US2019382351A1PendingUtilityA1
Hdac inhibitors
Est. expiryMar 15, 2033(~6.6 yrs left)· nominal 20-yr term from priority
A61P 43/00A61P 29/00A61P 25/36A61P 31/12A61P 25/14A61P 35/00A61P 25/28A61P 31/00A61P 21/04A61P 25/00A61P 21/00A61P 21/02C07D 231/56C07D 401/06C07D 403/06A61K 31/4439A61K 31/416
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Claims
Abstract
Disclosed herein are compounds of formula (I), and methods of inhibiting histone deacetylase (“HDAC”) enzymes (e.g., HDAC1, HDAC2, and HDAC3) using compounds of formula (I):
Claims
exact text as granted — not AI-modifiedWhat is claimed:
1 . A compound having formula (I), or a pharmaceutically acceptable salt thereof:
wherein:
R 1 —X is attached to only one of the ring nitrogen atoms;
X is:
(i) —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—;
(ii) direct bond; or
(iii) C═O, C(R 3 ) 2 —C(═O), C(═O)—C(R 3 ) 2 , SO 2 —NR k , NR k —SO 2 , C(═O)NR k or NR k —C(═O);
wherein:
Y is bond, CR c ═CR d , O, NR c , or S(O) m ;
each of A and B is, independently, a bond, O, NR f , or S(O) m ;
a is 1, 2, or 3;
b is 0, 1, 2, or 3;
m is 0, 1, or 2;
each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano; or
one or more of the following can apply with respect to R a and R b :
any two R a , together with the carbons to which each is attached, together form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the heterocyclyl ring atoms is selected from O, S(O) m and NR g ; or
one R a and one R b , together with the carbons to which each is attached, form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the heterocyclyl ring atoms is selected from O; S(O) m and NR g ; or
any two R h , together with the carbons to which each is attached, form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the ring atoms is selected from O; S(O) m and NR g ;
each of R c and R d is independently selected from H, F, OH, C1-C6 alkyl, C3-C5 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C5 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano;
or R c and R d , together with the carbons to which each is attached form a C5-C7 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which from 1-2 of the heterocyclyl ring atoms are independently selected from 0, S(O) m and NR g′ ;
each occurrence of R e , R f , R g and R g′ is independently selected from H, C1-C6 alkyl, —C(═O)H, —C(═O)R h , C(═O)O(C1-C6 alkyl), C(═O)N(R i ) 2 , and SO 2 —R h ; wherein R h is selected from C1-C6 alkyl, CH 2 -(heteroaryl including 5-10 ring atoms), CH 2 —(C6-C10 aryl), and C6-C10 aryl; and each occurrence of R a is independently selected from H, C1-C6 alkyl, CH 2 -(heteroaryl including 5-10 ring atoms), CH 2 —(C6-C10 aryl), and C6-C10 aryl;
each occurrence of R a is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano;
or R j —C—R j together form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the heterocyclyl ring atoms is selected from O; S(O) m and NR j′ ;
each occurrence of R j′ and R k is independently selected from H, C1-C6 alkyl, —C(═O)H, —C(═O)R m , C(═O)O(C1-C6 alkyl), C(═O)N(R n ) 2 , and SO 2 —R m , wherein R m is selected from C1-C6 alkyl, CH 2 -(heteroaryl including 5-10 ring atoms), CH 2 —(C6-C10aryl), and C6-C10aryl; and each occurrence of R n is independently selected from H, C1-C6 alkyl, CH 2 -(heteroaryl including 5-10 ring atoms), CH 2 —(C6-C10 aryl), and C6-C10 aryl, and wherein the aryl and heteroaryl portion in R m and R n can be optionally substituted with 1-3 independently selected substituents F, C1-C6 alkyl, fluoro C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, C1-C6 fluoroalkoxy, or cyano;
further wherein:
(a) when each of A and B is a bond, and b is 0, then X has the following formula: —Y—[C(R a ) 2 ] a —;
(b) when b is 0 or 1, then A and B cannot both be heteroatoms; and
