IP Library Patent Application 18263847
Patent Application
App. No. 18/263,847

A CRYSTALLINE FORM OF (4-METHYL-2-[1,2,3]TRIAZOL-2-YL-PHENYL)-[(R)-3-(3-[1,2,3]TRIAZOL-2-YL-BENZYL)-MORPHOLIN-4-YL]-METHANONE

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Patent No.
US None
App. No.
18/263,847
Abstract

The present invention relates to a crystalline form of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone, a process for the preparation thereof, pharmaceutical compositions comprising the same and its use as an orexin receptor antagonist in the prevention and/or treatment of various orexin receptor-mediated disorders such as Binge-Eating Disorder (BED).

Claims (57)

1 . A crystalline form of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone, characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 10.5°, 14.2°, and 18.4°.

2 . The crystalline form according to claim 1 , characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.5°, 14.2°, 18.4°, and 21.80.

3 . The crystalline form according to claim 1 , characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.5°, 12.5°, 13.7°, 14.2°, 14.60, 18.40, 21.40, 21.80, and 25.10.

4 . The crystalline form according to claim 1 , which essentially shows the X-ray powder diffraction pattern as depicted in FIG. 1 .

5 . The crystalline form according to claim 1 , characterized by a melting point of about 117.6° C. as determined by differential scanning calorimetry.

6 . The crystalline form according to claim 1 , obtainable by a process comprising

a. dissolving (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone in a solvent, said solvent comprising one or more lower alcohols;

b. awaiting formation of a solid product; and

c. isolating the solid product.

7 . A process for making the crystalline form according to claim 1 , said process comprising recrystallization of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone in a solvent, said solvent comprising one or more lower alcohols.

8 . A pharmaceutical composition comprising as active ingredient the crystalline form according to claim 1 , and at least one pharmaceutically acceptable carrier.

9 . A solid dosage form, wherein the solid dosage form comprises a crystalline form of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone, wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 10.5°, 14.2°, and 18.4°.

10 . The pharmaceutical composition according to claim 8 , in form of a tablet for oral use, said composition comprising

from about 3% w/w to about 40% w/w of said active ingredient;

from about 30% w/w to about 70% w/w microcrystalline cellulose;

from about 15% w/w to about 60% w/w mannitol;

from about 3% w/w to about 10% w/w crosspovidone;

from about 0.2% w/w to about 4% w/w sodium stearyl fumarate; and

from about 0.5% w/w to about 5% w/w silica colloidal hydrated.

11 . The pharmaceutical composition according to claim 8 , in form of a tablet for oral use, said composition comprising

from 22% to 25% w/w of said active ingredient;

from 39% to 44% w/w microcrystalline cellulose;

from 24% to 30% w/w mannitol;

from 4% to 6% w/w crosspovidone;

from 0.5% to 1.5% w/w sodium stearyl fumarate; and

from 1.5% to 2.5% w/w silica colloidal hydrated;

or

from 10% to 13% w/w of said active ingredient;

from 47% to 52% w/w microcrystalline cellulose;

from 29% to 34% w/w mannitol;

from 4% to 6% w/w crosspovidone;

from 0.5% to 1.5% w/w sodium stearyl fumarate; and

from 1% to 2% w/w silica colloidal hydrated;

or

from 6% to 8% w/w of said active ingredient;

from 48% to 54% w/w microcrystalline cellulose;

from 31% to 35% w/w mannitol;

from 4% to 6% w/w crosspovidone;

from 0.5% to 1.5% w/w sodium stearyl fumarate; and

from 1% to 2% w/w silica colloidal hydrated;

or

from 5% to 7% w/w of said active ingredient;

from 50% to 55% w/w microcrystalline cellulose;

from 30% to 35% w/w mannitol;

from 4% to 6% w/w crosspovidone;

from 0.5% to 1.5% w/w sodium stearyl fumarate; and

from 0.5% to 2% w/w silica colloidal hydrated.

12 . (canceled)

13 . A method for the prevention and/or treatment of anxiety disorders, addiction disorders, mood disorders, appetite disorders, cognitive dysfunctions, or sleep disorders in a patient in need thereof, wherein the method comprises administering to the patient a crystalline form of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone, wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 10.50, 14.20, and 18.40.

14 . The method according to claim 13 , wherein the method is for the prevention and/or treatment of an eating disorder selected from a group comprising Binge-Eating Disorder (BED); Bulimia Nervosa (BN); Anorexia Nervosa (AN); Pica; Other Specified Feeding and Eating Disorders (OSFED); Unspecified Feeding or Eating Disorder (UFED); Eating Disorder Not Otherwise Specified (EDNOS); Compulsive Overeating (CO); Loss of Control (LOC) Eating; and hyperphagia and/or binge-eating, associated with Prader-Willi Syndrome (PWS).

15 . The method according to claim 14 , wherein the method is for the prevention and/or treatment of Binge-Eating Disorder (BED).

16 . The pharmaceutical composition according to claim 8 , wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.5°, 12.5°, 13.7°, 14.2°, 14.6°, 18.4°, 21.4°, 21.8°, and 25.1°.

17 . The solid dosage form according to claim 9 , wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.80, 10.50, 12.50, 13.70, 14.20, 14.60, 18.40, 21.40, 21.80, and 25.1°.

18 . The method according to claim 14 , wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.50, 12.50, 13.70, 14.20, 14.60, 18.40, 21.40, 21.80, and 25.1°.

19 . The method according to claim 15 , wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.50, 12.50, 13.70, 14.20, 14.60, 18.40, 21.40, 21.80, and 25.1°.

20 . A method for preparing a solid pharmaceutical composition comprising (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone and at least one pharmaceutically acceptable carrier material, wherein the method comprises mixing a crystalline form of (4-Methyl-2-[1,2,3]triazol-2-yl-phenyl)-[(R)-3-(3-[1,2,3]triazol-2-yl-benzyl)-morpholin-4-yl]-methanone with the at least one pharmaceutically acceptable carrier material, and wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 10.5°, 14.2°, and 18.4°.

21 . The method according to claim 20 , wherein the crystalline form is characterized by the presence of peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 7.8°, 10.50, 12.50, 13.70, 14.20, 14.60, 18.40, 21.40, 21.80, and 25.1°.

Assignments (2)
PATENT SECURITY AGREEMENT Recorded Jun 25, 2026
From: IDORSIA PHARMACEUTICALS LTD
To: BIOPHARMA CREDIT PLC, AS COLLATERAL AGENT
Reel/Frame 076038/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 1, 2023
From: VON RAUMER, MARKUS
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 064458/0841 →