Granted Patent B2

US 12,365,655 · App. 17/392,356 · Granted Jul 22, 2025

Inventors: H. Rachel Lagiakos (Parkville, AU); Richard Charles Foitzik (Parkville, AU); Catherine Fae Hemley (Melbourne, AU); Michelle Ang Camerino (Parkville, AU); Paul Anthony Stupple (Parkville, AU); Ylva Elisabet Bergman Bozikis (Parkville, AU); Scott Raymond Walker (Parkville, AU)

Assignee: CTXT PTY LTD

C07D261/20C07D413/10C07D413/12C07D417/12

Abstract

Claims (65)

1. A compound of formula (I), or a pharmaceutically acceptable salt thereof:

wherein:

R 1 , R 2 , R 3 and R 4 are independently selected from the group consisting of:

(i) H;

(ii) C 1-3 alkyl, optionally substituted by:

hydroxy,

C 1-2 alkoxy,

NH 2 ,

phenyl,

C 5-6 heteroaryl,

C 1-4 alkyl carbamoyl, or

acylamido;

(iii) C 1-3 alkoxy, optionally substituted by C 3-6 cycloalkyl or by one or more fluoro groups;

(iv) C 3-6 cycloalkyl;

(v) halo;

(vi) COR C , where R C is selected from NR N1 R N2 , where R N1 and R N2 are independently selected from H and methyl;

(vii) cyano, NH 2 , or NO 2 ; and

(viii) phenyl or C 5-6 heteroaryl, optionally substituted by methyl, hydroxy or methoxy; and

Ar is a phenyl, optionally substituted by one or more groups selected from the group consisting of:

(i) C 1-4 alkyl, optionally substituted by hydroxy, C 1-2 alkoxy, NH 2 , C 1-4 alkyl carbamoyl, or by one or more fluoro groups;

(ii) C 3-6 cycloalkyl;

(iii) hydroxy; cyano; NR N3 R N4 , where R N3 and R N4 are independently selected from H and methyl; or acylamido;

(iv) halo;

(v) C 1-3 alkoxy, optionally substituted by hydroxy, C(O)NH 2 , C 3-6 cycloalkyl, phenyl, C 5-6 heteroaryl, or by one or more fluoro groups;

(vi) phenoxy, optionally substituted by fluoro;

(vii) phenyl or C 5-6 heteroaryl; and

(viii) SF 5 or SO 2 CH 3 ;

and wherein at least one of R 1 , R 2 , R 3 and R 4 is not H.

2. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is C 1-3 alkyl, optionally substituted by:

hydroxy,

C 1-2 alkoxy,

NH 2 ,

phenyl,

C 5-6 heteroaryl,

C 1-4 alkyl carbamoyl, or

acylamido.

3. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is C 1-3 alkoxy, optionally substituted by C 3-6 cycloalkyl or one of or more fluoro groups.

4. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is C 3-6 cycloalkyl.

5. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is halo.

6. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is COR C , where R C is selected from NR N1 R N2 , where R N1 and R N2 are independently selected from H and methyl.

7. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is cyano, NH 2 or NO 2 .

8. The compound or salt of claim 1 , wherein at least one of R 1 , R 2 , R 3 and R 4 is phenyl or C 5-6 heteroaryl, optionally substituted by methyl, cyano, hydroxy or methoxy.

9. The compound or salt of claim 1 , wherein:

(a) R 4 is methoxy, R 2 is CH 2 OCH 3 or CH 2 OCH 2 CH 3 , and R 1 and R 3 are H;

(b) R 4 is methoxy, R 2 is phenyl, optionally substituted by methyl or methoxy, and R 1 and R 3 are H;

(c) R 4 is methoxy, R 2 is C 5-6 heteroaryl, optionally substituted by methyl;

(d) R 4 is methoxy and R 1 , R 2 and R 3 are H;

(e) R 4 is chloro, R 2 is C 1-3 alkyl or bromo, and R 1 and R 3 are H;

(f) R 4 is chloro and R 1 , R 2 and R 4 are H; or

(g) R 3 is C 1-3 alkyl and R 1 , R 2 and R 4 are H.

10. The compound or salt of claim 1 , wherein:

(a) Ar is substituted by C 1-4 alkyl, optionally substituted by hydroxy, C 1-2 alkoxy, NH 2 , C 1-4 alkyl carbamoyl, or one or more fluoro groups;

(b) Ar is substituted by C 3-6 cycloalkyl;

(c) Ar is substituted by hydroxy; cyano; NR N3 R N4 , where R N3 and R N4 are independently selected from H and methyl; or acylamido; or

(d) Ar is substituted by halo.

11. The compound or salt of claim 1 , wherein Ar is substituted by C 1-3 alkoxy, optionally substituted by hydroxy, C(O)NH 2 , C 3-6 cycloalkyl, phenyl, C 5-6 heteroaryl, or one or more fluoro groups.

12. The compound or salt of claim 1 , wherein:

(a) Ar is substituted by phenoxy, optionally substituted by fluoro;

(b) Ar is substituted by phenyl or C 5-6 heteroaryl; or

(c) Ar is substituted by SF 5 or SO 2 CH 3 .

13. The compound or salt of claim 1 , wherein Ar is:

(a) 5-ethyl-2-methoxyphenyl;

(b) 5-CF 3 -2-methoxyphenyl; or

(c) 2,6-dimethoxyphenyl.

14. The compound or salt of claim 1 , wherein two of R 1 , R 2 , R 3 and R 4 are H.

Assignments (2)

Priority Claims (1)

Continuity (2)

References Cited (264)