Teijin Limited

Simpson Biotech Co., Ltd

Nippon Soda Co., Ltd.

The Green Cross Corporation

Kaken Pharmaceutical Company, Ltd.

Teijin Pharmaceutical Co., Ltd.

Yoshinobu Hashimoto

Chia-Chin Sheu

Sachio Ishimoto

Shigetoshi Kadota

Hiroyuki Kawashima

Kazumasa Yokoyama

Tadakazu Suyama

Yoshiki Suzuki

Seizi Kurozumi

Yutaka Mizushima

Takeshi Hara

Takeshi Toru

Seiji Kurozumi

Katsuhiro Uchida

Toru Takeshita

Makiko Kobayashi

Hiroyuki Okamoto

Masao Tohno

Tatsuyuki Naruchi

Yasutaka Kayama

Kazuhiko Itoh

Kiichiro Nabeta

Shozoh Masumoto

Masuo Morisaki

Nobuo Ikekawa

Toshiro Mori

Hitoshi Fujimori

Tamiko Sunami

Minoru Hayashi

Kinpei Kato

Mamoru Kiyoki

Nobuo Sato

Hiroyoshi Endo

A composition that effectively prevents the manifestation of osteoporosis, the formation of osteoclasts and suppresses a decrease of spongy bone density. The composition primarily containsor its processed product.

Agents for treating osteoporosis and inhibiting osteoclast formation

Compositions and methods for treating osteoporosis, the formation of osteoeclasts, and/or for the suppression of decreasing spongy bone density. Example methods include administeringor its processed product.

There is provided a fat emulsion of an ester of flurbiprofen having the formula ##STR1## wherein R is a group of the formula ##STR2## wherein R.sub.1 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, R.sub.2 is a C.sub.1 -C.sub.15 alkyl group or a C.sub.2 -C.sub.8 alkenyl group, and m is zero or an integer of 1; or a lactone group of the formula ##STR3## wherein R.sub.3 and R.sub.4 are same as or different from each other and are a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group, and n is an integer of 1 or 2. The emulsion containing particles of a vegetable oil dissolving the ester can be orally or parenterally administered to human or animal for analgesia, antiphlogosis and antipyresis in various diseases and exhibits a high activity with small amounts in terms of flurbiprofen as compared with flurbiprofen itself.

Ester of flurbiprofen and emulsion containing the same

A method for regulating the bone metabolism of a warm-blooded animal, which comprises administering pharmaceutically effective amounts of 1.alpha., 24-dihydroxycholecalciferol (1.alpha., 24-DHCC) and 24,25-dihydroxycholecalciferol (24,25-DHCC) to said warm-blooded animal, and a pharmaceutical composition comprising 1.alpha.,24-DHCC, 24,25-DHCC and a pharmaceutically acceptable carrier. According to the invention, a condition of abnormal bone metabolism requiring long-term therapy, such as osteoporosis, can be safely treated by administering 1.alpha., 24-DHCC and 24,25-DHCC over a long period of time because no substantial adverse effect of 1.alpha., 24-DHCC on the metabolis of 24,25-DHCC is observed.

Method for regulating bone metabolism of warm-blooded animals, and

This is a bone formation stimulant containing vitamin D.sub.3 or its derivative and acetylsalicylic acid or its formaceutically permissible salt. The present bone formation stimulant is used to cure or prevent the diseases caused by the deficiency of vitamin D or related diseases by dosing human beings or animals with it.

Bone formation stimulant

Organothiocyclopentanes of the formula ##STR1## wherein E represents &gt;C.dbd.O or ##STR2## in which Z' represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; X represents --S--, --CH.sub.2 --, --CH.dbd.;  represents a single or double bond; R' represents a monovalent or divalent organic group containing 1 to 25 carbon atoms; R represents a monovalent organic group containing 1 to 25 carbon atoms; Z represents a hydrogen atom, a hydroxyl group or a protected hydroxyl group; and when both E and Z represent a hydroxyl group or a protected hydroxyl group, X represents --S--. Also, 2-organothio-2-cyclopentenones of the formula ##STR3## wherein R and Z are as defined above. The compounds of formula (I) are prepared by reacting 2,3-epoxy-cyclopentanone or its derivatives with mercaptans in the presence of basic compounds. The compounds of formula (II) are prepared by reacting the compounds of formula (I) with mercaptans or organocopper-lithium compounds, and optionally reducing the resulting products, and optionally protecting the hydroxyl group at their cyclopentane ring. The compounds of formula (I) have an action of inhibiting ulcer formation, and are useful intermediates for the compounds of formula (II). The compounds of formula (II) are monothia- or dithia-prostanoic acid derivatives, and exhibit various superior pharmacological actions.

2-Organothio-2-cyclopentenones, organothio-cyclopentanes derived

Novel 4H-pyrrolo[1,2-a][1,4]benzodiazepine derivatives of the formula ##STR1## wherein at least one of R.sub.1, R.sub.2 and R.sub.3 represent lower alkyl and the remainder hydrogen, R.sub.4 represents hydrogen or lower alkyl, ring A optionally contains at least one substituent selected from halogen, nitro and trifluoromethyl, and ring B optionally contains at least one substituent selected from halogen, nitro, trifluoromethyl, lower alkyl and lower alkoxy; and novel intermediates thereof expressed by the formula ##STR2## wherein Z represents protected amino. Compounds of formula (I) are prepared by subjecting compounds of formula (II) to protective group-elimination and cyclization. The compounds of formula (I) and acid addition salts thereof have useful anti-anxietic, sedative, anti-convulsant, muscle relaxant and hypnotic, and their toxicity is low.

Benzodiazepine derivatives and pharmaceutical compositions containing

Novel 1.alpha., 24-dihydroxycholecalciferol and derivatives thereof which are useful with reduced side-effects for the treatment of abnormal metabolism of calcium and phosphorus caused by liver failure, renal failure, gastrointestinal tract failure and parathyroid failure, and related bone diseases. Preparation of the novel 1.alpha., 24-dihydroxycholecalciferol and their derivatives starts from 1.alpha., 24-dihydroxycholesterol prepared by reacting 1.alpha., 2.alpha.-epoxy-24-keto-cholesta-4,6-dien-3-one with an alkali metal and a proton donor in the presence of liquid ammonia or a liquid amine. Reaction of the 1.alpha., 24-dihydroxycholesterol with an allylic brominating agent, followed by contacting with a dehydrobrominating agent, affords 1.alpha.,3.beta., 24-trihydroxycholesta-5,7-diene derivative, which can then be converted to 1.alpha., 24-dihydroxycholocalciferol by ultraviolet irradiation in a organic solvent, followed by isomerization. Processes are also provided for separating 1.alpha., 24-dihydroxycholesterol into an (S)-epimer and an (R)-epimer, and also for separating at least one of 1.alpha., 3.beta., 24(S)-and 1.alpha., 3.beta., 24(R)-trihydroxycholesta-5,7-dienes from trihydroxycholesta-4,6-diene.

Novel 1.alpha.,24-dihydroxycholecalciferol compositions, novel

The thioallophanate compound represented by the following general formula ##EQU1## wherein X is hydrogen, chlorine atom, nitro or methyl group: Z is a substituting group selected from the group consisting of ##EQU2## and ##EQU3## has excellent anthelmintic activity and can be used for controlling helminthiasis of animals.

Anthelmintic methods of use

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Fujisawa, Japan

Yoshinobu Hashimoto