Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1988-10-07
1990-12-18
Lee, Mary C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514348, 514357, 546261, 546265, A61K 3144, C07D21389, C07D21340
Patent
active
049786709
DESCRIPTION:
BRIEF SUMMARY
SUMMARY OF THE INVENTION
This invention pertains to a new method for killing and controlling worms (Helminths), and new formulations for killing and controlling worms in animals and new chemical compounds The invention is more particularly directed to a new method for killing and controlling parasitic worms in animals with certain quaternaryalkyl acylhydrazones to new anthelmintic formulations comprising the same, and to new quaternaryalkyl acylhydrazones.
The anthelmintic quaternaryalkyl acylhydrazones have the general structural formula I.
BACKGROUND OF THE INVENTION
The diseases or groups of diseases described generally as helminthiasis are due to infection of the animal with parasitic worms known as helminths. Helminthiasis and helminthosis are prevalent and may lead to serious economic problems in valuable warm-blooded domestic animals such as sheep, swine, cattle, goats, dogs, cats, horses poultry and man. Among the helminths, the groups of worms known as nematodes trematodes and cestodes cause widespread and often-times serious infections in various species of animals including man. The most common genera of nematodes, trematodes and cestodes infecting the animals referred to above are Dityocaulus, Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Bunostomum, Oesouhagostomum, Chabertia, Strongyloides, Trichuris, Fasciola, Dicrocoelium, Enterobius, Ascaris, Toxascaris, Toxocara, Ascaridia, Capillaria, Heterakis, Ancylostoma, Uncinaria, Dirofilaria, Onchocerca, Taenia, Moniezia, Dipylidium, Metastrongylus, Triodontophorus, Macracanthorhynchus, Hyostroncylus, and Strongylus. Some of these genera attack primarily the intestinal tract while others, inhabit the stomach, lungs, liver and subcutaneous tissues. The parasitic infections causing helminthiasis and helminthosis lead to anemia, malnutrition, weakness, weight loss, unthriftiness, severe damage to the gastrointestinal tract wall and, if left to run their course, may result in death of the infected animals.
The anthelmintic activity of quaternaryalkyl acylhydrazones has not been previously reported.
DETAILED DESCRIPTION OF THE INVENTION
The quaternaryalkyl acylhydrazones of the invention, including hydrates thereof or pharmaceutically acceptable salts thereof, are represented by Formula I wherein W is selected from the group consisting of one or two C.sub.1 -C.sub.4 alkyl, preferably C.sub.1 -C.sub.3 alkyl; C.sub.1 -C.sub.3 alkoxy; C.sub.1 -C.sub.3 alkylthio; halo; trifluoromethyl; or hydroxy; with the proviso that only one substituent is hydroxy; -C.sub.6)alkyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.3 alkyl, preferably cyclo(C.sub.3 -C.sub.5)alkyl optionally substituted; phenyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, halo, trifluoromethyl, or C.sub.1 -C.sub.3 alkoxy; phenyl(C.sub.1 -C.sub.3)alkyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, halo, trifluoromethyl, or C.sub.1 -C.sub.3 alkoxy; or 1,3-dioxacyclohexan-5-yl; C.sub.1 -C.sub.4 alkyl; phenyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy; phenyl(C.sub.1 -C.sub.3)alkyl; or nitrogen to form a four to seven-member saturated or partially unsaturated nitrogen-containing ring optionally substituted with phenyl and/or one or two C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, said ring optionally containing an oxygen or sulfur atom as a ring member, and the third of R.sub.2, R.sub.3 and R.sub.4 is hydrogen; C.sub.1 -C.sub.4 alkyl; phenyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy; or phenyl(C.sub.1 -C.sub.3)alkyl; or form a 6 or 7 member nitrogen-containing aromatic ring optionally substituted with phenyl and/or one or 2 C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.3 alkoxy; or nitrogen to form an eight to ten-member saturated or partially unsaturated nitrogen-containing bicylic ring optionally substituted with phenyl and/or one or two C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, said ring optionally containing an oxygen or
REFERENCES:
patent: 3993760 (1976-11-01), Pohlke et al.
patent: 4087536 (1978-05-01), Budde et al.
Conder George A.
Folz Sylvester D.
Rector Douglas L.
Jameson William G.
Lee Mary C.
Russell J. A. H.
The Upjohn Company
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