CN115433140B - 一种阿福拉纳的合成方法 - Google Patents
一种阿福拉纳的合成方法 Download PDFInfo
- Publication number
- CN115433140B CN115433140B CN202211387937.XA CN202211387937A CN115433140B CN 115433140 B CN115433140 B CN 115433140B CN 202211387937 A CN202211387937 A CN 202211387937A CN 115433140 B CN115433140 B CN 115433140B
- Authority
- CN
- China
- Prior art keywords
- temperature
- drying
- reduced pressure
- synthesizing
- under reduced
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000010189 synthetic method Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 21
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 21
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims abstract description 14
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 13
- 238000009833 condensation Methods 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 54
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 39
- 238000001035 drying Methods 0.000 claims description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 23
- 238000003756 stirring Methods 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 15
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 claims description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
- 239000013067 intermediate product Substances 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 229910001868 water Inorganic materials 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 238000004321 preservation Methods 0.000 claims description 4
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 claims description 3
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims description 3
- 239000008213 purified water Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- JLRMRTRHBRVQMS-UHFFFAOYSA-N hydrogen peroxide;2-methylpropan-2-ol Chemical compound OO.CC(C)(C)O JLRMRTRHBRVQMS-UHFFFAOYSA-N 0.000 claims 2
- 238000003810 ethyl acetate extraction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 abstract description 10
- 125000000842 isoxazolyl group Chemical group 0.000 abstract description 7
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000012535 impurity Substances 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 4
- 238000000746 purification Methods 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 238000006170 formylation reaction Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000005882 aldol condensation reaction Methods 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- -1 4-bromonaphthalen-1-yl Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSVHMWORIJZGTJ-UHFFFAOYSA-N 1-(4-bromonaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=C(Br)C2=C1 CSVHMWORIJZGTJ-UHFFFAOYSA-N 0.000 description 2
- 241000238876 Acari Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000002163 Mesapamea fractilinea Species 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000000507 anthelmentic effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 108010062745 Chloride Channels Proteins 0.000 description 1
- 102000011045 Chloride Channels Human genes 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- 208000000291 Nematode infections Diseases 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 229940068682 chewable tablet Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 150000002547 isoxazolines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940058878 nexgard Drugs 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 230000003518 presynaptic effect Effects 0.000 description 1
