JP2013508404A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2013508404A5 JP2013508404A5 JP2012535385A JP2012535385A JP2013508404A5 JP 2013508404 A5 JP2013508404 A5 JP 2013508404A5 JP 2012535385 A JP2012535385 A JP 2012535385A JP 2012535385 A JP2012535385 A JP 2012535385A JP 2013508404 A5 JP2013508404 A5 JP 2013508404A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- diazabicyclo
- octane
- triazol
- fluoro
- 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
Links
- -1 2H-1,2,3-triazol-2-yl Chemical group 0.000 claims 197
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 24
- 125000000217 alkyl group Chemical group 0.000 claims 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 22
- 239000000126 substance Substances 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 18
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 125000005843 halogen group Chemical group 0.000 claims 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000001607 1,2,3-triazol-1-yl group Chemical group [*]N1N=NC([H])=C1[H] 0.000 claims 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 5
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000004498 isoxazol-4-yl group Chemical group O1N=CC(=C1)* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 3
- MKJZIZWXDYBQGT-UHFFFAOYSA-N 2-fluoro-6-(4-methylpyridin-2-yl)benzaldehyde Chemical compound FC1=CC=CC(=C1C=O)C1=NC=CC(=C1)C MKJZIZWXDYBQGT-UHFFFAOYSA-N 0.000 claims 3
- AVUGWWNPIYMWFM-UHFFFAOYSA-N 3-(1,2-oxazol-5-yl)-1,2-oxazole Chemical compound O1N=CC=C1C1=NOC=C1 AVUGWWNPIYMWFM-UHFFFAOYSA-N 0.000 claims 3
- WXFOIFCNLHJFKL-UHFFFAOYSA-N 3-fluoro-2-(4-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CC(=NC=C1)C2=C(C=CC=C2F)C=O WXFOIFCNLHJFKL-UHFFFAOYSA-N 0.000 claims 3
- VWMQXAYLHOSRKA-UHFFFAOYSA-N 5-chloro-1,3-benzoxazole Chemical compound ClC1=CC=C2OC=NC2=C1 VWMQXAYLHOSRKA-UHFFFAOYSA-N 0.000 claims 3
- JPUWQDQOTJPGPA-UHFFFAOYSA-N [6-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound C=1C=CC=C(C=2SC=CC=2)C=1C(=O)N(CC12)CC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 JPUWQDQOTJPGPA-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000004434 sulfur atom Chemical group 0.000 claims 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- YESCPKTWTUCNTK-UHFFFAOYSA-N 2-fluoro-6-(triazol-2-yl)benzaldehyde Chemical compound FC1=C(C(=CC=C1)N1N=CC=N1)C=O YESCPKTWTUCNTK-UHFFFAOYSA-N 0.000 claims 2
- USIFEQSDNJSTEZ-UHFFFAOYSA-N 3-fluoro-2-(1,3-oxazol-2-yl)benzaldehyde Chemical compound FC=1C(=C(C=CC=1)C=O)C=1OC=CN=1 USIFEQSDNJSTEZ-UHFFFAOYSA-N 0.000 claims 2
- RWIQUTTXNIBMEB-UHFFFAOYSA-N 3-fluoro-2-(3-fluoropyridin-2-yl)benzaldehyde Chemical compound C1=CC(=C(C(=C1)F)C2=C(C=CC=N2)F)C=O RWIQUTTXNIBMEB-UHFFFAOYSA-N 0.000 claims 2
- AQNUMUOUDSPGFZ-UHFFFAOYSA-N 3-fluoro-2-(6-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=NC(=CC=C1)C2=C(C=CC=C2F)C=O AQNUMUOUDSPGFZ-UHFFFAOYSA-N 0.000 claims 2
- QSYWKQLZNHTFCV-UHFFFAOYSA-N 3-fluoro-2-(triazol-2-yl)benzaldehyde Chemical compound FC1=CC=CC(C=O)=C1N1N=CC=N1 QSYWKQLZNHTFCV-UHFFFAOYSA-N 0.000 claims 2
- DHWCSMLTMQOFTF-UHFFFAOYSA-N 3-fluoro-2-pyridin-2-ylbenzaldehyde Chemical compound C1=CC=NC(=C1)C2=C(C=CC=C2F)C=O DHWCSMLTMQOFTF-UHFFFAOYSA-N 0.000 claims 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- IBBWBTSDCKSONR-UHFFFAOYSA-N 4-fluoro-2-(3-fluoropyridin-2-yl)benzaldehyde Chemical compound C1=CC(=C(N=C1)C2=C(C=CC(=C2)F)C=O)F IBBWBTSDCKSONR-UHFFFAOYSA-N 0.000 claims 2
- QMZYMTUJIDFLAL-UHFFFAOYSA-N 4-fluoro-2-(4-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CC(=NC=C1)C2=C(C=CC(=C2)F)C=O QMZYMTUJIDFLAL-UHFFFAOYSA-N 0.000 claims 2
- HPDVLTBRUZLFHQ-UHFFFAOYSA-N 4-fluoro-2-(6-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=NC(=CC=C1)C2=C(C=CC(=C2)F)C=O HPDVLTBRUZLFHQ-UHFFFAOYSA-N 0.000 claims 2
- WDSYURFPAZPOEH-UHFFFAOYSA-N 4-fluoro-2-(triazol-2-yl)benzaldehyde Chemical compound FC1=CC(=C(C=C1)C=O)N1N=CC=N1 WDSYURFPAZPOEH-UHFFFAOYSA-N 0.000 claims 2
- AEHCOTWWCZSIBH-UHFFFAOYSA-N 4-fluoro-2-pyridin-2-ylbenzaldehyde Chemical compound N1=C(C=CC=C1)C1=C(C=O)C=CC(=C1)F AEHCOTWWCZSIBH-UHFFFAOYSA-N 0.000 claims 2
- XEHHYSIYICDBID-UHFFFAOYSA-N 5-fluoro-2-(triazol-2-yl)benzaldehyde Chemical compound Fc1ccc(c(C=O)c1)-n1nccn1 XEHHYSIYICDBID-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- QIADRVMTVCXFSA-UHFFFAOYSA-N C1=CC(=C(C=C1F)C2=NC=CO2)C=O Chemical compound C1=CC(=C(C=C1F)C2=NC=CO2)C=O QIADRVMTVCXFSA-UHFFFAOYSA-N 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 206010033307 Overweight Diseases 0.000 claims 2
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 2
- 208000001871 Tachycardia Diseases 0.000 claims 2
- ACJPUSZQFBKUFF-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(C)=CC=C(N2N=CC=N2)C=1C(=O)N(CC12)CC1CN2C1=NC(C)=CC(C)=N1 ACJPUSZQFBKUFF-UHFFFAOYSA-N 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 206010022437 insomnia Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 235000020825 overweight Nutrition 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 230000006794 tachycardia Effects 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- NARYFSHFYGGAPX-RXVVDRJESA-N (1s,6r)-4-(2-phenylphenyl)sulfonyl-7-[5-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=CC(C(F)(F)F)=CC=C1N1[C@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)C=3C=CC=CC=3)CC[C@H]2C1 NARYFSHFYGGAPX-RXVVDRJESA-N 0.000 claims 1
- XMGUPEFWVBGCFK-PXNSSMCTSA-N (1s,6r)-4-(2-phenylphenyl)sulfonyl-7-[5-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octane Chemical compound N1=CC(C(F)(F)F)=CN=C1N1[C@H]2CN(S(=O)(=O)C=3C(=CC=CC=3)C=3C=CC=CC=3)CC[C@H]2C1 XMGUPEFWVBGCFK-PXNSSMCTSA-N 0.000 claims 1
- WCUGSLIJJFPUGV-HOTGVXAUSA-N (1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4-(2-methoxyphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octane Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C[C@@H]2N(C=3N=C(C)C=C(C)N=3)C[C@@H]2CC1 WCUGSLIJJFPUGV-HOTGVXAUSA-N 0.000 claims 1
- LQLJXTVERMXZOQ-UNMCSNQZSA-N (1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4-(2-phenylphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octane Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)S(=O)(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 LQLJXTVERMXZOQ-UNMCSNQZSA-N 0.000 claims 1
- QIBAJUSGSRFHMG-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-(7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CC2N(C=3N=C4C=CC=CC4=NC=3)CC2CC1 QIBAJUSGSRFHMG-UHFFFAOYSA-N 0.000 claims 1
- JONOPNXFMMCQAM-ZFWWWQNUSA-N (2,6-dimethoxyphenyl)-[(1s,6r)-7-[5-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C[C@@H]2N(C=3N=CC(=CC=3)C(F)(F)F)C[C@@H]2CC1 JONOPNXFMMCQAM-ZFWWWQNUSA-N 0.000 claims 1
- MDBBDWLUJSRULO-JSGCOSHPSA-N (2,6-dimethoxyphenyl)-[(1s,6r)-7-[5-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C[C@@H]2N(C=3N=CC(=CN=3)C(F)(F)F)C[C@@H]2CC1 MDBBDWLUJSRULO-JSGCOSHPSA-N 0.000 claims 1
- QIBAJUSGSRFHMG-YJBOKZPZSA-N (2,6-dimethoxyphenyl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 QIBAJUSGSRFHMG-YJBOKZPZSA-N 0.000 claims 1
- VURGMHJXNCHXIT-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-[7-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CC2N(C=3N=C(C=CN=3)C=3C=CC=CC=3)CC2CC1 VURGMHJXNCHXIT-UHFFFAOYSA-N 0.000 claims 1
- DICRKFALAXMPIZ-GUYCJALGSA-N (2-bromo-5-fluorophenyl)-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)Br)=N1 DICRKFALAXMPIZ-GUYCJALGSA-N 0.000 claims 1
- GZIRHUBRAHLBCA-LIRRHRJNSA-N (2-bromophenyl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound BrC1=CC=CC=C1C(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 GZIRHUBRAHLBCA-LIRRHRJNSA-N 0.000 claims 1
- CTTAQNIKFVJOHR-UHFFFAOYSA-N (2-bromophenyl)-[6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)Br)=N1 CTTAQNIKFVJOHR-UHFFFAOYSA-N 0.000 claims 1
