JPWO2018073251A5 - - Google Patents
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- Publication number
- JPWO2018073251A5 JPWO2018073251A5 JP2019541882A JP2019541882A JPWO2018073251A5 JP WO2018073251 A5 JPWO2018073251 A5 JP WO2018073251A5 JP 2019541882 A JP2019541882 A JP 2019541882A JP 2019541882 A JP2019541882 A JP 2019541882A JP WO2018073251 A5 JPWO2018073251 A5 JP WO2018073251A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- pyrazine
- imidazole
- tetrahydropyran
- 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- -1 methoxy, difluoromethoxy Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 17
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 208000028698 Cognitive impairment Diseases 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000014644 Brain disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 210000003141 lower extremity Anatomy 0.000 claims 2
- 201000003631 narcolepsy Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000020016 psychiatric disease Diseases 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- FYVMUFKHWSPDBW-UHFFFAOYSA-N 5-methyl-1-(oxan-4-yl)-6-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[3,4-d]pyrimidin-4-one Chemical compound Cn1c(Cc2ccc(cc2)-c2ccccn2)nc2n(ncc2c1=O)C1CCOCC1 FYVMUFKHWSPDBW-UHFFFAOYSA-N 0.000 claims 1
- FKCXABCEHFIBTK-UHFFFAOYSA-N 5-methyl-1-(oxan-4-yl)-6-[(4-pyridin-2-ylphenyl)methyl]pyrazolo[4,3-c]pyridin-4-one Chemical compound CN1C(C2=C(C=C1CC1=CC=C(C=C1)C1=NC=CC=C1)N(N=C2)C1CCOCC1)=O FKCXABCEHFIBTK-UHFFFAOYSA-N 0.000 claims 1
- TXRPELRRLFOWMZ-UHFFFAOYSA-N 5-methyl-6-[[4-(6-methylpyridin-2-yl)phenyl]methyl]-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound Cc1cccc(n1)-c1ccc(Cc2nc3n(ncc3c(=O)n2C)C2CCOCC2)cc1 TXRPELRRLFOWMZ-UHFFFAOYSA-N 0.000 claims 1
- ZJYOCMLPEHOFCR-UHFFFAOYSA-N 5-methyl-6-[[4-(6-methylpyridin-2-yl)phenyl]methyl]-1-(oxan-4-yl)pyrazolo[4,3-c]pyridin-4-one Chemical compound CN1C(C2=C(C=C1CC1=CC=C(C=C1)C1=NC(=CC=C1)C)N(N=C2)C1CCOCC1)=O ZJYOCMLPEHOFCR-UHFFFAOYSA-N 0.000 claims 1
- KRFUEFMKMDEURL-UHFFFAOYSA-N 6-[[4-(6-fluoropyridin-2-yl)phenyl]methyl]-5-methyl-1-(oxan-4-yl)pyrazolo[3,4-d]pyrimidin-4-one Chemical compound FC1=CC=CC(=N1)C1=CC=C(C=C1)CC=1N(C(C2=C(N=1)N(N=C2)C1CCOCC1)=O)C KRFUEFMKMDEURL-UHFFFAOYSA-N 0.000 claims 1
- DZLAMBPLEPUNMR-UHFFFAOYSA-N 6-[[4-(6-fluoropyridin-2-yl)phenyl]methyl]-5-methyl-1-(oxan-4-yl)pyrazolo[4,3-c]pyridin-4-one Chemical compound FC1=CC=CC(=N1)C1=CC=C(C=C1)CC1=CC2=C(C(N1C)=O)C=NN2C1CCOCC1 DZLAMBPLEPUNMR-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA201600643 | 2016-10-18 | ||
| DKPA201600643 | 2016-10-18 | ||
| DKPA201700191 | 2017-03-14 | ||
| DKPA201700191 | 2017-03-14 | ||
| PCT/EP2017/076481 WO2018073251A1 (en) | 2016-10-18 | 2017-10-17 | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2019534324A JP2019534324A (ja) | 2019-11-28 |
| JP2019534324A5 JP2019534324A5 (enExample) | 2020-11-26 |
| JPWO2018073251A5 true JPWO2018073251A5 (enExample) | 2022-02-17 |
