DE60001851T2 - Neue chalchone - Google Patents
Neue chalchoneInfo
- Publication number
- DE60001851T2 DE60001851T2 DE60001851T DE60001851T DE60001851T2 DE 60001851 T2 DE60001851 T2 DE 60001851T2 DE 60001851 T DE60001851 T DE 60001851T DE 60001851 T DE60001851 T DE 60001851T DE 60001851 T2 DE60001851 T2 DE 60001851T2
- Authority
- DE
- Germany
- Prior art keywords
- group
- ring atoms
- substituted
- ocor11
- vib
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- 239000003814 drug Substances 0.000 claims abstract description 19
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 230000001028 anti-proliverative effect Effects 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 6
- 208000017657 Menopausal disease Diseases 0.000 claims abstract description 3
- 208000001132 Osteoporosis Diseases 0.000 claims abstract description 3
- 210000000481 breast Anatomy 0.000 claims abstract description 3
- 210000001672 ovary Anatomy 0.000 claims abstract description 3
- 210000004291 uterus Anatomy 0.000 claims abstract description 3
- 125000006413 ring segment Chemical group 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 43
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 32
- 125000002837 carbocyclic group Chemical group 0.000 claims description 32
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229930012538 Paclitaxel Natural products 0.000 claims description 15
- 229960001592 paclitaxel Drugs 0.000 claims description 15
- 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 15
- -1 2-hydroxyphenyl Chemical group 0.000 claims description 11
- 239000002246 antineoplastic agent Substances 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 229940034982 antineoplastic agent Drugs 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
- 229960003668 docetaxel Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 238000002648 combination therapy Methods 0.000 claims description 4
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 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 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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
- 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
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 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 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001788 chalcone derivatives Chemical class 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 74
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 46
- 238000003756 stirring Methods 0.000 description 44
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
- 235000019441 ethanol Nutrition 0.000 description 25
- 239000002244 precipitate Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 238000001914 filtration Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 235000005513 chalcones Nutrition 0.000 description 11
- OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 10
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 8
- 150000001789 chalcones Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 201000011510 cancer Diseases 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
- 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
- 238000000034 method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 4
- RUSYQMLUEHJFPU-UHFFFAOYSA-N 4-acetyl-3-(3-methylbut-2-enoxy)xanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=C(OCC=C(C)C)C(C(C)=O)=C3OC2=C1 RUSYQMLUEHJFPU-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- 239000002253 acid Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 238000004587 chromatography analysis 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 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
- LOOZHKJLLIXWSP-UHFFFAOYSA-N 2-(1,2-benzothiazepin-3-yl)chromen-4-one Chemical class S1C2=CC=CC=C2C=CC(C2=CC(C3=CC=CC=C3O2)=O)=N1 LOOZHKJLLIXWSP-UHFFFAOYSA-N 0.000 description 1
- LWAISILEKXEBNH-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)chromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C=C1C=1C=CNN=1 LWAISILEKXEBNH-UHFFFAOYSA-N 0.000 description 1
