Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2002-03-25
2004-08-24
Levy, Neil S. (Department: 1616)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S919000, C424S405000
Reexamination Certificate
active
06780876
ABSTRACT:
The present invention relates essentially to a non-therapeutical process for deterring vermin, which is based on the usage of the largely known compounds of formula (I) shown below. Furthermore, it relates to corresponding vermin-deterring compositions which contain these substances as the active ingredient, to compounds of formula (I) for the preparation of vermin-deterring compositions, and to the use of compounds of formula (I) in the defence against vermin.
It has surprisingly been found that the compounds of formula (I) below
or their acid addition salts, wherein
R is hydrogen, C
1
-C
20
-alkyl or —C(O)—R
8
, whereby R
8
is C
1
-C
20
-alkyl, C
1
-C
20
-alkoxy, unsubstituted phenyl or phenyl which is substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, halogen, cyano, hydroxyl, alkoxy, amino or nitro;
R
1
is hydrogen, C
1
-C
20
-alkyl, —C(O)—R
3
, —C(S)—R
4
, C(O)—O—R
5
, —C(O)—NH—R
6
or —C(S)—NH—R
7
; whereby R
3
, R
4
, R
5
, R
6
and R
7
, independently of one another, signify C
1
-C
10
-alkyl, acetoxy, C
1
-C
10
-haloalkyl, C
1
-C
10
-alkoxy or C
1
-C
10
-haloalkoxy, or independently of one another, denote unsubstituted phenyl or phenyl which is substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, halogen, cyano, hydroxyl, C
1
-C
3
-alkoxy, amino, CHO or nitro;
R
2
and R
3
, independently of one another, are hydrogen, C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, halogen, cyano, hydroxyl, amino, aryl, or nitro;
R
a
denotes hydrogen, unsubstituted C
1
-C
20
-alkyl or C
1
-C
20
-alkyl which is substituted once or many times by halogen, cyano, hydroxyl, alkoxy, nitro, phenyl, biphenyl, benzyloxy or phenoxyphenyl, whereby each phenyl, biphenyl, benzyloxy or phenoxyphenyl in turn is unsubstituted or substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, C
1
-C
3
-alkoxy, halogen, cyano, hydroxyl, amino or nitro; or it denotes C
3
-C
8
-cycloalkyl, phenyl, biphenyl, phenoxyphenyl or heterocyclyl, whereby each of these cyclic radicals is unsubstituted or substituted once or many times by C
1
-C
3
-alkyl, C
2
-C
8
-alkenyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, C
1
-C
3
-alkoxy, halogen, cyano, hydroxyl, amino, (C
1
-C
3
-alkyl)
2
N, acetyl or nitro; or it denotes C
1
-C
6
-alkylene-aryl, whereby the aryl radical is unsubstituted or substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, halogen, cyano, hydroxyl or nitro; or it denotes C
1
-C
20
-alkyl which, depending on the number of carbon atoms, is interrupted by oxygen at one or several positions; and
R
b
signifies hydrogen, C
1
-C
20
-alkyl, heterocyclyl or aryl, whereby each of the cyclic radicals is unsubstituted or substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-haloalkoxy, C
2
-C
6
-alkenyl, halogen, cyano, hydroxyl, C
1
-C
3
-alkoxy, amino, (C
1
-C
3
-alkyl)
2
N, or nitro;
are eminently suitable for deterring vermin. Through the usage according to the invention of the above compounds, the most varied vermin of humans, animals, objects or certain places can be deterred, whereby numerous compounds within the scope of formula (I) are notable for their particularly long duration of efficacy.
Compounds of formula (I) having at least one basic centre may form e.g. acid addition salts. These are formed for example with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulphuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, typically C
1
-C
4
alkanecarboxylic acids substituted where appropriate for example by halogen, e.g. acetic acid, such as dicarboxylic acids that are unsaturated where appropriate, e.g. oxalic, malonic, succinic, maleic, fumaric or phthalic acid, typically hydroxycarboxylic acids, e.g. ascorbic, lactic, malic, tartaric or citric acid, or benzoic acid, or with organic sulphonic acids, typically C
1
-C
4
alkanesulphonic or arylsulphonic acids substituted where appropriate for example by halogen, e.g. methanesulphonic or p-toluenesulphonic acid. Of the salts, particular preference is given to those formed with strong acids, especially with mineral acids, in particular with the hydrohalic acids HCI and HBr.
