JP2014506875A - S−ニトロソグルタチオンレダクターゼ阻害薬としての新規な置換二環芳香族化合物 - Google Patents
S−ニトロソグルタチオンレダクターゼ阻害薬としての新規な置換二環芳香族化合物 Download PDFInfo
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- JP2014506875A JP2014506875A JP2013544827A JP2013544827A JP2014506875A JP 2014506875 A JP2014506875 A JP 2014506875A JP 2013544827 A JP2013544827 A JP 2013544827A JP 2013544827 A JP2013544827 A JP 2013544827A JP 2014506875 A JP2014506875 A JP 2014506875A
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- hydroxynaphthalen
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- benzoic acid
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- 0 *c(c(*)c1*)c(*)c(cc2)c1c(*)c2O Chemical compound *c(c(*)c1*)c(*)c(cc2)c1c(*)c2O 0.000 description 1
- LGHCXSKOLNFAKI-UHFFFAOYSA-N OC(c(cc1)ccc1-c(cc1cc2)ccc1c(F)c2O)=O Chemical compound OC(c(cc1)ccc1-c(cc1cc2)ccc1c(F)c2O)=O LGHCXSKOLNFAKI-UHFFFAOYSA-N 0.000 description 1
- JZJXIWIOECGMPN-UHFFFAOYSA-N OC(c(cc1)ccc1-c1ccc(cc(cc2)O)c2c1F)=O Chemical compound OC(c(cc1)ccc1-c1ccc(cc(cc2)O)c2c1F)=O JZJXIWIOECGMPN-UHFFFAOYSA-N 0.000 description 1
- OERRFGVWXVBAAB-UHFFFAOYSA-N OC(c(nc1)ncc1-c(ccc1c2)cc1ccc2O)=O Chemical compound OC(c(nc1)ncc1-c(ccc1c2)cc1ccc2O)=O OERRFGVWXVBAAB-UHFFFAOYSA-N 0.000 description 1
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
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- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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Abstract
【選択図】なし
Description
式中
R1は、H、F、およびClからなる群から選択され;
R2aおよびR2bは、独立して、H、F、Cl、Br、Me、OCH3、およびシアノからなる群から選択され;
R2cは、H、F、Cl、Br、Me、およびOCH3からなる群から選択され;
Xは、
Aは、
R3は、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され;
nは0、1、および2からなる群から選択され;
R4は、H、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され、ただしXが
式中
R1は、H、F、およびClからなる群から選択され;
R2aおよびR2bは、独立して、H、F、Cl、Br、Me、OCH3、およびシアノからなる群から選択され;
R2cは、H、F、Cl、Br、Me、およびOCH3からなる群から選択され;
Xは、
Aは、
R3は、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され;
nは0、1、および2からなる群から選択され;
R4は、H、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され、ただしXが
Z1は、CR2aおよびNからなる群から選択され;
Z2は、CR2bおよびNからなる群から選択され;
Z3は、CR2cおよびNからなる群から選択され;
ただしZ1、Z2、またはZ3の少なくとも1つはNでなければならず;
mは、0、1、2、または3からなる群から選択され;
R1は、独立して、クロロ、フルオロ、およびブロモからなる群から選択され;
R2a、R2b、およびR2cは、独立して、水素、ハロゲン、C1〜C3アルキル、フッ化C1〜C3アルキル、シアノ、C1〜C3アルコキシ、およびN(CH3)2からなる群から選択され;
Xは、
nは0、1、および2から選択され;
R3は、独立して、ハロゲン、C1〜C3アルキル、フッ化C1〜C3アルキル、シアノ、C1〜C3アルコキシ、およびNR4R4’からなる群から選択され、式中、R4およびR4’は、独立して、C1〜C3アルキルからなる群から選択され、またはR4はR4’と一緒になって3〜6員環を形成し;
Aは、
3−クロロ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
3−フルオロ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
6−ヒドロキシナフタレン−2−イル)−3−メトキシ安息香酸;
3−(ジメチルアミノ)−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
3−シアノ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシナフタレン−2−イル)−3−モルホリノ安息香酸;
4−(1−ブロモ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−1−メチルナフタレン−2−イル)安息香酸;
4−(1−シアノ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−3−メトキシナフタレン−2−イル)安息香酸;
4−(1−クロロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
6−(4−(1H−テトラゾール−5−イル)フェニル)ナフタレン−2−オール;
5−(6−ヒドロキシナフタレン−2−イル)ピコリン酸;
6−(6−ヒドロキシナフタレン−2−イル)ニコチン酸;
5−(6−ヒドロキシナフタレン−2−イル)ピラジン−2−カルボン酸;
2−(6−ヒドロキシナフタレン−2−イル)ピリミジン−5−カルボン酸;
6−(6−ヒドロキシナフタレン−2−イル)ピリダジン−3−カルボン酸;
5−(6−ヒドロキシナフタレン−2−イル)ピリミジン−2−カルボン酸;
