US4025623A
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US
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4'-Epi-6'-hydroxyadriamycin and method of use
Assignee: Pfizer Italia SRL
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Filing: 1975-10-10
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Granted: 1977-05-24
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Expires: 1995-10-10
Abstract
Abstract The novel glycoside antibiotic: 4'-epi-6'-hydroxydaunomycin is prepared by condensing daunomycin with a novel protected, reactive derivative, which is 1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabin o-hex-1-enepyranose and thereafter removing the protecting groups. A further novel glycoside antibiotic: 4'-epi-6'-hydroxyadriamycin is prepared by reacting 4'-epi-6'-hydroxydaunomycin with bromine to form an intermediate bromo derivative which is then mildly hydrolyzed to form 4'-epi-6'-hydroxyadriamycin. These novel glycoside antibiotics, while not as effective as the parent compounds daunomycin and adriamycin in the treatment of tumors, are considerably less toxic than the parent compounds.
Inventors
- 👤 Federico Arcamone
- 👤 Alberto Bargiotti
- 👤 Giuseppe Cassinelli
- 👤 Aurelio DIMarco
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 11:50
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/24; C07H15/252; A; A61; A61P; A61P35/00; C07D; C07D309/00; C07D309/16; C07D309/28; C07D309/30; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
27 words
A compound of the formula ##STR18## wherein R is H, OH or Br and, in the case where R is H or OH, the hydrochloride salts thereof.
Claim 2
Dependent Claim
27 words
A compound of the formula ##STR18## wherein R is H, OH or Br and, in the case where R is H or OH, the hydrochloride salts thereof.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein R is H.
Claim 4
Dependent Claim
10 words
A compound according to claim 1, wherein R is OH
Claim 5
Dependent Claim
10 words
A compound according to claim 1, wherein R is Br.
Claim 6
Dependent Claim
15 words
A compound of the formula ##STR19## wherein R 1 is H or CF 3 CO.
Claim 7
Dependent Claim
15 words
A compound of the formula ##STR19## wherein R 1 is H or CF 3 CO.
Claim 8
Dependent Claim
11 words
A compound according to claim 5, wherein R 1 is H.
Claim 9
Dependent Claim
13 words
A compound according to claim 5, wherein R 1 is CF 3 CO.
Claim 10
Dependent Claim
32 words
1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabino-hex-1-enepryanose comprising reacting 3-amino-2,3-dideoxy-L-arabino-hexose with trifluoroacetic anhydride, followed by treatment with a lower aliphatic alcohol, to form 2,3-dideoxy-3-trifluoroacetamido-L-arabinohexose, reacting the latter with p-nitrobenzoyl chloride in pyridine, followed by a mild alkaline hydrolysis.
Claim 11
Dependent Claim
32 words
1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabino-hex-1-enepryanose comprising reacting 3-amino-2,3-dideoxy-L-arabino-hexose with trifluoroacetic anhydride, followed by treatment with a lower aliphatic alcohol, to form 2,3-dideoxy-3-trifluoroacetamido-L-arabinohexose, reacting the latter with p-nitrobenzoyl chloride in pyridine, followed by a mild alkaline hydrolysis.
Claim 12
Dependent Claim
5 words
A process for preparing 1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabino-hex-1-enepyranose
Claim 13
Dependent Claim
5 words
A process for preparing 1,2,3-trideoxy-4,6-di-O-(p-nitrobenzoyl)-3-trifluoroacetamido-L-arabino-hex-1-enepyranose
Claim 14
Independent Claim
55 words
A method of inhibiting the growth of a tumor selected from the group consisting of Sarcoma 180 Ascites and L 1210 leukemia which comprises intraperitoneally administering to a host afflicted with said tumor an amount of a compound selected from the group consisting of 4'-epi-6'-hydroxydaunomycin and 4'-epi-6'-hydroxyadriamycin sufficient to inhibit the growth of said tumor.
Claim 15
Independent Claim
55 words
A method of inhibiting the growth of a tumor selected from the group consisting of Sarcoma 180 Ascites and L 1210 leukemia which comprises intraperitoneally administering to a host afflicted with said tumor an amount of a compound selected from the group consisting of 4'-epi-6'-hydroxydaunomycin and 4'-epi-6'-hydroxyadriamycin sufficient to inhibit the growth of said tumor.
References Cited (Backward Citations)
US3803124A
Cited
US3784541A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-05-23 | 1980-11-22 | 1981-05-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-05-23 | 1984-11-22 | 1985-05-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-05-23 | 1988-11-22 | 1989-05-24 | $7700.00 | Window Closed / Lapsed |