JP2013500247A5 - - Google Patents
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- JP2013500247A5 JP2013500247A5 JP2012521053A JP2012521053A JP2013500247A5 JP 2013500247 A5 JP2013500247 A5 JP 2013500247A5 JP 2012521053 A JP2012521053 A JP 2012521053A JP 2012521053 A JP2012521053 A JP 2012521053A JP 2013500247 A5 JP2013500247 A5 JP 2013500247A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- amide
- phenyl
- dihydro
- carboxylic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims 42
- 125000004414 alkyl thio group Chemical group 0.000 claims 39
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 28
- 150000003839 salts Chemical class 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 21
- -1 cyano, nitro, amino, aminocarbonyl Chemical group 0.000 claims 20
- 150000001408 amides Chemical class 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 7
- MNNQIBXLAHVDDL-UHFFFAOYSA-N 5-bromopyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)C=N1 MNNQIBXLAHVDDL-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- GJLOKYIYZIOIPN-UHFFFAOYSA-N 5-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)C=N1 GJLOKYIYZIOIPN-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- UTRZGSGCVSZCCL-UHFFFAOYSA-N 5-bromo-3-methoxypyridine-2-carboxylic acid Chemical compound COC1=CC(Br)=CN=C1C(O)=O UTRZGSGCVSZCCL-UHFFFAOYSA-N 0.000 claims 2
- HRLVPHGCEGTVLK-UHFFFAOYSA-N 5-cyanopyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)C=N1 HRLVPHGCEGTVLK-UHFFFAOYSA-N 0.000 claims 2
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 2
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 238000004220 aggregation Methods 0.000 claims 2
- 230000002776 aggregation Effects 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- DQPLXHBLVHXKCN-SFHVURJKSA-N n-[3-[(5s)-3-amino-5-(difluoromethyl)-6,7-dihydro-2h-1,4-oxazepin-5-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1COCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F DQPLXHBLVHXKCN-SFHVURJKSA-N 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 208000019553 vascular disease Diseases 0.000 claims 2
- LHGRUGVXZLHYKE-UHFFFAOYSA-N 2,5-dimethyl-1,3-oxazole-4-carboxylic acid Chemical compound CC1=NC(C(O)=O)=C(C)O1 LHGRUGVXZLHYKE-UHFFFAOYSA-N 0.000 claims 1
- NFAYXTPYAYLORM-IBGZPJMESA-N 3-amino-n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-methoxyethoxy)pyrazine-2-carboxamide Chemical compound NC1=NC(OCCOC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 NFAYXTPYAYLORM-IBGZPJMESA-N 0.000 claims 1
- DZICWSPROOMALF-KRWDZBQOSA-N 3-amino-n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)N)=CC=C1F DZICWSPROOMALF-KRWDZBQOSA-N 0.000 claims 1
- VUEPUGVSDIHZRM-KRWDZBQOSA-N 3-amino-n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)N)=CC=C1F VUEPUGVSDIHZRM-KRWDZBQOSA-N 0.000 claims 1
- PQNCTIXRVDHLMZ-KRWDZBQOSA-N 3-amino-n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound NC1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 PQNCTIXRVDHLMZ-KRWDZBQOSA-N 0.000 claims 1
- FZJRMPKLJZLTBX-ZWKOTPCHSA-N 3-amino-n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2C(=CC(Cl)=CN=2)N)=CC=C(F)C=1[C@]1(C)CO[C@@](C)(C(F)(F)F)C(N)=N1 FZJRMPKLJZLTBX-ZWKOTPCHSA-N 0.000 claims 1
- HXRMCZBDTDCCOP-UHFFFAOYSA-N 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(C(F)(F)F)C=C1Cl HXRMCZBDTDCCOP-UHFFFAOYSA-N 0.000 claims 1
- MOWNROZTCWULAF-UHFFFAOYSA-N 5-(2-methoxyethoxy)pyridine-2-carboxylic acid Chemical compound COCCOC1=CC=C(C(O)=O)N=C1 MOWNROZTCWULAF-UHFFFAOYSA-N 0.000 claims 1
- HSUQJQQFXFPGTI-INIZCTEOSA-N 5-amino-n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1N HSUQJQQFXFPGTI-INIZCTEOSA-N 0.000 claims 1
- KNYSNNRQXSFAGE-UHFFFAOYSA-N 5-bromo-3-hydroxypyridine-2-carboxylic acid Chemical compound OC(=O)C1=NC=C(Br)C=C1O KNYSNNRQXSFAGE-UHFFFAOYSA-N 0.000 claims 1
- GSOCTKHBFREQCV-UHFFFAOYSA-N 5-bromo-3-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(Br)=CN=C1C(O)=O GSOCTKHBFREQCV-UHFFFAOYSA-N 0.000 claims 1
- QQNDJNHLMAFNJI-UHFFFAOYSA-N 5-chloro-3-methylpyridine-2-carboxylic acid Chemical compound CC1=CC(Cl)=CN=C1C(O)=O QQNDJNHLMAFNJI-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 206010059245 Angiopathy Diseases 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052805 deuterium Inorganic materials 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000007306 functionalization reaction Methods 0.000 claims 1
- LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IAYMQIFBCQYYCB-UHFFFAOYSA-N n-[3-(3-amino-6,6-difluoro-5-methyl-2,7-dihydro-1,4-oxazepin-5-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)N=C(N)COCC1(F)F IAYMQIFBCQYYCB-UHFFFAOYSA-N 0.000 claims 1
- IXSJDCOYPCXMDO-UHFFFAOYSA-N n-[3-(3-amino-6,6-difluoro-5-methyl-2,7-dihydro-1,4-oxazepin-5-yl)-4-fluorophenyl]-5-bromo-3-methoxypyridine-2-carboxamide Chemical compound COC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)C(COCC(N)=N2)(F)F)=C1 IXSJDCOYPCXMDO-UHFFFAOYSA-N 0.000 claims 1
