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Amide derivatives of 1-oxa-4,9-diazaspiro undecane compounds having multimodal activity against pain

A compound, alkyl technology, applied in the field of pain treatment, diazaspiroundecane derivatives

Inactive Publication Date: 2017-02-22
ESTEVE PHARMA SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In the present invention, a family of structurally unique diazaspiroundecane derivatives with dual pharmacological activity against sigma (σ) receptors and mu-opioid receptors is identified, thereby providing such Dual Compounds Address the Above Problems of Identifying Alternative or Modified Pain Therapies

Method used

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  • Amide derivatives of 1-oxa-4,9-diazaspiro undecane compounds having multimodal activity against pain
  • Amide derivatives of 1-oxa-4,9-diazaspiro undecane compounds having multimodal activity against pain
  • Amide derivatives of 1-oxa-4,9-diazaspiro undecane compounds having multimodal activity against pain

Examples

Experimental program
Comparison scheme
Effect test

Embodiment D

[0162] In Example DA, the following conditions apply:

[0163] when Y is where R 3 and R 3' for hydrogen, R 1 for C(O)R 5 and X is not -C(R 4 R 4' )-, then n will be 2.

[0164] In Example DA, the following compounds are preferably excluded:

[0165] and / or

[0166] and / or

[0167] and / or

[0168]

[0169] In one embodiment (Example DB), the compound is a compound of general formula (I),

[0170]

[0171] in

[0172] Y is

[0173] n is 1 or 2;

[0174] q is 1, 2, 3, 4, 5 or 6;

[0175] X is a bond, -C(O)O-, -C(O)NR 8 -, -C(O)- or -O-;

[0176] R 1 for C(O)R 5 or S(O) 2 R 5 ;

[0177] R 2 is substituted or unsubstituted C 1-6 Alkyl, substituted or unsubstituted C 2-6 Alkenyl, substituted or unsubstituted C 2-6 Alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; wherein cycloalkyl, aryl or heterocyclyl (if substituted ) is substituted with a substituent se...

Embodiment DB

[0188] In the example DB, the following conditions apply:

[0189] where Y is and

[0190] -(CH 2 ) n -X-R 2 is an alkyl group, the alkyl group contains 6 or less C atoms.

[0191] In the example DB, the following conditions apply:

[0192] when Y is where R 3 and R 3' is hydrogen, and R 1 for C(O)R 5 , then n will be 2.

[0193] In Example DB, the following compounds are preferably excluded:

[0194]

[0195] In one embodiment (Example DC), the compound is a compound of general formula (I),

[0196]

[0197] in

[0198] Y is

[0199] n is 1 or 2;

[0200] q is 1, 2, 3, 4, 5 or 6;

[0201] X is a bond, -C(O)O-, -C(O)NR 8 -, -C(O)- or -O-;

[0202] R 1 for C(O)R 5 or S(O) 2 R 5 ;

[0203] R 2 is substituted or unsubstituted C 1-4 Alkyl, substituted or unsubstituted C 2-4 Alkenyl, substituted or unsubstituted C 2-4 Alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl;...

example

[0836] General experimental part (methods and equipment for synthesis and analysis)

[0837] Process 1

[0838] A 2-step process for the preparation of compounds of general formula (I) starting from compounds of formula II is described, as shown in the following scheme:

[0839]

[0840] Process 1

[0841] where R 1 , R 2 , R 10 , R 10' , n, Y and X have the meanings defined above for the compound of formula (I), p represents 0, 1 or 2, LG represents a leaving group such as halogen, mesylate, tosylate or Triflate, p represents a suitable protecting group (preferably Boc), and P' represents another suitable protecting group (preferably 4-methoxybenzyl or benzyl) and Z represents COOH, COW or SO 2 W, wherein W represents a halogen.

[0842] The 2-step method was performed as follows:

[0843] Step 1: The reduction reaction of the compound of formula II to produce the compound of formula III can use a suitable reducing agent such as lithium aluminum hydride, borane-...

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PUM

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Abstract

The present invention relates to compounds having dual pharmacological activity towards both the sigma receptor, and the mu-opioid receptor and more particularly to diazaspiro undecane compounds having this pharmacological activity, to processes of preparation of such compounds, to pharmaceutical compositions comprising them, and to their use in therapy, in particular for the treatment of pain. (formula 1) wherein Y is (formula 2) or (formula 3)n is 1 or 2; .q is 1, 2, 3, 4, 5 or 6; .X is a bond, -C(O)O-, -C(0)NR 8-, -C(O)-, -0- or -C(R 4R 4.)-; .R1is C(0)R 5or S(O) 2R 5.

Description

technical field [0001] The present invention relates to compounds having dual pharmacological activity against sigma (σ) receptors and μ-opiod receptors (μ-opiod receptor, MOR or μ-opioids), and more particularly, to compounds having such pharmacological activity. Pharmaceutically active diazaspiroundecane derivatives; processes for the preparation of such compounds; pharmaceutical compositions comprising them; and their use in therapy, in particular, in the treatment of pain. Background technique [0002] Adequate management of pain presents an important challenge as currently available treatments provide only modest improvement in many cases, leaving many patients without relief [Turk DC, Wilson HD, Cahana A. Treatment of chronic non-cancer pain. Lancet 377 , 2226-2235 (2011)]. Pain affects a large portion of the population, with an estimated prevalence of about 20% and its incidence, especially in the case of chronic pain, increases as the population ages. Furthermore, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/10A61K31/537A61K31/5386A61P25/04A61P23/00
CPCC07D498/10A61P23/00A61P25/04A61P25/06A61P29/00
Inventor 玛丽娜·维吉尔利-贝尔纳多莫妮卡·阿隆索-哈尔马卡洛斯·阿莱格雷特-莫利纳卡门·阿尔曼萨-罗萨莱斯拉蒙·梅尔塞-维达尔
Owner ESTEVE PHARMA SA
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