CA2371712C - Cyclothiocarbamate derivatives as progesterone receptor modulators - Google Patents

Info

Publication number

CA2371712C

CA2371712C CA002371712A CA2371712A CA2371712C CA 2371712 C CA2371712 C CA 2371712C CA 002371712 A CA002371712 A CA 002371712A CA 2371712 A CA2371712 A CA 2371712A CA 2371712 C CA2371712 C CA 2371712C

Authority

CA

Canada

Prior art keywords

substituted

alkyl

group

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.)

Expired - Fee Related

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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 150
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 146
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 99
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 89
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 83
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 73
• 125000003118 aryl group Chemical group 0.000 claims abstract description 68
• 125000001424 substituent group Chemical group 0.000 claims abstract description 60
• 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 49
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 48
• 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 44
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 38
• 150000003839 salts Chemical class 0.000 claims abstract description 26
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 25
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 19
• 229910052760 oxygen Inorganic materials 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 14
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 86
• 229910052739 hydrogen Inorganic materials 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 59
• 229910052799 carbon Inorganic materials 0.000 claims description 53
• 150000002367 halogens Chemical class 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 35
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 21
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
• 125000005157 alkyl carboxy group Chemical group 0.000 claims description 18
• 125000005309 thioalkoxy group Chemical group 0.000 claims description 18
• 125000005110 aryl thio group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 16
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 9
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 7
• 201000009273 Endometriosis Diseases 0.000 claims description 6
• 150000001555 benzenes Chemical group 0.000 claims description 6
• 210000000481 breast Anatomy 0.000 claims description 6
• 201000009030 Carcinoma Diseases 0.000 claims description 5
• 208000009956 adenocarcinoma Diseases 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 230000000740 bleeding effect Effects 0.000 claims description 5
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
• 210000001072 colon Anatomy 0.000 claims description 5
• 210000004696 endometrium Anatomy 0.000 claims description 5
• 210000001672 ovary Anatomy 0.000 claims description 5
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
• 210000002307 prostate Anatomy 0.000 claims description 5
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 4
• 206010046798 Uterine leiomyoma Diseases 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 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 description 4
• 125000002785 azepinyl group Chemical group 0.000 claims description 4
• 235000010290 biphenyl Nutrition 0.000 claims description 4
• 238000002657 hormone replacement therapy Methods 0.000 claims description 4
• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 201000010260 leiomyoma Diseases 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000005561 phenanthryl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
• 125000006089 thiamorpholinyl sulfoxide group Chemical group 0.000 claims description 4
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 4
• CUQLFUMXNAKZSH-UHFFFAOYSA-N 3-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)benzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(C#N)=C1 CUQLFUMXNAKZSH-UHFFFAOYSA-N 0.000 claims description 3
• 229910020008 S(O) Inorganic materials 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 3
• 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
• 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
• 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
• 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 2
• 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 2
• 125000005843 halogen group Chemical group 0.000 claims 19
• 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims 4
• 239000003814 drug Substances 0.000 claims 4
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 3
• 239000003433 contraceptive agent Substances 0.000 claims 2
• 230000002254 contraceptive effect Effects 0.000 claims 2
• 125000002971 oxazolyl group Chemical group 0.000 claims 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims 2
• 125000001544 thienyl group Chemical group 0.000 claims 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 1
• 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 1
• 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 1
• JWRMZXFZQZVKSD-UHFFFAOYSA-N 3-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(F)=CC(C#N)=C1 JWRMZXFZQZVKSD-UHFFFAOYSA-N 0.000 claims 1
• NGXWFLCNLTYJKI-UHFFFAOYSA-N 3-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-5-methylbenzonitrile Chemical compound CC1=CC(C#N)=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 NGXWFLCNLTYJKI-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 1
• XURBBVPMTVGZEP-UHFFFAOYSA-N 3-fluoro-5-(2-sulfanylidenespiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)benzonitrile Chemical compound FC1=CC(C#N)=CC(C=2C=C3C4(CCCCC4)OC(=S)NC3=CC=2)=C1 XURBBVPMTVGZEP-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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
• UCEMKOZZXFXATD-UHFFFAOYSA-N 4-(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=CSC(C#N)=C1 UCEMKOZZXFXATD-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 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 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
• BCDNJBDJBGOTIA-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-1h-pyrrole-2-carbothioamide Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(C(N)=S)N1 BCDNJBDJBGOTIA-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• NUQMIQUEODQESK-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)furan-2-carbonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(C#N)O1 NUQMIQUEODQESK-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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• 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 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
• 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 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
• 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 1
• 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 1
• 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 1
• 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 1
• HWFFFZIEYMMDDC-UHFFFAOYSA-N 6-(3-chlorophenyl)-4,4-diethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(CC)(CC)OC(=S)NC2=CC=C1C1=CC=CC(Cl)=C1 HWFFFZIEYMMDDC-UHFFFAOYSA-N 0.000 claims 1
• XCHOFVZQFUVVEB-UHFFFAOYSA-N 6-(3-chlorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(Cl)=C1 XCHOFVZQFUVVEB-UHFFFAOYSA-N 0.000 claims 1
• 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 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
• JKKKYMAGXVPMSE-UHFFFAOYSA-N 6-(3-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(F)=C1 JKKKYMAGXVPMSE-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• PIVCHRZUHMHWMD-UHFFFAOYSA-N 6-(4-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=C(F)C=C1 PIVCHRZUHMHWMD-UHFFFAOYSA-N 0.000 claims 1
• GHELUGIZMVFOKT-UHFFFAOYSA-N 6-(5-bromopyridin-3-yl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CN=CC(Br)=C1 GHELUGIZMVFOKT-UHFFFAOYSA-N 0.000 claims 1
• FXVPGONKQHRTRT-UHFFFAOYSA-N 6-[3-bromo-5-(trifluoromethoxy)phenyl]-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(Br)=CC(OC(F)(F)F)=C1 FXVPGONKQHRTRT-UHFFFAOYSA-N 0.000 claims 1
• KWEKPTTVUMVEHM-UHFFFAOYSA-N 6-[3-fluoro-5-(trifluoromethyl)phenyl]-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(F)=CC(C(F)(F)F)=C1 KWEKPTTVUMVEHM-UHFFFAOYSA-N 0.000 claims 1
• 229920001774 Perfluoroether Polymers 0.000 claims 1
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims 1
• PYVFWTPEBMRKSR-UHFFFAOYSA-N tanaproget Chemical compound CN1C(C#N)=CC=C1C1=CC=C(NC(=S)OC2(C)C)C2=C1 PYVFWTPEBMRKSR-UHFFFAOYSA-N 0.000 claims 1
• VTHCULBLEKIUTL-UHFFFAOYSA-N thiophene-3-carbonitrile Chemical compound N#CC1=[C]SC=C1 VTHCULBLEKIUTL-UHFFFAOYSA-N 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 110
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 abstract description 31
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