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US4471113A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Prodrugs based on phospholipid-nucleoside conjugates
Assignee: ENERGY United States, Department of
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Filing: 1982-02-03
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Granted: 1984-09-11
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Expires: 2002-02-03
Abstract
Abstract The invention relates to the production of a single diastereomeric form of a phospholipid araC conjugate as a prodrug.
Inventors
- 👤 Malcolm MacCoss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 15:27
CPC Classifications
C; C07; C07H; C07H23/00; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/16; C07H19/20
Claims Analysis
Total Claims: 7
Claim 1
Independent Claim
129 words
A method for producing a pure diastereomer of the following phospholipid-araC conjugate ##STR10## from a first compound ##STR11## where x and y are integers from 12-16, said process comprising the steps of: (a) reacting the first compound with t-butyldimethylsilyl chloride under silylation conditions to produce a second compound ##STR12## (b) reacting the second compound with levulinic anhydride under acylating conditions to produce a third compound ##STR13## where Lv is the levulinyl group (c) deblocking the third compound to produce a fourth compound ##STR14## (d) condensing the fourth compound with ##STR15## to produce a fifth compound ##STR16## (e) deblocking the fifth compound to produce a sixth compound as a mixture of diastereomers at phosphorous: ##STR17## (f) and hydrolyzing the sixth compound to produce said monophosphate-linked derivative as a single diastereomer.
Claim 2
Independent Claim
129 words
A method for producing a pure diastereomer of the following phospholipid-araC conjugate ##STR10## from a first compound ##STR11## where x and y are integers from 12-16, said process comprising the steps of: (a) reacting the first compound with t-butyldimethylsilyl chloride under silylation conditions to produce a second compound ##STR12## (b) reacting the second compound with levulinic anhydride under acylating conditions to produce a third compound ##STR13## where Lv is the levulinyl group (c) deblocking the third compound to produce a fourth compound ##STR14## (d) condensing the fourth compound with ##STR15## to produce a fifth compound ##STR16## (e) deblocking the fifth compound to produce a sixth compound as a mixture of diastereomers at phosphorous: ##STR17## (f) and hydrolyzing the sixth compound to produce said monophosphate-linked derivative as a single diastereomer.
Claim 3
Dependent Claim
13 words
The process of claim 1 wherein x and y are equal to 14.
Claim 4
Dependent Claim
48 words
A mixture of the single diastereomer ##STR18## where x and y are integers from 12-16, and the single diastereomer of the following compound ##STR19## where a and b are integers from 12-16, said diastereomers being present respectively, in a weight ratio in the order of 1:2 to 3:1.
Claim 5
Dependent Claim
48 words
A mixture of the single diastereomer ##STR18## where x and y are integers from 12-16, and the single diastereomer of the following compound ##STR19## where a and b are integers from 12-16, said diastereomers being present respectively, in a weight ratio in the order of 1:2 to 3:1.
Claim 6
Dependent Claim
16 words
The mixture of claim 3 wherein x and y and a and b each equal 14.
Claim 7
Dependent Claim
13 words
The mixture of claim 3 characterized by being soluble in a saline solution.
References Cited (Backward Citations)
US4096324A
Cited
US4291024A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-09-11 | 1988-03-12 | 1988-09-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-11 | 1992-03-12 | 1992-09-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-11 | 1996-03-12 | 1996-09-11 | $7700.00 | Window Closed / Lapsed |