- GATCPBZBYFRAAH-UHFFFAOYSA-N (2-bromophenyl)-[6-(4-methylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]methanone Chemical compound CC1=CC=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)Br)=N1 GATCPBZBYFRAAH-UHFFFAOYSA-N 0.000 claims 1
- YIGGCJGLRRXREG-YOEHRIQHSA-N (2-fluoro-6-pyrimidin-2-ylphenyl)-[(1s,6r)-7-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound FC(F)(F)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)C=2N=CC=CN=2)=N1 YIGGCJGLRRXREG-YOEHRIQHSA-N 0.000 claims 1
- IWVIDALMACPDIX-UHFFFAOYSA-N (2-methoxyphenyl)-(6-quinoxalin-2-yl-3,6-diazabicyclo[3.2.0]heptan-3-yl)methanone Chemical compound COC1=CC=CC=C1C(=O)N1CC2N(C=3N=C4C=CC=CC4=NC=3)CC2C1 IWVIDALMACPDIX-UHFFFAOYSA-N 0.000 claims 1
- JKDJAMNOQDSZFM-UHFFFAOYSA-N (2-methoxyphenyl)-[6-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)N1CC2N(C=3N=C(C=CN=3)C=3C=CC=CC=3)CC2C1 JKDJAMNOQDSZFM-UHFFFAOYSA-N 0.000 claims 1
- WBFFBCACAZRULE-UHFFFAOYSA-N (2-phenylphenyl)-(6-quinoxalin-2-yl-3,6-diazabicyclo[3.2.0]heptan-3-yl)methanone Chemical compound C1C2CN(C=3N=C4C=CC=CC4=NC=3)C2CN1C(=O)C1=CC=CC=C1C1=CC=CC=C1 WBFFBCACAZRULE-UHFFFAOYSA-N 0.000 claims 1
- HWBHNCKNXGKGOR-UHFFFAOYSA-N (2-phenylphenyl)-(7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl)methanone Chemical compound C1CC2CN(C=3N=C4C=CC=CC4=NC=3)C2CN1C(=O)C1=CC=CC=C1C1=CC=CC=C1 HWBHNCKNXGKGOR-UHFFFAOYSA-N 0.000 claims 1
- HWBHNCKNXGKGOR-CJFMBICVSA-N (2-phenylphenyl)-[(1r,6s)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@H]1N(C[C@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1C1=CC=CC=C1 HWBHNCKNXGKGOR-CJFMBICVSA-N 0.000 claims 1
- HWBHNCKNXGKGOR-CPJSRVTESA-N (2-phenylphenyl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1C1=CC=CC=C1 HWBHNCKNXGKGOR-CPJSRVTESA-N 0.000 claims 1
- FBXAORYHONSOPH-UHFFFAOYSA-N (2-phenylphenyl)-[6-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]methanone Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)N(CC12)CC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 FBXAORYHONSOPH-UHFFFAOYSA-N 0.000 claims 1
- ZYWRJPNACZTMSM-UHFFFAOYSA-N (2-phenylphenyl)-[7-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)N(CC12)CCC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 ZYWRJPNACZTMSM-UHFFFAOYSA-N 0.000 claims 1
- HNGPNDUPZZQYMH-CYFREDJKSA-N (2-pyridin-3-ylphenyl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1C1=CC=CN=C1 HNGPNDUPZZQYMH-CYFREDJKSA-N 0.000 claims 1
- AOTIXDWTXAREKJ-ZFWWWQNUSA-N (3-bromopyridin-2-yl)-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CN=2)Br)=N1 AOTIXDWTXAREKJ-ZFWWWQNUSA-N 0.000 claims 1
- XZFBUBSXLJEFOU-KSSFIOAISA-N (3-fluoro-2-pyrimidin-2-ylphenyl)-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C=CC=C(C=2C=2N=CC=CN=2)F)N1C1=CC(C(F)(F)F)=CC=N1 XZFBUBSXLJEFOU-KSSFIOAISA-N 0.000 claims 1
- KWJUCTIIYDCFRA-YOEHRIQHSA-N (3-methylfuran-2-yl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=COC(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C3C=CC=CC3=NC=2)=C1C KWJUCTIIYDCFRA-YOEHRIQHSA-N 0.000 claims 1
- RCPUSPJRILBGKC-LPHOPBHVSA-N (3-propoxypyridin-2-yl)-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CCCOC1=CC=CN=C1C(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 RCPUSPJRILBGKC-LPHOPBHVSA-N 0.000 claims 1
- GMXZJPCLCBRYSS-VXKWHMMOSA-N (5-methyl-3-phenyl-1,2-oxazol-4-yl)-[(1s,6r)-7-(2-phenylpyrimidin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=NOC=2C)C=2C=CC=CC=2)N1C(N=1)=CC=NC=1C1=CC=CC=C1 GMXZJPCLCBRYSS-VXKWHMMOSA-N 0.000 claims 1
- ARDNPMFDNCMLTK-ZFWWWQNUSA-N (6-bromo-2-fluoro-3-methoxyphenyl)-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound COC1=CC=C(Br)C(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C(C)C=C(C)N=2)=C1F ARDNPMFDNCMLTK-ZFWWWQNUSA-N 0.000 claims 1
- HGCUPVSMDWTYJY-UHFFFAOYSA-N (6-quinoxalin-2-yl-3,6-diazabicyclo[3.2.0]heptan-3-yl)-(2-thiophen-2-ylphenyl)methanone Chemical compound C1C2CN(C=3N=C4C=CC=CC4=NC=3)C2CN1C(=O)C1=CC=CC=C1C1=CC=CS1 HGCUPVSMDWTYJY-UHFFFAOYSA-N 0.000 claims 1
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims 1
- GHCFWKFREBNSPC-UHFFFAOYSA-N 2-Amino-4-methylpyrimidine Chemical compound CC1=CC=NC(N)=N1 GHCFWKFREBNSPC-UHFFFAOYSA-N 0.000 claims 1
- IBPUDGBNRKNXEN-PXNSSMCTSA-N 2-[(1s,6r)-4-(2,4-dimethylphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octan-7-yl]quinoxaline Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 IBPUDGBNRKNXEN-PXNSSMCTSA-N 0.000 claims 1
- LNJRVJRRAISZPA-YJBOKZPZSA-N 2-[(1s,6r)-4-(2-methoxyphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octan-7-yl]quinoxaline Chemical compound COC1=CC=CC=C1S(=O)(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 LNJRVJRRAISZPA-YJBOKZPZSA-N 0.000 claims 1
- OTIIKUIEKAFHKL-RDPSFJRHSA-N 2-[(1s,6r)-4-(2-phenylphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octan-7-yl]quinoxaline Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1S(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 OTIIKUIEKAFHKL-RDPSFJRHSA-N 0.000 claims 1
- KCVIQJNZQQPBRD-UHFFFAOYSA-N 2-[4-(2,5-dimethylphenyl)sulfonyl-4,7-diazabicyclo[4.2.0]octan-7-yl]quinoxaline Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2CC3N(CC3CC2)C=2N=C3C=CC=CC3=NC=2)=C1 KCVIQJNZQQPBRD-UHFFFAOYSA-N 0.000 claims 1
- PFRHAIZMYZWTLA-UHFFFAOYSA-N 2-fluoro-6-(3-fluoropyridin-2-yl)benzaldehyde Chemical compound C1=CC(=C(C(=C1)F)C=O)C2=C(C=CC=N2)F PFRHAIZMYZWTLA-UHFFFAOYSA-N 0.000 claims 1
- ZCGYAVOXRDPOJD-UHFFFAOYSA-N 2-fluoro-6-(5-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CN=C(C=C1)C2=C(C(=CC=C2)F)C=O ZCGYAVOXRDPOJD-UHFFFAOYSA-N 0.000 claims 1
- JDLXIDQAKPIYID-UHFFFAOYSA-N 2-fluoro-6-(6-methylpyridin-2-yl)benzaldehyde Chemical compound FC1=CC=CC(=C1C=O)C1=NC(=CC=C1)C JDLXIDQAKPIYID-UHFFFAOYSA-N 0.000 claims 1
- QEFIKOMWZLOAOD-UHFFFAOYSA-N 2-fluoro-6-pyridin-2-ylbenzaldehyde Chemical compound FC1=C(C(=CC=C1)C1=NC=CC=C1)C=O QEFIKOMWZLOAOD-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- GKVDLTTVBNOGNJ-UHFFFAOYSA-N 2-methylpyrimidin-4-amine Chemical compound CC1=NC=CC(N)=N1 GKVDLTTVBNOGNJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WUQUKLOIBGJNDE-UHFFFAOYSA-N 3-fluoro-2-(3-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=C(N=CC=C1)C2=C(C=CC=C2F)C=O WUQUKLOIBGJNDE-UHFFFAOYSA-N 0.000 claims 1
- STCDQSZPZSNVJV-UHFFFAOYSA-N 3-fluoro-2-(5-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CN=C(C=C1)C2=C(C=CC=C2F)C=O STCDQSZPZSNVJV-UHFFFAOYSA-N 0.000 claims 1
- UOGQXTVHJKVPLF-UHFFFAOYSA-N 3-fluoro-2-iodobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1I UOGQXTVHJKVPLF-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- JGRWWWRIELRNML-UHFFFAOYSA-N 3-methyl-5-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazole Chemical compound O1N=C(C)C=C1C1=NOC(C)=C1 JGRWWWRIELRNML-UHFFFAOYSA-N 0.000 claims 1
- DSMRYCOTKWYTRF-UHFFFAOYSA-N 3-methylfuran-2-carbaldehyde Chemical compound CC=1C=COC=1C=O DSMRYCOTKWYTRF-UHFFFAOYSA-N 0.000 claims 1
- ZQWQTAWWLCNIFT-UHFFFAOYSA-N 3-propoxypyridine-2-carbaldehyde Chemical compound CCCOC1=CC=CN=C1C=O ZQWQTAWWLCNIFT-UHFFFAOYSA-N 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JCYBCKCBKJIKFC-UHFFFAOYSA-N 4-(2,5-dimethylphenyl)sulfonyl-7-(4-phenylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octane Chemical compound CC1=CC=C(C)C(S(=O)(=O)N2CC3N(CC3CC2)C=2N=C(C=CN=2)C=2C=CC=CC=2)=C1 JCYBCKCBKJIKFC-UHFFFAOYSA-N 0.000 claims 1
- HHIMZKLIKHUKNH-JTSKRJEESA-N 4-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octane-4-carbonyl]fluoren-9-one Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C=3C4=CC=CC=C4C(=O)C=3C=CC=2)=N1 HHIMZKLIKHUKNH-JTSKRJEESA-N 0.000 claims 1
- KAPBBCMFJBSIIP-UHFFFAOYSA-N 5-fluoro-2-(3-fluoropyridin-2-yl)benzaldehyde Chemical compound C1=CC(=C(N=C1)C2=C(C=C(C=C2)F)C=O)F KAPBBCMFJBSIIP-UHFFFAOYSA-N 0.000 claims 1
- VWHFNRDBPSAOTA-UHFFFAOYSA-N 5-fluoro-2-(4-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CC(=NC=C1)C2=C(C=C(C=C2)F)C=O VWHFNRDBPSAOTA-UHFFFAOYSA-N 0.000 claims 1
