CD73 inhibitors

1. A compound of Formula (IV), or a pharmaceutically acceptable salt thereof:

wherein:

Ring A is

Q 2 is N or CW;

Q 3 is N and Q 4 is CW;

or Q 3 is CW and Q 4 is N;

each W is independently hydrogen, halogen, —CN, —OR b , NR c R d , C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

A is —O— or —CH 2 —;

X is —O—, —S—, —S(═O) 2 —, —NR 17 —, or —C(R 18 ) 2 —;

R 1 and R 2 are independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl); wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 1a ;

or R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three R 1b ;

each R 1a and R 1b is independently oxo (when feasible), halogen, —CN, —OR b , —SR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —NR b S(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl);

R 3 is hydrogen, halogen, —CN, —OR b , —SR b , —NR c R d , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl); wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 3a ;

each R 3a is independently oxo (when feasible) halogen, —CN, —OR b , —NR c R d , —C(═O)R a , —C(═O)OR b , —C(═O)NR c R d , C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R 4 and R 7 are independently hydrogen, halogen, —OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R 5 and R 6 are independently hydrogen, halogen, —OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

R 8 is hydrogen, halogen, —OR b , —NR c R d , C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

R 9 and R 10 are independently hydrogen, halogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

R 11 is halogen, —CN, —OR 13 , —SR 11 , —S(═O)R 14 , —NO 2 , —NR 15 R 16 , —S(═O) 2 R 14 , —NR 13 S(═O) 2 R 14 , —S(═O) 2 NR 15 R 16 , —C(═O)R 14 , —OC(═O)R 14 , —C(═O)OR 13 , —OC(═O)OR 13 , —C(═O)NR 15 R 16 , —OC(═O)NR 15 R 16 , —NR 13 C(═O)NR 15 R 16 , —NR 13 C(═O)R 14 , —NR 13 C(═O)OR 13 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 11a ;

R 12 is halogen, —CN, —OR 13 , —SR 13 , —S(═O)R 14 , —NO 2 , —NR 15 R 16 , —S(═O) 2 R 14 , —NR 13 S(═O) 2 R 14 , —S(═O) 2 NR 15 R 16 , —C(═O)R 14 , —OC(═O)R 14 , —C(═O)OR 13 , —OC(═O)OR 13 , —C(═O)NR 15 R 16 , —OC(═O)NR 15 R 16 , —NR 13 C(═O)NR 15 R 16 , —NR 13 C(═O)R 14 , —NR 13 C(═O)OR 13 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 12a ;

or R 11 and R 12 are taken together to form a cycloalkyl or heterocycloalkyl each optionally substituted with one, two, or three R 11b ;

each R 11a , R 11b , and R 12a is independently oxo (when feasible), halogen, —CN, —OR 13 , —SR 13 , —S(═O)R 14 , —NO 2 , —NR 15 R 16 , —S(═O) 2 R 14 , —NR 13 S(═O) 2 R 14 , —S(═O) 2 NR 15 R 16 , —C(═O)R 14 , —OC(═O)R 14 , —C(═O)OR 13 , —OC(═O)OR 13 , —C(═O)NR 15 R 16 , —OC(═O)NR 15 R 16 , —NR 13 C(═O)NR 15 R 16 , —NR 13 C(═O)R 14 , —NR 13 C(═O)OR 13 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 11c ;

each R 11c is independently oxo (when feasible), halogen, —CN, —OR b , —SR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —NR b S(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl);

each R 13 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 13a ;

each R 14 is independently C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 14a ;

each R 15 and R 16 is independently hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein each alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 15a ;

or R 15 and R 16 are taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three R 15b ;

each R 13a , R 14a , R 15a , and R 15b is independently oxo (when feasible), halogen, —CN, —OR b , —SR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —NR b S(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl); wherein each alkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo (when feasible), halogen, —CN, —OR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —C(═O)OR b , —C(═O)NR c R d , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl;

