IP Library Granted Patent US 12685731
Granted Patent B2
US 12685731 · App. 17/040,893 · Granted Jul 21, 2026

Organic compounds

Inventors: Peng Li (New Milford, NJ); Robert Davis (San Diego, CA)
Assignee: INTRA-CELLULAR THERAPIES, INC.
A61K31/4985A61K9/0019A61K45/06C07B59/002C07D471/16C07B2200/05
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Quick Facts
Patent No.
US 12685731
App. No.
17/040,893
Granted
Jul 21, 2026
Kind
B2
Abstract

The invention relates to particular substituted deuterated heterocycle fused gamma-carbolines, their prodrugs, in free, solid, pharmaceutically acceptable salt and/or substantially pure form as described herein, pharmaceutical compositions thereof, and methods of use in the treatment of diseases involving 5-HT 2A receptor, serotonin transporter (SERT) and/or pathways involving dopamine D 1 /D 2 receptor signaling systems, and/or the treatment of residual symptoms.

Claims (16)

1 . A compound of formula II,

wherein R 1 and R 2 are both D, in solid mono-tosylate salt form.

2 . The compound according to claim 1 , wherein the compound has greater than 90% incorporation of deuterium at the indicated deuterium positions of the structure.

3 . A pharmaceutical composition comprising the compound according to claim 1 in combination or association with a pharmaceutically acceptable diluent or carrier.

4 . The compound according to claim 1 , wherein the compound of Formula II is in crystalline form.

5 . The compound according to claim 1 , wherein the compound of Formula II is in amorphous form.

6 . The compound according to claim 1 , wherein the compound has greater than 95% incorporation of deuterium at the indicated deuterium positions of the structure.

7 . The pharmaceutical composition according to claim 3 , wherein the composition is a tablet or capsule.

8 . The compound according to claim 4 , wherein the compound has greater than 90% incorporation of deuterium at the indicated deuterium positions of the structure.

9 . The compound according to claim 4 , wherein the compound has greater than 95% incorporation of deuterium at the indicated deuterium positions of the structure.

10 . A pharmaceutical composition comprising the compound according to claim 4 in combination or association with a pharmaceutically acceptable diluent or carrier.

11 . The pharmaceutical composition according to claim 10 , wherein the composition is a tablet or capsule.

12 . The compound according to claim 5 , wherein the compound has greater than 90% incorporation of deuterium at the indicated deuterium positions of the structure.

13 . The compound according to claim 5 , wherein the compound has greater than 95% incorporation of deuterium at the indicated deuterium positions of the structure.

14 . A pharmaceutical composition comprising the compound according to claim 5 in combination or association with a pharmaceutically acceptable diluent or carrier.

15 . The pharmaceutical composition according to claim 14 , wherein the composition is a tablet or capsule.