Kuraray Co., Ltd.

Kyowa Gas Chemical Industry Company, Ltd.

Nihon Iyakuhin Kogyo Co., Ltd.

Yoichi Ninagawa

Takashi Nishida

Yoshiaki Omura

Kazuo Itoi

Yoshin Tamai

Yoshiji Fujita

Takeo Hosogai

Masao Mizuno

Fumio Mori

Yasuyuki Tanaka

Koichi Ibata

Osamu Yamada

Susumu Okabe

Sunao Kyo

Tsumoru Renge

Masahisa Tanomura

Takayoshi Osaki

Koichi Kushida

Manzo Shiono

Haruo Nagai

Yutaka Omura

Michitaka Ogawa

Muneo Kobayashi

Hiromasa Nakamoto

Kazuo Kumamoto

Hiroko Murakami

Yuki Nogami

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 process for producing isoprene in good yield is provided. The process is characterized in that an alkyl tertiary butyl ether and a formaldehyde source are fed, together with water, into a acidic aqueous solution continuously or intermittently while maintaining the reaction pressure in an adequate range and at the same time distilling off the product isoprene, unreacted starting materials, isobutene and tertiary butanol, together with water, from the reaction zone.

Process for producing isoprene

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.

Geranylgeranylacetamide compounds having a piperazine ring, salts

A process for producing isoprene in good yield is provided. The process is characterized in that isobutene and/or tertiary butanol and a formaldehyde source are fed, together with water, into an acidic aqueous solution continuously or intermittently while maintaining the reaction pressure in an adequate range and at the same time distilling off the product isoprene and unreacted starting materials, together with water, from the reaction zone.

Novel farnesylacetic acid amide compounds represented by general formula ##STR1## wherein A is alkylene of at least 2 carbon atoms, R.sup.1 is H or lower alkyl, and R.sup.2 and R.sup.3 are each independently H, alkyl, cycloalkyl, alkenyl, aryl or aralkyl, or either one of R.sup.2 and R.sup.3 is such a group that forms, together with A, a piperidine or pyrrolidine ring which contains as constituent thereof the nitrogen atom lying therebetween, or R.sup.2 and R.sup.3 combinedly represent a group which forms, together with the nitrogen atom to which they are bonded, a piperidine, pyrrolidine or piperazine ring; and salts thereof have antiulcerogenic and antibacterial activities.

Farnesylacetic acid amides

Novel farnesylacetic acid ester derivatives containing an amine nitrogen in the alcohol residue thereof and represented by the following general formula exhibit high levels of antiulcerogenic activity and very low levels of toxicity: ##STR1## wherein A is an alkylene radical containing at least 2 carbon atoms; R.sup.1 is H, alkyl, cycloalkyl, aryl, aralkyl or alkenyl; R.sup.2 and R.sup.3 are independently H, alkyl, aryl, aralkyl or alkenyl or one of R.sup.2 and R.sup.3 forms, together with A, a piperidine, pyrrolidine, tetrahydropyrimidine or piperazine ring which contains the nitrogen atom lying therebetween or R.sup.2 and R.sup.3 combine to form, together with the adjacent nitrogen atom, a piperazine ring; provided that the total number of carbon atoms contained in A, R.sup.1, R.sup.2 and R.sup.3 is at least 5.

Farnesylacetic acid ester derivatives

dl-.alpha.-Tocopherol is prepared by condensing trimethylhydroquinone with phytyl halide in a chlorinated lower aliphatic hydrocarbon solvent, in the presence of metallic tin and a Friedel-Crafts catalyst.

Preparation of dl-.alpha.-tocopherol

2,7,10,15,18,23-Hexamethyltetracosane is a novel compound. This compound is prepared [1] by hydrogenating 2,7,10,15,18,23-hexamethyltetracosa-1,6,18,23-tetraene-11,13-diyne-10,15-d iol [itself a novel compound] or 2,7,10,15,18,23-hexamethyltetracosa-11,13-diyne-10,15-diol, dehydrating the hydrogenated intermediates, and thence hydrogenating the dehydrated precursors, or [2] by selectively, partially hydrogenating the said 10,15-diol compounds and thence hydrogenolyzing the precursor diols, or [3] by hydrogenolyzing the said 10,15-diol compounds, or [4] by hydrogenolyzing the hydrogenated intermediates of the reaction [1]. The compound, 3,6,11-trimethyl-undeca-6,11-dien-1-yl-3-ol, a starting material intermediate, is also a novel compound.

2,7,10,15,18,23-Hexamethyltetra-cosane

Novel 2,6,10,15,19,23-hexamethyltetracosane-10,15-diol derivatives. Such derivatives are prepared by hydrogenation of 2,6,10,15,19,23-hexamethyltetracosa-11,13-diyne-10,15-diol derivatives and used as starting materials for preparing squalane.

Preparation of squalane by hydrogenolysis

Unsaturated alcohols represented by the general formulas (I) and (II) below ##STR1## wherein R is a substituted or unsubstituted hydrocarbon radical, R.sub.2 and R.sub.3 are hydrogen or lower alkyl groups, and R and R.sub.2 may be linked together are mutually isomerized in the presence of a catalyst comprising a transition metal compound of Groups V, VI and VII of the Mendeleev Periodic Table.

Isomerization of the unsaturated alcohols

Process for producing substituted ketones from the reaction between organic halides and ketones having replaceable active hydrogen atoms on the carbon atom(s) alpha to the carbonyl group, in the presence of an alkali metal hydroxide unitilizing phosphonium salts as the catalyst, which salts have the following formula: ##EQU1## wherein said R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are the same or different and are branched or straight chain alkyl of 1-30 carbon atoms, cycloalkyl of 6-10 carbon atoms, aryl of 6-10 carbon atoms aralkyl or alkaryl wherein the aryl and alkyl are as above defined and X.sup.- is an inorganic or organic anion.

Process for the production of substituted ketones

A process for producing substituted ketones is disclosed comprising reacting an organic halide with a ketone which has a replaceable hydrogen atom on the carbon atom in the .alpha.-position to the carbonyl group, in the presence of an aqueous alkali metal hydroxide and at least one basic nitrogen catalyst such as certain primary amines, secondary amines, tertiary amines, quaternary ammonium salts or betaine-type quaternary ammonium salts.

Process for the production of a substituted ketone

Novel 2,6,10,15,19,23-hexamethyltetracosa-11,13-diin-10,15-diol derivatives. Such derivatives are prepared by oxydative coupling of 3,7,11-trimethyldodeca-1-in-3-ol derivatives or by ethynylation of 6,10-dimethylundecan-2-on derivatives with diacetylene and used as starting materials for preparing squalane.

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Hasaki, Japan

Yoichi Ninagawa