Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-09-16
2001-10-09
Qazi, Sabiha (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S336000, C514S341000, C514S830000
Reexamination Certificate
active
06300348
ABSTRACT:
The present invention relates to formulations for the dermal control of parasitic insects and mites on humans by means of agonists or antagonists of the nicotinergic acetylcholine receptors of insects.
Agonists or antagonists of the nicotinergic acetylcholine receptors of insects are known. They include the nicotinyl insecticides and, very particularly, the chloronicotinyl insecticides.
PCT application WO 93/24 002 discloses that certain 1-[N-(halo-3-pyridylmethyl)]-N-methylamino-1-alkylarnino-2-nitroethylene derivatives are suitable for systemic use against fleas in domestic animals. According to WO 93/24 002, the nonsystemic—i.e. dermal—mode of application is unsuitable for the control of fleas on domestic animals.
This invention, then, provides novel formulations for the dermal application of agonists or antagonists of the nicotinergic acetylcholine receptors of insects which are particularly suitable for dermal control of parasitic insects and mites on humans.
The formulations according to the invention have the following composition:
agonists or antagonists of the nicotinergic acetylcholine receptors of insects in a concentration of from 0.0001 to 20% by weight based on the overall weight of the formulation;
solvents from the group of the cyclic carbonates in a concentration of from 2.5 up to 99.9999% by weight based on the overall weight of the formulation;
if desired, further solvents from the group of the alcohols in a concentration of from 0 to 95% by weight based on the overall weight of the formulation;
if desired, further auxiliaries from the group of the thickeners, spreading agents, colorants, antioxidants, propellants, preservatives, adhesives, 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 nicotinergic acetylcholine receptors of insects are known, for example, from European Offenlegungsschriften (European Published Applications) Nos. 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; German Offenlegungsschriften (German Published Specifications) Nos. 3 639 877, 3 712 307; Japanese Offenlegungsschriften (Japanese Published Applications) Nos. 03 220 176, 02 207 083, 63 307 857, 63 287 764, 03 246 283, 04 9371, 03 279 359, 03 255 072, U.S. Pat. Nos. 5,034,524, 4,948,798, 4,918,086, 5,039,686, 5,034,404; PCT Applications Nos. WO 91/17 659, 91/4965; French Application No. 2 611 114; Brazilian Application No. 88 03 621.
The compounds described in these publications and their preparation are hereby expressly incorporated herein by reference.
These compounds can be advantageously represented by the general formula (I)
in which
R represents, hydrogen, optionally substituted radicals from acyl, alkyl, aryl, aralkyl, heteroaryl or heteroarylalkyl;
A represents a monofunctional group from 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—, it being possible for the radical —CH═ instead of an H atom to be linked to the radical Z;
Z represents a monofunctional group from alkyl, —O—R, —S—R,
or represents a bifunctional group which is linked to the radical A or to the radical X.
Particularly preferred compounds of the formula (I) are those in which the radicals have the following meaning:
R represents hydrogen and represents optionally substituted radicals from acyl, alkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl.
Acyl radicals which may be mentioned are formyl, alkylcarbonyl, arylcarbonyl, alkylsulfonyl, arylsulfonyl, (alkyl)-(aryl)-phosphoryl, which may in turn be substituted.
As alkyl there may be mentioned C
1-10
-alkyl, especially C
1-4
-alkyl, specifically methyl, ethyl, i-propyl, sec- or t-butyl, which may in turn be substituted.
As aryl there may be mentioned phenyl, naphthyl, especially phenyl.
As aralkyl there may be mentioned phenylmethyl, phenethyl.
As heteroaryl there may be mentioned heteroaryl having, up to 10 ring atoms and N, O, S, especially N, as hetero atoms. Specifically there may be mentioned thienyl, furyl, thiazolyl, imidazolyl, pyridyl, benzothiazolyl,
As heteroarylalkyl there may be mentioned heteroarylmethyl, heteroarylethyl having up to 6 ring atoms and N, O, S, especially N, as hetero atoms.
Substituents which may be listed by way of example and preference are: alkyl having preferably 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 having preferably 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 having preferably 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 having preferably 1 to 4, in particular 1 or 2 carbon atoms and preferably 1 to 5, in particular 1 to 3 halogen atoms, the halogen atoms being identical or different and being preferably fluorine, chlorine or bromine, especially fluorine, such as trifluoromethyl; hydroxyl; halogen, preferably fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine; cyano; nitro; amino; monoalkyl- and dialkylamino having preferably 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 having preferably 2 to 4, in particular 2 or 3 carbon atoms, such as carbomethoxy and carboethoxy; sulpho (—SO
3
H); alkylsulfonyl having preferably 1 to 4, in particular 1 or 2 carbon atoms, such as methylsulfonyl and ethylsulfonyl; arylsulfonyl having preferably 6 or 10 aryl carbon atoms, such as phenylsulfonyl, and also heteroarylamino and heteroarylalkylamino such as chloropyridylamino and chloropyridylmethylamino.
A particularly preferably represents hydrogen and represents optionally substituted radicals from acyl, alkyl, aryl, which preferably have the meanings given for R. A additionally represents a bifunctional group. There may be mentioned optionally substituted alkylene having 1-4, in particular 1-2 C atoms, substituents which may be mentioned being the substituents listed earlier above, and it being possible for the alkylene groups to be interrupted by hetero atoms from the group consisting of N, O, S.
A and Z may, together with the atoms to which they are attached, form a saturated or unsaturated heterocyclic ring. The heterocyclic ring can contain a further 1 or 2 identical or different hetero atoms and/or hetero groups. Hetero atoms are preferably oxygen, sulfur or nitrogen, and hetero groups are preferably N-alkyl, where the alkyl in the N-alkyl group preferably contains 1 to 4, in particular 1 or 2 carbon atoms. As alkyl there may be mentioned 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 imidazolidine, pyrrolidine, piperidine, piperazine, hexamethyleneimine, hexahydro-1,3,5-triazine, hexahydrooxodiazine, morpholine, each of which may optionally be substituted, preferably by methyl.
E represents an electron-withdrawing radical, in which context particular mention may be made of NO
2
, CN, halogenoalkylcarbonyl such as 1,5-halogeno-C
1-4
-carbonyl, especially COCF
3
.
X represents —CH═ or —N═
Z represents optionally substituted radicals alkyl, —OR, —SR, —NRR, where R and the substituents preferably have the meaning given above.
Z can form, apart from the abovementioned ring, and together with the atom to which it is attached and with the radical
instead of X, a saturated or unsaturated heterocyclic ring. The heterocyclic ring can contain a further 1 or 2 identical or different hetero atoms and/or groups. The hetero atoms are preferably oxygen, sulfur or nitrogen, and t
Dorn Hubert
Heukamp Ulrich
Peter Rosemary
Sirinyan Kirkor
Sonneck Rainer
Akorli Godfried R.
Bayer Aktiengesellschaft
Gil Joseph C.
Qazi Sabiha
LandOfFree
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