JP2015510868A5 - - Google Patents
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- Publication number
- JP2015510868A5 JP2015510868A5 JP2014559833A JP2014559833A JP2015510868A5 JP 2015510868 A5 JP2015510868 A5 JP 2015510868A5 JP 2014559833 A JP2014559833 A JP 2014559833A JP 2014559833 A JP2014559833 A JP 2014559833A JP 2015510868 A5 JP2015510868 A5 JP 2015510868A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- benzyl
- amino
- piperidine
- fluoro
- 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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- -1 cyano, nitro, amino Chemical group 0.000 claims 84
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 52
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 22
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 21
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000006653 (C1-C20) heteroaryl group Chemical group 0.000 claims 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 18
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical group 0.000 claims 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 3
- 229920002554 vinyl polymer Polymers 0.000 claims 3
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims 2
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000003163 gonadal steroid hormone Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 201000010260 leiomyoma Diseases 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 238000011321 prophylaxis Methods 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 2
- 238000011282 treatment Methods 0.000 claims 2
- 125000006573 (C1-C10) heteroaryl group Chemical group 0.000 claims 1
- VTRIFTLAGXOFRH-QFIPXVFZSA-N 1'-acetyl-3-[(2r)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C1CN(C(=O)C)CCC21C(C(=O)N(C[C@H](N)C=1C=CC=CC=1)C(=O)N1CC=3C(=CC=CC=3F)C(F)(F)F)=C1CO2 VTRIFTLAGXOFRH-QFIPXVFZSA-N 0.000 claims 1
- CDSFMIKQRZWZQK-NDEPHWFRSA-N 2-[[3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-2,4-dioxospiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-1'-yl]methyl]-6-fluorobenzonitrile Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC1=C(C#N)C(=CC=C1)F)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 CDSFMIKQRZWZQK-NDEPHWFRSA-N 0.000 claims 1
- OGCCIDQQRPSRBO-NDEPHWFRSA-N 2-[[3-[(2r)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-2,4-dioxospiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-1'-yl]methyl]benzonitrile Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC=C1C#N OGCCIDQQRPSRBO-NDEPHWFRSA-N 0.000 claims 1
- IZOQAACJVHPALY-NDEPHWFRSA-N 3-[(2R)-2-amino-2-phenylethyl]-1'-(1-benzothiophen-7-ylmethyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC1=CC=CC2=C1SC=C2)CC2=C(C=CC=C2C(F)(F)F)F)=O)C2=CC=CC=C2 IZOQAACJVHPALY-NDEPHWFRSA-N 0.000 claims 1
- YUSCJUDVHMJTRP-DEOSSOPVSA-N 3-[(2R)-2-amino-2-phenylethyl]-1'-(2,2-dimethylpropyl)-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound CC(C)(C)CN1CCC2(CC1)OCc1c2c(=O)n(C[C@H](N)c2ccccc2)c(=O)n1Cc1c(F)cccc1C(F)(F)F YUSCJUDVHMJTRP-DEOSSOPVSA-N 0.000 claims 1
- VGKVUIZJSJJBQC-VWLOTQADSA-N 3-[(2R)-2-amino-2-phenylethyl]-1'-[(2-chloropyridin-3-yl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC=1C(=NC=CC1)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 VGKVUIZJSJJBQC-VWLOTQADSA-N 0.000 claims 1
- OSMNMVLWNHVRNA-MHZLTWQESA-N 3-[(2R)-2-amino-2-phenylethyl]-1'-[(3-chlorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC1=CC(=CC=C1)Cl)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 OSMNMVLWNHVRNA-MHZLTWQESA-N 0.000 claims 1
