CN1095845C - 制取冻干的1β,10β－环氧－13－二甲基氨基－愈创－3(4)－烯－6,12－内酯盐酸盐的方法和装置 - Google Patents
制取冻干的1β,10β－环氧－13－二甲基氨基－愈创－3(4)－烯－6,12－内酯盐酸盐的方法和装置 Download PDFInfo
- Publication number
- CN1095845C CN1095845C CN97181524A CN97181524A CN1095845C CN 1095845 C CN1095845 C CN 1095845C CN 97181524 A CN97181524 A CN 97181524A CN 97181524 A CN97181524 A CN 97181524A CN 1095845 C CN1095845 C CN 1095845C
- Authority
- CN
- China
- Prior art keywords
- extractor
- arglabine
- gas
- solution
- extraction agent
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000002699 waste material Substances 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 16
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 238000005576 amination reaction Methods 0.000 claims abstract description 11
- 238000004108 freeze drying Methods 0.000 claims abstract description 10
- 238000001953 recrystallisation Methods 0.000 claims abstract description 8
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 239000000284 extract Substances 0.000 claims description 33
- 239000007789 gas Substances 0.000 claims description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 239000006200 vaporizer Substances 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 230000005587 bubbling Effects 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 240000006891 Artemisia vulgaris Species 0.000 claims 1
- 238000000605 extraction Methods 0.000 abstract description 65
- 238000002360 preparation method Methods 0.000 abstract description 14
- 239000002245 particle Substances 0.000 abstract description 7
- 230000000259 anti-tumor effect Effects 0.000 abstract description 5
- 238000009423 ventilation Methods 0.000 abstract description 4
- UVJYAKBJSGRTHA-ZCRGAIPPSA-N arglabin Chemical compound C1C[C@H]2C(=C)C(=O)O[C@@H]2[C@@H]2C(C)=CC[C@]32O[C@]31C UVJYAKBJSGRTHA-ZCRGAIPPSA-N 0.000 abstract description 3
- UVJYAKBJSGRTHA-UHFFFAOYSA-N arglabin Natural products C1CC2C(=C)C(=O)OC2C2C(C)=CCC32OC31C UVJYAKBJSGRTHA-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002093 peripheral effect Effects 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract 3
- 238000004566 IR spectroscopy Methods 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 239000005445 natural material Substances 0.000 abstract 1
- 238000005192 partition Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 description 58
- 239000002994 raw material Substances 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 15
- 238000009833 condensation Methods 0.000 description 13
- 230000005494 condensation Effects 0.000 description 13
- 238000001035 drying Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000003708 ampul Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000005057 refrigeration Methods 0.000 description 4
- 244000030166 artemisia Species 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000002246 antineoplastic agent Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000007599 discharging Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000007038 hydrochlorination reaction Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000013441 quality evaluation Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 235000003826 Artemisia Nutrition 0.000 description 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001411320 Eriogonum inflatum Species 0.000 description 1
- MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 235000009052 artemisia Nutrition 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- -1 by handling Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012549 training Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D11/00—Solvent extraction
