CN1286455C - Pharmaceutical use of 5-hydroxymethyl furfural - Google Patents
Pharmaceutical use of 5-hydroxymethyl furfural Download PDFInfo
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- CN1286455C CN1286455C CN 200510075356 CN200510075356A CN1286455C CN 1286455 C CN1286455 C CN 1286455C CN 200510075356 CN200510075356 CN 200510075356 CN 200510075356 A CN200510075356 A CN 200510075356A CN 1286455 C CN1286455 C CN 1286455C
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Abstract
The present invention discloses the application of 5-hydroxymethyfurfural in preparing a medicine for treating endotoxemia and reducing death caused by multi-viscera function failure induced by endotoxemia. The present invention also discloses the application of 5-hydroxymethyfurfural in preparing a medicine for treating endotoxemia generated in a stress state of severe wounds, war wounds, infection, major operation, severe shock, radiotherapy, chemotherapy and viscera transplantation, endotoxemia complicated by severe hepatitis, hepatic cirrhosis, gastrointestinal tract diseases, malnutrition and biliary tract intestinal obstruction, or pyemia, septic shock and multi-viscera function disorder or failure induced by the endotoxemia, and the application of 5-hydroxymethyfurfural in preparing a medicine for treating septicemia, acute pneumonia, acute hepatic failure, acute DIC, jue exhaustion diseases of severe shock and diseases caused by cytomegalovirus, herpesvirus and influenza virus.
Description
Technical field
The present invention relates to a kind of medicinal usage of chemical compound, particularly the medicinal usage of 5 hydroxymethyl furfural.Patent application of the present invention is for dividing an application, and the original bill application number is 031020658, and the applying date is on January 30th, 2003, and denomination of invention is a kind of plant extract, chemical compound and extracting method thereof and purposes for the treatment of endotoxemia.
Background technology
Endotoxin (Endotoxin ET) is lipopolysaccharide (Lopipolysacharide LPS) composition of leather Lan Shi negative bacillus cell wall, is immunity of mediation human body and the unusual crucial virulence factor of inflammatory reaction.Endotoxemia is by endogenous and the excessive blood circulation that enters of exogenous endotoxin, excite the human body immunocyte to discharge the various kinds of cell factor in a large number, destroy human body inflammatory reaction balance, cause microcirculation disturbance and organize major injury, cause extensive and intensive pathological reaction, and then high-risk property disease such as the septic shock that causes, MOFE.In recent years, many studies show that, sepsis, organ function injury and intestinal endotoxemia that the trauma stress state takes place are closely related.The intestinal mucosa mechanical masking function that stress state occurs down is impaired, make than the little endotoxin of bacteria particles at first transposition enter blood, cause endotoxemia, activate inflammatory cell, discharge a large amount of inflammatory mediators and cytokine and form sepsis.Therefore, the generation of endotoxemia not merely is present in the various infectious disease of inside and outside section, serious wound, burn, shock, major operation and cancer are put, chemotherapy etc. all be the main diseases that produces endotoxemia because of.And endotoxemia be clinical many refractory diseases such as severe complication such as acute lung declines, acute hepatic failure, acute renal failure, acute dic, septic shock and multiple organs dysfunction main diseases because of.Clinical observation confirms that burn patients endotoxemia incidence rate is 58%, presents significant sepsis state more, finally can concurrent MODS and death.Occur tangible endotoxemia after the hemorrhagic shock, even blood volume is supplied, pressor agent has been used maximum dose, and shock still can not corrected, and finally is developed to death.The incidence rate of hepatitis gravis, hepatitis hepatitis interstitialis chronica, chronic hepatitis, acute hepatitis patient's intestinal endotoxemia (IETM) is respectively 93.3%, 84.3%, 79.0% and 75.0%.In bile duct obstruction and other abdomen operating endotoxemia progress of internal organs illness for renal insufficiency account for 51.4%, develop at last multiple organs failure death up to 28.3%.The multiple organ dysfunction syndrome that endotoxemia brought out (MODS) is one of modal dead cause of disease of intensive care unit(ICU).Antiendotoxin treatment at the endotoxemia and the MOFE of bringing out is the key subjects and the most active fields of current Chinese scholars research, but does not also have a kind of medicine official listing so far.
