Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-03-10
2000-10-10
Powers, Fiona T.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514919, 548513, 424405, 424DIG10, A01N 4338, C07D20952
Patent
active
061302414
DESCRIPTION:
BRIEF SUMMARY
This invention relates to insect- and acarid-repellent formulations, novel compounds for use in such formulations, and methods for repelling insects and acarids.
International patent application WO 87/04594 indicates a group of 1-substituted azacycloalkanes to be useful as insect repellents (see pages 51 and 52).
Japanese Patent Applications 59031702, 58120878, 58072504 and 58072503 claim a group of 1-substituted azacycloalkenes as insect repellents.
Japanese Patent Applications 7118112, 7046955, 6263605, 4225902 and 4036205, and European Patent Application EP 525893 disclose tricyclic azacycloalkanes indicated as insect repellents.
3-n-Butyl-3-azabicyclo[3.1.0]hexane-2,4-dione is disclosed as a chemical intermediate by Tufariello et al, Tetrahedron Letters, Vol 28, No 3, pp 267-270, 1987. 3-n-Octyl-3-azabicyclo[3.1.0]hexane-2,4-dione has been made available on a non-confidential basis.
According to the present invention, there is provided an insect- or acarid-repellent formulation comprising a compound of formula I, ##STR2## wherein R represents straight or branched chain C.sub.2-10 alkyl, straight or branched chain C.sub.2-10 alkenyl, or straight or branched chain C.sub.2-10 alkynyl, which groups are optionally substituted by one or more groups selected from halogen, C.sub.4-8 cycloalkyl and C.sub.4-8 cycloalkenyl;
The formulations of the invention may have the advantage that they are more potent or longer acting than those of the prior art. The nature of the compound of formula I may also confer a pleasant odour on the formulation to humans.
Preferred formulations include those in which: 6-hepten-1-yl); H.sub.17), optionally substituted by chlorine; and 2-cyclohexylethyl).
"Halogen" means fluorine, chlorine, bromine and iodine. Fluorine and chlorine are of particular interest.
According to the invention there is also provided a compound of formula I, as defined above, with the proviso that R does not represent n-butyl or n-octyl.
The invention further provides a method of repelling insects or acarids, which comprises applying a compound of formula I, as defined above, to the exterior of a mammal. The mammal may be a human, a companion animal (for example a dog or a cat) or a livestock animal. Insects of particular interest are mosquitoes, gnats and midges. Acarids of particular interest are ticks. Preferably, the compound of formula I will be applied in a formulation as defined above.
In addition, the invention provides a process for the production of a compound of formula I, as defined above, with the proviso that R does not represent n-butyl or n-octyl, which comprises: ##STR3## with a compound of formula RX, wherein R is as defined above, and X is halogen, in the presence of a base; ##STR4## with a compound of formula RNH.sub.2, wherein R is as defined above; (c) reacting the compound of formula II with diethyl azodicarboxylate, triphenylphosphine and a compound of formula ROH, wherein R is as defined above, in a Mitsunobu reaction; or ##STR5## in which R.sup.d has the same definition as R above except that it is substituted by OH or oxo, with diethylaminosulfurtrifluoride to give a corresponding compound of formula I in which each OH or oxo group is replaced with one or two fluorine atoms, respectively.
In process (a), the reaction is preferably carried out at or below room temperature in a solvent which does not adversely affect the reaction (for example dimethylformamide). Suitable bases include sodium hydride.
In process (b), the reaction may be carried out in an excess of amine as solvent, at an elevated temperature.
In process (c), the diethyl azodicarboxylate and the triphenyl phosphine are allowed to react together first, below room temperature, and then the compound of formula ROH is added, followed by the compound of formula II. The mixture is then allowed to warm to room temperature. The reaction is preferably carried out in a solvent which does not adversely affect the reaction (for example tetrahydrofuran). The Mitsunobu reaction is described more fully in J Am Chem Soc, 94, 679 (1972).
REFERENCES:
patent: 4183857 (1980-01-01), Kollmeyer
Poulter et al., Tetrahedron Letters, 1971, 25, 2255-2258.
Chemical Abstracts, Columbus, Ohio, US, vol. 99, 1983, Sep. 26, No. 13, 100966g.
Tufariello et al., Tetrahedron Letters, vol. 28, No. 3, pp. 267-270, 1987.
Benson Gregg C.
Pfizer Inc.
Powers Fiona T.
Richardson Peter C.
Ronau Robert T.
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