US3755296A
Expired / Lapsed
US
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Process for preparing 1-{62 -d-arabinofuranosyl-cytosine and 2,2{40 -cyclocytidine
Assignee: Kohjin Co
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Filing: 1970-07-17
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Granted: 1973-08-28
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Expires: 1990-07-17
Abstract
Abstract The present invention relates to a novel process for preparing 1- Beta -D-arabinofuranosylcytosine (spongocytidine) expressed by the general formula (I) and a process for preparing as an intermediate thereof 2,2''-cyclocytidine(2,2''-anhydro-1- Beta -Darabinofuranosylcytosine) (II) with good efficiency.
Inventors
- 👤 T Kanai
- 👤 K Kikugawa
- 👤 M Ichino
- 👤 T Nakamura
- 👤 S Asakura
- 👤 O Maruyama
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 08:50
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
45 words
A process according to claim 1 for preparing 1 Beta -D-arabinofuranosylcytosine or a salt thereof wherein the halogenating agent is at least one substance selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosgene and chlorine.
Claim 2
Dependent Claim
28 words
A process according to claim 1 for preparing 1- Beta -arabinofuranosylcytosine or said salt thereof wherein the halogenating agent is phosphorus pentachloride, phosphorus pentabromide or a combination thereof.
Claim 3
Dependent Claim
103 words
A process for preparing 1- Beta -D-arabinofuranosylcytosine or an inorganic acid salt or organic acid salt thereof consisting essentially of reacting cytidine, a mineral acid salt thereof, or a cytidine salt of an acid selected from the group consisting of formic acid, acetic acid, sulfosalicyclic acid and crotic acid, with at least one substance selected from the group consisting of diphalophosphoric acid, phosphorus oxyhalides and partially hydrated phosphorus oxyhalides to produce 2, 2'' cyclocytidine or said salt thereof and then hydrolyzing the 2, 2''-cyclocytidine or salt by mixing it with water and adjusting the pH to a value from about 9 to 12.
Claim 4
Dependent Claim
26 words
A process according to claim 4 for preparing 1- Beta -D-arabinofuranosylcytosine or said salt thereof wherein an acetic acid ester is used as the reaction solvent.
Claim 5
Dependent Claim
124 words
A procesS for preparing 1- Beta -D-arabinofuranosylcytosine or an inorganic acid salt or organic acid salt thereof consisting essentially of reacting cytidine, a mineral acid salt thereof, or a cytidine salt of an acid selected from the group consisting of formic acid, acetic acid, sulfosalicyclic acid and crotic acid, in an acetic acid ester as solvent with at least one substance selected from the group consisting of (a) dichlorophosphoric acid, (b) phosphorous oxychloride, (c) phosphorus oxybromide, (d) partially hydrated phosphorus oxychloride and (e) partially hydrated phosphorus oxybromide to produce 2, 2''-cyclocytidine or said salt thereof and then hydrolyzing the 2, 2''-cyclocytidine or said salt by mixing it with water and adjusting the pH of the mixture to a value from about 9 to 12.
Claim 6
Dependent Claim
38 words
A process according to claim 6 for preparing 1- Beta -D-arabinofuranosylcytosine or said salt thereof wherein phosphorus oxychloride or phosphorus oxybromide is added as a mixture with a tertiary alcohol to react with cytidine or said salt thereof.
Claim 7
Dependent Claim
22 words
A process according to claim 7 for preparing 1- Beta -D-arabinofuranosylcytosine or said salt thereof wherein the mentioned tertiary alcohol is tert-butanol.
Claim 8
Dependent Claim
35 words
A process according to claim 1 for preparing 1- Beta -D-arabinofuranosylcytosine or said salt thereof comprising directly hydrolyzing the 2,2''-cyclocytidine or said salt thereof as an intermediate without isolating the same from the reaction solution.
Claim 9
Dependent Claim
67 words
A process for preparing 2, 2''-cyclocytidine or an inorganic acid salt or organic acid salt thereof consisting essentially of reacting cytidine, a mineral salt thereof, or a cytidine salt of an acid selected from the group consisting of formic acid, acetic acid, sulfosalicyclic acid and crotic acid, with at least one material selected from the group consisting of (a) a halomethylenedimethylammonium halide expressed by the general formula
Claim 10
Dependent Claim
43 words
A process according to claim 10 for preparing 2,2''-cyclocytidine or said salt thereof wherein the halogenating agent is at least one substance selected from the group consisting of thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus oxybromide, phosphorus trichloride, phosphorus tribromide, phosgene and chlorine.
Claim 11
Dependent Claim
24 words
A process according to claim 10 for preparing 2,2''-cyclocytidine or said salt thereof wherein the halogenating agent being is phosphorus pentachloride or phosphorus pentabromide.
Claim 12
Dependent Claim
68 words
A process for preparing 2, 2''-cyclocytidine or an inorganic acid salt or organic acid salt thereof consisting essentially of reacting cytidine, a mineral acid salt thereof, or a cytidine salt of an acid selected from the group consisting of formic acid acetic acid, sulfosalicylic acid and crotic acid, with at least one substance selected from the group consisting of dihalophosphoric acids, phosphorus oxyhalides and partially hydrated phosphorus oxyhalides.
Claim 13
Dependent Claim
25 words
A process according to claim 13 for preparing 2,2''-cyclocytidine or said salt thereof wherein an ester of acetic acid is used as the reaction solvent.
Claim 14
Dependent Claim
87 words
A process for preparing 2, 2''-cyclocytidine or an inorganic acid salt or organic acid salt thereof consisting essentially of reacting cytidine, a mineral acid salt thereof, or a cytidine salt of an acid selected from the group consisting of formic acid, acetic acid, sulfosalicylic acid and crotic acid, in an ester of acetic acid as solvent with at least one substance selected from the group consisting of (a) dichlorophosphoric acid, (b) phosphorus oxychloride, (c) phosphorus oxybromide, (d) partially hydrated phosphorus oxychloride and (e) partially hydrated phosphorus oxybromide.
Claim 15
Dependent Claim
40 words
A process according to claim 15 for preparing 2,2''-cyclocytidine or a said salt theReof comprising applying phosphorus oxychloride or phosphorus oxybromide in the form of a mixture with a tertiary alcohol to react with cytidine or a said salt thereof.
Claim 16
Dependent Claim
19 words
A process according to claim 16 for preparing 2,2''-cyclocytidine or said salt thereof wherein the tertiary alcohol is tert-butanol.
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) | 1976-08-27 | 1977-02-26 | 1977-08-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1980-08-27 | 1981-02-26 | 1981-08-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1984-08-27 | 1985-02-26 | 1985-08-28 | $7700.00 | Window Closed / Lapsed |