JP2002543193A5 - - Google Patents
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- JP2002543193A5 JP2002543193A5 JP2000615601A JP2000615601A JP2002543193A5 JP 2002543193 A5 JP2002543193 A5 JP 2002543193A5 JP 2000615601 A JP2000615601 A JP 2000615601A JP 2000615601 A JP2000615601 A JP 2000615601A JP 2002543193 A5 JP2002543193 A5 JP 2002543193A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- dihydro
- oxazin
- benzo
- alkyl
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 description 67
- 125000003545 alkoxy group Chemical group 0.000 description 33
- 229910052799 carbon Inorganic materials 0.000 description 30
- 229910052736 halogen Inorganic materials 0.000 description 27
- -1 3-acetyl-phenyl Chemical group 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 21
- 150000002367 halogens Chemical class 0.000 description 21
- 125000004103 aminoalkyl group Chemical group 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- 125000000304 alkynyl group Chemical group 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 125000004426 substituted alkynyl group Chemical group 0.000 description 12
- 125000005842 heteroatom Chemical group 0.000 description 11
- 125000003107 substituted aryl group Chemical group 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 125000005017 substituted alkenyl group Chemical group 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 125000005309 thioalkoxy group Chemical group 0.000 description 8
- 125000000623 heterocyclic group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- QHWLPZYUNQBUGQ-UHFFFAOYSA-N (4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)boronic acid Chemical compound C1=C(B(O)O)C=C2C(C)(C)OC(=O)NC2=C1 QHWLPZYUNQBUGQ-UHFFFAOYSA-N 0.000 description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 150000001555 benzenes Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000005556 hormone Substances 0.000 description 5
- 229940088597 hormone Drugs 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 230000001613 neoplastic effect Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
- DGTZEHQWPNSIJS-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-cyclopropyl-4-prop-1-ynyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C#CC)(C3CC3)OC(=O)NC2=CC=C1C1=CC=CC(Cl)=C1 DGTZEHQWPNSIJS-UHFFFAOYSA-N 0.000 description 3
- OVZBDRQFIYMAJF-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-ethynyl-4-methyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C#C)OC(=O)NC2=CC=C1C1=CC=CC(Cl)=C1 OVZBDRQFIYMAJF-UHFFFAOYSA-N 0.000 description 3
- HZDVGBZUSRBRKH-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-methyl-4-prop-1-ynyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C#CC)(C)OC(=O)NC2=CC=C1C1=CC=CC(Cl)=C1 HZDVGBZUSRBRKH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 2
- 0 *C(*)(c1cc(*)ccc1N1*)OC1=O Chemical compound *C(*)(c1cc(*)ccc1N1*)OC1=O 0.000 description 2
- CZOVHBFQBUSVIK-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)benzenesulfonamide Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(S(N)(=O)=O)=C1 CZOVHBFQBUSVIK-UHFFFAOYSA-N 0.000 description 2
- DZRIKLQQKVBDJJ-UHFFFAOYSA-N 4,4-dimethyl-6-[3-(2-trimethylsilylethynyl)phenyl]-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(C#C[Si](C)(C)C)=C1 DZRIKLQQKVBDJJ-UHFFFAOYSA-N 0.000 description 2
- DTKBNYUNMFIZHZ-UHFFFAOYSA-N 4-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(C#N)C(F)=C1 DTKBNYUNMFIZHZ-UHFFFAOYSA-N 0.000 description 2
- WRAWKFUWOAFTDQ-UHFFFAOYSA-N 5-(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=CC=C(C#N)O1 WRAWKFUWOAFTDQ-UHFFFAOYSA-N 0.000 description 2
- UJOPEPOGMJPDOC-UHFFFAOYSA-N 5-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-2-sulfonamide Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(S(N)(=O)=O)S1 UJOPEPOGMJPDOC-UHFFFAOYSA-N 0.000 description 2
- RGFZPIHTBCRGJA-UHFFFAOYSA-N 6-(2-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC=C1F RGFZPIHTBCRGJA-UHFFFAOYSA-N 0.000 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 description 2
- PXPJJZAEWGAMEB-UHFFFAOYSA-N 6-(3-methoxyphenyl)-4-methyl-4-(trifluoromethyl)-1h-3,1-benzoxazin-2-one Chemical compound COC1=CC=CC(C=2C=C3C(C)(OC(=O)NC3=CC=2)C(F)(F)F)=C1 PXPJJZAEWGAMEB-UHFFFAOYSA-N 0.000 description 2
- IUVKLCLVLMLYNZ-UHFFFAOYSA-N 6-(6-aminopyridin-3-yl)-4,4-dimethyl-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(N)N=C1 IUVKLCLVLMLYNZ-UHFFFAOYSA-N 0.000 description 2
