CN106146456A - A kind of method of the erdosteine compound preparing treatment respiratory inflammation - Google Patents
A kind of method of the erdosteine compound preparing treatment respiratory inflammation Download PDFInfo
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- CN106146456A CN106146456A CN201610595356.3A CN201610595356A CN106146456A CN 106146456 A CN106146456 A CN 106146456A CN 201610595356 A CN201610595356 A CN 201610595356A CN 106146456 A CN106146456 A CN 106146456A
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- erdosteine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A kind of method that the invention discloses erdosteine compound preparing treatment respiratory inflammation, belongs to pharmaceutical technology field.The X ray powder diffraction pattern that the erdosteine compound use Cu K alpha ray measurement that the method prepares obtains is as shown in Figure 1.The stable chemical nature of erdosteine crystal prepared by the present invention, good water solubility, there is higher stability, bring conveniently to the preparation of various preparations, be especially suitable for clinical practice.
Description
The application is that the application for a patent for invention that applicant Miao Yiwen proposes is (invention entitled: one treats respiratory inflammation
Erdosteine compound and preparation method thereof, Application No.: 2015102153218, filing date: on April 30th, 2015)
Divisional application.
Technical field
The present invention relates to field of medicaments, be specifically related to the side of a kind of erdosteine compound preparing treatment respiratory inflammation
Method.
Background technology
Expectorant is the product of respiratory inflammation, can stimulate respiratory mucosa, causes cough and asthma, and can increase the weight of to infect.Anxious
When chronic bronchitis or chronic lung diseases respiratory failure, as patient's thick sputum spends height or forms expectorant bolt, can block and exhale
Inhale road and cause suffocating.Therefore, using viscous expectorant regulator, make patient's phlegm dissolving, thinning, viscosity reduces, and accelerates respiratory tract and glues
Film ciliary movement, improves transport function, and tool is of great significance.
At present this is smooth etc. for viscous expectorant regulator such as the bromhexine, mesna of listing, carboxylic first, is respectively provided with gluing in various degree
Expectorant regulation effect, but its pharmacology or there are some defects clinically.Sulfydryl free in molecular structure can adsorb gastrointestinal tract and glue egg
In vain, oral after can produce gastrointestinal tract local damage, side effect is relatively big, can weaken penicillin, cephalosporins, erythromycin, four
The antibacterial activity of ring element etc., unsuitable drug combination, the most high to the improvement effect of some respiration parameter such as expectorant viscosity etc..
Erdosteine is a kind of prodrug, with the sulfydryl of closing of non-free in its structure, to local mucin without
Active function, produces three metabolites containing free sulfhydryl groups through metabolism after being administered orally and plays pharmacological action, thus after being administered orally
Without obvious gastrointestinal side effect.It is demonstrated experimentally that erdosteine cylinder metabolism-ure can make mucinous two sulfur in bronchial secretion
Bond fission, and change secretions composition and rheological property, reduce sputum viscosity, improve downtrod respiratory function, this product energy
Removing free radical, effectively protection a1-antitrypsin is from cigarette, the oxidation deactivation of dirt induction, prevents elastance of lung albumen
And the damage of neutrophilic granulocyte.This product can also substantially increase IgA/ albumin, lactoferrin/albuminous ratio, weakens local
Inflammation, strengthens and improves the antibiotic osmosis to bronchial mucosa, the beneficially treatment of the various inflammation of respiratory tract.Abroad face
Bed clinical studies show: comparing with like product such as acetylcysteine, this smooth, ambroxol of carboxylic first etc., acute and chronic is propped up by this product
Tracheitis has good curative effect, and to the improvement of some respiratory function parameter more effectively, heavy dose of administration does not occurs medicine to store
Long-pending, this product characteristics of pharmacokinetics is changed by Liver and kidney function moderate obstacle without obvious.
The water solublity of erdosteine is poor, and the effective bioavailability in human body is low, and medicine infiltration rate in vivo
Usually being determined by the speed dissolved, the medicine in solid preparation is before being absorbed, it is necessary to then turn to through disintegrate and dissolving
The process of solution, if medicine is difficult to discharge from preparation or the dissolution velocity of medicine is extremely slow, then said preparation Chinese medicine
The infiltration rate of thing or degree are possible to existing problems.
The approach of existing solution erdosteine poorly water-soluble mainly includes changing dosage form, as CN101606931B is made
Become dispersible tablet, although above-mentioned preparation improves the water solublity of medicine to a certain extent, but there is also many defects.Therefore,
It is necessary to provide the erdosteine compound of a kind of performance improvement.
