Patent US2493720A successfully refreshed from Google Patents.
Patent US4278686A successfully refreshed from Google Patents.
US4278686A
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Carbapenum derivatives, a process for their preparation and their use in pharmaceutical compositions and intermediates
Assignee: Beecham Group PLC
•
Filing: 1979-04-27
•
Granted: 1981-07-14
•
Expires: 1999-04-27
Abstract
Abstract The present invention provides antibiotic compounds of the formula: ##STR1## and salts and cleavable esters thereof wherein X is a SCH 2 CH 2 NH 2 or YNH-COCH 3 group where Y is a SCH 2 CH 2 , trans --SO--CH═-- or cis or trans --S--CH═CH-- group and R is a lower alkyl, aryl, aralkyl, lower alkenyl, or substituted lower alkyl.
Inventors
- 👤 David F. Corbett
- 👤 Alfred J. Eglington
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 10:50
CPC Classifications
C; C07; C07D; C07D477/00; C07D477/10; C07D477/12; C07D477/16; C07D477/20
Claims Analysis
Total Claims: 98
Claim 1
Independent Claim
127 words
A compound of the formula (I): ##STR99## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO--CH═CH or cis or trans S--CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamide, or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 2
Dependent Claim
127 words
A compound of the formula (I): ##STR99## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO--CH═CH or cis or trans S--CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamide, or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 3
Dependent Claim
92 words
The compound of the formula (II): ##STR100## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 4
Dependent Claim
92 words
The compound of the formula (II): ##STR100## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 5
Dependent Claim
92 words
The compound of the formula (III): ##STR101## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 6
Dependent Claim
92 words
The compound of the formula (III): ##STR101## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 7
Dependent Claim
92 words
The compound of the formula (IV): ##STR102## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 8
Dependent Claim
92 words
The compound of the formula (IV): ##STR102## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 9
Dependent Claim
92 words
The compound of the formula (V): ##STR103## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 10
Dependent Claim
92 words
The compound of the formula (V): ##STR103## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 11
Dependent Claim
92 words
The compound of the formula (VI): ##STR104## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 12
Dependent Claim
92 words
The compound of the formula (VI): ##STR104## a pharmaceutically acceptable salt thereof, or an ester which is convertible by chemical or biological means to the corresponding acid or salt thereof wherein R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 13
Dependent Claim
11 words
A compound according to claim 1 which has the 8S configuration.
Claim 14
Dependent Claim
11 words
A compound according to claim 1 which has the 8R configuration.
Claim 15
Dependent Claim
15 words
A compound according to claim 1 which is a mixture of 8R and 8S forms.
Claim 16
Dependent Claim
22 words
A compound according to claim 1 wherein R is methyl, ethyl, n-propyl, n-butyl, benzyl, 2-phenylethyl, phenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, methoxycarbonylmethyl or ethoxycarbonylmethyl.
Claim 17
Dependent Claim
25 words
A compound according to claim 1 wherein R is 2-aminoethyl, 2-benzoyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzoyloxycarbonylaminoethyl, allyl, p-nitrobenzyl, p-chlorobenzyl, p-bromobenzyl, p-methoxybenzyl, p-methylbenzyl, 2-acetamidoethyl, benzyloxycarbonylmethyl, p-nitrobenzyloxycarbonylmethyl, 2-methoxyethyl or 2-acetoxyethyl.
Claim 18
Dependent Claim
14 words
A compound according to claim 1 wherein R is methyl, ethyl, benzyl or phenyl.
Claim 19
Dependent Claim
18 words
A compound according to claim 1 in the form of the free acid or a pharmaceutically acceptable salt.
Claim 20
Dependent Claim
12 words
A compound according to claim 1 in the form of an ester.
Claim 21
Dependent Claim
11 words
A compound according to claim 14 which is a p-nitrobenzyl ester.
Claim 22
Dependent Claim
11 words
A compound according to claim 2 which has the 8S configuration.
Claim 23
Dependent Claim
11 words
A compound according to claim 3 which has the 8S configuration.
Claim 24
Dependent Claim
11 words
A compound according to claim 4 which has the 8S configuration.
Claim 25
Dependent Claim
11 words
A compound according to claim 5 which has the 8S configuration.
Claim 26
Dependent Claim
11 words
A compound according to claim 6 which has the 8S configuration.
Claim 27
Dependent Claim
11 words
A compound according to claim 2 which has the 8R configuration.
Claim 28
Dependent Claim
11 words
A compound according to claim 3 which has the 8R configuration.
Claim 29
Dependent Claim
11 words
A compound according to claim 4 which has the 8R configuration.
Claim 30
Dependent Claim
11 words
A compound according to claim 5 which has the 8R configuration.
Claim 31
Dependent Claim
11 words
A compound according to claim 6 which has the 8R configuration.
Claim 32
Dependent Claim
15 words
A compound according to claim 2 which is a mixture of 8R and 8S forms.
Claim 33
Dependent Claim
15 words
A compound according to claim 3 which is a mixture of 8R and 8S forms.
