GB873244A - Improvements in or relating to penicillins - Google Patents
Improvements in or relating to penicillinsInfo
- Publication number
- GB873244A GB873244A GB11625/60A GB1162560A GB873244A GB 873244 A GB873244 A GB 873244A GB 11625/60 A GB11625/60 A GB 11625/60A GB 1162560 A GB1162560 A GB 1162560A GB 873244 A GB873244 A GB 873244A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetic acid
- cf2cf2
- tetrafluoro
- integer
- general 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Relates to penicillins of the general formula <FORM:0873244/IV (b)/1> wherein X is CF3 or H(CF2CF2)n and n is an integer from 1 to 5 such as (2,2,2-trifluorethoxy), (2,2,3,3-tetrafluoro-1-propoxy), (2,2,3, 3,4,4,5,5-octafluoro-1-pentoxy), (2,2,3,3,4,4,5,5, 6,6,7,7-dodecafluoro-1-heptoxy), (2,2,3,3,4,4,5,5, 6,6,7,7,8,8,9,9-hexadecafluoro - 1 - nonoxy) and (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11 - eicosafluoro-1-endecyl) methyl penicillin and to non-toxic salts thereof such as the sodium, potassium, calcium, aluminium, ammonium, triethylamine, procaine, dibenzylamine, N-benzyl-beta-phenethylamine, 1-ephenamine, N, N1-dibenzylethylenediamine, dehydroabietylamine and N,N1-bis-dehydroabietylethylenediamine salts. The penicillins may be prepared by aerobically growing a penicillin-producing mould of the genus Penicillium and group notatum-chrysogenum in a nutrient medium containing a precursor of the general formula CF3CH2OZ or H(CF2CF2)nCH2OZ wherein n is an integer from 1 to 5 and Z is the radical -CH2COOH, -CH2COOM, where M is a non-toxic ion which does not inhibit fermentation, -CH2CH2NH2, -CH2CONHCH2CH2OH, -CH2CONH2, -CH2CHO, -CH2CH2OH or a radical which is transformed into the equivalent of the -CH2COOH radical during the course of the fermentation, such as 2-(2,2,2-trifluorethoxy) acetic acid or 2-(2,2,3,3-tetrafluoropropoxy)-acetic acid, or by reacting 6-amino-penicillanic acid, preferably in the form of a neutral salt such as the sodium or triethylamine salt, with an acid chloride of the general formula: X.CH2OCH2CO.Cl where X is CF3 or H(CF2CF2)n and n is an integer from 1 to 5, or a functional equivalent thereof as an acylating agent for a primary amino group. Polyfluoroalkoxyacetic acids are prepared by dissolving the corresponding perfluoroalcohol in aqueous sodium hydroxide, adding sodium chloroacetate, refluxing and acidifying. In examples, 2(2,2,2-trifluoroethoxy) acetic acid and 2(2,2,3,3-tetrafluoro-propoxy) acetic acid are prepared from trifluoroethanol and 1H, 1H, 3H-tetrafluoro-1-propanol respectively.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US873244XA | 1959-04-10 | 1959-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB873244A true GB873244A (en) | 1961-07-19 |
Family
ID=22204495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB11625/60A Expired GB873244A (en) | 1959-04-10 | 1960-04-01 | Improvements in or relating to penicillins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB873244A (en) |
-
1960
- 1960-04-01 GB GB11625/60A patent/GB873244A/en not_active Expired
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