JP2014505688A - オキサジン誘導体および神経障害の処置におけるその使用 - Google Patents

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Publication number

JP2014505688A

JP2014505688A JP2013548830A JP2013548830A JP2014505688A JP 2014505688 A JP2014505688 A JP 2014505688A JP 2013548830 A JP2013548830 A JP 2013548830A JP 2013548830 A JP2013548830 A JP 2013548830A JP 2014505688 A JP2014505688 A JP 2014505688A

Authority

JP

Japan

Prior art keywords

amino

phenyl

fluoro

dihydro

pyridine

Prior art date

2011-01-12

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.)

Ceased

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• Global Dossier
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• 208000012902 Nervous system disease Diseases 0.000 title description 3
• 150000004893 oxazines Chemical class 0.000 title description 2
• 208000025966 Neurological disease Diseases 0.000 title 1
• 239000003814 drug Substances 0.000 claims abstract description 43
• 150000003839 salts Chemical group 0.000 claims abstract description 38
• 238000004519 manufacturing process Methods 0.000 claims abstract description 16
• 150000001875 compounds Chemical class 0.000 claims description 233
• -1 5-amino-3,6-dimethyl-6-trifluoromethyl-3,6-dihydro-2H- [1,4] oxazin-3-yl Chemical group 0.000 claims description 109
• 239000004480 active ingredient Substances 0.000 claims description 24
• 208000024827 Alzheimer disease Diseases 0.000 claims description 23
• 208000010877 cognitive disease Diseases 0.000 claims description 18
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 16
• VBXPXWWINCBYCW-UHFFFAOYSA-N 5-(5-amino-2-fluorophenyl)-5-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(N)=CC=C1F VBXPXWWINCBYCW-UHFFFAOYSA-N 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 239000008186 active pharmaceutical agent Substances 0.000 claims description 7
• 239000003085 diluting agent Substances 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 6
• NAKZTXHQHCNVHW-UHFFFAOYSA-N n-[3-[5-amino-6,6-bis(fluoromethyl)-3-methyl-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(C#N)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(CF)(CF)OC2)=C1 NAKZTXHQHCNVHW-UHFFFAOYSA-N 0.000 claims description 6
• WFNBWRYIRKVFGF-UHFFFAOYSA-N 3-(5-amino-2-fluorophenyl)-3,6-dimethyl-6-(trifluoromethyl)-2H-1,4-oxazin-5-amine Chemical compound C=1C(N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 WFNBWRYIRKVFGF-UHFFFAOYSA-N 0.000 claims description 5
• AJTJGMWIBKBTRW-UHFFFAOYSA-N 5-fluoro-3-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(F)=CN=C1C(O)=O AJTJGMWIBKBTRW-UHFFFAOYSA-N 0.000 claims description 4
• MYPMSNBWXOTPSY-UHFFFAOYSA-N n-[3-[5-amino-6,6-bis(fluoromethyl)-3-methyl-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethoxy)-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(OC(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(CF)(CF)OC2)=C1 MYPMSNBWXOTPSY-UHFFFAOYSA-N 0.000 claims description 3
• WRJNIDJAIBTADI-UHFFFAOYSA-N n-[3-[5-amino-6,6-bis(fluoromethyl)-3-methyl-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Cl)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(CF)(CF)OC2)=C1 WRJNIDJAIBTADI-UHFFFAOYSA-N 0.000 claims description 3
• 239000011570 nicotinamide Substances 0.000 claims description 3
• 229960003966 nicotinamide Drugs 0.000 claims description 3
• FDZVMGPNACCJOT-UHFFFAOYSA-N 2-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC(OCC(F)(F)F)=CC=2)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 FDZVMGPNACCJOT-UHFFFAOYSA-N 0.000 claims description 2
• VZHJJPJUBNSJKZ-UHFFFAOYSA-N 2-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-(cyclopropylmethoxy)pyridine-3-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC(OCC3CC3)=CC=2)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 VZHJJPJUBNSJKZ-UHFFFAOYSA-N 0.000 claims description 2
• LNMIAXJNZSZUNF-HPRDVNIFSA-N 2-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-(trideuteriomethoxy)pyridine-3-carboxamide Chemical compound NC1=NC(OC([2H])([2H])[2H])=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 LNMIAXJNZSZUNF-HPRDVNIFSA-N 0.000 claims description 2
• WLIYLCVDNRHBFA-UHFFFAOYSA-N 2-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-ethoxypyridine-3-carboxamide Chemical compound NC1=NC(OCC)=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 WLIYLCVDNRHBFA-UHFFFAOYSA-N 0.000 claims description 2