Summary of the invention
The object of the invention is to provide the effective site of Radix Isatidis and wherein main chemical constituent; The object of the invention also is to provide the effective site of Radix Isatidis and the preparation method of wherein main chemical constituent; The 3rd purpose of the present invention is to provide the new purposes of the treating endotoxemia of the effective site of Radix Isatidis and wherein main chemical constituent.
Extraction has the effective site for the treatment of endotoxemia effect from Radix Isatidis, can take following any method:
Raw medicinal material: the dry root of cruciferae isatis Isatis indigotica Fort..
1, ethanol is made the solvent extraction process of (containing immersion, percolation, backflow): repeatedly soak or reflux, extract, with 80% ethanol, or use 80% ethanol percolate extraction, merge extractive liquid, leaves standstill, and gets supernatant liquid filtering, and filtrate recycling ethanol gets the effective site fluid extract.
2, ion exchange resin extraction process: after a certain amount of Radix Isatidis soaked, decoct with water 2 times each 1.5h-2h, merge water decoction, leave standstill, get the supernatant centrifugalize, centrifugal liquid exchanges by storng-acid cation exchange resin, collect effluent, be concentrated into every milliliter of medicinal liquid and contain about 2 grams of crude drug, add 95% ethanol and make and contain the alcohol amount and reach 80%, staticly settle, get supernatant liquid filtering, filtrate recycling ethanol gets the effective site fluid extract.
3, macroporous adsorbent resin extraction process: after a certain amount of Radix Isatidis soaked, decoct with water 2 times each 1.5h-2h, merge water decoction, leave standstill, get the supernatant centrifugalize, separating medium passes through macroporous adsorbent resin, respectively with the resin after 10%, 20%, 40%, 50% the ethanol elution absorption, and the collection eluent, leave standstill, get supernatant liquid filtering, filtrate is reclaimed ethanol respectively, gets the effective site fluid extract.
4, other organic solvent extraction technology: the extractum thin up of ethanol extraction is become every milliliter of aqueous solution that contains crude drug 1 gram, use petroleum ether, chloroform extraction respectively successively, petroleum ether, ethyl acetate extraction, petroleum ether, n-butanol extraction.Reclaim the organic solvent in chloroform, ethyl acetate, the butanol extraction liquid respectively, get the effective site fluid extract.
Four compounds that contain in the effective site of the present invention are respectively: furfural compounds, lignin chemical compound, Benzazole compounds, organic acid chemical compound.Main effective ingredient in the classes of compounds is: the furfural compounds: 5 hydroxymethyl furfural, English name: 5-hydroxymethylfurfural (5-HMF), molecular formula: C
6H
6O
3, molecular weight: 126; Lignin chemical compound: isolarisiresinol.English name: Isolariciresinol molecular formula: C
20H
24O
6Molecular weight: 360; Benzazole compounds: 1-N-methoxyl group-2-oxygen-indole-3-acetamide; Organic acid chemical compound: the long-chain fatty acid of ortho-aminobenzoic acid, salicylic acid, benzoic acid, syringic acid, hydroxyl and two keys etc.Furfural compounds, lignin chemical compound, the Benzazole compounds content 5-60% in effective site comprises that the content of organic acid chemical compound in effective site of the long-chain fatty acid of ortho-aminobenzoic acid, salicylic acid, syringic acid, quinazolone acid and hydroxyl and two keys is 5-30%.
The part by weight of the best of breed of effective ingredient is in the effective site: 5 hydroxymethyl furfural 20-50: different larch resin alcohol 1-3: 1-N-methoxyl group-2-oxygen-indole-3-acetamide 10-40.
The compounds of this invention clinical practice dosage range is respectively: 5 hydroxymethyl furfural is 1.0mg～10.0mg/kg, and different larch resin alcohol is 0.1mg～1.0mg/kg, and 1-N-methoxyl group-2-oxygen-indole-3-acetamide is 0.8mg～8.0mg/kg.The pH scope of preparation of the present invention is at 2.0-5.0.
