Derivatives of docosahexaenoylethanolamide and uses thereof

Patent metadata

Field	Value
Publication number	US-9422308-B2
Application number	US-201314387410-A
Country	US
Kind code	B2
Filing date	Mar 15, 2013
Priority date	Apr 16, 2012
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The invention provides derivatives of DEA which have increased potency and hydrolysis resistance as compared to DEA, and compositions thereof, as well as methods of using these derivatives to promote neurogenesis, neurite growth and/or length, and/or promote synaptogenesis.

First claim

The invention claimed is:

1. A compound having the formula:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NR 1 R 2 , wherein the group NR 1 R 2 is selected from:

2. The compound of claim 1 , wherein the compound is:

3. The compound of claim 1 , wherein the compound is:

4. The compound of claim 1 , wherein the compound is:

5. The compound of claim 1 , wherein the compound is:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NHCH 2 CH 2 OCH 3 .

6. A composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

7. A method of increasing neurite growth and/or length within a mammal, the method comprising administering to the mammal an effective amount of a compound, wherein neurite growth and/or length is increased in the mammal, and wherein the compound has the formula:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NR 3 R 2 , wherein the group NR 3 R 2 is selected from:

8. The method of claim 7 , wherein the mammal has a neurological condition selected from traumatic brain injury, spinal cord injury, peripheral nerve injury, stroke, multiple sclerosis, autism, Alzheimer's disease, Huntington's disease, Parkinson's disease, amyotrophic lateral sclerosis.

9. The method of claim 7 , wherein the compound is provided in a pharmaceutically acceptable composition.

10. A method of increasing neurogenesis within a mammal, the method comprising administering to the mammal an effective amount of a compound, wherein neurogenesis is increased in the mammal, and wherein the compound has the formula:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NR 1 R 2 , wherein the group NR 1 R 2 is selected from:

11. The method of claim 10 , wherein the mammal has a neurological condition selected from traumatic brain injury, spinal cord injury, peripheral nerve injury, stroke, multiple sclerosis, autism, Alzheimer's disease, Huntington's disease, Parkinson's disease, amyotrophic lateral sclerosis.

12. The method of claim 10 , wherein the compound is provided in a pharmaceutically acceptable composition.

13. The method of claim 7 , wherein the compound has the formula:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NR 1 R 2 , wherein the group NR 1 R 2 is selected from:

14. The method of claim 10 , wherein the compound has the formula:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NR 1 R 2 , wherein the group NR 1 R 2 is selected from:

15. The method of claim 7 , wherein the compound is:

16. The method of claim 7 , wherein the compound is:

17. The method of claim 7 , wherein the compound:

18. The method of claim 7 , wherein the compound is:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NHCH 2 CH 2 OCH 3 .

19. The method of claim 10 , wherein the compound is:

20. The method of claim 10 , wherein the compound is:

21. The method of claim 10 , wherein the compound is:

22. The method of claim 10 , wherein the compound is:
CH 3 CH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 HC═CHCH 2 CH 2 CO—NHCH 2 CH 2 OCH 3 .

Assignees

• Us Health

Inventors

• Kim Hee-Yong
• Marugan Juan Jose
• Englund Erika E
• Patnaik Samarjit

Classifications

• C07C233/09

  with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton · CPC title

• C07D213/40

  Acylated substituent nitrogen atom · CPC title

• C07C255/29

  containing cyano groups and acylated amino groups bound to the carbon skeleton · CPC title

• C07D205/04

  having no double bonds between ring members or between ring members and non-ring members · CPC title

• C07D495/04 Primary

  Ortho-condensed systems · CPC title