CN1259363C - Transparent acid gel and its preparation method - Google Patents
Transparent acid gel and its preparation method Download PDFInfo
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- CN1259363C CN1259363C CN 03156633 CN03156633A CN1259363C CN 1259363 C CN1259363 C CN 1259363C CN 03156633 CN03156633 CN 03156633 CN 03156633 A CN03156633 A CN 03156633A CN 1259363 C CN1259363 C CN 1259363C
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- hyaluronic acid
- deproteinization
- weight
- glycidyl ether
- acid derivatives
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- Expired - Lifetime
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- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 239000002253 acid Substances 0.000 title description 5
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims abstract description 76
- 229920002674 hyaluronan Polymers 0.000 claims abstract description 51
- 229960003160 hyaluronic acid Drugs 0.000 claims abstract description 51
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 230000003544 deproteinization Effects 0.000 claims description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000002203 pretreatment Methods 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000004132 cross linking Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000376 reactant Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 229960004756 ethanol Drugs 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 238000011010 flushing procedure Methods 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 239000002994 raw material Substances 0.000 abstract description 9
- 241000894006 Bacteria Species 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- 230000002745 absorbent Effects 0.000 description 13
- 239000002250 absorbent Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 4
- CYCBPQPFMHUATH-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)butan-1-ol Chemical compound OCCCCOCC1CO1 CYCBPQPFMHUATH-UHFFFAOYSA-N 0.000 description 3
- 238000002791 soaking Methods 0.000 description 3
- 241000561734 Celosia cristata Species 0.000 description 2
- 210000001520 comb Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 206010018325 Congenital glaucomas Diseases 0.000 description 1
- 206010012565 Developmental glaucoma Diseases 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 208000007157 Hydrophthalmos Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- -1 after fully soaking Substances 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- AEMOLEFTQBMNLQ-QIUUJYRFSA-N beta-D-glucuronic acid Chemical compound O[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-QIUUJYRFSA-N 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 201000001024 buphthalmos Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000000247 postprecipitation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to hyaluronic acid gel and a preparation method thereof. The preparation method comprises the steps hyaluronic acid is deproteinized; then, glycidyl ether which accounts for 1 to 10% of the weight of the hyaluronic acid carries out isothermal reaction for 2 to 24 hours at the temperature of 15 to 35 DEG C in acidic or alkaline environment to prepare the hyaluronic acid gel. Because the raw materials of the hyaluronic acid of the present invention are preprocessed, the prepared gel is colorless and transparent, the growth of some harmful bacteria is prevented, and the gel can be stored for a long period. The prepared hyaluronic acid gel of the present invention has an optimal water absorption multiplying power range. Meanwhile, the reaction condition of the hyaluronic acid gel is mild, the chain breaking and the degradation of the raw materials of the hyaluronic acid are effectively prevented, and the quality of the hyaluronic acid gel is increased.
Description
Technical field
The present invention relates to a kind of hyaluronic acid derivatives and preparation method thereof, more particularly relate to a germplasm acid gel and in hyaluronic acid, add the method that linking agent prepares this hyaluronic acid derivatives.
Background technology
Hyaluronic acid is the straight chain shape macromolecule polysaccharide that β-D-N-acetylglucosamine and β-D-glucuronic acid mutually combine, be distributed widely in places such as mammiferous reticular tissue, cockscomb and streptococcic folder film, owing to do not have kind and internal organs specificity, the hyaluronic acid derivatives that is made by hyaluronic acid all shows good body consistency as weighting material transplanting or injection body, play crease-resistant, rich breast, fill effects such as pad, and human body is had no side effect widespread use medical treatment, beauty industry.
Existing hyaluronic acid raw material has two sources, and the one, animal tissues as cockscomb, buphthalmos etc., makes with extraction method usually; Another source is to utilize the preparation of fermentation using bacteria method, no matter but any method, the hyaluronic acid raw material that makes all contains more impurity such as protein, as not handling, can cause the gel product outward appearance to be turned white, opaque, and easily give birth to unwanted bacteria, so that staging life, is short.
Though U.S. Pat P5827937 discloses with 1,4-butyleneglycol glycidyl ether prepares the method for hyaluronic acid derivatives as linking agent, but in the time of 40 ℃, activate 4 hours, be diluted to 0.5-1% then, just can obtain gel through underpressure distillation again, international monopoly WO8600079 adds 1 in hyaluronic acid, 4-butyleneglycol glycidyl ether carries out crosslinked in the time of 50 ℃, obtain the matter acid gel, all there is the higher so that hyaluronic acid raw material chain rupture of temperature of reaction in they, degraded, product is produced detrimentally affect, simultaneously because linking agent selects the improper water absorbent rate of gel product that causes too high or too low with the ratio of raw material, so that the problem of liner weak effect behind the product injection human body.
