JP2015521990A - インデン誘導体、その製造方法および医薬品としての使用 - Google Patents
インデン誘導体、その製造方法および医薬品としての使用 Download PDFInfo
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- JP2015521990A JP2015521990A JP2015519201A JP2015519201A JP2015521990A JP 2015521990 A JP2015521990 A JP 2015521990A JP 2015519201 A JP2015519201 A JP 2015519201A JP 2015519201 A JP2015519201 A JP 2015519201A JP 2015521990 A JP2015521990 A JP 2015521990A
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- inden
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- 0 CCC(C)N1CCN(*)CCC1 Chemical compound CCC(C)N1CCN(*)CCC1 0.000 description 10
- XLZMWNWNBXSZKF-UHFFFAOYSA-N CC(C)N1CCOCC1 Chemical compound CC(C)N1CCOCC1 XLZMWNWNBXSZKF-UHFFFAOYSA-N 0.000 description 1
- BAUXVVCVEDWRGY-UHFFFAOYSA-N CC(C)c1cncnc1 Chemical compound CC(C)c1cncnc1 BAUXVVCVEDWRGY-UHFFFAOYSA-N 0.000 description 1
- YSDBJKNOEWSFGA-UHFFFAOYSA-N CC(N1CCN(C)CC1)=O Chemical compound CC(N1CCN(C)CC1)=O YSDBJKNOEWSFGA-UHFFFAOYSA-N 0.000 description 1
- UVVYFYLSZIMKMC-UHFFFAOYSA-N O=C(CC1)c2c1c(Br)ccc2 Chemical compound O=C(CC1)c2c1c(Br)ccc2 UVVYFYLSZIMKMC-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
R1、R2、およびR3は、独立して、水素、または任意選択により少なくとも一置換されている分岐鎖状もしくは非分岐鎖状の飽和もしくは不飽和脂肪族基C1〜10から選択され、ただし、R1およびR2は常に同一であり;
R4およびR5は、架橋窒素と共に、(任意選択により環員として少なくとも1つの追加のヘテロ原子を含み、ならびに任意選択により分岐鎖状もしくは非分岐鎖状の飽和もしくは不飽和脂肪族基C1〜10によって置換されているか、または任意選択によりC1〜6アルキルまたはハロゲンで任意に一置換されているアリール基によって置換されている)C3〜9ヘテロシクロアルキルを形成し;
R6は、C1〜6アルキル基、直鎖状もしくは分岐鎖状のC1〜6アルコキシ基、任意選択により少なくとも一置換されているフェニル基、−F、−Cl、−I、−Br、−CF3、−CH2F、−CHF2、−CN、−OH、−SH、−NH2、オキソ、−(C=O)R’、−SR’、−SOR’、−SO2R’、−N(C=O)OR’、−NHR’、−NR’R”(この場合、各置換基のR’および任意選択によりR”は、独立して、直鎖状もしくは分岐鎖状のC1〜6−アルキル基を表す)から独立して選択される置換基によって、任意選択により一置換もしくは多置換されている5員環もしくは6員環のアリールもしくはヘテロアリール基である]の化合物、またはそれらの薬学的に許容可能な塩、異性体、プロドラッグ、もしくは溶媒和物に関する。
R1、R2、およびR3が、水素またはC1〜6アルキルから独立して選択され、
R4およびR5が、架橋窒素と共に、以下:
R6が、以下:
[1]4−(2−(7−フェニル−1H−インデン−3−イル)エチル)モルホリンマレエート、
[2]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)アゼパンヒドロクロリド、
[3]4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[4]1−(2−(7−(3−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[5]1−メチル−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[6]1−フェニル−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[7]1−(3−クロロフェニル)−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[8]1−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[9]1−(2−(7−フェニル−1H−インデン−3−イル)エチル)アゼパンマレエート、
[10]4−フェニル−1−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[11]4−(2−(2−メチル−7−フェニル−1H−インデン−3−イル)エチル)モルホリンマレエート、
[12]1−メチル−4−(2−(2−メチル−7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[13]4−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[14]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−フェニルピペラジンマレエート、