| JP7112413B2 JP7112413B2 (ja) | 2022-08-03 |
Family
ID=60186253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019541882A Active JP7112413B2 (ja) | 2016-10-18 | 2017-10-17 | Ｐｄｅ１阻害剤としてのイミダゾピラジノン、ピラゾロピリミジノンおよびピラゾロピリジノン |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10633382B2 (enExample) |
| EP (1) | EP3529250B1 (enExample) |
| JP (1) | JP7112413B2 (enExample) |
| CN (1) | CN109843884B (enExample) |
| ES (1) | ES2967489T3 (enExample) |
| WO (1) | WO2018073251A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| EP3529250B1 (en) | 2016-10-18 | 2023-12-06 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| HUE050403T2 (hu) | 2016-10-28 | 2020-12-28 | H Lundbeck As | Imidazopirazinonokkal végzett kombinációs kezelések pszichiátriai és/vagy kognitív betegségek kezelésére |
| WO2018078042A1 (en) | 2016-10-28 | 2018-05-03 | H. Lundbeck A/S | Combination treatments comprising administration of imidazopyrazinones |
| US20210205310A1 (en) | 2018-05-25 | 2021-07-08 | Intra-Cellular Therapies, Inc. | Organic compounds |
| CN116874495B (zh) * | 2023-06-30 | 2025-10-10 | 中山大学 | 一种吡啶并二氢呋喃酮类衍生物及其制备方法和应用 |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB973361A (en) | 1960-05-11 | 1964-10-28 | Ciba Ltd | Pyrazolo-pyrimidines and process for their manufacture |
| DE19709877A1 (de) * | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| GB9722520D0 (en) * | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| DE10238723A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Phenyl-substituierte Pyrazolyprimidine |
| DE10238724A1 (de) | 2002-08-23 | 2004-03-04 | Bayer Ag | Alkyl-substituierte Pyrazolpyrimidine |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| AU2004235915B2 (en) | 2003-05-09 | 2010-08-05 | Boehringer Ingelheim International Gmbh | 6-cyclylmethyl- and 6-alkylmethyl-substituted pyrazolopyrimidines |
| US7872124B2 (en) | 2004-12-21 | 2011-01-18 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2007025103A2 (en) | 2005-08-23 | 2007-03-01 | Intra-Cellular Therapies, Inc. | Organic compounds for treating reduced dopamine receptor signalling activity |
| JP5837278B2 (ja) | 2006-12-05 | 2015-12-24 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規使用 |
| PT2152712E (pt) | 2007-05-11 | 2012-02-29 | Pfizer | Compostos amino-heterocíclicos |
| US20090143391A1 (en) | 2007-11-30 | 2009-06-04 | Norbert Hofgen | Aryl and heteroaryl fused imidazo [1,5-a] pyrazines as inhibitors of phosphodiesterase 10 |
| UA105362C2 (en) * | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| BRPI0918527A2 (pt) * | 2008-09-08 | 2015-12-01 | Boehring Ingelheim Internat Gmbh | compostos para o tratamento de disturbios do cns |
| MX2011005934A (es) | 2008-12-06 | 2011-12-16 | Intra Cellular Therapies Inc | Compuestos organicos. |
| TWI404721B (zh) | 2009-01-26 | 2013-08-11 | Pfizer | 胺基－雜環化合物 |
| US9434730B2 (en) | 2010-05-31 | 2016-09-06 | Intra-Cellular Therapies, Inc. | PDE1 inhibitor compounds |
