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US 2013/0172280 A1Published application
Hydrogen bond forming fluoro ketolides for treating diseases
AssigneeCempra Pharmaceuticals, Inc.
InventorDavid E. Pereira
Life of this patent
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Abstract
The invention described herein pertains to a novel macrolide antibacterial agent of formula (I): A-L-Q, as defined herein, and pharmaceutically acceptable salts, solvates, and hydrates thereof. Inter alia, the new macrolide antibacterial agent is active against a number of bacterial species, including resistant species.
Claims30
A compound of formula I,
- A-L-Q (I)
- or a pharmaceutically acceptable salt thereof, wherein:
- A is a hydrogen bond forming group;
- L is a bivalent linking group comprising one or more units selected from the group consisting of optionally substituted methylene, O, S, optionally substituted NH, sulfonyl, vinylene, and cyclic units selected from the group consisting of divalent monocyclic and bicyclic carbocyclic and aromatic rings, and monocyclic and bicyclic heterocyclic and heteroaromatic rings, where the monocyclic and bicyclic heterocyclic and heteroaromatic rings contain 1 to 4 hetero atoms each independently selected from oxygen, sulfur and nitrogen, and where the cyclic units contain 5 to 10 ring atoms which are optionally substituted;
- providing that L does not include —O—O— or —O—S—;
- Q is
- in which L is bonded to the 11-N of Q;
- R2 is H or F;
- R5 is an aminosaccharide residue;
- and
- R6 is H or (1-6C)alkyl;
- and where
- (a) A is capable of forming a hydrogen bond interaction in a bacterial ribosome selected from the group consisting of hydrogen bond donation to O4′ of A752, hydrogen bond donation to 06 of G748, and hydrogen bond acceptance from N1 of G748;
- or
- (b) the 3-keto group of Q is capable of forming a hydrogen bond interaction with U2609;
- or
- (c) the aminosaccharide of Q is capable of forming a hydrogen bond interaction with A2059;
- or
- (d) the aminosaccharide of Q is capable of forming a hydrogen bond interaction with G2505;
- or
- any combination of (a), (b), (c), and (d);
- and
- wherein A-L- is other than 4-[4-(3-aminophenyl)[1,2,3]triazol-1-yl]butyl or 4-[4-(6-aminopyridin-2-yl)[1,2,3]triazol-1-yl]butyl.
20 more elements
-8. (canceled)
-13. (canceled)
(canceled)
(canceled)
-30. (canceled)
-34. (canceled)
-41. (canceled)
(canceled)
-50. (canceled)
Dependencies are inferred from the claim text.