RU2252938C2 - Халконы и фармацевтическая композиция на их основе - Google Patents
Халконы и фармацевтическая композиция на их основе Download PDFInfo
- Publication number
- RU2252938C2 RU2252938C2 RU2002108566/04A RU2002108566A RU2252938C2 RU 2252938 C2 RU2252938 C2 RU 2252938C2 RU 2002108566/04 A RU2002108566/04 A RU 2002108566/04A RU 2002108566 A RU2002108566 A RU 2002108566A RU 2252938 C2 RU2252938 C2 RU 2252938C2
- Authority
- RU
- Russia
- Prior art keywords
- vib
- group
- methyl
- chalcones
- flavon
- Prior art date
Links
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 235000005513 chalcones Nutrition 0.000 title claims abstract description 24
- 150000001789 chalcones Chemical class 0.000 title claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
- 125000001424 substituent group Chemical group 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 20
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 19
- 229940079593 drug Drugs 0.000 claims abstract description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 14
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims abstract description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims abstract 3
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims abstract 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 3
- 125000004122 cyclic group Chemical group 0.000 claims description 26
- -1 3-methylbut-2-enyloxy Chemical group 0.000 claims description 23
- 229930012538 Paclitaxel Natural products 0.000 claims description 20
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 229960001592 paclitaxel Drugs 0.000 claims description 20
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound 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 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 16
- 230000002265 prevention Effects 0.000 claims description 10
- 239000002246 antineoplastic agent Substances 0.000 claims description 9
- 125000005336 allyloxy group Chemical group 0.000 claims description 7
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 229960003668 docetaxel Drugs 0.000 claims description 6
- 238000002648 combination therapy Methods 0.000 claims description 4
- LAWDSOAXOCOSPV-UHFFFAOYSA-N 3-(3-methylbut-2-enoxy)-4-(3-phenylprop-2-enoyl)xanthen-9-one Chemical compound CC(C)=CCOC1=CC=C(C(C2=CC=CC=C2O2)=O)C2=C1C(=O)C=CC1=CC=CC=C1 LAWDSOAXOCOSPV-UHFFFAOYSA-N 0.000 claims description 2
- CXKQXJPYPVCTRV-UHFFFAOYSA-N 3-(3-methylbut-2-enoxy)-4-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]xanthen-9-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)C=2C3=C(C(C4=CC=CC=C4O3)=O)C=CC=2OCC=C(C)C)=C1 CXKQXJPYPVCTRV-UHFFFAOYSA-N 0.000 claims description 2
- FSWITLPOTVKWFR-UHFFFAOYSA-N 3-methyl-7-(3-methylbut-2-enoxy)-2-phenyl-8-(3-phenylprop-2-enoyl)chromen-4-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=1C(OCC=C(C)C)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 FSWITLPOTVKWFR-UHFFFAOYSA-N 0.000 claims description 2
- AEQVLDDVEGAKDQ-UHFFFAOYSA-N 4-(3-phenylprop-2-enoyl)-3-prop-2-enoxyxanthen-9-one Chemical compound C=CCOC1=CC=C(C(C2=CC=CC=C2O2)=O)C2=C1C(=O)C=CC1=CC=CC=C1 AEQVLDDVEGAKDQ-UHFFFAOYSA-N 0.000 claims description 2
- NVLXRSGZLQABNZ-UHFFFAOYSA-N 4-[3-(3-methoxyphenyl)prop-2-enoyl]-3-(3-methylbut-2-enoxy)xanthen-9-one Chemical compound COC1=CC=CC(C=CC(=O)C=2C3=C(C(C4=CC=CC=C4O3)=O)C=CC=2OCC=C(C)C)=C1 NVLXRSGZLQABNZ-UHFFFAOYSA-N 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 210000005075 mammary gland Anatomy 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 208000017657 Menopausal disease Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 18
