JPH0544927B2 - - Google Patents
Info
- Publication number
- JPH0544927B2 JPH0544927B2 JP60292860A JP29286085A JPH0544927B2 JP H0544927 B2 JPH0544927 B2 JP H0544927B2 JP 60292860 A JP60292860 A JP 60292860A JP 29286085 A JP29286085 A JP 29286085A JP H0544927 B2 JPH0544927 B2 JP H0544927B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- epoxy
- anticancer
- methyl
- furan
- 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 - Lifetime
Links
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 21
- 229930195729 fatty acid Natural products 0.000 claims description 21
- 239000000194 fatty acid Substances 0.000 claims description 21
- -1 furan cyclic fatty acids Chemical class 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 239000002246 antineoplastic agent Substances 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 230000001093 anti-cancer Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SZNVIDWMWMWUCY-UHFFFAOYSA-N 8-(5-hexylfuran-2-yl)octanoic acid Chemical compound CCCCCCC1=CC=C(CCCCCCCC(O)=O)O1 SZNVIDWMWMWUCY-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- HDHYFCAMRUJRJJ-UHFFFAOYSA-N 11-(3,4-dimethyl-5-propylfuran-2-yl)undecanoic acid Chemical compound CCCC=1OC(CCCCCCCCCCC(O)=O)=C(C)C=1C HDHYFCAMRUJRJJ-UHFFFAOYSA-N 0.000 description 2
- QDTBMEGPXZUECM-UHFFFAOYSA-N 11-(3-Methyl-5-pentyl-2-furyl)undecanoic acid Chemical compound CCCCCC1=CC(C)=C(CCCCCCCCCCC(O)=O)O1 QDTBMEGPXZUECM-UHFFFAOYSA-N 0.000 description 2
- TUQVXFOSXOCQCM-UHFFFAOYSA-N 9-(3-Methyl-5-pentyl-2-furyl)nonanoic acid Chemical compound CCCCCC1=CC(C)=C(CCCCCCCCC(O)=O)O1 TUQVXFOSXOCQCM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229940041181 antineoplastic drug Drugs 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- ZKGJOTNOOSGNIW-UHFFFAOYSA-N methyl 8-[3-(2-oxooctyl)oxiran-2-yl]octanoate Chemical compound CCCCCCC(=O)CC1OC1CCCCCCCC(=O)OC ZKGJOTNOOSGNIW-UHFFFAOYSA-N 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XSXIVVZCUAHUJO-AVQMFFATSA-N (11e,14e)-icosa-11,14-dienoic acid Chemical compound CCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O XSXIVVZCUAHUJO-AVQMFFATSA-N 0.000 description 1
- QHEOVCWNVASAFS-XFXZXTDPSA-N (z)-12-oxooctadec-9-enoic acid Chemical compound CCCCCCC(=O)C\C=C/CCCCCCCC(O)=O QHEOVCWNVASAFS-XFXZXTDPSA-N 0.000 description 1
- JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
- MCTXSZNBSIMKTO-UHFFFAOYSA-N 3,4-Dimethyl-5-pentyl-2-furanundecanoic acid Chemical compound CCCCCC=1OC(CCCCCCCCCCC(O)=O)=C(C)C=1C MCTXSZNBSIMKTO-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000021297 Eicosadienoic acid Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 210000000683 abdominal cavity Anatomy 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- DIPHDXIHMQRKSX-UHFFFAOYSA-N methyl 12-oxooctadec-9-enoate Chemical compound CCCCCCC(=O)CC=CCCCCCCCC(=O)OC DIPHDXIHMQRKSX-UHFFFAOYSA-N 0.000 description 1
- ZZSFTHVENQKCDJ-UHFFFAOYSA-N methyl 8-(5-hexylfuran-2-yl)octanoate Chemical compound CCCCCCC1=CC=C(CCCCCCCC(=O)OC)O1 ZZSFTHVENQKCDJ-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60292860A JPS62153218A (ja) | 1985-12-27 | 1985-12-27 | 制癌剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60292860A JPS62153218A (ja) | 1985-12-27 | 1985-12-27 | 制癌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62153218A JPS62153218A (ja) | 1987-07-08 |
| JPH0544927B2 true JPH0544927B2 (enrdf_load_html_response) | 1993-07-07 |
Family
ID=17787307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60292860A Granted JPS62153218A (ja) | 1985-12-27 | 1985-12-27 | 制癌剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62153218A (enrdf_load_html_response) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE273703T1 (de) * | 2001-02-23 | 2004-09-15 | Sirs Lab Gmbh | Furanfettsäuren zur steigerung der effizienz der zytostatikatherapie und/oder bestrahlungstherapie |
| CA2995854A1 (en) * | 2015-09-14 | 2017-03-23 | The Regents Of The University Of California | Preparation of furan fatty acids from 5-(chloromethyl)furfural |
-
1985
- 1985-12-27 JP JP60292860A patent/JPS62153218A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62153218A (ja) | 1987-07-08 |
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