JP2013504523A5 - - Google Patents
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- JP2013504523A5 JP2013504523A5 JP2012528249A JP2012528249A JP2013504523A5 JP 2013504523 A5 JP2013504523 A5 JP 2013504523A5 JP 2012528249 A JP2012528249 A JP 2012528249A JP 2012528249 A JP2012528249 A JP 2012528249A JP 2013504523 A5 JP2013504523 A5 JP 2013504523A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- trifluoromethyl
- group
- oxo
- dimethyl
- 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.)
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- -1 tetrahydro-2H-pyranyl Chemical group 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 206010060862 Prostate cancer Diseases 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000002677 5-alpha reductase inhibitor Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 2
- 239000012453 solvate Chemical class 0.000 claims 35
- 150000003839 salts Chemical class 0.000 claims 34
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000001424 substituent group Chemical group 0.000 claims 15
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 9
- 239000011737 fluorine Chemical group 0.000 claims 9
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 8
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 5
- 239000000460 chlorine Chemical group 0.000 claims 5
- 229910052801 chlorine Inorganic materials 0.000 claims 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- 108700012941 GNRH1 Proteins 0.000 claims 4
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 4
- SOZGHDCEWOLLHV-UHFFFAOYSA-N 2-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=CC=C1C#N SOZGHDCEWOLLHV-UHFFFAOYSA-N 0.000 claims 3
- 125000005959 diazepanyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- RHOBTDQBNZMQNA-UHFFFAOYSA-N 4-[3-[(6-imidazol-1-ylpyridin-3-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=CN=C1 RHOBTDQBNZMQNA-UHFFFAOYSA-N 0.000 claims 2
- LGTPUPFZQOFLIO-UHFFFAOYSA-N 4-[3-[(6-methoxypyridin-3-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NC(OC)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S LGTPUPFZQOFLIO-UHFFFAOYSA-N 0.000 claims 2
- WVDXRFHMLCQHHK-UHFFFAOYSA-N 4-[3-[[6-(2-hydroxy-2-methylpropoxy)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NC(OCC(C)(O)C)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WVDXRFHMLCQHHK-UHFFFAOYSA-N 0.000 claims 2
- APZPTQCFVYYRAM-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[2-methyl-6-(trifluoromethyl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NC(C(F)(F)F)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S APZPTQCFVYYRAM-UHFFFAOYSA-N 0.000 claims 2
- ZFRXKMHBMKLZTP-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(2-methylimidazol-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NC=CN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S ZFRXKMHBMKLZTP-UHFFFAOYSA-N 0.000 claims 2
- UTFFSCUWBSEINO-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(2-methylmorpholin-4-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1COC(C)CN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S UTFFSCUWBSEINO-UHFFFAOYSA-N 0.000 claims 2
- ULROORUHAWRSRJ-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(2-morpholin-4-ylethoxy)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1OCCN1CCOCC1 ULROORUHAWRSRJ-UHFFFAOYSA-N 0.000 claims 2
- INVPXFWIDNEOIS-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-(trifluoromethyl)pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC1=CC=C(C(F)(F)F)N=C1 INVPXFWIDNEOIS-UHFFFAOYSA-N 0.000 claims 2
- DSMLVMACRTUXNV-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-[4-(trifluoromethyl)imidazol-1-yl]pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(C(F)(F)F)=C1 DSMLVMACRTUXNV-UHFFFAOYSA-N 0.000 claims 2
- 229940113178 5 Alpha reductase inhibitor Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 claims 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000005961 oxazepanyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- JWOKAJZCYYEKOL-UHFFFAOYSA-N 4-[3-[(2-imidazol-1-ylpyrimidin-5-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CN=C1N1C=CN=C1 JWOKAJZCYYEKOL-UHFFFAOYSA-N 0.000 claims 1
- OXSMUXJNNLYPNB-UHFFFAOYSA-N 4-[3-[(4-amino-2-morpholin-4-ylpyrimidin-5-yl)methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C(=N1)N)=CN=C1N1CCOCC1 OXSMUXJNNLYPNB-UHFFFAOYSA-N 0.000 claims 1
- OKHRCTLRYULJML-UHFFFAOYSA-N 4-[3-[[6-(2,2-difluoro-3-hydroxypropoxy)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC1=CC=C(OCC(F)(F)CO)N=C1 OKHRCTLRYULJML-UHFFFAOYSA-N 0.000 claims 1
