JP2009520685A5 - - Google Patents
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- JP2009520685A5 JP2009520685A5 JP2008541110A JP2008541110A JP2009520685A5 JP 2009520685 A5 JP2009520685 A5 JP 2009520685A5 JP 2008541110 A JP2008541110 A JP 2008541110A JP 2008541110 A JP2008541110 A JP 2008541110A JP 2009520685 A5 JP2009520685 A5 JP 2009520685A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heteroaryl
- heterocycloalkyl
- cycloalkyl
- Prior art date
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 72
- 125000003118 aryl group Chemical group 0.000 claims 70
- 125000001072 heteroaryl group Chemical group 0.000 claims 70
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims 63
- 125000003710 aryl alkyl group Chemical group 0.000 claims 57
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 51
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 44
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 44
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 34
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 32
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 32
- 125000005843 halogen group Chemical group 0.000 claims 27
- 229910052799 carbon Inorganic materials 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000000304 alkynyl group Chemical group 0.000 claims 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 4
- 208000024827 Alzheimer disease Diseases 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 238000001727 in vivo Methods 0.000 claims 3
- 239000002243 precursor Substances 0.000 claims 3
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- -1 (3′-methoxybiphenyl-3-yl) -1′H-spiro [cyclohexane-1,2′-quinazoline] -4′-amine trifluoroacetate Chemical compound 0.000 claims 1
- QDMVACSUPDWDLL-UHFFFAOYSA-N 1'-[3-(3-methoxyphenyl)phenyl]spiro[1h-quinazoline-2,3'-cyclohexene]-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(C=CC=2)C=2CCCC3(C=2)N=C(N)C2=CC=CC=C2N3)=C1 QDMVACSUPDWDLL-UHFFFAOYSA-N 0.000 claims 1
- ZFEGUWVJFDUVCO-UHFFFAOYSA-N 1-amino-3-(3-bromophenyl)-3-(trifluoromethyl)-4h-isoquinoline-6-carbonitrile Chemical compound C1C2=CC(C#N)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC(Br)=C1 ZFEGUWVJFDUVCO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- RXVNKLSJBYVTPV-UHFFFAOYSA-N 1-amino-3-phenyl-3-(trifluoromethyl)-4H-isoquinoline-6-carbonitrile hydrochloride Chemical compound Cl.C1C2=CC(C#N)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 RXVNKLSJBYVTPV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- HICQWLMPQMJNOW-UHFFFAOYSA-N 2-(3-bromophenyl)-2-methyl-1,3-benzoxazin-4-amine Chemical compound O1C2=CC=CC=C2C(N)=NC1(C)C1=CC=CC(Br)=C1 HICQWLMPQMJNOW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CBDCPWBARIEQJW-UHFFFAOYSA-N 2-(3-bromophenyl)-2-methyl-3h-1,3-benzoxazin-4-one Chemical compound N1C(=O)C2=CC=CC=C2OC1(C)C1=CC=CC(Br)=C1 CBDCPWBARIEQJW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- SORJLLJWDWPORX-UHFFFAOYSA-N 2-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-1,2-dimethylquinazolin-4-amine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(C=2C=C(CCC3(C)N(C4=CC=CC=C4C(N)=N3)C)C=CC=2)=C1 SORJLLJWDWPORX-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- YQYFQGAKNKITRN-UHFFFAOYSA-N 2-[3-(3-methoxyphenyl)phenyl]-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(C=CC=2)C2(C)N=C(N)C3=CC=CC=C3O2)=C1 