EA004511B1 - Циклотиокарбаматные производные в качестве модуляторов рецептора прогестерона - Google Patents

Info

Publication number

EA004511B1

EA004511B1 EA200101181A EA200101181A EA004511B1 EA 004511 B1 EA004511 B1 EA 004511B1 EA 200101181 A EA200101181 A EA 200101181A EA 200101181 A EA200101181 A EA 200101181A EA 004511 B1 EA004511 B1 EA 004511B1

Authority

EA

Eurasian Patent Office

Prior art keywords

substituted

alkyl

aryl

group

alkoxy

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
• 150000001875 compounds Chemical class 0.000 claims abstract description 156
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 119
• -1 izoxazolyl Chemical group 0.000 claims abstract description 113
• 125000003118 aryl group Chemical group 0.000 claims abstract description 93
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 92
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 82
• 125000001424 substituent group Chemical group 0.000 claims abstract description 81
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 79
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 75
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 69
• 150000002367 halogens Chemical class 0.000 claims abstract description 65
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 58
• 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 41
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 35
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 35
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 34
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 32
• 125000005415 substituted alkoxy 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
• 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 25
• 125000005157 alkyl carboxy group Chemical group 0.000 claims abstract description 25
• 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 25
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 22
• 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract description 22
• 150000003839 salts Chemical class 0.000 claims abstract description 20
• 125000005309 thioalkoxy group Chemical group 0.000 claims abstract description 19
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 14
• 125000003367 polycyclic group 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
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 12
• 125000006273 (C1-C3) alkyl 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
• 150000001555 benzenes Chemical group 0.000 claims abstract description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 7
• 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
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
• 239000001257 hydrogen Substances 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
• 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
• 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
• 125000005561 phenanthryl group Chemical group 0.000 claims abstract description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 5
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
• 125000002252 acyl group Chemical group 0.000 claims abstract description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 3
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract 8
• 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
• 238000000034 method Methods 0.000 claims description 115
• 229910052799 carbon Inorganic materials 0.000 claims description 60
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 54
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
• 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims description 29
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 14
• 241000124008 Mammalia Species 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• CUPOOAWTRIURFT-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=CS1 CUPOOAWTRIURFT-UHFFFAOYSA-N 0.000 claims description 7
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 5
• 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 description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 210000001672 ovary Anatomy 0.000 claims description 5
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
