NZ556433A - 1, 3-diaryl substituted ureas as modulators of kinase activity - Google Patents

Info

Publication number

NZ556433A

NZ556433A NZ556433A NZ55643306A NZ556433A NZ 556433 A NZ556433 A NZ 556433A NZ 556433 A NZ556433 A NZ 556433A NZ 55643306 A NZ55643306 A NZ 55643306A NZ 556433 A NZ556433 A NZ 556433A

Authority

NZ

New Zealand

Prior art keywords

pyridin

phenyl

indol

ylmethyl

urea

Prior art date

2005-01-14

Links

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• 230000000694 effects Effects 0.000 title claims abstract description 78
• 108091000080 Phosphotransferase Proteins 0.000 title claims description 90
• 102000020233 phosphotransferase Human genes 0.000 title claims description 90
• 235000013877 carbamide Nutrition 0.000 title abstract description 9
• 150000003672 ureas Chemical class 0.000 title abstract description 5
• 239000004202 carbamide Substances 0.000 claims abstract description 269
• 150000001875 compounds Chemical class 0.000 claims abstract description 129
• 102100033177 Vascular endothelial growth factor receptor 2 Human genes 0.000 claims abstract description 43
• 101000851007 Homo sapiens Vascular endothelial growth factor receptor 2 Proteins 0.000 claims abstract description 41
• 230000033115 angiogenesis Effects 0.000 claims abstract description 31
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 20
• 201000011510 cancer Diseases 0.000 claims abstract description 14
• ZXBFYBLSJMEBEP-UHFFFAOYSA-N 1-[1-[(2-aminopyridin-4-yl)methyl]indol-4-yl]-3-(5-bromo-2-methoxyphenyl)urea Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(N)=C1 ZXBFYBLSJMEBEP-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 186
• 150000005829 chemical entities Chemical class 0.000 claims description 156
• -1 amino, aminocarbonyl Chemical group 0.000 claims description 84
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 82
• 125000001072 heteroaryl group Chemical group 0.000 claims description 82
• 239000000203 mixture Substances 0.000 claims description 68
• 125000005843 halogen group Chemical group 0.000 claims description 60
• 201000010099 disease Diseases 0.000 claims description 54
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 54
• 239000001257 hydrogen Substances 0.000 claims description 54
• 229910052739 hydrogen Inorganic materials 0.000 claims description 54
• 238000000034 method Methods 0.000 claims description 53
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 102000016971 Proto-Oncogene Proteins c-kit Human genes 0.000 claims description 35
• 108010014608 Proto-Oncogene Proteins c-kit Proteins 0.000 claims description 35
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
• 125000003107 substituted aryl group Chemical group 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 150000003839 salts Chemical group 0.000 claims description 29
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 28
• 125000002252 acyl group Chemical group 0.000 claims description 27
• 239000003814 drug Substances 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 208000035475 disorder Diseases 0.000 claims description 26
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
• 238000003556 assay Methods 0.000 claims description 24
• 238000000338 in vitro Methods 0.000 claims description 22
• 102100031983 Ephrin type-B receptor 4 Human genes 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
• 150000002431 hydrogen Chemical class 0.000 claims description 18
• 239000012453 solvate Chemical group 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 101000692455 Homo sapiens Platelet-derived growth factor receptor beta Proteins 0.000 claims description 16
• 102100026547 Platelet-derived growth factor receptor beta Human genes 0.000 claims description 16
• 230000008859 change Effects 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
• 239000013078 crystal Chemical group 0.000 claims description 15
• 230000005764 inhibitory process Effects 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 229910052760 oxygen Inorganic materials 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
• 241000282414 Homo sapiens Species 0.000 claims description 9
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 230000002401 inhibitory effect Effects 0.000 claims description 7
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• 239000006188 syrup Substances 0.000 claims description 7
• 235000020357 syrup Nutrition 0.000 claims description 7
• 239000002671 adjuvant Substances 0.000 claims description 6
• YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 6
• 239000000499 gel Substances 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 230000001850 reproductive effect Effects 0.000 claims description 6
• 239000000969 carrier Substances 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 238000007911 parenteral administration Methods 0.000 claims description 5
• 229940080818 propionamide Drugs 0.000 claims description 5
