JPS6251277B2 - - Google Patents
Info
- Publication number
- JPS6251277B2 JPS6251277B2 JP2769780A JP2769780A JPS6251277B2 JP S6251277 B2 JPS6251277 B2 JP S6251277B2 JP 2769780 A JP2769780 A JP 2769780A JP 2769780 A JP2769780 A JP 2769780A JP S6251277 B2 JPS6251277 B2 JP S6251277B2
- Authority
- JP
- Japan
- Prior art keywords
- extract
- chloroform
- peak
- methanol
- concentrated
- 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
- 238000000926 separation method Methods 0.000 claims description 16
- 229930182470 glycoside Natural products 0.000 claims description 15
- 150000002338 glycosides Chemical class 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 239000002246 antineoplastic agent Substances 0.000 claims description 2
- 238000004811 liquid chromatography Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
- 239000000284 extract Substances 0.000 description 39
- 239000000203 mixture Substances 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 21
- 239000007788 liquid Substances 0.000 description 20
- 238000000605 extraction Methods 0.000 description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 10
- 206010028980 Neoplasm Diseases 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 238000001514 detection method Methods 0.000 description 8
- 238000010828 elution Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000011894 semi-preparative HPLC Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000010908 decantation Methods 0.000 description 6
- 239000012488 sample solution Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000003643 water by type Substances 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241000208327 Apocynaceae Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 208000006268 Sarcoma 180 Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 210000000683 abdominal cavity Anatomy 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 235000008504 concentrate Nutrition 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 210000004013 groin Anatomy 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- SGDAJMSNTKLPML-SKMKETMKSA-N Condurangogenin A Chemical compound O([C@@H]1[C@H]([C@@H]2[C@@]3(C)CC[C@H](O)C[C@@H]3CC[C@H]2[C@@]2(O)CC[C@@H]([C@]21C)C(C)=O)OC(=O)C)C(=O)\C=C\C1=CC=CC=C1 SGDAJMSNTKLPML-SKMKETMKSA-N 0.000 description 1
- NUPFZNSJJIZBGR-DSXGPZHDSA-N Condurangogenin C Chemical compound O([C@@H]1[C@@H](OC(C)=O)[C@@H]2[C@@]3(C)CC[C@H](O)C[C@@H]3CC[C@H]2[C@@]2(O)CC[C@@H]([C@@]12C)C(O)C)C(=O)\C=C\C1=CC=CC=C1 NUPFZNSJJIZBGR-DSXGPZHDSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010060891 General symptom Diseases 0.000 description 1
- 241001347462 Marsdenia cundurango Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 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
- 150000001298 alcohols Chemical class 0.000 description 1
- -1 aliphatic ester Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000004596 appetite loss Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 244000309464 bull Species 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
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 229930191727 condurangogenin Natural products 0.000 description 1
- FKXVPEBFIHNLPS-UHFFFAOYSA-N condurangogenin C Natural products CC(=O)OC1C2(C)C(C(O)C)CCC2(O)C2CCC3CC(O)CCC3(C)C2C1OC(=O)C=CC1=CC=CC=C1 FKXVPEBFIHNLPS-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007951 isotonicity adjuster Substances 0.000 description 1
- 235000021266 loss of appetite Nutrition 0.000 description 1
- 208000019017 loss of appetite Diseases 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel 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
- 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
- 208000006379 syphilis Diseases 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
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2769780A JPS56123999A (en) | 1980-03-05 | 1980-03-05 | Cundurango glycoside, its preparation and antitumor agent comprising it |
| US06/179,001 US4320120A (en) | 1979-10-22 | 1980-08-18 | Extracts of Marsdenia cundurango Reichenbach fil |
| SE8005919A SE8005919L (sv) | 1979-08-23 | 1980-08-22 | Extrakt av marsdenia cundurango reichenbach fil |
| DE19803031745 DE3031745A1 (de) | 1979-08-23 | 1980-08-22 | Extrakte von marsdenia cundurango reichenbach fil, verfahren zu deren herstellung, antitumormittel und arzneimittel, die diese extrakte enthalten, und anwendung der extrakte zur behandlung von tumoren |
| FR8018419A FR2463620A1 (fr) | 1979-08-23 | 1980-08-22 | Extraits de marsdenia cindurango reichenbach fil, des procedes de preparation de ceux-ci, des agents anti-tumeur les contenant et des compositions les contenant |
| NL8004751A NL8004751A (nl) | 1979-08-23 | 1980-08-22 | Werkwijze voor de bereiding van een geneesmiddel tegen kanker, het aldus bereide geneesmiddel en een werkwijze voor het bereiden van de actieve stof uit een plantenrest. |
| CA000358853A CA1144917A (en) | 1979-08-23 | 1980-08-22 | Extracts of marsdenia cundurango reichenbach fil |
| GB8027337A GB2060379A (en) | 1979-08-23 | 1980-08-22 | Extracts of Marsdenia cundurango Reichenbach fil |
| ES494468A ES8106684A1 (es) | 1979-08-23 | 1980-08-22 | Un procedimiento para la obtencion de un extracto de marsde-nia cundurango reichenbach fil. |
| PL22636980A PL226369A1 (enrdf_load_stackoverflow) | 1979-08-23 | 1980-08-22 | |
| IT68313/80A IT1141617B (it) | 1979-08-23 | 1980-08-25 | Estratti di marsdenia condurango reichenbach figlio |
| 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 |
| US06/320,974 US4452786A (en) | 1980-03-05 | 1981-03-05 | Condurango glycoside compounds, processes for their preparation, antitumor agents comprising them and compositions |
| 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 |
| DE19813137612 DE3137612A1 (de) | 1980-03-05 | 1981-03-05 | Novel cundurango glycosides,process for their preparation,antineoplastic agent,and composition containing same |
| AU67800/81A AU6780081A (en) | 1980-03-05 | 1981-03-05 | Novel cundurango glycosides, process for their preparation, antineoplastic agent, and composition containing same |
| NL8120043A NL8120043A (nl) | 1980-03-05 | 1981-03-05 | Nieuwe condurango glycoside-verbindingen, werkwijze voor de bereiding hiervan, anti-tumormiddelen die deze stoffen omvatten en samenstellingen, die deze middelen bevatten. |
| CH7326/81A CH647533A5 (de) | 1980-03-05 | 1981-03-05 | Cundurango-glycosid-verbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende tumorbekaempfende mittel. |
| CA000372389A CA1169852A (en) | 1980-03-05 | 1981-03-05 | Condurango glycoside compounds, antitumor agents comprising them and processes for their preparation |
| PCT/JP1981/000045 WO1981002577A1 (en) | 1980-03-05 | 1981-03-05 | Novel cundurango 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 |
|---|---|---|---|
| JP2769780A JPS56123999A (en) | 1980-03-05 | 1980-03-05 | Cundurango glycoside, its preparation and antitumor agent comprising it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56123999A JPS56123999A (en) | 1981-09-29 |
| JPS6251277B2 true JPS6251277B2 (enrdf_load_stackoverflow) | 1987-10-29 |
Family
ID=12228164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2769780A Granted JPS56123999A (en) | 1979-08-23 | 1980-03-05 | Cundurango glycoside, its preparation and antitumor agent comprising it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56123999A (enrdf_load_stackoverflow) |
-
1980
- 1980-03-05 JP JP2769780A patent/JPS56123999A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56123999A (en) | 1981-09-29 |
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