UA80763C2 - Pyrazolo-quinazoline derivatives, process for their preparation and their use as kinase inhibitors - Google Patents

Info

Publication number

UA80763C2

UA80763C2 UAA200512347A UAA200512347A UA80763C2 UA 80763 C2 UA80763 C2 UA 80763C2 UA A200512347 A UAA200512347 A UA A200512347A UA A200512347 A UAA200512347 A UA A200512347A UA 80763 C2 UA80763 C2 UA 80763C2

Authority

UA

Ukraine

Prior art keywords

formula

compound

group

compounds

interaction

Prior art date

2003-05-22

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• 238000000034 method Methods 0.000 title claims abstract description 107
• 238000002360 preparation method Methods 0.000 title claims abstract description 23
• GNOYRJIXSUNXIH-UHFFFAOYSA-N N1=CNC2=C3C=NN=C3C=CC2=C1 Chemical class N1=CNC2=C3C=NN=C3C=CC2=C1 GNOYRJIXSUNXIH-UHFFFAOYSA-N 0.000 title claims abstract description 15
• 229940043355 kinase inhibitor Drugs 0.000 title 1
• 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 427
• 230000000694 effects Effects 0.000 claims abstract description 37
• 238000011282 treatment Methods 0.000 claims abstract description 33
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 27
• 150000003839 salts Chemical class 0.000 claims abstract description 24
• 102000001253 Protein Kinase Human genes 0.000 claims abstract description 18
• 108060006633 protein kinase Proteins 0.000 claims abstract description 18
• 201000010099 disease Diseases 0.000 claims abstract description 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
• 201000011510 cancer Diseases 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 236
• 239000000203 mixture Substances 0.000 claims description 171
• 238000006243 chemical reaction Methods 0.000 claims description 83
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 71
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 66
• 230000003993 interaction Effects 0.000 claims description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims description 60
• -1 C3-C10-cycloalkyl Chemical group 0.000 claims description 51
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 48
• 125000003118 aryl group Chemical group 0.000 claims description 44
• 229910052700 potassium Inorganic materials 0.000 claims description 44
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• 229910052739 hydrogen Inorganic materials 0.000 claims description 43
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 41
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
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• 230000009466 transformation Effects 0.000 claims description 20
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
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• 239000000908 ammonium hydroxide Substances 0.000 claims description 15
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• 229910052740 iodine Inorganic materials 0.000 claims description 15
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• 239000012312 sodium hydride Substances 0.000 claims description 13
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 13
• WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 150000002496 iodine Chemical class 0.000 claims description 10
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• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims description 9
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• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
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• 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
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• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
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• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• WUSZGSMQYXOBRT-UHFFFAOYSA-N 2-methoxy-4,4-dimethylcyclohex-2-en-1-one Chemical compound COC1=CC(C)(C)CCC1=O WUSZGSMQYXOBRT-UHFFFAOYSA-N 0.000 claims description 6
• JRGZHRJEKVTXCX-UHFFFAOYSA-N 2-methoxy-5,5-dimethylcyclohex-2-en-1-one Chemical compound COC1=CCC(C)(C)CC1=O JRGZHRJEKVTXCX-UHFFFAOYSA-N 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
• 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
• 239000003054 catalyst Substances 0.000 claims description 6
• 238000003786 synthesis reaction Methods 0.000 claims description 6
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 108091007914 CDKs Proteins 0.000 claims description 5
• 102000003903 Cyclin-dependent kinases Human genes 0.000 claims description 5
• 108090000266 Cyclin-dependent kinases Proteins 0.000 claims description 5
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
• XQPRBTXUXXVTKB-UHFFFAOYSA-M caesium iodide Chemical compound [I-].[Cs+] XQPRBTXUXXVTKB-UHFFFAOYSA-M 0.000 claims description 5
• 238000002512 chemotherapy Methods 0.000 claims description 5
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 5
• OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 claims description 5
• 238000012545 processing Methods 0.000 claims description 5
• 238000001959 radiotherapy Methods 0.000 claims description 5
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
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• 235000010469 Glycine max Nutrition 0.000 claims description 4
• XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 4
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• 201000004681 Psoriasis Diseases 0.000 claims description 4
• 239000002253 acid Substances 0.000 claims description 4
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• 230000003394 haemopoietic effect Effects 0.000 claims description 4
• LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims description 4
• 210000000056 organ Anatomy 0.000 claims description 4
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• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 4
• 230000036262 stenosis Effects 0.000 claims description 4
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• JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 4
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