- QDHHHAQQULFCRZ-UHFFFAOYSA-N 5-fluoro-2-(5-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=CN=C(C=C1)C2=C(C=C(C=C2)F)C=O QDHHHAQQULFCRZ-UHFFFAOYSA-N 0.000 claims 1
- CRBYKCYXEVAHHQ-UHFFFAOYSA-N 5-fluoro-2-(6-methylpyridin-2-yl)benzaldehyde Chemical compound CC1=NC(=CC=C1)C2=C(C=C(C=C2)F)C=O CRBYKCYXEVAHHQ-UHFFFAOYSA-N 0.000 claims 1
- BCWREPKTFIRQMY-UHFFFAOYSA-N 5-fluoro-2-pyridin-2-ylbenzaldehyde Chemical compound FC=1C=CC(=C(C=1)C=O)C1=NC=CC=C1 BCWREPKTFIRQMY-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000006820 Arthralgia Diseases 0.000 claims 1
- 208000008035 Back Pain Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- WCDPTSBGTOUCQD-UHFFFAOYSA-N C1=CC(=C(C(=C1)F)C=O)C2=NC=CO2 Chemical compound C1=CC(=C(C(=C1)F)C=O)C2=NC=CO2 WCDPTSBGTOUCQD-UHFFFAOYSA-N 0.000 claims 1
- WCEZRNGFUKLRSV-UHFFFAOYSA-N C1=CC(=C(C=C1F)C=O)C2=NC=CO2 Chemical compound C1=CC(=C(C=C1F)C=O)C2=NC=CO2 WCEZRNGFUKLRSV-UHFFFAOYSA-N 0.000 claims 1
- NVAJUYOXGQSRHP-IRXDYDNUSA-N CC1=CC(=NC(=C1)N2C[C@H]3[C@@H]2CN(CC3)C(=O)C4=C(C=CC=C4OC)OC)C Chemical compound CC1=CC(=NC(=C1)N2C[C@H]3[C@@H]2CN(CC3)C(=O)C4=C(C=CC=C4OC)OC)C NVAJUYOXGQSRHP-IRXDYDNUSA-N 0.000 claims 1
- 206010007556 Cardiac failure acute Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 208000008930 Low Back Pain Diseases 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 102000002512 Orexin Human genes 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 claims 1
- 102000008834 Orexin receptor Human genes 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 208000005793 Restless legs syndrome Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- MZDGWJKFCYEWNJ-NFBKMPQASA-N [(1r,6s)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@@H]3CN(CC[C@@H]3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 MZDGWJKFCYEWNJ-NFBKMPQASA-N 0.000 claims 1
- MEVSCUGONDYNJE-NHYWBVRUSA-N [(1s,6r)-7-(2,6-diaminopyrimidin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound NC1=NC(N)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 MEVSCUGONDYNJE-NHYWBVRUSA-N 0.000 claims 1
- PMVLDLLANHWMOK-GUYCJALGSA-N [(1s,6r)-7-(2-amino-6-methylpyrimidin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound NC1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 PMVLDLLANHWMOK-GUYCJALGSA-N 0.000 claims 1
- XFGQCWIAUYOLMZ-LPHOPBHVSA-N [(1s,6r)-7-(3,6-dimethylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 XFGQCWIAUYOLMZ-LPHOPBHVSA-N 0.000 claims 1
- ICMQPIRTMWYWLC-YJBOKZPZSA-N [(1s,6r)-7-(3,6-dimethylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 ICMQPIRTMWYWLC-YJBOKZPZSA-N 0.000 claims 1
- ZTJVMFAEMRPFSN-YJBOKZPZSA-N [(1s,6r)-7-(3,6-dimethylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 ZTJVMFAEMRPFSN-YJBOKZPZSA-N 0.000 claims 1
- QXWZOPJMXHAPCO-KXBFYZLASA-N [(1s,6r)-7-(3,6-dimethylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 QXWZOPJMXHAPCO-KXBFYZLASA-N 0.000 claims 1
- QWFPALIULRJOIW-KXBFYZLASA-N [(1s,6r)-7-(3,6-dimethylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 QWFPALIULRJOIW-KXBFYZLASA-N 0.000 claims 1
- SHRHTMZZKNOJLZ-YJBOKZPZSA-N [(1s,6r)-7-(3-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=NC=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=CC=3)N3N=CC=N3)CC[C@H]2C1 SHRHTMZZKNOJLZ-YJBOKZPZSA-N 0.000 claims 1
- MBEKCIKDJYZYAN-PXNSSMCTSA-N [(1s,6r)-7-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(3-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)C=2N=CC=CN=2)=C1 MBEKCIKDJYZYAN-PXNSSMCTSA-N 0.000 claims 1
- LLGNRTNWYJCFTP-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=C1 LLGNRTNWYJCFTP-LPHOPBHVSA-N 0.000 claims 1
- CHAHXUDUKPFECQ-UWJYYQICSA-N [(1s,6r)-7-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)N1C1=CC(C)=CC(C)=N1 CHAHXUDUKPFECQ-UWJYYQICSA-N 0.000 claims 1
- XYAFDLIZOQHUIS-JXFKEZNVSA-N [(1s,6r)-7-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=C1 XYAFDLIZOQHUIS-JXFKEZNVSA-N 0.000 claims 1
- ZXRYYYFEJZOTBI-UWJYYQICSA-N [(1s,6r)-7-(4,6-dimethylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)N1C1=CC(C)=CC(C)=N1 ZXRYYYFEJZOTBI-UWJYYQICSA-N 0.000 claims 1
- ROYPKHBNXANUAO-YJBOKZPZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(1,8-naphthyridin-4-yl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C3=CC=CN=C3N=CC=2)=N1 ROYPKHBNXANUAO-YJBOKZPZSA-N 0.000 claims 1
- FMDLLJUHVSZUIY-FPOVZHCZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-ethoxynaphthalen-1-yl)methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=C3C=CC=CC3=CC=C2OCC)N1C1=NC(C)=CC(C)=N1 FMDLLJUHVSZUIY-FPOVZHCZSA-N 0.000 claims 1
- RMYCLEOMFLPDCU-WMZOPIPTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-fluoro-3-methoxy-6-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C(C)C=C(C)N=2)N1C(=O)C1=C(F)C(OC)=CC=C1C1=NC=CC=N1 RMYCLEOMFLPDCU-WMZOPIPTSA-N 0.000 claims 1
- GRZCUNDJSTYPFU-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-fluoro-6-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)C=2N=CC=CN=2)=N1 GRZCUNDJSTYPFU-LPHOPBHVSA-N 0.000 claims 1
- MZDGWJKFCYEWNJ-REWPJTCUSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 MZDGWJKFCYEWNJ-REWPJTCUSA-N 0.000 claims 1
- IYMMQDYNDIQIHJ-PXNSSMCTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)C=2N=CC=CN=2)=N1 IYMMQDYNDIQIHJ-PXNSSMCTSA-N 0.000 claims 1
- XBMJYTBILCSPGW-RXVVDRJESA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-pyrrol-1-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2C=CC=C2)=N1 XBMJYTBILCSPGW-RXVVDRJESA-N 0.000 claims 1
- GFFAVKDUYBZUHO-PXNSSMCTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 GFFAVKDUYBZUHO-PXNSSMCTSA-N 0.000 claims 1
- MEURXDCKHZIQND-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(3-fluoro-2-pyrazol-1-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=C2)=N1 MEURXDCKHZIQND-LPHOPBHVSA-N 0.000 claims 1
- ADBOZGRDDFIONY-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(3-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)C=2N=CC=CN=2)=N1 ADBOZGRDDFIONY-LPHOPBHVSA-N 0.000 claims 1
- FXJOBYDZYVFQIS-ICSRJNTNSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(3-methyl-2-pyrazol-1-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(C)C=CC=2)N2N=CC=C2)=N1 FXJOBYDZYVFQIS-ICSRJNTNSA-N 0.000 claims 1
- URROPVKRCHCUOU-JXFKEZNVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)C=2N=CC=CN=2)=N1 URROPVKRCHCUOU-JXFKEZNVSA-N 0.000 claims 1
- XUPCMGYHEMYXNZ-KKSFZXQISA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-fluoro-2-pyrimidin-5-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)C=2C=NC=NC=2)=N1 XUPCMGYHEMYXNZ-KKSFZXQISA-N 0.000 claims 1
- VUJVKLDUMVARNX-GJZGRUSLSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-methoxy-2-methylpyrimidin-4-yl)methanone Chemical compound COC1=CN=C(C)N=C1C(=O)N1C[C@@H]2N(C=3N=C(C)C=C(C)N=3)C[C@@H]2CC1 VUJVKLDUMVARNX-GJZGRUSLSA-N 0.000 claims 1
- COALYLDHKMSPID-RXVVDRJESA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C(C)C=C(C)N=2)N1C(=O)C1=CC(C)=CC=C1C1=NC=CC=N1 COALYLDHKMSPID-RXVVDRJESA-N 0.000 claims 1
- RUTAJQSZMQXFES-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-phenyl-1,2-oxazol-4-yl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C2=C(ON=C2)C=2C=CC=CC=2)=N1 RUTAJQSZMQXFES-HKUYNNGSSA-N 0.000 claims 1
- SCQSUMNRDUQLMN-REWPJTCUSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(9h-fluoren-4-yl)methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C=3C4=CC=CC=C4CC=3C=CC=2)=N1 SCQSUMNRDUQLMN-REWPJTCUSA-N 0.000 claims 1
- SALFTRQLKHQRSL-YJBOKZPZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(1h-1,2,4-triazol-5-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)C=2NN=CN=2)=N1 SALFTRQLKHQRSL-YJBOKZPZSA-N 0.000 claims 1
- MHLPBRRUNHDHLH-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound CC1=NOC(C=2C(=CC=CC=2)C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C(C)C=C(C)N=2)=N1 MHLPBRRUNHDHLH-LPHOPBHVSA-N 0.000 claims 1
