US4410544A
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Platinum-diamine complexes, a method for the preparation of a medicine using such a platinum-diamine complex for the treatment of malignant tumor in mice
Assignee: Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO
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Filing: 1981-07-27
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Granted: 1983-10-18
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Expires: 2001-07-27
Abstract
Abstract This invention relates to novel platinum-diamine complexes having the formula: ##STR1## wherein R 1 and R 2 independently of each other may be selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, a cycloalkyl group having from 3-7 carbon atoms in the ring, an aralkyl group, and an aryl group having 1-20 carbon atoms, whereas R 1 and R 2 together may form a cycloalkyl group having 3-7 carbon atoms in the ring and having the formula: ##STR2## wherein N is 2 to 7 and wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group, providing that when X is either chlorine or malonate, R 1 , R 2 , R 3 and R 4 are not each H; when X is chlorine and R 1 and R 2 are each H, R 3 and R 4 are not each methyl; when X is chlorine and R 1 and R 2 are each methyl, R 3 and R 4 are not each H, and when X is chlorine R 1 is hydrogen and R 2 is methyl and R 3 and R 4 are not each hydrogen.
Inventors
- 👤 Jan Berg
- 👤 Francois Verbeek
- 👤 Eric J. Bluten
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 08:40
CPC Classifications
C; C07; C07F; C07F15/00; C07F15/0006; C07F15/0086; C07F15/0093; A; A61; A61P; A61P35/00; A61P35/02
Claims Analysis
Total Claims: 55
Claim 1
Independent Claim
222 words
Platinum-diamine complexes having the formula: ##STR20## wherein R 1 and R 2 independently of each other may be selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, a cycloalkyl group having from 3-7 carbon atoms in the ring, an aralkyl group, and an aryl group having 1-20 carbon atoms, whereas R 1 and R 2 together may form a cycloalkyl group having 3-7 carbon atoms in the ring and having the formula: ##STR21## wherein n is 2 to 7 and wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group, providing that when X is either chlorine or malonato, R 1 , R 2 , R 3 and R 4 are not each H; when X is chlorine and R 1 and R 2 are each H, R 3 and R 4 are not each methyl; when X is chlorine and R 1 and R 2 are each methyl; R 3 and R 4 are not each H, and when X is chlorine R 1 is hydrogen and R 2 is methyl, R 3 and R 4 are not each hydrogen.
Claim 2
Dependent Claim
222 words
Platinum-diamine complexes having the formula: ##STR20## wherein R 1 and R 2 independently of each other may be selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, a cycloalkyl group having from 3-7 carbon atoms in the ring, an aralkyl group, and an aryl group having 1-20 carbon atoms, whereas R 1 and R 2 together may form a cycloalkyl group having 3-7 carbon atoms in the ring and having the formula: ##STR21## wherein n is 2 to 7 and wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group, providing that when X is either chlorine or malonato, R 1 , R 2 , R 3 and R 4 are not each H; when X is chlorine and R 1 and R 2 are each H, R 3 and R 4 are not each methyl; when X is chlorine and R 1 and R 2 are each methyl; R 3 and R 4 are not each H, and when X is chlorine R 1 is hydrogen and R 2 is methyl, R 3 and R 4 are not each hydrogen.
Claim 3
Dependent Claim
70 words
Platinum-diamine complexes having the formula: ##STR22## wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group, selected from the group consisting of chlorine, bromine, iodine, sulphate, phthalate, acetate, oxalate, malonate, substituted malonate, carboxylate, and isocitrate.
Claim 4
Dependent Claim
70 words
Platinum-diamine complexes having the formula: ##STR22## wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group, selected from the group consisting of chlorine, bromine, iodine, sulphate, phthalate, acetate, oxalate, malonate, substituted malonate, carboxylate, and isocitrate.
Claim 5
Dependent Claim
12 words
Cis-dichloro-1,1-di(aminomethyl)cycloalkyl platinum(II) having the formula: ##STR23## wherein n is 3 to 7.
Claim 6
Dependent Claim
12 words
Cis-dichloro-1,1-di(aminomethyl)cycloalkyl platinum(II) having the formula: ##STR23## wherein n is 3 to 7.
