Claims
- 1. A process for the preparation of a compound of the formula I or a pharmaceutically acceptable salt thereof ##STR12## wherein R.sup.1 is hydrogen, a trialkylamino, trialkylsilyl, trichloroethyl, acetoxymethyl, conventional penicillin phenacyl, phenyl or a benzyl group,
- R.sup.2 is hydrogen, alkyl, alkenyl, alkyl, having a conventional penicillin aryl heterocyclic substitutent, or a conventional penicillin aryl, aralkyl or heterocyclic group,
- R.sup.3 is hydrogen, aryl, alkyl, cycloalkyl or aralkyl, and
- X is a group selected from the formulae consisting of: ##STR13## by acylating a compound of the formula II ##STR14## wherein R.sup.4 is an easily removable ester-forming group selected from the group which consists of trialkylamino, trialkylsilyl, trichloroethyl, acetoxymethyl, phenacyl, phenyl and benzyl, or a salt formed with an alkali metal or a trialkylamine, in wich the acylation is performed at a temperature of -10.degree. C. to +30.degree. C. for a period up to 2 hours using an ester of the formula III ##STR15## wherein R.sup.5 is aryl, alkyl, cycloalkyl or aralkyl, and
- substituent R.sup.4 and R.sup.5 of the obtained product are split off.
- 2. The process defined in claim 1, in which the acylation is performed using an ester of the formula IV ##STR16## wherein R.sup.6 is
- (i) an aromatic group, having a halogen, nitro, alkyl, alkoxy, acyl, carbamoyl or dialkylamino substituent,
- (ii) a C.sub.3-7 unsubstituted cycloalkyl or substituted by a halogen or an alkyl substituent, or being condensed with an aryl group, or
- (iii) benzyl group or benzyl substituted by a halogen, alkyl, alkoxy, acyl, nitro or dialkylamino substituent.
- 3. A process as claimed in claim 1 in which the acylation is performed in the presence of a tertiary base selected from the group consisting of a trialkylamine, pyridine or N,N-dialkylaniline.
- 4. The process defined in claim 1 for the preparation of 7-(.alpha.-carboxy-phenylacetamido)-3-methyl-cephalosporanic acid or .alpha.-carboxy-benzylpenicillin, in which the acylation is performed in the presence of at least two molar equivalents of a tertiary base calculated for the amount of the acylating agent.
- 5. The process defined in claim 1 for the preparation of an .alpha.-(halogenated phenoxy)-carbonyl-benzylpenicillin, selected from the group consisting of .alpha.-(pentachlorophenoxy)-carbonyl-benzylpenicillin or .alpha.-benzyloxycarbonyl-benzylpenicillin, 7-(.alpha.)-benzyloxycarbonyl(-phenylacetamido)-3-methyl-cephalosporanic acid or a 7-(.alpha.)-halogenated phenoxycarbonyl(-phenylacetamido)-3-methyl-cephalosporanic acid, preferably 7-(.alpha.)-pentachlorophenoxycarbonyl(-phenylacetamido)-3-methyl-cephalosporanic acid, in which the acylation is performed in the presence of up to 1.5 molar equivalent of a tertiary base calculated for the amount of the acylating agent.
- 6. The process defined in claim 1 in which phenylmalonic acid di-pentachlorophenyl ester or 3-thienyl-3-furyl-, 3-methoxyphenyl-, 4-methoxyphenyl-, 3-pyridyl-, o-chlorophenyl-, o-bromophenyl-, p-chlorophenyl-, or o-butoxyphenylmalonic acid di-pentachlorophenyl ester is used as an acylating agent.
- 7. The process defined in claim 1, in which phenylmalonic acid pentachlorophenylester benzylester, phenylmalonic acid pentachlorophenylester 5-indanylester, phenylmalonic acid pentachlorophenylester ethylester, phenylmalonic acid pentachlorophenylester allylester, phenylmalonic acid pentachlorophenylester acetoxymethylester, phenylmalonic acid pentachlorophenylester 2,2,2-trichloroethylester, phenylmalonic acid pentachlorophenylester p-nitro-benzylester, phenylmalonic acid pentachlorophenylester phenacetylester, or phenylmalonic acid pentachlorophenylester p-nitro-phenylester is used as acylating agent.
- 8. The process defined in claim 1 in which the acylation is performed in the presence of an organic solvent, preferably benzene, dioxane, ether, tetrahydrofuran, dichloromethane or dichloroethane.
- 9. A process for the preparation of a compound of the formula I or a pharmaceutically acceptable salt thereof ##STR17## wherein R.sup.1 is hydrogen, a trialkylamino, trialkylsilyl, trichloroethyl, acetoxymethyl, conventional penicillin phenacyl, phenyl or a benzyl group,
- R.sup.2 is hydrogen, alkyl, alkenyl, alkyl, having a conventional penicillin aryl heterocyclic substituent, or a conventional penicillin aryl, aralkyl, cycloalkyl or aralkyl group, and
- X is a group selected from the formulae consisting of: ##STR18## which comprises: reacting a compound of the formula: ##STR19## with an alcohol of the formula R.sup.3 --OH wherein R.sup.3 is hydrogen, aryl, alkyl, cycloalkyl or aralkyl at a temperature of -10.degree. C. to +30.degree. C. for a period up to 2 hours.
Priority Claims (1)
Number |
Date |
Country |
Kind |
CI 1499 |
Jul 1974 |
HUX |
|
Parent Case Info
This application is a continuation-in-part of Ser. No. 598,692, July 24, 1975, now abandoned.
Foreign Referenced Citations (1)
Number |
Date |
Country |
1004670 |
Sep 1965 |
GBX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
598692 |
Jul 1975 |
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