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Details for Patent: 6,197,958

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Details for Patent: 6,197,958

Title: Carboxylic acid derivatives, their preparation and use
Abstract:Carboxylic acid derivatives ##STR1## where R--R.sup.6, X, Y and Z have the meanings stated in the description, and the preparation thereof, are described. The novel compounds are suitable for controlling diseases.
Inventor(s): Riechers; Hartmut (Neustadt, DE), Klinge; Dagmar (Heidelberg, DE), Amberg; Wilhelm (Friedrichsdorf, DE), Kling; Andreas (Mannheim, DE), Muller; Stefan (Speyer, DE), Baumann; Ernst (Dudenhofen, DE), Rheinheimer; Joachim (Lugwigshafen, DE), Vogelbacher; Uwe Josef (Lugwigshafen, DE), Wernet; Wolfgang (Hassloch, DE), Unger; Liliane (Ludwigshafen, DE), Raschack; Manfred (Weisenheim, DE)
Assignee: BASF Aktiengesellschaft (Ludwigshafen, DE)
Filing Date:May 11, 1999
Application Number:09/309,770
Claims:1. A compound of the formula I ##STR16##

where R is formyl, tetrazole, nitrile, a COOH group or a radical which can be hydrolyzed to COOH, and the other substituents have the following meanings:

R.sup.2 hydrogen, hydroxyl, NH.sub.2, NH(C.sub.1 -C.sub.4 -alkyl), N(C.sub.1 -C.sub.4 -alkyl).sub.2, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;

X CR.sup.14 which forms together with CR.sup.3 a 5-membered ring which can be substituted by one or two C.sub.1 -C.sub.4 -alkyl groups;

R.sup.3 is linked to CR.sup.14 as indicated above to give a 5-membered ring;

R.sup.4 and R.sup.5, which can be identical or different, are phenyl or naphthyl, which can be substituted by one or more of the following radicals: halogen, nitro, cyano, hydroxyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, phenoxy, C.sub.1 -C.sub.4 -alkylthio, amino, C.sub.1 -C.sub.4 -alkylamino, or C.sub.1 -C.sub.4 -dialkylamino; or

phenyl or naphthyl, which are connected together in the ortho position via a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or an SO.sub.2, NH or N-alkyl group; or C.sub.3 -C.sub.7 -cycloalkyl;

R.sup.6 hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl, where each of these radicals can be substituted one or more times by: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.8 -alkylcarbonylalkyl, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, phenyl or phenoxy which is substituted one or more times by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; phenyl or naphthyl, each of which can be substituted by one or more of the following radicals: halogen, nitro, cyano, hydroxyl, amino, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, phenoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -dialkylamino or dioxomethylene or dioxoethylene; a five or six-membered heteroaromatic moiety containing one to three nitrogen atoms and/or one sulfur or oxygen atom, which can carry one to four halogen atoms and/or one or two of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, phenyl, phenoxy or phenylcarbonyl, it being possible for the phenyl radicals in turn to carry one to five halogen atoms and/or one to three of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;

Y sulfur or oxygen or a single bond;

Z sulfur, oxygen, --SO-- or --SO.sub.2 --.

2. The compound of the formula I as defined in claim 1, wherein R.sup.14 together with R.sup.3 is a radical selected from the group consisting of --CH.sub.2 --CH.sub.2 --CH.sub.2 -- and --CH.dbd.CH--CH.sub.2 --.