- QGBORQFFMQILEL-UHFFFAOYSA-N n-[3-(3-amino-6,6-difluoro-5-methyl-2,7-dihydro-1,4-oxazepin-5-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Br)=CC=2)=CC=C(F)C=1C1(C)N=C(N)COCC1(F)F QGBORQFFMQILEL-UHFFFAOYSA-N 0.000 claims 1
- BAVSGDZAGDONMG-UHFFFAOYSA-N n-[3-(3-amino-6,6-difluoro-5-methyl-2,7-dihydro-1,4-oxazepin-5-yl)-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Cl)=CC=2)=CC=C(F)C=1C1(C)N=C(N)COCC1(F)F BAVSGDZAGDONMG-UHFFFAOYSA-N 0.000 claims 1
- GGQMMJIBNMOCPI-UHFFFAOYSA-N n-[3-(3-amino-6,6-difluoro-5-methyl-2,7-dihydro-1,4-oxazepin-5-yl)-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C(F)C=1C1(C)N=C(N)COCC1(F)F GGQMMJIBNMOCPI-UHFFFAOYSA-N 0.000 claims 1
- FXBGEPMHYXPSMX-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)COC2)=C1 FXBGEPMHYXPSMX-UHFFFAOYSA-N 0.000 claims 1
- AWWAZUFXKKZKCD-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Br)=CC=2)=CC=C(F)C=1C1(C)COCC(N)=N1 AWWAZUFXKKZKCD-UHFFFAOYSA-N 0.000 claims 1
- BBTMSQSMAGSWCB-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Cl)=CC=2)=CC=C(F)C=1C1(C)COCC(N)=N1 BBTMSQSMAGSWCB-UHFFFAOYSA-N 0.000 claims 1
- IHBPTEKOIRADAY-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C(F)C=1C1(C)COCC(N)=N1 IHBPTEKOIRADAY-UHFFFAOYSA-N 0.000 claims 1
- QCOIOASJNWMYBJ-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)-4-fluorophenyl]-5-methylpyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NC1=CC=C(F)C(C2(C)N=C(N)COC2)=C1 QCOIOASJNWMYBJ-UHFFFAOYSA-N 0.000 claims 1
- VAOTVYMHOSSUGC-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C=CC=2)C2(C)N=C(N)COC2)=C1C VAOTVYMHOSSUGC-UHFFFAOYSA-N 0.000 claims 1
- YGNQIPLXHYPNNV-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C=CC=2)C2(C)N=C(N)COC2)=C1 YGNQIPLXHYPNNV-UHFFFAOYSA-N 0.000 claims 1
- NXPMSJJJEIMDON-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)NC=2C=C(C=CC=2)C2(C)N=C(N)COC2)=C1 NXPMSJJJEIMDON-UHFFFAOYSA-N 0.000 claims 1
- NSQDLDKQMKWWRH-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-3-fluoropyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2C(=CC=CN=2)F)=CC=1C1(C)COCC(N)=N1 NSQDLDKQMKWWRH-UHFFFAOYSA-N 0.000 claims 1
- OSXUMSQYXNHEJV-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-4-bromobenzamide Chemical compound C=1C=CC(NC(=O)C=2C=CC(Br)=CC=2)=CC=1C1(C)COCC(N)=N1 OSXUMSQYXNHEJV-UHFFFAOYSA-N 0.000 claims 1
- CLRSFVMIVMUEJA-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-4-bromofuran-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2OC=C(Br)C=2)=CC=1C1(C)COCC(N)=N1 CLRSFVMIVMUEJA-UHFFFAOYSA-N 0.000 claims 1
- VOTXALWSGSHBMR-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-(3-methylpyrazol-1-yl)pyrazine-2-carboxamide Chemical compound N1=C(C)C=CN1C1=CN=C(C(=O)NC=2C=C(C=CC=2)C2(C)N=C(N)COC2)C=N1 VOTXALWSGSHBMR-UHFFFAOYSA-N 0.000 claims 1
- DKIJRIQOWUZUFU-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-(trifluoromethyl)furan-3-carboxamide Chemical compound C=1C=CC(NC(=O)C=2C=C(OC=2)C(F)(F)F)=CC=1C1(C)COCC(N)=N1 DKIJRIQOWUZUFU-UHFFFAOYSA-N 0.000 claims 1
- VZIVJCUBWLYNSB-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(=CC=2)C(F)(F)F)=CC=1C1(C)COCC(N)=N1 VZIVJCUBWLYNSB-UHFFFAOYSA-N 0.000 claims 1
- ZLPSIWKLMGIZEM-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-[3-(trifluoromethyl)pyrazol-1-yl]pyrazine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(=NC=2)N2N=C(C=C2)C(F)(F)F)=CC=1C1(C)COCC(N)=N1 ZLPSIWKLMGIZEM-UHFFFAOYSA-N 0.000 claims 1
- HALWMQVNBCAXRZ-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=1C1(C)COCC(N)=N1 HALWMQVNBCAXRZ-UHFFFAOYSA-N 0.000 claims 1
- SDRFKEHYIFLRFI-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-bromopyrimidine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Br)=CN=2)=CC=1C1(C)COCC(N)=N1 SDRFKEHYIFLRFI-UHFFFAOYSA-N 0.000 claims 1
- ZZUPAAPYPBQGKS-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Cl)=CC=2)=CC=1C1(C)COCC(N)=N1 ZZUPAAPYPBQGKS-UHFFFAOYSA-N 0.000 claims 1
- PVDUHQIYHKAWGX-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-cyanopyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=1C1(C)COCC(N)=N1 PVDUHQIYHKAWGX-UHFFFAOYSA-N 0.000 claims 1
- USQWUZBMLRCKEY-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=CC(C2(C)N=C(N)COC2)=C1 USQWUZBMLRCKEY-UHFFFAOYSA-N 0.000 claims 1
- KWLPFPXHUOTAAV-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-methylpyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NC1=CC=CC(C2(C)N=C(N)COC2)=C1 KWLPFPXHUOTAAV-UHFFFAOYSA-N 0.000 claims 1
- WBJSDDKRXQAZRI-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-5-methylpyridine-2-carboxamide Chemical compound N1=CC(C)=CC=C1C(=O)NC1=CC=CC(C2(C)N=C(N)COC2)=C1 WBJSDDKRXQAZRI-UHFFFAOYSA-N 0.000 claims 1
- NEVZUGJJPYBOQE-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-6-oxo-1h-pyrazine-3-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(O)=NC=2)=CC=1C1(C)COCC(N)=N1 NEVZUGJJPYBOQE-UHFFFAOYSA-N 0.000 claims 1
