JP2014504300A5 - - Google Patents
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- Publication number
- JP2014504300A5 JP2014504300A5 JP2013546075A JP2013546075A JP2014504300A5 JP 2014504300 A5 JP2014504300 A5 JP 2014504300A5 JP 2013546075 A JP2013546075 A JP 2013546075A JP 2013546075 A JP2013546075 A JP 2013546075A JP 2014504300 A5 JP2014504300 A5 JP 2014504300A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- imidazole
- indene
- dispiro
- amine
- 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.)
- Granted
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 62
- 125000000217 alkyl group Chemical group 0.000 claims 54
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 25
- 150000002367 halogens Chemical class 0.000 claims 25
- 125000001072 heteroaryl group Chemical group 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 21
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 12
- -1 OR 8 Chemical group 0.000 claims 11
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 9
- 125000001188 haloalkyl group Chemical group 0.000 claims 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 7
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 7
- 208000024827 Alzheimer disease Diseases 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- XCUAIINAJCDIPM-XVFCMESISA-N N(4)-hydroxycytidine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=NO)C=C1 XCUAIINAJCDIPM-XVFCMESISA-N 0.000 claims 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 4
- 206010012289 Dementia Diseases 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 230000007170 pathology Effects 0.000 claims 3
- 125000003367 polycyclic group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- NNEAKBWZBQOQDH-UHFFFAOYSA-N 3-(1h-inden-2-yl)pyridine Chemical compound C=1C2=CC=CC=C2CC=1C1=CC=CN=C1 NNEAKBWZBQOQDH-UHFFFAOYSA-N 0.000 claims 1
- XSQKUWZLKKUZPU-UHFFFAOYSA-N 3-(4''-amino-5''-methyl-3'h-dispiro[cyclopropane-1,2'-indene-1',2''-imidazol]-6'-yl)-5-chlorobenzonitrile Chemical compound N1=C(N)C(C)=NC21C1(CC1)CC1=CC=C(C=3C=C(C=C(Cl)C=3)C#N)C=C12 XSQKUWZLKKUZPU-UHFFFAOYSA-N 0.000 claims 1
- VOAYXBVNQZNDJQ-UHFFFAOYSA-N 4-methoxy-5''-methyl-6'-[4-methyl-5-(prop-1-yn-1-yl)pyridin-3-yl]-3'h-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C(=C(C#CC)C=NC=3)C)=CC=C2C1 VOAYXBVNQZNDJQ-UHFFFAOYSA-N 0.000 claims 1
- AMESWUXBYLEHJV-UHFFFAOYSA-N 6'-(3-chloro-4-fluorophenyl)-5-methyl-5'',6''-dihydro-4''h-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C(F)=CC=3)=CC=C2OC2(COCCC2)C1 AMESWUXBYLEHJV-UHFFFAOYSA-N 0.000 claims 1
- NDUICAHCFCQKCR-UHFFFAOYSA-N 6'-(3-chlorophenyl)-5-methyl-5'',6''-dihydro-4''h-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=CC=3)=CC=C2OC2(COCCC2)C1 NDUICAHCFCQKCR-UHFFFAOYSA-N 0.000 claims 1
- MKLSHCVZEOAEFB-UHFFFAOYSA-N 6'-(5-chloropyridin-3-yl)-5''-methyl-3'h-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical class N1=C(N)C(C)=NC21C1(CCC1)CC1=CC=C(C=3C=C(Cl)C=NC=3)C=C12 MKLSHCVZEOAEFB-UHFFFAOYSA-N 0.000 claims 1
