JP2009508900A - セレクチンリガンド活性を有する新規なフロログルシノール誘導体 - Google Patents
セレクチンリガンド活性を有する新規なフロログルシノール誘導体 Download PDFInfo
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- 0 C*C(C(C)(C)CC(C)(C)C)N Chemical compound C*C(C(C)(C)CC(C)(C)C)N 0.000 description 4
- KEUIAQWIESYADW-HMWJUTMASA-N CC(C)(/C=C/C=C\C=N/C)S Chemical compound CC(C)(/C=C/C=C\C=N/C)S KEUIAQWIESYADW-HMWJUTMASA-N 0.000 description 1
- KNDSDAUZINPACQ-UHFFFAOYSA-N CC(C)(C(C)=O)N Chemical compound CC(C)(C(C)=O)N KNDSDAUZINPACQ-UHFFFAOYSA-N 0.000 description 1
- ZFAOMXLKSPRYKP-UHFFFAOYSA-N CC(C)(C([IH]C)=O)N Chemical compound CC(C)(C([IH]C)=O)N ZFAOMXLKSPRYKP-UHFFFAOYSA-N 0.000 description 1
- WORGBHGLWVQFDG-UHFFFAOYSA-N CC(c1cc(SC)cnc1)=O Chemical compound CC(c1cc(SC)cnc1)=O WORGBHGLWVQFDG-UHFFFAOYSA-N 0.000 description 1
- AYYMFFXHDAHZIQ-UHFFFAOYSA-N CC(c1cc([IH]C)ccc1)=O Chemical compound CC(c1cc([IH]C)ccc1)=O AYYMFFXHDAHZIQ-UHFFFAOYSA-N 0.000 description 1
- WAIWKGWQKHZLKL-UHFFFAOYSA-N CC(c1nc([IH](C)=C)ccc1)=O Chemical compound CC(c1nc([IH](C)=C)ccc1)=O WAIWKGWQKHZLKL-UHFFFAOYSA-N 0.000 description 1
- FWCSKOSXNXUQEJ-UHFFFAOYSA-N OC(c1ccc(-c2ccccc2NC(c2cc(-c(c(O)cc(O)c3)c3O)ccc2)=O)[s]1)=O Chemical compound OC(c1ccc(-c2ccccc2NC(c2cc(-c(c(O)cc(O)c3)c3O)ccc2)=O)[s]1)=O FWCSKOSXNXUQEJ-UHFFFAOYSA-N 0.000 description 1
- BBKYGPKEERJGRD-UHFFFAOYSA-N Oc1cc(O)c(-c2cc(C(Nc3ccccc3-c3ccc[s]3)=O)ccc2)c(O)c1 Chemical compound Oc1cc(O)c(-c2cc(C(Nc3ccccc3-c3ccc[s]3)=O)ccc2)c(O)c1 BBKYGPKEERJGRD-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
−X−は、
(a)
(b)
(c)
(d)
(e)
(f)
(a)
R2は、CO2H、CO2アルキル、CO2アリール、CO2NH2、CO2アラルキル、SO3H、SO2NH2、PO(OH)2、1−H−テトラゾリル−、CHO、COCH3、CH2OH、NH2、NHアルキル、N(アルキル)アルキル’、OCH3、CH2OCH3、SH、F、Cl、Br、I、CH3、CH2CH3、CN、CF3であり、
R3は、R2から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2であり、そしてR4は、R2及びR3から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2、R2であり、
R5は、H、NO2、CF3、F、Cl、Br、I、CN、CH3、OCH3、SH、NH2であり、
そして−W−は、−(CH2−)v、シス−CH=CH−又はトランス−CH=CH−であり、そしてvは、0、1、2であり;
−W−が、シス−CH=CH−又はトランス−CH=CH−である場合には、R2は、NH2又はSHであってはならず;
(b)
(c)
(d)
(e)
(f)
(g)
(i)
(ii)
(iii)
(iv)
(v)
(vi)
(vii)
−W−R2である。
−X−は、
(a)
(b)
(c)
(a)
R2は、CO2H、CO2アルキル、CO2アリール、CO2NH2、CO2アラルキル、SO3H、SO2NH2、PO(OH)2、1−H−テトラゾリル−、CHO、COCH3、CH2OH、NH2、NHアルキル、N(アルキル)アルキル’、OCH3、CH2OCH3、SH、F、Cl、Br、I、CH3、CH2CH3、CN、CF3であり、