- WNWUDGHZOXYLNZ-PXNSSMCTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(furan-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)C=2OC=CC=2)=N1 WNWUDGHZOXYLNZ-PXNSSMCTSA-N 0.000 claims 1
- OUVHNDWXWOLNTO-HOCLYGCPSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-1-yl)-6-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=NC(=CC=2)C(F)(F)F)N2N=NC=C2)=N1 OUVHNDWXWOLNTO-HOCLYGCPSA-N 0.000 claims 1
- GCJLLSZIAIAWSK-LPHOPBHVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 GCJLLSZIAIAWSK-LPHOPBHVSA-N 0.000 claims 1
- LJZIGRNYUYTLML-ZFWWWQNUSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(trifluoromethyl)pyridin-3-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=NC=CC=2)C(F)(F)F)=N1 LJZIGRNYUYTLML-ZFWWWQNUSA-N 0.000 claims 1
- SJCRTLFZMYFXRM-YJBOKZPZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 SJCRTLFZMYFXRM-YJBOKZPZSA-N 0.000 claims 1
- CHLFYOFERFUEBH-RDJZCZTQSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-(triazol-1-yl)pyridin-2-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CN=2)N2N=NC=C2)=N1 CHLFYOFERFUEBH-RDJZCZTQSA-N 0.000 claims 1
- REZXBSRYXSQAPC-RDJZCZTQSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-(triazol-2-yl)pyridin-2-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CN=2)N2N=CC=N2)=N1 REZXBSRYXSQAPC-RDJZCZTQSA-N 0.000 claims 1
- ZLZXBOCSKUBSRY-KXBFYZLASA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)C2=NNC=C2)=N1 ZLZXBOCSKUBSRY-KXBFYZLASA-N 0.000 claims 1
- RHFCEWQBBZIMDX-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-methyl-2-(triazol-1-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(C)C=CC=2)N2N=NC=C2)=N1 RHFCEWQBBZIMDX-HKUYNNGSSA-N 0.000 claims 1
- WNFPOORBCVZXSS-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(C)C=CC=2)N2N=CC=N2)=N1 WNFPOORBCVZXSS-HKUYNNGSSA-N 0.000 claims 1
- OBZDRYNAXVTAJE-GJZGRUSLSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-methyl-5-(4-methylthiadiazol-5-yl)-1,2-oxazol-4-yl]methanone Chemical compound N1=NSC(C2=C(C(C)=NO2)C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C(C)C=C(C)N=2)=C1C OBZDRYNAXVTAJE-GJZGRUSLSA-N 0.000 claims 1
- SUAOPYDXJOMHPQ-RDJZCZTQSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-methyl-5-(5-methyl-1,2-oxazol-3-yl)-1,2-oxazol-4-yl]methanone Chemical compound O1C(C)=CC(C2=C(C(C)=NO2)C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C(C)C=C(C)N=2)=N1 SUAOPYDXJOMHPQ-RDJZCZTQSA-N 0.000 claims 1
- MVCRFRYMKXDRPT-KXBFYZLASA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 MVCRFRYMKXDRPT-KXBFYZLASA-N 0.000 claims 1
- CGLXSGZQQIHPAY-JXFKEZNVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)N1C1=NC(C)=CC(C)=N1 CGLXSGZQQIHPAY-JXFKEZNVSA-N 0.000 claims 1
- FTOSJNYBIZILBH-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5,6-dimethyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=NC(C)=C(C)C=2)N2N=NC=C2)=N1 FTOSJNYBIZILBH-HKUYNNGSSA-N 0.000 claims 1
- SHGQBCFNKNAGOO-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5,6-dimethyl-2-(triazol-2-yl)pyridin-3-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=NC(C)=C(C)C=2)N2N=CC=N2)=N1 SHGQBCFNKNAGOO-HKUYNNGSSA-N 0.000 claims 1
- ADLJMXGXMGUKOJ-YJBOKZPZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-(2-fluorophenyl)-1,3-oxazol-4-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C2=C(OC=N2)C=2C(=CC=CC=2)F)=N1 ADLJMXGXMGUKOJ-YJBOKZPZSA-N 0.000 claims 1
- KOAPULRKKGIKLA-HKUYNNGSSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-(4-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2N=C(SC=2C=2C=CC(F)=CC=2)C)N1C1=NC(C)=CC(C)=N1 KOAPULRKKGIKLA-HKUYNNGSSA-N 0.000 claims 1
- GWDTVNMVFNQNIK-KKSFZXQISA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(1-methylpyrazol-3-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)C2=NN(C)C=C2)=N1 GWDTVNMVFNQNIK-KKSFZXQISA-N 0.000 claims 1
- BZXSLNZHHPKYQK-YWZLYKJASA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(1h-pyrazol-5-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)C2=NNC=C2)=N1 BZXSLNZHHPKYQK-YWZLYKJASA-N 0.000 claims 1
- AIJWSTPDSILCOZ-KXBFYZLASA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 AIJWSTPDSILCOZ-KXBFYZLASA-N 0.000 claims 1
- QRPNMNBKGFDZLV-XIJCICFPSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-[2-(oxan-2-yl)pyrazol-3-yl]phenyl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)C=2N(N=CC=2)C2OCCCC2)=N1 QRPNMNBKGFDZLV-XIJCICFPSA-N 0.000 claims 1
- HNIYDSMNVPLFOY-JXFKEZNVSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)N1C1=NC(C)=CC(C)=N1 HNIYDSMNVPLFOY-JXFKEZNVSA-N 0.000 claims 1
- NEMWYHPNGUVQCK-WMZOPIPTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=NC=C(C=2)C)N2N=NC=C2)N1C1=NC(C)=CC(C)=N1 NEMWYHPNGUVQCK-WMZOPIPTSA-N 0.000 claims 1
- OQHCXNWWBQRUSP-PXNSSMCTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)N1C1=NC(C)=CC(C)=N1 OQHCXNWWBQRUSP-PXNSSMCTSA-N 0.000 claims 1
- TWRZQMSBBKPDSB-WMZOPIPTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methyl-2-(triazol-2-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=NC=C(C=2)C)N2N=CC=N2)N1C1=NC(C)=CC(C)=N1 TWRZQMSBBKPDSB-WMZOPIPTSA-N 0.000 claims 1
- IIGDQSZHCOLSQF-RDJZCZTQSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[6-methoxy-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(N=C2N2N=NC=C2)OC)N1C1=NC(C)=CC(C)=N1 IIGDQSZHCOLSQF-RDJZCZTQSA-N 0.000 claims 1
- BBZMSEWQYBHXNQ-WMZOPIPTSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[6-methyl-2-(triazol-1-yl)pyridin-3-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)N1C1=NC(C)=CC(C)=N1 BBZMSEWQYBHXNQ-WMZOPIPTSA-N 0.000 claims 1
- PBKCYYYZPATVTR-FPOVZHCZSA-N [(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[6-methyl-3-(3-methylpyridin-2-yl)pyridin-2-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(N=2)C)C=2C(=CC=CN=2)C)N1C1=NC(C)=CC(C)=N1 PBKCYYYZPATVTR-FPOVZHCZSA-N 0.000 claims 1
- ASFFYKJYANXDAE-LIRRHRJNSA-N [(1s,6r)-7-(5-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CN([C@H]1C1)C=2OC3=CC=C(C=C3N=2)Cl)CN1C(=O)C1=CC=CC=C1N1N=CC=N1 ASFFYKJYANXDAE-LIRRHRJNSA-N 0.000 claims 1
- MUXDWBWGCFZGSS-UGSOOPFHSA-N [(1s,6r)-7-(5-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2OC3=CC=C(Cl)C=C3N=2)N1C(=O)C=1C(F)=CC=CC=1N1N=CC=N1 MUXDWBWGCFZGSS-UGSOOPFHSA-N 0.000 claims 1
- KQVOXYJJSWYBFV-UGSOOPFHSA-N [(1s,6r)-7-(5-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=CC=CC(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2OC3=CC=C(Cl)C=C3N=2)=C1N1N=CC=N1 KQVOXYJJSWYBFV-UGSOOPFHSA-N 0.000 claims 1
- UGARRAULODPKDT-DJJJIMSYSA-N [(1s,6r)-7-(5-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C(F)=CC=C(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2OC3=CC=C(Cl)C=C3N=2)C=1N1N=CC=N1 UGARRAULODPKDT-DJJJIMSYSA-N 0.000 claims 1
- PMIGYMQOENSCRV-DJJJIMSYSA-N [(1s,6r)-7-(5-chloro-1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2OC3=CC=C(Cl)C=C3N=2)N1C(=O)C1=CC(F)=CC=C1N1N=CC=N1 PMIGYMQOENSCRV-DJJJIMSYSA-N 0.000 claims 1
- JOUNIVHBRMXUIX-YJBOKZPZSA-N [(1s,6r)-7-(5-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1=NC(C)=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=CC=3)N3N=CC=N3)CC[C@H]2C1 JOUNIVHBRMXUIX-YJBOKZPZSA-N 0.000 claims 1
- PAMNCOGCSYQICN-GUYCJALGSA-N [(1s,6r)-7-(6-amino-2-methylpyrimidin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=NC(N)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 PAMNCOGCSYQICN-GUYCJALGSA-N 0.000 claims 1
- LYHAZJWDNSWOIJ-SJCJKPOMSA-N [(1s,6r)-7-(6-chloropyridazin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)F)N2N=CC=N2)N1C1=CN=NC(Cl)=C1 LYHAZJWDNSWOIJ-SJCJKPOMSA-N 0.000 claims 1
- LQRWGYPSUWDZTR-YJBOKZPZSA-N [(1s,6r)-7-(6-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 LQRWGYPSUWDZTR-YJBOKZPZSA-N 0.000 claims 1
- HOQLYDYVYPJRAF-LPHOPBHVSA-N [(1s,6r)-7-(6-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 HOQLYDYVYPJRAF-LPHOPBHVSA-N 0.000 claims 1
- PKOGXQBGKRIGPC-YOEHRIQHSA-N [(1s,6r)-7-[2-(dimethylamino)-6-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound FC(F)(F)C1=NC(N(C)C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=C1 PKOGXQBGKRIGPC-YOEHRIQHSA-N 0.000 claims 1