- UAEMPXBCTYCXDD-UHFFFAOYSA-N 6'-(cyclopropylethynyl)-5''-methyl-3'h-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound N1=C(N)C(C)=NC21C1(CCC1)CC1=CC=C(C#CC3CC3)C=C12 UAEMPXBCTYCXDD-UHFFFAOYSA-N 0.000 claims 1
- SEMLTECGFLAMPC-UHFFFAOYSA-N 6'-bromo-4-(difluoromethyl)-5''-methyl-3'h-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound N1=C(N)C(C)=NC21C1(CCC(CC1)C(F)F)CC1=CC=C(Br)C=C12 SEMLTECGFLAMPC-UHFFFAOYSA-N 0.000 claims 1
- NYMXIKPEDWDOQL-UHFFFAOYSA-N 6'-bromo-4-methoxy-5''-methyl-3'h-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(Br)=CC=C2C1 NYMXIKPEDWDOQL-UHFFFAOYSA-N 0.000 claims 1
- VPPGDUMXGIDOQT-UHFFFAOYSA-N 6'-bromo-5''-methyl-3'h-dispiro[cyclobutane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound N1=C(N)C(C)=NC21C1(CCC1)CC1=CC=C(Br)C=C12 VPPGDUMXGIDOQT-UHFFFAOYSA-N 0.000 claims 1
- DFCZJGXXKNWQJL-UHFFFAOYSA-N 6'-bromo-5''-methyl-3'h-dispiro[cyclopropane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound N1=C(N)C(C)=NC21C1(CC1)CC1=CC=C(Br)C=C12 DFCZJGXXKNWQJL-UHFFFAOYSA-N 0.000 claims 1
- NTHHXIKGFGHHJO-UHFFFAOYSA-N 6'-bromo-5''-methyl-4-(trifluoromethyl)-3'h-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine Chemical compound N1=C(N)C(C)=NC21C1(CCC(CC1)C(F)(F)F)CC1=CC=C(Br)C=C12 NTHHXIKGFGHHJO-UHFFFAOYSA-N 0.000 claims 1
- OQJQQWGZYQBQJI-UHFFFAOYSA-N 6'-bromo-5-methyl-2'',3'',5'',6''-tetrahydro-3'h-dispiro[imidazole-2,1'-indene-2',4''-pyran]-4-amine Chemical compound N1=C(N)C(C)=NC21C1(CCOCC1)CC1=CC=C(Br)C=C12 OQJQQWGZYQBQJI-UHFFFAOYSA-N 0.000 claims 1
- IDOTUYBHWAHCGP-UHFFFAOYSA-N 6'-bromo-5-methyl-5'',6''-dihydro-4''h-dispiro[imidazole-2,4'-chromene-2',3''-pyran]-4-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(Br)=CC=C2OC2(COCCC2)C1 IDOTUYBHWAHCGP-UHFFFAOYSA-N 0.000 claims 1
- NMPGDLCHDFBBBC-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C(=C(F)C=CC=3)F)=CC=C2OCC1 NMPGDLCHDFBBBC-UHFFFAOYSA-N 0.000 claims 1
- OOCXJKMXIADCPK-UHFFFAOYSA-N 6-(2,5-dimethoxyphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound COC1=CC=C(OC)C(C=2C=C3C4(N=C(N)C(C)=N4)CCOC3=CC=2)=C1 OOCXJKMXIADCPK-UHFFFAOYSA-N 0.000 claims 1
- ASTARQOFIHHADR-UHFFFAOYSA-N 6-(2,5-dimethylphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C(=CC=C(C)C=3)C)=CC=C2OCC1 ASTARQOFIHHADR-UHFFFAOYSA-N 0.000 claims 1
- HZUBJQJZQJTUIS-UHFFFAOYSA-N 6-(2-fluoro-3-methoxyphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound COC1=CC=CC(C=2C=C3C4(N=C(N)C(C)=N4)CCOC3=CC=2)=C1F HZUBJQJZQJTUIS-UHFFFAOYSA-N 0.000 claims 1
- RSJMUFIUQMEIDV-UHFFFAOYSA-N 6-(2-fluoro-5-methoxyphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound COC1=CC=C(F)C(C=2C=C3C4(N=C(N)C(C)=N4)CCOC3=CC=2)=C1 RSJMUFIUQMEIDV-UHFFFAOYSA-N 0.000 claims 1
- MJCNDWZEGNXOEP-UHFFFAOYSA-N 6-(2-fluoro-5-methylphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C(=CC=C(C)C=3)F)=CC=C2OCC1 MJCNDWZEGNXOEP-UHFFFAOYSA-N 0.000 claims 1
- SVICWOABALJMFD-UHFFFAOYSA-N 6-(2-methoxy-5-methylphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound COC1=CC=C(C)C=C1C1=CC=C(OCCC23N=C(N)C(C)=N3)C2=C1 SVICWOABALJMFD-UHFFFAOYSA-N 0.000 claims 1
- BTQYJGMMVLMRIM-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=C(Cl)C=3)=CC=C2OCC1 BTQYJGMMVLMRIM-UHFFFAOYSA-N 0.000 claims 1
