EA006803B1 - 1,3-диарилпроп-2-ен-1-оны, композиция на их основе и применение - Google Patents
1,3-диарилпроп-2-ен-1-оны, композиция на их основе и применение Download PDFInfo
- Publication number
- EA006803B1 EA006803B1 EA200400764A EA200400764A EA006803B1 EA 006803 B1 EA006803 B1 EA 006803B1 EA 200400764 A EA200400764 A EA 200400764A EA 200400764 A EA200400764 A EA 200400764A EA 006803 B1 EA006803 B1 EA 006803B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- propenone
- amino
- methoxy
- methyl
- trimethoxyphenyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title abstract description 39
- -1 2,5-dimethoxyphenyl Chemical group 0.000 claims description 741
- 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 claims description 135
- 150000001875 compounds Chemical class 0.000 claims description 55
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 150000001413 amino acids Chemical class 0.000 claims description 20
- 206010028980 Neoplasm Diseases 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- MYDLRNGAQMXGBW-UHFFFAOYSA-N Cl.C1=C(N)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 Chemical compound Cl.C1=C(N)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 MYDLRNGAQMXGBW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical group 0.000 claims description 9
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 8
- 102000004243 Tubulin Human genes 0.000 claims description 8
- 108090000704 Tubulin Proteins 0.000 claims description 8
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- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 206010054094 Tumour necrosis Diseases 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N lysine Chemical compound NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
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- 201000011510 cancer Diseases 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- XDSHNNRBLSBDAP-UHFFFAOYSA-N (2E)-3-(3,4,5-trimethoxyphenyl)-2-propenal Natural products COC1=CC(C=CC=O)=CC(OC)=C1OC XDSHNNRBLSBDAP-UHFFFAOYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000013256 coordination polymer Substances 0.000 claims description 2
- 229960002449 glycine Drugs 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
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- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 176
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 97
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- 229910052700 potassium Inorganic materials 0.000 description 73
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
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- 210000004027 cell Anatomy 0.000 description 35
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
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- 229910002027 silica gel Inorganic materials 0.000 description 25
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 description 24
- 235000005513 chalcones Nutrition 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000001789 chalcones Chemical class 0.000 description 21
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 20
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 20
- 238000012360 testing method Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- 238000000921 elemental analysis Methods 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000003921 oil Substances 0.000 description 14
- 235000019198 oils Nutrition 0.000 description 14
- LRUWUXUUQXNWOM-UHFFFAOYSA-N 3-(3-amino-4-methoxyphenyl)-2-methyl-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound C1=C(N)C(OC)=CC=C1C=C(C)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 LRUWUXUUQXNWOM-UHFFFAOYSA-N 0.000 description 13
- 239000002609 medium Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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- 238000001819 mass spectrum Methods 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
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- 150000003254 radicals Chemical class 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- JEJJRYAITXRSFR-UHFFFAOYSA-N 3-(3-amino-4-methoxyphenyl)-1-(2,5-dimethoxyphenyl)-2-methylprop-2-en-1-one Chemical compound COC1=CC=C(OC)C(C(=O)C(C)=CC=2C=C(N)C(OC)=CC=2)=C1 JEJJRYAITXRSFR-UHFFFAOYSA-N 0.000 description 6
