Carboxylic acid derivatives, their preparation and use
View Patent ↗Carboxylic acid derivatives where R-R 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.
1. A carboxylic acid derivative of the formula I
wherein
R is —CO 2 H or another radical which can be hydrolyzed to —CO 2 H;
R 2 is C 1 -C 4 -alkoxy;
X is CR 14 , where R 14 is hydrogen or C 1 -C 5 -alkyl, or CR 14 forms together with CR 3 a 5- or 6-membered alkylene or alkenylene ring which can be substituted by one or two C 1 -C 4 -alkyl groups and in which in each case a methylene group can be replaced by oxygen;
R 3 is C 1 -C 4 -alkoxy or CR 3 is linked to CR 14 to give a 5- or 6-membered ring;
R 4 and R 5 are independently 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 2 , NH or N-alkyl group or a C 3 -C 7 -cycloalkyl group;
R 6 is hydrogen, C 1 -C 8 -alkyl or C 3 -C 8 -cycloalkyl, where each of these radicals can be substituted by one or more substituents selected from the group consisting of: halogen, nitro, cyano, C 1 -C 4 -alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, C 3 -C 8 -alkylcarbonylalkyl, C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, phenyl and phenoxy which is substituted by one or more substituents selected from the group consisting of: halogen, nitro, cyano, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy and C 1 -C 4 -alkylthio; or phenyl or naphthyl, each of which can be substituted by one or more of the following radicals selected from the group consisting of: halogen, nitro, cyano, hydroxyl, amino, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, phenoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, dioxomethylene and dioxoethylene;
Y is oxygen; and
Z is oxygen.
2. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a direct linkage, R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
3. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a methylene, R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
4. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via CH 2 —CH 2 , R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
5. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
6. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an oxygen atom, R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
7. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a sulfur atom, R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
8. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via NH(CH 3 ), R 1 is hydroxy, R 6 is methyl, R 2 and R 3 each is methoxy, and X is C—H.
9. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a direct linkage, R 1 is hydroxy, R 6 is isopropyl, R 2 and R 3 each is methoxy, and X is C—H.
10. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a direct linkage, R 1 is hydroxy, R 6 is p-isopropylphenyl, R 2 and R 3 each is methoxy, and X is C—H.
11. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a direct linkage, R 1 is hydroxy, R 6 is benzyl, R 2 and R 3 each is methoxy, and X is C—H.
12. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is ethyl, R 2 and R 3 each is methoxy, and X is C—H.
13. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is (CH 3 ) 2 —CH 2 —CH 2 , R 2 and R 3 each is methoxy, and X is C—H.
14. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is cyclopropylmethylene, R 2 and R 3 each is methoxy, and X is C—H.
15. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is methyl, R 2 is methoxy, R 3 is methyl, and X is C—CH 2 —CH 2 —O, wherein X and R 3 together forms a 4-membered ring.
16. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via CH 2 —CH 2 , R 1 is hydroxy, R 6 is ethyl, R 2 is methoxy, and X is C—CH═CH—O, wherein X and R 3 together forms a 4-membered ring.
17. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via an ethenylene, R 1 is hydroxy, R 6 is methyl, R 2 is methoxy, R 3 is methyl, and X is C—CH 2 —CH 2 , wherein X and R 3 together forms a 5-membered ring.
18. The carboxylic acid derivative of claim 1 , wherein R 4 and R 5 each is phenyl connected together in the ortho position via a direct linkage, R 1 is hydroxy, R 6 is methyl, R 2 is methoxy, R 3 is methyl, and X is C—CH 2 —CH 2 —O, wherein X and R 3 together forms a 5-membered ring.