CN116621763A - Preparation method of indole derivative - Google Patents
Preparation method of indole derivative Download PDFInfo
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- CN116621763A CN116621763A CN202310642202.5A CN202310642202A CN116621763A CN 116621763 A CN116621763 A CN 116621763A CN 202310642202 A CN202310642202 A CN 202310642202A CN 116621763 A CN116621763 A CN 116621763A
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- indole derivatives
- derivatives according
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- organic solvent
- indole
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- 150000002475 indoles Chemical class 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 238000003756 stirring Methods 0.000 claims abstract description 14
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 33
- -1 2-ethynyl aniline compound Chemical class 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 150000002148 esters Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- ALQPJHSFIXARGX-UHFFFAOYSA-N 2-ethynylaniline Chemical class NC1=CC=CC=C1C#C ALQPJHSFIXARGX-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 6
- 125000001041 indolyl group Chemical group 0.000 abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 230000035484 reaction time Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 3
- YJPIGAIKUZMOQA-UHFFFAOYSA-N Melatonin Natural products COC1=CC=C2N(C(C)=O)C=C(CCN)C2=C1 YJPIGAIKUZMOQA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 description 2
- 229960003987 melatonin Drugs 0.000 description 2
- 210000005036 nerve Anatomy 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- AHEUFXCMFDEOOW-UHFFFAOYSA-N 2-(1h-indol-3-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1.C1=CC=C2C(CC(=O)O)=CNC2=C1 AHEUFXCMFDEOOW-UHFFFAOYSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002726 vincamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
Abstract
The invention discloses a preparation method of indole derivatives, and belongs to the field of organic synthesis. Solves the problems of the existing indole skeleton structure that a metal reagent is needed to be used, the electrocatalytic reaction is performed, the reaction time is long and the temperature is high. The method comprises the following steps: mixing the raw materials to obtain a mixture, stirring the mixture under the air atmosphere and at room temperature for reaction, then distilling under reduced pressure to remove the solvent, and separating and purifying by silica gel column chromatography to obtain the indole derivative. The invention is used for preparing indole derivatives.
Description
Technical Field
The invention belongs to the field of organic synthesis.
Background
Indole derivatives are widely distributed in nature, many natural compounds have indole rings in their structures, and some indole derivatives are closely related to life activities. Indole skeleton structure is used as natural alkaloid, and widely exists in bioactive molecular structures such as medicines, pesticides and the like, for example, vincamine (Vincam) has the effects of regulating brain circulation, maintaining nerve dynamic balance, protecting nerves, resisting oxidation and the like to a certain extent; 3-indoleacetic acid (Indole-3-acetic acid) not only can promote growth in plants, but also has the effects of inhibiting growth and organ formation; melatonin (Melatonine) is a natural hormone indispensable to the human body and controls and influences the secretion of other different hormones. The indole derivatives can be efficiently, practically and flexibly synthesized into indole structures due to the unique application value, and the indole derivatives continuously arouse the interests of chemists in different research fields.
In the field of synthetic chemistry recently, cyclization of 2-ethynyl aniline compounds is one of a plurality of effective strategies for synthesizing indole frameworks, and the 2-ethynyl aniline compounds have important application significance in synthesizing indole frameworks due to the special chemical structure. The alkynyl has higher activity, and can be subjected to addition cyclization under special conditions, so that the aim of quickly constructing an indole skeleton structure is fulfilled. However, most of the existing methods still have certain disadvantages, such as the requirement of using some metal reagents (Cu, ag, pt, zn, etc.) for rapid construction of indole skeleton structures, such as the requirement of electro-catalysis, long reaction time, severe conditions of high temperature, etc., thus limiting the application thereof in some cases. Thus, there remains a need to develop more efficient methods for cyclizing indole derivatives using 2-ethynylanilines under milder conditions.
Disclosure of Invention
The invention aims to solve the problems that a metal reagent is needed for constructing the existing indole skeleton structure, the electrocatalytic reaction time is long and the reaction temperature is high, and provides a preparation method of an indole derivative.
The preparation method of the indole derivative comprises the following steps:
uniformly mixing a 2-ethynyl aniline compound, iodine, potassium hydroxide, an organic solvent and water under the conditions of air atmosphere, room temperature and stirring to obtain a mixture, stirring the mixture under the conditions of air atmosphere and room temperature for reaction, then distilling under reduced pressure to remove the solvent, and separating and purifying by silica gel column chromatography to obtain indole derivatives;
the structural general formula of the 2-ethynyl aniline compound isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the general structural formula of the indole derivative isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the molar ratio of the 2-ethynyl aniline compound to iodine is 1 (1.0-1.5); the molar ratio of the 2-ethynyl aniline compound to potassium hydroxide is 1 (1.0-1.5).