(c) when A or B serves as the point of connection of X to the nitrogen ring atoms, then A or B cannot be a heteroatom;
R1 is:
(i) monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(ii) C6-C10 aryl, which is optionally substituted with from 1-3 R o ; or
(iii) C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-6 R o ;
(iv) heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-6 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(v) hydrogen;
R4 is H or R o and each occurrence of R o is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—;
—N*(R o′ ) 2 , wherein R o′ —N*—R o′ together form a saturated ring having 5 or 6 ring atoms, in which 1 or 2 ring atoms are optionally a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S; formyl; formyl(C1-C4) alkyl; cyano; cyano(C1-C4) alkyl; benzyl;
benzyloxy; (heterocyclyl)-(C0-C6) alkyl, wherein the heterocyclyl portion includes 5 or 6 ring atoms, in which 1 or 2 of the ring atoms are a heteroatom independently selected from NH, N(alkyl), O, or S, and when said alkyl portion is present, said alkyl portion serves as the point of attachment to R, and when the alkyl portion is not present, a heterocyclyl carbon ring atom serves as the point of attachment of the heterocyclyl to R1; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o″ , and S, each of which is optionally substituted with from 1-3 R o″ ; SO 2 —(C1-C6)alkyl; SO—(C1-C6)alkyl; and nitro; each occurrence of 14 0 ″ is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; formyl; formyl(C1-C4) alkyl; cyano; cyano(C1-C4) alkyl; benzyl; benzyloxy; (heterocyclyl)-(C0-C6) alkyl, wherein the heterocyclyl portion includes 5 or 6 ring atoms, in which 1 or 2 of the ring atoms are a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S, and when said alkyl portion is present, said alkyl portion serves as the point of attachment to R1; and when the alkyl portion is not present, a heterocyclyl carbon ring atom serves as the point of attachment of the heterocyclyl to R1; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—(C1-C6 alkyl), and S; SO 2 —(C1-C6)alkyl; SO—(C1-C6)alkyl; and nitro;
R5 is selected from the group consisting of: hydrogen, halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; (C1-C6 alkyl)C(O)—; formyl; formyl(C1-C4) alkyl; cyano; cyano(C1-C4) alkyl; benzyl; (heterocyclyl)-(C0-C6)alkyl, wherein the heterocyclyl portion includes 5 or 6 ring atoms, in which 1 or 2 of the ring atoms are a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S, and when said alkyl portion is present, said alkyl portion serves as the point of attachment to R1; and when the alkyl portion is not present, a heterocyclyl carbon ring atom serves as the point of attachment of the heterocyclyl to R1; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R q″ , and S, each of which is optionally substituted with from 1-3 WI″; SO 2 —(C1-C6)alkyl; SO—(C1-C6)alkyl; and nitro;
R2 is selected from H, F, Cl, CF 3 , CF 2 CF 3 , CH 2 CF 3 , OCF 3 , OCHF 2 , phenyl; or phenyl substituted with 1-3 R o ; and
R3 is H, F, or Cl.
2 . The compound or salt of claim 1 , wherein the compound or salt has formula (Ia):
3 . The compound or salt of claim 1 , wherein the compound or salt has formula (Ib):
4 . The compound or salt of any one of claims 1 - 3 , wherein X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—.
5 . The compound or salt of claim 4 , wherein A is a bond, B is a bond, or both A and B are each a bond.
6 . The compound or salt of claim 4 or 5 , wherein each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano.
7 . The compound or salt according to any one of claims 4 - 6 , wherein each occurrence of R a and R b is independently selected from H, F, C1-C6 alkyl, and C3-C6 cycloalkyl.
8 . The compound or salt according to any one of claims 4 - 7 , wherein each occurrence of R a and R b is H.
9 . The compound or salt of claim 4 , wherein Y is a bond.
