RU2266291C2 - Халконовые кумарины - Google Patents
Халконовые кумарины Download PDFInfo
- Publication number
- RU2266291C2 RU2266291C2 RU2002108567/04A RU2002108567A RU2266291C2 RU 2266291 C2 RU2266291 C2 RU 2266291C2 RU 2002108567/04 A RU2002108567/04 A RU 2002108567/04A RU 2002108567 A RU2002108567 A RU 2002108567A RU 2266291 C2 RU2266291 C2 RU 2266291C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- methyl
- coumarin
- vib
- och
- Prior art date
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- -1 Chalcone coumarins Chemical class 0.000 title claims abstract description 16
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims abstract 15
- 235000001671 coumarin Nutrition 0.000 title claims abstract 15
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 title abstract description 14
- 235000005513 chalcones Nutrition 0.000 title abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000004429 atom Chemical group 0.000 claims abstract description 30
- 239000003814 drug Substances 0.000 claims abstract description 24
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 22
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 22
- 229930012538 Paclitaxel Natural products 0.000 claims abstract description 19
- 229960001592 paclitaxel Drugs 0.000 claims abstract description 19
- 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 abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 18
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 16
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 15
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 125000003118 aryl group Chemical group 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 9
- 239000002246 antineoplastic agent Substances 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 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 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 abstract description 7
- 229960003668 docetaxel Drugs 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 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 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 239000000654 additive Substances 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 229940079593 drug Drugs 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000005336 allyloxy group Chemical group 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 238000002648 combination therapy Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- MOFATXZICDYOJV-UHFFFAOYSA-N 4-methyl-7-(3-methylbut-2-enoxy)-8-(3-phenylprop-2-enoyl)chromen-2-one Chemical compound CC(C)=CCOC1=CC=C2C(C)=CC(=O)OC2=C1C(=O)C=CC1=CC=CC=C1 MOFATXZICDYOJV-UHFFFAOYSA-N 0.000 claims description 2
- MFFZJBPCZGGLDW-UHFFFAOYSA-N 4-methyl-7-(3-methylbut-2-enoxy)-8-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]chromen-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)C=2C=3OC(=O)C=C(C)C=3C=CC=2OCC=C(C)C)=C1 MFFZJBPCZGGLDW-UHFFFAOYSA-N 0.000 claims description 2
- HQRSAWROMLHMGI-UHFFFAOYSA-N 4-methyl-7-prop-2-ynoxy-8-[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]chromen-2-one Chemical compound COC1=C(OC)C(OC)=CC(C=CC(=O)C=2C=3OC(=O)C=C(C)C=3C=CC=2OCC#C)=C1 HQRSAWROMLHMGI-UHFFFAOYSA-N 0.000 claims description 2
- OVFATDDJFDOWGF-UHFFFAOYSA-N 4-methyl-8-(3-phenylprop-2-enoyl)-7-prop-2-ynoxychromen-2-one Chemical compound C#CCOC=1C=CC=2C(C)=CC(=O)OC=2C=1C(=O)C=CC1=CC=CC=C1 OVFATDDJFDOWGF-UHFFFAOYSA-N 0.000 claims description 2
- JKMJDKPUWIIOGL-UHFFFAOYSA-N 8-[3-(3-methoxyphenyl)prop-2-enoyl]-4-methyl-7-prop-2-ynoxychromen-2-one Chemical compound COC1=CC=CC(C=CC(=O)C=2C=3OC(=O)C=C(C)C=3C=CC=2OCC#C)=C1 JKMJDKPUWIIOGL-UHFFFAOYSA-N 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 210000005075 mammary gland Anatomy 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
- 210000004291 uterus Anatomy 0.000 claims description 2
- 150000004775 coumarins Chemical class 0.000 claims 13
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000009245 menopause Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 10
- 229940127089 cytotoxic agent Drugs 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 210000004027 cell Anatomy 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 210000004881 tumor cell Anatomy 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 42
