IP Library › Granted Patent US 12,006,306

Granted Patent B2

US 12,006,306 · App. 17/243,508 · Granted Jun 11, 2024

Substituted pyridazines as TYK2 inhibitors

Inventors: Bohan Jin (San Francisco, CA); Qing Dong (San Francisco, CA); Gene Hung (San Francisco, CA); Stephen W. Kaldor (San Francisco, CA)

Assignee: Alumis Inc.

C07D401/14 C07D401/12 C07D403/12

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Patent No.: US 12,006,306
App. No.: 17/243,508
Granted: Jun 11, 2024
Kind: B2

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Abstract

Described herein are compounds, for example, substituted pyridazines, that are useful in treating a TYK2-mediated disorder. In some embodiments, the TYK2-mediated disorder is an autoimmune disorder, an inflammatory disorder, a proliferative disorder, an endocrine disorder, a neurological disorder, or a disorder associated with transplantation.

Claims (95)

1. A compound of Formula (XII):

or a pharmaceutically acceptable salt or stereoisomer thereof,

wherein:

R x is H, D, halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , NR b C(O)R a , NR b C(O)NR c R d , NR b C(O)OR b , NHS(O) 2 R a , OR b , OC(O)R a , OC(O)NR c R d , OC(O)OR b , SR b , S(O)R a , S(O) 2 R a , or S(O) 2 NR c R d ;

R 5 is halogen, CN, NO 2 , C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(NCN)R 7 , C(NCN)NR 9 R 10 , C(NCN)OR 8 , C(O)R 7 , C(O)NR 9 R 10 , C(O)OR 8 , NR 9 R 10 , NR 8 C(NCN)R 7 , NR 8 S(NOH)R 7 , NR 8 C(NCN)NR 9 R 10 , NR 8 C(NCN)OR 8 , NR 8 C(O)R 7 , NR 8 C(O)NR 9 R 10 , NR 8 C(O)OR 8 , NR 8 S(O)R 7 , NR 8 S(NR 8 )(O)R 7 , NR 8 S(O) 2 R 7 , OR 8 , OC(NCN)R 7 , OC(NCN)NR 9 R 10 , OC(NCN)OR 8 , OC(O)R 7 , OC(O)NR 9 R 10 , OC(O)OR 8 , SR 8 , S(O)R 7 , S(O) 2 R 7 , S(O) 2 NR 9 R 10 , cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , =0, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;

wherein the cycloalkyl or heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 heteroalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkyl(cycloalkyl), C 1 -C 6 alkyl(heterocycloalkyl), C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , ═O, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;

wherein the aryl or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 heteroalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkyl(cycloalkyl), C 1 -C 6 alkyl(heterocycloalkyl), C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl substituent is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , and ═O;

wherein each cycloalkyl and heterocycloalkyl substituent is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , and ═O; and

wherein each aryl and heteroaryl substituent is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , and OR b ;

R 7 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

wherein the aryl or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, and OCH 3 ;

R 8 is H, CN, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

R 9 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , ═O, cycloalkyl, and heterocycloalkyl;

wherein the cycloalkyl or heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 hydroxydeuteroalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , ═O, cycloalkyl, and heterocycloalkyl; and

wherein the aryl or heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 hydroxydeuteroalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , cycloalkyl, and heterocycloalkyl;

R 10 is H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , ═O, cycloalkyl, and heterocycloalkyl;

wherein the cycloalkyl or heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 hydroxydeuteroalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , ═O, cycloalkyl, and heterocycloalkyl; and

R 8 and R 9 , taken together with the atoms to which they are attached, form a heterocycloalkyl, wherein the heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O; or

R 9 and R 10 , taken together with the nitrogen atom to which they are attached, form a heterocycloalkyl, wherein the heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

R 16 is C(O)R 11 ;

R 11 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein the C 1 -C 6 alkyl, C 2 -C 6 alkenyl, or C 2 -C 6 alkynyl is optionally substituted with one or more R 11a substituents independently selected from the group consisting of D, halogen, CN, NO 2 , C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , NR b C(O)R a , NR b C(O)NR c R d , NR b C(O)OR b , NHS(O) 2 R a , OR b , OC(O)R a , OC(O)NR c R d , OC(O)OR b , SR b , S(O)R a , S(O) 2 R a , and S(O) 2 NR c R d ; and

wherein the cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is optionally substituted with one or more R 11a substituents independently selected from the group consisting of D, halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , NR b C(O)R a , NR b C(O)NR c R d , NR b C(O)OR b , NHS(O) 2 R a , OR b , OC(O)R a , OC(O)NR c R d , OC(O)OR b , SR b , S(O)R a , S(O) 2 R a , and S(O) 2 NR c R d ;

R 3 is H, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, or C 1 -C 6 haloalkyl;

R 4 is H, D, halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , NR b C(O)R a , NR b C(O)NR c R d , NR b C(O)OR b , NHS(O) 2 R a , OR b , OC(O)R a , OC(O)NR c R d , OC(O)OR b , P(O)R b R b , SR b , S(O)R a , S(O) 2 R a , or S(O) 2 NR c R d ;

