US 2002/0160966 A1Published application

Bicyclic leucomycins

AssigneeEnanta Pharmaceuticals, Inc.

InventorsYat Sun Or, Sophie Binet, Ly Tam Phan

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Abstract

Bicyclic leucomycins and pharmaceutically acceptable compositions comprising a therapeutically effective amount of a compound of the invention in combination with a pharmaceutically acceptable carrier, 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, and processes for the preparation of such compounds

Claims15

Dependent claims

A compound represented by the Formula:

7
or a pharmaceutically acceptable salt, ester, or prodrug thereof, wherein
A is selected from the group consisting of;
(1) —CHO or a protected aldehyde,
(2) —CH2X, 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 hydrogen, aryl, heterocyclic, substituted aryl, substituted heterocyclic, C1-C6-alkyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, C2-C6-alkenyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic and C2-C6 alkynyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic;
or R7R8 taken 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. C2-C6-alkenyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
iii. C2-C6-alkynyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
iv. aryl,
v. substituted aryl,
vi. heterocyclic, and
vii. substituted heterocyclic
e. —NR7C(O)—NR8R9, where R7, R8, and R9 are as previously defined,
f. —S(O)n-(C1-C6-alkyl), optionally substituted with aryl substituted aryl, heterocyclic or substituted heterocyclic where n=0, 1 or 2,
g. —S(O)n-(C2-C6-alkenyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, where n is as previously defined,
h. —S(O)n-(C2-C6-alkynyl), optionally substituted with aryl, substituted aryl heterocyclic or substituted heterocyclic, where n=is as previously defined,
i. —S(O)n-(aryl or heterocyclic) where n is as previously defined,
j. —O—(aryl or heterocyclic),
k. —O—(C1-C6-alkyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
l. —O—(C2-C6-alkenyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, and
m. —O—(C2-C6 alkynyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
(3) substituted or unsubstituted imidazole, arylimidazole or heteroarylimidazole,
(4) substituted or unsubstituted oxazole, aryloxazole or heteroaryloxazole,
(5) substituted or unsubstituted thioxazole, arylthioxazole or heteroarylthioxazole,
(6) substituted or unsubstituted imidazoline, arylimidazoline or heteroarylimidazoline,
(7) substituted or unsubstituted oxazoline, aryloxazoline or heteroaryloxazoline, and
(8) substituted or unsubstituted thioxazoline, arylthioxazoline and heteroarylthioxazoline,
W and Z are each independently selected from the group consisting of carbon and nitrogen
B and Q are each independently selected from the group consisting of
(1) hydrogen
(2) —C(O)OR7 where R7 is as previously defined,
(3) —C(O)R7 where R7 is as previously defined,
(4) —C(O)NR7R8 where R7 and R8 are as previously defined,
(5) —CH2X, where X is as previously defined,
(6) —CN,
(7) —CHO,
(8) C1-C6-alkyl, optionally substituted with R9 where R9 is as previously defined,
(9) C2-C6-alkenyl, optionally substituted with R9 where R9 is as previously defined,
(10) C2-C6-alkynyl, optionally substituted with R9 where R9 is as previously defined, and
(11) B and Q are taken together to form
a. —C(O)OC(O)—, or
b. —C(O)YC(O)—, where Y is selected from the group consisting of;
i. C1-C6 alkyl optionally substituted with R7 where R7 is as previously defined,
ii. C2-C6 alkenyl optionally substituted with R7 where R7 is as previously defined, and
iii. —NR7-, where R7 is as previously defined,
provided that in Formulas IV and V, B is absent when W is nitrogen and Q is absent when Z is nitrogen,
L and M are each independently selected from the group consisting of;
(1) hydrogen,
(2) —C(O)OR7, where R7 is as previously defined,
(3) —C(O)R7, where R7 is as previously defined,
(4) —C(O)NR7R8, where R7 and R8 are as previously defined,
(5) —CHO,
(6) C1-C6-alkyl, optionally substituted with R9, where R9 is as previously defined,
(7) —CH2-(C2-C6-alkenyl), optionally substituted with R9, where R9 is as previously defined,
(8) —CH2-(C2-C6-alkynyl), optionally substituted with R9, where R9 is as previously defined, and
(9) L and M are taken together to form —C(O)YC(O)—, where Y is as previously defined,
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, —O—R7 or —NR7R8 where R7 and NR7R8 are as previously defined,
(5) D-forosamine, and
(6) L-mycarose
R3 and R4 are each independently selected from the group consisting of
(1) hydrogen,
(2) a hydroxy protecting group,
(3) —C(O)—(C1-C12-alkyl), optionally substituted with aryl, substituted aryl, heterocyclic, substituted heterocyclic, —O—R7 or —NR7R8 where R7 and R8 are as previously defined;
and
Rp is hydrogen or a hydroxy protecting group.