• 206010036618 Premenstrual syndrome Diseases 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001425 triazolyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• HQLLTDZFHPPOMB-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-(1-pyridin-4-ylindol-5-yl)urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(N(C=C2)C=3C=CN=CC=3)C2=C1 HQLLTDZFHPPOMB-UHFFFAOYSA-N 0.000 claims description 3
• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 3
• 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims description 3
• 239000006071 cream Substances 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 238000001990 intravenous administration Methods 0.000 claims description 3
• AJAJPCNOPZDPIZ-UHFFFAOYSA-N methyl n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]carbamate Chemical compound C1=NC(NC(=O)OC)=CC(CN2C3=CC=CC(NC(=O)NC=4C(=CC=C(Br)C=4)OC)=C3C=C2)=C1 AJAJPCNOPZDPIZ-UHFFFAOYSA-N 0.000 claims description 3
• MQSZGGUEGKYKRC-UHFFFAOYSA-N n-[4-[[4-[(3-chloro-4-methylphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(CN2C3=CC=CC(NC(=O)NC=4C=C(Cl)C(C)=CC=4)=C3C=C2)=C1 MQSZGGUEGKYKRC-UHFFFAOYSA-N 0.000 claims description 3
• UISMOGMDAKUXCE-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]-2-(dimethylamino)acetamide Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(=O)CN(C)C)=C1 UISMOGMDAKUXCE-UHFFFAOYSA-N 0.000 claims description 3
• FUSABTAFEIOLFH-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]-2-methylpropanamide Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(=O)C(C)C)=C1 FUSABTAFEIOLFH-UHFFFAOYSA-N 0.000 claims description 3
• UBCKVZJPRAKVDU-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]-2-pyrrolidin-1-ylacetamide Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(=O)CN2CCCC2)=C1 UBCKVZJPRAKVDU-UHFFFAOYSA-N 0.000 claims description 3
• BUVVREQLRRRLQF-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]acetamide Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(C)=O)=C1 BUVVREQLRRRLQF-UHFFFAOYSA-N 0.000 claims description 3
• FCDLTRRRVZNJAR-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]formamide Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC=O)=C1 FCDLTRRRVZNJAR-UHFFFAOYSA-N 0.000 claims description 3
• CVPZGGJMRTYSRL-UHFFFAOYSA-N n-[4-[[4-[(5-bromo-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]propanamide Chemical compound C1=NC(NC(=O)CC)=CC(CN2C3=CC=CC(NC(=O)NC=4C(=CC=C(Br)C=4)OC)=C3C=C2)=C1 CVPZGGJMRTYSRL-UHFFFAOYSA-N 0.000 claims description 3
• FAKLPVXVBMSKPQ-UHFFFAOYSA-N n-[4-[[4-[(5-chloro-2-methoxy-4-methylphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]acetamide Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(C)=O)=C1 FAKLPVXVBMSKPQ-UHFFFAOYSA-N 0.000 claims description 3
• LRPMOUJSDVQWBZ-UHFFFAOYSA-N n-[4-[[4-[(5-chloro-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]acetamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(C)=O)=C1 LRPMOUJSDVQWBZ-UHFFFAOYSA-N 0.000 claims description 3
• PQKJVXXAJNEJFE-UHFFFAOYSA-N n-[4-[[4-[[2-methoxy-5-(trifluoromethyl)phenyl]carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]cyclopropanecarboxamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(=O)C2CC2)=C1 PQKJVXXAJNEJFE-UHFFFAOYSA-N 0.000 claims description 3
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• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• YUJBRBUIEUFERZ-UHFFFAOYSA-N 1-(5-bromo-2-methoxyphenyl)-3-[1-[[2-(methanesulfonamido)pyridin-4-yl]methyl]indol-4-yl]urea Chemical compound COC1=CC=C(Br)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NS(C)(=O)=O)=C1 YUJBRBUIEUFERZ-UHFFFAOYSA-N 0.000 claims description 2
• OCSHMIVAXMBEBS-UHFFFAOYSA-N 1-(5-chloro-2-methoxy-4-methylphenyl)-3-[7-fluoro-1-(pyridin-4-ylmethyl)indol-4-yl]urea Chemical compound COC1=CC(C)=C(Cl)C=C1NC(=O)NC1=CC=C(F)C2=C1C=CN2CC1=CC=NC=C1 OCSHMIVAXMBEBS-UHFFFAOYSA-N 0.000 claims description 2
• BBRVGUAGUUBENF-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-[[2-(4-cyanoanilino)pyridin-4-yl]methyl]indol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC=2C=CC(=CC=2)C#N)=C1 BBRVGUAGUUBENF-UHFFFAOYSA-N 0.000 claims description 2
• ZRXMCSSZSIFTOK-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[1-[[2-(methanesulfonamido)pyridin-4-yl]methyl]indol-4-yl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NS(C)(=O)=O)=C1 ZRXMCSSZSIFTOK-UHFFFAOYSA-N 0.000 claims description 2
• VCEAIMUTAHEERT-UHFFFAOYSA-N 1-phenyl-3-[3-(2-pyridin-4-ylethyl)-1h-indol-5-yl]urea Chemical compound C=1C=C2NC=C(CCC=3C=CN=CC=3)C2=CC=1NC(=O)NC1=CC=CC=C1 VCEAIMUTAHEERT-UHFFFAOYSA-N 0.000 claims description 2
• ISONNBWXPQPYIZ-UHFFFAOYSA-N 3-[acetyl(methyl)amino]-n-[4-[[4-[(5-chloro-2-methoxyphenyl)carbamoylamino]indol-1-yl]methyl]pyridin-2-yl]propanamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC=CC2=C1C=CN2CC1=CC=NC(NC(=O)CCN(C)C(C)=O)=C1 ISONNBWXPQPYIZ-UHFFFAOYSA-N 0.000 claims description 2
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