JP5461402B2 - 置換三環式化合物およびその使用方法 - Google Patents

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Publication number

JP5461402B2

JP5461402B2 JP2010524375A JP2010524375A JP5461402B2 JP 5461402 B2 JP5461402 B2 JP 5461402B2 JP 2010524375 A JP2010524375 A JP 2010524375A JP 2010524375 A JP2010524375 A JP 2010524375A JP 5461402 B2 JP5461402 B2 JP 5461402B2

Authority

JP

Japan

Prior art keywords

alkyl

group

alkoxy

alkylamino

hydroxy

Prior art date

2007-09-14

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 311
• 238000000034 method Methods 0.000 title claims description 203
• -1 cyano, hydroxy Chemical group 0.000 claims description 241
• 239000001257 hydrogen Substances 0.000 claims description 202
• 229910052739 hydrogen Inorganic materials 0.000 claims description 202
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 148
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 133
• 125000001153 fluoro group Chemical group F* 0.000 claims description 128
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 125
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 123
• 150000002431 hydrogen Chemical class 0.000 claims description 121
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 102
• 239000002904 solvent Substances 0.000 claims description 89
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 84
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 74
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 58
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 55
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 50
• 206010028980 Neoplasm Diseases 0.000 claims description 45
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 43
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 37
• 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 32
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 30
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 27
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 27
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 27
• 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 25
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 25
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
• 239000002585 base Substances 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 23
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 21
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
• 230000002062 proliferating effect Effects 0.000 claims description 20
• 239000012453 solvate Substances 0.000 claims description 20
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 239000002253 acid Substances 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• 229910052717 sulfur Inorganic materials 0.000 claims description 15
• RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical group CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 12
• 229940124597 therapeutic agent Drugs 0.000 claims description 12
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 11
• 125000003545 alkoxy group Chemical group 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 239000003054 catalyst Substances 0.000 claims description 7
• 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
• 239000007822 coupling agent Substances 0.000 claims description 5
• 229910052763 palladium Inorganic materials 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 150000001408 amides Chemical class 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
• 150000004677 hydrates Chemical class 0.000 claims description 2
• 208000014081 polyp of colon Diseases 0.000 claims description 2
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 10
• 208000035269 cancer or benign tumor Diseases 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 150
• 239000000203 mixture Substances 0.000 description 149
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 123
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 96
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 68
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 210000004027 cell Anatomy 0.000 description 66
• 239000000243 solution Substances 0.000 description 66
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 62
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 238000000967 suction filtration Methods 0.000 description 37
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 36
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 36
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 35
• 229910052938 sodium sulfate Inorganic materials 0.000 description 35
• 235000011152 sodium sulphate Nutrition 0.000 description 35
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 32
• 238000002953 preparative HPLC Methods 0.000 description 31
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 30
• 201000010099 disease Diseases 0.000 description 29
• 239000003480 eluent Substances 0.000 description 29
• 239000012044 organic layer Substances 0.000 description 29
• 239000002244 precipitate Substances 0.000 description 28
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
• 102000001301 EGF receptor Human genes 0.000 description 23
• 239000003112 inhibitor Substances 0.000 description 22
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
• 239000013078 crystal Substances 0.000 description 21
• UUHNQHFOIVLAQX-BJILWQEISA-N (e)-4-(dimethylamino)but-2-enoic acid;hydrochloride Chemical compound Cl.CN(C)C\C=C\C(O)=O UUHNQHFOIVLAQX-BJILWQEISA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 239000000047 product Substances 0.000 description 20
• 238000012360 testing method Methods 0.000 description 20
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
• 238000000746 purification Methods 0.000 description 19
• 230000000694 effects Effects 0.000 description 18
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
• 108060006698 EGF receptor Proteins 0.000 description 16
• 238000004440 column chromatography Methods 0.000 description 16
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 16
• ZXRCAYWYTOIRQS-UHFFFAOYSA-N hydron;phenol;chloride Chemical compound Cl.OC1=CC=CC=C1 ZXRCAYWYTOIRQS-UHFFFAOYSA-N 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• DOTGZROJTAUYFQ-OWOJBTEDSA-N (e)-4-bromobut-2-enoic acid Chemical compound OC(=O)\C=C\CBr DOTGZROJTAUYFQ-OWOJBTEDSA-N 0.000 description 15
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 15
• OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 15
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• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
• DYTQGJLVGDSCLF-UHFFFAOYSA-N thieno[2,3-d]pyrimidin-4-amine Chemical class NC1=NC=NC2=C1C=CS2 DYTQGJLVGDSCLF-UHFFFAOYSA-N 0.000 description 12
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• 239000004480 active ingredient Substances 0.000 description 11
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• OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 11
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