NZ722487A - Heteroaryl amides as inhibitors of protein aggregation - Google Patents

Info

Publication number

NZ722487A

NZ722487A NZ722487A NZ72248715A NZ722487A NZ 722487 A NZ722487 A NZ 722487A NZ 722487 A NZ722487 A NZ 722487A NZ 72248715 A NZ72248715 A NZ 72248715A NZ 722487 A NZ722487 A NZ 722487A

Authority

NZ

New Zealand

Prior art keywords

compound

indolyl

acceptable salt

pharmaceutically acceptable

hexanyl

Prior art date

2014-01-29

Links

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• -1 Heteroaryl amides Chemical class 0.000 title claims abstract description 43
• 230000004845 protein aggregation Effects 0.000 title claims abstract description 21
• 239000003112 inhibitor Substances 0.000 title description 8
• 238000000034 method Methods 0.000 claims abstract description 46
• 208000018737 Parkinson disease Diseases 0.000 claims abstract description 37
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 201000010099 disease Diseases 0.000 claims abstract description 22
• 201000002832 Lewy body dementia Diseases 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 11
• 208000001089 Multiple system atrophy Diseases 0.000 claims abstract description 9
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
• 201000011240 Frontotemporal dementia Diseases 0.000 claims abstract description 7
• 208000009829 Lewy Body Disease Diseases 0.000 claims abstract description 7
• 201000011510 cancer Diseases 0.000 claims abstract description 7
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
• 206010012289 Dementia Diseases 0.000 claims abstract description 6
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 6
• 201000001441 melanoma Diseases 0.000 claims abstract description 5
• 208000023105 Huntington disease Diseases 0.000 claims abstract description 4
• 150000001875 compounds Chemical class 0.000 claims description 186
• 150000003839 salts Chemical class 0.000 claims description 60
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 30
• 102000004169 proteins and genes Human genes 0.000 claims description 27
• 108090000623 proteins and genes Proteins 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 210000004027 cell Anatomy 0.000 claims description 19
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 16
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• 238000009825 accumulation Methods 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 14
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 14
• 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 13
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 10
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 9
• 125000006578 monocyclic heterocycloalkyl group Chemical group 0.000 claims description 9
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 9
• 125000005843 halogen group Chemical group 0.000 claims description 8
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 7
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 238000002360 preparation method Methods 0.000 claims description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 238000000338 in vitro Methods 0.000 claims description 4
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
• 230000006919 peptide aggregation Effects 0.000 claims description 4
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
• 239000005977 Ethylene Substances 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
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• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
• 150000003852 triazoles Chemical class 0.000 claims description 2
• 150000003857 carboxamides Chemical class 0.000 claims 21
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 12
• QWEWLLNSJDTOKH-UHFFFAOYSA-N 1,3-thiazole-2-carboxamide Chemical compound NC(=O)C1=NC=CS1 QWEWLLNSJDTOKH-UHFFFAOYSA-N 0.000 claims 3
• INWVNNCOIIHEPX-UHFFFAOYSA-N thiadiazole-4-carboxamide Chemical compound NC(=O)C1=CSN=N1 INWVNNCOIIHEPX-UHFFFAOYSA-N 0.000 claims 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
• NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 1
• MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 claims 1
• WAJYSAZRVRVLBA-UHFFFAOYSA-N 4-[2-(1,3-thiazol-2-yl)ethyl]morpholine Chemical compound C(CC1=NC=CS1)N1CCOCC1 WAJYSAZRVRVLBA-UHFFFAOYSA-N 0.000 claims 1
• 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
• 125000004193 piperazinyl group Chemical group 0.000 claims 1
• 230000004770 neurodegeneration Effects 0.000 abstract description 10
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• 102000003802 alpha-Synuclein Human genes 0.000 description 99
• 108090000185 alpha-Synuclein Proteins 0.000 description 99
• 239000000203 mixture Substances 0.000 description 98
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 58
• 238000011830 transgenic mouse model Methods 0.000 description 50
• 239000000243 solution Substances 0.000 description 46
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 42
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• 235000019439 ethyl acetate Nutrition 0.000 description 29
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• 230000000694 effects Effects 0.000 description 27
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• 239000012267 brine Substances 0.000 description 21
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
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