CN104030984B - 一种吡唑衍生物的制备方法 - Google Patents
一种吡唑衍生物的制备方法 Download PDFInfo
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- CN104030984B CN104030984B CN201410247011.XA CN201410247011A CN104030984B CN 104030984 B CN104030984 B CN 104030984B CN 201410247011 A CN201410247011 A CN 201410247011A CN 104030984 B CN104030984 B CN 104030984B
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- mmol
- chalcone
- crude product
- reactant mixture
- organic facies
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- 150000003217 pyrazoles Chemical class 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 142
- 238000006243 chemical reaction Methods 0.000 claims abstract description 95
- 208000035126 Facies Diseases 0.000 claims abstract description 60
- 239000012043 crude product Substances 0.000 claims abstract description 60
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 239000000376 reactant Substances 0.000 claims abstract description 60
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 56
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical class [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims abstract description 31
- 238000001514 detection method Methods 0.000 claims abstract description 31
- 238000000926 separation method Methods 0.000 claims abstract description 31
- 235000002639 sodium chloride Nutrition 0.000 claims abstract description 31
- 239000007832 Na2SO4 Substances 0.000 claims abstract description 30
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000000284 extract Substances 0.000 claims abstract description 30
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 30
- 239000011780 sodium chloride Substances 0.000 claims abstract description 30
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 30
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 238000005406 washing Methods 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000010992 reflux Methods 0.000 claims abstract description 29
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000002561 ketenes Chemical class 0.000 claims abstract description 10
- 235000019439 ethyl acetate Nutrition 0.000 claims description 55
- 238000002156 mixing Methods 0.000 claims description 49
- 238000003756 stirring Methods 0.000 claims description 30
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 26
- 235000005513 chalcones Nutrition 0.000 claims description 26
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 26
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000002576 ketones Chemical class 0.000 claims description 13
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- XUFXKBJMCRJATM-FMIVXFBMSA-N (e)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(OC)=CC=C1\C=C\C(=O)C1=CC=CC=C1 XUFXKBJMCRJATM-FMIVXFBMSA-N 0.000 claims description 5
- BDYUEJNFECTVKN-UHFFFAOYSA-N 1-(2-nitro-1-phenylethyl)pyrazole Chemical class [N+](=O)([O-])CC(C1=CC=CC=C1)N1N=CC=C1 BDYUEJNFECTVKN-UHFFFAOYSA-N 0.000 claims description 4
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 4
- 229940017219 methyl propionate Drugs 0.000 claims description 4
- SMFBODMWKWBFOK-MDZDMXLPSA-N (e)-3-(3-nitrophenyl)-1-phenylprop-2-en-1-one Chemical compound [O-][N+](=O)C1=CC=CC(\C=C\C(=O)C=2C=CC=CC=2)=C1 SMFBODMWKWBFOK-MDZDMXLPSA-N 0.000 claims description 3
- XNLFHCPVTULKIV-VAWYXSNFSA-N (e)-3-(4-methylphenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(C)=CC=C1\C=C\C(=O)C1=CC=CC=C1 XNLFHCPVTULKIV-VAWYXSNFSA-N 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- WDZGGAFMGIOIQS-DHZHZOJOSA-N (e)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1\C=C\C(=O)C1=CC=CC=C1 WDZGGAFMGIOIQS-DHZHZOJOSA-N 0.000 claims description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 238000004440 column chromatography Methods 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 6
- ZDIACNVYSMNTGL-UHFFFAOYSA-N di(pyrazol-1-yl)methanone Chemical compound C1=CC=NN1C(=O)N1C=CC=N1 ZDIACNVYSMNTGL-UHFFFAOYSA-N 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 96
- 239000000047 product Substances 0.000 description 30
