Ectonucleotidase inhibitors and methods of use thereof

A compound selected from:

• Example #
• Compound
• 2
• 3
• 4
• 5
• 6
• 7
• 8
• 9
• 10
• 11
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• or a pharmaceutically acceptable salt thereof.

A compound of formula (I):

• or a pharmaceutically acceptable salt and/or prodrug thereof wherein
• Y is
• Het is
• wherein Z is N;
• Ra is selected from —NR7R8, aralkyl, aryl, and heteroaryl;
• Rb is selected from halo, alkyl, haloalkyl, hydroxyalkyl, alkylthio, amido, carbonyl, amido, and heteroaryl;
• R7 is selected from hydroxy, alkyl, aralkyl, heteroaralkyl, cycloalkyl, and heterocyclyl and R8 is H or alkyl;
• or R7 and R8, together with the nitrogen atom to which they are attached, form a 4- to 7-membered heterocyclyl ring;
• R1a is selected from H, halo, hydroxy, cyano, azido, amino, C1-6alkyl, hydroxyC1-6alkyl, amino-C1-6alkyl, —O—C(O)—O—C1-6alkyl, C1-6acyloxy, C1-6alkoxy, C2-6alkenyl, and C2-6alkynyl;
• R1b is selected from H, halo, C1-6alkyl, hydroxy-C1-6alkyl, amino-C1-6alkyl, C2-6alkenyl, and C2-6alkynyl;
• R2a is selected from halo, hydroxy, cyano, azido, amino, C1-6alkyl, hydroxy-C1-6alkyl, amino-C1-6alkyl, C1-6acyloxy, —O—C(O)—O—C1-6alkyl, C1-6alkoxy, C2-6alkenyl, and C2-6alkynyl;
• R2b is C2-6alkynyl;
• R3 is selected from H and alkyl;
• R4 is selected from H, alkyl, CN, aryl, heteroaryl, —C(O)OR9, —C(O)NR11R12, —S(O)2R10, —P(O)(OR11)(OR12), and —P(O)(OR11)(NR13R14);
• R5 is aralkyl or heteroaralkyl;
• R6 is selected from —C(O)OR9, —C(O)NR16R17, and —P(O)(OR11)(OR12);
• R9 is independently selected from H, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, and heteroaralkyl;
• R10 is independently selected from alkyl, alkenyl, alkynyl, amino, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, and heteroaralkyl;
• and
• each R11 and R12 is independently selected from H, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, and heteroaralkyl;
• or
• R11 and R12, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocyclyl;
• R13 is, independently for each occurrence, H or alkyl;
• R14 is, independently for each occurrence, alkyl or aralkyl;
• each R15 is independently selected from hydroxy, alkoxy acyloxy and NR13R14;
• each R16 and R17 is independently selected from H, hydroxy, alkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, heterocyclylalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl;
• or
• R16 and R17, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocyclyl.