JPS638088B2 - - Google Patents
Info
- Publication number
- JPS638088B2 JPS638088B2 JP60270494A JP27049485A JPS638088B2 JP S638088 B2 JPS638088 B2 JP S638088B2 JP 60270494 A JP60270494 A JP 60270494A JP 27049485 A JP27049485 A JP 27049485A JP S638088 B2 JPS638088 B2 JP S638088B2
- Authority
- JP
- Japan
- Prior art keywords
- meoh
- acetone
- cellulose
- chromatography
- cells
- 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
- 239000002246 antineoplastic agent Substances 0.000 claims description 6
- -1 lugosin D Chemical compound 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- JMGCAHRKIVCLFW-CNWXVVPTSA-N ellagitannin Chemical class OC1=C(O)C(O)=CC(C(=O)O[C@H]2C3=C4C(=O)O[C@@H]2[C@@H]2[C@@H]5OC(=O)C6=CC(O)=C(O)C(O)=C6C6=C(O)C(O)=C(O)C=C6C(=O)OC[C@H]5OC(=O)C5=CC(O)=C(O)C(O)=C5C=5C(O)=C(O)C(O)=C(C=5C(=O)O2)C4=C(O)C(O)=C3O)=C1 JMGCAHRKIVCLFW-CNWXVVPTSA-N 0.000 claims description 4
- BZIGXGRVQSNLNL-UHFFFAOYSA-N Gemin A Natural products Oc1ccc(C(=O)OC2C(OC(=O)c3cc(O)c(O)c(Oc4c(O)c(O)c(O)cc4C(=O)OC5OC6COC(=O)c7cc(O)c(O)c(O)c7c8c(O)c(O)c(O)cc8C(=O)OC6C9OC(=O)c%10cc(O)c(O)c(O)c%10c%11c(O)c(O)c(O)cc%11C(=O)OC59)c3)OC%12COC(=O)c%13cc(O)c(O)c(O)c%13c%14c(O)c(O)c(O)cc%14C(=O)OC%12C2OC(=O)c%15cc(O)c(O)c(O)c%15)c(O)c1O BZIGXGRVQSNLNL-UHFFFAOYSA-N 0.000 claims description 3
- ODXMIHPUPFEYDB-HISCDKSNSA-N Gemin A Chemical compound OC1=C(O)C(O)=CC(C(=O)O[C@@H]2[C@H]([C@@H]3OC(=O)C4=CC(O)=C(O)C(O)=C4C4=C(O)C(O)=C(O)C=C4C(=O)OC[C@H]3O[C@@H]2OC(=O)C=2C=C(OC=3C(=CC(O)=C(O)C=3O)C(=O)O[C@@H]3[C@@H]4OC(=O)C5=CC(O)=C(O)C(O)=C5C5=C(O)C(O)=C(O)C=C5C(=O)O[C@H]4[C@@H]4OC(=O)C5=CC(O)=C(O)C(O)=C5C5=C(O)C(O)=C(O)C=C5C(=O)OC[C@H]4O3)C(O)=C(O)C=2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 ODXMIHPUPFEYDB-HISCDKSNSA-N 0.000 claims description 3
- RSZMIQZFBLGYLQ-QWHYFGCJSA-N [(10R,11R,13R,14R,15S)-3,4,5,11,20,21,22-heptahydroxy-8,17-dioxo-13-[(3,4,5-trihydroxybenzoyl)oxymethyl]-9,12,16-trioxatetracyclo[16.4.0.02,7.010,15]docosa-1(22),2,4,6,18,20-hexaen-14-yl] 3,4,5-trihydroxy-2-[[(1R,2S,19R,20S,22R)-7,8,9,12,13,14,29,30,33,34,35-undecahydroxy-4,17,25,38-tetraoxo-20-(3,4,5-trihydroxybenzoyl)oxy-3,18,21,24,39-pentaoxaheptacyclo[20.17.0.02,19.05,10.011,16.026,31.032,37]nonatriaconta-5,7,9,11,13,15,26,28,30,32,34,36-dodecaen-28-yl]oxy]benzoate Chemical compound O[C@@H]1O[C@H](COC(=O)c2cc(O)c(O)c(O)c2)[C@@H](OC(=O)c2cc(O)c(O)c(O)c2Oc2cc3c(c(O)c2O)-c2c(O)c(O)c(O)cc2C(=O)O[C@@H]2[C@@H](COC3=O)O[C@@H](OC(=O)c3cc(O)c(O)c(O)c3)[C@@H]3OC(=O)c4cc(O)c(O)c(O)c4-c4c(O)c(O)c(O)cc4C(=O)O[C@@H]23)[C@@H]2OC(=O)c3cc(O)c(O)c(O)c3-c3c(O)c(O)c(O)cc3C(=O)O[C@@H]12 RSZMIQZFBLGYLQ-QWHYFGCJSA-N 0.000 claims description 3
- 229930195472 nobotanin Natural products 0.000 claims description 3
- OZVQDJVYMCYPAX-UHFFFAOYSA-N nobotanin A Natural products OCC1OC(O)C2OC(=O)c3cc(O)c(O)c(O)c3c4c(O)c(O)c(O)cc4C(=O)OC2C1OC(=O)c5cc(OC(=O)c6cc(O)c(O)c(O)c6)c(O)c(O)c5Oc7cc8C(=O)OC9C(OC(=O)c%10cc(O)c(O)c(O)c%10)OC%11COC(=O)c%12cc(O)c(O)c(O)c%12c%13c(O)c(O)c(O)cc%13C(=O)OC%11C9OC(=O)c%14cc(O)c(O)c(O)c%14c8c(O)c7O OZVQDJVYMCYPAX-UHFFFAOYSA-N 0.000 claims description 3
