US 9,808,464 B2
Compounds and compositions for ossification and methods related thereto
Scott D. Boden, Atlanta, GA (US); and Sreedhara Sangadala, Atlanta, GA (US)
Assigned to Emory University, Atlanta, GA (US); and The United States of America as represented by the Department of Veterans Affairs, Washington, DC (US)
Filed by Emory University, Atlanta, GA (US); and The United States of America as represented by the Department of Veterans Affairs, Washington, DC (US)
Filed on Oct. 25, 2016, as Appl. No. 15/334,030.
Application 15/334,030 is a division of application No. 13/816,312, granted, now 9,511,071, previously published as PCT/US2011/048252, filed on Aug. 18, 2011.
Claims priority of provisional application 61/479,910, filed on Apr. 28, 2011.
Claims priority of provisional application 61/374,667, filed on Aug. 18, 2010.
Prior Publication US 2017/0035771 A1, Feb. 9, 2017
Int. Cl. A61K 38/18 (2006.01); A61K 31/53 (2006.01); A61L 27/54 (2006.01); C07D 251/18 (2006.01)
CPC A61K 31/53 (2013.01) [A61K 38/1875 (2013.01); A61L 27/54 (2013.01); C07D 251/18 (2013.01); A61L 2300/412 (2013.01); A61L 2430/02 (2013.01)] 13 Claims
OG exemplary drawing
 
1. A method of forming bone or cartilage, comprising implanting a graft composition comprising a 2,4-diamino-1,3,5-triazine derivative or salt thereof in a subject under conditions such that bone or cartilage forms in the graft composition, wherein the 2,4-diamino-1,3,5-triazine derivative has the following formula:

OG Complex Work Unit Drawing
or salts thereof, wherein
if is a single bond then
R3 is alkyl, phenyl, benzyl, carbocyclyl, aryl, or heterocyclyl wherein R3 is optionally substituted with one or more the same or different R4;
R2 is hydrogen or alkyl; and
R1 is hydrogen or alkyl; or
if is a double bond then
R2 and R3 are absent;
R1 is alkyl, alkenyl, carbocyclyl, aryl, or heterocyclyl wherein R3 is optionally substituted with one or more the same or different R4, R4 is alkyl, halogen, nitro, cyano, hydroxy, amino, mercapto, formyl, carboxy, carbamoyl, alkoxy, alkylthio, alkylamino, (alkyl)2amino, alkylsulfinyl, alkylsulfonyl, arylsulfonyl, carbocyclyl, aryl, or heterocyclyl, wherein R4 is optionally substituted with one or more, the same or different, R5; and
R5 is halogen, nitro, cyano, hydroxy, trifluoromethoxy, trifluoromethyl, amino, formyl, carboxy, carbamoyl, mercapto, sulfamoyl, methyl, ethyl, methoxy, ethoxy, acetyl, acetoxy, methylamino, ethylamino, dimethylamino, diethylamino, N-methyl-N-ethylamino, acetylamino, N-methylcarbamoyl, N-ethylcarbamoyl, N,N-dimethylcarbamoyl, N,N-diethylcarbamoyl, N-methyl-N-ethylcarbamoyl, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, mesyl, ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamoyl, N-ethylsulfamoyl, N,N-dimethylsulfamoyl, N,N-diethylsulfamoyl, N-methyl-N-ethylsulfamoyl, carbocyclyl, aryl, or heterocyclyl.