Adenosine A2a receptor antagonists

A compound represented by the structural formula

• 96
• or a pharmaceutically acceptable salt thereof, wherein
• R is R1-heteroaryl, R10-phenyl, C4-C6 cycloalkenyl, —C(═CH2)CH3, —C≡C—CH3, —C≡C—CH2—OR2, —CH=C(CH3)2,
• 97
• X is C1-C6 alkylene, —C(O)CH2— or —C(O)N(R2)CH2—;
• Y is —N(R2)CH2CH2N(R3)—, —OCH2CH2N(R2)—, —O—, —S—, —CH2S—, —(CH2)2-3—N(R2)—, R5-divalent heteroaryl,
• 98
• and
• Z is R5-phenyl, R5-phenyl(C1-C6)alkyl, R5-heteroaryl, R5-bicyclic heteroaryl, R5-benzofused heteroaryl, diphenylmethyl or R6—C(O)—;
• or when Y is
• 99
• Z is also R6—SO2—, R7—N(R8)—C(O)—, R7—N(R8)—C(S)— or R6OC(O)—;
• or when Q is
• 100
• Z is also phenylamino or pyridylamino;
• or Z and Y together are
• 101
• or Y and Z together form a piperidinyl or pyrrolidinyl ring fused to a monocyclic or bicyclic aryl or a monocyclic or bicyclic heteroaryl ring wherein X is attached to the N atom of the piperidinyl or pyrrolidinyl ring;
• R1 is 1 to 3 substituents independently selected from hydrogen, C1-C6-alkyl, —CF3, halogen, —NO2, —NR12R13, C1-C6 alkoxy, C1-C6 alkylthio, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, —COOR7 or —C(O)NR2R3;
• R2 and R3 are independently selected from the group consisting of hydrogen and C1-C6 alkyl;
• m and n are independently 2-3;
• p and q are independently 0-2;
• Q and Q1 are independently selected from the group consisting of
• 102
• provided that at least one of Q and Q1 is
• R4 is 1-2 substituents independently selected from the group consisting of hydrogen, C1-C6alkyl, R1-aryl and R1-heteroaryl, or two R4 substituents on the same carbon can form ═O;
• R5 is 1 to 5 substituents independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, hydroxy, C1-C6 alkoxy, —CN, di-((C1-C6)alkyl)amino, —CF3, —OCF3, acetyl, —NO2, hydroxy(C1-C6)alkoxy, (C1-C6)-alkoxy(C1-C6)alkoxy, di-((C1-C6)-alkoxy)(C1-C6)alkoxy, (C1-C6)-alkoxy(C1-C6)alkoxy-(C1-C6)-alkoxy, carboxy(C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl(C1-C6)alkoxy, (C3-C6)cycloalkyl(C1-C6)alkoxy, di-((C1-C6)alkyl)amino(C1-C6)alkoxy, morpholinyl, (C1-C6)alkyl-SO2—, (C1-C6)alkyl-SO2—(C1-C6)alkoxy, tetrahydropyranyloxy, (C1-C6)alkylcarbonyl(C1-C6)-alkoxy, (C1-C6)-alkoxycarbonyl, (C1-C6)alkylcarbonyloxy(C1-C6)-alkoxy, —SO2NH2, phenoxy,
• 103
• (R2O)2—P(O)—CH2—O— and (R2O)2—P(O)—;
• or adjacent R5 substituents together are —O—CH2—O—, —O—CH2CH2—O—, —O—CF2—O— or —O—CF2CF2—O— and form a ring with the carbon atoms to which they are attached;
• R6 is (C1-C6)alkyl, R5-phenyl, R5-phenyl(C1-C6)alkyl, thienyl, pyridyl, (C3-C6)-cycloalkyl, (C1-C6)alkyl-OC(O)—NH—(C1-C6)alkyl-, di-((C1-C6)alkyl)aminomethyl, or
• 104
• R7 is (C1-C6)alkyl, R5-phenyl or R5-phenyl(C1-C6)alkyl;
• R8 is hydrogen or C1-C6 alkyl;
• or R7 and R8 together are —(CH2)p—A—CH2)q, wherein p and q are independently 2 or 3 and A is a bond, —CH2—, —S— or —O—, and form a ring with the nitrogen to which they are attached;
• R9 is 1-2 substituents independently selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxy, C1-C6 alkoxy, halogen, —CF3 and (C1-C6)alkoxy-(C1-C6)alkoxy;
• R10 is 1 to 5 substituents independently selected from the group consisting of hydrogen, halogen, C1-C6 alkyl, hydroxy, C1-C6 alkoxy, —CN, —NH2, C1-C6alkylamino, di-((C1-C6)alkyl)amino, —CF3, —OCF3, —S(O)0-2(C1-C6)alkyl and —CH2—SO2-phenyl;
• R11 is H, C1-C6 alkyl, phenyl, benzyl, C2-C6 alkenyl, C1-C6 alkoxy(C1-C6)alkyl, di-((C1-C6)alkyl)amino(C1-C6)alkyl, pyrrolidinyl(C1-C6)alkyl or piperidino(C1-C6)alkyl;
• R12 is H or C1-C6 alkyl;
• R13 is H, (C1-C6)alkyl-C(O)— or (C1-C6)alkyl-SO2—;
• R14 is H, halogen, C1-C6 alkyl, hydroxy(C1-C6)alkyl, C1-C6 alkoxy(C1-C6)alkyl, thio(C1-C6)alkyl, (C1-C6)alkylthio(C1-C6)alkyl or NR2R3-(C1-C6)alkyl;
• and
• R15 is H, halogen, C1-C6 alkyl or C1-C6 alkoxy.