JP2015511608A - ジンセノシドｃ−ｋの２つの結晶形およびその製造方法 - Google Patents
ジンセノシドｃ−ｋの２つの結晶形およびその製造方法 Download PDFInfo
- Publication number
- JP2015511608A JP2015511608A JP2015502084A JP2015502084A JP2015511608A JP 2015511608 A JP2015511608 A JP 2015511608A JP 2015502084 A JP2015502084 A JP 2015502084A JP 2015502084 A JP2015502084 A JP 2015502084A JP 2015511608 A JP2015511608 A JP 2015511608A
- Authority
- JP
- Japan
- Prior art keywords
- ginsenoside
- crystal form
- producing
- crystalline form
- 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
- 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 claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000013078 crystal Substances 0.000 title claims description 72
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- 238000001914 filtration Methods 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 8
- 238000001704 evaporation Methods 0.000 claims description 8
- 230000008020 evaporation Effects 0.000 claims description 8
- 239000012065 filter cake Substances 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 5
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 241001365789 Oenanthe crocata Species 0.000 claims 1
- 229930182494 ginsenoside Natural products 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 241000208340 Araliaceae Species 0.000 description 2
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
- 235000003140 Panax quinquefolius Nutrition 0.000 description 2
- 235000008434 ginseng Nutrition 0.000 description 2
- 229940089161 ginsenoside Drugs 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 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
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000463 material Substances 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
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000982 solution X-ray diffraction Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
Images
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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201210093293.3 | 2012-04-01 | ||
| 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 |
| PCT/CN2013/073562 WO2013149571A1 (zh) | 2012-04-01 | 2013-04-01 | 人参皂苷c-k的两种晶型及其制备方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2015511608A true JP2015511608A (ja) | 2015-04-20 |
Family
ID=49299992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015502084A Pending JP2015511608A (ja) | 2012-04-01 | 2013-04-01 | ジンセノシドｃ−ｋの２つの結晶形およびその製造方法 |
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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003519698A (ja) * | 2000-01-07 | 2003-06-24 | トランスフォーム ファーマスーティカルズ，インコーポレイテッド | 多様な固体形態のハイスループットでの形成、同定および分析 |
| CN1570133A (zh) * | 2004-04-27 | 2005-01-26 | 复旦大学 | 一种制备人参皂甙Compound－K的方法 |
| CN101139562A (zh) * | 2007-07-02 | 2008-03-12 | 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的工艺 |
| 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 (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1167805C (zh) * | 2001-11-06 | 2004-09-22 | 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 |
| CN1184305C (zh) * | 2002-06-20 | 2005-01-12 | 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 |
| 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 (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003519698A (ja) * | 2000-01-07 | 2003-06-24 | トランスフォーム ファーマスーティカルズ，インコーポレイテッド | 多様な固体形態のハイスループットでの形成、同定および分析 |
| CN1570133A (zh) * | 2004-04-27 | 2005-01-26 | 复旦大学 | 一种制备人参皂甙Compound－K的方法 |
| CN101139562A (zh) * | 2007-07-02 | 2008-03-12 | 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的工艺 |
| 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 |
Non-Patent Citations (13)
| Title |
|---|
| "新医薬品の規格及び試験方法の設定について", 医薬審発第５６８号, JPN6010021254, 2001, ISSN: 0003188830 * |
| ARCHIVE OF PHARMACAL RESEARCH, vol. １８, JPN6015044297, 1995, pages 454 - 457, ISSN: 0003188828 * |
| BYRN S: "PHARMACEUTICAL SOLIDS: A STRATEGIC APPROACH TO REGULATORY CONSIDERATIONS", PHARMACEUTICAL RESEARCH, vol. V12 N7, JPN5013009960, 1 July 1995 (1995-07-01), US, pages 945 - 954, XP055307460, ISSN: 0003188834, DOI: 10.1023/A:1016241927429 * |
| CHEMISTRY & BIODIVERSITY, vol. ６, JPN6015044290, 2009, pages 380 - 388, ISSN: 0003188825 * |
| CRYSTAL RESEARCH AND TECHNOLOGY, vol. ４７, JPN6015044283, 2012, pages 377 - 384, ISSN: 0003188822 * |
| JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, vol. ８, JPN6015044286, 2006, pages 519 - 527, ISSN: 0003188823 * |
| JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, vol. ３９, JPN6015044293, 2009, pages 99 - 103, ISSN: 0003188826 * |
| JOURNAL OF DALIAN POLYTECHNIC UNIVERSITY, vol. ２８, JPN6015044295, 2009, pages 87 - 89, ISSN: 0003188827 * |
| JOURNAL OF GINSENG RESEARCH, vol. ２７, JPN6015044289, 2003, pages 129 - 134, ISSN: 0003188824 * |
| 大島寛: "結晶多形・擬多形の析出挙動と制御", PHARM STAGE, vol. 6, no. 10, JPN6011001457, 15 January 2007 (2007-01-15), pages 48 - 53, ISSN: 0003188831 * |
| 山野光久: "医薬品のプロセス研究における結晶多形現象への取り組み", 有機合成化学協会誌, vol. 65, no. 9, JPN6010003277, 1 September 2007 (2007-09-01), pages 907 - 69, ISSN: 0003188833 * |
| 川口洋子ら: "医薬品と結晶多形", 生活工学研究, vol. 4, no. 2, JPN6014015069, 2002, pages 310 - 317, ISSN: 0003188829 * |
| 高田則幸: "創薬段階における原薬Formスクリーニングと選択", PHARM STAGE, vol. 6, no. 10, JPN6009053755, 15 January 2007 (2007-01-15), pages 20 - 25, ISSN: 0003188832 * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2835377B1 (en) | 2018-12-05 |
| CN105949264A (zh) | 2016-09-21 |
| US20150057440A1 (en) | 2015-02-26 |
| 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 |
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