US 12,134,608 B2
Benzimidazole derivatives as dual histamine H1 and histamine H4 receptor ligands
Isabelle Berrebi-Bertrand, Pace (FR); Xavier Billot, Saint-Grégoire (FR); Thierry Calmels, Rennes (FR); Marc Capet, Melesse (FR); Stéphane Krief, Rennes (FR); Olivier Labeeuw, Fougeres (FR); Jeanne-Marie Lecomte, Paris (FR); Nicolas Levoin, L'Hermitage (FR); Xavier Ligneau, Saint-Grégoire (FR); Philippe Robert, Pace (FR); and Jean-Charles Schwartz, Paris (FR)
Assigned to BIOPROJET, Paris (FR)
Filed by BIOPROJET, Paris (FR)
Filed on Feb. 10, 2022, as Appl. No. 17/668,575.
Application 17/668,575 is a division of application No. 16/192,162, filed on Nov. 15, 2018, granted, now 11,306,069.
Claims priority of application No. 17306587 (EP), filed on Nov. 15, 2017.
Prior Publication US 2022/0281839 A1, Sep. 8, 2022
Int. Cl. C07D 401/12 (2006.01); A61K 31/454 (2006.01); A61K 45/06 (2006.01); A61P 29/00 (2006.01); A61P 37/08 (2006.01)
CPC C07D 401/12 (2013.01) [A61K 31/454 (2013.01); A61K 45/06 (2013.01); A61P 29/00 (2018.01); A61P 37/08 (2018.01)] 18 Claims
 
1. A hydrochloride salt of an (S)-enantiomer of formula (II):

OG Complex Work Unit Chemistry
wherein:
* denotes the asymmetric carbon exhibiting a defined stereochemistry;
X represents F; and
R1, R2, R3, and R4 represent H;
wherein the hydrochloride salt of the (S)-enantiomer has dual affinity for H1 and H4 receptors, and
wherein the hydrochloride salt has the following X-ray powder diffraction peaks: (characteristic peaks, 2θ in°): 8.6, 12.4, 13.1, 15.9, 16.8, 18.8, 19.9, 20.4, 21.3, 23.4, 25.0, 25.7, 26.3, 26.9, 28.4, and 30.1.