JP2011510970A5 - - Google Patents
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- Publication number
- JP2011510970A5 JP2011510970A5 JP2010544814A JP2010544814A JP2011510970A5 JP 2011510970 A5 JP2011510970 A5 JP 2011510970A5 JP 2010544814 A JP2010544814 A JP 2010544814A JP 2010544814 A JP2010544814 A JP 2010544814A JP 2011510970 A5 JP2011510970 A5 JP 2011510970A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- compound
- triaza
- formula
- pyrimidin
- 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 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- -1 2-pyrimidin-4-yl-4,5,6,7,8,9-hexahydro-1,4a, 7-triaza-benzocyclohepten-9-yl Chemical group 0.000 description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- RJDMSNXYEMRJHW-UHFFFAOYSA-N 4-chloro-2-methoxy-n-(8-methyl-4-oxo-2-pyrimidin-4-yl-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepin-10-yl)benzamide Chemical compound COC1=CC(Cl)=CC=C1C(=O)NC1C2=NC(C=3N=CN=CC=3)=CC(=O)N2CCN(C)C1 RJDMSNXYEMRJHW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ARQRHOAJKHMUQA-UHFFFAOYSA-N ethyl 10-[(4-methoxyphenyl)methyl-methylamino]-4-oxo-2-pyridin-4-yl-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-8-carboxylate Chemical compound C=1C=C(OC)C=CC=1CN(C)C1CN(C(=O)OCC)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 ARQRHOAJKHMUQA-UHFFFAOYSA-N 0.000 description 1
- LRNYYPFYQYBQRC-UHFFFAOYSA-N ethyl 10-amino-4-oxo-2-pyridin-4-yl-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-8-carboxylate Chemical compound NC1CN(C(=O)OCC)CCN(C(C=2)=O)C1=NC=2C1=CC=NC=C1 LRNYYPFYQYBQRC-UHFFFAOYSA-N 0.000 description 1
- BZHLYBBTYSLEHJ-UHFFFAOYSA-N ethyl 4-oxo-2-pyridin-4-yl-6,7,9,10-tetrahydropyrimido[1,2-d][1,4]diazepine-8-carboxylate Chemical compound C=1C(=O)N2CCN(C(=O)OCC)CCC2=NC=1C1=CC=NC=C1 BZHLYBBTYSLEHJ-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- QWLISCJHYITNQF-UHFFFAOYSA-N n-methoxy-1-phenylmethanamine Chemical compound CONCC1=CC=CC=C1 QWLISCJHYITNQF-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000008318 pyrimidones Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08290074A EP2090578A1 (en) | 2008-01-29 | 2008-01-29 | Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of GSK3-beta |
| EP08290074.7 | 2008-01-29 | ||
| PCT/IB2009/000324 WO2009095789A1 (en) | 2008-01-29 | 2009-01-27 | Substituted arylamide diazepinopyrimidone derivatives for the treatment of neurodegenerative diseases caused by abnormal activity of gsk3-beta |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011510970A JP2011510970A (ja) | 2011-04-07 |
| JP2011510970A5 true JP2011510970A5 (enExample) | 2012-01-19 |
| JP5611836B2 JP5611836B2 (ja) | 2014-10-22 |
Family
ID=39638986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010544814A Expired - Fee Related JP5611836B2 (ja) | 2008-01-29 | 2009-01-27 | Ｇｓｋ３ベータの異常活性によって引き起こされる神経変性疾患の治療のための置換アリールアミドジアゼピノピリミドン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US8507476B2 (enExample) |
| EP (2) | EP2090578A1 (enExample) |
| JP (1) | JP5611836B2 (enExample) |
| KR (1) | KR20100116592A (enExample) |
| CN (1) | CN101981032A (enExample) |
| AR (1) | AR070274A1 (enExample) |
| AU (1) | AU2009208728A1 (enExample) |
| BR (1) | BRPI0906618A2 (enExample) |
| CA (1) | CA2713256A1 (enExample) |
| EA (1) | EA201070896A1 (enExample) |
| IL (1) | IL207193A0 (enExample) |
| MX (1) | MX2010008363A (enExample) |
| NZ (1) | NZ587069A (enExample) |
| TW (1) | TW200936589A (enExample) |
| WO (1) | WO2009095789A1 (enExample) |
| ZA (1) | ZA201005384B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2090579A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted heteroarylamide diazepinopyrimidone derivatives |
| EP2085399A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | substituted arylamide oxazepinopyrimidone derivatives |
