Sankyo Company, Limited

Takashi Yusa

Kiyoshi Sakai

Mitsuo Yamazaki

Osamu Oda

Shinsaku Kobayashi

Kazuhiko Sasagawa

Junya Ide

Masaaki Sasaki

Hamako Katano

Kenji Inoue

Prostanoic acid derivatives having the formula ##STR1## wherein A represents a straight or branched alkylene group having from one to 5 carbon atoms, R.sup.1 represents a straight or branched alkyl group having from 4 to 10 carbon atoms and R.sup.2 represents hydrogen atom or a straight or branched alkyl group having from one to 6 carbon atoms and pharmaceutically acceptable salts thereof. The compounds are useful as oxytocic agents and agents inhibiting the secretion of gastric acid and may be prepared by oxidizing a compound having the formula ##STR2## wherein A, R.sup.1 and R.sup.2 are the same as above, R.sup.3 and R.sup.4 are the same or different and each represents a protecting group for the hydroxyl group to give a compound having the formula ##STR3## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as above, removing the hydroxyl-protecting group from the latter compound and, if appropriate, salifying the product thus obtained.

16,16-Dimethyl

Prostanoic acid derivatives having the formula ##STR1## wherein A represents an alkylene group having from 4 to 8 carbon atoms, R.sup.1 represents an alkyl group having from one to 5 carbon atoms, R.sup.2 and R.sup.3 may be the same or different and each represents hydrogen atom or an alkyl group having from one to 4 carbon atoms and R.sup.4 represents hydrogen atom or an alkyl group having from one to 4 carbon atoms and the pharmaceutically acceptable salts thereof and also relates to a process for the preparation thereof. The compounds are useful as anti-ulcerogenic agents and may be prepared by reducing a compound having the formula ##STR2## wherein A, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same above and Z represents a carbonyl-protecting group to give a compound having the formula ##STR3## wherein A, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and Z are the same as above and removing the carbonyl-protecting group from the latter compound.

9-Oxo-11.alpha.-methyl-15.EPSILON.-hyroxyprost-13(trans)-enoic acid

Prostanoic acid derivatives having the formula ##SPC1## Wherein A represents an alkylene group having from 4 to 8 carbon atoms, R.sup.1 represents an alkyl group having from 4 to 10 carbon atoms, R.sup.2 represents hydrogen atom or an alkyl group having from one to 6 carbon atoms and R.sup.3 represents hydrogen atom or an alkoxycarbonyl group having from one to 6 carbon atoms in the alkyl moiety and the pharmaceutically acceptable salts thereof and also relates to a process for the preparation thereof. The compounds are useful as oxytocic agents and may be prepared by reducing the compound having the formula ##SPC2## Wherein A, R.sup.1, R.sup.2 and R.sup.3 are the same as above and Z represents a carbonyl-protecting group with a metal hydride complex in the presence or absence of an inert organic solvent to give a compound having the formula ##SPC3## Wherein A, R.sup.1, R.sup.2, R.sup.3 and Z are the same as above and removing the carbonyl-protecting group of the latter compound.

9-Oxo-11.alpha.-hydroxymethyl-15.epsilon.-hydroxyprost-13(trans)-enoic

New prostaglandin-like compounds, having brochodilating activity, of formula ##SPC1## (wherein A represents a direct bond or an alkylene group and R.sup.1 represents an alkyl group) and their pharmaceutically acceptable salts are prepared by oxidizing compounds of formula ##SPC2## (wherein R.sup.2 represents hydrogen or a carboxyl-protecting group, and R.sup.3 represents a hydroxyl-protecting group), removing protecting groups from the product and, when appropriate, salifying the compound obtained.

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Tokyo, Japan

Takashi Yusa