Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-01-20
2000-02-22
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514406, 5483711, 5483741, 5483751, A61K 31415, C07D23114, C07D23138
Patent
active
060280964
DESCRIPTION:
BRIEF SUMMARY
This invention relates to pyrazole derivatives having parasiticidal properties.
Certain parasiticidal pyrazole derivatives are already known. These include fipronil (5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethy lsulphinylpyrazole) and certain analogues thereof mentioned in International Patent Application WO 87/03781. Certain of the present compounds are generically disclosed in WO 87/03781, but none are specifically disclosed therein.
Farina et al describe the synthesis of 3-cyano-4-formyl-1-phenylpyrazole (Chemical Abstracts, vol.102(7), 62138j (1985), An.Quim.Ser.C(1983),79(3),333).
DE 195 18 054 A1 describes various 4-ketoxime derivatives of pyrazoles with insecticidal activity.
Kokai 8-311036 describes various 4-ketone derivatives of pyrazoles with pesticidal activity. Certain insecticidal 4-sulphurpentafluorophenylpyrazoles are disclosed in US Pat. No. 5,451,598.
A new group of parasiticidal pyrazole derivatives has now been found. Thus, according to the present invention, there is provided a compound of formula (I), ##STR2## wherein R.sup.2 is NH.sub.2, H, halogen, NH(C.sub.1-6 alkyl optionally substituted with one or more halogen), NH(allyl optionally substituted with one or more halogen), NH(benzyl optionally substituted with one or more halogen), NHSCF.sub.3, or R.sup.2 is C.sub.1-6 alkyl optionally substituted with one or more halogen; C.sub.1-6 alkyl optionally substituted with one or more halogen, C.sub.1-6 alkoxy optionally substituted with one or more halogen, or S(O).sub.n (C.sub.1-6 alkyl optionally substituted with one or more halogen) wherein n is 0,1 or 2; halogen, or C.sub.3-8 cycloalkyl optionally substituted by one or more halogen, or by one or more C.sub.1-4 alkyl optionally substituted with one or more halogen, or by C.sub.3-8 cycloalkylcarbonyl; 3-cyano-4-formyl-1-phenylpyrazole; thereof (hereinafter referred to together as "the compounds of the invention").
The compounds of the invention are generally more efficacious or have a reduced resistance factor or have a broader spectrum of activity or are safer (e.g. less toxic) or have other more advantageous properties than the compounds of the prior art.
Pharmaceutically- and veterinarily-acceptable salts are well know to those skilled in the art, and for example include those mentioned by Berge et al, in J.Pharm.Sci., 66, 1-19 (1977). Suitable acid addition salts are formed from acids which form non-toxic salts and include the hydrochloride, hydrobromide, hydroiodide, nitrate, sulphate, bisulphate, phosphate, hydrogenphosphate, acetate, gluconate, lactate, salicylate, citrate, tartrate, ascorbate, succinate, maleate, fumarate, gluconate, formate, benzoate, methanesulphonate, ethanesulphonate, benzenesulphonate and p-toluenenesulphonate salts. Suitable base addition salts are formed from bases which form non-toxic salts and include the aluminium, calcium, lithium, magnesium, potassium, sodium, zinc and diethanolamine salts.
Alkyl and alkoxy groups may be straight- or branched-chain where the number of carbon atoms allows.
Preferably R.sup.2 is NH.sub.2, H, NH(C.sub.1-6 alkly optionally substituted with one or more halogen), NH(allyl optionally substituted with one or more halogen), NH(benzyl optionally substituted with one or more halogen), NHSCF.sub.3, or R.sup.2 is C.sub.1-6 alkyl optionally substituted with one or more halogen.
More preferably, R.sup.2 is is H, NHCH.sub.3, NHCH.sub.2 Ph, NHCH.sub.2 CH.dbd.CH.sub.2, NHCH(CH.sub.3).sub.2, NHSCF.sub.3 or NH.sub.2.
Preferably R.sup.3 and R.sup.7 are halogen.
More preferably, R.sup.3 and R.sup.7 are Cl.
Preferably R.sup.5 is SF.sub.5, C.sub.1-6 alkyl optionally substituted with one or more halogen or C.sub.1-6 alkoxy optionally substituted with one or more halogen.
More preferably R.sup.5 is OCF.sub.3, CF.sub.3 or SF.sub.5.
Preferably X is O or NOY where Y is H or C.sub.1-6 alkyl;
More preferably X is O, NOH or NOCH.sub.3.
Most preferably, X is O.
Preferably R.sup.8 is H, C.sub.1-8 alkyl optionally substituted with one or more halogen, or C.sub.3-8 cycloalk
REFERENCES:
patent: 5232940 (1993-08-01), Hatton et al.
Farina et al., 1982, Anales de Quimica 79:333-338.
Chemical Abstracts, 1985, 102 (7):62138;.
Ginsburg Paul H.
Koller Alan L.
Pfizer Inc
Ramsuer Robert W.
Richardson Peter C.
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