Claim 34
Dependent Claim
15 words
A compound according to claim 4 which is a mixture of 8R and 8S forms.
Claim 35
Dependent Claim
15 words
A compound according to claim 5 which is a mixture of 8R and 8S forms.
Claim 36
Dependent Claim
15 words
A compound according to claim 6 which is a mixture of 8R and 8S forms.
Claim 37
Dependent Claim
143 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (I): ##STR105## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier, or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylamino, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 38
Dependent Claim
143 words
A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of the formula (I): ##STR105## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier, or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylamino, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 39
Dependent Claim
123 words
A composition according to claim 31 wherein the compound is of the formula (II): ##STR106## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO--CH═CH or cis or trans S--CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier.
Claim 40
Dependent Claim
123 words
A composition according to claim 31 wherein the compound is of the formula (III): ##STR107## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 C 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO--CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier.
Claim 41
Dependent Claim
123 words
A composition according to claim 31 wherein the compound is of the formula (IV): ##STR108## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier.
Claim 42
Dependent Claim
123 words
A composition according to claim 31 wherein the compound is of the formula (V): ##STR109## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier.
Claim 43
Dependent Claim
123 words
A compound according to claim 31 wherein the compound is of the formula (VI): ##STR110## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido, in combination with a pharmaceutically acceptable carrier.
Claim 44
Dependent Claim
13 words
A composition according to claim 31 wherein the compound has the 8S configuration.
Claim 45
Dependent Claim
13 words
A composition according to claim 31 wherein the compound has the 8R configuration.
Claim 46
Dependent Claim
17 words
A composition according to claim 31 wherein the compound is a mixture of 8R and 8S isomers.
Claim 47
Dependent Claim
23 words
A composition according to claim 31 wherein R is a methyl, ethyl, n-propyl, n-butyl, benzyl, 2-phenylethyl, phenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, methoxycarbonylmethyl or ethoxycarbonylmethyl.
Claim 48
Dependent Claim
25 words
A composition according to claim 31 wherein R is 2-aminoethyl, 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, allyl, p-nitrobenzyl, p-chlorobenzyl, p-bromobenzyl, p-methoxybenzyl, p-methylbenzyl, 2-acetaminoethyl, benzyloxycarbonylmethyl, p-nitrobenzyloxycarbonylmethyl, 2-methoxyethyl or 2-acetoxyethyl.
Claim 49
Dependent Claim
14 words
A composition according to claim 31 wherein R is methyl, ethyl, benzyl or phenyl.
Claim 50
Dependent Claim
21 words
A composition according to claim 31 wherein the compound is in the form of a free acid or pharmaceutically acceptable salt.
Claim 51
Dependent Claim
19 words
A composition according to claim 31 wherein the compound is in the form of an in vivo hydrolyzable ester.
Claim 52
Dependent Claim
13 words
A composition according to claim 44 wherein the ester is a p-nitrobenzyl ester.
Claim 53
Dependent Claim
13 words
A composition according to claim 32 wherein the compound has the 8S configuration.
Claim 54
Dependent Claim
13 words
A composition according to claim 33 wherein the compound has the 8S configuration.
Claim 55
Dependent Claim
13 words
A composition according to claim 34 wherein the compound has the 8s configuration.
Claim 56
Dependent Claim
13 words
A composition according to claim 35 wherein the compound has the 8S configuration.
Claim 57
Dependent Claim
13 words
A composition according to claim 36 wherein the compound has the 8S configuration.
Claim 58
Dependent Claim
13 words
A composition according to claim 32 wherein the compound has the 8R configuration.
Claim 59
Dependent Claim
13 words
A composition according to claim 33 wherein the compound has the 8R configuration.
Claim 60
Dependent Claim
13 words
A composition according to claim 34 wherein the compound has the 8R configuration.
Claim 61
Dependent Claim
13 words
A composition according to claim 35 wherein the compound has the 8R configuration.
Claim 62
Dependent Claim
13 words
A composition according to claim 36 wherein the compound has the 8R configuration.
Claim 63
Dependent Claim
17 words
A composition according to claim 32 wherein the compound is a mixture of 8R and 8S forms.
Claim 64
Dependent Claim
17 words
A composition according to claim 33 wherein the compound is a mixture of 8R and 8S forms.
Claim 65
Dependent Claim
17 words
A composition according to claim 34 wherein the compound is a mixture of 8R and 8S forms.
Claim 66
Dependent Claim
17 words
A composition according to claim 35 wherein the compound is a mixture of 8R and 8S forms.
Claim 67
Dependent Claim
17 words
A composition according to claim 36 wherein the compound is a mixture of 8R and 8S forms.
Claim 68
Independent Claim
143 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula (I): ##STR111## a pharmaceutically acceptable salt thereof or an in vivo hydroxylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 69
Independent Claim
143 words
A method of treating bacterial infections in humans and animals which comprises administering to a human or animal in need thereof an antibacterially effective amount of a compound of the formula (I): ##STR111## a pharmaceutically acceptable salt thereof or an in vivo hydroxylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido or R is 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, benzyloxycarbonylmethyl or p-nitrobenzyloxycarbonylmethyl.
