AU2008302099B2 - Substituted amides, methods of making, use thereof for the treatment of diseases such as cancer - Google Patents

Info

Publication number

AU2008302099B2

AU2008302099B2 AU2008302099A AU2008302099A AU2008302099B2 AU 2008302099 B2 AU2008302099 B2 AU 2008302099B2 AU 2008302099 A AU2008302099 A AU 2008302099A AU 2008302099 A AU2008302099 A AU 2008302099A AU 2008302099 B2 AU2008302099 B2 AU 2008302099B2

Authority

AU

Australia

Prior art keywords

methyl

oxo

phenyl

amino

carboxamide

Prior art date

2007-09-20

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

• 238000000034 method Methods 0.000 title claims abstract description 73
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 66
• 201000010099 disease Diseases 0.000 title claims abstract description 46
• 206010028980 Neoplasm Diseases 0.000 title claims description 30
• 201000011510 cancer Diseases 0.000 title claims description 28
• 238000011282 treatment Methods 0.000 title claims description 22
• 150000001408 amides Chemical class 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 233
• 230000000694 effects Effects 0.000 claims abstract description 74
• 210000003719 b-lymphocyte Anatomy 0.000 claims abstract description 50
• 230000005764 inhibitory process Effects 0.000 claims abstract description 37
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 239000002671 adjuvant Substances 0.000 claims abstract description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 8
• 239000000969 carrier Substances 0.000 claims abstract description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 211
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 146
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 114
• 229910052757 nitrogen Inorganic materials 0.000 claims description 111
• 239000000203 mixture Substances 0.000 claims description 105
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 103
• -1 N-methylpiperazinyl Chemical group 0.000 claims description 95
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 210000004027 cell Anatomy 0.000 claims description 47
• 150000003857 carboxamides Chemical class 0.000 claims description 41
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 125000004122 cyclic group Chemical group 0.000 claims description 38
• AAPBGMOKIJYMQB-UHFFFAOYSA-N 8h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C1=CC=CCC2=C1C=C(C(=O)N)S2 AAPBGMOKIJYMQB-UHFFFAOYSA-N 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 35
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 31
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
• 230000007423 decrease Effects 0.000 claims description 24
• 208000023275 Autoimmune disease Diseases 0.000 claims description 22
• 208000010668 atopic eczema Diseases 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• 208000027866 inflammatory disease Diseases 0.000 claims description 21
• 230000000172 allergic effect Effects 0.000 claims description 20
• 208000035475 disorder Diseases 0.000 claims description 20
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 18
• 239000013543 active substance Substances 0.000 claims description 18
• 239000002246 antineoplastic agent Substances 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 15
• 206010061218 Inflammation Diseases 0.000 claims description 14
• 230000001154 acute effect Effects 0.000 claims description 14
• 230000004054 inflammatory process Effects 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 14
• 208000020084 Bone disease Diseases 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 12
• 238000002512 chemotherapy Methods 0.000 claims description 12
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 12
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
• 229940127089 cytotoxic agent Drugs 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 11
• 230000035945 sensitivity Effects 0.000 claims description 10
• 125000003944 tolyl group Chemical group 0.000 claims description 10
• 230000001965 increasing effect Effects 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 238000000338 in vitro Methods 0.000 claims description 8
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 239000006188 syrup Substances 0.000 claims description 7
• 235000020357 syrup Nutrition 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 239000000499 gel Substances 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 208000004736 B-Cell Leukemia Diseases 0.000 claims description 3
• 208000003950 B-cell lymphoma Diseases 0.000 claims description 3
• 241000282326 Felis catus Species 0.000 claims description 3
• 239000002775 capsule Substances 0.000 claims description 3
• 239000006071 cream Substances 0.000 claims description 3
