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US4614811A
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Novel organoplatinum(II) complexes and method for the preparation thereof
Assignee: Yissum Research Development Co of Hebrew University of Jerusalem
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Filing: 1985-03-18
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Granted: 1986-09-30
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Expires: 2005-03-18
Abstract
Abstract Amino-substituted-malonato platinum(II) complexes represented by the gene formula L.sub.2 Pt.sup.II (OCO).sub.2 CH--NH.sub.2 wherein L and L 2 are monodentate and bidentate aliphatic amine ligands respectively. Typical examples of L and L 2 are: NH 3 , ethylendiamine, 1,2-diaminocyclohexane, ethylenimine, and cyclopropyl-, cyclobutyl-, cyclopentyl-, cyclohexyl-, isopropyl-, n-propyl-amine. The compounds are characterized by high antitumor activity in mice, chemical stability and solubility in aqueous fluids for i.v. administration. The invention provides also a preferred method for their preparation.
Inventors
- 👤 Ottavio Gandolfi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:35
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/0006; C07F15/0086; C07F15/0093
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
181 words
Amino-substituted malonato platinum complexes having the general formula: L.sub.2 Pt.sup.II (OCO).sub.2 CH--NH.sub.2 wherein: L is a monodentate aliphatic amine ligand of the type HNRR 1 or an amino acid, wherein, when R=H, R 1 is selected from the group consisting of H, hydroxy, lower alkyl, cycloalkyl, hydroxy lower alkyl, and lower alkoxy; R and R 1 can also be combined to form an imine group; L 2 is a bidentate aliphatic amine ligand of the type HNR 2 --CHR 3 --(CR 4 R 5 ) n --CHR 6 --NHR 7 , wherein n=0 or 1, and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different substituents and are selected from the group consisting of H, hydroxy, lower alkyl, lower alkoxy cycloalkyl; when n=0, R 3 and R 6 can be combined to form a cycloalkyl group; when n=1, R 3 can be combined with R 4 , or R 4 and R 5 can be combined with the carbon atom, to form in each case a cycloalkyl group.
Claim 2
Dependent Claim
181 words
Amino-substituted malonato platinum complexes having the general formula: L.sub.2 Pt.sup.II (OCO).sub.2 CH--NH.sub.2 wherein: L is a monodentate aliphatic amine ligand of the type HNRR 1 or an amino acid, wherein, when R=H, R 1 is selected from the group consisting of H, hydroxy, lower alkyl, cycloalkyl, hydroxy lower alkyl, and lower alkoxy; R and R 1 can also be combined to form an imine group; L 2 is a bidentate aliphatic amine ligand of the type HNR 2 --CHR 3 --(CR 4 R 5 ) n --CHR 6 --NHR 7 , wherein n=0 or 1, and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different substituents and are selected from the group consisting of H, hydroxy, lower alkyl, lower alkoxy cycloalkyl; when n=0, R 3 and R 6 can be combined to form a cycloalkyl group; when n=1, R 3 can be combined with R 4 , or R 4 and R 5 can be combined with the carbon atom, to form in each case a cycloalkyl group.
Claim 3
Dependent Claim
14 words
Aminomalonate(diamine)platinum(II), (AM--DP) of the formula of claim 1, wherein L is NH 3 .
Claim 4
Dependent Claim
13 words
Aminomalonate(ethylendiamine)platinum(II), (AM--EP), of the formula of claim 1, wherein L 2 is ethylendiamine.
Claim 5
Dependent Claim
13 words
Aminomalonate(1,2-diaminocyclohexane)platinum(II), (AM--DACHP), of the formula of claim 1, wherein L 2 is 1,2-diaminocyclohexane.
Claim 6
Dependent Claim
12 words
Aminomalonate(diethylenimine)platinum(II), (AM--AZP), of the formula of claim 1, wherein L is ethylenimine.
Claim 7
Dependent Claim
12 words
Aminomalonate(dicyclopropylamine)platinum(II), (AM--CPRP), of the formula of claim 1, wherein L is cyclopropylamine.
Claim 8
Dependent Claim
12 words
Aminomalonate(dicyclobutylamine)platinum(II), (AM--CBP), of the formula of claim 1, wherein L is cyclobutylamine.
Claim 9
Dependent Claim
12 words
Aminomalonate(dicyclopentylamine)platinum(II), (AM--CPP), of the formula of claim 1, wherein L is cyclopentylamine.
Claim 10
Dependent Claim
12 words
Aminomalonate(dicyclohexylamine)platinum(II), (AM--CHP), of the formula of claim 1, wherein L is cyclohexylamine.
Claim 11
Dependent Claim
12 words
Aminomalonate(diisopropylamine)platinum(II), (AM--IPA), of the formula of claim 1, wherein L is isopropylamine.
Claim 12
Dependent Claim
12 words
Aminomalonate(din-propylamine)platinum(II), (AM--NPA), of the formula of claim 1, wherein L is n-propylamine.
Claim 13
Independent Claim
239 words
A method for the preparation of amino-substituted malonato platinum complexes having the general formula: L.sub.2 Pt.sup.II (OCO).sub.2 CH--NH.sub.2 wherein: L is a monodentate aliphatic amine ligand of the type HNRR 1 or an aminoacid, wherein, when R=H, R 1 is selected from the group consisting of H, hydroxy, lower alkyl, cycloalkyl, hydroxy lower alkyl, and lower alkoxy; R and R 1 can also be combined to form an imine group; L 2 is a bidentate aliphatic amine ligand of the type HNR 2 --CHR 3 --(CR 4 R 5 ) n --CHR 6 --NHR 7 , wherein n=0 or 1, and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different substituents and are selected from the group consisting of H, hydroxy, lower alkyl, lower alkoxy, cycloalkyl; when n=0, R 3 and R 6 can be combined to form a cycloalkyl group; when n=1, R 3 can be combined with R 4 , or R 4 and R 5 can be combined with the carbon atom, to form in each case a cycloalkyl group; said method comprising reacting the barium salt of aminomalonic acid with a platinum(II) sulfate intermediate having the general formula L 2 PtSO 4 , wherein L and L 2 are defined as in the general formula above, to form the complex of the formula L 2 Pt II (OCO) 2 CH--NH 2 .
Claim 14
Independent Claim
239 words
A method for the preparation of amino-substituted malonato platinum complexes having the general formula: L.sub.2 Pt.sup.II (OCO).sub.2 CH--NH.sub.2 wherein: L is a monodentate aliphatic amine ligand of the type HNRR 1 or an aminoacid, wherein, when R=H, R 1 is selected from the group consisting of H, hydroxy, lower alkyl, cycloalkyl, hydroxy lower alkyl, and lower alkoxy; R and R 1 can also be combined to form an imine group; L 2 is a bidentate aliphatic amine ligand of the type HNR 2 --CHR 3 --(CR 4 R 5 ) n --CHR 6 --NHR 7 , wherein n=0 or 1, and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different substituents and are selected from the group consisting of H, hydroxy, lower alkyl, lower alkoxy, cycloalkyl; when n=0, R 3 and R 6 can be combined to form a cycloalkyl group; when n=1, R 3 can be combined with R 4 , or R 4 and R 5 can be combined with the carbon atom, to form in each case a cycloalkyl group; said method comprising reacting the barium salt of aminomalonic acid with a platinum(II) sulfate intermediate having the general formula L 2 PtSO 4 , wherein L and L 2 are defined as in the general formula above, to form the complex of the formula L 2 Pt II (OCO) 2 CH--NH 2 .
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