- XPBCXYLXDCQPPG-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(F)C=C(F)C=3)=CC=C2OCC1 XPBCXYLXDCQPPG-UHFFFAOYSA-N 0.000 claims 1
- XVHSHDMIBQAYGQ-UHFFFAOYSA-N 6-(3,5-dimethylphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(C)C=C(C)C=3)=CC=C2OCC1 XVHSHDMIBQAYGQ-UHFFFAOYSA-N 0.000 claims 1
- PNGMSULGCSIWPT-UHFFFAOYSA-N 6-(3-chlorophenyl)-2-(2,2-dimethyloxan-4-yl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=CC=3)=CC=C2OC(C2CC(C)(C)OCC2)C1 PNGMSULGCSIWPT-UHFFFAOYSA-N 0.000 claims 1
- MWVBEWBNSOHPSD-UHFFFAOYSA-N 6-(3-chlorophenyl)-5'-methyl-2-(oxan-3-yl)spiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=CC=3)=CC=C2OC(C2COCCC2)C1 MWVBEWBNSOHPSD-UHFFFAOYSA-N 0.000 claims 1
- ULLKDRHZBXMQBC-UHFFFAOYSA-N 6-(5-chloropyridin-3-yl)-5'-methylspiro[2,3-dihydro-1h-naphthalene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=NC=3)=CC=C2CCC1 ULLKDRHZBXMQBC-UHFFFAOYSA-N 0.000 claims 1
- XNFNZERRRUIVBJ-UHFFFAOYSA-N 6-(5-chloropyridin-3-yl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(C=3C=C(Cl)C=NC=3)=CC=C2OCC1 XNFNZERRRUIVBJ-UHFFFAOYSA-N 0.000 claims 1
- PVASJWZFVWATEB-UHFFFAOYSA-N 6-(5-fluoro-2-methoxyphenyl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound COC1=CC=C(F)C=C1C1=CC=C(OCCC23N=C(N)C(C)=N3)C2=C1 PVASJWZFVWATEB-UHFFFAOYSA-N 0.000 claims 1
- IBGZXUPONLUVLS-UHFFFAOYSA-N 6-bromo-2-(2,2-dimethyloxan-4-yl)-5'-methylspiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(Br)=CC=C2OC(C2CC(C)(C)OCC2)C1 IBGZXUPONLUVLS-UHFFFAOYSA-N 0.000 claims 1
- ONKRKKQEVGYQDK-UHFFFAOYSA-N 6-bromo-5'-methyl-2-(oxan-3-yl)spiro[2,3-dihydrochromene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(Br)=CC=C2OC(C2COCCC2)C1 ONKRKKQEVGYQDK-UHFFFAOYSA-N 0.000 claims 1
- QNHHDQXBRHSEHK-UHFFFAOYSA-N 6-bromo-5'-methylspiro[2,3-dihydro-1h-naphthalene-4,2'-imidazole]-4'-amine Chemical compound N1=C(N)C(C)=NC11C2=CC(Br)=CC=C2CCC1 QNHHDQXBRHSEHK-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
- 206010059245 Angiopathy Diseases 0.000 claims 1
- PJFLXADHRCSJTF-UHFFFAOYSA-N C1CC(OC)(C)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C=NC=3)C#CC)=CC=C2C1 Chemical compound C1CC(OC)(C)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C=NC=3)C#CC)=CC=C2C1 PJFLXADHRCSJTF-UHFFFAOYSA-N 0.000 claims 1
- IBJMVRAGTMDAFC-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C#N)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C#N)=CC=C2C1 IBJMVRAGTMDAFC-UHFFFAOYSA-N 0.000 claims 1
- MUPBWXCOUHZWEH-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C(=C(OC)C=CC=3)F)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C(=C(OC)C=CC=3)F)=CC=C2C1 MUPBWXCOUHZWEH-UHFFFAOYSA-N 0.000 claims 1
- JJDMMVKGGCIWNE-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C(=CC=C(OC)C=3)F)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C(=CC=C(OC)C=3)F)=CC=C2C1 JJDMMVKGGCIWNE-UHFFFAOYSA-N 0.000 claims 1
- UMCUVZSSUIPNCL-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(Br)C=NC=3)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(Br)C=NC=3)=CC=C2C1 UMCUVZSSUIPNCL-UHFFFAOYSA-N 0.000 claims 1
