US 7,547,702 B2
4-amino-quinazolines
Werner Mederski, Zwingenberg (Germany); Ralf Devant, Darmstadt (Germany); Maria Devant, legal representative; Gerhard Barnickel, Darmstadt (Germany); Sabine Bernotat-Danielowski, Bad Neuheim (Germany); James Vickers, Wolverhampton (United Kingdom); Bertram Cezanne, Moerfelden-Walldorf (Germany); Daljit Dhanoa, Wakefield, Mass. (US); Bao-Ping Zhao, Plainsboro, N.J. (US); James Rinker, Kenhurst, Pa. (US); Mark R. Player, Phoenixville, Pa. (US); Edward Jaegar, Trappe, Pa. (US); and Richard Soll, Lawrenceville, N.J. (US)
Assigned to Ortho-McNeil Pharmaceutical, Inc., Rantan, N.J. (US)
Appl. No. 10/380,908
PCT Filed Sep. 17, 2001, PCT No. PCT/EP01/10705
§ 371(c)(1), (2), (4) Date Jun. 30, 2005,
PCT Pub. No. WO02/24667, PCT Pub. Date Mar. 28, 2002.
Claims priority of provisional application 60/304188, filed on Sep. 20, 2000.
Prior Publication US 2006/0019974 A1, Jan. 26, 2006
Int. Cl. A61K 31/517 (2006.01); A61K 31/535 (2006.01); C07D 239/72 (2006.01); C07D 413/12 (2006.01)
U.S. Cl. 514—252.14  [514/252.17; 514/266.4; 514/235.8; 544/293; 544/116] 4 Claims
 
1. Compounds of the formula I

OG Complex Work Unit Drawing
in which
R and R1 are independently of each other H, alkyl of 1-6 carbon atoms, OR5, Hal, N(R5)2, NO2, CN, CHO, COalkyl of 1-6 carbon atoms, CON(R5)2, COOR5, allyl, CH═CH—COOR5, CH═CHCON(R5)2, SO2alkyl of 1-6 carbon atoms or phenyl, which is unsubstituted or mono-, di- or trisubstituted by alkyl of 1-6 carbon atoms,
R2 is H, alkyl of 1-6 carbon atoms, cycloalkyl, —(CH2)o—OR5, or —(CH2)o—OR6,
R3 is

OG Complex Work Unit Drawing
R4 is Ar,
R5 is H or alkyl of 1-6 carbon atoms,
R6 is benzo[1,3]dioxol-5-yl,
R7 is H, alkyl of 1-6 carbon atoms, cycloalkyl or (CH2)q—OR5,
Q is S,
Y is a direct bond,
Ar is phenyl, naphthyl or biphenyl, which is unsubstituxed or mono-, di- or trisubstituted by alkyl of 1-6 carbon atoms, OR5, cycloalkyloxy, O—(CH2)p-Ph, CF3,OCF3, Hal, CN, CHO, COalkyl of 1-6 carbon atoms, COOR5, —(CH2)p—N(R7)2, NR5—COalkyl of 1-6 carbon atoms, NO2, SO2N(R5)2, mor, SO2-mor, 5-methyl-3-oxo-2,4-dihydropyrazol-2-yl, naphthyl or Her2,
Het2 is a unsaturated mono- or bicyclic heterocyclic radical having 5 to 10 ring members, where 1 or 2 N and/or 1 or 2 S or O atoms can be present and the heterocyclic radical can be mono- or disubstituted by alkyl of 1-6 carbon atoms, Hal, OR5, CF3, OCF3, N(R5)2, —(CH2)p—(CHalkyl of 1-6 carbon atoms)q-N(R5)—(CH2)q—COR5, CHO, COalkyl of 1-6 carbon atoms or COOR5,
Hal is F, Cl, Br or I,
mor is morpholin-4-yl,
Ph is phenyl,
o is 1, 2, 3, 4, 5, 6 or 7,
p is 0, 1, 2, 3 or 4,
q is 1, 2, 3 or 4,
and their pharmaceutically acceptable salts.