Summary of the invention
The purpose of this invention is to provide effective hyaluronic acid derivatives of a kind of long preservative period, liner and preparation method thereof,, at room temperature cross-linking hyaluronic acid is prepared hyaluronic acid derivatives by the hyaluronic acid raw material is increased pre-treatment.
The object of the present invention is achieved like this:
A kind of hyaluronic acid derivatives, it is prepared by following method, and its water-intake rate is 650 times to 350 times:
(1) deproteinization pre-treatment:
With the water-soluble formation mass concentration of the hyaluronic acid solution that is 0.1-2%, the deproteinization product that adds hyaluronic acid weight 0.01-1% then, after stirring, leave standstill, to producing precipitation, filter, the gained filtering solution with 95% ethanol, methyl alcohol or dehydrated alcohol flushing of 2～10 times of volumes, filter, gained is filtered thing and is carried out vacuum-drying;
(2) crosslinking reaction:
It is 1%～2% NaOH, HCl or acetum that the hyaluronic acid of the deproteinization that obtains in (1) is dissolved in its weight 8-12 concentration doubly, add the glycidyl ether of hyaluronic acid weight 1～10%, left standstill at least 8 hours after 2～24 hours in isothermal reaction under 15～35 ℃ the condition; The gained reactant is put into deionized water and was soaked 4～24 hours, and transferring to pH with HCl or NaOH is 6-8.
The weight of the glycidyl ether that adds in the described step (2) is the 5-7.5% of hyaluronic acid weight.
Glycidyl ether in the described step (2) is a diglycidyl ether of ethylene glycol, 1, the glycidyl ether of 4-butyleneglycol.
In the deproteinization pre-treatment step of (1), the deproteinization product that is added is the BD series deproteinization product of vast company of University Of Tianjin.
A kind of preparation method of hyaluronic acid derivatives may further comprise the steps:
(1) deproteinization pre-treatment:
With the water-soluble formation mass concentration of the hyaluronic acid solution that is 0.1-2%, the deproteinization product that adds hyaluronic acid weight 0.01-1% then, after stirring, leave standstill, to producing precipitation, filter, the gained filtering solution with 95% ethanol, methyl alcohol or dehydrated alcohol flushing of 2～10 times of volumes, filter, gained is filtered thing and is carried out vacuum-drying:
(2) crosslinking reaction:
It is 1%～2% NaOH, HCl or acetum that the hyaluronic acid of the deproteinization that obtains in (1) is dissolved in its weight 8-12 concentration doubly, the glycidyl ether that adds hyaluronic acid weight 1～10%, left standstill at least 8 hours after 2～24 hours in isothermal reaction under 15～35 ℃ the condition: the gained reactant is put into deionized water and was soaked 4～24 hours, and transferring to pH with HCl or NaOH is 6-8.
The weight of the glycidyl ether that adds is the 5-7.5% of hyaluronic acid weight.
Described glycidyl ether is a diglycidyl ether of ethylene glycol, 1, the glycidyl ether of 4-butyleneglycol.
In (1) deproteinization pre-treatment step, the deproteinization product that is added is the BD series deproteinization product of vast company of University Of Tianjin.
The present invention has the good technical effect:
1. behind the hyaluronic acid deproteinization, through the crosslinked colorless transparent gel that obtains, electricity has prevented the growth of some unwanted bacteria simultaneously, but long-term storage, and do not use the product of deproteinization technology, place after 5 days, gel turns white, and muddiness this shows that the present invention has greatly improved quality product.
2. the present invention selects the operating weight ratio of raw material and linking agent rightly for use, can obtain the gel of appropriate water absorbent rate, and wherein water absorbent rate is by the water-intake rate formula
Obtain.Q is a water absorbent rate, m
1Be hyaluronic weight (gram), m
2Weight (gram) for the back hyaluronic acid derivatives that absorbs water, test shows, the add-on of linking agent is big more, the matter acid gel water absorbent rate that makes is low more, test shows when the glycidyl ether weight of using during as the 1-10% of hyaluronic acid weight, the water-intake rate of the hyaluronic acid derivatives that obtains is 650 times-350 times, when the glycidyl ether weight of using during as the 5-7.5% of hyaluronic acid weight, the water absorbent rate of resulting hyaluronic acid derivatives is 420-380 times, and the gel of this scope is the best matter acid gel that human body uses.
3. the present invention reacts hyaluronic acid and linking agent under 15-35 ℃ mild conditions, and extremely useful effect has been played in hyaluronic protection, has effectively prevented chain rupture, the degraded of hyaluronic acid raw material, and quality product is improved.
