JP2006519814A5 - - Google Patents
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- JP2006519814A5 JP2006519814A5 JP2006504813A JP2006504813A JP2006519814A5 JP 2006519814 A5 JP2006519814 A5 JP 2006519814A5 JP 2006504813 A JP2006504813 A JP 2006504813A JP 2006504813 A JP2006504813 A JP 2006504813A JP 2006519814 A5 JP2006519814 A5 JP 2006519814A5
- Authority
- JP
- Japan
- Prior art keywords
- pharmaceutical composition
- disease
- compound
- prophylactic
- therapeutic treatment
- 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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- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 3
- 230000001225 therapeutic Effects 0.000 claims 3
- 206010053643 Neurodegenerative disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000004736 B-Cell Leukemia Diseases 0.000 claims 1
- 206010004939 Bipolar I disease Diseases 0.000 claims 1
- 206010004938 Bipolar disease Diseases 0.000 claims 1
- 208000001183 Brain Injury Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims 1
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000002154 Non-Small-Cell Lung Carcinoma Diseases 0.000 claims 1
- 108009000071 Non-small cell lung cancer Proteins 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 208000001293 Peripheral Nervous System Disease Diseases 0.000 claims 1
- 206010034606 Peripheral neuropathy Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 206010038932 Retinopathy Diseases 0.000 claims 1
- 208000008513 Spinal Cord Injury Diseases 0.000 claims 1
- 208000000389 T-Cell Leukemia Diseases 0.000 claims 1
- 208000001072 Type 2 Diabetes Mellitus Diseases 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001154 acute Effects 0.000 claims 1
- 201000004384 alopecia Diseases 0.000 claims 1
- 231100000360 alopecia Toxicity 0.000 claims 1
- 201000001084 cerebrovascular disease Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 230000000069 prophylaxis Effects 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 201000002510 thyroid cancer Diseases 0.000 claims 1
- 230000000472 traumatic Effects 0.000 claims 1
- 201000004810 vascular dementia Diseases 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N DMA Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N n-methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical class OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Description
この方法に従い、上記の式(III)で表されるピリミジンオン誘導体（ここで、R1、R3、m、n、pおよびqは式(I)の化合物について定義したとおりである）は、水素化ナトリウム、炭酸ナトリウムまたは炭酸カリウムのような塩基と、N,N-ジメチルホルムアミド、N-メチルピロリドン、N,N-ジメチルアセトアミドまたはクロロホルムのような溶媒中、0〜130℃の範囲の適切な温度で、大気下で反応させ、次いで式(II)（ここで、R2、X、Yおよびnは式(l)の化合物について定義したとおりであり、Lは脱離基、好ましくは臭素またはメシル基を表す）の化合物と反応させて、前記の式(I)の化合物を得る。
Claims (6)
- 式(III)
の化合物。 - GSK3βの異常活性に起因する疾患の予防的および／または治療的処置のための、請求項１〜４のいずれか一つに記載の化合物を含む医薬組成物。
- 神経変性疾患の予防的および／または治療的処置のための、請求項１〜４のいずれか一つに記載の化合物を含む医薬組成物。
- 神経変性疾患がアルツハイマー病、パーキンソン病、タウ病、血管性痴呆、急性脳卒中、外傷性の障害、脳血管障害、脳損傷、脊髄損傷、末梢神経障害、網膜症または緑内障からなる群から選択される、請求項９に記載の医薬組成物。
- 非インスリン依存性糖尿病、肥満症、躁うつ病、統合失調症、脱毛症または癌の予防的および／または治療的処置のための、請求項１〜４のいずれか一つに記載の化合物を含む医薬組成物。
- 癌が乳癌、非小細胞肺癌、甲状腺癌、TもしくはB-細胞白血病またはウイルス誘発性腫瘍である、請求項１１に記載の医薬組成物。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03290569A EP1454909B1 (en) | 2003-03-07 | 2003-03-07 | 8'-pyridinyl-dihydrospiro (cycloalkyl) -pyrimido (1,2-a) pyrimidin-6-one and 8'-pyrimidinyl-dihydrospiro (cycloalkyl) pyrimido (1,2-a) pyrimidin-6 derivatives -one and their use against neurodegenerative diseases |
| PCT/EP2004/003051 WO2004078760A1 (en) | 2003-03-07 | 2004-03-05 | SUBSTITUTED 8'-PYRIDINYL-DIHYDROSPIRO-[CYCLOALKYL]-PYRIMIDO [1,2-a] PYRIMIDIN-6-ONE AND 8'-PYRIMIDINYL-DIHYDROSPIRO-[CYCLOALKYL]-PYRIMIDO [1,2-a] PYRIMIDIN-6-ONE DERIVATIVES AND THEIR USE AGAINST NEUROGENERATIVE DISEASES |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006519814A JP2006519814A (ja) | 2006-08-31 |