The present invention's chemical compound 1-N-methoxyl group-2-oxygen-indole-3-acetamide that separation obtains from this plant first is the main effective ingredient in the effective site.English name: the 1-N-methoxy-2-oxo-indolyl-3-acetamide structural formula is:
Molecular formula: C
11H
12O
3N
2, molecular weight: 220;
The extracting method of above-mentioned noval chemical compound is: the ethyl acetate extract of Radix Isatidis separates with silica gel column chromatography, uses chloroform successively: methanol=80: 1 (500ml*18), 40: 1 (500ml*20), 30: 1 (500ml*5), 20: 1 (500ml*32) eluting.At chloroform: among stream part 7B of methanol=40: 1 eluting two fluorescence speckles are arranged, will flow part 7B and continue a column chromatography, further use petroleum ether: chloroform: methanol=15: 15: 1 eluting obtains a white, needle-shaped crystals.
Effective site of the present invention or its chemical constituent can be made into pharmaceutically acceptable preparation, for example be prepared into oral Preparation: tablet, capsule, pill, granule, drop pill, oral liquid, be prepared into the rectally preparation: suppository, enema, be prepared into the percutaneous drug delivery preparation: unguentum, Emulsion, liniment, patch, transdermal absorption formulation are prepared into injecting and administering preparations: intramuscular dose, intravenous injection.When the treatment viral infection, active component can or be made compound preparation with suitable antiviral administration.This active component can be used as lyophilized formulations.
Following experimental example is used to further specify the present invention:
Experimental example 1: the present invention confirms that by animal vivo test Radix Isatidis has the effective site for the treatment of endotoxemia effect
The test medicinal liquid: the extract thin up that above each extraction process obtains is made into every milliliter of medicinal liquid that contains 2 gram crude drugs.
Test endotoxin: the O that is provided is provided with Chinese pharmaceutical biological product
111B
4Escherichia coli through this prepared in laboratory, purification endotoxin, and are identified the O that is provided with Chinese pharmaceutical biological product
111B
4The escherichia coli endotoxin demarcation of tiring.The mice dosage range of preparation endotoxemia model is a per kilogram of body weight 15-18 milligram.
Test animal: available from Chinese Academy of Medical Sciences animal reproduction field, Kunming kind, secondary mice.Weight range: 18-22 gram, male and female half and half.By the body weight random packet, every treated animal is no less than 30.And carry out the t check of each treated animal body weight, and there is not significant difference between each group, take out one group at random and make negative control.
Test method: each treated animal fasting be can't help water 12 hours before the test, the administration group irritates stomach for 0.5 milliliter for different process gained extracting solution by per 20 gram body weight, negative control group is irritated stomach with the volume distilled water, after the administration 45 minutes, inject the endotoxin solution of 80% lethal dose from mouse tail vein, preparation endotoxemia and MOFE model.
Observation index and data processing method: with survival rate and time-to-live be index, be leading indicator with the survival rate.Observe also and write down in 72 hours, the dead number of elements of every mouse diing time and every group calculates the time-to-live and the survival rate of every treated animal, and whether there were significant differences between the time-to-live with t inspection administration group and negative control group, uses X
2Whether there were significant differences between inspection administration group and the negative control group survival rate.Result of the test: see Table 1.
The anti-endotoxin effect of the extractive part that table 1 distinct methods extraction Radix Isatidis obtains
| Different process extracts component | Time-to-live (h) | Survival rate (%) | X 2Check | The T check | ||
| Matched group | The administration group | Matched group | The administration group | (X 2≥3.84) | (P≤0.05) | |
| Ethyl acetate fraction extracting n-butyl alcohol position, chloroform extraction position, 80% alcohol extract position cationic ion-exchange resin efflux alcohol extracting position macroporous absorbent resin 10%-50% alcohol wash-out position | 31.15 38.90 31.15 24.57 33.86 25.62 | 67.45 59.33 47.20 45.58 61.56 55.40 | 8/32 12/30 8/32 4/34 9/30 5/30 | 28/32 23/30 18/32 17/34 23/30 20/30 | 22.92 6.86 5.23 9.92 11.32 13.44 | 4.04*10 -9 3.33*10 -3 9.60*10 -3 3.80*10 -4 4.04*10 -5 3.17*10 -5 |
Conclusion: 6 kinds of extract parts that (1) obtains with above 4 kinds of extraction separation methods all have remarkable treating endotoxemia and reduce the effect of mortality rate due to its MOFE of bringing out.