- B01D11/02—Solvent extraction of solids
- B01D11/0215—Solid material in other stationary receptacles
- B01D11/0223—Moving bed of solid material
- B01D11/0226—Moving bed of solid material with the general transport direction of the solids parallel to the rotation axis of the conveyor, e.g. worm
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Extraction Or Liquid Replacement (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KZ9609951 | 1996-12-20 | ||
| KZ960995 | 1996-12-20 | ||
| KZ9703971 | 1997-04-26 | ||
| KZ970397 | 1997-04-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1245501A CN1245501A (zh) | 2000-02-23 |
| CN1095845C true CN1095845C (zh) | 2002-12-11 |
Family
ID=26639596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN97181524A Expired - Lifetime CN1095845C (zh) | 1996-12-20 | 1997-12-19 | 制取冻干的1β,10β－环氧－13－二甲基氨基－愈创－3(4)－烯－6,12－内酯盐酸盐的方法和装置 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0946565B1 (enExample) |
| JP (2) | JP2001505548A (enExample) |
| CN (1) | CN1095845C (enExample) |
| AT (1) | ATE252104T1 (enExample) |
| DE (1) | DE69725604T2 (enExample) |
| WO (1) | WO1998028303A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5994388A (en) | 1997-03-18 | 1999-11-30 | The Children's Medical Center Corporation | Cytochalasin and isoindolinone derivatives as inhibitors of angiogenesis |
| CA2397558A1 (en) | 2000-02-24 | 2001-08-30 | Janssen Pharmaceutica N.V. | Dosing regimen |
| DE60322686D1 (de) * | 2002-03-20 | 2008-09-18 | Matsushita Electric Industrial Co Ltd | Extraktionsvorrichtung |
| DE10326152A1 (de) * | 2003-06-06 | 2005-01-05 | Aventis Pharma Deutschland Gmbh | Verfahren und Vorrichtung zur quantitativen Analyse von Lösungen und Dispersionen mittels Nahinfrarot-Spektroskopie |
| US20050003422A1 (en) | 2003-07-01 | 2005-01-06 | Mitch Reponi | Methods for assessing and treating cancer |
| DE102004037002B4 (de) * | 2004-07-30 | 2006-06-14 | Chemieanlagenbau Chemnitz Gmbh | Verfahren zur Herstellung von Dimethylaminoarglabin-Hydrochlorid |
| WO2006052718A2 (en) | 2004-11-05 | 2006-05-18 | Janssen Pharmaceutica N.V. | Farnesyltransferase inhibitors for treating sepsis |
| US20060281788A1 (en) | 2005-06-10 | 2006-12-14 | Baumann Christian A | Synergistic modulation of flt3 kinase using a flt3 inhibitor and a farnesyl transferase inhibitor |
| US8697716B2 (en) | 2006-04-20 | 2014-04-15 | Janssen Pharmaceutica Nv | Method of inhibiting C-KIT kinase |
| WO2007124322A1 (en) | 2006-04-20 | 2007-11-01 | Janssen Pharmaceutica N.V. | Inhibitors of c-fms kinase |
| PL2021335T3 (pl) | 2006-04-20 | 2011-10-31 | Janssen Pharmaceutica Nv | Związki heterocykliczne jako inhibitory kinazy C-FMS |
| EP2069357B1 (en) * | 2006-09-19 | 2015-08-26 | Sergazy Mynzhasarovich Adekenov | Method for production of hydrochloride 1(10) beta-epoxy-13-dimethylamino-5,7alpha,6,11beta (h)-guaia-3(4)-en-6,12-olide, the lyophilized antitumor preparation "arglabin" |
| JO3240B1 (ar) | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| CN102190663B (zh) * | 2010-03-02 | 2013-11-13 | 石药集团中奇制药技术（石家庄）有限公司 | 一种二甲氨基阿格拉宾盐酸盐晶型 |
| CN102190662B (zh) * | 2010-03-02 | 2014-06-25 | 石药集团中奇制药技术（石家庄）有限公司 | 一种二甲氨基阿格拉宾盐酸盐的制备方法 |
| CN102372723B (zh) * | 2010-08-19 | 2014-03-26 | 石药集团中奇制药技术（石家庄）有限公司 | 一种从多花蒿中提取阿格拉宾的方法 |
| JOP20180012A1 (ar) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | عملية السلفنة باستخدام نونافلوروبوتانيسولفونيل فلوريد |
