CN105061291A - 一种杂稠环取代的吲哚酮类化合物的合成方法 - Google Patents
一种杂稠环取代的吲哚酮类化合物的合成方法 Download PDFInfo
- Publication number
- CN105061291A CN105061291A CN201510566465.8A CN201510566465A CN105061291A CN 105061291 A CN105061291 A CN 105061291A CN 201510566465 A CN201510566465 A CN 201510566465A CN 105061291 A CN105061291 A CN 105061291A
- Authority
- CN
- China
- Prior art keywords
- compound
- synthetic method
- formula
- silver
- organic
- 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.)
- Granted
Links
- 150000005624 indolones Chemical class 0.000 title abstract 2
- 238000001308 synthesis method Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 3
- 238000010189 synthetic method Methods 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- QUVCHIHRXFRSGU-UHFFFAOYSA-N silver;3,4,5,6-tetrachlorophthalic acid Chemical compound [Ag].OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O QUVCHIHRXFRSGU-UHFFFAOYSA-N 0.000 claims description 13
- CMTKJYPJPSONIT-UHFFFAOYSA-K trichlororuthenium;triphenylphosphane Chemical compound Cl[Ru](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMTKJYPJPSONIT-UHFFFAOYSA-K 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 11
- -1 indole ketone compound Chemical class 0.000 claims description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
- 150000003304 ruthenium compounds Chemical class 0.000 claims description 8
- 229940100890 silver compound Drugs 0.000 claims description 8
- 150000003379 silver compounds Chemical class 0.000 claims description 8
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- FWARNCMTCYKUBS-UHFFFAOYSA-N ethyl n-(ethoxycarbonylcarbamoyl)carbamate Chemical compound CCOC(=O)NC(=O)NC(=O)OCC FWARNCMTCYKUBS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 claims description 3
- FZHCFNGSGGGXEH-UHFFFAOYSA-N ruthenocene Chemical compound [Ru+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 FZHCFNGSGGGXEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 claims description 3
- 229940071536 silver acetate Drugs 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- SNOFKGQEUYMNCE-UHFFFAOYSA-N 2,2,2-trifluoro-1-$l^{1}-oxidanylethanone Chemical compound [O]C(=O)C(F)(F)F SNOFKGQEUYMNCE-UHFFFAOYSA-N 0.000 claims description 2
- WZHHYIOUKQNLQM-UHFFFAOYSA-N 3,4,5,6-tetrachlorophthalic acid Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(O)=O WZHHYIOUKQNLQM-UHFFFAOYSA-N 0.000 claims description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical group C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 229960003328 benzoyl peroxide Drugs 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 5
- 238000009776 industrial production Methods 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000007800 oxidant agent Substances 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 230000002349 favourable effect Effects 0.000 abstract 1
- 230000002195 synergetic effect Effects 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 230000010355 oscillation Effects 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000013459 approach Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- ZYXPMOIHQRKWGT-UHFFFAOYSA-N silver;2,2,2-trifluoroacetic acid Chemical compound [Ag].OC(=O)C(F)(F)F ZYXPMOIHQRKWGT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 0 CC1(C)O*OC1(C)C Chemical compound CC1(C)O*OC1(C)C 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Chemical