CN101735161B - 一种苯甲酸利扎曲坦中间体的制备方法 - Google Patents
一种苯甲酸利扎曲坦中间体的制备方法 Download PDFInfo
- Publication number
- CN101735161B CN101735161B CN2009102448948A CN200910244894A CN101735161B CN 101735161 B CN101735161 B CN 101735161B CN 2009102448948 A CN2009102448948 A CN 2009102448948A CN 200910244894 A CN200910244894 A CN 200910244894A CN 101735161 B CN101735161 B CN 101735161B
- Authority
- CN
- China
- Prior art keywords
- methyl
- triazole
- rizatriptan benzoate
- ether
- isophthalic acid
- 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 25
- JPRXYLQNJJVCMZ-UHFFFAOYSA-N Rizatriptan benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C2C(CC[NH+](C)C)=CNC2=CC=C1CN1C=NC=N1 JPRXYLQNJJVCMZ-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 229960004789 rizatriptan benzoate Drugs 0.000 title claims abstract description 20
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 claims abstract description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims abstract description 10
- 235000011150 stannous chloride Nutrition 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 31
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 23
- 239000000543 intermediate Substances 0.000 claims description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 239000012074 organic phase Substances 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012043 crude product Substances 0.000 claims description 12
- VVLIHSFFZJSLQO-UHFFFAOYSA-N NC(=O)C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C Chemical compound NC(=O)C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C VVLIHSFFZJSLQO-UHFFFAOYSA-N 0.000 claims description 11
- SXTKOHZKTJTGJL-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C1(C(=O)O)C(C(C(=O)O)=CC=C1)C SXTKOHZKTJTGJL-UHFFFAOYSA-N 0.000 claims description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000002798 polar solvent Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 5
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 5
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 5
- ZYVYEJXMYBUCMN-UHFFFAOYSA-N 1-methoxy-2-methylpropane Chemical compound COCC(C)C ZYVYEJXMYBUCMN-UHFFFAOYSA-N 0.000 claims description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 4
- 229940043232 butyl acetate Drugs 0.000 claims description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 4
- 229940011051 isopropyl acetate Drugs 0.000 claims description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 229940090181 propyl acetate Drugs 0.000 claims description 4
- -1 three fourth MEEs Substances 0.000 claims description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 229940093499 ethyl acetate Drugs 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000003810 ethyl acetate extraction Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000628997 Flos Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229960000425 rizatriptan Drugs 0.000 description 2
- TXHZXHICDBAVJW-UHFFFAOYSA-N rizatriptan Chemical compound C=1[C]2C(CCN(C)C)=CN=C2C=CC=1CN1C=NC=N1 TXHZXHICDBAVJW-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- DZKUKLGGGNLHNY-UHFFFAOYSA-N 1,1-dimethoxybutane Chemical compound CCCC(OC)OC DZKUKLGGGNLHNY-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- VHWPHYNZLCQCKS-UHFFFAOYSA-N 4-(3-methyl-1,2,4-triazol-1-yl)benzamide Chemical compound CC1=NN(C=N1)C1=CC=C(C(=O)N)C=C1 VHWPHYNZLCQCKS-UHFFFAOYSA-N 0.000 description 1
- 241000195493 Cryptophyta Species 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- ZGLQVRIVLWGDNA-UHFFFAOYSA-N Nc1ccc(C[n]2ncnc2)cc1 Chemical compound Nc1ccc(C[n]2ncnc2)cc1 ZGLQVRIVLWGDNA-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NVRYCUYVBBCXHT-UHFFFAOYSA-N [O-][N+](c1ccc(C[n]2ncnc2)cc1)=O Chemical compound [O-][N+](c1ccc(C[n]2ncnc2)cc1)=O NVRYCUYVBBCXHT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102448948A CN101735161B (zh) | 2009-12-18 | 2009-12-18 | 一种苯甲酸利扎曲坦中间体的制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009102448948A CN101735161B (zh) | 2009-12-18 | 2009-12-18 | 一种苯甲酸利扎曲坦中间体的制备方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101735161A CN101735161A (zh) | 2010-06-16 |
CN101735161B true CN101735161B (zh) | 2011-07-20 |
Family
