SK282259B6 - Estery chalkónov, ich komplexy, farmaceutické prostriedky s ich obsahom a ich použitie - Google Patents
Estery chalkónov, ich komplexy, farmaceutické prostriedky s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK282259B6 SK282259B6 SK781-97A SK78197A SK282259B6 SK 282259 B6 SK282259 B6 SK 282259B6 SK 78197 A SK78197 A SK 78197A SK 282259 B6 SK282259 B6 SK 282259B6
- Authority
- SK
- Slovakia
- Prior art keywords
- esters
- hydroxydericin
- acid
- cordoin
- isocordoin
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims abstract description 17
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 title description 8
- 150000001789 chalcones Chemical class 0.000 title description 8
- 235000005513 chalcones Nutrition 0.000 title description 8
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- CHWWSUSAPRACBZ-FMIVXFBMSA-N Isocordoin Chemical compound CC(C)=CCC1=C(O)C=CC(C(=O)\C=C\C=2C=CC=CC=2)=C1O CHWWSUSAPRACBZ-FMIVXFBMSA-N 0.000 claims abstract description 31
- DGUGLZYULGVSIZ-DHZHZOJOSA-N (e)-1-[2-hydroxy-4-(3-methylbut-2-enoxy)phenyl]-3-phenylprop-2-en-1-one Chemical compound OC1=CC(OCC=C(C)C)=CC=C1C(=O)\C=C\C1=CC=CC=C1 DGUGLZYULGVSIZ-DHZHZOJOSA-N 0.000 claims abstract description 18
- DGUGLZYULGVSIZ-UHFFFAOYSA-N derricidine Natural products OC1=CC(OCC=C(C)C)=CC=C1C(=O)C=CC1=CC=CC=C1 DGUGLZYULGVSIZ-UHFFFAOYSA-N 0.000 claims abstract description 18
- CHWWSUSAPRACBZ-UHFFFAOYSA-N Flemistricin-A Natural products CC(C)=CCC1=C(O)C=CC(C(=O)C=CC=2C=CC=CC=2)=C1O CHWWSUSAPRACBZ-UHFFFAOYSA-N 0.000 claims abstract description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 102000015694 estrogen receptors Human genes 0.000 claims abstract description 12
- 108010038795 estrogen receptors Proteins 0.000 claims abstract description 12
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims abstract description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 5
- 235000021314 Palmitic acid Nutrition 0.000 claims abstract description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 4
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims abstract description 3
- 230000001093 anti-cancer Effects 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- JUMSUVHHUVPSOY-RMKNXTFCSA-N (e)-1-(2,4-dihydroxyphenyl)-3-phenylprop-2-en-1-one Chemical compound OC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=CC=C1 JUMSUVHHUVPSOY-RMKNXTFCSA-N 0.000 claims 2
- JUMSUVHHUVPSOY-UHFFFAOYSA-N (E)-1-(2,4-dihydroxyphenyl)-3-phenylprop-2-en-1-one Natural products OC1=CC(O)=CC=C1C(=O)C=CC1=CC=CC=C1 JUMSUVHHUVPSOY-UHFFFAOYSA-N 0.000 claims 1
- ZUKLXLKVCGZHAA-UHFFFAOYSA-N 1-(2,4-Dihydroxy-phenyl)-3-phenyl-propan-1-on Natural products OC1=CC(O)=CC=C1C(=O)CCC1=CC=CC=C1 ZUKLXLKVCGZHAA-UHFFFAOYSA-N 0.000 claims 1
- LKNPFZQVNZFLIC-UHFFFAOYSA-N 2',4'-dihydroxychalcone Natural products OC1=CC(O)=CC=C1C=CC(=O)C1=CC=CC=C1 LKNPFZQVNZFLIC-UHFFFAOYSA-N 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- DXDRHHKMWQZJHT-FPYGCLRLSA-N isoliquiritigenin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)C1=CC=C(O)C=C1O DXDRHHKMWQZJHT-FPYGCLRLSA-N 0.000 claims 1
- DXDRHHKMWQZJHT-UHFFFAOYSA-N isoliquiritigenin chalcone Natural products C1=CC(O)=CC=C1C=CC(=O)C1=CC=C(O)C=C1O DXDRHHKMWQZJHT-UHFFFAOYSA-N 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 abstract description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 abstract description 5
- 230000002611 ovarian Effects 0.000 abstract description 5
- 230000001028 anti-proliverative effect Effects 0.000 abstract description 4
- 206010046766 uterine cancer Diseases 0.000 abstract description 4
- 206010006187 Breast cancer Diseases 0.000 abstract description 2
- 206010033128 Ovarian cancer Diseases 0.000 abstract 1
- 208000002495 Uterine Neoplasms Diseases 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 13
- 210000004027 cell Anatomy 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 201000011510 cancer Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 229960005309 estradiol Drugs 0.000 description 3
- 229930182833 estradiol Natural products 0.000 description 3
