JP2017536409A5 - - Google Patents
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- Publication number
- JP2017536409A5 JP2017536409A5 JP2017530034A JP2017530034A JP2017536409A5 JP 2017536409 A5 JP2017536409 A5 JP 2017536409A5 JP 2017530034 A JP2017530034 A JP 2017530034A JP 2017530034 A JP2017530034 A JP 2017530034A JP 2017536409 A5 JP2017536409 A5 JP 2017536409A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazolo
- methyl
- naphthyridin
- butoxy
- fluorophenyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000003839 salts Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 230000003340 mental effect Effects 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- TXMNAVBOXBRWRL-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3,5-dimethylpyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CN1C(=O)C2=C(N(N=C2C)C2=C(Cl)C=CC(Cl)=C2)C2=C1C=CC=N2 TXMNAVBOXBRWRL-UHFFFAOYSA-N 0.000 claims 1
- VFCZPATWIYOHJQ-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CC1=NN(C2=C1C(=O)NC1=C2N=CC=C1)C1=C(Cl)C=CC(Cl)=C1 VFCZPATWIYOHJQ-UHFFFAOYSA-N 0.000 claims 1
- CWYBEKQXIDZGCO-UHFFFAOYSA-N 1-(2-chlorophenyl)-3,5-dimethylpyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CN1C(=O)C2=C(N(N=C2C)C2=C(Cl)C=CC=C2)C2=C1C=CC=N2 CWYBEKQXIDZGCO-UHFFFAOYSA-N 0.000 claims 1
- WQYNZBWUUFOYLZ-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CC1=NN(C2=C1C(=O)NC1=C2N=CC=C1)C1=C(Cl)C=CC=C1 WQYNZBWUUFOYLZ-UHFFFAOYSA-N 0.000 claims 1
- KSGXFQJHUNDYRZ-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-3-methyl-3,3a,5,5a,6,7,8,9,9a,9b-decahydro-2H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOc1ccc(Cl)c(c1)N1NC(C)C2C1C1NCCCC1NC2=O KSGXFQJHUNDYRZ-UHFFFAOYSA-N 0.000 claims 1
- HLMDAEZBEKMIQP-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-8-chloro-3-methyl-3,3a,5,5a,6,7,8,9,9a,9b-decahydro-2H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOc1ccc(Cl)c(c1)N1NC(C)C2C1C1NC(Cl)CCC1NC2=O HLMDAEZBEKMIQP-UHFFFAOYSA-N 0.000 claims 1
- CBGSELCUTQWMFO-UHFFFAOYSA-N 1-(5-butoxy-2-chlorophenyl)-8-methoxy-3-methyl-3,3a,5,5a,6,7,8,9,9a,9b-decahydro-2H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOc1ccc(Cl)c(c1)N1NC(C)C2C1C1NC(CCC1NC2=O)OC CBGSELCUTQWMFO-UHFFFAOYSA-N 0.000 claims 1
- QDJBJYWUERRLGN-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-4-oxo-3aH-pyrazolo[4,3-h][1,5]naphthyridine-8-carboxamide Chemical compound CCCCOC1=CC(N2N=C(C)C3C2=C2N=C(C=CC2=NC3=O)C(N)=O)=C(F)C=C1 QDJBJYWUERRLGN-UHFFFAOYSA-N 0.000 claims 1
- LZYZEOLAPLNPLJ-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-4-oxo-5H-pyrazolo[4,3-h][1,5]naphthyridine-8-carbonitrile Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(=N2)C#N)=C(F)C=C1 LZYZEOLAPLNPLJ-UHFFFAOYSA-N 0.000 claims 1
- KCZWAWIWVZBEHK-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-4-oxo-5H-pyrazolo[4,3-h][1,5]naphthyridine-8-carboxylic acid Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(=N2)C(O)=O)=C(F)C=C1 KCZWAWIWVZBEHK-UHFFFAOYSA-N 0.000 claims 1
- GVCWNUHDYYGLHB-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound C(CCC)OC=1C=CC(=C(C=1)N1N=C(C=2C(NC=3C=CC=NC=3C=21)=O)C)F GVCWNUHDYYGLHB-UHFFFAOYSA-N 0.000 claims 1
- SFIZQWYZYMPKTG-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-8-(pyridin-2-ylamino)-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(NC3=NC=CC=C3)=N2)=C(F)C=C1 SFIZQWYZYMPKTG-UHFFFAOYSA-N 0.000 claims 1