- 230000000694 effects Effects 0.000 abstract description 3
- 238000011321 prophylaxis Methods 0.000 abstract description 2
- 230000000975 bioactive effect Effects 0.000 abstract 2
- 208000035269 cancer or benign tumor Diseases 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001788 chalcone derivatives Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 125000004429 atom Chemical group 0.000 description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 46
- 238000003756 stirring Methods 0.000 description 45
- 239000002244 precipitate Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 18
- 238000005160 1H NMR spectroscopy Methods 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 125000005842 heteroatom Chemical group 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 9
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 8
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- QTZKZSCYJPRVIR-UHFFFAOYSA-N 8-acetyl-3-methyl-7-(3-methylbut-2-enoxy)-2-phenylchromen-4-one Chemical compound CC(=O)C=1C(OCC=C(C)C)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 QTZKZSCYJPRVIR-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 229930003935 flavonoid Natural products 0.000 description 4
- 150000002215 flavonoids Chemical class 0.000 description 4
- 235000017173 flavonoids Nutrition 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- 229940041181 antineoplastic drug Drugs 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 3
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 2
- KIHOFAGVAMNMHH-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(methylamino)propane-1,3-diol Chemical compound CNC(CO)(CO)CO KIHOFAGVAMNMHH-UHFFFAOYSA-N 0.000 description 2
- ZWFLKUIBSHRXGV-UHFFFAOYSA-N 8-acetyl-3-methyl-2-phenyl-7-prop-2-ynoxychromen-4-one Chemical compound CC(=O)C1=C(OCC#C)C=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 ZWFLKUIBSHRXGV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002212 flavone derivatives Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- DMIYKWPEFRFTPY-UHFFFAOYSA-N 2,6-dichlorobenzaldehyde Chemical compound ClC1=CC=CC(Cl)=C1C=O DMIYKWPEFRFTPY-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- KYSINLVQQUGFHL-UHFFFAOYSA-N 4-[3-(7-methoxy-3-methyl-4-oxo-2-phenylchromen-8-yl)-3-oxoprop-1-enyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C=CC(=O)C=1C(OC)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 KYSINLVQQUGFHL-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- PIMQQGJMDMAZGT-UHFFFAOYSA-N 4-methylthiobenzaldehyde Chemical compound CC1=CC=C(C=S)C=C1 PIMQQGJMDMAZGT-UHFFFAOYSA-N 0.000 description 1
- LQSXIJMZDGZTQI-UHFFFAOYSA-N 8-[3-(4-chlorophenyl)prop-2-enoyl]-3-methyl-7-(3-methylbut-2-enoxy)-2-phenylchromen-4-one Chemical compound C=1C=C(Cl)C=CC=1C=CC(=O)C=1C(OCC=C(C)C)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 LQSXIJMZDGZTQI-UHFFFAOYSA-N 0.000 description 1
- VBUCSGMSTAORPZ-UHFFFAOYSA-N 8-acetyl-7-methoxy-3-methyl-2-phenylchromen-4-one Chemical compound CC(=O)C=1C(OC)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 VBUCSGMSTAORPZ-UHFFFAOYSA-N 0.000 description 1
- 208000036832 Adenocarcinoma of ovary Diseases 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 206010061328 Ovarian epithelial cancer Diseases 0.000 description 1
- 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 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 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 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 102000015694 estrogen receptors Human genes 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 208000013371 ovarian adenocarcinoma Diseases 0.000 description 1