Embodiment
The deproteinization pre-treatment:
Embodiment 1
Hyaluronic acid 10g is dissolved in the 1000ml water, forms 1% solution, adds the BD-2 of vast company of University Of Tianjin deproteinization product 5mg, after fully stirring, leaves standstill, and post precipitation directly occurs and filters.Filtrate adds 3000ml 95% edible ethanol, and violent stirring is filtered to white precipitate occurring, and filter cake carries out vacuum-drying.The 9.8g protein content less than 0.1% hyaluronic acid.
Crosslinking reaction:
Embodiment 1
The deproteinization hyaluronic acid 2g that makes with deproteinization pre-treatment embodiment 1 is dissolved in 1% NaOH 24ml, add the 40mg diglycidyl ether of ethylene glycol, after reacting 2 hours under 15 ℃ of conditions, standing over night, soak with deionized water then, transfer to neutrality, after fully soaking with HCl, so water absorbent gel weight 1000g is by the water-intake rate formula
The gained gel product is the hyaluronic acid derivatives of 500 times of water-intake rates as can be known.[Q is a water absorbent rate, m
1Be hyaluronic weight (gram), m
2Be the weight of the back hyaluronic acid derivatives that absorbs water, this hyaluronic acid gel (seeing Table 1).]
Embodiment 2
The deproteinization hyaluronic acid 2g that makes with deproteinization pre-treatment embodiment 1 is dissolved among the 1.5%NaOH solution 20ml, add 100mg 1,4-butyleneglycol glycidyl ether, stirred the back in 20 ℃ of placements 24 hours, reactant places deionized water, add HCl and regulate pH value to neutral, water absorbent gel is 840g after fully soaking, by the water-intake rate formula as can be known the gained gel product be the hyaluronic acid derivatives (seeing Table 1) of 420 times of water absorbent rates.
Embodiment 3
The deproteinization hyaluronic acid 2g that makes with deproteinization pre-treatment embodiment 1 is dissolved among the 1%HCl solution 20ml, add 200mg 1,4-butyleneglycol glycidyl ether, react under 35 ℃ of conditions, standing over night after 4 hours is inserted reactant in the deionized water then, regulate neutral with NaOH, after fully soaking, water absorbent gel weight is 700g, by the water-intake rate formula as can be known the gained gel product be 350 times of hyaluronic acid derivatives of water absorbent rate (seeing Table 1).
Table 1
| Hyaluronic acid weight (g) | Linking agent weight (g) | The ratio of linking agent and hyaluronic acid weight | Weight (g) after the hyaluronic acid derivatives suction | Water absorbent rate |
| 2 | 0.04 | 2％ | 1000 | 500 |
| 2 | 0.1 | 5％ | 840 | 420 |
| 2 | 0.2 | 10％ | 700 | 350 |
Claims (8)
1. hyaluronic acid derivatives, it is characterized in that: it is prepared by following method, and its water-intake rate is 650 times to 350 times:
(1) deproteinization pre-treatment:
With the water-soluble formation mass concentration of the hyaluronic acid solution that is 0.1-2%, the deproteinization product that adds hyaluronic acid weight 0.01-1% then, after stirring, leave standstill, to producing precipitation, filter, the gained filtering solution with 95% ethanol, methyl alcohol or dehydrated alcohol flushing of 2～10 times of volumes, filter, gained is filtered thing and is carried out vacuum-drying;
(2) crosslinking reaction:
It is 1%～2% NaOH, HCl or acetum that the hyaluronic acid of the deproteinization that obtains in (1) is dissolved in its weight 8-12 concentration doubly, add the glycidyl ether of hyaluronic acid weight 1～10%, left standstill at least 8 hours after 2～24 hours in isothermal reaction under 15～35 ℃ the condition; The gained reactant is put into deionized water and was soaked 4～24 hours, and transferring to pH with HCl or NaOH is 6-8.
2. hyaluronic acid derivatives according to claim 1 is characterized in that: the weight of the glycidyl ether that adds in the described step (2) is the 5-7.5% of hyaluronic acid weight.
3. hyaluronic acid derivatives according to claim 1 is characterized in that: the glycidyl ether in the described step (2) is a diglycidyl ether of ethylene glycol, 1, the glycidyl ether of 4-butyleneglycol.
4. hyaluronic acid derivatives according to claim 1 is characterized in that: in the deproteinization pre-treatment step of (1), the deproteinization product that is added is the BD series deproteinization product of vast company of University Of Tianjin.