- BWMDAFIQDYRKHB-BBRMVZONSA-N [(1s,6r)-7-[2-(dimethylamino)-6-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound FC(F)(F)C1=NC(N(C)C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=C1 BWMDAFIQDYRKHB-BBRMVZONSA-N 0.000 claims 1
- JHGJXSYUJSBXDY-GUYCJALGSA-N [(1s,6r)-7-[2-(dimethylamino)-6-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound FC(F)(F)C1=NC(N(C)C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=C1 JHGJXSYUJSBXDY-GUYCJALGSA-N 0.000 claims 1
- COQAGPWIRBBDQU-GUYCJALGSA-N [(1s,6r)-7-[2-(dimethylamino)-6-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound FC(F)(F)C1=NC(N(C)C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=C1 COQAGPWIRBBDQU-GUYCJALGSA-N 0.000 claims 1
- REABRJLCUXPAHI-LPHOPBHVSA-N [(1s,6r)-7-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 REABRJLCUXPAHI-LPHOPBHVSA-N 0.000 claims 1
- ICTFOQORRSBYLJ-YJBOKZPZSA-N [(1s,6r)-7-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 ICTFOQORRSBYLJ-YJBOKZPZSA-N 0.000 claims 1
- NMXLIXYKBDZGLU-KXBFYZLASA-N [(1s,6r)-7-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 NMXLIXYKBDZGLU-KXBFYZLASA-N 0.000 claims 1
- WTHWKCWNBUNRAF-KXBFYZLASA-N [(1s,6r)-7-[2-(dimethylamino)-6-methylpyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 WTHWKCWNBUNRAF-KXBFYZLASA-N 0.000 claims 1
- PGQUWZXMFPXHSD-JXFKEZNVSA-N [(1s,6r)-7-[4-(dimethylamino)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-(3-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound CN(C)C1=CC=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)C=2N=CC=CN=2)=C1 PGQUWZXMFPXHSD-JXFKEZNVSA-N 0.000 claims 1
- SEGXJUXXZMKYLL-KXBFYZLASA-N [(1s,6r)-7-[4-(dimethylamino)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=CC=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=C1 SEGXJUXXZMKYLL-KXBFYZLASA-N 0.000 claims 1
- RMVQTFNCMRGHFJ-PXNSSMCTSA-N [(1s,6r)-7-[4-(dimethylamino)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CN(C)C1=CC=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(C)C=CC=2)N2N=CC=N2)=C1 RMVQTFNCMRGHFJ-PXNSSMCTSA-N 0.000 claims 1
- QTRSJWYRFYJLCQ-KKSFZXQISA-N [(1s,6r)-7-[4-(dimethylamino)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)N1C1=CC(N(C)C)=CC=N1 QTRSJWYRFYJLCQ-KKSFZXQISA-N 0.000 claims 1
- KNIWFTMZQQINOZ-KKSFZXQISA-N [(1s,6r)-7-[4-(dimethylamino)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)N1C1=CC(N(C)C)=CC=N1 KNIWFTMZQQINOZ-KKSFZXQISA-N 0.000 claims 1
- OMIGRHBORNOVFI-LIRRHRJNSA-N [(1s,6r)-7-[6-(cyclopropylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)F)N2N=CC=N2)N1C(N=CN=1)=CC=1NC1CC1 OMIGRHBORNOVFI-LIRRHRJNSA-N 0.000 claims 1
- CWGQURLFXHAFQD-KSSFIOAISA-N [(1s,6r)-7-[6-(dimethylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C1=NC(N(C)C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 CWGQURLFXHAFQD-KSSFIOAISA-N 0.000 claims 1
- XVYQCSDBLWBGHX-YOEHRIQHSA-N [(1s,6r)-7-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound FC(F)(F)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 XVYQCSDBLWBGHX-YOEHRIQHSA-N 0.000 claims 1
- FKBFJEQPIKTRPN-JTSKRJEESA-N [(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1C1=CC=CS1 FKBFJEQPIKTRPN-JTSKRJEESA-N 0.000 claims 1
- NULXWPZWUYBRCG-KKSFZXQISA-N [(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1N1N=CC=N1 NULXWPZWUYBRCG-KKSFZXQISA-N 0.000 claims 1
- UDMDCPSUOZRRMH-JXFKEZNVSA-N [2-(3-chloropyridin-2-yl)-3-fluorophenyl]-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=C(F)C=CC=2)C=2C(=CC=CN=2)Cl)=N1 UDMDCPSUOZRRMH-JXFKEZNVSA-N 0.000 claims 1
- WBLFAGDVIJVAMF-LVXARBLLSA-N [2-(4-methylphenyl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N1C[C@@H]2N(C=3N=C4C=CC=CC4=NC=3)C[C@@H]2CC1 WBLFAGDVIJVAMF-LVXARBLLSA-N 0.000 claims 1
- CJWALWGZPZBUMF-JTSKRJEESA-N [2-(furan-2-yl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC=CC=C1C1=CC=CO1 CJWALWGZPZBUMF-JTSKRJEESA-N 0.000 claims 1
- HXGLBRDCFKNXJH-PXNSSMCTSA-N [2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(4,5,6-trimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=C(C)C(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 HXGLBRDCFKNXJH-PXNSSMCTSA-N 0.000 claims 1
- ICXYSAINLSBCNE-CVDCTZTESA-N [2-[6-(dimethylamino)pyridin-3-yl]-5-fluorophenyl]-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(N(C)C)=CC=C1C1=CC=C(F)C=C1C(=O)N1C[C@@H]2N(C=3N=C(C)C=C(C)N=3)C[C@@H]2CC1 ICXYSAINLSBCNE-CVDCTZTESA-N 0.000 claims 1
- QZHNTBOGFBBQGE-YOEHRIQHSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-(3-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=NC=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=CC=3F)N3N=CC=N3)CC[C@H]2C1 QZHNTBOGFBBQGE-YOEHRIQHSA-N 0.000 claims 1
- CKERJJVSZPKSBU-YOEHRIQHSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-(5-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(C)=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=CC=3F)N3N=CC=N3)CC[C@H]2C1 CKERJJVSZPKSBU-YOEHRIQHSA-N 0.000 claims 1
- HTDGQXHMLMPQGX-YOEHRIQHSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CN=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 HTDGQXHMLMPQGX-YOEHRIQHSA-N 0.000 claims 1
- IYROBDHTCYCLKD-YJBOKZPZSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 IYROBDHTCYCLKD-YJBOKZPZSA-N 0.000 claims 1
- WZFWVFYIORTRAG-WFASDCNBSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=C(C=CC=C2F)N2N=CC=N2)N1C1=NC=CC(C(F)(F)F)=N1 WZFWVFYIORTRAG-WFASDCNBSA-N 0.000 claims 1
- NOAUFFLMJAOCOG-YWZLYKJASA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C=1C(F)=CC=CC=1N1N=CC=N1 NOAUFFLMJAOCOG-YWZLYKJASA-N 0.000 claims 1
- HUDRHGDADFZPAQ-YOEHRIQHSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(3-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=NC=CN=C1N1[C@H]2CN(C(=O)C=3C(=C(F)C=CC=3)N3N=CC=N3)CC[C@H]2C1 HUDRHGDADFZPAQ-YOEHRIQHSA-N 0.000 claims 1
- ZQOKMPIGADWQHE-YOEHRIQHSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(5-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(C)=CN=C1N1[C@H]2CN(C(=O)C=3C(=C(F)C=CC=3)N3N=CC=N3)CC[C@H]2C1 ZQOKMPIGADWQHE-YOEHRIQHSA-N 0.000 claims 1
- WQEUMTUNQPIOJK-GUYCJALGSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C=CC=C(C=2N2N=CC=N2)F)N1C1=CC(C(F)(F)F)=CC=N1 WQEUMTUNQPIOJK-GUYCJALGSA-N 0.000 claims 1
- FLOMBNYPQJLSQF-YWZLYKJASA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound FC1=CC=CC(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C3C=CC=CC3=NC=2)=C1N1N=CC=N1 FLOMBNYPQJLSQF-YWZLYKJASA-N 0.000 claims 1
- UOIWGXKIAIQMDU-YJBOKZPZSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C=CC=C(C=2N2N=CC=N2)C)N1C1=CC(C(F)(F)F)=CC=N1 UOIWGXKIAIQMDU-YJBOKZPZSA-N 0.000 claims 1
- OOVZFBIAAYGBMA-KSSFIOAISA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(3-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=NC=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC(F)=CC=3)N3N=CC=N3)CC[C@H]2C1 OOVZFBIAAYGBMA-KSSFIOAISA-N 0.000 claims 1
- RNFZYXHJPPPWIF-KSSFIOAISA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(5-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(C)=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC(F)=CC=3)N3N=CC=N3)CC[C@H]2C1 RNFZYXHJPPPWIF-KSSFIOAISA-N 0.000 claims 1
- MQUOGPOCGAQVDA-KSSFIOAISA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CN=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 MQUOGPOCGAQVDA-KSSFIOAISA-N 0.000 claims 1
- FUVWHKNIXNMRLW-GUYCJALGSA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound FC(F)(F)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 FUVWHKNIXNMRLW-GUYCJALGSA-N 0.000 claims 1
- UQLKAWXIWWVWLO-BTYIYWSLSA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C=1C(F)=CC=C(C(=O)N2C[C@@H]3N(C[C@@H]3CC2)C=2N=C3C=CC=CC3=NC=2)C=1N1N=CC=N1 UQLKAWXIWWVWLO-BTYIYWSLSA-N 0.000 claims 1
