IP Library › Granted Patent US 11,174,242
Granted Patent B2
US 11,174,242 · App. 16/474,461 · Granted Nov 16, 2021

Heteroaryl compounds and their use

Inventors: Ana Maria García Collazo (Barcelona, ES); Xavier Barril Alonso (Barcelona, ES); Elena Cubero Jordà (Barcelona, ES); Marc Revés Vilaplana (Barcelona, ES); Richard Spurring Roberts (Barcelona, ES)
Assignee: Minoryx Therapeutics S.L.
C07D401/06A61P43/00C07D239/49C07D251/18C07D401/12C07D403/06C07D405/12
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Quick Facts
Patent No.
US 11,174,242
App. No.
16/474,461
Granted
Nov 16, 2021
Kind
B2
Abstract

The application is directed to compounds of formula (I): and their salts and solvates, wherein R 1 , R 2 , R 3 , A 1 , A 2 , A 3 , and n are as set forth in the specification, as well as to a method for their preparation, pharmaceutical compositions comprising the same, and use thereof for the treatment and/or prevention of a lysosomal storage disease, such as Gaucher's, and other diseases or disorders that are synucleinopathies.

Claims (71)

1. A compound of formula (I):

or a pharmaceutically acceptable salt or solvate thereof, wherein

A 1 , A 2 , and A 3 are each independently selected from the group consisting of N, CH and C(R 4 ), provided that at least one of A 1 , A 2 , or A 3 is N;

with the proviso that no more than two of A 1 , A 2 , or A 3 is N;

each R 4 is independently selected from the group consisting of halogen, —C 1-4 alkyl, —C 1-4 alkoxy, and —CN;

n is 1 or 2, wherein the alkylene chain can be optionally substituted with one or more —C 1-4 alkyl groups;

R 1 is selected from the group consisting of —C 1-4 alkyl substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, and optionally substituted —O—(C 6-10 aryl), —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl, and —C(═O)Ra, wherein said —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl groups are optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 halogen atoms, optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, and optionally substituted —O—(C 6-10 aryl),

wherein the optional substituents in said optionally substituted —C 6-10 aryl and —O—(C 6-10 aryl) are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, carbamoyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl groups;

and wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atoms; and wherein said —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl is optionally fused to a further (second) ring; and

R 2 is selected from the group consisting of hydrogen, —C 1-4 alkyl, and —C 3-6 cycloalkyl, wherein said —C 1-4 alkyl is optionally substituted with —O(C 1-4 )alkyl optionally substituted with —O(C 1-4 )NH 2 , hydroxy, —CN, halogen, or —N(Rb) 2 ; or

R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted 5- to 10-membered heterocyclic ring, wherein said 5- to 10-membered heterocyclic ring optionally contains 1, 2, or 3 additional heteroatoms selected from the group consisting of N, S, or O, and wherein said 5- to 10-membered heterocyclic ring is optionally fused to a phenyl ring;

Ra is selected from the group consisting of —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl, wherein said —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl groups are optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 halogen atoms, optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, and -(5- to 10-membered)-C 2-9 heterocyclyl,

wherein the optional substituents in said optionally substituted —C 6-10 aryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl; and

wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atoms;

and wherein said —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl is optionally fused to a further (second) ring;

each Rb is independently hydrogen, —C 1-4 alkyl, —C 3-10 cycloalkyl, or -(5- to 10-membered)-C 2-9 heterocyclyl, wherein said —C 1-4 alkyl, —C 3-10 cycloalkyl or -(5- to 10-membered)-C 2-9 heterocyclyl group is optionally substituted by 1, 2 or 3 fluorine atoms; and

R 3 is selected from the group consisting of —C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 3-10 cycloalkyl, and -(5- to 10-membered)-C 2-9 heterocyclyl, wherein said —C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 3-10 cycloalkyl, and -(5- to 10-membered)-C 2-9 heterocyclyl groups are optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 substituents each independently selected from the group consisting of halogen, —CN, —ORb, and —N(Rb) 2 , optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl and -(5- to 10-membered)-C 2-9 heterocyclyl,

wherein the optional substituents in said optionally substituted —C 6-10 aryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, carbamoyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl groups; and

wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atoms; and

wherein said —C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 3-10 cycloalkyl, and -(5- to 10-membered)-C 2-9 heterocyclyl is optionally fused to a further (second) ring;

provided that the compound is not:

2. A compound of formula (I):

or a pharmaceutically acceptable salt or solvate thereof, wherein

A 1 , A 2 , and A 3 are each independently selected from the group consisting of N, CH and C(R 4 ), provided that at least one of A 1 , A 2 , or A 3 is N;

with the proviso that no more than two of A 1 , A 2 , or A 3 is N;

each R 4 is independently selected from the group consisting of halogen, —C 1-4 alkyl, —C 1-4 alkoxy, and —CN;

n is 1 or 2;

R 1 is selected from the group consisting of —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl, and —C(═O)Ra, wherein said —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl groups are optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 halogen atoms, optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, and -(5- to 10-membered)-C 2-9 heterocyclyl,

wherein the optional substituents in said optionally substituted —C 6-10 aryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, carbamoyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl groups;

and wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atoms;

and wherein said —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl is optionally fused to a further (second) ring; and

R 2 is hydrogen or —C 1-4 alkyl; or

R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted 5- to 10-membered heterocyclic ring, wherein said 5- to 10-membered heterocyclic ring optionally contains 1, 2, or 3 additional heteroatoms selected from the group consisting of N, S, or O, and wherein said 5- to 10-membered heterocyclic ring is optionally fused to a phenyl ring;

Ra is selected from the group consisting of —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl, and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl, wherein said —C 1-4 alkyl, —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl groups are optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 halogen atoms, optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, and -(5- to 10-membered)-C 2-9 heterocyclyl,

wherein the optional substituents in said optionally substituted —C 6-10 aryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl; and

wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atoms;

and wherein said —C 3-10 cycloalkyl, —C 1-4 alkyl-C 3-10 cycloalkyl, —C 6-10 aryl, —C 1-4 alkyl-C 6-10 aryl, -(5- to 10-membered)-C 1-9 heteroaryl, —C 1-4 alkyl-(5- to 10-membered)-C 1-9 heteroaryl, -(5- to 10-membered)-C 2-9 heterocyclyl and —C 1-4 alkyl-(5- to 10-membered)-C 2-9 heterocyclyl is optionally fused to a further (second) ring;

each Rb is independently hydrogen, —C 1-4 alkyl, —C 3-10 cycloalkyl, or -(5- to 10-membered)-C 2-9 heterocyclyl, wherein said —C 1-4 alkyl, —C 3-10 cycloalkyl or -(5- to 10-membered)-C 2-9 heterocyclyl group is optionally substituted by 1, 2 or 3 fluorine atoms;

R 3 is —C 6-10 aryl or -(5- to 10-membered)-C 1-9 heteroaryl, wherein said —C 6-10 aryl or -(5- to 10-membered)-C 1-9 heteroaryl group is optionally substituted with 1, 2 or 3 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 substituents each independently selected from the group consisting of halogen, —CN, —ORb, and —N(Rb) 2 , optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl and -(5- to 10-membered)-C 2-9 heterocyclyl,

wherein the optional substituents in said optionally substituted —C 6-10 aryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, —OH, C 1-4 alkoxycarbonyl, hydroxycarbonyl, carbamoyl, —NO 2 , —CN, —C 1-4 alkyl optionally substituted by one or more halogen atoms, —C 1-4 alkoxy optionally substituted by one or more halogen atoms and C 1-4 hydroxyalkyl groups; and

wherein the optional substituents in said optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl are selected from 1, 2, or 3 substituents, which can be the same or different, selected from the group consisting of halogen, C 1-4 alkoxycarbonyl, carbamoyl, —NO 2 , —OH, —C 1-4 alkyl optionally substituted by one or more halogen atoms, and —C 1-4 alkoxy optionally substituted by one or more halogen atom; provided that the compound is not:

3. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 1 is N and A 2 and A 3 are each independently selected from the group consisting of CH and C(R 4 ).

4. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein n is 1.

5. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein n is 2.

6. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 3 is unsubstituted —C 6-10 aryl or —C 6-10 aryl substituted with 1 or 2 substituents each independently selected from the group consisting of halogen, hydroxy, —CN, —O(C 1-4 )alkyl, —S(C 1-4 )alkyl, —N(C 1-4 alkyl) 2 , —NH(C 1-4 alkyl), and —C 1-4 alkyl optionally substituted with 1, 2, or 3 substituents each independently selected from the group consisting of halogen, —CN, —O(C 1-4 )alkyl, —N(C 1-4 alkyl) 2 , and —NH(C 1-4 alkyl).

