CN1042361A - Produce the method for mannuronic acid propyl ester sulfuric ester sodium salt - Google Patents
Produce the method for mannuronic acid propyl ester sulfuric ester sodium salt Download PDFInfo
- Publication number
- CN1042361A CN1042361A CN 88109698 CN88109698A CN1042361A CN 1042361 A CN1042361 A CN 1042361A CN 88109698 CN88109698 CN 88109698 CN 88109698 A CN88109698 A CN 88109698A CN 1042361 A CN1042361 A CN 1042361A
- Authority
- CN
- China
- Prior art keywords
- mannuronic acid
- propyl ester
- acid propyl
- sodium salt
- hydrolysis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 title claims abstract description 29
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 title claims abstract description 29
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 title claims abstract description 20
- -1 ester sodium salt Chemical class 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title claims abstract description 11
- 235000010413 sodium alginate Nutrition 0.000 claims abstract description 7
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 claims abstract description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229940005550 sodium alginate Drugs 0.000 claims abstract description 5
- 239000000661 sodium alginate Substances 0.000 claims abstract description 5
- 238000006277 sulfonation reaction Methods 0.000 claims abstract description 5
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000007062 hydrolysis Effects 0.000 claims abstract 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 3
- 230000032050 esterification Effects 0.000 claims abstract 3
- 238000005886 esterification reaction Methods 0.000 claims abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 8
- 229940079593 drug Drugs 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 239000008280 blood Substances 0.000 abstract description 3
- 210000004369 blood Anatomy 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 238000007710 freezing Methods 0.000 abstract description 3
- 239000002547 new drug Substances 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 201000010099 disease Diseases 0.000 abstract description 2
- 230000002526 effect on cardiovascular system Effects 0.000 abstract description 2
- 230000000302 ischemic effect Effects 0.000 abstract description 2
- 230000009885 systemic effect Effects 0.000 abstract description 2
- 231100000956 nontoxicity Toxicity 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 238000010612 desalination reaction Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000012634 fragment Substances 0.000 description 4
- 229920001499 Heparinoid Polymers 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 229920000669 heparin Polymers 0.000 description 3
- 229960002897 heparin Drugs 0.000 description 3
- 239000002554 heparinoid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000003252 repetitive effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000879 anti-atherosclerotic effect Effects 0.000 description 1
- 230000000680 avirulence Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000002001 electrolyte material Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 229920005684 linear copolymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 201000005665 thrombophilia Diseases 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention is a method of producing mannuronic acid propyl ester sulfuric ester sodium salt.It is basic raw material with the sodium alginate, produces mannuronic acid earlier through step such as hydrolysis, again the latter and propylene oxide reaction esterification is obtained the mannuronic acid propyl ester, and then uses the chlorsulfonic acid sulfonation, just obtains mannuronic acid propyl ester sulfuric ester sodium salt.This is a kind of novel substance, also is a kind of heparitin new drug.Its nontoxicity has stronger bolt ability that presses down and anti-moving congee ability, and tangible anti-freezing is arranged, lipopenicillinase, and the characteristics of blood viscosity lowering are a kind of medicines of ideal prevent and treat ischemic cardiovascular systemic disease.
Description
The invention belongs to a kind of preparation method of heparitin new drug.
The prepared material mannuronic acid propyl ester sulfuric ester sodium salt of the present invention is a kind of novel substance, and it does not appear in the newspapers especially as the active drug of prevent and treat hypercoagulable disease.It belongs to a kind of polyanion electrolyte material, is a kind of heparinoid drug.
The inventor is in development heparinoid drug process, inquired into the precursor problem of quasi-heparin substance, and inquired into structure activity relationship, so that provide the data of usefulness at mannuronic acid propyl ester sulfuric ester sodium salt, purpose is really to find pharmacological action outstanding, this kind new medicine that the medicine source is wide again.
A kind of technology of producing mannuronic acid propyl ester sulfuric ester sodium salt is disclosed in the present invention, by this technology, the basic raw material sodium alginate source of producing above-mentioned new drug is wide, the drug toxicity that makes is atomic, even reaches avirulent degree, and has the very strong bolt ability that presses down, the atherosclerosis ability is arranged, and heparin sample activity such as anti-freezing, lipopenicillinase, blood viscosity lowering are arranged.Also can suppress lithangiuria salt crystalline growth velocity.
Because said medicine is not seen before, so its preparation method also is to propose first.
The raw material that this technology is used is a sodium alginate.Studies show that the algin molecule is β-D-(1 → 4) the mannopyranose aldehydic acid unit and α-L-(1 → 4 that connect) the unitary linear copolymers of ancient sieve pyranose aldehydic acid that is connected, i.e. M fragment and G fragment.They are to replace fragment by the M-G that accounts for major ingredient to link together.Therefore, it is a straight line block line style compound.
