EA004512B1 - Циклокарбаматные производные в качестве модуляторов рецептора прогестерона - Google Patents

Info

Publication number

EA004512B1

EA004512B1 EA200101176A EA200101176A EA004512B1 EA 004512 B1 EA004512 B1 EA 004512B1 EA 200101176 A EA200101176 A EA 200101176A EA 200101176 A EA200101176 A EA 200101176A EA 004512 B1 EA004512 B1 EA 004512B1

Authority

EA

Eurasian Patent Office

Prior art keywords

substituted

alkyl

oxazin

alkoxy

dimethyl

Prior art date

1999-05-04

Links

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• Global Dossier
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• 239000002379 progesterone receptor modulator Substances 0.000 title 1
• 229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title 1
• -1 -OH Chemical group 0.000 claims abstract description 279
• 150000001875 compounds Chemical class 0.000 claims abstract description 143
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 91
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 91
• 150000002367 halogens Chemical class 0.000 claims abstract description 91
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 89
• 125000001424 substituent group Chemical group 0.000 claims abstract description 84
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 64
• 125000003118 aryl group Chemical group 0.000 claims abstract description 63
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 62
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 55
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 52
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 49
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 49
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 45
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 42
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 37
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 36
• 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 32
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 30
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 30
• 125000004104 aryloxy group Chemical group 0.000 claims abstract description 29
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 28
• 125000005110 aryl thio group Chemical group 0.000 claims abstract description 28
• 125000005415 substituted alkoxy group Chemical group 0.000 claims abstract description 28
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 25
• 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 16
• 125000005309 thioalkoxy group Chemical group 0.000 claims abstract description 16
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 14
• 150000001555 benzenes Chemical group 0.000 claims abstract description 14
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 11
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims abstract description 7
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims abstract description 6
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 6
• 235000010290 biphenyl Nutrition 0.000 claims abstract description 6
• 239000004305 biphenyl Substances 0.000 claims abstract description 6
• 125000002541 furyl group Chemical group 0.000 claims abstract description 6
• 125000001041 indolyl group Chemical group 0.000 claims abstract description 6
• 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 6
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 6
• 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 6
• 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 6
• 125000003373 pyrazinyl group Chemical group 0.000 claims abstract description 6
• 125000002098 pyridazinyl group Chemical group 0.000 claims abstract description 6
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 6
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 6
• 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
• 229930192474 thiophene Natural products 0.000 claims abstract description 6
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
• 239000011737 fluorine Substances 0.000 claims abstract description 5
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 4
• 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims abstract 4
• JVTRZJXFAOQMRA-UHFFFAOYSA-N 1,3-oxazin-2-one Chemical compound O=C1N=CC=CO1 JVTRZJXFAOQMRA-UHFFFAOYSA-N 0.000 claims description 183
• 238000000034 method Methods 0.000 claims description 115
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 68
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 56
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 40
• 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims description 32
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 241000124008 Mammalia Species 0.000 claims description 17
• SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims description 14
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
• 235000010469 Glycine max Nutrition 0.000 claims description 11
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
• CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims description 10
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
• 244000068988 Glycine max Species 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
• 210000001672 ovary Anatomy 0.000 claims description 6
• YXDXXGXWFJCXEB-UHFFFAOYSA-N 2-furonitrile Chemical compound N#CC1=CC=CO1 YXDXXGXWFJCXEB-UHFFFAOYSA-N 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 210000000481 breast Anatomy 0.000 claims description 4
