Claims
- 1. A process for preparation of a compound of the formula ##STR12## wherein R.sup.1 is nitrophenacyl;
- R.sup.2 is hydrogen, alkyl, alkenyl, alkyl having a conventional penicillin aryl heterocyclic substituent, or a conventional penicillin aryl, alkyl, cycloalkyl or aralkyl group;
- R.sup.3 is hydrogen, aryl, alkyl, cycloalkyl or aralkyl; and
- X is a group selected from the formulae consisting of ##STR13## which comprises: reacting a compound of the formula ##STR14## with a compound of the formula R.sup.5 --OH wherein R.sup.5 is aryl, alkyl, cycloalkyl or aralkyl at a temperature of -10.degree. C. to +30.degree. C. for a period of up to 2 hours; and where R.sup.3 is hydrogen, splitting off the substituent R.sup.5.
- 2. A process for the preparation of a compound of the formula ##STR15## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is nitrophenacyl;
- R.sup.2 is hydrogen, alkyl, alkenyl, alkyl having a conventional penicillin aryl heterocyclic substituent, 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 ##STR16## by acylating a compound of the formula ##STR17## wherein R.sup.4 is nitrophenacyl, in which the acylation is performed at a temperature of -10.degree. C. to +30.degree. C. for a period of up to two hours using an ester of the formula ##STR18## wherein R.sup.5 is aryl, alkyl, cycloalkyl, or aralkyl; and wherein
- R.sup.3 is hydrogen, splitting off the substituent R.sup.5.
- 3. A process for the preparation of a compound of the formula ##STR19## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is nitrophenacyl;
- R.sup.2 is hydrogen, alkyl, alkenyl, alkyl having a conventional penicillin aryl heterocyclic substituent, or a conventional penicillin aryl, aralkyl, or heterocyclic group;
- R.sup.3 is hydrogen; an aromatic group having a halogen, nitro, alkyl, alkoxy, acyl, carbamoyl or dialkylamino substituent; a C.sub.3 to C.sub.7 unsubstituted cycloalkyl or substituted by a halogen or an alkyl substituent, or being condensed with an aryl group; or a benzyl group or benzyl substituted by a halogen, alkyl, alkoxy, acyl, nitro or dialkylamino substituent; and
- X is a group selected from the formulae consisting of ##STR20## by acylating a compound of the formula ##STR21## wherein R.sup.4 is nitrophenacyl, 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 at a temperature of -10.degree. C. to +30.degree. C. using an ester of the formula ##STR22## wherein R.sup.6 is an aromatic group having a halogen, nitro, alkyl, alkoxy, acyl, carbamoyl or dialkylamino substituent; a C.sub.3 to C.sub.7 unsubstituted cycloalkyl or substituted by a halogen or an alkyl substituent, or being condensed with an aryl group; or a benzyl group or benzyl substituted by a halogen, alkyl, alkoxy, acyl, nitro, or dialkylamino substituent; and
- wherein
- R.sup.3 is hydrogen, splitting off the substituent R.sup.6.
- 4. The process defined in claim 2 or claim 3 wherein R.sup.3 is an aromatic group having a halogen substituent.
- 5. The process defined in claim 3 wherein R.sup.3 is pentachlorophenyl.
- 6. The process defined in claim 3 wherein R.sup.3 is indanyl.
- 7. A process for the preparation of a compound of the formula ##STR23## or a pharmaceutically acceptable salt thereof wherein R.sup.1 is hydrogen, trialkylamino, trialkylsilyl, trichloroethyl, acetoxymethyl, phenacyl, nitrophenacyl, 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, or heterocyclic group;
- R.sup.3 is hydrogen; an aromatic group having a halogen, nitro, alkyl, alkoxy, acyl, carbamoyl or dialkylamino substituent; a C.sub.3 to C.sub.7 unsubstituted cycloalkyl or substituted by a halogen or an alkyl substituent, or being condensed with an aryl group; or a benzyl group or benzyl substituted by a halogen, alkyl, alkoxy, acyl, nitro or dialkylamino substituent; and
- X is a group selected from the formulae consisting of ##STR24## wherein the compound is selected from the group consisting of: 6-(.alpha.[5-indanyloxy-carbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 6-(.alpha.-[2,4-dimethylphenoxy-carbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 6-(.alpha.-[3,4-dimethylphenoxy-carbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 6-(.alpha.-phenoxy-carbonyl-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 6-(.alpha.-carboxy-p-chlorophenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 6-(.alpha.-carboxy-o-bromophenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid;
- 7-(.alpha.-phenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid;
- 7-(.alpha.-[5-indanyloxy-carbonyl]-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid;
- 7-(.alpha.-phenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid triethylammonium salt;
- 7-(.alpha.-carboxy-3-thienyl-acetamido)-3-methyl-ceph-3-em-4-carboxylic acid;
- 7-(.alpha.-[5-indanyloxy-carbonyl]-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-phenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-pentachlorophenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-benzyloxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-pentachlorophenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid p-nitro-phenacylester;
- 7-(.alpha.-phenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-phenoxy-carbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid;
- 7-(.alpha.-carboxy-propylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid;
- 7-(.alpha.-carboxy-propylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester;
- 7-(.alpha.-carboxy-p-chlorophenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid; and
- 7-(.alpha.-carboxy-o-bromophenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid, or a pharmaceutically acceptable salt thereof, which comprises the step of acylating a compound of the formula ##STR25## wherein R.sup.4 is an easily removable ester-forming group selected from the group which consists of trialkylamino, trialkylsilyl, trichloroethyl, acetoxymethyl, phenacyl, nitrophenacyl, phenyl and benzyl or a salt formed with an alkali metal or a trialkylamine 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 at a temperature of -10.degree. C. to +30.degree. C. using an ester of the formula ##STR26## wherein R.sup.6 is an aromatic group having a halogen, nitro, alkyl, alkoxy, acyl, carbamoyl or dialkylamino substituent; a C.sub.3 to C.sub.7 unsubstituted cycloalkyl or substituted by a halogen or an alkyl substituent, or being condensed with an aryl group; or a benzyl group or benzyl substituted by a halogen, alkyl, alkoxy, acyl, nitro, or dialkylamino substituent; and
- wherein
- R.sup.1 and R.sup.3 are hydrogen, splitting off the substituents R.sup.4 and R.sup.6.
Priority Claims (1)
Number |
Date |
Country |
Kind |
CI 1499 |
Jul 1974 |
HUX |
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CROSS REFERENCE TO RELATED APPLICATION
This application is a continuation of Ser. No. 812,735 filed July 5, 1977, now U.S. Pat. No. 4,171,303; which is a continuation-in-part of Ser. No. 598,692, filed July 24, 1975, now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4171303 |
Huhn et al. |
Oct 1979 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
1004670 |
Sep 1965 |
GBX |
Continuations (1)
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Number |
Date |
Country |
Parent |
812735 |
Jul 1977 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
598692 |
Jul 1975 |
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