• LNMIAXJNZSZUNF-UHFFFAOYSA-N 2-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-methoxypyridine-3-carboxamide Chemical compound NC1=NC(OC)=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 LNMIAXJNZSZUNF-UHFFFAOYSA-N 0.000 claims description 2
• YZLVVYVDLDJXFU-UHFFFAOYSA-N 3-amino-N-[3-[5-amino-6,6-bis(fluoromethyl)-3-methyl-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyrazine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC(=CN=2)C(F)F)N)=CC=C(F)C=1C1(C)COC(CF)(CF)C(N)=N1 YZLVVYVDLDJXFU-UHFFFAOYSA-N 0.000 claims description 2
• JLSDOXTUCNONSN-UHFFFAOYSA-N 3-amino-N-[3-[5-amino-6,6-bis(fluoromethyl)-3-methyl-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C(F)F)N)=CC=C(F)C=1C1(C)COC(CF)(CF)C(N)=N1 JLSDOXTUCNONSN-UHFFFAOYSA-N 0.000 claims description 2
• MAAODJKWXDTPIB-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3,6,6-tris(fluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1OC(CF)(CF)C(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(=CN=2)C#N)N)=CC=C1F MAAODJKWXDTPIB-UHFFFAOYSA-N 0.000 claims description 2
• WGNWSNJNKNTWKA-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyrazine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC(=CN=2)C(F)F)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 WGNWSNJNKNTWKA-UHFFFAOYSA-N 0.000 claims description 2
• WAHBMDQONARPPN-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C(F)F)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 WAHBMDQONARPPN-UHFFFAOYSA-N 0.000 claims description 2
• XGBNYYCTJVZIKG-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C#N)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 XGBNYYCTJVZIKG-UHFFFAOYSA-N 0.000 claims description 2
• DMAHFURJVQXREY-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-prop-2-ynoxypyrazine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=NC(OCC#C)=CN=2)N)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 DMAHFURJVQXREY-UHFFFAOYSA-N 0.000 claims description 2
• WWXHQUCOXMISMY-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyrazine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=NC(=CN=2)C(F)F)N)=CC=C1F WWXHQUCOXMISMY-UHFFFAOYSA-N 0.000 claims description 2
• KDVMERQNUMSGPJ-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(=CN=2)C(F)F)N)=CC=C1F KDVMERQNUMSGPJ-UHFFFAOYSA-N 0.000 claims description 2
• ZRDWBUZRZFYHGM-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(=CN=2)C#N)N)=CC=C1F ZRDWBUZRZFYHGM-UHFFFAOYSA-N 0.000 claims description 2
• BKKQMZVUMXGDAV-UHFFFAOYSA-N 3-amino-n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-prop-2-ynoxypyrazine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=NC(OCC#C)=CN=2)N)=CC=C1F BKKQMZVUMXGDAV-UHFFFAOYSA-N 0.000 claims description 2
• YMBBVCHEKPUTLS-UHFFFAOYSA-N 5-(5-amino-2,3-difluorophenyl)-5-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-amine Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(N)=CC(F)=C1F YMBBVCHEKPUTLS-UHFFFAOYSA-N 0.000 claims description 2
• NKKVZCJLIVGCTR-UHFFFAOYSA-N CC1=CC(C(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(CF)N=C(N)C(CF)(CF)OC2)=C1 Chemical compound CC1=CC(C(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(CF)N=C(N)C(CF)(CF)OC2)=C1 NKKVZCJLIVGCTR-UHFFFAOYSA-N 0.000 claims description 2
• JNUJPPCVGYDFCU-UHFFFAOYSA-N N-[3-[5-amino-3,6,6-tris(fluoromethyl)-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound C1OC(CF)(CF)C(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F JNUJPPCVGYDFCU-UHFFFAOYSA-N 0.000 claims description 2
• TUCLYFFZWVGEBJ-UHFFFAOYSA-N N-[3-[5-amino-3,6,6-tris(fluoromethyl)-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C1OC(CF)(CF)C(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(=CN=2)C(F)F)Cl)=CC=C1F TUCLYFFZWVGEBJ-UHFFFAOYSA-N 0.000 claims description 2
• XIHYOWBKOXBEIF-UHFFFAOYSA-N N-[3-[5-amino-3,6,6-tris(fluoromethyl)-2H-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C1OC(CF)(CF)C(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(=CN=2)C(F)(F)F)Cl)=CC=C1F XIHYOWBKOXBEIF-UHFFFAOYSA-N 0.000 claims description 2
• 229940088679 drug related substance Drugs 0.000 claims description 2
• NOLUMTIEHDRMEU-UHFFFAOYSA-N n-[3-[5-amino-3,6,6-tris(fluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-cyanopyridine-2-carboxamide Chemical compound C1OC(CF)(CF)C(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(=CN=2)C#N)Cl)=CC=C1F NOLUMTIEHDRMEU-UHFFFAOYSA-N 0.000 claims description 2
