Inhibitors of .beta.-lactamases and uses therefor
First Claim
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1. A method of treating a β
- -lactam-antibiotic-resistant bacterial infection comprising administering to an animal suffering from such an infectionan effective amount of a compound which is a β
-lactamase inhibitor, the compound having the formula;
##STR19## wherein;
R is naphthalene, phenanthrene, or has one of the following formulas;
##STR20## wherein ring system (2), (4), (5), (6), (7), (8), (9), (10), (13) or (14) is aromatic or nonaromatic;
the atom center * is (R) or (S) in the case of chiral compounds;
positions 1, 2, 3, 4, 5, 6, 7 or 8 each independently is C, O or S;
each R1 independently is a lone pair, H, B(OH)2, a halogen atom, CF3, CH2 CF3, CCl3, CH2 CCl3, CBr3, CH2 CBr3, NO2, lower alkyl, CO2 H, CHCHCOOH, CH2 CH2 CH2 COOOH, SO3 H, PO3 H, OSO3 H, OPO3 H, OH, NH2, CONH2, COCH3, OCH3, or phenyl boronic acid;
or a pharmaceutically-acceptable salt thereof; and
an effective amount of a β
-lactam antibiotic.
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Abstract
The invention provides novel non-β-lactam inhibitors of β-lactamases. In particular, the invention provides such inhibitors which are boronic acids of formula (1) which is set forth in the specification. These compounds may be used with β-lactam antibiotics to treat β-lactam-antibiotic-resistant bacterial infections. These compounds are also antibacterial by themselves. Finally, the invention provides a pharmaceutical composition comprising these compounds.
61 Citations
24 Claims
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1. A method of treating a β
- -lactam-antibiotic-resistant bacterial infection comprising administering to an animal suffering from such an infection
an effective amount of a compound which is a β
-lactamase inhibitor, the compound having the formula;
##STR19## wherein;
R is naphthalene, phenanthrene, or has one of the following formulas;
##STR20## wherein ring system (2), (4), (5), (6), (7), (8), (9), (10), (13) or (14) is aromatic or nonaromatic;the atom center * is (R) or (S) in the case of chiral compounds; positions 1, 2, 3, 4, 5, 6, 7 or 8 each independently is C, O or S; each R1 independently is a lone pair, H, B(OH)2, a halogen atom, CF3, CH2 CF3, CCl3, CH2 CCl3, CBr3, CH2 CBr3, NO2, lower alkyl, CO2 H, CHCHCOOH, CH2 CH2 CH2 COOOH, SO3 H, PO3 H, OSO3 H, OPO3 H, OH, NH2, CONH2, COCH3, OCH3, or phenyl boronic acid; or a pharmaceutically-acceptable salt thereof; and an effective amount of a β
-lactam antibiotic. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
- -lactam-antibiotic-resistant bacterial infection comprising administering to an animal suffering from such an infection
-
11. A method of inhibiting a β
- -lactamase comprising contacting the β
-lactamase with an effective amount of a compound having the formula;
##STR21## wherein;
R is naphthalene, phenanthrene, or has one of the following formulas;
##STR22## wherein;
ring system (2), (4), (5), (6), (7), (8), (9), (10), (13) or (14) is aromatic or nonaromatic;the atom center * is (R) or (S) in the case of chiral compounds; positions 1, 2, 3, 4, 5, 6, 7 or 8 each independently is C, N, O or S; each R1 independently is a lone pair, H, B(OH)2, a halogen atom, CF3, CH2 CF3, CCl3, CH2 CCl3, CBr3, CH2 CBr3, NO2, lower alkyl, CO2 H, CHCHCOOH, CH2 CH2 C2 CH2 COOH, SO3 H, PO3 H, OSO3 H, OPO3 H, OH, NH2, CONH2, COCH3, OCH3, or phenyl boronic acid; or pharmaceutically acceptable salts thereof. - View Dependent Claims (12, 13)
- -lactamase comprising contacting the β
-
14. A pharmaceutical composition comprising a compound which is a β
- -lactamase inhibitor having the formula;
##STR23## wherein;
R is naphthalene, phenanthrene, or has one of the following formulas;
##STR24## wherein;
ring system (2), (3), (4), (5), (6), (7), (8), (9), (10), (13) or (14) is aromatic or nonaromatic;the atom center * is (R) or (S) in the case of chiral compounds; positions 1, 2, 3, 4, 5, 6, 7 or 8 each independently is C, O or S; each R1 independently is a lone pair, H, B(OH)2, a halogen atom, CF3, CH2 CF3, CCl3, CH2 CCl3, CBr3, CH2 CBr3, NO2, lower alkyl, CO2 H, CHCHCOOH, CH2 CH2 CH2 COOH, SO3 H, PO3 H, OSO3 H, OPO3 H, OH, NH2, CONH2, COCH3, OCH3, or phenyl boronic acid; or pharrnaceutically-acceptable salts thereof. - View Dependent Claims (15, 16, 17, 18, 19, 20, 21, 22, 23, 24)
- -lactamase inhibitor having the formula;
Specification
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Current AssigneeNorthwestern University
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Original AssigneeNorthwestern University
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InventorsShoichet, Brian, Weston, Scott
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Primary Examiner(s)Weddington, Kevin E.
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Application NumberUS09/096,893Time in Patent Office732 DaysField of Search514/64, 514/330, 514/340, 514/451, 514/456, 514/481, 514/543US Class Current514/64CPC Class CodesA61K 2300/00 Mixtures or combinations of...A61K 31/18 Sulfonamides compounds cont...A61K 31/34 having five-membered rings ...A61K 31/38 having sulfur as a ring het...A61K 31/40 having five-membered rings ...A61K 31/405 Indole-alkanecarboxylic aci...A61K 31/69 Boron compoundsA61K 33/22 Boron compoundsA61P 31/04 Antibacterial agentsA61P 43/00 Drugs for specific purposes...
