Yamanouchi Pharmaceutical Company Ltd.

Teruya Kashiwagi

Masuo Murakami

Ichiro Isaka

Teruaki Ozasa

Kozo Takahashi

Akio Koda

Yukiyasu Murakami

Isao Souzu

Kohzi Nakano

Hidefumi Matsui

Hiroshi Horiguchi

Khozi Nakano

An improved process for the displacement of the acetoxy group of a 7-aminocephalosporanic acid by a heterocyclic thiol in the presence of sulfuric acid.

Heterocyclic thiomethylation of the 3-position of 7-aminocephalosporanic

An improved process of preparing a 6-alkoxy-substituted penicillin or penicillin sulfoxide is disclosed. This process comprises adding a halogenating agent to penicillin or penicillin sulfoxide while cooling, and then adding an alkali metal alcoholate to the hydrogenation product in the presence of an alcohol corresponding to the alcoholate.

Process for the preparation of 6-alkoxy-substituted penicillins

The oxofuryl ester derivatives of 6-(.alpha.-amino-phenylacetamido)penicillanic acid, 7-(.alpha.-aminophenylacetamido)-cephalosporanic acid, or 7-(.alpha. -aminophenylacetamide)desacetoxycephalosporanic acid represented by the general formula ##SPC1## Wherein A represents ##SPC2## Wherein R.sup.1 and R.sup.2, which may be the same or different, each represents a hydrogen atom or a lower alkyl group, said R.sup.1 and R.sup.2 may form together a 1,3-butadienylene group, R.sup.3 represents a hydrogen atom or an acetoxy group, and Means a single bond or a double bond, and acid addition salts of them. When those compounds are orally administered, they are readily absorbed by the intestines and show antibacterial activity by splitting their ester bonds. The rate of absorption of the compounds by the intestines are higher and the toxic property of them is less than those of known compounds similar to the above compounds.

Novel oxofuryl ester derivatives of penicillin and cephalosporin

The penicillin derivatives represented by the formula ##SPC1## Wherein ring A represents a 5- or 6-membered single or fused ring which may contain one or more nitrogen atoms, an oxygen atom, or a sulfur atom; R.sup.1, R.sup.2, and R.sup.3, which may be the same or different, each represents a hydrogen atom, a hydroxy group, a lower alkyl group, a nitro group, a halogen atom, or an oxo group; and B represents a p-hydroxyphenyl group or a 1,4-cyclohexadien -1-yl group, and their nontoxic pharmaceutically acceptable salts. The compounds are antibiotics having excellent antibacterial activity in particular with respect to the Pseudomonas genus.

Penicillin derivatives

A process for the preparation of cephalosporanic acid derivatives represented by the formula ##SPC1## Wherein R.sub.1 and R.sub.2, which may be the same or different, each represents a univalent group other than a hydrogen atom, said R.sub.1 and R.sub.2 may be combined to form a divalent group and A represents a divalent group represented by the formulae ##SPC2## Wherein R.sub.3 represents a hydrogen atom or a group which does not contribute to the reaction, which comprises heating a penicillin sulfoxide derivative represented by the formula ##SPC3## Wherein R.sub.1, R.sub.2 and R.sub.3 are as defined above. The cephalosporanic acid derivatives prepared by the process of this invention are useful as a starting material for the preparation of antibacterials.

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Ageo, Japan

Teruya Kashiwagi