The main processes that is adopted among the present invention is as follows.
1, produces mannuronic acid
Get 100 gram food grade sodium alginates, the distilled water that adds about 5000ml carries out swelling, and the swollen time is 1～3 day, then add certain density oxalic acid or hydrochloric acid about 5000ml, boiling water bath refluxed 6～12 hours, was hydrolyzed, subsequent filtration is removed acid solution.To filter gains towards rare, add the solid Na that is equivalent to filtrate weight 0.5～1.0%
2CO
2, make it change sodium salt into.Transfer pH to 2～3 with hydrochloric acid again, centrifugation is further removed the G fragment, with the resin desalination of its supernatant liquor, can also use the sephadex desalination again, adds ethanol after the desalination and precipitates repeatedly, promptly gets mannuronic acid.
2, produce the mannuronic acid propyl ester
With the mannuronic acid airing of above-mentioned gained to a certain amount of moisture content, it is joined in the retort that fills quantitative propylene oxide, mannuronic acid (gram) is W: V=1 with the ratio of propylene oxide (ml): 2～5, add 0.5～1%NaOH of mannuronic acid weight or KOH or sodium ethylate again and make catalyzer, at constant temperature (50～80 ℃), level pressure (1.5～3kg/cm
2) act on 2～4 hours under the condition, or adopt normal pressure (temperature is 40～55 ℃) circumfluence method to react, promptly get the mannuronic acid propyl ester.
3, produce mannuronic acid propyl ester sulfuric ester sodium salt
With the mannuronic acid propyl ester of above-mentioned gained with methyl alcohol or ethanol repetitive scrubbing, oven dry then, (sulphonating agent is a chlorsulfonic acid in temperature (60～80 ℃) sulfonation again, solvent is methane amide or pyridine etc.), promptly obtain the hydrosulfate of mannuronic acid propyl ester, it is used the alcohol purifying, neutralize with NaOH, be the sulfuric ester sodium salt of mannuronic acid propyl ester, i.e. mannose ester.
Embodiment
1, gets 100 gram food grade sodium alginates, added 5000ml distilled water swelling 24 hours, add 5000ml2N oxalic acid again, boiling water bath refluxed 10 hours, filter then to remove acid solution, will filter gains and use 3000ml distilled water, in the ratios adding solid Na of 100 gram filtrate, 1 gram towards rare
2CO
3Be collosol state this moment, transfer pH to 2.8 with hydrochloric acid, centrifugal then (whizzer, 3000 rev/mins) separate, get its supernatant liquor, with 717 and 732 anion and cation exchange resin desalinations, after removing resin, the ethanol that adds 3 times of solution amount precipitates, and the gained throw out 60 ℃ of oven dry down, is mannuronic acid.
2, get the above-mentioned mannuronic acid of 70 grams, sneak into 30 gram water, add the 300ml propylene oxide, put into autoclave, add 0.7 gram NaOH, use the ethanol repetitive scrubbing then three times,, promptly get the mannuronic acid propyl ester in 60 ℃ of oven dry.
3, get the above-mentioned mannuronic acid propyl ester of having dried of 100 grams, be placed in the there-necked flask of 3000ml, install whipping appts and thermometer, add the 1000ml formamide solvent, stirring is mixed, and slowly splashes into the 300ml chlorsulfonic acid, and temperature is not higher than 5 ℃ (use ice-water baths) in the dropping process, make it be warming up to 65～70 ℃ after dripping, reacted 3 hours.Cooling is filtered, and adds 4000ml ethanol and precipitates, and throw out 200ml dissolved in distilled water is used ethanol sedimentation again, three times so repeatedly.After molten again,, behind the deionizing exchange resin, transfer pH to 8, use alcohol precipitation again, be mannuronic acid propyl ester sulfuric ester sodium salt with 4N NaOH solution with 732 and 717 cationic, anionic exchange resin desalinations.
Product of the present invention is a kind of good quasi-heparin substance, its pharmacological testing proves, it has the stronger bolt ability that presses down, during 50mg/kg dosage, press down the bolt rate more than 80%, and the effect of obvious anti-freezing, lipopenicillinase, reduction blood viscosity is arranged, stronger antiatherosclerosis function is arranged, also can suppress the growth rate of lithangiuria salt crystallization. Common pharmacology evidence, it does not all have impact to blood pressure, electrocardiogram, breathing etc. This product avirulence shows that with 18～22 gram Experiment on white mices press 10g/kg dosage gavage, animal subject diet, growth, activity all do not have any anomaly. It is a kind of desirable heparinoid drug of preventing, controlling the ischemic cardiovascular systemic disease, is particularly suitable for prevention.