- MXSOOPALMZZQNG-QHCPKHFHSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-(2-methylpropanoyl)spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound CC(C)C(=O)N1CCC2(CC1)OCc1c2c(=O)n(C[C@H](N)c2ccccc2)c(=O)n1Cc1c(F)cccc1C(F)(F)F MXSOOPALMZZQNG-QHCPKHFHSA-N 0.000 claims 1
- GVTCTYIOHNARND-SANMLTNESA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-(2-morpholin-4-ylethyl)spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CCN1CCOCC1)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 GVTCTYIOHNARND-SANMLTNESA-N 0.000 claims 1
- LIMGOFOGIIJPTC-MHZLTWQESA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[(3-hydroxyphenyl)methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC1=CC(=CC=C1)O)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 LIMGOFOGIIJPTC-MHZLTWQESA-N 0.000 claims 1
- MPZYOJKQSHWECV-NDEPHWFRSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[(3-methoxyphenyl)methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound COc1cccc(CN2CCC3(CC2)OCc2c3c(=O)n(C[C@H](N)c3ccccc3)c(=O)n2Cc2c(F)cccc2C(F)(F)F)c1 MPZYOJKQSHWECV-NDEPHWFRSA-N 0.000 claims 1
- PNRRJKMEMKYSDB-NDEPHWFRSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[(3-methylsulfanylphenyl)methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](CN1C(N(C2=C(C1=O)C1(OC2)CCN(CC1)CC1=CC(=CC=C1)SC)CC1=C(C=CC=C1C(F)(F)F)F)=O)C1=CC=CC=C1 PNRRJKMEMKYSDB-NDEPHWFRSA-N 0.000 claims 1
- MMVBZKXGUCCNIL-NDEPHWFRSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[(4-methoxyphenyl)methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound COc1ccc(CN2CCC3(CC2)OCc2c3c(=O)n(C[C@H](N)c3ccccc3)c(=O)n2Cc2c(F)cccc2C(F)(F)F)cc1 MMVBZKXGUCCNIL-NDEPHWFRSA-N 0.000 claims 1
- HHKLWBNWCWSOPN-MHZLTWQESA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[(5-methylpyridin-3-yl)methyl]spiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound Cc1cncc(CN2CCC3(CC2)OCc2c3c(=O)n(C[C@H](N)c3ccccc3)c(=O)n2Cc2c(F)cccc2C(F)(F)F)c1 HHKLWBNWCWSOPN-MHZLTWQESA-N 0.000 claims 1
- NOQKRZONRQFIDH-NDEPHWFRSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-[[3-(trifluoromethyl)phenyl]methyl]spiro[6,7-dihydrocyclopenta[d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound N[C@@H](Cn1c(=O)c2c(CCC22CCN(Cc3cccc(c3)C(F)(F)F)CC2)n(Cc2c(F)cccc2C(F)(F)F)c1=O)c1ccccc1 NOQKRZONRQFIDH-NDEPHWFRSA-N 0.000 claims 1
- BKQSONWVITWCBF-NRFANRHFSA-N 3-[(2R)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-methylspiro[7H-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound CN1CCC2(CC1)OCc1c2c(=O)n(C[C@H](N)c2ccccc2)c(=O)n1Cc1c(F)cccc1C(F)(F)F BKQSONWVITWCBF-NRFANRHFSA-N 0.000 claims 1
- JZRQJSWGNZGQJA-SANMLTNESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(2,3-difluorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC(F)=C1F JZRQJSWGNZGQJA-SANMLTNESA-N 0.000 claims 1
- NWNHBLQVDGFZGD-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(2-chlorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC=C1Cl NWNHBLQVDGFZGD-MHZLTWQESA-N 0.000 claims 1
- LLZYIIBYXSSRAJ-SANMLTNESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound COC1=CC=CC(CN2CCC3(CC2)C2=C(N(C(=O)N(C[C@H](N)C=4C=CC=CC=4)C2=O)CC=2C(=CC=CC=2F)C(F)(F)F)CO3)=C1F LLZYIIBYXSSRAJ-SANMLTNESA-N 0.000 claims 1
- CXWFHGSQTPQUGG-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(2-fluorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC=C1F CXWFHGSQTPQUGG-MHZLTWQESA-N 0.000 claims 1
