Nisshin Flour Milling Co., Ltd.

Lederle (japan), Ltd.

Grelan Pharmaceutical Co., Ltd.

Yoshiyuki Tahara

Hiroyasu Koyama

Toshihiro Takahashi

Reiko Kubota

Yasuhiro Komatsu

Teruhito Yamaguchi

Shigeo Kawase

Katsura Kogure

Michiko Nagai

Yoshikuni Suzuki

Noriyoshi Sueda

Masahiro Tsuji

Toshiji Sugai

Hitoshi Inoue

Masanori Sugita

Masao Nagase

Ikuo Kishi

Osamu Ogawa

Yasushi Okamoto

Kaneto Uekama

Nobuhiro Kinoshita

Hiroyuki Yamazaki

Tatsuya Ohwaki

Kazuhiko Yamada

Hiroki Kato

Takanori Ijitsu

Masashi Toyoda

Tadashi Yamada

Osamu Irino

Noriyuki Misaki

Yoshio Mishima

Masako Yamada

Masatoshi Yasuda

Prophylactic and therapeutic agent for hepatic diseases

A pharmaceutical oil-in-water type microemulsion having an action of potentiating the activities of anti-cancer agents, said micro-emulsion comprises

Anti-cancer activity potentiator

Disclosed is a rhodanine derivative of formula (I). A rhodanine derivative of formula (I) ##STR1## wherein R.sup.1 is hdyrogen, C.sub.1 -C.sub.8 alkyl, carboxyl(C.sub.1 -C.sub.4)alkyl or (C.sub.1 -C.sub.4)alkoxycarbonyl(C.sub.1 -C.sub.4)alkyl;

Rhodanine derivatives and pharmaceutical compositions

A pharmaceutical oil-in-water type microemulsion having an action of potentiating the activities of anti-cancer agents, said micro-emulsion comprises fine particles of a vegetable oil or a triglyceride of a medium-chain fatty acid having 8 to 12 carbon atoms containing 0.1 to 10% (w/v) of N-solanesyl-N,N'-bis(3,4-dimethoxybenzyl)ethylenediamine malate of formula (I) below, ##STR1## an aqueous medium, and, 0.05 to 25% (w/v) of a physiologically acceptable phospholipid for dispersing said fine particles in said aqueous medium.

Polyprenols and polyprenyl phosphates are of the formula ##STR1## wherein ##STR2## represents a trans-isoprene unit, ##STR3## represents a cis-isoprene unit, ##STR4## represents a dihydroisoprene unit, l is an integer of 2 to 8, m is 0 or an integer of 5 to 18, n is 0 or 1, the sum of l and m is in the range of 8 to 20, and X represents a hydrogen atom or --PO.sub.3 MM' wherein M and M' may be the same or different and each is a hydrogen atom or a monovalent cation or both M and M' together form a divalent cation. They are useful as a medicament for the inhibition of tumor metastasis.

Pharmaceutical compositions for the inhibition of tumor metastasis

Anti-ulcer agents containing isoprenoid derivatives are provided. The isoprenoid derivatives are represented by the formula: ##STR1## wherein: R represents a group of formula ##STR2## In the above formula, R.sub.1, R.sub.2 and R.sub.3 may be the same or different each other and each represents a hydrogen atom, a hydroxy group, a lower alkanoyloxy group, a lower alkyl group or a lower alkoxy group, provided that two or more of them do not represent hydrogen atoms at the same time; R.sub.4 and R.sub.5 may be the same or different each other and each represents a hydrogen atom, a hydroxy group or a lower alkanoyloxy group   represents the signal or the double bond between the carbon atoms; m represents 0 or 1; n represents 0 or an integer of from 1 to 9, provided that the sum of m and n is an integer of from 1 to 9.

Isoprenoid derivatives and anti-ulcer agents containing the same

Now is provided a new sustained release drug preparation comprising such an inclusion complex of a medical compound with a hydrophobic cyclodextrin derivative, e.g. ethylated cyclodextrins, which sustains or retards the dissolution and release of the medical compound at a controlled rate from the inclusion complex and hence from the drug preparation containing the inclusion complex, so as to maintain the concentration of the medical compound in blood at an effective level for prolonged time. This drug preparation may further contain a second type of an inclusion complex of the medical compound with a hydrophilic cyclodextrin or hydrophilic cyclodextrin derivative, in mixture with the first type of the inclusion complex of the medical compound with a hydrophobic cyclodextrin derivative, to maintain the controlled release of the medical compound from the drug.

Sustained release drug preparation

New antiviral nonaprenylamine derivatives represented by the following formula ##STR1## wherein R is 4 or 5 atoms selected from the group consisting of C and N so as to complete, with the non-R nitrogen, a 5- or 6-membered heterocyclic ring, and X is selected from the group consisting of H and hydroxy-lower alkyl and non-toxic, pharmaceutically acceptable acid addition salts thereof and a pharmaceutically acceptable carrier.

Interferon inducing, anti-vaccinia, and/or anti-influenza compositions

Nonyl prenyl-N heterocyclic compounds are prepared, useful as antivirals.

Nonyl prenyl-N heterocyclics

Disclosed herein are saturated and unsaturated aliphatic acids and esters of formula R--Z as defined in the specification which are antiulcer agents.

Antiulcer compounds

A compound of the formula ##STR1## wherein R.sub.1 is a phenethyl group, R.sub.2 and R.sub.3, taken together with the nitrogen atom to which they are bonded, form an N' hydroxylalkyl substituted piperazine, and (aklylene) is a lower alkylene chain substituted with a hydroxyl group; or an acid addition salt thereof is described.

Isoprenylamine derivatives

This invention relates to isoprenylamine derivatives and acid addition salts thereof, which compounds are useful for controlling virus infection of vertebrate animals.

Four different optical isomers of a new compound, 1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy)-2-p ropanol are now provided as new substances. These four optical isomers are now named as (2R, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, (2S, 1'S)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, (2S, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanol, respectively. These four optical isomers have different activities for their .beta.-adrenergic-blocking effect and .alpha.-adrenergic-blocking effect and are useful as valuable agents for therapeutic treatment of various cardiovascular diseases, as compared to an optically inactive racemic mixture of said isomer compounds. These four optical isomers may be produced and isolated from each other by chromatographing (1'S)- or (1'R)-N-[2'-(o-methoxyphenoxy)-1'-methylethyl]-5-(4'-isocarbostyriloxymeth yl)-2-oxazolidones to isolate either its (5R, 1'S)-isomer and its (5S, 1'S)-isomer, or its (5S, 1'R)-isomer and its (5R, 1'R)-isomer therefrom separately and then hydrolyzing each of these isolated isomers under alkaline conditions to obtain separately (2R, 1'S)-, (2S, 1'S)-, (2S, 1'R)- and (2R, 1'R)-1-[2'-(o-methoxyphenoxy)-1'-methylethylamino]-3-(4'-isocarbostyriloxy )-2-propanols.

Optically active isocarbostyril derivatives and a method of preparing

A compound of the formula ##STR1## wherein R.sub.1 is a phenethyl group, R.sub.2 is a hydrogen atom, R.sub.3 is a lower alkyl group, and (alkylene) is a lower alkylene chain substituted with a hydroxyl group; or an acid addition salt thereof is described.

Compounds of the formula ##STR1## wherein R.sub.1 and R.sub.3 each is benzyl or substituted with up to 3 methoxy groups, R.sub.2 is a hydrogen atom and (alkylene) is lower alkyl and the compounds are useful for controlling viral infections.

Growing community of inventors

Tsurugashima, Japan

Yoshiyuki Tahara