- 238000003756 stirring Methods 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 10
- 150000001789 chalcones Chemical class 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-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
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 6
- DHOITHIKILTGSO-UHFFFAOYSA-N 8-acetyl-4-methyl-7-prop-2-enoxychromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=CC(OCC=C)=C2C(=O)C DHOITHIKILTGSO-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NPYLBDXWCVGPIO-UHFFFAOYSA-N 8-acetyl-4-methyl-7-prop-2-ynoxychromen-2-one Chemical compound CC1=CC(=O)OC2=C1C=CC(OCC#C)=C2C(=O)C NPYLBDXWCVGPIO-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 229930003935 flavonoid Natural products 0.000 description 4
- 150000002215 flavonoids Chemical class 0.000 description 4
- 235000017173 flavonoids Nutrition 0.000 description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
- LIPXLNAFVXUKJN-UHFFFAOYSA-N 8-acetyl-4-methyl-7-(3-methylbut-2-enoxy)chromen-2-one Chemical compound CC1=CC(=O)OC2=C(C(C)=O)C(OCC=C(C)C)=CC=C21 LIPXLNAFVXUKJN-UHFFFAOYSA-N 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 3
- KIHOFAGVAMNMHH-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(methylamino)propane-1,3-diol Chemical compound CNC(CO)(CO)CO KIHOFAGVAMNMHH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-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
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 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
- UCTUXUGXIFRVGX-UHFFFAOYSA-N 2,3,4-trimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1OC UCTUXUGXIFRVGX-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 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
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- OAEYLUPTDADMNB-UHFFFAOYSA-N 8-[3-(4-fluorophenyl)prop-2-enoyl]-4-methyl-7-prop-2-ynoxychromen-2-one Chemical compound C#CCOC=1C=CC=2C(C)=CC(=O)OC=2C=1C(=O)C=CC1=CC=C(F)C=C1 OAEYLUPTDADMNB-UHFFFAOYSA-N 0.000 description 1
- MZBGYMPFVMGVGE-UHFFFAOYSA-N 8-acetyl-7-methoxy-3-methylchromen-2-one Chemical compound C1=C(C)C(=O)OC2=C(C(C)=O)C(OC)=CC=C21 MZBGYMPFVMGVGE-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- OWNNJASGBXOEFL-BUHFOSPRSA-N CC(C)=C(COc1ccc(C(C)=CC(O2)=O)c2c1C([ClH]/C=C/c1ccccc1)=O)C=C Chemical compound CC(C)=C(COc1ccc(C(C)=CC(O2)=O)c2c1C([ClH]/C=C/c1ccccc1)=O)C=C OWNNJASGBXOEFL-BUHFOSPRSA-N 0.000 description 1
- 0 CC(c(c(O1)c2*C=Cc(cc3)ccc3F)ccc2*#C)=CC1=O Chemical compound CC(c(c(O1)c2*C=Cc(cc3)ccc3F)ccc2*#C)=CC1=O 0.000 description 1
- CRVRRAOAEHJJQF-CMDGGOBGSA-N CC(c(c(O1)c2C([ClH]/C=C/C3=CNCC=C3)=O)ccc2OCC=C)=CC1=O Chemical compound CC(c(c(O1)c2C([ClH]/C=C/C3=CNCC=C3)=O)ccc2OCC=C)=CC1=O CRVRRAOAEHJJQF-CMDGGOBGSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000017657 Menopausal disease Diseases 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000003632 chemoprophylactic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 230000007423 decrease Effects 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
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 238000000338 in vitro Methods 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
- 239000008101 lactose Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000007916 tablet composition Substances 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
- 235000021119 whey protein Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- 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
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Saccharide Compounds (AREA)
- General Preparation And Processing Of Foods (AREA)
- Glass Compositions (AREA)
- Fire-Extinguishing Compositions (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9920908.2 | 1999-09-03 | ||
| GBGB9920908.2A GB9920908D0 (en) | 1999-09-03 | 1999-09-03 | Chalcone coumarins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2002108567A RU2002108567A (ru) | 2004-01-10 |
| RU2266291C2 true RU2266291C2 (ru) | 2005-12-20 |
Family
ID=10860344
