14-membered macrolides derived from leucomycins
AssigneeEnanta Pharmaceuticals, Inc.
InventorsYat Sun Or, Tsvetelina Lazarova, Sophie Binet, Jianchao Wang
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Abstract
There is described a novel class of ring contracted 14-membered macrolides, and pharmaceutically acceptable salts, esters and prodrugs thereof, having antibacterial activity, compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier as well as a method for treating bacterial infections by administering to a mammal a pharmaceutical composition containing a therapeutically effective amount of a compound of the invention. There are also described synthetic processes for preparing the compounds of the invention.
Claims11
A compound represented by the Formula:
- or a pharmaceutically acceptable salt, ester and prodrug thereof, wherein
- A is:
- (1) CHO;
- (2) CH2-X, where X is selected from the group consisting of
- a. hydroxy or protected hydroxy,
- b. halogen,
- c. NR7R8 wherein R7 and R8 are each independently selected from the group consisting of hydrogen and C1-C6-alkyl optionally substituted with aryl, or heterocyclic groups;
- or R7and R8 taken together with the nitrogen atom to which they are connected form a 3- to 7-membered ring which, may optionally contain a hetero function selected from the group consisting of —O—, —NH—, —N(C1-C6-alkyl)-, —N(aryl)-, —N(heteroaryl)- , —S—, —S(O)— and —S(O)2-,
- d. NR7C(O)—R9, where R7 is as previously defined and R9 is selected from the group consisting of
- i. C1-C6-alkyl optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
- ii. aryl,
- iii. substituted aryl,
- iv. heterocyclic, and
- v. substituted heterocyclic,
- e. S(O)n-(C1-C6-alkyl) optionally substituted with aryl or a heterocyclic group where n=0, 1 or 2,
- f. S(O)n-(aryl or heterocyclic group) where n=0, 1 or 2, and
- g. O-(aryl or heterocyclic group);
- (3) an aldehyde protecting group
- (4) substituted or unsubstituted imidazole, arylimidazole or heteroarylimidazole
- (5) substituted or unsubstituted oxazole, aryloxazole or heteroaryloxazole
- (6) substituted or unsubstituted thioxazole, arylthioxazole or heteroarylthioxazole
- (7) substituted or unsubstituted imidazoline, arylimidazoline or heteroarylimidazoline
- (8) substituted or unsubstituted oxazoline, aryloxazoline or heteroaryloxazoline or
- (9) substituted or unsubstituted thioxazoline, arylthioxazoline or heteroarylthioxazoline
- R1 and R2 are each independently selected from the group consisting of
- (1) hydrogen,
- (2) hydroxy,
- (3) protected hydroxy,
- (4) OC(O)—C1-C12 alkyl, optionally substituted with aryl, substituted aryl, heterocyclic, substituted heterocyclic,
- (5) O—R7 where R7 is as previously defined,
- (6) halogen, and
- (7) R1and R2 taken together are oxo;
- R3, R4 and R5 are each independently selected from the group consisting of
- (1) hydrogen,
- (2) a hydroxy protecting group, and
- (3) C(O)—C1-C12 alkyl, optionally, substituted with aryl, substituted aryl, heterocyclic, substituted heterocyclic. O—R7 or NR7R8 where R7 and NR7R8 are as previously defined;
- and
- RP) is hydrogen or a hydroxy protecting group.
Dependencies are inferred from the claim text.