JPS6032793A - 新規ブルセオライド誘導体およびその製造法 - Google Patents
新規ブルセオライド誘導体およびその製造法Info
- Publication number
- JPS6032793A JPS6032793A JP58140268A JP14026883A JPS6032793A JP S6032793 A JPS6032793 A JP S6032793A JP 58140268 A JP58140268 A JP 58140268A JP 14026883 A JP14026883 A JP 14026883A JP S6032793 A JPS6032793 A JP S6032793A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- group
- carbon atoms
- formula
- acid residue
- 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.)
- Granted
Links
- YLWQKYSDNGHLAO-PWRINDRCSA-N bruceolide Chemical class CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](O)C(=O)O[C@@H]4C[C@H]21 YLWQKYSDNGHLAO-PWRINDRCSA-N 0.000 title abstract 3
- -1 methoxyethoxymethyl Chemical group 0.000 claims abstract description 25
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000004020 conductor Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 34
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- YLWQKYSDNGHLAO-UHFFFAOYSA-N Bruceolide Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(O)C(=O)OC4CC21 YLWQKYSDNGHLAO-UHFFFAOYSA-N 0.000 abstract 1
- 230000003327 cancerostatic effect Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000000259 anti-tumor effect Effects 0.000 description 6
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 229930014626 natural product Natural products 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- NTWSIWWJPQHFTO-AATRIKPKSA-N (2E)-3-methylhex-2-enoic acid Chemical group CCC\C(C)=C\C(O)=O NTWSIWWJPQHFTO-AATRIKPKSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001093 anti-cancer Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZZZYHIMVKOHVIH-VILODJCFSA-N Brusatol Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]4C[C@H]21 ZZZYHIMVKOHVIH-VILODJCFSA-N 0.000 description 2
- ZZZYHIMVKOHVIH-UHFFFAOYSA-N Brusatol Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C)C(=O)OC4CC21 ZZZYHIMVKOHVIH-UHFFFAOYSA-N 0.000 description 2
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WJUCVNVYISECTJ-BQYQJAHWSA-N (e)-3-methyloct-2-enoic acid Chemical group CCCCC\C(C)=C\C(O)=O WJUCVNVYISECTJ-BQYQJAHWSA-N 0.000 description 1
- RQCFUXLFOIOLFM-UHFFFAOYSA-N 1-chloro-3-(3-chloro-2-methoxypropoxy)-2-methoxypropane Chemical compound COC(CCl)COCC(CCl)OC RQCFUXLFOIOLFM-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- UOOWECZOWUNYLA-CMDGGOBGSA-N 3-methyl-2-nonenoic acid Chemical group CCCCCC\C(C)=C\C(O)=O UOOWECZOWUNYLA-CMDGGOBGSA-N 0.000 description 1
- RSFQOQOSOMBPEJ-PLNGDYQASA-N 3-methyl-2Z-pentenoic acid Chemical group CC\C(C)=C/C(O)=O RSFQOQOSOMBPEJ-PLNGDYQASA-N 0.000 description 1
- HSIBOIAYNONIBX-UHFFFAOYSA-N 3-methylhexadec-2-enoic acid Chemical group CCCCCCCCCCCCCC(C)=CC(O)=O HSIBOIAYNONIBX-UHFFFAOYSA-N 0.000 description 1
- RCXDKHZXABUNCU-UHFFFAOYSA-N 3-methyloctadec-2-enoic acid Chemical group CCCCCCCCCCCCCCCC(C)=CC(O)=O RCXDKHZXABUNCU-UHFFFAOYSA-N 0.000 description 1
- PAIJLRRCRATYTI-UHFFFAOYSA-N 3-methyltridec-2-ene Chemical compound CCCCCCCCCCC(C)=CC PAIJLRRCRATYTI-UHFFFAOYSA-N 0.000 description 1
- MWKLFHTYBDIXBW-UHFFFAOYSA-N 3-methylundec-2-enoic acid Chemical group CCCCCCCCC(C)=CC(O)=O MWKLFHTYBDIXBW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- IRQXZTBHNKVIRL-GOTQHHPNSA-N Bruceantin Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)\C=C(/C)C(C)C)C(=O)O[C@@H]4C[C@H]21 IRQXZTBHNKVIRL-GOTQHHPNSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 101000980900 Homo sapiens Sororin Proteins 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- IRQXZTBHNKVIRL-UHFFFAOYSA-N NSC 165563 Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C(C)C)C(=O)OC4CC21 IRQXZTBHNKVIRL-UHFFFAOYSA-N 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 102100024483 Sororin Human genes 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- IRQXZTBHNKVIRL-AYXPYFKUSA-N bruceantin Natural products CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C(C)C)C(=O)O[C@@H]4C[C@H]21 IRQXZTBHNKVIRL-AYXPYFKUSA-N 0.000 description 1
