US4427664A
Expired / Lapsed
US
⏱️ 0.0 years remaining
2'Halo derivatives of daunomycin, desmethoxy daunomycin, adriamycin and carminomycin
Assignee: United States Department of Health and Human Services
•
Filing: 1982-08-17
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Granted: 1984-01-24
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Expires: 2002-08-17
Abstract
Abstract The compounds are derived from aglycons which may be daunomycin, desmethoxy daunomycin, adriamycin and carminomycin. A preferred compound is ##STR1## (1) R'=H; R 2 =OMe; X; Y (2) R'=OH; R 2 =OMe; X; Y (3) R'=H; R 2 =H; X; Y (4) R'=H; R 2 =OH; X; Y where X=I, Cl, Br, or F and Y=OH or AcO (acetoxy) where Y is AcO or OH and R'=H and R 2 =OMe. These compounds are effective showing high anti-leukemic activity against P388 murine leukemia.
Inventors
- 👤 Derek Horton
- 👤 Waldemar Priebe
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:48
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/24; C07H15/252
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
90 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 2'-halo α-L-hexopyranose sugar selected from the group of α-L-manno and α-L-talo at the 1' position of the sugar molecule according to the following formula: ##STR4## (1) R'=H; R 2 =OMe; X; Y (2) R'=OH; R 2 =OMe; X; Y (3) R'=H; R 2 =H; X; Y (4) R'=H; R 2 =OH; X; Y where: X=I, Cl, Br, or F and Y=OH or AcO (acetoxy).
Claim 2
Dependent Claim
90 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 2'-halo α-L-hexopyranose sugar selected from the group of α-L-manno and α-L-talo at the 1' position of the sugar molecule according to the following formula: ##STR4## (1) R'=H; R 2 =OMe; X; Y (2) R'=OH; R 2 =OMe; X; Y (3) R'=H; R 2 =H; X; Y (4) R'=H; R 2 =OH; X; Y where: X=I, Cl, Br, or F and Y=OH or AcO (acetoxy).
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
Dependent Claim
4 words
The compound 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-manno-hexopyranosyl)daunomycinone ##STR5##
Claim 8
Dependent Claim
4 words
The compound 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-manno-hexopyranosyl)daunomycinone ##STR5##
Claim 9
Dependent Claim
4 words
The compound 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talo-hexopyranosyl)daunomycinone ##STR6##
Claim 10
Dependent Claim
4 words
The compound 7-O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-α-L-talo-hexopyranosyl)daunomycinone ##STR6##
Claim 11
Independent Claim
77 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## (1) R'=H; R 2 =OMe; X; Y (2) R'=OH; R 2 =OMe; X; Y (3) R'=H; R 2 =H; X; Y (4) R'=H; R 2 =OH; X; Y where: X=I, Cl, Br, or F; and Y=OH or AcO (acetoxy).
Claim 12
Independent Claim
77 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## (1) R'=H; R 2 =OMe; X; Y (2) R'=OH; R 2 =OMe; X; Y (3) R'=H; R 2 =H; X; Y (4) R'=H; R 2 =OH; X; Y where: X=I, Cl, Br, or F; and Y=OH or AcO (acetoxy).
Claim 13
Dependent Claim
11 words
The method of claim 8 wherein the aglycon utilized is daunomycinone.
Claim 14
Dependent Claim
12 words
The method of claim 8 wherein the aglycon utilized is desmethoxy daunomycinone.
Claim 15
Dependent Claim
11 words
The method of claim 8 wherein the aglycon utilized is adriamycinone.
Claim 16
Dependent Claim
11 words
The method of claim 8 wherein the aglycon utilized is carminomycinone.
References Cited (Backward Citations)
US4201773A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-01-23 | 1987-07-25 | 1988-01-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-23 | 1991-07-25 | 1992-01-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-23 | 1995-07-25 | 1996-01-24 | $7700.00 | Window Closed / Lapsed |