- RJBYXCDAMSXWIE-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(3-chlorophenyl)methyl]-1-[(2,6-difluorophenyl)methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC(Cl)=C1 RJBYXCDAMSXWIE-MHZLTWQESA-N 0.000 claims 1
- HWZJKDYRSZGMOV-NDEPHWFRSA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(3-chlorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[6,7-dihydrocyclopenta[d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1CCC2(CC1)CCN1CC1=CC=CC(Cl)=C1 HWZJKDYRSZGMOV-NDEPHWFRSA-N 0.000 claims 1
- AXEOVYRLDBREGX-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(3-fluorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=CC(F)=C1 AXEOVYRLDBREGX-MHZLTWQESA-N 0.000 claims 1
- MNANXXJRDZDWPG-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(4-chlorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=C(Cl)C=C1 MNANXXJRDZDWPG-MHZLTWQESA-N 0.000 claims 1
- GVAJYXKTBHSEOO-MHZLTWQESA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(4-fluorophenyl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=C(F)C=C1 GVAJYXKTBHSEOO-MHZLTWQESA-N 0.000 claims 1
- INPNCSMBGOGVML-VWLOTQADSA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(5-chlorofuran-2-yl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[6,7-dihydrocyclopenta[d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1CCC2(CC1)CCN1CC1=CC=C(Cl)O1 INPNCSMBGOGVML-VWLOTQADSA-N 0.000 claims 1
- FGHIRSMYKDHMIF-DEOSSOPVSA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(5-chlorofuran-2-yl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=C(Cl)O1 FGHIRSMYKDHMIF-DEOSSOPVSA-N 0.000 claims 1
- JTGUNEYXDVYRLY-VWLOTQADSA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-[(6-chloropyridin-3-yl)methyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=C(Cl)N=C1 JTGUNEYXDVYRLY-VWLOTQADSA-N 0.000 claims 1
- IRSPQGZZBIDNHL-NDEPHWFRSA-N 3-[(2r)-2-amino-2-phenylethyl]-1'-benzyl-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]spiro[6,7-dihydrocyclopenta[d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1CCC2(CC1)CCN1CC1=CC=CC=C1 IRSPQGZZBIDNHL-NDEPHWFRSA-N 0.000 claims 1
- COLADWQPOMUBEY-DEOSSOPVSA-N 3-[(2r)-2-amino-2-phenylethyl]-1-[(2,6-difluorophenyl)methyl]-1'-[[5-(trifluoromethyl)furan-2-yl]methyl]spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC1=CC=C(C(F)(F)F)O1 COLADWQPOMUBEY-DEOSSOPVSA-N 0.000 claims 1
- AHFCDOSOHIGNJG-DEOSSOPVSA-N 3-[(2r)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-(1,2-oxazol-3-ylmethyl)spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C([C@H](N)C=1C=CC=CC=1)N(C(N1CC=2C(=CC=CC=2F)C(F)(F)F)=O)C(=O)C2=C1COC2(CC1)CCN1CC=1C=CON=1 AHFCDOSOHIGNJG-DEOSSOPVSA-N 0.000 claims 1
- GLTBKBWMPBKTMU-QHCPKHFHSA-N 3-[(2r)-2-amino-2-phenylethyl]-1-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1'-(2-methoxyethyl)spiro[7h-furo[3,4-d]pyrimidine-5,4'-piperidine]-2,4-dione Chemical compound C1CN(CCOC)CCC21C(C(=O)N(C[C@H](N)C=1C=CC=CC=1)C(=O)N1CC=3C(=CC=CC=3F)C(F)(F)F)=C1CO2 GLTBKBWMPBKTMU-QHCPKHFHSA-N 0.000 claims 1
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| JP2014559833A Active JP6209171B2 (ja) | 2012-02-28 | 2013-02-28 | ゴナドトロピン放出ホルモン受容体アンタゴニスト、その製造方法および該アンタゴニストを含む医薬組成物 |
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| EP (1) | EP2820021B1 (https=) |
| JP (1) | JP6209171B2 (https=) |
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| CA (1) | CA2865547C (https=) |
| ES (1) | ES2613856T3 (https=) |
