CN102276526A - Synthesis method of 2-amino pyridine compounds - Google Patents
Synthesis method of 2-amino pyridine compounds Download PDFInfo
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- CN102276526A CN102276526A CN2011102247880A CN201110224788A CN102276526A CN 102276526 A CN102276526 A CN 102276526A CN 2011102247880 A CN2011102247880 A CN 2011102247880A CN 201110224788 A CN201110224788 A CN 201110224788A CN 102276526 A CN102276526 A CN 102276526A
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- 0 *C=C(*)*=C(*)C#N Chemical compound *C=C(*)*=C(*)C#N 0.000 description 2
- DGHRTJKLPOARKI-UHFFFAOYSA-N CCOC(c1ccc(-c(cc2)ccc2OC)nc1N)=O Chemical compound CCOC(c1ccc(-c(cc2)ccc2OC)nc1N)=O DGHRTJKLPOARKI-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention provides a synthesis method of 2-amino pyridine compounds, belonging to the technical field of organic synthesis. The existing synthesis method has the disadvantages of difficult acquisition of raw materials, high catalyst cost, complicated reaction steps, harsh reaction conditions, serious environmental pollution, low yield, few substituent groups, specific substituent positions and atomic diseconomy. The synthesis method provided by the invention is characterized by comprising the following steps of: adding a 2,4-pentadiene nitrile compound and an amine compound in a molar ratio of 1.0:(1.0-2.5) to a solvent to form a reaction mixture; adding a base the amount of which is 0-250mol% of a substrate while stirring the reaction mixture; and then stirring at the temperature from room temperature to 150 DEG C for 3-24 hours to obtain a product namely the 2-amino pyridine compound. The synthesis method provided by the invention lowers the catalyst cost, relieves the pollution, simplifies the synthesis processes, has the advantages of mild reaction conditions, easy acquisition of raw materials, light side reaction, many substituent groups and wide application range, and has the yield of 58-81% depending on different reactions.
Description
Technical field
The present invention relates to a kind of 2-aminopyridines synthetic method, with 2,4-pentadiene nitrile compounds becomes ring tactful one-step synthesis 2-aminopyridines with ammoniac compounds through [5C+1N] as five carbon synthons, belongs to technical field of organic synthesis.
Background technology
The 2-aminopyridines is important organic and medicine intermediate, can be used in synthetic multiple fine chemistry industry and pharmaceutical prod.For example, the amino 6-picoline of 2-can be used to make dyestuff and photographic developer; 2-amino-4-quinolyl base-1,4-dihydropyridine compounds are a kind of medicines for the treatment of cardiovascular disorder; 2-amino-5-bromopyridine is used for synthetic phospholipid acyl inositol PI3 kinase inhibitor, aminopyrazole derivatives selective dopamine D 3 receptor stimulant, and synthetic imidazo [1,2-a] medicine such as pyridine compounds VEGFR-2 inhibitor, can also be used for treating multiple diseases such as autoimmune disease, inflammatory disease, cardiovascular and cerebrovascular diseases, nerve degenerative diseases, allergy; 2-aminopyridine-3-methyl alcohol is the intermediate of synthetic thymoleptic mirtazapine, in addition, with 2-aminopyridine-3-methyl alcohol and derivative thereof is that nitrogen protoxide (NO) synthetase inhibitors of effective constituent can suppress the synthetic too much immunologic injury of mediation of NO, at treatment septic shock, chronic rheumatoid arthritis, disease aspects such as diabetes play a significant role.
The method of existing Synthetic 2-aminopyridines mainly contains following two classes:
One, modifies pyridine ring
Following four kinds of schemes are specifically arranged:
1) pyridine and sodium amide carry out aminating reaction synthetic (US4386209);
2) by haloperidid palladium carbon (Org.Lett.2001,3,2729-2732.) or mantoquita (Tetrahedron Lett.2001,42,3251-3254.) synthetic under the katalysis of Denging by ammonolysis reaction;
3) pyridine is through hydrogen peroxide oxidation, again by the nitrated one-tenth nitro of nitrosonitric acid pyridine oxide, carry out again reduction reaction obtain aminopyridine (Synth.Commun.2002,32,1681-1683.);
4) be raw material with the cyanopyridine through catalytic hydrolysis, Hofmann degradation obtain aminopyridine (applied chemistry, 2004,21,530-531.).
