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Spirocyclic derivatives as antiparasitic agents

A compound, cycloalkyl technology, applied in the field of manufacturing said spiro derivatives, can solve the problem of not indicating the range of life cycle stages of parasite species, etc.

Inactive Publication Date: 2015-05-06
ZOETIS SERVICE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, none of these citations exemplifies non-isoxazoline spiro molecules or methods of making spiro compounds, nor does the prior art show that such compounds target a range of parasitic species associated with companion animals, livestock, birds, or fish. Insect species, specific parasite morphological life cycle stage range will be applicable

Method used

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  • Spirocyclic derivatives as antiparasitic agents
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  • Spirocyclic derivatives as antiparasitic agents

Examples

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preparation example Construction

[0191] In the preparation of compounds of the present invention, protection of remote functional groups of intermediates from undesired reactions can be accomplished with protecting groups. The term "protecting group" or "Pg" refers to a substituent typically used to block or protect a particular functional group while allowing other functional groups on the compound to react. For example, an amine protecting group is an amine-attached substituent that blocks or protects the amine functionality of a compound or intermediate. Suitable amine protecting groups include: 1-tert-butoxycarbonyl (Boc); acyl groups including: formyl, acetyl, chloroacetyl, trichloro-acetyl, o-nitrophenylacetyl, o-nitrophenoxy Acetyl, trifluoroacetyl, acetoacetyl, 4-chlorobutyryl, isobutyryl, o-nitrocinnamoyl, picolinoyl, acyl isothiocyanate, aminocaproyl, benzoyl, etc.; and acyloxy, including: methoxycarbonyl, 9-fluorenyl-methoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-trimethylsilylethoxycarbonyl, v...

example

[0256] The following examples provide a more detailed description of the process conditions for preparing compounds of the invention. It should be understood, however, that the invention, as fully described herein and as recited in the claims, is not intended to be limited to the details of the following schemes or preparations. Applicable (E / Z) nomenclature for each of the preparation intermediates is also contemplated.

[0257] Intermediate 1 : tert-butyl 5'-bromo-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

[0258]

[0259] Compound 4-bromo-2-(chloromethyl)-1-iodobenzene (500 g, 1.509 mol) was dissolved in tetrahydrofuran (3750 mL) and cooled to -20°C. i-PrMgCl-LiCl (1.3M solution in THF) (1275 mL, 1.66 mol) was added at less than -15°C. The reaction mixture was cooled to -20°C. tert-butyl 3-oxo-azetidine-1-carboxylate (310 g, 1.81 mol) was added as a solution in tetrahydrofuran (750 mL). The reaction was allowed to warm to room temperature over 90 minute...

example 1

[0275] Example 1: 2-(methylsulfonyl)-1-(5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H -pyrrol-5-yl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-yl)ethanone

[0276]

[0277] To 5'-(3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-5-yl)-3' at room temperature To a stirred solution of H-spiro[azetidine-3,1'-isobenzofuran] hydrochloride (Preparation 5, 900 mg, 1.77 mmol) in THF (20 mL) was added DIPEA (3.01 mL, 17.65 mmol ), methanesulfonylacetic acid (488mg, 3.53mmol), then add T 3 P (5.12 mL, 8.82 mmol, 50% in ethyl acetate). The resulting reaction mixture was stirred at room temperature for 16 hours. The reaction was monitored by TLC, and after complete consumption of the starting material, the reaction mixture was quenched with water (30 mL) and extracted with ethyl acetate (3 x 25 mL). The combined organic layers were washed with NaHCO 3 The solution (30 mL) was washed with brine (30 mL), dried over sodium sulfate, and concentrated...

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Abstract

The invention recites spirocyclic derivatives of Formula (V.1) or (V.2), stereoisomers thereof, veterinary acceptable salts thereof, compositions thereof, processes for making, and their use as a parasiticide for an animal. The variables A, B, V, Z, Y, W1, W2, W3, R1a, R1b, R1c, R2, R3, R4, n, and "---" are as described herein.

Description

technical field [0001] The present invention relates to spirocyclic derivatives having parasiticidal activity. Compounds of interest are spiro derivatives having saturated or partially saturated heterocyclic moieties containing nitrogen and / or oxygen heteroatoms. The invention also relates to methods of making said spiro derivatives, compositions and methods of use thereof. Background technique [0002] There is a need for improved antiparasitic agents for animals, and in particular improved insecticides and acaricides. Furthermore, there is a need for improved topical and oral products that are convenient to administer and contain one or more of such antiparasitic agents that can be used to effectively treat the parasite. Such products would specifically be useful in the treatment of animals including: poultry (e.g. chickens and turkeys), fish, companion animals (e.g. cats, dogs, camels and horses) and livestock (e.g. cattle, bison, pigs, sheep , deer, elk and goat). ...

Claims

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Application Information

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IPC IPC(8): C07D491/10A61K31/397A61P33/00
CPCC07D491/10A61P33/00C07D491/107
Inventor S.M.K.希恩V.A.瓦利安考特
Owner ZOETIS SERVICE LLC
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