The present inventor starts with from the research of erdosteine solid chemical material existence, prepares through substantial amounts of test
A kind of erdosteine compound crystal, surprisingly finds through overtesting, this compound crystal significantly improves its dissolubility, has
Higher stability.
Summary of the invention
A kind of method that the invention provides erdosteine compound preparing treatment respiratory inflammation.
In order to realize the purpose of the present invention, the technical scheme of employing is:
A kind of method of erdosteine compound preparing treatment respiratory inflammation, it is characterised in that described erdosteine
The X-ray powder diagram that compound use Cu-K alpha ray measurement obtains is as shown in Figure 1;
Concrete preparation method is:
(1) erdosteine crude product is ground, crosses 100-200 mesh sieve, be then added to the mixing of isopropanol and propyl formate
In solution, stir 15-25 minute;
(2) add the mixed solution of oxolane, water under stirring, be warming up to 20-45 DEG C simultaneously;
(3) after solution adds, stand 2-3 hour, drip sodium chloride saturated solution under conditions of stirring, at the uniform velocity drip in 0.5h
Finish;
(4) lowering the temperature after being added dropwise to complete, continue stirring 0.5-2h, stand 2-4h and separate out crystal, filter, vacuum drying obtains E Duosi
Smooth crystal.
Wherein, in step (1), the volume of isopropanol and propyl formate mixed solution is 3-5 times of erdosteine weight,
The volume ratio of isopropanol and propyl formate is 1:4.5;Step (1) described mixing speed is 80-120 rev/min, step (2) institute
Stating mixing speed and be 430-560 rev/min, step (3) described mixing speed is 80-120 rev/min, step (4) described stirring
Speed is 10-15 rev/min;Oxolane described in step (2), the 8-12 that mixed liquor volume is erdosteine weight of water
Times, oxolane: water volume ratio is 1:3.5;Described in step (3), the temperature of sodium chloride saturated solution is-15 DEG C-5 DEG C;Step
(3) volume of sodium chloride saturated solution described in is 5-8 times of erdosteine weight;Step is cooled to-15 DEG C-5 DEG C in (4).
Below the summary of the invention of the present invention is further described:
Erdosteine compound prepared by the present invention, uses the X-ray powder diffraction that Cu-K alpha ray is measured as shown in Figure 1;
This erdosteine crystalline compounds is to be prepared via a method which to form:
(1) erdosteine crude product is ground, crosses 100-200 mesh sieve, be then added to the mixing of isopropanol and propyl formate
In solution, stir 15-25 minute;
(2) add the mixed solution of oxolane, water under stirring, be warming up to 20-45 DEG C simultaneously;
(3) after solution adds, stand 2-3 hour, drip sodium chloride saturated solution under conditions of stirring, at the uniform velocity drip in 0.5h
Finish;
(4) lowering the temperature after being added dropwise to complete, continue stirring 0.5-2h, stand 2-4h and separate out crystal, filter, vacuum drying obtains E Duosi
Smooth crystal.
By the volume of mixed solvent isopropanol and propyl formate, preferably isopropanol and propyl formate mixed solution it is
The volume ratio of 3-5 times of erdosteine weight, isopropanol and propyl formate is 1:4.5.At the mixed solution of this ratio by strategic point
After the smooth solid of many departments dissolves, then under the mixing speed of 430-560 rev/min, add oxolane, the mixed solution of water,
It is warming up to 20-45 DEG C simultaneously.The temperature finally using sodium chloride saturated solution, preferably sodium chloride saturated solution is-15 DEG C-5 DEG C,
Amassing the 5-8 times of recrystallization for erdosteine weight, cooling separates out crystal, and filtering vacuum is dried to obtain erdosteine crystal chemical combination
Thing.For the water solublity of this erdosteine crystalline compounds erdosteine solid compared to existing technology, its solubility property is
Improve, and stability and other performances also keep good.