- VSHKXJBZUXATST-LIRRHRJNSA-N [4-methoxy-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(C=C2N2N=CC=N2)OC)N1C1=CC(C(F)(F)F)=CC=N1 VSHKXJBZUXATST-LIRRHRJNSA-N 0.000 claims 1
- GQWQSRXZJIQFPF-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]-(6-quinoxalin-2-yl-3,6-diazabicyclo[3.2.0]heptan-3-yl)methanone Chemical compound S1C(C)=NC(C(=O)N2CC3N(CC3C2)C=2N=C3C=CC=CC3=NC=2)=C1C1=CC=CC=C1F GQWQSRXZJIQFPF-UHFFFAOYSA-N 0.000 claims 1
- JANFKWUUXNFEKA-UHFFFAOYSA-N [5-(2-fluorophenyl)-2-methyl-1,3-thiazol-4-yl]-[6-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]methanone Chemical compound C=1C=CC=C(F)C=1C=1SC(C)=NC=1C(=O)N(CC12)CC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 JANFKWUUXNFEKA-UHFFFAOYSA-N 0.000 claims 1
- VGVHYZBJMGKIJW-WMZOPIPTSA-N [5-(3-chlorophenyl)-1,3-oxazol-4-yl]-[(1s,6r)-7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC(C)=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C2=C(OC=N2)C=2C=C(Cl)C=CC=2)=N1 VGVHYZBJMGKIJW-WMZOPIPTSA-N 0.000 claims 1
- BQLBIUMHDBUEDU-KSSFIOAISA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(3-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=NC=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=C(F)C=3)N3N=CC=N3)CC[C@H]2C1 BQLBIUMHDBUEDU-KSSFIOAISA-N 0.000 claims 1
- IWLOIZWVNYUPSQ-KXBFYZLASA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(4-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC=NC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=C1 IWLOIZWVNYUPSQ-KXBFYZLASA-N 0.000 claims 1
- AXKXZMMWINVUTB-KSSFIOAISA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(5-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(C)=CN=C1N1[C@H]2CN(C(=O)C=3C(=CC=C(F)C=3)N3N=CC=N3)CC[C@H]2C1 AXKXZMMWINVUTB-KSSFIOAISA-N 0.000 claims 1
- LRUPPXLBYVSMRB-KXBFYZLASA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(5-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound N1=CC(C)=CC=C1N1[C@H]2CN(C(=O)C=3C(=CC=C(F)C=3)N3N=CC=N3)CC[C@H]2C1 LRUPPXLBYVSMRB-KXBFYZLASA-N 0.000 claims 1
- HAGQQHVHIKDPBI-KSSFIOAISA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyrazin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CN=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 HAGQQHVHIKDPBI-KSSFIOAISA-N 0.000 claims 1
- UBJATSKHGOXQKG-KXBFYZLASA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CC1=CC=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 UBJATSKHGOXQKG-KXBFYZLASA-N 0.000 claims 1
- VNLSECZYCDNMND-KSSFIOAISA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(6-methylpyrimidin-4-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 VNLSECZYCDNMND-KSSFIOAISA-N 0.000 claims 1
- ARQKAHQKXFVRJJ-UGSOOPFHSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)F)N2N=CC=N2)N1C1=CC(C(F)(F)F)=CC=N1 ARQKAHQKXFVRJJ-UGSOOPFHSA-N 0.000 claims 1
- CRIYJDODIBCTBX-LRDDRELGSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)F)N2N=CC=N2)N1C1=NC=CC(C(F)(F)F)=N1 CRIYJDODIBCTBX-LRDDRELGSA-N 0.000 claims 1
- DMZVAYVMPQPDCT-GUYCJALGSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[6-(methylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C1=NC(NC)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 DMZVAYVMPQPDCT-GUYCJALGSA-N 0.000 claims 1
- BUQBQTFWQAKRGN-GUYCJALGSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[6-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)F)N2N=CC=N2)N1C1=CC=CC(C(F)(F)F)=N1 BUQBQTFWQAKRGN-GUYCJALGSA-N 0.000 claims 1
- WRKJNPWDISJKIK-KSSFIOAISA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[6-methyl-2-(methylamino)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound CNC1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 WRKJNPWDISJKIK-KSSFIOAISA-N 0.000 claims 1
- KLCIUBIBYLAGQH-GUYCJALGSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound FC(F)(F)C1=NC(C)=CC(N2[C@H]3CN(CC[C@H]3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 KLCIUBIBYLAGQH-GUYCJALGSA-N 0.000 claims 1
- UOFXNRKZCLVAQG-BTYIYWSLSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=CC(F)=CC=C1N1N=CC=N1 UOFXNRKZCLVAQG-BTYIYWSLSA-N 0.000 claims 1
- RQDUWBHQTQOSSQ-JXFKEZNVSA-N [5-methoxy-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-(4-methylpyridin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)N1C1=CC(C)=CC=N1 RQDUWBHQTQOSSQ-JXFKEZNVSA-N 0.000 claims 1
- PCVRBMOCOCUDDO-LIRRHRJNSA-N [5-methoxy-2-(triazol-2-yl)phenyl]-[(1s,6r)-7-[4-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(C=2)OC)N2N=CC=N2)N1C1=CC(C(F)(F)F)=CC=N1 PCVRBMOCOCUDDO-LIRRHRJNSA-N 0.000 claims 1
- ARHFXSDSNOHZRP-UHFFFAOYSA-N [6-(3,6-dimethylpyrazin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 ARHFXSDSNOHZRP-UHFFFAOYSA-N 0.000 claims 1
- MRNWHYAAFSHWKP-UHFFFAOYSA-N [6-(3,6-dimethylpyrazin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CN=C(C)C(N2C3CN(CC3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 MRNWHYAAFSHWKP-UHFFFAOYSA-N 0.000 claims 1
- MWACBRSAFUHLQD-UHFFFAOYSA-N [6-(4,6-dimethoxypyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-ethoxynaphthalen-1-yl)methanone Chemical compound CCOC1=CC=C2C=CC=CC2=C1C(=O)N(CC12)CC1CN2C1=NC(OC)=CC(OC)=N1 MWACBRSAFUHLQD-UHFFFAOYSA-N 0.000 claims 1
- QZZLUCJJEVICBK-UHFFFAOYSA-N [6-(4,6-dimethoxypyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC(OC)=NC(N2C3CN(CC3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 QZZLUCJJEVICBK-UHFFFAOYSA-N 0.000 claims 1
- HDDZEXAXEGCJCU-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-ethoxynaphthalen-1-yl)methanone Chemical compound CCOC1=CC=C2C=CC=CC2=C1C(=O)N(CC12)CC1CN2C1=NC(C)=CC(C)=N1 HDDZEXAXEGCJCU-UHFFFAOYSA-N 0.000 claims 1
- GBJJYXHANNSQKY-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 GBJJYXHANNSQKY-UHFFFAOYSA-N 0.000 claims 1
- PXGILTMBIFWHHJ-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=N1 PXGILTMBIFWHHJ-UHFFFAOYSA-N 0.000 claims 1
- HSGJPHNFDOIBDA-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 HSGJPHNFDOIBDA-UHFFFAOYSA-N 0.000 claims 1
- UXGFCQUVIQGGCN-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 UXGFCQUVIQGGCN-UHFFFAOYSA-N 0.000 claims 1
- ZHTXNTPPRRBEQR-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[4-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC(F)=CC=2)N2N=CC=N2)=N1 ZHTXNTPPRRBEQR-UHFFFAOYSA-N 0.000 claims 1
- YQTPXDCYCMFPJY-UHFFFAOYSA-N [6-(4,6-dimethylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)=N1 YQTPXDCYCMFPJY-UHFFFAOYSA-N 0.000 claims 1
- QKNCGIRCYXKJSV-UHFFFAOYSA-N [6-(4-methoxypyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-phenylphenyl)methanone Chemical compound COC1=CC=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 QKNCGIRCYXKJSV-UHFFFAOYSA-N 0.000 claims 1
- VBUGEBALXLUROO-UHFFFAOYSA-N [6-(4-methoxypyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-thiophen-2-ylphenyl)methanone Chemical compound COC1=CC=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)C=2SC=CC=2)=N1 VBUGEBALXLUROO-UHFFFAOYSA-N 0.000 claims 1
- DJPBNQLBPNZGFT-UHFFFAOYSA-N [6-(4-methylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-(2-phenylphenyl)methanone Chemical compound CC1=CC=NC(N2C3CN(CC3C2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 DJPBNQLBPNZGFT-UHFFFAOYSA-N 0.000 claims 1
- UIAYSTIWMICWGB-UHFFFAOYSA-N [6-(4-phenylpyrimidin-2-yl)-3,6-diazabicyclo[3.2.0]heptan-3-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C=1C=CC=C(N2N=CC=N2)C=1C(=O)N(CC12)CC1CN2C(N=1)=NC=CC=1C1=CC=CC=C1 UIAYSTIWMICWGB-UHFFFAOYSA-N 0.000 claims 1
- FCTUBUGTPHYNDM-ZFWWWQNUSA-N [6-methyl-2-(triazol-1-yl)pyridin-3-yl]-[(1s,6r)-7-[4-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)N1C1=NC=CC(C(F)(F)F)=N1 FCTUBUGTPHYNDM-ZFWWWQNUSA-N 0.000 claims 1
- YQERGQKPVYVSHB-HOCLYGCPSA-N [6-methyl-2-(triazol-1-yl)pyridin-3-yl]-[(1s,6r)-7-[6-methyl-2-(trifluoromethyl)pyrimidin-4-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C2=CC=C(N=C2N2N=NC=C2)C)N1C1=CC(C)=NC(C(F)(F)F)=N1 YQERGQKPVYVSHB-HOCLYGCPSA-N 0.000 claims 1
