Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1986-10-03
1991-04-30
Rotman, Alan L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
546265, 546270, 546291, 546284, 546332, C07D40512, C07D40912, C07D21376
Patent
active
050119320
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 pyridinyl acylhydrazones, to new anthelmintic formulations comprising the same, and to new pyridinyl acylhydrazones.
The anthelmintic pyridinyl 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 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 and cestodes infecting the animals referred to above are Dictyocaulus, Haemonchus, Trichostrongylus, Ostertagia, Nematodirus, Cooperia, Bunostomum, Oesophagostomum, Chabertia, Strongyloides, Trichuris, Fasciola, Dicrocoelium, Enterobius, Ascaris, Toxascaris, Toxocara, Ascaridia, Capillaria, Heterakis, Ancylostoma, Uncinaria, Onchocerca, Taenia, Moniezia, Dipylidium, Metastrongylus, Macracanthorhynchus, Hyostrongylus, 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 pyridinyl acylhydrazones has not been previously reported.
DETAILED DESCRIPTION OF THE INVENTION
The pyridinyl acylhydrazones of this invention, including hydrates or pharmaceutically acceptable salts thereof, are represented by Formula I wherein X is (a) hydrogen; (b) C.sub.1 -C.sub.10 alkyl; (c) C.sub.2 -C.sub.6 alkenyl, preferably C.sub.2 -C.sub.4 alkenyl; (d) C.sub.2 -C.sub.6 alkynyl; (e) cyclo(C.sub.3 -C.sub.10)alkyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, C.sub.1 -C.sub.4 alkoxy, trifluoromethyl, or halo; (f) pyrrolidinyl; (g) piperidinyl; (h) 1-methylpyrrolidinyl; (i) 1-methylpiperidinyl; (j) C.sub.2 -C.sub.6 alkoxyalkyl; (k) cyclo(C.sub.3 -C.sub.10)alkyl(C.sub.1 -C.sub.4)alkyl; (l) phenyl(C.sub.1 -C.sub.4)alkyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, or trifluoromethyl; (m) phenoxy(C.sub.1 -C.sub.4)alkyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, or trifluoromethyl; (n) naphthyl(C.sub.1 -C.sub.3)alkyl optionally substituted with one or two C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, or trifluoromethyl; (o) C.sub.1 -C.sub.6 alkoxy, preferably C.sub.1 -C.sub.4 alkoxy; (p) diphenylmethoxy; (q) cyclo(C.sub.3 -C.sub.6)alkyloxy optionally substituted with one or two C.sub.1 -C.sub.3 alkyl; (r) phenoxy optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, or trifluoromethyl; (s) benzyloxy optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halo, or trifluoromethyl; with the proviso that when a 2-pyridinyl acylhydrazone and R.sub.1, R.sub.2, R.sub.4 are hydrogen, R.sub.3 is not benzyl; (t) heteroaromatic optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, C.sub.1 -C.sub.3 alkylthio, or trifluoromethyl; (u) phenyl optionally substituted with one, 2 or 3 C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.3 alkoxy, halo, trifluoromethyl, C.sub.2 -C.sub.6 dialkylamino, C.sub.1 -C.sub.3 alkylthio, nitro, or phenoxy optionally su
REFERENCES:
patent: 3073819 (1963-01-01), Straub et al.
patent: 4317776 (1982-03-01), Klayman et al.
Chem. Abstracts, vol. 52(2), pp. 1280-through 1281-(b), Jan. 25, 1958.
Chem. Abstracts, vol. 59(2), pp.-1600-h through 1601-(b), Jul. 22, 1963.
Chem. Abstracts, vol. 62(5), pp.-8065-f-g, Mar. 1, 1965.
F. Capitan, F. Salinas and J. Gimenez Plaza, Afinidad, 35, 263-5 (1978); C.A. vol. 84, (1876), Columbus OH (U.S.), Abstract No. 11787x (Previously Provided in S.N. 715,425, filed Mar. 25, 1985).
H. Bojarska-Dahlig, Rec. Trav. Chim. 83, pp. 177-185 (1964); C.A. 60, 14467d.
Gioacchino Mazzone et al, J. Heterocycl. Chem., vol. 21(1), 181-4 (1984).
E. Baker, M. L. Vitolo and J. Webb, Biochem. Pharmacol., vol. 34(17), 3011-17 (1985).
Chemical Abstracts, vol. 67, (1967), Columbus, OH (U.S.), Abstract No. 82098h.
Chemical Abstracts, vol. 70, (1969), Columbus OH (U.S.), Abstract No. 1153ou.
Conder George A.
Folz Sylvester D.
Rector Douglas L.
Rotman Alan L.
Upjohn Company
LandOfFree
Anthelmintic pyridinyl acylhydrazones derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Anthelmintic pyridinyl acylhydrazones derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Anthelmintic pyridinyl acylhydrazones derivatives will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-641209