CN101591310A - 一种马来酸桂哌齐特的制备方法 - Google Patents
一种马来酸桂哌齐特的制备方法 Download PDFInfo
- Publication number
- CN101591310A CN101591310A CNA2008102299578A CN200810229957A CN101591310A CN 101591310 A CN101591310 A CN 101591310A CN A2008102299578 A CNA2008102299578 A CN A2008102299578A CN 200810229957 A CN200810229957 A CN 200810229957A CN 101591310 A CN101591310 A CN 101591310A
- Authority
- CN
- China
- Prior art keywords
- preparation
- piperazine
- cinepazide
- reaction
- trimethoxy
- 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
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- 229960004201 cinepazide Drugs 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 44
- XSTJTOKYCAJVMJ-GVTSEVKNSA-N (z)-but-2-enedioic acid;(e)-1-[4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound OC(=O)\C=C/C(O)=O.COC1=C(OC)C(OC)=CC(\C=C\C(=O)N2CCN(CC(=O)N3CCCC3)CC2)=C1 XSTJTOKYCAJVMJ-GVTSEVKNSA-N 0.000 title claims abstract description 42
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 89
- 238000006243 chemical reaction Methods 0.000 claims abstract description 69
- -1 cinnamoyl Chemical group 0.000 claims abstract description 41
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 28
- YTFVRYKNXDADBI-SNAWJCMRSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-SNAWJCMRSA-N 0.000 claims abstract description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims abstract description 12
- YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003513 alkali Substances 0.000 claims abstract description 12
- RCUDFXMNPQNBDU-VOTSOKGWSA-N cinepazide Chemical compound COC1=C(OC)C(OC)=CC(\C=C\C(=O)N2CCN(CC(=O)N3CCCC3)CC2)=C1 RCUDFXMNPQNBDU-VOTSOKGWSA-N 0.000 claims abstract description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 238000000967 suction filtration Methods 0.000 claims description 25
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 23
- LXSMSGZJGPUNOF-UHFFFAOYSA-N CCCCCCCCCCCCCC[ClH]CN1CCCC1 Chemical compound CCCCCCCCCCCCCC[ClH]CN1CCCC1 LXSMSGZJGPUNOF-UHFFFAOYSA-N 0.000 claims description 21
- 229960001701 chloroform Drugs 0.000 claims description 20
- 239000000706 filtrate Substances 0.000 claims description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
- 150000008065 acid anhydrides Chemical class 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 9
- 235000007715 potassium iodide Nutrition 0.000 claims description 8
- 229960004839 potassium iodide Drugs 0.000 claims description 8
- 150000001263 acyl chlorides Chemical class 0.000 claims description 7
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 7
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000005660 chlorination reaction Methods 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 239000007810 chemical reaction solvent Substances 0.000 claims description 4
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- 150000001262 acyl bromides Chemical class 0.000 claims description 2
- 150000001265 acyl fluorides Chemical class 0.000 claims description 2
- 150000001267 acyl iodides Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 4
- 238000009776 industrial production Methods 0.000 abstract description 2
- AAOSLLBWWRKJIR-UHFFFAOYSA-N 2-chloro-1-pyrrolidin-1-ylethanone Chemical compound ClCC(=O)N1CCCC1 AAOSLLBWWRKJIR-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000001035 drying Methods 0.000 description 17
- 239000012044 organic layer Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 229960004756 ethanol Drugs 0.000 description 13
