Otsuka Pharmaceutical Company, Limited

Tadao Sato

Kazuyuki Nakagawa

Hiraki Ueda

Wasei Miyazaki

Yasuo Nakayama

Tsuneo Sato

This invention provides a process for preparing a fibrin-adsorable protein-urokinase complex characterized by reacting a protein adsorbable by fibrin with urokinase in the presence of a protein coupling reagent represented by the formula ##STR1## wherein R is phenylene or cycloalkylene, A is lower alkylene, B is lower alkylene which may optionally be substituted by lower alkylthio or phenyl-lower alkylthio, and l, m and n are each 0 or 1 provided that l, m and n are not 0 at the same time. The complex is useful as a thrombolytic agent.

Process for preparing urokinase complex

Novel method optically active oxazaphosphorin derivatives represented by the general formula (I), ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are respectively different from each other and are hydrogen atom(s), lower alkyl group(s), aralkyl group(s), or aryl group(s); and X is a halogen atom. The novel oxazaphosphorin derivative is prepared by reacting an optically active amino alcohol derivative represented by the general formula (II), ##STR2## wherein R.sup.1, R.sup.2 and R.sup.3 are the same as defined above, with a phosphorus compound represented by the general formula (III),

Process for preparing optically active oxazaphosphorins

A novel process for preparing cyclo-1,3,2-oxazaphosphoryl derivatives represented by the formula (II), ##STR1## wherein R.sup.2 and R.sup.3 are respectively a lower alkyl group which may have halogen atom(s) or lower alkane-sulfonyloxy group(s) as substituted group(s) and n is an integer of 2 to 6, by acid cleaving the R.sup.1 --N bond of the compound represented by the formula (I), ##STR2## wherein R.sup.1 is an .alpha.-arylalkyl group, by using a strong acid, the compound represented by the formula (II) being effective as an anticancer agent.

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Tokushima, Japan

Tadao Sato