| EP2085400A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | Substituted heteroarylamide oxazepinopyrimidone derivatives |
| EP2138494A1 (en) * | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EA201891620A1 (ru) * | 2016-02-05 | 2019-02-28 | Денали Терапьютикс Инк. | Ингибиторы взаимодействующей с рецептором протеинкиназы 1 |
| PL3552017T3 (pl) | 2016-12-09 | 2022-08-08 | Denali Therapeutics Inc. | Związki użyteczne jako inhibitory RIPK1 |
| CN107987090A (zh) * | 2017-12-19 | 2018-05-04 | 杨文思 | 一种用于治疗疟疾的恶性疟原虫糖原合成酶激酶-3抑制剂的合成方法 |
| US11382889B2 (en) * | 2018-04-19 | 2022-07-12 | Institut D'investigació Biomèdica De Bellvitge (Idibell) | NRF2 activators for the prevention and/or treatment of axonal degeneration |
| CN112516337B (zh) * | 2020-12-11 | 2022-08-12 | 南京邮电大学 | 近红外二区有机共轭聚合物荧光探针的制备方法及其应用 |
| MX2024008648A (es) | 2022-01-12 | 2024-09-23 | Denali Therapeutics Inc | Formas cristalinas de (s)-5-bencil-n-(5-metil-4-oxo-2,3,4,5-tetrah idropirido [3,2- b][1,4]oxacepin-3-il)-4h-1,2,4-triazol-3-carboxam ida. |
| CN116102488B (zh) * | 2023-01-05 | 2025-06-17 | 宁夏医科大学 | 3位具有不同氨基的2,3-二氨基丙酸衍生物的制备方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EG13192A (en) | 1976-02-10 | 1982-12-31 | Rhone Poulenc Ind | Nouveaux derives du dithiole-1,2 leur preparation et les compositions qui les contiennent |
| US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
| JP3188715B2 (ja) | 1995-11-01 | 2001-07-16 | メルク エンド カンパニー インコーポレーテッド | 一酸化窒素シンターゼの阻害物質としてのヘキサヒドロ−５−イミノ−１，４−ヘテロアゼピン誘導体 |
| US20030096813A1 (en) * | 2001-04-20 | 2003-05-22 | Jingrong Cao | Compositions useful as inhibitors of GSK-3 |
| CN1247586C (zh) * | 2001-09-21 | 2006-03-29 | 赛诺菲安万特 | 治疗神经退化性疾病的取代的2－嘧啶基－6,7,8,9－四氢嘧啶并[1,2－a]嘧啶－4－酮及7－嘧啶基－2,3－二氢咪唑并[1,2－a]嘧啶－5(1h)酮衍生物 |
| EP1557417B1 (en) | 2003-12-19 | 2007-03-07 | Sanofi-Aventis | Substituted 8'-pyri(mi)dinyl-dihydrospiro-[cycloalkylamine]-pyrimido[1,2-a] pyrimidin-6-one derivatives |
| EP1790649A1 (en) * | 2005-11-21 | 2007-05-30 | Sanofi-Aventis | Substituted bicyclic pyrimidone derivatives |
| EP2090579A1 (en) * | 2008-01-29 | 2009-08-19 | Sanofi-Aventis | Substituted heteroarylamide diazepinopyrimidone derivatives |
| EP2085399A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | substituted arylamide oxazepinopyrimidone derivatives |
| EP2085400A1 (en) * | 2008-01-29 | 2009-08-05 | Sanofi-Aventis | Substituted heteroarylamide oxazepinopyrimidone derivatives |
-
2008
- 2008-01-29 EP EP08290074A patent/EP2090578A1/en not_active Withdrawn
-
2009
- 2009-01-23 TW TW098103053A patent/TW200936589A/zh unknown
- 2009-01-27 CN CN2009801107249A patent/CN101981032A/zh active Pending
- 2009-01-27 CA CA2713256A patent/CA2713256A1/en not_active Abandoned
- 2009-01-27 KR KR1020107016906A patent/KR20100116592A/ko not_active Withdrawn
- 2009-01-27 EA EA201070896A patent/EA201070896A1/ru unknown
- 2009-01-27 MX MX2010008363A patent/MX2010008363A/es not_active Application Discontinuation
- 2009-01-27 NZ NZ587069A patent/NZ587069A/en not_active IP Right Cessation
- 2009-01-27 EP EP09706634.4A patent/EP2238141B1/en active Active
- 2009-01-27 AU AU2009208728A patent/AU2009208728A1/en not_active Abandoned
- 2009-01-27 JP JP2010544814A patent/JP5611836B2/ja not_active Expired - Fee Related
- 2009-01-27 BR BRPI0906618-7A patent/BRPI0906618A2/pt not_active IP Right Cessation
- 2009-01-27 WO PCT/IB2009/000324 patent/WO2009095789A1/en not_active Ceased
- 2009-01-28 AR ARP090100257A patent/AR070274A1/es unknown
-
2010
- 2010-07-25 IL IL207193A patent/IL207193A0/en unknown
- 2010-07-27 US US12/844,278 patent/US8507476B2/en not_active Expired - Fee Related
- 2010-07-28 ZA ZA2010/05384A patent/ZA201005384B/en unknown
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