US 10,376,511 B2
Pyrazole pyrimidine derivative and uses thereof
Yinon Ben Neriah, Mevasseret Zion (IL); Guy Brachya, Jerusalem (IL); Ido Burstain, Moshav Sde-Yaakov (IL); Waleed Minzel, Kafr-Kanna (IL); Irit Snir-Alkalay, Mevasseret Zion (IL); Joseph Vacca, Telford, PA (US); and Dansu Li, Warrington, PA (US)
Assigned to Yissum Research Development Company of the Hebrew University of Jerusalem LTD., Jerusalem (IL)
Appl. No. 15/748,536
Filed by Yissum Research Development Company of the Hebrew University of Jerusalem LTD, Jerusalem (IL)
PCT Filed Aug. 4, 2016, PCT No. PCT/IL2016/050852
§ 371(c)(1), (2) Date Jan. 29, 2018,
PCT Pub. No. WO2017/021969, PCT Pub. Date Feb. 9, 2017.
Claims priority of provisional application 62/268,750, filed on Dec. 17, 2015.
Claims priority of provisional application 62/200,846, filed on Aug. 4, 2015.
Prior Publication US 2018/0214447 A1, Aug. 2, 2018
Int. Cl. A61K 31/506 (2006.01); A61P 35/02 (2006.01); C07D 405/14 (2006.01); C07D 413/14 (2006.01); C07D 403/04 (2006.01)
CPC A61K 31/506 (2013.01) [A61P 35/02 (2018.01); C07D 403/04 (2013.01); C07D 405/14 (2013.01); C07D 413/14 (2013.01)] 39 Claims
 
1. A compound having formula (I), or a stereoisomer or a pharmaceutically acceptable salt thereof:

OG Complex Work Unit Drawing
wherein:
R1 and R2 are each independently selected from H; and straight or branched C1-C8 alkyl, straight or branched C1-C5 alkoxy, straight or branched C1-C5 acyl, C5-C15 aryl, and C3-C7 heteroaryl, each of which is optionally substituted by at least one of halide, hydroxyl, an ester, an ether, C5-C15 aryl, C3-C7 heteroaryl, and an amide; or
R1 and R2 together with the nitrogen atom they are connected to form a 4-7 membered saturated, unsaturated, or aromatic ring that optionally includes at least one of N, O, NH, C═N, C═O, and SO2, and is optionally substituted with at least one of straight or branched C1-C5 alkyl, C5-C15 aryl, C3-C7 heteroaryl, hydroxyl, halide, and cyano;
R3 and R4 are each independently selected from H, and straight or branched C1-C8 alkyl optionally substituted by at least one of halide, hydroxyl, C1-C5 alkoxy, C5-C15 aryl, C3-C7 heteroaryl, an ester, and an amide; or
R1 or R2 together with R3 and the carbon and nitrogen atoms they are each connected to form a 4-7 membered saturated , unsaturated, or aromatic ring that optionally includes at least one of N, NH, O, C═N, C═O, and SO2, and is optionally substituted with at least one of straight or branched C1-C5 alkyl, C5-C15 aryl, C3-C7 heteroaryl, hydroxyl, and halide;
R5 and R8 are each independently selected from H and halide; and straight or branched C1-C8 alkyl, straight or branched C2-C8 alkenyl, and straight or branched C2-C8 alkynyl, each optionally substituted by at least one halide;
R6 is selected from straight or branched C1-C8 alkyl, straight or branched C2-C8 alkenyl, straight or branched C2-C8 alkynyl, C5-C10 cycloalkyl, and saturated or unsaturated 4-6 membered heterocyclyl, each of which is optionally substituted by at least one of straight or branched C1-C8 alkyl, C3-C7 cycloalkyl, 4-6 membered heterocyclyl, C5-C15 aryl, C3-C7 heteroaryl, halide, and hydroxyl; and
R7 is selected from straight or branched C1-C8 alkyl, straight or branched C2-C8 alkenyl, and straight or branched C2-C8 alkynyl, each of which is substituted by at least one of C3-C7 cycloalkyl, 4-6 membered heterocyclyl, C5-C15 aryl, C3-C7 heteroaryl, halide, and hydroxyl.