- PCGYKQMQQGCBKT-UHFFFAOYSA-N 4-[3-[[6-(2-hydroxy-2-methylpropoxy)-2-methylpyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NC(OCC(C)(C)O)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S PCGYKQMQQGCBKT-UHFFFAOYSA-N 0.000 claims 1
- KUHRTZWWSAPQNC-UHFFFAOYSA-N 4-[3-[[6-(2-methoxyethoxy)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NC(OCCOC)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S KUHRTZWWSAPQNC-UHFFFAOYSA-N 0.000 claims 1
- HYJCFOZUGWNRCW-UHFFFAOYSA-N 4-[3-[[6-(4,4-dimethyl-2-oxopyrrolidin-1-yl)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound O=C1CC(C)(C)CN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S HYJCFOZUGWNRCW-UHFFFAOYSA-N 0.000 claims 1
- KLKQEZMEYBOCMI-UHFFFAOYSA-N 4-[3-[[6-(4,5-dichloroimidazol-1-yl)pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(Cl)=C1Cl KLKQEZMEYBOCMI-UHFFFAOYSA-N 0.000 claims 1
- PRXMTRSOZRZLCB-UHFFFAOYSA-N 4-[3-[[6-[4-(hydroxymethyl)imidazol-1-yl]pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(CO)=C1 PRXMTRSOZRZLCB-UHFFFAOYSA-N 0.000 claims 1
- LZMLDWHYWHCQMY-UHFFFAOYSA-N 4-[3-[[6-[4-(hydroxymethyl)piperidin-1-yl]pyridin-3-yl]methyl]-4,4-dimethyl-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1CCC(CO)CC1 LZMLDWHYWHCQMY-UHFFFAOYSA-N 0.000 claims 1
- WHIQABQLQGWBCV-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(1-methylpyrazol-4-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NN(C)C=C1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WHIQABQLQGWBCV-UHFFFAOYSA-N 0.000 claims 1
- UKJSICXNIWAFHT-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(2-methylpyrazol-3-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CN1N=CC=C1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S UKJSICXNIWAFHT-UHFFFAOYSA-N 0.000 claims 1
- LGMXJTSZOZHILY-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(4-methyl-1,4-diazepan-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1CN(C)CCCN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S LGMXJTSZOZHILY-UHFFFAOYSA-N 0.000 claims 1
- AMJWLRAHKCPZOA-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(4-methylimidazol-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C1=NC(C)=CN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S AMJWLRAHKCPZOA-UHFFFAOYSA-N 0.000 claims 1
- WNVXGCCNACRRBU-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(5-methylpyrazol-1-yl)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=CC=NN1C(N=C1)=CC=C1CN1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WNVXGCCNACRRBU-UHFFFAOYSA-N 0.000 claims 1
- FOPFPJNAKKDYAM-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[[6-(oxan-4-yloxy)pyridin-3-yl]methyl]-5-oxo-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1OC1CCOCC1 FOPFPJNAKKDYAM-UHFFFAOYSA-N 0.000 claims 1
- XMPRPUJWELKBGN-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-(tetrazol-1-yl)pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NN=N1 XMPRPUJWELKBGN-UHFFFAOYSA-N 0.000 claims 1
- INQSQGKIWMOGON-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-(triazol-1-yl)pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=CN=N1 INQSQGKIWMOGON-UHFFFAOYSA-N 0.000 claims 1
- MSBIXCPKNNJENE-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-(triazol-2-yl)pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1N=CC=N1 MSBIXCPKNNJENE-UHFFFAOYSA-N 0.000 claims 1
- DRMMKXZBPFROFE-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-2-sulfanylidene-3-[[6-[3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyridin-3-yl]methyl]imidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1C=NC(C(F)(F)F)=N1 DRMMKXZBPFROFE-UHFFFAOYSA-N 0.000 claims 1
- DFSNMLVHGDCRDN-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-3-[[6-(2-oxoimidazolidin-1-yl)pyridin-3-yl]methyl]-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1N1CCNC1=O DFSNMLVHGDCRDN-UHFFFAOYSA-N 0.000 claims 1
- TYPIQCVZXDXIIX-UHFFFAOYSA-N 4-[4,4-dimethyl-5-oxo-3-[[6-[2-(2-oxoimidazolidin-1-yl)ethoxy]pyridin-3-yl]methyl]-2-sulfanylideneimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound S=C1N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C(=O)C(C)(C)N1CC(C=N1)=CC=C1OCCN1CCNC1=O TYPIQCVZXDXIIX-UHFFFAOYSA-N 0.000 claims 1
- 229940123407 Androgen receptor antagonist Drugs 0.000 claims 1
- 229940122014 Lyase inhibitor Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003936 androgen receptor antagonist Substances 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 229940046836 anti-estrogen Drugs 0.000 claims 1
- 230000001833 anti-estrogenic effect Effects 0.000 claims 1