- 238000010992 reflux Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000012065 filter cake Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000006837 decompression Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- ZOIHAPJGSMQVCR-UHFFFAOYSA-N 5-(3-chloroprop-1-enyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(C=CCCl)=CC(OC)=C1OC ZOIHAPJGSMQVCR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 230000017531 blood circulation Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- LCXSXBYYVYTYDY-BTJKTKAUSA-N (z)-but-2-enedioic acid;piperazine Chemical compound C1CNCCN1.OC(=O)\C=C/C(O)=O LCXSXBYYVYTYDY-BTJKTKAUSA-N 0.000 description 1
- 102000001707 3',5'-Cyclic-AMP Phosphodiesterases Human genes 0.000 description 1
- 108010054479 3',5'-Cyclic-AMP Phosphodiesterases Proteins 0.000 description 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 206010047163 Vasospasm Diseases 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000033904 relaxation of vascular smooth muscle Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN2008102299578A CN101591310B (zh) | 2008-12-19 | 2008-12-19 | 一种马来酸桂哌齐特的制备方法 |
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CN2008102299578A CN101591310B (zh) | 2008-12-19 | 2008-12-19 | 一种马来酸桂哌齐特的制备方法 |
Publications (2)
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CN101591310A true CN101591310A (zh) | 2009-12-02 |
CN101591310B CN101591310B (zh) | 2012-03-21 |
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CN2008102299578A Expired - Fee Related CN101591310B (zh) | 2008-12-19 | 2008-12-19 | 一种马来酸桂哌齐特的制备方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012176621A1 (ja) * | 2011-06-24 | 2012-12-27 | 株式会社ダイセル | 不飽和カルボン酸アミド組成物の製造方法 |
JPWO2012176693A1 (ja) * | 2011-06-24 | 2015-02-23 | 東京応化工業株式会社 | 新規化合物 |
CN110963983A (zh) * | 2018-09-28 | 2020-04-07 | 康普药业股份有限公司 | 一种马来酸桂哌齐特的制备方法 |
CN112028856A (zh) * | 2019-06-03 | 2020-12-04 | 康普药业股份有限公司 | 一种马来酸桂哌齐特中间体的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1151104B (it) * | 1982-02-04 | 1986-12-17 | Delalande Sa | Impiego terapeutico di derivati (1-cinnamoil oppure 1-fenetil-carbonil)piperazinici |
FR2522325B1 (fr) * | 1982-02-26 | 1985-08-09 | Delalande Sa | Nouveaux derives aryliques de la piperazine, de l'homopiperazine et de n,n'-dialkyl diamino-1,2 ethane, leur procede de preparation et leur application en therapeutique |
CN1246310C (zh) * | 2004-11-22 | 2006-03-22 | 北京四环制药有限公司 | 马来酸桂哌齐特合成方法 |
CN101362738B (zh) * | 2008-09-22 | 2011-01-26 | 福建金山生物制药股份有限公司 | 一种马来酸桂哌齐特的制备方法 |
-
2008
- 2008-12-19 CN CN2008102299578A patent/CN101591310B/zh not_active Expired - Fee Related
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012176621A1 (ja) * | 2011-06-24 | 2012-12-27 | 株式会社ダイセル | 不飽和カルボン酸アミド組成物の製造方法 |
JP2013006795A (ja) * | 2011-06-24 | 2013-01-10 | Daicel Corp | 不飽和カルボン酸アミド組成物の製造方法 |
JPWO2012176693A1 (ja) * | 2011-06-24 | 2015-02-23 | 東京応化工業株式会社 | 新規化合物 |
EP2725011A4 (en) * | 2011-06-24 | 2015-03-04 | Tokyo Ohka Kogyo Co Ltd | NEW COMPOUND |
CN110963983A (zh) * | 2018-09-28 | 2020-04-07 | 康普药业股份有限公司 | 一种马来酸桂哌齐特的制备方法 |
CN112028856A (zh) * | 2019-06-03 | 2020-12-04 | 康普药业股份有限公司 | 一种马来酸桂哌齐特中间体的制备方法 |
CN112028856B (zh) * | 2019-06-03 | 2024-03-26 | 康普药业股份有限公司 | 一种马来酸桂哌齐特中间体的制备方法 |
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Publication number | Publication date |
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CN101591310B (zh) | 2012-03-21 |
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