CN1740166A - Industrial miglitol producing process - Google Patents
Industrial miglitol producing process Download PDFInfo
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- CN1740166A CN1740166A CN 200510105202 CN200510105202A CN1740166A CN 1740166 A CN1740166 A CN 1740166A CN 200510105202 CN200510105202 CN 200510105202 CN 200510105202 A CN200510105202 A CN 200510105202A CN 1740166 A CN1740166 A CN 1740166A
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- miglitol
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- tetrahydrofuran
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Abstract
The present invention discloses process of preparing miglitol with tetrafuran sugar derivative as material. The present invention has the advantages of simple operation, high yield and less environmental pollution, and the process is suitable for industrial production.
Description
Invention field
The present invention relates to the synthetic method of a kind of suitability for industrialized production Remedies for diabetes miglitol (Miglitol).
Background technology
Diabetes are diseases that modal a kind of endocrine metabolism imbalance causes.Diabetes are No. second diseases that are only second to cardiovascular disorder, and the WHO investigation result shows that there are several hundred million diabetic subjects in the whole world at present, wherein, is the type ii diabetes patient more than 90%.Along with the raising of living standards of the people and the improvement of trophic structure, chronic uninfection such as diabetes is being fashion trend.Annual newly-increased diabetic subject 1,200,000 people of China.
The medicine of treatment diabetes mainly contains biguanides (as metformin), sulfourea (as Glipizide), alpha-glucosidase inhibitors (as acarbose, miglitol) and thiazolidine diketone para-insulin sensitizer (as rosiglitazone) etc.Miglitol (Miglitol) is a kind of novel antidiabetic drug of research exploitation at the beginning of the 1980's of Bayer drugmaker, and chemistry is by name: [2R, 3R, 4R, 5S-1-(2-hydroxyethyl)-2-(methylol)-3,4,5-trihydroxy-piperidines triol].Chemical structural formula is:
Miglitol is a kind of oral alpha-glucosidase inhibitor, is applicable to that cooperating dietetic treatment type ii diabetes, its function mainly is to reduce patient's level of postprandial blood sugar, reduces the generation of diabetic complication.
People such as Fonacea are at Tetrahedron Lett., have introduced by the synthetic miglitol of chemical process in 2000,41,7313.The synthetic of miglitol also described among patent EP49858, EP55431, the DE3024901.According to these patents, it is feedstock production that miglitol can replace glucosamine with glucosamine or N-.But these three parts of patent contents all do not design the preparation of glucosamine or N-replacement glucosamine.U.S. Pat 4611058 has been described by the tetrahydrofuran (THF) sugar derivatives and has been synthesized miglitol through borohydride reduction, but this method yield is lower, thereby causes cost too high, is unfavorable for suitability for industrialized production.
According to the present invention, provide the productive rate of all technology relatively to want high, the reaction times will lack, cost is lower, the synthetic method of oligosaprobic miglitol.
Disclosure of an invention
In view of the difficult point that present miglitol synthetic method exists, the invention provides and a kind ofly be raw material with the tetrahydrofuran (THF) sugar derivatives, easy and simple to handle, cost is low, yield is high, reaction conditions is easy to realize and be suitable for the large-scale industrial production miglitol.
It is raw material that the present invention adopts the tetrahydrofuran (THF) sugar derivatives, prepares miglitol through catalytic hydrogenation.
Above-mentioned reaction scheme is:
The catalyzer that the present invention adopts is RaNi, 1%～5%Pd/C, Pd-CaCO
3In a kind of; The solvent that adopts is alcohols, water or its mixture; For example: methyl alcohol, ethanol, propyl alcohol, Virahol, the trimethyl carbinol, water, or its mixture; Hydrogenation pressure is 0.01～10Mpa; Temperature of reaction is 0～100 ℃; Reaction times is 1～24 hour.
Embodiment
The following examples can make those skilled in the art understand the present invention more comprehensively, but do not limit the present invention in any way.