- QFWCYNPOPKQOKV-UHFFFAOYSA-N 2-(2-amino-3-methoxyphenyl)chromen-4-one Chemical compound COC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1N QFWCYNPOPKQOKV-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
- UBGDFRKKWBNQDF-UHFFFAOYSA-N 3-methyl-2-phenyl-8-(3-phenylprop-2-enoyl)-7-prop-2-ynoxychromen-4-one Chemical compound C#CCOC1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)C=CC1=CC=CC=C1 UBGDFRKKWBNQDF-UHFFFAOYSA-N 0.000 description 1
- NFDQAALGUIXWTD-UHFFFAOYSA-N 3-methyl-7-(3-methylbut-2-enoxy)-2-phenyl-8-(3-thiophen-2-ylprop-2-enoyl)chromen-4-one Chemical compound C=1C=CSC=1C=CC(=O)C=1C(OCC=C(C)C)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 NFDQAALGUIXWTD-UHFFFAOYSA-N 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
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 230000002634 anti-blastic effect Effects 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002113 chemopreventative effect Effects 0.000 description 1
- 229940044683 chemotherapy drug Drugs 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical group C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003937 drug carrier Substances 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
- 238000002474 experimental method Methods 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 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
- 208000032839 leukemia Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000035755 proliferation Effects 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
- 230000002441 reversible effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- DHNUAKOQUGJUGA-UHFFFAOYSA-N silicon;sulfane Chemical compound [Si].S DHNUAKOQUGJUGA-UHFFFAOYSA-N 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
- 125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Physical Education & Sports Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Endocrinology (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 |
|---|---|---|---|
| GBGB9920910.8A GB9920910D0 (en) | 1999-09-03 | 1999-09-03 | Novel chalcones |
| PCT/EP2000/008366 WO2001017988A1 (en) | 1999-09-03 | 2000-08-28 | Novel chalcones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60001851D1 DE60001851D1 (de) | 2003-04-30 |
| DE60001851T2 true DE60001851T2 (de) | 2003-12-11 |
Family
ID=10860346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60001851T Expired - Fee Related DE60001851T2 (de) | 1999-09-03 | 2000-08-28 | Neue chalchone |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US6620842B2 (https=) |
| EP (1) | EP1212315B1 (https=) |
| JP (1) | JP2003508527A (https=) |
| KR (1) | KR100819576B1 (https=) |
| CN (1) | CN1177843C (https=) |
| AT (1) | ATE235483T1 (https=) |
| AU (1) | AU776226B2 (https=) |
| CA (1) | CA2382130A1 (https=) |
| CZ (1) | CZ2002787A3 (https=) |
| DE (1) | DE60001851T2 (https=) |
| DK (1) | DK1212315T3 (https=) |
| ES (1) | ES2193106T3 (https=) |
| GB (1) | GB9920910D0 (https=) |
| HK (1) | HK1043999B (https=) |
| HU (1) | HUP0202579A3 (https=) |
| NO (1) | NO20021049L (https=) |
| PL (1) | PL353064A1 (https=) |
| PT (1) | PT1212315E (https=) |
| RU (1) | RU2252938C2 (https=) |
| SK (1) | SK3112002A3 (https=) |
| WO (1) | WO2001017988A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003234733B2 (en) | 2002-04-17 | 2009-01-29 | Cytokinetics, Inc. | Compounds, compositions, and methods |
| 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 |
| JP2005533119A (ja) | 2002-07-17 | 2005-11-04 | サイトキネティクス・インコーポレーテッド | 化合物、組成物、及び方法 |
| 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1990006921A1 (en) * | 1988-12-21 | 1990-06-28 | The Upjohn Company | Antiatherosclerotic and antithrombotic 1-benzopyran-4-ones and 2-amino-1,3-benzoxazine-4-ones |
| US5023341A (en) * | 1989-09-19 | 1991-06-11 | Allergan, Inc. | Compounds having a disubstituted acetylene moiety and retinoic acid-like biological activity |
| US4996230A (en) * | 1990-02-16 | 1991-02-26 | Eli Lilly And Company | Leukotriene antagonists |
| WO1991017749A1 (en) * | 1990-05-17 | 1991-11-28 | Baylor College Of Medicine | Growth inhibitors and methods of treating cancer and cell proliferative diseases |