- 125000005330 8 membered heterocyclic group Chemical group 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 206010009944 Colon cancer Diseases 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 206010014733 Endometrial cancer Diseases 0.000 description 2
- 206010014759 Endometrial neoplasm Diseases 0.000 description 2
- 201000009273 Endometriosis Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 2
- 206010033128 Ovarian cancer Diseases 0.000 description 2
- 208000007913 Pituitary Neoplasms Diseases 0.000 description 2
- 201000007552 Pituitary carcinoma Diseases 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 2
- 208000009956 adenocarcinoma Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 201000008275 breast carcinoma Diseases 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 201000003914 endometrial carcinoma Diseases 0.000 description 2
- 230000002357 endometrial effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 201000010260 leiomyoma Diseases 0.000 description 2
- 206010027191 meningioma Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002632 myometrial effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000002611 ovarian Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 208000011866 pituitary adenocarcinoma Diseases 0.000 description 2
- 230000001817 pituitary effect Effects 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 201000001514 prostate carcinoma Diseases 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 125000004001 thioalkyl group Chemical group 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SDEAGACSNFSZCU-UHFFFAOYSA-N (3-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1 SDEAGACSNFSZCU-UHFFFAOYSA-N 0.000 description 1
- JVTRZJXFAOQMRA-UHFFFAOYSA-N 1,3-oxazin-2-one Chemical compound O=C1N=CC=CO1 JVTRZJXFAOQMRA-UHFFFAOYSA-N 0.000 description 1
- APLKINOTQCGFDO-UHFFFAOYSA-N 1-(2-amino-5-bromophenyl)cyclohexan-1-ol Chemical compound NC1=CC=C(Br)C=C1C1(O)CCCCC1 APLKINOTQCGFDO-UHFFFAOYSA-N 0.000 description 1
- IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
- UUZYFBXKWIQKTF-UHFFFAOYSA-N 2-(3-bromophenyl)acetonitrile Chemical compound BrC1=CC=CC(CC#N)=C1 UUZYFBXKWIQKTF-UHFFFAOYSA-N 0.000 description 1
- WBRVELFLQXWPBG-UHFFFAOYSA-N 2-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)thiophene-3-carbonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C=1SC=CC=1C#N WBRVELFLQXWPBG-UHFFFAOYSA-N 0.000 description 1
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 description 1
- AJDVWADIJRNVOJ-UHFFFAOYSA-N 2-[2-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)phenyl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC=C1CC#N AJDVWADIJRNVOJ-UHFFFAOYSA-N 0.000 description 1
- YYYDOHPSIISMSM-UHFFFAOYSA-N 2-[3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-4-fluorophenyl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(CC#N)=CC=C1F YYYDOHPSIISMSM-UHFFFAOYSA-N 0.000 description 1
- IDIRENXOSJYSCR-UHFFFAOYSA-N 2-[3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)phenyl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(CC#N)=C1 IDIRENXOSJYSCR-UHFFFAOYSA-N 0.000 description 1
- ZDCSCJIYANFAOX-UHFFFAOYSA-N 2-[4-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorophenyl]acetonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=C(CC#N)C(F)=C1 ZDCSCJIYANFAOX-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
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- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- JCVNKUXCFVBCQO-UHFFFAOYSA-N 3-(1-ethyl-4,4-dimethyl-2-oxo-3,1-benzoxazin-6-yl)-5-fluorobenzonitrile Chemical compound C=1C=C2N(CC)C(=O)OC(C)(C)C2=CC=1C1=CC(F)=CC(C#N)=C1 JCVNKUXCFVBCQO-UHFFFAOYSA-N 0.000 description 1
- VHIBSIPZVHZJEI-UHFFFAOYSA-N 3-(2-oxospiro[1h-3,1-benzoxazine-4,1'-cyclohexane]-6-yl)benzonitrile Chemical compound O1C(=O)NC2=CC=C(C=3C=C(C=CC=3)C#N)C=C2C21CCCCC2 VHIBSIPZVHZJEI-UHFFFAOYSA-N 0.000 description 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 description 1
- MMRUWYPAERDHDX-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-2-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CC(C#N)=C1F MMRUWYPAERDHDX-UHFFFAOYSA-N 0.000 description 1
- VRFFPOVHAWBDBG-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-4-fluorobenzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(C#N)=CC=C1F VRFFPOVHAWBDBG-UHFFFAOYSA-N 0.000 description 1
- NLEVEIAQKTVSTO-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-(trifluoromethoxy)benzonitrile Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC(OC(F)(F)F)=CC(C#N)=C1 NLEVEIAQKTVSTO-UHFFFAOYSA-N 0.000 description 1