10 . The compound or salt according to claim 9 , wherein A is a bond, O, or NR e .
11 . The compound or salt according to claim 9 or 10 , wherein A is a bond.
12 . The compound or salt according to any one of claims 9 - 11 , wherein each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano.
13 . The compound or salt according to any one of claims 9 - 12 , wherein each occurrence of R a and R b is independently selected from H, F, C1-C6 alkyl, and C3-C6 cycloalkyl.
14 . The compound or salt according to any one of any one of claims 9 - 13 , wherein each occurrence of R a and R b is H.
15 . The compound or salt according to any one of claims 9 - 14 , wherein a is 1.
16 . The compound or salt according to any one of claims 9 - 15 , wherein b is 0.
17 . The compound or salt according to any one of claims 9 - 16 , wherein X is CH 2 .
18 . The compound or salt according to any one of claims 9 - 15 , wherein b is 1, 2, or 3.
19 . The compound or salt according to any one of claims 9 - 15 and 18 , wherein X is (CH 2 ) 2-4 .
20 . The compound or salt of claim 4 , wherein Y is CR c ═CR d .
21 . The compound or salt of claim 20 , wherein the double bond between CR c and CR d has the trans configuration.
22 . The compound or salt of claim 20 or 21 , wherein each of R c and R d is H.
23 . The compound or salt according to any one of claims 20 - 22 , wherein A is a bond, B is a bond, or each of A and B is a bond.
24 . The compound or salt according to any one of claims 20 - 23 , wherein each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano.
25 . The compound or salt according to any one of claims 20 - 24 , wherein each occurrence of R a and R b is independently selected from H, F, C1-C6 alkyl, and C3-C6 cycloalkyl.
26 . The compound or salt according to any one of claims 20 - 25 , wherein each occurrence of R a and R b is H.
27 . The compound or salt according to any one of claims 20 - 26 , wherein one or both of the following apply: (i) a is 1 or 2, and (ii) b is 0 or 1.
28 . The compound or salt according to any one of claims 20 - 27 , wherein b is O.
29 . The compound or salt according to any one of claims 20 - 28 , wherein X is —CH═CH—C(R a ) 2 — or —CH═CHC(R a ) 2 C(R a ) 2 —.
30 . The compound or salt of claim 4 , wherein Y is O.
31 . The compound or salt of claim 4 , wherein Y is NR e .
32 . The compound or salt according to claim 30 or 31 , wherein A is a bond, B is a bond, or each of A and B is a bond.
33 . The compound or salt according to any one of claims 30 - 32 , wherein each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano.
34 . The compound or salt according to any one of claims 30 - 33 , wherein each occurrence of R a and R b is independently selected from H, F, C1-C6 alkyl, and C3-C6 cycloalkyl.
35 . The compound or salt according to any one of claims 30 - 34 , wherein each occurrence of R a and R b is H.
36 . The compound or salt according to any one of claims 30 - 35 , wherein a is 2 or 3 and b is optionally other than 0.
37 . The compound or salt according to any one of claims 30 - 36 , wherein X is —O—(CH 2 ) 2-3 or —N(CH 3 )—(CH 2 ) 2-3 .
38 . The compound or salt according to any one of claims 4 , 5 , 9 - 11 15 , 16 , 18 , 20 - 23 , 27 , 28 , and 30 - 32 , wherein one or more of the following apply:
any two R a , together with the carbons to which each is attached, together form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the heterocyclyl ring atoms is selected from O, S(O) m and NR g ; or one R a and one R b , together with the carbons to which each is attached, form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the heterocyclyl ring atoms is selected from O, S(O) m and NR g ; or any two R b , together with the carbons to which each is attached, form C3-C6 cycloalkyl or heterocyclyl including 3-6 ring atoms, in which one of the ring atoms is selected from O, S(O) m and NR g .
39 . The compound or salt according to any one of claims 1 - 3 , wherein X is a bond.
40 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-3 R o .
