US4617386A
Expired / Lapsed
US
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Process for the production of 18 F-2-deoxy-2-fluoro-D-glucose
Assignee: United States Department of Energy
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Filing: 1983-04-25
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Granted: 1986-10-14
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Expires: 2003-04-25
Abstract
Abstract Process for the production of 2-deoxy-2-fluoro-D-glucose and the corresponding 18F-compound in which methyl 4,6-O-benzylidine-3-O-methyl-2-O-trifluoromethanesulfonyl- beta -D-mannopyranoside is reacted with a triflating reagent, the resulting compound reacted with CsHF2, RbF or the corresponding 18F-compounds, and thereafter the alkyl groups removed by hydrolysis.
Inventors
- 👤 David R. Elmaleh
- 👤 Shlomo Levy
- 👤 Chyng-Yann Shiue
- 👤 Alfred P. Wolf
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 20:56
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 6
Claim 1
Independent Claim
123 words
A process for the production of 18 F-2-deoxy-2-fluoro-D-glucose which comprises the steps of: (a) producing a compound of the formula: ##STR3## where R is methyl, ethyl or propyl and Tf is trifluoromethanesulfonyl by reaction of the corresponding methyl, ethyl or propyl compounds with trifluoromethanesulfonyl anhydride at 0° C. to 30° C. in an inert organic solvent in the presence of a nitrogenous organic base which is soluble in the solvent; (b) reacting the resulting compound with a fluorinating agent which is [ 18 F]CsHF 2 or [ 18 F]RbF in an inert organic solvent with heating at 100° C. to 150° C.; and (c) hydrolyzing the resulting compounds to remove the alkyl groups with BBr 3 , BCl 3 or concentrated hydrochloric acid.
Claim 2
Dependent Claim
123 words
A process for the production of 18 F-2-deoxy-2-fluoro-D-glucose which comprises the steps of: (a) producing a compound of the formula: ##STR3## where R is methyl, ethyl or propyl and Tf is trifluoromethanesulfonyl by reaction of the corresponding methyl, ethyl or propyl compounds with trifluoromethanesulfonyl anhydride at 0° C. to 30° C. in an inert organic solvent in the presence of a nitrogenous organic base which is soluble in the solvent; (b) reacting the resulting compound with a fluorinating agent which is [ 18 F]CsHF 2 or [ 18 F]RbF in an inert organic solvent with heating at 100° C. to 150° C.; and (c) hydrolyzing the resulting compounds to remove the alkyl groups with BBr 3 , BCl 3 or concentrated hydrochloric acid.
Claim 3
Dependent Claim
37 words
The process of claim 1, wherein the reaction described in step a is conducted at a temperature in the range of from about 20° C. to 30° C. for a period of from 1 to 2 hours.
Claim 4
Dependent Claim
37 words
The process of claim 1, wherein the reaction described in step b is conducted at a temperature in the range of from about 120° C. to 140° C. for a period of from 10 to 30 minutes.
Claim 5
Dependent Claim
37 words
The process of claim 1, wherein the reaction described in step c is conducted at a temperature in the range of from about 20° C. to 40° C. for a period of from 25 to 50 minutes.
Claim 6
Dependent Claim
10 words
A process as in claim 1, wherein R is methyl.
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) | 1989-10-13 | 1990-04-14 | 1990-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-10-13 | 1994-04-14 | 1994-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-10-13 | 1998-04-14 | 1998-10-14 | $7700.00 | Window Closed / Lapsed |