JP2009525302A - 筋ジストロフィーの治療用薬剤のニトロオキシ誘導体の使用 - Google Patents
筋ジストロフィーの治療用薬剤のニトロオキシ誘導体の使用 Download PDFInfo
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- 0 CC(C(*)=O)c1ccc(C(C(C)=CC=CC=C)=O)[s]1 Chemical compound CC(C(*)=O)c1ccc(C(C(C)=CC=CC=C)=O)[s]1 0.000 description 6
- COTWZIQEUDZRBI-UHFFFAOYSA-N CC(C(C)=O)c(cc1)cc(C2)c1Sc1ccccc1C2=O Chemical compound CC(C(C)=O)c(cc1)cc(C2)c1Sc1ccccc1C2=O COTWZIQEUDZRBI-UHFFFAOYSA-N 0.000 description 1
- PJVBKPGGXKPZHF-UHFFFAOYSA-N CC(C(C)=O)c(cc1C(C2)=O)ccc1Oc1c2cc(C)cc1 Chemical compound CC(C(C)=O)c(cc1C(C2)=O)ccc1Oc1c2cc(C)cc1 PJVBKPGGXKPZHF-UHFFFAOYSA-N 0.000 description 1
- YUUJGKMRMPHITH-UHFFFAOYSA-N CCCSC(C(C)c1cccc(C(c2ccccc2)=O)c1)=O Chemical compound CCCSC(C(C)c1cccc(C(c2ccccc2)=O)c1)=O YUUJGKMRMPHITH-UHFFFAOYSA-N 0.000 description 1
- VYYQCVXROGXRGU-UHFFFAOYSA-N CCCSC(C(C)c1cccc(Oc2ccccc2)c1)=O Chemical compound CCCSC(C(C)c1cccc(Oc2ccccc2)c1)=O VYYQCVXROGXRGU-UHFFFAOYSA-N 0.000 description 1
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Abstract
【選択図】なし
Description
M-X-Y-ONO2 (Ia)
[一般式(Ia)中、M、XおよびYは次の意味を有する:
Mは、
Xは、-O-、-S-または-NR1-(ここで、R1はHまたは直鎖状もしくは分枝鎖状のC1-C6アルキルである)であり、
a)
−ハロゲン原子、ヒドロキシ、-ONO2またはT(ここで、Tは-OC(O)(C1-C10アルキル)-ONO2または-O(C1-C10アルキル)-ONO2である)からなる群から選択される1以上の置換基で任意に置換されていてもよい、直鎖状または分枝鎖状のC1-C20アルキレン、好ましくはC1-C10アルキレン;
より好ましくはYはC1-C10アルキレンである;
−直鎖状または分枝鎖状のC1-C10アルキル基、好ましくはCH3で任意に置換されていてもよいC5-C7シクロアルキレン基;
n1は1〜20の整数であり、好ましくはn1は1〜5の整数であり、より好ましくはn1は1である);
但し、Yがb)およびc)で挙げられた2価の基から選択されるとき、式(I)の-ONO2基は-(CH2)n 1-に結合している;
但し、Yがd)〜f)で挙げられた2価の基から選択されるとき、式(I)の-ONO2基は-(CH2)naに結合しており;
Xが-NR1-(ここで、R1は上記で定義されたとおりである)であるとき、Yはf)でない;
を有する2価の基である]
の一酸化窒素放出性薬物、またはそのエナンチオマーもしくはジアステレオマーの使用である。
[1S-[1α(βS*,δS*),2α,6α,8β-(R*),8aα]]-1,2,6,7,8,8a-ヘキサヒドロ-β,δ,6-トリヒドロキシ-2-メチル-8-(2-メチル-1-オキソブトキシ)-1-ナフタレンヘプタン酸 4-(ニトロオキシ)ブチルエステルまたはプラバスタチン4-(ニトロオキシ)ブチルエステルとして知られている:
本発明の化合物は、例えば経口投与用の固体組成物、液体組成物またはその他の組成物、非経口投与用の注射剤、塗布剤または坐剤の形態で投与され得る。
式(Ib)の2-(アセチルオキシ)安息香酸 3-(ニトロオキシメチル)フェニルエステルの合成方法は、EP 1 194 397に記載されている。
筋ジストロフィーモデル(α-サルコグリカン-欠乏マウス)。
動物モデルの参考:Duclos F. et al. J Cell Biol. 1998 Sep 21; 142(6):1461-71。
試験化合物は:
− 式(Ib)の2-アセチルオキシ安息香酸 3-(ニトロオキシメチル)ベンゾエート;
− 式(XXXVb)のプラバスタチン4-(ニトロオキシ)ブチルエステル;
− 式(IIIb)の2-フルオロ-α-メチル-4[1,1'-ビフェニル]4-酢酸の4-ニトロオキシブチルエステル;
− 参考のコルチコステロイド薬物としてプレドニゾロン