- HERLEGFVQLSJDB-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]-6-oxo-1h-pyridazine-3-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=NC(O)=CC=2)=CC=1C1(C)COCC(N)=N1 HERLEGFVQLSJDB-UHFFFAOYSA-N 0.000 claims 1
- FQFLVGMKEDQOGB-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]furan-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2OC=CC=2)=CC=1C1(C)COCC(N)=N1 FQFLVGMKEDQOGB-UHFFFAOYSA-N 0.000 claims 1
- ZWMZTUXDXPWHKA-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=C3C=CC=CN3C=2)=CC=1C1(C)COCC(N)=N1 ZWMZTUXDXPWHKA-UHFFFAOYSA-N 0.000 claims 1
- FFUNHRRXZYUZCU-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC=CC=2)=CC=1C1(C)COCC(N)=N1 FFUNHRRXZYUZCU-UHFFFAOYSA-N 0.000 claims 1
- ONXPSTRUSLRMOR-UHFFFAOYSA-N n-[3-(5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl)phenyl]pyridine-3-carboxamide Chemical compound C=1C=CC(NC(=O)C=2C=NC=CC=2)=CC=1C1(C)COCC(N)=N1 ONXPSTRUSLRMOR-UHFFFAOYSA-N 0.000 claims 1
- GKUQBILDQJOXTH-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-1,5-dimethyltriazole-4-carboxamide Chemical compound N1=NN(C)C(C)=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 GKUQBILDQJOXTH-INIZCTEOSA-N 0.000 claims 1
- FBNZAZZZKUMSCC-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-1-ethylimidazole-2-carboxamide Chemical compound CCN1C=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 FBNZAZZZKUMSCC-KRWDZBQOSA-N 0.000 claims 1
- WHIJATQLCPCKPU-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-1-methyl-4-nitropyrazole-3-carboxamide Chemical compound CN1C=C([N+]([O-])=O)C(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=N1 WHIJATQLCPCKPU-INIZCTEOSA-N 0.000 claims 1
- UTJRCQHYZVFEDY-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-1-methylimidazole-2-carboxamide Chemical compound CN1C=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 UTJRCQHYZVFEDY-INIZCTEOSA-N 0.000 claims 1
- CBLDZBBQCRNDJM-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-1-methylpyrazole-3-carboxamide Chemical compound CN1C=CC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=N1 CBLDZBBQCRNDJM-INIZCTEOSA-N 0.000 claims 1
- ZZZPIVDRDSYYLA-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1C ZZZPIVDRDSYYLA-KRWDZBQOSA-N 0.000 claims 1
- UEOXQEPMCSIOKT-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-2-ethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(CC)=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1 UEOXQEPMCSIOKT-KRWDZBQOSA-N 0.000 claims 1
- XZXBUWVLCCTZNZ-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1 XZXBUWVLCCTZNZ-INIZCTEOSA-N 0.000 claims 1
- OUSIXFSEDPAPFO-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-2-methyl-1,3-thiazole-4-carboxamide Chemical compound S1C(C)=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1 OUSIXFSEDPAPFO-INIZCTEOSA-N 0.000 claims 1
- RANYUTVQHPXCFQ-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F RANYUTVQHPXCFQ-KRWDZBQOSA-N 0.000 claims 1
- WTCPZYAUXDJZGB-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3,5-difluoropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(F)=CN=2)F)=CC=C1F WTCPZYAUXDJZGB-KRWDZBQOSA-N 0.000 claims 1
- CBZXJHNIGVYMNJ-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3,5-dimethoxypyridine-2-carboxamide Chemical compound COC1=CC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 CBZXJHNIGVYMNJ-IBGZPJMESA-N 0.000 claims 1
- DVBOVNPSLIMVII-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(difluoromethoxy)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(OC(F)F)=CN=2)Cl)=CC=C1F DVBOVNPSLIMVII-SFHVURJKSA-N 0.000 claims 1
- UNXLSXAPWMBKPT-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(fluoromethoxy)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(OCF)=CN=2)Cl)=CC=C1F UNXLSXAPWMBKPT-SFHVURJKSA-N 0.000 claims 1
- AGGCPSHNHGXPJR-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(methoxymethyl)pyridine-2-carboxamide Chemical compound ClC1=CC(COC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 AGGCPSHNHGXPJR-IBGZPJMESA-N 0.000 claims 1
- DLWZVWXIFIDOTB-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-chloro-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(=CN=2)C(F)(F)F)Cl)=CC=C1F DLWZVWXIFIDOTB-KRWDZBQOSA-N 0.000 claims 1
- RPHZZKXVDZPWGK-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-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([C@]2(N=C(N)COC2)C(F)F)=C1 RPHZZKXVDZPWGK-SFHVURJKSA-N 0.000 claims 1
- HJVKJVKFIJNIQM-FQEVSTJZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-fluoro-5-(2-methoxyethoxy)pyridine-2-carboxamide Chemical compound FC1=CC(OCCOC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 HJVKJVKFIJNIQM-FQEVSTJZSA-N 0.000 claims 1
- IQZCFTCUADKAEQ-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-4-bromofuran-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2OC=C(Br)C=2)=CC=C1F IQZCFTCUADKAEQ-INIZCTEOSA-N 0.000 claims 1
