NZ560607A - Proteasome inhibitors and methods of using the same - Google Patents

Info

Publication number

NZ560607A

NZ560607A NZ560607A NZ56060706A NZ560607A NZ 560607 A NZ560607 A NZ 560607A NZ 560607 A NZ560607 A NZ 560607A NZ 56060706 A NZ56060706 A NZ 56060706A NZ 560607 A NZ560607 A NZ 560607A

Authority

NZ

New Zealand

Prior art keywords

amino

methylbutyl

carbonyl

methano

hexahydro

Prior art date

2005-02-11

Links

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• Global Dossier
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• 238000000034 method Methods 0.000 title claims abstract description 61
• 229940079156 Proteasome inhibitor Drugs 0.000 title description 18
• 239000003207 proteasome inhibitor Substances 0.000 title description 18
• 150000001875 compounds Chemical class 0.000 claims abstract description 236
• 239000000203 mixture Substances 0.000 claims abstract description 89
• 150000002148 esters Chemical class 0.000 claims abstract description 85
• 108090000708 Proteasome Endopeptidase Complex Proteins 0.000 claims abstract description 67
• 102000004245 Proteasome Endopeptidase Complex Human genes 0.000 claims abstract description 66
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 43
• 230000000694 effects Effects 0.000 claims abstract description 38
• 201000011510 cancer Diseases 0.000 claims abstract description 24
• 201000010099 disease Diseases 0.000 claims abstract description 24
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 434
• -1 thialkoxy Chemical group 0.000 claims description 192
• 125000000217 alkyl group Chemical group 0.000 claims description 160
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 137
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 126
• 125000003118 aryl group Chemical group 0.000 claims description 77
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 76
• UHBGYFCCKRAEHA-UHFFFAOYSA-N P-toluamide Chemical compound CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 claims description 60
• 125000000623 heterocyclic group Chemical group 0.000 claims description 60
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 54
• 125000004122 cyclic group Chemical group 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 46
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
• 125000001188 haloalkyl group Chemical group 0.000 claims description 43
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000001072 heteroaryl group Chemical group 0.000 claims description 40
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• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• 125000005842 heteroatom Chemical group 0.000 claims description 32
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 30
• 125000000304 alkynyl group Chemical group 0.000 claims description 30
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• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 29
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
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• 125000001424 substituent group Chemical group 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 27
• 125000003282 alkyl amino group Chemical group 0.000 claims description 27
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• DCMVWHTVPMXOMG-UHFFFAOYSA-N 6-butylpyridine-2-carboxamide Chemical compound CCCCC1=CC=CC(C(N)=O)=N1 DCMVWHTVPMXOMG-UHFFFAOYSA-N 0.000 claims description 5
• RBDSXZOUEOSXFY-UHFFFAOYSA-N 6-thiophen-2-ylpyridine-2-carboxamide Chemical compound NC(=O)C1=CC=CC(C=2SC=CC=2)=N1 RBDSXZOUEOSXFY-UHFFFAOYSA-N 0.000 claims description 5
• 208000034578 Multiple myelomas Diseases 0.000 claims description 5
• KKSZSACCVDIWIE-UHFFFAOYSA-N isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(=O)N)=CC2=C1 KKSZSACCVDIWIE-UHFFFAOYSA-N 0.000 claims description 5
• 210000004185 liver Anatomy 0.000 claims description 5
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• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• CGJMVNVWQHPASW-UHFFFAOYSA-N quinoxaline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)N)=CN=C21 CGJMVNVWQHPASW-UHFFFAOYSA-N 0.000 claims description 5
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• OTUPVOMRCZCXNK-UHFFFAOYSA-N 4-phenylpyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC(C=2C=CC=CC=2)=C1 OTUPVOMRCZCXNK-UHFFFAOYSA-N 0.000 claims description 4
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• YZDXFUGIDTUCDA-UHFFFAOYSA-N isoquinoline-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=NC=CC2=C1 YZDXFUGIDTUCDA-UHFFFAOYSA-N 0.000 claims description 4
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