KR20010114250A - 프로게스테론 수용체 조절인자인 시클로카르바메이트 유도체 - Google Patents

Info

Publication number

KR20010114250A

KR20010114250A KR1020017013970A KR20017013970A KR20010114250A KR 20010114250 A KR20010114250 A KR 20010114250A KR 1020017013970 A KR1020017013970 A KR 1020017013970A KR 20017013970 A KR20017013970 A KR 20017013970A KR 20010114250 A KR20010114250 A KR 20010114250A

Authority

KR

South Korea

Prior art keywords

substituted

alkyl

oxazin

dihydro

dimethyl

Prior art date

1999-05-04

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

Links

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• 239000002379 progesterone receptor modulator Substances 0.000 title description 2
• 229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 134
• 238000000034 method Methods 0.000 claims abstract description 117
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 60
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 59
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 43
• 150000002367 halogens Chemical class 0.000 claims abstract description 43
• 125000003118 aryl group Chemical group 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 33
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 29
• 125000001424 substituent group Chemical group 0.000 claims abstract description 26
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 19
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 18
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 17
• 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims abstract description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 79
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 70
• -1 (3-chloro-phenyl) -4-ethyl-1,4-dihydro-benzo [d] [1,3] oxazin-2-one Chemical compound 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 30
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• KVMSWMUZFCLLFV-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(F)=CC(C#N)=C1 KVMSWMUZFCLLFV-UHFFFAOYSA-N 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 241000124008 Mammalia Species 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 8
• 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 229940088597 hormone Drugs 0.000 claims description 7
• 239000005556 hormone Substances 0.000 claims description 7
• HVXMMYUSBANZAI-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(C#N)=C1 HVXMMYUSBANZAI-UHFFFAOYSA-N 0.000 claims description 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
• UWIIXWIVGXAFAN-UHFFFAOYSA-N 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(F)=CC(Br)=C1 UWIIXWIVGXAFAN-UHFFFAOYSA-N 0.000 claims description 5
• PPDYGKBOJSGKBD-UHFFFAOYSA-N 6-(3-bromophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(Br)=C1 PPDYGKBOJSGKBD-UHFFFAOYSA-N 0.000 claims description 5
• 230000001419 dependent effect Effects 0.000 claims description 5
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 206010028980 Neoplasm Diseases 0.000 claims description 4
• 150000001555 benzenes Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
• IDIRENXOSJYSCR-UHFFFAOYSA-N 2-[3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)phenyl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(CC#N)=C1 IDIRENXOSJYSCR-UHFFFAOYSA-N 0.000 claims description 3
• LTCHZBXTHMXHAR-UHFFFAOYSA-N 3-(4,4-dicyclopropyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(C=2C=C3C(C4CC4)(C4CC4)OC(=O)NC3=CC=2)=C1 LTCHZBXTHMXHAR-UHFFFAOYSA-N 0.000 claims description 3
• YMIYWAUOFRPGBF-UHFFFAOYSA-N 3-fluoro-5-[1-(methoxymethyl)-4,4-dimethyl-2-oxo-3,1-benzoxazin-6-yl]benzonitrile Chemical compound C=1C=C2N(COC)C(=O)OC(C)(C)C2=CC=1C1=CC(F)=CC(C#N)=C1 YMIYWAUOFRPGBF-UHFFFAOYSA-N 0.000 claims description 3
• PNEKYSUBNQXRHM-UHFFFAOYSA-N 4,4-dimethyl-6-(1-methylpyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound CN1C=CC=C1C1=CC=C(NC(=O)OC2(C)C)C2=C1 PNEKYSUBNQXRHM-UHFFFAOYSA-N 0.000 claims description 3