- ZYKHATRVIWWARX-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2,2,2-trifluoroethoxy)pyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OCC(F)(F)F)=NC=2)=CC=C1F ZYKHATRVIWWARX-KRWDZBQOSA-N 0.000 claims 1
- KADQXWUYWQGVBV-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2,2-difluoroethoxy)pyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OCC(F)F)=NC=2)=CC=C1F KADQXWUYWQGVBV-SFHVURJKSA-N 0.000 claims 1
- ZOPGZMQBNBVSOI-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-fluoroethoxy)pyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OCCF)=NC=2)=CC=C1F ZOPGZMQBNBVSOI-SFHVURJKSA-N 0.000 claims 1
- YQNKMDOJYUDEDD-FQEVSTJZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-methoxyethoxy)-3-methylpyrazine-2-carboxamide Chemical compound CC1=NC(OCCOC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 YQNKMDOJYUDEDD-FQEVSTJZSA-N 0.000 claims 1
- SBZDOFNVPNDDLA-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-methoxyethoxy)pyrazine-2-carboxamide Chemical compound C1=NC(OCCOC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 SBZDOFNVPNDDLA-IBGZPJMESA-N 0.000 claims 1
- QFVHGARCQKVZOL-FQEVSTJZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-methoxyethoxy)pyridine-2-carboxamide Chemical compound N1=CC(OCCOC)=CC=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 QFVHGARCQKVZOL-FQEVSTJZSA-N 0.000 claims 1
- NSVDKFCBXGHJRA-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-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([C@]2(N=C(N)COC2)C(F)F)=C1 NSVDKFCBXGHJRA-IBGZPJMESA-N 0.000 claims 1
- KOFGSVGFHARRGP-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethoxy)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OC(F)F)=CC=2)=CC=C1F KOFGSVGFHARRGP-SFHVURJKSA-N 0.000 claims 1
- AOIJYHFJBXMXBN-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(=NC=2)C(F)F)=CC=C1F AOIJYHFJBXMXBN-KRWDZBQOSA-N 0.000 claims 1
- GWYQULIPMMGJAU-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(difluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C(F)F)=CC=C1F GWYQULIPMMGJAU-SFHVURJKSA-N 0.000 claims 1
- WUHYZWNJZPFRRZ-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(fluoromethoxy)-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(OCF)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 WUHYZWNJZPFRRZ-IBGZPJMESA-N 0.000 claims 1
- MORMZRVYZMOYHE-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(fluoromethoxy)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OCF)=CC=2)=CC=C1F MORMZRVYZMOYHE-SFHVURJKSA-N 0.000 claims 1
- XSTVHCYQAAOEHC-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C(F)(F)F)=CC=C1F XSTVHCYQAAOEHC-KRWDZBQOSA-N 0.000 claims 1
- JOOYEPMWNZTNNB-DEOSSOPVSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-[(dimethylamino)methyl]-3-methyl-1-benzofuran-2-carboxamide Chemical compound CC=1C2=CC(CN(C)C)=CC=C2OC=1C(=O)NC(C=1)=CC=C(F)C=1[C@]1(C(F)F)COCC(N)=N1 JOOYEPMWNZTNNB-DEOSSOPVSA-N 0.000 claims 1
- KLDFTGBUBUASGA-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-chloropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)Cl)=CC=C1F KLDFTGBUBUASGA-KRWDZBQOSA-N 0.000 claims 1
- UCRIOEOLCJOIOL-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-hydroxypyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)O)=CC=C1F UCRIOEOLCJOIOL-KRWDZBQOSA-N 0.000 claims 1
- QWVPXISELPMSGX-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methoxypyridine-2-carboxamide Chemical compound COC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 QWVPXISELPMSGX-SFHVURJKSA-N 0.000 claims 1
- BQYRVARYDSJDJF-NRFANRHFSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methyl-1-benzofuran-2-carboxamide Chemical compound O1C2=CC=C(Br)C=C2C(C)=C1C(=O)NC(C=1)=CC=C(F)C=1[C@]1(C(F)F)COCC(N)=N1 BQYRVARYDSJDJF-NRFANRHFSA-N 0.000 claims 1
- NSHIOKOUABVPPT-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 NSHIOKOUABVPPT-SFHVURJKSA-N 0.000 claims 1
- NSHIOKOUABVPPT-XBCJLSAZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-4,6-dideuterio-3-(trideuteriomethyl)pyridine-2-carboxamide Chemical compound [2H]C1=C(Br)C([2H])=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1C([2H])([2H])[2H] NSHIOKOUABVPPT-XBCJLSAZSA-N 0.000 claims 1
- WLOOOUPMVOAGDW-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F WLOOOUPMVOAGDW-KRWDZBQOSA-N 0.000 claims 1
- GYPHJLCLFZEIHF-NRFANRHFSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-but-2-ynoxy-3-methylpyrazine-2-carboxamide Chemical compound CC1=NC(OCC#CC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 GYPHJLCLFZEIHF-NRFANRHFSA-N 0.000 claims 1
- MEWAOSOFVZTZLU-FQEVSTJZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-but-2-ynoxypyrazine-2-carboxamide Chemical compound C1=NC(OCC#CC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 MEWAOSOFVZTZLU-FQEVSTJZSA-N 0.000 claims 1
- YIFSQGWDENNRQO-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-fluoropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)F)=CC=C1F YIFSQGWDENNRQO-KRWDZBQOSA-N 0.000 claims 1
