Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-10-16
2003-05-13
Pryor, Alton (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S330000
Reexamination Certificate
active
06562841
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a method for selecting the most effective arthropod repellent from stereoisomers of a compound, involving testing each stereoisomer of the compound for its effectiveness as an arthropod repellent against an arthropod of a particular genus and species, comparing the test results and selecting the most effective arthropod repellent stereoisomer from the stereoisomers of the compound, wherein the compound is a piperidine analog of the formula
in which R
2
, R
3
, R
4
, R
5
and R
6
may be the same or different and represent hydrogen, methyl, ethyl, isopropyl, or butyl groups, wherein said methyl, ethyl, isopropyl, or butyl groups are optionally substituted in their primary or secondary position with a hydroxyl (—OH) group, and R
1
represents unbranched or branched C1-8 alkanes, unbranched or branched C1-8 alkenes, C5-8 cycloalkanes, C5-8 cycloalkenes, methyl substituted C5-8 cycloalkanes, or methyl substituted C5-8 cycloalkenes or R
1
is —O—R
7
wherein a carbon atom of R
7
is attached to the O of —O—R
7
and wherein R
7
represents unbranched C1-8 alkanes, branched C1-8 alkanes, unbranched C1-8 alkenes, branched C1-8 alkenes, C5-8 cycloalkanes, C5-8 cycloalkenes, methyl substituted C5-8 cycloalkanes, or methyl substituted C5-8 cycloalkenes, and wherein said compound has at least one asymmetric center. Generally, the compound has one or two asymmetric centers.
The present invention also relates to a composition for repelling arthropods, containing a carrier material and an arthropod repelling effective amount of a stereoisomer of a compound selected by the above method.
In addition, the present invention also relates to a method for repelling arthropods from an object (e.g., mammals such as humans) or area (e.g., a surface such as human skin), involving treating the object or area with the above composition.
Racemic 1-(3-cyclohexen-1-ylcarbonyl)-2-methylpiperidine was first identified as an insect repellent twenty-two years ago (McGovern, T. P., et al., Mosq. News, 38: 346-349 (1978)). The U.S. Department of Agriculture assigned the compound a code number, AI3-37220, hereafter referred to as 220 (FIG.
1
). The so-called repellent does not necessarily reduce the number of blood-sucking arthropods visiting a site where the compound has been applied, but it does reduce the number of bites sustained by an individual whose skin has been treated topically with the compound; the term repellent is used herein in this context. Field and laboratory studies against many species of blood-sucking arthropods have consistently shown that 220 is more or as effective as the commonly used arthropod repellent deet (N,N-diethyl-3-methyltoluamide) in reducing bites (Robert, L. L., et al., J. Med. Entomol., 29: 267-272 (1992); Coleman, R. E., et al., J. Med. Entomol., 30(3): 499-502 (1993); Walker, T. W., et al., J. Am. Mosq. Control. Assoc., 12: 172-176 (1996); Frances, S. P., et al., J. Med. Entomol. 33, 511-515 (1996); Frances, S. P., et al., J. Am. Entomol., 35(5): 690-693 (1998)).
Compound 220 contains two asymmetric centers and standard symmetric synthesis yields a equal mixture of four stereoisomers. All previous repellent studies were conducted using the stereoisomeric mixture (racemate). Up to now, the repellent properties of the individual stereoisomers of 220 or of other known repellents were never evaluated. The present study determined if chirality plays a role in repellents (e.g., 220).
SUMMARY OF THE INVENTION
A method is disclosed for selecting the most effective arthropod repellent from stereoisomers of a compound, involving testing each stereoisomer of the compound for its effectiveness as an arthropod repellent against an arthropod of a particular genus and species, comparing the test results and selecting the most effective arthropod repellent stereoisomer from the stereoisomers of the compound, wherein the compound is a piperidine analog of the formula
in which R
2
, R
3
, R
4
, R
5
and R
6
may be the same or different and represent hydrogen, methyl, ethyl, isopropyl, or butyl groups, wherein said methyl, ethyl, isopropyl, or butyl groups are optionally substituted in their primary or secondary position with a hydroxyl (—OH) group, and R
1
represents unbranched or branched C1-8 alkanes, unbranched or branched C1-8 alkenes, C5-8 cycloalkanes, C5-8 cycloalkenes, methyl substituted C5-8 cycloalkanes, or methyl substituted C5-8 cycloalkenes or R
1
is —O—R
7
wherein a carbon atom of R
7
is attached to the O of —O—R
7
and wherein R
7
represents unbranched C1-8 alkanes, branched C1-8 alkanes, unbranched C1-8 alkenes, branched C1-8 alkenes, C5-8 cycloalkanes, C5-8 cycloalkenes, methyl substituted C5-8 cycloalkanes, or methyl substituted C5-8 cycloalkenes, and wherein said compound has at least one asymmetric center. Generally, the compound has one or two asymmetric centers.