All multiple substitutions are to be interpreted such that identical or different substituents may occur simultaneously.
The alkyl groups present in the definitions of the substituents may be straight-chained or branched, depending on the number of carbon atoms, and they may be for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tetradecyl, hexadecyl, octadecyl or eicosyl, as well as the branched isomers thereof, for example isopropyl, isobutyl, sec.-butyl, tert.-butyl, isopentyl, neopentyl or isohexyl. Alkoxy, haloalkyl and haloalkoxy radicals are derived from the said alkyl groups.
Halo denotes halogen and normally signifies fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine, especially chlorine, whereby the corresponding substituent may contain one or more identical or different halogen atoms.
Halogen-substituted carbon-containing groups, such as haloalkyl or haloalkoxy, may be partially halogenated or perhalogenated, whereby in the case of multiple halogenation, the halogen substituents may be identical or different. Examples of haloalkyl—as a group per se and as structural element of other groups and compounds such as haloalkoxy—are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF
2
or CF
3
; ethyl which is mono- to pentasubstituted by fluorine, chlorine and/or bromine, such as CH
2
CF
3
, CF
2
CF
3
, CF
2
CCl
3
, CF
2
CHCl
2
, CF
2
CHF
2
, CF
2
CFCl
2
, CF
2
CHBr
2
, CF
2
CHClF, CF
2
CHBrF or CClFCHClF; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine and/or bromine, such as CH
2
CHBrCH
2
Br, CF
2
CHFCF
3
, CH
2
CF
2
CF
3
or CH(CF
3
)
2
; and butyl or one of its isomers, mono- to nonasubstituted by fluorine, chlorine and/or bromine, such as CF(CF
3
)CHFCF
3
or CH
2
(CF
2
)
2
CF
3
.
Alkenyl—as a group per se and as structural element of other groups and compounds such as alkeneoxy, halogenalkenyl or halogenalkeneoxy—is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, for example vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, or branched, for example isopropenyl.
Appropriate cycloalkyl substituents contain 3 to 8 carbon atoms and are, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl. Corresponding cycloalkenyl substituents may be mono- or also repeatedly unsaturated, for example cyclopentadienyl or cyclooctatetraenyl. Cyclopentyl and cyclohexyl are preferred.
In the context of the present invention, aryl is understood to be phenyl or naphthyl, especially phenyl. These aryl groups are either unsubstituted or are substituted once or many times by C
1
-C
3
-alkyl, C
1
-C
3
-haloalkyl, C
1
-C
3
-alkoxy, C
1
-C
3
-haloalkoxy, halogen, cyano, hydroxyl, amino or nitro, whereby each multiple substitution is not limited to identical substituents; instead, mixed substituents may appear.
In the context of the present invention, heterocyclyl is understood to mean aliphatic or aromatic and additionally also benzo-condensed cyclic radicals, which contain at least one oxygen, sulphur or nitrogen atom. Five- and six-membered heterocycles are preferred. Heterocyclyl typically includes substituents such as dioxolanyl, pyrrolidinyl, piperidinyl, morpholinyl, pyridyl, pyrryl, furyl, thienyl, imidazolyl, tetrahydrofuryl, tetrahydropyrryl, tetrahydropyranyl, dihydrofuryl, dihydropyranyl, benzofuryl, benzothienyl, isoxazolyl, oxazolyl, thiazolyl, oxazolinyl, oxazolidinyl, indolyl, imidazolinyl, imidazolidinyl and dioxanyl. Preference is given especially to those which are unsubstituted or have one or two halogen atoms, halogen in this case denoting fluorine,
Bouvier Jacques
Christinaz Catherine
Di Criscio Nicola
Froelich Olivier
Levy Neil S.
Marks David L.
Novartis Animal Health US Inc.
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