GB1078077A - 6-aminothiopenicillanic acid and thiopenicillins - Google Patents
6-aminothiopenicillanic acid and thiopenicillinsInfo
- Publication number
- GB1078077A GB1078077A GB36162/64A GB3616264A GB1078077A GB 1078077 A GB1078077 A GB 1078077A GB 36162/64 A GB36162/64 A GB 36162/64A GB 3616264 A GB3616264 A GB 3616264A GB 1078077 A GB1078077 A GB 1078077A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alkoxy
- alkyl
- alkanoylamino
- alkanoyl
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to 6-aminothiopenicillanic acid and thiopenicillins of formula <FORM:1078077/C2/1> Wherein R is <FORM:1078077/C2/2> or <FORM:1078077/C2/3> or <FORM:1078077/C2/4> wherein R1, R2 and R3 are each hydrogen, chloro, bromo, fluoro, iodo, nitro, sulphamyl, trifluoromethyl, alkyl, alkoxy, alkylthio, dialkylamino, alkanoylamino, alkanoyl, alkanoyloxy, alkylsulphonyl, phenyl or benzyl; R4 and R5 are each hydrogen, chloro, bromo, fluoro, iodo, nitro, alkoxy, phenoxy, benzyloxy, trifluoromethyl, alkanoylamino or alkyl; and R6, R7 and R8 are each hydrogen, chloro, bromo, fluoro, iodo, nitro, alkyl, alkoxy, phenyl, phenoxy, benzyloxy, alkylthio, dialkylamino, alkanoylamino, alkanoyl, alkylsulphonyl, cycloalkyl radicals having from 5 to 7 carbon atoms inclusive or cycloalkoxy radicals having from 5 to 7 carbon atoms inclusive; and non-toxic salts thereof. The aforesaid alkyl, alkoxy and alkanoyl groups have 1 to 10 carbon atoms. 6-Aminothiopenicillanic acid is produced by (a) enzymatic hydrolysis of benzylthiopenicillin or (b) converting the 3-carboxylic acid group of 6-aminopenicillanic acid in which the 6-amino group is protected, to a reactive acylating derivative such as the acid anhydride, reacting the acylating derivative with a source of sulfhydryl groups, e.g. sodium hydrogen sulphide and then removing the protective group. The thio-penicillins are produced by (a) acylation of 6-aminothio-penicillanic acid or (b) converting the 3-carboxylic acid group of the corresponding penicillin having its amino group protected, to a reactive acylating derivative and reacting said acylating derivative of penicillin with a source of sulfhydryl groups to obtain the desired thiopenicillin with protected amino group, and removing the protected amino group, and removing the protecting group. The reactive acylating derivative is an acid anhydride, mixed acid anhydride, acid chloride or azolide. Typical thiopenicillins are the 6-(a -aminophenylacetamido)-6-(a -aminonaphthylacetamido) - and 6-[a -amino-(2- or 3-thienyl) acetamido] thiopenicillanic acids. The thiopenicillins and their non-toxic salts may be incorporated into pharmaceutical compositions for oral and parenteral use, e.g. solutions, dispersions, emulsions, tablets and capsules. They may be used for the treatment of infectious diseases caused by Gram-positive bacteria in poultry and animals and may be used for the treatment of mastitis in cattle. They are used as nutritional supplements in animal feeds.ALSO:An animal or poultry feed contains, as nutritional supplement, a thiopenicillin of formula:- <FORM:1078077/A1-A3/1> Wherein R is <FORM:1078077/A1-A3/2> or <FORM:1078077/A1-A3/3> or <FORM:1078077/A1-A3/4> and R1, R2 and R3 are H, Cl, Br, F, I, NO2, sulphamyl, trifluoromethyl, alkyl, alkoxy, alkylthio, di-alkylamino, alkanoylamino, alkanoyl, alkanoyloxy, alkylsulphonyl, phenyl or benzyl; R4 and R5 is H, Cl, Br, F, I, NO2, alkoxy, phenoxy, benzyloxy, trifluoromethyl, alkanoylamino, or alkyl; and R6, R7 and R8 are H, Cl, Br, F, I, NO2, alkyl, alkoxy, phenyl, phenoxy, benzyloxy, alkylthio, di-alkylamino, alkanoylamino, alkanoyl, alkylsulphonyl, cycloalkyl of C5-7 or cycloalkoxy of C5-7, and non-toxic salts thereof. The aforesaid alkyl, alkoxy and alkanoyl groups have 1 to 10 carbon atoms. Typical thiopenicillins are 6-(a -aminophenylacetamido)-thiopenicillanic acid and 6 - [a -amino-2-thienylacetamido]-thiopenicillanic acid.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30659563A | 1963-09-04 | 1963-09-04 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1078077A true GB1078077A (en) | 1967-08-02 |
Family
ID=23185997
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB36162/64A Expired GB1078077A (en) | 1963-09-04 | 1964-09-03 | 6-aminothiopenicillanic acid and thiopenicillins |
Country Status (4)
Country | Link |
---|---|
BE (1) | BE652599A (en) |
FR (1) | FR3984M (en) |
GB (1) | GB1078077A (en) |
IL (1) | IL21947A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5861455A (en) * | 1995-10-25 | 1999-01-19 | Fina Technology, Inc. | Monovinylaromatic polymer with improved stress crack resistance |
-
0
- BE BE652599D patent/BE652599A/xx unknown
-
1964
- 1964-08-20 IL IL21947A patent/IL21947A/en unknown
- 1964-09-02 FR FR986938A patent/FR3984M/fr not_active Expired
- 1964-09-03 GB GB36162/64A patent/GB1078077A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5861455A (en) * | 1995-10-25 | 1999-01-19 | Fina Technology, Inc. | Monovinylaromatic polymer with improved stress crack resistance |
Also Published As
Publication number | Publication date |
---|---|
IL21947A (en) | 1968-03-28 |
FR3984M (en) | 1966-03-07 |
BE652599A (en) | 1900-01-01 |
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