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Ciclesonide nitrate derivative

A technology of ciclesonide and nitrate, which is used in the treatment of allergic diseases or allergic diseases, and can solve the problems affecting the application of ciclesonide in the field of inflammatory diseases.

Active Publication Date: 2011-05-04
TIANJIN JINYAO GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since the esterase that can decompose CIC to des-CIC is only present in organs such as the lung, it affects the application of ciclesonide in the treatment of other inflammatory diseases

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] Example 1: Deisobutyryl ciclesonide 21-(3-nitrooxy)propionate

[0061]

[0062] Desisobutyryl ciclesonide 21-(3-chloro)propionate

[0063]

[0064] method 1:

[0065] 40ml of triethylamine, 0.1g of DMAP and 0.015mol of 3-chloropropionyl chloride were stirred in the reaction chamber and cooled to 0°C, slowly added 0.01mol of des-CIC and kept at a temperature of 0-5°C, the reaction was Thermal reaction, so the addition speed and temperature need to be carefully controlled. Keep the temperature of the above reaction solution below 10°C, and slowly rise to 10-15°C within 1 hour after the addition is completed. After keeping at this temperature for 15 hours, dilute to 50ml , the pH is 1-2, and the temperature is 0 degrees in water, slowly add hydrochloric acid to adjust the pH to 3-5, the liquid is extracted three times with 90ml of dichloromethane (30ml×3), and then washed three times with 90ml of water (30ml×3) The pH value of the methyl chloride layer was adjusted...

Embodiment 2

[0073] Example 2: Deisobutyryl ciclesonide 21-(5-nitrooxy)valerate

[0074]

[0075] With deisobutyryl ciclesonide as raw material, according to the method of Example 1 with 5-bromovaleryl chloride, AgNO 3 The reaction affords the title compound.

[0076] Elemental analysis measured value: C32H43NO10C, 63.91; H, 7.20; N, 2.32; O, 26.57 13 C-NMR:

[0077]

Embodiment 3

[0078] Example 3: Deisobutyryl ciclesonide-21-(4-nitrooxymethyl)benzoate

[0079]

[0080] With deisobutyryl ciclesonide as raw material, according to the method of embodiment 1 and (4-chloromethyl) benzoyl chloride, AgNO 3 The reaction affords the title compound.

[0081] Elemental analysis measured values: C36H43NO10C, 66.49; H, 6.68; N, 2.17; O, 24.66 13 C-NMR:

[0082]

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Abstract

The invention relates to a ciclesonide nitrate derivative (I) shown in the specification, wherein X is -CO(O)a(CR4R5)b' D(CR4R5)b''-, a is 0 or 1, b' and b'' can be same or different and are integers from 0 to 6, R4 and R5 are same or different and are selected from H and hydrocarbon compounds with 1-6 carbons, D can be nonexistent and also can be a hydrocarbon compound with 1-8 carbons containing 0-2 heteroatoms, the heteroatom is one or two of N, O and S, and X and 21 hydroxyl groups of des-ciclesonide (des-CIC) are connected through ester bonds.

Description

field of invention [0001] The present invention relates to nitrate steroids and their preparation. The invention also relates to pharmaceutical preparations containing this compound and to the therapeutic use of this compound, in particular for the treatment of inflammatory, allergic or allergic diseases. Background technique: [0002] Ciclesonide (CAS: 126544-47-6, 141845-82-1, referred to as: CIC) is a new type of corticosteroid used to treat airway inflammation such as asthma and rhinitis. Its anti-inflammatory effect is mainly through the active metabolite des-butyryl ciclesonide (des-CIC), which is metabolized by esterase in the lungs on the spot, and the anti-inflammatory effect of des-CIC is 100 times that of ciclesonide times, which is 12 times that of dexamethasone (Xin Zhou, Progress in Research on New Drugs for Asthma Treatment, Journal of Clinical Pulmonology, Volume 14, No. 6, June 2009, 711-712). However, since the esterase that can decompose CIC into des-CIC...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J71/00A61K31/58A61K9/14A61P29/00A61P37/08A61P17/00A61P11/00A61P27/02A61P1/04A61P19/02A61P9/00A61P9/10A61P35/00A61P11/06
Inventor 卢彦昌陈立营
Owner TIANJIN JINYAO GRP
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