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Industrial miglitol producing process

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.

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Pharmaceuticals Containing Other Organic And Inorganic Compounds Organic Low-Molecular-Weight Compounds And Preparation Thereof
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CN1740166A

China

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Chinese
Inventor
赵志全
彭立增
Current Assignee
Lunan New Era Biological Technology Co., Ltd.
Worldwide applications
2005 CN
Application CN 200510105202 events
2005-09-26
Application filed by Lunan Pharmaceutical Group Corp
2005-09-26
Priority to CNB2005101052023A
2006-03-01
Publication of CN1740166A
2007-07-25
Application granted
2007-07-25
Publication of CN1328270C
Status
Active
2025-09-26
Anticipated expiration
Info
Patent citations (3)
Cited by (1)
Legal events
Similar documents
Priority and Related Applications
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Description

A kind of method of industrial miglitol producing
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:
Figure A20051010520200031
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:
Figure A20051010520200041
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)
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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:
Figure A2005101052020002C1
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.

Patent Citations (3)

Publication number Priority date Publication date Assignee Title
Family To Family Citations
DE3038901A1 * 1980-10-15 1982-05-06 Bayer Ag, 5090 Leverkusen METHOD FOR PRODUCING N-SUBSTITUTED DERIVATIVES OF 1-DESOXYNOJIRIMYCIN
DE3049446A1 * 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
JP3162123B2 * 1990-09-20 2001-04-25 モンサント カンパニー Method for producing N-substituted-1-deoxynojirimycin
* Cited by examiner, † Cited by third party

Cited By (1)

Publication number Priority date Publication date Assignee Title
CN107746385A * 2017-10-31 2018-03-02 浙江工业大学 A kind of preparation method of Miglitol
Family To Family Citations
* Cited by examiner, † Cited by third party, ‡ Family to family citation

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Priority And Related Applications

Priority Applications (1)

Application Priority date Filing date Title
CNB2005101052023A 2005-09-26 2005-09-26 Industrial miglitol producing process

Applications Claiming Priority (1)

Application Filing date Title
CNB2005101052023A 2005-09-26 Industrial miglitol producing process

Legal Events

Date Code Title Description
2006-03-01 C06 Publication
2006-03-01 PB01 Publication
2006-06-07 C10 Entry into substantive examination
2006-06-07 SE01 Entry into force of request for substantive examination
2007-07-25 C14 Grant of patent or utility model
2007-07-25 GR01 Patent grant
2010-11-10 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
2013-02-20 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
2013-02-20 LICC Enforcement, change and cancellation of record of contracts on the licence for exploitation of a patent or utility model
2016-01-13 C41 Transfer of patent application or patent right or utility model
2016-01-13 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.