JP5409783B2 - 置換n−オキシドピラジン誘導体 - Google Patents
置換n−オキシドピラジン誘導体 Download PDFInfo
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Description
R1は、4−ピリジン環、ハロゲン原子を表し;
R2は、水素原子を表し;
R3は、水素原子を表し;
R4は、
−フェニルC1−3アルキル基(この基は、C1−6アルキル基、ハロゲン原子、C1−2過ハロゲン化アルキル基、C1−3ハロゲン化アルキル基、ヒドロキシル基、C1−6アルコキシ基、C1−2過ハロゲン化アルコキシ基、C1−6アルキルスルホニル基、ニトロ、シアノ、アミノ、C1−6モノアルキルアミノ基またはC2−12ジアルキルアミノ基、アセトキシ基、アミノスルホニル基から選択される1−4個の置換基により場合によって置換されている。)を表し;
R5は、水素原子を表す。]。
「フェニルC1−3アルキル基(この基は、場合によって置換されている。)」は、フェニルC1−3アルキル基のアルキル部分またはフェニル部分での場合による置換を表す。
R1は、4−ピリジン環、ハロゲン原子を表し;
R2は、水素原子を表し;
R3は、水素原子を表し;
R4は、フェニルC1−3アルキル基(この基は、ハロゲン原子、ヒドロキシル基から選択される1−4個の置換基により場合によって置換されている。)を表し;
R5は、水素原子を表す。]
が提供される。
1. N−(2−フェニルエチル)−6−ピリジン−4−イルピラジン−2−アミン4−オキシド
2. (+/−)2−[(4−オキシド−6−ピリジン−4−イルピラジン−2−イル)アミノ]−1−フェニルエタノール
3. (+/−)6−2−[(6−クロロ−4−オキシドピラジン−2−イル)アミノ]−1−フェニルエタノール
4. 6−クロロ−N−(2−フェニルエチル)ピラジン−2−アミン4−オキシド
前述の式(I)によって表されるN−オキシドピラジン化合物は、スキーム1に記載されている方法に従って調製することができる。
6−クロロ−N−(2−フェニルエチル)ピラジン−2−アミン4−オキシド
2,6−ジクロロ−ピラジン4−オキシド0.330g(2.0mmol)のフェネチルアミン0.485g(4.0mmol)中懸濁液を還流下で10分撹拌させた。冷却した水を加え、混合物をジクロロメタンで抽出し、硫酸ナトリウムで乾燥し蒸留乾固した。
Mp:142−143℃
RMN 1H(CDCl3;200MHz):
δ(ppm):7.50(s,1H)、7.30−7.10(m,5H)、5.10(br s,1H)、3.60(dd,2H)、2.90(dd,2H)。
N−(2−フェニルエチル)−6−ピリジン−4−イルピラジン−2−アミン4−オキシド
5/1の割合のエタノール/水の混合物5mL中で、6−クロロ−N−(2−フェニルエチル)ピラジン−2−アミン4−オキシド0.250g(1.0mmol)、4−ピリジンボロン酸0.296g(2.40mmol)、炭酸ナトリウムの2M水溶液0.60mL(1.2mmol)およびテトラキス(トリフェニルホスフィン)パラジウム(0)0.116g(0.1mmol)を含む混合物を還流下で16時間撹拌した。冷却した水を加え、混合物をジクロロメタンで抽出し、硫酸ナトリウムで乾燥し、蒸留乾固した。得られた残留物を、98/2/0.2の割合のジクロロメタン/メタノール/ジエチルアミンの混合物を溶離液とするシリカゲルのクロマトグラフィによって精製してジエチルエーテルですり混ぜた後、黄色固形物として純粋な生成物0.058g(20%)を得た。
Mp:184−185℃
RMN 1H(CDCl3;200MHz):
δ(ppm):8.70(d,2H);7.90(s,1H);7.70(d,2H);7.45(s,1H);7.30−7.00(m,5H);4.80(br t,1H)、3.70(m,2H);2.90(t,2H)。
(1)錠剤
以下の成分を、通常の方法によって混合し、従来の装置を用いて圧縮した。
実施例1の化合物 30mg
結晶セルロース 60mg
トウモロコシデンプン 100mg
乳糖 200mg
ステアリン酸マグネシウム 4mg
(2)軟カプセル剤
以下の成分を、通常の方法によって混合し、軟カプセル剤に充填した。
実施例1の化合物 30mg
オリーブ油 300mg
レシチン 20mg
(3)非経口製剤
以下の成分を、通常の方法によって混合して、アンプル1ml中に含まれる注射剤を調製した。
実施例1の化合物 3mg
塩化ナトリウム 4mg
注射用蒸留水 1ml
Claims (15)
- 遊離塩基の形態または酸との付加塩の形態の、式(I)によって表されるN−オキシドピラジン誘導体またはその塩:
R1は、4−ピリジン環、ハロゲン原子を表し;
R2は、水素原子を表し;
R3は、水素原子を表し;
R4は、
−フェニルC1−3アルキル基(この基は、C1−6アルキル基、ハロゲン原子、C1−2過ハロゲン化アルキル基、C1−3ハロゲン化アルキル基、ヒドロキシル基、C1−6アルコキシ基、C1−2過ハロゲン化アルコキシ基、C1−6アルキルスルホニル基、ニトロ、シアノ、アミノ、C1−6モノアルキルアミノ基またはC2−12ジアルキルアミノ基、アセトキシ基、アミノスルホニル基から選択される1−4個の置換基により場合によって置換されている。)を表し;
R5は、水素原子を表す。]。 - N−(2−フェニルエチル)−6−ピリジン−4−イルピラジン−2−アミン4−オキシド
(+/−)2−[(4−オキシド−6−ピリジン−4−イルピラジン−2−イル)アミノ]−1−フェニルエタノール
(+/−)6−2−[(6−クロロ−4−オキシドピラジン−2−イル)アミノ]−1−フェニルエタノール
6−クロロ−N−(2−フェニルエチル)ピラジン−2−アミン4−オキシド
からなる群から選択される、請求項1および2に記載の、N−オキシドピラジン誘導体またはこれらの塩、またはこれらの溶媒和物またはこれらの水和物。 - 請求項1から3に記載の、式(I)によって表されるN−オキシドピラジン誘導体またはこれらの塩からなる群から選択される物質を有効成分として含む医薬品。
- 請求項1に記載の、式(I)によって表されるN−オキシドピラジン誘導体またはこれらの塩、またはこれらの溶媒和物またはこれらの水和物の群から選択される、GSK3β阻害剤。
- 異常なGSK3β活性によって引き起こされ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から3に記載の化合物。
- 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から3に記載の化合物。
- 神経変性疾患がアルツハイマー病、パーキンソン病、タウオパシー、血管性認知症;急性脳卒中、外傷;脳血管発作、脳外傷、脊髄外傷;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1から3に記載の化合物。
- インスリン非依存性糖尿病;肥満症;躁うつ病;統合失調症;脱毛症;癌;実質性腎疾患または筋萎縮症の予防的および/または治療的処置のための、請求項1から3に記載の化合物。
- 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導腫瘍である、請求項9に記載の化合物。
- マラリアの予防的および/または治療的処置のための、請求項1から3に記載の化合物。
