US 10,889,561 B2
Process of making somatostatin modulators
Jayachandra P. Reddy, West Palm Beach, FL (US); and Mahmoud Mirmehrabi, Halifax (CA)
Assigned to CRINETICS PHARMACEUTICALS, INC., San Diego, CA (US)
Filed by Crinetics Pharmaceuticals, Inc., San Diego, CA (US)
Filed on Oct. 3, 2019, as Appl. No. 16/592,595.
Application 16/592,595 is a continuation of application No. 16/249,729, filed on Jan. 16, 2019, granted, now 10,464,918.
Claims priority of provisional application 62/618,538, filed on Jan. 17, 2018.
Prior Publication US 2020/0048219 A1, Feb. 13, 2020
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 401/04 (2006.01)
CPC C07D 401/04 (2013.01) [C07B 2200/13 (2013.01)] 10 Claims
 
1. A method of treating acromegaly or a neuroendocrine tumor, or combination thereof, in a human comprising orally administering to the human with acromegaly or a neuroendocrine tumor, or combination thereof, a pharmaceutical composition comprising the compound 3-[4-(4-amino-piperidin-1-yl)-3-(3,5-difluoro-phenyl)-quinolin-6-yl]-2-hydroxy-benzonitrile monohydrochloride, or solvate thereof; and at least one pharmaceutically acceptable excipient, wherein 3-[4-(4-amino-piperidin-1-yl)-3-(3,5-difluoro-phenyl)-quinolin-6-yl]-2-hydroxy-benzonitrile monohydrochloride, or solvate thereof is crystalline and is characterized as having: an X-ray powder diffraction (XRPD) pattern with peaks at 4.5° 2-Theta, 9.1° 2-Theta, 10.2° 2-Theta, 16.3° 2-Theta, 18.4° 2-Theta, and 19.1° 2-Theta; an X-ray powder diffraction (XRPD) pattern substantially the same as shown in FIG. 1; a Differential Scanning calorimetry (DSC) thermogram with an endotherm having an onset at about 207° C. and a peak at about 220° C.; a Differential Scanning calorimetry (DSC) thermogram substantially the same as shown in FIG. 2(a); an infrared (IR) spectrum with peaks at 2223 cm−1, 1620 cm−1, 1595 cm−1, 1457 cm−1, 1238 cm−1, 1220 cm−1, and 1117 cm−1; an infrared (IR) spectrum substantially the same as shown in FIG. 3; an unchanged XRPD when heated up to about 200° C., upon exposure to more than 90% relative humidity for about 24 hours, or upon exposure to about 75% RH and 40° C. over one week, or combinations thereof; or combinations thereof.