AU2008258366B2 - 2-oxo-3-benzyl-benzoxazol-2-one derivatives and related compounds as Met kinase inhibitors for the treatment of tumors - Google Patents

Info

Publication number

AU2008258366B2

AU2008258366B2 AU2008258366A AU2008258366A AU2008258366B2 AU 2008258366 B2 AU2008258366 B2 AU 2008258366B2 AU 2008258366 A AU2008258366 A AU 2008258366A AU 2008258366 A AU2008258366 A AU 2008258366A AU 2008258366 B2 AU2008258366 B2 AU 2008258366B2

Authority

AU

Australia

Prior art keywords

methyl

phenyl

ylmethyl

methylpiperazin

mmol

Prior art date

2007-06-06

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.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 147
• 238000011282 treatment Methods 0.000 title claims description 51
• 206010028980 Neoplasm Diseases 0.000 title claims description 43
• FPYJSJDOHRDAMT-KQWNVCNZSA-N 1h-indole-5-sulfonamide, n-(3-chlorophenyl)-3-[[3,5-dimethyl-4-[(4-methyl-1-piperazinyl)carbonyl]-1h-pyrrol-2-yl]methylene]-2,3-dihydro-n-methyl-2-oxo-, (3z)- Chemical compound C=1C=C2NC(=O)\C(=C/C3=C(C(C(=O)N4CCN(C)CC4)=C(C)N3)C)C2=CC=1S(=O)(=O)N(C)C1=CC=CC(Cl)=C1 FPYJSJDOHRDAMT-KQWNVCNZSA-N 0.000 title claims description 24
• 229940043355 kinase inhibitor Drugs 0.000 title description 7
• 239000003757 phosphotransferase inhibitor Substances 0.000 title description 7
• 238000000034 method Methods 0.000 claims description 190
• 239000000203 mixture Substances 0.000 claims description 154
• -1 propyl [3-(5-methyl-2-oxobenzoxa zol-3-ylmethyl)phenyl]carbamate Chemical compound 0.000 claims description 154
• 238000002360 preparation method Methods 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 70
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 47
• 201000010099 disease Diseases 0.000 claims description 45
• 239000003814 drug Substances 0.000 claims description 44
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• 239000004480 active ingredient Substances 0.000 claims description 38
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 239000012453 solvate Substances 0.000 claims description 30
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
• 230000005764 inhibitory process Effects 0.000 claims description 20
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
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• 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims description 17
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• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 108060006633 protein kinase Proteins 0.000 claims description 7
• JQMCCHXCRZUYKD-UHFFFAOYSA-N 5-methyl-3-[[3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]phenyl]methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C1CN(C)CCN1C1=CN=C(C=2C=C(CN3C(OC4=CC=C(C)N=C43)=O)C=CC=2)N=C1 JQMCCHXCRZUYKD-UHFFFAOYSA-N 0.000 claims description 6
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• FRNTUFQKHQMLSE-UHFFFAOYSA-N 1,3-benzoxazole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=COC2=C1 FRNTUFQKHQMLSE-UHFFFAOYSA-N 0.000 claims description 4
• MWNBUROLPQTKQO-UHFFFAOYSA-N 3-[[3-[5-[2-(dimethylamino)ethoxy]pyrimidin-2-yl]phenyl]methyl]-5-methyl-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound N1=CC(OCCN(C)C)=CN=C1C1=CC=CC(CN2C(OC3=CC=C(C)N=C32)=O)=C1 MWNBUROLPQTKQO-UHFFFAOYSA-N 0.000 claims description 4