[15]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[16]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[17]1−(2−(7−(3−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[18]4−(2−(7−(3−フルオロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[19]4−(2−(7−(3,4−ジクロロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[20]1−(2−(7−(3,4−ジクロロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[21]4−(2−(7−(4−メトキシフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[22]1−(2−(7−(4−メトキシフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[23]1−(2−(7−(3,4−ジメトキシフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[24]4−(2−(7−(3,4−ジメトキシフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[25]4−(2−(7−(チオフェン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[26]1−メチル−4−(2−(7−(チオフェン−3−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[27]1−(2−(7−(1H−1,2,3−トリアゾール−1−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[28]3,5−ジメチル−4−(3−(2−(4−メチルピペラジン−1−イル)エチル)−1H−インデン−7−イル)イソオキサゾールマレエート、
[29]5−(3−(2−(4−メチルピペラジン−1−イル)エチル)−1H−インデン−7−イル)ピリミジンマレエート、
[30]1−メチル−4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[31]1−メチル−4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)−1,4−ジアゼパンマレエート、
[32]1−メチル−4−(2−(2−メチル−7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[33]1−(2−(7−(2−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[34]4−(2−(7−(ピリジン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[35]1−メチル−4−(2−(7−(ピリジン−3−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[36]1−(2−(7−(6−メトキシピリジン−3−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[37]1−(2−(7−(6−フルオロピリジン−3−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[38]1−メチル−4−(2−(7−(1−メチル−1H−ピラゾール−5−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[39]4−(2−(7−(6−メトキシピリジン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[40]1−メチル−4−(2−(6−ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[41]1−(2−(6−(2−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
またはこれらの薬学的に許容可能な塩、プロドラッグ、もしくは溶媒和物、
から選択される。
第一プロセスにおいて、一般式(I):
第二プロセスにおいて、下記の一般式(I):
本発明の別の態様は、少なくとも一般式(I)の化合物またはそれらの薬学的に許容可能な塩、プロドラッグ、異性体、もしくは溶媒和物と、少なくとも薬学的に許容可能な担体、添加剤、補助剤、もしくはビヒクルとを含む医薬組成物である。
1H-NMR (CDCl3, 400 MHz) d: 7.78 (dd, J= 7.6, 1.2 Hz, 1H), 7.6 (dd, J= 7.2, 1.2 Hz, 1H), 7.50-7.45 (m, 5H), 7.41 (m, 1H), 3.17 (t, J= 6 Hz, 2H), 2.70 (m, 2H) ppm.
EI-MS m/z: 208.1 (M).
1H-NMR (DMSO-d6, 300 MHz) d: 7.60 (dd, J=8.4, 1.5 Hz, 2H), 7.50-7.44 (m, 4H), 7.40 (m, 1H), 7.26 (dd, J=6.0, 2.4 Hz, 1H), 6.40 (s, 1H), 6.04 (s, 2H), 3.79 (m, 4H), 3.47 (s, 2H), 3.31 (m, 8H), 2.95 (m, 2H) ppm.
ESI(+)-HRMS: 306.1852 [M+H]+.
1H-NMR (CDCl3, 300 MHz) d: 3.52 (t, J= 5.7 Hz, 2H), 3.42 (t, J= 6 Hz, 2H), 2.09 (s, 3H), 1.71 (m, 4H), 1.57 (m, 4H) ppm.
1H-NMR (CDCl3, 400 MHz) d: 7.78 (dd, J= 7.6, 1.2 Hz, 1H), 7.56 (dd, J= 7.2, 1.2 Hz, 1H), 7.47 (d, J= 7.6 Hz, 1H), 7.42 (m, 3H), 7.17 (m, 2H), 3.14 (t, J= 5.8 Hz, 2H), 2.70 (m, 2H).
EI-MS m/z: 226.1 (M).
1H-NMR (DMSO-d6, 400 MHz) d: 9.90 (s, 1H), 7.64 (m, 2H), 7.51 (d, J= 6.4 Hz, 1H), 7.44 (t, J= 7.6 Hz, 1H), 7.31-7.25 (m, 2H), 6.45 (s, 1H), 3.48 (m, 2H), 3.41 (m, 2H), 3.31 (s, 4H), 3.20 (m, 2H), 3.01 (m, 2H), 1.84 (4H), 1.64 (m, 4H) ppm.