Further the summary of the invention of the present invention is elaborated:
Prepared by the present invention, erdosteine compound, used X-ray powder diffraction such as accompanying drawing 1 institute that Cu-K alpha ray is measured
Show;
This erdosteine crystalline compounds is to be prepared via a method which to form:
(1) erdosteine crude product is ground, crosses 200 mesh sieves, be then added to that volume is erdosteine weight 5 times different
In the mixed solution of propanol and propyl formate, the volume ratio of isopropanol and propyl formate is 1:4.5, and 120 revs/min are stirred 25 points
Clock;
(2) 560 revs/min of lower oxolanes adding 12 times that volume is erdosteine weight of stirring: water volume ratio is 1:3.5
Mixed solution, be warming up to 45 DEG C simultaneously;
(3) after solution adds, stand 3 hours, under conditions of 120 revs/min of stirrings, drip the sodium chloride saturated solution of 5 DEG C, chlorine
Change sodium saturated solution volume is erdosteine weight 8 times, at the uniform velocity drip complete in 0.5h;
(4) it is cooled to 5 DEG C after being added dropwise to complete, under the stir speed (S.S.) of 15 revs/min, continues stirring 2h, stand 4h and separate out crystal,
Filtering, vacuum drying obtains erdosteine crystal.
The erdosteine crystal of gained can be prepared as different dosage forms.Can be oral formulations or liquid preparation, institute
The oral formulations stated is conventional tablet, capsule, granule etc., and described liquid preparation is oral liquid, freeze-dried powder, injection
Deng.Relative proportions those skilled in the art between adjuvant and each component used by various dosage forms can be according to the actual requirements
Go to adjust.
The stable chemical nature of erdosteine crystal prepared by the present invention, water solublity improves a lot, and has higher
Stability, the convenience brought to the preparation of various preparations.
Accompanying drawing explanation
Fig. 1 is the X-ray powder diagram of the erdosteine compound of embodiment 1 preparation.
Detailed description of the invention
The detailed description of the invention of the present invention is only limitted to be explained further and the present invention is described, not to present disclosure structure
Become to limit.
Embodiment 1: the preparation of erdosteine compound
(1) erdosteine crude product is ground, crosses 100 mesh sieves, be then added to that volume is erdosteine weight 3 times different
In the mixed solution of propanol and propyl formate, the volume ratio of isopropanol and propyl formate is 1:4.5, and 80 revs/min are stirred 15 points
Clock;
(2) 430 revs/min of lower oxolanes adding 8 times that volume is erdosteine weight of stirring: water volume ratio is 1:3.5
Mixed solution, be warming up to 20 DEG C simultaneously;
(3) after solution adds, stand 2 hours, under conditions of 80 revs/min of stirrings, drip the sodium chloride saturated solution of-15 DEG C, chlorine
Change sodium saturated solution volume is erdosteine weight 5 times, at the uniform velocity drip complete in 0.5h;
(4) it is cooled to-15 DEG C DEG C after being added dropwise to complete, under the stir speed (S.S.) of 10 revs/min, continues stirring 0.5h, stand 2h and separate out
Crystal, filters, and vacuum drying obtains erdosteine crystal.
This compound crystal detects through high performance liquid chromatography, and purity is 99.99%, yield 98.3%;Cu-K alpha ray is used to survey
The X-ray powder diagram measured is as shown in Figure 1.
Embodiment 2: the preparation of erdosteine compound
(1) erdosteine crude product is ground, crosses 150 mesh sieves, be then added to that volume is erdosteine weight 4 times different
In the mixed solution of propanol and propyl formate, the volume ratio of isopropanol and propyl formate is 1:4.5, and 100 revs/min are stirred 20 points
Clock;
(2) 495 revs/min of lower oxolanes adding 10 times that volume is erdosteine weight of stirring: water volume ratio is 1:3.5
Mixed solution, be warming up to 33 DEG C simultaneously;
(3) after solution adds, stand 2.5 hours, under conditions of 100 revs/min of stirrings, drip the sodium chloride saturated solution of-5 DEG C,
The volume of sodium chloride saturated solution is 6.5 times of erdosteine weight, at the uniform velocity drips complete in 0.5h;
(4) it is cooled to-5 DEG C DEG C after being added dropwise to complete, under the stir speed (S.S.) of 12.5 revs/min, continues stirring 1.3h, stand 3h analysis
Going out crystal, filter, vacuum drying obtains erdosteine crystal.
This compound crystal detects through high performance liquid chromatography, and purity is 99.99%, yield 98.3%;Cu-K alpha ray is used to survey
The X-ray powder diagram measured is as shown in Figure 1.