YQYFQGAKNKITRN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GUZQPEQUNBMUCL-UHFFFAOYSA-N 3-(3-bromophenyl)-1-ethylsulfanyl-3-methyl-4h-isoquinoline Chemical compound C1C2=CC=CC=C2C(SCC)=NC1(C)C1=CC=CC(Br)=C1 GUZQPEQUNBMUCL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- YRWAUSCCJAWRNU-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)phenyl]-3,4-dihydroisoquinolin-1-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)C3=CC=CC=C3C2)=C1 YRWAUSCCJAWRNU-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- UNSMGVCQMIQVKA-UHFFFAOYSA-N 3-methyl-5-trimethylsilylthiophene-2-carbonitrile Chemical compound CC=1C=C([Si](C)(C)C)SC=1C#N UNSMGVCQMIQVKA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- XHKQMNMOWLESNO-UHFFFAOYSA-N 5-(3-bromophenyl)-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound N1=C(N)C=2SC([Si](C)(C)C)=CC=2CC1C1=CC=CC(Br)=C1 XHKQMNMOWLESNO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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
- 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 1
- UIRYHPCELAYYKQ-UHFFFAOYSA-N 5-phenyl-5-(trifluoromethyl)-4h-thieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 UIRYHPCELAYYKQ-UHFFFAOYSA-N 0.000 claims 1
- 208000000044 Amnesia Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 208000011990 Corticobasal Degeneration Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 206010036631 Presenile dementia Diseases 0.000 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 1
- 230000006984 memory degeneration Effects 0.000 claims 1
- 208000023060 memory loss Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- KMSJFRPNIYWPMV-UHFFFAOYSA-N n-[[1-amino-3-phenyl-3-(trifluoromethyl)-4h-isoquinolin-6-yl]methyl]acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C2=CC(CNC(=O)C)=CC=C2C(N)=NC1(C(F)(F)F)C1=CC=CC=C1 KMSJFRPNIYWPMV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73732705P | 2005-11-15 | 2005-11-15 | |
| PCT/SE2006/001283 WO2007058583A2 (en) | 2005-11-15 | 2006-11-13 | Novel 2-amino-heterocycles useful in the treatment of abeta-related pathologies |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009520685A JP2009520685A (ja) | 2009-05-28 |
| JP2009520685A5 true JP2009520685A5 (https=) | 2010-01-07 |
Family
ID=38049090
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008541110A Pending JP2009520685A (ja) | 2005-11-15 | 2006-11-13 | 化合物およびそれらの使用ｉｖ |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080293709A1 (https=) |
| EP (1) | EP1957462A4 (https=) |
| JP (1) | JP2009520685A (https=) |
| KR (1) | KR20080070744A (https=) |
| CN (1) | CN101360714A (https=) |
| AR (1) | AR056217A1 (https=) |
| AU (1) | AU2006316256A1 (https=) |
| BR (1) | BRPI0618607A2 (https=) |
| CA (1) | CA2629831A1 (https=) |
| IL (1) | IL191057A0 (https=) |
| NO (1) | NO20082481L (https=) |
| TW (1) | TW200804290A (https=) |
| UY (1) | UY29919A1 (https=) |
| WO (1) | WO2007058583A2 (https=) |
| ZA (1) | ZA200803859B (https=) |
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| US7592348B2 (en) | 2003-12-15 | 2009-09-22 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7763609B2 (en) | 2003-12-15 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| RU2008100164A (ru) | 2005-06-14 | 2009-07-20 | Шеринг Корпорейшн (US) | Получение и применение соединений в качестве ингибиторов протеаз |