ESI(+)-HRMS: 336.2021 [M+H]+
a)4(−ピリジン−4−イル)−2,3−ジヒドロ−1H−インデン−1−オンの合成
1H-NMR (DMSO-d6, 400 MHz) d: 8.75 (m, 2H), 7.84 (d, J= 7.6 Hz, 1H), 7.63 (dd, J= 7.6, 0.8 Hz, 1H), 7.53 (d, J= 7.6 Hz, 1H), 7.42 (d, J= 5.2 Hz, 2H), 3.19 (t, J= 6 Hz, 2H), 2.73 (t, J= 5.8 Hz, 2H) ppm.
EI-MS m/z: 209.2 (M).
1H-NMR (DMSO-d6, 400 MHz) d: 8.65 (d, J= 5.2 Hz, 2H), 7.65 (d, J= 4.4 Hz, 2H), 7.56-7.48 (m, 2H), 7.37 (dd, J= 7.4, 1 Hz, 1H), 6.48 (s, 1H), 6.05 (s, 2H), 3.82 (m, 4H), 3.55 (s, 2H), 3.36 (m, 2H), 3.25 (m, 4H), 2.96 (m, 2H) ppm.
ESI(+)-HRMS: 307.1809 [M+H]+
a)1−(4−メチルピペラジン−1−イル)エタノンの合成
1H-NMR (CDCl3, 300 MHz) d: 3.65 (t, J= 6.8 Hz, 2H), 3.49 (t, J= 6.8 Hz, 2H), 2.46-2.39 (m, 4H), 2.32 (s, 3H), 2.10 (s, 3H) ppm.
1H-NMR (CDCl3, 300 MHz) d: 7.32 (m, 2H), 7.18 (t, J= 7.6 Hz, 1H), 6.30 (s, 1H), 3.31 (d, J= 1.8 Hz, 2H), 2.72 (m, 4H), 2.60 (m, 4H), 2.51 (m, 4H), 2.30 (s, 3H) ppm.
EI-MS m/z: 320.1 (M).
1H-NMR (DMSO-d6, 400 MHz) d: 8.32 (d, J= 5.2 Hz, 1H), 7.62 (dt, J= 5.2, 2 Hz, 1H), 7.53 (dd, J= 7.8, 1 Hz, 1H), 7.50-7.45 (m, 2H), 7.39 (d, J= 7.4 Hz, 1H), 6.43 (s, 1H), 6.12 (s, 2H), 3.54 (s, 2H), 3.29 (m, 8H), 2.85 (m, 2H), 2.79 (m, 2H), 2.70 (m, 3H) ppm.
ESI(+)-HRMS: 338.2025 [M+H]
薬理学的研究
脳膜標品およびσ1−レセプターに対する結合アッセイを、いくつかの変更を加えて、(DeHaven−Hudkins,D.L.,LC.Fleissner,and F.Y.Ford−Rice,1992,Characterization of the binding of [3H](+)pentazocine to σ recognition sites in guinea pig brain,Eur.J.Pharmacol.227,371−378)に記載されているように実施した。モルモット(Guinea pig)の脳を、Kinematica Polytron PT 3000を用いて15000 r.p.mで30秒間、50mMのTris−HClおよび0.32Mのショ糖(pH7.4)の10倍容量(w/v)においてホモジナイズした。当該ホモジネートを1000gにおいて4℃で10分間遠心分離し、上清を収集して、再び48000gにおいて4℃で15分間遠心分離した。当該ペレットを、10倍量のTris−HCl緩衝液(50mM、pH7.4)に再懸濁させ、37℃で30分間インキュベートし、48000gにおいて4℃で20分間遠心分離した。続いて、当該ペレットを新鮮なTris−HCl緩衝液(50mM、pH7.4)に再懸濁させ、使用するまで氷上で保存した。
Claims (15)
- 一般式(I):
R1、R2、およびR3は、独立して、水素または任意選択により少なくとも一置換されている分岐鎖状もしくは非分岐鎖状の飽和もしくは不飽和脂肪族基C1〜10から選択され、ただし、R1およびR2は常に同一であり;
R4およびR5は、架橋窒素と共に、C3〜9ヘテロシクロアルキルを形成し、前記C3〜9ヘテロシクロアルキルは、任意選択により環員として少なくとも1つの追加のヘテロ原子を含み、ならびに任意選択により分岐鎖状もしくは非分岐鎖状の飽和もしくは不飽和脂肪族基C1〜10によって置換されているか、または任意選択によりC1〜6アルキルまたはハロゲンで任意に一置換されるアリール基によって置換されており;
R6は、C1〜6アルキル基、直鎖状もしくは分岐鎖状のC1〜6アルコキシ基、任意選択により少なくとも一置換されているフェニル基、−F、−Cl、−I、−Br、−CF3、−CH2F、−CHF2、−CN、−OH、−SH、−NH2、オキソ、−(C=O)R’、−SR’、−SOR’、−SO2R’、−N(C=O)OR’、−NHR’、及び−NR’R”(この場合、各置換基のR’および任意選択によりR”は、独立して、直鎖状もしくは分岐鎖状のC1〜6アルキル基を表す)からなる群から独立して選択される置換基によって、任意選択により一置換もしくは多置換されている5員環もしくは6員環のアリールもしくはヘテロアリール基である]の化合物、またはそれらの薬学的に許容可能な塩、異性体、プロドラッグ、もしくは溶媒和物。 - R1、R2、およびR3が、水素またはC1〜6アルキル基から独立して選択される、請求項1に記載の化合物。
- 以下:
[1]4−(2−(7−フェニル−1H−インデン−3−イル)エチル)モルホリンマレエート、
[2]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)アゼパンヒドロクロリド、
[3]4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[4]1−(2−(7−(3−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[5]1−メチル−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[6]1−フェニル−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[7]1−(3−クロロフェニル)−4−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[8]1−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[9]1−(2−(7−フェニル−1H−インデン−3−イル)エチル)アゼパンマレエート、