Yet the such scheme raw material is not easy to obtain, catalyzer cost height, reactions steps are numerous and diverse, severe reaction conditions, contaminate environment is serious, yield is not high.
Two, directly make up pyridine compounds and their and the derivative thereof that has amino replacement
For example, by the 2-aminopyridines of the synthetic one type of replacement of the dithio keteal that contains cyano group (J.Org.Chem.2008,73,2442-2445).
This method has reduced the catalyzer cost, has alleviated pollution, and the reaction conditions gentleness has improved yield, still, have still that raw material is not easy to obtain, the numerous and diverse problem of reactions steps, and substituting group is few, the position of substitution is specific, the atom diseconomy.
Summary of the invention
The objective of the invention is to, in the preparation of 2-aminopyridines, reducing catalyzer cost, pollution abatement, in the time of reaction conditions gentleness, raising yield, make and select for use the raw material that is easy to get, simplification to synthesize link, alleviate side reaction, we have invented a kind of 2-aminopyridines synthetic method.
The present invention is characterized in that, in solvent, add 2 of 1.0: 1.0～2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, the alkali that in the process of stirred reaction mixture, adds 0～250% mole of multiple of substrate, stirred 3～24 hours under ℃ temperature of room temperature～150 afterwards, obtain product 2-aminopyridines, reaction formula is as follows:
Positively effect of the present invention is, in the present invention's synthetic method, adopt 2,4-pentadiene nitrile compounds is as five carbon synthons, make up pyridine ring with ammoniac compounds through [5C+1N] step, synthesize and comprise that part replaces or be substituted in full the 2-aminopyridines of interior various replacements.This method adopts alkali as catalyzer, reduces catalyzer cost, pollution abatement; The reaction conditions gentleness is finished synthetic in lesser temps, short period; Improve yield, productive rate is looked differential responses between 58～81%; Raw material is easy to get, and reactant is 2,4-pentadiene nitrile compounds and ammoniac compounds; Synthetic link is simplified, and promptly finishes synthetic through a step; Light side-reaction, substituting group is many, the scope of application is wide, and its general formula of synthetic product 2-aminopyridines is:
Wherein, R
1Be cyano group, ester group; R
2For hydrogen, phenyl and on phenyl ring, be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro; R
3Be hydrogen, alkyl; R
4Be connected with fluorine, chlorine, bromine, iodine, amino, hydroxyl, alkoxyl group, nitro for phenyl and on phenyl ring.
Embodiment
In solvent, add 2 of 1.0: 1.0～2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, the alkali that in the process of stirred reaction mixture, adds 0～250% mole of multiple of substrate, under ℃ temperature of room temperature～150, stirred 3～24 hours, obtain product 2-aminopyridines, reaction formula is as follows:
Described solvent is organic solvent or organic solvent and water blended mixed solvent.Organic solvent comprises the alcohols of C1-C6 alkyl, is one of methyl alcohol, ethanol, propyl carbinol, ethylene glycol; Amides is one of dimethyl formamide, N,N-DIMETHYLACETAMIDE; And methyl-sulphoxide, methylene dichloride.In the alcohols of C1-C6 alkyl, amides, methyl-sulphoxide, methylene dichloride, select one.
Described 2,4-pentadiene nitrile compounds is one of following:
2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile,
2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile.
Described ammoniac compounds is azanol or oxammonium hydrochloride.
Described alkali is mineral alkali or organic bases.Wherein mineral alkali is one of sodium hydroxide, potassium hydroxide, salt of wormwood; Organic bases is one of triethylamine, 1.8-diazabicylo (5.4.0) hendecene-7, triethylene diamine.
Embodiment 1:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-6-(4-p-methoxy-phenyl) pyridine 0.280 gram, productive rate 62.2%.Reaction formula is as follows:
The data characterization of product:
Mp：191～192℃；
1H?NMR(400MHz，CDCl
3，25℃)δ＝3.87(3H)，5.19(2H)，6.98(2H)，.10(1H)，7.70，(1H)，7.94(2H)；
13C?NMR(125MHz，CDCl
3，25℃)δ＝55.4，88.4，109.5，114.2，117.2，128.8，130.3，141.7，159.0，160.0，161.5。
Illustrate that product is 2-amino-3-cyano group-6-(4-p-methoxy-phenyl) pyridine.
