US 6,720,308 B1Granted

Anhydrolide derivatives having antibacterial activity

AssigneeEnanta Pharmaceuticals, Inc.

InventorsNha Huu Vo, Ying Hou, Ly Tam Phan, Yat Sun Or

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Abstract

Novel 11-12 substituted lactone anhydrolide derivatives and pharmaceutically-acceptable compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically-acceptable carrier are described. Also described are a method for treating bacterial infections by administering to an animal a pharmaceutical composition containing a therapeutically effective amount of a compound of the invention and processes for the preparation of such compounds.

Claims6

Dependent claims

A compound represented by the formula

and the pharmaceutically acceptable salts, esters and prodrugs thereof, wherein
L is selected from the group consisting of:
(1) —CH(OH)CH3;
(2) C1-C6 alkyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
(3) C2-C6 alkenyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
and
(4) C2-C6 alkynyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
R1 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, each optionally substituted with one or more substituents selected from the group consisting of:
(1) halogen;
(2) aryl;
(3) substituted aryl;
(4) heteroaryl;
(5) substituted heteroaryl;
(6) —O—R5, where R5 is selected from the group consisting of:
a. hydrogen;
b. aryl;
c. substituted aryl;
d. heteroaryl;
and
e. substituted heteroaryl;
(7) —O—C1-C6-alkyl-R5;
(8) —O—C2-C6-alkenyl-R5;
(9) —O—C2-C6-alkynyl-R5;
and
(10) —NR6R7, where R6 and R7 are each independently selected from the group consisting of:
hydrogen;
C1-C6-alkyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
C2-C6-alkenyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
and C2-C6-alkynyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
or R6R7 taken together with the nitrogen atom to which they are connected form a 3- to 7-membered ring which may optionally contain one or more hetero functions selected from the group consisting of —O—, —NH—, —N(C1-C6-alkyl)-, —N(aryl)-, —N(heteroaryl)-, —S—, —S(O)— and —S(O)2—;
R2 is selected from the group consisting of:
(1) hydrogen;
(2) C1-C6-alkyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3, where R3 is selected from the group consisting of:
i. hydrogen;
ii. aryl;
iii. substituted aryl;
iv. heteroaryl;
and
v. substituted heteroaryl;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
(3) C2-C6-alkenyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
and
(4) C2-C6-alkynyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
X is selected from the group consisting of:
(a) S(O)n, where n is 0, 1, or 2;
(b) O;
and
(c) NR5;
and
Rp is hydrogen or a hydroxy protecting group.

79 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound represented by the formula

and the pharmaceutically acceptable salts, esters and prodrugs thereof, wherein
L is selected from the group consisting of:
(1) —CH(OH)CH3;
(2) C1-C6 alkyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
(3) C2-C6 alkenyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
and
(4) C2-C6 alkynyl, optionally substituted with one or more substituents selected from the group consisting of aryl, substituted aryl, heteroaryl and substituted heteroaryl;
R1 is selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl and C2-C6-alkynyl, each optionally substituted with one or more substituents selected from the group consisting of:
(1) halogen;
(2) aryl;
(3) substituted aryl;
(4) heteroaryl;
(5) substituted heteroaryl;
(6) —O—R5, where R5 is selected from the group consisting of:
a. hydrogen;
b. aryl;
c. substituted aryl;
d. heteroaryl;
and
e. substituted heteroaryl;
(7) —O—C1-C6-alkyl-R5;
(8) —O—C2-C6-alkenyl-R5;
(9) —O—C2-C6-alkynyl-R5;
and
(10) —NR6R7, where R6 and R7 are each independently selected from the group consisting of:
hydrogen;
C1-C6-alkyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
C2-C6-alkenyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
and C2-C6-alkynyl, optionally substituted with one or more substituents selected from the group consisting of halogen, aryl, substituted aryl, heterocyclic and substituted heterocyclic;
or R6R7 taken together with the nitrogen atom to which they are connected form a 3- to 7-membered ring which may optionally contain one or more hetero functions selected from the group consisting of —O—, —NH—, —N(C1-C6-alkyl)-, —N(aryl)-, —N(heteroaryl)-, —S—, —S(O)— and —S(O)2—;
R2 is selected from the group consisting of:
(1) hydrogen;
(2) C1-C6-alkyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3, where R3 is selected from the group consisting of:
i. hydrogen;
ii. aryl;
iii. substituted aryl;
iv. heteroaryl;
and
v. substituted heteroaryl;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
(3) C2-C6-alkenyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
and
(4) C2-C6-alkynyl, optionally substituted with one or more substituents selected from the group consisting of:
a. halogen;
b. aryl;
c. substituted aryl;
d. heterocyclic;
e. substituted heterocyclic;
f. —O—R3;
g. —O—C1-C6-alkyl-R3;
h. —O—C2-C6-alkenyl-R3;
i. —O—C2-C6-alkynyl-R3;
and
j. —NR6R7;
X is selected from the group consisting of:
(a) S(O)n, where n is 0, 1, or 2;
(b) O;
and
(c) NR5;
and
Rp is hydrogen or a hydroxy protecting group.

79 more elements