である。
自発的ホイールランニングが、強制トレッドミル(treadmill)ランニングのストレスにより起こり得るあらゆる生理学的変化を避けるために、運動の実例として用いられた。マウスは、速度計に送られるその出力が1日当りの回転数の定量化を可能にする、磁気カウンターを備えたポリカーボネートランニングホイール中、24時間、単独で収容された。そのデータを表2に報告する。
コントロールおよび薬物処処理動物の血清中のクレアチンキナーゼ活性の定量的および動的な測定が、クレアチンキナーゼ試薬(Sigma)を用いて、製造業者の指示に従って行なわれた。血液は、2〜7ヶ月齢マウスの尾から採取され、13.000 rmp、10分間の遠心分離後に得られた血清が、測定前に-80℃で保存された。そのデータを表1に報告する。
無処処理および薬物処理マウスの横隔膜および前脛骨筋が分離され、Killik凍結切片媒体中に入れられ、直ぐに凍結され、低温保持装置を用いて、横の方向に筋肉線維を有する8-μmの厚さの断面に切断された。断面は、炎症性浸潤物および壊死線維(組織に対して18〜10断面)の数を評価するために、Hematoxylin & Eosinまたはアザン‐マロリーのどちらかで染色された。そのデータを表1に報告する。
全体で、本データは、本発明の化合物が、この病理の選択薬であるプレドニゾロンと比較してより改善されたプロファイルを有することを示している。
Claims (5)
- 筋ジストロフィーの治療用医薬を製造するための、式(Ia):
M-X-Y-ONO2 (Ia)
[一般式(Ia)中、M、XおよびYは次の意味を有する:
Mは、
Xは、-O-、-S-または-NR1-(ここで、R1はHまたは直鎖状もしくは分枝鎖状のC1-C6アルキルである)であり、
Yは次の意味:
a)
−ハロゲン原子、ヒドロキシ、-ONO2またはT(ここで、Tは-OC(O)(C1-C10アルキル)-ONO2または-O(C1-C10アルキル)-ONO2である)からなる群から選択される1以上の置換基で任意に置換されていてもよい、直鎖状または分枝鎖状のC1-C20アルキレン、好ましくはC1-C10アルキレン;
より好ましくはYはC1-C10アルキレンである;
−直鎖状または分枝鎖状のC1-C10アルキル基、好ましくはCH3で任意に置換されていてもよいC5-C7シクロアルキレン基;
n1は1〜20の整数であり、好ましくはn1は1〜5の整数であり、より好ましくはn1は1である);
但し、Yがb)およびc)で挙げられた2価の基から選択されるとき、式(I)の-ONO2基は-(CH2)n 1-に結合している;
d)
naは1〜20の整数であり;好ましくはnは1〜5の整数であり;
n2は0〜2の整数である);
e)
X1、na、n2およびR2は上記で定義されたとおりである);
f)
但し、Yがd)〜f)で挙げられた2価の基から選択されるとき、式(I)の-ONO2基は-(CH2)naに結合しており;
Xが-NR1-(ここで、R1は上記で定義されたとおりである)であるとき、Yはf)でない;
g)
を有する2価の基である]
の一酸化窒素放出性化合物、またはそのエナンチオマーもしくはジアステレオマーの使用。
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US76475506P | 2006-02-03 | 2006-02-03 | |
US60/764,755 | 2006-02-03 | ||
PCT/EP2007/050630 WO2007088123A2 (en) | 2006-02-03 | 2007-01-23 | Use of nitrooxyderivative of drug for the treatment of muscular dystrophies |
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JP2009525302A true JP2009525302A (ja) | 2009-07-09 |
JP2009525302A5 JP2009525302A5 (ja) | 2010-03-11 |
JP5745210B2 JP5745210B2 (ja) | 2015-07-08 |
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US (1) | US8575222B2 (ja) |
EP (2) | EP1978947B1 (ja) |
JP (1) | JP5745210B2 (ja) |
KR (1) | KR20080097989A (ja) |
CN (1) | CN101378739B (ja) |
AU (1) | AU2007211508B2 (ja) |
CA (1) | CA2641816C (ja) |
DK (1) | DK1978947T3 (ja) |
ES (1) | ES2520893T3 (ja) |
HK (1) | HK1129592A1 (ja) |
IL (1) | IL192299A0 (ja) |
