JP2002543192A5 - - Google Patents
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- JP2002543192A5 JP2002543192A5 JP2000615600A JP2000615600A JP2002543192A5 JP 2002543192 A5 JP2002543192 A5 JP 2002543192A5 JP 2000615600 A JP2000615600 A JP 2000615600A JP 2000615600 A JP2000615600 A JP 2000615600A JP 2002543192 A5 JP2002543192 A5 JP 2002543192A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- dihydro
- group
- alkoxy
- 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
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- 125000000623 heterocyclic group Chemical group 0.000 description 33
- 125000003118 aryl group Chemical group 0.000 description 28
- 229910052736 halogen Inorganic materials 0.000 description 28
- 125000003107 substituted aryl group Chemical group 0.000 description 28
- 150000002367 halogens Chemical class 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 24
- 125000000217 alkyl group Chemical group 0.000 description 23
- 125000001424 substituent group Chemical group 0.000 description 23
- 125000005842 heteroatom Chemical group 0.000 description 16
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 125000006697 (C1-C3) aminoalkyl group Chemical group 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 0 *C(*)(c(cc(*)cc1)c1N1*)OC1=* Chemical compound *C(*)(c(cc(*)cc1)c1N1*)OC1=* 0.000 description 10
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 10
- 125000005309 thioalkoxy group Chemical group 0.000 description 10
- -1 4,4-dimethyl-2-thioxo-1,4-dihydro-2H-3,1-benzoxazin-6-yl Chemical group 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 125000000547 substituted alkyl group Chemical group 0.000 description 7
- 125000004426 substituted alkynyl group Chemical group 0.000 description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000005017 substituted alkenyl group Chemical group 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 150000001555 benzenes Chemical group 0.000 description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000004103 aminoalkyl group Chemical group 0.000 description 3
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 201000010260 leiomyoma Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KNXQDJCZSVHEIW-UHFFFAOYSA-N (3-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(F)=C1 KNXQDJCZSVHEIW-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- HDIUXGGZFPVMFR-UHFFFAOYSA-N 1-[2-amino-5-(3-fluorophenyl)phenyl]ethanone Chemical compound C1=C(N)C(C(=O)C)=CC(C=2C=C(F)C=CC=2)=C1 HDIUXGGZFPVMFR-UHFFFAOYSA-N 0.000 description 1
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- HPBRUWHVFSFZTL-UHFFFAOYSA-N 2-amino-5-(3-fluorophenyl)benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C1=CC=CC(F)=C1 HPBRUWHVFSFZTL-UHFFFAOYSA-N 0.000 description 1
- CUKXRHLWPSBCTI-UHFFFAOYSA-N 2-amino-5-bromobenzoic acid Chemical compound NC1=CC=C(Br)C=C1C(O)=O CUKXRHLWPSBCTI-UHFFFAOYSA-N 0.000 description 1
- OATYCBHROMXWJO-UHFFFAOYSA-N 2-amino-5-bromobenzonitrile Chemical compound NC1=CC=C(Br)C=C1C#N OATYCBHROMXWJO-UHFFFAOYSA-N 0.000 description 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 description 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 description 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 description 1
- 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 description 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 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 1
- CGXGBWUORDRNLY-UHFFFAOYSA-N 4,4-dimethyl-6-(3-methylthiophen-2-yl)-1H-3,1-benzoxazine-2-thione Chemical compound CC1=C(SC=C1)C2=CC3=C(C=C2)NC(=S)OC3(C)C CGXGBWUORDRNLY-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- 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 description 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 description 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 description 1
- 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 description 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 description 1
- 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 description 1
- 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 description 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 description 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 description 1
- 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 description 1
- KEODZYDOBHDZOT-UHFFFAOYSA-N 5-bromobenzene-1,3-dicarbonitrile Chemical compound BrC1=CC(C#N)=CC(C#N)=C1 KEODZYDOBHDZOT-UHFFFAOYSA-N 0.000 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 description 1
- 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 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 1
- 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 description 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 description 1
- ORNHFHBXIGMXLN-UHFFFAOYSA-N 6-(4-fluorophenyl)-4,4-dimethyl-1H-3,1-benzoxazine-2-thione 6-(4-fluorophenyl)-4,4-dimethyl-1H-3,1-benzoxazin-2-one Chemical compound FC1=CC=C(C=C1)C1=CC2=C(NC(OC2(C)C)=O)C=C1.FC1=CC=C(C=C1)C=1C=CC2=C(C(OC(N2)=S)(C)C)C1 ORNHFHBXIGMXLN-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
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- BUUPJTGMZSARMB-UHFFFAOYSA-N NC1=C(C=C(C=C1)Br)C1(CCCCC1)O.S=C1NC2=C(C3(O1)CCCCC3)C=C(C=C2)C=2C=C(SC2)C#N Chemical compound NC1=C(C=C(C=C1)Br)C1(CCCCC1)O.S=C1NC2=C(C3(O1)CCCCC3)C=C(C=C2)C=2C=C(SC2)C#N BUUPJTGMZSARMB-UHFFFAOYSA-N 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
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- 239000003937 drug carrier Substances 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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- 125000001979 organolithium group Chemical group 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 201000001514 prostate carcinoma Diseases 0.000 description 1