- 229930003935 flavonoid Natural products 0.000 description 3
- 150000002215 flavonoids Chemical class 0.000 description 3
- 235000017173 flavonoids Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- 208000025421 tumor of uterus Diseases 0.000 description 3
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- PYMCFHVCMWMRLO-UHFFFAOYSA-N Dihydrocordoin Chemical compound OC1=CC(OCC=C(C)C)=CC=C1C(=O)CCC1=CC=CC=C1 PYMCFHVCMWMRLO-UHFFFAOYSA-N 0.000 description 2
- -1 Isocordoin Acetates Chemical class 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 2
- 229960000452 diethylstilbestrol Drugs 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 2
- 230000004614 tumor growth Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RQIDQEBURXNDKG-MDZDMXLPSA-N ximenic acid Chemical compound CCCCCCCC\C=C\CCCCCCCCCCCCCCCC(O)=O RQIDQEBURXNDKG-MDZDMXLPSA-N 0.000 description 2
- CEJRXJDIPVWROP-UHFFFAOYSA-N 1-cyclohex-2-en-1-yl-3-phenylprop-2-en-1-one Chemical class C1CCC=CC1C(=O)C=CC1=CC=CC=C1 CEJRXJDIPVWROP-UHFFFAOYSA-N 0.000 description 1
- SFXYAAFUXNWNQF-UHFFFAOYSA-N 4-Hydroxycordoin Natural products OC1=CC(OCC=C(C)C)=CC=C1C(=O)C=CC1=CC=C(O)C=C1 SFXYAAFUXNWNQF-UHFFFAOYSA-N 0.000 description 1
- SFXYAAFUXNWNQF-BJMVGYQFSA-N 4-hydroxycordoin Chemical compound OC1=CC(OCC=C(C)C)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1 SFXYAAFUXNWNQF-BJMVGYQFSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 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 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007640 basal medium Substances 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000005917 in vivo anti-tumor Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004264 monolayer culture Methods 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical class O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/017—Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI942568A IT1271301B (it) | 1994-12-20 | 1994-12-20 | Calconi naturali e sintetici e loro esteri ad attivita' antiproliferativa nei tumori dell'utero,dell'ovaio e del seno e formulazioni che li contengono |
| PCT/EP1995/004770 WO1996019209A1 (en) | 1994-12-20 | 1995-12-04 | Chalcones and esters thereof with antiproliferative activity in uterus, ovary and breast tumours |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK78197A3 SK78197A3 (en) | 1997-12-10 |
| SK282259B6 true SK282259B6 (sk) | 2001-12-03 |
Family
ID=11370023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK781-97A SK282259B6 (sk) | 1994-12-20 | 1995-12-04 | Estery chalkónov, ich komplexy, farmaceutické prostriedky s ich obsahom a ich použitie |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5808137A (it) |
| EP (1) | EP0800387B1 (it) |
| JP (1) | JP2004131509A (it) |
| KR (1) | KR100264369B1 (it) |
| CN (1) | CN1087609C (it) |
| AT (1) | ATE222756T1 (it) |
| AU (1) | AU689357B2 (it) |
| CA (1) | CA2208351C (it) |
| CZ (1) | CZ288043B6 (it) |
| DE (1) | DE69527980T2 (it) |
| DK (1) | DK0800387T3 (it) |
| ES (1) | ES2181806T3 (it) |
| FI (1) | FI972641A (it) |
| HU (1) | HU225501B1 (it) |
| IT (1) | IT1271301B (it) |
| NO (1) | NO307926B1 (it) |
| PL (1) | PL183772B1 (it) |
| PT (1) | PT800387E (it) |
| RU (1) | RU2181284C2 (it) |
| SI (1) | SI9520139B (it) |
| SK (1) | SK282259B6 (it) |
| WO (1) | WO1996019209A1 (it) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9712966D0 (en) * | 1997-06-19 | 1997-08-27 | Indena Spa | Novel chalcones |
| US6423740B1 (en) | 1997-06-19 | 2002-07-23 | Indena S.P.A. | Chalcones having antiproliferative activity |
| US6239114B1 (en) * | 1997-09-26 | 2001-05-29 | Kgk Synergize | Compositions and methods for treatment of neoplastic diseases with combinations of limonoids, flavonoids and tocotrienols |
| GB9920910D0 (en) | 1999-09-03 | 1999-11-10 | Indena Spa | Novel chalcones |
| GB9920908D0 (en) * | 1999-09-03 | 1999-11-10 | Indena Spa | Chalcone coumarins |
| KR20030031500A (ko) | 2000-06-20 | 2003-04-21 | 아테로제닉스, 인코포레이티드 | 1,3-비스-(치환된-페닐)-2-프로펜-1-온 및 ｖｃａｍ-1매개된 질환을 치료하기 위한 그의 용도 |
| WO2002040021A2 (en) | 2000-11-17 | 2002-05-23 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of hiv using topically applied substituted 6-benzyl-4-oxopyrimidines |
