BG106535A - Хиназолинови производни - Google Patents
Хиназолинови производни Download PDFInfo
- Publication number
- BG106535A BG106535A BG106535A BG10653502A BG106535A BG 106535 A BG106535 A BG 106535A BG 106535 A BG106535 A BG 106535A BG 10653502 A BG10653502 A BG 10653502A BG 106535 A BG106535 A BG 106535A
- Authority
- BG
- Bulgaria
- Prior art keywords
- alkyl
- apos
- group
- hydrogen
- optionally substituted
- Prior art date
Links
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 219
- 239000001257 hydrogen Substances 0.000 claims abstract description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 123
- 108090000461 Aurora Kinase A Proteins 0.000 claims abstract description 36
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
- 102100032311 Aurora kinase A Human genes 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 150000001408 amides Chemical class 0.000 claims abstract description 16
- 238000011282 treatment Methods 0.000 claims abstract description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 306
- -1 cyano, amino Chemical group 0.000 claims description 101
- 125000000623 heterocyclic group Chemical group 0.000 claims description 96
- 238000002360 preparation method Methods 0.000 claims description 76
- 125000003545 alkoxy group Chemical group 0.000 claims description 71
- 125000005843 halogen group Chemical group 0.000 claims description 65
- 125000000524 functional group Chemical group 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 125000001424 substituent group Chemical group 0.000 claims description 49
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 45
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000004122 cyclic group Chemical group 0.000 claims description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 25
- 125000003282 alkyl amino group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 239000000651 prodrug Substances 0.000 claims description 12
- 229940002612 prodrug Drugs 0.000 claims description 12
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 11
- 125000001589 carboacyl group Chemical group 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 5
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 2
- 125000004979 cyclopentylene group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 34
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 239000004202 carbamide Substances 0.000 claims 3
- 235000013877 carbamide Nutrition 0.000 claims 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 17
- 201000011510 cancer Diseases 0.000 abstract description 7
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000962 organic group Chemical group 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 113
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 112
- 238000006243 chemical reaction Methods 0.000 description 69
- 238000005160 1H NMR spectroscopy Methods 0.000 description 67
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 38
- 210000004027 cell Anatomy 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- 239000000203 mixture Substances 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 15
- 230000022131 cell cycle Effects 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 108090000629 orphan nuclear receptors Proteins 0.000 description 12
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 201000010099 disease Diseases 0.000 description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 108090000623 proteins and genes Proteins 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 108020004414 DNA Proteins 0.000 description 8
- 102000004190 Enzymes Human genes 0.000 description 8
- 108090000790 Enzymes Proteins 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 7
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 7
