GB964449A - Derivatives of 6-amino penicillanic acid - Google Patents
Derivatives of 6-amino penicillanic acidInfo
- Publication number
- GB964449A GB964449A GB6084962A GB6084962A GB964449A GB 964449 A GB964449 A GB 964449A GB 6084962 A GB6084962 A GB 6084962A GB 6084962 A GB6084962 A GB 6084962A GB 964449 A GB964449 A GB 964449A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- compound
- radical
- formula
- trimethylsilyl
- 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
Penicillins of the general formula: <FORM:0964449/C1/1> in which R represents an alkyl radical, which may be substituted or may be interrupted by hetero atoms, or a cycloaliphatic, aromatic, heterocyclic or araliphatic radical, which may be substituted, X represents a -CO- or -SO2- group are prepared by reacting 6-aminopenicillanic acid or a salt thereof with a compound of the formula: <FORM:0964449/C1/2> in which R1, R2 and R3 which may be the same or different represent alkyl, aralkyl, cycloalkyl or aryl radicals and Z represents a halogen atom or the radical: <FORM:0964449/C1/3> in which R4 and R5, which may be the same or different, represent hydrogen atoms, lower alkyl radicals or the group: <FORM:0964449/C1/4> and if Z represents a halogen atom the reaction takes place in the presence of a compound or compounds able to fix hydrogen halides, to give a compound of the formula: <FORM:0964449/C1/5> in which Q represents a hydrogen atom or the radical: <FORM:0964449/C1/6> or a mixture of such compounds which is or are reacted with an acid of the formula R-Y wherein Y represents a -COOH or -SO3H group or with an anhydride or halide of such an acid, preferably in the presence of a compound able to fix water or acids, followed by hydrolysis or alcoholysis to give the desired penicillin. In examples 6-aminopenicillanic acid or its potassium salt is reacted with trimethylchlorosilane or hexamethyldisilazane and the product reacted with one of a number of specified acid chlorides and anhydrides, followed by hydrolysis or alcoholysis to give a penicillin either as the free acid or in salt form.ALSO:Trimethylsilyl-6-aminopenicillanate and trimethylsilyl N-trimethylsilyl 6-aminopenicillanate may be prepared by reacting 6-aminopencillanic acid with appropriate quantities of trimethylchlorosilane, trimethylaminosilane or hexamethyldisilazane. In addition to methyl, the radicals attached to silicon may be cycloalkyl, aryl, aralkyl or other alkyl groups.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC23708A DE1159449B (en) | 1961-03-22 | 1961-03-22 | Process for the preparation of 6-acylaminopenicillanic acids and their salts |
| DEC0025516 | 1961-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB964449A true GB964449A (en) | 1964-07-22 |
Family
ID=25969395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB6084962A Expired GB964449A (en) | 1961-03-22 | 1962-03-21 | Derivatives of 6-amino penicillanic acid |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH421110A (en) |
| DK (1) | DK120595B (en) |
| GB (1) | GB964449A (en) |
| MY (1) | MY6900129A (en) |
| SE (1) | SE322512B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2100925A1 (en) * | 1970-07-17 | 1972-03-24 | Hoffmann La Roche | |
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
-
1962
- 1962-03-05 SE SE239562A patent/SE322512B/xx unknown
- 1962-03-20 CH CH328262A patent/CH421110A/en unknown
- 1962-03-21 GB GB6084962A patent/GB964449A/en not_active Expired
- 1962-03-21 DK DK130162A patent/DK120595B/en unknown
-
1969
- 1969-12-31 MY MY6900129A patent/MY6900129A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2100925A1 (en) * | 1970-07-17 | 1972-03-24 | Hoffmann La Roche | |
| US4182709A (en) * | 1976-01-15 | 1980-01-08 | Glaxo Group Limited | Manufacture of semi-synthetic penicillin antibiotics |
Also Published As
| Publication number | Publication date |
|---|---|
| MY6900129A (en) | 1969-12-31 |
| DK120595B (en) | 1971-06-21 |
| SE322512B (en) | 1970-04-13 |
| CH421110A (en) | 1966-09-30 |
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