Sankyo Company, Limited

Junya Ide

Shigeki Muramatsu

Yoshio Tsujita

Shinsaku Kobayashi

Noritoshi Kitano

Kiyoshi Sakai

Koichi Kojima

Koichi Fujimoto

Mitsuo Yamazaki

Masao Kuroda

Takashi Yusa

Yasuo Nakada

Msao Kuroda

A storage stable form of the crystalline sulfate of 7-[2-(2-aminothiazol-4-yl)-(Z)-2-methoxyiminoacetamido]-3-[5-(2-hydroxyeth yl)-4-methylthiazoliomethyl]-3-cephem-4-carboxylate has a specified X-ray diffraction pattern and is prepared by adding aqueous sulfuric acid to an aqueous solution of the compound under controlled conditions.

Crystalline cephem carboxylic acid addition salt

5-Carbonate derivatives of milbemycins A.sub.3, A.sub.4 and A.sub.5 have valuable acaricidal, anthelmintic and other activities, especially against endo- and exoparasites.

Milbemycin 5-carbonate derivatives and compositions containing them

Compounds of formula (I): ##STR1## [wherein X represents a hydrogen atom or a 2-methylbutyryl group, Y represents a hydrogen atom or a methyl group and R.sup.1 and R.sup.2 are the same or different and each represents an oxygen atom or a group of formula .dbd.N--OR.sup.3 (wherein R.sup.3 represents a hydrogen atom or an alkyl group)], the free hydroxy-carboxylic acids corresponding thereto and salts and esters of said acids may be prepared by oxidizing and, if necessary, oximating a corresponding ML-236A, ML-236B, MB-530A or MB-530B compound, and these compounds have valuable antihypercholesteraemic activity.

Octahydronaphthalene derivatives and their preparation

Oxime derivatives of 5-didehydromilbemycins A.sub.3, A.sub.4 and D are represented by the formula: ##STR1## (wherein R.sup.1 represents methyl, ethyl or isopropyl, and R.sup.2 represents hydrogen, lower alkyl, optionally substituted aralkyl or --CH.sub.2 COOR.sup.3, wherein R.sup.3 represents hydrogen or lower alkyl). These and their salts and esters have valuable anthelmintic, acaricidal and insecticidal activity.

5-Oxime derivatives of milbemycins and veterinary and agricultural use

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 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.

Growing community of inventors

Hiromachi, Japan

Junya Ide