JP2008516946A5 - - Google Patents
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- JP2008516946A5 JP2008516946A5 JP2007536656A JP2007536656A JP2008516946A5 JP 2008516946 A5 JP2008516946 A5 JP 2008516946A5 JP 2007536656 A JP2007536656 A JP 2007536656A JP 2007536656 A JP2007536656 A JP 2007536656A JP 2008516946 A5 JP2008516946 A5 JP 2008516946A5
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- JP
- Japan
- Prior art keywords
- amino
- alkyl
- ethyl
- dimethyl
- phenyl
- 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 158
- 125000003118 aryl group Chemical group 0.000 claims 62
- 125000000623 heterocyclic group Chemical group 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 34
- 238000001727 in vivo Methods 0.000 claims 21
- 239000002243 precursor Substances 0.000 claims 21
- 150000003839 salts Chemical class 0.000 claims 21
- -1 C (═O) H Chemical group 0.000 claims 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 208000024827 Alzheimer disease Diseases 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 8
- 206010012289 Dementia Diseases 0.000 claims 6
- 230000007170 pathology Effects 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 4
- 230000002265 prevention Effects 0.000 claims 4
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 3
- SIIBDWSCKNFHDU-UHFFFAOYSA-N 2-amino-3-methyl-6-[2-(3-thiophen-2-ylphenyl)ethyl]pyrimidin-4-one Chemical compound O=C1N(C)C(N)=NC(CCC=2C=C(C=CC=2)C=2SC=CC=2)=C1 SIIBDWSCKNFHDU-UHFFFAOYSA-N 0.000 claims 2
- VDFBMQAUECXNKR-UHFFFAOYSA-N 2-amino-6-[2-[3-(3-methoxyphenyl)phenyl]ethyl]-3,6-dimethyl-5h-pyrimidin-4-one Chemical compound COC1=CC=CC(C=2C=C(CCC3(C)N=C(N)N(C)C(=O)C3)C=CC=2)=C1 VDFBMQAUECXNKR-UHFFFAOYSA-N 0.000 claims 2
- FYAOKEFZAGKDCO-UHFFFAOYSA-N 2-amino-6-[2-[3-(furan-2-yl)phenyl]ethyl]-3-[2-[(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)amino]ethyl]pyrimidin-4-one Chemical compound C1C(C)(C)N(O)C(C)(C)CC1NCCN1C(=O)C=C(CCC=2C=C(C=CC=2)C=2OC=CC=2)N=C1N FYAOKEFZAGKDCO-UHFFFAOYSA-N 0.000 claims 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- XNLWJFYYOIRPIO-UHFFFAOYSA-N 3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 XNLWJFYYOIRPIO-UHFFFAOYSA-N 0.000 claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 2
- 206010059245 Angiopathy Diseases 0.000 claims 2
- 102100021257 Beta-secretase 1 Human genes 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 201000010374 Down Syndrome Diseases 0.000 claims 2
- 101000894895 Homo sapiens Beta-secretase 1 Proteins 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010036631 Presenile dementia Diseases 0.000 claims 2
- 206010039966 Senile dementia Diseases 0.000 claims 2
- 125000005466 alkylenyl group Chemical group 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000001054 cortical effect Effects 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 230000007850 degeneration Effects 0.000 claims 2
- 230000003412 degenerative effect Effects 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 206010027175 memory impairment Diseases 0.000 claims 2