The beneficial effects of the invention are as follows:
the invention can rapidly and efficiently synthesize the indole derivative under mild conditions, solves the problems that the construction of the existing indole skeleton structure needs to use a metal reagent, is electrically catalyzed, has long reaction time and high temperature, and has the characteristics of high efficiency, universality and no pollution to the environment, and the purity of the indole derivative prepared by the invention can reach more than 95 percent and the yield can reach more than 85 percent.
The invention is used for a preparation method of indole derivatives.
Drawings
FIG. 1 is a 1H NMR spectrum of an indole derivative prepared in example one;
FIG. 2 is a 13C NMR spectrum of an indole derivative prepared in example one.
Detailed Description
The first embodiment is as follows: the preparation method of the indole derivative comprises the following steps:
uniformly mixing a 2-ethynyl aniline compound, iodine, potassium hydroxide, an organic solvent and water under the conditions of air atmosphere, room temperature and stirring to obtain a mixture, stirring the mixture under the conditions of air atmosphere and room temperature for reaction, then distilling under reduced pressure to remove the solvent, and separating and purifying by silica gel column chromatography to obtain indole derivatives;
the structural general formula of the 2-ethynyl aniline compound isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the general structural formula of the indole derivative isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the molar ratio of the 2-ethynyl aniline compound to iodine is 1 (1.0-1.5); the molar ratio of the 2-ethynyl aniline compound to potassium hydroxide is 1 (1.0-1.5).
The preparation route of the indole derivative in the specific embodiment is as follows:
wherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl.
The beneficial effects of this concrete implementation are:
the specific embodiment can be used for rapidly and efficiently synthesizing the indole derivative under mild conditions, solves the problems that a metal reagent is needed for constructing the existing indole skeleton structure, the electrocatalytic reaction time is long and the reaction temperature is high, can reach more than 95 percent of purity and more than 85 percent of yield, and has the characteristics of high efficiency, universality and no pollution to the environment.
The second embodiment is as follows: the first difference between this embodiment and the specific embodiment is that: the organic solvent is acetonitrile, dichloroethane, tetrahydrofuran or dimethyl sulfoxide. The other is the same as in the first embodiment.
And a third specific embodiment: this embodiment differs from one or both of the embodiments in that: the volume ratio of the mol of the 2-ethynyl aniline compound to the organic solvent is 1mmol (10-20) mL. The other is the same as the first or second embodiment.
The specific embodiment IV is as follows: this embodiment differs from one of the first to third embodiments in that: the volume ratio of the organic solvent to the water is (3.5-4.0): 1. The other embodiments are the same as those of the first to third embodiments.
Fifth embodiment: this embodiment differs from one to four embodiments in that: the solvent used for separating and purifying the silica gel column is a mixed solvent of petroleum ether and ethyl acetate. The other embodiments are the same as those of the first to fourth embodiments.
Specific embodiment six: this embodiment differs from one of the first to fifth embodiments in that: the volume ratio of petroleum ether to ethyl acetate is (2-10): 1. The other embodiments are the same as those of the first to fifth embodiments.
Seventh embodiment: this embodiment differs from one of the first to sixth embodiments in that: under the conditions of air atmosphere, room temperature and stirring speed of 200-400 r/min, mixing the 2-ethynyl aniline compound, iodine, potassium hydroxide, an organic solvent and water for 5-10 min to obtain a mixture. The other embodiments are the same as those of the first to sixth embodiments.
Eighth embodiment: this embodiment differs from one of the first to seventh embodiments in that: and stirring the mixture for 2 to 2.5 hours under the conditions of air atmosphere, room temperature and stirring speed of 200 to 400 r/min. The other is the same as in embodiments one to seven.
Detailed description nine: this embodiment differs from one to eight of the embodiments in that: the molar ratio of the 2-ethynyl aniline compound to iodine is 1:1.5. The others are the same as in embodiments one to eight.
Detailed description ten: this embodiment differs from one of the embodiments one to nine in that: the molar ratio of the 2-ethynyl aniline compound to potassium hydroxide is 1:1.5. The others are the same as in embodiments one to nine.
