JP2017501193A5 - - Google Patents
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- Publication number
- JP2017501193A5 JP2017501193A5 JP2016543726A JP2016543726A JP2017501193A5 JP 2017501193 A5 JP2017501193 A5 JP 2017501193A5 JP 2016543726 A JP2016543726 A JP 2016543726A JP 2016543726 A JP2016543726 A JP 2016543726A JP 2017501193 A5 JP2017501193 A5 JP 2017501193A5
- Authority
- JP
- Japan
- Prior art keywords
- trifluoromethyl
- dimethyl
- phenyl
- buten
- methylsulfonyl
- 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
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 150000001721 carbon Chemical group 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- -1 4- (methylsulfonyl) -3- (trifluoromethyl) phenyl Chemical group 0.000 claims 6
- 206010028980 Neoplasm Diseases 0.000 claims 6
- 201000011510 cancer Diseases 0.000 claims 5
- 229910052757 nitrogen Inorganic materials 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 4
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- LWFVRJYWAVMIMJ-UHFFFAOYSA-N 5-[3-[(Z)-4-[4-(3-chloro-4-methylsulfonylphenyl)pyrazol-1-yl]but-2-enyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound ClC=1C=C(C=CC1S(=O)(=O)C)C=1C=NN(C1)CC=C/CN1C(N(C(C1(C)C)=O)C=1C=C(C(=NC1)C#N)C(F)(F)F)=O LWFVRJYWAVMIMJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- FVIMUGZVBGCPIR-UHFFFAOYSA-N 3-(3-chloro-4-methylsulfonylphenyl)-5,5-dimethylimidazolidine-2,4-dione Chemical compound ClC=1C=C(C=CC=1S(=O)(=O)C)N1C(NC(C1=O)(C)C)=O FVIMUGZVBGCPIR-UHFFFAOYSA-N 0.000 claims 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- IKIYOBLVGDFJEF-UHFFFAOYSA-N 4-[1-[(Z)-4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]but-2-enyl]pyrazol-4-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C(#N)C1=C(C=C(C=C1)C=1C=NN(C1)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)C(F)(F)F IKIYOBLVGDFJEF-UHFFFAOYSA-N 0.000 claims 1
- RMGYJFDAMUXQIW-UHFFFAOYSA-N 4-[1-[(Z)-4-[3-[4-cyano-3-(trifluoromethyl)phenyl]-5,5-dimethyl-2,4-dioxoimidazolidin-1-yl]but-2-enyl]triazol-4-yl]-2-(trifluoromethyl)benzonitrile Chemical compound C(#N)C1=C(C=C(C=C1)C=1N=NN(C1)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)C(F)(F)F RMGYJFDAMUXQIW-UHFFFAOYSA-N 0.000 claims 1
- CIUXWMZWYIONRO-UHFFFAOYSA-N 4-[3-[(Z)-4-[3,5-dimethyl-4-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]pyrazol-1-yl]but-2-enyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1=NN(C(=C1C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)C)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O CIUXWMZWYIONRO-UHFFFAOYSA-N 0.000 claims 1
- CFPHXUHDFBGHIC-UHFFFAOYSA-N 4-[3-[(Z)-4-[4-(3,4-dichlorophenyl)triazol-1-yl]but-2-enyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound ClC=1C=C(C=CC1Cl)C=1N=NN(C1)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O CFPHXUHDFBGHIC-UHFFFAOYSA-N 0.000 claims 1
- HMNWTOLFPWTSLC-UHFFFAOYSA-N 4-[3-[(Z)-4-[4-(3-chloro-4-methylsulfonylphenyl)-2-oxopyrrolidin-1-yl]but-2-enyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound ClC=1C=C(C=CC1S(=O)(=O)C)C1CC(N(C1)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)=O HMNWTOLFPWTSLC-UHFFFAOYSA-N 0.000 claims 1
- DPDOQQRLOXUFQY-UHFFFAOYSA-N 4-[3-[(Z)-4-[4-(4-fluoro-3-methylphenyl)triazol-1-yl]but-2-enyl]-4,4-dimethyl-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound FC1=C(C=C(C=C1)C=1N=NN(C1)CC=C/CN1C(N(C(C1(C)C)=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)C DPDOQQRLOXUFQY-UHFFFAOYSA-N 0.000 claims 1
- NHMJEJIQKWODCI-UHFFFAOYSA-N 4-[3-[(Z)-4-[5,5-dimethyl-3-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-2,4-dioxoimidazolidin-1-yl]but-2-enyl]-4,4-dimethyl-2-oxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1(C(N(C(N1CC=C/CN1C(N(CC1(C)C)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)=O)C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)=O)C NHMJEJIQKWODCI-UHFFFAOYSA-N 0.000 claims 1
