JP2020523309A5 - - Google Patents
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- Publication number
- JP2020523309A5 JP2020523309A5 JP2019567341A JP2019567341A JP2020523309A5 JP 2020523309 A5 JP2020523309 A5 JP 2020523309A5 JP 2019567341 A JP2019567341 A JP 2019567341A JP 2019567341 A JP2019567341 A JP 2019567341A JP 2020523309 A5 JP2020523309 A5 JP 2020523309A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidine
- pyrazolo
- carbonitrile
- dihydro
- oxo
- 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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- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 63
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 150000001875 compounds Chemical class 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- -1 pyridadinyl Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000024254 Delusional disease Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- RHCPXBWBWPXEFT-UHFFFAOYSA-N 4-cyclopropylpyrimidine Chemical compound C1CC1C1=CC=NC=N1 RHCPXBWBWPXEFT-UHFFFAOYSA-N 0.000 claims 1
- HPFLLZGQKSUDNM-UHFFFAOYSA-N BrC=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound BrC=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O HPFLLZGQKSUDNM-UHFFFAOYSA-N 0.000 claims 1
- XFDDEQWMKKNJEL-UHFFFAOYSA-N C(#C)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(#C)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O XFDDEQWMKKNJEL-UHFFFAOYSA-N 0.000 claims 1
- DCEDXXOLOACMFX-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-UHFFFAOYSA-N 0.000 claims 1
- DCEDXXOLOACMFX-COXVUDFISA-N C(#N)C1=CC=C(C=C1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-COXVUDFISA-N 0.000 claims 1
- DCEDXXOLOACMFX-KBRIMQKVSA-N C(#N)C1=CC=C(C=C1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-KBRIMQKVSA-N 0.000 claims 1
- DCEDXXOLOACMFX-JQFCIGGWSA-N C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-JQFCIGGWSA-N 0.000 claims 1
- DCEDXXOLOACMFX-IAOVAPTHSA-N C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-IAOVAPTHSA-N 0.000 claims 1
- LRHPAFNLNDNUCK-UHFFFAOYSA-N C(#N)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(#N)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O LRHPAFNLNDNUCK-UHFFFAOYSA-N 0.000 claims 1
- VMABGNBOHHGZNG-UHFFFAOYSA-N C(C)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(C)C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O VMABGNBOHHGZNG-UHFFFAOYSA-N 0.000 claims 1
- DFKCKCZESWJKRM-UHFFFAOYSA-N C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N DFKCKCZESWJKRM-UHFFFAOYSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-UHFFFAOYSA-N C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-UHFFFAOYSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XYPHTWIQSA-N C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-XYPHTWIQSA-N 0.000 claims 1
- DFKCKCZESWJKRM-DQYPLSBCSA-N C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=C(C=N1)F)C#N DFKCKCZESWJKRM-DQYPLSBCSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-COXVUDFISA-N C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-COXVUDFISA-N 0.000 claims 1
- DFKCKCZESWJKRM-CSMYWGQOSA-N C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=C(C=N1)F)C#N DFKCKCZESWJKRM-CSMYWGQOSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XOKHGSTOSA-N C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-XOKHGSTOSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XKQJLSEDSA-N C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-XKQJLSEDSA-N 0.000 claims 1
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- GFVBNEXQGQGAKO-JQFCIGGWSA-N C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-JQFCIGGWSA-N 0.000 claims 1
- DFKCKCZESWJKRM-JCURWCKSSA-N C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=C(C=N1)F)C#N DFKCKCZESWJKRM-JCURWCKSSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-IAOVAPTHSA-N C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-IAOVAPTHSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-RRQGHBQHSA-N C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-RRQGHBQHSA-N 0.000 claims 1
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- SFIWAZKKXJUERW-UHFFFAOYSA-N CN1N=CC(=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound CN1N=CC(=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N SFIWAZKKXJUERW-UHFFFAOYSA-N 0.000 claims 1
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| US5294612A (en) | 1992-03-30 | 1994-03-15 | Sterling Winthrop Inc. | 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof |
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| US6770645B2 (en) | 2001-03-16 | 2004-08-03 | Pfizer Inc. | Pharmaceutically active compounds |
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2018
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- 2018-06-06 JP JP2019567341A patent/JP2020523309A/ja active Pending
- 2018-06-06 MX MX2019014597A patent/MX2019014597A/es unknown
- 2018-06-06 EP EP18735038.4A patent/EP3634964B1/en active Active
- 2018-06-06 WO PCT/US2018/036172 patent/WO2018226771A1/en not_active Ceased
- 2018-06-06 TW TW107119410A patent/TW201902898A/zh unknown
- 2018-06-06 MA MA053841A patent/MA53841A/fr unknown
- 2018-06-06 BR BR112019025813-2A patent/BR112019025813A2/pt not_active Application Discontinuation
- 2018-06-06 CN CN201880037972.4A patent/CN111051308A/zh active Pending
- 2018-06-06 AU AU2018281131A patent/AU2018281131B2/en not_active Ceased
- 2018-06-06 RU RU2019144010A patent/RU2019144010A/ru unknown
- 2018-06-06 CA CA3064938A patent/CA3064938A1/en active Pending
- 2018-06-06 KR KR1020207000123A patent/KR20200013758A/ko not_active Withdrawn
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2019
- 2019-10-31 US US16/670,093 patent/US11028092B2/en active Active
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