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1. 发明专利

GB595235A Improvements in or relating to the manufacture of substituted sulphonamido compounds 未知
公开(公告)号：GB595235A
公开(公告)日：1947-11-28
申请号：GB2577047
申请日：1943-07-19
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , HERBERT WILLIAM GODDARD , PETER ALFRED WILKINSON
IPC分类号： C07C311/64
摘要： Sulphonamides of the general formula or in which X is a chlorine or bromine atom or an amino or acylamino group are prepared by heating the sulphonamide with a guanidine salt in the presence of a strong base at a temperature such that ammonia is formed. In a modification, the guanidine salt is reacted with the alkali metal derivative of the sulphonamide. The process may be effected at 110 DEG to 200 DEG C., if desired in the presence of a solvent such as ethylene glycol. Guanidine sulphate and carbonate are specified as suitable guanidine salts. In an example, sulphanilamide, guanidine sulphate, potassium hydroxide and ethylene glycol are heated to 160 DEG C. for 45 minutes, and p-aminobenzene-sulphonyl guanidine is separated from the product.

2. 发明专利

GB614193A Improvements in and relating to the preparation of derivatives of cholesterol 未知
公开(公告)号：GB614193A
公开(公告)日：1948-12-10
申请号：GB2017646
申请日：1946-07-05
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , PETER ALFRED WILKINSON
IPC分类号： C07J9/00 , C07J75/00
摘要： 7-Halogenocholesteryl halides are obtained by treating cholesteryl chloride or bromide in a suitable solvent with a halogenating agent, e.g. N-bromosuccimide, N-bromophthalimide, unsubstituted N-chloro- or bromo-amides of fatty acids having not more than 6 carbon atoms in the molecule, N-chloro- or bromo-acetanilides, having on the para position and, if desired, on either or both of the ortho positions of the benzene ring, groupings such as will prevent the migration of the N-halogen into the para and/or ortho position, these substituents being of such a nature as to be inert to the reagents or products in the reaction mixture, substances having the formula R.CO.NH.X, where X is chlorine or bromine and R is phenyl or substituted phenyl, excluding such substituents as would react under the conditions of the reaction either with the halogenating agent or with the halogenated steroid. Suitable solvents are those which under reaction conditions are inert both to the reaction components and products, e.g. petrol b.p. about 80 DEG C. Preferably, the reaction is brought about by heating to the b.p. of the solvent. The 7-halogencholesteryl halide may with or without isolation be dehydrohalogenated by methods described in Specification 574,432. Detailed examples are given of methods using N-bromosuccinimide as a halogenating agent.

3. 发明专利

GB609913A Improvements in and relating to the preparation of derivatives of cholesterol 未知
公开(公告)号：GB609913A
公开(公告)日：1948-10-08
申请号：GB914746
申请日：1946-03-25
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , RALPH JOHN NICHOLLS , PETER ALFRED WILKINSON
摘要： 7-Halogeno derivatives of cholesteryl esters are obtained by reacting a 3-ester of cholesterol, i.e. a carboxylic acid ester in an inert solvent, e.g. 60-80 DEG C. petrol, carbon tetrachloride, benzene and cyclohexane with a halogenator of the formula R.CO.NH.X, where X is bromine or chlorine and R is phenyl or substituted phenyl, e.g. the N-bromo-derivative of benzamide, m - nitrobenzamide, p - nitrobenzamide and p-methoxybenzamide. The ester, solvent and halogenator must be such as will not react with the halogenated steroid. The resulting 7-halogeno compound may be dehydrohalogenated, e.g. by methods described in Specification 574,432, to the 7-dehydro compound with or without hydrolysis of the ester group. In examples: (1) cholesteryl acetate is treated with N-bromobenzamide in petroleum ether and after heating with diethylaniline and hydrolysing, 7-dehydrocholesterol is obtained; (2) to (8) as in (1) using as halogenators, N-bromo - m - nitrobenzamide, N - bromo - p - benzamide and N-bromo-3 : 5-dinitrobenzamide.

