CN105949264A - 人参皂苷c-k的两种晶型及其制备方法 - Google Patents
人参皂苷c-k的两种晶型及其制备方法 Download PDFInfo
- Publication number
- CN105949264A CN105949264A CN201610297739.2A CN201610297739A CN105949264A CN 105949264 A CN105949264 A CN 105949264A CN 201610297739 A CN201610297739 A CN 201610297739A CN 105949264 A CN105949264 A CN 105949264A
- Authority
- CN
- China
- Prior art keywords
- crystal formation
- ginseng saponin
- water
- organic solvent
- crystal
- 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.)
- Pending
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- FVIZARNDLVOMSU-IRFFNABBSA-N ginsenoside C-K Chemical compound O([C@@](C)(CCC=C(C)C)[C@@H]1[C@@H]2[C@@]([C@@]3(CC[C@H]4C(C)(C)[C@@H](O)CC[C@]4(C)[C@H]3C[C@H]2O)C)(C)CC1)[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O FVIZARNDLVOMSU-IRFFNABBSA-N 0.000 title abstract description 4
- 241000208340 Araliaceae Species 0.000 claims description 68
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 68
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 68
- 235000008434 ginseng Nutrition 0.000 claims description 68
- 239000001397 quillaja saponaria molina bark Substances 0.000 claims description 64
- 229930182490 saponin Natural products 0.000 claims description 64
- 150000007949 saponins Chemical class 0.000 claims description 64
- 230000015572 biosynthetic process Effects 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 13
- 239000007787 solid Substances 0.000 claims description 10
- 239000012065 filter cake Substances 0.000 claims description 8
- 239000012046 mixed solvent Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000001704 evaporation Methods 0.000 claims description 5
- 230000008020 evaporation Effects 0.000 claims description 5
- 239000000725 suspension Substances 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 2
- -1 wherein Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 description 50
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 238000000034 method Methods 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229930182494 ginsenoside Natural products 0.000 description 3
- 229940089161 ginsenoside Drugs 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 238000000982 solution X-ray diffraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610297739.2A CN105949264A (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610297739.2A CN105949264A (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
| CN201210093293.3A CN103360450B (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210093293.3A Division CN103360450B (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105949264A true CN105949264A (zh) | 2016-09-21 |
Family
ID=49299992
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610297739.2A Pending CN105949264A (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
| CN201210093293.3A Active CN103360450B (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201210093293.3A Active CN103360450B (zh) | 2012-04-01 | 2012-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9643992B2 (enExample) |
| EP (1) | EP2835377B1 (enExample) |
| JP (1) | JP2015511608A (enExample) |
| CN (2) | CN105949264A (enExample) |
| IN (1) | IN2014MN01941A (enExample) |
| WO (1) | WO2013149571A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3925966T3 (pl) * | 2020-05-04 | 2025-03-31 | Curacle Co., Ltd. | Nowa krystaliczna postać związku blokującego przeciek naczyniowy |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1417345A (zh) * | 2001-11-06 | 2003-05-14 | 中国科学院大连化学物理研究所 | 用酶水解人参皂甙制备20－β－D－吡喃葡萄糖基原人参二醇 |
