CA2671614A1 - Substituted 2,3-dihydroimidazo[1,2-c]quinazoline derivatives useful for treating hyper-proliferative disorders and diseases associated with angiogenesis - Google Patents

Info

Publication number

CA2671614A1

CA2671614A1 CA002671614A CA2671614A CA2671614A1 CA 2671614 A1 CA2671614 A1 CA 2671614A1 CA 002671614 A CA002671614 A CA 002671614A CA 2671614 A CA2671614 A CA 2671614A CA 2671614 A1 CA2671614 A1 CA 2671614A1

Authority

CA

Canada

Prior art keywords

methoxy

dihydroimidazo

quinazolin

morpholin

ylpropoxy

Prior art date

2006-12-05

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 44
• 201000010099 disease Diseases 0.000 title claims abstract description 11
• 230000003463 hyperproliferative effect Effects 0.000 title claims abstract description 10
• 208000035475 disorder Diseases 0.000 title claims description 32
• 230000033115 angiogenesis Effects 0.000 title abstract description 9
• NTTQCLSBWRKUIJ-UHFFFAOYSA-N 2,3-dihydroimidazo[1,2-c]quinazoline Chemical class C1=CC=C2C3=NCCN3C=NC2=C1 NTTQCLSBWRKUIJ-UHFFFAOYSA-N 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 194
• 230000005764 inhibitory process Effects 0.000 claims abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 159
• -1 nitro, hydroxy Chemical group 0.000 claims description 140
• 206010028980 Neoplasm Diseases 0.000 claims description 77
• 210000004027 cell Anatomy 0.000 claims description 68
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 64
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 58
• 201000011510 cancer Diseases 0.000 claims description 47
• 238000000034 method Methods 0.000 claims description 46
• 235000005152 nicotinamide Nutrition 0.000 claims description 38
• 239000011570 nicotinamide Substances 0.000 claims description 38
• 229960003966 nicotinamide Drugs 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 35
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 32
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 30
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 239000012453 solvate Substances 0.000 claims description 22
• 239000003814 drug Substances 0.000 claims description 21
• 229910052757 nitrogen Inorganic materials 0.000 claims description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
• 229940079593 drug Drugs 0.000 claims description 17
• 229910052760 oxygen Inorganic materials 0.000 claims description 17
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 16
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 16
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 16
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 16
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 16
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• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 16
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 15
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
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• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
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• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
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• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 6
• DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims description 6
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• 125000003545 alkoxy group Chemical group 0.000 claims description 6
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