GB733394A - Penicillin salts of n-methyl-n-(1,2-bis-p-methoxyphenyl-2-hydroxyethyl) amine - Google Patents
Penicillin salts of n-methyl-n-(1,2-bis-p-methoxyphenyl-2-hydroxyethyl) amineInfo
- Publication number
- GB733394A GB733394A GB17000/53A GB1700053A GB733394A GB 733394 A GB733394 A GB 733394A GB 17000/53 A GB17000/53 A GB 17000/53A GB 1700053 A GB1700053 A GB 1700053A GB 733394 A GB733394 A GB 733394A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amine
- bis
- methyl
- penicillin
- threo
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Penicillin salts of N-methyl-N-(1,2 bis-p-methoxyphenyl - 2 - hydroxyethyl) amine are prepared by mixing an aqueous solution of a water-soluble salt of penicillin, e.g. the potassium salt, with an aqueous solution of a water-soluble salt of N-methyl-N-(1,2 bis-p-methoxyphenyl-2 hydroxyethyl) amine, e.g. the hydrochloride. Any penicillin may be used; specified are penicillins G, F and K. The preparation of the following salts of penicillin G is described: (a) l - erythro - N - methyl - (1,2 bis-p - methoxyphenyl - 2 - hydroxy ethyl) amine from the dl-erythro isomer; (b) d-erythro-N-methyl (1,2 bis - p - methoxyphenyl - 2 - hydroxy ethyl) amine (M.P. 217 DEG \sB 5 DEG C.) from the residual mother liquor obtained in (a) and also from the d-erythro isomer; (c) l-threo-N-methyl (1,2 bis - p - methoxy phenyl - 2-hydroxy ethyl) amine (M.P. 167-168) from the l-threo isomer; (d) d-threo-N-methyl(1,2 bis-p-methoxy phenyl-2-hydroxy ethyl) amine from the d - threo - isomer. dl - Erythro - N - methyl-N - (1,2 bis - p - methoxy phenyl - 2 - hydroxyethyl) amine is prepared by hydrogenating a mixture of anisoin and anhydrous monomethylamine in the presence of a nickel catalyst. d - Threo - N - methyl - N - (1,2 bis - p - methoxy phenyl - 2 - hydroxy ethyl) amine is prepared by treating d - erythro - N - methyl - (1,2 bis-p - methoxy phenyl - 2 - hydroxy ethyl) amine with acetic anhydride at 70-80 DEG C., cooling, adding water to precipitate the N-acetyl derivative, which is then hydrolysed with 5 per cent hydrochloric acid and the d-threo compound precipitated by the adjustment of the pH to 11 with sodium hydroxide. The l-threo isomer can be prepared in a similar manner.ALSO:A therapeutic preparation for oral or parenteral use, which may be in the form of an aqueous suspension, comprises as an essential ingredient thereof a penicillin salt of N-methyl -N-(1,2 - bis - p - methoxyphenyl - 2 - hydroxyethyl)amine. The penicillin may be any penicillin, e.g. penicillin G, K and K and the amine may be the form of the d- or l-erythro, or d- or l-threo isomer.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US733394XA | 1952-07-30 | 1952-07-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB733394A true GB733394A (en) | 1955-07-13 |
Family
ID=22113152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB17000/53A Expired GB733394A (en) | 1952-07-30 | 1953-06-19 | Penicillin salts of n-methyl-n-(1,2-bis-p-methoxyphenyl-2-hydroxyethyl) amine |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB733394A (en) |
-
1953
- 1953-06-19 GB GB17000/53A patent/GB733394A/en not_active Expired
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