Amino amides, peptides and peptidomimetics

• US 7,247,701 B2
• Filed: 09/14/2005
• Issued: 07/24/2007
• Est. Priority Date: 04/01/2002
• Status: Expired due to Fees

• Current Assignee: University of Southern California
• Original Assignee: University of Southern California
• Inventors: Petasis, Nicos A., Yao, Xin
• Primary Examiner(s): Chism; B. Dell
• Application Number:
  US11/227,986
• Publication Number:
  US 20060063206A1
• Time in Patent Office: 678 Days
• Field of Search: None
• US Class Current: 530/300
• CPC Class Codes: C07C 231/12 by reactions not involving the formation of carboxamide groups
• CPC Class Codes: C07D 333/24 Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

Synthetic methods and compounds involving amino amides, peptides and peptidomimetics. Amino amide derivatives are prepared via the one-step three-component reaction of a glyoxamide, an amine, and an organoboron derivative. Conversion of the product to another glyoxamide intermediate allows the iterative use of this chemistry for the synthesis of peptides and peptidomimetics.

Claims

1. A method for preparing a compound represented by formula 5:

2. The method of claim 1, further comprising:

converting the amino amide of formula 5 to an amino amide of formula 6

3. The method of claim 1, wherein one of R¹, R², R³, Ra, Rb, Rw, X and Y is connected to a polymeric chain or other solid phase material.

4. The method of claim 1, wherein the amino amide of formula 5 is formed as a member of a combinatorial library.

5. The method of claim 3, wherein the amino amide of formula 5 is formed as a member of a combinatorial library.

6. The method of claim 1, wherein the compound prepared by the method is represented by formula 17′

;

7. The method of claim 6, wherein one of R¹, R², R³, R⁴, R⁹, R¹⁰, R¹¹, R¹², Rw, X or Y is connected to a polymeric chain or other solid phase material.

8. The method of claim 6, wherein the compound of formula 17 is formed as a member of a combinatorial library.

9. The method of claim 7, wherein the compound of formula 17 is formed as a member of a combinatorial library.

10. The method of claim 1, wherein Rw is hydrogen.

11. The method of claim 6, wherein Rw is hydrogen.