- JXMIZSIVCHFRDW-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C)C=NC=3)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C)C=NC=3)=CC=C2C1 JXMIZSIVCHFRDW-UHFFFAOYSA-N 0.000 claims 1
- YNWCSWFGCSURHN-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C=CC=3)C#CC)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(C=CC=3)C#CC)=CC=C2C1 YNWCSWFGCSURHN-UHFFFAOYSA-N 0.000 claims 1
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- RJIJEEIOHDLRFZ-UHFFFAOYSA-N C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C4C(C)=CNC4=CC=3)=CC=C2C1 Chemical compound C1CC(OC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C4C(C)=CNC4=CC=3)=CC=C2C1 RJIJEEIOHDLRFZ-UHFFFAOYSA-N 0.000 claims 1
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- GOOGDNLQKOSOJY-UHFFFAOYSA-N C1CC(OCC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(Cl)C=NC=3)=CC=C2C1 Chemical compound C1CC(OCC)CCC11C2(N=C(N)C(C)=N2)C2=CC(C=3C=C(Cl)C=NC=3)=CC=C2C1 GOOGDNLQKOSOJY-UHFFFAOYSA-N 0.000 claims 1
- FBRMBFBHYONUMR-UHFFFAOYSA-N C1CCC2(CC1)C3(C4=CC=CC=C4O2)N=CC(=N3)N Chemical compound C1CCC2(CC1)C3(C4=CC=CC=C4O2)N=CC(=N3)N FBRMBFBHYONUMR-UHFFFAOYSA-N 0.000 claims 1
- LJSQZUIHVXHZEP-UHFFFAOYSA-N CC=1C=NC2(CCCC3=CC=C(C=C23)C=2C=NC=C(C2)C#CC)N1 Chemical compound CC=1C=NC2(CCCC3=CC=C(C=C23)C=2C=NC=C(C2)C#CC)N1 LJSQZUIHVXHZEP-UHFFFAOYSA-N 0.000 claims 1
- OJULZIHGKOEUGD-UHFFFAOYSA-N COCC1=CC=CC(C=2C=C3C4(N=C(N)C(C)=N4)C4(CCC(CC4)OC)CC3=CC=2)=C1 Chemical compound COCC1=CC=CC(C=2C=C3C4(N=C(N)C(C)=N4)C4(CCC(CC4)OC)CC3=CC=2)=C1 OJULZIHGKOEUGD-UHFFFAOYSA-N 0.000 claims 1
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 229940122041 Cholinesterase inhibitor Drugs 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US8779355B2 (en) * | 2011-12-28 | 2014-07-15 | Quest Diagnostics Investments, Inc. | Methods for detecting lacosamide by mass spectrometry |
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| TW201422592A (zh) | 2012-08-27 | 2014-06-16 | Boehringer Ingelheim Int | β－分泌酶抑制劑 |
| EP2900650A1 (en) * | 2012-09-28 | 2015-08-05 | Vitae Pharmaceuticals, Inc. | Inhibitors of beta-secretase |
| CN104995176B (zh) | 2013-02-12 | 2019-02-22 | 巴克老龄化研究所 | 调节bace所介导的app加工的乙内酰脲 |
| AR102202A1 (es) | 2014-10-07 | 2017-02-08 | Astrazeneca Ab | Compuestos de oxazol y su uso como inhibidores de bace de oxazol |
| AU2017232277A1 (en) | 2016-03-15 | 2018-10-04 | Astrazeneca Ab | Combination of a BACE inhibitor and an antibody or antigen-binding fragment for the treatment of a disorder associated with the accumulation of amyloid beta |
| TW201740944A (zh) | 2016-03-15 | 2017-12-01 | 美國禮來大藥廠 | 組合療法 |
| JPWO2017169503A1 (ja) * | 2016-04-01 | 2019-02-14 | 国立大学法人千葉大学 | 含窒素芳香族アミドの製造方法、ピロール・イミダゾールポリアミドの製造方法、及び化合物 |
| CN107892697B (zh) | 2016-12-26 | 2020-11-03 | 郑州泰基鸿诺医药股份有限公司 | 一种[1,3]噻嗪-2-胺类化合物及应用，药物组合物 |
| CN107954927A (zh) * | 2017-10-30 | 2018-04-24 | 广东莱佛士制药技术有限公司 | 一种3-溴-5-(丙炔-1-基)吡啶的制备方法 |
| WO2019122268A1 (en) | 2017-12-21 | 2019-06-27 | Astrazeneca Ab | Processes for the stereoselective preparation of bace inhibitors |
