Phenyl indole allosteric inhibitors of p97 ATPase

1. A compound having the structure of formula (I):

or a pharmaceutically acceptable salt thereof; wherein:

R 1 is H, D, halo, cyano, hydroxyl, nitro, —C(O)NR 5 R 6 , —C(O)OR 5 , —N═N + ═N − , C 1 -C 3 alkyl, C 1 -C 3 alkoxy, —S(O) 2 NR 5 R 6 , —S(O) 2 R 5 , —OCZ 3 , —OCHZ 2 , —OCH 2 Z, —SZ 3 , —SCZ 3 , or —S(Z) 5 ;

each of R 5 or R 6 is independently H, D, C 1 -C 5 alkyl, or C l -C 3 alkoxy optionally substituted with one or more halo;

Z is a halo;

R 2 is H, D, halo, cyano, or C 1 -C 3 alkyl optionally substituted with one or more halo;

m is 0, 1, 2, 3, or 4;

R 3 is H, D, or C 1 -C 3 alkyl optionally substituted with one or more halo;

each R 3 ′ is independently CH or N, and at least one R 3 ′ is N;

M is C 1 -C 6 alkyl;

Y is a bond, CH, CH 2 , N, NH, O, or S;

L 2 is C 1 -C 5 alkyl optionally substituted with one or more oxo;

p is 0, 1, 2,3, or 4; and

denotes a single or double bond.

2. The compound of claim 1 , wherein Y is NH.

3. The compound of claim 1 , wherein each R 3′ is N.

4. The compound of claim 1 , wherein M is a C 1 -C 3 alkyl.

5. The compound of claim 1 , wherein L 2 is C 1 -C 3 alkyl.

6. The compound of claim 1 , wherein L 2 is C 2 alkyl.

7. The compound of claim 1 , wherein R 1 is halo, cyano, N(O) 2 , hydroxyl, or —C(O)NR 5 R 6 .

8. The compound of claim 1 , wherein p is 0.

9. A compound selected from the group consisting of:

consisting of:

or a pharmaceutically acceptable salt thereof.

10. A pharmaceutical composition comprising a compound of claim 1 , and at least one pharmaceutically acceptable excipient.

11. A pharmaceutical composition comprising a compound of claim 9 , and at least one pharmaceutically acceptable excipient.