A composition is disclosed for repelling arthropods, containing a carrier material and an arthropod repelling effective amount of a stereoisomer of a compound selected by the above method.
A method is also disclosed for repelling arthropods from mammals, involving treating the mammal with the above composition.
REFERENCES:
patent: 4797408 (1989-01-01), McGovern et al.
patent: 5008261 (1991-04-01), Kruger et al.
Frances et al, Field evaluation of repellent, 1999, J. Am. Mosq. Control Assoc., 15(3), 339-341.*
Schreck et al, Repellents and other personal protection, 1989, J. Am. Mosq. Control Assoc., 5(2), 247-250.*
Allinger, N.L., et al., “Molecular Mechanics. The MM3 Force Field for Hydrocarbons”,J. American Chemical Society, vol. 111(23), pp. 8551-8566, Nov. 8, 1989.
Coleman, R.E., et al., “Laboratory Evaluation of Repellents Against Four Anopheline Mosquitoes (Diptera: Culicidae) and Two Phlebotomine Sand Flies (Diptera: Psychodidae)”,J. Medical Entomology, vol. 30(3), pp. 499-502, May 1993.
Frances, S.P., et al., “Laboratory and Field Evaluation of the Repellents Deet, CIC-4, and AI3-37220 AgainstAnopheles farauti(Diptera: Culicidae) in Australia”,J. Medical Entomology, vol. 35(5), pp. 690-693, Sep. 1998.
Frances, S.P., et al., “Laboratory and Field Evaluation of Deet, CIC-4, and AI3-37220 Against Anopheles dirus (Diptera:Culicidae) in Thailand”,J. Medical Entomology, vol. 33, pp. 511-515, Jul. 1996.
Harris, R.K., “Nuclear Magnetic Resonance Spectroscopy, A Physiochemical View”, Longman Scientific & Techincal, Longman Group UK Limited, pp. 121-127, 1986.
Hoch, A.L., et al., “Laboratory Evaluation of a New Repellent Camouflage Face Paint”,J. American Mosquito Control Association, vol. 11(2), pp. 172-175, Jun. 1995.
Klun, J.A., et al., “A New Module for Quantitative Evaluation of Repellent Efficacy Using Human Subjects”,J. Medical Entomology, vol. 37(1), pp. 177-181, Jan. 2000.
Klun, J.A., et al., “Optically Active Arthropod Repellents for Use Against Disease Vectors”,J. Medical Entomology, vol. 37(1), pp. 182-186, Jan. 2000.
McGovern, T.P., et al., “Mosquito Repellents: Alicyclic Amides as Repellents ForAedes aegyptiandAnopheles quadrimaculatus”,Mosquito News, pp. 346-349, Sep. 1978.
Robert, L.L., et al., Toxicology Study No. 86-8104-98, “Laboratory and Field Evaluation of Five Repellents Against the Black FliesProsimulium mixtumandP. fuscum(Diptera: Simuliidae)”,J. Medical Entomology, vol. 29(2), pp. 267-272, Mar. 1992.
Snodgrass, H.L., et al., “The Acute Toxicity of the Diastereomers of the Insect Repellent AI3-37220”,U.S. Army Center for Health Promotion and Preventive Medicine, pp. 1-7, Jun. 1998.
Vries, T., et al., “The Family Approach to the Resolution of Racemates”,Angew. Chem. Int. Ed., vol. 37(17), pp. 2349-2354, 1998.
Walker, T.W., et al., “Field Evaluation of Arthropod Repellents, Deet and A Piperidine Compound, AI3-37220, AgainstAnopheles funestusandAnopheles arabiensisin Western Kenya”,J. American Mosquito Control Association, vol. 12(2), pp. 172-176, Jul. 1996.
Schreck, C.E., et al., “Repellents and Other Personal Protection Strategies AgainstAedes albopictus”, J. American Mosquito Control Association, vol. 5(2), pp. 247-250,
Klun Jerome A.
Schmidt Walter F.
Fado John D.
Pryor Alton
Silverstein M. Howard
Stover G. Byron
The United States of America as represented by the Secretary of
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