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Details for Patent: 5,102,888

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Details for Patent: 5,102,888

Title: Quinoline type mevalonolactones useful for treating hyperlipidemia and related diseases
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, or 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 (Shiraoka, JP), Kitahara; Masaki (Shiraoka, JP)
Assignee: Nissan Chemical Industries Ltd. (Tokyo, JP)
Filing Date:Feb 23, 1990
Application Number:07/483,724
Claims:1. A compound of the formula ##STR18## wherein R.sup.1 and R.sup.2 are ortho to each other and together form --OCR.sup.15 R.sup.16 O--, wherein R.sup.15 and R.sup.16 are independently H or C.sub.1-3 alkyl; 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-butoxy, i-butoxy, sec-butoxy, R.sup.7 R.sup.8 N--, (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), 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.sub.3 and R.sub.4 together form --CH.dbd.CH--CH.dbd.CH--; 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, ##STR19## (where Q is --(CO)--, --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 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 alkylamine, di-lower alkylamine or tri-lower alkylamine)); two R.sup.13 are independently primary or secondary C.sub.16 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, ##STR20## (wherein R.sup.9 is hydrogen, C.sub.1-4 alkyl, C.sub.1-3 alkyl, fluoro, chloro, bromo trifluoromethyl), phenyl--(CH.sub.2).sub.n CH(CH.sub.3)--phenyl or phenyl--(CH.sub.2).sub.n CH(CH.sub.3)--phenyl (wherein n is 0, 1 or 2).

2. The compound of claim 1, wherein R.sup.1 and R.sup.2 together form methylenedioxy.

3. The compound of claim 2, wherein said methylenedioxy is attached to the quinoline moiety at positions 6 and 7 or 7 and 8.

4. The compound of claim 3, wherein R.sup.6 is hydrogen.

5. The compound of claim 3, wherein R.sup.3 is hydrogen.

6. The compound according to claim 1, which is (E)-3,5-dihydroxy-7-[4'-(4"-fluorophenyl)-6',7'-methylenedioxy-2'-(1"-meth ylethyl)-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.

7. The compound according to claim 1, which is (E)-3,5-dihydroxy-7-[4'-(4"-fluorophenyl)-7',8'-methylenedioxy-2'-(1"-meth ylethyl)-6'-chloro-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.

8. The compound according to claim 1, which is (E)-3,5-dihydroxy-7-[2'-cyclopropyl-4'-(4"-fluorophenyl)-6',7'-methylenedi oxy-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.

9. The compound according to claim 1, which is (E)-3,5-dihydroxy-7-[2'-cyclopropyl-4'-(4"-fluorophenyl)-7',8'-methylenedi oxy-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.

10. A method for treating hyperlipidemia, which comprises administering an effective amount of the compound of the formula I as defined in claim 1.

11. A method for treating hyperlipoproteinemia which comprises administering an effective amount of the compound of the formula I as defined in claim 1.

12. A method for treating atherosclerosis which comprises adminstering an effective amount of the compound of the formula I as defined in claim 1.
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