EA032255B1 - ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ 4,5,6,7-ТЕТРАГИДРОПИРАЗОЛО[1,5-a]ПИРАЗИНА И ПРОИЗВОДНЫЕ 5,6,7,8-ТЕТРАГИДРО-4H-ПИРАЗОЛО[1,5-a][1,4]ДИАЗЕПИНА В КАЧЕСТВЕ ИНГИБИТОРОВ Ros1 - Google Patents

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Publication number

EA032255B1

EA032255B1 EA201691930A EA201691930A EA032255B1 EA 032255 B1 EA032255 B1 EA 032255B1 EA 201691930 A EA201691930 A EA 201691930A EA 201691930 A EA201691930 A EA 201691930A EA 032255 B1 EA032255 B1 EA 032255B1

Authority

EA

Eurasian Patent Office

Prior art keywords

alkyl

formula

alkyloxy

substituted

mmol

Prior art date

2014-03-27

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• 239000003112 inhibitor Substances 0.000 title claims abstract description 21
• POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical class N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 title abstract 2
• 101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 title abstract 2
• 102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 title abstract 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 373
• 239000003814 drug Substances 0.000 claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 239000004480 active ingredient Substances 0.000 claims abstract description 12
• 125000000217 alkyl group Chemical group 0.000 claims description 403
• 229910052739 hydrogen Inorganic materials 0.000 claims description 223
• 239000001257 hydrogen Substances 0.000 claims description 219
• 230000015572 biosynthetic process Effects 0.000 claims description 180
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 177
• 125000003545 alkoxy group Chemical group 0.000 claims description 158
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 145
• 125000001424 substituent group Chemical group 0.000 claims description 121
• 150000003839 salts Chemical class 0.000 claims description 110
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 109
• 150000002367 halogens Chemical class 0.000 claims description 71
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 69
• 229910052736 halogen Inorganic materials 0.000 claims description 67
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
• 125000000623 heterocyclic group Chemical group 0.000 claims description 60
• 238000011282 treatment Methods 0.000 claims description 54
• 206010028980 Neoplasm Diseases 0.000 claims description 46
• 229920006395 saturated elastomer Polymers 0.000 claims description 46
• 125000004429 atom Chemical group 0.000 claims description 41
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 36
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 26
• 201000010099 disease Diseases 0.000 claims description 24
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 230000002265 prevention Effects 0.000 claims description 12
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 10
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 7
• 206010033128 Ovarian cancer Diseases 0.000 claims description 7
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 6
• 201000003076 Angiosarcoma Diseases 0.000 claims description 6
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 6
• 208000001258 Hemangiosarcoma Diseases 0.000 claims description 6
• 208000009956 adenocarcinoma Diseases 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 201000006585 gastric adenocarcinoma Diseases 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 208000007207 Epithelioid hemangioendothelioma Diseases 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 229940079593 drug Drugs 0.000 claims description 5
• 230000002757 inflammatory effect Effects 0.000 claims description 5
• 210000000651 myofibroblast Anatomy 0.000 claims description 5
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 4
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 4
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims description 4
• 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 3
• DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims description 2
• 210000004907 gland Anatomy 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 29
• 150000003216 pyrazines Chemical class 0.000 abstract 1
• 239000000543 intermediate Substances 0.000 description 457
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• 239000000203 mixture Substances 0.000 description 303
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• 238000003786 synthesis reaction Methods 0.000 description 150
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 148
• 239000007787 solid Substances 0.000 description 140
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 132
• -1 acyclic pyrazole compounds Chemical class 0.000 description 118
• 239000000243 solution Substances 0.000 description 105
• 239000012044 organic layer Substances 0.000 description 103
• 239000012453 solvate Substances 0.000 description 97
• 239000002585 base Chemical class 0.000 description 66
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 55
• 239000003921 oil Substances 0.000 description 54
• 235000019198 oils Nutrition 0.000 description 54
• 238000002360 preparation method Methods 0.000 description 52
• 238000006243 chemical reaction Methods 0.000 description 49
• 239000012298 atmosphere Substances 0.000 description 47
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• 239000000725 suspension Substances 0.000 description 37
• 229940125904 compound 1 Drugs 0.000 description 30
• 239000002253 acid Substances 0.000 description 29
• 239000003054 catalyst Substances 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
• 239000012230 colorless oil Substances 0.000 description 25
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 25
• 239000000047 product Substances 0.000 description 23
• 230000001788 irregular Effects 0.000 description 22
• 201000011510 cancer Diseases 0.000 description 21
• 239000012074 organic phase Substances 0.000 description 21
• 239000013058 crude material Substances 0.000 description 20
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
• 239000000706 filtrate Substances 0.000 description 19
• 230000005526 G1 to G0 transition Effects 0.000 description 17
• 239000003153 chemical reaction reagent Substances 0.000 description 17
• 210000004027 cell Anatomy 0.000 description 16
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• 150000001721 carbon Chemical group 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 239000007864 aqueous solution Substances 0.000 description 14
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
• 239000011521 glass Substances 0.000 description 13
• 238000012545 processing Methods 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• 150000002431 hydrogen Chemical group 0.000 description 12
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 12
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 11
• 239000002246 antineoplastic agent Substances 0.000 description 11
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• 239000000843 powder Substances 0.000 description 11
• 125000006239 protecting group Chemical group 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
• 108091000080 Phosphotransferase Proteins 0.000 description 10
• 238000002844 melting Methods 0.000 description 10
• 230000008018 melting Effects 0.000 description 10
• 102000020233 phosphotransferase Human genes 0.000 description 10
• 150000003254 radicals Chemical class 0.000 description 10
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• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
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• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 229910002091 carbon monoxide Inorganic materials 0.000 description 9
• 229940125782 compound 2 Drugs 0.000 description 9
• 239000000377 silicon dioxide Substances 0.000 description 9
• 239000011734 sodium Substances 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
• 230000000259 anti-tumor effect Effects 0.000 description 8
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• 239000002244 precipitate Substances 0.000 description 8
• 229910000104 sodium hydride Inorganic materials 0.000 description 8
• 230000001225 therapeutic effect Effects 0.000 description 8
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 7
• 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 7
• 241001465754 Metazoa Species 0.000 description 7
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• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
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