6−(1H−ベンゾ[d][1,2,3]トリアゾール−6−イル)ナフタレン−2−オール
4−(6−ヒドロキシナフタレン−2−イル)−3−(トリフルオロメチル)安息香酸;
3−クロロ−4−(3−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(3−クロロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(3−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−1−メトキシナフタレン−2−イル)安息香酸;
4−(1−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−3−メチルナフタレン−2−イル)安息香酸;
4−(1−シアノ−5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(1−シアノ−6−ヒドロキシナフタレン−2−イル)−3−フルオロ安息香酸;
3−クロロ−4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
3−フルオロ−4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;および
4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)−3−メチル安息香酸
が挙げられるが、これらに限定されない。
実施例
中間体の合成
GSNORアッセイ
実験的喘息におけるGSNORiの有効性
マウス薬物動態(PK)試験
IV部分のPKパラメータ−AUC最終;AUCINF;T1/2;Cl;Vss;Cmax;MRT
PO部分のPKパラメータ−AUC最終;AUCINF;T1/2;Cmax;Cl;MRT。
実験的炎症性腸疾患(IBD)におけるGSNOR阻害薬の有効性
実験的慢性閉塞性肺疾患(COPD)におけるGSNOR阻害薬の有効性
アセトアミノフェン毒性の探究マウス試験
−6日目 マウスを入手し標準ケージ内に置く
−1日目 動物を一晩断食させる
0日目 加重、PO ACAP時間=0、時間=2IV GSNOまたはGSNORi、全群をACAP6時間後に出血させる
1日目 加重、LFT、IV GSNOまたはGSNORi24時間において全群を出血させる
2日目 加重、IV GSNOまたはGSNORi
3日目 LFT72時間において出血させ、肝重量および組織病理を収集する
STAMマウスにおけるGSNORiの抗NASH線維性活性を評価する探究試験
* * * *
Claims (32)
- 式1の化合物:
式中
R1がH、F、およびClからなる群から選択され;
R2aおよびR2bは、独立して、H、F、Cl、Br、Me、OCH3、およびシアノからなる群から選択され;
R2cがH、F、Cl、Br、Me、およびOCH3からなる群から選択され;
Xは、
Aは、
R3は、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され;
nは0、1、および2からなる群から選択され;
R4がH、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択され、ただしXが
- R2cが水素である、請求項3の化合物。
- R2bが水素である、請求項3の化合物。
- R1がHおよびFからなる群から選択され;
R2aがH、F、Cl、Br、およびシアノからなる群から選択され;
R2bがH、F、およびClからなる群から選択され;
R2cがHであり、ならびに
R4がH、F、Cl、およびシアノからなる群から選択される、
請求項6の化合物。 - R1が、FおよびClからなる群から選択される、請求項6の化合物。
- R2aが、F、Cl、Br、Me、OCH3、およびシアノからなる群から選択される、請求項6の化合物。
- R2bが、F、Cl、Br、Me、OCH3、およびシアノからなる群から選択される、請求項6の化合物。
- R2cが、F、Cl、Br、Me、およびOCH3からなる群から選択され、請求項6の化合物;
- R4が、F、Cl、Br、CH3、CF3、OCH3、シアノ、N(CH3)2、およびモルホリノからなる群から選択される、請求項6の化合物。
- AがCOOHである、請求項14の化合物。
- R2cがHである、請求項16の化合物。
- R2bがHである、請求項16の化合物。
- R1がHおよびFからなる群から選択され;
R2bがH、F、およびClからなる群から選択され;
R2cがHであり、ならびに
R4がH、F、Cl、およびシアノからなる群から選択される、
請求項16の化合物。 - AがCOOHである、請求項21の化合物。
- R2cがHである、請求項23の化合物。
- R2bがHである、請求項23の化合物。
- R2aがH、F、Cl、Br、およびシアノからなる群から選択され;
R2bがH、F、およびClからなる群から選択され;
R2cがHであり、ならびに
R4がH、F、Cl、およびシアノからなる群から選択される、
請求項23の化合物。 - 化合物が、
3−クロロ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
3−フルオロ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシナフタレン−2−イル)−3−メトキシ安息香酸;
3−(ジメチルアミノ)−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
3−シアノ−4−(6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシナフタレン−2−イル)−3−モルホリノ安息香酸;
4−(1−ブロモ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−1−メチルナフタレン−2−イル)安息香酸;
4−(1−シアノ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−3−メトキシナフタレン−2−イル)安息香酸;
4−(1−クロロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
6−(4−(1H−テトラゾール−5−イル)フェニル)ナフタレン−2−オール;
5−(6−ヒドロキシナフタレン−2−イル)ピコリン酸;
6−(6−ヒドロキシナフタレン−2−イル)ニコチン酸;
5−(6−ヒドロキシナフタレン−2−イル)ピラジン−2−カルボン酸;
2−(6−ヒドロキシナフタレン−2−イル)ピリミジン−5−カルボン酸;
6−(6−ヒドロキシナフタレン−2−イル)ピリダジン−3−カルボン酸;
5−(6−ヒドロキシナフタレン−2−イル)ピリミジン−2−カルボン酸;
6−(1H−ベンゾ[d][1,2,3]トリアゾール−6−イル)ナフタレン−2−オール;
4−(6−ヒドロキシナフタレン−2−イル)−3−(トリフルオロメチル)安息香酸;
3−クロロ−4−(3−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(3−クロロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(3−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−1−メトキシナフタレン−2−イル)安息香酸;