NZ (1) | NZ569396A (ja) |
PL (1) | PL1978947T3 (ja) |
PT (1) | PT1978947E (ja) |
RU (2) | RU2429828C2 (ja) |
SI (1) | SI1978947T1 (ja) |
WO (1) | WO2007088123A2 (ja) |
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Cited By (1)
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MX2018014032A (es) | 2017-03-20 | 2019-08-21 | Forma Therapeutics Inc | Composiciones de pirrolopirrol como activadores de piruvato cinasa (pkr). |
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CN113226356A (zh) | 2018-09-19 | 2021-08-06 | 福马治疗股份有限公司 | 活化丙酮酸激酶r |
KR102329853B1 (ko) | 2021-03-25 | 2021-11-23 | 주식회사 엔테로바이옴 | 아커만시아 뮤시니필라 균주를 포함하는 근위축증 예방 또는 치료용 약학적 조성물 |
KR102272616B1 (ko) | 2021-03-25 | 2021-07-05 | 주식회사 엔테로바이옴 | 피컬리박테리움 프로스니치 균주를 포함하는 근위축증 예방 또는 치료용 약학적 조성물 |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8852568B2 (en) | 2007-12-17 | 2014-10-07 | The Regents Of The University Of Michigan | Compositions and methods for treating and preventing skeletal muscle deficiencies |
US9107940B2 (en) | 2007-12-17 | 2015-08-18 | The Regents Of The University Of Michigan | Compositions and methods for treating and preventing skeletal muscle deficiencies |
Also Published As
Publication number | Publication date |
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CA2641816C (en) | 2016-01-05 |
KR20080097989A (ko) | 2008-11-06 |
RU2008135153A (ru) | 2010-03-10 |
CN101378739A (zh) | 2009-03-04 |
WO2007088123A3 (en) | 2007-09-20 |
EP2786749A1 (en) | 2014-10-08 |
ZA200805716B (en) | 2009-11-25 |
WO2007088123A2 (en) | 2007-08-09 |
IL192299A0 (en) | 2009-08-03 |
CA2641816A1 (en) | 2007-08-09 |
RU2011118522A (ru) | 2012-11-20 |
US8575222B2 (en) | 2013-11-05 |
RU2560144C2 (ru) | 2015-08-20 |
ES2520893T3 (es) | 2014-11-12 |
US20090093510A1 (en) | 2009-04-09 |
EP1978947B1 (en) | 2014-08-13 |
AU2007211508B2 (en) | 2012-08-23 |
SI1978947T1 (sl) | 2014-12-31 |
DK1978947T3 (da) | 2014-11-03 |
AU2007211508A1 (en) | 2007-08-09 |
RU2429828C2 (ru) | 2011-09-27 |
HK1129592A1 (en) | 2009-12-04 |
CN101378739B (zh) | 2014-06-04 |
EP1978947A2 (en) | 2008-10-15 |
JP5745210B2 (ja) | 2015-07-08 |
PT1978947E (pt) | 2014-11-03 |
PL1978947T3 (pl) | 2015-03-31 |
NZ569396A (en) | 2011-06-30 |
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