| 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 CA CA002382130A patent/CA2382130A1/en not_active Abandoned
- 2000-08-28 ES ES00964042T patent/ES2193106T3/es not_active Expired - Lifetime
- 2000-08-28 CN CNB008123039A patent/CN1177843C/zh not_active Expired - Fee Related
- 2000-08-28 CZ CZ2002787A patent/CZ2002787A3/cs unknown
- 2000-08-28 SK SK311-2002A patent/SK3112002A3/sk unknown
- 2000-08-28 HU HU0202579A patent/HUP0202579A3/hu unknown
- 2000-08-28 DK DK00964042T patent/DK1212315T3/da active
- 2000-08-28 HK HK02105661.5A patent/HK1043999B/en unknown
- 2000-08-28 EP EP00964042A patent/EP1212315B1/en not_active Expired - Lifetime
- 2000-08-28 PL PL00353064A patent/PL353064A1/xx not_active IP Right Cessation
- 2000-08-28 AU AU75109/00A patent/AU776226B2/en not_active Ceased
- 2000-08-28 RU RU2002108566/04A patent/RU2252938C2/ru not_active IP Right Cessation
- 2000-08-28 DE DE60001851T patent/DE60001851T2/de not_active Expired - Fee Related
- 2000-08-28 AT AT00964042T patent/ATE235483T1/de not_active IP Right Cessation
- 2000-08-28 WO PCT/EP2000/008366 patent/WO2001017988A1/en not_active Ceased
- 2000-08-28 KR KR1020027002798A patent/KR100819576B1/ko not_active Expired - Fee Related
- 2000-08-28 PT PT00964042T patent/PT1212315E/pt unknown
- 2000-08-28 JP JP2001522211A patent/JP2003508527A/ja not_active Withdrawn
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| EP1212315B1 (en) | 2003-03-26 |
| GB9920910D0 (en) | 1999-11-10 |
| DK1212315T3 (da) | 2003-06-23 |
| ES2193106T3 (es) | 2003-11-01 |
| NO20021049D0 (no) | 2002-03-01 |
| DE60001851D1 (de) | 2003-04-30 |
| WO2001017988A1 (en) | 2001-03-15 |
| JP2003508527A (ja) | 2003-03-04 |
| US6620842B2 (en) | 2003-09-16 |
| HUP0202579A3 (en) | 2003-07-28 |
| CN1177843C (zh) | 2004-12-01 |
| CA2382130A1 (en) | 2001-03-15 |
| EP1212315A1 (en) | 2002-06-12 |
| SK3112002A3 (en) | 2003-10-07 |
| HK1043999B (en) | 2003-08-15 |
| KR20020031598A (ko) | 2002-05-02 |
| KR100819576B1 (ko) | 2008-04-22 |
| CN1371372A (zh) | 2002-09-25 |
| ATE235483T1 (de) | 2003-04-15 |
| NO20021049L (no) | 2002-05-03 |
| PT1212315E (pt) | 2003-08-29 |
| HUP0202579A2 (hu) | 2002-11-28 |
| AU7510900A (en) | 2001-04-10 |
| US20030055056A1 (en) | 2003-03-20 |
| RU2252938C2 (ru) | 2005-05-27 |
| HK1043999A1 (en) | 2002-10-04 |
| AU776226B2 (en) | 2004-09-02 |
| CZ2002787A3 (cs) | 2002-06-12 |
| PL353064A1 (en) | 2003-10-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60001974T2 (de) | Derivate von flavonen, xanthonen und kumarinen | |
| DE60001850T2 (de) | Chalcon coumarine | |
| DE69831409T2 (de) | Chalcon-derivate mit antiproliferativer aktivität | |
| JP2006508147A (ja) | 新規ラパコン化合物およびその使用方法 | |
| AU2011292144A1 (en) | 1,5-diphenyl-penta-1,4-dien-3-one compounds | |
| EP0433233B1 (de) | Heterocyclische Verbindungen | |
| DE60001851T2 (de) | Neue chalchone | |
| Mostafa et al. | Synthesis of novel benzopyran-connected pyrimidine and pyrazole derivatives via a green method using Cu (II)-tyrosinase enzyme catalyst as potential larvicidal, antifeedant activities | |
| DE60108354T2 (de) | 2H-1-Benzopyranderivate, Verfahren zu ihrer Herstellung und deren pharmazeutische Zusammensetzungen | |
| WO1999032115A1 (en) | Modulators of ryanodine receptors comprising 2-(aryl)-4,7-dioxobenzothiazoles and analogues thereof | |
| EP0381661B1 (de) | 1-E3-(2-Hydroxy-3-alkylaminopropoxy)-2-thienyl]-3-phenyl-1-propanone und Verfahren zu deren Herstellung | |
| Groutas et al. | Synthesis and antitumor activity of some aromatic selenolactones | |
| DE3824446A1 (de) | Verwendung substituierter 3,4-dihydro-2h-benzopyrane als heilmittel gegen obstruktive funktionsstoerungen der lunge und/oder stoerungen der ableitenden harnwege | |
| RU2707972C1 (ru) | 4-(2,4-диметоксифенил)-2-(2-гидроксифенил)-5,6-дигидро-4н-бензо[h]хромен-3-карбоновая кислота, обладающая цитотоксической активностью | |
| DE10253746A1 (de) | 10-Benzyliden-1,8-dichlor-9(10H)-anthracenone als neue Inhibitoren der Tubulin-Polymerisation | |
| DE10253720A1 (de) | 10-Phenylimino-9(10H)-anthracenone als neue Inhibitoren der Tubulin-Polymerisation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8339 | Ceased/non-payment of the annual fee |