Kuraray Co., Ltd.

Other

Nihon Iyakuhin Kogyo Co., Ltd.

Masao Mizuno

Takashi Nishida

Tetsuo Takigawa

Koichi Ibata

Yoichi Ninagawa

Yasuyuki Tanaka

Masafumi Okada

Michiya Shimamura

Shigeaki Suzuki

Yoshiji Fujita

Yoshiaki Omura

Takashi Onishi

Fumio Mori

Naoshi Nakagawa

Akio Urabe

Tsutomu Kameyama

Akira Kageyu

Hiromasa Nakamoto

Kazuo Kumamoto

Hiroko Murakami

Yuki Nogami

Jiro Kitamura

Fumimaro Takak

Michitaka Ogawa

Muneo Kobayashi

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

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

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.

A medicament containing a compound of the formula ##STR1## wherein ##STR2## is a trans-isoprene unit, ##STR3## is a cis-isoprene unit, and n is an integer of from 12 to 18, or a pharmaceutically acceptable ester thereof. The medicament is useful for the treatment of anemia, particularly aplastic anemia.

Methods for enhancing differentiation and proliferation of hematopoietic

A method of producing .alpha.-dihydropolyprenyl monophosphates from .alpha.-dihydropolyprenols through .alpha.-dihydropolyprenyl dichlorophosphates in good yield and with ease is provided. A method of producing .alpha.-dihydropolyprenyl dichlorophosphates which are intermediate compounds useful for the first-mentioned method is also provided.

Method of producing .alpha.-dihydropolyprenyl monophosphates

A compound which is 4-(3,5-dihydroxy-3-methylpentylamide)butyric acid or its pharmaceutically acceptable salt or ester; this compound being produced by reacting a salt or an ester of gamma-aminobutyric acid with beta-hydroxy-beta-methyl-delta-valerolactone, and as required, converting the resulting compound in the form of a salt or ester to a free acid, or as required, converting the resulting compound in the form of a free acid to its pharmaceutically acceptable salt or ester; and useful as a medicament for preventing or treating an impediment in cerebral function.

Gamma-aminobutyric acid derivatives, process for production thereof, and

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 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

A geranylgeranylacetamide compound having a piperazine ring represented by the following formula (I) ##STR1## wherein R represents a member selected from the class consisting of a hydrogen atom, C.sub.1 -C.sub.5 alkyl groups which are unsubstituted or mono-substituted by a halogen atom, C.sub.2 -C.sub.5 alkenyl groups and C.sub.7 -C.sub.8 aralkyl groups, R.sub.1 represents a C.sub.1 -C.sub.3 alkyl group, and n represents 0, 1 or 2, and a pharmaceutically acceptable acid addition salt thereof. The aforesaid compound can be prepared by reacting geranylgeranylacetic acid or its reactive derivative with a piperazine compound, and thereafter, if desired, transforming the free geranylgeranylacetamide compound thus obtained into its pharmaceutically acceptable acid addition salt. A pharmaceutical composition containing said compound exhibits antiulcerogenic activity, particularly excellent antipeptic ulcerogenic activity, and is useful as an agent for treating ulcers.

Growing community of inventors

Kurashiki, Japan

Masao Mizuno