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Claims for Patent: 5,420,319

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Claims for Patent: 5,420,319

Title: Cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex having high optical purity and process of preparing same
Abstract: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##
Inventor(s): Okamoto; Koji (Kanagawa, JP), Nakanishi; Chihiro (Kanagawa, JP), Taniuchi; Junichi (Kanagawa, JP), Ohnishi; Junji (Kanagawa, JP), Komoda; Yasunobu (Kanagawa, JP)
Assignee: Tanaka Kikinzoku Kogyo K.K. (JP)
Application Number:08/117,892
Patent Claims: 1. Cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex having high optical purity represented by Formula 1 which possesses optical purity of 99.94% or more and a melting point between 198.3.degree. C. and 199.7.degree. C. ##STR8##

2. In a process for the preparation of cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex of high optical purity and a melting point between 198.3.degree. C. and 199.7.degree. C., the improvement which comprises utilizing as the starting material for the synthesis of the complex trans-1-1,2-cyclohexanediamine or a derivative thereof which has been optically resoluted by high performance liquid chromatography, said complex being represented by the Formula: ##STR9##

3. The process of claim 2 wherein the optically resoluted trans-1-1,2-cyclohexanediamine or derivative thereof is dissolved in water and reacted with a tetrahalogenoplatinum (IV) acid salt to produce cis-tetrahalogeno(trans-1-1,2-cyclohexanediamine) Pt(IV).

4. The process of claim 2 wherein the tetrahalogenoplatinum (IV) salt comprises potassium tetrachloroplatinate and the cis-tetratetrahalogeno(trans-1-1,2-cyclohexanediamine) Pt(IV) comprises cis-tetrachloro(trans-1-1,2-cyclohexanediamine) Pt(IV).

5. The process of claim 4 wherein the cis-tetrachloro(trans-1-1,2-cyclohexanediamine) Pt(IV) is reacted with 2 moles of silver oxalate per mole of cis-tetrachloro(trans-1-1,2-cyclohexane-diamine) Pt(IV) to produce cis-oxalato(trans-1-1,2-cyclohexane-diamine) Pt(II) complex.

6. The process of claim 4 wherein the cis-tetrachloro(trans-1-1,2-cyclohexanediamine) Pt(IV) is reacted with equimolar silver oxalate and thereafter reduced with a suitable reducing agent to produce cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex.

7. The process of claim 2 wherein the optically resoluted trans-1-1,2-cyclohexanediamine or derivative thereof is dissolved in water and reacted with potassium tetrachloroplatinate to produce cis-dichloro(trans-1-1,2-cyclohexanediamine) Pt(IV).

8. The process of claim 7 wherein the cis-dichloro(trans-1-1,2-cyclohexanediamine) Pt(IV) is suspended in water and reacted with equimolar silver oxalate to produce cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex.

9. The process of claim 7 wherein the cis-dichloro(trans-1-1,2-cyclohexanediamine) Pt(IV) is suspended in water and reacted with silver nitrate or silver sulfate followed by elution with an anion exchange resin (OH form) to produce cis-dihydroxy(trans-1-1,2-cyclohexanediamine) Pt(IV) which is thereafter reacted with oxalic acid to produce cis-oxalato(trans-1-1,2-cyclohexanediamine) Pt(II) complex.

10. The process of claim 2 wherein the high performance liquid chromatography is carried out in a column packed with a filler comprised of a material selected from the group consisting of cellulose, a cellulose ester derivative, a cellulose carbamate derivative, an amylose carbamate derivative, a polymethacryl acid ester, .beta.- and .gamma.-cyclodextrin, a polymethacrylamide derivative, an acidic glycoprotein, L-proline, hydroxyproline, L-valine, a material prepared by adsorbing or binding (1R,2S)-2-carboxy-methylamino-1,2-diphenylethanol to silica gel, a material prepared by coordinating a metal ion to one of the aforesaid materials, a material prepared by adsorbing or binding a protein to aminated silica gel, a crown ether, a urea derivative chiral to silica gel treated with (3-aminopropyl)triethoxysilane, N(3,5-dinitrobenzoyl)-(R)-phenylglycine, a material chemically bonded to DNB-L-leucine and (S)-1-(.alpha.-naphthyl)-ethylamino-(S)-2-(4-chlorophenyl)isovaleric acid, an octadecylsilane and a silica gel.

11. The process of claim 2 wherein the optically resoluted trans-1-1,2-cyclohexanediamine derivative is prepared by reacting 1,2-cyclohexanediamine with a compound selected from the group consisting of L-(+)-tartaric acid, D-(-)-tartaric acid, L-(+)-benzoyltartaric acid and D-(-)-benzoyltartaric acid to form the diastereomer and optically resoluting the diastereomer by high performance liquid chromatography.

12. The process of claim 2 wherein derivative utilized as the optically resoluted trans-1-1,2-cyclohexane-diamine derivative is selected from the group consisting of an isoindolin derivative, a benzoyl derivative, an acetyl derivative, a 3,5-dinitrobenzoyl derivative and a para-nitrobenzoyl derivative.

13. The process of claim 2 wherein the high performance liquid chromatography is carried out by utilizing a column packed with a chiral filler and a polarimeter as a detector.
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