- 208000027061 mild cognitive impairment Diseases 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 201000002212 progressive supranuclear palsy Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- VDFBMQAUECXNKR-OAQYLSRUSA-N (6r)-2-amino-6-[2-(3'-methoxybiphenyl-3-yl)ethyl]-3,6-dimethyl-5,6-dihydropyrimidin-4(3h)-one Chemical compound COC1=CC=CC(C=2C=C(CC[C@@]3(C)N=C(N)N(C)C(=O)C3)C=CC=2)=C1 VDFBMQAUECXNKR-OAQYLSRUSA-N 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- ADVKDZKKBVYRJF-UHFFFAOYSA-N 1-[2-[2-amino-4-[2-[3-(furan-2-yl)phenyl]ethyl]-6-oxopyrimidin-1-yl]ethyl]pyrrolidine-2,5-dione Chemical compound C=1C(=O)N(CCN2C(CCC2=O)=O)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 ADVKDZKKBVYRJF-UHFFFAOYSA-N 0.000 claims 1
- MPZXFSNOHMDCGM-UHFFFAOYSA-N 2-[2-[2-amino-4-[2-[3-(furan-2-yl)phenyl]ethyl]-6-oxopyrimidin-1-yl]ethylcarbamoyl]benzoic acid Chemical compound C=1C(=O)N(CCNC(=O)C=2C(=CC=CC=2)C(O)=O)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 MPZXFSNOHMDCGM-UHFFFAOYSA-N 0.000 claims 1
- ZHWYFHHFKMVBHE-UHFFFAOYSA-N 2-[3-(2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl)phenyl]benzaldehyde Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C(=CC=CC=2)C=O)=C1 ZHWYFHHFKMVBHE-UHFFFAOYSA-N 0.000 claims 1
- RVGNQDOIKMXHFJ-UHFFFAOYSA-N 2-[4-[3-[2-(2-amino-1-methyl-6-oxopyrimidin-4-yl)ethyl]phenyl]phenyl]acetonitrile Chemical compound O=C1N(C)C(N)=NC(CCC=2C=C(C=CC=2)C=2C=CC(CC#N)=CC=2)=C1 RVGNQDOIKMXHFJ-UHFFFAOYSA-N 0.000 claims 1
- NXTUSBJPYKPBPG-UHFFFAOYSA-N 2-[[2-amino-4-[2-[3-(furan-2-yl)phenyl]ethyl]-6-oxopyrimidin-1-yl]methyl]benzonitrile Chemical compound C=1C(=O)N(CC=2C(=CC=CC=2)C#N)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 NXTUSBJPYKPBPG-UHFFFAOYSA-N 0.000 claims 1
- MXAMSXRLYWZDKM-UHFFFAOYSA-N 2-amino-1-methyl-4-phenyl-4,5-dihydropyrimidin-6-one Chemical compound N1=C(N)N(C)C(=O)CC1C1=CC=CC=C1 MXAMSXRLYWZDKM-UHFFFAOYSA-N 0.000 claims 1
- NHJCZSSEYRWDOJ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(2-phenylethyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)CCC1=CC=CC=C1 NHJCZSSEYRWDOJ-UHFFFAOYSA-N 0.000 claims 1
- WYRYUPJXYGZYMQ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-naphthalen-1-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C3=CC=CC=C3C=CC=2)=C1 WYRYUPJXYGZYMQ-UHFFFAOYSA-N 0.000 claims 1
- CJCGUFPWXVYBOP-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-naphthalen-2-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=C3C=CC=CC3=CC=2)=C1 CJCGUFPWXVYBOP-UHFFFAOYSA-N 0.000 claims 1
- LLWQVDGSPOLZCX-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-phenylmethoxyphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(OCC=2C=CC=CC=2)=C1 LLWQVDGSPOLZCX-UHFFFAOYSA-N 0.000 claims 1
- JOISLKSETFBBHA-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-phenylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=CC=CC=2)=C1 JOISLKSETFBBHA-UHFFFAOYSA-N 0.000 claims 1
- UXSBRZQVDSXACZ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-pyridin-3-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=NC=CC=2)=C1 UXSBRZQVDSXACZ-UHFFFAOYSA-N 0.000 claims 1
- LOKQKXXEUIHEML-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-quinolin-5-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C3=CC=CN=C3C=CC=2)=C1 LOKQKXXEUIHEML-UHFFFAOYSA-N 0.000 claims 1