4−(1−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(6−ヒドロキシ−3−メチルナフタレン−2−イル)安息香酸;
4−(1−シアノ−5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(1−シアノ−6−ヒドロキシナフタレン−2−イル)−3−フルオロ安息香酸;
3−クロロ−4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸;
3−フルオロ−4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)安息香酸、ならびに
4−(5−フルオロ−6−ヒドロキシナフタレン−2−イル)−3−メチル安息香酸
からなる群から選択される、請求項1の化合物。 - 請求項1に定義される式1の化合物またはその医薬上許容される塩のGSNOR阻害薬としての使用。
- 請求項27の化合物またはその医薬上許容される塩のGSNOR阻害薬としての使用。
- 製薬的に許容される担体または賦形剤と共に請求項1による化合物の治療有効量を含む医薬組成物。
- 請求項1に定義される治療有効量の式1の化合物を必要とする患者にそれを投与することを含む、疾患または状態の治療法。
- 請求項1に定義される式1の化合物の作製法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US42379910P | 2010-12-16 | 2010-12-16 | |
US61/423,799 | 2010-12-16 | ||
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AU2011343518B2 (en) | 2010-12-16 | 2016-11-10 | Nivalis Therapeutics, Inc. | Novel substituted bicyclic aromatic compounds as S-nitrosoglutathione reductase inhibitors |
US20140094465A1 (en) * | 2011-06-10 | 2014-04-03 | N30 Pharmaceuticals, Inc. | Compounds as S-Nitrosoglutathione Reductase Inhibitors |
WO2016128905A1 (en) * | 2015-02-10 | 2016-08-18 | Glenmark Pharmaceuticals S.A. | Thienopyrrole compounds as s-nitrosoglutathione reductase inhibitors |
WO2017044766A1 (en) * | 2015-09-10 | 2017-03-16 | Nivalis Therapeutics, Inc. | Solid forms of an s-nitrosoglutathione reductase inhibitor |
WO2017151725A1 (en) * | 2016-03-03 | 2017-09-08 | Nivalis Therapeutics, Inc. | Formulations of an s-nitrosoglutathione reductase inhibitor |
EP3448842A1 (en) | 2016-04-26 | 2019-03-06 | AbbVie S.À.R.L. | Modulators of cystic fibrosis transmembrane conductance regulator protein |
CN109999029B (zh) * | 2019-03-07 | 2020-03-31 | 南京医科大学 | N6022在治疗糖尿病外周动脉疾病中的医药用途 |
US20230121865A1 (en) * | 2020-03-04 | 2023-04-20 | National University Corporation Tokai National Higher Education And Research System | Method for producing naphthylsilole, naphthylsilole containing heterocyclic group, and graphene nanoribbon containing heterocyclic group |
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US20140329821A1 (en) | 2014-11-06 |
US9012646B2 (en) | 2015-04-21 |
KR20130138292A (ko) | 2013-12-18 |
EP2651871A1 (en) | 2013-10-23 |
WO2012083171A1 (en) | 2012-06-21 |
AU2011343518B2 (en) | 2016-11-10 |
US8785643B2 (en) | 2014-07-22 |
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CN103328430A (zh) | 2013-09-25 |
US9249132B2 (en) | 2016-02-02 |
US20160108011A1 (en) | 2016-04-21 |
US20160279117A1 (en) | 2016-09-29 |
EP2651223A1 (en) | 2013-10-23 |
JP2013545821A (ja) | 2013-12-26 |
AU2011343518A1 (en) | 2013-07-04 |
EP2651223A4 (en) | 2015-07-22 |
RU2013127155A (ru) | 2015-01-27 |
US20130261123A1 (en) | 2013-10-03 |
EP2651871A4 (en) | 2015-07-22 |
JP5898230B2 (ja) | 2016-04-06 |
JP5990187B2 (ja) | 2016-09-07 |
US20150183774A1 (en) | 2015-07-02 |
US20130261122A1 (en) | 2013-10-03 |
US9364481B2 (en) | 2016-06-14 |
CA2821412A1 (en) | 2012-06-21 |
IL226834A (en) | 2016-09-29 |
WO2012083165A1 (en) | 2012-06-21 |
US9221810B2 (en) | 2015-12-29 |
BR112013014681A2 (pt) | 2016-10-04 |
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