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

8. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 2 is —C 1-4 alkyl.

9. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is —C 6-10 aryl or —C 1-4 alkyl-C 6-10 aryl, wherein said —C 6-10 aryl or —C 1-4 alkyl-C 6-10 aryl is optionally substituted with 1, 2 or 3 groups each independently selected from the group consisting of halogen, hydroxy, —CN, —ORb, —SRb, —N(Rb) 2 , —C 1-4 alkyl optionally substituted with 1, 2, or 3 halogen atoms, optionally substituted —C 6-10 aryl, optionally substituted -(5- to 10-membered)-C 1-9 heteroaryl, and -(5- to 10-membered)-C 2-9 heterocyclyl, wherein Rb is as defined in claim 1 , and wherein the optional substituents in said optionally substituted —C 6-10 aryl and -(5- to 10-membered)-C 1-9 heteroaryl are as defined in claim 1 .

10. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein Rb is hydrogen or —C 1-4 alkyl.

11. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 and R 2 together with the nitrogen atom to which they are attached form an optionally substituted 5- to 10-membered heterocyclic ring, wherein said 5- to 10-membered heterocyclic ring optionally contains 1, 2, or 3 additional heteroatoms selected from the group consisting of N, S, or O, and wherein said 5- to 10-membered heterocyclic ring is optionally fused to a phenyl ring.

12. The compound of claim 1 , which is selected from the group consisting of

or a pharmaceutically acceptable salt or solvate thereof.

13. The compound of claim 1 , which is selected from the group consisting of

or a pharmaceutically acceptable salt or solvate thereof.

14. A compound selected from the group consisting of

or a pharmaceutically acceptable salt or solvate thereof.

15. A compound selected from the group consisting of

or a pharmaceutically acceptable salt or solvate thereof.

16. A pharmaceutical composition, comprising an effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, and at least one pharmaceutically acceptable excipient.

17. A pharmaceutical composition, comprising an effective amount of a compound of claim 14 , or a pharmaceutically acceptable salt or solvate thereof, and at least one pharmaceutically acceptable excipient.

18. A pharmaceutical composition, comprising an effective amount of a compound of claim 15 , or a pharmaceutically acceptable salt or solvate thereof, and at least one pharmaceutically acceptable excipient.

19. A pharmaceutical composition, comprising an effective amount of a compound of claim 2 , or a pharmaceutically acceptable salt or solvate thereof, and at least one pharmaceutically acceptable excipient.

20. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 2 is N and A 1 and A 3 are each independently selected from the group consisting of CH and C(R 4 ).

21. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 3 is N and A 1 and A 2 are each independently selected from the group consisting of CH and C(R 4 ).

22. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 1 and A 2 are both N and A 3 is CH or C(R 4 ).

23. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 1 and A 3 are both N and A 2 is CH or C(R 4 ).

24. The compound of claim 1 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 2 and A 3 are both N and A 1 is CH or C(R 4 ).

25. The compound of claim 2 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 1 and A 3 are both N and A 2 is CH or C(R 4 ).

26. The compound of claim 2 , or a pharmaceutically acceptable salt or solvate thereof, wherein A 2 and A 3 are both N and A 1 is CH or C(R 4 ).

27. The compound of claim 9 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 is unsubstituted phenyl or unsubstituted benzyl.

28. The compound of claim 11 , or a pharmaceutically acceptable salt or solvate thereof, wherein R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- or 6-membered ring optionally fused to a phenyl ring.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 23, 2019
From: GARCÍA COLLAZO, ANA MARIA; BARRIL ALONSO, XAVIER; CUBERO JORDÀ, ELENA; REVÉS VILAPLANA, MARC; ROBERTS, RICHARD SPURRING
To: MINORYX THERAPEUTICS S.L.
Reel/Frame 050801/0398 →
Priority Claims (1)
EP 16382672 · Dec 29, 2016 · regional
Continuity (1)
Related Publication 20190337922A1 · Nov 7, 2019
Cited By (1)
US 12,661,342