TWI532742B - 激酶之三環抑制劑 - Google Patents

Info

Publication number

TWI532742B

TWI532742B TW101106325A TW101106325A TWI532742B TW I532742 B TWI532742 B TW I532742B TW 101106325 A TW101106325 A TW 101106325A TW 101106325 A TW101106325 A TW 101106325A TW I532742 B TWI532742 B TW I532742B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

amino

pyrimido

phenyl

Prior art date

2011-02-28

Links

• Espacenet
• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title description 30
• 108091000080 Phosphotransferase Proteins 0.000 title description 15
• 102000020233 phosphotransferase Human genes 0.000 title description 15
• 125000000217 alkyl group Chemical group 0.000 claims description 384
• -1 C 1-6 alkane Oxy Chemical group 0.000 claims description 333
• 150000001875 compounds Chemical class 0.000 claims description 274
• 125000005843 halogen group Chemical group 0.000 claims description 189
• 125000001072 heteroaryl group Chemical group 0.000 claims description 174
• 125000003118 aryl group Chemical group 0.000 claims description 171
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 167
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 156
• 125000001424 substituent group Chemical group 0.000 claims description 150
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 144
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 94
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 93
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 81
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 77
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 73
• 125000003545 alkoxy group Chemical group 0.000 claims description 65
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 57
• 229910052799 carbon Inorganic materials 0.000 claims description 47
• 229910052736 halogen Inorganic materials 0.000 claims description 42
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 42
• 229920006395 saturated elastomer Polymers 0.000 claims description 42
• 125000000623 heterocyclic group Chemical group 0.000 claims description 38
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 150000002367 halogens Chemical class 0.000 claims description 34
• 150000003839 salts Chemical class 0.000 claims description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000006413 ring segment Chemical group 0.000 claims description 19
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 18
• 125000001188 haloalkyl group Chemical group 0.000 claims description 18
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 17
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 15
• 229910052717 sulfur Inorganic materials 0.000 claims description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000004429 atom Chemical class 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
• 238000006467 substitution reaction Methods 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 230000037429 base substitution Effects 0.000 claims description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• LHLGMQAZACYFPV-UHFFFAOYSA-N 7-(2-chlorophenyl)-3-methyl-12-[4-(4-methylpiperazin-1-yl)anilino]-2,4,5,7,11,13-hexazatricyclo[7.4.0.02,6]trideca-1(13),3,5,9,11-pentaen-8-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC=C2C(=O)N(C=3C(=CC=CC=3)Cl)C3=NN=C(C)N3C2=N1 LHLGMQAZACYFPV-UHFFFAOYSA-N 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 354
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 153
• 235000019439 ethyl acetate Nutrition 0.000 description 145
• 238000005481 NMR spectroscopy Methods 0.000 description 130
• 239000000203 mixture Substances 0.000 description 105
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 51
• MOZNZNKHRXRLLF-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)aniline Chemical compound C1CN(C)CCN1C1=CC=C(N)C=C1 MOZNZNKHRXRLLF-UHFFFAOYSA-N 0.000 description 49
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
• 238000006243 chemical reaction Methods 0.000 description 48
• 239000011541 reaction mixture Substances 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 35
• 125000001624 naphthyl group Chemical group 0.000 description 34
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 32
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• 239000002904 solvent Substances 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 239000013058 crude material Substances 0.000 description 21
• 206010028980 Neoplasm Diseases 0.000 description 20
• 125000004076 pyridyl group Chemical group 0.000 description 20
• 206010057190 Respiratory tract infections Diseases 0.000 description 19
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 19
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 18
• 238000004128 high performance liquid chromatography Methods 0.000 description 17
• 239000012948 isocyanate Substances 0.000 description 17
• 238000000034 method Methods 0.000 description 17
• 125000002098 pyridazinyl group Chemical group 0.000 description 17
• 239000000243 solution Substances 0.000 description 17
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 16
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 16
• 125000004432 carbon atom Chemical group C* 0.000 description 16
• 125000003226 pyrazolyl group Chemical group 0.000 description 16
• 150000001412 amines Chemical class 0.000 description 15
• 239000012267 brine Substances 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 14
• 239000002585 base Substances 0.000 description 14
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• 238000011282 treatment Methods 0.000 description 14
• 101150040313 Wee1 gene Proteins 0.000 description 13
• 101150012716 CDK1 gene Proteins 0.000 description 12
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 201000011510 cancer Diseases 0.000 description 12
• 125000002837 carbocyclic group Chemical group 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• UKAFWJUARMVPPH-UHFFFAOYSA-N 8h-pyrimido[4,5-d]pyrimidin-5-one Chemical compound C1=NC=C2C(=O)N=CNC2=N1 UKAFWJUARMVPPH-UHFFFAOYSA-N 0.000 description 11
• 125000002971 oxazolyl group Chemical group 0.000 description 11
• 125000003367 polycyclic group Chemical group 0.000 description 11
• FAPREGZSIDHQBT-UHFFFAOYSA-N C1=NC=C2C(=O)NC3=NC=CN3C2=N1 Chemical compound C1=NC=C2C(=O)NC3=NC=CN3C2=N1 FAPREGZSIDHQBT-UHFFFAOYSA-N 0.000 description 10
• 102000014914 Carrier Proteins Human genes 0.000 description 10
• 108091008324 binding proteins Proteins 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• 125000002950 monocyclic group Chemical group 0.000 description 10
• 125000003386 piperidinyl group Chemical group 0.000 description 10
• 238000000746 purification Methods 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 9
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 229940043355 kinase inhibitor Drugs 0.000 description 9
• 125000002757 morpholinyl group Chemical group 0.000 description 9
• 239000003757 phosphotransferase inhibitor Substances 0.000 description 9
• 125000004193 piperazinyl group Chemical group 0.000 description 9
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 9
• OQHQOOLVQDEIGL-UHFFFAOYSA-N 2-methyl-2,7-diazaspiro[4.4]nonane Chemical compound C1N(C)CCC11CNCC1 OQHQOOLVQDEIGL-UHFFFAOYSA-N 0.000 description 8
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 8
• 101000721661 Homo sapiens Cellular tumor antigen p53 Proteins 0.000 description 8
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
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• 108091007433 antigens Proteins 0.000 description 8
• 102000036639 antigens Human genes 0.000 description 8
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 8
• 125000005959 diazepanyl group Chemical group 0.000 description 8
• 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 8
• 239000003814 drug Substances 0.000 description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
• 239000001257 hydrogen Substances 0.000 description 8
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
• 230000011278 mitosis Effects 0.000 description 8
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• 238000003756 stirring Methods 0.000 description 8
• 125000004300 thiazolidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])SC1([H])* 0.000 description 8
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• BFWOXWLQVUGAMG-UHFFFAOYSA-N tert-butyl 7-aminospiro[1,3-dihydroisoquinoline-4,1'-cyclopropane]-2-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC2=CC(N)=CC=C2C21CC2 BFWOXWLQVUGAMG-UHFFFAOYSA-N 0.000 description 7
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