Patent US3687931A successfully refreshed from Google Patents.
US3687931A
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Halogenated purine and pyrimidine nucleosides and process therefor
Assignee: Roche Palo Alto LLC
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Filing: 1970-03-19
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Granted: 1972-08-29
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Expires: 1990-03-19
Abstract
Abstract Reacting suitably protected pyrimidine nucleoside and suitably protected purine nucleoside with triphenylphosphine and carbon tetrabromide or carbon tetrachloride in a dipolar aprotic solvent yields the corresponding 5''-deoxy-5''-halo nucleoside derivative. Reacting 5''-protected 2''-deoxy pyrimidine nucleoside in a similar fashion yields a mixture of the two possible isomeric 2'', 3''dideoxy-3''-halo-5''-protected pyrimidine nucleosides. Reacting 5''protected uridine derivatives in a similar fashion yields the corresponding 2''-deoxy-2''-chloro derivative. These compounds and disclosed derivatives thereof have antibiotic properties and are useful in controlling metabolic processes.
Inventors
- 👤 Julien P Verheyden
- 👤 John G Moffatt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 18:17
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
20 words
The compound of claim 1 selected from those represented by Formula (A) wherein each of R1 and R2 is hydroxy.
Claim 2
Dependent Claim
12 words
The compound of claim 2 selected from those wherein B1 is 2-fluoroadenin-9-yl.
Claim 3
Dependent Claim
12 words
The compound of claim 2 selected from those wherein B1 is 7-cyano-7-deazaadenin-9-yl.
Claim 4
Dependent Claim
12 words
The compound of claim 2 selected from those wherein B1 is 8-aza-9-deazaadenin-9-yl.
Claim 5
Dependent Claim
12 words
The compound of claim 2 selected from those wherein B1 is 6-chloropurin-9-yl.
Claim 6
Dependent Claim
13 words
The compound of claim 2 selected from those wherein B1 is 2, 6-dichloropurin-9-yl.
Claim 7
Dependent Claim
16 words
The compound of claim 1 selected from those represented by Formula (B) wherein R3 is hydroxy.
Claim 8
Dependent Claim
12 words
The compound of claim 8 selected from those wherein B2 is 2-fluoroadenin-9-yl.
Claim 9
Dependent Claim
12 words
The compound of claim 8 selected from those wherein B2 is 7-cyano-7-deazaadenin-9-yl.
Claim 10
Dependent Claim
12 words
The compound of claim 8 selected from those wherein B2 is 6-chloropurin-9-yl.
Claim 11
Dependent Claim
13 words
The compound of claim 8 selected from those wherein B2 is 2, 6-dichloropurin-9-yl.
Claim 12
Dependent Claim
16 words
The compound of claim 1 selected from those represented by Formula (C) wherein R4 is hydroxy.
Claim 13
Dependent Claim
12 words
The compound of claim 13 selected from those wherein B2 is 7-deazaadenin-9-yl.
Claim 14
Dependent Claim
12 words
The compound of claim 13 selected from those wherein B2 is 2-fluoroadenin-9-yl.
Claim 15
Dependent Claim
12 words
The compound of claim 13 selected from those wherein 82 is 8-aza-9-deazaadenin-9-yl.
Claim 16
Dependent Claim
12 words
The compound of claim 13 selected from those wherein B2 is 6-chloropurin-9-yl.
Claim 17
Dependent Claim
12 words
The compound of claim 13 selected from those wherein B2 is 2,6-dichloropurin-9-yl.
Claim 18
Dependent Claim
24 words
The compound of claim 1 selected from those represented by Formula (D) wherein each of R5 and R6 is hydroxy and B2 is 6-mercaptopurin-9-yl.
Claim 19
Dependent Claim
16 words
The compound of claim 1 selected from those represented by Formula (E) wherein R7 is hydroxy.
Claim 20
Dependent Claim
14 words
The compound of claim 20 selected from those wherein B3 is uracil-1-yl or thymin-1-yl.
Claim 21
Dependent Claim
12 words
The compound of claim 20 selected from those wherein B3 is 5-fluorouracil-1-yl.
Claim 22
Dependent Claim
12 words
The compound of claim 20 selected from those wherein B3 is 5-ioduracil-1-yl.
Claim 23
Dependent Claim
12 words
The compound of claim 20 selected from those wherein B3 is 5-nitrouracil-1-yl.
Claim 24
Dependent Claim
12 words
The compound of claim 20 selected from those wherein B3 is 5-trifluoromethyluracil-1-yl.
Claim 25
Dependent Claim
13 words
The process for producing compounds selected from those represented by the following formulas:
Claim 26
Dependent Claim
42 words
The process of claim 26 for producing compounds selected from those represented by Formulas (F), (G), (H), and (I) wherein there is reacted a 5''-monohydroxy starting compound in the ribopentofuranosyl, 2''-deoxypentofuranosyl, 3'' -deoxypentofuranosyl, and arabinopentofuranosyl series to prepare the corresponding 5''-deoxy-5''-halo product.
Claim 27
Dependent Claim
38 words
The process of claim 26 for producing compounds selected from those represented by Formulas (J) and (K) wherein there is reacted a 3''-monohydroxy-2''-deoxyerythropentofuranosyl or 3'',5''-dihydroxy-2''-deoxyerythropentofuranosyl starting compound to prepare the corresponding 2'',3''dideoxy-3'' -halothreopentofurnaosyl, 2'',3''-dideoxy-3''-haloerythropentofuranosyl, 3'',5''-dihalo-2'',3'',5''-trideoxythreopentofuranosyl and 3'',5''-dihalo-2'',3'',5''-trideoxyerythropentofuranosyl products.
Claim 28
Dependent Claim
34 words
The process of claim 26 for producing compounds selected from those represented by Formula (L) wherein there is reacted a ribopentofuranosyl starting compound having optional protection at C-5'' to prepare the corresponding 2''-deoxy-2''-chlororibopentofuranosyl product.
Claim 29
Dependent Claim
12 words
The process of claim 26 conducted at from 10* to 100* C.
Claim 30
Dependent Claim
12 words
The process of claim 26 wherein the dipolar aprotic solvent is dimethylformamide.
Claim 31
Dependent Claim
9 words
The process of claim 26 wherein 5''-chloro-5''-deoxyadenosine is prepared.
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) | 1975-08-29 | 1976-02-28 | 1976-08-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1979-08-29 | 1980-02-28 | 1980-08-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1983-08-29 | 1984-02-28 | 1984-08-29 | $7700.00 | Window Closed / Lapsed |