Ring B is phenyl or a 5- to 10-membered heteroaryl;

L is a bond;

Ring A is cycloalkyl, heterocycloalkyl, aryl, or heteroaryl, wherein the cycloalkyl, heterocycloalkyl, aryl, or heteroaryl is optionally substituted with one or more independently selected R A substituents;

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

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , and ═O;

wherein each cycloalkyl and heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , and ═O; and

wherein each aryl and heteroaryl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , and OR b ; or

two geminal R A , taken together with the carbon atom to which they are attached, form —C(O)—;

each R a is independently C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

wherein each cycloalkyl and heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O; and

each R b is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

wherein each cycloalkyl and heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O; and

each R c is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

wherein each cycloalkyl and heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O; and

wherein each aryl and heteroaryl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, and OCH 3 ; and

each R d is independently H, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, cycloalkyl, heterocycloalkyl, aryl, or heteroaryl;

wherein each C 1 -C 6 alkyl, C 2 -C 6 alkenyl, and C 2 -C 6 alkynyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O;

wherein each cycloalkyl and heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O; and

wherein each aryl and heteroaryl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, and OCH 3 ; or

any R c and R d , taken together with the nitrogen atom to which they are attached, independently forms a heterocycloalkyl, wherein each heterocycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O.

2. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R x is H.

3. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 5 is NR 8 C(O)NR 9 R 10 or heterocycloalkyl;

wherein the heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 heteroalkyl, C 1 -C 6 aminoalkyl, C 1 -C 6 hydroxyalkyl, C 1 -C 6 alkyl(cycloalkyl), C 1 -C 6 alkyl(heterocycloalkyl), C 1 -C 6 alkyl(aryl), C 1 -C 6 alkyl(heteroaryl), C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , ═O, cycloalkyl, heterocycloalkyl, aryl, and heteroaryl;

4. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 5 is NR 8 C(O)NR 9 R 10 .

5. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 5 is heterocycloalkyl;

6. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 9 and R 10 , taken together with the nitrogen atom to which they are attached, form a heterocycloalkyl, wherein the heterocycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C(O)CH 3 , C(O)OH, C(O)OCH 3 , NH 2 , OH, OCH 3 , and ═O.

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

R 5 is NR 8 C(O)R 7 or NR 8 C(O)NR 9 R 10 ;

R 7 is cycloalkyl;

R 8 is H; and

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

R 11 is C 1 -C 6 alkyl or cycloalkyl, wherein the C 1 -C 6 alkyl is optionally substituted with one or more independently selected R 11a substituents; and

each R 11a is an independently selected halogen substituent.

9. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 3 is H.

10. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R 4 is H, D, halogen, CN, C 1 -C 6 alkyl, C 1 -C 6 deuteroalkyl, C 1 -C 6 haloalkyl, C(O)R a , C(O)NR c R d , C(O)OR b , NR c R d , OR b , or OC(O)NR c R d .

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

R 4 is H or OR b ; and

R b is C 1 -C 6 alkyl, wherein the C 1 -C 6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of D and halogen.

12. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Ring B is a bicyclic 5- to 10-membered heteroaryl.

13. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Ring A is heterocycloalkyl or heteroaryl;

wherein the heterocycloalkyl or heteroaryl is 3- to 6-membered; and

wherein the heterocycloalkyl or heteroaryl is optionally substituted with one or more independently selected R A substituents.

14. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Ring A is heterocycloalkyl or heteroaryl;

wherein the heterocycloalkyl or heteroaryl is 5-membered; and

wherein the heterocycloalkyl or heteroaryl is optionally substituted with one or more independently selected R A substituents.

15. The compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof, wherein each R A is independently D, halogen, or C 1 -C 6 alkyl, wherein each C 1 -C 6 alkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of D and halogen.

16. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a therapeutically effective amount of the compound of claim 1 , or a pharmaceutically acceptable salt or stereoisomer thereof.

Assignments (2)

CHANGE OF NAME Recorded Feb 10, 2022

From: ESKER THERAPEUTICS, INC.

To: ALUMIS INC.

Reel/Frame 059009/0623 →

ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 6, 2021

From: JIN, BOHAN; DONG, QING; HUNG, GENE; KALDOR, STEPHEN W.

To: ESKER THERAPEUTICS, INC.

Reel/Frame 057107/0874 →

Continuity (9)

Continuation 16938183 · Jul 24, 2020

Continuation PCTUS2019057485 · Oct 22, 2019

Provisional Application 62749003 · Oct 22, 2018

Provisional Application 62756942 · Nov 7, 2018

Provisional Application 62839459 · Apr 26, 2019

Provisional Application 62875449 · Jul 17, 2019

Provisional Application 62893721 · Aug 29, 2019

Provisional Application 62907354 · Sep 27, 2019

Related Publication 20230023761A1 · Jan 26, 2023

Cited By (1)

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