JPH07502009A - クエルセチン化合物を活性物質として含有する腫瘍、特に卵巣及び造血系の腫瘍の治療用薬剤 - Google Patents
クエルセチン化合物を活性物質として含有する腫瘍、特に卵巣及び造血系の腫瘍の治療用薬剤Info
- Publication number
- JPH07502009A JPH07502009A JP4505072A JP50507292A JPH07502009A JP H07502009 A JPH07502009 A JP H07502009A JP 4505072 A JP4505072 A JP 4505072A JP 50507292 A JP50507292 A JP 50507292A JP H07502009 A JPH07502009 A JP H07502009A
- Authority
- JP
- Japan
- Prior art keywords
- quercetin
- tumors
- compounds
- compound
- reacting
- 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.)
- Pending
Links
- 206010028980 Neoplasm Diseases 0.000 title claims description 15
- 150000003243 quercetin Chemical class 0.000 title claims description 6
- 239000013543 active substance Substances 0.000 title claims description 4
- 210000000777 hematopoietic system Anatomy 0.000 title description 3
- 210000001672 ovary Anatomy 0.000 title description 3
- 239000003795 chemical substances by application Substances 0.000 title 1
- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 claims description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- 235000005875 quercetin Nutrition 0.000 claims description 33
- ZVOLCUVKHLEPEV-UHFFFAOYSA-N Quercetagetin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=C(O)C(O)=C(O)C=C2O1 ZVOLCUVKHLEPEV-UHFFFAOYSA-N 0.000 claims description 32
- HWTZYBCRDDUBJY-UHFFFAOYSA-N Rhynchosin Natural products C1=C(O)C(O)=CC=C1C1=C(O)C(=O)C2=CC(O)=C(O)C=C2O1 HWTZYBCRDDUBJY-UHFFFAOYSA-N 0.000 claims description 32
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 32
- 229960001285 quercetin Drugs 0.000 claims description 32
- 239000000126 substance Substances 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 229940079593 drug Drugs 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011701 zinc Substances 0.000 claims description 7
- 229910052725 zinc Inorganic materials 0.000 claims description 7
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 5
- 229910052711 selenium Inorganic materials 0.000 claims description 5
- 239000011669 selenium Substances 0.000 claims description 5
- -1 fluorinated quercetin compound Chemical class 0.000 claims description 4
- KWVVTSALYXIJSS-UHFFFAOYSA-L silver(ii) fluoride Chemical compound [F-].[F-].[Ag+2] KWVVTSALYXIJSS-UHFFFAOYSA-L 0.000 claims description 4
- JQUHMSXLZZWRHU-UHFFFAOYSA-N [2-acetyloxy-4-(3,5,7-triacetyloxy-4-oxochromen-2-yl)phenyl] acetate Chemical compound C=1C(OC(=O)C)=CC(OC(C)=O)=C(C(C=2OC(C)=O)=O)C=1OC=2C1=CC=C(OC(C)=O)C(OC(C)=O)=C1 JQUHMSXLZZWRHU-UHFFFAOYSA-N 0.000 claims description 3
- 229930182470 glycoside Natural products 0.000 claims description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
- VSNHAPZACGYDJL-UHFFFAOYSA-N acetyloxyselanyl acetate Chemical compound CC(=O)O[Se]OC(C)=O VSNHAPZACGYDJL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004246 zinc acetate Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- KPCRYSMUMBNTCK-UHFFFAOYSA-N 3',5-dihydroxy-3,4',7-trimethoxyflavone Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC)C(O)=C1 KPCRYSMUMBNTCK-UHFFFAOYSA-N 0.000 claims 1
- HHGPYJLEJGNWJA-UHFFFAOYSA-N 5-hydroxy-3,3',4',7-tetramethoxyflavone Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HHGPYJLEJGNWJA-UHFFFAOYSA-N 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 230000001028 anti-proliverative effect Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 230000035772 mutation Effects 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WRASMIGJWWJAAJ-UHFFFAOYSA-N 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-methoxy-6,8-dimethylchromen-4-one Chemical compound O1C2=C(C)C(O)=C(C)C(O)=C2C(=O)C(OC)=C1C1=CC=C(O)C(O)=C1 WRASMIGJWWJAAJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 101100323029 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) alc-1 gene Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000206602 Eukaryota Species 0.000 description 1