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2002108567/04A RU2266291C2 (ru) | 1999-09-03 | 2000-08-28 | Халконовые кумарины |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6767916B2 (enExample) |
| EP (1) | EP1212311B1 (enExample) |
| JP (1) | JP2003508523A (enExample) |
| KR (1) | KR100819574B1 (enExample) |
| CN (1) | CN1142927C (enExample) |
| AT (1) | ATE235480T1 (enExample) |
| AU (1) | AU775083B2 (enExample) |
| CA (1) | CA2382112A1 (enExample) |
| CZ (1) | CZ2002786A3 (enExample) |
| DE (1) | DE60001850T2 (enExample) |
| DK (1) | DK1212311T3 (enExample) |
| ES (1) | ES2191643T3 (enExample) |
| GB (1) | GB9920908D0 (enExample) |
| HK (1) | HK1043997B (enExample) |
| HU (1) | HUP0202581A3 (enExample) |
| NO (1) | NO20021048L (enExample) |
| PL (1) | PL353245A1 (enExample) |
| PT (1) | PT1212311E (enExample) |
| RU (1) | RU2266291C2 (enExample) |
| SE (1) | SE1212311T5 (enExample) |
| SK (1) | SK3102002A3 (enExample) |
| WO (1) | WO2001017984A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2760006C1 (ru) * | 2017-11-16 | 2021-11-22 | Дзе Инститьют оф Кансер Рисерч: Ройал Кансер Хоспитал | Производное кумарина для лечения или профилактики расстройства пролиферации клеток |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030229136A1 (en) | 2002-04-18 | 2003-12-11 | Nurulain Zaveri | Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| US7638554B2 (en) | 2002-04-18 | 2009-12-29 | Sri International | Flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| WO2006132947A2 (en) | 2005-06-08 | 2006-12-14 | Temple University- Of The Commonwealth System Of Higher Education | 3-acyl coumarins, thiochromones and quinolones and therapeutic uses thereof |
| CN101041646B (zh) * | 2007-04-30 | 2011-07-20 | 浙江大学 | 含氮查耳酮衍生物的制备方法和用途 |
| CN101121706B (zh) * | 2007-09-18 | 2010-11-24 | 南京中瑞药业有限公司 | 一种香豆素衍生物及其制备方法和用途 |
| JP5479105B2 (ja) * | 2007-11-05 | 2014-04-23 | 国立大学法人佐賀大学 | 新規ユビキリン結合性小分子 |
| EP2601183A1 (en) | 2010-08-05 | 2013-06-12 | Council Of Scientific & Industrial Research | Coumarin-chalcones as anticancer agents |
| US10071945B2 (en) | 2011-06-15 | 2018-09-11 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Nuclear receptor modulators and their use for the treatment and prevention of cancer |
| CN104987328A (zh) * | 2012-05-23 | 2015-10-21 | 复旦大学 | 7-氧、硫或氮杂取代香豆素及其衍生物和用途 |
| CN102731457A (zh) * | 2012-06-25 | 2012-10-17 | 西南石油大学 | 一种水溶性荧光示踪聚合物及其制备方法 |
| CN109293616B (zh) * | 2018-09-29 | 2022-06-21 | 贵州大学 | 一种含香豆素查尔酮类衍生物、其制备方法及应用 |
| JP2022547358A (ja) | 2019-09-13 | 2022-11-14 | ジ インスティテュート オブ キャンサー リサーチ：ロイヤル キャンサー ホスピタル | 治療組成物、組み合わせ、及び使用方法 |
| US11873296B2 (en) | 2022-06-07 | 2024-01-16 | Verastem, Inc. | Solid forms of a dual RAF/MEK inhibitor |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991017749A1 (en) * | 1990-05-17 | 1991-11-28 | Baylor College Of Medicine | Growth inhibitors and methods of treating cancer and cell proliferative diseases |
| WO1995018803A1 (en) * | 1994-01-07 | 1995-07-13 | Allergan | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
| WO1996019209A1 (en) * | 1994-12-20 | 1996-06-27 | Indena S.P.A. | Chalcones and esters thereof with antiproliferative activity in uterus, ovary and breast tumours |
| WO1996022985A1 (en) * | 1995-01-24 | 1996-08-01 | Warner-Lambert Company | 2-(2-amino-3-methoxyphenyl)-4-oxo-4h-[1]benzopyran for treating proliferative disorders |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2387956A1 (fr) * | 1977-04-20 | 1978-11-17 | Unicler | Derives de la pyridine et leur preparation |
| US5023341A (en) * | 1989-09-19 | 1991-06-11 | Allergan, Inc. | Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
-
1999
- 1999-09-03 GB GBGB9920908.2A patent/GB9920908D0/en not_active Ceased
-
2000
- 2000-08-28 CN CNB00812163XA patent/CN1142927C/zh not_active Expired - Fee Related
- 2000-08-28 PT PT00965902T patent/PT1212311E/pt unknown
- 2000-08-28 CA CA002382112A patent/CA2382112A1/en not_active Abandoned
- 2000-08-28 CZ CZ2002786A patent/CZ2002786A3/cs unknown
- 2000-08-28 ES ES00965902T patent/ES2191643T3/es not_active Expired - Lifetime
- 2000-08-28 DK DK00965902T patent/DK1212311T3/da active