• SMKZYKBPVNAOJL-UHFFFAOYSA-N 4,4-dimethyl-6-(1h-pyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CN1 SMKZYKBPVNAOJL-UHFFFAOYSA-N 0.000 claims description 3
• DZRIKLQQKVBDJJ-UHFFFAOYSA-N 4,4-dimethyl-6-[3-(2-trimethylsilylethynyl)phenyl]-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(C#C[Si](C)(C)C)=C1 DZRIKLQQKVBDJJ-UHFFFAOYSA-N 0.000 claims description 3
• QYXWQJJMCRIUKE-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(F)C(C#N)=C1 QYXWQJJMCRIUKE-UHFFFAOYSA-N 0.000 claims description 3
• WRAWKFUWOAFTDQ-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)furan-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(C#N)O1 WRAWKFUWOAFTDQ-UHFFFAOYSA-N 0.000 claims description 3
• MESNIJJPCGWIQB-UHFFFAOYSA-N 6-(3-acetylphenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound CC(=O)C1=CC=CC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 MESNIJJPCGWIQB-UHFFFAOYSA-N 0.000 claims description 3
• JRDFVXBVDLMFJH-UHFFFAOYSA-N 6-(3-bromo-5-methylphenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound CC1=CC(Br)=CC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 JRDFVXBVDLMFJH-UHFFFAOYSA-N 0.000 claims description 3
• PRCXSDHAGJJCKC-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(F)C(Cl)=C1 PRCXSDHAGJJCKC-UHFFFAOYSA-N 0.000 claims description 3
• UNTRVRJHIUBUIT-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-methyl-1,4-dihydro-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)OC(=O)NC2=CC=C1C1=CC=CC(Cl)=C1 UNTRVRJHIUBUIT-UHFFFAOYSA-N 0.000 claims description 3
• QTVMSASXEDWDST-UHFFFAOYSA-N 6-(5-bromopyridin-3-yl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CN=CC(Br)=C1 QTVMSASXEDWDST-UHFFFAOYSA-N 0.000 claims description 3
• FKJUYZPFOJIRIG-UHFFFAOYSA-N 6-chloro-4-methyl-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C(Cl)C=C2C(C)(C(F)(F)F)OC(=O)NC2=C1 FKJUYZPFOJIRIG-UHFFFAOYSA-N 0.000 claims description 3
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
• FEVGHBLMPKIPFU-UHFFFAOYSA-N tert-butyl 2-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)pyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C=CC=C1C1=CC=C(NC(=O)OC2(C)C)C2=C1 FEVGHBLMPKIPFU-UHFFFAOYSA-N 0.000 claims description 3
• WBRVELFLQXWPBG-UHFFFAOYSA-N 2-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C=1SC=CC=1C#N WBRVELFLQXWPBG-UHFFFAOYSA-N 0.000 claims description 2
• MMRUWYPAERDHDX-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(C#N)=C1F MMRUWYPAERDHDX-UHFFFAOYSA-N 0.000 claims description 2
• VRFFPOVHAWBDBG-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-4-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(C#N)=CC=C1F VRFFPOVHAWBDBG-UHFFFAOYSA-N 0.000 claims description 2
• NLEVEIAQKTVSTO-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-(trifluoromethoxy)benzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(OC(F)(F)F)=CC(C#N)=C1 NLEVEIAQKTVSTO-UHFFFAOYSA-N 0.000 claims description 2
• JGYMUYVJOIEFFQ-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 JGYMUYVJOIEFFQ-UHFFFAOYSA-N 0.000 claims description 2
• GRRPAAFLOYWEHA-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 GRRPAAFLOYWEHA-UHFFFAOYSA-N 0.000 claims description 2
• NTBMICWLTLYFGW-UHFFFAOYSA-N 3-chloro-5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(Cl)=CC(C#N)=C1 NTBMICWLTLYFGW-UHFFFAOYSA-N 0.000 claims description 2
• PKVIKTBQZZTING-UHFFFAOYSA-N 3-fluoro-5-(8-fluoro-4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=C(F)C=C1C1=CC(F)=CC(C#N)=C1 PKVIKTBQZZTING-UHFFFAOYSA-N 0.000 claims description 2
• MEIWUXZPJSPWJO-UHFFFAOYSA-N 4,4-diethyl-6-(3-nitrophenyl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(CC)(CC)OC(=O)NC2=CC=C1C1=CC=CC([N+]([O-])=O)=C1 MEIWUXZPJSPWJO-UHFFFAOYSA-N 0.000 claims description 2
• YYHMNNAXMFGWBB-UHFFFAOYSA-N 4,4-dimethyl-6-(1-methyl-5-nitropyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 YYHMNNAXMFGWBB-UHFFFAOYSA-N 0.000 claims description 2