Embodiment 3: the preparation of erdosteine compound
(1) erdosteine crude product is ground, crosses 200 mesh sieves, be then added to that volume is erdosteine weight 5 times different
In the mixed solution of propanol and propyl formate, the volume ratio of isopropanol and propyl formate is 1:4.5, and 120 revs/min are stirred 25 points
Clock;
(2) 560 revs/min of lower oxolanes adding 12 times that volume is erdosteine weight of stirring: water volume ratio is 1:3.5
Mixed solution, be warming up to 45 DEG C simultaneously;
(3) after solution adds, stand 3 hours, under conditions of 120 revs/min of stirrings, drip the sodium chloride saturated solution of 5 DEG C, chlorine
Change sodium saturated solution volume is erdosteine weight 8 times, at the uniform velocity drip complete in 0.5h;
(4) it is cooled to 5 DEG C after being added dropwise to complete, under the stir speed (S.S.) of 15 revs/min, continues stirring 2h, stand 4h and separate out crystal,
Filtering, vacuum drying obtains erdosteine crystal.
This compound crystal detects through high performance liquid chromatography, and purity is 99.99%, yield 98.3%;Cu-K alpha ray is used to survey
The X-ray powder diagram measured is as shown in Figure 1.
Experimental example 1: the stability test of product prepared by the present invention
1, accelerated test
Three batches of products of Example 1, in temperature be 40 ± 2 DEG C, relative humidity be to place 6 months under conditions of 75 ± 5%, point
Do not sample once 0,1,2,3,6 the end of month, be measured by high spot reviews project, be shown in Table 1.
Table 1, accelerated test result (temperature 40 ± 2 DEG C, relative humidity 75% ± 5%)
Result shows, this product temperature be 40 ± 2 DEG C, relative humidity be to place 6 months under the conditions of 75 ± 5%, have related substance to contain
Measuring low, each index has no significant change, and this product quality stability is good.
2, long term test
Example 1 product, in temperature be 25 DEG C, relative humidity be 60% ± 10% to place, respectively at 0,3,6,9,12,18,24
Individual the end of month sampling and measuring.Measure character, content according to pertinent regulations under " quality standard " item and have related substance, record result (knot
Fruit see table 2), and compare with batch 0 month record.
Table 2, long-term test results (temperature 25 ± 2 DEG C, relative humidity 60% ± 5%)
Being shown by long-term test results: erdosteine compound prepared by the present invention is 25 ± 2 DEG C in temperature, relative humidity is
Placing under conditions of 60% ± 5% 24 months and stablize, indices is without significant change.
Other embodiments also pass through as above to be accelerated and stability test, and result is similar to Example 1.
Experimental example 2:
The water solublity experiment of erdosteine compound prepared by embodiment of the present invention 1-3, compared with commercially available erdosteine.Concrete real
Proved recipe method is: add appropriate distilled water in the low capacity bottle with constant temperature jacket, adds erdosteine to not at 25 DEG C
Till re-dissolved, starting magnetic stirrer, continuously stirred under constant temperature, in experimentation, system is in the shape of two-phase coexistent all the time
State, the dissolubility at a temperature of the concentration of erdosteine is this in the liquid phase of system after 70 minutes.It is sampled after 2 hours point
Analysis, takes the close meansigma methods of adjacent two times result as measured value of experiment, before sampling, in order to make solid-liquid be sufficiently separated, stops stirring
After mixing, the most molten erdosteine is deposited to the bottom of low capacity bottle, extracts a small amount of upper clear supernate with syringe, with 0.45 micron
Filter filters, and takes sample, measured the content of erdosteine by HPLC, be specifically shown in Table 3 from filtrate.
The water solublity of erdosteine compound prepared by the present invention under table 3 room temperature
In analysis, table understands, and compared with prior art, the water solublity of erdosteine compound prepared by the present invention is greatly improved.
Claims (1)
1. the method for the erdosteine compound preparing treatment respiratory inflammation, it is characterised in that: described erdosteine
The X-ray powder diagram that compound use Cu-K alpha ray measurement obtains is as shown in Figure 1;Concrete preparation method is as follows:
(1) erdosteine crude product is ground, crosses 200 mesh sieves, be then added to that volume is erdosteine weight 5 times different
In the mixed solution of propanol and propyl formate, the volume ratio of isopropanol and propyl formate is 1:4.5, and 120 revs/min are stirred 25 points
Clock;
(2) 560 revs/min of lower oxolanes adding 12 times that volume is erdosteine weight of stirring: water volume ratio is 1:3.5
Mixed solution, be warming up to 45 DEG C simultaneously;
(3) after solution adds, stand 3 hours, under conditions of 120 revs/min of stirrings, drip the sodium chloride saturated solution of 5 DEG C, chlorine
Change sodium saturated solution volume is erdosteine weight 8 times, at the uniform velocity drip complete in 0.5h;
(4) it is cooled to 5 DEG C after being added dropwise to complete, under the stir speed (S.S.) of 15 revs/min, continues stirring 2h, stand 4h and separate out crystal,
Filtering, vacuum drying obtains erdosteine crystal.
