.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Claims for Patent: 5,703,017

« Back to Dashboard

Claims for Patent: 5,703,017

Title: 3-(Het) arylcarboxylic acid derivatives, their preparation and intermediates for their preparation
Abstract:3-(Het)arylcarboxylic acid derivatives of the formula I ##STR1## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and the other substituents have the following meanings: R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms an alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen; R.sup.4 is phenyl or naphthyl, each of which is unsubstituted or substituted or an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom; R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or phenyl; R.sup.6 is 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.4 -cyclo-alkyl, each of which may be mono- or polysubstituted; Y is sulfur, oxygen or a single bond; and Z is sulfur or oxygen; with the proviso that R.sup.6 is not unsubstituted C.sub.1 -C.sub.4 -alkyl when R.sup.4 is unsubstituted phenyl, Z is oxygen and simultaneously R.sup.5 is methyl or hydrogen.
Inventor(s): Baumann; Ernst (Dudenhofen, DE), Rheinheimer; Joachim (Ludwigshafen, DE), Vogelbacher; Uwe Josef (Ludwigshafen, DE), Bratz; Matthias (Speyer, DE), Theobald; Hans (Limburgerhof, DE), Gerber; Matthias (Limburgerhof, DE), Westphalen; Karl-Otto (Speyer, DE), Walter; Helmut (Obrigheim, DE), Rademacher; Wilhelm (Limburgerhof, DE)
Assignee: BASF Aktiengesellschaft (Ludwigshafen, DE)
Application Number:08/537,843
Patent Claims: 1. A 3-(het)arylcarboxylic acid derivative of the formula I ##STR15## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and R.sub.2 is 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 is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms a 3-membered or 4-membered alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen;

R.sup.3 is 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 or R.sup.3 is linked to R.sup.14 as stated above to form a 5-membered or 6-membered ring;

R.sup.4 is phenyl or naphthyl which may be substituted by one or more, in particular one to three, of the following radicals: halogen, nitro, cyano, hydroxyl, mercapto, 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl;

a five-membered or six-membered heteroaromatic structure which contains one to three nitrogen atoms and/or one sulfur or oxygen atom and may carry one or more of the following radicals: halogen, nitro, cyano, hydroxyl, mercapto, 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, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -dialkylamino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or phenyl;

R.sup.5 is hydrogen, 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, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkylthioalkyl or phenyl;

R.sup.6 is 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, it being possible for these radicals to be mono- or polysubstituted in each case 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.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, phenyl or phenyl or phenoxy which is mono- or polysubstituted, for example mono- to trisubstituted, 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;

Y is sulfur or oxygen or a single bond; and

Z is sulfur or oxygen;

with the proviso that R.sup.6 is not unsubstituted C.sub.1 -C.sub.4 -alkyl when R.sup.4 is unsubstituted phenyl, Z is oxygen and simultaneously R.sup.5 is methyl or hydrogen.

2. A 3-(het)arylcarboxylic acid derivative of the general formula I as claimed in claim 1, where R is ##STR16## where R.sup.1 has the following meanings: a) hydrogen;

b) a succinylimidoxy group;

c) a 5-membered heteroaromatic structure which is bonded via a nitrogen atom, contains two or three nitrogen atoms and may carry one or two halogen atoms 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.1 -C.sub.4 -alkylthio;

d) a radical ##STR17## where m is 0 or 1 and R.sup.7 and R.sup.8, which may 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 or C.sub.3 -C.sub.8 -cycloalkyl, where each of these radicals may carry one to five halogen atoms or one or two of the following groups: 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.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkynylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, C.sub.3 -C.sub.6 -alkynyloxycarbonyl, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkyl, phenyl or phenyl which is monosubstituted or polysubstituted 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 which may be substituted by 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;

R.sup.7 and R.sup.8 together form a cyclic, optionally substituted C.sub.4 -C.sub.7 -alkylene chain or together form a cyclic, optionally substituted C.sub.3 -C.sub.6 -alkylene chain containing a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen;

e) R.sup.1 is furthermore a group ##STR18## where R.sup.9 is C.sub.1 -C.sub.4 -alkyl, phenyl or phenyl which is monosubstituted or polysubstituted 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, or C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, p may be 1, 2, 3 or 4 and k may be 0, 1 or 2;