[10]4−フェニル−1−(2−(7−フェニル−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[11]4−(2−(2−メチル−7−フェニル−1H−インデン−3−イル)エチル)モルホリンマレエート、
[12]1−メチル−4−(2−(2−メチル−7−フェニル−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[13]4−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[14]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−フェニルピペラジンマレエート、
[15]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)ピペリジンマレエート、
[16]1−(2−(7−(4−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[17]1−(2−(7−(3−フルオロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[18]4−(2−(7−(3−フルオロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[19]4−(2−(7−(3,4−ジクロロフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[20]1−(2−(7−(3,4−ジクロロフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[21]4−(2−(7−(4−メトキシフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[22]1−(2−(7−(4−メトキシフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[23]1−(2−(7−(3,4−ジメトキシフェニル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[24]4−(2−(7−(3,4−ジメトキシフェニル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[25]4−(2−(7−(チオフェン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[26]1−メチル−4−(2−(7−(チオフェン−3−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[27]1−(2−(7−(1H−1,2,3−トリアゾール−1−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[28]3,5−ジメチル−4−(3−(2−(4−メチルピペラジン−1−イル)エチル)−1H−インデン−7−イル)イソオキサゾールマレエート、
[29]5−(3−(2−(4−メチルピペラジン−1−イル)エチル)−1H−インデン−7−イル)ピリミジンマレエート、
[30]1−メチル−4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[31]1−メチル−4−(2−(7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)−1,4−ジアゼパンマレエート、
[32]1−メチル−4−(2−(2−メチル−7−(ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[33]1−(2−(7−(2−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[34]4−(2−(7−(ピリジン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[35]1−メチル−4−(2−(7−(ピリジン−3−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[36]1−(2−(7−(6−メトキシピリジン−3−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[37]1−(2−(7−(6−フルオロピリジン−3−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
[38]1−メチル−4−(2−(7−(1−メチル−1H−ピラゾール−5−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[39]4−(2−(7−(6−メトキシピリジン−3−イル)−1H−インデン−3−イル)エチル)モルホリンマレエート、
[40]1−メチル−4−(2−(6−ピリジン−4−イル)−1H−インデン−3−イル)エチル)ピペラジンマレエート、
[41]1−(2−(6−(2−フルオロピリジン−4−イル)−1H−インデン−3−イル)エチル)−4−メチルピペラジンマレエート、
またはこれらの薬学的に許容可能な塩、プロドラッグ、もしくは溶媒和物、
からなる群より選択される、請求項1〜5のいずれか一項に記載の化合物。 - 医薬品としての使用のための請求項1〜6のいずれか一項に記載の化合物。
- シグマレセプター媒介性疾患または症状の処置または予防における使用のための、請求項1〜6のいずれか一項に記載の化合物。
- 前記疾患または症状が、疼痛、とりわけ神経因性疼痛、炎症性疼痛、あるいは異痛および/または痛覚過敏を伴う他の疼痛の症状である、請求項8に記載の化合物。
- 前記異痛が、機械的異痛または熱的異痛である、請求項9に記載の化合物。
- 前記神経因性疼痛が痛覚過敏である、請求項9に記載の化合物。
- 前記疾患が、下痢、リポタンパク異常、高脂血症、高トリグリセリド血症、高コレステロール血症、肥満、偏頭痛、関節炎、高血圧症、不整脈、潰瘍、緑内障、学習障害、記憶障害、注意欠落、認知障害、神経変性疾患、脱髄性疾患、薬物中毒および化学物質中毒(コカイン、アンフェタミン、エタノール、およびニコチンなど)、遅発性ジスキネジア、てんかん、脳卒中、ストレス、癌、神経疾患(特に、鬱病、不安神経症、統合失調症);炎症または自己免疫疾患である、請求項8に記載の化合物。
