CA2687786A1 - Combination of chk and parp inhibitors for the treatment of cancers - Google Patents

Info

Publication number

CA2687786A1

CA2687786A1 CA2687786A CA2687786A CA2687786A1 CA 2687786 A1 CA2687786 A1 CA 2687786A1 CA 2687786 A CA2687786 A CA 2687786A CA 2687786 A CA2687786 A CA 2687786A CA 2687786 A1 CA2687786 A1 CA 2687786A1

Authority

CA

Canada

Prior art keywords

6alkyl

optionally substituted

cancer

aryl

heterocyclyl

Prior art date

2007-05-25

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 206010028980 Neoplasm Diseases 0.000 title claims description 51
• 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 title claims description 51
• 239000012661 PARP inhibitor Substances 0.000 title claims description 46
• 238000011282 treatment Methods 0.000 title claims description 28
• 239000003112 inhibitor Substances 0.000 claims abstract description 59
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims abstract description 15
• 108091000080 Phosphotransferase Proteins 0.000 claims abstract description 7
• 102000020233 phosphotransferase Human genes 0.000 claims abstract description 7
• -1 -NR11R12 Chemical group 0.000 claims description 104
• 125000003118 aryl group Chemical group 0.000 claims description 91
• 125000000623 heterocyclic group Chemical group 0.000 claims description 91
• 150000001875 compounds Chemical class 0.000 claims description 68
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
• 201000011510 cancer Diseases 0.000 claims description 36
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• 125000004432 carbon atom Chemical group C* 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000000468 ketone group Chemical group 0.000 claims description 20
• 229910052799 carbon Inorganic materials 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 19
• 229930194542 Keto Natural products 0.000 claims description 18
• 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 18
• 238000000034 method Methods 0.000 claims description 18
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• 150000002367 halogens Chemical class 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
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• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
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• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
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• 125000002252 acyl group Chemical group 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
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• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 2
• YHONVYJMVUMQAJ-UHFFFAOYSA-N 2-(carbamoylamino)-n-(1-ethylpiperidin-3-yl)-5-methylthiophene-3-carboxamide Chemical compound C1N(CC)CCCC1NC(=O)C1=C(NC(N)=O)SC(C)=C1 YHONVYJMVUMQAJ-UHFFFAOYSA-N 0.000 claims description 2
• LVPSFHZWXVDGBY-VIFPVBQESA-N 4-(carbamoylamino)-2-morpholin-4-yl-n-[(3s)-piperidin-3-yl]-1,3-thiazole-5-carboxamide Chemical compound NC(=O)NC=1N=C(N2CCOCC2)SC=1C(=O)N[C@H]1CCCNC1 LVPSFHZWXVDGBY-VIFPVBQESA-N 0.000 claims description 2
• HHLBKMZLPNCYAP-DLBZAZTESA-N 5-(4-chlorophenyl)-n-[(3s)-piperidin-3-yl]-3-[[(3r)-1-(2,2,2-trifluoroacetyl)piperidin-3-yl]carbamoylamino]thiophene-2-carboxamide Chemical compound C1N(C(=O)C(F)(F)F)CCC[C@H]1NC(=O)NC1=C(C(=O)N[C@@H]2CNCCC2)SC(C=2C=CC(Cl)=CC=2)=C1 HHLBKMZLPNCYAP-DLBZAZTESA-N 0.000 claims description 2
• DBYUDINEBGVYEV-ZETCQYMHSA-N 5-(carbamoylamino)-2-methyl-n-[(3s)-piperidin-3-yl]-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)N[C@@H]2CNCCC2)=C1NC(N)=O DBYUDINEBGVYEV-ZETCQYMHSA-N 0.000 claims description 2
• QNKJYHQPXXAMHX-VIFPVBQESA-N [3-[(3s)-3-aminoazepane-1-carbonyl]-5-ethylthiophen-2-yl]urea Chemical compound S1C(CC)=CC(C(=O)N2C[C@@H](N)CCCC2)=C1NC(N)=O QNKJYHQPXXAMHX-VIFPVBQESA-N 0.000 claims description 2
• CJCKGXRROSPGDG-NSHDSACASA-N [3-[(3s)-3-aminoazepane-1-carbonyl]-5-pyridin-2-ylthiophen-2-yl]urea Chemical compound C1[C@@H](N)CCCCN1C(=O)C1=C(NC(N)=O)SC(C=2N=CC=CC=2)=C1 CJCKGXRROSPGDG-NSHDSACASA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 230000001394 metastastic effect Effects 0.000 claims description 2
• 206010061289 metastatic neoplasm Diseases 0.000 claims description 2
• 230000000683 nonmetastatic effect Effects 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 78
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 8
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
• 101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 1
• 208000024770 Thyroid neoplasm Diseases 0.000 claims 1
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
• 210000000481 breast Anatomy 0.000 claims 1
• 239000003085 diluting agent Substances 0.000 claims 1
• 210000004072 lung Anatomy 0.000 claims 1
• 201000002510 thyroid cancer Diseases 0.000 claims 1
• 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 abstract description 14
• 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 abstract description 14
• 125000000217 alkyl group Chemical group 0.000 description 38
• 210000004027 cell Anatomy 0.000 description 34
• 125000001424 substituent group Chemical group 0.000 description 27
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 24
• 125000006413 ring segment Chemical group 0.000 description 24
• 230000000694 effects Effects 0.000 description 19
• 125000004429 atom Chemical group 0.000 description 17
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 14
• 125000003277 amino group Chemical group 0.000 description 13
• 239000004215 Carbon black (E152) Substances 0.000 description 12
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• 125000001072 heteroaryl group Chemical group 0.000 description 12
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
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