- 229930182816 L-glutamine Natural products 0.000 description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 7
- 229930182555 Penicillin Natural products 0.000 description 7
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 230000014509 gene expression Effects 0.000 description 7
- 229940049954 penicillin Drugs 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 230000002062 proliferating effect Effects 0.000 description 7
- 229960005322 streptomycin Drugs 0.000 description 7
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 6
- WOVKYSAHUYNSMH-RRKCRQDMSA-N 5-bromodeoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(Br)=C1 WOVKYSAHUYNSMH-RRKCRQDMSA-N 0.000 description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 108091000080 Phosphotransferase Proteins 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000002609 medium Substances 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 102000020233 phosphotransferase Human genes 0.000 description 6
- 239000003755 preservative agent Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- LLLHRNQLGUOJHP-UHFFFAOYSA-N 4-chloro-6,7-dimethoxyquinazoline Chemical compound C1=NC(Cl)=C2C=C(OC)C(OC)=CC2=N1 LLLHRNQLGUOJHP-UHFFFAOYSA-N 0.000 description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 230000004663 cell proliferation Effects 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 235000014113 dietary fatty acids Nutrition 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 239000000194 fatty acid Substances 0.000 description 5
- 229930195729 fatty acid Natural products 0.000 description 5
- 150000004665 fatty acids Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 5
- 108090000765 processed proteins & peptides Proteins 0.000 description 5
- 102000004169 proteins and genes Human genes 0.000 description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 4
- OUJRTEVIUYGUQY-UHFFFAOYSA-N 4-[3-(4-chloro-6-methoxyquinazolin-7-yl)oxypropyl]morpholine Chemical compound COC1=CC2=C(Cl)N=CN=C2C=C1OCCCN1CCOCC1 OUJRTEVIUYGUQY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 108091007914 CDKs Proteins 0.000 description 4
- 108091026890 Coding region Proteins 0.000 description 4
- MWAYRGBWOVHDDZ-UHFFFAOYSA-N Ethyl vanillate Chemical compound CCOC(=O)C1=CC=C(O)C(OC)=C1 MWAYRGBWOVHDDZ-UHFFFAOYSA-N 0.000 description 4
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catching Or Destruction (AREA)
- Ropes Or Cables (AREA)
- Earth Drilling (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9922173.1A GB9922173D0 (en) | 1999-09-21 | 1999-09-21 | Chemical compounds |
| PCT/GB2000/003562 WO2001021595A1 (en) | 1999-09-21 | 2000-09-18 | Quinazoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG106535A true BG106535A (bg) | 2002-12-29 |
Family
ID=10861219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG106535A BG106535A (bg) | 1999-09-21 | 2002-03-20 | Хиназолинови производни |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7105669B1 (cs) |
| EP (1) | EP1218357B1 (cs) |
| JP (1) | JP2003509498A (cs) |
| KR (1) | KR20020029136A (cs) |
| CN (1) | CN1391560A (cs) |
| AT (1) | ATE292628T1 (cs) |
| AU (1) | AU7433000A (cs) |
| BG (1) | BG106535A (cs) |
| BR (1) | BR0014136A (cs) |
| CA (1) | CA2384284A1 (cs) |
| CZ (1) | CZ20021007A3 (cs) |
| DE (1) | DE60019317T2 (cs) |
| EE (1) | EE200200148A (cs) |
| GB (1) | GB9922173D0 (cs) |
| HK (1) | HK1046687A1 (cs) |
| HU (1) | HUP0204226A3 (cs) |
| IL (1) | IL148498A0 (cs) |
| IS (1) | IS6309A (cs) |
| NO (1) | NO20021395L (cs) |
| PL (1) | PL354972A1 (cs) |
| SK (1) | SK3842002A3 (cs) |
| WO (1) | WO2001021595A1 (cs) |
| ZA (1) | ZA200201831B (cs) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
| EP1313727A1 (en) | 2000-08-21 | 2003-05-28 | AstraZeneca AB | Quinazoline derivatives |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| EP1330444B1 (en) | 2000-11-01 | 2011-03-23 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic compounds and process for making them |