- CEOKSNMREUEXFC-PXNSSMCTSA-N [6-methyl-3-(3-methylpyridin-2-yl)pyridin-2-yl]-[(1s,6r)-7-[5-(trifluoromethyl)pyridin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(N=2)C)C=2C(=CC=CN=2)C)N1C1=CC=C(C(F)(F)F)C=N1 CEOKSNMREUEXFC-PXNSSMCTSA-N 0.000 claims 1
- MYHJSNVNRMJOSO-LPHOPBHVSA-N [6-methyl-3-(3-methylpyridin-2-yl)pyridin-2-yl]-[(1s,6r)-7-[5-(trifluoromethyl)pyrimidin-2-yl]-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1CCN(C[C@@H]11)C(=O)C=2C(=CC=C(N=2)C)C=2C(=CC=CN=2)C)N1C1=NC=C(C(F)(F)F)C=N1 MYHJSNVNRMJOSO-LPHOPBHVSA-N 0.000 claims 1
- LQALCIIIVFXHFV-CVDCTZTESA-N [6-methyl-3-(3-methylpyridin-2-yl)pyridin-2-yl]-[(1s,6r)-7-quinoxalin-2-yl-4,7-diazabicyclo[4.2.0]octan-4-yl]methanone Chemical compound C([C@@H]1N(C[C@@H]1CC1)C=2N=C3C=CC=CC3=NC=2)N1C(=O)C1=NC(C)=CC=C1C1=NC=CC=C1C LQALCIIIVFXHFV-CVDCTZTESA-N 0.000 claims 1
- XZILTLXRCKGKCU-UHFFFAOYSA-N [7-(1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2,6-dimethoxyphenyl)methanone Chemical compound COC1=CC=CC(OC)=C1C(=O)N1CC2N(C=3OC4=CC=CC=C4N=3)CC2CC1 XZILTLXRCKGKCU-UHFFFAOYSA-N 0.000 claims 1
- YFDJIMJVVGFZJM-UHFFFAOYSA-N [7-(1,3-benzoxazol-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-phenylphenyl)methanone Chemical compound C1CC2CN(C=3OC4=CC=CC=C4N=3)C2CN1C(=O)C1=CC=CC=C1C1=CC=CC=C1 YFDJIMJVVGFZJM-UHFFFAOYSA-N 0.000 claims 1
- QAFFSVOOPXEZBT-UHFFFAOYSA-N [7-(4,6-dimethoxypyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC(OC)=NC(N2C3CN(CCC3C2)C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)=N1 QAFFSVOOPXEZBT-UHFFFAOYSA-N 0.000 claims 1
- OXMKVTUMMCUKNW-UHFFFAOYSA-N [7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(2-phenylpyrazol-3-yl)methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CCC3C2)C(=O)C=2N(N=CC=2)C=2C=CC=CC=2)=N1 OXMKVTUMMCUKNW-UHFFFAOYSA-N 0.000 claims 1
- RUTAJQSZMQXFES-UHFFFAOYSA-N [7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-(5-phenyl-1,2-oxazol-4-yl)methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CCC3C2)C(=O)C2=C(ON=C2)C=2C=CC=CC=2)=N1 RUTAJQSZMQXFES-UHFFFAOYSA-N 0.000 claims 1
- ZIRWOJYFULNHJD-UHFFFAOYSA-N [7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(3-fluorophenyl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CCC3C2)C(=O)C=2C(=CC=CC=2)C=2C=C(F)C=CC=2)=N1 ZIRWOJYFULNHJD-UHFFFAOYSA-N 0.000 claims 1
- TUTAWSGKGPLSHI-UHFFFAOYSA-N [7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[2-(4-methylphenyl)phenyl]methanone Chemical compound C1=CC(C)=CC=C1C1=CC=CC=C1C(=O)N1CC2N(C=3N=C(C)C=C(C)N=3)CC2CC1 TUTAWSGKGPLSHI-UHFFFAOYSA-N 0.000 claims 1
- CLWDSMCHKJFZFZ-UHFFFAOYSA-N [7-(4,6-dimethylpyrimidin-2-yl)-4,7-diazabicyclo[4.2.0]octan-4-yl]-[3-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC(C)=NC(N2C3CN(CCC3C2)C(=O)C=2C(=C(F)C=CC=2)N2N=CC=N2)=N1 CLWDSMCHKJFZFZ-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000008784 apnea Diseases 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 150000005829 chemical entities Chemical class 0.000 claims 1
- 201000001883 cholelithiasis Diseases 0.000 claims 1
- 125000006005 fluoroethoxy group Chemical group 0.000 claims 1
- 208000001130 gallstones Diseases 0.000 claims 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims 1
- 208000000509 infertility Diseases 0.000 claims 1
- 230000036512 infertility Effects 0.000 claims 1
- 231100000535 infertility Toxicity 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- MSXIOWULDXZJLX-UHFFFAOYSA-N n,n-dimethylpyrimidin-4-amine Chemical compound CN(C)C1=CC=NC=N1 MSXIOWULDXZJLX-UHFFFAOYSA-N 0.000 claims 1
- DEEVLMZIRQYUEJ-UHFFFAOYSA-N n-cyclopropylpyrimidin-4-amine Chemical compound C1CC1NC1=CC=NC=N1 DEEVLMZIRQYUEJ-UHFFFAOYSA-N 0.000 claims 1
- VERCQLOBLOLFMW-UHFFFAOYSA-N n-methylpyrimidin-4-amine Chemical compound CNC1=CC=NC=N1 VERCQLOBLOLFMW-UHFFFAOYSA-N 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 108060005714 orexin Proteins 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25452909P | 2009-10-23 | 2009-10-23 | |
| US61/254,529 | 2009-10-23 | ||
| PCT/US2010/053609 WO2011050200A1 (en) | 2009-10-23 | 2010-10-21 | Fused heterocyclic compounds as orexin receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013508404A JP2013508404A (ja) | 2013-03-07 |
| JP2013508404A5 true JP2013508404A5 (enExample) | 2013-11-28 |
| JP5847087B2 JP5847087B2 (ja) | 2016-01-20 |
Family
ID=43430851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012535385A Expired - Fee Related JP5847087B2 (ja) | 2009-10-23 | 2010-10-21 | オレキシン受容体調節因子としての縮合複素環式化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8680275B2 (enExample) |
| EP (1) | EP2491034B1 (enExample) |
| JP (1) | JP5847087B2 (enExample) |
| AR (1) | AR078733A1 (enExample) |
| CL (1) | CL2010001159A1 (enExample) |
| PE (1) | PE20110296A1 (enExample) |
| TW (1) | TW201121966A (enExample) |
| UY (1) | UY32968A (enExample) |
| WO (1) | WO2011050200A1 (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012004753A (es) | 2009-10-23 | 2012-09-07 | Janssen Pharmaceutica Nv | Octahidropirrolo[3,4-c]pirrolos disustituidos como moduladores del receptor de orexina. |
| WO2012085857A1 (en) * | 2010-12-22 | 2012-06-28 | Actelion Pharmaceuticals Ltd | 3,8-diaza-bicyclo[4.2.0]oct-3-yl amides |
| WO2013050938A1 (en) * | 2011-10-04 | 2013-04-11 | Actelion Pharmaceuticals Ltd | 3,7-diazabicyclo[3.3.1]nonane and 9-oxa-3,7-diazabicyclo[3.3.1]nonane derivatives |
| EA024106B1 (ru) | 2011-11-08 | 2016-08-31 | Актелион Фармасьютиклз Лтд. | Производные 2-(1,2,3-триазол-2-ил)бензамида и 3-(1,2,3-триазол-2-ил)пиколинамида |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| RU2014136339A (ru) | 2012-02-07 | 2016-03-27 | Иолас Терапьютикс, Инк. | Замещенные пролины/пиперидины как антагонисты орексиновых рецепторов |
| PT2855453T (pt) | 2012-06-04 | 2017-03-09 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazol-prolina |
| WO2014057435A1 (en) | 2012-10-10 | 2014-04-17 | Actelion Pharmaceuticals Ltd | Orexin receptor antagonists which are [ortho bi (hetero )aryl]-[2-(meta bi (hetero )aryl)-pyrrolidin-1-yl]-methanone derivatives |
| CN103012293A (zh) * | 2012-12-13 | 2013-04-03 | 同济大学 | 一种抗失眠药物mk-4305中间体的合成方法 |
| WO2014113303A1 (en) * | 2013-01-16 | 2014-07-24 | Merck Sharp & Dohme Corp. | 4-fluoropiperidine orexin receptor antagonists |
| EP2970241A1 (en) | 2013-03-12 | 2016-01-20 | Actelion Pharmaceuticals Ltd. | Azetidine amide derivatives as orexin receptor antagonists |
| TW201444849A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代的7-氮雜雙環類及其作為食慾激素受體調節劑之用途 |
| TWI621618B (zh) | 2013-03-13 | 2018-04-21 | 比利時商健生藥品公司 | 經取代２－氮雜雙環類及其作為食慾素受體調控劑之用途 |
| TW201444821A (zh) | 2013-03-13 | 2014-12-01 | Janssen Pharmaceutica Nv | 經取代之哌啶化合物及其作為食慾素受體調節劑之用途 |
| SG11201600082VA (en) * | 2013-07-10 | 2016-02-26 | Vertex Pharma | Fused piperidine amides as modulators of ion channels |
| UA116053C2 (uk) | 2013-12-04 | 2018-01-25 | Ідорсія Фармасьютікалз Лтд | Застосування похідних бензоімідазолу-проліну |
| US9790220B2 (en) * | 2014-02-20 | 2017-10-17 | Takeda Pharmaceutical Company Limited | Substituted cyclopentanes, tetrahydrofuranes and pyrrolidines as orexin receptor antagonists |
| EP3180332B1 (en) | 2014-08-13 | 2021-10-27 | Eolas Therapeutics Inc. | Difluoropyrrolidines as orexin receptor modulators |
| WO2016040789A1 (en) | 2014-09-11 | 2016-03-17 | Janssen Pharmaceutica Nv | Substituted 2-azabicycles and their use as orexin receptor modulators |
| WO2016085784A1 (en) * | 2014-11-26 | 2016-06-02 | Merck Sharp & Dohme Corp. | Methyl diazepane orexin receptor antagonists |
| US9938276B2 (en) | 2014-12-19 | 2018-04-10 | Merck Sharp & Dohme Corp. | 6,5-bicyclic octahydropyrrolopyridine orexin receptor antagonists |
| JP6454418B2 (ja) * | 2015-06-23 | 2019-01-16 | キッセイ薬品工業株式会社 | ピラゾール誘導体、またはその薬理学的に許容される塩 |
| US10196383B2 (en) | 2015-07-17 | 2019-02-05 | Sunshine Lake Pharma Co., Ltd. | Substituted quinazoline compounds and preparation and uses thereof |