| JP2006519814A5 true JP2006519814A5 (ja) | 2007-04-19 |
| JP4639182B2 JP4639182B2 (ja) | 2011-02-23 |
Family
ID=32799103
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006504813A Expired - Fee Related JP4639182B2 (ja) | 2003-03-07 | 2004-03-05 | 置換された８’−ピリジニル−ジヒドロスピロ−［シクロアルキル］−ピリミド［１，２−ａ］ピリミジン−６−オンおよび８’−ピリミジニル−ジヒドロスピロ−［シクロアルキル］−ピリミド［１，２−ａ］ピリミジン−６−オン誘導体 |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US7294632B2 (ja) |
| EP (2) | EP1454909B1 (ja) |
| JP (1) | JP4639182B2 (ja) |
| KR (1) | KR101069984B1 (ja) |
| CN (1) | CN100463908C (ja) |
| AR (1) | AR043485A1 (ja) |
| AT (1) | ATE469153T1 (ja) |
| AU (1) | AU2004218250B2 (ja) |
| BR (1) | BRPI0408189A (ja) |
| CA (1) | CA2516937C (ja) |
| CY (1) | CY1111057T1 (ja) |
| DE (1) | DE602004027354D1 (ja) |
| DK (1) | DK1603915T3 (ja) |
| EA (1) | EA008172B1 (ja) |
| ES (1) | ES2346311T3 (ja) |
| HK (1) | HK1085740A1 (ja) |
| IL (1) | IL170461A (ja) |
| MX (1) | MXPA05009574A (ja) |
| NO (1) | NO20054140L (ja) |
| NZ (1) | NZ542135A (ja) |
| PL (1) | PL1603915T3 (ja) |
| PT (1) | PT1603915E (ja) |
| SI (1) | SI1603915T1 (ja) |
| TW (1) | TWI320785B (ja) |
| WO (1) | WO2004078760A1 (ja) |
| ZA (1) | ZA200507107B (ja) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006138217A1 (en) | 2005-06-14 | 2006-12-28 | Schering Corporation | Aspartyl protease inhibitors |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| CA2625210A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP1992620A1 (en) * | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone derivatives for the treatment of neurodegenerative diseases |
| EP1992625A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Arylamide pyrimidone compounds |
| EP1992621A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide-substituted pyrimidone derivatives for the treatment of neurodegenerative diseases |
| EP1992624A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
| EP2138498A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted tricyclic derivatives against neurodegenerative diseases |
| EP2138485A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted N-Oxide pyrazine derivatives |
| EP2138495A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted pyrimido[2,1-a]isoquinolin-4-one derivatives |
| EP2138494A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
| EP2138488A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | 4-(pyridin-4-yl)-1H-[1,3,5]triazin-2-one derivatives as GSK3-beta inhibitors for the treatment of neurodegenerative diseases |
| EP2138493A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidone derivatives |
| EP2138492A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidin-4-one derivatives |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| WO2011001113A2 (fr) | 2009-07-02 | 2011-01-06 | Sanofi-Aventis | NOUVEAUX DERIVES DE 1,2,3,4-TETRAHYDRO-PYRIMIDO{1,2-a}PYRIMIDIN-6-ONE,LEUR PREPARATION ET LEUR UTILISATION PHARMACEUTIQUE |
| PL2655375T3 (pl) | 2010-12-23 | 2015-05-29 | Sanofi Sa | Pochodne pirymidynonu, ich wytwarzanie i ich farmaceutyczne zastosowanie |
| FR2992316A1 (fr) | 2012-06-22 | 2013-12-27 | Sanofi Sa | Derives de pyrimidinones, leur preparation et leur application en therapeutique |
| FR2992314B1 (fr) | 2012-06-22 | 2015-10-16 | Sanofi Sa | Nouveaux derives de 2,3-dihydro-1h-imidazo{1,2-a}pyrimidin-5-one et 1,2,3,4-tetrahydro-pyrimido{1,2-a}pyrimidin-6-one comportant une morpholine substituee, leur preparation et leur utilisation pharmaceutique |
| CA2945263A1 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2812636A1 (fr) * | 2000-08-02 | 2002-02-08 | Novapharme | Nouveaux derives 2-phenyl imidazo[1.2-a]pyrimidin-5-ones et 2-phenyl 2,3-dihydro imidazo[1,2-a]pyrimidin-5-ones |
