US4466952A
Expired / Lapsed
US
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Compositions and process for the treatment of cancer
Assignee: Indiana University Research and Technology Corp
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Filing: 1983-01-12
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Granted: 1984-08-21
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Expires: 2003-01-12
Abstract
Abstract Novel estratriene and estratetraene compositions bearing a dicarbadodecaboranyl substituent at the 17-position have been prepared which possess high uterotropic and estrophilic activity useful in boron neutron capture destruction of cancerous cells.
Inventors
- 👤 Harry E. Hadd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 00:52
CPC Classifications
C; C07; C07J; C07J51/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
57 words
A member selected from the group consisting of an estratriene composition of the formula: ##STR5## and an estratetraene composition of the formula: ##STR6## wherein R, and R' are independently selected from the group consisting of hydrogen, acetyl, and methyl groups, and wherein X is a dicarbadodecaboranyl substituent of the formula C 2 B 10 H 11 .
Claim 2
Dependent Claim
57 words
A member selected from the group consisting of an estratriene composition of the formula: ##STR5## and an estratetraene composition of the formula: ##STR6## wherein R, and R' are independently selected from the group consisting of hydrogen, acetyl, and methyl groups, and wherein X is a dicarbadodecaboranyl substituent of the formula C 2 B 10 H 11 .
Claim 3
Dependent Claim
21 words
An estrogen composition selected from the group consisting of: (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene, 3,17-diol diacetate (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol 17-acetate (17β)-17-(1,2-Dicarbadodecaobran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)-3-methoxyestra-1,3,5(10)-trien-17-ol acetate 1-(3-Methoxyestra, 1,3,5(10),16-tetraen-17-yl)-1,2-dicarbadodecaborane(12) 17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10),16-tetraen-3-ol acetate.
Claim 4
Dependent Claim
21 words
An estrogen composition selected from the group consisting of: (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene, 3,17-diol diacetate (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol 17-acetate (17β)-17-(1,2-Dicarbadodecaobran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)-3-methoxyestra-1,3,5(10)-trien-17-ol acetate 1-(3-Methoxyestra, 1,3,5(10),16-tetraen-17-yl)-1,2-dicarbadodecaborane(12) 17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10),16-tetraen-3-ol acetate.
Claim 5
Independent Claim
71 words
A method of preparation of estrogen compositions having a dicarbadodecaboranyl substituent at the 17-position comprising the steps of: reacting an estratriene composition of the formula: ##STR7## wherein X is an acetylenic substituent; and wherein R and R' are independently selected from the group comprising hydrogen, acetyl, and methyl; with decaborane in a refluxing, dry organic solvent, for such a time as is necessary to effect condensation; and, separating the reaction products.
Claim 6
Independent Claim
71 words
A method of preparation of estrogen compositions having a dicarbadodecaboranyl substituent at the 17-position comprising the steps of: reacting an estratriene composition of the formula: ##STR7## wherein X is an acetylenic substituent; and wherein R and R' are independently selected from the group comprising hydrogen, acetyl, and methyl; with decaborane in a refluxing, dry organic solvent, for such a time as is necessary to effect condensation; and, separating the reaction products.
Claim 7
Dependent Claim
26 words
A method, as claimed in claim 3, wherein said estrogen composition is selected from the group consisting of: (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol diacetate (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)-3-methoxyestra-1,3,5(10)-trien-17-ol acetate 1-(3-Methoxyestra- 1,3,5(10),16-tetraen-17-yl)-1,2-dicarbadodecaborane(12) 17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10),16-tetraen-3-ol acetate.
Claim 8
Independent Claim
28 words
A method of preparation of (17β)-17-(1,2-dicarbadodecaboran(12)-1yl)estra-1,3,5(10)-triene-3,17-diol or (17β)-17-(1,2-dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol 17-acetate comprising the step of: reacting (17β)-17-(1,2-dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol diacetate with base for such a time as necessary to bring about hydrolysis.
Claim 9
Independent Claim
28 words
A method of preparation of (17β)-17-(1,2-dicarbadodecaboran(12)-1yl)estra-1,3,5(10)-triene-3,17-diol or (17β)-17-(1,2-dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol 17-acetate comprising the step of: reacting (17β)-17-(1,2-dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol diacetate with base for such a time as necessary to bring about hydrolysis.
Claim 10
Independent Claim
68 words
A method for the destruction of cancerous tissues containing estrogen receptors comprising the steps of: administering an effective dose of an estratriene or estratetraene composition bearing a dicarbadodecaboranyl substituent at the 17-position; irradiating the area of the cancerous tissue with low energy thermal neutrons of about 10 10 to about 10 12 fluence for such a time as is necessary to bring about destruction of the cancerous cells.
Claim 11
Independent Claim
68 words
A method for the destruction of cancerous tissues containing estrogen receptors comprising the steps of: administering an effective dose of an estratriene or estratetraene composition bearing a dicarbadodecaboranyl substituent at the 17-position; irradiating the area of the cancerous tissue with low energy thermal neutrons of about 10 10 to about 10 12 fluence for such a time as is necessary to bring about destruction of the cancerous cells.
Claim 12
Dependent Claim
30 words
A method, as claimed in claim 6, wherein said estratriene or estratetraene composition is selected from the group consisting of: (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol diacetate (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol 17-acetate (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10)-triene-3,17-diol (17β)-17-(1,2-Dicarbadodecaboran(12)-1-yl)-3-methoxyestra-1,3,5(10)-trien-17-ol acetate 1-(3-Methoxyestra-1,3,5(10),16-tetraen-17-yl)-1,2-dicarbadodecaborane(12) 17-(1,2-Dicarbadodecaboran(12)-1-yl)estra-1,3,5(10),16-tetraen-3-ol acetate.
Claim 13
Dependent Claim
37 words
A method, as claimed in claim 7, wherein the effective dose is a 10 5 B concentration of at least about 15 micrograms per gram of cell, but less than about 300 micrograms per gram of cell.
References Cited (Backward Citations)
US4260736A
Cited
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