CN108084013A - 一种3-溴-2-氟苯甲酸的合成方法 - Google Patents
一种3-溴-2-氟苯甲酸的合成方法 Download PDFInfo
- Publication number
- CN108084013A CN108084013A CN201711465018.9A CN201711465018A CN108084013A CN 108084013 A CN108084013 A CN 108084013A CN 201711465018 A CN201711465018 A CN 201711465018A CN 108084013 A CN108084013 A CN 108084013A
- Authority
- CN
- China
- Prior art keywords
- bromo
- reaction
- fluobenzoic acids
- synthetic method
- trimethylsilyl
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 38
- 238000010189 synthetic method Methods 0.000 title claims abstract description 17
- 150000007513 acids Chemical class 0.000 title claims description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 54
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 claims abstract description 23
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 18
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 9
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- 230000005595 deprotonation Effects 0.000 claims abstract description 7
- 238000010537 deprotonation reaction Methods 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 5
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 13
- 229940043279 diisopropylamine Drugs 0.000 claims description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 10
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 8
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 claims description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 6
- 229940094989 trimethylsilane Drugs 0.000 claims description 6
- NVTNGGKVRVPJDW-UHFFFAOYSA-N (2-fluorophenyl)-trimethylsilane Chemical class C[Si](C)(C)C1=CC=CC=C1F NVTNGGKVRVPJDW-UHFFFAOYSA-N 0.000 claims description 5
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical class CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical class BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 claims description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 3
- 235000019253 formic acid Nutrition 0.000 claims description 3
- RCOFRHAHVGHIEV-UHFFFAOYSA-N [Li].C[Si](C=1C(=CC=CC1)F)(C)C Chemical class [Li].C[Si](C=1C(=CC=CC1)F)(C)C RCOFRHAHVGHIEV-UHFFFAOYSA-N 0.000 claims description 2
- HDPRNQWMIFKNKS-UHFFFAOYSA-N benzene;lithium Chemical class [Li].C1=CC=CC=C1 HDPRNQWMIFKNKS-UHFFFAOYSA-N 0.000 claims description 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- HQTJYTVKYNLWBJ-UHFFFAOYSA-N silane trimethyl-lambda3-chlorane Chemical compound [SiH4].CCl(C)C HQTJYTVKYNLWBJ-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 3
- -1 2 fluorophenyl trimethyl silanes Chemical class 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- SPIOKNPWOZFWDI-UHFFFAOYSA-N fluorobenzene;lithium Chemical class [Li].FC1=CC=CC=C1 SPIOKNPWOZFWDI-UHFFFAOYSA-N 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FFWQLZFIMNTUCZ-UHFFFAOYSA-N 1-(bromomethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CBr FFWQLZFIMNTUCZ-UHFFFAOYSA-N 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KQRCBMPPEPNNDS-UHFFFAOYSA-N 2-bromo-3-fluorobenzoic acid Chemical class OC(=O)C1=CC=CC(F)=C1Br KQRCBMPPEPNNDS-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960002465 dabrafenib Drugs 0.000 description 1
- BFSMGDJOXZAERB-UHFFFAOYSA-N dabrafenib Chemical compound S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 BFSMGDJOXZAERB-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/363—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711465018.9A CN108084013B (zh) | 2017-12-28 | 2017-12-28 | 一种3-溴-2-氟苯甲酸的合成方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201711465018.9A CN108084013B (zh) | 2017-12-28 | 2017-12-28 | 一种3-溴-2-氟苯甲酸的合成方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN108084013A true CN108084013A (zh) | 2018-05-29 |
CN108084013B CN108084013B (zh) | 2020-09-01 |
Family
ID=62180437
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201711465018.9A Active CN108084013B (zh) | 2017-12-28 | 2017-12-28 | 一种3-溴-2-氟苯甲酸的合成方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN108084013B (zh) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110204433A (zh) * | 2019-06-26 | 2019-09-06 | 湖南师范大学 | 一种3,4-二氟-2-甲基苯甲酸的合成方法 |
CN111909078A (zh) * | 2020-09-02 | 2020-11-10 | 阿里生物新材料(常州)有限公司 | 一种(2-氟-6-(三氟甲基)吡啶-3-基)甲醇的合成方法 |
