2-Substituted cyclic AMP derivatives

• US 3,917,583 A
• Filed: 02/07/1973
• Issued: 11/04/1975
• Est. Priority Date: 08/04/1972
• Status: Expired due to Term

• Current Assignee: Viratek, Inc. (Bausch Health Cos., Inc.)
• Original Assignee: Dennis A. Shuman, Rich B. Meyer
• Inventors: Meyer, Rich B., Shuman, Dennis A.
• Primary Examiner(s): Brown, Johnnie R.
• Application Number:
  US05/330,306
• Time in Patent Office: 1,000 Days
• Field of Search: 260/211.5R
• US Class Current: 536/26.12
• CPC Class Codes: C07H 19/052 Imidazole radicals
• CPC Class Codes: C07H 19/20 with the saccharide radical esterified by phosphoric or polyphosphoric acids

Abstract

2-Substituted derivatives of cyclic AMP and a process of making the same are disclosed which are useful to inhibit the enzyme phosphodiesterase, to activate protein kinase and steriodogenesis, and as intermediates in the synthesis process.

Claims

1. A COMPOUND OF THE STRUCTURE:

2. The compound of claim 1 in which X is N, Z is NH2 and Y is CR1.

3. The compound of claim 1 in which R1 is C1 C6 alkyl.

4. The compound of claim 1 in which R2 is C1 to C6 alkyl.

5. The compound of claim 1 in which X and Y are N.

6. The compound of claim 5 in which Z is NH.

7. A process of synthesizing 2-substituted derivatives of cyclic AMP comprising condensing 5-amino-1- Beta -D-ribofuranosylimidazole-4-carboxamidine 3'"'"''"'"',5'"'"''"'"'-cyclic phosphate with a carboxaldehyde selected from the group consisting of alkyl, aryl, aralkyl and pyridyl carboxaldehyde in refluxing alcohol to provide the corresponding 2-substituted adenine derivative.

8. The process of claim 7 in which the carboxaldehyde is a C1 to C8 alkyl carboxaldehyde and condensation occurs in refluxing ethanol for from about 5 minutes to approximately 1 hour.

9. The process of claim 7 in which the carboxaldehyde is benzaldehyde and condensation occurs in refluxing ethanol for from about 5 minutes to about 1 hour.

10. The process of claim 7 in which the carboxaldehyde is pyridine-2-carboxaldehyde and condensation occurs in refluxing ethanol for from about 5 minutes to about 1 hour.

11. A process of synthesizing 2-substituted derivatives of cyclic AMP comprising condensing 5-amino-1- Beta -D-ribofuranosylimidazole-4-carboxamidine 3'"'"''"'"' ,5'"'"''"'"'-cyclic phosphate with a carboxaldehyde selected from the group consisting of alkyl, aryl, aralkyl and pyridyl carboxaldehyde in an aqueous organic water-miscible solvent, and reacting such condensation product with a dehydrogenation reagent to provide the corresponding 2-substituted adenine derivative.