Process for the production of 2,5 -diketopiperazines,2,5-diketopiperazines , dipeptides and their use thereof

• US 20040024180A1
• Filed: 05/28/2003
• Published: 02/05/2004
• Est. Priority Date: 04/20/2000
• Status: Abandoned Application

• Current Assignee: Degussa AG (Rag-Stiftung)
• Original Assignee: Degussa AG (Rag-Stiftung)
• Inventors: Drauz, Karlheinz, Knaup, Gunter
• Application Number:
  US10/258,029
• Publication Number:
  US 20040024180A1
• Time in Patent Office: Days
• US Class Current: 530/331
• CPC Class Codes: C07D 241/08 with oxygen atoms directly attached to ring carbon atoms
• CPC Class Codes: C07K 5/06086 with the first amino acid being basic
• CPC Class Codes: C07K 5/06191 containing heteroatoms different from O, S, or N
• CPC Class Codes: C07K 5/12 Cyclic peptides with only normal peptide bonds in the ring

Abstract

Process for the production of 2,5-diketopiperazines of general formula I,

by heating dipeptides of general formula II

in an organic solvent whilst removing water by distillation.

Novel 2,5-diketopiperazines, dipeptides and their use.

Claims

1. Process for the production of 2,5-diketopiperazines of general formula I,

2. Process according to claim 1,

characterised in that

an organic solvent is used, which forms an azeotrope with water.

3. Process according to claim 2,

characterised in that

n-butanol is used as the organic solvent.

4. Process according to one or more of the preceding claims,

characterised in that

the reaction is carried out at temperatures of 80-150°

C.

5. Process according to one or more of the preceding claims,

characterised in that

the reaction is carried out in a pH range of 3 to 7.

6. Process according to one or more of the preceding claims,

characterised in that

the dipeptides of formula (II) are used in the reaction in the form of an aqueous solution.

12. Use of the compounds produced according to claim 1 in the synthesis of bio-active compounds.

7. 2,5-diketopiperazines of general formula III,

8. 2,5-diketopiperazine according to claim 7,

characterised in that

it is present in the (S,S) configuration.

9. Dipeptides of general formula (IV),

10. Dipeptide according to claim 9,

characterised in that

it is present in the (S,S) configuration.

11. Use of the compounds according to one or more of claims 7 to 10 for the production of cyclo[Lys-Lys].