| JP6359537B2 (ja) | 2012-08-07 | 2018-07-18 | ヤンセン ファーマシューティカ エヌ．ベー． | 複素環エステル誘導体の調製プロセス |
| CN102850372A (zh) * | 2012-10-15 | 2013-01-02 | 河北医科大学 | 一种蓍草倍半萜内酯化合物及其提取方法和应用 |
| CN103833766B (zh) * | 2012-11-23 | 2016-12-21 | 天津尚德药缘科技股份有限公司 | 阿格拉滨二甲胺富马酸盐及其在药物制备中的用途 |
| CN107787373B (zh) | 2015-08-17 | 2021-11-26 | 库拉肿瘤学公司 | 法尼基转移酶抑制剂在制备用于治疗癌症的药物中的用途 |
| CN105251236B (zh) * | 2015-11-02 | 2018-01-16 | 济宁金百特生物机械有限公司 | 逆流提取装置 |
| WO2017184968A1 (en) | 2016-04-22 | 2017-10-26 | Kura Oncology, Inc. | Methods of selecting cancer patients for treatment with farnesyltransferase inhibitors |
| HUE053927T2 (hu) | 2016-11-03 | 2021-07-28 | Kura Oncology Inc | Farneziltranszferáz inhibitorok rák kezelésében történõ alkalmazásra |
| US10137121B2 (en) | 2017-02-21 | 2018-11-27 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| EP3432883B1 (en) | 2017-02-21 | 2021-07-28 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| AU2018313738B2 (en) | 2017-08-07 | 2024-07-04 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| US10806730B2 (en) | 2017-08-07 | 2020-10-20 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| WO2019113269A1 (en) | 2017-12-08 | 2019-06-13 | Kura Oncology, Inc. | Methods of treating cancer patients with farnesyltransferase inhibitors |
| US20220002396A1 (en) | 2018-11-01 | 2022-01-06 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| CN113365630A (zh) | 2018-12-21 | 2021-09-07 | 库拉肿瘤学公司 | 用于鳞状细胞癌的疗法 |
| WO2020180663A1 (en) | 2019-03-01 | 2020-09-10 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| WO2020190604A1 (en) | 2019-03-15 | 2020-09-24 | Kura Oncology, Inc. | Methods of treating cancer patients with farnesyltransferase inhibitors |
| EP3946338B1 (en) | 2019-03-29 | 2025-06-18 | Kura Oncology, Inc. | Methods of treating squamous cell carcinomas with farnesyltransferase inhibitors |
| US20220168296A1 (en) | 2019-04-01 | 2022-06-02 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| WO2020223583A1 (en) | 2019-05-02 | 2020-11-05 | Kura Oncology, Inc. | Methods of treating acute myeloid leukemia with farnesyltransferase inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1627208A1 (ru) * | 1988-05-24 | 1991-02-15 | Всесоюзный научно-исследовательский институт консервной и овощесушильной промышленности | Секционный лопастной экстрактор дл сухого растительного сырь |
-
1997
- 1997-12-19 DE DE69725604T patent/DE69725604T2/de not_active Expired - Lifetime
- 1997-12-19 EP EP97947981A patent/EP0946565B1/en not_active Expired - Lifetime
- 1997-12-19 CN CN97181524A patent/CN1095845C/zh not_active Expired - Lifetime
- 1997-12-19 JP JP51603098A patent/JP2001505548A/ja not_active Ceased
- 1997-12-19 AT AT97947981T patent/ATE252104T1/de not_active IP Right Cessation
- 1997-12-19 WO PCT/KZ1997/000006 patent/WO1998028303A1/en not_active Ceased
-
2007
- 2007-01-31 JP JP2007020702A patent/JP2007137890A/ja active Pending
Non-Patent Citations (2)
| Title |
|---|
| ADVANCED ORGANIC CHEMISTRY(第3版) 1985.1.1 J.MARCH * |
| C.A.VOL.98.NO.11,86299Q 1983.3.1 S.M.ADEKENOV * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0946565A1 (en) | 1999-10-06 |
| ATE252104T1 (de) | 2003-11-15 |
| DE69725604T2 (de) | 2005-03-03 |
| JP2007137890A (ja) | 2007-06-07 |
| CN1245501A (zh) | 2000-02-23 |
| JP2001505548A (ja) | 2001-04-24 |
| EP0946565B1 (en) | 2003-10-15 |
| WO1998028303A1 (en) | 1998-07-02 |
| DE69725604D1 (de) | 2003-11-20 |
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