compound C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000002153 concerted effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229930005303 indole alkaloid Natural products 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Indole Compounds (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510566465.8A CN105061291B (zh) | 2015-09-08 | 2015-09-08 | 一种杂稠环取代的吲哚酮类化合物的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510566465.8A CN105061291B (zh) | 2015-09-08 | 2015-09-08 | 一种杂稠环取代的吲哚酮类化合物的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN105061291A true CN105061291A (zh) | 2015-11-18 |
CN105061291B CN105061291B (zh) | 2017-08-04 |
Family
ID=54490863
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510566465.8A Active CN105061291B (zh) | 2015-09-08 | 2015-09-08 | 一种杂稠环取代的吲哚酮类化合物的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN105061291B (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106432049A (zh) * | 2016-09-27 | 2017-02-22 | 李纪焕 | 一种苯并丁二酰亚胺化合物的合成方法 |
CN106432050A (zh) * | 2016-09-27 | 2017-02-22 | 李纪焕 | 一种亚胺类化合物的改进合成方法 |
CN108101830A (zh) * | 2018-01-27 | 2018-06-01 | 中国科学院成都生物研究所 | 一种3-取代氧化吲哚及衍生物的制备方法 |
KR20200145116A (ko) * | 2019-06-20 | 2020-12-30 | 영남대학교 산학협력단 | 신규한 옥시인돌 유도체 및 이를 유효성분으로 함유하는 항균용 조성물 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005074387A2 (en) * | 2003-12-30 | 2005-08-18 | Sun Pharmaceutical Industries Limited | Novel crystal forms of 4-[2-di-n-propylamino)ethyl]-2 (3h)- indolone hydrochloride |
CN102015642A (zh) * | 2008-02-19 | 2011-04-13 | 赛诺菲-安万特 | 新的3-氨基烷基-1,3-二氢-2h-吲哚-2-酮衍生物、其制备方法和其治疗用途 |
WO2013119774A1 (en) * | 2012-02-10 | 2013-08-15 | Virginia Commonwealth University | 3-(2-amino-ethyl)-alkylidene)-thiazolidine-2,4-dione and 1-(2-amino-ethyl)-alkylidene-1,3-dihydro-indol-2-one derivatives as selective sphingosine kinase 2 inhibitors |
CN103288708A (zh) * | 2013-04-02 | 2013-09-11 | 中国人民解放军防化学院 | 1-芳基-2-二氢吲哚酮衍生物的制备方法 |
-
2015
- 2015-09-08 CN CN201510566465.8A patent/CN105061291B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005074387A2 (en) * | 2003-12-30 | 2005-08-18 | Sun Pharmaceutical Industries Limited | Novel crystal forms of 4-[2-di-n-propylamino)ethyl]-2 (3h)- indolone hydrochloride |
CN102015642A (zh) * | 2008-02-19 | 2011-04-13 | 赛诺菲-安万特 | 新的3-氨基烷基-1,3-二氢-2h-吲哚-2-酮衍生物、其制备方法和其治疗用途 |
WO2013119774A1 (en) * | 2012-02-10 | 2013-08-15 | Virginia Commonwealth University | 3-(2-amino-ethyl)-alkylidene)-thiazolidine-2,4-dione and 1-(2-amino-ethyl)-alkylidene-1,3-dihydro-indol-2-one derivatives as selective sphingosine kinase 2 inhibitors |
CN103288708A (zh) * | 2013-04-02 | 2013-09-11 | 中国人民解放军防化学院 | 1-芳基-2-二氢吲哚酮衍生物的制备方法 |
Non-Patent Citations (1)
Title |
---|
FENG LIN,等: "Silver-catalyzed TEMPO oxidative homocoupling of indoles for the synthesis of 3,3,-biindolin-2-ones", 《RSC ADVANCES》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106432049A (zh) * | 2016-09-27 | 2017-02-22 | 李纪焕 | 一种苯并丁二酰亚胺化合物的合成方法 |
CN106432050A (zh) * | 2016-09-27 | 2017-02-22 | 李纪焕 | 一种亚胺类化合物的改进合成方法 |
CN108101830A (zh) * | 2018-01-27 | 2018-06-01 | 中国科学院成都生物研究所 | 一种3-取代氧化吲哚及衍生物的制备方法 |
CN108101830B (zh) * | 2018-01-27 | 2019-08-23 | 中国科学院成都生物研究所 | 一种3-取代氧化吲哚及衍生物的制备方法 |
KR20200145116A (ko) * | 2019-06-20 | 2020-12-30 | 영남대학교 산학협력단 | 신규한 옥시인돌 유도체 및 이를 유효성분으로 함유하는 항균용 조성물 |
KR102214988B1 (ko) | 2019-06-20 | 2021-02-10 | 영남대학교 산학협력단 | 신규한 옥시인돌 유도체 및 이를 유효성분으로 함유하는 항균용 조성물 |