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• JNJMXOGQVXFPRX-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[(5-methoxy-2-oxo-1,3-benzoxazol-3-yl)methyl]phenyl]carbamate Chemical compound C12=CC(OC)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1NC(=O)OCCCN1CCN(C)CC1 JNJMXOGQVXFPRX-UHFFFAOYSA-N 0.000 claims description 3
• FBVSXQVJMQPEQH-UHFFFAOYSA-N 5-methyl-3-[[3-(3-methyl-6-oxopyridazin-1-yl)phenyl]methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound N1=C(C)C=CC(=O)N1C1=CC=CC(CN2C(OC3=CC=C(C)N=C32)=O)=C1 FBVSXQVJMQPEQH-UHFFFAOYSA-N 0.000 claims description 3
• OHCHLZCPHLPHBY-UHFFFAOYSA-N 5-methyl-3-[[3-(5-methylpyridin-2-yl)phenyl]methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound N1=CC(C)=CC=C1C1=CC=CC(CN2C(OC3=CC=C(C)N=C32)=O)=C1 OHCHLZCPHLPHBY-UHFFFAOYSA-N 0.000 claims description 3
• OYMMFCMSWOQHGG-UHFFFAOYSA-N 5-methyl-3-[[3-[5-(1-methylpyrazol-4-yl)pyrimidin-2-yl]phenyl]methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C12=NC(C)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1C(N=C1)=NC=C1C=1C=NN(C)C=1 OYMMFCMSWOQHGG-UHFFFAOYSA-N 0.000 claims description 3
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• HMGAIVGWBYPGNQ-UHFFFAOYSA-N n'-[3-[(6-chloro-2-oxo-1,3-benzoxazol-3-yl)methyl]phenyl]-n-[2-(dimethylamino)ethyl]oxamide Chemical compound CN(C)CCNC(=O)C(=O)NC1=CC=CC(CN2C(OC3=CC(Cl)=CC=C32)=O)=C1 HMGAIVGWBYPGNQ-UHFFFAOYSA-N 0.000 claims description 3
• QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims description 3
• 238000010361 transduction Methods 0.000 claims description 3
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• LKPOSUSYJWBWGB-UHFFFAOYSA-N 1-[3-[(6-chloro-2-oxo-1,3-benzoxazol-3-yl)methyl]phenyl]-3-[3-(4-methylpiperazin-1-yl)propyl]urea Chemical compound C1CN(C)CCN1CCCNC(=O)NC1=CC=CC(CN2C(OC3=CC(Cl)=CC=C32)=O)=C1 LKPOSUSYJWBWGB-UHFFFAOYSA-N 0.000 claims description 2
• KRMGHPJHLMAAHF-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[(5-chloro-2-oxo-1,3-benzoxazol-3-yl)methyl]phenyl]carbamate Chemical compound C1CN(C)CCN1CCCOC(=O)NC1=CC=CC(CN2C(OC3=CC=C(Cl)C=C32)=O)=C1 KRMGHPJHLMAAHF-UHFFFAOYSA-N 0.000 claims description 2
• QPJWKPLTQLWVEB-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[(5-methyl-2-oxo-[1,3]oxazolo[4,5-b]pyridin-3-yl)methyl]phenyl]carbamate Chemical compound C1CN(C)CCN1CCCOC(=O)NC1=CC=CC(CN2C(OC3=CC=C(C)N=C32)=O)=C1 QPJWKPLTQLWVEB-UHFFFAOYSA-N 0.000 claims description 2
• GIMDOGRZMMZPTH-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[(6-chloro-2-oxo-1,3-benzoxazol-3-yl)methyl]phenyl]carbamate Chemical compound C1CN(C)CCN1CCCOC(=O)NC1=CC=CC(CN2C(OC3=CC(Cl)=CC=C32)=O)=C1 GIMDOGRZMMZPTH-UHFFFAOYSA-N 0.000 claims description 2
• HREVEQFWQQFLHI-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[[2-oxo-5-(propylcarbamoyl)-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound C12=CC(C(=O)NCCC)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1NC(=O)OCCCN1CCN(C)CC1 HREVEQFWQQFLHI-UHFFFAOYSA-N 0.000 claims description 2
• KYQFWRYSGYIYDP-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propyl n-[3-[[5-(dimethylcarbamoyl)-2-oxo-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound C12=CC(C(=O)N(C)C)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1NC(=O)OCCCN1CCN(C)CC1 KYQFWRYSGYIYDP-UHFFFAOYSA-N 0.000 claims description 2
• CVWWPXNMFZKOKY-UHFFFAOYSA-N 3-(dimethylamino)propyl n-[3-[[2-oxo-5-(propylcarbamoyl)-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound C12=CC(C(=O)NCCC)=CC=C2OC(=O)N1CC1=CC=CC(NC(=O)OCCCN(C)C)=C1 CVWWPXNMFZKOKY-UHFFFAOYSA-N 0.000 claims description 2
