BRPI0618607A2 - composto, composição farmacêutica, uso de um composto, e, métodos para inibir atividade de bace, e para tratar ou prevenir uma patologia relacionada a a-beta em um mamìfero - Google Patents

Info

Publication number

BRPI0618607A2

BRPI0618607A2 BRPI0618607-6A BRPI0618607A BRPI0618607A2 BR PI0618607 A2 BRPI0618607 A2 BR PI0618607A2 BR PI0618607 A BRPI0618607 A BR PI0618607A BR PI0618607 A2 BRPI0618607 A2 BR PI0618607A2

Authority

BR

Brazil

Prior art keywords

aryl

heteroaryl

alkyl

cycloalkyl

heterocycloalkyl

Prior art date

2005-11-15

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 286
• 238000000034 method Methods 0.000 title claims abstract description 37
• 230000000694 effects Effects 0.000 title claims abstract description 23
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
• 241000124008 Mammalia Species 0.000 title claims description 13
• 230000002401 inhibitory effect Effects 0.000 title claims description 6
• 101150058765 BACE1 gene Proteins 0.000 title 1
• 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 96
• 150000003839 salts Chemical class 0.000 claims abstract description 61
• 206010012289 Dementia Diseases 0.000 claims abstract description 39
• 208000010877 cognitive disease Diseases 0.000 claims abstract description 32
• 208000028698 Cognitive impairment Diseases 0.000 claims abstract description 18
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 17
• 230000007170 pathology Effects 0.000 claims abstract description 7
• 102100021257 Beta-secretase 1 Human genes 0.000 claims abstract description 5
• 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims abstract description 4
• 125000003118 aryl group Chemical group 0.000 claims description 427
• 125000001072 heteroaryl group Chemical group 0.000 claims description 379
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 332
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 316
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 267
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 242
• 125000000217 alkyl group Chemical group 0.000 claims description 228
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 184
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 162
• 125000005843 halogen group Chemical group 0.000 claims description 145
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 142
• -1 arioalkyl Chemical group 0.000 claims description 130
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 128
• 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 122
• 229910052799 carbon Inorganic materials 0.000 claims description 97
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 97
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 96
• 125000001424 substituent group Chemical group 0.000 claims description 94
• 125000000304 alkynyl group Chemical group 0.000 claims description 85
• 125000001188 haloalkyl group Chemical group 0.000 claims description 79
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 61
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 60
• 229910052717 sulfur Inorganic materials 0.000 claims description 52
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 45
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
• 229910052701 rubidium Inorganic materials 0.000 claims description 35
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 34
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 29
• 238000001727 in vivo Methods 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 27
• 239000002243 precursor Substances 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 23