Embodiment 2:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-6-(4-chloro-phenyl-) pyridine 0.290 gram, productive rate 63.1%.Reaction formula is as follows:
Embodiment 3:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Get white solid product 2-amino-3-cyano group-4-(3-p-methoxy-phenyl) pyridine 0.301 gram, productive rate 66.8%.Reaction formula is as follows:
Embodiment 4:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-4-(2-p-methoxy-phenyl) pyridine 0.295 gram, productive rate 65.6%.Reaction formula is as follows:
Embodiment 5:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-acetoxyl group-6-(4-p-methoxy-phenyl) pyridine 0.355 gram, productive rate 65.3%.Reaction formula is as follows:
Embodiment 6:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-4-(4-chloro-phenyl-)-6-phenylpyridine 0.467 gram, productive rate 76.3%.Reaction formula is as follows:
Embodiment 7:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-4-phenyl-6-phenylpyridine 0.405 gram, productive rate 74.7%.Reaction formula is as follows:
Embodiment 8:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; Under stirring at room, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.487 gram, productive rate 80.9%.Reaction formula is as follows:
Embodiment 9:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.5 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.488 gram, productive rate 81.0%.Reaction formula is as follows:
Embodiment 10:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-4-phenyl-5-methyl-6-phenylpyridine 0.418 gram, productive rate 73.4%.Reaction formula is as follows:
Embodiment 11:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile, 0.13 milliliter of 50% aqueous hydroxylamine, 10 milliliters of dimethyl formamides; At room temperature stir, then reaction system is stirred 3.5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get white solid product 2-amino-3-cyano group-6-(4-p-methoxy-phenyl) pyridine 0.295 gram, productive rate 65.5%.Reaction formula is as follows:
Embodiment 12:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylene diamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.482 gram, productive rate 80.1%.Reaction formula is as follows:
Embodiment 13:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmoles 1 simultaneously, 8-diazabicylo (5.4.0) hendecene-7 stirs 5h with reaction system then under 80 ℃ of temperature, and reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.474 gram, productive rate 78.7%.Reaction formula is as follows:
Embodiment 14:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of methyl-sulphoxides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, then reaction system is stirred 5h under 80 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.468 gram, productive rate 77.7%.Reaction formula is as follows:
Embodiment: 15:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of ethanol; At room temperature stir, add 4.4 mmole triethylamines simultaneously, reflux 12h stops heating, and reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.453 gram, productive rate 75.2%.Reaction formula is as follows:
Embodiment 16:
In 50 milliliters of round-bottomed flasks, add 2 mmole 2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile, 2.1 mmole oxammonium hydrochlorides, 10 milliliters of dimethyl formamides; At room temperature stir, add 4.4 mmole triethylamines simultaneously, and then heat 3h under 120 ℃ of temperature, reaction finishes; Through column chromatography, get faint yellow solid product 2-amino-3-cyano group-4-(4-p-methoxy-phenyl)-6-phenylpyridine 0.479 gram, productive rate 79.6%.Reaction formula is as follows:
Claims (5)
1. 2-aminopyridines synthetic method, it is characterized in that, in solvent, add 2 of 1.0: 1.0～2.5 molar ratios, 4-pentadiene nitrile compounds and ammoniac compounds, form reaction mixture, in the process of stirred reaction mixture, add the alkali of 0～250% mole of multiple of substrate, under ℃ temperature of room temperature～150, stirred 3～24 hours afterwards, obtain product 2-aminopyridines, reaction formula is as follows:
2. synthetic method according to claim 1 is characterized in that, described solvent is organic solvent or organic solvent and water blended mixed solvent; Organic solvent comprises the alcohols of C1-C6 alkyl, is one of methyl alcohol, ethanol, propyl carbinol, ethylene glycol; Amides is one of dimethyl formamide, N,N-DIMETHYLACETAMIDE; And methyl-sulphoxide, methylene dichloride; In the alcohols of C1-C6 alkyl, amides, methyl-sulphoxide, methylene dichloride, select one.