(2) in 6 kinds of extract parts, 80% ethanol extraction part treating endotoxemia and to reduce due to its MOFE of bringing out the effect of mortality rate the strongest, n-butyl alcohol, ethyl acetate and chloroform extraction part also have extremely significant treating endotoxemia and reduce the effect of mortality rate due to its MOFE of bringing out, the 50% following ethanol elution that obtains from macroporous adsorbent resin technology partly has remarkable treating endotoxemia and reduces the effect of mortality rate due to its MOFE of bringing out, and composition is the middle polarity material in the prompting effective site.
(3) storng-acid cation exchange resin effluent 80% ethanol extraction partly has remarkable treating endotoxemia and reduces the effect of mortality rate due to its MOFE of bringing out, and the part main active in the prompting effective site is not by cationic exchange resin adsorption.
(4) after deliberation, mainly contain following four compounds in the effective site of discovery Radix Isatidis treating endotoxemia: furfural compounds, lignin chemical compound, Benzazole compounds and organic acid chemical compound.
Experimental example 2: the separation of effective ingredient monomeric compound in the effective site of the present invention: the effective extract part that proves through animal experiment in the above-mentioned table 1, its high performance liquid chromatography has 3 main absworption peaks, and the thin layer chromatography chromatograph has 3 main speckles and curative effect closely related.Because 3 main component content are higher at the ethyl acetate extraction position, are about to the ethyl acetate extraction position and carry out column chromatography for separation.
Material: Haiyang Chemical Plant, Qingdao produces column chromatography silica gel, thin layer chromatography G plate and GF254 plate.The analytical reagent chloroform of the sharp chemical company of Beijing benefit, methanol, petroleum ether, ethyl acetate etc.Development system: petroleum ether-chloroform-methanol=4: 4: 1,2: 4: 1, chloroform-methanol=80: 1,40: 1,20: 1.
The Spectrum Analysis of monomeric compound and structural identification: from above component, isolate monomeric compound, determine 25 chemical compounds that have of structure through analysis center of Military Medical Science Institute mass spectrum, hydrogen spectrum, carbon analysis of spectrum and spectrum unscrambling, wherein 22 is known compound, and 3 for separating the chemical compound that obtains first from this plant.
The present invention's chemical compound 1-N-methoxyl group-2-oxygen-indole-3-acetamide that separation obtains from this plant first is the main effective ingredient in the effective site.Its spectral data is as follows: FAB-MS m/z[M+H]
+Be 221.
1HNMR(CDCL3)，δ：2.71(1H，dd，J＝15.9，7.0Hz H-10a)，2.97(1H，dd，J＝15.9，5.7Hz H-10b)，3.85(1H，t，J＝6.4Hz H-3)，4.03(3H，S，OCH
3)，6.09(1H，br.s，-NH)，6.28(1H，br.s，-NH)，6.99(1H，dd，J＝7.8，1.0Hz H-7)，7.09(1H，td，J＝7.8，1.0Hz H-5)，7.32(1H，dd，J＝7.8，1.0Hz H-4)，7.33(1H，td，J＝7.8，1.0Hz H-6)。By
13The CNMR spectrum can infer further that there are two hydroxyls in chemical compound.This chemical compound bismuth potassium iodide test is positive, and is illustrated as alkaloid compound.By mass spectrometric data and combination
1HNMR,
13The CNMR spectrum infers that the molecular formula of chemical compound 6 is C
11H
12N
2O
3According to the source of students relation, this chemical compound may be Benzazole compounds, and has 2-indolone skeleton.By
1Observed two active hydrogens reach among the HNMR
13Existence-C=O-NH2 (amide) group is inferred in carbonylation displacement in the CNMR spectrum.
13In the CNMR spectrum δZhi be 63.42-OCH3 links to each other with 1 N atom and conforms to this compounds numerical value in the document.The molecular formula of inferring this chemical compound in view of the above is: C
11H
12O
3N
2, structural formula is: called after: 1-N-methoxyl group-2-oxygen-indole-3-acetamide.
