Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2000-08-03
2002-04-09
Pryor, Alton (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06369054
ABSTRACT:
The present invention relates to water-containing formulations for the dermal control of parasitic insects and mites on humans by means of agonists or antagonists of the nicotinic acetylcholine receptors of insects.
Agonists or antagonists of the nicotinic acetylcholine receptors of insects are known. They include the nicotinyl insecticides and, very particularly, the chloronicotinyl insecticides.
DE-A-19 613 334 discloses formulations for dermal application of agonists or antagonists of the nicotinic acetylcholine receptors which are suitable for controlling parasitic insects and mites on humans. These formulations are based on mixtures of organic solvents.
This invention, accordingly, provides novel water-containing formulations for dermal application of agonists or antagonists of the nicotinic acetylcholine receptors which are suitable for controlling parasitic insects and mites, of the following composition:
a—agonists or antagonists of the nicotinic acetylcholine receptors of insects in a concentration of from 0.0001 to 7.5% by weight, based on the overall weight of the formulation;
b—water in a concentration of from 20 to 50% by weight, based on the overall weight of the formulation;
c—acyclic alcohols in a concentration of from 20 to 50% by weight, based on the overall weight of the formulation;
d—cyclic carbonates in a concentration of from 2.5 up to 20.0% by weight, based on the overall weight of the formulation;
e—optionally further auxiliaries from the group consisting of thickeners, spreading agents, colorants, antioxidants, propellants, preservatives, tackifiers, emulsifiers, in a concentration of from 0 up to 30% by weight, based on the overall weight of the formulation.
Agonists or antagonists of the nicotinic acetylcholine receptors of insects are known, for example, from the European Published Specifications No. 580 553, 464 830, 428 941, 425 978, 386 565, 383 091, 375 907, 364 844, 315 826, 259 738, 254 859, 235 725, 212 600, 192 060, 163 855, 154 178, 136 636, 303 570, 302 833, 306 696, 189 972, 455 000, 135 956, 471 372, 302 389; the German Published Specifications No. 3 639 877, 3 712 307; the Japanese Published Specifications No. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072; the U.S. Pat. Specifications No. 5,034,524, 4,948,798, 4,918,086, 5,039,686, 5,034,404; the PCT Applications No. WO 91/17 659, 91/4965; the French J Application No. 2 611 114; the Brazilian Application No. 88 03 621.
The compounds described in these publications and their preparation is expressly incorporated herein by reference.
These compounds are preferably represented by the general formula (I)
in which
R represents hydrogen, optionally substituted radicals from the group consisting of acyl, alkyl, aryl, aralkyl, heteroaryl or heteroarylalkyl;
A represents a monofunctional group from the group consisting of hydrogen, acyl, alkyl, aryl or represents a bifunctional group which is linked to the radical Z;
E represents an electron-withdrawing radical;
X represents the radicals —CH═ or ═N— where the radical —CH═ may be linked to the radical Z instead of an H atom;
Z represents a monofunctional group from the group consisting of alkyl, —O—R, —S—R,
or represents a bifunctional group which is linked to the radical A or the radical X.
Particular preference is given to the compounds of the formula (I) in which the radicals are as defined below:
R represents hydrogen and also represents optionally substituted radicals from the group consisting of acyl, alkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclylalkyl.
Acyl radicals which may be mentioned are formyl, alkylcarbonyl, arylcarbonyl, alkylsulphonyl, arylsulphonyl, (alkyl-)-(aryl-)-phosphoryl, which for their part may be substituted.
Alkyls which may be mentioned are C
1-10
-alkyls, in particular C
1-4
-alkyl, specifically methyl, ethyl, i-propyl, sec- or t-butyl, which for their part may be substituted.
Aryls which may be mentioned are phenyl, naphthyl, in particular phenyl.
Aralkyls which may be mentioned are phenylmethyl, phenylethyl.
Heteroaryls which may be mentioned are heteroaryl having up to 10 ring atoms and N, O or S, in particular N, as heteroatoms. Specifically, mention may be made of thienyl, furyl, thiazolyl, imidazolyl, pyridyl, benzothiazolyl.
Heteroarylalkyls which may be mentioned are heteroarylmethyl, heteroarylethyl, where the heteroaryl preferably contains up to 6 ring atoms and N, O or S, in particular N, as heteroatoms. Particular preference is given to the abovementioned heteroaryl radicals.
Heterocyclylalkyl which may be mentioned is tetrahydrofuranylmethyl.
Substituents which may be mentioned by way of example and by way of preference are:
alkyl preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methyl, ethyl, n- and i-propyl and n-, i- and t-butyl; alkoxy preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i- and t-butyloxy; alkylthio preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methylthio, ethylthio, n- and i-propylthio and n-, i- and t-butylthio; halogenoalkyl preferably having 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 5, in particular 1 to 3, halogen atoms, where the halogen atoms are identical or different and are preferably fluorine, chlorine or bromine, in particular fluorine, such as trifluoromethyl; hydroxyl, halogen, preferably fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl- and dialkylamino preferably having 1 to 4, in particular 1 or 2, carbon atoms per alkyl group, such as methylamino, methyl-ethyl-amino, n- and i-propylamino and methyl-n-butylamino; carboxyl; carbalkoxy preferably having 2 to 4, in particular 2 or 3, carbon atoms, such as carbomethoxy and carboethoxy; sulpho (—SO
3
H); alkylsulphonyl preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methylsulphonyl and ethylsulphonyl; arylsulphonyl preferably having 6 or 10 aryl carbon atoms, such as phenylsulphonyl, and also heteroarylamino and heteroarylalkylamino, such as chloropyridylamino and chloropyridylmethylamino.
A particularly preferably represents hydrogen and also represents optionally substituted radicals from the group consisting of acyl, alkyl, aryl, which are preferably defined as for R. A furthermore represents a bifunctional group. Mention may be made of optionally substituted alkylene having 1-4, in particular 1-2, carbon atoms, where the substituents which may be mentioned are the substituents listed further above and where the alkylene groups may be interrupted by heteroatoms from the group consisting of N, O and S.
A and Z together with the atoms to which they are attached may form a saturated or unsaturated heterocyclic ring. The heterocyclic ring may contain a further 1 or 2 identical or different heteroatoms and/or hetero groups. Preferred heteroatoms are oxygen, sulphur or nitrogen and preferred hetero groups are N-alkyl, where the alkyl of the N-alkyl group preferably contains 1 to 4, in particular 1 or 2, carbon atoms. Alkyls which may be mentioned are methyl, ethyl, n- and i-propyl and n-, i- and t-butyl. The heterocyclic ring contains 5 to 7, preferably 5 or 6, ring members.
Examples of the heterocyclic ring which may be mentioned are: pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-1,3,5-triazine, morpholine, oxadiazine, each of which may optionally be substituted, preferably by methyl.
E represents an electron-withdrawing radical, and mention may be made in particular of NO
2
, CN, halogenoalkylcarbonyl such as 1-5-halogeno-C
1-4
-carbonyl, in particular COCF
3
, and also alkylsulphonyl and halogenoalkylsulphonyl, such as 1-5-halogeno-C
1
-C
4
-sulphonyl, in particular SO
2
CF
3
.
X represents —CH═ or —N═.
Z represents optionally substituted radicals alkyl, —OR, —SR, —NRR (the radicals R are identical or different), where R and the substituents are preferably as defined above.
Z may, in addition
Horn Karin
Sirinyan Kirkor
Sonneck Rainer
Stöcker Ronald Helmut
Bayer AG
Pryor Alton
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