- VLDQODACOIIKER-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-3-hydroxypyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)O)=CC=C1F VLDQODACOIIKER-KRWDZBQOSA-N 0.000 claims 1
- RFBSKPMTVVJHML-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-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([C@]2(N=C(N)COC2)C(F)F)=C1 RFBSKPMTVVJHML-SFHVURJKSA-N 0.000 claims 1
- RFBSKPMTVVJHML-XBCJLSAZSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-4,6-dideuterio-3-(trideuteriomethyl)pyridine-2-carboxamide Chemical compound [2H]C1=C(Cl)C([2H])=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1C([2H])([2H])[2H] RFBSKPMTVVJHML-XBCJLSAZSA-N 0.000 claims 1
- TXEZTBDCHBLADF-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Cl)=NC=2)=CC=C1F TXEZTBDCHBLADF-INIZCTEOSA-N 0.000 claims 1
- RASUIEXPAHHRBC-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Cl)=CC=2)=CC=C1F RASUIEXPAHHRBC-KRWDZBQOSA-N 0.000 claims 1
- AFSICNVPEFPHPM-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyrimidine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Cl)=CN=2)=CC=C1F AFSICNVPEFPHPM-INIZCTEOSA-N 0.000 claims 1
- DHIZXRDJXNCTKQ-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-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([C@]2(N=C(N)COC2)C(F)F)=C1 DHIZXRDJXNCTKQ-IBGZPJMESA-N 0.000 claims 1
- DHIZXRDJXNCTKQ-JMLBKJCDSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyano-4,6-dideuterio-3-(trideuteriomethyl)pyridine-2-carboxamide Chemical compound [2H]C1=C(C#N)C([2H])=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=C1C([2H])([2H])[2H] DHIZXRDJXNCTKQ-JMLBKJCDSA-N 0.000 claims 1
- KDQIGIVWGQPWCQ-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C1F KDQIGIVWGQPWCQ-SFHVURJKSA-N 0.000 claims 1
- HEFWYMDXBRQJHR-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-ethoxypyrazine-2-carboxamide Chemical compound C1=NC(OCC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 HEFWYMDXBRQJHR-SFHVURJKSA-N 0.000 claims 1
- IGQHGMYJUNSIQV-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-ethoxypyridine-2-carboxamide Chemical compound N1=CC(OCC)=CC=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 IGQHGMYJUNSIQV-IBGZPJMESA-N 0.000 claims 1
- QCCWNEWVJSSXTH-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methoxy-3-methylpyrazine-2-carboxamide Chemical compound CC1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 QCCWNEWVJSSXTH-SFHVURJKSA-N 0.000 claims 1
- UYSCUNKHTZQTPR-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methoxypyrazine-2-carboxamide Chemical compound C1=NC(OC)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 UYSCUNKHTZQTPR-KRWDZBQOSA-N 0.000 claims 1
- AWJDBGIBIVHLLE-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methoxypyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 AWJDBGIBIVHLLE-SFHVURJKSA-N 0.000 claims 1
- UXEQXTWIWPXCHM-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methyl-1,3-thiazole-2-carboxamide Chemical compound S1C(C)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 UXEQXTWIWPXCHM-INIZCTEOSA-N 0.000 claims 1
- KJIDRFGYFHIELN-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methyl-1h-pyrazole-3-carboxamide Chemical compound N1C(C)=CC(C(=O)NC=2C=C(C(F)=CC=2)[C@]2(N=C(N)COC2)C(F)F)=N1 KJIDRFGYFHIELN-INIZCTEOSA-N 0.000 claims 1
- WHJTYFYIOWGETK-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methylpyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 WHJTYFYIOWGETK-KRWDZBQOSA-N 0.000 claims 1
- AJMKTUYJMOEGBB-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methylpyridine-2-carboxamide Chemical compound N1=CC(C)=CC=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 AJMKTUYJMOEGBB-SFHVURJKSA-N 0.000 claims 1
- ANBUSERKTHLJHR-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-prop-2-ynoxypyrazine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(OCC#C)=NC=2)=CC=C1F ANBUSERKTHLJHR-IBGZPJMESA-N 0.000 claims 1
- DWDJFKJCOUIPTR-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-propan-2-yloxypyrazine-2-carboxamide Chemical compound C1=NC(OC(C)C)=CN=C1C(=O)NC1=CC=C(F)C([C@]2(N=C(N)COC2)C(F)F)=C1 DWDJFKJCOUIPTR-IBGZPJMESA-N 0.000 claims 1
- BGSHPXXXXFROSF-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-6-oxo-1h-pyrazine-3-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(O)=NC=2)=CC=C1F BGSHPXXXXFROSF-INIZCTEOSA-N 0.000 claims 1
- ATTNJTIPIGYNKV-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-6-oxo-1h-pyridazine-3-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=NC(O)=CC=2)=CC=C1F ATTNJTIPIGYNKV-INIZCTEOSA-N 0.000 claims 1
- QCTPETFOENNYDB-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-6-oxo-1h-pyridine-3-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C2=CNC(=O)C=C2)=CC=C1F QCTPETFOENNYDB-KRWDZBQOSA-N 0.000 claims 1
- ZXPKASSOYIQBIN-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-7h-pyrrolo[2,3-d]pyrimidine-6-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2NC3=NC=NC=C3C=2)=CC=C1F ZXPKASSOYIQBIN-SFHVURJKSA-N 0.000 claims 1
