IP Library Granted Patent US 7,323,570
Granted Patent B2
US 7,323,570 · App. 11/459,745 · Granted Jan 29, 2008

Farnesyltransferase inhibitors

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 7,323,570
App. No.
11/459,745
Granted
Jan 29, 2008
Kind
B2
Abstract

Substituted imidazoles and thiazoles having the formula are useful for inhibiting farnesyltransferase. Also disclosed are farnesyltransferase-inhibiting compositions and methods of inhibiting farnesyltransferase in a patient.

Claims (39)

1. A compound of formula (I)

or a therapeutically acceptable salt thereof, wherein

E is pyridinyl;

F and G are independently selected from the group consisting of C and N;

with the proviso that when one of F and G is N, the other is C;

L 1 is O;

L 2 is selected from the group consisting of a bond, C 2 alkenylene, C 2 alkynylene, O, NR 9 , C(O), S, S(O), SO 2 , SO 2 NR 9 , NR 9 SO 2 , C(O)NR 9 , NR 9 C(O), and CO 2 ;

X is NR 7 ;

R 1 is phenyl optionally substituted by hydrogen, halo or cyano;

R 2 is selected the group consisting of hydrogen, alkyl, aminoalkyl, cyanoalkyl, halo, haloalkyl, and hydroxyalkyl;

R 3 is phenyl optionally substituted by a halo;

R 4-6 are each independently selected from the group consisting of hydrogen, alkanoyl, alkenyl, alkoxy, alkoxyalkyl, alkyl, alkylsulfonyl, alkynyl, amido, amino, aminoalkyl, aminosulfonyl, azido, carboxy, cyano, cyanoalkyl, halo, haloalkoxy, haloalkyl, hydroxy, hydroxyalkyl, nitro, nitroalkyl, oxo, and thio(oxo);

R 7 is selected from the group consisting of hydrogen, alkyl, aryl, cycloalkyl, cycloalkylalkyl;

R 9 is selected from the group consisting of hydrogen, alkoxyalkyl, alkyl, amidoalkyl, aminoalkyl, aryl, arylalkyl, cycloalkyl, and cycloalkylalkyl, carboxyalkyl, and hydroxyalkyl;

each R 12 is independently selected from the group consisting of hydrogen, alkoxy, alkyl, amino, halo, and hydroxy;

m is 0, 1, 2, 3 or 4;

n is 0, 1, 2, 3 or 4;

p is 0, 1, 2, 3 or 4; and

q is 0, 1, 2, 3 or 4.

2. A compound according to claim 1 of formula (II)

or a therapeutically acceptable salt thereof, wherein

E, F, G, L 1 , L 2 , X, R 2 , R 3 , R 4-6 , R 12 , and p are as defined in claim 1 and

R 18 , R 19 , and R 20 are each independently selected from the group consisting of hydrogen, cyano, and halo.

3. A compound according to claim 2 wherein

L 2 is selected from the group consisting of a bond, NR 9 SO 2 , and C(O)NR 9 ;

wherein each group is drawn with its left end attached to F and its right end attached to R 3 ;

R 2 is hydrogen;

R 12 is hydrogen; and

p is 0 or 1.

4. A compound according to claim 3 wherein

R 18 is cyano; and

R 19 R 20 are hydrogen.

5. A compound according to claim 4 selected from the group consisting of

4-(((6-chloro-2-(3-chlorophenyl)-3-pyridinyl)methoxy)(1-methyl-1H-imidazol-5-yl)methyl)benzonitrile;

4-(((2-(3-chlorophenyl)-6-methyl-3-pyridinyl)methoxy)(1-methyl-1H-imidazol-5-yl)methyl)benzonitrile;

4-(((4-(3-chlorophenyl)-6-fluoro-3-pyridinyl)methoxy)(1-methyl-1H-imidazol-5-yl)methyl)benzonitrile;

4-(((4-(3-chlorophenyl)-6-methoxy-3-pyridinyl)methoxy)(1-methyl-1H-imidazol-5-yl)methyl)benzonitrile;

4-(3-chlorophenyl)-5-(((4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy)methyl)-2-pyridinecarbonitrile; and

5-(((4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy)methyl)-6-(3,5-difluorophenyl)pyridine-2-carbonitrile.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 8, 2013
From: ABBOTT LABORATORIES
To: ABBVIE INC.
Reel/Frame 030167/0733 →