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CN1276911C - 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 - Google Patents

具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 Download PDF

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CN1276911C
CN1276911C CNB011282347A CN01128234A CN1276911C CN 1276911 C CN1276911 C CN 1276911C CN B011282347 A CNB011282347 A CN B011282347A CN 01128234 A CN01128234 A CN 01128234A CN 1276911 C CN1276911 C CN 1276911C
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amino
ethyl amine
amine compounds
phenyl ethyl
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CN1408703A (zh
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程卯生
潘莉
冀蕾
张莉
沈建民
宋桂兰
李志清
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Jiutai Pharmaceutical Co Ltd Jinzhou City
Shenyang Pharmaceutical University
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Jiutai Pharmaceutical Co Ltd Jinzhou City
Shenyang Pharmaceutical University
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Priority to AU2002338124A priority patent/AU2002338124A1/en
Priority to DK02771983T priority patent/DK1439164T3/da
Priority to PCT/CN2002/000676 priority patent/WO2003093219A1/zh
Priority to RU2004112212/04A priority patent/RU2264382C1/ru
Priority to DE60219500T priority patent/DE60219500T2/de
Priority to AT02771983T priority patent/ATE359261T1/de
Priority to EP02771983A priority patent/EP1439164B1/en
Priority to ES02771983T priority patent/ES2284926T3/es
Priority to US10/491,028 priority patent/US7098364B2/en
Priority to JP2004501359A priority patent/JP3990399B2/ja
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/68Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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    • C07C255/58Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C07C255/59Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract

本发明是一种具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法,它可以有效的治疗哮喘及支气管炎。所说的化合物结构式如下:它可以采用两种化合物合成反应的方法实现,反应在无水条件下进行,反应溶剂为醇类或芳香烃类,反应温度为回流温度,反应时间为10~15小时。本发明合成了一种具有β2-受体兴奋作用的新化合物,为治疗哮喘及支气管炎提供新的途径。