- PLPIYYJZGBRCAN-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]imidazo[1,2-a]pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=C3C=CC=CN3C=2)=CC=C1F PLPIYYJZGBRCAN-IBGZPJMESA-N 0.000 claims 1
- MDXODTFMFWDTKY-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]pyrazolo[1,5-a]pyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C2=NN3C=CC=CC3=C2)=CC=C1F MDXODTFMFWDTKY-IBGZPJMESA-N 0.000 claims 1
- MPKZNNPGWQZKGY-IBGZPJMESA-N n-[3-[(3r)-5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C1OCC(N)=N[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CN3C=CC=C3C=2)=CC=C1F MPKZNNPGWQZKGY-IBGZPJMESA-N 0.000 claims 1
- UYYHMVGSGAVEBQ-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-hydroxypyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(CF)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)O)=CC=C1F UYYHMVGSGAVEBQ-KRWDZBQOSA-N 0.000 claims 1
- BUEDFMDBDCERNC-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methoxypyridine-2-carboxamide Chemical compound COC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C([C@@]2(CF)N=C(N)COC2)=C1 BUEDFMDBDCERNC-SFHVURJKSA-N 0.000 claims 1
- AMOKELNCOZWYQG-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C([C@@]2(CF)N=C(N)COC2)=C1 AMOKELNCOZWYQG-SFHVURJKSA-N 0.000 claims 1
- NQNLROFWOGGJGK-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-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([C@@]2(CF)N=C(N)COC2)=C1 NQNLROFWOGGJGK-SFHVURJKSA-N 0.000 claims 1
- NQNLROFWOGGJGK-XBCJLSAZSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloro-4,6-dideuterio-3-(trideuteriomethyl)pyridine-2-carboxamide Chemical compound [2H]C1=C(Cl)C([2H])=NC(C(=O)NC=2C=C(C(F)=CC=2)[C@@]2(CF)N=C(N)COC2)=C1C([2H])([2H])[2H] NQNLROFWOGGJGK-XBCJLSAZSA-N 0.000 claims 1
- NPOMRTKJJJPJGY-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-chloropyridine-2-carboxamide Chemical compound C1OCC(N)=N[C@]1(CF)C1=CC(NC(=O)C=2N=CC(Cl)=CC=2)=CC=C1F NPOMRTKJJJPJGY-KRWDZBQOSA-N 0.000 claims 1
- DIDQGOKRIHNPTF-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C=C(Br)C=2)[C@@]2(C)N=C(N)COC2)=C1 DIDQGOKRIHNPTF-INIZCTEOSA-N 0.000 claims 1
- VJKFTSHRTGUDKU-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C=1C(Br)=CC(NC(=O)C=2N=CC(=CC=2)C(F)(F)F)=CC=1[C@]1(C)COCC(N)=N1 VJKFTSHRTGUDKU-KRWDZBQOSA-N 0.000 claims 1
- TWKMHWRNTKWHTK-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC(Br)=CC([C@@]2(C)N=C(N)COC2)=C1 TWKMHWRNTKWHTK-SFHVURJKSA-N 0.000 claims 1
- KIOJRAYIOQQHOD-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C(Br)=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=1[C@]1(C)COCC(N)=N1 KIOJRAYIOQQHOD-KRWDZBQOSA-N 0.000 claims 1
- OZAUFAJWFVOUMG-INIZCTEOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-bromopyrimidine-2-carboxamide Chemical compound C=1C(Br)=CC(NC(=O)C=2N=CC(Br)=CN=2)=CC=1[C@]1(C)COCC(N)=N1 OZAUFAJWFVOUMG-INIZCTEOSA-N 0.000 claims 1
- SQFPBQIACZLVBC-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-chloropyridine-2-carboxamide Chemical compound C=1C(Br)=CC(NC(=O)C=2N=CC(Cl)=CC=2)=CC=1[C@]1(C)COCC(N)=N1 SQFPBQIACZLVBC-KRWDZBQOSA-N 0.000 claims 1
- CRJLKTGWDGDYOO-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C=1C(Br)=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=1[C@]1(C)COCC(N)=N1 CRJLKTGWDGDYOO-SFHVURJKSA-N 0.000 claims 1
- DHKBQTABDSGIGV-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]-5-bromophenyl]-5-methylpyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NC1=CC(Br)=CC([C@@]2(C)N=C(N)COC2)=C1 DHKBQTABDSGIGV-KRWDZBQOSA-N 0.000 claims 1
- OZEVKAHYVCDJGB-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=CC([C@@]2(C)N=C(N)COC2)=C1 OZEVKAHYVCDJGB-SFHVURJKSA-N 0.000 claims 1
- HALWMQVNBCAXRZ-KRWDZBQOSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=1[C@]1(C)COCC(N)=N1 HALWMQVNBCAXRZ-KRWDZBQOSA-N 0.000 claims 1
- OPELDBZJLLBNMM-SFHVURJKSA-N n-[3-[(3r)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-methoxypyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(=O)NC1=CC=CC([C@@]2(C)N=C(N)COC2)=C1 OPELDBZJLLBNMM-SFHVURJKSA-N 0.000 claims 1
- UGWMYSHLUPGEQV-VQTJNVASSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-(2-methoxyethoxy)pyrazine-2-carboxamide Chemical compound C1=NC(OCCOC)=CN=C1C(=O)NC1=CC=C(F)C([C@@]2(C)N=C(N)[C@@](C)(OC2)C(F)(F)F)=C1 UGWMYSHLUPGEQV-VQTJNVASSA-N 0.000 claims 1
- XXUKTXRJOFQHLP-ZWKOTPCHSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Br)=CC=2)=CC=C(F)C=1[C@]1(C)CO[C@@](C)(C(F)(F)F)C(N)=N1 XXUKTXRJOFQHLP-ZWKOTPCHSA-N 0.000 claims 1
- MONBOQDZSLNZSN-DLBZAZTESA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyrimidine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(Br)=CN=2)=CC=C(F)C=1[C@]1(C)CO[C@@](C)(C(F)(F)F)C(N)=N1 MONBOQDZSLNZSN-DLBZAZTESA-N 0.000 claims 1
- BQFHTVUWPJXLOW-VQTJNVASSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-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([C@@]2(C)N=C(N)[C@@](C)(OC2)C(F)(F)F)=C1 BQFHTVUWPJXLOW-VQTJNVASSA-N 0.000 claims 1
