Isomeric O-phosphonylmethyl derivatives of enantiomeric and racemic 9-(2,3-dihydroxypropyl)adenine

• US 4,659,825 A
• Filed: 01/06/1984
• Issued: 04/21/1987
• Est. Priority Date: 01/06/1983
• Status: Expired due to Term

• Current Assignee: Institute Of Organic Chemistry And Biochemistry Of The Ascr, V.V.I.
• Original Assignee: Ceskoslovenska Akademie
• Inventors: Slama, Karel, Holy, Antonin, Rosenberg, Ivan
• Primary Examiner(s): Berch, Mark L.
• Assistant Examiner(s): Rivers, Diana G.
• Application Number:
  US06/568,719
• Time in Patent Office: 1,201 Days
• Field of Search: 544/244
• US Class Current: 544/244
• CPC Class Codes: A01N 57/20 containing acyclic or cycloaliphatic radicals
• CPC Class Codes: A01N 57/24 containing heterocyclic radicals
• CPC Class Codes: C07F 9/3808 Acyclic saturated acids which can have further substituents on alkyl
• CPC Class Codes: C07F 9/65616 containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
• CPC Class Codes: C07H 19/00 Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
• CPC Class Codes: C07H 19/16 Purine radicals

Abstract

This invention relates to isomeric O-phosphonylmethyl derivatives of the formula I ##STR1## wherein R⁵ designates an adenin-9-yl moiety, R⁴ are alternately a hydrogen atom and a --CH₂ P(O)(OH)₂ group, and the configuration at the carbon atom in the position 2 is S, R or RS.

The compounds according to the invention are biologically active as inhibitors of metabolic processes and in organism they are stable towards enzymes, cleaving phosphomonoester bonds.

The said compounds exhibit also chemosterilizing action on insects.

Claims

1. Isomeric O-phosphonymethyl derivatives of enantiomeric and racemic vicinal diols having the formula I ##STR4## wherein one R⁴ is a hydrogen atom and the other R⁴ is a --CH₂ P(O)(OH)₂ group, and the configuration at the carbon atom in the position 2 is R, S or RS.