41 . The compound or salt according to any one of claims 1 - 40 , wherein R1 is C3-C10 cycloalkyl, which is optionally substituted with from 1-3 R o .
42 . The compound or salt according to any one of claims 1 - 41 , wherein R1 is C3-C6 cycloalkyl, which is optionally substituted with from 1-3 R o .
43 . The compound or salt according to any one of claims 1 - 42 , wherein R1 is cyclopropyl, which is optionally substituted with from 1-3 R o .
44 . The compound or salt according to any one of claims 1 - 43 , wherein R1 is unsubstituted C3-C6 cycloalkyl.
45 . The compound or salt according to any one of claims 1 - 44 , wherein R1 is unsubstituted cyclopropyl.
46 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is C6-C10 aryl, which is optionally substituted with from 1-3 R o .
47 . The compound or salt according to any one of claims 1 - 39 and 46 , wherein R1 is phenyl or naphthyl, which is optionally substituted with from 1-3 R o .
48 . The compound or salt according to any one of claims 1 - 39 and 46 , wherein R1 is C8-C10 aryl, which contains a phenyl ring fused to a non-aromatic ring and which is optionally substituted with from 1-3 R o .
49 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S.
50 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is monocyclic heteroaryl including from 5-6 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S.
51 . The compound or salt according to any one of claims 1 - 39 and 49 , wherein R1 is bicyclic heteroaryl including from 8-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S.
52 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S.
53 . The compound or salt according to any one of claims 1 - 39 , wherein R1 is H.
54 . The compound or salt according to any one of claims 1 - 53 , wherein R4 is H or halo.
55 . The compound or salt according to any one of claims 1 - 54 , wherein R4 is H.
56 . The compound or salt according to any one of claims 1 - 55 , wherein R5 is H.
57 . The compound or salt according to any one of claims 1 - 56 , wherein R2 is a substituent other than hydrogen, and R3 is hydrogen.
58 . The compound or salt according to any one of claims 1 - 56 , wherein R2 is hydrogen, and R3 is F or Cl.
59 . The compound or salt according to any one of claims 1 - 56 and 58 , wherein R2 is hydrogen, and R3 is fluoro.
60 . The compound or salt according to any one of claims 1 - 56 , wherein each of R2 and R3 is hydrogen.
61 . The compound or salt according to any one of claims 1 - 60 , wherein each R o is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; —N*(R o′ ) 2 , wherein R o′ —N*—R o′ together form a saturated ring having 5 or 6 ring atoms, in which 1 or 2 ring atoms are optionally a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S; cyano; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o″ , and S, each of which is optionally substituted with from 1-3 R o″ ; and SO 2 —(C1-C6)alkyl.
62 . The compound or salt according to any one of claims 1 - 61 , wherein each R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl.
63 . The compound or salt according to any one of claims 1 - 62 , wherein each R o is independently selected from the group consisting of halogen, C1-C6 alkyl, and fluoro(C1-C6)alkyl.
