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US5023358A
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Vanadyl organo-mineral compound, method for obtaining such a compound, pharmaceutical composition containing this organo-mineral compound
Assignee: University of British Columbia
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Filing: 1988-08-10
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Granted: 1991-06-11
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Expires: 2008-08-10
Abstract
Abstract The present invention concerns a vanadyl organo-mineral compound which is in the form of a complex of vanadyl and of cystein, having the following general formula: ##STR1## wherein, either x is 1 and y is 0, or x is 0 and y is 1, and wherein n, p and m are respectively integers with a value of 1 or 2.
Inventors
- 👤 Rene Lazaro
- 👤 Gerard Cros
- 👤 John H. McNeill
- 👤 Jean-Jacques Serrano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:35
CPC Classifications
C; C07; C07F; C07F5/00; C07F9/00; C07F9/005; A; A61; A61P; A61P3/00; A61P3/08
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
223 words
A vanadyl organo-mineral compound in the form of a complex of vanadyl and of cysteine with the following general formula: ##STR16## wherein n, p and m are integers equal to 1 or 2 respectively and wherein when p=1 then: Y is selected from the group consisting of a hydrogen atom and a R'--CO group; and (a) when n=1 and m=2, X is selected from the group consisting of an OH group, an OR group and a NHR group wherein R is selected from the group consisting of an alkyl group different from a methyl group comprising from 2 to 9 carbon atoms; wherein: when X=an OH group: Y=a R'--CO group wherein R' is selected from the group consisting of an alkyl group comprising from 2 to 9 carbon atoms, and, when X is selected from the group consisting of an OR group and an NHR group: Y is H; and (b) when n=2 and m=1, X is selected from the group consisting of: ##STR17## wherein R is selected from the group consisting of an alkyl group other than butyl comprising from 2 to 9 carbon atoms; and wherein p=2 then: n=1, m=1, X=an OH group, Y is selected from the group consisting of ##STR18## wherein R' is selected from the group consisting of an alkyl group comprising from 2 to 9 carbon atoms.
Claim 2
Dependent Claim
223 words
A vanadyl organo-mineral compound in the form of a complex of vanadyl and of cysteine with the following general formula: ##STR16## wherein n, p and m are integers equal to 1 or 2 respectively and wherein when p=1 then: Y is selected from the group consisting of a hydrogen atom and a R'--CO group; and (a) when n=1 and m=2, X is selected from the group consisting of an OH group, an OR group and a NHR group wherein R is selected from the group consisting of an alkyl group different from a methyl group comprising from 2 to 9 carbon atoms; wherein: when X=an OH group: Y=a R'--CO group wherein R' is selected from the group consisting of an alkyl group comprising from 2 to 9 carbon atoms, and, when X is selected from the group consisting of an OR group and an NHR group: Y is H; and (b) when n=2 and m=1, X is selected from the group consisting of: ##STR17## wherein R is selected from the group consisting of an alkyl group other than butyl comprising from 2 to 9 carbon atoms; and wherein p=2 then: n=1, m=1, X=an OH group, Y is selected from the group consisting of ##STR18## wherein R' is selected from the group consisting of an alkyl group comprising from 2 to 9 carbon atoms.
Claim 3
Dependent Claim
14 words
The compound according to claim 1, wherein the cystein is in its L form.
Claim 4
Dependent Claim
14 words
The compound according to claim 1, wherein the cystein is in its D form.
Claim 5
Dependent Claim
37 words
The compound according to claim 1, PG,22 wherein p=1, n=1 and m=2, and which corresponds to the following formula II: ##STR19## wherein X is selected from the group consisting of an OR group and a NHR group.
Claim 6
Dependent Claim
26 words
The compound according to claim 1 wherein p=1, n=2, and m=2, wherein X represents an OH group and which corresponds to the following formula IV: ##STR20##
Claim 7
Dependent Claim
20 words
The compound according to claim 1 wherein p=1, n=2, and m=1 and which corresponds to the following formula III: ##STR21##
Claim 8
Dependent Claim
20 words
The compound according to claim 1 wherein p=2, n=1, and m=1 and which corresponds to the following formula V: ##STR22##
Claim 9
Dependent Claim
153 words
A method for preparing the compound of formula I of claim 1, which comprises: a. preparing in a first step a cystein derivative by reacting a first compound, selected from the group consisting of a mono- or difunctional amine, a mono- or difunctional alcohol, and an amine-alcohol, with a second compound, selected from the group consisting of the cystein and a derivative of the cystein, which second compound is protected on the amine function and on the thiol function by a tertiobutyloxycarbonyl group in the presence of dicyclohexylcarbodiimide/hydroxybenzotriazole, by eliminating the tertiobutyloxycarbonyl group by acidolysis; and b. in a second step adding a vanadyl sulfate dissolved in water, under a nitrogen atmosphere, to a solution of said cystein derivative, in a dimethylformamide-borate buffer mixture at a pH of about 10, with a cystein:vanadyl ratio of 5:1; recovering the precipitated complex obtained; and washing said precipitated complex with water and drying said precipitated complex.
Claim 10
Dependent Claim
104 words
Method for preparing the compound of formula I according to claim 1, which comprises: reacting a first compound, selected from the group consisting of the cystein and a derivative thereof, with a vanadyl sulfate at a pH of about 7 in water, recovering a first complex obtained after evaporation, redissolving said first complex in dimethylformamide, coupling a second compound selected from the group consisting of a mono- or difunctional amine, a mono- or difunctional alcohol and an amine-alcohol, through the medium of the dimethylaminopropylethylcarbodiimide, recovering a second complex after vacuum evaporation of the solvent, and washing the second complex with ether and with water.
References Cited (Backward Citations)
US3076830A
Cited
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