CN112661632A (zh) * | 2020-12-25 | 2021-04-16 | 杭州澳赛诺生物科技有限公司 | 一种2-氟-4-卤素苯甲酸的合成方法 |
CN113861034A (zh) * | 2021-10-15 | 2021-12-31 | 浙江工业大学 | 2-氟-3-硝基苯甲酸的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764525A (en) * | 1987-02-25 | 1988-08-16 | Warner-Lambert Company | N-1H-tetrazol-5-ylbenzamides having use as antiallergy and antiinflammatory agents |
CN101050176A (zh) * | 2007-05-11 | 2007-10-10 | 上海康鹏化学有限公司 | 4-溴-2,6-二氟苯甲酸的制备方法 |
-
2017
- 2017-12-28 CN CN201711465018.9A patent/CN108084013B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4764525A (en) * | 1987-02-25 | 1988-08-16 | Warner-Lambert Company | N-1H-tetrazol-5-ylbenzamides having use as antiallergy and antiinflammatory agents |
CN101050176A (zh) * | 2007-05-11 | 2007-10-10 | 上海康鹏化学有限公司 | 4-溴-2,6-二氟苯甲酸的制备方法 |
Non-Patent Citations (2)
Title |
---|
CHRISTOPHE HEISS, ET AL.: "Remote trimethylsilyl groups interfering with the ortho deprotonation of fluoroarenes and chloroarenes", 《EUROPEAN JOURNAL OF ORGANIC CHEMISTRY》 * |
赵昊昱 等: "3-溴-2-氟苯甲酸的合成", 《化学世界》 * |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110204433A (zh) * | 2019-06-26 | 2019-09-06 | 湖南师范大学 | 一种3,4-二氟-2-甲基苯甲酸的合成方法 |
CN111909078A (zh) * | 2020-09-02 | 2020-11-10 | 阿里生物新材料(常州)有限公司 | 一种(2-氟-6-(三氟甲基)吡啶-3-基)甲醇的合成方法 |
CN111909078B (zh) * | 2020-09-02 | 2022-03-11 | 阿里生物新材料(常州)有限公司 | 一种(2-氟-6-(三氟甲基)吡啶-3-基)甲醇的合成方法 |
CN112661632A (zh) * | 2020-12-25 | 2021-04-16 | 杭州澳赛诺生物科技有限公司 | 一种2-氟-4-卤素苯甲酸的合成方法 |
CN113861034A (zh) * | 2021-10-15 | 2021-12-31 | 浙江工业大学 | 2-氟-3-硝基苯甲酸的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN108084013B (zh) | 2020-09-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN108084013A (zh) | 一种3-溴-2-氟苯甲酸的合成方法 | |
CN111100067A (zh) | 一种新的扑尔敏杂质及其制备工艺 | |
CN107721912B (zh) | 一种2-氯-5-甲基吡啶的制备方法 | |
CN110590569B (zh) | 一种合成妥洛特罗的方法 | |
KR102513651B1 (ko) | 에테르 화합물 제조 방법 | |
CN110498744B (zh) | 一种1-乙基-3-硝基苯的制备方法 | |
CN110669002A (zh) | 一种2-氟-3-羟基吡啶-4-羧酸的合成方法 | |
CN112812059A (zh) | 一种2-氨基磺酰基-n,n-二甲基烟酰胺的制备方法 | |
CN109134204B (zh) | 中间体2-溴-4-氟-5-氯苯酚的合成法 | |
CN108546266B (zh) | 一种1,4,6,7-四氢吡喃[4,3-c]吡唑-3-羧酸的合成方法 | |
CN105601639B (zh) | 一种6-叔丁氧羰基八氢-2H-吡喃[3,2-c]并吡啶-8-羧酸的合成方法 | |
US20230348390A1 (en) | Method for preparing methyl(s)-2-amino-3-(4-(2,3-dimethylpyridin-4-yl)phenylpropionate and salt thereof | |
CN109678738A (zh) | 一种合成(2s,3s)-3-氨基-二环[2.2.2]辛烷-2-甲酸酯的方法 | |
CN104478913A (zh) | 2-氟吡啶-4-硼酸的制备方法 | |
WO2019240033A1 (ja) | ジシクロヘキサンジカルボン酸ジエステルの製造方法およびジシクロヘキサンジカルボン酸の製造方法 | |
CN115215803B (zh) | 一种4-卤代-1-(二氟甲基)-1h-咪唑的制备方法 | |
CN113816890B (zh) | 一种那拉曲坦制备用中间体化合物的制备方法 | |
CN114105821B (zh) | 一种七氟异丁腈的制备方法 | |
CN110092746B (zh) | 一种2-氨基-5-卤代吡啶的简便制备方法 | |
JPS61151194A (ja) | チオフアン誘導体の製造法 | |
CN108976182A (zh) | 一种制备达格列净五元环杂质的方法 | |
CN109232417B (zh) | 4-苯氧基喹啉类化合物的制备方法 | |
CN110105361B (zh) | 一种Evodiakine及其衍生物的制备方法 | |
CN107915570B (zh) | 一种4-溴-1-甲基-2-(三氟甲基)苯的制备方法 | |
CN108383719B (zh) | 一种环己甲酸的生产工艺 |
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 | ||
CB03 | Change of inventor or designer information |
Inventor after: Gu Zhaoye Inventor after: Gao Feng Inventor after: Zeng Sailan Inventor after: Jiang Junqiang Inventor after: Zhang Xingxing Inventor before: Gao Feng Inventor before: Zeng Sailan Inventor before: Jiang Junqiang Inventor before: Zhang Xingxing |
|
CB03 | Change of inventor or designer information | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20200805 Address after: 265601 north of middle section of Huasheng West Road, BEIGOU Town, Penglai City, Yantai City, Shandong Province Applicant after: Penglai Qianwei Chemical Co., Ltd Address before: 201512 Shanghai City, Jinshan District Jinshanwei town Qiushi Road No. 688 Building 1, unit 2, room 404 Applicant before: SHANGHAI TBBMED Co.,Ltd. |
|
TA01 | Transfer of patent application right | ||
GR01 | Patent grant | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right |
Effective date of registration: 20210519 Address after: 265601 north of middle section of Huasheng West Road, BEIGOU Town, Penglai District, Yantai City, Shandong Province Patentee after: Yantai Penglai Rongxin Chemical Co.,Ltd. Address before: 265601 north of middle section of Huasheng West Road, BEIGOU Town, Penglai City, Yantai City, Shandong Province Patentee before: Penglai Qianwei Chemical Co., Ltd |
|
TR01 | Transfer of patent right |