Unique, valuable and multifariously utile macromolecular complexes are comprised of: (i) non-ionic, amidocarbonylic, water-soluble polymers (and, for some embodimental purposes, the monomeric precursor(s) thereof), including such known materials as (poly)N-vinylpyrrolidone (i.e., "PVP") and/or (poly)N-vinyl-5-methyl-2-oxazolidinone (i.e., "PVO-M") and the hereinafter disclosed like(s) and/or equivalent(s) thereof which, for convenience, may be herein generically identified as "WSP"; and (ii) square planar configured platinous and, for instant applicancy, equivalently metalled organometallic compounds characterized in containing in ligandal inclusion an aromatic moiety from which depends and to which is connected at least a single distinctly polar substituent group (or "handle", as it were), such as an hydroxide (i.e., "--OH"), carboxylic acid (i.e., "--COOH") or sulfonic acid - (i.e., "--SO.sub.3 H") unit and/or equivalents thereof as herein disclosed which, for convenience, may for generic identification be herein called an "SPOM". The WSP:SPOM complex(es) are associated by non-ionic or other bonding attachment in the nature of hydrogen bonding and/or closely related electrostatic interaction between or through and to the polar substituent in the SPOM and the amidocarbonylic unit in the WSP.

This invention relates to a novel platinum-diamine complexes represented by the general formula: ##STR1## wherein R.sub.1 and R.sub.2 each represents a lower alkyl group having 1 to 3 carbon atoms or jointly represent an alkylene group having 3 to 6 carbon atoms; two X's each represents a halogen atom, ##STR2## or jointly represent a group represented by ##STR3## in which R.sub.3 is a lower alkyl group or a group represented by --OM (wherein M is an atom which can become a monovalent cation); Y is --OH or a halogen atom; and n is 0 or 1, and n is 1 when R.sub.1 and R.sub.2 jointly represent an alkylene group having 5 carbon atoms and X is chlorine. The platinum-diamine complex of this invention has an excellent antitumor activity and a lower renal toxicity than cis-Platin now widely used as a carcinostatic as clinical medicine, and is expected as a carcinostatic lowered in toxicity.

Disclosed herein is a process of optically resoluting optically active platinum complex compounds which comprises optically resoluting a d-isomer and an 1-isomer of a cis-Pt(II) complex of a 1,2-cyclohexanediamine isomer characterized in that the mixture of the d-isomer and the 1-isomer is optically resoluted by means of high performance liquid chromatography employing a column packed with a chiral filler. The chiral filler include, for example, a cellulose ester derivative, a cellulose carbamate derivative, an amylose carbamate derivative, a polymethacryl acid ester and .beta.- and .gamma.-cyclodextrin. According to the present invention, the optical resolution of a platinum complex compound essentially consisting of the mixture of two optical isomers which cannot be resoluted in accordance with a normal resolution method due to the small structural difference can be easily performed utilizing the characteristics of a chiral filler.

Disclosed is cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex having high optical purity and no toxicity and exhibiting anticancer performance, as shown in the below Formula. Cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex of the invention possesses high optical purity or 99.94% or more e.e. and a melting point of 198.3.degree. to 199.7.degree. C. The complex is synthesized employing as starting material trans-1-1,2-cyclohexamediamine or a derivative of the trans-1-1,2-cyclohexanediamine optically resoluted by means of a high performance liquid chromatography. ##STR1##

Platinum diamine complexes of the general formulae ##STR1## wherein R.sub.1 and R.sub.2 independently from each other are a hydrogen atom or a substituted or unsubstituted alkyl, cyclo-alkyl, aryl or aralkyl group, while R.sub.1 and R.sub.2 may be together a substituted or unsubstituted cyclo-alkyl group, R.sub.3 and R.sub.4 independently of each other are a hydrogen atom or a substituted or unsubstituted alkyl, aryl or aralkyl group and X is a chlorine, bromine or iodine atom, a sulphate radical, a substituted or unsubstituted carboxylate rest like an acetate or substituted acetate radical, an oxalate, malonate, hydroxymalonate or otherwise substituted malonate group or a carboxylate group, the group Y, independently from X is a chlorine, bromine or iodine atom, a hydroxyl group, a nitrate group of a carboxylate group have been found to exhibit antitumor activity together with little or none kidney toxicity and are thus of interest as a medicament. Processes for the preparation of the platinum complexes are described and exemplified.