C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/254
C07D 239/80 (2006.01)
Patent
CA 1224468
ORTHO SUBSTITUTED DIHYDROXY-2(1H)QUINAZOLINONE-1-ALKANOIC ACIDS ABSTRACT The synthesis of substituted quinazolinones is described. The novel quinazolinones are renal vasodilators and thereby increase renal blood flow, and are useful as cardiovascular agents. The substituted quinazolinones have the following formula Image wherein R1 is hydrogen, amino or nitro; R2 is hydrogen, alkyl having 1-20 carbon atoms, cycloalkyl having 4-8 carbon atoms, cycloalkylalkyl wherein the cycloalkyl group has 4-8 carbon atoms and the alkyl group has 1-3 carbon atoms, haloalkyl having 1-3 halogen atoms and 1-4 carbon atoms and the halogen is chloro, bromo or fluoro, and bicycloalkyl such as norbornyl and norbornylmethyl; R3 and R4 may be the same or different and are hydrogen, lower alkyl having 1-6 carbon atoms, aryl and substituted aryl such as phenyl, 2-, 3-, and 4-pyridyl, o-, m-, and p- hydroxyphenyl, halophenyl such as p-chlorophenyl, p- fluorophenyl, o-chlorophenyl, 2,4-difluorophenyl, lower alkoxyphenyl such as methoxy, ethoxy, and butoxyphenyl, alkylphenyl wherein the alkyl group contains 1-6 carbon atoms; X is benzyl, carboxy, carboalkoxy wherein the alkoxy group has 1-3 carbon atoms, cyano, carboxamido, methanesulfonyl, formyl, aroyl, such as benzoyl, substitu- ted benzoyl wherein the substituent is an alkyl group having 1-4 carbon atoms, heteroaryl such as 2-, 3-, and 4- pyridyl, and 2-thienyl; heteroaroyl, such as 2-, 3-, and 4-pyridoyl, 2-thienoyl, 2-furoyl and 3-(1,2,5-) thiadia- zolyl; R5 is hydrogen, lower alkyl having 1-6 carbons; benzyl or substituted benzyl wherein the substituent is fluoro, chloro, bromo, alkyl or alkoxy wherein the alkyl group has 1-6 carbon atoms; provided that when R5 is other than hydrogen the compound is a quaternary salt when the 3,4-imine linkage is unsaturated; (the presence of an unsaturated imine linkage between N3 and C4 is optional and N3 may or may not be substituted); Y and Z are hydrogen or hydroxy.
509685
Bandurco Victor T.
Levine Seymour D.
Mulvey Dennis M.
Tobia Alfonso J.
Gowling Lafleur Henderson Llp
Ortho Pharmaceutical Corporation
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