| WO2019122421A1 (en) | 2017-12-22 | 2019-06-27 | Astrazeneca Ab | Stereoselective ketone reduction using a ketoreductase enzyme |
| WO2019129755A1 (en) | 2017-12-29 | 2019-07-04 | Astrazeneca Ab | Ketal hydrogenation |
| WO2019129750A1 (en) | 2017-12-29 | 2019-07-04 | Astrazeneca Ab | Processes for the racemization of dihydroimidazole ring systems |
| CN110615751B (zh) * | 2018-06-19 | 2021-08-17 | 上海医药工业研究院 | 一种2-氧代硫代丙酰胺的制备方法 |
| US20220175749A1 (en) * | 2019-03-14 | 2022-06-09 | Astrazeneca Ab | Lanabecestat for weight loss |
| CN111253427A (zh) * | 2020-03-13 | 2020-06-09 | 苏州大学 | 正丁基锂在催化醛和硅烷的氰硅化反应中的应用 |
| CN114989103B (zh) * | 2022-06-09 | 2024-07-09 | 杭州科巢生物科技有限公司 | 一种2-甲氧基-3-(1-甲基-1h-1,2,4-三唑-3-基)苯胺的制备方法 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100452491B1 (ko) | 2001-03-29 | 2004-10-12 | 한미약품 주식회사 | 신규한 결정형 암로디핀 캠실레이트 염 및 그의 제조방법 |
| WO2002098462A1 (en) * | 2001-06-01 | 2002-12-12 | Ono Pharmaceutical Co., Ltd. | Remedies containing aldose reductase inhibitor as the active ingredient for demyelinating diseases or diseases associated with demyelination |
| US7592348B2 (en) * | 2003-12-15 | 2009-09-22 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| EP1729771B1 (en) | 2004-03-22 | 2009-10-14 | Eli Lilly & Company | Pyridyl derivatives and their use as mglu5 receptor antagonists |
| CA2609582A1 (en) | 2005-06-14 | 2006-12-28 | Schering Corporation | Aspartyl protease inhibitors |
| WO2007058601A1 (en) | 2005-11-21 | 2007-05-24 | Astrazeneca Ab | Novel 2-amino-imidazole-4-one compounds and their use in the manufacture of a medicament to be used in the treatment of cognitive impairment, alzheimer’s disease, neurodegeneration and dementia |
| WO2007076247A1 (en) | 2005-12-21 | 2007-07-05 | Boehringer Ingelheim International Gmbh | Pyrimidine derivatives useful as inhibitors of pkc-theta |
| WO2007100536A1 (en) | 2006-02-24 | 2007-09-07 | Wyeth | DIHYDROSPIRO[DIBENZO[A,D][7]ANNULENE-5,4'-IMIDAZOL] COMPOUNDS FOR THE INHIBITION OF β-SECRETASE |
| CN101506162B (zh) * | 2006-06-22 | 2012-06-27 | 阿斯利康(瑞典)有限公司 | 作为β位淀粉样前体蛋白裂解酶抑制剂的取代的异吲哚和它们的用途 |
| WO2008076044A1 (en) * | 2006-12-20 | 2008-06-26 | Astrazeneca Ab | Novel 2-amino-5, 5-diaryl-imidazol-4-ones |
| WO2008092877A2 (en) * | 2007-02-01 | 2008-08-07 | Glaxo Group Limited | 8-oxa-1, 4-diazaspiro [4,5] dec-3-en-1-yl and 1,4, 8-triazaspiro [4,5] dec- 3-en-1-yl acetamides as glyti transporter inhibitors in treatment of neurological and neuropsychiatric disorders |
| MX2009012177A (es) * | 2007-05-07 | 2009-11-23 | Schering Corp | Moduladores de gamma-secretasa. |
| EP2249646A4 (en) | 2008-02-06 | 2013-09-25 | Glaxo Group Ltd | PDE4 muscarinic Antagonist-DOPPELPHARMACOPHOREN |
| FR2929943B1 (fr) | 2008-04-15 | 2010-09-24 | Inst Rech Developpement Ird | Sels de quinoleines 2-substituees |
| KR20110048491A (ko) | 2008-07-28 | 2011-05-11 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 스피로아미노디하이드로티아진 유도체들 |
| US8450308B2 (en) | 2008-08-19 | 2013-05-28 | Vitae Pharmaceuticals, Inc. | Inhibitors of beta-secretase |
| MX2011002705A (es) | 2008-09-11 | 2011-09-09 | Amgen Inc | Compuestos con anillos espiro-triciclicos como moduladores de beta-secretasas y metodos de uso. |
