Bicyclic heteroaryl derivatives and preparation and uses thereof

• US 10,640,476 B2
• Filed: 09/30/2019
• Issued: 05/05/2020
• Est. Priority Date: 03/30/2017
• Status: Active Grant

• Current Assignee: XWPharma Ltd.
• Original Assignee: XW Laboratories, Inc.
• Inventors: Xiang, Jia-Ning, Xu, Xuesong, Zhou, Wei
• Primary Examiner(s): Stockton, Laura L
• Application Number:
  US16/587,571
• Publication Number:
  US 20200017456A1
• Time in Patent Office: 218 Days
• CPC Class Codes: A61K 31/095 Sulfur, selenium, or tellurium compounds, e.g. thiols
• CPC Class Codes: A61K 31/41 having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
• CPC Class Codes: A61K 31/423 condensed with carbocyclic rings
• CPC Class Codes: A61K 31/425 Thiazoles
• CPC Class Codes: A61K 31/428 condensed with carbocyclic rings
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61K 9/0019 Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner non-active ingredients are additionally classified in A61K47/00
• CPC Class Codes: A61K 9/0053 Mouth and digestive tract, i.e. intraoral and peroral administration rectal administration A61K9/0031
• CPC Class Codes: A61K 9/7023 Transdermal patches and similar drug-containing composite devices, e.g. cataplasms galenical aspects of iontophoretic devices A61K9/0009; microneedle arrays A61K9/0021; buccal patches A61K9/006
• CPC Class Codes: A61P 23/00 Anaesthetics
• CPC Class Codes: A61P 25/16 Anti-Parkinson drugs
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 235/30 Nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 263/58 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
• CPC Class Codes: C07D 277/82 Nitrogen atoms
• CPC Class Codes: C07D 293/12 Selenazoles; Hydrogenated selenazoles

Abstract

The present invention relates compounds of Formula (A), as well as their preparation and uses, and further relates pharmaceutical compositions comprising these compounds and their uses as modulators of dysfunctional glutamate transmission. The present invention also relates to uses of the compounds or pharmaceutical compositions in treating or preventing certain neurological and psychiatric disorders and diseases as well as cancer in humans.

Claims

1. The compound 6-(pentafluoro-λ

⁶-sulfaneyl)benzo[d]thiazol-2-amine (I);

5. A pharmaceutical composition comprising:

a therapeutically effective amount of the compound of claim 1 or a pharmaceutically acceptable salt thereof; and

a pharmaceutically acceptable excipient, carrier, adjuvant, solvent, or a combination of any of the foregoing.

6. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is a transdermal formulation.

7. The pharmaceutical composition of claim 5, wherein the pharmaceutical composition is an oral formulation.

2. The compound 6-(pentafluoro-λ

⁶-sulfaneyl)benzo[d][1,3]selenazol-2-amine (V);

8. A pharmaceutical composition comprising:

a therapeutically effective amount of the compound of claim 2 or a pharmaceutically acceptable salt thereof; and

a pharmaceutically acceptable excipient, carrier, adjuvant, solvent, or a combination of any of the foregoing.

9. The pharmaceutical composition of claim 8, wherein the pharmaceutical composition is a transdermal formulation.

10. The pharmaceutical composition of claim 8, wherein the pharmaceutical composition is an oral formulation.

3. The compound 6-(trifluoromethyl)benzo[d][1,3]selenazol-2-amine (VI):

11. A pharmaceutical composition comprising:

a therapeutically effective amount of the compound of claim 3 or a pharmaceutically acceptable salt thereof; and

a pharmaceutically acceptable excipient, carrier, adjuvant, solvent, or a combination of any of the foregoing.

12. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is a transdermal formulation.

13. The pharmaceutical composition of claim 11, wherein the pharmaceutical composition is an oral formulation.

4. The compound 6-((trifluoromethyl)thio)benzo[d][1,3]selenazol-2-amine (IX):

14. A pharmaceutical composition comprising:

a therapeutically effective amount of the compound of claim 4 or a pharmaceutically acceptable salt thereof; and

a pharmaceutically acceptable excipient, carrier, adjuvant, solvent, or a combination of any of the foregoing.

15. The pharmaceutical composition of claim 14, wherein the pharmaceutical composition is a transdermal formulation.

16. The pharmaceutical composition of claim 14, wherein the pharmaceutical composition is an oral formulation.