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CN201610595356.3A CN106146456A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
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CN201510215321.8A CN104788421B (en) | 2015-04-30 | 2015-04-30 | A kind of erdosteine compound treating respiratory inflammation and preparation method thereof |
CN201610595356.3A CN106146456A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
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CN201610595340.2A Withdrawn CN106220604A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
CN201610595361.4A Withdrawn CN106220605A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
CN201510215321.8A Expired - Fee Related CN104788421B (en) | 2015-04-30 | 2015-04-30 | A kind of erdosteine compound treating respiratory inflammation and preparation method thereof |
CN201610595315.4A Withdrawn CN106187992A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
CN201610595356.3A Withdrawn CN106146456A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
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CN201610595361.4A Withdrawn CN106220605A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
CN201510215321.8A Expired - Fee Related CN104788421B (en) | 2015-04-30 | 2015-04-30 | A kind of erdosteine compound treating respiratory inflammation and preparation method thereof |
CN201610595315.4A Withdrawn CN106187992A (en) | 2015-04-30 | 2015-04-30 | A kind of method of the erdosteine compound preparing treatment respiratory inflammation |
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IT202000016816A1 (en) | 2020-07-10 | 2022-01-10 | Edmond Pharma Srl | COMPOSITIONS INCLUDING ANTIOXIDANT COMPOUNDS AS AID IN THE TREATMENT OF VIRAL INFECTIONS |
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CN104983693A (en) * | 2015-08-13 | 2015-10-21 | 青岛蓝盛洋医药生物科技有限责任公司 | Medicine erdosteine composition granules for treating respiratory tract infection |
CN105078901A (en) * | 2015-09-10 | 2015-11-25 | 青岛蓝盛洋医药生物科技有限责任公司 | Erdosteine pharmaceutical composition dry suspension for treating diseases of respiratory system |
CN106187991B (en) * | 2016-07-19 | 2019-04-30 | 山东罗欣药业集团股份有限公司 | A kind of compound and preparation method thereof for treating respiratory disease |
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CN1699337A (en) * | 2004-05-20 | 2005-11-23 | 江苏豪森药业股份有限公司 | Ambroxol cysteine analogs and their preparation process and use thereof |
US20100249435A1 (en) * | 2007-11-16 | 2010-09-30 | Edmond Pharma S.R.L | Polymorphs of enantiopure erdosteine |
CN101941963A (en) * | 2010-04-22 | 2011-01-12 | 浙江康乐药业股份有限公司 | Synthesis method of erdosteine |
-
2015
- 2015-04-30 CN CN201610595340.2A patent/CN106220604A/en not_active Withdrawn
- 2015-04-30 CN CN201610595361.4A patent/CN106220605A/en not_active Withdrawn
- 2015-04-30 CN CN201510215321.8A patent/CN104788421B/en not_active Expired - Fee Related
- 2015-04-30 CN CN201610595315.4A patent/CN106187992A/en not_active Withdrawn
- 2015-04-30 CN CN201610595356.3A patent/CN106146456A/en not_active Withdrawn
Patent Citations (3)
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CN1699337A (en) * | 2004-05-20 | 2005-11-23 | 江苏豪森药业股份有限公司 | Ambroxol cysteine analogs and their preparation process and use thereof |
US20100249435A1 (en) * | 2007-11-16 | 2010-09-30 | Edmond Pharma S.R.L | Polymorphs of enantiopure erdosteine |
CN101941963A (en) * | 2010-04-22 | 2011-01-12 | 浙江康乐药业股份有限公司 | Synthesis method of erdosteine |
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IT202000016816A1 (en) | 2020-07-10 | 2022-01-10 | Edmond Pharma Srl | COMPOSITIONS INCLUDING ANTIOXIDANT COMPOUNDS AS AID IN THE TREATMENT OF VIRAL INFECTIONS |
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CN104788421B (en) | 2016-08-24 |
CN106187992A (en) | 2016-12-07 |
CN106220604A (en) | 2016-12-14 |
CN104788421A (en) | 2015-07-22 |
CN106220605A (en) | 2016-12-14 |
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Inventor after: Sun Zongwen Inventor after: Wang Yumei Inventor before: Wang Yumei |
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Application publication date: 20161123 |
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