R3は、R2から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2であり、そしてR4は、R2及びR3から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2、R2であり、
R5は、H、NO2、CF3、F、Cl、Br、I、CN、CH3、OCH3、SH、NH2であり、
そして−W−は、−(CH2−)v、シス−CH=CH−又はトランス−CH=CH−であり、そしてvは、0、1、2であり;
−W−が、シス−CH=CH−又はトランス−CH=CH−である場合には、R2は、NH2又はSHであってはならず;
(b)
(c)
(e)
(i)
(iv)
(v)
ここですべての他の指標、記号及び置換基は、上記で定義される通りである。
2−メチル−5−{4−[2−(2,4,6−トリヒドロキシ−フェニル)−アセチルアミノ]−フェニル}−フラン−3−カルボン酸(19)
60PF、CyH/EtOAc 3+1)により粗生成物を精製して、黄色固体としてアミド(61)を得た(722mg、41%)。1H NMR(400MHz,CDCl3):3.69(s,6H);3.72(s,3H);3.80(s,2H);3.86(s,3H);6.21(s,2H);6.92(d,1H,J=3.5Hz);7.01(d,1H,J=3.5Hz);7.14(t,1H,J=7.3Hz);7.36−7.42(m,2H);7.44(d,1H,J=7.8Hz);7.48(br.d,1H,J=7.6Hz);7.61(br.d,1H,7.3Hz);7.78(br.s,1H);8.35(br.s,1H);8.50(d,1H,J=8.3Hz)。
(5−{2−[2−(2,4,6−トリヒドロキシ−フェニル)−アセチルアミノ]−フェニル}−チオフェン−2−イル)−酢酸(25) REV989、DU27
5−{2−[(2’,4’,6’−トリヒドロキシ−ビフェニル−3−カルボニル)−アミノ]−フェニル}−チオフェン−2−カルボン酸(26) REV971、LE37
(5−{3−[(2’,4’,6’−トリヒドロキシ−ビフェニル−3−カルボニル)−アミノ]−フェニル}−チオフェン−2−イル)−酢酸(64) REV996、KM7
2’,4’,6’−トリヒドロキシ−ビフェニル−3−カルボン酸(2−チオフェン−2−イル−フェニル)−アミド(65) REV965、AB437
2’,4’,6’−トリヒドロキシ−ビフェニル−3−カルボン酸(3−トリフルオロメチル−フェニル)−アミド(66) REV961、DU15
3−[(2’,4’,6’−トリヒドロキシ−ビフェニル−3−カルボニル)−アミノ]−安息香酸(67) REV1007、LE80
本発明の化合物を、PSGL−1代替物のようなポリマーマトリックスに連結されたsLex及びチロシンスルフェート残基とのP−セレクチン、L−セレクチン又はE−セレクチンキメラ分子の結合を阻害する能力について分子レベルでアッセイした。選択されたIC50値を測定した。
血管での流動に似ている動力学的条件下で化合物が細胞結合を阻害する能力を評価するために、P−セレクチン、L−セレクチン及びE−セレクチンキメラ分子とのHL−60細胞/種々の細胞株の結合を検討/試験する流動チャンバーアッセイを行った。
Claims (12)
- 式(I):
上記式中、
−X−は、
(a)
(b)
(c)
−Yは、
(a)
R2は、CO2H、CO2アルキル、CO2アリール、CO2NH2、CO2アラルキル、SO3H、SO2NH2、PO(OH)2、1−H−テトラゾリル−、CHO、COCH3、CH2OH、NH2、NHアルキル、N(アルキル)アルキル’、OCH3、CH2OCH3、SH、F、Cl、Br、I、CH3、CH2CH3、CN、CF3であり、
R3は、R2から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2であり、そしてR4は、R2及びR3から独立してH、CH3、CH2CH3、CF3、F、Cl、Br、I、CN、NO2、R2であり、
R5は、H、NO2、CF3、F、Cl、Br、I、CN、CH3、OCH3、SH、NH2であり、
そして−W−は、−(CH2−)v、シス−CH=CH−又はトランス−CH=CH−であり、そしてvは、0、1、2であり;
−W−が、シス−CH=CH−又はトランス−CH=CH−である場合には、R2は、NH2又はSHであってはならず;
(b)
(c)
(e)
−Zは、
(i)
(iv)
(v)
- 請求項4又は5に記載の式(C)又は式(D)の一般構造を有する化学物質。
- 慢性閉塞性肺疾患(COPD)、急性肺障害(ALI)、心肺バイパス、急性呼吸促迫症候群(ARDS)、クローン病、敗血症性ショック、敗血症、慢性炎症性疾患(例えば乾癬、アトピー性皮膚炎及び慢性関節リウマチ)、並びに心臓発作、脳卒中、アテローム性動脈硬化症及び器官移植後に生じる再灌流障害、外傷性ショック、多臓器不全、多発性硬化症のような自己免疫疾患、経皮経管的血管形成術、喘息並びに炎症性腸疾患を処置するための医薬の製造のための、請求項1で定義される式(I)の構造を有する化合物の使用。
- 炎症性疾患を処置、診断又は予防するための医薬の製造のための、請求項1で定義される式(I)の構造を有する化合物の使用。