Experimental example 3: the action intensity of each main component and ratio in the effective site of the present invention
The preparation of test liquid: acetic acid ethyl ester extract is carried out silica gel column chromatography separate, with chloroform eluting position and chloroform: methanol=solvent was reclaimed at the eluting position in 10: 1, adding water, to be made into concentration be the background solution that contains crude drug amount 2g/ml, 5 hydroxymethyl furfural, different fallen leaves pinaster alcohol ester, 1-N-methoxyl group-2-oxygen-indole-3-acetamide that chloroform-methanol different proportion eluting is obtained than adding in the background liquid, screen best proportioning by Different Weight.For guaranteeing the stability of effective ingredient, the background solution of No. 3 effective sites is transferred pH=2.5 with 5% hydrochloric acid, and the background solution of No. 6 effective sites is transferred pH=4.5 with 5% sodium hydroxide, and it is the same that experimental animal, medication and result add up.Result of the test sees Table 2.
Each main component ratio of table 2 and corresponding results of pharmacodynamic test
| The medicine-feeding part numbering | Each position proportion (weight ratio) | The animal experiment data | ||||
| 5-HMF | Different fallen leaves pinaster alcohol ester | 1-N-methoxyl group-2-oxygen-indole-3-acetamide | Medicinal liquid pH value | X 2Check (X 2≥3.84) | T checks (P≤0.05) | |
| Medicine-feeding part 1 medicine-feeding part 2 medicine-feeding parts 3 medicine-feeding parts 4 medicine-feeding parts 5 medicine-feeding parts 6 background solution 7 | 17.00 17.00 51.00 0.00 0.00 0.00 0.00 | 1.00 1.00 0.00 1.00 1.50 0.00 0.00 | 15.0 0.00 0.00 7.5 0.00 30.0 0.00 | 4.00 2.80 2.50 3.80 3.50 4.50 3.50 | 20.43 13.08 4.19 4.22 3.95 4.19 0.00 | 5.16*10 -9 7.04*10 -5 0.05 0.01 0.00 0.05 0.00 |
Conclusion:
(1) in the 5 hydroxymethyl furfural in the effective site, different larch resin alcohol, 1-N-methoxyl group-3 main component individualisms of the 2-oxygen-indole-3-acetamide background solution, all can reduce the mouse death rate due to the MOFE that endotoxemia brings out significantly.
(2) with under the dosage condition, the action intensity of various combinations is: 5 hydroxymethyl furfural+different larch resin alcohol+1-N-methoxyl group-2-oxygen-indole-3-acetamide＞5 hydroxymethyl furfural+different larch resin alcohol＞different larch resin alcohol+1-N-methoxyl group-2-oxygen-indole-3-acetamide.
(3) part by weight of the best of breed of effective ingredient is in the effective site: 5 hydroxymethyl furfural 20-50: different larch resin alcohol 1-3: 1-N-methoxyl group-2-oxygen-indole-3-acetamide 10-40.
(4) action intensity of each effective ingredient, the combination of effective ingredient different proportion is relevant with concentration separately in the effective site, strengthens with concentration increase effect.
(5) the main effective ingredient in the effective site is that 5 hydroxymethyl furfural, different larch resin alcohol, 1-N-methoxyl group-2-oxygen-indole-3-acetamide, organic acid can be used as the quality control index that the present invention treats the effective site of endotoxemia.
(6) 5 hydroxymethyl furfural to the treatment concentration range of the mice endotoxemia and the MOFE of bringing out at per kilogram of body weight 10mg～100mg/kg, at per kilogram of body weight 1mg～10.0mg/kg, the treatment concentration range of 1-N-methoxyl group-2-oxygen-indole-3-acetamide is at per kilogram of body weight 8mg～80.0mg/kg to the treatment concentration range of mice for different larch resin alcohol.
The principal indication of effective site of the present invention: effective site of the present invention can reduce the mortality rate of the sepsis that brought out by endotoxemia, septic shock, MOFE effectively.Be applicable to serious wound (burn, fight) wound, infection, major operation, severe hemorrhagic shock, put the endotoxemia that produces under the stress state such as (change) treatment, organ transplantation, concurrent endotoxemias such as hepatitis gravis, liver cirrhosis, gastroenteropathy, malnutrition, biliary tract/intestinal obstruction, sepsis, septic shock, multiple organs dysfunction even the depletion brought out by endotoxemia.This effective site has the heat-clearing and toxic substances removing of theory of Chinese medical science, activating blood circulation to dissipate blood stasis, the recuperating depleted YANG and rescuing the patient from collapse effect, be applicable to the epidemic febrile disease witness of the evil direct attack defensive-qi-nutrient-blood of pyretic toxicity: as the excessive noxious heat of septicemia, the pyretic toxicity of acute pneumonia becomes silted up to wet to stop up and stagnates in lung the scorchingly hot string of attacking of acute hepatic failure, damp-heat gluing each other, the heresy of the pyretic toxicity of acute dic is gone into nutrient blood, the syncope of severe hemorrhagic shock etc.