- BKAYIFDRRZZKNF-VIFPVBQESA-N N-acetylcarnosine Chemical compound CC(=O)NCCC(=O)N[C@H](C(O)=O)CC1=CN=CN1 BKAYIFDRRZZKNF-VIFPVBQESA-N 0.000 description 1
- 206010033128 Ovarian cancer Diseases 0.000 description 1
- 206010061535 Ovarian neoplasm Diseases 0.000 description 1
- 244000078856 Prunus padus Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 210000004748 cultured cell Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000003471 mutagenic agent Substances 0.000 description 1
- 231100000707 mutagenic chemical Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003244 quercetin derivatives Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 108010009635 type II estrogen binding site Proteins 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT91A000085 | 1991-02-05 | ||
| ITRM910085A IT1244647B (it) | 1991-02-05 | 1991-02-05 | Prodotto farmaceutico per la terapia dei tumori, in particolare di quelli ovarici e del sistema emopoietico, contenente quercitina come principio attivo. |
| PCT/IT1992/000007 WO1992013851A1 (en) | 1991-02-05 | 1992-01-31 | Pharmaceutical product for the therapy of tumors, particularly ovarian and haemopoietic system tumors, containing quercetin compounds as active substances |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH07502009A true JPH07502009A (ja) | 1995-03-02 |
Family
ID=11399834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4505072A Pending JPH07502009A (ja) | 1991-02-05 | 1992-01-31 | クエルセチン化合物を活性物質として含有する腫瘍、特に卵巣及び造血系の腫瘍の治療用薬剤 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0570475A1 (it) |
| JP (1) | JPH07502009A (it) |
| AU (1) | AU1269192A (it) |
| IT (1) | IT1244647B (it) |
| WO (1) | WO1992013851A1 (it) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021073295A (ja) * | 2010-11-24 | 2021-05-13 | デュレクト コーポレイション | 生分解性薬物送達組成物 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITRM20010600A1 (it) * | 2001-10-04 | 2003-04-04 | Brane Tech S R L | Composti flavonoidici capaci di modificare lo stato fisico e/o dinamico di membrane biologiche e di stimolare la sintesi endogena di protein |
| TWI660680B (zh) | 2012-11-26 | 2019-06-01 | 美商通路實業集團國際公司 | 抗氧化膳食增補劑及其相關方法 |
| CN111068095B (zh) * | 2020-02-07 | 2021-07-13 | 中国科学院上海硅酸盐研究所 | 高效诱导烧伤创面毛囊再生的生物活性离子改性槲皮素螯合剂组合物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892845A (en) * | 1957-11-26 | 1959-06-30 | Jurd Leonard | Selective etherification of the 7-hydroxyl group in polyhydroxy flavonoids |
| FR3541M (fr) * | 1964-05-12 | 1965-09-13 | Laroche Navarron Lab | Médicament a propriétés natriurétiques a base d'une nouvelle flavone. |
-
1991
- 1991-02-05 IT ITRM910085A patent/IT1244647B/it active IP Right Grant
-
1992
- 1992-01-31 WO PCT/IT1992/000007 patent/WO1992013851A1/en not_active Ceased
- 1992-01-31 AU AU12691/92A patent/AU1269192A/en not_active Abandoned
- 1992-01-31 EP EP92905230A patent/EP0570475A1/en not_active Withdrawn
- 1992-01-31 JP JP4505072A patent/JPH07502009A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021073295A (ja) * | 2010-11-24 | 2021-05-13 | デュレクト コーポレイション | 生分解性薬物送達組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| ITRM910085A0 (it) | 1991-02-05 |
| WO1992013851A1 (en) | 1992-08-20 |
| EP0570475A1 (en) | 1993-11-24 |
| AU1269192A (en) | 1992-09-07 |
| IT1244647B (it) | 1994-08-08 |
| ITRM910085A1 (it) | 1992-08-05 |
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