- 診断又は治療の薬剤標的のためのビヒクルの製造のための、請求項1で定義される式(I)の構造を有する化合物の使用。
- 化粧用組成物又は皮膚科学的組成物の製造のための、請求項1で定義される式(I)の構造を有する化合物の使用。
- 請求項1に記載の式(I)の少なくとも1つの化合物及び少なくとも1つの化粧用に許容される成分を含む化粧用組成物。
- 請求項1に記載の式(I)の少なくとも1つの化合物及び少なくとも1つの皮膚科学的に許容される成分を含む皮膚科学的組成物。
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EP05020509A EP1764096A1 (en) | 2005-09-20 | 2005-09-20 | Novel phloroglucinol derivatives having selectin ligand activity |
EP0520509.5 | 2005-09-20 | ||
PCT/EP2006/009153 WO2007039112A1 (en) | 2005-09-20 | 2006-09-20 | Novel phloroglucinol derivatives having selectin ligand activity |
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EP (2) | EP1764096A1 (ja) |
JP (1) | JP5122463B2 (ja) |
CN (1) | CN101312719A (ja) |
AU (1) | AU2006299182B2 (ja) |
BR (1) | BRPI0616388A2 (ja) |
CA (1) | CA2622467A1 (ja) |
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JP6616790B2 (ja) | 2014-06-27 | 2019-12-04 | ノグラ ファーマ リミテッド | アリール受容体モジュレーターならびにその作製および使用方法 |
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2006
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- 2006-09-20 CA CA002622467A patent/CA2622467A1/en not_active Abandoned
- 2006-09-20 US US12/067,059 patent/US7919532B2/en not_active Expired - Fee Related
- 2006-09-20 BR BRPI0616388-2A patent/BRPI0616388A2/pt not_active IP Right Cessation
- 2006-09-20 AU AU2006299182A patent/AU2006299182B2/en not_active Ceased
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2008
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JP2009508899A (ja) * | 2005-09-20 | 2009-03-05 | レボタール・バイオファーマシューティカルズ・アーゲー | 新規な多環式化合物 |
Also Published As
Publication number | Publication date |
---|---|
US7919532B2 (en) | 2011-04-05 |
EP1764096A1 (en) | 2007-03-21 |
AU2006299182A1 (en) | 2007-04-12 |
IL190085A0 (en) | 2008-08-07 |
WO2007039112A1 (en) | 2007-04-12 |
AU2006299182B2 (en) | 2012-06-28 |
US8461207B2 (en) | 2013-06-11 |
RU2418584C2 (ru) | 2011-05-20 |
BRPI0616388A2 (pt) | 2011-06-21 |
CN101312719A (zh) | 2008-11-26 |
CA2622467A1 (en) | 2007-04-12 |
US20110142765A1 (en) | 2011-06-16 |
IL190085A (en) | 2013-06-27 |
US20080207741A1 (en) | 2008-08-28 |
EP1937237A1 (en) | 2008-07-02 |
WO2007039112A8 (en) | 2008-07-03 |
JP5122463B2 (ja) | 2013-01-16 |
RU2008115434A (ru) | 2009-10-27 |
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