TW200418466A - Chemical compounds - Google Patents

Info

Publication number

TW200418466A

TW200418466A TW092130770A TW92130770A TW200418466A TW 200418466 A TW200418466 A TW 200418466A TW 092130770 A TW092130770 A TW 092130770A TW 92130770 A TW92130770 A TW 92130770A TW 200418466 A TW200418466 A TW 200418466A

Authority

TW

Taiwan

Prior art keywords

alkyl

group

aryl

heteroaryl

cvc4

Prior art date

2002-11-06

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 174
• 238000000034 method Methods 0.000 claims abstract description 62
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
• 201000010099 disease Diseases 0.000 claims abstract description 34
• 238000011282 treatment Methods 0.000 claims abstract description 29
• 125000000217 alkyl group Chemical group 0.000 claims description 355
• -1 c ^ c: 7-cycloalkyl Chemical group 0.000 claims description 167
• 125000001072 heteroaryl group Chemical group 0.000 claims description 79
• 150000003839 salts Chemical class 0.000 claims description 66
• 239000000203 mixture Substances 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 61
• 125000001188 haloalkyl group Chemical group 0.000 claims description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 239000012453 solvate Substances 0.000 claims description 49
• 230000000694 effects Effects 0.000 claims description 48
• 101000753291 Homo sapiens Angiopoietin-1 receptor Proteins 0.000 claims description 45
• 102100022014 Angiopoietin-1 receptor Human genes 0.000 claims description 43
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 125000000304 alkynyl group Chemical group 0.000 claims description 36
• 108010053099 Vascular Endothelial Growth Factor Receptor-2 Proteins 0.000 claims description 34
• 206010028980 Neoplasm Diseases 0.000 claims description 32
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims description 32
• 201000011510 cancer Diseases 0.000 claims description 31
• 230000033115 angiogenesis Effects 0.000 claims description 30
• 241000124008 Mammalia Species 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 108010053100 Vascular Endothelial Growth Factor Receptor-3 Proteins 0.000 claims description 25
• BJHCYTJNPVGSBZ-YXSASFKJSA-N 1-[4-[6-amino-5-[(Z)-methoxyiminomethyl]pyrimidin-4-yl]oxy-2-chlorophenyl]-3-ethylurea Chemical compound CCNC(=O)Nc1ccc(Oc2ncnc(N)c2\C=N/OC)cc1Cl BJHCYTJNPVGSBZ-YXSASFKJSA-N 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
• 102000009929 raf Kinases Human genes 0.000 claims description 18
• 108010077182 raf Kinases Proteins 0.000 claims description 18
• 102000004190 Enzymes Human genes 0.000 claims description 17
• 108090000790 Enzymes Proteins 0.000 claims description 17
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 230000006870 function Effects 0.000 claims description 16
• 125000004043 oxo group Chemical group O=* 0.000 claims description 15
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 239000003112 inhibitor Substances 0.000 claims description 13
• 102000009484 Vascular Endothelial Growth Factor Receptors Human genes 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 12
• 230000005764 inhibitory process Effects 0.000 claims description 12
• 108091008605 VEGF receptors Proteins 0.000 claims description 10
• 239000002246 antineoplastic agent Substances 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 210000004369 blood Anatomy 0.000 claims description 8
• 239000008280 blood Substances 0.000 claims description 8
• 210000004204 blood vessel Anatomy 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 239000003102 growth factor Substances 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 108091000080 Phosphotransferase Proteins 0.000 claims description 6
• 102000001253 Protein Kinase Human genes 0.000 claims description 6
• 239000003153 chemical reaction reagent Substances 0.000 claims description 6
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 102000020233 phosphotransferase Human genes 0.000 claims description 6
• 108060006633 protein kinase Proteins 0.000 claims description 6
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 102000009465 Growth Factor Receptors Human genes 0.000 claims description 5
• 108010009202 Growth Factor Receptors Proteins 0.000 claims description 5
• 101100481410 Mus musculus Tek gene Proteins 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 5
• 238000011394 anticancer treatment Methods 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
• 230000035699 permeability Effects 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 101100481408 Danio rerio tie2 gene Proteins 0.000 claims description 4
• 239000004615 ingredient Substances 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 230000035790 physiological processes and functions Effects 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
• 101150009274 nhr-1 gene Proteins 0.000 claims description 3
• PLXPTFQGYWXIEA-UHFFFAOYSA-N nitroformonitrile Chemical compound [O-][N+](=O)C#N PLXPTFQGYWXIEA-UHFFFAOYSA-N 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 238000007639 printing Methods 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
• 125000002837 carbocyclic group Chemical group 0.000 claims description 2
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
• 239000000779 smoke Substances 0.000 claims description 2
• 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 claims 3
• 101710100968 Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 claims 3
• 108010034265 Vascular Endothelial Growth Factor Receptors Proteins 0.000 claims 3
• 125000000565 sulfonamide group Chemical group 0.000 claims 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• 102000044591 ErbB-4 Receptor Human genes 0.000 claims 2
• 101710100963 Receptor tyrosine-protein kinase erbB-4 Proteins 0.000 claims 2
• 108010090091 TIE-2 Receptor Proteins 0.000 claims 2
• 102000012753 TIE-2 Receptor Human genes 0.000 claims 2
• 150000004820 halides Chemical class 0.000 claims 2
• 125000002971 oxazolyl group Chemical group 0.000 claims 2
• RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims 2
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
• 108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims 1
• 102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims 1
• 101100153409 Solanum lycopersicum Tm-2 gene Proteins 0.000 claims 1
• 102100033179 Vascular endothelial growth factor receptor 3 Human genes 0.000 claims 1
• 125000005741 alkyl alkenyl group Chemical group 0.000 claims 1
• 125000003710 aryl alkyl group Chemical group 0.000 claims 1
• AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
• 230000010261 cell growth Effects 0.000 claims 1
• RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 claims 1
• 210000004268 dentin Anatomy 0.000 claims 1
• 239000004575 stone Substances 0.000 claims 1
• 229940043355 kinase inhibitor Drugs 0.000 abstract description 3
• 239000003757 phosphotransferase inhibitor Substances 0.000 abstract description 3
• 239000002253 acid Substances 0.000 description 63
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 40
• 230000002079 cooperative effect Effects 0.000 description 38
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
• 238000009472 formulation Methods 0.000 description 27
• 150000001412 amines Chemical class 0.000 description 26
• 210000004027 cell Anatomy 0.000 description 25
• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 25
• 102000016663 Vascular Endothelial Growth Factor Receptor-3 Human genes 0.000 description 24
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
• 238000012360 testing method Methods 0.000 description 21
• 101150041968 CDC13 gene Proteins 0.000 description 20
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• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
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• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 10
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• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
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• XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 6
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• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
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