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Beta2-receptorexcitant and preparation method and application thereof

A solvate, C1-C4 technology, applied in the field of medicine

Active Publication Date: 2017-01-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned patent does not have the report of 2-(substituted aromatic heterocyclic group)-2-(substituted amino) ethanol and its salt, the present invention discloses 2-(substituted aromatic heterocyclic group)-2-(substituted Amino)ethanol and its salts have excitatory β 2 -Action of receptors, can be used in the treatment of heart failure, asthma and obstructive or inflammatory airway diseases

Method used

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  • Beta2-receptorexcitant and preparation method and application thereof
  • Beta2-receptorexcitant and preparation method and application thereof
  • Beta2-receptorexcitant and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Synthesis of 8-Hydroxy-5-(2-Hydroxy-1-isopropylaminoethyl)-(1H)-quinolin-2-one Hydrochloride

[0068] a. Synthesis of 8-benzyloxy-5-(1-bromo-2-hydroxyethyl)-(1H)-quinolin-2-one

[0069] 40g (0.108mol) 8-benzyloxy-5-bromoacetyl-(1H)-quinolin-2-one (according to WO2006023457A 1 The preparation) was dissolved in a mixed solution of 800mL methanol and 400mL dichloromethane, and 1.64g (0.0429mol) sodium borohydride was added in batches under an ice bath. After the reaction was completed, 2N hydrochloric acid was added to make the solution acidic, and the solvent was evaporated to dryness. Add water and stir thoroughly, and obtain 38.0 g of a yellow solid after suction filtration and drying, with a yield of 94.5%.

[0070] b. Synthesis of 8-benzyloxy-5-oxiranyl-(1H)-quinolin-2-one

[0071] Dissolve 38.0g (0.102mol) of 8-benzyloxy-5-(1-bromo-2-hydroxyethyl)-(1H)-quinolin-2-one in a mixed solution of 760mL methanol and 380mL dichloromethane , drop 5.71g (0.102mol) of potassi...

Embodiment 2

[0078] According to the method similar to Example 1, 8-hydroxyl-5-(2-hydroxyl-1-tert-butylamine was prepared from 8-benzyloxy-5-oxiranyl-(1H)-quinolin-2-one as raw material Ethyl)-(1H)-quinolin-2-one hydrochloride.

[0079] 1 H-NMR (300MHz, DMSO-d 6 ,ppm):1.23(9H,s),3.79-3.85(2H,m),4.87(1H,m),5.50(1H,s),6.58-6.61(1H,d,J=9.90Hz),7.03- 7.06 (1H, d, J = 8.28Hz), 7.43-7.46 (1H, d, J = 8.28Hz), 8.31-8.35 (1H, d, J = 9.99Hz), 8.54 (1H, s), 9.06 (1H ,s), 10.53(1H,s), 10.70(1H,s).

Embodiment 3

[0081] According to the method similar to Example 1, 8-hydroxyl-5-(2-hydroxyl-1-n- Propylaminoethyl)-(1H)-quinolin-2-one hydrochloride.

[0082] 1 H-NMR (300MHz, DMSO-d 6 ,ppm):0.79-0.84(3H,t),1.59-1.73(2H,m),2.67(1H,m),2.84(1H,m),3.75-3.90(2H,m),4.86(1H,m ),5.53(1H,s),6.57-6.60(1H,d,J=9.90Hz),7.05-7.08(1H,d,J=8.28Hz),7.38-7.40(1H,d,J=8.28Hz) , 8.18-8.22 (1H, d, J = 10.08Hz), 9.08 (1H, s), 9.36 (1H, s), 10.54 (1H, s), 10.74 (1H, s).

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PUM

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Abstract

The invention relates to a following formula I showed compound in a free form, a salt form or a solvated form and having a beta2-receptor exciting effect. II and III are contained in R1, Ar are following formula groups IV and V, definition of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R13, R14, R15, R16, m and o is shown in the description. The invention further relates to a preparation method of the compound and application of a compound serving as a drug, in particular to treatment of diseases such as a chronic obstructive pulmonary disease, asthma and heart failure the aspects of a respiratory and cardiovascular system and a cardiovascular system.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to 2 - A series of compounds with receptor stimulant effect, their preparation method and their preparation with beta 2 - Use in a drug for receptor agonism. Background technique [0002] Quinolone derivatives have useful pharmacological activity and stronger activity, U.S. Patent 4022776 / 1977 discloses 5-[1-hydroxyl-2-(substituted amino)] ethyl-8-hydroxyquinolone derivatives and salts thereof are beta 2 - Compounds with receptor stimulant effects. Chinese patent ZL011282347 / 2006 discloses that 2-(substituted phenyl)-2-(substituted amino)ethanol and its salts also have β 2 - Compounds with receptor stimulant effects. But above-mentioned patent does not have the report of 2-(substituted aromatic heterocyclic group)-2-(substituted amino) ethanol and its salt, the present invention discloses 2-(substituted aromatic heterocyclic group)-2-(substituted Amino)ethanol and its salts have...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/26C07D401/12C07D265/36C07D413/12A61K31/4704A61K31/4709A61K31/538A61P11/00A61P11/06A61P9/00A61P9/04
CPCY02P20/55C07D215/26C07D265/36C07D401/12C07D413/12
Inventor 潘莉程卯生胡耀豪肖瑞平葛新月李小强安会
Owner SHENYANG PHARMA UNIVERSITY
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