US4611058A
Expired / Lapsed
US
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Process for the preparation of 1,5-didesoxy-1,5-imino-D-glucitol and N-derivatives thereof
Assignee: Bayer AG
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Filing: 1985-05-14
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Granted: 1986-09-09
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Expires: 2005-05-14
Abstract
Abstract The invention relates to a process for preparing 1,5-didesoxy-1,5-imino-D-glucitol (desoxynojirimicin) and N-derivative thereof, which are known to be powerful inhibitors for α-glycosidases. The process of the invention involves reducing with a complex borohydride, a 6-amino-6-desoxy-L-sorbose.
Inventors
- 👤 Wolfgang Koebernick
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 14:45
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/44; C07D211/46
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
76 words
A process for the production of 1,5-didesoxy-1,5-imino-D-glucitol or an N-derivative of the formula ##STR3## in which R 1 denotes a hydrogen atom or an optionally substituted akyl, alkenyl, alkinyl or alkadienyl radical, or an acid addition salt thereof with the acid HX, which comprises reducing with dimethylamino borane, optionally in the presence of an auxiliary base, a compound of the formula ##STR4## wherein R 1 has the abovementioned meaning mentioned, and HX is a strong acid.
Claim 2
Dependent Claim
76 words
A process for the production of 1,5-didesoxy-1,5-imino-D-glucitol or an N-derivative of the formula ##STR3## in which R 1 denotes a hydrogen atom or an optionally substituted akyl, alkenyl, alkinyl or alkadienyl radical, or an acid addition salt thereof with the acid HX, which comprises reducing with dimethylamino borane, optionally in the presence of an auxiliary base, a compound of the formula ##STR4## wherein R 1 has the abovementioned meaning mentioned, and HX is a strong acid.
Claim 3
Dependent Claim
23 words
A process according to claim 1, in which the dimethylamino borane is a mixture of dimethylamino borane and water or water/organic solvent mixture.
Claim 4
Dependent Claim
25 words
A process according to claim 2, in which the organic solvent is a C 1 to C 6 alcohol or an ether or ether alcohol.
Claim 5
Dependent Claim
15 words
A process according to claim 3, in which the alcohol is methanol, ethanol or isopropanol.
Claim 6
Dependent Claim
21 words
A process according to claim 1, in which the reduction is carried out at a temperature from 60° to 100° C.
Claim 7
Dependent Claim
21 words
A process according to claim 5, in which the reduction is carried out at a temperature from 60° to 80° C.
Claim 8
Dependent Claim
26 words
A process according to claim 1, in which the molar ratio between the compounds of the formula (II) and the dimethylamino borane is at least 1:0.25.
Claim 9
Dependent Claim
22 words
A process according to claim 1, in which a basic auxiliary material for binding the acid HX is present in the reduction.
Claim 10
Dependent Claim
23 words
A process according to claim 8, in which the basic auxiliary material is NaOH, KOH, Na 2 CO 3 , diethylamine or triethylamine.
References Cited (Backward Citations)
US2898379A
Cited
US4220782A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-09-08 | 1990-03-10 | 1990-09-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-09-08 | 1994-03-10 | 1994-09-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-09-08 | 1998-03-10 | 1998-09-09 | $7700.00 | Window Closed / Lapsed |