Claim 7
Dependent Claim
6 words
Cis-diiodo-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR24##
Claim 8
Dependent Claim
6 words
Cis-diiodo-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR24##
Claim 9
Dependent Claim
7 words
Cis-cyclopentamethylene malonato-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR25##
Claim 10
Dependent Claim
7 words
Cis-cyclopentamethylene malonato-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR25##
Claim 11
Dependent Claim
7 words
Cis-dichloro-(2-methyl-2-ethyl)-1,3-propane diamine platinum(II) having the formula: ##STR26##
Claim 12
Dependent Claim
7 words
Cis-dichloro-(2-methyl-2-ethyl)-1,3-propane diamine platinum(II) having the formula: ##STR26##
Claim 13
Dependent Claim
7 words
Cis-dichloro-2,2-diethyl-1,3-propane diamine platinum(II) having the formula: ##STR27##
Claim 14
Dependent Claim
7 words
Cis-dichloro-2,2-diethyl-1,3-propane diamine platinum(II) having the formula: ##STR27##
Claim 15
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclopentane platinum(II) having the formula: ##STR28##
Claim 16
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclopentane platinum(II) having the formula: ##STR28##
Claim 17
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane platinum(II) sulphate having the formula: ##STR29##
Claim 18
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane platinum(II) sulphate having the formula: ##STR29##
Claim 19
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclobutane platinum(II) having the formula: ##STR30##
Claim 20
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclobutane platinum(II) having the formula: ##STR30##
Claim 21
Dependent Claim
7 words
Cis-dichloro-2,2-dibenzyl-1,3-propane diamine platinum(II) having the formula: ##STR31##
Claim 22
Dependent Claim
7 words
Cis-dichloro-2,2-dibenzyl-1,3-propane diamine platinum(II) having the formula: ##STR31##
Claim 23
Dependent Claim
7 words
Cis-dichloro-2,2-diisopropyl-1,3-propane diamine platinum(II) having the formula: ##STR32##
Claim 24
Dependent Claim
7 words
Cis-dichloro-2,2-diisopropyl-1,3-propane diamine platinum(II) having the formula: ##STR32##
Claim 25
Dependent Claim
6 words
Cis-4-carboxyphtalato-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR33##
Claim 26
Dependent Claim
6 words
Cis-4-carboxyphtalato-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR33##
Claim 27
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)-cyclohexane-bis(chloroacetato) platinum(II) having the formula: ##STR34##
Claim 28
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)-cyclohexane-bis(chloroacetato) platinum(II) having the formula: ##STR34##
Claim 29
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-propanediamine platinum(II) sulphate having the formula: ##STR35##
Claim 30
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-propanediamine platinum(II) sulphate having the formula: ##STR35##
Claim 31
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)cyclohexanemalonato platinum(II) having the formula: ##STR36##
Claim 32
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)cyclohexanemalonato platinum(II) having the formula: ##STR36##
Claim 33
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)cyclohexanehydroxymalonato platinum(II) having the formula: ##STR37##
Claim 34
Dependent Claim
6 words
Cis-1,1-di(aminomethyl)cyclohexanehydroxymalonato platinum(II) having the formula: ##STR37##
Claim 35
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 2-ethylmalonato platinum(II) having the formula: ##STR38##
Claim 36
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 2-ethylmalonato platinum(II) having the formula: ##STR38##
Claim 37
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 2-hydroxymalonato platinum(II) having the formula: ##STR39##
Claim 38
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 2-hydroxymalonato platinum(II) having the formula: ##STR39##
Claim 39
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclhexane 2-ethylmalonato platinum(II) having the formula: ##STR40##
Claim 40
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclhexane 2-ethylmalonato platinum(II) having the formula: ##STR40##
Claim 41
Dependent Claim
9 words
Cis-2,2-diethyl-1,3-diaminopropane 2-hydroxymalonato platinum(II) sodium salt, having the formula: ##STR41##
Claim 42
Dependent Claim
9 words
Cis-2,2-diethyl-1,3-diaminopropane 2-hydroxymalonato platinum(II) sodium salt, having the formula: ##STR41##
Claim 43
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane 1,1-cyclobutanedicarboxylato platinum(II) having the formula: ##STR42##
Claim 44
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane 1,1-cyclobutanedicarboxylato platinum(II) having the formula: ##STR42##
Claim 45
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 1,1-cyclobutanedicarboxylato platinum(II) having the formula: ##STR43##
Claim 46
Dependent Claim
7 words
Cis-2,2-diethyl-1,3-diaminopropane 1,1-cyclobutanedicarboxylato platinum(II) having the formula: ##STR43##
Claim 47
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane platinum(II) isocitrate having the formula: ##STR44##
Claim 48
Dependent Claim
7 words
Cis-1,1-di(aminomethyl)cyclohexane platinum(II) isocitrate having the formula: ##STR44##
Claim 49
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR45##
Claim 50
Dependent Claim
6 words
Cis-dichloro-1,1-di(aminomethyl)cyclohexane platinum(II) having the formula: ##STR45##
Claim 51
Dependent Claim
55 words
A pharmaceutical composition comprising a liquid or solid carrier and an amount of at least one of the compounds described in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 sufficient to treat malignant tumors in mice.
Claim 52
Dependent Claim
53 words
A method of treating malignant tumors in mice which consists of administering a therapuetically effective amount of the composition described in claim 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24 or 25 to mice having malignant tumors.
Claim 53
Dependent Claim
157 words
A pharmaceutical composition comprising a liquid or solid carrier and an amount sufficient to treat malignant tumors in mice of at least one of a platinum diamine complex having the formula: ##STR46## wherein R 1 and R 2 independently of each other may be selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, a cycloalkyl group having from 3-7 carbon atoms in the ring, an aralkyl group and an aryl group having 1-20 carbon atoms, whereas R 1 and R 2 together may form a cycloalkyl group having 3-7 carbon atoms in the ring and having the formula: ##STR47## wherein n is 2 to 7 and wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group.
Claim 54
Dependent Claim
157 words
A pharmaceutical composition comprising a liquid or solid carrier and an amount sufficient to treat malignant tumors in mice of at least one of a platinum diamine complex having the formula: ##STR46## wherein R 1 and R 2 independently of each other may be selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, a cycloalkyl group having from 3-7 carbon atoms in the ring, an aralkyl group and an aryl group having 1-20 carbon atoms, whereas R 1 and R 2 together may form a cycloalkyl group having 3-7 carbon atoms in the ring and having the formula: ##STR47## wherein n is 2 to 7 and wherein R 3 and R 4 independently of each other are selected from the group consisting of hydrogen, an alkyl group having 1-20 carbon atoms, an aryl group or an aralkyl group having 1-20 carbon atoms in the alkyl group and X is an anionic group.
Claim 55
Dependent Claim
28 words
A method of treating malignant tumors in mice which consists of administering a therapeutically effective amount of the composition described in claim 28 to mice having malignant tumors.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-10-17 | 1987-04-18 | 1987-10-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-10-17 | 1991-04-18 | 1991-10-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-10-17 | 1995-04-18 | 1995-10-18 | $7700.00 | Window Closed / Lapsed |