US 7,547,705 B2
Substituted 8′-pyri(MI)dinyl-dihydrospiro-[cycloalkylamine]-pyrimido[1,2-a]pyrimidin-6-one derivatives
Nathalie Chereze, Bourg la Reine (France); Alistair Lochead, Charenton le Pont (France); Mourad Saady, Paris (France); Franck Slowinski, Thieux (France); and Philippe Yaiche, Les Lilas (France)
Assigned to Sanofi-Aventis, Paris (France); and Mitsubishi Pharma Corporation, Osaka (Japan)
Filed on Oct. 03, 2007, as Appl. No. 11/866,687.
Application 11/866687 is a division of application No. 11/423557, filed on Jun. 12, 2006, granted, now 7,294,631.
Application 11/423557 is a continuation of application No. PCT/EP2004/014846, filed on Dec. 17, 2004.
Claims priority of application No. 03293236 (EP), filed on Dec. 19, 2003.
Prior Publication US 2008/0081820 A1, Apr. 03, 2008
Int. Cl. A61K 31/397 (2006.01); A61K 31/551 (2006.01); A61K 31/527 (2006.01); A61K 31/4162 (2006.01); C07D 225/00 (2006.01); C07D 223/00 (2006.01); C07D 487/20 (2006.01); C07D 239/00 (2006.01); A61P 3/10 (2006.01); A61P 25/28 (2006.01); A61P 25/16 (2006.01); A61P 25/18 (2006.01)
U.S. Cl. 514—267  [514/210.16; 514/212.02; 514/220; 540/466; 540/543] 5 Claims
 
1. A method of inhibiting the activity of glycogen synthase kinase 3-beta (GSK3-β), which comprises administering to a patient in need of said inhibition a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Drawing
wherein:
X represents two hydrogen atoms, a sulfur atom, an oxygen atom or a C1-2 alkyl group and a hydrogen atom;
Y represents a bond, a carbonyl group, a methylene group optionally substituted by one or two groups chosen from a C1-6 alkyl group, a hydroxyl group, a C1-4 alkoxy group, a C1-2 perhalogenated alkyl group or an amino group;
R1 represents a 2, 3 or 4-pyridine ring or a 2, 4 or 5-pyrimidine ring, the rings being optionally substituted by a C1-4 alkyl group, a C1-4 alkoxy group or a halogen atom;
R2 represents a benzene ring or a naphthalene ring; the rings being optionally substituted by 1 to 4 substituents selected from a C1-6 alkyl group, a methylenedioxy group, a halogen atom, a C1-2 perhalogenated alkyl group, a C1-3 halogenated alkyl group, a hydroxyl group, a C1-4 alkoxy group, a nitro, a cyano, an amino, a C1-5 monoalkylamino group or a C2-10 dialkylamino group;
R3 represents a hydrogen atom, a C1-6 alkyl group or a halogen atom;
R4 represents a hydrogen atom, a C1-4 alkoxy carbonyl group, a C3-6 cycloalkyl carbonyl group, a benzoyl group, a C1-6 alkyl group, the groups being optionally substituted by 1 to 4 substituents selected from a halogen atom, a hydroxyl group or a C1-4 alkoxy group;
o and m represent 1 to 2;
n represents 0 to 3;
p represents 0 to 2; and
q represents 0 to 2.