GB905778A - Improvements in or relating to penicillins - Google Patents
Improvements in or relating to penicillinsInfo
- Publication number
- GB905778A GB905778A GB1141260A GB1141260A GB905778A GB 905778 A GB905778 A GB 905778A GB 1141260 A GB1141260 A GB 1141260A GB 1141260 A GB1141260 A GB 1141260A GB 905778 A GB905778 A GB 905778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carboxylic acid
- prepared
- chloride
- followed
- bromo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Relates to penicillins of the general formula: <FORM:0905778/IV (b)/1> and non-toxic salts thereof, where Z is the residue of a substituted or unsubstituted heterocyclic ring system and R1 and R2 are the same of different and are each an alkyl, aryl, acyl, aralkyl, cycloalkyl, heterocyclic, alkoxy, aryloxy, aralkoxy, alkylthio, arylthio or aralkylthio group which may be substituted or a halogen atom, or R1 or R2 may form part of a further substituted or unsubstituted cyclic system fused to the ring containing Z. The Specification contains many examples of penicillins of the above formula of which the following are typical:- 5 - methyl - 3 - phenyl-4-isoxayolyl, 3-methyl-5-phenyl-4-isoxayolyl, 3 - p-chlorophenyl-5-methyl-4-isoxayolyl, 2:4-dichloro-6-methyl-3-pyridyl, 3-ethoxy-2-methyl-4-quinolyl, and 3:7-dimethoxy-4-coumarinyl penicillins. The penicillins may be prepared by reacting 6-amino-penicillanic acid or a liqour containing it with an acid chloride, bromide, anhydride or mixed anhydride derived from a carboxylic acid of the general formula <FORM:0905778/IV (b)/2> where Z, R1 and R2 are as above. 2,4,5-Triphenyl-3-furoyl chloride is prepared by warming the corresponding acid with thionyl chloride and a trace of pyridine. 2,4-Dimethoxyquinoline-3-carboxylic acid is prepared by the action of methanolic sodium methoxide on ethyl 2,4-dichloroquinoline-3-carboxylate, followed by saponification. 5-Benzyl-3-methylisoxazole-4-carboxylic acid is obtained by reacting ethyl a -(phenylacetyl) acetoacetate and hydroxylamine hydrochloride in aqueous ethanol followed by hydrolysis of the ester product. Reaction of the acid with thionyl chloride gives 5-benzyl-3-methylisoxazole-4-carbonyl chloride. 5-(2-furyl)-3-methylisoxazole - 4 - carboxylic acid is prepared by reacting ethyl a -(2-furoyl)-acetoacetate and hydroxylamine hydrochloride in aqueous ethanol, followed by hydrolysis of the ester product. 3 - Methyl - 5 - (31,51-dimethyl-41-isoxazolyl) -isoxazole-4-carboxylic acid is prepared by reacting ethyl a -3,5 - dimethylisoxazole-4-carbonyl)-acetoacetate and hydroxylamine hydrochloride in aqueous ethanol, followed by hydrolysis of the ester product. 3 - Methyl-5-(2-thienyl),isoxazole-4-carboxylic acid is prepared by hydrolysis of the ester product of the reaction between ethyl a -(2-thenoyl) - acetoacetate and hydroxylamine hydrochloride in aqueous alcohol. 3 - p-chlorophenyl-5-methylisoxazole-4-carboxylic acid is prepared by hydrolysis of the ester product of the reaction between p-chlorobenzo-hydroxamic chloride and ethyl acetoacetate in methanolic sodium methoxide. 4,5-Dimethyl-2-phenyl-3-furoic acid is obtained by condensing acetoin with ethyl benzoylacetate in the presence of anhydrous zinc chloride, followed by saponification of the resulting ester. 2,4 - Dimethoxy-6-methylpyridine-3-carboxylic acid is prepared by reacting 2,4-dichloro-3-ethoxycarbonyl-6-methylpyridine with sodium methoxide followed by hydrolysis. 2 - Diethylamine - 4,6-dimethylpyrimidine-5-carboxylic acid is obtained by treating 5-bromo-4,6-dimethyl-2-hydroxypyrimidine, first with phosphorus oxychloride to give 5-bromo-4,6-dimethyl-2-chloropyrimidine, then with diethylamine to give 5-bromo-2-diethylamino-4,6-dimethylpyrimidine which on treatment with butyl lithium followed by CO2 gives the desired pyrimidine acid. 4,6-Dimethyl-2-methoxypyrimidine-5-carboxylic acid is obtained from 5-bromo-4,6-dimethyl-2-methoxypyrimidine by reaction with butyl lithium followed by carbonation with carbon dioxide, the starting material having been obtained by the reaction of 5-bromo-2-chloro-4,6-dimethylpyrimidine with sodium methoxide. 4,6-Dimethoxypyrimidine-5-carboxylic acid is obtained from 5-bromo-4,6-dimethoxypyrimidine by reaction with butyl lithium followed by carbonation, the starting material having been prepared by the reaction of 5-bromo-4,6-dichloropyrimidine with sodium methoxide. 