| MX (1) | MX357841B (https=) |
| WO (1) | WO2013129879A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10005781B2 (en) | 2013-10-30 | 2018-06-26 | Shanghai Hengrui Pharmaceutical Co., Ltd. | Pyrazolopyrimidone or pyrrolotriazone derivatives, method of preparing same, and pharmaceutical applications thereof |
| JP2020528060A (ja) * | 2017-07-28 | 2020-09-17 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ピリミドンヘテロアリール誘導体の製造方法およびピリミドンヘテロアリール誘導体の中間体 |
| KR101973074B1 (ko) * | 2018-11-30 | 2019-04-26 | 주식회사 티움바이오 | 퓨로피리미딘 화합물의 염 및 결정형, 및 이를 포함하는 약학적 조성물 |
| CN109651265A (zh) * | 2019-02-16 | 2019-04-19 | 安徽诺全药业有限公司 | 一种Elagolix的制备方法 |
| ES2944511T3 (es) | 2019-03-26 | 2023-06-21 | Novel Pharma Inc | Derivado de GnRH que se une a ácido graso de acción prolongada y composición farmacéutica que comprende el mismo |
| KR20210155350A (ko) | 2020-06-15 | 2021-12-22 | 한상왕 | 녹차 추출물 및 비타민 d3를 유효성분으로 포함하는 자궁근종 개선용 조성물 |
| CN115124545B (zh) * | 2022-08-31 | 2023-01-03 | 南京远淑医药科技有限公司 | 一种促性腺激素释放激素受体拮抗剂中间体的合成方法 |
| KR102738115B1 (ko) | 2024-03-25 | 2024-12-05 | 한상왕 | 자궁근종 예방, 개선 또는 치료용 약학 조성물 |
| WO2025230335A1 (ko) * | 2024-05-03 | 2025-11-06 | 주식회사 티움바이오 | 에스트로겐-의존성 질환 치료 또는 예방용 약학적 조성물 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2163325A1 (en) * | 1994-11-21 | 1996-05-22 | Kaneyoshi Kato | Amine compounds, their production and use |
| US6156772A (en) | 1997-06-05 | 2000-12-05 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
| TWI225863B (en) * | 1999-03-24 | 2005-01-01 | Takeda Chemical Industries Ltd | Thienopyrimidine compounds, their production and use |
| DE60022769T2 (de) * | 1999-10-15 | 2006-07-06 | Neurocrine Biosciences, Inc., San Diego | Gonadotropin freisetzenden hormon rezeptor antagonisten und ihre verwandten verwendungen |
| JP2005500356A (ja) * | 2001-08-02 | 2005-01-06 | ニューロクライン バイオサイエンシーズ， インコーポレイテッド | ゴナドトロピン放出ホルモンレセプターアンタゴニスト |
| FR2833948B1 (fr) * | 2001-12-21 | 2004-02-06 | Sod Conseils Rech Applic | Nouveaux derives de benzimidazole et leur utilisation en tant que medicament |
| BR0312123A (pt) | 2002-06-13 | 2005-03-29 | Pfizer | Agentes de gnrh não peptìdicos, composições farmacêuticas e métodos para o seu uso |
| ES2494842T3 (es) * | 2005-07-22 | 2014-09-16 | Takeda Pharmaceutical Company Limited | Agente que previene la ovulación precoz |
| US9034850B2 (en) * | 2009-11-20 | 2015-05-19 | Sk Chemicals Co., Ltd. | Gonadotropin releasing hormone receptor antagonist, preparation method thereof and pharmaceutical composition comprising the same |
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2013
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- 2013-02-28 WO PCT/KR2013/001660 patent/WO2013129879A1/en not_active Ceased
- 2013-02-28 KR KR20130022105A patent/KR101495260B1/ko active Active
- 2013-02-28 BR BR112014021331-3A patent/BR112014021331B1/pt active IP Right Grant
- 2013-02-28 CN CN201380011513.6A patent/CN104136441B/zh active Active
- 2013-02-28 JP JP2014559833A patent/JP6209171B2/ja active Active
- 2013-02-28 EP EP13754960.6A patent/EP2820021B1/en active Active
- 2013-02-28 CA CA2865547A patent/CA2865547C/en active Active
- 2013-02-28 ES ES13754960T patent/ES2613856T3/es active Active
- 2013-02-28 MX MX2014010345A patent/MX357841B/es active IP Right Grant
- 2013-02-28 AU AU2013226661A patent/AU2013226661B2/en active Active
- 2013-02-28 US US14/381,371 patent/US9481684B2/en active Active
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