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Patent US4325946A successfully refreshed from Google Patents.
US4325946A
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Anthracycline glycosides, their preparation, use and compositions thereof
Assignee: Pfizer Italia SRL
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Filing: 1980-08-28
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Granted: 1982-04-20
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Expires: 2000-08-28
Abstract
Abstract Anthracycline glycosides of the formula I <IMAGE> I wherein R is hydrogen or hydroxy, one of R1 and R2 is methyl and the other of R1 and R2 is hydroxy, and pharmaceutically acceptable acid addition salts thereof, which are useful in treating certain mammalian tumors, are prepared by condensing daunomycinone with certain novel sugars in an inert organic solvent and in the presence of a soluble silver salt and a dehydrating agent to form the corresponding protected glycosides from which the protecting groups are removed. This gives the compounds wherein R is hydrogen. The former are converted to the corresponding hydroxyl compounds by treatment with bromine and sodium formate.
Inventors
- 👤 Alberto Bargiotti
- 👤 Giueseppe Cassinelli
- 👤 Sergio Penco
- 👤 Federico Arcamone
- 👤 Aurelio Di Marco
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:58
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/08; A; A61; A61P; A61P35/00; A61P35/02; C07H15/00; C07H15/20; C07H15/24; C07H15/252; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
40 words
An anthracycline glycoside of the formula: ##STR7## wherein R is hydrogen or hydroxy, one of R 1 and R 2 is methyl and the other of R 1 and R 2 is hydroxy, and pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
40 words
An anthracycline glycoside of the formula: ##STR7## wherein R is hydrogen or hydroxy, one of R 1 and R 2 is methyl and the other of R 1 and R 2 is hydroxy, and pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
10 words
An anthracycline glycoside according to claim 1, which is 4'-C-methyl-daunorubicin.
Claim 4
Dependent Claim
10 words
An anthracycline glycoside according to claim 1, which is 4'-C-methyl-doxorubicin.
Claim 5
Dependent Claim
10 words
An anthracycline glycoside according to claim 1, which is 4'-epi-4'-C-methyl-daunorubicin.
Claim 6
Dependent Claim
10 words
An anthracycline glycoside according to claim 1, which is 4'-epi-4'-C-methyl-doxorubicin.
Claim 7
Dependent Claim
41 words
A sugar of the formula: ##STR8## wherein X is hydroxyl, chloro or p-nitrobenzoyl, R 1 is methyl, or p-nitrobenzoyl and R 2 is methyl, or p-nitrobenzoyl, wherein one of R 1 and R 2 is methyl and the other is P-nitrobenzoyl.
Claim 8
Dependent Claim
41 words
A sugar of the formula: ##STR8## wherein X is hydroxyl, chloro or p-nitrobenzoyl, R 1 is methyl, or p-nitrobenzoyl and R 2 is methyl, or p-nitrobenzoyl, wherein one of R 1 and R 2 is methyl and the other is P-nitrobenzoyl.
Claim 9
Dependent Claim
19 words
A sugar according to claim 6 wherein X is chloro, R 1 is methyl and R 2 is p-nitrobenzoyl.
Claim 10
Dependent Claim
19 words
A sugar according to claim 6 wherein X is chloro, R 1 is p-nitrobenzoyl and R 2 is methyl.
Claim 11
Dependent Claim
19 words
A sugar according to claim 6 wherein X is p-nitrobenzoyl, R 1 is methyl and R 2 is p-nitrobenzoyl.
Claim 12
Dependent Claim
19 words
A sugar according to claim 6 wherein X is p-nitrobenzoyl, R 1 is p-nitrobenzoyl and R 2 is methyl.
Claim 13
Dependent Claim
125 words
A process for preparing the sugars according to claim 6 wherein X is chloro, one of R 1 and R 2 is methyl and the other is p-nitrobenzoyl, said process comprising separately subjecting 2,3,6-trideoxy-4-C-methyl-α-L-lyxo-hexopyranose(IV-A) and 2,3,6-trideoxy-4-C-methyl-α-L-arabinohexopyranose (IV-B) to acid hydrolysis to form respectively, sugars wherein X is hydroxy, one of R 1 and R 2 is methyl and the other is hydroxy, reacting each said sugar with p-nitrobenzoyl chloride to form the sugars wherein X is p-nitrobenzoyl, one of R 1 and R 2 is methyl and the other is p-nitrobenzoyl, and separately subjecting each said sugar to treatment with anhydrous hydrogen chloride to form said sugars wherein X is chloro, one of R 1 and R 2 is methyl and the other is p-nitrobenzoyl.
Claim 14
Dependent Claim
63 words
A process according to claim 11 wherein the acid hydrolysis is effected with acetic acid at about 100° C. for about 2 hours, the reaction with p-nitrobenzoyl chloride is effected in the presence of triethylamine and a catalytic amount of 4-dimethylamino pyridine at about 45° C. for about 1.5 hours and the treatment with anhydrous hydrogen chloride is effected at about 0° C.
Claim 15
Dependent Claim
29 words
An antitumor pharmaceutical composition, for a transplanted tumor, comprising a therapeutically effective amount of an anthracycline glycoside as claimed in claim 1 in combination with an inert carrier therefor.
Claim 16
Dependent Claim
32 words
A method of inhibiting the growth of transplanted P 388 leukemia comprising intraperitoneally administering to a host afflicted therewith, a therapeutically effective amount of an anthracycline glycoside as claimed in claim 1.
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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) | 1985-04-19 | 1985-10-19 | 1986-04-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-19 | 1989-10-19 | 1990-04-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-19 | 1993-10-19 | 1994-04-20 | $7700.00 | Window Closed / Lapsed |