4-oxoquinoline compounds

Patent metadata

Field	Value
Publication number	US-10522767-B2
Application number	US-201515526866-A
Country	US
Kind code	B2
Filing date	Sep 29, 2015
Priority date	Nov 26, 2014
Publication date	Dec 31, 2019
Grant date	Dec 31, 2019

Abstract

Provided is a 4-oxoquinoline compounds of the formula (I) (I) wherein A is selected from diradicals of the formulae (A.1), (A.2), (A.3), (A.4), (A.5) and (A.6), (A.1) (A.2) (A.3) (A.4) (A.5) (A.6) wherein R 1 , R 2a , R 2b , R 3 , R 3a , if present R 4a , R 4b , R 5a , R 5b , R 6a , R 6b , R 6c , R 6d , R n1 , R n2 , R n3 , R n4 , R m5 , R m6 , R m7 , R m8 , R 7 , R 8a , R 9 and R 9a are as defined in the claims and in the description. Also provided is a method for their preparation and their use.

First claim

The invention claimed is:

1. A compound of formula (I):

wherein:
R 1 , R 2a and R 2b are independently of one another selected from the group consisting of hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, formyl, acyl, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, diaklaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, akisulfonyl, arylsulfonyl, amidino, NE 1 E 2 ,
in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, (monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloakythio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino;
R 3 is hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, alkylsulfonyl, arylsulfonyl, amidino, NE 1 E 2 ,
in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylthio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino;
R 3a is hydrogen, in each case unsubstituted or substituted alkyl or aryl;
X 1 is O or C(CN) 2 ;
A is a diradical selected from diradicals of the general formulae, (A.2), (A.3), (A.4), (A.5), and (A.6):

wherein:
* in each case denotes the point of attachments to the quinoline skeleton and the carbonyl carbon atom;
n is 1, 2, 3 or 4;
m is 1, 2, 3 or 4;
R 4a , R 4b , R 5a , R 5b , R 6a , R 6b , R 6c , R 6d , at each occurrence, R n1 , R n2 , R n3 , R n4 , R m5 , R m6 , R m7 and R m8 , are independently of one another selected from hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, formyl, acyl, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, alkylsulfonyl, arylsulfonyl, amidino, NE 1 E 2 ,
in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, (monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylthio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino;
R 7 , R 8a , R 8b are independently of one another selected from hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, formyl, acyl, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, dialkylaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, alkylsulfonyl, arylsulfonyl, amidino, NE 1 E 2 ,
in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, (monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylthio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino;
R 9 is hydrogen, F, Cl, Br, I, CN, hydroxy, mercapto, nitro, cyanato, thiocyanato, carboxy, carboxylate, alkylcarbonyloxy, carbamoyl, alkylaminocarbonyl, diaklaminocarbonyl, sulfo, sulfonate, sulfoamino, sulfamoyl, akisulfonyl, arylsulfonyl, amidino, NE 1 E 2 ,
in each case unsubstituted or substituted alkyl, alkoxy, alkylthio, (monoalkyl)amino, (dialkyl)amino, cycloalkyl, cycloalkoxy, cycloalkylthio, (monocycloalkyl)amino, (dicycloalkyl)amino, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylthio, (monoheterocycloalkyl)amino, (diheterocycloalkyl)amino, aryl, aryloxy, arylthio, (monoaryl)amino, (diaryl)amino, hetaryl, hetaryloxy, hetarylthio, (monohetaryl)amino and (dihetaryl)amino;
R 9a is hydrogen, in each case unsubstituted or substituted alkyl or aryl; and
X 2 is O or C(CN) 2 ;
wherein:
E 1 and E 2 , at each occurrence, are each independently selected from hydrogen, alkyl, cycloalkyl, heterocycloalkyl, aryl and hetaryl.

2. The compound according to claim 1 , wherein R 1 is hydrogen, chlorine, bromine, C 1 -C 30 -alkyl or C 1 -C 30 -haloalkyl.

3. The compound according to claim 1 , wherein R 2a , R 2b , R 3 and R 3a are hydrogen.

4. The compound according to claim 1 , which corresponds to the formula (I-A):

5. The compound according to claim 4 , wherein R n1 , R n2 , R n3 , R n4 , R 6a , R 6b , are independently of one another, selected from the group consisting of hydrogen, C 1 -C 30 -alkoxy, C 1 -C 30 -alkylsulfanyl, aryloxy and arylthio where the two last mentioned radicals are unsubstituted or carry 1, 2 or 3 substituents selected from the group consisting of SO 3 H, C 1 -C 10 -alkoxy and C 1 -C 10 -alkyl which is unsubstituted or substituted by COOH.

6. The compound according to claim 4 , wherein n is 1 or 2.

7. The compound according to claim 4 , wherein n is 2, and 2 or 4 of the R 12 , R 14 , R 21 and R 23 radicals are each phenyloxy which is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of SO 3 H, C 1 -C 10 -alkoxy and C 1 -C 10 -alkyl which is unsubstituted or substituted by COOH and the remaining radicals R 6a , R 6b , R 11 , R 12 ,R 13 , R 14 , R 21 , R 22 ,R 23 and R 24 are each hydrogen.

8. The compound according to claim 1 , which is selected from the group consisting of compounds of formulae (I-B) and (I-C)

and mixtures thereof.

9. The compound according to claim 8 , wherein R m5 , R m6 , R m7 and R m8 are, independently of one another, selected from the group consisting of hydrogen, C 1 -C 30 -alkoxy, C 1 -C 30 -alkylsulfanyl, aryloxy and arylthio where the two last mentioned radicals are unsubstituted or carry 1, 2 or 3 substituents selected from the group consisting of SO 3 H, C 1 -C 10 -alkoxy and C 1 -C 10 -alkyl, which is unsubstituted or substituted by COOH.

10. The compound according to claim 8 , wherein m is 1 or 2.

11. The compound according to claim 8 , wherein m is 2, and 2 or 4 of the radicals R 15 , R 16 , R 17 , R 18 , R 25 , R 26 , R 27 and R 28 are selected from the group consisting of phenyloxy which is unsubstituted or substituted by 1, 2 or 3 substituents selected from the group consisting of SO 3 H, C 1 -C 10 -alkoxy and C 1 -C 10 -alkyl which is unsubstituted or substituted by COOH and the remaining radicals R 15 ,R 16 , R 17 , R 18 , R 25 , R 26 , R 27 and R 28 are each hydrogen.

12. The compound according to claim 8 , wherein R 2a , R 2b , R 3 , R 8a , R 8b and R 9 are each hydrogen.

13. The compound according to claim 8 , wherein R 1 and R 7 are, indepen

Assignees

• Basf Se
• Max Planck Gesellschaft

Inventors

• Gessner Thomas
• Reichelt Helmut
• Reichert Hans
• Jaensch Daniel
• Chen Long
• Muellen Klaus

Classifications

• C08K5/3437

  condensed with carbocyclic rings · CPC title

• C09B5/62

  Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series · CPC title

• C09D11/50

  Sympathetic, colour changing or similar inks · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09D11/32

  characterised by colouring agents · CPC title