- LNPSTXLOXOUAHD-UHFFFAOYSA-N 4-[4,4-dimethyl-3-[(Z)-4-[4-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-2-oxopyrrolidin-1-yl]but-2-enyl]-2,5-dioxoimidazolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC1(N(C(N(C1=O)C1=CC(=C(C#N)C=C1)C(F)(F)F)=O)CC=C/CN1C(CC(C1)C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)=O)C LNPSTXLOXOUAHD-UHFFFAOYSA-N 0.000 claims 1
- NAFQNTULXDLNAB-UHFFFAOYSA-N 5,5-dimethyl-3-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-1-[(Z)-4-[4-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]-2-oxopyrrolidin-1-yl]but-2-enyl]imidazolidine-2,4-dione Chemical compound CC1(C(N(C(N1CC=C/CN1C(CC(C1)C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)=O)=O)C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)=O)C NAFQNTULXDLNAB-UHFFFAOYSA-N 0.000 claims 1
- XPNIEZCKJYBXPI-UHFFFAOYSA-N 5-[4,4-dimethyl-3-[(Z)-4-[4-[4-methylsulfonyl-3-(trifluoromethyl)phenyl]pyrazol-1-yl]but-2-enyl]-2,5-dioxoimidazolidin-1-yl]-3-(trifluoromethyl)pyridine-2-carbonitrile Chemical compound CC1(N(C(N(C1=O)C=1C=C(C(=NC1)C#N)C(F)(F)F)=O)CC=C/CN1N=CC(=C1)C1=CC(=C(C=C1)S(=O)(=O)C)C(F)(F)F)C XPNIEZCKJYBXPI-UHFFFAOYSA-N 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- HKIBFLJAOOOVGB-UHFFFAOYSA-N CC(C)(C(N1C2=CC=CC(C#N)=C2C(F)(F)F)=O)N(CC=CCN2N=NC(C3=CC=CC=C3)=C2)C1=O Chemical compound CC(C)(C(N1C2=CC=CC(C#N)=C2C(F)(F)F)=O)N(CC=CCN2N=NC(C3=CC=CC=C3)=C2)C1=O HKIBFLJAOOOVGB-UHFFFAOYSA-N 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 102000001307 androgen receptors Human genes 0.000 claims 1
- 108010080146 androgen receptors Proteins 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000005556 hormone Substances 0.000 claims 1
- 229940088597 hormone Drugs 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 0 *C(C1)C(*)*CC1N(C(C(*)(*)N1CC=CCN(*)***(C2CCCCC2)I)=O)C1=O Chemical compound *C(C1)C(*)*CC1N(C(C(*)(*)N1CC=CCN(*)***(C2CCCCC2)I)=O)C1=O 0.000 description 1
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2013/091118 WO2015100617A1 (en) | 2013-12-31 | 2013-12-31 | Novel imidazolidine-2,4-dione derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017501193A JP2017501193A (ja) | 2017-01-12 |
| JP2017501193A5 true JP2017501193A5 (enExample) | 2017-02-16 |
| JP6258508B2 JP6258508B2 (ja) | 2018-01-10 |
Family
ID=53492968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016543726A Expired - Fee Related JP6258508B2 (ja) | 2013-12-31 | 2013-12-31 | 新規のイミダゾリジン−２，４−ジオン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9975880B2 (enExample) |
| EP (1) | EP3089974B1 (enExample) |
| JP (1) | JP6258508B2 (enExample) |
| CN (1) | CN105849101B (enExample) |
| ES (1) | ES2725881T3 (enExample) |
| RU (1) | RU2650678C2 (enExample) |
| WO (1) | WO2015100617A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5656651A (en) | 1995-06-16 | 1997-08-12 | Biophysica Inc. | Androgenic directed compositions |
| US6472415B1 (en) * | 1998-12-18 | 2002-10-29 | Biophysica, Inc. | Androgen receptor suppressors in the therapy and diagnosis of prostate cancer, alopecia and other hyper-androgenic syndromes |
| DE10322108B4 (de) * | 2003-05-09 | 2008-12-11 | Bayer Schering Pharma Aktiengesellschaft | Antiandrogene Pyrrolidine mit tumorhemmender Wirksamkeit |
| SE0403085D0 (sv) * | 2004-12-17 | 2004-12-17 | Astrazeneca Ab | Novel componds |
| LT2656841T (lt) * | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| FR2944525B1 (fr) * | 2009-04-17 | 2011-06-24 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
| FR2944524B1 (fr) * | 2009-04-17 | 2012-11-30 | Ipsen Pharma Sas | Derives d'imidazolidine-2,4-dione et leur utilisation comme medicament |
-
2013
- 2013-12-31 JP JP2016543726A patent/JP6258508B2/ja not_active Expired - Fee Related
- 2013-12-31 EP EP13900705.8A patent/EP3089974B1/en not_active Not-in-force
- 2013-12-31 ES ES13900705T patent/ES2725881T3/es active Active
- 2013-12-31 RU RU2016131297A patent/RU2650678C2/ru active
- 2013-12-31 CN CN201380081816.5A patent/CN105849101B/zh not_active Expired - Fee Related
- 2013-12-31 WO PCT/CN2013/091118 patent/WO2015100617A1/en not_active Ceased
- 2013-12-31 US US15/108,746 patent/US9975880B2/en not_active Expired - Fee Related
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