TWI719478B - Mcl-1抑制劑 - Google Patents

Info

Publication number

TWI719478B

TWI719478B TW108116508A TW108116508A TWI719478B TW I719478 B TWI719478 B TW I719478B TW 108116508 A TW108116508 A TW 108116508A TW 108116508 A TW108116508 A TW 108116508A TW I719478 B TWI719478 B TW I719478B

Authority

TW

Taiwan

Prior art keywords

group

formula

alkyl

pharmaceutically acceptable

acceptable salt

Prior art date

2018-05-14

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• 101001056180 Homo sapiens Induced myeloid leukemia cell differentiation protein Mcl-1 Proteins 0.000 title claims description 14
• 102100026539 Induced myeloid leukemia cell differentiation protein Mcl-1 Human genes 0.000 title claims description 14
• 239000003112 inhibitor Substances 0.000 title description 40
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 64
• 201000011510 cancer Diseases 0.000 claims abstract description 54
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 194
• 150000003839 salts Chemical class 0.000 claims description 191
• 125000000623 heterocyclic group Chemical group 0.000 claims description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims description 102
• 239000001257 hydrogen Substances 0.000 claims description 102
• 125000003118 aryl group Chemical group 0.000 claims description 100
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 96
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 84
• -1 -OR 7 Chemical group 0.000 claims description 80
• 125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 71
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
• 239000000460 chlorine Substances 0.000 claims description 54
• 125000005843 halogen group Chemical group 0.000 claims description 47
• 125000001424 substituent group Chemical group 0.000 claims description 46
• 239000003814 drug Substances 0.000 claims description 41
• 150000002431 hydrogen Chemical class 0.000 claims description 41
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 28
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 16
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 201000001441 melanoma Diseases 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
• 125000003003 spiro group Chemical group 0.000 claims description 8
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 239000011593 sulfur Substances 0.000 claims description 7
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 230000001225 therapeutic effect Effects 0.000 claims description 6
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 5
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
• 125000004432 carbon atom Chemical group C* 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 229910052698 phosphorus Inorganic materials 0.000 claims description 5
• 239000011574 phosphorus Substances 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
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• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000002250 Hematologic Neoplasms Diseases 0.000 claims description 3
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• 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 3
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• 208000000453 Skin Neoplasms Diseases 0.000 claims description 3
• 206010041067 Small cell lung cancer Diseases 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 201000010982 kidney cancer Diseases 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 3
• 201000000849 skin cancer Diseases 0.000 claims description 3
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• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 2
• 206010066476 Haematological malignancy Diseases 0.000 claims description 2
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 7
• 125000003367 polycyclic group Chemical group 0.000 claims 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 150000001335 aliphatic alkanes Chemical group 0.000 claims 1
• 125000002009 alkene group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 76
• HTNUUDFQRYBJPH-UHFFFAOYSA-N 3-methoxypropanehydrazide Chemical compound COCCC(=O)NN HTNUUDFQRYBJPH-UHFFFAOYSA-N 0.000 description 489
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 202
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 158
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• 239000000543 intermediate Substances 0.000 description 123
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 122
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
• 238000005481 NMR spectroscopy Methods 0.000 description 109
• 239000000243 solution Substances 0.000 description 98
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• 235000019439 ethyl acetate Nutrition 0.000 description 85
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 82
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 77
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 74
• 238000006243 chemical reaction Methods 0.000 description 72
• 238000002360 preparation method Methods 0.000 description 66
• 239000011541 reaction mixture Substances 0.000 description 62
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
• 238000005160 1H NMR spectroscopy Methods 0.000 description 46
• 239000002904 solvent Substances 0.000 description 45
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 230000002829 reductive effect Effects 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 36
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• 125000005605 benzo group Chemical group 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
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• 238000002953 preparative HPLC Methods 0.000 description 28
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 23
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• 102100040678 Programmed cell death protein 1 Human genes 0.000 description 21
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• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 17
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