Yoshitomi Pharmaceutical Industries, Ltd.

Kuraray Co., Ltd.

Taiho Pharmaceutical Company Limited

Michio Terasawa

Minoru Moriwaki

Tomonori Imayoshi

Tetsuya Tahara

Kenzo Arizono

Takashi Nishida

Yutaka Mizushima

Koichi Kanehira

Takanori Oe

Rie Igarashi

Noriyuki Yamamoto

Hirofusa Ajioka

Keiko Hoshi

Masahito Komuro

Masayuki Inoue

Manzo Shiono

Kenji Chiba

Yukio Hoshino

Hiroshi Tanaka

Kazuyuki Kawasaki

Hirotsugu Komatsu

Tsuguo Ikebe

Minoru Kawakami

Masao Abe

Hiroyuki Sueoka

Takeki Okumoto

Mitsuyoshi Yasumoto

Mitsuhiro Konishi

Toshio Hamasaki

Hiroyuki Kitani

Hiroshi Yuki

Michiharu Nobutoki

Yukihiro Yasunaga

Kazuyuji Kawasaki

Syuji Yuasa

Mariko Nagasawa

Hidekazu Aratani

Immunosuppressive drug

Stable crystals of an acid addition salt of an optically active thienotriazolodiazepine compound or its hydrate of the formula ##STR1## wherein R.sup.1 is hydrogen, R.sup.2 is 2-phenylethyl substituted by alkyl having 1 to 5 carbon atoms, 2-morpholinocarbonylethyl or alkyl having 6 to 12 carbon atoms, or R.sup.1 and R.sup.2 may combinedly form a saturated 5-membered ring having one substituent selected from the group consisting of morpholinomethyl, morpholinocarbonyl and N,N-dipropylcarbamoyl, R.sup.3 is halogen, alkyl having 1 to 5 carbon atoms or alkoxy having 1 to 5 carbon atoms, R.sup.4 is trifluoromethyl or alkyl having 1 to 5 carbon atoms, R.sup.5 is hydrogen or methyl, m is 1-2, and n is 0-2. The present invention provides optically active thienotriazolodiazepine compounds having strong PAF-antagonistic activity as markedly stable crystals which are excellent in crystalline property, permit purification by recrystallization, and have high chemical purity and optical purity, thereby rendering industrial large-scale synthesis attainable. In addition, crystallization thereof facilitates medicinal standardization and pharmaceutical formulation.

Optically active thienotriazolodiazepine compounds

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 styryl compound of the formula(I): ##STR1## wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt or an ester thereof is disclosed. Since the compounds of the present invention possess potent and long-lasting leukotriene-antagonistic actions and inhibitory actions against leukotriene, and exhibit better absorption by the oral administration. Further, the compounds of the present invention possess 5-lipoxygenase-inhibitory actions and/or cyclooxygenase-inhibitory actions, inhibitory actions to biosynthesis of LTB4, chemotactic actions against human leucoccyte, chymase-inhibitory actions, inhibitory actions to release of histamine or antihistamine actions. Therefore, they are useful as the prophylactic and therapeutic medicines for brochial asthma, chronic bronchitis, atopic dermatitis, allergic rhinitis, allergic arthritis, allergic conjunctivitis, hay fever, urticaria, alimentary allergy, pain, pyretolysis, rheumatoid, thrombosis, coronary vascular diseases, ischemic heart disease, peptic or duodenal ulcer and the like.

Styryl phridyl compounds and their pharmaceutical compositions

Ester-substituted thienotriazolodiazepine compounds and pharmaceutical

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

A thienotriazolodiazepine compound of the formula: ##STR1## wherein each symbol is as defined in the specification or a pharmaceutically acceptable salt thereof, and pharmaceutical uses thereof. Said compounds exhibit PAF-antagonistic activity and are useful for the prevention or treatment of various PAF-induced diseases.

Thienotriazolodiazepine compounds and pharmaceutical uses thereof

Benzopyranopyridineacetic acid ester compounds of the formula: ##STR1## wherein R.sup.1, and R.sup.2 and R.sup.3 independently represent hydrogen or C.sub.1-4 alkyl; and n is 1 or 2, and their pharmaceutical use are disclosed. These compounds possess antiinflammatory, analgesic and antipyretic activities with less adverse action on the gastrointestinal tract.

Benzopyranopyridineacetic acid ester compounds and their pharmaceutical

A pyrazolopyridine compound of the formula: ##STR1## or a salt thereof, wherein each symbol is as defined in the specification. Said compounds exhibit antiinflammatory, analgesic, antipyretic, antiallergic, antiarthritic, antirheumatic activities or inhibitory activities on platelet aggregation.

Pyrazolopyridine compounds, their preparation and use as platelet

Purine derivative and pharmaceutical composition

3-Indolecarboxamide compounds of the formula: ##STR1## inclusive of pharmaceutically acceptable acid addition salt and/or hydrate forms thereof, wherein R.sup.1 is C.sub.1-8 alkyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkyl-C.sub.1-8 alkyl, allyl, propargyl, or phenyl or phenyl-C.sub.1-4 alkyl which may be optionally substituted, on the benzene ring, by at least one substituent selected from the group consisting of halogen, trifluoromethyl, C.sub.1-4 alkyl and C.sub.1-4 alkoxy; R.sup.2 is H or C.sub.1-6 alkyl; R.sup.3 is H, halogen, C.sub.2-6 alkanoyloxy, benzoyloxy, C.sub.1-4 alkoxy, benzyloxy, hydroxy or C.sub.1-4 alkyl; R.sup.4 is H, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or hydroxy; R.sup.5 is H or C.sub.1-4 alkoxy; A is ethylene or trimethylene, which may be optionally substituted by C.sub.1-4 alkyl; n is zero, 1 or 2; and m is zero or 1, are useful as drugs for the prevention and treatment of various allergic diseases.

Anti-allergic 3-indolecarboxamides

An antiinflammatory and analgesic gelled ointment contains pranoprofen, at least one member selected from the group consisting of lower aliphatic alcohol, polyethylene glycol, methyl ethyl ketone and acetone, a gelling agent selected from the group consisting of carboxyvinyl polymer, hydroxyethyl cellulose, alginic acid and carboxymethyl cellulose, a water-soluble basic substance selected from the group consisting of ammonia, sodium hydroxide, potassium hydroxide, triethanolamine, diethanolamine, diisopropanolamine, triisopropanolamine and triethylamine, and water.

Pranoprofen gelled ointment

Growing community of inventors

Nakatsu, Japan

Michio Terasawa