Cephem compounds
First Claim
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1. A compound of the formula (II):
- ##STR33## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR34## wherein one of R6, R7 and R8 is alkyl to 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is --(CH2)n -- wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen.
1 Assignment
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Accused Products
Abstract
β-Lactam antibiotics are disclosed which have the formulae (Ia) or pharmaceutically acceptable salts or pharmaceutically acceptable in vivo hydrolysable esters thereof: ##STR1## wherein R1 is phenyl, substituted phenyl, cyclohexenyl, cyclohexadienyl, or an optionally substituted 5- or 6-membered heterocyclic ring containing up to three hetero-atoms selected from oxygen, sulphur or nitrogen; R2 is hydrogen or optionally substituted C1-6 alkyl; R3 is an optionally substituted 5- or 6- membered heterocyclic group containing one or two nitrogen heteroatoms; or R2 and R3 together with the nitrogen atom to which they are attached form an optionally substituted 5- or 6- membered heterocyclic group contaning one or two nitrogen heteroatoms; R4 is a substituted pyridinium group; and CO2 R is carboxy or a carboxylate anion; and also the use thereof.
Processes for the preparation of the compounds are disclosed together with intermediates for use therein.
15 Citations
15 Claims
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1. A compound of the formula (II):
- ##STR33## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR34## wherein one of R6, R7 and R8 is alkyl to 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is --(CH2)n -- wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen. - View Dependent Claims (2, 11)
- ##STR33## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
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3. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of formula (II):
- ##STR35## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR36## wherein one of R6, R7 and R8 is alkyl of 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is--(CH2)n -- wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen, in combination with a pharmaceutically acceptable carrier. - View Dependent Claims (4, 12)
- ##STR35## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, R1 is 2-thienyl or 2-furyl;
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5. 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 formula (II):
- ##STR37## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR38## wherein one of R6, R7 and R8 is alkyl of 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is--(CH2)n --wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen. - View Dependent Claims (6, 13)
- ##STR37## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
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7. A pharmaceutical composition useful for treating bacterial infections in humans and animals which comprises an antibacterially effective amount of a compound of formula (II):
- ##STR39## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR40## wherein one of R6, R7 and R8 is alkyl of 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is--(CH2)n -- wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen, and a β
-lactam inhibitory amount of a β
-lactam inhibitor, in combination with a pharmaceutically acceptable carrier. - View Dependent Claims (8, 14)
- ##STR39## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
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9. 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 formula (II):
- ##STR41## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
R4 is a substituted pyridinium moiety of the formula (a) or (b);
##STR42## wherein one of R6, R7 and R8 is alkyl of 1 to 6 carbon atoms;
or cycloalkyl of 3 to 7 carbon atoms; and
the other 2 of R6, R7 and R8 are hydrogen;
or R6 is 2-pyridyl and R7 and R8 are hydrogen;
X is--(CH2)n -- wherein n is an integer having the value 2, 3 or 4;
or X together with the bond in the ring to which it is joined forms a 6-membered aromatic carbocyclic ring, R10 is alkyl of 1 to 4 carbon atoms; and
R11 and R12 are each hydrogen, and a β
-lactam inhibitory amount of a β
-lactam inhibitor, in combination with a pharmaceutically acceptable carrier. - View Dependent Claims (10, 15)
- ##STR41## a pharmaceutically acceptable salt thereof or an in vivo hydrolyzable ester thereof wherein R1 is phenyl unsubstituted or substituted with up to 3 moieties selected from the group consisting of acetoxy, hydroxy and chloro, or R1 is 2-thienyl or 2-furyl;
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Current AssigneeBeecham Group PLC (GlaxoSmithKline PLC)
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Original AssigneeBeecham Group PLC (GlaxoSmithKline PLC)
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InventorsPearson, Michael J., Finch, Stephen C.
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Primary Examiner(s)Rizzo, Nicholas S.
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Application NumberUS06/894,926Time in Patent Office1,432 DaysField of Search540/221, 540/225, 514/201US Class Current514/201CPC Class CodesC07D 501/57 with a further substituent ...Y02P 20/55 Design of synthesis routes,...