- 201000006588 ovary adenocarcinoma Diseases 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 229960001285 quercetin Drugs 0.000 description 1
- 235000005875 quercetin Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 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 1
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9920910.8 | 1999-09-03 | ||
| GBGB9920910.8A GB9920910D0 (en) | 1999-09-03 | 1999-09-03 | Novel chalcones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002108566A RU2002108566A (ru) | 2003-11-10 |
| RU2252938C2 true RU2252938C2 (ru) | 2005-05-27 |
Family
ID=10860346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002108566/04A RU2252938C2 (ru) | 1999-09-03 | 2000-08-28 | Халконы и фармацевтическая композиция на их основе |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6620842B2 (enExample) |
| EP (1) | EP1212315B1 (enExample) |
| JP (1) | JP2003508527A (enExample) |
| KR (1) | KR100819576B1 (enExample) |
| CN (1) | CN1177843C (enExample) |
| AT (1) | ATE235483T1 (enExample) |
| AU (1) | AU776226B2 (enExample) |
| CA (1) | CA2382130A1 (enExample) |
| CZ (1) | CZ2002787A3 (enExample) |
| DE (1) | DE60001851T2 (enExample) |
| DK (1) | DK1212315T3 (enExample) |
| ES (1) | ES2193106T3 (enExample) |
| GB (1) | GB9920910D0 (enExample) |
| HK (1) | HK1043999B (enExample) |
| HU (1) | HUP0202579A3 (enExample) |
| NO (1) | NO20021049L (enExample) |
| PL (1) | PL353064A1 (enExample) |
| PT (1) | PT1212315E (enExample) |
| RU (1) | RU2252938C2 (enExample) |
| SK (1) | SK3112002A3 (enExample) |
| WO (1) | WO2001017988A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003088903A2 (en) | 2002-04-17 | 2003-10-30 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| US7638554B2 (en) * | 2002-04-18 | 2009-12-29 | Sri International | Flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| US20030229136A1 (en) * | 2002-04-18 | 2003-12-11 | Nurulain Zaveri | Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| DE60326248D1 (de) | 2002-07-17 | 2009-04-02 | Cytokinetics Inc | Verbindungen, zusammensetzungen und verfahren zur behandlung von zellulären proliferativen erkrankungen |
| US6864264B1 (en) | 2002-08-20 | 2005-03-08 | Gloria L. Anderson | 1-adamantyl chalcones for the treatment of proliferative disorders |
| 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 |
| WO2013127361A1 (en) * | 2012-03-01 | 2013-09-06 | The Hong Kong Polytechnic University | Alkyne-, azide- and triazole-containing flavonoids as modulators for multidrug resistance in cancers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2007401C1 (ru) * | 1990-02-16 | 1994-02-15 | Эли Лилли Энд Компани | Способ получения трициклических соединений |
| RU2118321C1 (ru) * | 1988-12-21 | 1998-08-27 | Дзе Апджон Компани | Замещенные бензопираноны и их фармацевтически приемлемые соли и гидраты |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5023341A (en) * | 1989-09-19 | 1991-06-11 | Allergan, Inc. | Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
| JPH05509078A (ja) * | 1990-05-17 | 1993-12-16 | ベイラー カレッジ オブ メディシン | 成長抑制因とガンおよび細胞増殖性疾患措置法 |
| IT1271301B (it) * | 1994-12-20 | 1997-05-27 | Indena Spa | Calconi naturali e sintetici e loro esteri ad attivita' antiproliferativa nei tumori dell'utero,dell'ovaio e del seno e formulazioni che li contengono |
| US5525625A (en) * | 1995-01-24 | 1996-06-11 | Warner-Lambert Company | 2-(2-Amino-3-methoxyphenyl)-4-oxo-4H-[1]benzopyran for treating proliferative disorders |
-
1999
- 1999-09-03 GB GBGB9920910.8A patent/GB9920910D0/en not_active Ceased
-
2000