- 骨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から3に記載の化合物。
- 尋常性天疱瘡の予防的および/または治療的処置のための、請求項1から3に記載の化合物。
- 癌の化学療法によって誘発される好中球減少症の予防的および/または治療的処置のための、請求項1から3に記載の化合物。
- 失認および記憶欠損を特徴とする疾患の治療的処置のための、請求項1から3に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP08290619.9 | 2008-06-26 | ||
EP08290619A EP2138485A1 (en) | 2008-06-26 | 2008-06-26 | Substituted N-Oxide pyrazine derivatives |
PCT/IB2009/006445 WO2009156857A1 (en) | 2008-06-26 | 2009-06-25 | Substituted n-oxide pyrazine derivatives |
Publications (2)
Publication Number | Publication Date |
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JP2011525903A JP2011525903A (ja) | 2011-09-29 |
JP5409783B2 true JP5409783B2 (ja) | 2014-02-05 |
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Application Number | Title | Priority Date | Filing Date |
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JP2011515665A Expired - Fee Related JP5409783B2 (ja) | 2008-06-26 | 2009-06-25 | 置換n−オキシドピラジン誘導体 |
Country Status (22)
Country | Link |
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US (1) | US8202874B2 (ja) |
EP (2) | EP2138485A1 (ja) |
JP (1) | JP5409783B2 (ja) |
KR (1) | KR20110028367A (ja) |
CN (1) | CN102076669A (ja) |
AR (1) | AR072229A1 (ja) |
AT (1) | ATE545635T1 (ja) |
AU (1) | AU2009263843A1 (ja) |
BR (1) | BRPI0914676A2 (ja) |
CA (1) | CA2728680A1 (ja) |
DK (1) | DK2321286T3 (ja) |
EA (1) | EA201170093A1 (ja) |
ES (1) | ES2382677T3 (ja) |
IL (1) | IL210170A0 (ja) |
MX (1) | MX2010013939A (ja) |
NZ (1) | NZ590047A (ja) |
PL (1) | PL2321286T3 (ja) |
PT (1) | PT2321286E (ja) |
SI (1) | SI2321286T1 (ja) |
TW (1) | TW201006814A (ja) |
WO (1) | WO2009156857A1 (ja) |
ZA (1) | ZA201009267B (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
EP2138495A1 (en) * | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted pyrimido[2,1-a]isoquinolin-4-one derivatives |
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 |
EP2138498A1 (en) * | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted tricyclic derivatives against neurodegenerative diseases |
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 |
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 |
TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, 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 |
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 |
WO2014106606A1 (en) * | 2013-01-05 | 2014-07-10 | F. Hoffmann-La Roche Ag | Nove phenyl/pyridine series substitued by hydroxyethylamino for the treatment of cancer |
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JPS5170780A (ja) | 1974-12-17 | 1976-06-18 | Nippon Shinyaku Co Ltd | Shinkinabenzoguanidoruino seiho |
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 |
HU178496B (en) | 1977-12-29 | 1982-05-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing 6,7,8,9-tetrahydro-4h-pyrido/1,2-a/pyrimidine derivatives with antiallergic activity |
US4406897A (en) | 1981-07-06 | 1983-09-27 | William H. Rorer, Inc. | 6-Aryl-4-hydrazinyl-s-triazin-2-ones |
US4804663A (en) | 1985-03-27 | 1989-02-14 | Janssen Pharmaceutica N.V. | 3-piperidinyl-substituted 1,2-benzisoxazoles and 1,2-benzisothiazoles |
US5629322A (en) | 1994-11-15 | 1997-05-13 | Merck & Co., Inc. | Cyclic amidine analogs as inhibitors of nitric oxide synthase |