| CN1465694A (zh) * | 2002-06-20 | 2004-01-07 | 中国科学院大连化学物理研究所 | 一种黑曲霉及用其酵解人参皂甙制备稀有低极性人参皂甙的方法 |
| CN101921304A (zh) * | 2009-06-17 | 2010-12-22 | 浙江海正药业股份有限公司 | 一种运用大孔树脂纯化人参皂甙compound-K的方法 |
| CN102251009A (zh) * | 2011-06-09 | 2011-11-23 | 华侨大学 | 一种稀有人参皂甙ih-901结晶的简易生产方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK9742002A3 (en) * | 2000-01-07 | 2003-02-04 | Transform Pharmaceuticals Inc | High-throughput formation, identification, and analysis of diverse solid-forms |
| CN100487131C (zh) | 2004-04-27 | 2009-05-13 | 复旦大学 | 一种制备人参皂甙Compound-K的方法 |
| CN101139562B (zh) | 2007-07-02 | 2010-06-09 | 昆明诺唯金参生物工程有限责任公司 | 一种链霉菌发酵三七皂苷制备稀有人参皂苷Compound K的方法 |
| CN103087138B (zh) | 2013-01-10 | 2015-06-24 | 天津大学 | 一种人参皂苷c-k一水合物晶体及制备方法 |
-
2012
- 2012-04-01 CN CN201610297739.2A patent/CN105949264A/zh active Pending
- 2012-04-01 CN CN201210093293.3A patent/CN103360450B/zh active Active
-
2013
- 2013-04-01 EP EP13772541.2A patent/EP2835377B1/en not_active Not-in-force
- 2013-04-01 US US14/389,345 patent/US9643992B2/en active Active
- 2013-04-01 IN IN1941MUN2014 patent/IN2014MN01941A/en unknown
- 2013-04-01 WO PCT/CN2013/073562 patent/WO2013149571A1/zh not_active Ceased
- 2013-04-01 JP JP2015502084A patent/JP2015511608A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1417345A (zh) * | 2001-11-06 | 2003-05-14 | 中国科学院大连化学物理研究所 | 用酶水解人参皂甙制备20－β－D－吡喃葡萄糖基原人参二醇 |
| CN1465694A (zh) * | 2002-06-20 | 2004-01-07 | 中国科学院大连化学物理研究所 | 一种黑曲霉及用其酵解人参皂甙制备稀有低极性人参皂甙的方法 |
| CN101921304A (zh) * | 2009-06-17 | 2010-12-22 | 浙江海正药业股份有限公司 | 一种运用大孔树脂纯化人参皂甙compound-K的方法 |
| CN102251009A (zh) * | 2011-06-09 | 2011-11-23 | 华侨大学 | 一种稀有人参皂甙ih-901结晶的简易生产方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2835377B1 (en) | 2018-12-05 |
| US20150057440A1 (en) | 2015-02-26 |
| JP2015511608A (ja) | 2015-04-20 |
| EP2835377A4 (en) | 2016-03-30 |
| US9643992B2 (en) | 2017-05-09 |
| CN103360450A (zh) | 2013-10-23 |
| IN2014MN01941A (enExample) | 2015-07-10 |
| EP2835377A1 (en) | 2015-02-11 |
| CN103360450B (zh) | 2016-05-11 |
| WO2013149571A1 (zh) | 2013-10-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103641822B (zh) | 一种卡格列净化合物及其药物组合物 | |
| CN101255180B (zh) | 二苯乙烯苷衍生物 | |
| CN104177370A (zh) | 一种从芝麻粕中制备高含量芝麻素的方法 | |
| CN108211417B (zh) | 一种植物提取黄酮用提取辅助物的制备方法与应用 | |
| CN103896930B (zh) | 卡格列净半水合物药用晶型的制备方法 | |
| CN102924467B (zh) | 一种从鸦胆子中提取纯化鸦胆子素d的制备方法 | |
| CN102000066B (zh) | 水朝阳旋覆花提取物,以其为有效成分的抗肿瘤药物及其制备方法和应用 | |
| CN105949264A (zh) | 人参皂苷c-k的两种晶型及其制备方法 | |
| CN105384686B (zh) | 一种博舒替尼结晶方法 | |
| CN107629065A (zh) | 一种从狭叶白鲜皮中分离富集呋喃喹啉类生物碱的方法 | |
| CN106496007B (zh) | 生姜中6-姜酚的分离提取方法 | |
| CN104628564A (zh) | 非诺贝特酸胆碱盐晶型及其制备方法 | |
| CN106632521A (zh) | 一种从山茱萸果实中提纯马钱苷的方法 | |
| CN101514143A (zh) | 一种白果酚的制备方法 | |
| CN112898263B (zh) | 一种从佛手中分离的香豆素骈木脂素化合物及其保肝用途 | |
| CN104311615B (zh) | 从陇蜀杜鹃叶中提取分离金丝桃苷和棉花皮素‑3‑O‑β‑D‑半乳糖苷的方法 | |
| CN103232503A (zh) | 一种马鞭草苷的制备方法 | |
| CN102351835B (zh) | 芒果苷元晶型及其组合物、制备方法与应用 | |
| CN106008646A (zh) | 人参皂苷c-k化合物多晶型及其制备方法 | |
| CN106565479A (zh) | 朝鲜蓟中绿原酸的提取方法 | |
| CN102911241A (zh) | 从土贝母中制备贝萼皂苷元的方法 | |
| CN102805759A (zh) | 红旱莲总黄酮及其提取方法与应用 | |
| CN102372753A (zh) | 一种提取哈巴俄苷的方法 | |
| CN104447785A (zh) | 一种小钻中长南五味子素d的提取方法 | |
| CN103102316A (zh) | ZD1839Form 1晶型的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20160921 |
|
| WD01 | Invention patent application deemed withdrawn after publication |