| EP1411046B1 (en) * | 2001-06-22 | 2009-09-16 | Kirin Pharma Kabushiki Kaisha | Quinoline derivative and quinazoline derivative inhibiting self-phosphorylation of hepatocytus proliferator receptor, and medicinal composition containing the same |
| WO2003062209A2 (en) | 2002-01-17 | 2003-07-31 | Neurogen Corporation | Substituted quinazolin-4-ylamine analogues as modulators of capsaicin |
| US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
| CA2491191C (en) | 2002-07-15 | 2014-02-04 | Exelixis, Inc. | Receptor-type kinase modulators and methods of use |
| US8309562B2 (en) | 2003-07-03 | 2012-11-13 | Myrexis, Inc. | Compounds and therapeutical use thereof |
| JP5129957B2 (ja) | 2003-07-03 | 2013-01-30 | ミリアド ジェネティクス， インコーポレイテッド | カスパーゼの活性化因子およびアポトーシスの誘発因子としての４−アリールアミノ−キナゾリン |
| US7329664B2 (en) | 2003-07-16 | 2008-02-12 | Neurogen Corporation | Substituted (7-pyridyl-4-phenylamino-quinazolin-2-yl)-methanol analogues |
| GB0317665D0 (en) | 2003-07-29 | 2003-09-03 | Astrazeneca Ab | Qinazoline derivatives |
| RU2378268C2 (ru) | 2003-09-16 | 2010-01-10 | Астразенека Аб | Производные хиназолина в качестве ингибиторов тирозинкиназы |
| GB0326459D0 (en) | 2003-11-13 | 2003-12-17 | Astrazeneca Ab | Quinazoline derivatives |
| JP2007514759A (ja) | 2003-12-19 | 2007-06-07 | タケダ サン ディエゴ インコーポレイテッド | キナーゼ阻害剤 |
| WO2005072731A1 (en) * | 2004-01-29 | 2005-08-11 | X-Ceptor Therapeutics, Inc. | 3-phenyl-n- ((1, 3, 4) thiadiazol-2-yl) -acrylamide derivatives and related compounds as modulators of estrogen-related receptors for the treatment of e.g. cancer, rheumatoid arthritis or neurological disorders |
| EP1778669A2 (en) | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| US7285569B2 (en) | 2004-09-24 | 2007-10-23 | Hoff Hoffmann-La Roche Inc. | Tricycles, their manufacture and use as pharmaceutical agents |
| TW200624431A (en) | 2004-09-24 | 2006-07-16 | Hoffmann La Roche | Phthalazinone derivatives, their manufacture and use as pharmaceutical agents |
| MX2007004403A (es) | 2004-10-12 | 2007-04-27 | Astrazeneca Ab | Derivados de quinazolina. |
| DE602005023333D1 (de) | 2004-10-15 | 2010-10-14 | Takeda Pharmaceutical | Kinaseinhibitoren |
| EP1833482A4 (en) | 2005-01-03 | 2011-02-16 | Myriad Genetics Inc | COMPOUNDS AND ITS THERAPEUTIC USE |
| US8258145B2 (en) | 2005-01-03 | 2012-09-04 | Myrexis, Inc. | Method of treating brain cancer |
| EP1856053A1 (en) | 2005-01-14 | 2007-11-21 | Millennium Pharmaceuticals, Inc. | Cinnamide and hydrocinnamide derivatives with raf-kinase inhibitory activity |
| WO2006108489A1 (en) | 2005-04-14 | 2006-10-19 | F. Hoffmann-La Roche Ag | Aminopyrazole derivatives, their manufacture and use as pharmaceutical agents |
| ES2545382T3 (es) | 2005-04-28 | 2015-09-10 | Mitsubishi Tanabe Pharma Corporation | Derivado de cianopiridina y su uso como medicamento |
| GB0510963D0 (en) * | 2005-05-28 | 2005-07-06 | Astrazeneca Ab | Chemical compounds |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| US20090076075A1 (en) * | 2006-03-02 | 2009-03-19 | Frederic Henri Jung | Quinoline derivatives |
| UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
| US20080033000A1 (en) * | 2006-05-15 | 2008-02-07 | Senex Biotechnology, Inc. | Identification of CDKI pathway inhibitors |
| EA200970361A1 (ru) | 2006-10-09 | 2010-02-26 | Такеда Фармасьютикал Компани Лимитед | Ингибиторы киназы |
| EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
| US7998949B2 (en) | 2007-02-06 | 2011-08-16 | Boehringer Ingelheim International Gmbh | Bicyclic heterocycles, drugs containing said compounds, use thereof, and method for production thereof |
| CA2712367C (en) | 2008-01-17 | 2016-01-19 | Bayer Schering Pharma Aktiengesellschaft | Sulphoximine-substituted quinazoline derivatives as immunomodulators, their preparation and use as medicaments |
