JP2007137890A5 - - Google Patents
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- Publication number
- JP2007137890A5 JP2007137890A5 JP2007020702A JP2007020702A JP2007137890A5 JP 2007137890 A5 JP2007137890 A5 JP 2007137890A5 JP 2007020702 A JP2007020702 A JP 2007020702A JP 2007020702 A JP2007020702 A JP 2007020702A JP 2007137890 A5 JP2007137890 A5 JP 2007137890A5
- Authority
- JP
- Japan
- Prior art keywords
- solution
- alcohol
- hydrochloride
- algravin
- aminoalgravin
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 238000005576 amination reaction Methods 0.000 claims description 6
- 229930002875 chlorophyll Natural products 0.000 claims description 4
- 235000019804 chlorophyll Nutrition 0.000 claims description 4
- 238000004440 column chromatography Methods 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
- 150000002632 lipids Chemical class 0.000 claims description 4
- 102000004169 proteins and genes Human genes 0.000 claims description 4
- 108090000623 proteins and genes Proteins 0.000 claims description 4
- 239000013557 residual solvent Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000004566 IR spectroscopy Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000005445 natural material Substances 0.000 claims description 2
- 238000005273 aeration Methods 0.000 claims 1
- 239000001752 chlorophylls and chlorophyllins Substances 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- 239000000047 product Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 235000003826 Artemisia Nutrition 0.000 description 3
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- 244000030166 artemisia Species 0.000 description 3
- 235000009052 artemisia Nutrition 0.000 description 3
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000005192 partition Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007799 cork Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water 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
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012931 lyophilized formulation Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 241000196324 Embryophyta 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 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 description 1
- UVJYAKBJSGRTHA-UHFFFAOYSA-N arglabin Natural products C1CC2C(=C)C(=O)OC2C2C(C)=CCC32OC31C UVJYAKBJSGRTHA-UHFFFAOYSA-N 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
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229930009674 sesquiterpene lactone Natural products 0.000 description 1
- 150000002107 sesquiterpene lactone derivatives Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KZ960995.1 | 1996-12-20 | ||
| KZ960995 | 1996-12-20 | ||
| KZ970397.1 | 1997-04-23 | ||
| KZ970397 | 1997-04-26 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51603098A Division JP2001505548A (ja) | 1996-12-20 | 1997-12-19 | 凍結乾燥ハイドロクロライド−１β，１０β−エポキシ−１３−ジメチルアミノ−グアヤ−３（４）−エン−６，１２−オリドの生成方法および装置 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007137890A JP2007137890A (ja) | 2007-06-07 |
| JP2007137890A5 true JP2007137890A5 (OSRAM) | 2007-09-13 |
| JP2007137890A6 JP2007137890A6 (ja) | 2007-11-08 |
Family
ID=26639596
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51603098A Ceased JP2001505548A (ja) | 1996-12-20 | 1997-12-19 | 凍結乾燥ハイドロクロライド−１β，１０β−エポキシ−１３−ジメチルアミノ−グアヤ−３（４）−エン−６，１２−オリドの生成方法および装置 |
| JP2007020702A Pending JP2007137890A (ja) | 1996-12-20 | 2007-01-31 | 凍結乾燥ハイドロクロライド−１β，１０β−エポキシ−１３−ジメチルアミノ−グアヤ−３（４）−エン−６，１２−オリドの生成方法および装置 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51603098A Ceased JP2001505548A (ja) | 1996-12-20 | 1997-12-19 | 凍結乾燥ハイドロクロライド−１β，１０β−エポキシ−１３−ジメチルアミノ−グアヤ−３（４）−エン−６，１２−オリドの生成方法および装置 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0946565B1 (OSRAM) |
