Avermectin derivatives

Details Avermectin derivatives Avermectin derivatives

1991-10-15

1993-08-31

Brown, Johnnie R.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Carbohydrate doai

536 71, 549264, 514450, C07H 1708, C07D49322, A61K 3170, A61K 31365

Patent

active

052409155

ABSTRACT:
There are disclosed avermectin derivatives which are avermectin modified at the 3- and 4-positions. The 3-hydroxy and 4-keto, epoxide and hydroxy (hydroxymethyl) derivatives and the 4-oxo compound are prepared from the natural avermectin by moving the 3,4-double bond exocyclic at 4 and forming a 3-hydroxy group. Osmolation gave an .alpha.,.beta.-diol across the double bond and cleavage of the diol provided the 4-oxo compound. The 4-oxo compound is epoxidized with an ylide reagent. The compounds are useful as anthelmintic agents and compositions for that use using the compounds as the active ingredient thereof are also described.

REFERENCES:
patent: Re32006 (1985-10-01), Chabala et al.
patent: Re32034 (1985-11-01), Chabala et al.
patent: 4199569 (1980-04-01), Chabala et al.
patent: 4200581 (1980-04-01), Fisher et al.
patent: 4201861 (1980-05-01), Mrozik et al.
patent: 4206205 (1980-06-01), Mrozik et al.
patent: 4289760 (1981-09-01), Mrozik et al.
patent: 4310519 (1982-01-01), Albers-Schonberg et al.
patent: 4427663 (1989-01-01), Mrozik
patent: 4457920 (1989-07-01), Mrozik
patent: 4916120 (1990-04-01), Roben et al.
patent: 4954484 (1990-09-01), Gehret
Chen, et al. (I) Abstr. Pap. Am. Chem. Soc. 186 Mtg. MBTD 28, 1983.
Chen, et al (II) ARch. Biochem. Biophys 269 pp. 544-547 (1989).
Schulman, et al (II) J. Antibiotic 38, pp. 1494-1498 (1985).
Schulman, et al (II) Antimicrobial Agents & Chemo. 31 pp. 744-747 (1986).
Fisher, et al (II) Macrolide Antibiotics Omura, Ed. Aca. Press, NY 553-606 (1984).
Davies-Reid, et al J. Org. Chem. 53 pp. 923-925 (1988).B. Fraser-Reid et al. "Avermectin Chemistry", J. Org. Chem., 53:4, pp. 923-925, 1988.
E. J. Corey et al. "Dimethyloxosulfonium Methylide and Dimethylsulfonium Methylide", JACS 87:6 pp. 1353-1364, 1965.
H. H. Szmant, Organic Chemistry, 1957.

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