64 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is:
(i) —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—;
(ii) direct bond; or
(iii) C═O, C(R 3 ) 2 —C(═O), C(═O)—C(R 3 ) 2 , SO 2 —NR k , NR k —SO 2 , C(═O)NR k or
NR k —C(═O);
R1 is:
(i) monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(ii) C6-C10 aryl, which is optionally substituted with from 1-3 R o ;
(iii) C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-3 R o ;
(iv) heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; or
(v) hydrogen;
R o is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; —N*(R o′ ) 2 , wherein R o′ —N*—R o′ together form a saturated ring having 5 or 6 ring atoms, in which 1 or 2 ring atoms are optionally a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S; cyano; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o″ , and S, each of which is optionally substituted with from 1-3 R o″ ; and SO 2 —(C1-C6)alkyl;
R4 is hydrogen or halo;
R5 is hydrogen; and
(i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or
(iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
65 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is:
(i) monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(ii) C6-C10 aryl, which is optionally substituted with from 1-3 R o ; or
(iii) C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-3 R o ;
(iv) heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; or
(v) hydrogen;
R o is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; —N*(R o′ ) 2 , wherein R o′ —N*—R o′ together form a saturated ring having 5 or 6 ring atoms, in which 1 or 2 ring atoms are optionally a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S; cyano; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o″ , and S, each of which is optionally substituted with from 1-3 R o″ ; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
66 . The compound or salt according to any one claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, and Y is a bond; R1 is:
(i) monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(ii) C6-C10 aryl, which is optionally substituted with from 1-3 R o ; or
(iii) C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-3 R o ;
(iv) heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; or
(v) hydrogen;
R o is independently selected from the group consisting of halogen, C1-C6 alkyl, and fluoro(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
67 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, Y is a bond, and each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano; R1 is:
(i) monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S;
(ii) C6-C10 aryl, which is optionally substituted with from 1-3 R o ; or
(iii) C3-C10 cycloalkyl or C3-C10 cycloalkenyl, each of which is optionally substituted with from 1-3 R o ;
(iv) heterocyclyl including from 3-10 ring atoms, which is optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; or
(v) hydrogen;
R o is independently selected from the group consisting of halogen, C1-C6 alkyl, and fluoro(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and
(i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
68 . The compound or salt according to any one claims 1 - 63 , wherein:
X is:
(i) —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—;
(ii) direct bond; or
(iii) C═O, C(R 3 ) 2 —C(═O), or C(═O)—C(R 3 ) 2 , SO 2 —NR k , NR k —SO 2 , C(═O)NR k and NR k —C(═O);
R1 is C3-C10 cycloalkyl or C3-C10 cycloalkenyl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of halogen, C1-C6 alkyl, and fluoro(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
69 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is C3-C10cycloalkyl or C3-C10cycloalkenyl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)C(O)—; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; —N*(R o′ ) 2 , wherein R o′ —N*—R o′ together form a saturated ring having 5 or 6 ring atoms, in which 1 or 2 ring atoms are optionally a heteroatom independently selected from NH, N(C1-C6alkyl), O, or S; cyano; phenyl; heteroaryl including from 5-6 ring atoms, wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o″ , and S, each of which is optionally substituted with from 1-3 R o″ ; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
70 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is C3-C10cycloalkyl or C3-C10 cycloalkenyl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
71 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, and Y is a bond; R1 is C3-C10 cycloalkyl or C3-C10 cycloalkenyl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of halogen, C1-C6 alkyl, and fluoro(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
72 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, Y is a bond, and each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano; R1 is C3-C10cycloalkyl or C3-C10cycloalkenyl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
73 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is:
(i) —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—;
(ii) direct bond; or
(iii) C═O, C(R j ) 2 —C(═O), or C(═O)—C(R j ) 2 , SO 2 —NR k , NR k —SO 2 , C(═O)NR k and NR k —C(═O);
R1 is monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
74 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
75 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a )] a -A-[C(R b ) 2 ] b —B—, and Y is a bond; R1 is monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
76 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, Y is a bond, and each occurrence of R a and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano; R1 is monocyclic or bicyclic heteroaryl including from 5-10 ring atoms, optionally substituted with from 1-3 R o ; wherein from 1-4 of the ring atoms are a heteroatom independently selected from O, N, N—H, N—R o , and S; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
77 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is: (i) —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; (ii) direct bond; or (iii) C═O, C(R 3 ) 2 —C(═O), C(═O)—C(R 3 ) 2 , SO 2 —NR k , NR k —SO 2 , C(═O)NR k and NR k —C(═O); R1 is C6-C10 aryl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
78 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is C6-C10 aryl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
79 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—; R1 is C6-C10 aryl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
80 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, and Y is a bond; R1 is C6-C10 aryl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
81 . The compound or salt according to any one of claims 1 - 63 , wherein:
X is —Y—[C(R a ) 2 ] a -A-[C(R b ) 2 ] b —B—, Y is a bond, and each occurrence of W and R b is independently selected from H, F, OH, C1-C6 alkyl, C3-C6 cycloalkyl, NH 2 , OCO—(C1-C6 alkyl), OCO—(C3-C6 cycloalkyl), C1-C6 alkoxy, C1-C6 fluoroalkoxy, and cyano; R1 is C6-C10 aryl, optionally substituted with from 1-3 R o ; R o is independently selected from the group consisting of: halogen; C1-C6 alkyl; fluoro(C1-C6)alkyl; hydroxyl; hydroxy(C1-C4)alkyl; C1-C6 alkoxy; fluoro(C1-C6)alkoxy; (C1-C6 alkyl)NH—; (C1-C6 alkyl) 2 N—; cyano; and SO 2 —(C1-C6)alkyl; R4 is hydrogen or halo; R5 is hydrogen; and (i) each of R2 and R3 is hydrogen; or (ii) R2 is hydrogen, and R3 is fluoro; or (iii) R2 is a substituent other than hydrogen, and R3 is hydrogen.
