Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-06-03
2000-06-13
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, 5483717, 5483751, 5483771, 5462754, A01N 4356, C07D23114, C07D23138
Patent
active
06075043&
DESCRIPTION:
BRIEF SUMMARY
This invention relates to pyrazole derivatives having parasiticidal properties. More particularly, it relates to 1-aryl-4-cyclopropylpyrazoles.
Certain pyrazole derivatives possessing, inter alia, antiparasitic activity are already known. For example, EP-A-0234119 discloses 1-arylpyrazoles for the control of arthropod, plant nematode and helminth pests. 1-Arylpyrazoles are also disclosed in EP-A-0295117; in addition to having arthropodicidal, plant nematocidal and anthelmintic activity, these compounds are reported to display antiprotozoal properties. Similar profiles of activity are also displayed by the 1-arylpyrazoles disclosed in EP-A-0295118.
Furthermore, EP-A-0280991 discloses certain 1-arylpyrazoles having insecticidal activity, WO-A-97/07102 describes other 1-arylpyrazoles with parasiticidal properties and EP-A-0780378 relates to 1-arylpyrazoles and 1-heteroarylpyrazoles and their use as pesticides.
The present invention provides a compound of formula (I): ##STR1## or a pharmaceutically, veterinarily or agriculturally acceptable salt thereof, or a pharmaceutically, veterinarily or agriculturally acceptable solvate (including hydrate) of either entity, are each independently selected from halo and the 4-substituent is selected from C.sub.1 to C.sub.4 alkyl optionally substituted with one or more halo, C.sub.1 to C.sub.4 alkoxy optionally substituted with one or more halo, S(O).sub.n C.sub.1 to C.sub.4 alkyl optionally substituted with one or more halo, halo and pentafluorothio; or 3,5-disubstituted pyridin-2-yl wherein the 3-substituent is halo and the 5-substituent is selected from C.sub.1 to C.sub.4 alkyl optionally substituted with one or more halo, C.sub.1 to C.sub.4 alkoxy optionally substituted with one or more halo, S(O).sub.n C.sub.1 to C.sub.4 alkyl optionally substituted with one or more halo, halo and pentafluorothio; with one or more halo; cyano, C.sub.1 to C.sub.5 alkanoyl or phenyl; to C.sub.4 alkyl, fluoro, chloro and bromo or, together with the carbon atom to which they are attached, form a C.sub.3 to C.sub.6 cycloalkyl group; to C.sub.4 alkyl, fluoro, chloro and bromo, R.sup.2 and R.sup.6, together with the carbon atoms to which they are attached, may form a C.sub.5 to C.sub.7 cycloalkyl group; one or more halo, or C.sub.1 to C.sub.4 alkoxy; and
In the above definition, unless otherwise indicated, alkyl and alkoxy groups having three or more carbon atoms and alkanoyl groups having four or more carbon atoms may be straight chain or branched chain; halo means fluoro, chloro, bromo or iodo.
The compounds of formula (I) may contain one or more chiral centres and therefore can exist as stereoisomers, i.e. as enantiomers or diastereoisomers, as well as mixtures thereof. The invention includes both the individual stereoisomers of the compounds of formula (I) together with mixtures thereof. Separation of diastereoisomers may be achieved by conventional techniques, e.g. by fractional crystallisation or chromatography (including HPLC) of a diastereoisomeric mixture of a compound of formula (I) or a suitable salt or derivative thereof. An individual enantiomer of a compound of formula (I) may be prepared from a corresponding optically pure intermediate or by resolution, either by HPLC of the racemate using a suitable chiral support or, where appropriate, by fractional crystallisation of the diastereoisomeric salts formed by reaction of the racemate with a suitable optically active acid.
Also included in the invention are radiolabelled derivatives of compounds of formula (I) which are suitable for biological studies.
The pharmaceutically, veterinarily and agriculturally acceptable salts of the compounds of formula (I) are, for example, non-toxic acid addition salts formed with inorganic acids such as hydrochloric, hydrobromic, sulphuric and phosphoric acid, with organo-carboxylic acids, or with organo-sulphonic acids. For a review of suitable salts, see J. Pharm. Sci., 1977, 66, 1.
A preferred group of compounds of formula (I) is that wherein R.sup.1 is 2,6-dichloro-4-trifluoromethylphenyl, 2,6
REFERENCES:
patent: 5232940 (1993-08-01), Hatton et al.
patent: 5547974 (1996-08-01), Hatton et al.
Elkaschef et al., Chemical Abstracts, vol. 81, No. 1520695, 1974.
Donahue E. Victor
Ginsburg Paul H.
Pfizer Inc.
Ramsuer Robert W.
Richardson Peter C.
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