Geigy Corporation O-Substituted phenylsulfonamides
US4510325A (en) * 1980-07-17 1985-04-09 Ciba-Geigy Corporation Phenyl sulfonamides
US4678855A (en) * 1985-10-09 1987-07-07 Merck & Co., Inc. Substituted benzenesulfonamides

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