- PNNKYDFJHCUHIQ-UHFFFAOYSA-N Rugosin E Natural products OC1OC2COC(=O)c3cc(Oc4c(O)c(O)c(O)cc4C(=O)OC5OC6COC(=O)c7cc(O)c(O)c(O)c7c8c(O)c(O)c(O)cc8C(=O)OC6C(OC(=O)c9cc(O)c(O)c(O)c9)C5OC(=O)c%10cc(O)c(O)c(O)c%10)c(O)c(O)c3c%11c(O)c(O)c(O)cc%11C(=O)OC2C(OC(=O)c%12cc(O)c(O)c(O)c%12)C1OC(=O)c%13cc(O)c(O)c(O)c%13 PNNKYDFJHCUHIQ-UHFFFAOYSA-N 0.000 claims 1
- 229940041181 antineoplastic drug Drugs 0.000 claims 1
- FJVMRJWMETUPFP-AIGHVOLPSA-N rugosin e Chemical compound O([C@H]1[C@@H]2OC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC[C@H]2O[C@H]([C@@H]1OC(=O)C=1C=C(O)C(O)=C(O)C=1)OC(=O)C1=CC(O)=C(O)C(O)=C1OC=1C=C2C(=O)OC[C@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3C2=C(O)C=1O)[C@H](OC(=O)C=1C=C(O)C(O)=C(O)C=1)[C@@H](OC(=O)C=1C=C(O)C(O)=C(O)C=1)C=O)O)C(=O)C1=CC(O)=C(O)C(O)=C1 FJVMRJWMETUPFP-AIGHVOLPSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- 239000000843 powder Substances 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 17
- 239000004480 active ingredient Substances 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 12
- 230000004083 survival effect Effects 0.000 description 12
- 239000001913 cellulose Substances 0.000 description 11
- 235000010980 cellulose Nutrition 0.000 description 11
- 229920002678 cellulose Polymers 0.000 description 11
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 10
- 238000000921 elemental analysis Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 208000006268 Sarcoma 180 Diseases 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- 239000002021 butanolic extract Substances 0.000 description 5
- 229920001968 ellagitannin Polymers 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 206010003445 Ascites Diseases 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000004185 countercurrent chromatography Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 208000024891 symptom Diseases 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- 210000004881 tumor cell Anatomy 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 231100000357 carcinogen Toxicity 0.000 description 3
- 239000003183 carcinogenic agent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- JMGCAHRKIVCLFW-UHFFFAOYSA-N 1-O-Galloylcastalagin Natural products Oc1cc(cc(O)c1O)C(=O)OC2C3OC(=O)c4c2c(O)c(O)c(O)c4c5c(O)c(O)c(O)c6c5C(=O)OC3C7OC(=O)c8cc(O)c(O)c(O)c8c9c(O)c(O)c(O)cc9C(=O)OCC7OC(=O)c%10cc(O)c(O)c(O)c6%10 JMGCAHRKIVCLFW-UHFFFAOYSA-N 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920002079 Ellagic acid Polymers 0.000 description 2
- AFSDNFLWKVMVRB-UHFFFAOYSA-N Ellagic acid Chemical compound OC1=C(O)C(OC2=O)=C3C4=C2C=C(O)C(O)=C4OC(=O)C3=C1 AFSDNFLWKVMVRB-UHFFFAOYSA-N 0.000 description 2
