# US 5,702,924 A · Process for preparing antiparasitic agents

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- Number: US 5,702,924 A
- Document ID: US5702924A
- Status: Granted
- Kind: A
- Application number: 07/647,674
- Filed: 1991-01-25
- Granted: 1997-12-30
- Earliest claimed: 1987-11-14
- Assignees: Pfizer Inc.
- Inventors: Christopher J. Dutton; Stephen P. Gibson; Shih-Jen E. Lee
- Web page: https://patentgrep.com/patent/US5702924A

## CPC

- C07H 19/01: sharing oxygen
- A61P 33/00: Antiparasitic agents
- Y10S 435/886: Streptomyces
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Compounds of the formula: ##STR1## wherein X represents a single or a double bond; R.sup.1 is H or OH; provided that when X is a single bond, R.sup.1 is H or OH, and when X is a double bond, R.sup.1 is absent; R.sup.2 is H, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, alkoxy-alkyl or alkylthioalkyl containing from 1 to 6 carbon atoms in each alkyl or alkoxy group, wherein any of said alkyl, alkoxy alkenyl or alkynyl groups may be substituted by one or more halo atoms; or a C.sub.3 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkenyl group, either of which may be substituted by methylene or one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a group of the formula SR.sup.5 wherein R.sup.5 is C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, phenyl or substituted phenyl wherein the substituent is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo, or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; R.sup.3 is hydrogen or methyl; and R.sup.4 is H or a 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy group of the formula ##STR2## with the proviso that when R.sup.4 and R.sup.1 are both H and the double bond is absent, R.sup.2 is not H or CH.sub.3, are broad spectrum antiparasitic agents having utility as anthelmintics, ectoparasiticides, insecticides and acaricides.

## Claims

### Claim 1

A process for preparing a compound of the formula ##STR5## wherein X represents a single or double bond; R.sup.1 is OH; provided that when X is a single bond, R.sup.1 is OH, and when X is a double bond, R.sup.1 is absent;
R.sup.2 is H, C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, alkoxyalkyl or alkylthioalkyl containing from 1 to 6 carbon atoms in each alkyl or alkoxy group, wherein any of said alkyl, alkoxy alkenyl or alkynyl groups may be substituted by one or more halo atoms; or a C.sub.3 -C.sub.8 cycloalkyl or C.sub.5 -C.sub.8 cycloalkenyl group, either of which may be substituted by methylene or one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms; or a group of the formula SR.sup.5 wherein R.sup.5 is C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.8 alkenyl, C.sub.2 -C.sub.8 alkynyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.5 -C.sub.8 cycloalkenyl, phenyl or substituted phenyl wherein the substituent is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo, or a 3 to 6 membered oxygen or sulphur containing heterocyclic ring which may be saturated, or fully or partially unsaturated and which may be substituted by one or more C.sub.1 -C.sub.4 alkyl groups or halo atoms;
R.sup.3 is hydrogen or methyl;
and R.sup.4 is a 4'-(alpha-L-oleandrosyl)-alpha-L-oleandrosyloxy group of the formula ##STR6## which comprises fermenting a Streptomyces avermitilis mutant organism ATCC 53567 or 53568, in the presence of a carboxylic acid of the formula R.sup.2 CH.sub.2 CO.sub.2 H, wherein R.sup.2 is as previously defined, or a salt, ester, or amide thereof or oxidative precursor therefor, and isolating the compound of formula (I).