- ZZHGIUCYKGFIPV-UHFFFAOYSA-N butylcarbamic acid Chemical group CCCCNC(O)=O ZZHGIUCYKGFIPV-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbamic acid group Chemical group C(N)(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- RUDATBOHQWOJDD-BSWAIDMHSA-N chenodeoxycholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-BSWAIDMHSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- HPNLSQVULJRWNL-UHFFFAOYSA-N decylcarbamic acid Chemical group CCCCCCCCCCNC(O)=O HPNLSQVULJRWNL-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- KYXMJYWUKCNPSD-UHFFFAOYSA-N dodecylcarbamic acid Chemical group CCCCCCCCCCCCNC(O)=O KYXMJYWUKCNPSD-UHFFFAOYSA-N 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- KWBIXTIBYFUAGV-UHFFFAOYSA-N ethylcarbamic acid Chemical group CCNC(O)=O KWBIXTIBYFUAGV-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- PUZGLYHQMAZKGK-UHFFFAOYSA-N gold;methanol Chemical compound [Au].OC PUZGLYHQMAZKGK-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- NDCHRBWMPJFJPY-UHFFFAOYSA-N hexadecylcarbamic acid Chemical group CCCCCCCCCCCCCCCCNC(O)=O NDCHRBWMPJFJPY-UHFFFAOYSA-N 0.000 description 1
- YAQPZDICKJDHTR-UHFFFAOYSA-N hexylcarbamic acid Chemical group CCCCCCNC(O)=O YAQPZDICKJDHTR-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- BXXLBMBLLVIOKO-UHFFFAOYSA-N octadecylcarbamic acid Chemical group CCCCCCCCCCCCCCCCCCNC(O)=O BXXLBMBLLVIOKO-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- SGQFQIOHTBBYFS-UHFFFAOYSA-N octylcarbamic acid Chemical group CCCCCCCCNC(O)=O SGQFQIOHTBBYFS-UHFFFAOYSA-N 0.000 description 1
- RMNWSXOHQSHSRE-UHFFFAOYSA-N pentadecylcarbamic acid Chemical group CCCCCCCCCCCCCCCNC(O)=O RMNWSXOHQSHSRE-UHFFFAOYSA-N 0.000 description 1
- MYDQAEQZZKVJSL-UHFFFAOYSA-N pentyl carbamate Chemical group CCCCCOC(N)=O MYDQAEQZZKVJSL-UHFFFAOYSA-N 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- YMPIMNUYOUEPHI-UHFFFAOYSA-N tetradecylcarbamic acid Chemical group CCCCCCCCCCCCCCNC(O)=O YMPIMNUYOUEPHI-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QCBWOGJHFGKNTE-UHFFFAOYSA-N tridecylcarbamic acid Chemical group CCCCCCCCCCCCCNC(O)=O QCBWOGJHFGKNTE-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- WSNOKGKQOHFPPC-UHFFFAOYSA-N undecylcarbamic acid Chemical compound CCCCCCCCCCCNC(O)=O WSNOKGKQOHFPPC-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58140268A JPS6032793A (ja) | 1983-07-30 | 1983-07-30 | 新規ブルセオライド誘導体およびその製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58140268A JPS6032793A (ja) | 1983-07-30 | 1983-07-30 | 新規ブルセオライド誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6032793A true JPS6032793A (ja) | 1985-02-19 |
| JPH0454672B2 JPH0454672B2 (enrdf_load_stackoverflow) | 1992-08-31 |
Family
ID=15264818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58140268A Granted JPS6032793A (ja) | 1983-07-30 | 1983-07-30 | 新規ブルセオライド誘導体およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6032793A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002062334A3 (en) * | 2001-02-05 | 2003-02-27 | John M Pezzuto | Cancer chemopreventative compounds and compositions and methods of treating cancers |
| JP2006272055A (ja) * | 2005-03-28 | 2006-10-12 | Idx Corp | マイクロ波化学反応装置 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969369A (en) * | 1973-06-20 | 1976-07-13 | Research Corporation | Bruceantin |
-
1983
- 1983-07-30 JP JP58140268A patent/JPS6032793A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969369A (en) * | 1973-06-20 | 1976-07-13 | Research Corporation | Bruceantin |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002062334A3 (en) * | 2001-02-05 | 2003-02-27 | John M Pezzuto | Cancer chemopreventative compounds and compositions and methods of treating cancers |
| JP2006272055A (ja) * | 2005-03-28 | 2006-10-12 | Idx Corp | マイクロ波化学反応装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0454672B2 (enrdf_load_stackoverflow) | 1992-08-31 |
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