• DRHADCQMUUVGBR-UHFFFAOYSA-N 3-(dimethylamino)propyl n-[3-[[5-(dimethylcarbamoyl)-2-oxo-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound CN(C)CCCOC(=O)NC1=CC=CC(CN2C(OC3=CC=C(C=C32)C(=O)N(C)C)=O)=C1 DRHADCQMUUVGBR-UHFFFAOYSA-N 0.000 claims description 2
• JFPHZKKZDRGUHF-UHFFFAOYSA-N 3-[[3-[5-[3-(dimethylamino)propoxy]pyrimidin-2-yl]phenyl]methyl]-5-(1-methylpyrazol-4-yl)-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound N1=CC(OCCCN(C)C)=CN=C1C1=CC=CC(CN2C(OC3=CC=C(N=C32)C2=CN(C)N=C2)=O)=C1 JFPHZKKZDRGUHF-UHFFFAOYSA-N 0.000 claims description 2
• IWPVYVFNSLQERK-UHFFFAOYSA-N 3-[[3-[5-[3-(dimethylamino)propoxy]pyrimidin-2-yl]phenyl]methyl]-6-(1-hydroxyethyl)-1,3-benzoxazol-2-one Chemical compound O=C1OC2=CC(C(O)C)=CC=C2N1CC(C=1)=CC=CC=1C1=NC=C(OCCCN(C)C)C=N1 IWPVYVFNSLQERK-UHFFFAOYSA-N 0.000 claims description 2
• BXHFAKHBFCKTAK-UHFFFAOYSA-N 3-piperazin-1-ylpropyl n-[3-[[2-oxo-5-(propylcarbamoyl)-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound C12=CC(C(=O)NCCC)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1NC(=O)OCCCN1CCNCC1 BXHFAKHBFCKTAK-UHFFFAOYSA-N 0.000 claims description 2
• SWPQPBFWWQMONT-UHFFFAOYSA-N 3-piperazin-1-ylpropyl n-[3-[[5-(dimethylcarbamoyl)-2-oxo-1,3-benzoxazol-3-yl]methyl]phenyl]carbamate Chemical compound C12=CC(C(=O)N(C)C)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1NC(=O)OCCCN1CCNCC1 SWPQPBFWWQMONT-UHFFFAOYSA-N 0.000 claims description 2
• RQMCWMFHVWHVRG-UHFFFAOYSA-N 5-methyl-3-[(3-pyrimidin-5-ylphenyl)methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C12=NC(C)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1C1=CN=CN=C1 RQMCWMFHVWHVRG-UHFFFAOYSA-N 0.000 claims description 2
• HRWFKUPAEQIQON-UHFFFAOYSA-N 5-methyl-3-[[3-(4-piperazin-1-ylpyrimidin-2-yl)phenyl]methyl]-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C12=NC(C)=CC=C2OC(=O)N1CC(C=1)=CC=CC=1C(N=1)=NC=CC=1N1CCNCC1 HRWFKUPAEQIQON-UHFFFAOYSA-N 0.000 claims description 2
• 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 2
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• OOGSCZHBZWRNNK-UHFFFAOYSA-N methyl 3-[[3-[3-(dimethylamino)propoxycarbonylamino]phenyl]methyl]-2-oxo-1,3-benzoxazole-6-carboxylate Chemical compound O=C1OC2=CC(C(=O)OC)=CC=C2N1CC1=CC=CC(NC(=O)OCCCN(C)C)=C1 OOGSCZHBZWRNNK-UHFFFAOYSA-N 0.000 claims description 2
• UYMUZNAMQYGWJH-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-oxo-3-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-1,3-benzoxazole-5-carboxamide Chemical compound C1=C2NC(=O)NC2=CC(CN2C(=O)OC3=CC=C(C=C32)C(=O)NCCN(C)C)=C1 UYMUZNAMQYGWJH-UHFFFAOYSA-N 0.000 claims description 2
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• GJKDXYTZWNMUNF-UHFFFAOYSA-N n-[4-(dimethylamino)butyl]-2-oxo-3-[(2-oxo-1,3-dihydrobenzimidazol-5-yl)methyl]-1,3-benzoxazole-5-carboxamide Chemical compound C1=C2NC(=O)NC2=CC(CN2C(=O)OC3=CC=C(C=C32)C(=O)NCCCCN(C)C)=C1 GJKDXYTZWNMUNF-UHFFFAOYSA-N 0.000 claims description 2
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• IICOWCXZQQVGLH-UHFFFAOYSA-N ethyl n-[3-[1-[5-[3-(dimethylamino)propylcarbamoyl]-2-oxo-1,3-benzoxazol-3-yl]ethyl]phenyl]carbamate Chemical compound CCOC(=O)NC1=CC=CC(C(C)N2C(OC3=CC=C(C=C32)C(=O)NCCCN(C)C)=O)=C1 IICOWCXZQQVGLH-UHFFFAOYSA-N 0.000 claims 1
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