CN102643255B - 一种炎琥宁化合物 - Google Patents
一种炎琥宁化合物 Download PDFInfo
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- CN102643255B CN102643255B CN 201210085433 CN201210085433A CN102643255B CN 102643255 B CN102643255 B CN 102643255B CN 201210085433 CN201210085433 CN 201210085433 CN 201210085433 A CN201210085433 A CN 201210085433A CN 102643255 B CN102643255 B CN 102643255B
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- China
- Prior art keywords
- potassium sodium
- dehydroandroan drographolide
- sodium dehydroandroan
- drographolide succinate
- preparation
- 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.)
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- -1 Andrographolide compound Chemical class 0.000 title claims abstract description 29
- ASLUCFFROXVMFL-UHFFFAOYSA-N andrographolide Natural products CC1(CO)C(O)CCC2(C)C(CC=C3/C(O)OCC3=O)C(=C)CCC12 ASLUCFFROXVMFL-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 66
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 15
- 229910017488 Cu K Inorganic materials 0.000 claims abstract description 9
- 229910017541 Cu-K Inorganic materials 0.000 claims abstract description 9
- KYEPHZAHIRDQSR-SXASYTFBSA-L potassium;sodium;4-[[(1r,2r,4ar,5r,8as)-2-(3-carboxylatopropanoyloxy)-1,4a-dimethyl-6-methylidene-5-[(e)-2-(5-oxo-2h-furan-4-yl)ethenyl]-3,4,5,7,8,8a-hexahydro-2h-naphthalen-1-yl]methoxy]-4-oxobutanoate Chemical compound [Na+].[K+].C(/[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@H]([C@]2(COC(=O)CCC([O-])=O)C)OC(=O)CCC([O-])=O)=C\C1=CCOC1=O KYEPHZAHIRDQSR-SXASYTFBSA-L 0.000 claims description 92
- 239000000243 solution Substances 0.000 claims description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- 238000003756 stirring Methods 0.000 claims description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 52
- 238000002360 preparation method Methods 0.000 claims description 41
- 238000002156 mixing Methods 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 18
- 229910052700 potassium Inorganic materials 0.000 claims description 18
- 239000011591 potassium Substances 0.000 claims description 18
- 239000000725 suspension Substances 0.000 claims description 18
- 239000007788 liquid Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- YTHKMAIVPFVDNU-GPTWTFMPSA-N 4-[[(1r,2r,4ar,5r,8as)-2-(3-carboxypropanoyloxy)-1,4a-dimethyl-6-methylidene-5-[(e)-2-(5-oxo-2h-furan-4-yl)ethenyl]-3,4,5,7,8,8a-hexahydro-2h-naphthalen-1-yl]methoxy]-4-oxobutanoic acid Chemical compound C(/[C@@H]1C(=C)CC[C@H]2[C@@]1(C)CC[C@H]([C@]2(COC(=O)CCC(O)=O)C)OC(=O)CCC(O)=O)=C\C1=CCOC1=O YTHKMAIVPFVDNU-GPTWTFMPSA-N 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 13
- 239000000706 filtrate Substances 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000000967 suction filtration Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 9
- 230000005260 alpha ray Effects 0.000 claims description 8
- 238000001291 vacuum drying Methods 0.000 claims description 8
- 238000010792 warming Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 abstract description 37
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000012360 testing method Methods 0.000 description 32
- 238000000034 method Methods 0.000 description 24
- 239000000843 powder Substances 0.000 description 23
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- 230000000052 comparative effect Effects 0.000 description 15
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- 238000002347 injection Methods 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 230000008859 change Effects 0.000 description 10
- 238000012856 packing Methods 0.000 description 10
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- 238000013112 stability test Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
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- 238000012552 review Methods 0.000 description 8
- 238000004088 simulation Methods 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000005286 illumination Methods 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910001415 sodium ion Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000012982 microporous membrane Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical compound [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 description 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 2
- 229960000258 corticotropin Drugs 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 2
- 239000008227 sterile water for injection Substances 0.000 description 2
- 150000003900 succinic acid esters Chemical class 0.000 description 2
- 238000000108 ultra-filtration Methods 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- 241000746375 Andrographis Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241001113283 Respirovirus Species 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000003470 adrenal cortex hormone Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000003570 biosynthesizing effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000004856 capillary permeability Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
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- 238000006297 dehydration reaction Methods 0.000 description 1
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- 238000004108 freeze drying Methods 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000008354 sodium chloride injection Substances 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
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- 241000701161 unidentified adenovirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Images
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
实施例3 | 对比例1 | 对比例2 | 对比例3 | |
步骤(1) | 6℃ | 25℃ | 1℃ | 6℃ |
步骤(2) | 6℃ | 25℃ | 1℃ | 6℃ |
步骤(3) | 10℃ | 25℃ | 1℃ | 6℃ |
步骤(4) | 6℃ | 25℃ | 1℃ | 6℃ |
纯度(HPLC) | 99.96% | 95.18% | 97.03% | 99.15% |
收率 | 99.2% | 92.3% | 87.8% | 98.8% |
实施例3 | 对比例4 | 对比例5 | 对比例6 | |
炎琥宁水溶液与不良溶剂的比例 | 1∶3 | 1∶3 | 1∶0.5 | 1∶10 |
乙醇∶乙醚体积比为 | 1∶3 | 1∶1 | 1∶3 | 1∶3 |
纯度(HPLC) | 99.96% | 96.35% | 93.74% | 99.21% |
收率 | 99.2% | 96.1% | 89.3% | 91.6% |
Claims (13)
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CN 201210085433 CN102643255B (zh) | 2012-03-27 | 2012-03-27 | 一种炎琥宁化合物 |
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CN102643255A CN102643255A (zh) | 2012-08-22 |
CN102643255B true CN102643255B (zh) | 2013-05-01 |
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Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103193738B (zh) * | 2013-04-16 | 2014-08-20 | 成都天台山制药有限公司 | 炎琥宁结晶及其用途 |
CN104744412A (zh) * | 2015-04-07 | 2015-07-01 | 重庆药友制药有限责任公司 | 一种炎琥宁化合物 |
CN106854190A (zh) * | 2016-11-18 | 2017-06-16 | 珠海同源药业有限公司 | 一种新的炎琥宁化合物及其药物组合物 |
CN108658905B (zh) * | 2018-04-25 | 2023-02-14 | 四川子仁制药有限公司 | 一种用于降低炎琥宁原料药成品中有关物质的方法 |
CN110467589B (zh) * | 2019-08-28 | 2023-04-07 | 武汉大学 | 一种炎琥宁无菌原料药的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101260097B (zh) * | 2008-04-18 | 2012-05-02 | 长春迈灵生物工程有限公司 | 以穿琥宁为原料制备穿心莲内酯琥珀酸半酯钾钠盐的工艺 |
CN102030731B (zh) * | 2010-12-28 | 2012-07-11 | 哈药集团三精制药股份有限公司 | 一种溶媒结晶法低温制备高纯度炎琥宁的方法 |
CN102367243B (zh) * | 2011-08-26 | 2013-03-27 | 贺金凤 | 一种更为稳定的炎琥宁化合物及其药物组合物 |
CN102382082B (zh) * | 2011-09-07 | 2012-07-18 | 周晓东 | 一种炎琥宁化合物及其药物组合物 |
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