3. synthetic method according to claim 1 is characterized in that, and is described 2, and 4-pentadiene nitrile compounds is one of following:
2-cyano group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-5-(4-chloro-phenyl-)-2,4-pentadiene nitrile,
2-cyano group-3-(3-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(2-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-acetoxyl group-5-(4-p-methoxy-phenyl)-2,4-pentadiene nitrile,
2-cyano group-3-(4-chloro-phenyl-)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-(4-p-methoxy-phenyl)-5-phenyl-2,4-pentadiene nitrile,
2-cyano group-3-phenyl-4-methyl-5-phenyl-2,4-pentadiene nitrile.
4. synthetic method according to claim 1 is characterized in that, described ammoniac compounds is azanol or oxammonium hydrochloride.
5. synthetic method according to claim 1 is characterized in that, described alkali is mineral alkali or organic bases; Wherein mineral alkali is one of sodium hydroxide, potassium hydroxide, salt of wormwood; Organic bases is one of triethylamine, 1.8-diazabicylo (5.4.0) hendecene-7, triethylene diamine.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013144191A1 (en) * | 2012-03-29 | 2013-10-03 | Bayer Intellectual Property Gmbh | Substituted 2-amino-3-cyanopyridines as inhibitors of sodium-calcium exchange and use thereof for cardiovascular diseases |
| CN104447528A (en) * | 2014-11-15 | 2015-03-25 | 浙江大学 | Preparation method of diethylpyridine-2,3-dicarboxylate |
| CN108017577A (en) * | 2018-01-06 | 2018-05-11 | 怀化学院 | The process for catalytic synthesis of 2- pyridones |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4386209A (en) * | 1982-04-08 | 1983-05-31 | Reilly Tar & Chemical Corporation | Chichibabin reaction |
-
2011
- 2011-08-08 CN CN 201110224788 patent/CN102276526B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4386209A (en) * | 1982-04-08 | 1983-05-31 | Reilly Tar & Chemical Corporation | Chichibabin reaction |
Non-Patent Citations (3)
| Title |
|---|
| JIANGLEI HU ET AL.: "Temperature-Controlled Synthesis of Substituted Pyridine Derivatives via the [5C + 1N] Annulation of 1,1-Bisalkylthio-1,4-pentanedienes and Ammonium Acetate", 《J.ORG.CHEM》 * |
| 戴立言等: "Synthesis of 2-pyridinamines and heir alkyl derivatives from 2-cyanopyridines", 《化工学报》 * |
| 毕锡和等: "[5C+1N]成环反应：一种合成多取代2，3-二氢-4-吡啶酮的新方法", 《有机化学》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013144191A1 (en) * | 2012-03-29 | 2013-10-03 | Bayer Intellectual Property Gmbh | Substituted 2-amino-3-cyanopyridines as inhibitors of sodium-calcium exchange and use thereof for cardiovascular diseases |
| CN104447528A (en) * | 2014-11-15 | 2015-03-25 | 浙江大学 | Preparation method of diethylpyridine-2,3-dicarboxylate |
| CN104447528B (en) * | 2014-11-15 | 2016-08-24 | 浙江大学 | The preparation method of pyridine-2,3-diethyl dicarboxylate |
| CN108017577A (en) * | 2018-01-06 | 2018-05-11 | 怀化学院 | The process for catalytic synthesis of 2- pyridones |
| CN108017577B (en) * | 2018-01-06 | 2019-03-01 | 怀化学院 | The process for catalytic synthesis of 2- pyridone |
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Inventor after: Dong Dewen Inventor after: Xin Xiaoqing Inventor after: Liang Yongjiu Inventor after: Zhang Rui Inventor after: Xiang Dexuan Inventor after: Liu Xu Inventor after: Wang Zikun Inventor after: Yang Jiming Inventor before: Dong Dewen Inventor before: Xin Xiaoqing Inventor before: Liang Yongjiu Inventor before: Zhang Rui Inventor before: Xiang Dexuan Inventor before: Liu Xu Inventor before: Wang Zikun Inventor before: Yang Jiming |
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