CN110105219A - A method of preparing antiviral drugs intermediate - Google Patents
A method of preparing antiviral drugs intermediate Download PDFInfo
- Publication number
- CN110105219A CN110105219A CN201910480220.1A CN201910480220A CN110105219A CN 110105219 A CN110105219 A CN 110105219A CN 201910480220 A CN201910480220 A CN 201910480220A CN 110105219 A CN110105219 A CN 110105219A
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- China
- Prior art keywords
- ferrozirconium
- nano material
- loaded
- graphene oxide
- nano
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Links
- 238000000034 method Methods 0.000 title claims abstract description 15
- 239000003443 antiviral agent Substances 0.000 title claims abstract description 8
- 239000002086 nanomaterial Substances 0.000 claims abstract description 70
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 52
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 48
- 239000002131 composite material Substances 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 claims abstract description 7
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 claims abstract description 6
- DFMDAJMTLJGKFW-UHFFFAOYSA-N 3-chloro-2-nitrophenol Chemical compound OC1=CC=CC(Cl)=C1[N+]([O-])=O DFMDAJMTLJGKFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 239000003054 catalyst Substances 0.000 claims description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
- 239000000706 filtrate Substances 0.000 claims description 14
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000008213 purified water Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- GFHCXVJXSLGRJR-UHFFFAOYSA-N 3-fluoro-2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(F)=C1O GFHCXVJXSLGRJR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 238000002604 ultrasonography Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000006396 nitration reaction Methods 0.000 abstract description 22
- 229910002651 NO3 Inorganic materials 0.000 abstract description 12
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract description 12
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract description 5
- 229910017604 nitric acid Inorganic materials 0.000 abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 5
- 230000007547 defect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000013021 overheating Methods 0.000 abstract description 2
- 230000001376 precipitating effect Effects 0.000 abstract description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- NRGQRZHYRCJTKV-UHFFFAOYSA-N methyl 3-fluoro-2-hydroxybenzoate Chemical class COC(=O)C1=CC=CC(F)=C1O NRGQRZHYRCJTKV-UHFFFAOYSA-N 0.000 description 18
- 238000001514 detection method Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical group [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 5
- 229910002804 graphite Inorganic materials 0.000 description 5
- 239000010439 graphite Substances 0.000 description 5
- 230000000802 nitrating effect Effects 0.000 description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010033128 Ovarian cancer Diseases 0.000 description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001336 alkenes Chemical group 0.000 description 3
- DGHBWVVOJLVMFF-UHFFFAOYSA-N methyl 5-fluoro-2-hydroxybenzoate Chemical class COC(=O)C1=CC(F)=CC=C1O DGHBWVVOJLVMFF-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229950004707 rucaparib Drugs 0.000 description 3
- INBJJAFXHQQSRW-STOWLHSFSA-N rucaparib camsylate Chemical compound CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.CNCc1ccc(cc1)-c1[nH]c2cc(F)cc3C(=O)NCCc1c23 INBJJAFXHQQSRW-STOWLHSFSA-N 0.000 description 3
- 239000004317 sodium nitrate Substances 0.000 description 3
- 235000010344 sodium nitrate Nutrition 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KIYZJLUJJJZSNO-UHFFFAOYSA-N FC1=C(C(=C(C(=O)O)C=C1)O)[N+](=O)[O-] Chemical compound FC1=C(C(=C(C(=O)O)C=C1)O)[N+](=O)[O-] KIYZJLUJJJZSNO-UHFFFAOYSA-N 0.000 description 2
- 235000014676 Phragmites communis Nutrition 0.000 description 2
- NDUKHFILUDZSHZ-UHFFFAOYSA-N [Fe].[Zr] Chemical compound [Fe].[Zr] NDUKHFILUDZSHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- HSJPMRKMPBAUAU-UHFFFAOYSA-N cerium(3+);trinitrate Chemical compound [Ce+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O HSJPMRKMPBAUAU-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012450 pharmaceutical intermediate Substances 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- KUCWUAFNGCMZDB-UHFFFAOYSA-N 2-amino-3-nitrophenol Chemical compound NC1=C(O)C=CC=C1[N+]([O-])=O KUCWUAFNGCMZDB-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 208000007571 Ovarian Epithelial Carcinoma Diseases 0.000 description 1
- 229940127397 Poly(ADP-Ribose) Polymerase Inhibitors Drugs 0.000 description 1
- 208000026149 Primary peritoneal carcinoma Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 201000001343 fallopian tube carcinoma Diseases 0.000 description 1
- 238000009432 framing Methods 0.000 description 1