82 . The compound or salt according to any one of claims 64 - 81 , wherein the compound or salt has formula (Ia):
83 . The compound or salt according to any one of claims 64 - 81 , wherein the compound or salt has formula (Ib):
84 . The compound or salt according to any one of claims 64 - 82 , wherein A is a bond.
85 . The compound or salt according to any one of claims 64 - 84 , wherein each occurrence of R a and R b is independently selected from H, F, C1-C6 alkyl, and C3-C6 cycloalkyl.
86 . The compound or salt according to any one of any one of claims 64 - 85 , wherein each occurrence of R a and R b is H.
87 . The compound or salt according to any one of claims 64 - 86 , wherein a is 1.
88 . The compound or salt according to any one of claims 64 - 87 , wherein b is 0.
89 . The compound or salt according to any one of claims 64 - 88 , wherein X is CH 2 .
90 . The compound or salt according to any one of claims 64 - 87 and 89 , wherein b is 1, 2, or 3.
91 . The compound or salt according to any one of claims 64 - 88 and 90 , wherein X is (CH 2 ) 2-4 .
92 . The compound or salt according to any one of claims 64 - 72 and 82 - 91 , wherein R1 is C3-C10 cycloalkyl, optionally substituted with from 1-3 R o .
93 . The compound or salt according to claim 92 , wherein R1 is C3-C6 cycloalkyl, optionally substituted with from 1-3 R o .
94 . The compound or salt according to claim 93 , wherein R1 is cyclopropyl, optionally substituted with from 1-3 R o .
95 . The compound or salt according to claim 93 , wherein R1 is unsubstituted C3-C6 cycloalkyl.
96 . The compound or salt according to claim 95 , wherein R1 is unsubstituted cyclopropyl.
97 . The compound or salt according to any one of claims 1 - 96 , wherein the compound is selected from the compounds delineated in Table 1.
98 . The compound or salt according to claim 97 , wherein the compound is selected from A1-A16.
99 . The compound or salt according to claim 97 , wherein the compound is selected from A6-A8, A10, and A12.
100 . The compound or salt according to claim 97 , wherein the compound is selected from A1, A4-A8, and A13-A15.
101 . The compound or salt according to claim 97 , wherein the compound is selected from A2, A3, A9, and A10.
102 . The compound or salt according to any one of claims 1 - 96 , wherein —X—R1 is CH 2 phenyl, optionally substituted with one or more substituents selected from halo and methyl.
103 . The compound or salt according to any one of claims 1 - 96 , wherein —XR 1 is CH 2 pyridyl, optionally substituted with one or more substituents selected from halo and methyl.
104 . The compound or salt according to any one of claims 1 - 96 , wherein —XR 1 is CH 2 cycloalkyl, and the cycloalkyl is selected from cyclopropyl, cyclopentyl, and cyclohexyl, and is optionally substituted with one or more of C1-C3alkyl, C1-C3alkoxy, and halo.