3. The compound of the formula I as defined in claim 1, wherein R is CO.sub.2 H.

4. The compound of the formula I as defined in claim 1, wherein R.sup.2 is methoxy.

5. The compound of the formula I as defined in claim 1, wherein R.sup.4 and R.sup.5 each are phenyl.

6. The compound of the formula I as defined in claim 1, wherein R.sup.6 is C.sub.1 -C.sub.8 -alkyl.

7. The compound of the formula I as defined in claim 1, wherein Y is oxygen.

8. The compound of the formula I as defined in claim 1, wherein Z is oxygen or sulfur.

9. The compound of the formula I as defined in claim 1, wherein Z is oxygen.

10. The compound of the formula I as defined in claim 1, wherein R is tetrazole, nitrile or a group ##STR17##

where R.sup.1 has the following meanings:

a) hydrogen;

b) succinylimidoxy;

c) a five-membered heteroaromatic ring linked by a nitrogen atom, selected from the group consisting of: pyrrolyl, pyrazolyl, imidazolyl and triazolyl, which ring can carry one or two halogen atoms and or one or two of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.4 -alkylthio;

d) a radical ##STR18##

where m is 0 or 1 and R.sup.7 and R.sup.8, which can be identical or different, have the following meanings:

hydrogen,

C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, where these alkyl, cycloalkyl, alkenyl and alkynyl groups can each carry one to five halogen atoms and/or one or two of the following groups: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkynyloxy or C.sub.3 -C.sub.6 alkynylthio,

C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.5 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl or C.sub.3 -C.sub.6 -alkynyloxycarbonyl,

phenyl, which can be substituted one or more times by halogen, nitro, cyano, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio,

di-C.sub.1 -C.sub.4 -alkylamino, or

R.sup.7 and R.sup.6 together form a C.sub.4 -C.sub.7 -alkylene chain which can be substituted by C.sub.1 -C.sub.4 -alkyl, and may contain a hetero atom selected from the group consisting of oxygen, sulfur and nitrogen, or R.sup.7 and R.sup.8 together form a CH.sub.2 --CH.dbd.CH--CH.sub.2 or CH.dbd.CH--(CH.sub.2).sub.3 chain;

e) a radical ##STR19##

where k is 0, 1 and 2, p is 1, 2, 3 and 4, and R.sup.9 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or phenyl, which can be substituted one or more times by halogen, nitro, cyano, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;

f) a radical OR.sup.10, where R.sup.10 is

hydrogen, the cation of an alkali metal or an alkaline earth metal or an environmentally compatible organic ammonium ion;

C.sub.3 -C.sub.8 -cycloalkyl which may carry one to three C.sub.1 -C.sub.4 -alkyl groups;

C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms and/or one of the following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenyl, phenoxy or phenylcarbonyl, where the aromatic radicals in turn may carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;

C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms and which carries one of the following radicals: a 5-membered heteroaromatic ring containing one to three nitrogen atoms or a nitrogen atom and an oxygen or sulfur atom, which may carry one to four halogen atoms and/or one or two of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;

C.sub.2 -C.sub.6 -alkyl which carries one of the following radicals in position 2: C.sub.1 -C.sub.4 -alkoxyimino, C.sub.3 -C.sub.6 -alkynyloxyimino, C.sub.3 -C.sub.6 -haloalkenyloxyimino or benzyloxyimino;

C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl which may carry one to five halogen atoms;

phenyl which may carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;

a 5-membered heteroaromatic ring which is bonded via a nitrogen atom and containing one to three nitrogen atoms, which may carry one or two halogen atoms and or one or two of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, phenyl, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio;

a radical ##STR20##

where R.sup.11 and R.sup.12, which may be identical or different are:

C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, it being possible for these radicals to carry a C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and/or phenyl which may carry one to five halogen atoms and/or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, CL-C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio; phenyl which may carry one or more of the following radicals: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; or R.sup.11 and R.sup.12 together form a C.sub.3 -C.sub.12 -alkylene chain which may carry one to three C.sub.1 -C.sub.4 -alkyl groups and which may contain a hetero atom selected from the group consisting of nitrogen, oxygen and sulfur;

g) a radical ##STR21##

where R.sup.13 is

C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, it being possible for these radicals to carry a C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio and/or a phenyl radical, or

phenyl which may carry one or more of the following radicals: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio.
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