JP2013507426A5 - - Google Patents
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- Publication number
- JP2013507426A5 JP2013507426A5 JP2012533623A JP2012533623A JP2013507426A5 JP 2013507426 A5 JP2013507426 A5 JP 2013507426A5 JP 2012533623 A JP2012533623 A JP 2012533623A JP 2012533623 A JP2012533623 A JP 2012533623A JP 2013507426 A5 JP2013507426 A5 JP 2013507426A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- trifluoromethyl
- pyrrolo
- pyridin
- pyrimidinamine
- 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 15
- 150000003839 salts Chemical class 0.000 claims 14
- 239000003814 drug Substances 0.000 claims 10
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 208000002193 Pain Diseases 0.000 claims 4
- 208000028017 Psychotic disease Diseases 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 3
- IUMCLDLDFCNOFJ-UHFFFAOYSA-N 6-(1-fluoroethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(F)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 IUMCLDLDFCNOFJ-UHFFFAOYSA-N 0.000 claims 2
- JKAMURCWMVPXTD-UHFFFAOYSA-N 6-(2-fluoropropan-2-yl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(C)(F)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 JKAMURCWMVPXTD-UHFFFAOYSA-N 0.000 claims 2
- 208000028698 Cognitive impairment Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- FREIUWXTFVJFNQ-UHFFFAOYSA-N 1-[6-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methylamino]pyrimidin-4-yl]ethanone Chemical compound C1=NC(C(=O)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 FREIUWXTFVJFNQ-UHFFFAOYSA-N 0.000 claims 1
- TUENMRJBXXNJPV-UHFFFAOYSA-N 2-[6-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methylamino]pyrimidin-4-yl]acetonitrile Chemical compound C=1N=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(CC#N)=NC=N1 TUENMRJBXXNJPV-UHFFFAOYSA-N 0.000 claims 1
- FCRALRGMLXTNAF-UHFFFAOYSA-N 5-methyl-6-(trifluoromethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound N1=CN=C(C(F)(F)F)C(C)=C1NCC1=CN=C(NC(=C2)C(F)(F)F)C2=C1 FCRALRGMLXTNAF-UHFFFAOYSA-N 0.000 claims 1
- AKNAYEKEJDAGNU-UHFFFAOYSA-N 6-(1,1-difluoroethyl)-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound N1=CN=C(C(C)(F)F)C(C)=C1NCC1=CN=C(NC(=C2)C(F)(F)F)C2=C1 AKNAYEKEJDAGNU-UHFFFAOYSA-N 0.000 claims 1
- VYXXCPIEGAVSGI-UHFFFAOYSA-N 6-(1,1-difluoroethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(F)(F)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 VYXXCPIEGAVSGI-UHFFFAOYSA-N 0.000 claims 1
- GJHFMWYJYAQNNB-UHFFFAOYSA-N 6-(1-fluoroethyl)-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound CC(F)C1=NC=NC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=C1C GJHFMWYJYAQNNB-UHFFFAOYSA-N 0.000 claims 1
- NXNBTILLKPTYFL-UHFFFAOYSA-N 6-(difluoromethyl)-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound N1=CN=C(C(F)F)C(C)=C1NCC1=CN=C(NC(=C2)C(F)(F)F)C2=C1 NXNBTILLKPTYFL-UHFFFAOYSA-N 0.000 claims 1
- UVXAUCOUBLXSTB-UHFFFAOYSA-N 6-(difluoromethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(F)F)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 UVXAUCOUBLXSTB-UHFFFAOYSA-N 0.000 claims 1