5 - Bromo-4-chloro-6-methoxyprimidine is prepared by reacting 5-bromo-4,6-dichloropyrimidine with one mole of sodium methoxide, and converted to 4-chloro-6-methoxypyrimidine-5-carboxylic acid by reaction with butyl lithium followed by carbonation. 2-Ethylbenzofuran-3-carbonyl chloride is obtained by reacting oxalyl chloride and 2-ethylbenzofuran in carbon disulphide in the presence of aluminium chloride. 2,4-dichloroquinoline-3-carbonyl chloride is prepared by refluxing 2,4-dihydroxquinoline-3-carboxylic acid in phosphorus oxychloride. 2-Ethyl-3-methoxyquinoline-4-carboxylic acid is obtained from 2-ethyl-3-hydroxy-quinoline-4-carboxylic acid by treatment with diazomethane in ether, followed by saponification. The Specification refers also to the acid chlorides of the above carboxylic acids (other than the penicillins) and to 3-methyl-5-methyl-mercaptoisoxazole-4-carbonyl chloride, 2-carbethoxy-3,5-dimethyl-pyrrole-4-carbonyl chloride, 1,3,5-triphenylpyrazole-4-carbonyl chloride, 3,7-dimethoxycoumarin-4-carbonyl chloride, acridine-9-carbonyl chloride and 1,2-dimethylindole-3-carbonyl chloride. The penicillins and non-toxic salts thereof may be used pharmaceutically in admixture with suitable carriers, and are suitable for oral administration. Specification 876,662 also is referred to.
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1141260A GB905778A (en) | 1960-03-31 | 1960-03-31 | Improvements in or relating to penicillins |
NO00139438A NO127106B (en) | 1960-03-31 | 1961-03-10 | |
SE2737/61A SE346003B (en) | 1960-03-31 | 1961-03-14 | |
BR127716/61A BR6127716D0 (en) | 1960-03-31 | 1961-03-17 | PROCESS FOR THE PREPARATION OF NEW PENICILLINS |
ES0265959A ES265959A1 (en) | 1960-03-31 | 1961-03-22 | Procedure for the preparation of new penicillins (Machine-translation by Google Translate, not legally binding) |
DK132661AA DK137049B (en) | 1960-03-31 | 1961-03-28 | Analogous process for the preparation of penicillins or their salts. |
BE601969A BE601969A (en) | 1960-03-31 | 1961-03-29 | Penicillins |
CH371661A CH401976A (en) | 1960-03-31 | 1961-03-29 | Process for the preparation of penicillin derivatives |
FR857298A FR1305382A (en) | 1960-03-31 | 1961-03-30 | Process for the preparation of penicillins and their non-toxic salts |
FR857297A FR1033M (en) | 1960-03-31 | 1961-03-30 | New penicillin and its non-toxic salts. |
CY26263A CY262A (en) | 1960-03-31 | 1963-08-09 | Improvements in or relating to penicillins |
CH1243863A CH419135A (en) | 1960-03-31 | 1963-10-10 | Process for the production of new penicillins |
MY87/63A MY6300087A (en) | 1960-03-31 | 1963-12-30 | Improvements in or relating to penicillins |
OA50917A OA01036A (en) | 1960-03-31 | 1964-12-18 | Process for the preparation of penicillins and their non-toxic salts. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1141260A GB905778A (en) | 1960-03-31 | 1960-03-31 | Improvements in or relating to penicillins |
Publications (1)
Publication Number | Publication Date |
---|---|
GB905778A true GB905778A (en) | 1962-09-12 |
Family
ID=9985733
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1141260A Expired GB905778A (en) | 1960-03-31 | 1960-03-31 | Improvements in or relating to penicillins |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB905778A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3284446A (en) * | 1964-11-24 | 1966-11-08 | R & L Molecular Research Ltd | Ortho-(5-tetrazolyl) phenylpenicillins |
US3290291A (en) * | 1964-05-22 | 1966-12-06 | Bristol Myers Co | 5-methyl-3-(2'-chloro-3'-thienyl)-4-isoxazolylpenicillin and salts thereof |
US3311611A (en) * | 1965-12-20 | 1967-03-28 | R & L Molecular Research Ltd | Derivatives of 6-aminopenicillanic acid |
-
1960
- 1960-03-31 GB GB1141260A patent/GB905778A/en not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3290291A (en) * | 1964-05-22 | 1966-12-06 | Bristol Myers Co | 5-methyl-3-(2'-chloro-3'-thienyl)-4-isoxazolylpenicillin and salts thereof |
US3284446A (en) * | 1964-11-24 | 1966-11-08 | R & L Molecular Research Ltd | Ortho-(5-tetrazolyl) phenylpenicillins |
US3311611A (en) * | 1965-12-20 | 1967-03-28 | R & L Molecular Research Ltd | Derivatives of 6-aminopenicillanic acid |
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