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 150000002148 esters Chemical class 0.000 claims description 4
• HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
• 239000001257 hydrogen Substances 0.000 claims description 4
• 201000010260 leiomyoma Diseases 0.000 claims description 4
• 210000002307 prostate Anatomy 0.000 claims description 4
• QRNMAUBTQDBSSM-UHFFFAOYSA-N 3-fluoro-5-(2-oxospiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)benzonitrile Chemical compound FC1=CC(C#N)=CC(C=2C=C3C4(CCCCC4)OC(=O)NC3=CC=2)=C1 QRNMAUBTQDBSSM-UHFFFAOYSA-N 0.000 claims description 3
• QHHQRGUMAXRMAY-UHFFFAOYSA-N 4-(2-oxospiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)thiophene-2-carbonitrile Chemical compound O1C(=O)NC2=CC=C(C=3C=C(SC=3)C#N)C=C2C21CCCCC2 QHHQRGUMAXRMAY-UHFFFAOYSA-N 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• SVVIWFMTYDOJQX-UHFFFAOYSA-N 5-(2-oxospiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)thiophene-2-carbonitrile Chemical compound O1C(=O)NC2=CC=C(C=3SC(=CC=3)C#N)C=C2C21CCCCC2 SVVIWFMTYDOJQX-UHFFFAOYSA-N 0.000 claims description 3
• HQEDEYRIOUJUKO-UHFFFAOYSA-N 6-(3-nitrophenyl)spiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-2-one Chemical compound [O-][N+](=O)C1=CC=CC(C=2C=C3C4(CCCCC4)OC(=O)NC3=CC=2)=C1 HQEDEYRIOUJUKO-UHFFFAOYSA-N 0.000 claims description 3
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 3
• 206010046798 Uterine leiomyoma Diseases 0.000 claims description 3
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
• 210000001072 colon Anatomy 0.000 claims description 3
• 201000003908 endometrial adenocarcinoma Diseases 0.000 claims description 3
• 208000029382 endometrium adenocarcinoma Diseases 0.000 claims description 3
• 235000011389 fruit/vegetable juice Nutrition 0.000 claims description 3
• 238000002657 hormone replacement therapy Methods 0.000 claims description 3
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 claims description 3
• 201000007954 uterine fibroid Diseases 0.000 claims description 3
• YDZNRNHKJQTGCG-UHFFFAOYSA-N 1,1'-binaphthyl-2,2'-dicarboxylic acid Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3C(=O)O)=C(C(O)=O)C=CC2=C1 YDZNRNHKJQTGCG-UHFFFAOYSA-N 0.000 claims description 2
• KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 2
• CSNZQRXRUXBYAA-UHFFFAOYSA-N 2-[6-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(CC#N)=N1 CSNZQRXRUXBYAA-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• UOARKAQAGLVLOK-UHFFFAOYSA-N 6-(3-chlorophenyl)spiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-2-one Chemical compound ClC1=CC=CC(C=2C=C3C4(CCCCC4)OC(=O)NC3=CC=2)=C1 UOARKAQAGLVLOK-UHFFFAOYSA-N 0.000 claims description 2
• GKEMTHTTWRREOR-UHFFFAOYSA-N 6-(3-chlorophenyl)spiro[1h-3,1-benzoxazine-4,1'-cyclopentane]-2-one Chemical compound ClC1=CC=CC(C=2C=C3C4(CCCC4)OC(=O)NC3=CC=2)=C1 GKEMTHTTWRREOR-UHFFFAOYSA-N 0.000 claims description 2
• BZIHMJOJAJSHGD-UHFFFAOYSA-N 6-[5-(hydroxyiminomethyl)furan-3-yl]-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=COC(C=NO)=C1 BZIHMJOJAJSHGD-UHFFFAOYSA-N 0.000 claims description 2
• LNDJVIYUJOJFSO-UHFFFAOYSA-N cyanoacetylene Chemical compound C#CC#N LNDJVIYUJOJFSO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• STPGCJZTCFWRGC-UHFFFAOYSA-N n-[4-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorophenyl]acetamide Chemical compound C1=C(F)C(NC(=O)C)=CC=C1C1=CC=C(NC(=O)OC2(C)C)C2=C1 STPGCJZTCFWRGC-UHFFFAOYSA-N 0.000 claims description 2
• 208000005605 Hormone-Dependent Neoplasms Diseases 0.000 claims 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 3
• BXVSAYBZSGIURM-UHFFFAOYSA-N 2-phenoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound O1CC2=CC=CC=C2OP1(=O)OC1=CC=CC=C1 BXVSAYBZSGIURM-UHFFFAOYSA-N 0.000 claims 2
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
• 206010014733 Endometrial cancer Diseases 0.000 claims 2
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
• 201000003914 endometrial carcinoma Diseases 0.000 claims 2
• 230000012173 estrus Effects 0.000 claims 2
• 206010027191 meningioma Diseases 0.000 claims 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
• 230000001817 pituitary effect Effects 0.000 claims 2
• KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 1
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• KQMGQUQOZSZRBI-UHFFFAOYSA-N 4-methylthiophene-2-carbonitrile Chemical compound CC1=CSC(C#N)=C1 KQMGQUQOZSZRBI-UHFFFAOYSA-N 0.000 claims 1
• FUMWUTSVOOBPCJ-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1C FUMWUTSVOOBPCJ-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• BGAWWRLMFNCAKP-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(C#N)S1 BGAWWRLMFNCAKP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• 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 1
• 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 1
• LGLOOLWMNDHTKN-UHFFFAOYSA-N 6-(3-bromo-5-fluorophenyl)-4,4-dicyclopropyl-1h-3,1-benzoxazin-2-one Chemical compound FC1=CC(Br)=CC(C=2C=C3C(C4CC4)(C4CC4)OC(=O)NC3=CC=2)=C1 LGLOOLWMNDHTKN-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• ZFMGZMLOROWZPV-UHFFFAOYSA-N 6-(3-chlorophenyl)-4,4-diethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(CC)(CC)OC(=O)NC2=CC=C1C1=CC=CC(Cl)=C1 ZFMGZMLOROWZPV-UHFFFAOYSA-N 0.000 claims 1
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