Eisai Company, Limited

Agency of Industrial Science and Technology

Yuichi Inai

Isao Yamatsu

Shinya Abe

Takeshi Suzuki

Shizumasa Kijima

Toshiji Igarashi

Yoshikazu Suzuki

Osamu Tagaya

Kouji Yamada

Manabu Murakami

Kouichi Suzuki

Norio Minami

Hideaki Watanabe

Yoshio Tanabe

Hiroyuki Shiojiri

Seiichi Kobayashi

Kimio Hamamura

Yoshikage Nakajima

Kouzi Yamada

Yoshinori Katoh

Kensaku Kinoshita

Mannen Mishima

Kouichi Abe

Yoshimasa Takahara

Youji Yamagishi

Koichi Abe

Tomio Tsurugi

Kenji Nakajima

Yoshiyuki Kawakami

Akio Sato

Toshiharu Ohgoh

Kuniko Hara

Yoshiyuki Kohara

Kumiko Hara

Nozomu Koyanagi

Kiyoshi Oketani

Hideaki Fujisaki

Noriyasu Hirose

Takashi Banba

Kiiti Ema

Masaru Satoh

Naosuke Seto

Isao Yamatu

2,3,5-trimethyl-benzoquinone is produced by oxidizing 2,3,6-trimethyl-phenol in the presence of a catalyst of cupric chloride and lithium chloride in a solvent mixture of an aromatic hydrocarbon and a lower aliphatic alcohol having 1 to 4 carbon atoms.

Process for preparing 2,3,5-trimethylbenzoquinone

A novel compound, 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid, and a salt thereof are disclosed together with a number of different processes for the preparation of the compound. The uses of the novel compound as an agent for treating papillomata are also disclosed.

3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid composition

Skin diseases with keratinization and allergic or inflammatory skin diseases are treated by orally or parenterally administering to an adult human patient from 40 mg to 4 g/day of a polyprenyl compound having the formula (I): ##STR1## in which each of n and m is 0, 1, or 2, n+m is 0, 1 or 2, A is ##STR2## and B is ##STR3## [in which R represents the hydroxyl group, a lower alkoxy group, or ##STR4## (wherein each of R.sub.1 and R.sub.2 is the hydrogen atom, a lower alkyl group or an aryl group)]; provided that R is a lower alkoxy or ##STR5## if n is 1, m is 0, a is ##STR6## and B is ##STR7##

Method of treating skin diseases

A novel compound, 3,7,11,15-tetramethyl-2,4,6,10,14-hexadecapentaenoic acid, and a salt thereof are disclosed together with a number of different processes for the preparation of the compound. The uses of the novel compound as an anticancer agent are also disclosed.

3,7,11,15-Tetramethyl-2,4,6,10,14,-hexadecapentaendic acid

An anti-cancer agent which comprises a polyprenvl compound having the formula (I): ##STR1## in which each of n and m is 0, 1 or 2, n+m is 0, 1 or 2, A is ##STR2## and B is ##STR3## in which R represents the hydroxyl group, a lower alkoxy group, or ##STR4## (wherein each of R.sub.1 and R.sub.2 is the hydrogen atom, a lower alkyl group or an aryl group)]; provided that R is a lower alkoxy or ##STR5## if n is 1, m is 0, A is ##STR6## and B is ##STR7##

Method of treating cancerous and precancerous conditions

Non-steroidal, anti-inflammatory drugs are disclosed which are polyprenyl alcohol esters of indolyl lower carboxylic acids, phenyl lower carboxylic acids, acetyl salicyclic acid, anthranilic acid and derivatives thereof.

Polyprenyl compounds, process for the production thereof and medicines

A conjugated polyprenylcarboxylic acid and its derivative having the formula: ##STR1## in which each of n and m is 0, 1 or 2, n+m is 1 or 2, A is ##STR2## and R is the hydroxyl group, a lower alkoxy group or ##STR3## wherein each of R.sub.1 and R.sub.2 represents the hydrogen atom, a lower alkyl group, or an aryl group; provided that R is ##STR4## if A is ##STR5## n is 1 and m is 0.

