Granted Patent B2

US 12,398,130 · App. 18/062,295 · Granted Aug 26, 2025

Inventors: Anna Quattropani (Rolle, CH); Santosh S. Kulkarni (Bangalore, IN); Awadut Gajendra Giri (Bangalore, IN); Dawn V. Toronto (Saint Lamain, FR); David Malcolm Crowe (Reading, GB)

Assignee: Asceneuron SA

C07D417/14C07D405/12C07D405/14C07D417/12C07D513/04

Abstract

Claims (25)

1. An acid addition salt of a compound of formula (I):

and an acid that is hydrochloric acid, maleic acid, tartaric acid, sulfuric acid, or p-toluolsulfonic acid;

wherein:

X is O or CH 2 ;

n is 0 or 1;

Q is:

Z 1 is S, O, or NR 3 ;

each of Z 2 , Z 2′ , and Z 3 , independently, are selected from CR 5 , CR 6 , and N;

each of R 5 , R 5′ , R 6 , and R 7 , independently, are selected from H, Hal, NR 3 R 4 , NO 2 , Ar, Het, Cyc, and straight chain or branched alkyl having 1 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups may be replaced by a group selected from O, NR 3 , S, SO, SO 2 , CO, COO, OCO, CONR 3 , and NR 3 CO, and wherein 1 to 5 hydrogen atoms are optionally replaced by Hal, NR 3 R 4 , NO 2 , OR 3 , Het, Ar, or Cyc;

R 8 is H, methyl, or straight chain or branched alkyl having 2 to 12 carbon atoms, wherein 1 to 3 CH 2 -groups are optionally replaced by a group selected from O, NR 3 , S, SO, SO 2 , CO, COO, OCO, CONR 3 , and NR 3 CO, and wherein 1 to 5 hydrogen atoms are optionally replaced by Hal, NR 3 R 4 , or NO 2 ;

each of R 3 and R 4 , independently, are selected from H and straight chain or branched alkyl group having 1 to 12 carbon atoms;

Hal is F, Cl, Br, or I;

Het is a saturated, unsaturated, or aromatic ring, being monocyclic, bicyclic, or fused-bicyclic, and having 3- to 8-members and containing 1 to 4 heteroatoms selected from N, O and S, which may be substituted by 1 to 3 substituents selected from R 5 , Hal, and OR 3 ;

Ar is a 6-membered carbocyclic aromatic ring or a fused or non-fused bicyclic aromatic ring system, which is optionally substituted by 1 to 3 substituents independently selected from R 5 , OR 3 , and Hal;

Cyc is a saturated or an unsaturated carbocyclic ring having from 3 to 8 carbon atoms which is optionally substituted by 1 to 3 substituents independently selected from R 5 , Hal, or OH;

or a solid form thereof.

2. The acid addition salt of claim 1 , or a solid form thereof, wherein the compound of formula (I) is formula (Ia):

3. The acid addition salt of claim 1 , or a solid form thereof, wherein Q is

4. The acid addition salt of claim 1 , or a solid form thereof, wherein the molar ratio of the compound of formula (I) to acid is 1:1.

5. A solid oral dosage form comprising the acid addition salt of claim 1 or a solid form thereof.

6. A method for the preparation of the acid addition salt of claim 1 , comprising the following steps:

a) suspending or dissolving the compound of formula (I) and the acid in a suitable solvent or solvent mixture to prepare a mixture;

b) heating the mixture obtained in step a) to a temperature of between 30° C. to the boiling point of the selected solvent or solvent mixture, and then allowing the mixture to cool to room temperature;

c) optionally repeating step b) several times;

d) separating and drying the acid addition salt.

Assignments (1)

Priority Claims (1)

Continuity (3)

References Cited (296)