IP Library Granted Patent US 8,445,499
Granted Patent B2
US 8,445,499 · App. 13/426,418 · Granted May 21, 2013

Bipiperidinyl compounds, compositions, containing such compounds and methods of treatment

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Quick Facts
Patent No.
US 8,445,499
App. No.
13/426,418
Granted
May 21, 2013
Kind
B2
Abstract

Bipiperidinyl compounds of the formula: are disclosed as useful for treating or preventing type 2 diabetes and similar conditions. Pharmaceutically acceptable salts and solvates are included as well. The compounds are useful as agonists of the g-protein coupled receptor GPR-119.

Claims (25)

1. A compound represented by formula I:

or a pharmaceutically acceptable salt thereof wherein:

ring

represents phenyl or a 5-10 membered mono or bicyclic heteroaryl group containing at least one nitrogen atom, 0-2 additional nitrogen atoms, and 0-1 additional oxygen or sulfur atoms;

ring

is pyrimidine;

one R 1 group is selected from the group consisting of:

(1) CN;

(2) N(CH 3 ) 2 ;

(3) C(O)NR d R e , wherein R d is H and R e is selected from the group consisting of: cyclopropyl and cyclopropylmethyl;

and the remaining R 1 groups are H or halo selected from F and Cl, and

each R 2 is H or halo, or 1-2 are H or halo and the remainder are selected from the group consisting of:

1) CN;

2) NR f R g , wherein R f and R g each represent H or C 1-3 alkyl,

3) C 1-6 alkyl or OC 1-6 alkyl, said alkyl and alkyl portion being optionally substituted with 1-3 halo groups and 0-1 of NR f R g , S(O) x C 1-3 alkyl, S(O) 2 NR f R g and phenyl; wherein R f and R g are as defined above and x is 0, 1 or 2,

4) S(O) x C 1-3 alkyl, wherein x is as defined above, and

5) S(O) 2 NR f R g , wherein R f and R g are as defined above.

2. A compound in accordance with claim 1 wherein ring A represents phenyl or a 5-10 membered mono or bicyclic heteroaryl group containing at least one nitrogen atom and 0-2 additional nitrogen atoms, and 0-1 additional oxygen or sulfur atom.

3. A compound in accordance with claim 2 wherein ring A represents a member selected from the group consisting of: phenyl, thiazole, thiadiazole, pyridyl, pyrimidine and pyrazine.

4. A compound in accordance with claim 3 wherein ring A represents a member selected from the group consisting of: phenyl, pyridyl, pyrimidine and pyrazine.

5. A pharmaceutical composition comprised of a compound in accordance with claim 1 in combination with a pharmaceutically acceptable carrier.

6. A compound which is:

6-[1′-(5-chloropyrimidin-2-yl)-4,4′-bipiperidin-1-yl]pyrimidine-4-carbonitrile;

6-(1′-pyrimidin-2-yl-4,4′-bipiperidin-1-yl)pyrimidine-4-carbonitrile;

or a pharmaceutically acceptable salt thereof.

Assignments (2)
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 →