4. 发明专利

GB604563A Improvements in and relating to the purification of penicillin salts 未知
公开(公告)号：GB604563A
公开(公告)日：1948-07-06
申请号：GB3203245
申请日：1945-11-27
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , WILLIAM GRAHAM , ERNEST LESTER SMITH , PETER ALFRED WILKINSON
IPC分类号： C07D499/00 , C07D499/26
摘要： Salts of penicillin of a high degree of purity are prepared by dissolving a crude metallic (preferably sodium or calcium) salt of penicillin (preferably of not less than 20 per cent purity) in water (preferably in such quantity as to give a concentration of about 1 per cent w/v.), acidifying (preferably to about pH 2.5) with a strong acid, and combining the liberated penicillin acid with one or more tertiary organic bases selected from N-alkylated piperidines, with or without one or more methyl groups as substituents on the carbon atoms of the ring, or N-alkylated pyrrolidines, with or without one or more methyl or ethyl groups (or both) as substituents on the carbon atoms of the ring, the total number of exocyclic carbon atoms in either case not exceeding 5. Preferably, the free penicillin is extracted, before combination with the base, into a suitable solvent (i.e. one into which penicillin can be extracted readily from acidified aqueous solution and which is relatively inert to penicillin, and in which the tertiary base salts of penicillin are relatively insoluble), preferably so as to give a concentration of penicillin therein of 0.25-5 per cent w/v, and advantageously after adding to the aqueous solution a highly soluble neutral inorganic salt commonly used for salting out purposes, and there is added to the extract a suitable secondary solvent (capable of retaining the tertiary base salts of the impurities in solution). As an alternative or in addition to adding the secondary solvent, the precipitate subsequently produced by the addition of at least (and usually considerably more than) one molar equivalent of the tertiary base or bases is washed with (or crystallized from) the secondary solvent or a mixture thereof with the first solvent, and may, if desired, be further purified by recrystallization from an organic solvent or mixture of solvents. To obtain a metal salt of penicillin of a similar high degree of purity, an aqueous solution of the tertiary base salt is treated with a mineral acid, the liberated penicillin is extracted into an organic solvent, and there is added to the extract an aqueous solution or suspension of a metallic hydroxide. In examples: (1) crude penicillin sodium or calcium salt is dissolved in ice-cold water with the addition of sodium chloride followed by ether and then by dilute phosphoric acid, the ether layer is separated the residue extracted with more ether, the combined ethered extracts filtered at -80 DEG C. and shaken with charcoal which is separated by filtration and eluted with ether, then acetone is added to the eluate, followed by a solution of N-ethyl-piperidine in ether, the precipitated salt is filtered off, washed with acetone, dried, and recrystallized if desired by dissolving in warm methylene chloride, adding acetone and then slowly adding carbon tetrachloride; the product may be converted into the pure sodium salt by dissolving it in ice-cold water, shaking with chloroform while adding dilute phosphoric acid, again extracting the aqueous layer with chloroform, neutralizing the combined extracts with aqueous sodium hydroxide, freeze-drying and crystallizing from acetone; (2) the ethereal solution obtained as in (1) is treated with N-n-propylpiperidine, either with the preliminary addition of acetone or with recrystallization of the precipitated salt therefrom; (3) crude penicillin calcium salt is treated as in (1) but using methyl isobutyl ketone instead of ether; (4) crude penicillin calcium salt is treated as in (1) but using methyl ethyl ketone as the secondary solvent and N-ethylhexahydro-a -picoline as the base; (5) the N-ethylpiperidine in (1) is replaced by N-ethylpyrrolidine. Amyl acetate is additionally specified as a suitable first solvent, and sodium nitrate, sodium sulphate, ammonium sulphate, magnesium sulphate and potassium chloride as salting out agents.