Embodiment
In the 100L autoclave, add 5.0Kg tetrahydrofuran (THF) sugar derivatives (purity 98%), 95% ethanol 60L.With adding RaNi 600 grams behind the nitrogen replacement, blast hydrogen, the maintenance hydrogen pressure is 0.5～1MPa, slowly is warming up to 80 ℃ of reactions.
Follow the tracks of reaction with TLC, to reacting completely.The removal hydrogen pressure is used nitrogen replacement, the nitrogen press filtration, and filter residue (RaNi) can be used for the next batch reaction; Filtrate is cooled off with ice-water bath, gets miglitol crude product 4.6 (purity 97.5%); With ethanol/water (10: 1) recrystallization, get miglitol elaboration 4.5Kg (purity 98.9%).
Owing to described the present invention according to its special embodiment, some is modified and equivalent variations is conspicuous for the technician who is proficient in this field and comprises within the scope of the invention.
Claims (3)
1. one kind is the method for feedstock production miglitol with the tetrahydrofuran (THF) sugar derivatives, and this method is suitable for suitability for industrialized production.
2. the method for claim 1, raw material tetrahydrofuran (THF) sugar derivatives gets structure and is:
3. the method for claim 1 is characterized in that the catalyzer that adopts is RaNi, 1%～5%Pd/C, Pd-CaCO
3In a kind of; The solvent that adopts is alcohols, water or its mixture; For example: methyl alcohol, ethanol, propyl alcohol, Virahol, the trimethyl carbinol, water, or its mixture; Hydrogenation pressure is 0.01～10Mpa; Temperature of reaction is 0～100 ℃; Reaction times is 1～24 hour.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101052023A CN1328270C (en) | 2005-09-26 | 2005-09-26 | Industrial miglitol producing process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005101052023A CN1328270C (en) | 2005-09-26 | 2005-09-26 | Industrial miglitol producing process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1740166A true CN1740166A (en) | 2006-03-01 |
| CN1328270C CN1328270C (en) | 2007-07-25 |
Family
ID=36092713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2005101052023A Active CN1328270C (en) | 2005-09-26 | 2005-09-26 | Industrial miglitol producing process |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1328270C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746385A (en) * | 2017-10-31 | 2018-03-02 | 浙江工业大学 | A kind of preparation method of Miglitol |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3038901A1 (en) * | 1980-10-15 | 1982-05-06 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING N-SUBSTITUTED DERIVATIVES OF 1-DESOXYNOJIRIMYCIN |
| DE3049446A1 (en) * | 1980-12-30 | 1982-07-29 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING 1,5-DIDESOXY-1,5-IMINO-D-GLUCITOL AND ITS N-DERIVATIVES |
| DK0477160T3 (en) * | 1990-09-20 | 1996-05-20 | Monsanto Co | Process for the preparation of N-substituted 1-deoxynojirimycin |
-
2005
- 2005-09-26 CN CNB2005101052023A patent/CN1328270C/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107746385A (en) * | 2017-10-31 | 2018-03-02 | 浙江工业大学 | A kind of preparation method of Miglitol |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1328270C (en) | 2007-07-25 |
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| Date | Code | Title | Description |
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| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| EE01 | Entry into force of recordation of patent licensing contract |
Assignee: Shandong Xinshidai Pharmaceutical Industry Co., Ltd. Assignor: Lunan Pharmaceutical Group Co., Ltd. Contract record no.: 2010370000510 Denomination of invention: Industrial miglitol producing process Granted publication date: 20070725 License type: Exclusive License Open date: 20060301 Record date: 20100908 |
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| EC01 | Cancellation of recordation of patent licensing contract |
Assignee: Shandong Xinshidai Pharmaceutical Industry Co., Ltd. Assignor: Lunan Pharmaceutical Group Co., Ltd. Contract record no.: 2010370000510 Date of cancellation: 20121226 |
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| LICC | Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20151223 Address after: 273400 Shandong province Feixian County North Ring Road No. 1 Patentee after: Lunan New Era Biological Technology Co., Ltd. Address before: 276005 Hongqi Road, Shandong, Linyi, No. 209 Patentee before: Lunan Pharmaceutical Group Co., Ltd. |