Details for Patent: 5,011,930
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Title: | Quinoline type mevalonolactones |
Abstract: | A compound of the formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.6 are independently hydrogen, C.sub.1-6 alkyl, C.sub.1-6 cycloalkyl, C.sub.1-3 alkoxy, n-botoxy, i-botoxy, sec-butoxy, R.sup.7 R.sup.8 N-- (wherein R.sup.7 and R.sup.8 are independently hydrogen or C.sub.1-3 alkyl), trifluoromethyl, trifluoromethoxy, difluoromethoxy, fluoro, chloro, bromo, phenyl, phenoxy, benzyloxy, hydroxy, trimethylsilyloxy, diphenyl-t-butylsilyloxy, hydroxymethyl or --O(CH.sub.2).sub.l OR.sup.19 (wherein R.sup.19 is hydrogen or C.sub.1-3 alkyl, and l is 1,2 or 3); or when located at the ortho position to each other, R.sup.1 and R.sup.2, and R.sup.3 and R.sup.4 together form --CH.dbd.CH--CH.dbd.CH--; or when located at the ortho position to each other, R.sup.1 and R.sup.2 together form --OC(R.sup.15)(R.sup.16)O-- (wherein R.sup.15 and R.sup.16 are independently hydrogen or C.sub.1-3 alkyl); Y is --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH.sub.2 CH.dbd.CH-- or --CH.dbd.CH-- CH.sub.2 --; and Z is --Q--CH.sub.2 WCH.sub.2 --CO.sub.2 R.sup.12, ##STR2## (wherein Q is --C(O)--, --C(OR.sup.13).sub.2 -- or --CH(OH)--; W is --C(O)--, --C(OR.sup.13).sub.2 -- or --C(R.sup.11)(OH)--; R.sup.11 is hydrogen atom or C.sub.1-3 alkyl; R.sup.12 is hydrogen or R.sup.14 (wherein R.sup.14 is physiologically hydrolyzable alkyl or M (wherein M is NH.sub.4, sodium, potassium, 1/2 calcium or a hydrate of lower alkyl amine, di-lower alkyl amine or tri-lower alkyl amine)); two R.sup.13 are independently primary or secondary C.sub.1-6 alkyl; or two R.sup.13 together form --(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.3 ; R.sup.17 and R.sup.18 are independently hydrogen or C.sub.1-3 alkyl; and R.sup.5 is hydrogen, C.sub.1-6 alkyl, C.sub.2-3 alkenyl, C.sub.3-6 cycloalkyl, ##STR3## (wherein R.sup.9 is a hydrogen atom, C.sub.1-4 alkyl, C.sub.1-3 alkoxy, fluoro, chloro, bromo or trifluoromethyl), phenyl-(CH.sub.2).sub.m -- (wherein m is 1,2 or 3), --(CH.sub.2).sub.n CH(CH.sub.3)-phenyl or phenyl-(CH.sub.2).sub.n CH(CH.sub.3)-- (wherein n is 0,1 or 2). |
Inventor(s): | Fujikawa; Yoshihiro (Funabashi, JP), Suzuki; Mikio (Funabashi, JP), Iwasaki; Hiroshi (Funabashi, JP), Sakashita; Mitsuaki (Shitaoka, JP), Kitahara; Masaki (Shitaoka, JP) |
Assignee: | Nissan Chemical Industries Ltd. (Tokyo, JP) |
Filing Date: | Feb 23, 1990 |
Application Number: | 07/483,720 |
Claims: | 1. A compound of the formula ##STR17## wherein R.sup.1 is hydrogen, 5-fluoro, 6-fluoro, 7-fluoro, 8-fluoro, 5-chloro, 6-chloro, 7-chloro, 8-chloro, 5-bromo, 6-bromo, 7-bromo, 8-bromo, 5-methyl, 6-methyl, 7-methyl, 8-methyl, 5-methoxy, 6-methoxy, 7-methoxy, 8-methoxy, 5-trifluoromethyl, 6-trifluoromethyl, 7-trifluoromethyl, 8-trifluoromethyl, 6-trifluoromethoxy, 6-difluoromethoxy, 8-hydroxyethyl, 5-hydroxy, 6-hydroxy, 7-hydroxy, 8-hydroxy, 6-ethyl, 6-n-butyl or 7-dimethylamino; R.sup.2, R.sup.3 and R.sup.6 are hydrogen, R.sup.4 is hydrogen, 4'-chloro or 4'-fluoro, R.sup.5 is i-propyl or cyclopropyl, Y is (E) --CH.dbd.CH--, and Z is ##STR18## --CH(OH)CH.sub.2 CH(OH)CH.sub.2 CO.sub.2 R.sup.12, --CH(OH)CH.sub.2 C(O)CH.sub.2 CO.sub.2 R.sup.12 or --CH(OH)CH.sub.2 C(OR.sup.13).sub.2 CH.sub.2 CO.sub.2 R.sup.12, wherein R.sup.12 is hydrogen, physiologically hydrolyzable alkyl, NH.sub.4. sodium, potassium 1/2 calcium, or a hydrate of lower alkylamine, di-lower alkylamine or tri-lower alkylamine; two R.sup.13 are independently primary or secondary C.sub.1-6 alkyl; or two R.sup.13 together form --(CH.sub.2).sub.2 -- or --CH.sub.2).sub.3 --. 2. The compound (E)-3,5-dihydroxy-7[5',6'-(1",3"-butadienyl)-4'-(4"-fluorophenyl)-2'-(1"-m ethylethyl)-quinolin-3'-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt or C.sub.1-3 alkyl ester of the carboxylic acid. 3. The compound (E)-3,5-dihydroxy-7-[6',7'-(1",3"-butadienyl)-4'-(4"-fluorophenyl)-2'-(1"- methylethyl)-6'-chloro-quinolin-3,-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt or C.sub.1-3 alkyl ester of the carboxylic acid. 4. The compound (E)-3,5-dihydroxy-7-[7',8'-(1",3"-butadienyl)-4'-(4"-fluorophenyl)-2'-(1"- methylethyl)-quinolin-3'-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt or C.sub.1-3 alkyl ester of the carboxylic acid. 5. The compound (E)-3,5-dihydroxy-7-[5',6'-(1",3"-butadienyl)-2'-cyclopropyl-4'-(4"-fluoro phenyl)-quinolin-3'-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt or C.sub.1-3 alkyl ester of the carboxylic acid. 6. The compound (E)-3,5-dihydroxy-7-[5',6'-(1",3"-butadienyl)-2'-cyclopropyl-4'-(4"-fluoro phenyl)quinolin-3'-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt of C.sub.1-3 alkyl ester of the carboxylic acid. 7. The compound (E)-3,5-dihydroxy-7-[7',8'-(1",3"-butadienyl)-2'-cyclopropyl-4'-(4"-fluoro phenyl)-quinolin-3'-yl]-hept-6-enoic acid, a lactone formed by the condensation of the carboxylic acid with hydroxy at the 5-position, or a sodium salt or C.sub.1-3 alkyl ester of the carboxylic acid. |