Sankyo Company, Limited

Kiyoshi Sakai

Takashi Yusa

Shinsaku Kobayashi

Koichi Kojima

Mitsuo Yamazaki

Junya Ide

Osamu Oda

Kazuhiko Sasagawa

Kenji Inoue

Masaaki Sasaki

Hamako Katano

Prostacyclin derivatives of formula (I): ##STR1## (wherein R.sup.1 represents a hydrogen atom or a lower alkyl group; R.sup.2 represents an alkenyl group having from 8 to 12 carbon atoms; and n represents an integer of from 1 to 8, inclusive) and pharmaceutically acceptable salts thereof, are valuable pharmaceuticals, showing excellent thrombocyte agglutination inhibitory, coronary blood vessel dilatory and bronchodilatory effects, and may be prepared by introducing the .dbd.CH(CH.sub.2).sub.n COOR.sup.1 side chain onto an appropriate compound by means of a Wittig reaction.

Prostacyclin compounds

Prostanoic acid derivatives having the formula ##STR1## wherein A represents ethylene group or cis-vinylene group, R.sup.1 and R.sup.2 may be the same or different and each represents hydrogen atom or an alkyl group having 1-3 carbon atoms, R.sup.3 and R.sup.4 may be the same or different and each represents an alkyl group having 1-3 carbon atoms and R.sup.5 represents hydrogen atom or hydroxyl group and the pharmaceutically acceptable salts thereof and a process for the preparation thereof. The compounds are useful as anti-ulcerogenic or bronchodilating agents and may be prepared by oxidizing 9.xi.-hydroxy-15.xi.-protected-hydroxy-20-alkylideneprost-13(trans)-enoic acid derivatives.

9-OXO-15 .xi.-HYDROXY-20-ALKYLIDENEPROST-13(TRANS)-ENOIC ACID DERIVATIVES

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

Kiyoshi Sakai