Kuraray Co., Ltd.

Taisho Pharmaceutical Co., Ltd.

Taiho Pharmaceutical Company Limited

Kyowa Gas Chemical Industry Company, Ltd.

Takashi Nishida

Yoshiji Fujita

Kazuo Itoi

Yoshiaki Omura

Fumio Mori

Takeo Hosogai

Yoshin Tamai

Yoichi Ninagawa

Fumio Wada

Sukeji Aihara

Manzo Shiono

Masao Mizuno

Takashi Ohnishi

Koichi Ibata

Michihiro Ishiguro

Masafumi Okada

Koichi Kanehira

Tetsuo Takigawa

Yasuyuki Tanaka

Masahisa Tanomura

Shigeaki Suzuki

Tetsuo Takematsu

Makoto Konnai

Yutaka Mizushima

Takashi Onishi

Takehiro Amano

Michio Terasawa

Kensei Yoshikawa

Yutaka Ohuchi

Rie Igarashi

Tatsuhiko Sano

Iwao Ebashi

Noriyuki Yamamoto

Shigeru Tsukagoshi

Hirofusa Ajioka

Kenzo Arizono

Shuji Miki

Keiko Hoshi

Masahito Komuro

Tazuko Tashiro

Kouichiro Kawai

Masayuki Inoue

Sigeru Torii

Johji Yamahara

Kenji Uneyama

Kozo Nakao

Haruo Nagai

Toshiaki Takagi

Yutaka Omura

Hiroyuki Nomori

Takuo Kawaguchi

Shizuo Mawatari

11.beta.,17.alpha.,21-Trihydroxy-1,4-pregnadiene-3,20-dione 21-[(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienoate] of the formula ##STR1## an antiinflammatory composition thereof and a method for the production thereof. 11.beta.,17.alpha.,21-Trihydroxy-1,4-pregnadiene-3,20-dione 21-[(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienoate] of the present invention exhibits remarkably excellent antiinflammatory action and besides, displays reduced side effects and can be produced in high selectivity and good yield and conveniently.

11-beta, 17-alpha, 21-trihydroxy-1, 4-pregnadiene-3, 20 21-[(E-E)-3,7,

A pullulan derivative having one or more active sites resulting from introduction of sulfuric acid, phosphoric acid, a sulfonic acid or a carboxylic acid, wherein one hydrogen atom of the group of the formula ##STR1## occurring at said active sites is partly substituted by a group of the general formula ##STR2## wherein L.sup.1 and L.sup.2 each independently is amine or a unidentate ligand amine or combinedly represent a bidentate ligand amine and Y is an anionic ligand, and/or two hydrogen atoms of the group ##STR3## groups bound to one and the same carbon atom or to two neighboring carbon atoms as occurring at said active sites are, each independently, partly substituted by a group of the general formula ##STR4## wherein L.sup.1 and L.sup.2 are as defined above, and a pharmacologically acceptable salt thereof. The above compound has anticancer activity and is useful as anticancer agents. The present invention is concerned with said compound, a process for producing the same and a pharmaceutical use thereof.

Platinum containing pullulan derivatives and pharmaceutical compositions

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mamammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Polyprenyl composition or compounds and process for the production

11.beta., 17.alpha.,21-trihydroxy-1,4-pregnadiene-3,20-dione

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Polyprenyl composition of compounds and process for the production

Platinum containing pullulan derivatives and compositions containing the

A polyprenyl composition consisting essentially of a mixture of polyprenyl compounds represented by the following formula ##STR1## wherein A.sub.1 represents a hydroxyl or acetyloxy group, ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, and n is an integer of from 11 to 19, said mixture containing substantial amounts of at least three compounds of formula (I) wherein n represents 14, 15 and 16 respectively as essential ingredients in a total amount of at least 70% by weight based on the weight of the mixture; and new compounds derived from the polyprenyl compounds of formula (I). These composition and compounds are useful for the synthesis of mammalian dolichols. The polyprenyl composition can be prepared by extracting the leaves of Ginkgo biloba or Cedrus deodara with an oil-soluble organic solvent; if required, hydrolyzing the extract; and subjecting the extract to one or more of chromatography, fractional dissolution, fractional refrigerating precipitation and molecular distillation, thereby separating and recovering a fraction having a specified Rf value in silica thin-layer chromatography.

Novel chroman compounds which have excellent antioxidant activity and/or analgesic activity or serve as precursors for such active compounds are provided. There are also provided uses of these active compounds as an antioxidant and/or analgesic.