5. 发明专利

GB614194A Improvements in and relating to the preparation of derivatives of cholesterol 未知
公开(公告)号：GB614194A
公开(公告)日：1948-12-10
申请号：GB2017746
申请日：1946-07-05
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , PETER ALFRED WILKINSON
IPC分类号： C07J9/00 , C07J75/00
摘要： 7-Halogenocholesteryl ethers are obtained by treating cholesterol etherified in the 3-position in a suitable solvent with a halogenating agent, e.g. N-bromosuccinimide, N-bromophthalimide, unsubstituted N-chloro- or bromo-amides of fatty acids, having not more than six carbon atoms in the molecule, N-chloro- or bromoacetanilides, having on the para p position and, if desired, on either or both of the ortho positions of the benzene ring, groupings such as will prevent the migration of the N-halogen into the para and/or ortho position, these substituents being of such a nature as to be inert to the reagents or products in the reaction mixture, substances having the formula R.CO.NH.X, where X is bromine or chlorine and R is phenyl or substituted phenyl, excluding such substituents as would react under the conditions of the reaction either with the halogenating agent or with the halogenated steroid. Suitable solvents are those which under reaction conditions are inert both to the reaction components and products, e.g. petrol b.p. about 80 DEG C. Preferably, the reaction is brought about by heating to the b.p. of the solvent. The 7-halogen cholesteryl ether may, with or without isolation, be dehydrohalogenated by methods described in Specification 574,432. Detailed examples are given of methods using N - bromosuccimide as a halogenating agent.

6. 发明专利

GB595177A Improvements in or relating to the manufacture of substituted sulphonamido compounds 未知
公开(公告)号：GB595177A
公开(公告)日：1947-11-28
申请号：GB1171543
申请日：1943-07-19
申请人： GLAXO LAB LTD , AUSTIN ERNEST BIDE , HERBERT WILLIAM GODDARD , PETER ALFRED WILKINSON
IPC分类号： C07C311/37
摘要： Substituted sulphonamido compounds of therapeutic interest are formed by heating a benzenesulphonamide of the general formula or an alkali metal derivative thereof, with a compound, other than guanidine, of the type (X representing a chlorine or bromine atom, or an amino, or mono-acyl amino group; Y representing an alkyl, aryl or aralkyl radical, or an amino group; and R representing a hydrogen atom or alkyl, aryl or aralkyl radical), which may be generated in situ in the reaction-mixture by decomposing a salt thereof, e.g. the carbonate or sulphate, at a temperature generally within the approximate range 110 DEG to 200 DEG C., so as to eliminate a compound of the formula R.NH2. The process may be effected in the presence of a solvent or diluent, e.g. ethylene glycol, of boiling-point not less than the temperature of reaction. The reaction yields a compound of the general formula with elimination of the compound R.NH2, or may produce this derivative together with a compound of the general formula each of these types existing in their corresponding tautomeric forms. Numerous examples are given. Ethylguanidine sulphate is prepared by refluxing methyl iso-thiourea sulphate, water and alcoholic ethylamine solution. o-4-Xylylguanidine sulphate is prepared by heating a well-ground mixture of o-4-xylidine and methyl iso-thiourea sulphate, triturating the cooled melt with 95 per cent ethyl alcohol and standing for 10-12 hours. o-4-Xylylguanidine carbonate is prepared by treating with sodium hydroxide solution an aqueous solution of crude o-4-xylylguanidine sulphate and extracting with chloroform. Nonamidine hydrochloride is prepared by treating a mixture of nononitrile and dry ethyl alcohol with dry hydrogen chloride and then refrigerating for 3 days to crystallise noniminoethyl-ether hydrochloride; dry ethyl alcohol is stirred in, followed by dry alcoholic ammonia solution and the mixture maintained at 30-40 DEG C. for 36 hours, prior to evaporating the filtrate to dryness and recrystallizing the residue. n-Octylguanidine sulphate is prepared by refluxing together methyl iso-thiourea sulphate, n-octylamine, water and ethyl alcohol until methyl mercaptan is no longer evolved.

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