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

i) hydrogen, an alkali metal cation, one equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion;

ii) C.sub.3 -C.sub.8 -cycloalkyl Which may carry one to three C.sub.1 -C.sub.4 -alkyl radicals;

iii)C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms 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 each carry one to five halogen atoms 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 or C.sub.1 -C.sub.4 -alkylthio;

iv) C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic structure containing one to three nitrogen atoms or a 5-membered heteroaromatic structure containing one nitrogen atom and one oxygen or sulfur atom, which may carry one to four halogen atoms 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, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;

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

vi) C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, where these groups in turn may carry one to five halogen atoms;

vii)phenyl which may carry one to five halogen atoms 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 or C.sub.1 -C.sub.4 -alkylthio;

viii) a 5-membered heteroaromatic structure which has bonded via a nitrogen atom, contains one to three nitrogen atoms and may carry one or two halogen atoms 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, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio;

ix) R.sup.10 is furthermore a group ##STR19## where R.sup.11 and R.sup.12 , may be identical or different and are each:

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 these radicals may carry one C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio or one phenyl radical;

phenyl which may be substituted by 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;

g) or R.sup.1 forms a radical ##STR20## 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 or C.sub.3 -C.sub.8 -cycloalkyl, where these radicals may carry one C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio or one phenyl radical;

phenyl which may be substituted by one to five halogen atoms 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 or C.sub.1 -C.sub.4 -alkylthio.

3. A 3-arylcarboxylic acid derivative of the formula I as claimed in claim 1, in which R.sup.4 is phenyl which may be substituted as stated in claim 1, and the remaining substituents have the meanings stated in claim 1.

4. A 3-arylcarboxylic acid derivative of the formula I as claimed in claim 1, in which Z is oxygen, R.sup.4 is phenyl which may be substituted as stated in claim 1, R.sup.5 is methyl, X is CH, R.sup.2 and R.sup.3 are each methoxy and Y, R.sup.1 and R.sup.6 have the meanings stated in claim 1.

5. A 3-hetarylcarboxylic acid derivative of the formula I as claimed in claim 1, in which R.sup.4 is a five- or six-membered heteroaromatic structure as claimed in claim 1 and the remaining substituents have the meanings stated in claim 1.

6. A 3-hetarylcarboxylic acid derivative of the formula I as claimed in claim 1, in which Z is oxygen, R.sup.4 is a five- or six-membered heteroaromatic structure as claimed in claim 1, R.sup.5 is methyl, X is CH, R.sup.2 and R.sup.3 are methoxy and Y, R.sup.1 and R.sup.6 have the meanings stated in claim 1.

7. A herbicide containing a compound of the formula I as claimed in claim 1 and conventional inert additives.

8. A method for controlling undesirable plant growth, wherein a herbicidal amount of a compound of the formula I as claimed in claim 1 is allowed to act on the plants or on their habitat.

9. An agent for influencing plant growth, containing a compound of the formula I as claimed in claim 1 and conventional inert additives.

10. A method for regulating plant growth, wherein a bioregulatory amount of a compound of the formula I as claimed in claim 1 is allowed to act on the plants or on their habitat.

11. A 3-(het)arylcarboxylic acid derivative of the formula VI ##STR21## where R, R.sup.4, R.sup.5, R.sup.6 and Z have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen.

12. A process for the preparation of a 3-(het)arylcarboxylic acid derivative of the formula VI ##STR22## wherein an epoxide of the formula IV ##STR23## where R, R.sup.4 and R.sup.5 have the meanings stated in claim 1, is reacted with a compound of the formula V

where R.sup.6 and Z have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen, if required in an inert solvent or with the addition of a suitable catalyst.

13. A process for the preparation of 3-(het)arylcarboxylic acid derivatives of the formula I as claimed in claim 1, where is oxygen wherein the 3-het(aryl)carboxylic acid derivative of the formula VI ##STR24## where the substituents have the meanings stated in claim 1, is reacted with a pyrimidyl or triazinyl derivative of the formula VII ##STR25## where R.sup.15 is halogen or R.sup.16 SO.sub.2 -- and R.sup.16 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or phenyl, in an inert solvent in the presence of a base.

14. A process for the preparation of a 3-het(aryl)carboxylic acid derivative of the formula I as claimed in claim 1, where Y is sulfur, wherein a 3-het(aryl)carboxylic acid derivative of the formula VIII ##STR26## where the substituents have the meanings stated in claim 12, is reacted with a pyrimidyl--or triazinylthiol of the formula IX ##STR27## where R.sup.2, R.sup.3 and X have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

`abc