- GEWLDLSFZCTLFZ-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-8-pyrazol-1-yl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(=N2)N2C=CC=N2)=C(F)C=C1 GEWLDLSFZCTLFZ-UHFFFAOYSA-N 0.000 claims 1
- HABNVWFXKMBDEC-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-3-methyl-8-pyrrolidin-1-yl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(=N2)N2CCCC2)=C(F)C=C1 HABNVWFXKMBDEC-UHFFFAOYSA-N 0.000 claims 1
- OYJBYVZPNLLRDF-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-8-(4-fluorophenoxy)-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(OC3=CC=C(F)C=C3)=N2)=C(F)C=C1 OYJBYVZPNLLRDF-UHFFFAOYSA-N 0.000 claims 1
- IMAOQPNOONDYGN-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-8-(dimethylamino)-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound C(CCC)OC=1C=CC(=C(C=1)N1N=C(C=2C(NC=3C=CC(=NC=3C=21)N(C)C)=O)C)F IMAOQPNOONDYGN-UHFFFAOYSA-N 0.000 claims 1
- MXVWSDWPQOLZHX-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-8-ethylsulfanyl-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound C(CCC)OC=1C=CC(=C(C=1)N1N=C(C=2C(NC=3C=CC(=NC=3C=21)SCC)=O)C)F MXVWSDWPQOLZHX-UHFFFAOYSA-N 0.000 claims 1
- GAJCDBSBYDXXKD-UHFFFAOYSA-N 1-(5-butoxy-2-fluorophenyl)-N-ethyl-3-methyl-4-oxo-5H-pyrazolo[4,3-h][1,5]naphthyridine-8-carboxamide Chemical compound CCCCOC1=CC(N2N=C(C)C3=C2C2=C(NC3=O)C=CC(=N2)C(=O)NCC)=C(F)C=C1 GAJCDBSBYDXXKD-UHFFFAOYSA-N 0.000 claims 1
- FVKTYFNDUDJLCL-UHFFFAOYSA-N 1-[2-chloro-5-(cyclobutylmethoxy)phenyl]-8-methoxy-3-methyl-3,3a,5,5a,6,7,8,9,9a,9b-decahydro-2H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound COC1CCC2NC(=O)C3C(C)NN(C3C2N1)c1cc(OCC2CCC2)ccc1Cl FVKTYFNDUDJLCL-UHFFFAOYSA-N 0.000 claims 1
- GHKSZQKFAPBQJP-UHFFFAOYSA-N 8-chloro-1-(2,5-dichlorophenyl)-3-methyl-3,3a,5,5a,6,7,8,9,9a,9b-decahydro-2H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CC1NN(C2C1C(=O)NC1CCC(Cl)NC21)c1cc(Cl)ccc1Cl GHKSZQKFAPBQJP-UHFFFAOYSA-N 0.000 claims 1
- LUJYZELYBGDWBN-UHFFFAOYSA-N 8-chloro-1-[2-chloro-5-(cyclopropylmethoxy)phenyl]-3-methyl-5H-pyrazolo[4,3-c][1,5]naphthyridin-4-one Chemical compound CC1=NN(C2=C1C(=O)NC1=C2N=C(Cl)C=C1)C1=C(Cl)C=CC(OCC2CC2)=C1 LUJYZELYBGDWBN-UHFFFAOYSA-N 0.000 claims 1
- 206010003805 Autism Diseases 0.000 claims 1
- 208000020706 Autistic disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 101100135859 Dictyostelium discoideum regA gene Proteins 0.000 claims 1
- 241000023320 Luma <angiosperm> Species 0.000 claims 1
- 208000036626 Mental retardation Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 101100082606 Plasmodium falciparum (isolate 3D7) PDEbeta gene Proteins 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 101100135860 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PDE2 gene Proteins 0.000 claims 1
- -1 alkyl luma Chemical compound 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- CSYSETGWAJKQLE-UHFFFAOYSA-N ethyl 1-(5-butoxy-2-fluorophenyl)-3-methyl-4-oxo-5H-pyrazolo[4,3-h][1,5]naphthyridine-8-carboxylate Chemical compound C(CCC)OC=1C=CC(=C(C=1)N1N=C(C=2C(NC=3C=CC(=NC=3C=21)C(=O)OCC)=O)C)F CSYSETGWAJKQLE-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000005032 impulse control Effects 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 230000000698 schizophrenic effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462088540P | 2014-12-06 | 2014-12-06 | |
| US62/088,540 | 2014-12-06 | ||
