JPS6256160B2 - - Google Patents
Info
- Publication number
- JPS6256160B2 JPS6256160B2 JP12517580A JP12517580A JPS6256160B2 JP S6256160 B2 JPS6256160 B2 JP S6256160B2 JP 12517580 A JP12517580 A JP 12517580A JP 12517580 A JP12517580 A JP 12517580A JP S6256160 B2 JPS6256160 B2 JP S6256160B2
- Authority
- JP
- Japan
- Prior art keywords
- hplc
- chloroform
- under reduced
- glycoside
- reduced pressure
- 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
Links
- 229930182470 glycoside Natural products 0.000 claims description 16
- 150000002338 glycosides Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 5
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 150000001875 compounds Chemical class 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
- 239000003480 eluent Substances 0.000 description 11
- 238000010828 elution Methods 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000843 powder Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001514 detection method Methods 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- 238000011894 semi-preparative HPLC Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 238000004305 normal phase HPLC Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000004007 reversed phase HPLC Methods 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- CETRJNFIKWWGQO-UHFFFAOYSA-N methanol;oxalic acid Chemical compound OC.OC(=O)C(O)=O CETRJNFIKWWGQO-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 241000208327 Apocynaceae Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000000434 field desorption mass spectrometry Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229940100688 oral solution Drugs 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12517580A JPS5748998A (en) | 1980-09-09 | 1980-09-09 | Novel condurango glycoside, its preparation and antitumor agent containing the same |
| IT8167295A IT1144136B (it) | 1980-03-05 | 1981-03-03 | Glucosidi di condurango agenti antitumorali che li comprendono e procedimento per la loro preparazione |
| BE0/204013A BE887793A (fr) | 1980-03-05 | 1981-03-04 | Nouveaux condurango-glycosides, agents antitumeurs en comprenant et procede pour les preparer |
| AU67800/81A AU6780081A (en) | 1980-03-05 | 1981-03-05 | Novel cundurango glycosides, process for their preparation, antineoplastic agent, and composition containing same |
| DE19813137612 DE3137612A1 (de) | 1980-03-05 | 1981-03-05 | Novel cundurango glycosides,process for their preparation,antineoplastic agent,and composition containing same |
| US06/320,974 US4452786A (en) | 1980-03-05 | 1981-03-05 | Condurango glycoside compounds, processes for their preparation, antitumor agents comprising them and compositions |
| CH7326/81A CH647533A5 (de) | 1980-03-05 | 1981-03-05 | Cundurango-glycosid-verbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende tumorbekaempfende mittel. |
| PCT/JP1981/000045 WO1981002577A1 (en) | 1980-03-05 | 1981-03-05 | Novel cundurango glycosides,process for their preparation,antineoplastic agent,and composition containing same |
| CA000372389A CA1169852A (en) | 1980-03-05 | 1981-03-05 | Condurango glycoside compounds, antitumor agents comprising them and processes for their preparation |
| EP19810900551 EP0054570A4 (en) | 1980-03-05 | 1981-03-05 | NOVEL CONDURANGO GLYCOSIDES, PROCESS FOR THE PREPARATION THEREOF, ANTINEOPLAST AGENTS, AND COMPOSITION CONTAINING THE SAME. |
| GB8209580A GB2093032B (en) | 1980-03-05 | 1981-03-05 | Novel condurango glycosides process for their preparation antineoplastic agent and composition containing same |
| SE8202140A SE8202140L (sv) | 1980-03-05 | 1982-04-02 | Nya condurango-glykosidforeningar, forfarande for deras framstellning, antitumormedel som omfattar dem och kompositioner der de ingar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12517580A JPS5748998A (en) | 1980-09-09 | 1980-09-09 | Novel condurango glycoside, its preparation and antitumor agent containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5748998A JPS5748998A (en) | 1982-03-20 |
| JPS6256160B2 true JPS6256160B2 (enrdf_load_stackoverflow) | 1987-11-24 |
Family
ID=14903741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12517580A Granted JPS5748998A (en) | 1980-03-05 | 1980-09-09 | Novel condurango glycoside, its preparation and antitumor agent containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5748998A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS588314Y2 (ja) * | 1980-12-08 | 1983-02-15 | 株式会社 タカラ | 玩具ハンマ− |
-
1980
- 1980-09-09 JP JP12517580A patent/JPS5748998A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5748998A (en) | 1982-03-20 |
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