| US7094801B2 (en) * | 2001-12-19 | 2006-08-22 | Atherogenics, Inc. | Chalcone derivatives and their use to treat diseases |
| AU2003243594A1 (en) * | 2002-06-13 | 2003-12-31 | Johns Hopkins University | Novel boronic chalcone derivatives and uses thereof |
| WO2004056727A2 (en) * | 2002-12-19 | 2004-07-08 | Atherogenics, Inc. | Process of making chalcone derivatives |
| CN1890205A (zh) * | 2003-12-05 | 2007-01-03 | 宝生物工程株式会社 | 治疗剂 |
| WO2006004903A2 (en) * | 2004-06-28 | 2006-01-12 | Atherogenics, Inc. | 1,2-bis-(substituted-phenyl)-2-propen-1-ones and pharmaceutical compositions thereof |
| CN100336797C (zh) * | 2005-08-19 | 2007-09-12 | 浙江大学 | 四取代查耳酮衍生物及制备方法和用途 |
| GB0609386D0 (en) * | 2006-05-11 | 2006-06-21 | Active Botan Ltd | Treating drug resistant cancers |
| US9132117B2 (en) | 2013-06-17 | 2015-09-15 | Kgk Synergize, Inc | Compositions and methods for glycemic control of subjects with impaired fasting glucose |
| ES2540457B2 (es) * | 2013-06-19 | 2015-12-28 | Universidad De Sevilla | Procedimiento de obtención de extractos de hojas de Corema album y su aplicación terapéutica |
| KR101731159B1 (ko) | 2015-02-04 | 2017-04-28 | 계명대학교 산학협력단 | 2',4'-디하이드록시칼콘 화합물을 유효성분으로 포함하는 항진균용 조성물 |
| CZ307046B6 (cs) * | 2015-09-02 | 2017-12-13 | Univerzita PalackĂ©ho v Olomouci | Komplexy mědi s deriváty (E)-1-(2´-hydroxyfenyl)-3-fenylprop-2-en-1-onu a jejich použití jako léčiv v protinádorové terapii |
| CN111138264B (zh) * | 2019-11-29 | 2023-08-04 | 温州医科大学 | 一种丁香醛衍生物及其在制备抗妇科肿瘤药物中的应用 |
| CN113564103B (zh) * | 2021-05-17 | 2023-01-06 | 南京医科大学 | 4,4’-二甲氧基查耳酮在延缓卵母细胞体内外老化中的应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH593224A5 (it) * | 1973-10-30 | 1977-11-30 | Taisho Pharmaceutical Co Ltd | |
| HU203515B (en) * | 1986-12-12 | 1991-08-28 | Tsumura & Co | Process for producing new calcon derivatives and pharmaceutical compositions containing them as active components |
| US5234951A (en) * | 1986-12-12 | 1993-08-10 | Tsumura Juntendo, Inc. | Anti-ulcer agent comprising chalcone derivative |
| CA2084208A1 (en) * | 1990-05-17 | 1991-11-18 | Barry Markaverich | Growth inhibitors and methods of treating cancer and cell proliferative diseases |
| WO1993001824A1 (en) * | 1991-07-24 | 1993-02-04 | Baylor College Of Medicine | Combination therapy using bioflavonoid compounds with anti-cancer drugs |
-
1994
- 1994-12-20 IT ITMI942568A patent/IT1271301B/it active IP Right Grant
-
1995
- 1995-12-04 SI SI9520139A patent/SI9520139B/sl not_active IP Right Cessation
- 1995-12-04 PL PL95320787A patent/PL183772B1/pl not_active IP Right Cessation
- 1995-12-04 KR KR1019970704130A patent/KR100264369B1/ko not_active IP Right Cessation
- 1995-12-04 PT PT95941665T patent/PT800387E/pt unknown
- 1995-12-04 CZ CZ19971869A patent/CZ288043B6/cs not_active IP Right Cessation
- 1995-12-04 AT AT95941665T patent/ATE222756T1/de not_active IP Right Cessation
- 1995-12-04 DE DE69527980T patent/DE69527980T2/de not_active Expired - Fee Related
- 1995-12-04 CN CN95196940A patent/CN1087609C/zh not_active Expired - Fee Related
- 1995-12-04 EP EP95941665A patent/EP0800387B1/en not_active Expired - Lifetime
- 1995-12-04 CA CA002208351A patent/CA2208351C/en not_active Expired - Fee Related
- 1995-12-04 RU RU97112461/14A patent/RU2181284C2/ru not_active IP Right Cessation
- 1995-12-04 US US08/849,767 patent/US5808137A/en not_active Expired - Fee Related
- 1995-12-04 DK DK95941665T patent/DK0800387T3/da active
- 1995-12-04 WO PCT/EP1995/004770 patent/WO1996019209A1/en active IP Right Grant
- 1995-12-04 HU HU9702094A patent/HU225501B1/hu not_active IP Right Cessation
- 1995-12-04 AU AU43019/96A patent/AU689357B2/en not_active Ceased
- 1995-12-04 ES ES95941665T patent/ES2181806T3/es not_active Expired - Lifetime
- 1995-12-04 SK SK781-97A patent/SK282259B6/sk unknown
-
1997
- 1997-06-19 NO NO972842A patent/NO307926B1/no unknown
- 1997-06-19 FI FI972641A patent/FI972641A/fi unknown
-
2003
- 2003-12-26 JP JP2003434456A patent/JP2004131509A/ja active Pending
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