| WO2017088759A1 (en) * | 2015-11-23 | 2017-06-01 | Sunshine Lake Pharma Co., Ltd. | OCTAHYDROPYRROLO [3, 4-c] PYRROLE DERIVATIVES AND USES THEREOF |
| KR102738491B1 (ko) | 2016-02-12 | 2024-12-03 | 아스트라제네카 아베 | 오렉신 수용체 조정제로서의 할로-치환된 피페리딘 |
| RS63296B1 (sr) | 2016-03-10 | 2022-07-29 | Janssen Pharmaceutica Nv | Metode lečenja depresije korišćenjem antagonista receptora oreksin-2 |
| JP6654614B2 (ja) * | 2016-12-21 | 2020-02-26 | キッセイ薬品工業株式会社 | Ｔｒｐｍ８阻害薬 |
| CA3059394C (en) | 2017-05-03 | 2023-09-12 | Idorsia Pharmaceuticals Ltd | Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives |
| EP3668864B1 (en) | 2017-09-28 | 2021-07-21 | Boehringer Ingelheim International GmbH | N-(2,2-difluoroethyl)-n-[(pyrimidinylamino)propanyl]arylcarboxamides |
Family Cites Families (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6375897B1 (en) | 2000-02-14 | 2002-04-23 | Ansys Technologies, Inc. | Urine collection cup |
| US6809105B2 (en) | 2000-04-27 | 2004-10-26 | Abbott Laboratories | Diazabicyclic central nervous system active agents |
| MY145722A (en) | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| US7470710B2 (en) | 2001-06-28 | 2008-12-30 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| US6455722B1 (en) | 2001-06-29 | 2002-09-24 | Pabu Services, Inc. | Process for the production of pentaerythritol phosphate alcohol |
| GB0130341D0 (en) | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
| ES2278197T3 (es) | 2002-07-09 | 2007-08-01 | Actelion Pharmaceuticals Ltd. | Derivados de 7,8,9,10-tetrahidro-6h-azepino, 6,7,8,9-tetrahidro-pirido y 2,3-dihidro-2h-pirrolo(1,2-b)-quinazolinona. |
| WO2004033418A2 (en) | 2002-10-11 | 2004-04-22 | Actelion Pharmaceuticals Ltd. | Sulfonylamino-acetic derivatives and their use as orexin receptor antagonists |
| GB0225944D0 (en) | 2002-11-06 | 2002-12-11 | Glaxo Group Ltd | Novel compounds |
| US20040242641A1 (en) * | 2003-05-27 | 2004-12-02 | Buckley Michael J. | (1S,5S)-3-(5,6-dichloro-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane is an effective analgesic agent |
| US7399765B2 (en) | 2003-09-19 | 2008-07-15 | Abbott Laboratories | Substituted diazabicycloalkane derivatives |
| US20050065178A1 (en) | 2003-09-19 | 2005-03-24 | Anwer Basha | Substituted diazabicycloakane derivatives |
| CA2587141A1 (en) | 2004-11-24 | 2006-06-01 | Pfizer Inc. | Octahydropyrrolo[3,4-c]pyrrole derivatives |
| RU2007146444A (ru) | 2005-05-13 | 2009-06-20 | Лексикон Фармасьютикалз, Инк. (Us) | Полициклические соединения и способы их применения |
| US20060258691A1 (en) | 2005-05-13 | 2006-11-16 | Joseph Barbosa | Methods and compositions for improving cognition |
| GB0510204D0 (en) | 2005-05-19 | 2005-06-22 | Chroma Therapeutics Ltd | Enzyme inhibitors |
| JP2009506061A (ja) * | 2005-08-26 | 2009-02-12 | メルク エンド カムパニー インコーポレーテッド | ジアザスピロデカンオレキシン受容体拮抗薬 |
| WO2007126935A2 (en) | 2006-03-29 | 2007-11-08 | Merck & Co., Inc. | Diazepan orexin receptor antagonists |
| US20090105318A1 (en) | 2006-03-29 | 2009-04-23 | Coleman Paul J | Amidoethylthioether Orexin Receptor Antagonists |
| DK2049529T3 (da) | 2006-07-14 | 2010-11-29 | Merck Sharp & Dohme | Substituerede diazepan-orexin-receptor- antagonister |
| EP2049110B1 (en) | 2006-07-14 | 2014-08-20 | Merck Sharp & Dohme Corp. | Bridged diazepan orexin receptor antagonists |
| AU2007272795A1 (en) | 2006-07-14 | 2008-01-17 | Merck & Co., Inc. | 2-substituted proline bis-amide orexin receptor antagonists |
| DE602007007497D1 (de) | 2006-09-18 | 2010-08-12 | Hoffmann La Roche | Octahydropyrroloä3,4-cüpyrrolderivate und ihre verwendung als antivirale mittel |
| EP2089018A2 (en) | 2006-11-07 | 2009-08-19 | Lexicon Pharmaceuticals, Inc. | Methods of treating cognitive impairment and dementia |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| EP2150114A4 (en) | 2007-05-18 | 2012-01-18 | Merck Sharp & Dohme | OXO-BRIDGED DIAZEPANOREXINE RECEPTOR ANTAGONISTS |
| FR2918061B1 (fr) | 2007-06-28 | 2010-10-22 | Sanofi Aventis | Derives de 6-cycloamino-3-(pyridin-4-yl)imidazo°1,2-b!- pyridazine,leur preparation et leur application en therapeutique. |
| FR2918986B1 (fr) | 2007-07-19 | 2009-09-04 | Sanofi Aventis Sa | Derives de 6-cycloamino-3-(pyridazin-4-yl)imidazo[1,2-b]- pyridazine, leur preparation et leur application en therapeutique |
| ES2400830T3 (es) | 2007-08-15 | 2013-04-12 | Actelion Pharmaceuticals Ltd. | Derivados de 1,2-diamido-etileno como antagonistas de orexina |
| JP2011502146A (ja) | 2007-10-29 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 置換ジアゼパンオレキシン受容体アンタゴニスト |
| KR20100099742A (ko) | 2007-12-21 | 2010-09-13 | 아스트라제네카 아베 | 안드로겐 수용체 관련 병태의 치료에서 사용하기 위한 이환식 유도체 |
| WO2009080533A1 (en) | 2007-12-21 | 2009-07-02 | F. Hoffmann-La Roche Ag | Heteroaryl derivatives as orexin receptor antagonists |
| GB0806536D0 (en) | 2008-04-10 | 2008-05-14 | Glaxo Group Ltd | Novel compounds |
| AR072899A1 (es) | 2008-08-07 | 2010-09-29 | Merck Sharp & Dohme | Derivados de terpiridina-carboxamida antagonistas de receptores de orexina, composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento del insomnio y la obesidad. |
| US8093255B2 (en) | 2008-10-09 | 2012-01-10 | Glaxo Group Limited | Imidazo[1,2-A]pyrimidines as orexin receptor antagonists |
| US8129384B2 (en) | 2008-10-09 | 2012-03-06 | Glaxo Group Limited | Imidazo[1,2-a]pyrazines as orexin receptor antagonists |
| CA2739916A1 (en) | 2008-10-21 | 2010-04-29 | Merck Sharp & Dohme Corp. | 2,5-disubstituted piperidine orexin receptor antagonists |
| JP2012506374A (ja) | 2008-10-21 | 2012-03-15 | メルク・シャープ・エンド・ドーム・コーポレイション | ２，５−二置換ピペリジンオレキシン受容体アンタゴニスト |
| EP2349270B1 (en) | 2008-10-21 | 2015-09-09 | Merck Sharp & Dohme Corp. | 2,5-disubstituted morpholine orexin receptor antagonists |
| US8623863B2 (en) | 2008-10-21 | 2014-01-07 | Merck Sharp & Dohme Corp. | Disubstituted azepan orexin receptor antagonists |
| WO2010048014A1 (en) | 2008-10-21 | 2010-04-29 | Merck Sharp & Dohme Corp. | 2,4-disubstituted pyrrolidine orexin receptor antagonists |
| MX2011004551A (es) | 2008-10-30 | 2011-05-25 | Merck Sharp & Dohme | Antagonistas del receptor de orexina de isonicotinamida. |
| US8703770B2 (en) | 2008-10-30 | 2014-04-22 | Merck Sharp & Dohme Corp. | Pyridazine carboxamide orexin receptor antagonists |
| EP2349262B1 (en) | 2008-10-30 | 2014-06-25 | Merck Sharp & Dohme Corp. | 2,5-disubstituted phenyl carboxamide orexin receptor antagonists |
| JP2012509912A (ja) | 2008-11-26 | 2012-04-26 | グラクソ グループ リミテッド | 新規の化合物 |
| WO2010060470A1 (en) | 2008-11-26 | 2010-06-03 | Glaxo Group Limited | Piperidine derivatives useful as orexin receptor antagonists |
| JP2012509911A (ja) | 2008-11-26 | 2012-04-26 | グラクソ グループ リミテッド | 新規の化合物 |
| AU2009324238A1 (en) | 2008-12-02 | 2010-06-10 | Glaxo Group Limited | N-{[(IR,4S,6R-3-(2-pyridinylcarbonyl)-3-azabicyclo [4.1.0] hept-4-yl] methyl}-2-heteroarylamine derivatives and uses thereof |
| AU2009324239A1 (en) | 2008-12-02 | 2010-06-10 | Glaxo Group Limited | N-{[(IR,4S,6R-3-(2-pyridinylcarbonyl)-3-azabicyclo [4.1.0]hept-4-yl] methyl}-2-heteroarylamine derivatives and uses thereof |
| GB0823467D0 (en) | 2008-12-23 | 2009-01-28 | Glaxo Group Ltd | Novel Compounds |
-
2010
- 2010-10-21 WO PCT/US2010/053609 patent/WO2011050200A1/en not_active Ceased
- 2010-10-21 US US13/503,312 patent/US8680275B2/en active Active
- 2010-10-21 EP EP10774359.3A patent/EP2491034B1/en active Active
- 2010-10-21 JP JP2012535385A patent/JP5847087B2/ja not_active Expired - Fee Related
- 2010-10-22 AR ARP100103876A patent/AR078733A1/es unknown
- 2010-10-22 TW TW099136020A patent/TW201121966A/zh unknown
- 2010-10-22 CL CL2010001159A patent/CL2010001159A1/es unknown
- 2010-10-22 PE PE2010000999A patent/PE20110296A1/es not_active Application Discontinuation
- 2010-10-25 UY UY0001032968A patent/UY32968A/es not_active Application Discontinuation