Derivatives of antibiotic X-537A

Abstract

Compound of the formula ##STR1## where R 1 is hydrogen, lower alkyl, phenyl, or phenyl substituted by halogen, nitro or lower alkyl; R 2 is hydrogen; lower alkyl; lower alkanoyl; benzoyl; benzoyl substituted by halogen, nitro or lower alkyl; or R 3 is hydrogen, halogen; nitro, amino, loweralkylamido or lower alkylamino; R 4 is --OH, =O or =NOH which compound is useful as a coccidiostatic agent and as an anti-bacterial agent.

We claim: 
     
       1. A compound selected from the group of compounds of the formula ##STR10## wherein R 1  is selected from the group consisting of hydrogen, .[.lower alkyl.]., phenyl, and phenyl substituted by a member of the group consisting of halogen, nitro and lower alkyl; R 2  is selected from the group consisting of hydrogen, lower alkyl, lower alkanoyl, ##STR11## benzoyl, and benzoyl substituted by a member of the group consisting of halogen, nitro and lower alkyl; R 3  is selected from the group consisting of hydrogen, halogen, nitro, amino, lower alkylamido and lower alkylamino; R 4  is selected from the group consisting of --OH, ═O and ═N--OH, provided that at least one of R 1 , R 2  and R 3  is other than hydrogen, or R 4  is other than ═O; and the pharmaceutically acceptable alkali metal, alkaline earth metal and ammonium salts thereof. 
     
     
       2. The compound of claim 1 which is 5-nitro-3-methyl-6-{7-ethyl .Iadd.4-hydroxy.Iaddend.-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl] -4-.[.heptenyl.]..Iadd.heptyl.Iaddend.}salicylic acid. 
     
     
       3. A compound selected from the group of compounds of the formula ##STR12## wherein R 2  ' is hydrogen or lower alkanoyl, R 3  ' is hydrogen or halogen, and at least one of R 2  ' or R 3  ' is other than hydrogen and the pharmaceutically acceptable alkali metal, alkaline earth metal and ammonium salts thereof. 
     
     
       4. A compound of claim 3 wherein R 2  ' is lower alkanoyl and R 3  ' is hydrogen. 
     
     
       5. The compound of claim 4 which is 3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}acetyl salicylic acid. 
     
     
       6. The compound of claim 4  which is 3-methyl-2-propionyloxy-6-{-7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}benzoic acid. 
     
     
       7. The compound of claim 4 which is 2-butyryloxy-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-.Badd..[.3-5.]..Baddend. .Iadd.3-methyl-5.Iaddend.-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}benzoic acid. 
     
     
       8. A compound of claim 3 wherein R 2  ' is hydrogen and R 3  ' is halogen. 
     
     
       9. The compound of claim 8 which is 5-bromo-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}salicylic acid. 
     
     
       10. The compound of claim 8 which is 5-chloro-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}salicylic acid. 
     
     
       11. The compound of claim 8 which is 5-iodo-3-methyl-6-{7-ethyl-4-hydroxy-3,5-dimethyl-6-oxo-7-[5-ethyl- .[.2-methyl.]..Iadd.3-methyl.Iaddend.-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]heptyl}salicylic acid. 
     
     
       12. A compound selected from the group of compounds of the formula ##STR13## wherein R 1  is selected from the group consisting of hydrogen, lower alkyl, phenyl, and phenyl substituted by a member of the group consisting of halogen, nitro and lower alkyl; R 2  is selected from the group consisting of hydrogen, lower alkyl, lower alkanoyl, ##STR14## benzoyl, and benzoyl substituted by a member of the group consisting of halogen, nitro and lower alkyl, and R 3  is selected from the group consisting of hydrogen, halogen, nitro, amino, lower alkylamido and lower alkylamino and the pharmaceutically acceptable alkali metal, alkaline earth metal and ammonium salts thereof. 
     
     
       13. The compound of claim 12 which is 5-bromo-3-methyl-6-{7-ethyl-3,5-dimethyl-6-oxo-7-[5-ethyl-3-methyl-5-(5-ethyl-5-hydroxy-6-methyl-2-tetrahydropyranyl)-2-tetrahydrofuryl]-4-heptenyl}salicylic acid.