Monosaccharide and aglycone derivatives of C-076

• US 4,206,205 A
• Filed: 04/17/1978
• Issued: 06/03/1980
• Est. Priority Date: 10/03/1977
• Status: Expired due to Term

• Current Assignee: Merck & Co., Inc.
• Original Assignee: Merck & Co., Inc.
• Inventors: Mrozik, Helmut H., Albers-Schonberg, George
• Primary Examiner(s): Brown, Johnnie R.
• Application Number:
  US05/896,867
• Time in Patent Office: 778 Days
• Field of Search: 536/9, 536/17, 536/4, 424/180, 424/279, 260/343.41
• US Class Current: 514/30
• CPC Class Codes: A01N 43/90 having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
• CPC Class Codes: C07D 493/22 in which the condensed system contains four or more hetero rings
• CPC Class Codes: C07H 17/08 Hetero rings containing eight or more ring members, e.g. erythromycins
• CPC Class Codes: C12P 17/181 Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
• CPC Class Codes: C12P 19/623 Avermectin; Milbemycin; Ivermectin; C-076

Abstract

Derivatives of C-076 are described in which the C-076 molecule, a series of macrolides in which one of the substituents is a 4-(α-L-oleandrosyl)-α-L-oleandrose has one or both of the carbohydrate moieties removed therefrom. The compounds thus produced have profound anthelmintic, insecticidal, ectoparasiticidal and acaracidal activity and compositions for such use are also disclosed.

Claims

1. A compound having the formula:

##STR3## wherein R is hydrogen or α

-L-oleandrosyl of the structure;

##STR4## and wherein the broken line indicates a single or a double bond;

R₁ is hydroxy and is present only when said broken line indicates a single bond;

R₂ is iso-propyl or sec-butyl; and

R₃ is methoxy or hydroxy.

2. The compound of claim 1 wherein R₂ is iso-propyl.

3. The compound of claim 1 wherein R₂ is sec-butyl.

4. The compound of claim 3 which is C-076 Ala monosaccharide.

5. The compound of claim 3 which is C-076 Ala aglycone.

6. The compound of claim 3 which is C-076 A2a monosaccharide.

7. The compound of claim 3 which is C-076 A2a aglycone.

8. The compound of claim 3 which is C-076 B1a monosaccharide.

9. The compound of claim 3 which is C-076 B1a aglycone.

10. The compound of claim 3 which is C-076 B2a monosaccharide.

11. The compound of claim 3 which is C-076 B2a aglycone.

12. An anti-parasitic composition which comprises an inert carrier and the monosaccharide or aglycone of C-076.