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- JGYMUYVJOIEFFQ-UHFFFAOYSA-N 3-(4,4-dimethyl-2-oxo-1h-3,1-benzoxazin-6-yl)-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 JGYMUYVJOIEFFQ-UHFFFAOYSA-N 0.000 description 1
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- YYHMNNAXMFGWBB-UHFFFAOYSA-N 4,4-dimethyl-6-(1-methyl-5-nitropyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2C=C3C(C)(C)OC(=O)NC3=CC=2)=C1 YYHMNNAXMFGWBB-UHFFFAOYSA-N 0.000 description 1
- PNEKYSUBNQXRHM-UHFFFAOYSA-N 4,4-dimethyl-6-(1-methylpyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound CN1C=CC=C1C1=CC=C(NC(=O)OC2(C)C)C2=C1 PNEKYSUBNQXRHM-UHFFFAOYSA-N 0.000 description 1
- SMKZYKBPVNAOJL-UHFFFAOYSA-N 4,4-dimethyl-6-(1h-pyrrol-2-yl)-1h-3,1-benzoxazin-2-one Chemical compound C1=C2C(C)(C)OC(=O)NC2=CC=C1C1=CC=CN1 SMKZYKBPVNAOJL-UHFFFAOYSA-N 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 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 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18301299P | 1999-05-04 | 1999-05-04 | |
| US60/183,012 | 1999-05-04 | ||
| US09/552,633 | 2000-04-19 | ||
| US09/552,633 US6509334B1 (en) | 1999-05-04 | 2000-04-19 | Cyclocarbamate derivatives as progesterone receptor modulators |
| PCT/US2000/011822 WO2000066571A1 (en) | 1999-05-04 | 2000-05-01 | Cyclocarbamate derivatives as progesterone receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002543193A JP2002543193A (ja) | 2002-12-17 |
| JP2002543193A5 true JP2002543193A5 (https=) | 2007-06-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000615601A Pending JP2002543193A (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カルバメート誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP1173426A1 (https=) |
| JP (1) | JP2002543193A (https=) |
| KR (1) | KR20010114250A (https=) |
| CN (1) | CN1145618C (https=) |
| AU (1) | AU766428B2 (https=) |
| BG (1) | BG106079A (https=) |
| BR (1) | BR0010213A (https=) |
| CA (1) | CA2371726A1 (https=) |
| CZ (1) | CZ20013951A3 (https=) |
| EA (1) | EA004512B1 (https=) |
| HU (1) | HUP0201609A3 (https=) |
| IL (1) | IL146280A0 (https=) |
| MX (1) | MXPA01011286A (https=) |
| NO (1) | NO321361B1 (https=) |
| NZ (1) | NZ515355A (https=) |
| PL (1) | PL351127A1 (https=) |
| SG (1) | SG114650A1 (https=) |
| SK (1) | SK15912001A3 (https=) |
| TR (1) | TR200103286T2 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2562160C (en) * | 2004-04-27 | 2013-05-28 | Wyeth | Cyanopyrrole containing cyclic carbamate and thiocarbamate biaryls and methods for preparing the same |
| EP1844768A1 (en) * | 2005-01-19 | 2007-10-17 | Dainippon Sumitomo Pharma Co., Ltd. | Aromatic sulfone compound as aldosterone receptor modulator |
| JP5470043B2 (ja) | 2007-10-05 | 2014-04-16 | Ｍｓｄ株式会社 | ベンゾオキサジノン誘導体 |
| CN111925353B (zh) * | 2020-08-31 | 2022-04-08 | 苏州大学附属第二医院 | 一种2-噻吩甲腈的制备方法 |
Family Cites Families (4)
| 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 |
| WO1995020389A1 (en) * | 1994-01-28 | 1995-08-03 | Merck & Co., Inc. | Benzoxazinones as inhibitors of hiv reverse transcriptase |
| 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. |
-
2000
- 2000-05-01 CN CNB008071004A patent/CN1145618C/zh not_active Expired - Fee Related
- 2000-05-01 CA CA002371726A patent/CA2371726A1/en not_active Abandoned
- 2000-05-01 EA EA200101176A patent/EA004512B1/ru not_active IP Right Cessation
- 2000-05-01 BR BR0010213-0A patent/BR0010213A/pt not_active Application Discontinuation
- 2000-05-01 NZ NZ515355A patent/NZ515355A/xx unknown
- 2000-05-01 KR KR1020017013970A patent/KR20010114250A/ko not_active Ceased
- 2000-05-01 SK SK1591-2001A patent/SK15912001A3/sk unknown
- 2000-05-01 PL PL00351127A patent/PL351127A1/xx not_active Application Discontinuation
- 2000-05-01 AU AU46886/00A patent/AU766428B2/en not_active Ceased
- 2000-05-01 TR TR2001/03286T patent/TR200103286T2/xx unknown
- 2000-05-01 CZ CZ20013951A patent/CZ20013951A3/cs unknown
- 2000-05-01 HU HU0201609A patent/HUP0201609A3/hu unknown
- 2000-05-01 EP EP00928689A patent/EP1173426A1/en not_active Withdrawn
- 2000-05-01 JP JP2000615601A patent/JP2002543193A/ja active Pending
- 2000-05-01 IL IL14628000A patent/IL146280A0/xx unknown
- 2000-05-01 SG SG200400080A patent/SG114650A1/en unknown
- 2000-05-01 MX MXPA01011286A patent/MXPA01011286A/es unknown
-
2001
- 2001-11-02 BG BG106079A patent/BG106079A/xx unknown
- 2001-11-02 NO NO20015378A patent/NO321361B1/no not_active Application Discontinuation
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