The following examples are used to verify the benefits of the present invention:
embodiment one:
the preparation method of the indole derivative comprises the following steps:
under the conditions of air atmosphere, room temperature and stirring speed of 300r/min, 69.4mg (0.2 mmol) of 2-ethynylaniline compound, 76.1mg (0.3 mmol) of iodine, 16.8mg (0.3 mmol) of potassium hydroxide, 2mL of organic solvent and 0.5mL of water are mixed for 10min to obtain a mixture, the mixture is stirred and reacted for 2h under the conditions of air atmosphere, room temperature and stirring speed of 300r/min, then the solvent is removed by reduced pressure distillation, and the indole derivative is obtained by separation and purification through silica gel column chromatography;
the structural formula of the 2-ethynyl aniline compound isWherein Ts is p-toluenesulfonyl;
the indole derivative is 3-iodine-2-phenyl-1-tolyl-1H-indole, and the structural formula isWherein Ts is p-toluenesulfonyl;
the organic solvent is dimethyl sulfoxide.
The solvent used for separating and purifying the silica gel column is a mixed solvent of petroleum ether and ethyl acetate.
The volume ratio of petroleum ether to ethyl acetate is 5:1.
The indole derivatives prepared in example one were prepared by the following schemes:
the indole derivative prepared in test example one was 97% pure and 85% yield.
FIG. 1 is a 1H NMR spectrum of an indole derivative prepared in example one; FIG. 2 is a 13C NMR spectrum of an indole derivative prepared in example one; the nuclear magnetic data analysis of indole derivatives were: 1H NMR (400 MHz, CDCl 3) delta 8.36-8.28 (m, 1H), 7.54-7.41 (m, 5H), 7.40-7.30 (m, 5H), 7.10 (dd, J=8.4, 1.9Hz, 2H), 2.33 (s, 3H). 13C NMR (101 MHz, CDCl 3) delta 145.14,141.19,137.10,135.16,132.36,131.86,131.66,129.60,129.43,127.63,127.03,126.20,124.77,122.31,116.13,75.93,21.71.
Claims (10)
1. The preparation method of the indole derivative is characterized by comprising the following steps of:
uniformly mixing a 2-ethynyl aniline compound, iodine, potassium hydroxide, an organic solvent and water under the conditions of air atmosphere, room temperature and stirring to obtain a mixture, stirring the mixture under the conditions of air atmosphere and room temperature for reaction, then distilling under reduced pressure to remove the solvent, and separating and purifying by silica gel column chromatography to obtain indole derivatives;
the structural general formula of the 2-ethynyl aniline compound isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the general structural formula of the indole derivative isWherein R is phenyl, ester, alkyl or cyano, and Ts is p-toluenesulfonyl;
the molar ratio of the 2-ethynyl aniline compound to iodine is 1 (1.0-1.5); the molar ratio of the 2-ethynyl aniline compound to potassium hydroxide is 1 (1.0-1.5).
2. The method for preparing indole derivatives according to claim 1, wherein the organic solvent is acetonitrile, dichloroethane, tetrahydrofuran or dimethyl sulfoxide.
3. The process for preparing indole derivatives according to claim 2, wherein the volume ratio of the mol of the 2-ethynylaniline compounds to the organic solvent is 1mmol (10-20) mL.
4. A process for preparing indole derivatives according to claim 3, wherein the volume ratio of the organic solvent to water is 1 (3.5 to 4.0).
5. The method for preparing indole derivatives according to claim 1, wherein the solvent used for the separation and purification by silica gel column chromatography is a mixed solvent of petroleum ether and ethyl acetate.
6. The process for preparing indole derivatives according to claim 5, wherein the ratio of petroleum ether to ethyl acetate is 1 (2-10).
7. The process for preparing indole derivatives according to claim 1, wherein the mixture is obtained by mixing 2-ethynylaniline compound, iodine, potassium hydroxide, organic solvent and water for 5 to 10 minutes under an air atmosphere at room temperature at a stirring speed of 200 to 400 r/min.
8. The process for preparing indole derivatives according to claim 1, wherein the mixture is stirred for 2 to 2.5 hours under an air atmosphere at room temperature at a stirring speed of 200 to 400 r/min.
9. The process for preparing indole derivatives according to claim 1, wherein the molar ratio of 2-ethynylaniline compounds to iodine is 1:1.5.
10. The method for preparing indole derivatives according to claim 1, wherein the molar ratio of the 2-ethynylaniline compound to potassium hydroxide is 1:1.5.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310642202.5A CN116621763A (en) | 2023-06-01 | 2023-06-01 | Preparation method of indole derivative |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310642202.5A CN116621763A (en) | 2023-06-01 | 2023-06-01 | Preparation method of indole derivative |
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| Publication Number | Publication Date |
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| CN116621763A true CN116621763A (en) | 2023-08-22 |
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| CN202310642202.5A Pending CN116621763A (en) | 2023-06-01 | 2023-06-01 | Preparation method of indole derivative |
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| Country | Link |
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| CN (1) | CN116621763A (en) |
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- 2023-06-01 CN CN202310642202.5A patent/CN116621763A/en active Pending
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