IP Library › Granted Patent US 7,524,850
Granted Patent B2
US 7,524,850 · App. 11/704,105 · Granted Apr 28, 2009

Substituted pyrazine inhibitors of AKT

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Quick Facts
Patent No.
US 7,524,850
App. No.
11/704,105
Granted
Apr 28, 2009
Kind
B2
Abstract

The compounds of Formula E are useful as anti-cancer agents:

Claims (32)

1. A compound according to Formula E:

wherein:

n is 0, 1 or 2;

R 1 is independently selected from:

1) OH, and

2) C 1 -C 10 alkyl, said alkyl optionally substituted with phenyl, 1H-indol-3-yl and OH,

or a pharmaceutically acceptable salt thereof.

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

3. A compound which is selected from:

1-{1-[4-(6-hydroxy-5-isobutyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(5-hydroxy-6-isobutyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one;

1-(1-{4-[5-hydroxy-6-(1H-indol-3-ylmethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one; and

1-(1-{4-[6-hydroxy-5-(1H-indol-3-ylmethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl)-1,3-dihydro-2H-benzimidazol-2-one;

or a pharmaceutically acceptable salt thereof.

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

5. A compound which is selected from:

1-{1-[4-(5-hydroxy-6-isobutyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(6-hydroxy-5-isobutyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(5 -hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(6-hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(6-benzyl-5-hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(5-benzyl-6-hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(6-sec-butyl-5-hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(5-sec-butyl-6-hydroxy-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

1-(1-{4-[5-hydroxy-6-(hydroxymethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl-)-1,3-dihydro-2H-benzimidazol-2-one;

1-(1-{4-[6-hydroxy-5-(hydroxymethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl-)-1,3-dihydro-2H-benzimidazol-2-one;

1-(1-{4-[5 -hydroxy-6-(1-H-imidazol-5-ylmethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl-)-1,3-dihydro-2H-benzimidazol-2-one;

1-(1-{4-[6-hydroxy-5-(1-H-imidazol-5-ylmethyl)-3-phenylpyrazin-2-yl]benzyl}piperidin-4-yl-)-1,3-dihydro-2H-benzimidazol-2-one;

1-{1-[4-(5-hydroxy-6-methyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one; and

1-{1-[4-(6-hydroxy-5-methyl-3-phenylpyrazin-2-yl)benzyl]piperidin-4-yl-}-1,3-dihydro-2H-benzimidazol-2-one;

or a pharmaceutically acceptable salt thereof.

6. A pharmaceutical composition comprising a pharmaceutical carrier, and dispersed therein, a therapeutically effective amount of a compound of claim 5 .

Assignments (3)
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 29, 2010
From: MERCK & CO., INC.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 023870/0001 →