Description

具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法
技术领域
本发明涉及医药工业技术领域,确切地说它是一种用于治疗哮喘和支气管炎的具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法。
背景技术
哮喘和支气管炎是一种常见的疾病,目前的治疗方法大多采用抗菌素治疗,疗效并不好,并且长期使用还有一定的副作用。而一些用于治疗哮喘的β2-受体激动剂已被公知,这些已知化合物在药效和理化性质等方面都存在着不足。
发明内容
本发明是提供一系列具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法,我们进行了结构改造,合成出了一系列未见报道的具有β2-受体兴奋作用的新化合物。
本发明提供了具有β2-受体兴奋作用的新型苯乙醇胺类化合物,所说的新化合物的结构式为:
Figure C0112823400031
其中,R1为H、Cl或Br;R2为CN或CF3;R3为C1-6直链烷烃及其异构体、C1-6脂肪醇或C3-6环烷烃;X为Cl或Br;n为0-2。
本发明还提供了一种具有β2-受体兴奋作用的新型苯乙醇胺类式(I)化合物的制备方法,其特征在于:它包括
将式(III)化合物
其中R1为H、Cl或Br,R2为CN或CF3
与式(IV)化合物反应
                 H2N-R3(IV)
其中R3为C1-6直链烷烃及其异构体、C1-6脂肪醇或C3-6环烷烃。
在按照本发明的式(I)化合物的制备方法中,化合物(III)和化合物(IV)的反应在无水条件下进行,反应溶剂为醇类或芳香烃类,反应温度为回流温度,反应时间为10-15小时。
具体地,此反应在无水条件下进行,反应溶剂为醇类(例如无水乙醇等)或芳香烃类(例如甲苯等),反应温度为回流温度,反应时间为13小时,产品收率一般为20%-30%。
原料(II)游离碱或其盐,可采用市售的对-氨基苯乙酮。
原料(III)的制备方法如下:
原料(V)的合成见相关文献
原料(V)与硼氢化钾反应,生成化合物(III)。使用溶剂甲醇水溶液,反应温度为室温,反应时间为5小时。
原料(4-氨基-3-氯-5-三氟甲基苯基)环氧乙烷的制备:
将5.6g(0.01769moL)4-氨基-3-氯-5-三氟甲基-α-溴代苯乙酮溶于56mL甲醇中,加水4.9mL,分批加入0.96g(0.1769moL)硼氢化钾,室温反应5小时,冰水冷却下用2N盐酸调至PH=2,减压蒸净溶剂,加水11.2mL,用3×10mL氯仿提取,有机层水洗至中性,无水硫酸镁干燥,蒸净溶剂得油状产品,收率85%~95%,NMR(d6-DMSO)δ:2.88(2H,d),3.89(1H,t),7.08(1H,s),7.24(1H,s)。
在以下实例中,将详细说明化合物(I)的制备。
具体实施方式:
实施例1:
2-(4-氨基-3-氯-5-三氟甲基苯基)-2-叔丁氨基乙醇盐酸盐
第一步:
将5.2g(0.0163moL)(4-氨基-3-氯-5-三氟甲基苯基)环氧乙烷溶于26mL无水乙醇中,加入5.1mL(0.049moL)叔丁胺,加热回流13小时,蒸净溶剂,用2N盐酸提取数次,合并水层,用甲苯提取,活性炭脱色,冷却下用20%氢氧化钠调至PH=10,固化,抽滤得产品2-(4-氨基-3-氯-5-三氟甲基苯基)-2-叔丁氨基乙醇,收率20%~30%,m.p85~90℃。
第二步:
将1.00g2-(4-氨基-3-氯-5-三氟甲基苯基)-2-叔丁氨基乙醇溶于20mL无水乙醚中,滤掉不溶物,搅拌下滴加饱和的氯化氢异丙醇液至PH=2,冷却,抽滤,用少量无水乙醚洗涤,烘干,得粗品2-(4-氨基-3-氯-5-三氟甲基苯基)-2-叔丁氨基乙醇盐酸盐。将粗品溶于无水乙醇中(比例1g:5Ml),滤除不溶物,滴加无水乙醚到有少量晶体析出,冷冻,抽滤,得精品2-(4-氨基-3-氯-5-三氟甲基苯基)-2-叔丁氨基乙醇盐酸盐,收率80%~90%,mp205℃~207℃(dec)。NMR(d6-DMSO)δ:1.24(9H,s),3.77(2H,d),4.43(1H,m),7.72(1H,s),7.87(1H,s)。
实施例2:
2-(4-氨基-3-氯-5-三氟甲基苯基)-2-异丙氨基乙醇
NMR(d6-DMSO)δ:1.08(6H,d),2.85(1H,m),3.80(2H,d),4.38(1H,m),7.70(1H,s),7.80(1H,s)。
实施例3:
2-(4-氨基-3-氯-5-三氟甲基苯基)-2-环戊氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.62(4H,m),1.68(4H,m),2.66(1H,m),3.79(2H,d),4.45(1H,m),7.62(1H,s),7.77(1H,s)。
实施例4:
2-(4-氨基-3-氯-5-三氟甲基苯基)-2-环己氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.30(6H,m),1.42(4H,m),2.80(1H,m),3.74(2H,d),4.40(1H,m),7.62(1H,s),7.89(1H,s)。
实施例5:
2-(4-氨基-3-溴-5-三氟甲基苯基)-2-叔丁氨基乙醇
NMR(d6-DMSO)δ:1.25(9H,m),3.76(2H,d),4.41(1H,m),7.62(1H,s),7.78(1H,s)。
实施例6:
2-(4-氨基-3-溴-5-三氟甲基苯基)-2-异丙氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.08(6H,d),2.85(2H,d),4.33(1H,m),7.76(1H,s),7.90(1H,s)。
实施例7:
2-(4-氨基-3-溴-5-三氟甲基苯基)-2-环丙氨基乙醇
NMR(d6-DMSO)δ:0.82(4H,m),1.62(1H,m),3.82(2H,d),4.41(1H,m),7.79(1H,s),7.88(1H,s)。
实施例8:
2-(4-氨基-3-溴-5-三氟甲基苯基)-2-环丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:2.02(2H,m),2.14(4H,m),3.15(1H,m),3.79(2H,d),4.41(1H,m),7.68(1H,s),7.78(1H,s)。
实施例9:
2-(4-氨基-3-氯-5-氰基苯基)-2-叔丁氨基乙醇
NMR(d6-DMSO)δ:1.26(9H,s),3.75(2H,d),4.41(1H,m),7.79(1H,s),7.92(1H,s)。
实施例10:
2-(4-氨基-3-氯-5-氰基苯基)-2-异丙氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.08(6H,d),2.85(1H,m),3.78(2H,d),4.39(1H,m),7.75(1H,s),7.89(1H,s)。
实施例11:
2-(4-氨基-3-氯-5-氰基苯基)-2-环丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:2.08(2H,m),2.12(4H,m),3.13(1H,m),3.77(2H,d),4.43(1H,m),7.78(1H,s),7.88(1H,s)。
实施例12:
2-(4-氨基-3-氯-5-氰基苯基)-2-环戊氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.62(4H,m),1.69(4H,m),2.56(1H,m),3.75(2H,d),4.45(1H,m),7.72(1H,s),7.97(1H,s)。
实施例13:
2-(4-氨基-3-溴-5-氰基苯基)-2-叔丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.24(9H,s),3.72(2H,d),4.38(1H,m),7.75(1H,s),7.92(1H,s)。
实施例14:
2-(4-氨基-3-溴-5-氰基苯基)-2-异丙氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.06(6H,d),2.87(1H,m),3.75(2H,d),4.42(1H,m),7.79(1H,s),7.89(1H,s)。
实施例15:
2-(4-氨基-3-溴-5-氰基苯基)-2-环丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:2.11(2H,m),2.16(4H,m),3.15(1H,m),3.76(2H,d),4.41(1H,m),7.78(1H,s),7.92(1H,s)。
实施例16:
2-(4-氨基-3-溴-5-氰基苯基)-2-环戊氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.60(4H,m),1.66(4H,m),2.52(1H,m),3.73(2H,d),4.43(1H,m),7.78(1H,s),7.87(1H,s)。
实施例17:
2-(4-氨基-3-溴-5-氰基苯基)-2-环己氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.30(6H,m),1.42(4H,m),2.82(1H,m),3.76(2H,d),4.39(1H,m),7.76(1H,s),7.89(1H,s)。
实施例18:
2-(4-氨基-3-氰基苯基)-2-叔丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.25(9H,s),3.72(2H,d),4.41(1H,m),7.62(1H,d),7.70(1H,s),7.85(1H,d)。
实施例19:
2-(4-氨基-3-氰基苯基)-2-异丙氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.08(6H,d),2.77(1H,m),3.79(2H,d),4.40(1H,m),7.69(1H,d),7.72(1H,s),7.80(1H,d)。
实施例20:
2-(4-氨基-3-氰基苯基)-2-环丁氨基乙醇盐酸盐
NMR(d6-DMSO)δ:2.09(2H,m),2.13(4H,m),3.18(1H,m),3.75(2H,d),4.38(1H,m),7.68(1H,d),7.75(1H,s),7.92(1H,d)。
实施例21:
2-(4-氨基-3-氰基苯基)-2-环戊氨基乙醇盐酸盐
NMR(d6-DMSO)δ:1.62(4H,m),1.64(4H,m),2.53(1H,m),3.70(2H,d),4.48(1H,m),7.68(1H,d),7.73(1H,s),7.87(1H,d)。
实施例22:
2-(4-氨基-3-氰基苯基)-2-环丙氨基乙醇盐酸盐
NMR(d6-DMSO)δ:0.89(4H,m),1.23(1H,m),3.75(2H,d),4.38(1H,m),7.69(1H,d),7.76(1H,s),7.80(1H,d)。

