JP2017525700A5 - - Google Patents
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- Publication number
- JP2017525700A5 JP2017525700A5 JP2017508553A JP2017508553A JP2017525700A5 JP 2017525700 A5 JP2017525700 A5 JP 2017525700A5 JP 2017508553 A JP2017508553 A JP 2017508553A JP 2017508553 A JP2017508553 A JP 2017508553A JP 2017525700 A5 JP2017525700 A5 JP 2017525700A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazole
- pyrazol
- phenyl
- halo
- 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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- 125000005843 halogen group Chemical group 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 51
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 150000002367 halogens Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- -1 polymorph Chemical class 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 239000012453 solvate Substances 0.000 claims description 24
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 21
- 208000035475 disorder Diseases 0.000 claims description 21
- 150000001204 N-oxides Chemical class 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 108010054200 NR2B NMDA receptor Proteins 0.000 claims description 6
- 208000028552 Treatment-Resistant Depressive disease Diseases 0.000 claims description 6
- 208000024714 major depressive disease Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
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- 208000020925 Bipolar disease Diseases 0.000 claims description 3
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- SBFDBMKEWKLRSB-UHFFFAOYSA-N FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F Chemical compound FC(C=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F SBFDBMKEWKLRSB-UHFFFAOYSA-N 0.000 claims description 3
- LHMLJRCNGQZNHL-UHFFFAOYSA-N FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F Chemical compound FC(OC=1C=C(C=CC=1F)C=1C=NN(C=1)CC1=NNC=C1)F LHMLJRCNGQZNHL-UHFFFAOYSA-N 0.000 claims description 3
- 208000019022 Mood disease Diseases 0.000 claims description 3
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 claims description 3
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- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
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| CA3142998A1 (en) | 2019-06-14 | 2020-12-17 | Janssen Pharmaceutica Nv | Pyrazine carbamates and their use as glun2b receptor modulators |
| KR20220020917A (ko) | 2019-06-14 | 2022-02-21 | 얀센 파마슈티카 엔.브이. | 치환된 피라졸로[4,3-b]피리딘 및 GLUN2B 수용체 조절제로서의 이들의 용도 |
| TW202112774A (zh) | 2019-06-14 | 2021-04-01 | 比利時商健生藥品公司 | 經取代之吡唑并－吡啶醯胺及其作為ｇｌｕｎ２ｂ受體調節劑之用途 |
| PH12021552839A1 (en) | 2019-06-14 | 2022-10-03 | Janssen Pharmaceutica Nv | Substituted pyrazolo-pyridine amides and their use as glun2b receptor modulators |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610723B2 (en) * | 2001-01-29 | 2003-08-26 | Hoffmann-La Roche Inc. | Imidazole derivatives |
| EP1490364B1 (en) | 2002-03-28 | 2007-09-26 | Eisai R&D Management Co., Ltd. | 7-azaindoles as inhibitors of c-jun n-terminal kinases for the treatment of neurodegenerative disorders |
| TW200604183A (en) | 2004-02-18 | 2006-02-01 | Astrazeneca Ab | Triazole compounds and their use as metabotropic glutamate receptor antagonists |
| EP1963268B1 (en) | 2005-12-07 | 2010-12-01 | NSAB, Filial af NeuroSearch Sweden AB, Sverige | Disubstituted phenylpiperidines as modulators of cortical catecholaminergic neurotransmission |
| US7807704B2 (en) | 2006-03-30 | 2010-10-05 | Chemocentryx, Inc. | Bicyclic, nitrogen-containing compounds modulating CXCR4 and/or CCXCKR2 |
| PE20090717A1 (es) | 2007-05-18 | 2009-07-18 | Smithkline Beecham Corp | Derivados de quinolina como inhibidores de la pi3 quinasa |
| KR20100017372A (ko) * | 2007-05-25 | 2010-02-16 | 애보트 게엠베하 운트 콤파니 카게 | 향대사성 글루타메이트 수용체 2（ｍｇｌｕ2 수용체）의 포지티브 조절자로서의 헤테로사이클릭 화합물 |
| EP2194045A4 (en) | 2007-08-30 | 2011-09-21 | Takeda Pharmaceutical | Substituted pyrazole derivative |
| EP2215073A4 (en) | 2007-10-31 | 2011-04-06 | Merck Sharp & Dohme | SLEEP MODULATION WITH NR2B RECEPTOR ANTAGONISTS |
| RU2499598C2 (ru) * | 2008-03-27 | 2013-11-27 | Евотек Интернациональ Гмбх | Способы лечения нарушений с применением селективного антагониста nr2b-подтипа nmda рецепторов |
| JP5411927B2 (ja) | 2008-05-06 | 2014-02-12 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | Ｃｃｒ１アンタゴニストとしてのピラゾール化合物 |
| WO2010016490A1 (ja) | 2008-08-05 | 2010-02-11 | 第一三共株式会社 | イミダゾピリジン－２－オン誘導体 |
| AU2009304293B2 (en) | 2008-10-16 | 2012-04-26 | Addex Pharma S.A. | Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors |
| EP3037421A3 (en) | 2008-11-25 | 2016-11-30 | University Of Rochester | Mlk inhibitors and methods of use |
| CN102985424B (zh) | 2010-04-14 | 2015-03-11 | 阵列生物制药公司 | 5,7-取代的-咪唑并[1,2-c]嘧啶 |
| WO2013130855A1 (en) | 2012-03-02 | 2013-09-06 | Takeda Pharmaceutical Company Limited | Indazole derivatives |
| WO2014124651A1 (en) | 2013-02-15 | 2014-08-21 | Københavns Universitet | Pyrrolidine-2-carboxylic acid derivatives as iglur antagonists |
| EP2970200A1 (en) | 2013-03-13 | 2016-01-20 | Abbvie Inc. | Pyridine cdk9 kinase inhibitors |
| PT3180329T (pt) | 2014-08-15 | 2020-06-08 | Janssen Pharmaceuticals Inc | Triazóis como inibidores do recetor nr2b |
| HRP20200410T1 (hr) | 2015-07-09 | 2020-08-21 | Janssen Pharmaceutica Nv | Supstituirani 4-azaindoli i njihova upotreba kao modulatora glun2b receptora |
| CN109071488B (zh) | 2016-02-10 | 2021-08-13 | 詹森药业有限公司 | 取代的1,2,3-三唑作为nr2b-选择性nmda调节剂 |
| TW201819376A (zh) | 2016-10-06 | 2018-06-01 | 比利時商健生藥品公司 | 經取代之１Ｈ－咪唑並［４，５－ｂ］吡啶－２（３Ｈ）－酮及其作為ＧＬＵＮ２Ｂ受體調節劑之用途 |
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2015
- 2015-08-14 US US17/124,879 patent/USRE49517E1/en active Active
- 2015-08-14 WO PCT/US2015/045413 patent/WO2016025918A1/en not_active Ceased
- 2015-08-14 DK DK15775837.6T patent/DK3180315T3/da active
- 2015-08-14 US US15/503,875 patent/US10155727B2/en not_active Ceased
- 2015-08-14 JP JP2017508553A patent/JP6618525B2/ja active Active
- 2015-08-14 ES ES15775837T patent/ES2791252T3/es active Active
- 2015-08-14 PL PL15775837T patent/PL3180315T3/pl unknown
- 2015-08-14 EP EP15775837.6A patent/EP3180315B1/en active Active
- 2015-08-14 PT PT157758376T patent/PT3180315T/pt unknown
- 2015-08-14 HU HUE15775837A patent/HUE049278T2/hu unknown
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