- 請求項1〜6のいずれか一項に記載の一般式(I)の化合物またはそれらの薬学的に許容される塩、異性体、プロドラッグ、もしくは溶媒和物と、少なくとも薬学的に許容される担体、添加剤、助剤、またはビヒクルとを含む、医薬組成物。
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US (1) | US9493434B2 (ja) |
EP (2) | EP2682391A1 (ja) |
JP (1) | JP6243416B2 (ja) |
CN (1) | CN104520280B (ja) |
CA (1) | CA2878346A1 (ja) |
ES (1) | ES2608338T3 (ja) |
HK (1) | HK1211570A1 (ja) |
IN (1) | IN2015MN00064A (ja) |
MX (1) | MX358721B (ja) |
PT (1) | PT2870145T (ja) |
WO (1) | WO2014006071A1 (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2682391A1 (en) * | 2012-07-03 | 2014-01-08 | Laboratorios Del. Dr. Esteve, S.A. | Indene derivatives, their preparation and use as medicaments |
US11046670B2 (en) | 2015-10-19 | 2021-06-29 | Board Of Regents, The University Of Texas System | Piperazinyl norbenzomorphan compounds and methods for using the same |
WO2017190107A1 (en) * | 2016-04-29 | 2017-11-02 | Board Of Regents, The University Of Texas System | Sigma receptor binders |
AU2017257153A1 (en) | 2016-04-29 | 2018-11-22 | Board Of Regents, The University Of Texas System | Sigma receptor binders |
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US5292736A (en) * | 1993-02-26 | 1994-03-08 | Sterling Winthrop Inc. | Morpholinoalkylindenes as antiglaucoma agents |
WO2007098961A1 (en) * | 2006-03-02 | 2007-09-07 | Laboratorios Del Dr. Esteve, S.A. | 4, 5, 6,7-tetrahydrobenzo[b]thiophene derivatives and their use as sigma receptor ligands |
JP2008510768A (ja) * | 2004-08-27 | 2008-04-10 | ラボラトリオス デル ドクトール エステベ エセ.ア. | シグマ受容体阻害剤 |
JP2009514915A (ja) * | 2005-11-08 | 2009-04-09 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | インデン誘導体、それらの製造および薬剤としての使用 |
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US5092827A (en) | 1989-09-28 | 1992-03-03 | International Paper Box Machine Co., Inc. | Apparatus for folding paper boxes |
US5965619A (en) | 1996-06-13 | 1999-10-12 | Cell Pathways Inc. | Method for treating patients having precancerous lesions with substituted indene derivatives |
US6028116A (en) | 1998-04-03 | 2000-02-22 | Cell Pathways, Inc. | Substituted condensation products of 1H-indenyl-hydroxyalkanes with aldehydes for neoplasia |
US20010006965A1 (en) | 1998-04-17 | 2001-07-05 | Rifat Pamukcu | Method for treating patients with diabetic retinopathy by administering substituted sulfonyl indenyl acetic acids and alcohols |
US5958982A (en) | 1998-04-17 | 1999-09-28 | Cell Pathways, Inc. | Method for treating patients with sarcoidosis by administering substituted sulfonyl indenyl acetic acids, esters and alcohols |
US20010020020A1 (en) | 1998-04-17 | 2001-09-06 | Rifat Pamukcu | Method for treating patients with macular degeneration by administering substituted sulfonyl indenyl acetic acids and alcohols |
US6025394A (en) | 1999-01-29 | 2000-02-15 | Cell Pathways, Inc. | Method for treating patients with acne by administering substituted sulfonyl indenyl acetic acids, amides and alcohols |
