Thiobarbituric acid derivatives and their use as anthelminthics

• US 4,670,441 A
• Filed: 07/05/1985
• Issued: 06/02/1987
• Est. Priority Date: 07/06/1984
• Status: Expired due to Fees

• Current Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Original Assignee: Ciba-Geigy Corporation (Novartis Ag)
• Inventors: Kuhne, Manfred, Gallay, Jean J.
• Primary Examiner(s): NOT, DEFINED
• Assistant Examiner(s): Kapner, Stephan M.
• Application Number:
  US06/751,715
• Time in Patent Office: 697 Days
• Field of Search: 544/300, 514/270
• US Class Current: 514/270
• CPC Class Codes: A61P 33/10 Anthelmintics
• CPC Class Codes: C07C 265/12 having isocyanate groups bound to carbon atoms of six-membered aromatic rings
• CPC Class Codes: C07C 65/24 polycyclic
• CPC Class Codes: C07D 213/643 2-Phenoxypyridines; Derivatives thereof
• CPC Class Codes: C07D 239/66 Thiobarbituric acids
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links

Abstract

The invention relates to novel 5-phenylcarbamoylthiobarbituric acid derivatives of the general formula ##STR1## wherein R₁ and R₂ are each independently C₁ -C₅ alkyl or methoxy,

R₃ is unsubstituted phenyl, unsubstituted pyridyl, or phenyl which is substituted by 1 to 3 identical or different members selected from the group consisting of C₁ -C₅ alkyl, C₁ -C₄ cyanoalkyl, halogen, nitro and C₁ -C₅ haloalkyl containing 1 to 5 halogen atoms, or is pyridyl which is substituted by 1 to 3 identical or different members selected from the group consisting of C₁ -C₅ alkyl, halogen, nitro and C₁ -C₅ haloalkyl containing 1 to 5 halogen atoms and

R₄ and R₅ are each independently hydrogen, halogen, C₁ -C₅ alkyl, C₁ -C₂ haloalkyl containing 1 to 3 halogen atoms, or are C₁ -C₃ -alkoxy or nitro,

and to the tautomers and salts thereof, as anthelmintics.

The compounds may be used by themselves or together with suitable carriers and further adjuvants for controlling helminths which are parasites of animals.

Claims

1. A 5-phenylcarbamoylthiobarbituric acid compound of the formula I ##STR20## wherein R₁ and R₂ are each independently C₁ -C₅ alkyl or methoxy,

R₃ is unsubstituted pyridyl or pyridyl which is substituted by 1 to 3 identical or different members selected from the group consisting of C₁ -C₅ alkyl, halogen, nitro and C₁ -C₅ haloalkyl having 1 to 5 halogen atoms, and

R₄ and R₅ are each independently hydrogen, halogen, C₁ -C₅ alkyl, C₁ -C₅ haloalkyl having 1 to 3 halogen atoms, or are C₁ -C₃ alkoxy or nitro,

or a tautomer or salt thereof.

2. A compound according to claim 1 wherein R₄ and R₅ are each independently hydrogen, halogen, C₁ -C₅ -alkyl, nitro or C₁ -C₂ -haloalkyl having 1 to 3 halogen atoms.

3. A compound according to claim 1, wherein R₁ is methyl, ethyl or methoxy, R₂ is methyl, R₃ is unsubstituted pyridyl or pyridyl which is substituted by 1 or 2 identical or different members selected from the group consisting of C₁ -C₅ alkyl, halogen, nitro and C₁ -C₅ haloalkyl containing 1 to 3 halogen atoms and R₄ and R₅ are each independently hydrogen, C₁ -C₅ alkyl or halogen.

4. A compound according to claim 1, wherein R₁ is methyl or methoxy, R₂ is methyl, R₃ is pyridyl which is substituted by methyl, chlorine, fluorine or trifluoromethyl and R₄ and R₅ are each independently hydrogen, C₁ -C₃ alkyl, chlorine or nitro.

5. A compound according to claim 1, wherein R₁ is methyl or methoxy, R₂ is methyl, R₃ is pyridyl which is substituted by methyl, chlorine or trifluoromethyl and R₄ and R₅ are each independently hydrogen or C₁ -C₃ alkyl and the radical --O--R₃ is in the 2- or 4-position.

6. A compound according to claim 1, wherein R₁ is methyl or ethyl, R₂ is methyl, R₃ is 2-pyridyl which is substituted by 1 or 2 identical or different members selected from the group consisting of fluorine, chlorine, nitro and trifluoromethyl, R₄ is hydrogen, chlorine, methyl, isopropyl or methoxy and R₅ is hydrogen, chlorine or methyl, or a triethylamine salt thereof.

7. A compound according to claim 1, wherein each of R₁ and R₂ is methyl, R₃ is 2-pyridyl which is substituted by 1 or 2 identical or different members selected from the group consisting of chlorine and trifluoromethyl, R₄ is hdyrogen, methyl, isopropyl or methoxy and R₅ is hydrogen or methyl, the radical --OR₃ being in meta or para-position to the nitrogen atom of the carbamoyl group, or a triethylamine salt thereof.

8. A compound according to claim 1, wherein each of R₁ and R₂ is methyl, R₃ is 2-pyridyl which is substituted by 1 or 2 identical or different members selected from the group consisting of chlorine and trifluoromethyl, R₄ is hydrogen or methoxy and R₅ is hydrogen, the radical --OR₃ being in meta- or para-position to the nitrogen atom of the carbamoyl group.

11. 1,3-Dimethyl-5-[4-methoxy-3-(3,5-dichloropyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid according to claim 1.

12. An anthelmintic composition which contains, as active ingredient, at least one compound of formula I according to claim 1, or a tautomer or salt thereof, together with carriers and further adjuvants.

13. A method of controlling parasitic helminths, which comprises administering to an animal an anthelmintically effective amount of a compound of formula I according to claim 1.

9. A compound selected from the group consisting of

1,3-dimethyl-5-[2-isopropyl-4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid,

1,3-dimethyl-5-[4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid, triethylamine salt,

1,3-dimethyl-5-[4-(3-chloro-5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid,

1,3-dimethyl-5-[2,6-dimethyl-4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid and

1,3-dimethyl-5-[4-(3,5-dichloropyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid.

10. 1,3-Dimethyl-5-[4-(5-trifluoromethylpyrid-2-yloxy)phenylcarbamoyl]-2-thiobarbituric acid.