| EP1184385A1 (en) * | 2000-09-01 | 2002-03-06 | Sanofi-Synthelabo | 1-[Alkyl], 1-[(heteroaryl)alkyl] and 1-[(aryl)alkyl]-7-pyridin-4-yl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)-one derivatives |
| DE60103909T2 (de) * | 2000-09-01 | 2005-09-22 | Sanofi-Aventis | 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-on- und 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5 1honderivate |
| EP1184383A1 (en) * | 2000-09-01 | 2002-03-06 | Sanofi-Synthelabo | 9-[Alkyl], 9-[(heteroaryl)alkyl] and 9-[(aryl)alkyl]-2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one derivatives |
| EP1295885A1 (en) * | 2001-09-21 | 2003-03-26 | Sanofi-Synthelabo | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido(1,2-a)pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo(1,2-a)pyrimidin-5(1H)one derivatives |
| NZ531244A (en) * | 2001-09-21 | 2006-06-30 | Sanofi Aventis | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-A]pyrimidin-4-one and 7-pyrimidinyl-2,3-dihydroimidazo [1,2-A]pyrimidin-5(1H)one derivatives for neurodegenerative disorders |
| NZ547205A (en) * | 2001-09-21 | 2007-11-30 | Sanofi Aventis | Intermediates of substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1H)one derivatives |
| EP1295884A1 (en) * | 2001-09-21 | 2003-03-26 | Sanofi-Synthelabo | 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a]Pyrimidin-4-one and 7-Pyrimidinyl-2,3-Dihydroimidazo[1,2-a]Pyrimidin-5(1H)one derivatives |
-
2003
- 2003-03-07 EP EP03290569A patent/EP1454909B1/en not_active Withdrawn - After Issue
-
2004
- 2004-03-05 CA CA2516937A patent/CA2516937C/en not_active Expired - Fee Related
- 2004-03-05 ES ES04717643T patent/ES2346311T3/es not_active Expired - Lifetime
- 2004-03-05 EP EP04717643A patent/EP1603915B1/en not_active Expired - Lifetime
- 2004-03-05 SI SI200431465T patent/SI1603915T1/sl unknown
- 2004-03-05 ZA ZA200507107A patent/ZA200507107B/en unknown
- 2004-03-05 MX MXPA05009574A patent/MXPA05009574A/es active IP Right Grant
- 2004-03-05 BR BRPI0408189-7A patent/BRPI0408189A/pt not_active IP Right Cessation
- 2004-03-05 PT PT04717643T patent/PT1603915E/pt unknown
- 2004-03-05 DE DE602004027354T patent/DE602004027354D1/de not_active Expired - Lifetime
- 2004-03-05 CN CNB2004800109973A patent/CN100463908C/zh not_active Expired - Fee Related
- 2004-03-05 AR ARP040100694A patent/AR043485A1/es not_active Application Discontinuation
- 2004-03-05 TW TW093105914A patent/TWI320785B/zh not_active IP Right Cessation
- 2004-03-05 WO PCT/EP2004/003051 patent/WO2004078760A1/en active Application Filing
- 2004-03-05 AU AU2004218250A patent/AU2004218250B2/en not_active Ceased
- 2004-03-05 PL PL04717643T patent/PL1603915T3/pl unknown
- 2004-03-05 AT AT04717643T patent/ATE469153T1/de active
- 2004-03-05 NZ NZ542135A patent/NZ542135A/en not_active IP Right Cessation
- 2004-03-05 EA EA200501241A patent/EA008172B1/ru not_active IP Right Cessation
- 2004-03-05 JP JP2006504813A patent/JP4639182B2/ja not_active Expired - Fee Related
- 2004-03-05 DK DK04717643.3T patent/DK1603915T3/da active
-
2005
- 2005-08-23 IL IL170461A patent/IL170461A/en not_active IP Right Cessation
- 2005-09-06 NO NO20054140A patent/NO20054140L/no not_active Application Discontinuation
- 2005-09-06 KR KR1020057016622A patent/KR101069984B1/ko not_active IP Right Cessation
- 2005-09-07 US US11/220,999 patent/US7294632B2/en not_active Expired - Fee Related
-
2006
- 2006-07-14 HK HK06107902.6A patent/HK1085740A1/xx not_active IP Right Cessation
-
2007
- 2007-10-02 US US11/866,142 patent/US7507743B2/en not_active Expired - Fee Related
-
2010
- 2010-08-17 CY CY20101100761T patent/CY1111057T1/el unknown
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