Also Published As
Publication number | Publication date |
---|---|
CN105061291B (zh) | 2017-08-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN105061291A (zh) | 一种杂稠环取代的吲哚酮类化合物的合成方法 | |
GB2056973A (en) | Camptothecin derivatives useful as antitumour agents | |
CN104892623B (zh) | 一种5‑单硝酸异山梨酯的制备方法 | |
CN106117224A (zh) | 苯并菲十二烷氧基桥连十二烷氧基苯基卟啉二元化合物盘状液晶材料的合成方法 | |
CN102612507A (zh) | 制备青蒿素中间体的方法 | |
CN113620891B (zh) | 一种可控催化制备喹喔啉-2-酮类衍生物的方法 | |
CN101407513A (zh) | 一种核苷类似物的合成方法 | |
CN105237372A (zh) | 一种药物中间体芳基酮类化合物的催化合成方法 | |
JP6010605B2 (ja) | クロマン誘導体 | |
CN101585780A (zh) | 一种不对称合成手性紫杉醇侧链的方法 | |
CN105085272A (zh) | 一种芳基或杂芳基酯类化合物的合成方法 | |
CN105669746A (zh) | 一种二芳基磷酸酯类化合物的合成方法 | |
CN105085458A (zh) | 一种香豆素类衍生物的合成方法 | |
CN105198791A (zh) | 一种药物中间体氮杂螺环化合物的合成方法 | |
CN107973755B (zh) | 一种3-乙酰氨基喹喔啉酮衍生物的制备方法 | |
CN109651149B (zh) | 一种制备1,2-环己烷二甲酸酯或邻苯二甲酸酯的方法 | |
CN106117220A (zh) | 苯并菲十二烷氧基桥连异辛烷氧基苯基卟啉金属Zn配合物的合成方法 | |
CN105330690A (zh) | 一种药物中间体芳基酮磷酸酯化合物的合成方法 | |
CN100593538C (zh) | 一种n-取代丙烯酰基-2,5-吡咯二酮类化合物的制备方法 | |
CN104876809B (zh) | 一种芳酮类化合物的合成方法 | |
CN104387317A (zh) | 一种6-氯烟酸的制备方法及分离纯化方法 | |
CN100460394C (zh) | 一种3-氨基-4-甲基吡啶的制备方法 | |
CN105481767A (zh) | 一种喹啉酰胺类化合物的合成方法 | |
CN103254112A (zh) | 一种双吲哚生物碱衍生物及其合成方法和应用 | |
CN110577483B (zh) | 一种3,3-二取代-2-吲哚酮的绿色合成方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
CB03 | Change of inventor or designer information |
Inventor after: Xie Meifang Inventor after: Di Zhaolei Inventor before: Zhang Tao |
|
CB03 | Change of inventor or designer information | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20170706 Address after: 350208 Fuzhou Province, Changle City, the town of crane on the river, the village of No. 16 Applicant after: Jiang Yu Address before: 250100, Li Jia Wo 118, Sun Town, Licheng District, Shandong, Ji'nan Applicant before: Zhang Tao |
|
TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
CP02 | Change in the address of a patent holder |
Address after: 210098 Xikang Road, Drum Tower District, Nanjing, Jiangsu Province, No. 1 Patentee after: Jiang Yu Address before: 350208 16 Yun Jiang Village, Heshang Town, Changle City, Fuzhou, Fujian Patentee before: Jiang Yu |
|
CP02 | Change in the address of a patent holder | ||
TR01 | Transfer of patent right |
Effective date of registration: 20190326 Address after: 445000 Xiaocun, Xiaocun Township, Xianfeng County, Enshi Tujia and Miao Autonomous Prefecture, Hubei Province, Group 9 Patentee after: Huang Qi Address before: 210098 Xikang Road, Drum Tower District, Nanjing, Jiangsu Province, No. 1 Patentee before: Jiang Yu |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20191211 Address after: 063000 No.75, caoxiqin East Road, Fengrun District, Tangshan City, Hebei Province Patentee after: Hebei Sanshi Pharmaceutical Co., Ltd Address before: 445000 Xiaocun, Xiaocun Township, Xianfeng County, Enshi Tujia and Miao Autonomous Prefecture, Hubei Province, Group 9 Patentee before: Huang Qi |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20211029 Address after: No.75, East CaoXueqin Road, Fengrun District, Tangshan City, Hebei Province 063000 Patentee after: Hebei Huizheng Biotechnology Co.,Ltd. Address before: No.75, East CaoXueqin Road, Fengrun District, Tangshan City, Hebei Province 063000 Patentee before: Hebei Sanshi Pharmaceutical Co.,Ltd. |
|
TR01 | Transfer of patent right |