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Compositions comprising c-13 alkoxyether macrolide compounds and phenylpyrazole compounds

A compound, alkyl alkoxy technology, applied in the field of composition of ivermectin derivatives, can solve problems such as sensitivity

Inactive Publication Date: 2010-03-24
MERIAL LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this patent application does not provide a person skilled in the art with specific instructions on how to formulate 1-N-pyrazole derivatives and avermectin or milbemycin type compounds, let alone how to formulate bullet points including these compounds. Composition (spot-on composition)
Furthermore, the application does not address which specific parasites are susceptible to which specific compositions

Method used

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  • Compositions comprising c-13 alkoxyether macrolide compounds and phenylpyrazole compounds
  • Compositions comprising c-13 alkoxyether macrolide compounds and phenylpyrazole compounds
  • Compositions comprising c-13 alkoxyether macrolide compounds and phenylpyrazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0655] Embodiment 1: the synthetic process of the MEM derivative of preparation ivermectin

[0656] The MEM derivative of ivermectin has the following formula:

[0657]

[0658] where R 16 =-CH 2 CH 3 When it is B1a type, R 15 =-CH 3 When the B1b type.

[0659] In order to synthesize the MEM derivative of ivermectin, the disaccharide group at the C-13 position of ivermectin is partially cleaved by acid solvolysis using 1% acid solution, resulting in cleavage into ivermectin aglycon. The -OH groups at C-5, C-7 and C-13 were then protected with tert-butyldimethylchlorosilane (TBDMS) followed by trimethylchlorosilyl (TMS) to obtain 7,13-Di-O-TMS-5-O-TBDMS ivermectin aglycone.

[0660] The 7,13-di-O-TMS-5-O-TBDMS ivermectin aglycon was then selectively deprotected using dichloroacetic acid to obtain the 7-O-TMS-5-O-TBDMS ivermectin glycoside Yuan. This aglycon was then alkylated with 2-methoxyethoxymethyl chloride (MEM chloride), followed by purification by crystalliza...

Embodiment 2

[0663] Embodiment 2: the anti-flea effect of the MEM derivative of ivermectin

[0664] Two ivermectin derivatives (formula (III) and formula (IV)) were tested for their antiflea effect on male dogs. The efficacy of the compounds of formula (III) and (IV) against fleas was shown using 20 female dogs and 16 male dogs of different breeds with a body weight ranging from 9.3 to 21.6 kg. Dogs were assigned to treatment by limiting randomization based on pre-treatment (day 0) flea numbers. Treatment was vehicle control, 1.5% or 2.5% solution of compound of formula (III) applied topically at 1 ml / kg to provide doses of 15 or 25 mg / kg, 1% or 1.5% solution of compound of formula IV applied topically at 1 ml / kg to provide Doses of 10 or 15 mg / kg. Dogs are single-accommodated in cages or run wild indoors. On days -1, 13, 20 and 27 each dog was infected with 100 fleas (Ctentocephalus felis). On days 0, 1, 2, 3, 14, 15, 16, 21, 22, 23, 28, 29, 30, and 31, flea counts were performed by h...

Embodiment 3

[0666] Example 3: Effect of MEM derivatives of ivermectin against sarcoptic mangae

[0667] Two ivermectin derivatives (formula (III) and formula (IV)) were tested for their anti-scabies effect on male dogs. Twenty-three hybrid dogs and one Heeler (Australian Shepherd), weighing 2.9 to 20.0 kg, with an estimated age of 3 months to 7 years, and naturally infected with sarcoidosis canis, were topically applied according to the multi-point application system, and the These dogs were used to compare the effects of compounds of formula (III) and formula (IV). There are 12 male dogs and 12 female dogs.

[0668] The dogs were placed individually in the kennel. Replication groups of four dogs were formed based on animal availability and mite count; in the repetition groups, dogs were randomly assigned to either vehicle treatment (L-930,870) or to receive the following: Formula (III) at 15 mg / kg body weight The groups of compounds were either 10 mg / kg of the compound of formula IV o...

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Abstract

Provided is a novel ivermectin derivative and compositions for the treatment or prophylaxis of parasite infestations in mammals or birds which comprise: (A) a pharmaceutically effective amount of a 1-N-phenylpyrazole compound; (B) a pharmaceutically effective amount of an ivermectin derivative of formula (II) wherein: R14 represents -(CH2)S-O-Z wherein, s is 1 or 2; Y represents -CH(OR, 15)-, -C(=O)- or -C(=NOR 15); R15 represents hydrogen, alkyl or phenyl; and R16 represents -CH3 or -CH2CH3; Z is alkyl, alkenyl, alkynyl, acyl, alkylalkoxy, aryl, alkanoyloxy, alkoxycarbonyl, alkenoyl, alkynoyl, or aroyl.

Description

[0001] related application [0002] This application is by reference to U.S. Application Serial No. 11 / 317,932 filed 12 / 22 / 2005 and U.S. Application Serial No. 10 / 279,356 filed October 24, 2002, which are hereby acknowledged as U.S. applications filed May 24, 2002 Continuation-in-Part of Serial No. 10 / 155,397, now U.S. Patent No. 6,962,713, which is a divisional application of U.S. Application Serial No. 09 / 376,736, filed August 17, 1999, now U.S. Patent No. 6,426,333, which was filed in 1999 Continuation-in-Part of U.S. Application Serial No. 09 / 271,470, filed March 17, now U.S. Patent No. 6,482,425, which is a continuation-in-part of International Application No. PCT / FR97 / 01548, filed September 15, 1997, and designating the United States , and claims priority from French application No. 96 / 11446, filed September 19, 1996. [0003] Any of the above applications, and all materials cited therein or during its proceedings (application-cited materials) and all materials cited or ...

Claims

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Application Information

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IPC IPC(8): C07D493/10A01N43/90A61K31/365A61P33/00
CPCC07D493/20A61P33/00A61P43/00
Inventor M·D·索尔A·伯克N·舒伯
Owner MERIAL LTD
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