Sankyo Company, Limited

Fujirebio Inc.

Eiko Mori

Tomoyuki Kurumada

Toshimasa Toda

Katsuaki Matsui

Takao Yoshioka

Keisuke Murayama

Hideo Horiuchi

Susumu Higashida

Syoji Morimura

Noriyuki Ohta

Nobuko Watanabe

Masakatsu Matsumoto

Hisayou Ohsawa

Hiroshi Ikawa

Hisako Kobayashi

Hisayou Osawa

Tetsuaki Yamaura

Misao Aoyama

Miwa Ishihara

Noriyuki Ohata

Jun Kusunoki

Noriyuki Onta

Ichiro Watanabe

Masakatsu Matumoto

Keisuku Murayama

Syoji Moriyama

Methods of producing carboxylic acid ester derivatives of formulae (I) and (II), which are useful, for instance, as intermediates for producing an anti-hypercholesterolemic agent having an inhibitory effect on HMG-CoA Reductase: ##STR1## wherein R.sup.1 and R.sup.2 are independently a protective group for hydroxyl group, or R.sup.1 and R.sup.2 integrally constitute a protective group for hydroxyl groups; R.sup.3 is an alkyl group, or an aryl group; and R.sup.4 is a substituted aryl group, a substituted heterocyclic group, a substituted vinyl group, or a substituted cycloalkenyl group; and ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are respectively the same as defined in the above formula (I), are disclosed. In addition, intermediates for use in these methods of producing the carboxylic acid ester derivatives are disclosed.

Methods of producing carboxylic acid ester derivatives and intermediates

A 4-fluorobiphenyl derivative of formula (I), which is useful as a cholesterol lowering agent or a lipid lowering agent because of its strong inhibitory effect on HMG-CoA reductase), and which is also useful as an intermediate for producing the above-mentioned cholesterol lowering agent or lipid lowering agent: ##STR1## wherein A is a .omega.-oxycarbonyldihydroxybutyl group, a tetrahydropyranyl group, a .omega.-oxycarbonyl-3-oxobutyl group, a formyl group, or a cyano group; R.sup.1 is a halogen atom, an alkyl group, or a group represented by R.sup.5 O--, wherein R.sup.5 is a hydrogen atom, or an alkyl group; R.sup.2 is a hydrogen atom, an alkyl group; R.sup.3 is a hydrogen atom, or an alkyl group; R.sup.5 and R.sup.2 may form a five-membered ring or a six-membered ring in combination with the oxygen atoms to which R.sup.5 and R.sup.2 are respectively bonded, and R.sup.5 and R.sup.3 may form a five-membered ring or a six-membered ring in combination with the oxygen atom to which R.sup.5 is bonded.

4-fluorobiphenyl derivatives

A 4-fluorobiphenyl derivative of formula (I): ##STR1## wherein A is a .omega.-oxycarbonyldihydroxybutyl group of formula (II): ##STR2## wherein R.sup.2 is a hydrogen atom, an alkyl group, an alkaline metal or an alkaline earth metal; a tetrahydropyranyl group of formula (III): ##STR3## or a .omega.-oxycarbonyl-3-oxobutyl group of formula (IV): ##STR4## wherein R.sup.3 is an alkyl group; R.sup.1 is an alkyl group. This 4-fluorobiphenyl derivative is useful as an effective component for a cholesterol or lipid lowering agent.

4-hydroxytetrahydropyran-2-one and 3,5-Dihydroxyheptanoic acid derivatives of formula (I) and formula (II) have an inhibition effect on HMG-CoA reductase, a cholesterol value reduction effect, and an antioxidation function, thus serving as cholesterol reducing agent or lipid reducing agents: ##STR1## wherein R.sup.1 represents hydrogen, a nitro group, or -N(R.sup.4)R.sup.5 in which R.sup.4 and R.sup.5 each represent an alkyl group, an alkenyl group, an aryl group, an aralkyl group; an acyl group, an aroyl group, a carbamoyl group, or a thiocarbamoyl group, and R.sup.4 and R.sup.5 may be combined to form a cyclic amino group; and R.sup.2 and R.sup.3 each represent hydrogen or an alkyl group; and R.sup.6 represents hydrogen, an alkyl group, an alkali metal, or an alkaline earth metal.

3,5-dihydroxyheptanoic acid derivatives

4-hydroxytetrahydropyran-2-one derivatives with general formula (I) are useful as cholesterol reducing agents as well as lipid reducing agents, serving as inhibitors of HMG-CoA reductase, and capable of inhibiting the biosynthesis of peroxidized lipids, and therefore effective for curing arteriosclerosis: ##STR1## wherein R.sub.1 represent hydrogen or a 2-tetrahydropyranyl group; R.sub.2 and R.sub.3 each represent hydrogen or an alkyl group having 1 to 6 carbon atoms; R.sub.4 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an aryl group, an aralkyl group, an acyl group, an aroyl group or a substituted sulfonyl group; A represents --CH.sub.2 CH.sub.2 --, or --CH.dbd.CH--; and n is an integer of 1 or 2, and intermediates for synthesizing the 4-hydroxytetrahydropyran-2-one derivatives are disclosed.

4-Hydroxytetrahydropyran-2-one derivatives

Piperidine derivatives having the formula ##STR1## wherein R' represents an alkyl, an acyl, an alkoxycarbonyl, an amino or nitroso group;

Piperidine derivatives

A novel piperidine derivative having a stabilizing effect on a synthetic polymeric material and a composition comprising said piperidine derivative and a synthetic polymeric material.

A synthetic polymer composition stabilized against photo- and thermal-deterioration comprising a stabilizing amount of a compound having the formula ##STR1## wherein R' represents an alkyl, an acyl, an alkoxycarbonyl, an amino or nitroso group;

Polymer compositions containing piperidine derivatives as stabilizers

Novel piperidine derivatives of formula: ##STR1## (wherein 2 or 3 of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent alkyl groups having from 1 to 4 carbon atoms and the remainder of R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen atoms, and R.sub.6 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, a substituted alkyl group, an aliphatic acyl group, an alkoxycarbonyl group or an aralkoxycarbonyl group) are useful as stabilizers for synthetic polymers.

Novel piperidine derivatives for the stabilization of synthetic polymers

Piperidine-spiro-hydrantoin derivatives having the formula ##STR1## wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive; and

Piperidine-spiro-hydantoin derivatives

Piperidine-spiro-hydantoin derivatives having the formula ##SPC1## Wherein X represents oxygen atom or sulfur atom; n is an integer of 1 to 4 inclusive, and R represents various aliphatic or aromatic groups depending on the value of n. These compounds (I) are useful as stabilizers against photo and thermal deterioration of various synthetic polymers and can be prepared, for example, by reacting the corresponding 3-unsubstituted piperidine-spiro-hydantoin compound with the halide R-(X.sub.1).sub.n in which R and n are as defined herein and X.sub.1 is a halogen atom.

Piperidine-spiro-hydantoin derivatives and their use as stabilizers

Piperidine derivatives having the formula ##SPC1## Wherein

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Eiko Mori