- GFPFXHKWLIAQID-UHFFFAOYSA-N 6-(fluoromethyl)-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound CC1=C(CF)N=CN=C1NCC1=CN=C(NC(=C2)C(F)(F)F)C2=C1 GFPFXHKWLIAQID-UHFFFAOYSA-N 0.000 claims 1
- CSHHZEBRHRZGPY-UHFFFAOYSA-N 6-(fluoromethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(CF)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 CSHHZEBRHRZGPY-UHFFFAOYSA-N 0.000 claims 1
- ZTEZMHCDSJDBEB-UHFFFAOYSA-N 6-(trifluoromethyl)-n-[[2-(trifluoromethyl)-1h-indol-5-yl]methyl]pyrimidin-4-amine Chemical compound C=1C=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(C(F)(F)F)=NC=N1 ZTEZMHCDSJDBEB-UHFFFAOYSA-N 0.000 claims 1
- YXAGCXOSBLOFKK-UHFFFAOYSA-N 6-(trifluoromethyl)-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C=1N=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(C(F)(F)F)=NC=N1 YXAGCXOSBLOFKK-UHFFFAOYSA-N 0.000 claims 1
- SOAQBBLXQCKMMI-UHFFFAOYSA-N 6-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methylamino]pyrimidine-4-carbonitrile Chemical compound C=1N=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(C#N)=NC=N1 SOAQBBLXQCKMMI-UHFFFAOYSA-N 0.000 claims 1
- XMOCDLVUVKZFOH-UHFFFAOYSA-N 6-chloro-n-[[2-(trifluoromethyl)-1h-indol-5-yl]methyl]pyrimidin-4-amine Chemical compound C=1C=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(Cl)=NC=N1 XMOCDLVUVKZFOH-UHFFFAOYSA-N 0.000 claims 1
- OAUOPEJWJZKLMI-UHFFFAOYSA-N 6-chloro-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C=1N=C2NC(C(F)(F)F)=CC2=CC=1CNC1=CC(Cl)=NC=N1 OAUOPEJWJZKLMI-UHFFFAOYSA-N 0.000 claims 1
- UMMATLWYSLQOHJ-UHFFFAOYSA-N 6-cyclopropyl-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound CC1=C(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)N=CN=C1C1CC1 UMMATLWYSLQOHJ-UHFFFAOYSA-N 0.000 claims 1
- YGQRGSRQUZUQSC-UHFFFAOYSA-N 6-cyclopropyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C=1N=C2NC(C(F)(F)F)=CC2=CC=1CNC(N=CN=1)=CC=1C1CC1 YGQRGSRQUZUQSC-UHFFFAOYSA-N 0.000 claims 1
- JRSJFFRBCQYSGE-UHFFFAOYSA-N 6-ethyl-5-fluoro-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound CCC1=NC=NC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=C1F JRSJFFRBCQYSGE-UHFFFAOYSA-N 0.000 claims 1
- UBHNANZOCDYQTI-UHFFFAOYSA-N 6-ethyl-5-methyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound CCC1=NC=NC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=C1C UBHNANZOCDYQTI-UHFFFAOYSA-N 0.000 claims 1
- PAANAFBEJPFWLS-UHFFFAOYSA-N 6-ethyl-n-[[2-(trifluoromethyl)-1h-indol-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(CC)=CC(NCC=2C=C3C=C(NC3=CC=2)C(F)(F)F)=N1 PAANAFBEJPFWLS-UHFFFAOYSA-N 0.000 claims 1
- GWENXCQJRLYZNY-UHFFFAOYSA-N 6-ethyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(CC)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 GWENXCQJRLYZNY-UHFFFAOYSA-N 0.000 claims 1
- LGGKFTAEVJBJBR-UHFFFAOYSA-N 6-propan-2-yl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(C)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 LGGKFTAEVJBJBR-UHFFFAOYSA-N 0.000 claims 1
- CLKRSHRCUSHUAL-UHFFFAOYSA-N 6-tert-butyl-n-[[2-(trifluoromethyl)-1h-pyrrolo[2,3-b]pyridin-5-yl]methyl]pyrimidin-4-amine Chemical compound C1=NC(C(C)(C)C)=CC(NCC=2C=C3C=C(NC3=NC=2)C(F)(F)F)=N1 CLKRSHRCUSHUAL-UHFFFAOYSA-N 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- -1 chloro, acetyl Chemical group 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25230709P | 2009-10-16 | 2009-10-16 | |