R 17 is hydrogen, —CN, —OR b , —S(═O) 2 R a , —C(═O)R a , —C(═O)OR b , —C(═O)NR c R d , C 1 -C 6 alkyl, C 1 -C 6 fluoroalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl);

each R 18 is independently hydrogen, halogen, —CN, —OR b , —SR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl);

R 21 and R 22 are independently hydrogen, C 1 -C 20 alkyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), C 1 -C 6 alkyl(heterocycloalkyl); wherein each alkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 21a ;

or R 21 and R 22 are taken together with the atoms to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three R 21b ;

each R 21a and R 21b is independently oxo (when feasible), halogen, —CN, —OR b , —SR b , —S(═O)R a , —NO 2 , —NR c R d , —S(═O) 2 R a , —NHS(═O) 2 R a , —S(═O) 2 NR c R d , —C(═O)R a , —OC(═O)R a , —C(═O)OR b , —OC(═O)OR b , —C(═O)NR c R d , —OC(═O)NR c R d , —NR b C(═O)NR c R d , —NR b C(═O)R a , —NR b C(═O)OR b , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl);

each R a is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo (when feasible), halogen, —OH, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

each R b is independently hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo (when feasible), halogen, —OH, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl; and

each R c and R d is independently hydrogen, C 1 -C 6 alkyl C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl; wherein the alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three oxo (when feasible), halogen, —OH, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl;

or R c and R d are taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl optionally substituted with one, two, or three oxo, halogen, C 1 -C 6 alkyl, or C 1 -C 6 haloalkyl.

2. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

Q 2 is CW.

3. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

Q 2 is N.

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

Q 3 is N and Q 4 is CW.

5. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

Q 4 is N and Q 3 is CW.

6. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

each W is independently hydrogen, halogen, or C 1 -C 6 alkyl.

7. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

R 3 is halogen, —OR b , C 1 -C 6 alkyl, C 1 -C 6 alkynyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, or C 1 -C 6 heteroalkyl; wherein each alkyl and alkynyl is independently optionally substituted with one, two, or three R 3a .

8. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein:

R 3 is halogen, —OR b , C 2 -C 6 alkynyl, or C 1 -C 6 hydroxyalkyl; wherein each alkyl and alkynyl is independently optionally substituted with one, two, or three R 3a .

9. The compound of claim 1 , or a pharmaceutically acceptable salt, solvate thereof, wherein:

R 1 is C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, cycloalkyl, heterocycloalkyl, C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 1 -C 6 alkyl(cycloalkyl), or C 1 -C 6 alkyl(heterocycloalkyl), wherein each alkyl, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl is independently optionally substituted with one, two, or three R 1a .

10. The compound of claim 9 , or a pharmaceutically acceptable salt thereof, wherein:

R 1 is C 1 -C 6 alkyl, cycloalkyl, C 1 -C 6 alkyl(aryl), or C 1 -C 6 alkyl(cycloalkyl); wherein each alkyl, cycloalkyl, and aryl is independently optionally substituted with one, two, or three R 1a .

11. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

each R 1a is independently halogen or C 1 -C 6 alkyl.

12. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

R 2 is hydrogen or C 1 -C 6 alkyl.

13. The compound of claim 12 , or a pharmaceutically acceptable salt thereof, wherein:

R 2 is hydrogen.

14. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

R 8 is hydrogen or C 1 -C 6 alkyl.

15. The compound of claim 14 , or a pharmaceutically acceptable salt thereof, wherein:

R 8 is hydrogen.

16. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

R 9 and R 10 are independently hydrogen or C 1 -C 6 alkyl.

17. The compound of claim 16 , or a pharmaceutically acceptable salt thereof, wherein:

R 9 and R 10 are hydrogen.

18. The compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein:

A is —O—.

19. A pharmaceutical composition comprising a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

20. A method of treating cancer in a subject, comprising administering to the subject a compound of claim 1 , or a pharmaceutically acceptable salt thereof.