Heteroatom containing cyclic dimers

• US 9,011,832 B2
• Filed: 02/08/2013
• Issued: 04/21/2015
• Est. Priority Date: 02/09/2012
• Status: Active Grant

• Current Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Original Assignee: Novus International, Inc. (Nippon Soda Company Limited)
• Inventors: Arhancet, Graciela B., Mahoney, Matthew, Wang, Xiaojun
• Primary Examiner(s): Jarrell, Noble
• Assistant Examiner(s): Kenyon, John S
• Application Number:
  US13/763,101
• Publication Number:
  US 20130209392A1
• Time in Patent Office: 802 Days
• US Class Current: 424/78.38
• CPC Class Codes: A23K 20/10 Organic substances
• CPC Class Codes: A23K 50/10 for ruminants
• CPC Class Codes: A23K 50/75 for poultry
• CPC Class Codes: C07D 265/33 Two oxygen atoms, in positions 3 and 5
• CPC Class Codes: C07D 319/12 not condensed with other rings
• CPC Class Codes: C08G 63/6882 derived from hydroxy carboxylic acids
• CPC Class Codes: C08G 63/85 Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof C08G63/823 takes precedence
• CPC Class Codes: C08G 67/00 Macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing oxygen or oxygen and carbon, not provided for in groups C08G2/00 - C08G65/00
• CPC Class Codes: C08G 75/02 Polythioethers
• CPC Class Codes: C08L 67/00 Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain of polyester-amides C08L77/12; of polyester-imides C08L79/08; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence

Abstract

The present invention provides cyclic dimers of alpha acids and polymers derived therefrom. Also provided are processes for preparing and methods of using the cyclic dimers and the polymers derived from the cyclic dimers.

Claims

1. A compound of Formula (I):

2. The compound of claim 1, wherein X¹ and X² are oxygen.

3. The compound of claim 1, wherein X¹ is nitrogen and X² is oxygen.

4. The compound of claim 1, wherein X¹ is oxygen and X² is nitrogen.

5. The compound of claim 1, wherein Z is sulfur.

6. The compound of claim 1, wherein Z is selenium.

7. A compound of Formula (Ia):

8. The compound of claim 7, wherein X¹ and X² are oxygen.

9. The compound of claim 7, wherein X¹ is nitrogen and X² is oxygen.

10. The compound of claim 7, wherein X¹ is oxygen and X² is nitrogen.

11. The compound of claim 7, wherein Y and Z are sulfur.

12. The compound of claim 7, wherein Y and Z are selenium.

13. A compound of Formula (IIa):

14. The compound of claim 13, wherein Z and Y are sulfur.

15. The compound of claim 13, wherein Z and Y are selenium.

16. The compound of claim 13, wherein the compound is a compound of Formula (V):

17. The compound of claim 16, wherein the compound hydrolyzes in an aqueous solution at a pH below 5.0.

18. The compound of claim 16 and at least one nutritive agent or at least one pharmaceutical agent.

19. The compound of claim 16, wherein the compound is chosen from D-, L-, or meso-stereochemistry.

20. A compound of Formula (II):

21. A compound of Formula (IIb):

22. The compound of claim 21, wherein R¹ is methyl.

23. The compound of claim 21, where in R⁶ is alkyl.

24. A compound of Formula (III):

25. The compound of claim 24, wherein Z is sulfur.

26. The compound of claim 24, wherein Z is sulfoxide.

27. The compound of claim 24, wherein Z is sulfone.

28. The compound of claim 24, wherein Z is selenium.

29. The compound of Formula (V):

30. The compound of claim 29, wherein the compound is chosen from D-, L-, or meso-stereochemistry.