| EP3181566A1 (en) | 2010-09-20 | 2017-06-21 | Ironwood Pharmaceuticals, Inc. | Imidazotriazinone compounds |
| EP2619204A4 (en) | 2010-09-21 | 2014-08-27 | Merck Sharp & Dohme | TRIAZOLOPYRAZINONE AS P2X7 RECEPTOR ANTAGONISTS |
| JO3089B1 (ar) | 2010-11-19 | 2017-03-15 | H Lundbeck As | مشتقات ايميدازول كمثبطات لانزيمات pde10a |
| JP6051210B2 (ja) | 2011-06-10 | 2016-12-27 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 有機化合物 |
| HK1211023A1 (zh) * | 2011-10-10 | 2016-05-13 | H. Lundbeck A/S | 具有咪唑并吡嗪骨架pde9i |
| HK1199879A1 (en) | 2012-01-26 | 2015-07-24 | H.隆德贝克有限公司 | Pde9 inhibitors with imidazo triazinone backbone |
| US9499562B2 (en) | 2012-06-18 | 2016-11-22 | Dart Neuroscience (Cayman) Ltd. | Substituted thiophene- and furan-fused azolopyrimidine-5-(6H)-one compounds |
| ES2836129T3 (es) | 2013-03-15 | 2021-06-24 | Intra Cellular Therapies Inc | Compuestos orgánicos |
| JP5783297B2 (ja) | 2013-08-06 | 2015-09-24 | 株式会社デンソー | 力学量センサ |
| JP5797815B1 (ja) | 2014-06-27 | 2015-10-21 | 細田建設株式会社 | 後施工アンカー及びその施工方法 |
| US20170273985A1 (en) | 2014-09-18 | 2017-09-28 | Sunovion Pharmaceuticals Inc. | Tricyclic derivative |
| US20160083400A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic guanidine derivative |
| US20160083391A1 (en) | 2014-09-18 | 2016-03-24 | Sunovion Pharmaceuticals Inc. | Tricyclic piperazine derivative |
| TW201629064A (zh) | 2014-10-10 | 2016-08-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之三唑並吡酮 |
| US20180044343A1 (en) | 2015-03-16 | 2018-02-15 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic imidazolo derivative |
| TW201643167A (zh) | 2015-04-22 | 2016-12-16 | Ｈ 朗德貝克公司 | 作爲ｐｄｅ１抑制劑之咪唑並三酮 |
| JO3627B1 (ar) | 2015-04-30 | 2020-08-27 | H Lundbeck As | إيميدازو بيرازينونات على هيئة مثبطات pde1 |
| TWI609870B (zh) | 2016-02-12 | 2018-01-01 | 美國禮來大藥廠 | Pde1抑制劑 |
| TWI729109B (zh) | 2016-04-12 | 2021-06-01 | 丹麥商Ｈ 朗德貝克公司 | 作爲PDE1抑制劑的1,5-二氫-4H-吡唑并[3,4-d]嘧啶-4-酮和1,5-二氫-4H-吡唑并[4,3-c]吡啶-4-酮 |
| JP2018076285A (ja) | 2016-09-14 | 2018-05-17 | 大日本住友製薬株式会社 | 二環性イミダゾロ誘導体を含む医薬 |
| EP3529250B1 (en) | 2016-10-18 | 2023-12-06 | H. Lundbeck A/S | Imidazopyrazinones, pyrazolopyrimidinones and pyrazolopyridinones as pde1 inhibitors |
| WO2018078042A1 (en) | 2016-10-28 | 2018-05-03 | H. Lundbeck A/S | Combination treatments comprising administration of imidazopyrazinones |
| HUE050403T2 (hu) | 2016-10-28 | 2020-12-28 | H Lundbeck As | Imidazopirazinonokkal végzett kombinációs kezelések pszichiátriai és/vagy kognitív betegségek kezelésére |
-
2017
- 2017-10-17 EP EP17791007.2A patent/EP3529250B1/en active Active
- 2017-10-17 WO PCT/EP2017/076481 patent/WO2018073251A1/en not_active Ceased
- 2017-10-17 CN CN201780060932.7A patent/CN109843884B/zh not_active Expired - Fee Related
- 2017-10-17 JP JP2019541882A patent/JP7112413B2/ja active Active
- 2017-10-17 ES ES17791007T patent/ES2967489T3/es active Active
- 2017-10-17 US US16/340,429 patent/US10633382B2/en active Active
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