US 12,391,684 B2
Pharmaceutical formulations and methods for the treatment of gastrointestinal disorders
Pascal Jean Druzgala, Santa Rosa, CA (US); Peter Milner, Mountain View, CA (US); and Jien Heh Tien, Evanston, IL (US)
Assigned to RENEXXION, LLC, Los Altos, CA (US)
Filed by Renexxion, LLC, Los Altos, CA (US)
Filed on Aug. 12, 2024, as Appl. No. 18/801,407.
Application 18/157,783 is a division of application No. 17/887,325, filed on Aug. 12, 2022, granted, now 11,643,409, issued on May 9, 2023.
Application 16/734,961 is a division of application No. 16/181,177, filed on Nov. 5, 2018, granted, now 10,570,127, issued on Feb. 25, 2020.
Application 18/801,407 is a continuation of application No. 18/363,600, filed on Aug. 1, 2023, granted, now 12,098,149.
Application 18/363,600 is a continuation of application No. 18/157,783, filed on Jan. 20, 2023, granted, now 11,827,631, issued on Nov. 28, 2023.
Application 17/887,325 is a continuation of application No. 16/734,961, filed on Jan. 6, 2020, granted, now 11,498,918, issued on Nov. 15, 2022.
Prior Publication US 2025/0223287 A1, Jul. 10, 2025
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 453/02 (2006.01); A61K 9/00 (2006.01); A61K 31/439 (2006.01); A61P 1/04 (2006.01); A61P 1/10 (2006.01)
CPC C07D 453/02 (2013.01) [A61K 9/0029 (2013.01); A61K 9/0053 (2013.01); A61K 31/439 (2013.01); A61P 1/04 (2018.01); A61P 1/10 (2018.01); C07B 2200/13 (2013.01)] 18 Claims
 
1. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a trihydrate form of (3S, 4R, 3′R)-6-[4-(4-amino-5-chloro-2-methoxy-benzoylamino)-3-methoxy-piperidin-1-yl]-hexanoic acid 1-azabicyclo[2.2.2]oct-3′-yl ester di-hydrochloride salt having the following formula:

OG Complex Work Unit Chemistry
wherein the trihydrate form is in a crystalline form characterized by XRPD 2θ peaks at (i) 7.74±0.5° and 20.95±0.5°; (ii) 7.74±0.5° and 15.0±0.2°; or (iii) 7.74±0.5°, 20.95±0.5°, and 15.0±0.2°;
wherein the pharmaceutical composition comprises between about 6.5% to about 10% by weight water relative to the total weight of (3S, 4R, 3′R)-6-[4-(4-amino-5-chloro-2-methoxy-benzoylamino)-3-methoxy-piperidin-1-yl]-hexanoic acid 1-azabicyclo[2.2.2]oct-3′-yl ester di-hydrochloride salt present;
wherein the pharmaceutical composition comprises less than about 5,000 ppm organic A solvent.