Dainippon Pharmaceutical Company, Limited

Asahi Glass Company, Limited

Naonobu Hatano

Masanao Shimizu

Yasushi Matsumura

Hitoshi Uno

Arata Yasuda

Keiichi Uchida

Haruki Nishimura

Fuminori Sato

Mikio Kurokawa

Toshiaki Kadokawa

Kunihiko Takeyama

Buichi Fujitani

Tomoyuki Asai

Hiroaki Kinugasa

Masahisa Hashimoto

Katsuyoshi Nakatsuzi

Hiroko Kon

Kiyoshi Nakamura

Kouji Hayashi

A 6-fluoroprostaglandin having the formula: ##STR1## wherein A is a carbonyl group or a hydroxymethylene group, R.sup.1 is a substituted or unsubstituted C.sub.1 -C.sub.10 alkyl group or a substituted or unsubstituted 5- or 6-membered cycloalkyl group, R.sup.2 is a hydrogen atom or a C.sub.1 -C.sub.10 alkyl group, each of R.sup.3 and R.sup.4 which may be the same or different is a hydrogen atom or a protecting group, R.sup.5 is a hydrogen atom or a hydroxyl group, and is a single bond or a double bond, and its salt when R.sup.2 is a hydrogen atom.

6-fluoroprostaglandins

Calcium antagonist piperazine derivatives, and compositions therefor

A compound of the formula ##STR1## wherein R.sub.1 represents a hydrogen atom or a lower alkyl group, and R.sub.2 represents a hydrogen or halogen atom or a trifluoromethyl group, And its pharmaceutically acceptable salt. The compound is prepared by reacting the corresponding 1,2,4-benzothiadiazine 1,1-dioxide with a piperazine compound or alkylating 1,2,4-benzothiadiazine 1,1-dioxide whose corresponding 3-position is substituted by a piperazinyl group. The above compound has superior antihypertensive activity separated from diuretic, antidiuretic and hyperglycemic activities, and is free from side-effects.

3-Piperazinyl 1,2,4-benzothiadiazine 1,1-dioxide derivatives their

New .omega.-(N-acylamino)alkylphosphoryl ethanolamines and their pharmaceutically acceptable acid addition salts have superior renin-inhibitory activities, antihypertensive activities and cholesterol-lowering activities. The .omega.-(N-acylamino)alkylphosphoryl ethanolamines are prepared by (1) reacting an .omega.-(N-acylamino) alkanol with a 2-(N-substituted amino)ethyl phosphate or its derivative, hydrolyzing the resulting product or splitting off the phosphoric acid-protective group of the resulting product thereby to form an .omega.-(N-acylamino) alkyl 2-(N-substituted amino) ethyl phosphate, and splitting off the amino-protective groups of the resulting phosphate, or (2) reacting an .omega.-(N-acylamino) alkanol with a phosphorus oxyhalide, reacting the resulting .omega.-(N-acylamino)alkyl dichlorophosphate with a 2-(N-substituted amino) ethanol, hydrolyzing the reaction product to form an .omega.-(N-acylamino) alkyl 2-(N-substituted)ethyl phosphate, and splitting off the amino-protective groups of said phosphate.

.omega.-(N-acylamino)alkylphosphoryl ethanolamines, pharmaceutical

Growing community of inventors

Takaishi, Japan

Naonobu Hatano