| KR101908255B1 (ko) | 2009-03-13 | 2018-10-15 | 비타이 파마슈티컬즈, 인코포레이티드 | 베타세크리타아제 저해제 |
| TW201105650A (en) | 2009-07-02 | 2011-02-16 | Astrazeneca Ab | New compounds |
| UY32750A (es) | 2009-07-02 | 2011-01-31 | Astrazeneca Ab | Imidazoles sustituidos y uso de los mismos |
| JP5828848B2 (ja) | 2010-02-24 | 2015-12-09 | ヴァイティー ファーマシューティカルズ，インコーポレイテッド | ベータセクレターゼインヒビター |
| US20120065195A1 (en) | 2010-03-31 | 2012-03-15 | Clark Christopher T | Compounds for treating neurodegenerative diseases |
| WO2011130741A1 (en) | 2010-04-16 | 2011-10-20 | Array Biopharma Inc. | Compounds for treating neurodegenerative diseases |
| US8921363B2 (en) | 2010-08-05 | 2014-12-30 | Amgen Inc. | Derivatives of 1 H-isoindol-3-amine, 1 H-iso-aza-indol-3amine, 3,4-dihydroisoquinolin-1-amine, and 1,4-dihydroisoquinolin-3-amine as beta-secretase inhibitors |
| WO2012040641A2 (en) | 2010-09-24 | 2012-03-29 | Array Biopharma Inc. | Compounds for treating neurodegenerative diseases |
| AR083953A1 (es) | 2010-11-22 | 2013-04-10 | Array Biopharma Inc | Compuestos para tratar enfermedades neurodegenerativas |
| US8415483B2 (en) * | 2010-12-22 | 2013-04-09 | Astrazeneca Ab | Compounds and their use as BACE inhibitors |
| US9650336B2 (en) | 2011-10-10 | 2017-05-16 | Astrazeneca Ab | Mono-fluoro beta-secretase inhibitors |
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| US10548882B2 (en) | 2012-06-21 | 2020-02-04 | Astrazeneca Ab | Camsylate salt |
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- 2013-06-20 GT GT201300165A patent/GT201300165A/es unknown
- 2013-06-20 NI NI201300055A patent/NI201300055A/es unknown
- 2013-06-20 DO DO2013000147A patent/DOP2013000147A/es unknown
- 2013-06-21 CR CR20130308A patent/CR20130308A/es unknown
- 2013-06-21 EC ECSP13012708 patent/ECSP13012708A/es unknown
- 2013-06-21 CL CL2013001849A patent/CL2013001849A1/es unknown
- 2013-06-21 CO CO13148240A patent/CO6781485A2/es active IP Right Grant
- 2013-07-19 ZA ZA2013/05495A patent/ZA201305495B/en unknown
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2014
- 2014-09-15 US US14/486,959 patent/US9248129B2/en not_active Expired - Fee Related
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2015
- 2015-12-22 US US14/978,756 patent/US20160184303A1/en not_active Abandoned
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2016
- 2016-01-29 AU AU2016200538A patent/AU2016200538B2/en not_active Ceased
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- 2016-07-29 JP JP2016149234A patent/JP6333317B2/ja active Active
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2017
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- 2017-07-26 US US15/659,816 patent/US9918985B2/en active Active
- 2017-11-14 AU AU2017261475A patent/AU2017261475A1/en not_active Abandoned
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2018
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- 2018-01-31 US US15/884,752 patent/US10231967B2/en not_active Expired - Fee Related
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