Uracil derivatives

• US 4,267,326 A
• Filed: 02/26/1979
• Issued: 05/12/1981
• Est. Priority Date: 09/06/1976
• Status: Expired due to Term

• Current Assignee: Mitsui Toatsu Kagaku Kabushiki Kaisha
• Original Assignee: Mitsui Chemicals Incorporated (Mitsui Chemicals)
• Inventors: Mori, Haruki, Ozaki, Shoichiro, Ike, Yoshimasa, Ishikawa, Katsutoshi
• Primary Examiner(s): Coughlan, Jr., Paul M.
• Application Number:
  US06/015,149
• Time in Patent Office: 806 Days
• Field of Search: 544/313
• US Class Current: 544/313
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: C07D 239/553 with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil

Abstract

New uracil derivatives of the general formula: ##STR1## wherein R¹ stands for a hydrogen atom or a grouping of the formula: ##STR2## R² for a hydrogen atom, an alkyl group or a phenyl group and R³ for an alkyl group or a phenyl group, with the proviso that when both R¹ and R² stand for a hydrogen atom, R³ stands for a phenyl group or a straight chain alkyl group with 3˜11 carbon atoms, that when R¹ stands for a hydrogen atom and R² for methyl group, R³ stands for an alkyl group with at least 2 carbon atoms or a phenyl group, and that when R¹ stands for a hydrogen atom and R³ for methyl group, R² stands for an alkyl group with at least 2 carbon atoms or a phenyl group. These uracil derivatives are prepared by reacting 5-fluorouracil with an α-haloalkyl carboxylate or with an aldehyde diacylate or by hydrolyzing a 1,3-bis(acyloxymethyl)-5-fluorouracil with an acid or alkali. These uracil derivatives are useful as improved anti-tumor agents especially for oral administration and injection.

Claims

1. Uracil derivatives of the general formula:

##STR16## wherein;

R¹ stands for a hydrogen atom;

R² is a hydrogen atom and R³ is phenyl or straight chain alkyl with 5-11 carbon atoms;

or

R² is n-propyl and R³ is methyl;

or

R² is methyl and R³ is n-butyl;

or

R² is phenyl and R³ is methyl.

2. 1-Caproyloxymethyl-5-fluorouracil.

3. 1-Enanthoyloxymethyl-5-fluorouracil.

4. 1-Capryloxymethyl-5-fluorouracil.

5. 1-Lauroyloxymethyl-5-fluorouracil.

6. 1-Benzoyloxymethyl-5-fluorouracil.

7. 1-(α

-acetoxy-α

-phenyl)methyl-5-fluorouracil.