| MX2007016180A (es) | 2005-06-14 | 2008-03-07 | Schering Corp | Inhibidores de aspartil proteasas. |
| RU2416603C9 (ru) | 2005-10-25 | 2012-06-20 | Сионоги Энд Ко., Лтд. | Производные аминодигидротиазина |
| TW200815349A (en) | 2006-06-22 | 2008-04-01 | Astrazeneca Ab | New compounds |
| EP2151435A4 (en) | 2007-04-24 | 2011-09-14 | Shionogi & Co | PHARMACEUTICAL COMPOSITION FOR THE TREATMENT OF ALZHEIMER'S DISEASE |
| EP2147914B1 (en) | 2007-04-24 | 2014-06-04 | Shionogi&Co., Ltd. | Aminodihydrothiazine derivatives substituted with cyclic groups |
| KR20100059919A (ko) | 2007-09-24 | 2010-06-04 | 코멘티스, 인코포레이티드 | 치료를 위한 베타-세크레타제 억제제로서 (3-히드록시-4-아미노-부탄-2일)-3-(2-티아졸-2-일-피롤리딘-1-카르보닐) 벤즈아미드 유도체 및 관련 화합물 |
| JP2011507909A (ja) * | 2007-12-20 | 2011-03-10 | エンビボ ファーマシューティカルズ インコーポレイテッド | 四置換ベンゼン |
| WO2009151098A1 (ja) | 2008-06-13 | 2009-12-17 | 塩野義製薬株式会社 | βセクレターゼ阻害作用を有する含硫黄複素環誘導体 |
| WO2010042796A1 (en) | 2008-10-10 | 2010-04-15 | Purdue Research Foundation | Compounds for treatment of alzheimer's disease |
| CN102186841A (zh) | 2008-10-22 | 2011-09-14 | 盐野义制药株式会社 | 具有bace1抑制活性的2-氨基嘧啶-4-酮及2-氨基吡啶衍生物 |
| TW201020244A (en) | 2008-11-14 | 2010-06-01 | Astrazeneca Ab | New compounds |
| US8394807B2 (en) | 2008-11-20 | 2013-03-12 | Purdue Research Foundation | Quinazoline inhibitors of BACE 1 and methods of using |
| WO2010065861A2 (en) | 2008-12-05 | 2010-06-10 | Purdue Research Foundation | Inhibitors of bace 1 and methods for treating alzheimer's disease |
| US8952034B2 (en) | 2009-07-27 | 2015-02-10 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| UA108363C2 (uk) | 2009-10-08 | 2015-04-27 | Похідні імінотіадіазиндіоксиду як інгібітори bace, композиція на їх основі і їх застосування | |
| TWI488852B (zh) | 2009-12-11 | 2015-06-21 | Shionogi & Co | 衍生物 |
| US20120258961A1 (en) | 2009-12-24 | 2012-10-11 | Shionogi & Co., Ltd. | 4-amino-1,3-thiazine or oxazine derivative |
| KR101730937B1 (ko) | 2010-06-09 | 2017-04-27 | 얀센 파마슈티카 엔.브이. | 베타-세크레타아제(ｂａｃｅ) 저해제로 유용한 5,6-디하이드로-2ｈ-[1,4]옥사진-3-일-아민 유도체 |
| BR112012033402A2 (pt) | 2010-07-02 | 2017-01-24 | Gilead Sciences Inc | moduladores de canais de íons conforme os compostos heterocíclicos fundidos |
| US8609660B2 (en) * | 2010-09-22 | 2013-12-17 | Janssen Pharmaceutica Nv | 4,7-dihydro-pyrazolo[1,5-a]pyrazin-6-ylamine derivatives useful as inhibitors of beta-secretase (BACE) |
| JP5816630B2 (ja) * | 2010-10-29 | 2015-11-18 | 塩野義製薬株式会社 | ナフチリジン誘導体 |
| JP5766198B2 (ja) * | 2010-10-29 | 2015-08-19 | 塩野義製薬株式会社 | 縮合アミノジヒドロピリミジン誘導体 |
| SG191097A1 (en) | 2010-12-22 | 2013-08-30 | Janssen Pharmaceutica Nv | 5,6-DIHYDRO-IMIDAZO[1,2-a]PYRAZIN-8-YLAMINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE) |
| JP5853033B2 (ja) | 2011-03-01 | 2016-02-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | β−セクレターゼ（ＢＡＣＥ）の阻害剤として有用な６，７−ジヒドロ−ピラゾロ［１，５−ａ］ピラジン−４−イルアミン誘導体 |
| EP2683721B1 (en) | 2011-03-09 | 2015-01-28 | Janssen Pharmaceutica N.V. | 3,4-DIHYDRO-PYRROLO[1,2-a]PYRAZIN-1-YLAMINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE) |
| EP2694489B1 (en) | 2011-04-07 | 2017-09-06 | Merck Sharp & Dohme Corp. | C5-c6 oxacyclic-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| EP2694521B1 (en) | 2011-04-07 | 2015-11-25 | Merck Sharp & Dohme Corp. | Pyrrolidine-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use |
