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Organometallic n-2-cyano-1-hydroxypropan-2-yl for use as anthelmintics

An organometallic, -SO2CF3 technology, applied in metallocene, organic chemistry, anti-infective drugs, etc., can solve the problem of unknown mode of action of monepal

Inactive Publication Date: 2016-06-15
UNIV ZURICH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Although the interaction of AAD with specific acetylcholine receptor (nAChR) subunits has been proposed, the exact mode of action of monepal is unknown

Method used

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  • Organometallic n-2-cyano-1-hydroxypropan-2-yl for use as anthelmintics
  • Organometallic n-2-cyano-1-hydroxypropan-2-yl for use as anthelmintics
  • Organometallic n-2-cyano-1-hydroxypropan-2-yl for use as anthelmintics

Examples

Experimental program
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Embodiment 1

[0296] Example 1 : Synthesis of Compound 1

[0297] The proposed synthetic route is depicted in Scheme 4.

[0298]

[0299] Scheme 4: Reagents and conditions: (a) metal tert-butoxide, t-BuLi, CO 2 , THF, -78°C → room temperature, 35%; (b) CH 2 Cl 2 , oxalyl chloride, reflux → room temperature, overnight; (c) THF, NEt 3 , room temperature, overnight, 29%; (d) THF, NaH, 3-fluoro-4-(trifluoromethyl)benzonitrile, overnight, 0°C→room temperature, 26%.

[0300] Compound 11 was reacted with metal tert-butoxide, t-BuLi and CO 2 The reaction produces compound 2a. The synthesis of ferrocenecarboxylic acid 2a (step a) was adapted from the method from Witte et al. (Organometallics, 1999, 18, 4147). Compound 2a is reacted with oxalyl chloride at reflux to give compound 2b. The synthesis of ferrocenecarbonyl chloride 2b (step b) was adapted from the method of Cormode et al. (Dalton Trans. 2010, 39, 6532). Optionally, the adapted method of Lorkowski et al. (VIII. Preparation of ...

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Abstract

The invention relates to a compound characterized by a general formula (1), wherein OM is an organometallic compound independently selected from the group of an unsubstituted or substituted metal sandwich compound, an unsubstituted or substituted half metal sandwich compound or a metal carbonyl compound, wherein Z is a group described by a general formula -Kr-Fi -Kt-, wherein -Fi is -O-, -S-, -O-C(=O)-, -O-C(=S)-, -S-C(=O)- or NH-(C=O)-with i being 0 or 1, -Kr is a Cr-alkyl with r being 0, 1, 2, 3 or 4, -Kt is a Ct-alkyl with t being 0, 1, 2, 3 or 4, and wherein each RX1 independently from any other RX1 is -C(=O)ORX2,-C(=O)NRX22, -C(=O)SRX2, -C(=S)ORX2, -C(NH)NRX22, CN4H2, -NRX22,-C(=O)RX2, -C(=S)RX2, -ORX2, -SRX2, -CF3,-OCF3, -SCF3, -SOCF3, -SO2CF3,-CN,-NO2,-F,-Cl, -Br or -I, and wherein n of R X1 n is 0, 1, 2, 3, 4 or 5, and with each RX2 independently from any other RX2 being hydrogen or an unsubstituted or substituted C1-C4 alkyl and their use in a method for treatment of infections by helminths.

Description

technical field [0001] The present invention relates to organometallic 2-cyano-2-aminobenzoyl-propyl derivatives and their use as anthelmintics. Background technique [0002] Parasites cause significant economic losses in agriculture all over the world due to low productivity, limited growth rates and mortality. In particular, the decline in productivity not only affects the livestock sector, but also significantly affects global food production. The economic losses caused by parasites to the livestock industry are estimated to be in the tens of billions of dollars each year. Many anti-helminth drugs have been discovered and marketed over the past few decades. However, the problem of parasites persists due to the prevalence of multidrug resistance to most types of anthelmintics. Therefore, the development of novel anthelmintics is a major priority. Any anti-helminth drug developed against parasites in livestock may also be applied against parasites in humans and other an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N55/02C07F15/00C07F15/02A61K31/28A61K31/295
CPCA01N55/00C07F17/00C07F17/02A61P33/10
Inventor 吉勒斯·加塞尔罗宾·B·加塞尔让尼娜·埃斯阿卜杜勒·贾巴尔马来·帕特拉
Owner UNIV ZURICH