Chroman compounds useful as analgerics and antioxidants

Novel 3,4-dihydrobenzopyran compounds of the formula: ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are each hydrogen or nicotinoyl group and at least one of them is nicotinoyl group, m is an integer of 0, 1 or 2, and n is an integer of 0 or 1, which is useful for prophylaxis and treatment of hyperlipemia and the compounds wherein R.sup.1 and R.sup.3 being nicotinoyl group and n is 0 being also effective for prophylaxis and treatment of hepatic diseases, and pharmaceutical composition containing said compounds as an active ingredient.

3,4-dihydrobenzopyran compounds and pharmaceutical composition

Polyprenols or esters thereof, which are similar in the trans and cis configurations to dolichol, or mixtures thereof are obtained from the leaves of plants belonging to the genus Pinus L. of the family Pinaceae by extraction, if necessary followed by hydrolysis, esterification or transesterification or a combination thereof. These polyprenyl compounds and mixtures thereof are useful as favorable starting materials for the synthesis of dolichol.

Method of preparing polyprenyl compounds or mixtures thereof

Novel trimethylcyclohexenyl compounds of the 1,3,3-trimethyl-1-cyclohexene type having a 3-hydroxy-3-lower alkylpropionyl group at the 6-position of the cyclohexene are provided. These trimethylcyclohexenyl compounds have a floral note reminiscent of a variety of odors. There are also provided aroma compositions containing these compounds.

Trimethylcyclohexenyl compounds and aroma compositions containing the

Novel polyprenyl compounds have the general formula: ##STR1## represents a cis-isoprene unit, n is an integer of 11-19, Z.sup.1 is --CH.sub.2 OH or a functional precursor thereof, and either one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is --S(O).sub.m R.sup.3 in which m is an integer of 0 (zero), 1 or 2 and R.sup.3 is a phenyl, naphthyl, pyridyl or thiazolinyl group or such group substituted with at least one lower alkyl and/or halogen substituent. The topic novel polyprenyl compounds can be synthesized from derivatives of the polyprenol which is obtainable from leaves of Ginkgo biloba or Cedrus deodara, among others, by extraction, if necessary followed by hydrolytic treatment. The novel polyprenyl compounds can be converted to mammalian dolichols or precursors thereof by reductive elimination of the --S(O).sub.m R.sup.3 group.

Certain polyprenyl intermediates

There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group. These polyprenyl compounds can be synthesized starting with a polyprenol obtainable from leaves of a plant such as Ginkgo biloba or Cedrus deodara by extraction and as necessary followed by hydrolysis, or a reactive derivative thereof. The polyprenyl compounds are useful as intermediates for the synthesis of dolichol without the use of an expensive C.sub.5 chain extender.

Polyprenyl compounds and method of producing the same

Novel pesticidal compositions are comprised of a 2,2-dimethyl-3-(substituted ethyl)cyclopropanecarboxylic acid ester as the active ingredient, said cyclopropanecarboxylate having the structural formula: ##STR1## wherein X, Y and Z are the same or different and at least two of same are chlorine or bromine, with the remaining one being hydrogen, methyl, chlorine or bromine; R is an alcohol residue represented by one of the following structural formulae (II), (III), (IV) and (V): ##STR2## where A represents hydrogen, cyano, ethynyl or thiocarbamoyl; Q is hydrogen, chlorine, bromine, fluorine, methyl or trifluoromethyl; R.sup.1 is propargyl or benzyl; R.sup.2 represents 2-halogeno-3-phenyl-1-propen-1-yl, (dihalogenovinyloxy)phenyl, benzylphenyl, phthalimido, thiophthalimido, di- or tetrahydrophthalimido or dialkylmaleimido; R.sup.3 represents allyl, 2,4-pentadienyl, propargyl or benzyl.

Certain cyclopropane carboxylic acid esters and their pesticidal use

There is provided a class of novel 3,4-dihydro-2H-benzopyran derivatives which either have excellent inhibitory activity against unfavorable effects of heat, light and oxidative factors or are of use as precursors of compounds having such activity, and methods for producing these derivatives. Also provided are methods of using such 3,4-dihydro-2H-benzopyran derivatives as stabilizers for organic materials sensitive to heat, light or/and oxidative factors, and organic compositions containing such stabilizers.

3,4-Dihydro-2H-benzopyran derivatives, a method of producing them, a

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Kurashiki, Japan

Takashi Nishida