- 239000007788 liquid Substances 0.000 description 28
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 24
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 7
- -1 pyrazole compound Chemical class 0.000 description 5
- 238000006957 Michael reaction Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- QLXBMZAOTHBHSM-IZZDOVSWSA-N (e)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)\C=C\C1=CC=CC=C1 QLXBMZAOTHBHSM-IZZDOVSWSA-N 0.000 description 1
- FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 229910020323 ClF3 Inorganic materials 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910003865 HfCl4 Inorganic materials 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- JJEDWBQZCRESJL-UHFFFAOYSA-N N-[(5-methyl-2-furanyl)methylideneamino]-2-phenoxybenzamide Chemical compound O1C(C)=CC=C1C=NNC(=O)C1=CC=CC=C1OC1=CC=CC=C1 JJEDWBQZCRESJL-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 229910018057 ScCl3 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- 229950004502 bromindione Drugs 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 238000010523 cascade reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (4)
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CN201410247011.XA CN104030984B (zh) | 2014-06-06 | 2014-06-06 | 一种吡唑衍生物的制备方法 |
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CN201410247011.XA CN104030984B (zh) | 2014-06-06 | 2014-06-06 | 一种吡唑衍生物的制备方法 |
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CN104030984A CN104030984A (zh) | 2014-09-10 |
CN104030984B true CN104030984B (zh) | 2016-07-13 |
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Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107759623B (zh) * | 2016-08-23 | 2020-08-14 | 苏州旺山旺水生物医药有限公司 | Jak抑制剂的中间体及其制备方法 |
CN110003110B (zh) * | 2019-04-29 | 2022-09-06 | 南京工业大学 | 一种芳基β-氨基酮化合物及其制备方法 |
CN110483399A (zh) * | 2019-08-09 | 2019-11-22 | 上海应用技术大学 | 一种碱催化合成β-(N-吡唑基)酮类化合物的方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100331302A1 (en) * | 2007-06-22 | 2010-12-30 | Chemocentryx, Inc. | N-(2-(hetaryl)aryl) arylsulfonamides and n-(2-(hetaryl)hetaryl arylsulfonamides |
CN102000605A (zh) * | 2010-10-25 | 2011-04-06 | 南京大学 | 一价铜的催化起始物Cu2(L)Cl2及其制备方法、氮杂环芳香化产物的制备方法 |
EP2308850A1 (en) * | 2009-10-06 | 2011-04-13 | Laboratorios Del. Dr. Esteve, S.A. | Heterocycyl-substituted-alkylamino phenyl derivatives, their preparation and use as medicaments |
-
2014
- 2014-06-06 CN CN201410247011.XA patent/CN104030984B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100331302A1 (en) * | 2007-06-22 | 2010-12-30 | Chemocentryx, Inc. | N-(2-(hetaryl)aryl) arylsulfonamides and n-(2-(hetaryl)hetaryl arylsulfonamides |
EP2308850A1 (en) * | 2009-10-06 | 2011-04-13 | Laboratorios Del. Dr. Esteve, S.A. | Heterocycyl-substituted-alkylamino phenyl derivatives, their preparation and use as medicaments |
CN102000605A (zh) * | 2010-10-25 | 2011-04-06 | 南京大学 | 一价铜的催化起始物Cu2(L)Cl2及其制备方法、氮杂环芳香化产物的制备方法 |
Non-Patent Citations (1)
Title |
---|
MILD AND EFFICIENT PROCEDURE FOR MICHAEL ADDITION OF N-HETEROCYCLES TO a,b-UNSATURATED COMPOUNDS USING ANHYDROUS K3PO4 AS CATALYST;Xueling Hou,等;《Synthetic Communications》;20101231;第40卷;第973-979页 * |
Also Published As
Publication number | Publication date |
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CN104030984A (zh) | 2014-09-10 |
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Inventor after: Zhou Hongyan Inventor after: Yang Jingya Inventor after: Ma Ben Inventor after: Li Zheng Inventor before: Yang Jingya Inventor before: Zhou Hongyan Inventor before: Ma Ben Inventor before: Zhan Baohua Inventor before: Li Zheng |
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Effective date of registration: 20160601 Address after: 730070 Anning District, Gansu, Lanzhou Camp Village Gate No. 1 Applicant after: Gansu Agricultural University Address before: 730070 Anning Road, Anning District, Gansu, Lanzhou, China, No. 805 Applicant before: Northwest Normal University Applicant before: Gansu Agricultural University |
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