IP Library Granted Patent US 7,705,014
Granted Patent B2
US 7,705,014 · App. 11/918,386 · Granted Apr 27, 2010

Inhibitors of AKT activity

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Quick Facts
Patent No.
US 7,705,014
App. No.
11/918,386
Granted
Apr 27, 2010
Kind
B2
Abstract

The instant invention provides for compounds that inhibit Akt activity. In particular, the compounds disclosed selectively inhibit one or two of the Akt isoforms. The invention also provides for compositions comprising such inhibitory compounds and methods of inhibiting Akt activity by administering the compound to a patient in need of treatment of cancer.

Claims (20)

1. A compound according to Formula D:

wherein:

R 5 is: NR 7′ R 8′ ;

R 6a is selected from: (C═O) a O b (C 1 -C 10 )alkyl, O a (C 1 -C 3 )perfluoroalkyl, (C 0 -C 6 )alkylene-S(O) m R a , oxo, OH, halo, CN, (C 2 -C 10 )alkenyl, (C 2 -C 10 )alkynyl, (C 3 -C 6 )cycloalkyl, (C 0 -C 6 )alkylene-aryl, (C 0 -C 6 )alkylene-heterocyclyl, (C 0 -C 6 )alkylene-N(R b ) 2 , C(O)R a , (C 0 -C 6 )alkylene-CO 2 R a , C(O)H, and (C 0 -C 6 )alkylene-CO 2 H, said alkyl, alkenyl, alkynyl, cycloalkyl, aryl, and heterocyclyl is optionally substituted with up to three substituents selected from R b , OH, (C 1 -C 6 )alkoxy, halogen, CO 2 H, CN, O(C═O)C 1 -C 6 alkyl, oxo, and N(R b ) 2 ;

R 7′ and R 8′ are attached to form a bicyclic or trycyclic heterocycle with 3-7 members in each ring and optionally containing, in addition to the nitrogen, one or more additional heteroatoms selected from N, O and S, said bicyclic or tricyclic heterocycle optionally substituted with one or more substituents selected from R 6a ;

R a is (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, aryl, or heterocyclyl; and

R b is H, (C 1 -C 6 )alkyl, aryl, heterocyclyl, (C 3 -C 6 )cycloalkyl, (C═O) a O b (C 1 -C 6 )alkyl, or S(O) 2 R a ;

or a pharmaceutically acceptable salt or a stereoisomer thereof.

2. A compound according to claim 1 which is selected from:

2-{4-[(3-hydroxy-4,7-dihydroisoxazolo[5,4-c]pyridin-6(5H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one;

3-phenyl-2-(4-{[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]methyl}phenyl)-1,6-naphthyridin-5(6H)-one;

methyl 2-[4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzyl]-1,2,3,4-tetrahydroisoquinoline-6-carboxylate;

methyl 2-[4-(5-oxo-3-phenyl-5,6-dihydro-1,6-naphthyridin-2-yl)benzyl]-1,2,3,4-tetrahydroisoquinoline-7-carboxylate;

2-{4-[(6-amino-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one;

3-phenyl-2-[4-(1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-ylmethyl)phenyl]-1,6-naphthyridin-5(6H)-one;

3-phenyl-2-(4-{[3-(trifluoromethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl]methyl}phenyl)-1,6-naphthyridin-5(6H)-one;

3-phenyl-2-[4-(1,3,4,9-tetrahydro-2H-b-carbolin-2-ylmethyl)phenyl]-1,6-naphthyridin-5(6H)-one; and

2-{4-[(6,7-dihydroxy-3,4-dihydroisoquinolin-2(1H)-yl)methyl]phenyl}-3-phenyl-1,6-naphthyridin-5(6H)-one;

or a pharmaceutically acceptable salt or stereoisomer thereof.

3. A pharmaceutical composition comprising a pharmaceutical carrier, and dispersed therein, a therapeutically effective amount of a compound of claim 1 .

Assignments (4)
CHANGE OF NAME Recorded Aug 29, 2012
From: SCHERING CORPORATION
To: MERCK SHARP & DOHME CORP.
Reel/Frame 028866/0511 →
MERGER Recorded Aug 27, 2012
From: MERCK SHARP & DOHME CORP.
To: SCHERING CORPORATION
Reel/Frame 028850/0515 →
CHANGE OF NAME Recorded Jan 26, 2010
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 023906/0803 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 15, 2008
From: CHEN, CHIXU; EASTMAN, BRIAN W.; HU, ESSA H.
To: MERCK & CO., INC.
Reel/Frame 021978/0857 →