- 230000001846 repelling effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211387937.XA CN115433140B (zh) | 2022-11-08 | 2022-11-08 | 一种阿福拉纳的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211387937.XA CN115433140B (zh) | 2022-11-08 | 2022-11-08 | 一种阿福拉纳的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115433140A CN115433140A (zh) | 2022-12-06 |
CN115433140B true CN115433140B (zh) | 2023-01-31 |
Family
ID=84253019
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211387937.XA Active CN115433140B (zh) | 2022-11-08 | 2022-11-08 | 一种阿福拉纳的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115433140B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116143652A (zh) * | 2023-01-13 | 2023-05-23 | 四川青木制药有限公司 | 一种阿福拉纳中间体及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010235590A (ja) * | 2009-03-09 | 2010-10-21 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
CN101990530A (zh) * | 2008-04-09 | 2011-03-23 | 杜邦公司 | 用于制备3-三氟甲基查耳酮的方法 |
CN106459019A (zh) * | 2014-02-26 | 2017-02-22 | 巴斯夫欧洲公司 | 唑啉类化合物 |
CN111533663A (zh) * | 2020-06-17 | 2020-08-14 | 常州工程职业技术学院 | 一种合成美沙拉嗪的方法 |
CN112457267A (zh) * | 2020-11-27 | 2021-03-09 | 麦蒂辛生物医药科技成都有限公司 | 一种异噁唑啉杀虫剂的制备方法 |
-
2022
- 2022-11-08 CN CN202211387937.XA patent/CN115433140B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101990530A (zh) * | 2008-04-09 | 2011-03-23 | 杜邦公司 | 用于制备3-三氟甲基查耳酮的方法 |
JP2010235590A (ja) * | 2009-03-09 | 2010-10-21 | Nissan Chem Ind Ltd | 置換イソキサゾリン化合物及び有害生物防除剤 |
CN106459019A (zh) * | 2014-02-26 | 2017-02-22 | 巴斯夫欧洲公司 | 唑啉类化合物 |
CN111533663A (zh) * | 2020-06-17 | 2020-08-14 | 常州工程职业技术学院 | 一种合成美沙拉嗪的方法 |
CN112457267A (zh) * | 2020-11-27 | 2021-03-09 | 麦蒂辛生物医药科技成都有限公司 | 一种异噁唑啉杀虫剂的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN115433140A (zh) | 2022-12-06 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN110028462B (zh) | 一种制备异噁唑啉类中间体及异噁唑啉的方法 | |
CN115433140B (zh) | 一种阿福拉纳的合成方法 | |
CN112062712A (zh) | 一种2-(5-溴-3-甲基吡啶-2-基)乙酸盐酸盐的制备方法 | |
CA2351528C (en) | Process for the preparation of a piperazine derivative | |
CN114315748A (zh) | 一种氟雷拉纳的合成方法 | |
CN113735681A (zh) | 一种氟雷拉纳中间体及其制备氟雷拉纳的方法 | |
CN111732544B (zh) | 一种合成3-(4-甲基-1h-咪唑-1-基)-5-(三氟甲基)苯胺的方法 | |
CN115536541A (zh) | 氟雷拉纳和阿福拉纳共同中间体的合成方法 | |
CN115504971B (zh) | 一种洛替拉纳的合成方法 | |
CN105111161B (zh) | 一种高效偶联串联合成2‑苯基苯并恶唑及其衍生物的方法 | |
CN111333512A (zh) | 阿福拉纳关键中间体4-乙酰基-1-萘甲酸酯的制备 | |
CN113354530A (zh) | 一种制备4-乙酰基-1-萘甲酸的方法 | |
CN111675672A (zh) | 一种制备阿塔鲁伦的方法 | |
CN115594645B (zh) | 一种氟雷拉纳的合成方法 | |
CN101654426B (zh) | 制备伊洛马司他的方法 | |
KR100564072B1 (ko) | α,α-디메틸벤질 시아나이드로부터 α,α-디메틸페닐아세트산을 비가압적으로 제조하는 방법 | |
CN107935858B (zh) | 5-氟-2-硝基苯酚的制备方法 | |
CN111848538A (zh) | 一种帕瑞昔布钠杂质的合成方法 | |
CN110563721A (zh) | 一种新的盐酸阿扎司琼的制备方法 | |
CN114957147A (zh) | 一种异噁唑啉类衍生物的制备方法 | |
CN109320418B (zh) | 1,3,5-苯三甲酸三甲酯的合成方法及其应用 | |
CN112898221A (zh) | 苯并噁嗪二酮类化合物c的制备方法及其中间体 | |
CN106631811A (zh) | 一种3‑氯‑4‑氟硝基苯的制备方法 | |
KR101170192B1 (ko) | 1,2-벤즈이속사졸-3-메탄술폰아미드의 원-포트 제조방법 | |
CN117126117A (zh) | 一种阿福拉纳的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20230808 Address after: 262100 Dongcheng Entrepreneurship Park, Dawenhe Tourism Development Zone, Anqiu City, Weifang City, Shandong Province Patentee after: Yahua Pet Food (Shandong) Co.,Ltd. Address before: 261,000 North 500 meters east of Xiangshan Town Community, Dawenhe Tourism Development Zone, Anqiu City, Weifang City, Shandong Province Patentee before: Shihua Hechuang Biotechnology Development (Shandong) Co.,Ltd. |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A Synthetic Method of Alfrana Effective date of registration: 20231107 Granted publication date: 20230131 Pledgee: Anqiu Shandong rural commercial bank Limited by Share Ltd. Pledgor: Yahua Pet Food (Shandong) Co.,Ltd. Registration number: Y2023980064404 |