• 201000009273 Endometriosis Diseases 0.000 claims description 4
• 206010046798 Uterine leiomyoma Diseases 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 4
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
• 201000010260 leiomyoma Diseases 0.000 claims description 4
• 210000002307 prostate Anatomy 0.000 claims description 4
• GSXCEVHRIVLFJV-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC=1C=CSC=1 GSXCEVHRIVLFJV-UHFFFAOYSA-N 0.000 claims description 4
• YWXXMWYKYMGQIQ-UHFFFAOYSA-N 1,3-oxazine-2-thione Chemical compound S=C1N=CC=CO1 YWXXMWYKYMGQIQ-UHFFFAOYSA-N 0.000 claims description 3
• NAQUDAIOMWNXJF-UHFFFAOYSA-N 6-(3-fluorophenyl)-4-methyl-1,4-dihydro-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)OC(=S)NC2=CC=C1C1=CC=CC(F)=C1 NAQUDAIOMWNXJF-UHFFFAOYSA-N 0.000 claims description 3
• 208000032843 Hemorrhage Diseases 0.000 claims description 3
• 208000034158 bleeding Diseases 0.000 claims description 3
• 230000000740 bleeding effect Effects 0.000 claims description 3
• 210000000481 breast Anatomy 0.000 claims description 3
• 210000001072 colon Anatomy 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
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• JHWNSFIRRIBDRF-UHFFFAOYSA-N tert-butyl 2-cyano-5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)pyrrole-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C#N)=CC=C1C1=CC=C(NC(=S)OC2(C)C)C2=C1 JHWNSFIRRIBDRF-UHFFFAOYSA-N 0.000 claims description 3
• 201000007954 uterine fibroid Diseases 0.000 claims description 3
• DCBOJAHTRJNPIJ-UHFFFAOYSA-N 2-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)thiophene-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C=1SC=CC=1C#N DCBOJAHTRJNPIJ-UHFFFAOYSA-N 0.000 claims description 2
• LTTWZTLIENERDL-UHFFFAOYSA-N 2-[6-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)pyridin-2-yl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(CC#N)=N1 LTTWZTLIENERDL-UHFFFAOYSA-N 0.000 claims description 2
• SHWQSMSSKKIGRW-UHFFFAOYSA-N 3-(2-sulfanylidenespiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)benzonitrile Chemical compound O1C(=S)NC2=CC=C(C=3C=C(C=CC=3)C#N)C=C2C21CCCCC2 SHWQSMSSKKIGRW-UHFFFAOYSA-N 0.000 claims description 2
• GMQRDVATRSGMLF-UHFFFAOYSA-N 3-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-4-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(C#N)=CC=C1F GMQRDVATRSGMLF-UHFFFAOYSA-N 0.000 claims description 2
• CTTIMHOODJRMMQ-UHFFFAOYSA-N 3-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 CTTIMHOODJRMMQ-UHFFFAOYSA-N 0.000 claims description 2
• RILXTHFMVLBOPN-UHFFFAOYSA-N 3-(8-bromo-4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=C(Br)C=C1C1=CC(F)=CC(C#N)=C1 RILXTHFMVLBOPN-UHFFFAOYSA-N 0.000 claims description 2
• HDYOFEAGTBBGEN-UHFFFAOYSA-N 3-chloro-5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(Cl)=CC(C#N)=C1 HDYOFEAGTBBGEN-UHFFFAOYSA-N 0.000 claims description 2
• YLRADUODZWLKHG-UHFFFAOYSA-N 3-fluoro-5-(8-fluoro-4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=C(F)C=C1C1=CC(F)=CC(C#N)=C1 YLRADUODZWLKHG-UHFFFAOYSA-N 0.000 claims description 2
• JSOJTUILYANJMW-UHFFFAOYSA-N 4-benzyl-6-(3-chlorophenyl)-4-methyl-1h-3,1-benzoxazine-2-thione Chemical compound O1C(=S)NC2=CC=C(C=3C=C(Cl)C=CC=3)C=C2C1(C)CC1=CC=CC=C1 JSOJTUILYANJMW-UHFFFAOYSA-N 0.000 claims description 2
• VSPMRIXKBGUPJW-UHFFFAOYSA-N 4-butyl-5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1CCCC VSPMRIXKBGUPJW-UHFFFAOYSA-N 0.000 claims description 2
• UKMZDGICTYHTEO-UHFFFAOYSA-N 4-methyl-5-(2-sulfanylidenespiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)thiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C4(CCCCC4)OC(=S)NC3=CC=2)=C1C UKMZDGICTYHTEO-UHFFFAOYSA-N 0.000 claims description 2
• KBUBDEWGNXRLKX-UHFFFAOYSA-N 5-(2-sulfanylidenespiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)thiophene-2-carbonitrile Chemical compound O1C(=S)NC2=CC=C(C=3SC(=CC=3)C#N)C=C2C21CCCCC2 KBUBDEWGNXRLKX-UHFFFAOYSA-N 0.000 claims description 2
• HYELXXFFGVQXLM-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-1h-pyrrole-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(C#N)N1 HYELXXFFGVQXLM-UHFFFAOYSA-N 0.000 claims description 2
