Asta Pharma Aktiengesellschaft

Basf Aktiengesellschaft

Zentaris Gmbh

Asta-werke Aktiengesellschaft, Chemische Fabrik

Henri Brunner

Jurgen Engel

Peter Hilgard

Wolfgang Schumacher

Rainer Voegeli

Friedrich Maiterth

Peter Hankofer

Manfred Schmidt

Helmut Schonenberger

Gerfried Unger

Guenther Bernhardt

Karl Christian Bart

Christian Lottner

Willigis Pieronczyk

Ulrich Holzinger

The invention relates to novel, water-soluble porphyrin platinum compounds of the tetraarylporphyrin platinum derivatives type or of the hematoporphyrin platinum derivatives type with high tumor selectivity and their use for the treatment of benign and malignant tumor diseases. In particular, the compounds are suitable for photodynamic anti-tumor therapy.

Water-soluble porphyrin platinum compounds with high tumor selectivity and their use for the treatment of benign and malignant tumor diseases

Antitumor acting platinum(II or IV) complexes of the general formula ##STR1## where B represents a phenyl-C.sub.1 -C.sub.4 -alkyl radical which is optionally substituted in the phenyl nucleus by the radical R.sub.1 and R.sub.1 is hydrogen, halogen, trihalogen methyl, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy or C.sub.2 -C.sub.6 -alkanoyloxy or where B together with the structural part H.sub.2 N-CR.sub.2 &lt; forms a tetrahydroisoquinoline radical, if B contains benzyl and R.sub.2 hydrogen and the benzyl radical in the 2-position contains the CH.sub.2 -radical or where B together with the structural part --CR.sub.2 &lt; represents a tetrahydronaphthyl radical in which one CH.sub.2 group is optionally replaced by oxygen, or where B together with the structural part --CR.sub.2 &lt; represents a decahydronaphthyl radical or an indanyl radical; R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, it also being possible for the phenyl ring of this group R.sub.2 to be substituted by hydroxy, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkanoyloxy or halogen; the radicals R.sub.3 and R.sub.4 are the same or different and represent hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl and X stands for the equivalent of a physiologically acceptable anion or X can also be a water molecule, where in the latter case the missing negative charge is saturated by a corresponding physiologically acceptable acid anion, where in the case of platinum(II) complexes, two of the groups X are absent.

Ethylene-substituted phenylalkylethylenediamine-platinum (II or IV)

Antitumor acting platinum(II or IV) complexes of the general formula ##STR1## where B represents a phenyl-C.sub.1 -C.sub.4 -alkyl radical which is optionally substituted in the phenyl nucleus by the radical R.sub.1 and R.sub.1 is hydrogen, halogen, trihalogen methyl, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy or C.sub.2 -C.sub.6 -alkanoyloxy or where B together with the structural part H.sub.2 N--CR.sub.2 &lt;forms a tetrahydroisoquinoline radical, if B contains benzyl and R.sub.2 hydrogen and the benzyl radical in the 2-position contains the CH.sub.2 -radical or where B together with the structural part --CR.sub.2 &lt; represents a tetrahydronaphthyl radical in which one CH.sub.2 group is optionally replaced by oxygen, or where B together with the structural part --CR.sub.2 &lt; represents a decahydronaphthyl radical or an indanyl radical; R.sub.2 represents hydrogen, C.sub.1 -C.sub.6 -alkyl, phenyl or phenyl-C.sub.1 -C.sub.4 -alkyl, it also being possible for the phenyl ring of this group R.sub.2 to be substituted by hydroxy, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.6 -alkanoyloxy or halogen; the radicals R.sub.3 and R.sub.4 are the same or different and represent hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl and X stands for the equivalent of a physiologically acceptable anion or X can also be a water molecule, where in the latter case the missing negative charge is saturated by a corresponding physiologically acceptable acid anion, where in the case of platinum(II) complexes, two of the groups X are absent.

Ethylene-substituted phenylalkylethylene-diamine-platinum (II or IV)

There are described (1-benzylethylenediamine)-platin(II)-complexes of the general formula: ##STR1## wherein the radicals R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are the same or different and are hydrogen, a C.sub.1 -C.sub.6 -alkyl group, a benzyl group, or a phenylethyl group, and B is a thienyl radical, an indolyl radical, an imidazolyl radical, or a phenyl radical substituted by the radicals R.sub.5, R.sub.6, an R.sub.7 which are the same or different and are hydrogen, halogen, trihalomethyl, C.sub.1 -C.sub.6 -alkyl, hydroxy, C.sub.1 -C.sub.6 -alkoxy, phenoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyloxy, benzoyloxy, C.sub.1 -C.sub.6 -alkanesulfonyloxy, carboxy, C.sub.1 -C.sub.6 -carbalkoxy, cyano, aminocarboxyl, aminocarbonyl, which contains one or two C.sub.1 -C.sub.6 -alkyl radicals, C.sub.1 -C.sub.6 -alkylcarbonyl, nitro, amino, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, (C.sub.1 -C.sub.6 -alkyl).sub.3 N.sup.+, C.sub.1 -C.sub.6 -alkanoylamino, C.sub.1 -C.sub.6 -alkyl-C.sub.1 -C.sub.6 -alkanoylamino, C.sub.1 -C.sub.6 -alkanesulfonylamino, C.sub.1 -C.sub.6 -alkyl-C.sub.1 -C.sub.6 -alkanesulfonylamino, aminosulfonyl, aminosulfonyl which contains one or two C.sub.1 -C.sub.6 -alkyl radicals, C.sub.1 -C.sub.6 -alkoxysulfonyl (--SO.sub.2 --O--C.sub.1 --C.sub.6 -alkyl), sulfo (--SO.sub.3 H) or C.sub.1 -C.sub.6 -alkanesulfonyl and two of these groups can be the methylenedioxy group and X is the equivalent of a physiologically compatible anion, as well as optionally their salts with physiologically compatible cations and anions and process of their production.

Tumor retarding (1-benzyl-ethylenediamine)-platin (II)-complexes

A process for the preparation of pure optically active tertiary phosphines by resolving the corresponding racemic compounds, wherein

Optically active tertiary phosphine oxides and tertiary phosphines and

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Lappersdorf, Germany

Henri Brunner