• 125000004432 carbon atom Chemical group C* 0.000 claims description 20
• 201000010374 Down Syndrome Diseases 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 17
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
• 102000013455 Amyloid beta-Peptides Human genes 0.000 claims description 16
• 108010090849 Amyloid beta-Peptides Proteins 0.000 claims description 16
• 206010059245 Angiopathy Diseases 0.000 claims description 16
• 208000024891 symptom Diseases 0.000 claims description 16
• 125000005466 alkylenyl group Chemical group 0.000 claims description 15
• 230000006735 deficit Effects 0.000 claims description 15
• 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims description 14
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• 206010039966 Senile dementia Diseases 0.000 claims description 14
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• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
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• 125000003282 alkyl amino group Chemical group 0.000 claims description 12
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
• 230000002792 vascular Effects 0.000 claims description 11
• 229910052705 radium Inorganic materials 0.000 claims description 10
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
• 206010044688 Trisomy 21 Diseases 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
• OBIOITWOYDDXBX-UHFFFAOYSA-N 2-(3-bromophenyl)-4-chloro-2-methyl-1,3-benzoxazine Chemical compound O1C2=CC=CC=C2C(Cl)=NC1(C)C1=CC=CC(Br)=C1 OBIOITWOYDDXBX-UHFFFAOYSA-N 0.000 claims description 4
• UANBHJOGMLSYJJ-UHFFFAOYSA-N 2-[2-(3-bromophenyl)ethyl]-2-methyl-1,3-benzoxazin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O1C2=CC=CC=C2C(N)=NC1(C)CCC1=CC=CC(Br)=C1 UANBHJOGMLSYJJ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• NJNNIZZZQLHDQT-UHFFFAOYSA-N 1-amino-3-(3-bromophenyl)-3-(trifluoromethyl)-4h-isoquinoline-6-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC(C(=O)N)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC(Br)=C1 NJNNIZZZQLHDQT-UHFFFAOYSA-N 0.000 claims description 3
• GGANFIZMIYZCQB-UHFFFAOYSA-N 1-amino-3-[3-(3-methoxyphenyl)phenyl]-3-(trifluoromethyl)-4h-isoquinoline-6-carbonitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C3=CC=C(C=C3C2)C#N)C(F)(F)F)=C1 GGANFIZMIYZCQB-UHFFFAOYSA-N 0.000 claims description 3
• DBEQWEKSSBSANW-UHFFFAOYSA-N 1-amino-3-[3-(3-methoxyphenyl)phenyl]-3-(trifluoromethyl)-4h-isoquinoline-6-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C3=CC=C(C=C3C2)C(O)=O)C(F)(F)F)=C1 DBEQWEKSSBSANW-UHFFFAOYSA-N 0.000 claims description 3
• CVEMAFPNUJWPBK-UHFFFAOYSA-N 2-(3-bromophenyl)-2-methyl-1h-quinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C2=CC=CC=C2C(N)=NC1(C)C1=CC=CC(Br)=C1 CVEMAFPNUJWPBK-UHFFFAOYSA-N 0.000 claims description 3
• ASJPNAGKSRTSOU-UHFFFAOYSA-N 2-[2-(3-bromophenyl)ethyl]-2-methyl-1h-quinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C2=CC=CC=C2C(N)=NC1(C)CCC1=CC=CC(Br)=C1 ASJPNAGKSRTSOU-UHFFFAOYSA-N 0.000 claims description 3
• IVZRBDBEWXWNCG-UHFFFAOYSA-N 2-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-2-methyl-1,3-benzoxazin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(C)N=C(N)C4=CC=CC=C4O3)C=CC=2)=C1 IVZRBDBEWXWNCG-UHFFFAOYSA-N 0.000 claims description 3
• NCSVTMDNYOUHMB-UHFFFAOYSA-N 2-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-2-methyl-1h-quinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(C)N=C(N)C4=CC=CC=C4N3)C=CC=2)=C1 NCSVTMDNYOUHMB-UHFFFAOYSA-N 0.000 claims description 3
