CN101805292B - Pyrazolines compound as well as application and preparation method thereof - Google Patents
Pyrazolines compound as well as application and preparation method thereof Download PDFInfo
- Publication number
- CN101805292B CN101805292B CN 201010156628 CN201010156628A CN101805292B CN 101805292 B CN101805292 B CN 101805292B CN 201010156628 CN201010156628 CN 201010156628 CN 201010156628 A CN201010156628 A CN 201010156628A CN 101805292 B CN101805292 B CN 101805292B
- Authority
- CN
- China
- Prior art keywords
- edaravone
- preparation
- compound
- sodium pyrosulfite
- solution
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- -1 Pyrazolines compound Chemical class 0.000 title 1
- QELUYTUMUWHWMC-UHFFFAOYSA-N edaravone Chemical compound O=C1CC(C)=NN1C1=CC=CC=C1 QELUYTUMUWHWMC-UHFFFAOYSA-N 0.000 claims abstract description 25
- 229950009041 edaravone Drugs 0.000 claims abstract description 24
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims abstract description 10
- 235000010262 sodium metabisulphite Nutrition 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 5
- 239000012535 impurity Substances 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 3
- 239000007788 liquid Substances 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 4
- 239000013558 reference substance Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 abstract description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 2
- 238000004007 reversed phase HPLC Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FXXMNCZOYVUJEE-UHFFFAOYSA-N C1(=CC=CC=C1)N1N=CCC1=O.CC1(CC(C(=O)O)=CC=C1)C(=O)O Chemical compound C1(=CC=CC=C1)N1N=CCC1=O.CC1(CC(C(=O)O)=CC=C1)C(=O)O FXXMNCZOYVUJEE-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010156628 CN101805292B (en) | 2010-04-27 | 2010-04-27 | Pyrazolines compound as well as application and preparation method thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 201010156628 CN101805292B (en) | 2010-04-27 | 2010-04-27 | Pyrazolines compound as well as application and preparation method thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101805292A CN101805292A (en) | 2010-08-18 |
CN101805292B true CN101805292B (en) | 2012-01-25 |
Family
ID=42607262
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 201010156628 Active CN101805292B (en) | 2010-04-27 | 2010-04-27 | Pyrazolines compound as well as application and preparation method thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101805292B (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102140080B (en) * | 2011-01-24 | 2013-05-22 | 江苏先声药物研究有限公司 | Method for synthesizing sulfoacid organic compounds in one step |
CN102336710B (en) * | 2011-07-11 | 2014-03-12 | 宁波大学 | Method for synthesizing edaravone derivative |
CN105646530B (en) * | 2014-12-03 | 2020-05-12 | 南京先声东元制药有限公司 | Phenylpyrazole compound and preparation method and application thereof |
CN106316957B (en) * | 2015-06-15 | 2018-12-28 | 江苏正大丰海制药有限公司 | A kind of intermediate of impurity phenylhydrazine and its preparation method and application |
CN106167465B (en) * | 2016-07-06 | 2018-06-22 | 扬子江药业集团江苏海慈生物药业有限公司 | A kind of Edaravone dimer impurity compound and preparation method thereof |
CN108072710B (en) * | 2016-11-14 | 2020-10-02 | 江苏正大丰海制药有限公司 | Detection method for related substances of edaravone sodium chloride injection |
US20230364059A1 (en) * | 2020-08-17 | 2023-11-16 | Simcere Pharmaceutical Co., Ltd. | Stable pharmaceutical composition |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1241565C (en) * | 2003-04-16 | 2006-02-15 | 浙江震元制药有限公司 | Edaravone medicine composition and preparation thereof |
CN101288650B (en) * | 2008-06-04 | 2010-12-15 | 江苏先声药物研究有限公司 | Edaravone lyophilized preparation and preparation technique thereof |
-
2010
- 2010-04-27 CN CN 201010156628 patent/CN101805292B/en active Active
Also Published As
Publication number | Publication date |
---|---|
CN101805292A (en) | 2010-08-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101805292B (en) | Pyrazolines compound as well as application and preparation method thereof | |
CN102558182B (en) | Ertapenem sodium crystal form E and preparation method thereof | |
CN104072549B (en) | The production technique of Gastrodine | |
CN103570622B (en) | Preparation method of celecoxib | |
CN104402838B (en) | The process for purification of valsartan | |