• AXVHYEZJTTVOJH-UHFFFAOYSA-N 4,4-dimethyl-6-(3-nitrophenyl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC([N+]([O-])=O)=C1 AXVHYEZJTTVOJH-UHFFFAOYSA-N 0.000 claims description 2
• SSSVZQDFTSCDPK-UHFFFAOYSA-N 4,4-dimethyl-6-(5-nitro-1h-pyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C([N+]([O-])=O)N1 SSSVZQDFTSCDPK-UHFFFAOYSA-N 0.000 claims description 2
• QWIQKRAABPUAGQ-UHFFFAOYSA-N 4,4-dimethyl-6-[2-(1,2,4-thiadiazol-3-yl)phenyl]-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC=C1C=1N=CSN=1 QWIQKRAABPUAGQ-UHFFFAOYSA-N 0.000 claims description 2
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• RHSCGZFJZHKZNC-UHFFFAOYSA-N 4,4-dimethyl-6-[3-(2h-tetrazol-5-yl)phenyl]-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C(C=1)=CC=CC=1C1=NN=NN1 RHSCGZFJZHKZNC-UHFFFAOYSA-N 0.000 claims description 2
• IRWYDKDYOSVIDZ-UHFFFAOYSA-N 4-(4,4-dicyclopropyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile Chemical compound O1C(=O)NC2=CC=C(C=3C=C(SC=3)C#N)C=C2C1(C1CC1)C1CC1 IRWYDKDYOSVIDZ-UHFFFAOYSA-N 0.000 claims description 2
• IJSGDARRCNDONL-UHFFFAOYSA-N 4-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)furan-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=COC(C#N)=C1 IJSGDARRCNDONL-UHFFFAOYSA-N 0.000 claims description 2
• JXNHGWCUOXLKRL-UHFFFAOYSA-N 4-benzyl-6-(3-chlorophenyl)-4-methyl-1h-3,1-benzoxazin-2-one Chemical compound O1C(=O)NC2=CC=C(C=3C=C(Cl)C=CC=3)C=C2C1(C)CC1=CC=CC=C1 JXNHGWCUOXLKRL-UHFFFAOYSA-N 0.000 claims description 2
• DNRMTRMFSKNGIV-UHFFFAOYSA-N 4-butyl-5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1CCCC DNRMTRMFSKNGIV-UHFFFAOYSA-N 0.000 claims description 2
• QAXWFQCRQFUILZ-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-4-ethylthiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1CC QAXWFQCRQFUILZ-UHFFFAOYSA-N 0.000 claims description 2
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• OUVMNSFSOSJAQL-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)benzene-1,3-dicarbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(C#N)=CC(C#N)=C1 OUVMNSFSOSJAQL-UHFFFAOYSA-N 0.000 claims description 2
• HEGVHYGSMSJKPP-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)pyridine-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CN=CC(C#N)=C1 HEGVHYGSMSJKPP-UHFFFAOYSA-N 0.000 claims description 2
• BGHLZYDCBNMWCU-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(C#N)=CS1 BGHLZYDCBNMWCU-UHFFFAOYSA-N 0.000 claims description 2
• MGCPANQAGXWBFT-UHFFFAOYSA-N 6-(2-chlorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC=C1Cl MGCPANQAGXWBFT-UHFFFAOYSA-N 0.000 claims description 2
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• XKXYGOFFUINVOY-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(F)=CC(F)=C1 XKXYGOFFUINVOY-UHFFFAOYSA-N 0.000 claims description 2
• DUGCMPPGABAONL-UHFFFAOYSA-N 6-(3,5-dinitrophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 DUGCMPPGABAONL-UHFFFAOYSA-N 0.000 claims description 2
• SNZNCFSHRLBZQL-UHFFFAOYSA-N 6-(3-benzoylphenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C(C=1)=CC=CC=1C(=O)C1=CC=CC=C1 SNZNCFSHRLBZQL-UHFFFAOYSA-N 0.000 claims description 2
• COCHTGRDEIHWSU-UHFFFAOYSA-N 6-(3-bromo-5-fluorophenyl)-1,4,4-trimethyl-3,1-benzoxazin-2-one Chemical compound C=1C=C2N(C)C(=O)OC(C)(C)C2=CC=1C1=CC(F)=CC(Br)=C1 COCHTGRDEIHWSU-UHFFFAOYSA-N 0.000 claims description 2
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• QXXOGHDDSWRZPI-UHFFFAOYSA-N 6-(3-chloro-4-fluorophenyl)-8-fluoro-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=C(F)C=C1C1=CC=C(F)C(Cl)=C1 QXXOGHDDSWRZPI-UHFFFAOYSA-N 0.000 claims description 2
• QFJFPUFDMQGULL-UHFFFAOYSA-N 6-(3-chloro-5-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(F)=CC(Cl)=C1 QFJFPUFDMQGULL-UHFFFAOYSA-N 0.000 claims description 2
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