ID=42459242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009102448948A Active CN101735161B (zh) | 2009-12-18 | 2009-12-18 | 一种苯甲酸利扎曲坦中间体的制备方法 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101735161B (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104478858A (zh) * | 2014-11-25 | 2015-04-01 | 浙江康多利药业有限公司 | 一种高纯度苯甲酸利札曲坦的制备方法 |
-
2009
- 2009-12-18 CN CN2009102448948A patent/CN101735161B/zh active Active
Also Published As
Publication number | Publication date |
---|---|
CN101735161A (zh) | 2010-06-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107663190B (zh) | 一种尼拉帕尼及其中间体的制备方法以及中间体化合物 | |
CN109134521A (zh) | 2-氟苯硼酸类化合物的连续化合成方法 | |
CN110092757A (zh) | 一种安全可靠的咪鲜胺的制备方法 | |
CN111848607B (zh) | 一种新型bcl-2/bcl-xl抑制剂、药物组合物及用途 | |
CN106749259B (zh) | 一种环戊基嘧啶并吡咯类化合物的合成方法 | |
CN108947949B (zh) | 抗焦虑氘代化合物及其医药用途 | |
CN101735161B (zh) | 一种苯甲酸利扎曲坦中间体的制备方法 | |
CN107176929A (zh) | 一种高效制备高纯度1h‑戊唑醇的方法 | |
JPH0474711A (ja) | 希土類金属の分離精製法 | |
CN103467445B (zh) | 苯甲酸阿格列汀的制备方法 | |
CN104803978A (zh) | 一种埃索美拉唑镁的制备方法 | |
CN102464661A (zh) | 一种5,6,7,8-四氢-咪唑并[1,5-a]吡嗪-1-羧酸乙酯的制备方法 | |
CN111116493B (zh) | 一种制备Apabetalone的方法、中间体及其中间体的制备方法 | |
CN103848756B (zh) | 特立氟胺及其中间体的制备方法 | |
CN118206434B (zh) | 一种烷基(烷基环己基甲氧基)环己烷的制备方法 | |
CN109574830A (zh) | 一种瑞舒伐他汀钙中间体及其制备方法和应用 | |
JP4014926B2 (ja) | アダマンタントリオール類の再結晶方法 | |
CN104558103B (zh) | 一种阿加曲班中间体的制备方法 | |
CN111747879A (zh) | 一种大工艺合成艾瑞昔布的方法 | |
CN114573467B (zh) | 2,4-二甲基-3-氨基苯甲酸的合成工艺 | |
CN116789527A (zh) | 一种卡泊三醇杂质及其制备方法和应用 | |
CN112538097B (zh) | 金属有机配合物及其制备方法和应用 | |
CN111196781B (zh) | 一种改进的制备五氟利多的方法 | |
CN107857739A (zh) | 一种氘代利伐沙班关键中间体及其制备方法 | |
CN112979688B (zh) | 2-氟-4-三氟甲基苯硼酸的制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20111011 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2011990000387 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20130128 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2011990000387 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20130128 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2013990000066 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20160119 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2013990000066 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20160119 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2016990000061 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20170110 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2016990000061 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20170111 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2017990000009 |
|
PLDC | Enforcement, change and cancellation of contracts on pledge of patent right or utility model | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20180110 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2017990000009 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20180110 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2018990000026 |
|
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20190108 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2018990000026 |
|
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: Preparation method of rizatriptan benzoate intermediate Effective date of registration: 20190108 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2019990000017 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20201208 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: 2019990000017 |
|
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: Preparation of rizatriptan benzoate intermediate Effective date of registration: 20201208 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: Y2020990001426 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Date of cancellation: 20211109 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: Y2020990001426 |
|
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 preparation method of rizatriptan benzoate intermediate Effective date of registration: 20211115 Granted publication date: 20110720 Pledgee: Bank of Dalian Co. Tianjin branch Pledgor: Tianjin Weijie Technology Co.,Ltd. Registration number: Y2021120000060 |
|
PP01 | Preservation of patent right | ||
PP01 | Preservation of patent right |
Effective date of registration: 20230414 Granted publication date: 20110720 |