JP2012087129A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2012087129A5 JP2012087129A5 JP2011249051A JP2011249051A JP2012087129A5 JP 2012087129 A5 JP2012087129 A5 JP 2012087129A5 JP 2011249051 A JP2011249051 A JP 2011249051A JP 2011249051 A JP2011249051 A JP 2011249051A JP 2012087129 A5 JP2012087129 A5 JP 2012087129A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- dihydro
- dimethyl
- benzoxazine
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 78
- 229910052799 carbon Inorganic materials 0.000 claims 55
- 125000000623 heterocyclic group Chemical group 0.000 claims 40
- 125000003118 aryl group Chemical group 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 125000003107 substituted aryl group Chemical group 0.000 claims 30
- 239000000203 mixture Substances 0.000 claims 27
- 125000003545 alkoxy group Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 125000004103 aminoalkyl group Chemical group 0.000 claims 16
- 125000001424 substituent group Chemical group 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 12
- 125000003342 alkenyl group Chemical group 0.000 claims 12
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- -1 R 2 is H Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 9
- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001555 benzenes Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 6
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 4
- 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 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 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 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 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 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 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 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 2
- 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 2
- 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 2
- 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 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 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 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 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 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 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 2
- 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 2
- 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 2
- OEVOYVHAFYXKNX-UHFFFAOYSA-N 4-(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=COC(C#N)=C1 OEVOYVHAFYXKNX-UHFFFAOYSA-N 0.000 claims 2
- 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 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 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 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 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 2
- 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 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 2
- 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 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 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 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 2
- 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 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 2
- IBEVIFARERDACQ-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)thiophene-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC(C#N)=CS1 IBEVIFARERDACQ-UHFFFAOYSA-N 0.000 claims 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 2
- 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 2
- 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 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 2
- 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 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 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 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 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 2
- IUQHQDMKFBMQME-UHFFFAOYSA-N 6-(3-chloro-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(Cl)=C1 IUQHQDMKFBMQME-UHFFFAOYSA-N 0.000 claims 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 2
- 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 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 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 2
- 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 2
- 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 2
- 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 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 229940123788 Progesterone receptor antagonist Drugs 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 2
- 238000009472 formulation Methods 0.000 claims 2
- LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 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 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
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 206010014733 Endometrial cancer Diseases 0.000 claims 1
- 206010014759 Endometrial neoplasm Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 229940122880 Estrogen receptor agonist Drugs 0.000 claims 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- 230000003796 beauty Effects 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 210000001072 colon Anatomy 0.000 claims 1
- 208000029742 colonic neoplasm Diseases 0.000 claims 1
- 239000003433 contraceptive agent Substances 0.000 claims 1
- 230000002254 contraceptive effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002357 endometrial effect Effects 0.000 claims 1
- 238000002657 hormone replacement therapy Methods 0.000 claims 1
- 201000010260 leiomyoma Diseases 0.000 claims 1
- 230000002611 ovarian Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 1
- 229940044551 receptor antagonist Drugs 0.000 claims 1
- 239000002464 receptor antagonist Substances 0.000 claims 1
- 210000002460 smooth muscle Anatomy 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 0 Cc1cccc(*)c1 Chemical compound Cc1cccc(*)c1 0.000 description 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18301399P | 1999-05-04 | 1999-05-04 | |
| US60/183,013 | 1999-05-04 | ||
| US09/552,354 | 2000-04-19 | ||
| US09/552,354 US6436929B1 (en) | 1999-05-04 | 2000-04-19 | Cyclothiocarbamate derivatives as progesterone receptor modulators |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000615600A Division JP4958338B2 (ja) | 1999-05-04 | 2000-05-01 | プロゲステロン受容体モジュレーターとしてのシクロチオカルバメート誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012087129A JP2012087129A (ja) | 2012-05-10 |
| JP2012087129A5 true JP2012087129A5 (https=) | 2012-06-21 |
| JP5523430B2 JP5523430B2 (ja) | 2014-06-18 |
Family
ID=26878649
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000615600A Expired - Fee Related JP4958338B2 (ja) | 1999-05-04 | 2000-05-01 | プロゲステロン受容体モジュレーターとしてのシクロチオカルバメート誘導体 |
| JP2011249051A Expired - Fee Related JP5523430B2 (ja) | 1999-05-04 | 2011-11-14 | プロゲステロン受容体モジュレーターとしてのシクロチオカルバメート誘導体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000615600A Expired - Fee Related JP4958338B2 (ja) | 1999-05-04 | 2000-05-01 | プロゲステロン受容体モジュレーターとしてのシクロチオカルバメート誘導体 |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1175411B1 (https=) |
| JP (2) | JP4958338B2 (https=) |
| KR (1) | KR100732692B1 (https=) |
| CN (1) | CN1131856C (https=) |
| AT (1) | ATE386729T1 (https=) |
| AU (1) | AU766801B2 (https=) |
| BG (1) | BG65277B1 (https=) |
| BR (1) | BR0010214A (https=) |
| CA (1) | CA2371712C (https=) |
| CZ (1) | CZ20013952A3 (https=) |
| DE (1) | DE60038108T2 (https=) |
| DK (1) | DK1175411T3 (https=) |
| EA (1) | EA004511B1 (https=) |
| ES (1) | ES2301482T3 (https=) |
| GE (1) | GEP20043181B (https=) |
| HU (1) | HUP0203332A3 (https=) |
| IL (1) | IL146298A0 (https=) |
| MX (1) | MXPA01011287A (https=) |
| NO (1) | NO321370B1 (https=) |
| NZ (1) | NZ515353A (https=) |
| PL (1) | PL351083A1 (https=) |
| SG (1) | SG120970A1 (https=) |
| SK (1) | SK15922001A3 (https=) |
| TR (1) | TR200103285T2 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG120970A1 (en) * | 1999-05-04 | 2006-04-26 | Ligand Pharm Inc | Cyclothiocarbamate derivatives as progesterone receptor modulators |
| US6407101B1 (en) * | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| ES2317223T3 (es) * | 2004-04-08 | 2009-04-16 | Wyeth | Derivados de tioamida como moduladores del receptor de progesterona. |
| JP4950027B2 (ja) * | 2004-04-08 | 2012-06-13 | ワイス・エルエルシー | チオアミド不純物を最小限に抑えるための方法 |
| BRPI0510278A (pt) * | 2004-04-27 | 2007-10-30 | Wyeth Corp | método para produzir compostos, produto, e, composto |
| MXPA06012403A (es) | 2004-04-27 | 2007-01-17 | Wyeth Corp | Purificacion de moduladores de receptor progesterona. |
| US20060009428A1 (en) * | 2004-07-07 | 2006-01-12 | Wyeth | Cyclic progestin regimens and kits |
| MX2007001812A (es) * | 2004-08-13 | 2007-03-26 | Wyeth Corp | Derivados de tanaproget, metabolitos, y usos de los mismos. |
| CN101166532B (zh) | 2005-04-28 | 2011-06-22 | 惠氏公司 | 微粒化的他那普戈特、组合物及其制备方法 |
| CN101166521A (zh) * | 2005-04-28 | 2008-04-23 | 惠氏公司 | 通过湿制粒法制备包含微粒化他那普戈特的组合物 |
| CN101166736B (zh) * | 2005-04-28 | 2013-02-06 | 惠氏公司 | 他那普戈特的多晶型ⅱ |
| AU2006241189B2 (en) * | 2005-04-28 | 2012-01-19 | Wyeth Llc | Purified form of tanaproget |
| MX2007013467A (es) | 2005-04-28 | 2008-01-21 | Wyeth Corp | Tanaproget micronizado y composiciones que contienen el mismo. |