5. the preparation method of a kind of hyaluronic acid derivatives as claimed in claim 1 is characterized in that: may further comprise the steps:
(1) deproteinization pre-treatment:
With the water-soluble formation mass concentration of the hyaluronic acid solution that is 0.1-2%, the deproteinization product that adds hyaluronic acid weight 0.01-1% then, after stirring, leave standstill, to producing precipitation, filter, the gained filtering solution with 95% ethanol, methyl alcohol or dehydrated alcohol flushing of 2～10 times of volumes, filter, gained is filtered thing and is carried out vacuum-drying;
(2) crosslinking reaction:
It is 1%～2% NaOH, HCl or acetum that the hyaluronic acid of the deproteinization that obtains in (1) is dissolved in its weight 8-12 concentration doubly, add the glycidyl ether of hyaluronic acid weight 1～10%, left standstill at least 8 hours after 2～24 hours in isothermal reaction under 15～35 ℃ the condition; The gained reactant is put into deionized water and was soaked 4～24 hours, and transferring to pH with HCl or NaOH is 6-8.
6. the preparation method of hyaluronic acid derivatives according to claim 5 is characterized in that the weight of the glycidyl ether that adds is the 5-7.5% of hyaluronic acid weight.
7. the preparation method of hyaluronic acid derivatives according to claim 5 is characterized in that described glycidyl ether is a diglycidyl ether of ethylene glycol, 1, the glycidyl ether of 4-butyleneglycol.
8. the preparation method of hyaluronic acid derivatives according to claim 5 is characterized in that in (1) deproteinization pre-treatment step, and the deproteinization product that is added is the BD series deproteinization product of vast company of University Of Tianjin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03156633 CN1259363C (en) | 2003-09-05 | 2003-09-05 | Transparent acid gel and its preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03156633 CN1259363C (en) | 2003-09-05 | 2003-09-05 | Transparent acid gel and its preparation method |
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| Publication Number | Publication Date |
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| CN1590444A CN1590444A (en) | 2005-03-09 |
| CN1259363C true CN1259363C (en) | 2006-06-14 |
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| CN 03156633 Expired - Lifetime CN1259363C (en) | 2003-09-05 | 2003-09-05 | Transparent acid gel and its preparation method |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110431154A (en) * | 2017-01-26 | 2019-11-08 | 美容系统制药有限责任公司 | With the hyaluronic acid of natural or semi-synthetic cross-linking agents |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101502675B (en) * | 2008-02-04 | 2013-02-13 | 山东省药学科学院 | Suspension of hyaluronic acid or salt thereof containing macromolecule hydrogel for injection and preparation method thereof |
| US8197849B2 (en) * | 2010-02-12 | 2012-06-12 | National Health Research Institutes | Cross-linked oxidated hyaluronic acid for use as a vitreous substitute |
| CN102805880A (en) * | 2011-05-31 | 2012-12-05 | 上海国睿生命科技有限公司 | Tissue engineering gel scaffold material, preparation method and use thereof |
| FR2983483B1 (en) * | 2011-12-02 | 2014-11-14 | Vivacy Lab | PROCESS FOR SIMULTANEOUS SUBSTITUTION AND RETICULATION OF A POLYSACCHARIDE VIA ITS HYDROXYL FUNCTIONS |
| CN102660040B (en) * | 2012-05-03 | 2014-03-12 | 杭州协合医疗用品有限公司 | Method for preparing sodium hyaluronic acid gel |
| CN103146003A (en) * | 2013-03-06 | 2013-06-12 | 上海其胜生物制剂有限公司 | Preparation method of low-temperature secondary cross-linked sodium hyaluronate gel |
| CN113278170B (en) * | 2021-06-15 | 2021-11-16 | 苏州大学 | A kind of chemically cross-linked hyaluronic acid hydrogel and preparation method and application thereof |
-
2003
- 2003-09-05 CN CN 03156633 patent/CN1259363C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110431154A (en) * | 2017-01-26 | 2019-11-08 | 美容系统制药有限责任公司 | With the hyaluronic acid of natural or semi-synthetic cross-linking agents |
| CN110431154B (en) * | 2017-01-26 | 2022-07-05 | 美容系统制药有限责任公司 | Hyaluronic acid cross-linked with natural or semi-synthetic cross-linking agents |
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| CN1590444A (en) | 2005-03-09 |
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Owner name: SHANDONG KAILEPU BIOLOGICAL ENGINEERING CO., LTD. Free format text: FORMER OWNER: JINAN YONGLI BIOTECHNOLOGY CO., LTD. Effective date: 20070601 |
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| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20070601 Address after: 1, Ji'nan, Shandong, Qilihe Road, North Section 2 No. 250100 floor, 12 floor, East Unit Patentee after: Shandong Kailepu Pharmaceuticals Co.,Ltd. Address before: Ji'nan city of Shandong Province Yu Hang Road 250002 No. 55 19-4 Patentee before: Ji'nan Lee Biotechnology Co.,Ltd. |
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| CX01 | Expiry of patent term |
Granted publication date: 20060614 |
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| CX01 | Expiry of patent term |