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Spiroindoline antiparasitic derivatives

A compound, C1-C6 technology, applied in biocides, drug combinations, anti-infectives, etc., can solve problems such as how to prepare bicyclic compounds that have not been pointed out

Inactive Publication Date: 2016-08-03
ZOETIS SERVICE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, there is no indication in this application of how to prepare the bicyclic compound or of the biological data supporting the bicyclic

Method used

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  • Spiroindoline antiparasitic derivatives
  • Spiroindoline antiparasitic derivatives
  • Spiroindoline antiparasitic derivatives

Examples

Experimental program
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Effect test

preparation example Construction

[0282] In the preparation of compounds of the present invention, protecting groups may be used to effect protection of remote functional groups of intermediates from undesired reactions. The term "protecting group" or "Pg" refers to a substituent commonly used to block or protect a specific functional group while reacting with other functional groups on the compound. For example, an amine protecting group is a substituent attached to an amine 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-nitrophenyl phenylphenoxyacetyl, trifluoroacetyl, acetoacetyl, 4-chlorobutyryl, isobutyryl, o-nitrocinnamoyl, picolilyl, acyl isothiocyanate, aminocaproyl, benzyl Acyl, etc.; and acyloxy groups, including: methoxycarbonyl, 9-fluorenyl-methoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, 2-trimethylsilyl...

Embodiment 1

[0414] Example 1. (E)-N-((2-chloropyridin-4-yl)methyl)-1'-(3-(3,4-dichlorophenyl)allyl)-5,7- Dihydrospiro[furo[3,4-f]indole-3,4'-piperidine]-1(2H)-carboxamide

[0415]

[0416] Step 1: 1-((2-Chloropyridin-4-yl)methylcarbamoyl)-1,2,5,7-tetrahydrospiro[furo[3,4-f]indole-3,4 Preparation of tert-butyl '-piperidine]-1'-carboxylate

[0417]

[0418] In a 10 mL vial, to a stirred solution of (2-chloro-pyridin-4-yl)-methylamine hydrochloride (135 mg, 0.758 mmol, 1 equiv) in dichloromethane (6 mL) at 0 °C was added Tris Ethylamine (0.426 mL, 3.034 mmol, 4 eq) followed by 1,1-carbonyldiimidazole (160 mg, 0.986 mmol, 1.3 eq) was added. The reaction was allowed to warm slowly to room temperature and stir for 4 hours. After the starting material was consumed, the reaction was cooled to 0°C and 1,2,5,7-tetrahydrospiro-[furo[3,4-f]indole-3,4'-piperidine]-1'- tert-Butyl formate (Intermediate 1.12b, 201 mg, 0.607 mmol, 0.8 equiv) and stirred at room temperature for 16 hours. After c...

Embodiment 2

[0423] Example 2: (E)-1'-(3-(4-chlorophenyl)allyl)-N-((2-fluoropyridin-4-yl)methyl)-5,7-dihydrospiro [Furo[3,4-f]indole-3,4'-piperidine]-1(2H)-carboxamide

[0424]

[0425] Example 2 was prepared analogously to Example 1 except that (2-fluoro-pyridin-4-yl)-methylamine hydrochloride was used in step 1 instead of (2-chloro-pyridin-4-yl) - methylamine hydrochloride and replace (E)-3-(3,4-dichloro-phenyl)-propenal with (E)-3-(4-chloro-phenyl)-propenal. 1H NMR (400MHz, DMSO) δ: 1.62(d, J=1.216Hz, 2H), 1.82-1.85(m, 2H), 2.08(t, J=11.24Hz, 2H), 2.90(d, J=11.44Hz, 2H), 3.14(d, J=6.4Hz, 2H), 3.89(s, 2H), 4.38(d, J=5.64Hz, 2H), 4.90(d, J=4.4Hz, 4H)6.34-6.41(m ,1H),6.56(d,J=15.88Hz,1H),7.10(d,J=5.64Hz,2H),7.30(d,J=4.76Hz,1H),7.37(d,J=8.46Hz,2H ), 7.45-7.50 (m, 3H), 7.74 (s, 1H), 8.16 (d, J=5.08Hz, 1H). LC-MS (m / z): 532.8 (M+H).

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Abstract

The invention discloses spiroindoline antiparasitic derivatives. The invention describes novel spiropiperidines of Formula (1A), (1B), and (1C) stereoisomers thereof, veterinarily acceptable salts thereof, compositions thereof, processes for making, and their use in animals as an antiparasitic. The variables A, R1, R2, R3, R4, v, m, 5, and n are as described herein.

Description

technical field [0001] The present invention describes novel bicyclic and cyclic spiroindoline piperidine derivatives having parasiticidal activity, their stereoisomers and veterinary acceptable salts thereof. The present invention also relates to processes for the manufacture of spiroindoline piperidine derivatives, their compositions and methods of use. Background technique [0002] There is a need for improved antiparasiticides for use in animals, and in particular improved endoparasiticides and ectoparasiticides. Furthermore, there is a need for improved topical and oral products that are convenient to administer and contain one or more of said antiparasitic derivatives that are useful in the effective treatment of ectoparasites, such as insects (e.g., fleas, lice, and flies) and acarids (e.g., mites and ticks); and internal parasites such as helminths (nematodes, tapeworms, and flukes). The novel derivatives of the present invention are particularly useful in the trea...

Claims

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Application Information

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IPC IPC(8): C07D471/10C07D471/20C07D513/20C07D491/20A61K31/444A61K31/438A61K31/506A61K31/497A61P33/10A61P33/14
CPCC07D471/10C07D471/20C07D491/20C07D513/20C07D493/20A61P33/00A61P33/10A61P33/14A01N43/90A61K31/435A61K31/444A61K31/4709A61K31/497A61K31/501A61K31/506A61K45/06
Inventor J.文特M.考克斯S.M.K.希恩M.P.柯蒂斯T.雷斯庞德克R.A.尤因G.M.凯恩P.D.约翰逊
Owner ZOETIS SERVICE LLC
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