• QLNYJNLJIJPEAO-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-2-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(F)C(C#N)=C1 QLNYJNLJIJPEAO-UHFFFAOYSA-N 0.000 claims description 2
• JXEZBFHBHFDRCM-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1C JXEZBFHBHFDRCM-UHFFFAOYSA-N 0.000 claims description 2
• YULOLNRYBCOJDS-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-4-propylthiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1CCC YULOLNRYBCOJDS-UHFFFAOYSA-N 0.000 claims description 2
• XSBJYXLVQYKJTL-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)thiophene-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(C#N)S1 XSBJYXLVQYKJTL-UHFFFAOYSA-N 0.000 claims description 2
• WVQKUAAPNOSAJW-UHFFFAOYSA-N 6-(2,3-difluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(F)=C1F WVQKUAAPNOSAJW-UHFFFAOYSA-N 0.000 claims description 2
• SMBQGFBYNMMQJM-UHFFFAOYSA-N 6-(3,4-difluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(F)C(F)=C1 SMBQGFBYNMMQJM-UHFFFAOYSA-N 0.000 claims description 2
• KTBKDGMHHINKLK-UHFFFAOYSA-N 6-(3,5-difluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(F)=CC(F)=C1 KTBKDGMHHINKLK-UHFFFAOYSA-N 0.000 claims description 2
• BUGHELVCJWKCPY-UHFFFAOYSA-N 6-(3-bromo-5-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(F)=CC(Br)=C1 BUGHELVCJWKCPY-UHFFFAOYSA-N 0.000 claims description 2
• WUJWTXWFRXJYKR-UHFFFAOYSA-N 6-(3-bromo-5-methylphenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound CC1=CC(Br)=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 WUJWTXWFRXJYKR-UHFFFAOYSA-N 0.000 claims description 2
• WYHOTGLZCWQZME-UHFFFAOYSA-N 6-(3-bromophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(Br)=C1 WYHOTGLZCWQZME-UHFFFAOYSA-N 0.000 claims description 2
• JGZLNKUOAMAIAG-UHFFFAOYSA-N 6-(3-chloro-5-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(F)=CC(Cl)=C1 JGZLNKUOAMAIAG-UHFFFAOYSA-N 0.000 claims description 2
• YBBTTYFZWTXGQD-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-methyl-4-phenyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C=3C=CC=CC=3)OC(=S)NC2=CC=C1C1=CC=CC(Cl)=C1 YBBTTYFZWTXGQD-UHFFFAOYSA-N 0.000 claims description 2
• UMQGDADSFKJZKD-UHFFFAOYSA-N 6-(3-methoxyphenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound COC1=CC=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 UMQGDADSFKJZKD-UHFFFAOYSA-N 0.000 claims description 2
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
• 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 17
• IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
• 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 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
• COIUOECSBDDSNQ-UHFFFAOYSA-N 4,4-diethyl-6-(3-nitrophenyl)-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(CC)(CC)OC(=S)NC2=CC=C1C1=CC=CC([N+]([O-])=O)=C1 COIUOECSBDDSNQ-UHFFFAOYSA-N 0.000 claims 1
• FEWVQKWESAUNPQ-UHFFFAOYSA-N 4,4-dimethyl-6-(3-nitrophenyl)-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC([N+]([O-])=O)=C1 FEWVQKWESAUNPQ-UHFFFAOYSA-N 0.000 claims 1
• YXZAVJPXYUAVKV-UHFFFAOYSA-N 4-(2-sulfanylidenespiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)thiophene-2-carbonitrile Chemical compound O1C(=S)NC2=CC=C(C=3C=C(SC=3)C#N)C=C2C21CCCCC2 YXZAVJPXYUAVKV-UHFFFAOYSA-N 0.000 claims 1
• MQYRSOFJNHXZHN-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-1-ethylpyrrole-2-carbonitrile Chemical compound CCN1C(C#N)=CC=C1C1=CC=C(NC(=S)OC2(C)C)C2=C1 MQYRSOFJNHXZHN-UHFFFAOYSA-N 0.000 claims 1
• IUJHXSNSAUOSSH-UHFFFAOYSA-N 6-(2-chlorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC=C1Cl IUJHXSNSAUOSSH-UHFFFAOYSA-N 0.000 claims 1
• GQLJJGUGKUYGRM-UHFFFAOYSA-N 6-(2-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC=C1F GQLJJGUGKUYGRM-UHFFFAOYSA-N 0.000 claims 1
• IACXCHAZSQLGJN-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(Cl)=CC(Cl)=C1 IACXCHAZSQLGJN-UHFFFAOYSA-N 0.000 claims 1
• PJOQVYGNJMPLKZ-UHFFFAOYSA-N 6-(3-fluoro-5-methoxyphenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound COC1=CC(F)=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 PJOQVYGNJMPLKZ-UHFFFAOYSA-N 0.000 claims 1
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