- XODWQPOSMCSFCW-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-thianthren-1-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=3SC4=CC=CC=C4SC=3C=CC=2)=C1 XODWQPOSMCSFCW-UHFFFAOYSA-N 0.000 claims 1
- OCWPZYGEUQDNRF-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-thiophen-2-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2SC=CC=2)=C1 OCWPZYGEUQDNRF-UHFFFAOYSA-N 0.000 claims 1
- KTXFMDPRNFUCLM-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-(3-thiophen-3-ylphenyl)-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C2=CSC=C2)=C1 KTXFMDPRNFUCLM-UHFFFAOYSA-N 0.000 claims 1
- CWIATWAMZSVNNY-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[2-(3-phenylphenyl)ethyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)CCC1=CC=CC(C=2C=CC=CC=2)=C1 CWIATWAMZSVNNY-UHFFFAOYSA-N 0.000 claims 1
- WIMXZMWLRDLYFX-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[2-[3-(4-methylsulfonylphenyl)phenyl]ethyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)CCC1=CC=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 WIMXZMWLRDLYFX-UHFFFAOYSA-N 0.000 claims 1
- JVPBWWGEKGIECR-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(1h-pyrazol-5-yl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C2=NNC=C2)=C1 JVPBWWGEKGIECR-UHFFFAOYSA-N 0.000 claims 1
- MYMUYIBICLFZEU-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(2,4,6-trimethylphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C(=CC(C)=CC=2C)C)=C1 MYMUYIBICLFZEU-UHFFFAOYSA-N 0.000 claims 1
- BLOQXMKUUCLYOZ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(2-phenoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C(=CC=CC=2)OC=2C=CC=CC=2)=C1 BLOQXMKUUCLYOZ-UHFFFAOYSA-N 0.000 claims 1
- JERASWJSJYHBTD-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(2-phenylmethoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=C1 JERASWJSJYHBTD-UHFFFAOYSA-N 0.000 claims 1
- DNLPBNLQGOCXHV-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3,4,5-trifluorophenyl)phenyl]-5h-pyrimidin-4-one Chemical compound C1C(=O)N(C)C(N)=NC1(C)C1=CC=CC(C=2C=C(F)C(F)=C(F)C=2)=C1 DNLPBNLQGOCXHV-UHFFFAOYSA-N 0.000 claims 1
- FRAOCQOLHIXTQV-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3,4,5-trimethoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C=CC=2)C2(C)N=C(N)N(C)C(=O)C2)=C1 FRAOCQOLHIXTQV-UHFFFAOYSA-N 0.000 claims 1
- ZQINEYPCAZXPIJ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3-phenylmethoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 ZQINEYPCAZXPIJ-UHFFFAOYSA-N 0.000 claims 1
- ZPJNACZKUZLHMZ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3-propan-2-yloxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound CC(C)OC1=CC=CC(C=2C=C(C=CC=2)C2(C)N=C(N)N(C)C(=O)C2)=C1 ZPJNACZKUZLHMZ-UHFFFAOYSA-N 0.000 claims 1
- OHTUIZFWOGWLGX-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3-propoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound CCCOC1=CC=CC(C=2C=C(C=CC=2)C2(C)N=C(N)N(C)C(=O)C2)=C1 OHTUIZFWOGWLGX-UHFFFAOYSA-N 0.000 claims 1
- NAIAHBIYZSKZBM-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(3-pyrazol-1-ylphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=C(C=CC=2)N2N=CC=C2)=C1 NAIAHBIYZSKZBM-UHFFFAOYSA-N 0.000 claims 1