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- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 201000007954 uterine fibroid Diseases 0.000 description 1
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| 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 |
| PCT/US2000/011749 WO2000066570A1 (en) | 1999-05-04 | 2000-05-01 | Cyclothiocarbamate derivatives as progesterone receptor modulators |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2011249051A Division 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 |
Publications (3)
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|---|---|
| JP2002543192A JP2002543192A (ja) | 2002-12-17 |
| JP2002543192A5 true JP2002543192A5 (https=) | 2007-06-21 |
| JP4958338B2 JP4958338B2 (ja) | 2012-06-20 |
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| 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 |
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|---|---|---|---|
| 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 |
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=) |
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Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE386729T1 (de) * | 1999-05-04 | 2008-03-15 | Wyeth Corp | Cyclothiocarbamatderivate als progesteron- rezeptormodulatoren |
| US6407101B1 (en) * | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| ATE409699T1 (de) * | 2004-04-08 | 2008-10-15 | Wyeth Corp | Verfahren zur minimierung von thioamidverunreinigungen |
| ATE413398T1 (de) * | 2004-04-08 | 2008-11-15 | Wyeth Corp | Thioamidderivate als progesteronrezeptormodulatoren |
| EP1756072A2 (en) * | 2004-04-27 | 2007-02-28 | Wyeth | Purification of progesterone receptor modulators |
| CA2562160C (en) * | 2004-04-27 | 2013-05-28 | Wyeth | Cyanopyrrole containing cyclic carbamate and thiocarbamate biaryls and methods for preparing the same |
| WO2006014476A1 (en) * | 2004-07-07 | 2006-02-09 | Wyeth | Cyclic progestin regimens and kits |
| SI1778710T1 (sl) | 2004-08-13 | 2012-05-31 | Wyeth Llc | Derivati tanaprogeta metaboliti in njihove uporabe |
| EP1877059B8 (en) | 2005-04-28 | 2010-05-19 | Wyeth a Corporation of the State of Delaware | Micronized tanaproget and compostions containing same |
| JP2008539254A (ja) * | 2005-04-28 | 2008-11-13 | ワイス | タナプロゲットの精製形態 |
| SI1896034T1 (sl) | 2005-04-28 | 2010-07-30 | Wyeth Llc | Mikronizirani sestavki tanaprogeta in postopki priprave le-tega |
| WO2007030153A2 (en) * | 2005-04-28 | 2007-03-15 | Wyeth | Compositions containing micronized tanaproget |
| BRPI0610433A2 (pt) * | 2005-04-28 | 2010-11-23 | Wyeth Corp | forma polimórfica ii de tanaproget, processos para preparar a mesma, e para preparar forma micronizada de um composto, composição farmacêutica, método de preparação de uma composição farmacêutica, e, uso da forma polimórfica ii de tanaproget ou da forma micronizada |
| CN103989687A (zh) * | 2005-06-09 | 2014-08-20 | 惠氏公司 | 含有炔雌醇的tanaproget组合物 |
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 |
| WO1995020389A1 (en) * | 1994-01-28 | 1995-08-03 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
| US5696130A (en) * | 1994-12-22 | 1997-12-09 | Ligand Pharmaceuticals Incorporated | Tricyclic steroid receptor modulator compounds and methods |
| EP1043325B1 (en) * | 1994-12-22 | 2004-06-16 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| ES2203790T3 (es) * | 1996-10-02 | 2004-04-16 | Bristol-Myers Squibb Pharma Company | 1,4-dihidro-2h-3,1-benzoxacin-2-onas 4,4-disustituidas utiles como inhibidores de la transcriptasa reversa del hiv e intermedios y procedimientos para su preparacion. |
| ATE386729T1 (de) * | 1999-05-04 | 2008-03-15 | Wyeth Corp | Cyclothiocarbamatderivate als progesteron- rezeptormodulatoren |
| EP1877059B8 (en) * | 2005-04-28 | 2010-05-19 | Wyeth a Corporation of the State of Delaware | Micronized tanaproget and compostions containing same |
| CN103989687A (zh) * | 2005-06-09 | 2014-08-20 | 惠氏公司 | 含有炔雌醇的tanaproget组合物 |
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2000
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- 2000-05-01 HU HU0203332A patent/HUP0203332A3/hu unknown
- 2000-05-01 SG SG200400081A patent/SG120970A1/en unknown
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- 2000-05-01 SK SK1592-2001A patent/SK15922001A3/sk unknown
- 2000-05-01 JP JP2000615600A patent/JP4958338B2/ja not_active Expired - Fee Related
- 2000-05-01 EA EA200101181A patent/EA004511B1/ru not_active IP Right Cessation
- 2000-05-01 ES ES00930266T patent/ES2301482T3/es not_active Expired - Lifetime
- 2000-05-01 BR BR0010214-8A patent/BR0010214A/pt active Search and Examination
- 2000-05-01 DE DE60038108T patent/DE60038108T2/de not_active Expired - Lifetime
- 2000-05-01 DK DK00930266T patent/DK1175411T3/da active
- 2000-05-01 MX MXPA01011287A patent/MXPA01011287A/es active IP Right Grant
- 2000-05-01 TR TR2001/03285T patent/TR200103285T2/xx unknown
- 2000-05-01 EP EP00930266A patent/EP1175411B1/en not_active Expired - Lifetime
- 2000-05-01 CZ CZ20013952A patent/CZ20013952A3/cs unknown
- 2000-05-01 IL IL14629800A patent/IL146298A0/xx 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 AU AU48119/00A patent/AU766801B2/en not_active Ceased
- 2000-05-01 CN CN008070997A patent/CN1131856C/zh not_active Expired - Fee Related
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2001
- 2001-11-02 NO NO20015381A patent/NO321370B1/no unknown
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- 2011-11-14 JP JP2011249051A patent/JP5523430B2/ja not_active Expired - Fee Related
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