Claim 70
Dependent Claim
116 words
A method according to claim 61 wherein the compound is of the formula (II): ##STR112## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 71
Dependent Claim
116 words
A method according to claim 61 wherein the compound is of the formula (III): ##STR113## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 72
Dependent Claim
116 words
A method according to claim 61 wherein the compound is of the formula (IV): ##STR114## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 73
Dependent Claim
116 words
A method according to claim 61 wherein the compound is of the formula (V): ##STR115## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 74
Dependent Claim
116 words
A method according to claim 61 wherein the compound is of the formula (VI): ##STR116## a pharmaceutically acceptable salt thereof or an in vivo hydrozylable ester thereof, wherein X is SCH 2 CH 2 NH 2 or YNH.CO.CH 3 wherein Y is SCH 2 CH 2 , trans SO-CH═CH or cis or trans S-CH═CH and R is lower alkyl, phenyl unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkyl substituted by phenyl which phenyl moiety is itself unsubstituted or substituted by nitro, fluoro, chloro, bromo, lower alkyl or lower alkyloxy, lower alkenyl or lower alkyl substituted by lower alkoxy, lower alkanoyloxy, lower alkyl esterified carboxyl, carboxyl, amino or lower alkylamido.
Claim 75
Dependent Claim
13 words
A method according to claim 61 wherein the compound has the 8S configuration.
Claim 76
Dependent Claim
13 words
A method according to claim 61 wherein the compound has the 8R configuration.
Claim 77
Dependent Claim
17 words
A method according to claim 61 wherein the compound is a mixture of 8R and 8S isomers.
Claim 78
Dependent Claim
23 words
A method according to claim 61 wherein R is a methyl, ethyl, n-propyl, n-butyl, benzyl, 2-phenylethyl, phenyl, p-methylphenyl, p-methoxyphenyl, p-chlorophenyl, methoxycarbonylmethyl or ethoxycarbonylmethyl.
Claim 79
Dependent Claim
25 words
A method according to claim 61 wherein R is 2-aminoethyl, 2-benzyloxycarbonylaminoethyl, 2-p-nitrobenzyloxycarbonylaminoethyl, 2-p-methoxybenzyloxycarbonylaminoethyl, allyl, p-nitrobenzyl, p-chlorobenzyl, p-bromobenzyl, p-methoxybenzyl, p-methylbenzyl, 2-acetaminoethyl, benzyloxycarbonylmethyl, p-nitrobenzyloxycarbonylmethyl, 2-methoxyethyl or 2-acetoxyethyl.
Claim 80
Dependent Claim
14 words
A method according to claim 61 wherein R is methyl, ethyl, benzyl or phenyl.
Claim 81
Dependent Claim
21 words
A method according to claim 61 wherein the compound is in the form of a free acid or pharmaceutically acceptable salt.
Claim 82
Dependent Claim
19 words
A method according to claim 61 wherein the compound is in the form of an in vivo hydrolyzable ester.
Claim 83
Dependent Claim
13 words
A method according to claim 74 wherein the ester is a p-nitrobenzyl ester.
Claim 84
Dependent Claim
13 words
A method according to claim 62 wherein the compound has the 8S configuration.
Claim 85
Dependent Claim
13 words
A method according to claim 63 wherein the compound has the 8S configuration.
Claim 86
Dependent Claim
13 words
A method according to claim 64 wherein the compound has the 8S configuration.
Claim 87
Dependent Claim
13 words
A method according to claim 65 wherein the compound has the 8S configuration.
Claim 88
Dependent Claim
13 words
A method according to claim 66 wherein the compound has the 8S configuration.
Claim 89
Dependent Claim
13 words
A method according to claim 62 wherein the compound has the 8R configuration.
Claim 90
Dependent Claim
13 words
A method according to claim 63 wherein the compound has the 8R configuration.
Claim 91
Dependent Claim
13 words
A method according to claim 64 wherein the compound has the 8R configuration.
Claim 92
Dependent Claim
13 words
A method according to claim 65 wherein the compound has the 8R configuration.
Claim 93
Dependent Claim
13 words
A method according to claim 66 wherein the compound has the 8R configuration.
Claim 94
Dependent Claim
17 words
A method according to claim 62 wherein the compound is a mixture of 8R and 8S forms.
Claim 95
Dependent Claim
17 words
A method according to claim 63 wherein the compound is a mixture of 8R and 8S forms.
Claim 96
Dependent Claim
17 words
A method according to claim 64 wherein the compound is a mixture of 8R and 8S forms.
Claim 97
Dependent Claim
17 words
A method according to claim 65 wherein the compound is a mixture of 8R and 8S forms.
Claim 98
Dependent Claim
17 words
A method according to claim 66 wherein the compound is a mixture of 8R and 8S forms.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-07-13 | 1985-01-12 | 1985-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-07-13 | 1989-01-12 | 1989-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-07-13 | 1993-01-12 | 1993-07-14 | $7700.00 | Window Closed / Lapsed |