- JJHCXFCAJLPZIQ-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-methylsulfonylphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=C1 JJHCXFCAJLPZIQ-UHFFFAOYSA-N 0.000 claims 1
- BYFFNCHVOCRLCE-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-phenoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=CC(OC=3C=CC=CC=3)=CC=2)=C1 BYFFNCHVOCRLCE-UHFFFAOYSA-N 0.000 claims 1
- RHBOESYJNWTMNO-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-phenylmethoxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 RHBOESYJNWTMNO-UHFFFAOYSA-N 0.000 claims 1
- HSOKMXIOOAJZID-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-propan-2-yloxyphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound C1=CC(OC(C)C)=CC=C1C1=CC=CC(C2(C)N=C(N)N(C)C(=O)C2)=C1 HSOKMXIOOAJZID-UHFFFAOYSA-N 0.000 claims 1
- JMGILWACKTWTEW-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-propylphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound C1=CC(CCC)=CC=C1C1=CC=CC(C2(C)N=C(N)N(C)C(=O)C2)=C1 JMGILWACKTWTEW-UHFFFAOYSA-N 0.000 claims 1
- CCGJDSDFNXBMTM-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(4-trimethylsilylphenyl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=CC(=CC=2)[Si](C)(C)C)=C1 CCGJDSDFNXBMTM-UHFFFAOYSA-N 0.000 claims 1
- OTJZDEZUWSQZLC-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-(5-methylthiophen-2-yl)phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2SC(C)=CC=2)=C1 OTJZDEZUWSQZLC-UHFFFAOYSA-N 0.000 claims 1
- KDPKTUDYRNMPMO-VAWYXSNFSA-N 2-amino-3,6-dimethyl-6-[3-[(e)-2-(4-phenylphenyl)ethenyl]phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(\C=C\C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 KDPKTUDYRNMPMO-VAWYXSNFSA-N 0.000 claims 1
- LEYREUVKBKVYEV-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[2-(morpholin-4-ylmethyl)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C(=CC=CC=2)CN2CCOCC2)=C1 LEYREUVKBKVYEV-UHFFFAOYSA-N 0.000 claims 1
- BWVYPUNCFWITBH-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[2-(trifluoromethyl)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound C1C(=O)N(C)C(N)=NC1(C)C1=CC=CC(C=2C(=CC=CC=2)C(F)(F)F)=C1 BWVYPUNCFWITBH-UHFFFAOYSA-N 0.000 claims 1
- SGPBTOFBJHNEHK-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[3-(trifluoromethoxy)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC(C=2C=C(OC(F)(F)F)C=CC=2)=C1 SGPBTOFBJHNEHK-UHFFFAOYSA-N 0.000 claims 1
- ISQWXMJRDUTFQR-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[3-(trifluoromethyl)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound C1C(=O)N(C)C(N)=NC1(C)C1=CC=CC(C=2C=C(C=CC=2)C(F)(F)F)=C1 ISQWXMJRDUTFQR-UHFFFAOYSA-N 0.000 claims 1
- ZARNYONTEHLFTM-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[4-(2-methylpropyl)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC=CC(C2(C)N=C(N)N(C)C(=O)C2)=C1 ZARNYONTEHLFTM-UHFFFAOYSA-N 0.000 claims 1
- WLFGCOATMGBIMK-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-[3-[4-(trifluoromethyl)phenyl]phenyl]-5h-pyrimidin-4-one Chemical compound C1C(=O)N(C)C(N)=NC1(C)C1=CC=CC(C=2C=CC(=CC=2)C(F)(F)F)=C1 WLFGCOATMGBIMK-UHFFFAOYSA-N 0.000 claims 1
