2-isocephem and oxacephem derivatives, and use as antibacterial agents
First Claim
Patent Images
1. A compound of formula (I) or a salt thereof:
- ##STR21## wherein R1 is hydrogen, methoxy or formamido;
R2 is an acyl group of the formulae (a) to (f);
##STR22## wherein p is 0, 1 or 2;
m is 0, 1 or 2;
A1 is (C1-6) alkyl, substituted (C1-6) alkyl wherein the substituents are selected from the list from which R4 is selected, (C3-6) cycloalkyl, cyclohexenyl, cyclohexadienyl, phenyl, substituted phenyl, thienyl1 pyridyl, or an optionally substituted thiazolyl group, a (C1-6) akylthio group or (C1-6) alkyloxy;
X1 is a hydrogen or halogen atom, a carboxylic acid, carboxylic ester, sulphonic acid, azido, tetrazolyl, hydroxy, amino, ureido, heterocyclylamino, or guanidino;
A2 is an aryl group, a substituted C1-6 alkyl group;
or a substituted dithietane;
X2 is a --CH2 OCH2 --, --CH2 SCH2 -- or C2-6 alkylene group;
X3 is an oxygen or sulphur atom;
A3 is an aryl or heteroaryl group; and
A4 is hydrogen, (C1-6) alkyl, (C3-8) cycloalkyl, (C3-8) cycloalkyl(C1-6)alkyl, (C1-6) alkoxycarbonyl(C1-6)alkyl, (C2-6) alkenyl, carboxy(C1-6)alkyl, (C2-6) alkynyl, aryl or (C1-6)alkyl substituted by up to three aryl groups;
wherein said substituent is R4 as defined below;
CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolyzable ester group;
R4 represents hydrogen or up to four substituents, which may be present on any of the carbon atoms in the ring system shown, selected from C1-6 alkyl, C2-6 alkenyl, alkynyl, C2-6 alkoxy, hydroxy, halogen, amino, C2-6 alkylamino, acylamino, di( C1-6 alkyl)amino, CO2 R, CONR2, SO2 NR2 where R is hydrogen or C1-6 alkyl, aryl or heterocyclyl, which may be the same or different and wherein any R4 alkyl substituent is optionally substituted by one or more substituents selected from the list from which R4 is selected;
X is S, SO or SO2 ;
Y is S, SO or SO2 ;
n is 0 or 1; and
m is 1 or 2;
wherein said alkyl, alkenyl and alkynyl each are straight and branched chain groups;
said aryl is phenyl or naphthyl, each of which may be substituted with up to five groups selected from halogen, mercapto, (C1-6) alkyl, phenyl, (C1-6) alkyl, hydroxy, amino, nitro, carboxy, (C1-6) alkylcarbonyloxy, (C1-6) alkcoxycarbonyl, formyl, or (C1-6) alkylcarbonyl groups; and
wherein said heteroaryl is a heteroaromatic heterocyclic ring or ring system, having 5 or 6 ring atoms in each ring.
2 Assignments
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Accused Products
Abstract
Compounds of the formula: ##STR1## wherein R1 is hydrogen, methoxy or formamido;
R2 is an acyl group, in particular that of an antibacterially active cephalosporin;
CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a readily removable carboxy promoting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolysable ester group;
R4 represents hydrogen or up to four substituents, which my be present on any of the carbon atoms in the ring system shown, selected from alkyl, alkenyl, alkynyl, alkoxy, hydroxy, halogen, amino, alkylamino, acylamino, dialkylamino, CO2 R, CONR2, SO2 NR2 where R is hydrogen or alkyl, aryl and heterocyclyl, which may be the same or different and wherein any R4 aryl substituent is optionally substituted by one or more substituents selected from the list from which R4 is selected
Y is O, S, SO or SO2 ; n is 0 or 1; and m is 1 or 2;
for use in the treatment of bacterial infections in humans and animals.