| JP5336516B2 (ja) | 2008-02-07 | 2013-11-06 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | スピロ環式複素環化合物、該化合物を含む医薬品、その使用及びその製造方法 |
| AU2009247782C1 (en) | 2008-05-13 | 2013-09-19 | Astrazeneca Ab | Fumarate salt of 4- (3-chloro-2-fluoroanilino) -7-methoxy-6- { [1- (N-methylcarbamoylmethyl) piperidin- 4-yl] oxy } quinazoline |
| JP5539351B2 (ja) | 2008-08-08 | 2014-07-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | シクロヘキシルオキシ置換ヘテロ環、これらの化合物を含有する医薬、およびそれらを生成するための方法 |
| CN105777654B (zh) * | 2016-03-28 | 2018-03-27 | 贵州大学 | 一种含喹唑啉的阿魏酸酯类衍生物、其制备方法和用途 |
| EP3762379A1 (en) | 2018-03-07 | 2021-01-13 | Bayer Aktiengesellschaft | Identification and use of erk5 inhibitors |
| CN117693505A (zh) * | 2021-04-22 | 2024-03-12 | 沃若诺伊公司 | 杂芳基衍生物化合物及其用途 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2161290T3 (es) * | 1995-03-30 | 2001-12-01 | Pfizer | Derivados de quinazolina. |
| GB9708265D0 (en) * | 1997-04-24 | 1997-06-18 | Nycomed Imaging As | Contrast agents |
| WO2004013091A2 (en) * | 2002-08-01 | 2004-02-12 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | 4-anilido substituted quinazolines and use thereof as inhibitors of epidermal growth factor receptor kinases |
-
1999
- 1999-09-21 GB GBGB9922173.1A patent/GB9922173D0/en not_active Ceased
-
2000
- 2000-09-18 AT AT00962682T patent/ATE292628T1/de not_active IP Right Cessation
- 2000-09-18 IL IL14849800A patent/IL148498A0/xx unknown
- 2000-09-18 DE DE60019317T patent/DE60019317T2/de not_active Expired - Fee Related
- 2000-09-18 EE EEP200200148A patent/EE200200148A/xx unknown
- 2000-09-18 CA CA002384284A patent/CA2384284A1/en not_active Abandoned
- 2000-09-18 US US10/088,852 patent/US7105669B1/en not_active Expired - Fee Related
- 2000-09-18 HU HU0204226A patent/HUP0204226A3/hu unknown
- 2000-09-18 JP JP2001524974A patent/JP2003509498A/ja active Pending
- 2000-09-18 HK HK02108373.8A patent/HK1046687A1/zh unknown
- 2000-09-18 BR BR0014136-4A patent/BR0014136A/pt not_active IP Right Cessation
- 2000-09-18 WO PCT/GB2000/003562 patent/WO2001021595A1/en active IP Right Grant
- 2000-09-18 CN CN00816000A patent/CN1391560A/zh active Pending
- 2000-09-18 AU AU74330/00A patent/AU7433000A/en not_active Abandoned
- 2000-09-18 CZ CZ20021007A patent/CZ20021007A3/cs unknown
- 2000-09-18 PL PL00354972A patent/PL354972A1/xx not_active Application Discontinuation
- 2000-09-18 KR KR1020027003679A patent/KR20020029136A/ko not_active Withdrawn
- 2000-09-18 SK SK384-2002A patent/SK3842002A3/sk unknown
- 2000-09-18 EP EP00962682A patent/EP1218357B1/en not_active Expired - Lifetime
-
2002
- 2002-03-05 ZA ZA200201831A patent/ZA200201831B/xx unknown
- 2002-03-19 IS IS6309A patent/IS6309A/is unknown
- 2002-03-20 BG BG106535A patent/BG106535A/bg unknown
- 2002-03-20 NO NO20021395A patent/NO20021395L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR0014136A (pt) | 2002-05-21 |
| PL354972A1 (en) | 2004-03-22 |
| US7105669B1 (en) | 2006-09-12 |
| IL148498A0 (en) | 2002-09-12 |
| NO20021395L (no) | 2002-05-15 |
| EE200200148A (et) | 2003-04-15 |
| CN1391560A (zh) | 2003-01-15 |
| SK3842002A3 (en) | 2002-10-08 |
| ZA200201831B (en) | 2003-08-27 |
| EP1218357B1 (en) | 2005-04-06 |
| DE60019317D1 (de) | 2005-05-12 |
| CZ20021007A3 (cs) | 2002-06-12 |
| WO2001021595A1 (en) | 2001-03-29 |
| AU7433000A (en) | 2001-04-24 |
| CA2384284A1 (en) | 2001-03-29 |
| DE60019317T2 (de) | 2006-03-09 |
| HUP0204226A3 (en) | 2003-07-28 |
| HK1046687A1 (zh) | 2003-01-24 |
| ATE292628T1 (de) | 2005-04-15 |
| EP1218357A1 (en) | 2002-07-03 |
| IS6309A (is) | 2002-03-19 |
| NO20021395D0 (no) | 2002-03-20 |
| GB9922173D0 (en) | 1999-11-17 |
| KR20020029136A (ko) | 2002-04-17 |
| HUP0204226A2 (en) | 2003-05-28 |
| JP2003509498A (ja) | 2003-03-11 |
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