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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- 2013-06-21 EC ECSP13012708 patent/ECSP13012708A/es unknown
- 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
- 2016-07-25 DO DO2016000191A patent/DOP2016000191A/es unknown
- 2016-07-29 JP JP2016149234A patent/JP6333317B2/ja active Active
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2017
- 2017-01-31 DO DO2017000030A patent/DOP2017000030A/es unknown
- 2017-05-31 CY CY20171100566T patent/CY1119211T1/el unknown
- 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
- 2018-01-26 JP JP2018011088A patent/JP6527255B2/ja not_active Expired - Fee Related
- 2018-01-31 US US15/884,752 patent/US10231967B2/en not_active Expired - Fee Related
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