• IOFNDJLWBOSVRD-UHFFFAOYSA-N n-[3-[5-amino-3,6,6-tris(fluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(C#N)=CN=C1C(=O)NC1=CC=C(F)C(C2(CF)N=C(N)C(CF)(CF)OC2)=C1 IOFNDJLWBOSVRD-UHFFFAOYSA-N 0.000 claims description 2
• DLSOBYBAIDXDOQ-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-2-chloro-6-ethoxypyridine-3-carboxamide Chemical compound ClC1=NC(OCC)=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 DLSOBYBAIDXDOQ-UHFFFAOYSA-N 0.000 claims description 2
• VGMNAYXQJZIGFP-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-2-chloro-6-methoxypyridine-3-carboxamide Chemical compound ClC1=NC(OC)=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 VGMNAYXQJZIGFP-UHFFFAOYSA-N 0.000 claims description 2
• WAZXJCCRJQZNHV-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(difluoromethoxy)pyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(OC(F)F)=CN=2)Cl)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 WAZXJCCRJQZNHV-UHFFFAOYSA-N 0.000 claims description 2
• WXMXSKJDIPTGDI-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C(F)F)Cl)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 WXMXSKJDIPTGDI-UHFFFAOYSA-N 0.000 claims description 2
• AHIYNAVMWKHOGT-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C(F)(F)F)Cl)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 AHIYNAVMWKHOGT-UHFFFAOYSA-N 0.000 claims description 2
• HYRSOCCYHCESGJ-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-cyanopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(=CN=2)C#N)Cl)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 HYRSOCCYHCESGJ-UHFFFAOYSA-N 0.000 claims description 2
• ZNGUFHSNIRZKIS-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-methoxypyridine-2-carboxamide Chemical compound ClC1=CC(OC)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 ZNGUFHSNIRZKIS-UHFFFAOYSA-N 0.000 claims description 2
• NAMXPJWEEFVLOZ-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-4-(difluoromethyl)-6-methoxypyridazine-3-carboxamide Chemical compound N1=NC(OC)=CC(C(F)F)=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 NAMXPJWEEFVLOZ-UHFFFAOYSA-N 0.000 claims description 2
• NGPXAOWJBUFQFX-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethoxy)-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(OC(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 NGPXAOWJBUFQFX-UHFFFAOYSA-N 0.000 claims description 2
• CRIDHYGDBXOMEF-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(C(F)F)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 CRIDHYGDBXOMEF-UHFFFAOYSA-N 0.000 claims description 2
• JQKKMDKUHFHSNI-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-fluoropyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(Cl)=CN=2)F)=CC=C(F)C=1C1(C)COC(C)(C(F)(F)F)C(N)=N1 JQKKMDKUHFHSNI-UHFFFAOYSA-N 0.000 claims description 2
• QWMJKTKXIPTJBE-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Cl)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 QWMJKTKXIPTJBE-UHFFFAOYSA-N 0.000 claims description 2
• HPMAQFNYRBPHHD-UHFFFAOYSA-N n-[3-[5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-6-methoxy-2-methylpyridine-3-carboxamide Chemical compound CC1=NC(OC)=CC=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)C(C)(OC2)C(F)(F)F)=C1 HPMAQFNYRBPHHD-UHFFFAOYSA-N 0.000 claims description 2
• REPYBSHAIRPIAJ-FIBGUPNXSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4,5-difluorophenyl]-3-chloro-5-(trideuteriomethoxy)pyridine-2-carboxamide Chemical compound ClC1=CC(OC([2H])([2H])[2H])=CN=C1C(=O)NC1=CC(F)=C(F)C(C2(N=C(N)COC2)C(F)F)=C1 REPYBSHAIRPIAJ-FIBGUPNXSA-N 0.000 claims description 2
• AGYZHWLVQUIXGN-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4,5-difluorophenyl]-5-cyano-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(C#N)=CN=C1C(=O)NC1=CC(F)=C(F)C(C2(N=C(N)COC2)C(F)F)=C1 AGYZHWLVQUIXGN-UHFFFAOYSA-N 0.000 claims description 2
• CIQGBHJCFGIZBE-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-1h-pyrrolo[2,3-b]pyridine-6-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2N=C3NC=C(Cl)C3=CC=2)=CC=C1F CIQGBHJCFGIZBE-UHFFFAOYSA-N 0.000 claims description 2
• BENYVODADSRWMT-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-cyanopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(=CN=2)C#N)Cl)=CC=C1F BENYVODADSRWMT-UHFFFAOYSA-N 0.000 claims description 2
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