| TW201247635A (en) | 2011-04-26 | 2012-12-01 | Shionogi & Co | Oxazine derivatives and a pharmaceutical composition for inhibiting BAC1 containing them |
| CA2834164A1 (en) | 2011-05-10 | 2012-11-15 | Gilead Sciences, Inc. | Fused benzoxazinones as ion channel modulators |
| NO3175985T3 (https=) | 2011-07-01 | 2018-04-28 | ||
| TW201837023A (zh) | 2011-07-01 | 2018-10-16 | 美商基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| RU2014111055A (ru) | 2011-08-22 | 2015-09-27 | Мерк Шарп И Доум Корп. | 2-спирозамещенные иминотиазины и их моно- и диоксиды в качестве ингибиторов bace, композиции и их применение |
| EP2912035A4 (en) | 2012-10-24 | 2016-06-15 | Shionogi & Co | DERIVATIVES OF DIHYDROOXAZINE OR OXAZEPINE HAVING BACE1 INHIBITING ACTIVITY |
| CA2912156C (en) | 2013-06-12 | 2021-07-20 | Janssen Pharmaceutica Nv | 4-amino-6-phenyl-5,6-dihydroimidazo[1,5-a]pyrazin-3(2h)-one derivatives as inhibitors of beta-secretase (bace) |
| WO2014198854A1 (en) | 2013-06-12 | 2014-12-18 | Janssen Pharmaceutica Nv | 4-amino-6-phenyl-6,7-dihydro[1,2,3]triazolo[1,5-a]pyrazine derivatives as inhibitors of beta-secretase (bace) |
| KR102243134B1 (ko) | 2013-06-12 | 2021-04-22 | 얀센 파마슈티카 엔.브이. | 베타-세크레타제(bace) 저해제로서의 4-아미노-6-페닐-5,6-디하이드로이미다조[1,5-a]피라진 유도체 |
| MX2017008083A (es) | 2014-12-18 | 2017-10-31 | Janssen Pharmaceutica Nv | Compuestos 2,3,4,5-tetrahidropiridin-6-amina y 3,4-dihidro-2h-pirrol-5-amina inhibidores de beta-secretasa. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4515696A (en) * | 1994-12-12 | 1996-07-03 | Merck & Co., Inc. | Substituted 2-aminopyridines as inhibitors of nitric oxide synthase |
| NZ319673A (en) * | 1995-10-17 | 2000-06-23 | Astra Pharma Prod | Quinazoline compounds for inflammatory disorders such rheumatoid arthritis or osteoarthritis |
| US6063789A (en) * | 1996-04-13 | 2000-05-16 | Astra Pharmaceuticals, Ltd. | Aminoisoquinolines and aminotheinopyridine derivatives and their use as anti-inflammatory agents |
| DE60236322D1 (de) * | 2001-12-07 | 2010-06-17 | Vertex Pharma | Verbindungen auf pyrimidin-basis als gsk-3-hemmer |
| CA2609562A1 (en) * | 2005-06-14 | 2006-12-28 | Schering Corporation | Macrocyclic heterocyclic aspartyl protease inhibitors |
-
2006
- 2006-11-08 TW TW095141352A patent/TW200804290A/zh unknown
- 2006-11-13 CN CNA2006800511195A patent/CN101360714A/zh active Pending
- 2006-11-13 US US12/093,631 patent/US20080293709A1/en not_active Abandoned
- 2006-11-13 AU AU2006316256A patent/AU2006316256A1/en not_active Abandoned
- 2006-11-13 WO PCT/SE2006/001283 patent/WO2007058583A2/en not_active Ceased
- 2006-11-13 KR KR1020087014418A patent/KR20080070744A/ko not_active Withdrawn
- 2006-11-13 JP JP2008541110A patent/JP2009520685A/ja active Pending
- 2006-11-13 EP EP06813006A patent/EP1957462A4/en not_active Withdrawn
- 2006-11-13 BR BRPI0618607-6A patent/BRPI0618607A2/pt not_active IP Right Cessation
- 2006-11-13 CA CA002629831A patent/CA2629831A1/en not_active Abandoned
- 2006-11-13 AR ARP060104956A patent/AR056217A1/es not_active Application Discontinuation
- 2006-11-14 UY UY29919A patent/UY29919A1/es not_active Application Discontinuation
-
2008
- 2008-04-27 IL IL191057A patent/IL191057A0/en unknown
- 2008-05-06 ZA ZA200803859A patent/ZA200803859B/xx unknown
- 2008-06-03 NO NO20082481A patent/NO20082481L/no not_active Application Discontinuation
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