- 239000003418 antiprogestin Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 239000000824 cytostatic agent Substances 0.000 claims 1
- 230000001085 cytostatic effect Effects 0.000 claims 1
- 229940011871 estrogen Drugs 0.000 claims 1
- 239000000262 estrogen Substances 0.000 claims 1
- 239000000328 estrogen antagonist Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 229940043355 kinase inhibitor Drugs 0.000 claims 1
- 239000002697 lyase inhibitor Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- ZBZMKIRXPGQRFJ-UHFFFAOYSA-N n-oxomethanimidamide Chemical compound N=CN=O ZBZMKIRXPGQRFJ-UHFFFAOYSA-N 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 238000007614 solvation Methods 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 description 10
- 102000001307 androgen receptors Human genes 0.000 description 7
- 108010080146 androgen receptors Proteins 0.000 description 7
- 239000003098 androgen Substances 0.000 description 6
- 201000011510 cancer Diseases 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000002018 overexpression Effects 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002280 anti-androgenic effect Effects 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
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| US9199976B2 (en) * | 2010-06-01 | 2015-12-01 | The University Of Queensland | Haematopoietic-prostaglandin D2 synthase inhibitors |
| UA117095C2 (uk) | 2011-12-22 | 2018-06-25 | Аліос Біофарма, Інк. | Нуклеозидна сполука або її фармацевтично прийнятна сіль |
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| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| SG11201407336PA (en) | 2012-05-25 | 2015-03-30 | Janssen Sciences Ireland Uc | Uracyl spirooxetane nucleosides |
| TW201418243A (zh) | 2012-11-15 | 2014-05-16 | Bayer Pharma AG | 含有磺醯亞胺基團之ｎ－（吡啶－２－基）嘧啶－４－胺衍生物 |
| GEP201706757B (en) | 2012-12-21 | 2017-10-25 | Alios Biopharma Inc | Substituted nucleosides, nucleotides and analogs thereof |
| WO2014153280A1 (en) * | 2013-03-22 | 2014-09-25 | Merck Sharp & Dohme Corp. | 2-pyridyl carboxamide-containing spleen tyrosine kinase (syk) inhibitors |
| CN104341351B (zh) * | 2013-07-30 | 2018-02-06 | 北京海美源医药科技有限公司 | 一种二芳基硫代乙内酰脲衍生物及其应用 |
| SI3080100T1 (sl) * | 2013-12-11 | 2023-04-28 | Celgene Quanticel Research, Inc. | Inhibitorji lizin specifične demetilaze-1 |
| CN105829296A (zh) | 2013-12-18 | 2016-08-03 | 巴斯夫欧洲公司 | 带有亚胺衍生的取代基的唑类化合物 |
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| CN103896847B (zh) * | 2014-04-09 | 2016-01-20 | 沈江 | 一种非甾体类抗雄激素化合物及其制备方法和应用 |
| EP3140300B1 (en) | 2014-05-07 | 2019-08-14 | Evotec International GmbH | Sulfoximine substituted quinazolines for pharmaceutical compositions |
| TWI700283B (zh) | 2014-08-04 | 2020-08-01 | 德商拜耳製藥公司 | ２-(嗎啉-４-基)-１,７-萘啶 |
| CN106187905B (zh) * | 2015-05-05 | 2020-02-21 | 北京海步医药科技股份有限公司 | 丁鲁他胺的结晶形式及其制备方法 |
| JP6888000B2 (ja) | 2015-10-08 | 2021-06-16 | バイエル ファーマ アクチエンゲゼルシャフト | 新規な修飾された大環状化合物 |
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| TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
| EP3601253B1 (en) | 2017-03-28 | 2021-09-15 | Bayer Aktiengesellschaft | Novel ptefb inhibiting macrocyclic compounds |
| CA3057891A1 (en) | 2017-03-28 | 2018-10-04 | Bayer Aktiengesellschaft | Novel ptefb inhibiting macrocyclic compounds |
| CN110770210A (zh) | 2017-05-18 | 2020-02-07 | Pi工业有限公司 | 新颖的脒化合物 |
| MA51820A (fr) | 2018-02-13 | 2021-05-19 | Bayer Ag | Utilisation de 5-fluoro-4-(4-fluoro-2-méthoxyphényl)-n-(4-[(s-méthylsulfonimidoyl)méthyl]pyridin-2-yl)pyridin-2-amine pour traiter un lymphome diffus à grandes cellules b |
| EP3953342B1 (en) * | 2019-04-11 | 2025-09-24 | University of Miami | Improved inhibitors of the notch transcriptional activation complex and methods for use of the same |
| CA3165120A1 (en) * | 2020-01-21 | 2021-07-29 | Berkley E. GRYDER | Aryl hydantoin heterocycles and methods of use |
| WO2022206742A1 (zh) * | 2021-03-30 | 2022-10-06 | 苏州开拓药业股份有限公司 | 一种一步法合成乙内酰硫脲衍生物的方法 |
| WO2025103470A1 (zh) * | 2023-11-17 | 2025-05-22 | 中国药科大学 | 作为雄激素受体(ar)拮抗剂的化合物及其应用 |
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| TWI469971B (zh) | 2007-10-26 | 2015-01-21 | Univ California | 二芳基乙內醯脲類化合物 |
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- 2012-03-09 CR CR20120113A patent/CR20120113A/es unknown
- 2012-03-09 CL CL2012000623A patent/CL2012000623A1/es unknown
- 2012-03-09 EC ECSP12011716 patent/ECSP12011716A/es unknown
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