| PCT/US2015/064331 WO2016090382A1 (en) | 2014-12-06 | 2015-12-07 | Organic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017536409A JP2017536409A (ja) | 2017-12-07 |
| JP2017536409A5 true JP2017536409A5 (enExample) | 2019-01-24 |
| JP6608933B2 JP6608933B2 (ja) | 2019-11-20 |
Family
ID=56092609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017530034A Expired - Fee Related JP6608933B2 (ja) | 2014-12-06 | 2015-12-07 | 有機化合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10105349B2 (enExample) |
| EP (1) | EP3226862B1 (enExample) |
| JP (1) | JP6608933B2 (enExample) |
| KR (1) | KR102562576B1 (enExample) |
| CN (1) | CN107205993B (enExample) |
| AU (1) | AU2015357498B2 (enExample) |
| BR (1) | BR112017012005B1 (enExample) |
| CA (1) | CA2969597C (enExample) |
| HK (2) | HK1244427A1 (enExample) |
| IL (1) | IL252578B (enExample) |
| MX (1) | MX373320B (enExample) |
| RU (1) | RU2702732C1 (enExample) |
| WO (1) | WO2016090382A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9503189B2 (en) | 2014-10-10 | 2016-11-22 | At&T Intellectual Property I, L.P. | Method and apparatus for arranging communication sessions in a communication system |
| CA2969597C (en) * | 2014-12-06 | 2023-10-24 | Intra-Cellular Therapies, Inc. | 1h-pyrazolo[4,3-c][1,5]naphthyridin-4(5h)-one compounds and their use as pde2 inhibitors |
| US9628116B2 (en) | 2015-07-14 | 2017-04-18 | At&T Intellectual Property I, L.P. | Apparatus and methods for transmitting wireless signals |
| TWI795381B (zh) | 2016-12-21 | 2023-03-11 | 比利時商健生藥品公司 | 作為ｍａｌｔ１抑制劑之吡唑衍生物 |
| TWI782056B (zh) | 2017-07-14 | 2022-11-01 | 日商鹽野義製藥股份有限公司 | 具有ｍｇａｔ２抑制活性的縮合環衍生物 |
| CN112334475B (zh) | 2018-04-13 | 2024-10-29 | 癌症研究技术有限公司 | Bcl6抑制剂 |
| JP7296408B2 (ja) * | 2018-06-18 | 2023-06-22 | ヤンセン ファーマシューティカ エヌ．ベー． | Ｍａｌｔ１阻害剤としてのピラゾール誘導体 |
| EP3909583A4 (en) | 2019-01-11 | 2022-08-17 | Shionogi & Co., Ltd | DIHYDROPYRAZOLOPYRAZINONE DERIVATIVES WITH MGAT2 INHIBITORY ACTIVITY |
| MX2021012417A (es) | 2019-04-11 | 2021-11-12 | Janssen Pharmaceutica Nv | Anillos de piridina que contienen derivados como inhibidores de malt1. |
| GB201914860D0 (en) * | 2019-10-14 | 2019-11-27 | Cancer Research Tech Ltd | Inhibitor compounds |
| CN112851667B (zh) * | 2019-11-28 | 2022-09-09 | 暨南大学 | 含氮并杂环类化合物及其药用组合物和应用 |
| KR20210109406A (ko) | 2020-02-27 | 2021-09-06 | 주식회사 재원인더스트리 | 열 교환기능을 구비한 환기모듈 |
| CN114539263B (zh) * | 2020-11-11 | 2023-04-25 | 暨南大学 | 一类含氮并杂环化合物及其药用组合物和应用 |
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-
2015
- 2015-12-07 CA CA2969597A patent/CA2969597C/en active Active
- 2015-12-07 RU RU2017123680A patent/RU2702732C1/ru active
- 2015-12-07 BR BR112017012005-4A patent/BR112017012005B1/pt not_active IP Right Cessation
- 2015-12-07 HK HK18103143.0A patent/HK1244427A1/zh unknown
- 2015-12-07 HK HK18103466.9A patent/HK1243935A1/zh unknown
- 2015-12-07 JP JP2017530034A patent/JP6608933B2/ja not_active Expired - Fee Related
- 2015-12-07 AU AU2015357498A patent/AU2015357498B2/en not_active Ceased
- 2015-12-07 WO PCT/US2015/064331 patent/WO2016090382A1/en not_active Ceased
- 2015-12-07 EP EP15866060.5A patent/EP3226862B1/en active Active
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- 2015-12-07 CN CN201580073716.7A patent/CN107205993B/zh not_active Expired - Fee Related
- 2015-12-07 MX MX2017007377A patent/MX373320B/es active IP Right Grant
- 2015-12-07 KR KR1020177018725A patent/KR102562576B1/ko active Active
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