| JP (2) | JP2001505548A (OSRAM) |
| CN (1) | CN1095845C (OSRAM) |
| AT (1) | ATE252104T1 (OSRAM) |
| DE (1) | DE69725604T2 (OSRAM) |
| WO (1) | WO1998028303A1 (OSRAM) |
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 |
| EP1267848B1 (en) | 2000-02-24 | 2007-10-17 | Janssen Pharmaceutica N.V. | Dosing regimen comprising a farnesyl protein transferase inhibitor for the treatment of cancer |
| EP1491245B1 (en) * | 2002-03-20 | 2008-08-06 | Matsushita Electric Industrial Co., Ltd. | Extractor |
| 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 |
| WO2007124316A1 (en) | 2006-04-20 | 2007-11-01 | Janssen Pharmaceutica N.V. | Heterocyclic compounds as inhibitors of c-fms kinase |
| NZ572072A (en) | 2006-04-20 | 2011-09-30 | Janssen Pharmaceutica Nv | Inhibitors of c-fms kinase |
| GEP20115246B (en) * | 2006-09-19 | 2011-06-27 | Sergazy Adekenov | Method for production of hydrochloride 1(10) beta-epoxy-13-dimethylamino-5,7 alpha,6,11 beta (h)-guaia-3(4)-en-6,12-olide, 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 |
| ES2608628T3 (es) | 2012-08-07 | 2017-04-12 | Janssen Pharmaceutica Nv | Procedimiento para la preparacion de derivados de ester heterociclicos |
| JOP20180012A1 (ar) | 2012-08-07 | 2019-01-30 | Janssen Pharmaceutica Nv | عملية السلفنة باستخدام نونافلوروبوتانيسولفونيل فلوريد |
| 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 |
| HUE057306T2 (hu) | 2015-08-17 | 2022-04-28 | Kura Oncology Inc | Módszerek rákos páciensek kezelésére farneziltranszferáz inhibitorokkal |
| 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 |
| US20190119758A1 (en) | 2016-04-22 | 2019-04-25 | Kura Oncology, Inc. | Methods of selecting cancer patients for treatment with farnesyltransferase inhibitors |
| TW201818965A (zh) | 2016-11-03 | 2018-06-01 | 美商庫拉腫瘤技術股份有限公司 | 以法呢基轉移酶（ｆａｒｎｅｓｙｌ ｔｒａｎｓｆｅｒａｓｅ）抑制劑治療癌症病患之方法 |
| 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 |
| US10806730B2 (en) | 2017-08-07 | 2020-10-20 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| TW201919628A (zh) | 2017-08-07 | 2019-06-01 | 美商庫拉腫瘤技術股份有限公司 | 以法尼基轉移酶(farnesyltransferase)抑制劑治療癌症之方法 |
| WO2019113269A1 (en) | 2017-12-08 | 2019-06-13 | Kura Oncology, Inc. | Methods of treating cancer patients with farnesyltransferase inhibitors |
| CN113286591A (zh) | 2018-11-01 | 2021-08-20 | 库拉肿瘤学公司 | 用法尼基转移酶抑制剂治疗癌症的方法 |
| JP2022514654A (ja) | 2018-12-21 | 2022-02-14 | クラ オンコロジー， インコーポレイテッド | 扁平上皮癌のための治療法 |
| US20220142983A1 (en) | 2019-03-01 | 2022-05-12 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| US20220143006A1 (en) | 2019-03-15 | 2022-05-12 | Kura Oncology, Inc. | Methods of treating cancer with farnesyltransferase inhibitors |
| WO2020205486A1 (en) | 2019-03-29 | 2020-10-08 | Kura Oncology, Inc. | Methods of treating squamous cell carcinomas with farnesyltransferase inhibitors |
| TW202102218A (zh) | 2019-04-01 | 2021-01-16 | 美商庫拉腫瘤技術股份有限公司 | 以法呢基(farnesyl)轉移酶抑制劑治療癌症的方法 |
| US20220305001A1 (en) | 2019-05-02 | 2022-09-29 | 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 WO PCT/KZ1997/000006 patent/WO1998028303A1/en not_active Ceased
- 1997-12-19 AT AT97947981T patent/ATE252104T1/de not_active IP Right Cessation
- 1997-12-19 DE DE69725604T patent/DE69725604T2/de not_active Expired - Lifetime
- 1997-12-19 JP JP51603098A patent/JP2001505548A/ja not_active Ceased
- 1997-12-19 CN CN97181524A patent/CN1095845C/zh not_active Expired - Lifetime
- 1997-12-19 EP EP97947981A patent/EP0946565B1/en not_active Expired - Lifetime
-
2007
- 2007-01-31 JP JP2007020702A patent/JP2007137890A/ja active Pending
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