71 more elements

Dependencies are inferred from the claim text.

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Abstract

A compound represented by the Formula:

7
or a pharmaceutically acceptable salt, ester, or prodrug thereof, wherein
A is selected from the group consisting of;
(1) —CHO or a protected aldehyde,
(2) —CH2X, 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 hydrogen, aryl, heterocyclic, substituted aryl, substituted heterocyclic, C1-C6-alkyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, C2-C6-alkenyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic and C2-C6 alkynyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic;
or R7R8 taken 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. C2-C6-alkenyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
iii. C2-C6-alkynyl, optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
iv. aryl,
v. substituted aryl,
vi. heterocyclic, and
vii. substituted heterocyclic
e. —NR7C(O)—NR8R9, where R7, R8, and R9 are as previously defined,
f. —S(O)n-(C1-C6-alkyl), optionally substituted with aryl substituted aryl, heterocyclic or substituted heterocyclic where n=0, 1 or 2,
g. —S(O)n-(C2-C6-alkenyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, where n is as previously defined,
h. —S(O)n-(C2-C6-alkynyl), optionally substituted with aryl, substituted aryl heterocyclic or substituted heterocyclic, where n=is as previously defined,
i. —S(O)n-(aryl or heterocyclic) where n is as previously defined,
j. —O—(aryl or heterocyclic),
k. —O—(C1-C6-alkyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
l. —O—(C2-C6-alkenyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic, and
m. —O—(C2-C6 alkynyl), optionally substituted with aryl, substituted aryl, heterocyclic or substituted heterocyclic,
(3) substituted or unsubstituted imidazole, arylimidazole or heteroarylimidazole,
(4) substituted or unsubstituted oxazole, aryloxazole or heteroaryloxazole,
(5) substituted or unsubstituted thioxazole, arylthioxazole or heteroarylthioxazole,
(6) substituted or unsubstituted imidazoline, arylimidazoline or heteroarylimidazoline,
(7) substituted or unsubstituted oxazoline, aryloxazoline or heteroaryloxazoline, and
(8) substituted or unsubstituted thioxazoline, arylthioxazoline and heteroarylthioxazoline,
W and Z are each independently selected from the group consisting of carbon and nitrogen
B and Q are each independently selected from the group consisting of
(1) hydrogen
(2) —C(O)OR7 where R7 is as previously defined,
(3) —C(O)R7 where R7 is as previously defined,
(4) —C(O)NR7R8 where R7 and R8 are as previously defined,
(5) —CH2X, where X is as previously defined,
(6) —CN,
(7) —CHO,
(8) C1-C6-alkyl, optionally substituted with R9 where R9 is as previously defined,
(9) C2-C6-alkenyl, optionally substituted with R9 where R9 is as previously defined,
(10) C2-C6-alkynyl, optionally substituted with R9 where R9 is as previously defined, and
(11) B and Q are taken together to form
a. —C(O)OC(O)—, or
b. —C(O)YC(O)—, where Y is selected from the group consisting of;
i. C1-C6 alkyl optionally substituted with R7 where R7 is as previously defined,
ii. C2-C6 alkenyl optionally substituted with R7 where R7 is as previously defined, and
iii. —NR7-, where R7 is as previously defined,
provided that in Formulas IV and V, B is absent when W is nitrogen and Q is absent when Z is nitrogen,
L and M are each independently selected from the group consisting of;
(1) hydrogen,
(2) —C(O)OR7, where R7 is as previously defined,
(3) —C(O)R7, where R7 is as previously defined,
(4) —C(O)NR7R8, where R7 and R8 are as previously defined,
(5) —CHO,
(6) C1-C6-alkyl, optionally substituted with R9, where R9 is as previously defined,
(7) —CH2-(C2-C6-alkenyl), optionally substituted with R9, where R9 is as previously defined,
(8) —CH2-(C2-C6-alkynyl), optionally substituted with R9, where R9 is as previously defined, and
(9) L and M are taken together to form —C(O)YC(O)—, where Y is as previously defined,
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, —O—R7 or —NR7R8 where R7 and NR7R8 are as previously defined,
(5) D-forosamine, and
(6) L-mycarose
R3 and R4 are each independently selected from the group consisting of
(1) hydrogen,
(2) a hydroxy protecting group,
(3) —C(O)—(C1-C12-alkyl), optionally substituted with aryl, substituted aryl, heterocyclic, substituted heterocyclic, —O—R7 or —NR7R8 where R7 and R8 are as previously defined;
and
Rp is hydrogen or a hydroxy protecting group.

71 more elements