AU700078B2 (en) | 1995-11-01 | 1998-12-17 | Merck & Co., Inc. | Hexahydro-5-imino-1,4-heteroazepine derivatives as inhibitors of nitric oxide synthases |
IL123986A (en) | 1997-04-24 | 2011-10-31 | Organon Nv | Medicinal compounds |
EP1136484A1 (en) | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-(Arylalkylamino)pyrimidone derivatives |
WO2002087589A1 (fr) | 2001-04-26 | 2002-11-07 | Daiichi Pharmaceutical Co., Ltd. | Medicament permettant d'inhiber une pompe d'elimination de medicament |
EP1430056B1 (en) | 2001-09-21 | 2005-10-26 | 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 |
CA2495661C (en) | 2002-08-16 | 2011-06-14 | Kinacia Pty Ltd. | Inhibition of phosphoinositide 3-kinase beta |
SE0203754D0 (sv) * | 2002-12-17 | 2002-12-17 | Astrazeneca Ab | New compounds |
EP1454909B1 (en) | 2003-03-07 | 2008-08-20 | Sanofi Aventis | 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 |
EP1460076A1 (en) | 2003-03-21 | 2004-09-22 | Sanofi-Synthelabo | Substituted 8-perfluoroalkyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one derivatives |
EP1790649A1 (en) | 2005-11-21 | 2007-05-30 | Sanofi-Aventis | Substituted bicyclic pyrimidone derivatives |
WO2007067802A2 (en) | 2005-12-09 | 2007-06-14 | Brunswick Bowling & Billiards Corporation | Method for controlling a manufacturing process of a bowling ball |
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 |
EP2138494A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted alkyl pyrimidin-4-one derivatives |
EP2138493A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidone derivatives |
EP2138495A1 (en) | 2008-06-26 | 2009-12-30 | sanofi-aventis | Substituted pyrimido[2,1-a]isoquinolin-4-one derivatives |
EP2138492A1 (en) | 2008-06-26 | 2009-12-30 | Sanofi-Aventis | Substituted pyrimidin-4-one derivatives |
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2008
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- 2009-06-25 KR KR1020117001903A patent/KR20110028367A/ko not_active Application Discontinuation
- 2009-06-25 CA CA2728680A patent/CA2728680A1/en not_active Abandoned
- 2009-06-25 PL PL09769668T patent/PL2321286T3/pl unknown
- 2009-06-25 ES ES09769668T patent/ES2382677T3/es active Active
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Also Published As
Publication number | Publication date |
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ZA201009267B (en) | 2012-03-28 |
CA2728680A1 (en) | 2009-12-30 |
US8202874B2 (en) | 2012-06-19 |
CN102076669A (zh) | 2011-05-25 |
IL210170A0 (en) | 2011-03-31 |
PL2321286T3 (pl) | 2012-07-31 |
EA201170093A1 (ru) | 2011-06-30 |
EP2138485A1 (en) | 2009-12-30 |
DK2321286T3 (da) | 2012-06-11 |
AU2009263843A1 (en) | 2009-12-30 |
WO2009156857A1 (en) | 2009-12-30 |
SI2321286T1 (sl) | 2012-06-29 |
ES2382677T3 (es) | 2012-06-12 |
ATE545635T1 (de) | 2012-03-15 |
NZ590047A (en) | 2011-11-25 |
PT2321286E (pt) | 2012-05-02 |
TW201006814A (en) | 2010-02-16 |
MX2010013939A (es) | 2011-09-27 |
BRPI0914676A2 (pt) | 2015-10-20 |
EP2321286B1 (en) | 2012-02-15 |
KR20110028367A (ko) | 2011-03-17 |
EP2321286A1 (en) | 2011-05-18 |
AR072229A1 (es) | 2010-08-11 |
JP2011525903A (ja) | 2011-09-29 |
US20110136828A1 (en) | 2011-06-09 |
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