105 . The compound or salt according to claim 104 , wherein —XR 1 is CH 2 cyclopropyl, optionally substituted with one or more of C1-C3alkyl, C1-C3alkoxy, and halo.
106 . The compound or salt according to any one of claims 1 - 96 , wherein —XR 1 is CH 2 pyrazolyl, optionally substituted with one or more substituents selected from methyl and halo.
107 . The compound or salt according to any one of claims 1 - 106 , wherein R 2 and R 3 are each hydrogen.
108 . The compound or salt according to any one of claims 1 - 106 , wherein R 2 is hydrogen and R 3 is F or Cl.
109 . The compound or salt according to any one of claims 1 - 108 , wherein R 4 is hydrogen.
110 . A pharmaceutical composition comprising a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 and a pharmaceutically acceptable carrier.
111 . A method of inhibiting HDAC3, the method comprising contacting a cell with an effective amount of a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 .
112 . The method of claim 111 , wherein the compound or composition selectively inhibits HDAC3.
113 . A method of inhibiting HDAC1 or HDAC2, the method comprising contacting a cell with an effective amount of a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 .
114 . The method of claim 113 , wherein the compound or composition selectively inhibits HDAC1 or HDAC2.
115 . A method of inhibiting HDAC1, HDAC2, and HDAC3, the method comprising contacting a cell with an effective amount of a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 .
116 . A method of treating a disease or disorder mediated by HDAC1 or HDAC2 in a subject in need thereof, the method comprising administering a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 to said subject.
117 . A method of treating a disease or disorder mediated by HDAC3 in a subject in need thereof, the method comprising administering a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 to said subject.
118 . A method of treating a disease or disorder mediated by HDAC1, HDAC2, and HDAC3 in a subject in need thereof, the method comprising administering a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 to said subject.
119 . A method of treating a neurological disorder selected from Friedreich's ataxia, myotonic dystrophy, spinal muscular atrophy, fragile X syndrome, Huntington's disease, spinocerebellar ataxia, Kennedy's disease, amyotrophic lateral sclerosis, Niemann Pick, Pitt Hopkins, spinal and bulbar muscular atrophy, Alzheimer's disease; a cancer; an inflammatory disease; a memory impairment condition; and a drug addiction in a patient in need thereof, the method comprising administering a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , or a composition according to claim 110 to said patient.
120 . The method of claim 119 , wherein the disorder is Friedreich's ataxia.
121 . The method of claim 119 , wherein the disorder is Huntington's disease.
122 . A compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , for use in the preparation of a medicament.
123 . A compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , for the treatment of a disease or disorder mediated by HDAC1 or HDAC2, a disease or disorder mediated by HDAC3, or a neurological disorder selected from Friedreich's ataxia, myotonic dystrophy, spinal muscular atrophy, fragile X syndrome, Huntington's disease, spinocerebellar ataxia, Kennedy's disease, amyotrophic lateral sclerosis, spinal and bulbar muscular atrophy, Alzheimer's disease; an infection including microbial or viral infection; a cancer; an inflammatory disease; a memory impairment condition and a drug addiction.
124 . Use of a compound, or pharmaceutically acceptable salt thereof, as claimed in any one of claims 1 - 109 , in the preparation of a medicament for the treatment or prevention of a disease or disorder mediated by HDAC1 or HDAC2, a disease or disorder mediated by HDAC3, or a neurological disorder selected from Friedreich's ataxia, myotonic dystrophy, spinal muscular atrophy, fragile X syndrome, Huntington's disease, a spinocerebellar ataxia, Kennedy's disease, amyotrophic lateral sclerosis, Niemann Pick, Pitt Hopkins, spinal and bulbar muscular atrophy, Alzheimer's disease; a cancer; an inflammatory disease; a memory impairment condition and a drug addiction.Join the waitlist — get patent alerts
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