EA031639B1 - ЗАМЕЩЕННЫЕ 4,5,6,7-ТЕТРАГИДРОПИРАЗОЛО[1,5-а]ПИРИМИДИНОВЫЕ ПРОИЗВОДНЫЕ И 2,3-ДИГИДРО-1H-ИМИДАЗО[1,2-b]ПИРАЗОЛЬНЫЕ ПРОИЗВОДНЫЕ В КАЧЕСТВЕ ИНГИБИТОРОВ ROS1 - Google Patents

Info

Publication number

EA031639B1

EA031639B1 EA201691934A EA201691934A EA031639B1 EA 031639 B1 EA031639 B1 EA 031639B1 EA 201691934 A EA201691934 A EA 201691934A EA 201691934 A EA201691934 A EA 201691934A EA 031639 B1 EA031639 B1 EA 031639B1

Authority

EA

Eurasian Patent Office

Prior art keywords

formula

compound

mmol

hydrogen

represents hydrogen

Prior art date

2014-03-27

Links

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• 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 title abstract description 22
• 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 title abstract description 22
• 239000003112 inhibitor Substances 0.000 title abstract description 18
• 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title abstract 2
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical class C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 383
• 239000004480 active ingredient Substances 0.000 claims abstract description 18
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 145
• 239000001257 hydrogen Substances 0.000 claims description 141
• 230000015572 biosynthetic process Effects 0.000 claims description 80
• 150000003839 salts Chemical class 0.000 claims description 80
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 75
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 71
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000001424 substituent group Chemical group 0.000 claims description 28
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
• 238000000034 method Methods 0.000 abstract description 68
• 239000003814 drug Substances 0.000 abstract description 22
• 150000003217 pyrazoles Chemical class 0.000 abstract description 2
• 150000003230 pyrimidines Chemical class 0.000 abstract description 2
• 239000000543 intermediate Substances 0.000 description 277
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 230
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 222
• 239000000203 mixture Substances 0.000 description 171
• 239000002904 solvent Substances 0.000 description 160
• 239000007787 solid Substances 0.000 description 116
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
• -1 acyclic pyrazole compounds Chemical class 0.000 description 108
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 96
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
• 239000012071 phase Substances 0.000 description 63
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
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• 239000002585 base Chemical class 0.000 description 53
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 45
• 229910020175 SiOH Inorganic materials 0.000 description 42
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
• 238000002360 preparation method Methods 0.000 description 37
• ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
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• 230000005526 G1 to G0 transition Effects 0.000 description 23
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
• 239000012230 colorless oil Substances 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
• 239000000706 filtrate Substances 0.000 description 19
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• 230000014759 maintenance of location Effects 0.000 description 17
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
• 230000001788 irregular Effects 0.000 description 16
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• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 15
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• 239000002244 precipitate Substances 0.000 description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
• 239000000377 silicon dioxide Substances 0.000 description 14
• 229910000104 sodium hydride Inorganic materials 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 241000699670 Mus sp. Species 0.000 description 12
• 239000000047 product Substances 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
• 101150003085 Pdcl gene Proteins 0.000 description 11
• 239000002246 antineoplastic agent Substances 0.000 description 11
• 239000003999 initiator Substances 0.000 description 11
• 208000002154 non-small cell lung carcinoma Diseases 0.000 description 11
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 10
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• 230000002265 prevention Effects 0.000 description 10
• 150000003254 radicals Chemical class 0.000 description 10
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
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• 229910052799 carbon Inorganic materials 0.000 description 9
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• 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 description 8
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