- 2000-08-28 JP JP2001522211A patent/JP2003508527A/ja not_active Withdrawn
- 2000-08-28 DE DE60001851T patent/DE60001851T2/de not_active Expired - Fee Related
- 2000-08-28 PT PT00964042T patent/PT1212315E/pt unknown
- 2000-08-28 EP EP00964042A patent/EP1212315B1/en not_active Expired - Lifetime
- 2000-08-28 ES ES00964042T patent/ES2193106T3/es not_active Expired - Lifetime
- 2000-08-28 HK HK02105661.5A patent/HK1043999B/en unknown
- 2000-08-28 RU RU2002108566/04A patent/RU2252938C2/ru not_active IP Right Cessation
- 2000-08-28 HU HU0202579A patent/HUP0202579A3/hu unknown
- 2000-08-28 AU AU75109/00A patent/AU776226B2/en not_active Ceased
- 2000-08-28 DK DK00964042T patent/DK1212315T3/da active
- 2000-08-28 PL PL00353064A patent/PL353064A1/xx not_active IP Right Cessation
- 2000-08-28 SK SK311-2002A patent/SK3112002A3/sk unknown
- 2000-08-28 KR KR1020027002798A patent/KR100819576B1/ko not_active Expired - Fee Related
- 2000-08-28 AT AT00964042T patent/ATE235483T1/de not_active IP Right Cessation
- 2000-08-28 CN CNB008123039A patent/CN1177843C/zh not_active Expired - Fee Related
- 2000-08-28 WO PCT/EP2000/008366 patent/WO2001017988A1/en not_active Ceased
- 2000-08-28 CZ CZ2002787A patent/CZ2002787A3/cs unknown
- 2000-08-28 CA CA002382130A patent/CA2382130A1/en not_active Abandoned
-
2002
- 2002-02-15 US US10/075,626 patent/US6620842B2/en not_active Expired - Fee Related
- 2002-03-01 NO NO20021049A patent/NO20021049L/no not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2118321C1 (ru) * | 1988-12-21 | 1998-08-27 | Дзе Апджон Компани | Замещенные бензопираноны и их фармацевтически приемлемые соли и гидраты |
| RU2007401C1 (ru) * | 1990-02-16 | 1994-02-15 | Эли Лилли Энд Компани | Способ получения трициклических соединений |
Non-Patent Citations (1)
| Title |
|---|
| Chem. Abstr., v.116, n.12,1992. Chem.Abstr., v.112, n.5, 1990. * |
Also Published As
| Publication number | Publication date |
|---|---|
| ATE235483T1 (de) | 2003-04-15 |
| AU7510900A (en) | 2001-04-10 |
| DE60001851D1 (de) | 2003-04-30 |
| ES2193106T3 (es) | 2003-11-01 |
| AU776226B2 (en) | 2004-09-02 |
| HUP0202579A2 (hu) | 2002-11-28 |
| JP2003508527A (ja) | 2003-03-04 |
| EP1212315B1 (en) | 2003-03-26 |
| NO20021049L (no) | 2002-05-03 |
| CN1371372A (zh) | 2002-09-25 |
| US20030055056A1 (en) | 2003-03-20 |
| DK1212315T3 (da) | 2003-06-23 |
| PT1212315E (pt) | 2003-08-29 |
| SK3112002A3 (en) | 2003-10-07 |
| NO20021049D0 (no) | 2002-03-01 |
| WO2001017988A1 (en) | 2001-03-15 |
| GB9920910D0 (en) | 1999-11-10 |
| HUP0202579A3 (en) | 2003-07-28 |
| PL353064A1 (en) | 2003-10-06 |
| US6620842B2 (en) | 2003-09-16 |
| KR20020031598A (ko) | 2002-05-02 |
| CZ2002787A3 (cs) | 2002-06-12 |
| EP1212315A1 (en) | 2002-06-12 |
| HK1043999A1 (en) | 2002-10-04 |
| CN1177843C (zh) | 2004-12-01 |
| DE60001851T2 (de) | 2003-12-11 |
| HK1043999B (en) | 2003-08-15 |
| KR100819576B1 (ko) | 2008-04-22 |
| CA2382130A1 (en) | 2001-03-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2252221C2 (ru) | Производные флавонов, ксантонов и кумаринов и фармацевтическая композиция на их основе | |
| RU2266291C2 (ru) | Халконовые кумарины | |
| RU2252938C2 (ru) | Халконы и фармацевтическая композиция на их основе | |
| WO2008092352A1 (en) | Antitumor compounds and their preparation method | |
| JP2019523230A (ja) | 抗転移性２Ｈ‐セレノフェノ［３，２‐ｈ］クロメン、それらの合成、および同薬剤の使用方法 | |
| WO2011009826A2 (en) | Novel chalcone derivatives with cytotoxic activity | |
| RU2707972C1 (ru) | 4-(2,4-диметоксифенил)-2-(2-гидроксифенил)-5,6-дигидро-4н-бензо[h]хромен-3-карбоновая кислота, обладающая цитотоксической активностью |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20080829 |