The process route that the present invention produces mannuronic acid propyl ester sulfuric ester sodium salt is stablized feasible, does not have three wastes problem, is convenient to organize large-scale production.
Claims (4)
1, a kind ofly produces the method for mannuronic acid propyl ester sulfuric ester sodium salt, it is characterized in that earlier the sodium alginate hydrolysis being separated esterification then, sulfonation again by sodium alginate;
2, preparation method as claimed in claim 1, it is characterized in that said hydrolysis is separated under the acidic conditions carries out, and needs boiling water bath to reflux 6～12 hours;
3, preparation method as claimed in claim 1 is characterized in that said esterification is meant the mannuronic acid that made by hydrolysis and the reaction of propylene oxide, and this is reflected at and carries out under constant temperature, the level pressure condition or adopt the atmospheric pressure reflux method, and is catalyzer with NaOH; The temperature and pressure scope is respectively 50～80 ℃, 1.5～3kg/cm
2, when adopting Chang Ya rotation stream method, temperature is 40～55 ℃;
4, preparation method as claimed in claim 1 is characterized in that said sulfonation is meant the middle mannuronic acid propyl ester that makes and the reaction of chlorsulfonic acid, and wherein solvent is methane amide or pyridine, and sulfonation is carried out under mesophilic condition.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 88109698 CN1030454C (en) | 1988-10-30 | 1988-10-30 | Process for preparing sodium salt of propyl mannuronate sulfate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 88109698 CN1030454C (en) | 1988-10-30 | 1988-10-30 | Process for preparing sodium salt of propyl mannuronate sulfate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1042361A true CN1042361A (en) | 1990-05-23 |
| CN1030454C CN1030454C (en) | 1995-12-06 |
Family
ID=4835422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 88109698 Expired - Fee Related CN1030454C (en) | 1988-10-30 | 1988-10-30 | Process for preparing sodium salt of propyl mannuronate sulfate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1030454C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10247073A1 (en) * | 2002-10-09 | 2004-04-22 | Westfälische Wilhelms-Universität Münster | Monomeric uronic acid compound production, for use e.g. as immunosuppressive, antirheumatic or cardiovascular agents, by hydrolyzing bacterially produced polyuronic acid |
| CN100467492C (en) * | 2001-11-30 | 2009-03-11 | Fmc生物高聚物股份有限公司 | Process for the preparation of alginates having a high mannuronic acid content |
| CN102212148A (en) * | 2011-03-21 | 2011-10-12 | 中国海洋大学 | Antithrombotic medicament for intravenous injection and preparation method and application thereof |
| CN102743409A (en) * | 2012-06-18 | 2012-10-24 | 中国海洋大学 | Application of poly mannuronic acid propyl ester sulfate in preparing anti- H1N1 influenza A virus medication |
| CN117064067A (en) * | 2023-08-07 | 2023-11-17 | 湖北工业大学 | Dietary fiber with controllable glycolysis rate, and preparation method and application thereof |
-
1988
- 1988-10-30 CN CN 88109698 patent/CN1030454C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100467492C (en) * | 2001-11-30 | 2009-03-11 | Fmc生物高聚物股份有限公司 | Process for the preparation of alginates having a high mannuronic acid content |
| DE10247073A1 (en) * | 2002-10-09 | 2004-04-22 | Westfälische Wilhelms-Universität Münster | Monomeric uronic acid compound production, for use e.g. as immunosuppressive, antirheumatic or cardiovascular agents, by hydrolyzing bacterially produced polyuronic acid |
| DE10247073B4 (en) * | 2002-10-09 | 2010-08-05 | Mirshafiey, Abbas, Prof. Dr. | Process for the preparation of monomeric uronic acids, in particular D-mannuronic acid and D-guluronic acid and their use as medicaments |
| CN102212148A (en) * | 2011-03-21 | 2011-10-12 | 中国海洋大学 | Antithrombotic medicament for intravenous injection and preparation method and application thereof |
| CN102743409A (en) * | 2012-06-18 | 2012-10-24 | 中国海洋大学 | Application of poly mannuronic acid propyl ester sulfate in preparing anti- H1N1 influenza A virus medication |
| CN102743409B (en) * | 2012-06-18 | 2013-11-20 | 中国海洋大学 | Application of poly mannuronic acid propyl ester sulfate in preparing anti- H1N1 influenza A virus medication |
| CN117064067A (en) * | 2023-08-07 | 2023-11-17 | 湖北工业大学 | Dietary fiber with controllable glycolysis rate, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1030454C (en) | 1995-12-06 |
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