ZA200506861B - Novel cyanopyridine derivatives useful in the treatment of cancer and other disorders - Google Patents

Info

Publication number

ZA200506861B

ZA200506861B ZA200506861A ZA200506861A ZA200506861B ZA 200506861 B ZA200506861 B ZA 200506861B ZA 200506861 A ZA200506861 A ZA 200506861A ZA 200506861 A ZA200506861 A ZA 200506861A ZA 200506861 B ZA200506861 B ZA 200506861B

Authority

ZA

South Africa

Prior art keywords

cyano

pyridyloxy

carboxamide

compound

dioxan

Prior art date

2003-02-28

Links

• Espacenet
• Global Dossier
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• 206010028980 Neoplasm Diseases 0.000 title claims description 50
• 201000011510 cancer Diseases 0.000 title claims description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 15
• 238000011282 treatment Methods 0.000 title claims description 10
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 title description 2
• -1 diaryl ureas Chemical class 0.000 claims abstract description 86
• 150000001875 compounds Chemical class 0.000 claims abstract description 76
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• 239000000203 mixture Substances 0.000 claims abstract description 12
• 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• 229920006395 saturated elastomer Polymers 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 14
• 125000000217 alkyl group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 12
• 125000004432 carbon atom Chemical group C* 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 150000003839 salts Chemical class 0.000 claims description 11
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• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 125000001188 haloalkyl group Chemical group 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
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• 125000002619 bicyclic group Chemical group 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• 239000002207 metabolite Substances 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229940002612 prodrug Drugs 0.000 claims description 5
• 239000000651 prodrug Substances 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 claims description 4
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• 125000004429 atom Chemical group 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 4
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• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
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• 239000000460 chlorine Chemical group 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
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• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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• 150000003857 carboxamides Chemical class 0.000 claims 44
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• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
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• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
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• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
• 229910052794 bromium Inorganic materials 0.000 claims 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
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• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
• 230000001850 reproductive effect Effects 0.000 claims 3
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
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