- BWSBDDXEXFOUFF-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-naphthalen-1-yl-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=CC2=CC=CC=C12 BWSBDDXEXFOUFF-UHFFFAOYSA-N 0.000 claims 1
- WUMVZIVQSDNFIS-UHFFFAOYSA-N 2-amino-3,6-dimethyl-6-naphthalen-2-yl-5h-pyrimidin-4-one Chemical compound N1=C(N)N(C)C(=O)CC1(C)C1=CC=C(C=CC=C2)C2=C1 WUMVZIVQSDNFIS-UHFFFAOYSA-N 0.000 claims 1
- BUGYZPIJZAJBJE-UHFFFAOYSA-N 2-amino-3-(1,3-dioxolan-2-ylmethyl)-6-[2-(1h-indol-6-yl)ethyl]pyrimidin-4-one Chemical compound NC1=NC(CCC=2C=C3NC=CC3=CC=2)=CC(=O)N1CC1OCCO1 BUGYZPIJZAJBJE-UHFFFAOYSA-N 0.000 claims 1
- NVNLUJHTXMMHAJ-UHFFFAOYSA-N 2-amino-3-(cyclohexylmethyl)-6-[2-[3-(furan-2-yl)phenyl]ethyl]pyrimidin-4-one Chemical compound C=1C(=O)N(CC2CCCCC2)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 NVNLUJHTXMMHAJ-UHFFFAOYSA-N 0.000 claims 1
- HAHGTEFAWHMEPW-UHFFFAOYSA-N 2-amino-3-[2-(1,3-dioxan-2-yl)ethyl]-6-[2-[3-(furan-2-yl)phenyl]ethyl]pyrimidin-4-one Chemical compound C=1C(=O)N(CCC2OCCCO2)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 HAHGTEFAWHMEPW-UHFFFAOYSA-N 0.000 claims 1
- CGUDCPJIDBXKOB-UHFFFAOYSA-N 2-amino-3-[2-(benzylamino)ethyl]-6-[2-[3-(furan-2-yl)phenyl]ethyl]pyrimidin-4-one Chemical compound C=1C(=O)N(CCNCC=2C=CC=CC=2)C(N)=NC=1CCC(C=1)=CC=CC=1C1=CC=CO1 CGUDCPJIDBXKOB-UHFFFAOYSA-N 0.000 claims 1
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| US20030114445A1 (en) * | 2001-06-15 | 2003-06-19 | Chengxin Zhi | N3-substituted 6-anilinopyrimidines and methods to treat-Gram-positive bacterial and mycoplasmal infections |
| US7138403B2 (en) * | 2001-08-13 | 2006-11-21 | Janssen Pharmaceutica N.V. | 2,4,5-trisubstituted thiazolyl derivatives and their antiinflammatory activity |
| CN100488958C (zh) * | 2001-09-21 | 2009-05-20 | 三菱制药株式会社 | 3-取代的-4-嘧啶酮衍生物 |
| US6951875B2 (en) * | 2001-10-29 | 2005-10-04 | Hoffmann-La Roche Inc. | Conjugated aromatic compounds with a pyridine substituent |
| AU2002950853A0 (en) * | 2002-08-19 | 2002-09-12 | Fujisawa Pharmaceutical Co., Ltd. | Aminopyrimidine compound and pharmaceutical use thereof |
| ZA200505258B (en) * | 2002-12-16 | 2006-09-27 | Mitsubishi Pharma Corp | 3-Substituted-4-pyrimidone derivatives |
| TWI357408B (en) * | 2003-03-26 | 2012-02-01 | Mitsubishi Tanabe Pharma Corp | 3-substituted-4-pyrimidone derivatives |
| KR20080025079A (ko) * | 2005-06-14 | 2008-03-19 | 쉐링 코포레이션 | 아스파르틸 프로테아제 억제제 |
| CN101193892A (zh) * | 2005-06-14 | 2008-06-04 | 先灵公司 | 大环杂环天冬氨酰基蛋白酶抑制剂 |
| US7763606B2 (en) * | 2005-10-27 | 2010-07-27 | Schering Corporation | Heterocyclic aspartyl protease inhibitors |
| US7560451B2 (en) * | 2005-10-31 | 2009-07-14 | Schering Corporation | Aspartyl protease inhibitors |
-
2005
- 2005-10-14 WO PCT/SE2005/001534 patent/WO2006041405A1/en not_active Ceased
- 2005-10-14 EP EP05794248A patent/EP1802588A4/en not_active Withdrawn
- 2005-10-14 JP JP2007536656A patent/JP2008516946A/ja active Pending
- 2005-10-14 US US11/577,154 patent/US20090062282A1/en not_active Abandoned
- 2005-10-14 CN CNA200580043143XA patent/CN101084198A/zh active Pending
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