- KSZDQDUDHWUQCJ-ZWKOTPCHSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyrimidine-2-carboxamide Chemical compound C=1C(NC(=O)C=2N=CC(=CN=2)C#N)=CC=C(F)C=1[C@]1(C)CO[C@@](C)(C(F)(F)F)C(N)=N1 KSZDQDUDHWUQCJ-ZWKOTPCHSA-N 0.000 claims 1
- OGFOGSCUHZKSAF-RBUKOAKNSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-methoxypyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(=O)NC1=CC=C(F)C([C@@]2(C)N=C(N)[C@@](C)(OC2)C(F)(F)F)=C1 OGFOGSCUHZKSAF-RBUKOAKNSA-N 0.000 claims 1
- YGNDEESWZOXXLA-ZWKOTPCHSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]phenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=1[C@]1(C)CO[C@@](C)(C(F)(F)F)C(N)=N1 YGNDEESWZOXXLA-ZWKOTPCHSA-N 0.000 claims 1
- OPAXOXPTFOUJHW-RBUKOAKNSA-N n-[3-[(3r,6r)-5-amino-3,6-dimethyl-6-(trifluoromethyl)-2h-1,4-oxazin-3-yl]phenyl]-5-methoxypyridine-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(=O)NC1=CC=CC([C@@]2(C)N=C(N)[C@@](C)(OC2)C(F)(F)F)=C1 OPAXOXPTFOUJHW-RBUKOAKNSA-N 0.000 claims 1
- QJCNKLUUFWNMEO-DGIBIBHMSA-N n-[3-[(3r,6r)-5-amino-3-(difluoromethyl)-6-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-cyanopyridine-2-carboxamide Chemical compound N1=C(N)[C@@H](C)OC[C@@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC=CN=2)C#N)=CC=C1F QJCNKLUUFWNMEO-DGIBIBHMSA-N 0.000 claims 1
- SJRMJSRRAFSJFY-LZVRBXCZSA-N n-[3-[(3r,6r)-5-amino-3-(difluoromethyl)-6-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)[C@@H](C)OC[C@@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F SJRMJSRRAFSJFY-LZVRBXCZSA-N 0.000 claims 1
- QJCNKLUUFWNMEO-OVWNDWIMSA-N n-[3-[(3r,6s)-5-amino-3-(difluoromethyl)-6-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3-cyanopyridine-2-carboxamide Chemical compound N1=C(N)[C@H](C)OC[C@@]1(C(F)F)C1=CC(NC(=O)C=2C(=CC=CN=2)C#N)=CC=C1F QJCNKLUUFWNMEO-OVWNDWIMSA-N 0.000 claims 1
- HALWMQVNBCAXRZ-QGZVFWFLSA-N n-[3-[(3s)-5-amino-3-methyl-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-bromopyridine-2-carboxamide Chemical compound C=1C=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=1[C@@]1(C)COCC(N)=N1 HALWMQVNBCAXRZ-QGZVFWFLSA-N 0.000 claims 1
- SJRMJSRRAFSJFY-DYBLOJMWSA-N n-[3-[(3s,6r)-5-amino-3-(difluoromethyl)-6-methyl-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)[C@@H](C)OC[C@]1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F SJRMJSRRAFSJFY-DYBLOJMWSA-N 0.000 claims 1
- KMCJEHUJVCXPEJ-UHFFFAOYSA-N n-[3-[3-amino-5-(trifluoromethyl)-6,7-dihydro-2h-1,4-oxazepin-5-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1COCC(N)=NC1(C(F)(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F KMCJEHUJVCXPEJ-UHFFFAOYSA-N 0.000 claims 1
- XAUNGQDZJFRKNL-UHFFFAOYSA-N n-[3-[3-amino-5-(trifluoromethyl)-6,7-dihydro-2h-1,4-oxazepin-5-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1COCC(N)=NC1(C(F)(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C1F XAUNGQDZJFRKNL-UHFFFAOYSA-N 0.000 claims 1
- NSPDTJIIXCMMAO-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-2,5-dimethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C=CC=2)C2(N=C(N)COC2)C(F)F)=C1C NSPDTJIIXCMMAO-UHFFFAOYSA-N 0.000 claims 1
- GFKFSIFXBJUBPL-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-2-ethyl-1,3-oxazole-4-carboxamide Chemical compound O1C(CC)=NC(C(=O)NC=2C=C(C=CC=2)C2(N=C(N)COC2)C(F)F)=C1 GFKFSIFXBJUBPL-UHFFFAOYSA-N 0.000 claims 1
- GBUZSUPNECMGRX-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound O1C(C)=NC(C(=O)NC=2C=C(C=CC=2)C2(N=C(N)COC2)C(F)F)=C1 GBUZSUPNECMGRX-UHFFFAOYSA-N 0.000 claims 1
- TUIVXRVANQYRAV-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-3-chloro-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2C(=CC(=CN=2)C(F)(F)F)Cl)=C1 TUIVXRVANQYRAV-UHFFFAOYSA-N 0.000 claims 1
- ICTVRTWUBXQZOS-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-4-bromofuran-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2OC=C(Br)C=2)=C1 ICTVRTWUBXQZOS-UHFFFAOYSA-N 0.000 claims 1
- MNMKHNPNWDQPIY-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-(difluoromethyl)pyrazine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=CC(=NC=2)C(F)F)=C1 MNMKHNPNWDQPIY-UHFFFAOYSA-N 0.000 claims 1
- UPWBBCVLDKVJAK-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=CC(=CC=2)C(F)(F)F)=C1 UPWBBCVLDKVJAK-UHFFFAOYSA-N 0.000 claims 1
- ICJYNQVYBWGPSY-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-bromopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=CC(Br)=CC=2)=C1 ICJYNQVYBWGPSY-UHFFFAOYSA-N 0.000 claims 1
- HCATWODWZYGFTA-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-chloropyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CC=2)=C1 HCATWODWZYGFTA-UHFFFAOYSA-N 0.000 claims 1
- UEQKQBJMYJQCGH-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=CC(=CC=2)C#N)=C1 UEQKQBJMYJQCGH-UHFFFAOYSA-N 0.000 claims 1
- OICGRZJIBVPJPN-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-methylpyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NC1=CC=CC(C2(N=C(N)COC2)C(F)F)=C1 OICGRZJIBVPJPN-UHFFFAOYSA-N 0.000 claims 1