• CDVOQPAKADWWQB-UHFFFAOYSA-N 3-(3-bromophenyl)-3,4-dihydroisoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(Br)=C1 CDVOQPAKADWWQB-UHFFFAOYSA-N 0.000 claims description 3
• HMUSTCPHRCSDBS-UHFFFAOYSA-N 3-(3-bromophenyl)-3-(trifluoromethyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC(Br)=C1 HMUSTCPHRCSDBS-UHFFFAOYSA-N 0.000 claims description 3
• QCHPNHZJJILPFX-UHFFFAOYSA-N 3-(3-bromophenyl)-3-phenyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C=1C=C(Br)C=CC=1)C1=CC=CC=C1 QCHPNHZJJILPFX-UHFFFAOYSA-N 0.000 claims description 3
• VHWWEIXPSUUANW-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-phenyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C=1C=C(Cl)C=CC=1)C1=CC=CC=C1 VHWWEIXPSUUANW-UHFFFAOYSA-N 0.000 claims description 3
• IZGOILZIFQOLCH-UHFFFAOYSA-N 3-(3-phenylphenyl)-3,4-dihydroisoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1C(C=1)=CC=CC=1C1=CC=CC=C1 IZGOILZIFQOLCH-UHFFFAOYSA-N 0.000 claims description 3
• GTMLVVUMMNMOPR-UHFFFAOYSA-N 3-[2-(3-bromophenyl)ethyl]-3-methyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C)CCC1=CC=CC(Br)=C1 GTMLVVUMMNMOPR-UHFFFAOYSA-N 0.000 claims description 3
• MMSHNXHHAKRLCP-UHFFFAOYSA-N 3-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-3-methyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(C)N=C(N)C4=CC=CC=C4C3)C=CC=2)=C1 MMSHNXHHAKRLCP-UHFFFAOYSA-N 0.000 claims description 3
• HOPNUIGTNSSOGT-UHFFFAOYSA-N 3-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-3-phenyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(N=C(N)C4=CC=CC=C4C3)C=3C=CC=CC=3)C=CC=2)=C1 HOPNUIGTNSSOGT-UHFFFAOYSA-N 0.000 claims description 3
• BVPXFERMHNAQCD-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3-(trifluoromethyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C3=CC=CC=C3C2)C(F)(F)F)=C1 BVPXFERMHNAQCD-UHFFFAOYSA-N 0.000 claims description 3
• XAYJAKJNEMKLKS-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3-methyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C)N=C(N)C3=CC=CC=C3C2)=C1 XAYJAKJNEMKLKS-UHFFFAOYSA-N 0.000 claims description 3
• VDCYXNQJWQEAEF-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3-phenyl-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C3=CC=CC=C3C2)C=2C=CC=CC=2)=C1 VDCYXNQJWQEAEF-UHFFFAOYSA-N 0.000 claims description 3
• XQRYHJYTPLAAOZ-UHFFFAOYSA-N 3-methyl-3-(3-phenylphenyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C)C(C=1)=CC=CC=1C1=CC=CC=C1 XQRYHJYTPLAAOZ-UHFFFAOYSA-N 0.000 claims description 3
• RTJBVUVZUZULEL-UHFFFAOYSA-N 3-phenyl-3-(trifluoromethyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 RTJBVUVZUZULEL-UHFFFAOYSA-N 0.000 claims description 3
• KSNHYZMGOLDAAD-UHFFFAOYSA-N 3-phenyl-6-(2h-tetrazol-5-yl)-3-(trifluoromethyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C(N)=NC(C(F)(F)F)(C=3C=CC=CC=3)CC2=CC=1C1=NN=NN1 KSNHYZMGOLDAAD-UHFFFAOYSA-N 0.000 claims description 3
• OVYSOCDQHHFLLW-UHFFFAOYSA-N 4-amino-2-[2-(3-bromophenyl)ethyl]-2-methyl-1h-quinazoline-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C2=CC(C(O)=O)=CC=C2C(N)=NC1(C)CCC1=CC=CC(Br)=C1 OVYSOCDQHHFLLW-UHFFFAOYSA-N 0.000 claims description 3
• IGMQUPUPIVTFBY-UHFFFAOYSA-N 5-(3-bromophenyl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C=2C=CSC=2C(N)=NC1C1=CC=CC(Br)=C1 IGMQUPUPIVTFBY-UHFFFAOYSA-N 0.000 claims description 3
• SZIYTRZVMUIROZ-UHFFFAOYSA-N 5-[3-(3-methoxyphenyl)phenyl]-4,5-dihydrothieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2N=C(N)C=3SC=CC=3C2)=C1 SZIYTRZVMUIROZ-UHFFFAOYSA-N 0.000 claims description 3