CN104098512A (en) | Edaravone derivative, and preparation method, detection method and application thereof | |
CN105254569A (en) | Preparation method of ornidazole injection impurity 1-(3-chloro-propenyl)-2-methyl-5-nitroimidazole | |
CN110627703B (en) | Difluoromethylation synthesis method of aromatic amine compound | |
CN102391259B (en) | Nifuratel compound and preparation method thereof | |
CN105646530B (en) | Phenylpyrazole compound and preparation method and application thereof | |
CN104177294A (en) | Preparation method of celecoxib | |
CN103003295A (en) | Intermediate for synthesizing caspofungin and preparation method therefor | |
CN107001284B (en) | A kind of crystal form and preparation method thereof of androgen receptor inhibitor | |
CN107011322B (en) | Preparation and purification method of dehydrophenylahistine compound | |
CN103059098B (en) | Preparation method of dutasteride | |
WO2021218275A1 (en) | Method for synthesizing and refining 4-fluorobenzoylacetonitrile | |
CN105367481B (en) | A kind of synthetic method of bis- fluoro- 2- oxoindole derivatives of 3,3- | |
CN113045583B (en) | Preparation method of pinoxaden metabolite | |
CN108101911A (en) | A kind of synthesis technology of sitagliptin intermediate | |
CN105001197B (en) | A kind of Egelieting derivatives I and preparation method and application | |
CN103396373A (en) | Preparation method of deferasirox and intermediate compound of deferasirox | |
CN112125889A (en) | Preparation method of 7-bromo-2- (1-methyl-1H-pyrazol-4-yl) quinoxaline | |
CN113135862A (en) | Synthetic method of 6-fluoro-3-hydroxypyrazine-2-carboxylic acid | |
CN104356126A (en) | Preparation method of arotinolol hydrochloride | |
CN104387332B (en) | A kind of method of synthetic aroma enzyme inhibitors |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
ASS | Succession or assignment of patent right |
Owner name: BODA PHARMACEUTICAL CO., LTD., JILIN PROVINCE Effective date: 20130327 |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20130327 Address after: 210042 Xuanwu Avenue, Jiangsu, Nanjing, No. 699 -18 Patentee after: JIANGSU SIMCERE PHARMACEUTICAL R & D Co.,Ltd. Patentee after: JILIN BODA PHARMACEUTICAL Co.,Ltd. Address before: 210042 Xuanwu Avenue, Jiangsu, Nanjing, No. 699 -18 Patentee before: JIANGSU SIMCERE PHARMACEUTICAL R & D Co.,Ltd. |
|
C41 | Transfer of patent application or patent right or utility model | ||
TR01 | Transfer of patent right |
Effective date of registration: 20160725 Address after: 210042 Xuanwu District, Xuanwu District, Jiangsu, Nanjing No. 699 -18 Patentee after: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Patentee after: JILIN BODA PHARMACEUTICAL Co.,Ltd. Address before: 210042 Xuanwu Avenue, Jiangsu, Nanjing, No. 699 -18 Patentee before: JIANGSU SIMCERE PHARMACEUTICAL R & D Co.,Ltd. Patentee before: Jilin Boda Pharmaceutical Co.,Ltd. |
|
CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Co-patentee after: Jilin Boda pharmaceutical Limited by Share Ltd. Patentee after: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Address before: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Co-patentee before: Jilin Boda Pharmaceutical Co.,Ltd. Patentee before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180921 Address after: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Co-patentee after: Jilin Boda pharmaceutical Limited by Share Ltd. Patentee after: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Co-patentee after: NANJING SIMCERE DONGYUAN PHARMACEUTICA Co.,Ltd. Address before: 210042 699 Xuanwu Road, Xuanwu District, Nanjing, Jiangsu -18 Co-patentee before: Jilin Boda pharmaceutical Limited by Share Ltd. Patentee before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. |
|
CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 210042 -18, Xuanwu Avenue, Xuanwu District, Jiangsu, Nanjing, 699 Co-patentee after: Jilin Boda pharmaceutical Limited by Share Ltd. Patentee after: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Co-patentee after: SIMCERE PHARMACEUTICAL Co.,Ltd. Address before: 210042 -18, Xuanwu Avenue, Xuanwu District, Jiangsu, Nanjing, 699 Co-patentee before: Jilin Boda pharmaceutical Limited by Share Ltd. Patentee before: JIANGSU SIMCERE PHARMACEUTICAL Co.,Ltd. Co-patentee before: NANJING SIMCERE DONGYUAN PHARMACEUTICA Co.,Ltd. |