• ZDQYITFLOBEZOA-UHFFFAOYSA-N n-[3-[5-[[5-(1,4-dimethyl-3-oxopiperazin-2-yl)pyridin-2-yl]amino]-1-methyl-6-oxopyridin-3-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound CN1CCN(C)C(=O)C1C(C=N1)=CC=C1NC1=CC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O ZDQYITFLOBEZOA-UHFFFAOYSA-N 0.000 claims description 3
• KNGKJQJHVUAPTP-HKBQPEDESA-N n-[3-[6-[4-[(1s)-2-(dimethylamino)-1-[methyl(propan-2-yl)amino]-2-oxoethyl]anilino]-4-methyl-5-oxopyrazin-2-yl]-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound C1=CC([C@@H](C(=O)N(C)C)N(C)C(C)C)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C=CC=2)C)=CN(C)C1=O KNGKJQJHVUAPTP-HKBQPEDESA-N 0.000 claims description 3
• 239000003826 tablet Substances 0.000 claims description 3
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• VLVJSLJPYOEYMO-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-cyclohepta[b]thiophene-2-carboxamide Chemical compound C1CCCCC2=C1C=C(C(=O)N)S2 VLVJSLJPYOEYMO-UHFFFAOYSA-N 0.000 claims description 2
• 241000282472 Canis lupus familiaris Species 0.000 claims description 2
• 239000000443 aerosol Substances 0.000 claims description 2
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 2
• IHLZEXWATBHHIT-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-2,6-difluorophenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)F)=CN(C)C1=O IHLZEXWATBHHIT-UHFFFAOYSA-N 0.000 claims description 2
• 239000002997 ophthalmic solution Substances 0.000 claims description 2
• RLZZZVKAURTHCP-UHFFFAOYSA-N phenanthrene-3,4-diol Chemical compound C1=CC=C2C3=C(O)C(O)=CC=C3C=CC2=C1 RLZZZVKAURTHCP-UHFFFAOYSA-N 0.000 claims 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
• YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 2
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 2
• 241000907681 Morpho Species 0.000 claims 1
• XAXXTYXMWOFKLW-UHFFFAOYSA-N [C-]1=CC=[NH+]1 Chemical compound [C-]1=CC=[NH+]1 XAXXTYXMWOFKLW-UHFFFAOYSA-N 0.000 claims 1
• 239000012530 fluid Substances 0.000 claims 1
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 1
• KKMUBLXRAKGXOV-UHFFFAOYSA-N n-[3-[6-[4-(4-ethyl-1-methyl-3-oxopiperazin-2-yl)anilino]-4-methyl-5-oxopyrazin-2-yl]-6-fluoro-2-methylphenyl]-4,5,6,7-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound O=C1N(CC)CCN(C)C1C(C=C1)=CC=C1NC1=NC(C=2C(=C(NC(=O)C=3SC=4CCCCC=4C=3)C(F)=CC=2)C)=CN(C)C1=O KKMUBLXRAKGXOV-UHFFFAOYSA-N 0.000 claims 1
• 235000005152 nicotinamide Nutrition 0.000 claims 1
• 239000011570 nicotinamide Substances 0.000 claims 1
• 239000006187 pill Substances 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• 238000006243 chemical reaction Methods 0.000 description 64
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
• 239000007787 solid Substances 0.000 description 53
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
• 238000010992 reflux Methods 0.000 description 48
• 239000000243 solution Substances 0.000 description 48
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
• 230000002829 reductive effect Effects 0.000 description 39
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
• 238000005481 NMR spectroscopy Methods 0.000 description 36
• 239000000725 suspension Substances 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 26
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 25
• 239000012065 filter cake Substances 0.000 description 24
• 239000012453 solvate Substances 0.000 description 23
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• 229910052799 carbon Inorganic materials 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 19
• 238000003556 assay Methods 0.000 description 18
• 239000000706 filtrate Substances 0.000 description 18
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 230000001363 autoimmune Effects 0.000 description 17
• 235000019441 ethanol Nutrition 0.000 description 17
• 208000024891 symptom Diseases 0.000 description 17
• XTTSSRIQACCPCW-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzothiophene-2-carboxamide Chemical compound S1C(CC2C1=CC=CC2)C(=O)N XTTSSRIQACCPCW-UHFFFAOYSA-N 0.000 description 16
• 235000019439 ethyl acetate Nutrition 0.000 description 16
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
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• 108091000080 Phosphotransferase Proteins 0.000 description 14
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• 238000012360 testing method Methods 0.000 description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
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• 239000001257 hydrogen Substances 0.000 description 12
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 12
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• NDXZYCKYJSHECJ-UHFFFAOYSA-N 4,5,6,7-tetrahydro-1-benzothiophene-2-carbonyl chloride Chemical compound C1CCCC2=C1C=C(C(=O)Cl)S2 NDXZYCKYJSHECJ-UHFFFAOYSA-N 0.000 description 10
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