- ATJXMQHAMYVHRX-CPCISQLKSA-N Ellagic acid Natural products OC1=C(O)[C@H]2OC(=O)c3cc(O)c(O)c4OC(=O)C(=C1)[C@H]2c34 ATJXMQHAMYVHRX-CPCISQLKSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 231100000111 LD50 Toxicity 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 230000004663 cell proliferation Effects 0.000 description 2
- 238000001142 circular dichroism spectrum Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229960002852 ellagic acid Drugs 0.000 description 2
- 235000004132 ellagic acid Nutrition 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 238000002143 fast-atom bombardment mass spectrum Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229920001461 hydrolysable tannin Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000010255 intramuscular injection Methods 0.000 description 2
- 239000007927 intramuscular injection Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- FAARLWTXUUQFSN-UHFFFAOYSA-N methylellagic acid Natural products O1C(=O)C2=CC(O)=C(O)C3=C2C2=C1C(OC)=C(O)C=C2C(=O)O3 FAARLWTXUUQFSN-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 235000018553 tannin Nutrition 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241001326573 Coriaria japonica Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 244000196929 Oenothera glazioviana Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005377 adsorption chromatography Methods 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008408 compound extracted from plant Substances 0.000 description 1
- 229920002770 condensed tannin Polymers 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60270494A JPS62129220A (ja) | 1985-11-30 | 1985-11-30 | 制癌剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60270494A JPS62129220A (ja) | 1985-11-30 | 1985-11-30 | 制癌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62129220A JPS62129220A (ja) | 1987-06-11 |
| JPS638088B2 true JPS638088B2 (fr) | 1988-02-19 |
Family
ID=17487055
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60270494A Granted JPS62129220A (ja) | 1985-11-30 | 1985-11-30 | 制癌剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62129220A (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2712594B1 (fr) * | 1993-11-16 | 1996-12-27 | Roussel Uclaf | Procédé de préparation de l'oenotheine B à partir d'Epilobium Parviflorum. |
| FR2712495B1 (fr) * | 1993-11-16 | 1996-01-05 | Roussel Uclaf | Application de l'Óoenotheine B pour obtenir un médicament destiné au traitement des troubles liés à l'hyperandrogénie, et les compositions pharmaceutiques le contenant. |
| KR100371085B1 (ko) * | 2000-08-04 | 2003-02-06 | 한솔제지주식회사 | 신규 엘라지탄닌 배당체 화합물 |
| ES2540912T3 (es) * | 2005-10-27 | 2015-07-14 | Lead Billion Limited | Composición farmacéutica y método de neoangiogénesis/revascularización útiles en el tratamiento de enfermedades cardíacas isquémicas |
-
1985
- 1985-11-30 JP JP60270494A patent/JPS62129220A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62129220A (ja) | 1987-06-11 |
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