CN101987863A - 一种齐墩果酸哌嗪盐及其制备方法 - Google Patents
一种齐墩果酸哌嗪盐及其制备方法 Download PDFInfo
- Publication number
- CN101987863A CN101987863A CN2009100557052A CN200910055705A CN101987863A CN 101987863 A CN101987863 A CN 101987863A CN 2009100557052 A CN2009100557052 A CN 2009100557052A CN 200910055705 A CN200910055705 A CN 200910055705A CN 101987863 A CN101987863 A CN 101987863A
- Authority
- CN
- China
- Prior art keywords
- oleanolic acid
- solvent
- preparation
- piperazine salt
- crystal seed
- 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
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 title claims abstract description 133
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 title claims abstract description 133
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 title claims abstract description 133
- 229940100243 oleanolic acid Drugs 0.000 title claims abstract description 133
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 title claims abstract description 133
- -1 Oleanolic acid piperazine salt Chemical class 0.000 title claims abstract description 96
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 claims abstract description 45
- 239000000126 substance Substances 0.000 claims abstract description 9
- 239000013078 crystal Substances 0.000 claims description 92
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- 238000001816 cooling Methods 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical class CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- 238000003756 stirring Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
- 238000002425 crystallisation Methods 0.000 claims description 21
- 239000012296 anti-solvent Substances 0.000 claims description 20
- 230000008025 crystallization Effects 0.000 claims description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 14
- 238000006386 neutralization reaction Methods 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 5
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000000935 solvent evaporation Methods 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 230000008901 benefit Effects 0.000 abstract description 3
- 239000003814 drug Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
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- 238000001291 vacuum drying Methods 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 12
- 229940079593 drug Drugs 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 241000795633 Olea <sea slug> Species 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
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- 230000000694 effects Effects 0.000 description 5
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- 239000000203 mixture Substances 0.000 description 4
- 238000010899 nucleation Methods 0.000 description 4
- 230000006911 nucleation Effects 0.000 description 4
- 238000012216 screening Methods 0.000 description 4
- 229940079833 sodium oleanolate Drugs 0.000 description 4
- QNELTPKHJFMSNK-RLFONNADSA-M sodium;(4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate Chemical compound [Na+].C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C([O-])=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C QNELTPKHJFMSNK-RLFONNADSA-M 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
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- 238000002474 experimental method Methods 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
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- 208000006454 hepatitis Diseases 0.000 description 2
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- 102100036475 Alanine aminotransferase 1 Human genes 0.000 description 1
- 108010082126 Alanine transaminase Proteins 0.000 description 1
- 206010008909 Chronic Hepatitis Diseases 0.000 description 1
- 229910016860 FaSSIF Inorganic materials 0.000 description 1
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- 206010020852 Hypertonia Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
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- 239000002585 base Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
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- 238000001514 detection method Methods 0.000 description 1
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- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
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- 210000004185 liver Anatomy 0.000 description 1
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- 239000012452 mother liquor Substances 0.000 description 1
- 239000011858 nanopowder Substances 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000006191 orally-disintegrating tablet Substances 0.000 description 1
- 150000002966 pentacyclic triterpenoids Chemical class 0.000 description 1
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- 239000006187 pill Substances 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
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CN 200910055705 CN101987863B (zh) | 2009-07-31 | 2009-07-31 | 一种齐墩果酸哌嗪盐及其制备方法 |
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CN 200910055705 CN101987863B (zh) | 2009-07-31 | 2009-07-31 | 一种齐墩果酸哌嗪盐及其制备方法 |
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CN101987863A true CN101987863A (zh) | 2011-03-23 |
CN101987863B CN101987863B (zh) | 2013-10-16 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102234304A (zh) * | 2010-04-29 | 2011-11-09 | 上海开拓者医药发展有限公司 | 一种熊果酸盐、其制备方法及其晶体 |
CN102675405A (zh) * | 2012-05-24 | 2012-09-19 | 贵州大学 | 熊果酸哌嗪酰胺类化合物及其制备方法和用途 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449372A (zh) * | 2000-08-08 | 2003-10-15 | 日清奥利友株式会社 | 齐墩果酸和/或山楂酸的制备方法 |
CN1558942A (zh) * | 2001-09-28 | 2004-12-29 | 日清奥利友株式会社 | 含有齐墩果酸和/或山楂酸的油脂组合物的制造方法 |
-
2009
- 2009-07-31 CN CN 200910055705 patent/CN101987863B/zh not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1449372A (zh) * | 2000-08-08 | 2003-10-15 | 日清奥利友株式会社 | 齐墩果酸和/或山楂酸的制备方法 |
CN1558942A (zh) * | 2001-09-28 | 2004-12-29 | 日清奥利友株式会社 | 含有齐墩果酸和/或山楂酸的油脂组合物的制造方法 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102234304A (zh) * | 2010-04-29 | 2011-11-09 | 上海开拓者医药发展有限公司 | 一种熊果酸盐、其制备方法及其晶体 |
CN102234304B (zh) * | 2010-04-29 | 2014-11-05 | 上海开拓者医药发展有限公司 | 一种熊果酸盐、其制备方法及其晶体 |
CN102675405A (zh) * | 2012-05-24 | 2012-09-19 | 贵州大学 | 熊果酸哌嗪酰胺类化合物及其制备方法和用途 |
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CN101987863B (zh) | 2013-10-16 |
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Address after: 201203 Shanghai City Harley Road, Zhangjiang hi tech Park No. 965 Room 303 Patentee after: SHANGHAI PHARMAEXPLORER Co.,Ltd. Address before: 201203 Shanghai City Harley Road, Zhangjiang hi tech Park No. 965 Room 303 Patentee before: Shanghai PharmaExplorer Co.,Ltd. |
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