- ITKSWDNVBCEALA-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-6-oxo-1h-pyridazine-3-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC=CC(NC(=O)C=2N=NC(O)=CC=2)=C1 ITKSWDNVBCEALA-UHFFFAOYSA-N 0.000 claims 1
- QYJJAJOYUWJUAO-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-6,6-dimethyl-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound N1=C(N)C(C)(C)OCC1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=CC=C1F QYJJAJOYUWJUAO-UHFFFAOYSA-N 0.000 claims 1
- LGSRJXIWGAGWHY-UHFFFAOYSA-N n-[3-[5-amino-3-(difluoromethyl)-6,6-dimethyl-2h-1,4-oxazin-3-yl]-4-fluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound N1=C(N)C(C)(C)OCC1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=CC=C1F LGSRJXIWGAGWHY-UHFFFAOYSA-N 0.000 claims 1
- BHTMIZYGXBKFIO-UHFFFAOYSA-N n-[3-[5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-3,5-dichloropyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(CF)C1=CC(NC(=O)C=2C(=CC(Cl)=CN=2)Cl)=CC=C1F BHTMIZYGXBKFIO-UHFFFAOYSA-N 0.000 claims 1
- AMOKELNCOZWYQG-UHFFFAOYSA-N n-[3-[5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-4-fluorophenyl]-5-bromo-3-methylpyridine-2-carboxamide Chemical compound CC1=CC(Br)=CN=C1C(=O)NC1=CC=C(F)C(C2(CF)N=C(N)COC2)=C1 AMOKELNCOZWYQG-UHFFFAOYSA-N 0.000 claims 1
- GWTUALKYCOKUGL-UHFFFAOYSA-N n-[3-[5-amino-3-(fluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]phenyl]-5-bromopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(CF)C1=CC=CC(NC(=O)C=2N=CC(Br)=CC=2)=C1 GWTUALKYCOKUGL-UHFFFAOYSA-N 0.000 claims 1
- ZVTWRQBMXRBNQH-UHFFFAOYSA-N n-[5-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-2,4-difluorophenyl]-5-bromo-3-hydroxypyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2C(=CC(Br)=CN=2)O)=C(F)C=C1F ZVTWRQBMXRBNQH-UHFFFAOYSA-N 0.000 claims 1
- JFBAPCCCHNRWQY-UHFFFAOYSA-N n-[5-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-2,4-difluorophenyl]-5-bromopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2N=CC(Br)=CC=2)=C(F)C=C1F JFBAPCCCHNRWQY-UHFFFAOYSA-N 0.000 claims 1
- GMMXGOGXNYUONU-UHFFFAOYSA-N n-[5-[5-amino-3-(difluoromethyl)-2,6-dihydro-1,4-oxazin-3-yl]-2,4-difluorophenyl]-5-cyanopyridine-2-carboxamide Chemical compound C1OCC(N)=NC1(C(F)F)C1=CC(NC(=O)C=2N=CC(=CC=2)C#N)=C(F)C=C1F GMMXGOGXNYUONU-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
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2010
- 2010-07-22 UY UY0001032799A patent/UY32799A/es not_active Application Discontinuation
- 2010-07-22 AR ARP100102667A patent/AR077328A1/es unknown
- 2010-07-23 US US12/842,360 patent/US8207164B2/en active Active
- 2010-07-23 TW TW099124438A patent/TW201107316A/zh unknown
- 2010-07-23 MA MA34558A patent/MA33450B1/fr unknown
- 2010-07-23 KR KR1020137033812A patent/KR20140004810A/ko not_active Withdrawn
- 2010-07-23 NZ NZ597529A patent/NZ597529A/xx not_active IP Right Cessation
- 2010-07-23 EP EP10737870.5A patent/EP2456763B1/en not_active Revoked
- 2010-07-23 CN CN201080035169.0A patent/CN102471293B/zh not_active Expired - Fee Related
- 2010-07-23 ES ES10737870.5T patent/ES2534315T3/es active Active
- 2010-07-23 KR KR1020127001651A patent/KR101422965B1/ko not_active Expired - Fee Related
- 2010-07-23 JP JP2012521053A patent/JP5767214B2/ja not_active Expired - Fee Related
- 2010-07-23 CA CA2768980A patent/CA2768980A1/en not_active Abandoned
- 2010-07-23 EA EA201200174A patent/EA201200174A1/ru unknown
- 2010-07-23 PE PE2012000094A patent/PE20121440A1/es not_active Application Discontinuation
- 2010-07-23 SG SG2011096823A patent/SG177397A1/en unknown
- 2010-07-23 CU CU2012000013A patent/CU24083B1/es not_active IP Right Cessation
- 2010-07-23 AU AU2010274913A patent/AU2010274913B2/en not_active Ceased
- 2010-07-23 MX MX2012001070A patent/MX2012001070A/es active IP Right Grant
- 2010-07-23 WO PCT/EP2010/060718 patent/WO2011009943A1/en not_active Ceased
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2012
- 2012-01-05 IL IL217378A patent/IL217378A/en not_active IP Right Cessation
- 2012-01-09 ZA ZA2012/00155A patent/ZA201200155B/en unknown
- 2012-01-09 CR CR20120002A patent/CR20120002A/es unknown
- 2012-01-19 CO CO12007858A patent/CO6491058A2/es active IP Right Grant
- 2012-01-23 CL CL2012000185A patent/CL2012000185A1/es unknown
- 2012-01-24 GT GT201200016A patent/GT201200016A/es unknown
- 2012-01-24 EC EC2012011622A patent/ECSP12011622A/es unknown
- 2012-04-24 US US13/454,751 patent/US20120238560A1/en not_active Abandoned
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2013
- 2013-07-12 US US13/940,354 patent/US20140088084A1/en not_active Abandoned
- 2013-12-20 US US14/136,679 patent/US8846658B2/en active Active
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2014
- 2014-07-07 US US14/324,883 patent/US20150018338A1/en not_active Abandoned
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