EP1634873A1 (en) * | 2004-08-27 | 2006-03-15 | Laboratorios Del Dr. Esteve, S.A. | Sigma receptor inhibitors |
CN101356149A (zh) * | 2005-11-08 | 2009-01-28 | 戴尔·德·艾斯提夫实验室有限公司 | 茚衍生物,其制备方法和作为药物的用途 |
EP1847542A1 (en) | 2006-04-21 | 2007-10-24 | Laboratorios del Dr. Esteve S.A. | Spiro[benzopyran] or spiro[benzofuran] derivatives which inhibit the sigma receptor |
ES2358288T3 (es) * | 2007-08-01 | 2011-05-09 | Laboratorios Del Dr. Esteve S.A. | Combinación de al menos dos ligandos de 5ht6. |
EP2070933A1 (en) | 2007-12-07 | 2009-06-17 | Laboratorios del Dr. Esteve S.A. | Tricyclic triazolic compounds |
EP2682391A1 (en) * | 2012-07-03 | 2014-01-08 | Laboratorios Del. Dr. Esteve, S.A. | Indene derivatives, their preparation and use as medicaments |
-
2012
- 2012-07-03 EP EP12382268.6A patent/EP2682391A1/en not_active Withdrawn
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2013
- 2013-07-03 EP EP13734724.1A patent/EP2870145B1/en active Active
- 2013-07-03 PT PT137347241T patent/PT2870145T/pt unknown
- 2013-07-03 WO PCT/EP2013/063989 patent/WO2014006071A1/en active Application Filing
- 2013-07-03 CN CN201380041256.0A patent/CN104520280B/zh not_active Expired - Fee Related
- 2013-07-03 ES ES13734724.1T patent/ES2608338T3/es active Active
- 2013-07-03 CA CA2878346A patent/CA2878346A1/en not_active Abandoned
- 2013-07-03 US US14/412,021 patent/US9493434B2/en active Active
- 2013-07-03 JP JP2015519201A patent/JP6243416B2/ja not_active Expired - Fee Related
- 2013-07-03 IN IN64MUN2015 patent/IN2015MN00064A/en unknown
- 2013-07-03 MX MX2015000055A patent/MX358721B/es active IP Right Grant
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Patent Citations (4)
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US5292736A (en) * | 1993-02-26 | 1994-03-08 | Sterling Winthrop Inc. | Morpholinoalkylindenes as antiglaucoma agents |
JP2008510768A (ja) * | 2004-08-27 | 2008-04-10 | ラボラトリオス デル ドクトール エステベ エセ.ア. | シグマ受容体阻害剤 |
JP2009514915A (ja) * | 2005-11-08 | 2009-04-09 | ラボラトリオス・デル・ドクトル・エステベ・ソシエダッド・アノニマ | インデン誘導体、それらの製造および薬剤としての使用 |
WO2007098961A1 (en) * | 2006-03-02 | 2007-09-07 | Laboratorios Del Dr. Esteve, S.A. | 4, 5, 6,7-tetrahydrobenzo[b]thiophene derivatives and their use as sigma receptor ligands |
Also Published As
Publication number | Publication date |
---|---|
PT2870145T (pt) | 2016-12-23 |
HK1211570A1 (en) | 2016-05-27 |
WO2014006071A1 (en) | 2014-01-09 |
EP2682391A1 (en) | 2014-01-08 |
CN104520280A (zh) | 2015-04-15 |
CN104520280B (zh) | 2016-09-07 |
EP2870145B1 (en) | 2016-09-21 |
IN2015MN00064A (ja) | 2015-10-16 |
US20150158831A1 (en) | 2015-06-11 |
CA2878346A1 (en) | 2014-01-09 |
US9493434B2 (en) | 2016-11-15 |
EP2870145A1 (en) | 2015-05-13 |
ES2608338T3 (es) | 2017-04-07 |
MX2015000055A (es) | 2015-07-17 |
JP6243416B2 (ja) | 2017-12-06 |
MX358721B (es) | 2018-09-03 |
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