Quinoline compounds
AssigneesThe Green Cross Corporation, Asahi Glass Company, Limited
InventorsYoshihisa Inoue, Hajime Ebisu, Naomichi Ishida, Norifumi Nakamura, Jun Sasaki, Takashi Okazoe, Yoshitomi Morizawa, Arata Yasuda
Life of this patent
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Abstract
A quinoline compound represented by the formula (1) or a salt thereof: ##STR1## wherein the definition of each substituents are described in the specification, which have angiotensin II antagonism and hypotensive action and are useful as an agent for the prevention and treatment of cardiovascular system diseases such as hypertension, heart failure and the like.
Claims8
A 2-(2-carboxyphenyl)-6-methyl-4-quinoline carboxylic acid compound of formula (4):
- ##STR15## wherein R.sup.25 is --COOH or --COOR.sup.11 ;
- R.sup.26 is --COOH or --COOR.sup.12 ;
- R.sup.24, R.sup.27 and R.sup.28 may be the same or different and each independently is a hydrogen atom, a halogen atom, a lower alkyl, alkoxy or C.sub.m F.sub.2m+1 --group, wherein m is an integer of 1 to 6;
- and R.sup.11 and R.sup.12 are the same or different and each independently is a lower alkyl, alkenyl, cyclo lower alkyl, aryl or aralkyl group.
A process for producing a 2-(2-carboxyphenyl)-6-methyl-4-quinoline carboxylic acid compound of formula (4):
- ##STR16## comprising reacting a 5-methylisatin compound of formula (5):
- ##STR17## with a 2-acetyl benzoic acid compound of formula (6):
- ##STR18## wherein R.sup.25 is --COOH or --COOR.sup.11 ;
- R.sup.26 is --COOH or --COOR.sup.12 ;
- R.sup.24 R.sup.27 and R.sup.28 may be the same or different and each independently is a hydrogen atom, a halogen atom, a lower alkyl, alkoxy or C.sub.m F.sub.2m+1 -- group, wherein m is an integer of 1 to 6;
- and R.sup.11 and R.sup.12 are the same or different and each independently is a lower alkyl, alkenyl, cyclo lower alkyl, aryl or aralkyl group.
A process for producing a 2-(6-methylquinolin-2-yl)benzoic acid of formula (4):
- ##STR19## wherein R.sup.25 is a hydrogen atom;
- R.sup.26 is --COOR.sup.12, R.sup.24, R.sup.27 and R.sup.28 may be the same or different and each independently is a hydrogen atom, a halogen atom, a lower alkyl, alkoxy or C.sub.m F.sub.2m+1 -- group, wherein m is an integer of 1 to 6;
- and R.sup.12 is a lower alkyl, alkenyl, cyclo lower alkyl, aryl or aralkyl group, comprising subjecting a 2-(2-carboxyphenyl)-6-methyl-4-quinoline carboxylic acid compound of formula (4) in which R.sup.25 is --COOH and R.sup.26 is --COOR.sup.12 to decarboxylation by heating.
A process for producing a 2-(6-methylquinolin-2-yl)benzoic acid compound of formula (4):
- ##STR20## wherein R.sup.25 is a hydrogen atom;
- R.sup.26 is --COOR.sup.12, R.sup.24, R.sup.27 and R.sup.28 may be the same or different and each independently is a hydrogen atom, a halogen atom, a lower alkyl, alkoxy or C.sub.m F.sub.2m+1 -- group, wherein m is an integer of 1 to 6;
- and R.sup.12 is a lower alkyl, alkenyl, cyclo lower alkyl, aryl or aralkyl group, comprising reacting a 5-methylisatin compound of formula ( 5 ):
- ##STR21## with a 2-acetyl benzoic acid compound of formula (6):
- ##STR22## wherein R.sup.26 is --COOH, thereby converting the resulting 2-(2-carboxyphenyl)-6-methyl-4-quinoline carboxylic acid compound of formula (4) in which R.sup.25 and R.sup.26 each is --COOH into a 2-(2-carboxyphenyl)-6-methyl-4-quinoline carboxylic acid compound of formula (4) wherein R.sup.25 is --COOH and R.sup.26 is --COOR.sup.12 ;
- and subjecting the resulting compound to decarboxylation by heating.
Dependencies are inferred from the claim text.