• SYERAYVVVVBYAX-UHFFFAOYSA-N 6-(aminomethyl)-3-phenyl-3-(trifluoromethyl)-4h-isoquinolin-1-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F.C1C2=CC(CN)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 SYERAYVVVVBYAX-UHFFFAOYSA-N 0.000 claims description 3
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• 230000002708 enhancing effect Effects 0.000 claims description 3
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 3
• 230000006883 memory enhancing effect Effects 0.000 claims description 3
• UMTXFOGGWYZSOA-UHFFFAOYSA-N n-[[1-amino-3-phenyl-3-(trifluoromethyl)-4h-isoquinolin-6-yl]methyl]methanesulfonamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC(CNS(=O)(=O)C)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 UMTXFOGGWYZSOA-UHFFFAOYSA-N 0.000 claims description 3
• AMIKLZSNQVTNNN-UHFFFAOYSA-N 1-amino-3-[3-(3-methoxyphenyl)phenyl]-3-(trifluoromethyl)-4h-isoquinoline-6-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C3=CC=C(C=C3C2)C(N)=O)C(F)(F)F)=C1 AMIKLZSNQVTNNN-UHFFFAOYSA-N 0.000 claims description 2
• IDGGKHZOFFZFNT-UHFFFAOYSA-N 1-amino-3-phenyl-3-(trifluoromethyl)-4h-isoquinoline-6-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC(C(O)=O)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 IDGGKHZOFFZFNT-UHFFFAOYSA-N 0.000 claims description 2
• IFKZSHQHLMNYJN-UHFFFAOYSA-N 2-(3-bromophenyl)-n-methoxy-2-methyl-1,3-benzoxazin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O1C2=CC=CC=C2C(NOC)=NC1(C)C1=CC=CC(Br)=C1 IFKZSHQHLMNYJN-UHFFFAOYSA-N 0.000 claims description 2
• WAYHGSVZWAQZSE-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)phenyl]-2-methyl-1h-quinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(C)N=C(N)C3=CC=CC=C3N2)=C1 WAYHGSVZWAQZSE-UHFFFAOYSA-N 0.000 claims description 2
• GZJMZQOFUSGTBS-UHFFFAOYSA-N 3'-[3-(3-methoxyphenyl)phenyl]spiro[1h-quinazoline-2,1'-cyclohexane]-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2CC3(CCC2)N=C(N)C2=CC=CC=C2N3)=C1 GZJMZQOFUSGTBS-UHFFFAOYSA-N 0.000 claims description 2
• YYZVPIDGLYBUAJ-UHFFFAOYSA-N 4-amino-2-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-2-methyl-1h-quinazoline-7-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(C)N=C(N)C4=CC=C(C=C4N3)C(O)=O)C=CC=2)=C1 YYZVPIDGLYBUAJ-UHFFFAOYSA-N 0.000 claims description 2
• FDRKMWYKESHPNS-UHFFFAOYSA-N 5-(3-bromophenyl)-5-(trifluoromethyl)-2-trimethylsilyl-4h-thieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1(C(F)(F)F)C1=CC=CC(Br)=C1 FDRKMWYKESHPNS-UHFFFAOYSA-N 0.000 claims description 2
• JENRFFTXYHALCY-UHFFFAOYSA-N 5-(3-bromophenyl)-5-(trifluoromethyl)-4h-thieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C=2C=CSC=2C(N)=NC1(C(F)(F)F)C1=CC=CC(Br)=C1 JENRFFTXYHALCY-UHFFFAOYSA-N 0.000 claims description 2
• OCHYFOFDNRHDRX-UHFFFAOYSA-N 5-phenyl-5-(trifluoromethyl)-2-trimethylsilyl-4h-thieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1(C(F)(F)F)C1=CC=CC=C1 OCHYFOFDNRHDRX-UHFFFAOYSA-N 0.000 claims description 2
• 125000005025 alkynylaryl group Chemical group 0.000 claims description 2
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
• 125000005215 cycloalkylheteroaryl group Chemical group 0.000 claims description 2
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• GAHWLYOYDYMKPM-UHFFFAOYSA-N 5-[3-(3-methoxyphenyl)phenyl]-5-(trifluoromethyl)-4h-thieno[2,3-c]pyridin-7-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C2(N=C(N)C=3SC=CC=3C2)C(F)(F)F)=C1 GAHWLYOYDYMKPM-UHFFFAOYSA-N 0.000 claims 1
• 208000012186 Alzheimer disease 3 Diseases 0.000 claims 1
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• 239000002329 esterase inhibitor Substances 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 43
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