JP2010510215A5 - - Google Patents

Info

Publication number

JP2010510215A5

JP2010510215A5 JP2009537199A JP2009537199A JP2010510215A5 JP 2010510215 A5 JP2010510215 A5 JP 2010510215A5 JP 2009537199 A JP2009537199 A JP 2009537199A JP 2009537199 A JP2009537199 A JP 2009537199A JP 2010510215 A5 JP2010510215 A5 JP 2010510215A5

Authority

JP

Japan

Prior art keywords

compound

group

aliphatic

fluoro

cancer

Prior art date

2007-11-14

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.)

Granted

Links

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• 150000001875 compounds Chemical class 0.000 claims description 41
• 125000001931 aliphatic group Chemical group 0.000 claims description 24
• -1 N-methylpyrrolidinyl Chemical group 0.000 claims description 13
• 102000003989 Aurora kinases Human genes 0.000 claims description 11
• 108090000433 Aurora kinases Proteins 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 238000000034 method Methods 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 201000011510 cancer Diseases 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000001544 thienyl group Chemical group 0.000 claims description 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• 230000001404 mediated effect Effects 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 4
• 206010006187 Breast cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
• 201000002528 pancreatic cancer Diseases 0.000 claims description 3
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
• 102000004000 Aurora Kinase A Human genes 0.000 claims description 2
• 108090000461 Aurora Kinase A Proteins 0.000 claims description 2
• 101150065749 Churc1 gene Proteins 0.000 claims description 2
• 206010033128 Ovarian cancer Diseases 0.000 claims description 2
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
• 206010060862 Prostate cancer Diseases 0.000 claims description 2
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
• 102100038239 Protein Churchill Human genes 0.000 claims description 2
• 208000005718 Stomach Neoplasms Diseases 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 230000000694 effects Effects 0.000 claims description 2
• 206010017758 gastric cancer Diseases 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 230000002401 inhibitory effect Effects 0.000 claims description 2
• 230000005764 inhibitory process Effects 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 201000011549 stomach cancer Diseases 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
• 239000000203 mixture Substances 0.000 claims 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000000338 in vitro Methods 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• 229910052708 sodium Inorganic materials 0.000 claims 1
• 239000011734 sodium Substances 0.000 claims 1
• 230000001225 therapeutic effect Effects 0.000 claims 1
• 150000002431 hydrogen Chemical class 0.000 description 3
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• SRFVRJILPIASPG-UHFFFAOYSA-N 4-[[7-(2-fluoro-6-methoxyphenyl)-9-(1-methylpyrrol-2-yl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC=2N=C3C4=CC=C(C=C4C(=NCC3=CN=2)C=2C(=CC=CC=2F)OC)C=2N(C=CC=2)C)=C1 SRFVRJILPIASPG-UHFFFAOYSA-N 0.000 description 1
• ZLHFILGSQDJULK-UHFFFAOYSA-N 4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5H-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC=2N=C3C4=CC=C(Cl)C=C4C(=NCC3=CN=2)C=2C(=CC=CC=2F)OC)=C1 ZLHFILGSQDJULK-UHFFFAOYSA-N 0.000 description 1
• NRJOLMQQQLDIPP-UHFFFAOYSA-N 4-[[9-ethynyl-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC(NC=2N=C3C4=CC=C(C=C4C(=NCC3=CN=2)C=2C(=CC=CC=2F)OC)C#C)=C1 NRJOLMQQQLDIPP-UHFFFAOYSA-N 0.000 description 1
• 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
• AIUYVPGHBMKGAC-UHFFFAOYSA-M sodium;4-[[9-chloro-7-(2-fluoro-6-methoxyphenyl)-5h-pyrimido[5,4-d][2]benzazepin-2-yl]amino]-2-methoxybenzoate Chemical compound [Na+].C1=C(C([O-])=O)C(OC)=CC(NC=2N=C3C4=CC=C(Cl)C=C4C(=NCC3=CN=2)C=2C(=CC=CC=2F)OC)=C1 AIUYVPGHBMKGAC-UHFFFAOYSA-M 0.000 description 1
• 125000003107 substituted aryl group Chemical group 0.000 description 1