- IKFPHBSKPMQGFN-UHFFFAOYSA-N 3-(3-amino-4-methoxyphenyl)-1-(7-methoxy-1,3-benzodioxol-5-yl)-2-methylprop-2-en-1-one Chemical compound C=1C=2OCOC=2C(OC)=CC=1C(=O)C(C)=CC1=CC=C(OC)C(N)=C1 IKFPHBSKPMQGFN-UHFFFAOYSA-N 0.000 description 6
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- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 5
- WDNDMVGQGRDIBC-UHFFFAOYSA-N 3,4,5-Trimethoxyphenyl-2-propanone Chemical compound COC1=CC(CC(C)=O)=CC(OC)=C1OC WDNDMVGQGRDIBC-UHFFFAOYSA-N 0.000 description 5
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
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- FPVKHBSQESCIEP-JQCXWYLXSA-N pentostatin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(N=CNC[C@H]2O)=C2N=C1 FPVKHBSQESCIEP-JQCXWYLXSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NFGGQMYSOLVBLF-UHFFFAOYSA-N phenyl(1h-pyrrol-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CN1 NFGGQMYSOLVBLF-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229940080469 phosphocellulose Drugs 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960004694 prednimustine Drugs 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- XKMLYUALXHKNFT-UHFFFAOYSA-N rGTP Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O XKMLYUALXHKNFT-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930002330 retinoic acid Natural products 0.000 description 1
- 235000013974 saffron Nutrition 0.000 description 1
- 239000004248 saffron Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960003440 semustine Drugs 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 210000003625 skull Anatomy 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000003270 steroid hormone Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 229960005314 suramin Drugs 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 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 description 1
- 229960004964 temozolomide Drugs 0.000 description 1
- 229960001278 teniposide Drugs 0.000 description 1
- NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 229960001196 thiotepa Drugs 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 229960003087 tioguanine Drugs 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 229960001727 tretinoin Drugs 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- UGGWPQSBPIFKDZ-KOTLKJBCSA-N vindesine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(N)=O)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1N=C1[C]2C=CC=C1 UGGWPQSBPIFKDZ-KOTLKJBCSA-N 0.000 description 1
- 229960004355 vindesine Drugs 0.000 description 1
- GBABOYUKABKIAF-GHYRFKGUSA-N vinorelbine Chemical compound C1N(CC=2C3=CC=CC=C3NC=22)CC(CC)=C[C@H]1C[C@]2(C(=O)OC)C1=CC([C@]23[C@H]([C@]([C@H](OC(C)=O)[C@]4(CC)C=CCN([C@H]34)CC2)(O)C(=O)OC)N2C)=C2C=C1OC GBABOYUKABKIAF-GHYRFKGUSA-N 0.000 description 1
- 229960002066 vinorelbine Drugs 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/30—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to nitro or nitroso groups
- C07C279/32—N-nitroguanidines
- C07C279/36—Substituted N-nitroguanidines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Bending Of Plates, Rods, And Pipes (AREA)
- Detergent Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0115739A FR2833008B1 (fr) | 2001-12-05 | 2001-12-05 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
| FR0214217 | 2002-11-14 | ||
| PCT/FR2002/004143 WO2003048106A2 (fr) | 2001-12-05 | 2002-12-03 | 1,3-diarylprop-2-en-1-ones, compositions les contenant et utilisation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200400764A1 EA200400764A1 (ru) | 2004-12-30 |
| EA006803B1 true EA006803B1 (ru) | 2006-04-28 |
Family
ID=26213287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200400764A EA006803B1 (ru) | 2001-12-05 | 2002-12-03 | 1,3-диарилпроп-2-ен-1-оны, композиция на их основе и применение |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP1453790A2 (fr) |
| JP (1) | JP2005531494A (fr) |
| KR (1) | KR20050044712A (fr) |
| CN (1) | CN1612856A (fr) |
| AR (1) | AR037479A1 (fr) |