- -1 graphite alkene Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- MCNNSMNUBBQHPT-UHFFFAOYSA-N nitric acid;phenol Chemical compound O[N+]([O-])=O.OC1=CC=CC=C1 MCNNSMNUBBQHPT-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000002572 peristaltic effect Effects 0.000 description 1
- 201000002524 peritoneal carcinoma Diseases 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004323 potassium nitrate Substances 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/002—Mixed oxides other than spinels, e.g. perovskite
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/745—Iron
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910480220.1A CN110105219B (en) | 2018-09-20 | 2018-09-20 | Method for preparing intermediate for antiviral drug |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201811096802.1A CN108976130B (en) | 2018-09-20 | 2018-09-20 | A method of preparing treatment ovarian cancer intermediate |
CN201910480220.1A CN110105219B (en) | 2018-09-20 | 2018-09-20 | Method for preparing intermediate for antiviral drug |
Related Parent Applications (1)
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CN201811096802.1A Division CN108976130B (en) | 2018-09-20 | 2018-09-20 | A method of preparing treatment ovarian cancer intermediate |
Publications (2)
Publication Number | Publication Date |
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CN110105219A true CN110105219A (en) | 2019-08-09 |
CN110105219B CN110105219B (en) | 2020-04-14 |
Family
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CN201910494405.8A Active CN110078625B (en) | 2018-09-20 | 2018-09-20 | Method for preparing intermediate for ovarian cancer medicine |
CN201910480220.1A Active CN110105219B (en) | 2018-09-20 | 2018-09-20 | Method for preparing intermediate for antiviral drug |
CN201811096802.1A Active CN108976130B (en) | 2018-09-20 | 2018-09-20 | A method of preparing treatment ovarian cancer intermediate |
Family Applications Before (1)
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CN201910494405.8A Active CN110078625B (en) | 2018-09-20 | 2018-09-20 | Method for preparing intermediate for ovarian cancer medicine |
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CN201811096802.1A Active CN108976130B (en) | 2018-09-20 | 2018-09-20 | A method of preparing treatment ovarian cancer intermediate |
Country Status (1)
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CN (3) | CN110078625B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111205196A (en) * | 2020-03-04 | 2020-05-29 | 中国科学院昆明植物研究所 | Phenol AB ring structure compound and preparation method and application thereof |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102974350A (en) * | 2012-11-27 | 2013-03-20 | 复旦大学 | Graphene-supported metallic oxide nanometer material as well as preparation method and application thereof |
CN103432992A (en) * | 2013-08-23 | 2013-12-11 | 中国科学院东北地理与农业生态研究所 | Method for preparing graphene coated nanometer material composite |
CN106631810A (en) * | 2016-12-21 | 2017-05-10 | 湘潭大学 | Method for preparing aromatic nitro compounds by using immobilized Lewis acid nitration catalyst |
CN108003031A (en) * | 2017-11-23 | 2018-05-08 | 南京偌赛医药科技有限公司 | A kind of method for preparing nitro compound using graphene catalysis nitrogen dioxide |
CN108003029A (en) * | 2017-11-23 | 2018-05-08 | 南京偌赛医药科技有限公司 | A kind of method for preparing nitro compound using graphene catalysis nitric oxide |
-
2018
- 2018-09-20 CN CN201910494405.8A patent/CN110078625B/en active Active
- 2018-09-20 CN CN201910480220.1A patent/CN110105219B/en active Active
- 2018-09-20 CN CN201811096802.1A patent/CN108976130B/en active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102974350A (en) * | 2012-11-27 | 2013-03-20 | 复旦大学 | Graphene-supported metallic oxide nanometer material as well as preparation method and application thereof |
CN103432992A (en) * | 2013-08-23 | 2013-12-11 | 中国科学院东北地理与农业生态研究所 | Method for preparing graphene coated nanometer material composite |
CN106631810A (en) * | 2016-12-21 | 2017-05-10 | 湘潭大学 | Method for preparing aromatic nitro compounds by using immobilized Lewis acid nitration catalyst |
CN108003031A (en) * | 2017-11-23 | 2018-05-08 | 南京偌赛医药科技有限公司 | A kind of method for preparing nitro compound using graphene catalysis nitrogen dioxide |
CN108003029A (en) * | 2017-11-23 | 2018-05-08 | 南京偌赛医药科技有限公司 | A kind of method for preparing nitro compound using graphene catalysis nitric oxide |
Non-Patent Citations (1)
Title |
---|
DAVID A. CONLON等: "Nitrous Acid-Catalyzed Nitration of 4-Bromo-2,5-dichlorophenol. Observation of an Unusually Facile Rearrangement of a 4-Bromo-2-nitrophenol during Nitration", 《J. ORG. CHEM.》 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111205196A (en) * | 2020-03-04 | 2020-05-29 | 中国科学院昆明植物研究所 | Phenol AB ring structure compound and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
CN108976130B (en) | 2019-07-16 |
CN110078625B (en) | 2020-04-14 |
CN110078625A (en) | 2019-08-02 |
CN110105219B (en) | 2020-04-14 |
CN108976130A (en) | 2018-12-11 |
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