6 Citations
14 Claims
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1. A compound of formula (I) or a salt thereof:
- ##STR21## wherein R1 is hydrogen, methoxy or formamido;
R2 is an acyl group of the formulae (a) to (f);
##STR22## wherein p is 0, 1 or 2;
m is 0, 1 or 2;
A1 is (C1-6) alkyl, substituted (C1-6) alkyl wherein the substituents are selected from the list from which R4 is selected, (C3-6) cycloalkyl, cyclohexenyl, cyclohexadienyl, phenyl, substituted phenyl, thienyl1 pyridyl, or an optionally substituted thiazolyl group, a (C1-6) akylthio group or (C1-6) alkyloxy;
X1 is a hydrogen or halogen atom, a carboxylic acid, carboxylic ester, sulphonic acid, azido, tetrazolyl, hydroxy, amino, ureido, heterocyclylamino, or guanidino;
A2 is an aryl group, a substituted C1-6 alkyl group;
or a substituted dithietane;
X2 is a --CH2 OCH2 --, --CH2 SCH2 -- or C2-6 alkylene group;
X3 is an oxygen or sulphur atom;
A3 is an aryl or heteroaryl group; and
A4 is hydrogen, (C1-6) alkyl, (C3-8) cycloalkyl, (C3-8) cycloalkyl(C1-6)alkyl, (C1-6) alkoxycarbonyl(C1-6)alkyl, (C2-6) alkenyl, carboxy(C1-6)alkyl, (C2-6) alkynyl, aryl or (C1-6)alkyl substituted by up to three aryl groups;
wherein said substituent is R4 as defined below;CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolyzable ester group; R4 represents hydrogen or up to four substituents, which may be present on any of the carbon atoms in the ring system shown, selected from C1-6 alkyl, C2-6 alkenyl, alkynyl, C2-6 alkoxy, hydroxy, halogen, amino, C2-6 alkylamino, acylamino, di( C1-6 alkyl)amino, CO2 R, CONR2, SO2 NR2 where R is hydrogen or C1-6 alkyl, aryl or heterocyclyl, which may be the same or different and wherein any R4 alkyl substituent is optionally substituted by one or more substituents selected from the list from which R4 is selected; X is S, SO or SO2 ;
Y is S, SO or SO2 ;
n is 0 or 1; and
m is 1 or 2;wherein said alkyl, alkenyl and alkynyl each are straight and branched chain groups; said aryl is phenyl or naphthyl, each of which may be substituted with up to five groups selected from halogen, mercapto, (C1-6) alkyl, phenyl, (C1-6) alkyl, hydroxy, amino, nitro, carboxy, (C1-6) alkylcarbonyloxy, (C1-6) alkcoxycarbonyl, formyl, or (C1-6) alkylcarbonyl groups; and
wherein said heteroaryl is a heteroaromatic heterocyclic ring or ring system, having 5 or 6 ring atoms in each ring. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12)
- ##STR21## wherein R1 is hydrogen, methoxy or formamido;
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13. A compound of formula (I) or a salt thereof:
- ##STR24## wherein R1 is hydrogen, methoxy or formamido;
R2 is an acyl group of the formulae (a) to (f);
##STR25## wherein p is 0, 1 or 2;
m is 0, 1 or 2;
A1 is (C1-6) alkyl, substituted (C1-6) alkyl wherein the substituents are selected from the list from which R4 is selected, (C3-6) cycloalkyl, cyclohexenyl, cyclohexadienyl, phenyl, substituted phenyl, thienyl1 pyridyl, or thiazolyl group, a (C1-6) akylthio group or (C1-6) alkyloxy;
X1 is a hydrogen or halogen atom, a carboxylic acid, carboxylic ester, sulphonic acid, azido, tetrazolyl, hydroxy, amino, ureido, heterocyclylamino, or guanidino;
A2 is an aryl group, a substituted alkyl group;
or a substituted dithietane;
X2 is a --CH2 OCH2 --, --CH2 SCH2 -- or C2-6 alkylene group;
X3 is an oxygen or sulphur atom;
A3 is an aryl or heteroaryl group; and
A4 is hydrogen, (C1-6) alkyl, (C3-8) cycloalkyl, (C3-8) cycloalkyl(C1-6)alkyl, (C1-6) alkoxycarbonyl(C1-6)alkyl, (C2-6) alkenyl, carboxy(C1-6)alkyl, (C2-6) alkynyl, aryl or (C1-6)alkyl substituted by up to three aryl groups;
wherein said substituents are R4 as defined below;CO2 R3 is a carboxy group or a carboxylate anion, or R3 is a readily removable carboxy protecting group or a pharmaceutically acceptable salt-forming group or in vivo hydrolyzable ester group; R4 represents hydrogen or up to four substituents, which may be present on any of the carbon atoms in the ring system shown, selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C2-6 alkoxy, hydroxy, halogen, amino, C2-6 alkylamino, acylamino, di(C1-6 alkyl)amino, CO2 R, CONR2, SO2 NR2 where R is hydrogen or C1-6 alkyl, aryl or heterocyclyl, which may be the same or different and wherein any R4 alkyl substituent is optionally substituted by one or more substituents selected from the list from which R4 is selected; X is S, SO or SO2;
Y is O;
n is 0 or 1; and
m is 1 or 2;
wherein said alkyl, alkenyl and alkynyl each are straight and branched chain groups;said aryl is phenyl or naphthyl, each of which may be substituted with up to five groups selected from halogen, mercapto, (C1-6) alkyl, phenyl, (C1-6) alkyl, hydroxy, amino, nitro, carboxy, (C1-6) alkylcarbonyloxy, (C1-6) alkcoxycarbonyl, formyl, or (C1-6) alkylcarbonyl groups; and
wherein said heteroaryl is a heteroaromatic heterocyclic ring or ring system, having 5 or 6 ring atoms in each ring. - View Dependent Claims (14)
- ##STR24## wherein R1 is hydrogen, methoxy or formamido;
Specification
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Current AssigneePfizer Inc.
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Original AssigneePfizer Inc.
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InventorsGasson, Brian C., Burton, George, Fell, Stephen C. M.
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Primary Examiner(s)Shah, Mukund J.
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Assistant Examiner(s)MYERS, RICHARD
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Application NumberUS08/256,677Time in Patent Office860 DaysField of Search540/214, 540/215, 514/210US Class Current514/210.05CPC Class CodesA61P 31/04 Antibacterial agentsC07D 405/06 linked by a carbon chain co...C07D 513/04 Ortho-condensed systemsY02P 20/55 Design of synthesis routes,...