| AU (1) | AU2002365644A1 (fr) |
| BR (1) | BR0214694A (fr) |
| CA (1) | CA2469193A1 (fr) |
| CO (1) | CO5580759A2 (fr) |
| EA (1) | EA006803B1 (fr) |
| HR (1) | HRP20040508A2 (fr) |
| HU (1) | HUP0500100A2 (fr) |
| IL (1) | IL162223A0 (fr) |
| MA (1) | MA27351A1 (fr) |
| MX (1) | MXPA04005226A (fr) |
| NZ (1) | NZ533224A (fr) |
| PA (1) | PA8558501A1 (fr) |
| PE (1) | PE20030758A1 (fr) |
| PL (1) | PL370676A1 (fr) |
| RS (1) | RS47804A (fr) |
| SV (1) | SV2003001422A (fr) |
| TW (1) | TW200300685A (fr) |
| WO (1) | WO2003048106A2 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2854399B1 (fr) * | 2003-04-30 | 2006-11-17 | Aventis Pharma Sa | 1-aryl-3-(indol-5-yl)-prop-2-en-1-ones, compositions les contenant et utilisation |
| EP1598353A1 (fr) * | 2004-05-17 | 2005-11-23 | Boehringer Ingelheim International GmbH | Pyrrolobenzimidazolones et leur utilisation en tant qu'agents antiproliferatifs |
| WO2017103637A1 (fr) | 2015-12-18 | 2017-06-22 | Blirt S.A. | Composés de diphénylpropane et leur activité cytotoxique |
| KR102636496B1 (ko) | 2018-09-14 | 2024-02-15 | 삼성전자주식회사 | 통신 장치 및 이를 포함하는 전자 장치 |
| CN109467549B (zh) * | 2018-12-07 | 2021-02-09 | 中国药科大学 | 喹啉取代查尔酮类化合物、其制备方法及用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
| JPH08277242A (ja) * | 1995-02-08 | 1996-10-22 | Kyowa Hakko Kogyo Co Ltd | プロペノン誘導体 |
| BR9607708A (pt) * | 1995-12-01 | 1998-01-13 | Kyowa Hakko Kogyo Kk | Derivado de propenona |
| WO1999000114A2 (fr) * | 1997-06-26 | 1999-01-07 | Statens Serum Institut | 1,3-bis-aromatique-prop-2-en-1-ones, 1,3-bis-aromatique-propane-1-ones et 1,3-bis-aromatique-prop-2-yn-1-ones a action biologique |
-
2002
- 2002-11-21 PE PE2002001118A patent/PE20030758A1/es not_active Application Discontinuation
- 2002-11-22 PA PA20028558501A patent/PA8558501A1/es unknown
- 2002-11-26 TW TW091134346A patent/TW200300685A/zh unknown
- 2002-11-29 AR ARP020104618A patent/AR037479A1/es unknown
- 2002-12-02 SV SV2002001422A patent/SV2003001422A/es not_active Application Discontinuation
- 2002-12-03 MX MXPA04005226A patent/MXPA04005226A/es unknown
- 2002-12-03 HR HR20040508A patent/HRP20040508A2/hr not_active Application Discontinuation
- 2002-12-03 RS YU47804A patent/RS47804A/sr unknown
- 2002-12-03 EP EP02804242A patent/EP1453790A2/fr not_active Withdrawn
- 2002-12-03 NZ NZ533224A patent/NZ533224A/xx unknown
- 2002-12-03 AU AU2002365644A patent/AU2002365644A1/en not_active Abandoned
- 2002-12-03 IL IL16222302A patent/IL162223A0/xx unknown
- 2002-12-03 CN CNA028268601A patent/CN1612856A/zh active Pending
- 2002-12-03 KR KR1020047008656A patent/KR20050044712A/ko not_active Withdrawn
- 2002-12-03 JP JP2003549299A patent/JP2005531494A/ja not_active Abandoned
- 2002-12-03 HU HU0500100A patent/HUP0500100A2/hu unknown
- 2002-12-03 EA EA200400764A patent/EA006803B1/ru not_active IP Right Cessation
- 2002-12-03 WO PCT/FR2002/004143 patent/WO2003048106A2/fr not_active Ceased
- 2002-12-03 CA CA002469193A patent/CA2469193A1/fr not_active Abandoned
- 2002-12-03 BR BR0214694-0A patent/BR0214694A/pt not_active IP Right Cessation
- 2002-12-03 PL PL02370676A patent/PL370676A1/xx unknown
-
2004
- 2004-06-01 MA MA27708A patent/MA27351A1/fr unknown
- 2004-06-03 CO CO04052091A patent/CO5580759A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20050044712A (ko) | 2005-05-12 |
| AR037479A1 (es) | 2004-11-10 |
| SV2003001422A (es) | 2003-07-10 |
| IL162223A0 (en) | 2005-11-20 |
| NZ533224A (en) | 2006-03-31 |
| JP2005531494A (ja) | 2005-10-20 |
| PE20030758A1 (es) | 2003-10-07 |
| WO2003048106A3 (fr) | 2004-03-25 |
| RS47804A (sr) | 2006-12-15 |
| PL370676A1 (en) | 2005-05-30 |
| HUP0500100A2 (hu) | 2005-05-30 |
| CA2469193A1 (fr) | 2003-06-12 |
| BR0214694A (pt) | 2004-12-14 |
| AU2002365644A1 (en) | 2003-06-17 |
| CN1612856A (zh) | 2005-05-04 |
| MXPA04005226A (es) | 2004-10-11 |
| TW200300685A (en) | 2003-06-16 |
| CO5580759A2 (es) | 2005-11-30 |
| WO2003048106A2 (fr) | 2003-06-12 |
| EA200400764A1 (ru) | 2004-12-30 |
| EP1453790A2 (fr) | 2004-09-08 |
| MA27351A1 (fr) | 2005-06-01 |
| PA8558501A1 (es) | 2003-09-05 |
| HRP20040508A2 (en) | 2005-08-31 |
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