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US4096324A
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US
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Cytidine nucleoside compound
Assignee: Pharmacia and Upjohn Co
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Filing: 1976-01-30
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Granted: 1978-06-20
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Expires: 1996-01-30
Abstract
Abstract 5'-Esters of ara-cytidine (1-β-D-arabinofuranosylcytosine) are prepared by reacting ara-cytidine with β,β,β-trihaloethoxycarbonyl halide or other protective agency to form a protective amido group on the primary amino nitrogen of ara-cytidine and then reacting the thus-protected compound with a reagent reactive with the 5'-O-hydroxyl group, e.g., an acylating agent, to form the 5'-O-derivative. The β,β,β-trihaloethoxycarbonyl or other protective group is then removed. Alternately, the primary amino group of ara-cytidine can be protected from acylation by protonation. The 5'-O-derivatives in their free base of salt form are characterized in that they display the property of sustained release of the compound, ara-cytidine, when administered intramuscularly or subcutaneously. Ara-cytidine is known for its anti-viral action and for its usefulness as an agent for controlling leukemias, including acute leukemia, and the sustained release property extends the usefulness of ara-cytidine for these purposes and as an inmunosuppressive agent. The 5'-O-derivartives of this invention can also be administered orally.
Inventors
- 👤 Robert C. Kelly
- 👤 William J. Wechter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 13:31
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
81 words
A compound having the following structural formula: ##STR125## in which A and B are the same or different radicals selected from the group consisting of H, aliphatic of from 1 to 10 carbon atoms, monocyclic aliphatic of from 4 to 10 carbon atoms, and aromatic of from 6 to 10 carbon atoms, and further in which A and B together can make up an aliphatic chain of from 3 to 6 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 2
Dependent Claim
81 words
A compound having the following structural formula: ##STR125## in which A and B are the same or different radicals selected from the group consisting of H, aliphatic of from 1 to 10 carbon atoms, monocyclic aliphatic of from 4 to 10 carbon atoms, and aromatic of from 6 to 10 carbon atoms, and further in which A and B together can make up an aliphatic chain of from 3 to 6 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 3
Dependent Claim
62 words
A compound having the following structural formula: ##STR126## in which M is a radical selected from the group consisting of aliphatic of from 1 to 10 carbon atoms, monocyclic aliphatic of from 4 to 10 carbon atoms, aromatic of from 6 to 10 carbon atoms, and aralkyl of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
62 words
A compound having the following structural formula: ##STR126## in which M is a radical selected from the group consisting of aliphatic of from 1 to 10 carbon atoms, monocyclic aliphatic of from 4 to 10 carbon atoms, aromatic of from 6 to 10 carbon atoms, and aralkyl of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
53 words
A compound having the following structural formula: ##STR127## wherein M 1 is a radical selected from the group consisting of aliphatic of from 1 to 10 carbon atoms, aromatic of from 6 to 10 carbon atoms, and araliphatic of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
53 words
A compound having the following structural formula: ##STR127## wherein M 1 is a radical selected from the group consisting of aliphatic of from 1 to 10 carbon atoms, aromatic of from 6 to 10 carbon atoms, and araliphatic of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
52 words
A compound having the following structural formula: ##STR128## wherein A 1 and B 1 are the same or different radicals selected from the group consisting of H, alkyl of from 1 to 7 carbon atoms, and aromatic of from 6 to 10 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 8
Dependent Claim
52 words
A compound having the following structural formula: ##STR128## wherein A 1 and B 1 are the same or different radicals selected from the group consisting of H, alkyl of from 1 to 7 carbon atoms, and aromatic of from 6 to 10 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 9
Dependent Claim
53 words
A compound of the following structural formula: ##STR129## wherein R 6 is a radical selected from the group consisting of aliphatic of from 1 to 20 carbon atoms, aromatic of from 6 to 10 carbon atoms, and araliphatic of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
Claim 10
Dependent Claim
53 words
A compound of the following structural formula: ##STR129## wherein R 6 is a radical selected from the group consisting of aliphatic of from 1 to 20 carbon atoms, aromatic of from 6 to 10 carbon atoms, and araliphatic of from 7 to 12 carbon atoms, or the pharmaceutically acceptable acid addition salts thereof.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-06-19 | 1981-12-19 | 1982-06-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-06-19 | 1985-12-19 | 1986-06-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-06-19 | 1989-12-19 | 1990-06-20 | $7700.00 | Window Closed / Lapsed |