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7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone
Assignee: United States Department of Health and Human Services
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Filing: 1978-07-26
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Granted: 1980-05-06
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Expires: 1998-07-26
Abstract
Abstract A series of compounds showing high antileukemic activity against P388 murine leukemia and increased aqueous solubility due to substitution of -OH for the known -NH2 at the 3' position of the hexopyranose sugar, i.e., daunosamine. These compounds are coupled products of aglycon selected from daunomycinone, desmethoxy daunomycinone, adriamycinone and carminomycinone. These compounds are coupled at the 0-7 position of the aglycon with an alpha -L-lyxo hexopyranose sugar, which sugar isomer particularly sustains or potentiates the biological activity of the coupled compound as well as ameliorates the dose related cardiotoxicity of the parent and known compounds set out below: <IMAGE>
Inventors
- 👤 Derek Horton
- 👤 Wolfgang Weckerle
- 👤 Ernst F. Fuchs
- 👤 Tak M. Cheung
- 👤 Beat Winter
- 👤 Roderick J. Sorenson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:10
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; A; A61; A61P; A61P31/00; A61P31/04; A61P35/00; A61P35/02; C07H13/00; C07H13/02; C07H13/04; C07H15/20; C07H15/24; C07H15/252; C07H3/00; C07H3/02
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
45 words
A compound selected from one member of the group of aglycons consisting of daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone coupled at the 0-7 position to a 3' desamino α-L-lyxo hexose sugar at the 1' position of the sugar molecule according to the following formula: ##STR6##
Claim 2
Dependent Claim
45 words
A compound selected from one member of the group of aglycons consisting of daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone coupled at the 0-7 position to a 3' desamino α-L-lyxo hexose sugar at the 1' position of the sugar molecule according to the following formula: ##STR6##
Claim 3
Dependent Claim
12 words
The compound according to claim 1 wherein the aglycon utilized is daunomycinone.
Claim 4
Dependent Claim
13 words
The compound according to claim 1 wherein the aglycon utilized is desmethoxy daunomycinone.
Claim 5
Dependent Claim
12 words
The compound according to claim 1 wherein the aglycon utilized is adriamycinone.
Claim 6
Dependent Claim
12 words
The compound according to claim 1 wherein the aglycon utilized is carminomycinone.
Claim 7
Independent Claim
38 words
A method of treating murine leukemia in mice which comprises injecting a mouse infected with P388 leukemia with a biologically palliative amount and in a dosage regimen of up to 22 days of a compound selected from ##STR7##
Claim 8
Independent Claim
38 words
A method of treating murine leukemia in mice which comprises injecting a mouse infected with P388 leukemia with a biologically palliative amount and in a dosage regimen of up to 22 days of a compound selected from ##STR7##
Claim 9
Dependent Claim
11 words
The method of claim 6 wherein the aglycon utilized is daunomycinone.
Claim 10
Dependent Claim
12 words
The method of claim 6 wherein the aglycon utilized is desmethoxy daunomycinone.
Claim 11
Dependent Claim
11 words
The method of claim 6 wherein the aglycon utilized is adriamycinone.
Claim 12
Dependent Claim
11 words
The method of claim 6 wherein the aglycon utilized is carminomycinone.
Claim 13
Dependent Claim
18 words
The compound according to claim 1 wherein the 3'-desamino α-L-lyxo hexose sugar is in the following configuration ##STR8##
References Cited (Backward Citations)
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-06 | 1983-11-05 | 1984-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-06 | 1987-11-05 | 1988-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-06 | 1991-11-05 | 1992-05-06 | $7700.00 | Window Closed / Lapsed |