Conjugated polyprenylcarboxylic acids and their derivatives

This invention relates to polyprenylcarboxylic acid amides represented by the following general formula (I): ##STR1## wherein n is an integer of from 1 to 4, a and b stand for hydrogen atoms or a direct valence bond between the carbon atoms to which a and b are attached, c and d stand for hydrogen atoms or a direct valence bond between the carbon atoms to which c and d are attached, and R.sub.1 and R.sub.2 stand for a hydrogen atom, a lower alkyl group, a phenyl group which may be substituted or an aralkyl group which may be substituted, or R.sub.1 and R.sub.2 form, together with the adjacent nitrogen atom, a 5- or 6-membered heterocyclic ring which may contain other hetero atoms or may be substituted, and also to a process for the preparation of said polyprenylcarboxylic acid amide and to a pharmaceutical composition for treating liver dysfunction comprising said polyprenylcarboxylic acid amide.

Polyprenylcarboxylic acid morpholides and pharmaceutical compositions

Non-steroidal, anti-inflammatory drugs are disclosed which are polyprenyl alcohol esters of indolyl lower carboxylic acids, phenyl lower carboxylic acids, acetyl salicylic acid, anthranilic acid and derivatives thereof.

An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or an alkyl group having one to four carbon atoms and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.

.alpha.,.beta.-Dihydropolyprenyl derivatives for treating hepatitis

Polyprenyl carboxylic acid derivatives having the general formula (I): ##STR1## in which n is an integer of from 2 to 4, R.sub.1 represents the hydrogen atom or a protecting group for the carboxylic acid group, and R.sub.2 represents a hydroxymethyl, formyl or carboxyl group, are disclosed. A process for the preparation of the polyprenyl carboxylic acid derivative involving microbiological oxidation using a strain belonging to the genus Nocardia is disclosed. The compounds have anti-ulcer activity and hypotensive activity. The compounds also are useful as intermediates for preparing polyprenyl carboxylic acids of the formula ##STR2## and esters thereof, wherein l is an integer of from 4 to 11. The polyprenyl carboxylic acids and esters thereof have hypotensive activity and anti-ulcer activity.

Polyprenyl carboxylic acid derivatives

The polyprenyl compound having the formula: ##STR1## wherein X represents a group of the formula: --CH.dbd.CH--, a group of the formula: ##STR2## or a group of the formula: ##STR3## and Y represents a group of the formula: --COOR.sup.1 in which R.sup.1 represents a hydrogen atom or a lower alkyl group or a group of the formula: ##STR4## in which R.sup.2 represents a hydrogen atom or a lower alkyl group, is new and useful as a medicine.

Polyprenyl compounds

An .alpha.,.beta.-dihydropolyprenyl derivative having the formula (I): ##STR1## wherein X represents a group of --COOR.sub.1 or --CH.sub.2 OR.sub.2 in which R.sub.1 is the hydrogen atom or a lower alkyl group and R.sub.2 is the hydrogen atom or an aliphatic acyl group having one to four carbon atoms; and n is an integer of one to four. A process for the preparation of the .alpha.,.beta.-dihydropolyprenyl derivative and a therapeutic agent for treatment of liver diseases comprising the same are also disclosed.

.alpha.,.beta.-Dihydropolyprenyl derivatives useful in treating hepatitis

A process is disclosed for the preparation of a compound having the general formula: ##STR1## wherein n is an integer of from 2 to 4, R.sub.1 is an ester-forming moiety effective as a protecting group for a carboxyl group, and R.sub.2 is hydroxymethyl, formyl or carboxyl. The compounds (I) are useful as intermediates for the preparation of polyprenyl compounds having hypotensive and anti-ulcer activity. The process of the invention includes cultivating a microorganism selected from a strain of the genus Nocardia called BPM 1613, FERM-P No. 1609, Corynebacterium equi IAM 1038, Candida lipolytica IFO 0746, and Mycobacterium smegmatis IFO 3083, in a nutritive culture medium, in the presence of a compound having the general formula: ##STR2## wherein R.sub.3 is an ester-forming moiety effective as a protecting group for a carboxyl group, whereby the microorganism utilizes the compound (II) as a carbon source and oxidizes the compound (II), thereby converting the compound (II) into the compound (I).

Process for preparing polyprenyl carboxylic acid derivatives

Polyprenyl carboxylic acid amides of the formula ##STR1## process for their preparation and use thereof for treating liver dysfunction are disclosed.

Growing community of inventors

Tokyo, Japan

Yuichi Inai