This effective site can be treated or prevent any and the LPS diseases associated effectively, and described disease includes, but are not limited to endotoxemia (or sepsis syndrome), also suppresses the generation of the virus of LPS stimulation.The effect of duplicating of these viruses is the control that directly or indirectly is subjected to the NF-KB regulatory region.These viruses comprise cytomegalovirus, herpesvirus, but be not limited to this, in addition, because the activation of influenza virus is subjected to that the effect of LPS strengthens and the increase of TNF-α burst size is relevant with the comprehensive condition of influenza virus A and bacterial infection, the present invention also may play inhibitory action to the activation of influenza virus.
Embodiment 1:
5 hydroxymethyl furfural 120 gram adds excipient system granule 300 grams routinely, fills and makes 1000 of 0.3 gram/capsules, and modulator ph value is 2-5, day 3 times, each 1 oral.
Embodiment 2:
Different larch resin alcohol 2 grams add PEG-6000 48 grams, and modulator ph value is 2-5, and heating and melting drips and makes 1000 of 50 milligrams of/drop pill, day 3 times, each 5, sublingual administration.
Embodiment 3:
1-N-methoxyl group-2-oxygen-indole-3-acetamide 120g adds excipient routinely, modulator, system granule 300 gram is pressed into 1000 in the tablet of 0.3 gram/sheet, day 3 times, each 1 oral.
Embodiment 4:
5 hydroxymethyl furfural: different larch resin alcohol: 1-N-methoxyl group-2-oxygen-indole-3-acetamide=15.0: 1.0: 15.0, totally 100.0 grams add excipient routinely, modulator, system granule 300 grams are filled and are made 1000 of 0.3 gram/capsules.Days 3 times, each 1 oral.
Claims (2)
1, the application of 5 hydroxymethyl furfural in medicine dead due to the MOFE for preparing treatment endotoxemia and reduction so bring out.
2, the endotoxemia that endotoxemia is meant that the serious wound of treatment burning, war wound, infection, major operation, severe hemorrhagic shock, radiotherapy, chemotherapy, organ transplantation stress state produce is down wherein treated in application as claimed in claim 1; Hepatitis gravis, liver cirrhosis, gastroenteropathy, malnutrition, the concurrent endotoxemia of biliary tract/intestinal obstruction; Wherein bring out MOFE and be meant sepsis, septic shock, multiple organs dysfunction or the depletion of bringing out by endotoxemia.
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| CN101544624B (en) * | 2009-05-11 | 2011-06-08 | 吉林大学 | 5-methylol-furfural-5-furfural-methanol, preparation method thereof and medical application thereof |
| CN102614206A (en) * | 2011-01-31 | 2012-08-01 | 澳门科技大学 | Application of 7S,8R,8'R-(+)-lariciresinol-4,4'-bi-O-beta-D-glucopyranoside in preparing medicines |
| CN104352486B (en) * | 2014-09-05 | 2016-08-17 | 贵州省生物技术研究开发基地 | 5 hydroxymethyl furfural purposes in preparing stomach motility enhancing medicine |
| CN104856986A (en) * | 2015-04-29 | 2015-08-26 | 吉林农业大学 | New application of 5-hydroxymethyl-2-furaldehyde (5-HMF) in preparation of anti-liver fibrosis medicine |
| CN105997983B (en) * | 2016-06-20 | 2018-09-11 | 贵州省生物技术研究开发基地 | Application of the 5 hydroxymethyl furfural in preparing Anti-helicobacter pylori drugs |
| CN113854299B (en) * | 2020-06-30 | 2023-07-21 | 中国科学院宁波材料技术与工程研究所 | Application of 2, 5-substituted furan compounds and/or metal complexes thereof in antibacterial and mildew-proof disinfection field |
| CN113197887B (en) * | 2021-06-07 | 2022-05-27 | 杭州师范大学 | Application of 5-hydroxymethylfurfural in preparation of antiviral drugs |
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| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20061129 Termination date: 20150130 |
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| EXPY | Termination of patent right or utility model |