| US61/252,307 | 2009-10-16 | ||
| GB1012686.0 | 2010-07-28 | ||
| GBGB1012686.0A GB201012686D0 (en) | 2010-07-28 | 2010-07-28 | Novel compounds |
| PCT/EP2010/065368 WO2011045353A1 (en) | 2009-10-16 | 2010-10-14 | Indole and azaindole modulators of the alpha 7 nachr |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013507426A JP2013507426A (ja) | 2013-03-04 |
| JP2013507426A5 true JP2013507426A5 (enExample) | 2013-11-14 |
| JP5746703B2 JP5746703B2 (ja) | 2015-07-08 |
Family
ID=42799245
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012533623A Expired - Fee Related JP5746703B2 (ja) | 2009-10-16 | 2010-10-14 | α７ｎＡＣｈＲ調節因子としてのインドール及びアザインドール |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8796283B2 (enExample) |
| EP (1) | EP2488514B1 (enExample) |
| JP (1) | JP5746703B2 (enExample) |
| GB (1) | GB201012686D0 (enExample) |
| WO (1) | WO2011045353A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201012686D0 (en) * | 2010-07-28 | 2010-09-15 | Glaxo Group Ltd | Novel compounds |
| JP5951600B2 (ja) | 2010-05-21 | 2016-07-13 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | キナーゼ調節のための、化合物、組成物および方法 |
| US8785470B2 (en) | 2011-08-29 | 2014-07-22 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| JP2016000697A (ja) * | 2012-10-02 | 2016-01-07 | 大日本住友製薬株式会社 | ピリミジン誘導体 |
| US9481667B2 (en) | 2013-03-15 | 2016-11-01 | Infinity Pharmaceuticals, Inc. | Salts and solid forms of isoquinolinones and composition comprising and methods of using the same |
| CN203873004U (zh) * | 2014-05-07 | 2014-10-15 | 林光榕 | 一种双电压电子烟控制组件 |
| CN108059617B (zh) * | 2018-02-06 | 2020-04-07 | 成都倍特药业股份有限公司 | 伏立康唑起始物料4-氯-6-乙基-5-氟嘧啶的杂质及其合成方法 |
| CN108997340B (zh) * | 2018-09-29 | 2020-03-20 | 山东轩德医药科技有限公司 | 一种5-溴-7-氮杂吲哚的合成方法 |
| CN110372601A (zh) * | 2019-06-24 | 2019-10-25 | 南京普锐达医药科技有限公司 | 一种4-氯-6-甲基嘧啶的制备方法 |
| CN111217758A (zh) * | 2020-03-18 | 2020-06-02 | 湖南复瑞生物医药技术有限责任公司 | 一种6-乙基-5-氟-4-氯嘧啶的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0530149A1 (de) | 1991-08-30 | 1993-03-03 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| JP4800216B2 (ja) * | 2003-10-24 | 2011-10-26 | エグゼリクシス， インコーポレイテッド | ｐ７０Ｓ６キナーゼモジュレーターおよび使用方法 |
| UY31769A1 (es) * | 2008-04-17 | 2009-09-30 | Derivados del indol con actividad modulatoria del receptor nicotínico de acetilcolina | |
| JP5642154B2 (ja) * | 2009-04-16 | 2014-12-17 | プロキシマジェン エルティーディーＰｒｏｘｉｍａｇｅｎ Ｌｔｄ． | α７ｎＡＣｈＲのインドール誘導体モジュレータ |
| GB201012686D0 (en) * | 2010-07-28 | 2010-09-15 | Glaxo Group Ltd | Novel compounds |
-
2010
- 2010-07-28 GB GBGB1012686.0A patent/GB201012686D0/en not_active Ceased
- 2010-10-14 JP JP2012533623A patent/JP5746703B2/ja not_active Expired - Fee Related
- 2010-10-14 US US13/501,418 patent/US8796283B2/en not_active Expired - Fee Related
- 2010-10-14 WO PCT/EP2010/065368 patent/WO2011045353A1/en not_active Ceased
- 2010-10-14 EP EP10763718.3A patent/EP2488514B1/en not_active Not-in-force
-
2014
- 2014-06-04 US US14/295,593 patent/US20150005321A1/en not_active Abandoned