Deuterated analogs of D-serine and uses thereof

• US 10,668,036 B2
• Filed: 07/02/2019
• Issued: 06/02/2020
• Est. Priority Date: 11/22/2017
• Status: Active Grant

• Current Assignee: Sun Pharmaceutical Industries, Inc. (Sun Pharmaceutical Industries Limited)
• Original Assignee: Concert Pharmaceuticals Inc. (Sun Pharmaceutical Industries Limited)
• Inventors: Doller, Dario, Brummel, Christopher L., Liu, Julie F., Tung, Roger D.
• Primary Examiner(s): Lundgren, Jeffrey S
• Assistant Examiner(s): Schmitt, Michael J
• Application Number:
  US16/459,916
• Publication Number:
  US 20190328692A1
• Time in Patent Office: 336 Days
• Field of Search: None
• CPC Class Codes: A61K 31/197 the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid carnitine A61K31/205
• CPC Class Codes: A61K 31/198 Alpha-amino acids, e.g. alanine or edetic acid [EDTA] betaine A61K31/205; proline A61K31/401; tryptophan A61K31/405; histidine A61K31/4172; peptides not degraded to individual amino acids A61K38/00
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia

Abstract

This disclosure relates to deuterated D-serine, pharmaceutically acceptable salts thereof, analogs and prodrugs thereof, pharmaceutical compositions thereof, and methods of use.

Claims

1. A method of treating schizophrenia, the method comprising administering to a subject in need thereof an effective amount of Compound 100:

2. The method of claim 1, wherein the method further comprises administering an antipsychotic therapeutic agent to the subject.

3. The method of claim 1, wherein in Compound 100, the position designated specifically as deuterium has at least 95% incorporation of deuterium.

4. The method of claim 1, wherein in Compound 100, the position designated specifically as deuterium has at least 97% incorporation of deuterium.

5. The method of claim 1, wherein in Compound 100, any atom not designated as deuterium is present at its natural isotopic abundance.

6. The method of claim 1, wherein Compound 100 is administered in a pharmaceutical composition that is suitable for oral administration.

7. The method of claim 1, wherein the method comprises administering an amount of Compound 100 in the range of 1 g to 4 g.

8. The method of claim 1, wherein less than 2% of the enantiomer of Compound 100 is present.

9. The method of claim 1, wherein the method comprises administering an amount of Compound 100 in the range of 1 to 4 g per day.