| CA2610767C (en) * | 2005-06-09 | 2014-09-23 | Wyeth | Tanaproget compositions containing ethinyl estradiol |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0510235A1 (en) * | 1991-04-26 | 1992-10-28 | Dong-A Pharm. Co., Ltd. | Novel benzoxazine or benzothiazine derivatives and process for the preparation of the same |
| JPH0510235A (ja) * | 1991-07-05 | 1993-01-19 | Nippondenso Co Ltd | 内燃機関の点火時期制御装置 |
| AU1694295A (en) * | 1994-01-28 | 1995-08-15 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
| US5696127A (en) * | 1994-12-22 | 1997-12-09 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| EP1043325B1 (en) * | 1994-12-22 | 2004-06-16 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| DE69724630T2 (de) * | 1996-10-02 | 2004-07-29 | Bristol-Myers Squibb Pharma Co. | 4,4-disubstituierte 1,4-dihydro-2h-3,1-benzoxazin-2-one die anwendbar sind als hiv-reverstranskriptase-inhibitoren, zwischenprodukte und verfahren zu ihrer herstellung |
| SG120970A1 (en) * | 1999-05-04 | 2006-04-26 | Ligand Pharm Inc | Cyclothiocarbamate derivatives as progesterone receptor modulators |
| MX2007013467A (es) * | 2005-04-28 | 2008-01-21 | Wyeth Corp | Tanaproget micronizado y composiciones que contienen el mismo. |
| CA2610767C (en) * | 2005-06-09 | 2014-09-23 | Wyeth | Tanaproget compositions containing ethinyl estradiol |
-
2000
- 2000-05-01 SG SG200400081A patent/SG120970A1/en unknown
- 2000-05-01 NZ NZ515353A patent/NZ515353A/xx unknown
- 2000-05-01 PL PL00351083A patent/PL351083A1/xx not_active Application Discontinuation
- 2000-05-01 CA CA002371712A patent/CA2371712C/en not_active Expired - Fee Related
- 2000-05-01 KR KR1020017014085A patent/KR100732692B1/ko not_active Expired - Fee Related
- 2000-05-01 EP EP00930266A patent/EP1175411B1/en not_active Expired - Lifetime
- 2000-05-01 GE GEAP20006120A patent/GEP20043181B/en unknown
- 2000-05-01 MX MXPA01011287A patent/MXPA01011287A/es active IP Right Grant
- 2000-05-01 IL IL14629800A patent/IL146298A0/xx unknown
- 2000-05-01 TR TR2001/03285T patent/TR200103285T2/xx unknown
- 2000-05-01 BR BR0010214-8A patent/BR0010214A/pt active Search and Examination
- 2000-05-01 EA EA200101181A patent/EA004511B1/ru not_active IP Right Cessation
- 2000-05-01 CN CN008070997A patent/CN1131856C/zh not_active Expired - Fee Related
- 2000-05-01 HU HU0203332A patent/HUP0203332A3/hu unknown
- 2000-05-01 AU AU48119/00A patent/AU766801B2/en not_active Ceased
- 2000-05-01 DE DE60038108T patent/DE60038108T2/de not_active Expired - Lifetime
- 2000-05-01 ES ES00930266T patent/ES2301482T3/es not_active Expired - Lifetime
- 2000-05-01 DK DK00930266T patent/DK1175411T3/da active
- 2000-05-01 SK SK1592-2001A patent/SK15922001A3/sk unknown
- 2000-05-01 CZ CZ20013952A patent/CZ20013952A3/cs unknown
- 2000-05-01 JP JP2000615600A patent/JP4958338B2/ja not_active Expired - Fee Related
- 2000-05-01 AT AT00930266T patent/ATE386729T1/de not_active IP Right Cessation
-
2001
- 2001-11-02 NO NO20015381A patent/NO321370B1/no unknown
- 2001-11-02 BG BG106080A patent/BG65277B1/bg unknown
-
2011
- 2011-11-14 JP JP2011249051A patent/JP5523430B2/ja not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2012087129A5 (https=) | ||
| RU2005101625A (ru) | Производные циклотиокарбамата как модуляторы рецепторов прогестерона и их применение для лечения кожных заболеваний | |
| RU2005101638A (ru) | Использование циклокарбаматных производных для лечения гормонзависимых состояний | |
| RU2426731C2 (ru) | Производные арил-изоксазоло-4-ил-оксадиазола | |
| RU2007107177A (ru) | Соединения и композиции, как модуляторы ядерных рецепторов стероидных гормонов | |
| RU2492167C2 (ru) | Производные аминотриазола в качестве агонистов alх | |
| JP2013525438A5 (https=) | ||
| RU2014124640A (ru) | Производные аминопиримидина в качестве модуляторов богатой лейцином повторной киназы 2 (lrrk2) | |
| CA2737999A1 (en) | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma | |
| AR110403A1 (es) | Fungicidas de oxadiazoles | |
| DK2922848T3 (da) | Oxazolidin-2-on-pyrimidinderivater | |
| JP2014526500A5 (https=) | ||
| RU2016111138A (ru) | Гетероциклические соединения и способы их применения | |
| JP2008507539A5 (https=) | ||
| CA2636077A1 (en) | Thiazole compounds as protein kinase b (pkb) inhibitors | |
| JP2013517279A5 (https=) | ||
| JP2009525960A5 (https=) | ||
| RU2012134306A (ru) | Азотосодержащие производные гетероарилов | |
| PE20081228A1 (es) | Compuesto heteromonociclico | |
| HRP20180371T1 (hr) | Novi derivati piridina | |
| RU2013138834A (ru) | N-[3-(5-амино-3,3а,7,7а-тетрагидро-1н-2,4-диокса-6-аза-инден-7-ил)-фенил]-амиды в качестве ингибиторов васе1 и(или) васе2 | |
| JP2017501983A5 (https=) | ||
| JP2018507234A5 (https=) | ||
| JP2010502576A5 (https=) | ||
| RU2017118562A (ru) | Соединения-антагонисты дофаминового d3-рецептора |