- 2000-08-28 AT AT00965902T patent/ATE235480T1/de not_active IP Right Cessation
- 2000-08-28 WO PCT/EP2000/008367 patent/WO2001017984A1/en not_active Ceased
- 2000-08-28 JP JP2001521731A patent/JP2003508523A/ja not_active Withdrawn
- 2000-08-28 HK HK02105581.2A patent/HK1043997B/en unknown
- 2000-08-28 EP EP00965902A patent/EP1212311B1/en not_active Expired - Lifetime
- 2000-08-28 RU RU2002108567/04A patent/RU2266291C2/ru not_active IP Right Cessation
- 2000-08-28 SK SK310-2002A patent/SK3102002A3/sk unknown
- 2000-08-28 DE DE60001850T patent/DE60001850T2/de not_active Expired - Fee Related
- 2000-08-28 PL PL00353245A patent/PL353245A1/xx not_active IP Right Cessation
- 2000-08-28 AU AU76488/00A patent/AU775083B2/en not_active Ceased
- 2000-08-28 HU HU0202581A patent/HUP0202581A3/hu unknown
- 2000-08-28 SE SE00965902T patent/SE1212311T5/xx unknown
- 2000-08-28 KR KR1020027002799A patent/KR100819574B1/ko not_active Expired - Fee Related
-
2002
- 2002-02-15 US US10/075,625 patent/US6767916B2/en not_active Expired - Fee Related
- 2002-03-01 NO NO20021048A patent/NO20021048L/no not_active Application Discontinuation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991017749A1 (en) * | 1990-05-17 | 1991-11-28 | Baylor College Of Medicine | Growth inhibitors and methods of treating cancer and cell proliferative diseases |
| WO1995018803A1 (en) * | 1994-01-07 | 1995-07-13 | Allergan | Acetylenes disubstituted with a phenyl or heteroaryl group and a 2-oxochromanyl, 2-oxothiochromanyl or 2-oxo-1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity |
| WO1996019209A1 (en) * | 1994-12-20 | 1996-06-27 | Indena S.P.A. | Chalcones and esters thereof with antiproliferative activity in uterus, ovary and breast tumours |
| WO1996022985A1 (en) * | 1995-01-24 | 1996-08-01 | Warner-Lambert Company | 2-(2-amino-3-methoxyphenyl)-4-oxo-4h-[1]benzopyran for treating proliferative disorders |
Non-Patent Citations (1)
| Title |
|---|
| KHAN M.S.Y. et al. Synthesis of new alpha-pyronoflavones and related products. Part II. Indian J. Chem. Sect.B (1993), 32(8), p.817-821. SHARAN P. et al. Synthesis of some 7-hydroxy-4-methylcoumarin-8-yl chalcones and related izoxasoles as potential fungicides. Indian J. Chem. Soc. (1989), 66(6), p.393-394. SANGWAN, NARESH K. et al. Synthesis and biological properties of substituted 2H-1-benzopyran-2-ones and 2H,10H-benzo '1,2-b:3.4-b' dipyran-2,10-diones. J. Prakt. Chem. (1988), 330(1), p.137-141. AHLUWALIA V.K. et al. New route to synthesis of some 8-(dihydrocinnamoyl)dihydrocoumarin derivatives. Indian J. Chem. Sect.B. (1988), 27B (1), p.70-71. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2760006C1 (ru) * | 2017-11-16 | 2021-11-22 | Дзе Инститьют оф Кансер Рисерч: Ройал Кансер Хоспитал | Производное кумарина для лечения или профилактики расстройства пролиферации клеток |
Also Published As
| Publication number | Publication date |
|---|---|
| NO20021048D0 (no) | 2002-03-01 |
| NO20021048L (no) | 2002-05-03 |
| KR100819574B1 (ko) | 2008-04-04 |
| ATE235480T1 (de) | 2003-04-15 |
| AU775083B2 (en) | 2004-07-15 |
| EP1212311B1 (en) | 2003-03-26 |
| CZ2002786A3 (cs) | 2002-06-12 |
| CN1371370A (zh) | 2002-09-25 |
| DE60001850D1 (de) | 2003-04-30 |
| KR20020030800A (ko) | 2002-04-25 |
| US20020161036A1 (en) | 2002-10-31 |
| AU7648800A (en) | 2001-04-10 |
| HK1043997B (en) | 2003-08-15 |
| SE1212311T3 (enExample) | 2003-05-06 |
| CA2382112A1 (en) | 2001-03-15 |
| DE60001850T2 (de) | 2003-12-11 |
| CN1142927C (zh) | 2004-03-24 |
| US6767916B2 (en) | 2004-07-27 |
| RU2002108567A (ru) | 2004-01-10 |
| EP1212311A1 (en) | 2002-06-12 |
| JP2003508523A (ja) | 2003-03-04 |
| SK3102002A3 (en) | 2003-10-07 |
| WO2001017984A1 (en) | 2001-03-15 |
| HUP0202581A3 (en) | 2003-07-28 |
| HK1043997A1 (en) | 2002-10-04 |
| DK1212311T3 (da) | 2003-06-23 |
| HUP0202581A2 (hu) | 2002-11-28 |
| SE1212311T5 (enExample) | 2003-06-10 |
| GB9920908D0 (en) | 1999-11-10 |
| ES2191643T3 (es) | 2003-09-16 |
| PL353245A1 (en) | 2003-11-03 |
| PT1212311E (pt) | 2003-08-29 |
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Legal Events
| Date | Code | Title | Description |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20080829 |