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Azetidine derivatives as antiparasitic agents

A technology of alkyl and compound, applied in the field of azetidine derivatives

Inactive Publication Date: 2015-01-07
ZOETIS SERVICE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, some agents are actually becoming ineffective due to parasite resistance

Method used

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  • Azetidine derivatives as antiparasitic agents
  • Azetidine derivatives as antiparasitic agents
  • Azetidine derivatives as antiparasitic agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0296] Example 1.1-(3-{4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-phenyl }-3-fluoro-azetidin-1-yl)-2-methylsulfonyl-ethanone

[0297]

[0298] Step 1: Preparation of tert-butyl 3-(4-acetyl-phenyl)-3-fluoro-azetidine-1-carboxylate

[0299]

[0300] In a 100 mL autoclave vessel, tert-butyl 3-(4-bromo-phenyl)-3-fluoro-azetidine-1-carboxylate (intermediate from Step 5a; 5 g, 15.142 mmol , 1 equivalent) in ethanol (17.5 mL) was degassed with nitrogen for 30 minutes. At room temperature, TEA (3.79 mL, 27.256 mmol, 1.8 equiv), butyl vinyl ether (BVE, 3.91 mL, 30.282 mmol, 2 equiv), 1,3-bis(diphenylphosphino)propane (DPPP, 0.375g, 0.909mmol, 0.06 equiv), followed by adding Pd(OAc) 2 (0.102g, 0.454mmol, 0.03 equiv). The resulting reaction mixture was heated in an autoclave at 96 °C for 16 hours. After the starting material was completely consumed, the reaction mixture was quenched with 1N HCl (5 mL, pH-2-3) and stirred at room temperature for 2 h...

Embodiment 2

[0314] Example 2.1-(3-{4-[4-(3,5-dichloro-phenyl)-4-trifluoromethyl-4,5-dihydro-3H-pyrrol-2-yl]-phenyl }-3-fluoro-azetidin-1-yl)-2-methyl-propan-1-one

[0315]

[0316] This compound was prepared using a procedure similar to that of Example 1, but using isobutyric acid instead of methanesulfonylacetic acid. Yield: 0.155 g (28.92%). 1 H NMR (400MHz, CDCl 3 )δ: 1.15(t, J=5.86Hz, 6H), 2.47-2.54(m, 1H), 3.45(d, J=17.52Hz, 1H), 3.81(d, J=17.56Hz, 1H), 4.34- 4.51(m,4H),4.58-4.66(m,1H),4.89(d,J=16.96Hz,1H),7.25-7.26(m,2H),7.37(s,1H),7.53(d,J= 8.28Hz, 2H), 7.91 (d, J = 8.16Hz, 2H). LC-MS (m / z): 500.8 (M+H). HPLC purity: 98.85%.

Embodiment 3

[0317] Example 3.3-(3,5-dichloro-4-fluorophenyl)-5-(4-{3-fluoro-1-[(methylsulfonyl)-acetyl]azetidine-3- Base}phenyl)-3-(trifluoromethyl)-3,4-dihydro-2H-pyrrole

[0318]

[0319]Step 1: 3-{4-[(Z)-3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-phenyl Preparation of}-3-fluoro-azetidine-1-carboxylic acid tert-butyl ester

[0320]

[0321] This compound was prepared analogously to the intermediate procedure of Example 1, except that 1-(3,5-dichloro-4-fluoro-phenyl)-2,2,2-trifluoro-ethanone was used instead of 1-( 3,5-Dichloro-phenyl)-2,2,2-trifluoro-ethanone. Yield: 4.1 g (64.06%). 1 H NMR (400MHz, CDCl 3 )δ: 1.47(s, 9H), 4.16(d, J=10.32Hz, 1H), 4.21(d, J=10.44Hz, 1H), 4.39(d, J=10.52Hz, 1H), 4.45(d, J=10.32Hz, 1H), 7.23(d, J=6.08Hz, 2H), 7.40(d, J=1.08Hz, 1H), 7.58(d, J=8.4Hz, 2H), 7.88(d, J= 8.28Hz, 2H). LC-MS (m / z): 535.9 (M+H).

[0322] Step 2: 3-{4-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-3-nitromethyl-butyryl]-phenyl} Preparation of tert...

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Abstract

This invention recites substituted azetidine derivatives of Formula (1) stereoisomers thereof, veterinarily acceptable salts thereof, compositions thereof, and their use as a parasiticide in animals. The substituents A, B, R1a, R1b, R1c, R2, R3, R4, R6, and n are as described herein.

Description

technical field [0001] The present invention relates to azetidine derivatives having parasiticidal activity. The target compound is a heterocyclic derivative substituted by phenyl-azetidine, naphthyl-azetidine or heteroaryl-azetidine. The invention also relates to compositions and methods of their use. Background technique [0002] There is a need for improved antiparasitic agents for animals, particularly for improved long-acting (ie, 6-month) insecticides and acaricides. In addition, there is a need for improved topical and oral products that are convenient to administer and contain one or more antiparasitic agents that can be used to effectively treat ectoparasites, such as insects (e.g., fleas, lice and flies), ticks (eg, mites and ticks), and copepods (eg, sea lice). The compounds of the invention may also be used as endoparasiticides to effectively treat helminths, for example, cestodes (cestodes), nematodes (nematodes) and trematodes (liver leeches). Such products...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10C07D413/10A01N43/80
CPCA01N43/36C07D413/10C07D403/10A01N43/56A01N43/82A01N43/76A01N43/20C07D401/14C07D409/14C07D413/14A61K31/4025A61K31/4155A61K31/422A61K31/4439A61K31/444A61P33/00A01N43/44A61K45/06
Inventor V·威兰科特S·M·K·施汉
Owner ZOETIS SERVICE LLC
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