CA2841932A1 - 4 - piperidinyl compounds for use as tankyrase inhibitors - Google Patents

Info

Publication number

CA2841932A1

CA2841932A1 CA 2841932 CA2841932A CA2841932A1 CA 2841932 A1 CA2841932 A1 CA 2841932A1 CA 2841932 CA2841932 CA 2841932 CA 2841932 A CA2841932 A CA 2841932A CA 2841932 A1 CA2841932 A1 CA 2841932A1

Authority

CA

Canada

Prior art keywords

piperidin

oxo

methoxy

pyrrolidin

pyrimidin

Prior art date

2011-07-13

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

• 108010017601 Tankyrases Proteins 0.000 title abstract description 56
• 239000003112 inhibitor Substances 0.000 title abstract description 11
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 title description 2
• 102000004535 Tankyrases Human genes 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 199
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 38
• 201000011510 cancer Diseases 0.000 claims abstract description 30
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
• 150000003839 salts Chemical class 0.000 claims description 62
• 238000000034 method Methods 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000005843 halogen group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical class C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 17
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 15
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims description 6
• WENGDWNRTBJJRP-UHFFFAOYSA-N 1h-cyclohepta[d]imidazol-4-one Chemical compound O=C1C=CC=CC2=C1N=CN2 WENGDWNRTBJJRP-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 3
• 125000003003 spiro group Chemical group 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• KAECKBGXSOKYSN-UHFFFAOYSA-N 2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]-n-(1-methyltetrazol-5-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3N(N=NN=3)C)CC2)=O)CC1 KAECKBGXSOKYSN-UHFFFAOYSA-N 0.000 claims 1
• IDOVFINGMNNDBX-UHFFFAOYSA-N 2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]-n-([1,2,4]triazolo[4,3-a]pyridin-3-yl)acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3N4C=CC=CC4=NN=3)CC2)=O)CC1 IDOVFINGMNNDBX-UHFFFAOYSA-N 0.000 claims 1
• FMURKSCWRQGCFO-OAQYLSRUSA-N 2-[[(3r)-3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CC[C@H]1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-OAQYLSRUSA-N 0.000 claims 1
• DUCZLEBAUSAZOC-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 DUCZLEBAUSAZOC-OAQYLSRUSA-N 0.000 claims 1
• QWYIBGOLIBASGM-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-OAQYLSRUSA-N 0.000 claims 1
• NVYDBKBQXGPVQD-OAQYLSRUSA-N 2-[[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 NVYDBKBQXGPVQD-OAQYLSRUSA-N 0.000 claims 1
• DUCZLEBAUSAZOC-NRFANRHFSA-N 2-[[(3s)-3-[4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=C(C)C(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 DUCZLEBAUSAZOC-NRFANRHFSA-N 0.000 claims 1
• QOUNQNYSBYTMLY-QFIPXVFZSA-N 2-[[(3s)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopiperidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CCC2)=O)CC1 QOUNQNYSBYTMLY-QFIPXVFZSA-N 0.000 claims 1
• QWYIBGOLIBASGM-NRFANRHFSA-N 2-[[(3s)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-NRFANRHFSA-N 0.000 claims 1
• NVYDBKBQXGPVQD-NRFANRHFSA-N 2-[[(3s)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1h-cyclohepta[d]imidazol-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC=3NC4=C(C(C=CC=C4)=O)N=3)CC2)=O)CC1 NVYDBKBQXGPVQD-NRFANRHFSA-N 0.000 claims 1
• FMURKSCWRQGCFO-UHFFFAOYSA-N 2-[[3-(6-methoxy-3-oxospiro[1h-indene-2,4'-piperidine]-1'-yl)-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1OCCC(N2)=C1C(=O)N=C2CN(C1=O)CCC1N(CC1)CCC11C(=O)C2=CC=C(OC)C=C2C1 FMURKSCWRQGCFO-UHFFFAOYSA-N 0.000 claims 1
• LJLQEWDFIMKBSL-UHFFFAOYSA-N 2-[[3-[4-(4-chlorobenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(Cl)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 LJLQEWDFIMKBSL-UHFFFAOYSA-N 0.000 claims 1
• QWYIBGOLIBASGM-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1,5,7,8-tetrahydropyrano[4,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC=4CCOCC=4C(=O)N=3)CC2)=O)CC1 QWYIBGOLIBASGM-UHFFFAOYSA-N 0.000 claims 1
• ZOLNILZRLCDHDN-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-4a,7a-dihydro-3h-thieno[3,2-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4SC=CC4N=3)CC2)=O)CC1 ZOLNILZRLCDHDN-UHFFFAOYSA-N 0.000 claims 1
• DVIHZULFCIMZGZ-UHFFFAOYSA-N 2-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-6-methyl-4a,7a-dihydro-3h-thieno[2,3-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C=C(C)SC4N=3)CC2)=O)CC1 DVIHZULFCIMZGZ-UHFFFAOYSA-N 0.000 claims 1
• PERWUJINIMBCAY-UHFFFAOYSA-N 2-chloro-5-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C=C(C(Cl)=CC=3)C#N)CC2)=O)CC1 PERWUJINIMBCAY-UHFFFAOYSA-N 0.000 claims 1
• OXTYNMCLCNPCJW-UHFFFAOYSA-N 2-chloro-6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3C(=C(Cl)C=CC=3)C#N)CC2)=O)CC1 OXTYNMCLCNPCJW-UHFFFAOYSA-N 0.000 claims 1
• BHLYXUCYNUOODH-UHFFFAOYSA-N 6-[[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]methyl]-1-methyl-5,7a-dihydro-3ah-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC=3NC(=O)C4C(N(N=C4)C)N=3)CC2)=O)CC1 BHLYXUCYNUOODH-UHFFFAOYSA-N 0.000 claims 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
• JDZOLLKCZDHXOE-UHFFFAOYSA-N n-(3,4-dihydro-2h-pyrano[2,3-d]pyridazin-5-yl)-2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3C=4CCCOC=4C=NN=3)CC2)=O)CC1 JDZOLLKCZDHXOE-UHFFFAOYSA-N 0.000 claims 1
• PADREXIRIZBNMQ-GOSISDBHSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[(3r)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@H]2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-GOSISDBHSA-N 0.000 claims 1
• PADREXIRIZBNMQ-SFHVURJKSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[(3s)-3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN([C@@H]2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-SFHVURJKSA-N 0.000 claims 1
• PADREXIRIZBNMQ-UHFFFAOYSA-N n-(5,6-dihydro-[1,3]thiazolo[2,3-c][1,2,4]triazol-3-yl)-2-[3-[4-(4-methoxybenzoyl)piperidin-1-yl]-2-oxopyrrolidin-1-yl]acetamide Chemical compound C1=CC(OC)=CC=C1C(=O)C1CCN(C2C(N(CC(=O)NC=3N4CCSC4=NN=3)CC2)=O)CC1 PADREXIRIZBNMQ-UHFFFAOYSA-N 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 67
• 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 abstract description 61
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• -1 methoxy, ethoxy, propoxy, 2-propoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy Chemical group 0.000 description 80
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