Claims (3)

1、具有β2-受体兴奋作用的新型苯乙醇胺类化合物,其特征在于:所说的新化合物的结构式为:
其中,R1为H、Cl或Br;R2为CN或CF3;R3为C1-6直链烷烃及其异构体、C1-6脂肪醇或C3-6环烷烃;X为Cl或Br;n为0-2。
2、一种如权利要求1所述的具有β2-受体兴奋作用的新型苯乙醇胺类化合物的制备方法,其特征在于:它包括
将式(III)化合物
其中R1、R2如权利要求1所定义,
与式(IV)化合物反应
                    H2N-R3(IV)
其中R3如权利要求1所定义。
3、根据权利要求2所述的具有β2-受体兴奋作用的新型苯乙醇胺类化合物的制备方法,其特征在于:化合物(III)和化合物(IV)的反应在无水条件下进行,反应溶剂为醇类或芳香烃类,反应温度为回流温度,反应时间为10-15小时。
CNB011282347A 2001-09-30 2001-09-30 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法 Expired - Fee Related CN1276911C (zh)

Priority Applications (12)

Application Number Priority Date Filing Date Title
CNB011282347A CN1276911C (zh) 2001-09-30 2001-09-30 具有β2-受体兴奋作用的新型苯乙醇胺类化合物及其制法
ES02771983T ES2284926T3 (es) 2001-09-30 2002-09-25 Nuevos compuestos de feniltanolaminas con una funcion de exticion de un receptor beta2 y metodo para su preparacion.
PCT/CN2002/000676 WO2003093219A1 (fr) 2001-09-30 2002-09-25 Nouveaux composes de phenylethanolamine ayant une fonction d'excitation d'un $g(b)2-accepteur et leur procede de preparation
RU2004112212/04A RU2264382C1 (ru) 2001-09-30 2002-09-25 Новые фенилэтаноламиновые соединения в качестве агонистов и бета2-рецептора и способ их получения
DE60219500T DE60219500T2 (de) 2001-09-30 2002-09-25 Neue phenylethanolaminverbindungen mit erregender wirkung an beta2-akzeptor und verfahren zu deren herstellung
AT02771983T ATE359261T1 (de) 2001-09-30 2002-09-25 Neue phenylethanolaminverbindungen mit erregender wirkung an beta2-akzeptor und verfahren zu deren herstellung
AU2002338124A AU2002338124A1 (en) 2001-09-30 2002-09-25 NOVEL PHENYLETHANOLAMINE COMPOUNDS HAVING Beta2-ACCEPTOR EXCITATORY FUNCTION AND THEIR PREPARATION METHOD
DK02771983T DK1439164T3 (da) 2001-09-30 2002-09-25 Hidtil ukendte phenylethanolaminforbindelser, der har beta2- acceptorexcitatorisk funktion, og deres fremstillingsmetode
US10/491,028 US7098364B2 (en) 2001-09-30 2002-09-25 Phenylethanolamine compounds as β2-receptor agonists, and methods of use and preparation thereof
JP2004501359A JP3990399B2 (ja) 2001-09-30 2002-09-25 β2−受容体興奮作用を有する新規フェニルエタノールアミン類化合物及びそれらの製造方法
EP02771983A EP1439164B1 (en) 2001-09-30 2002-09-25 Novel phenylethanolamine compounds having beta2-acceptor excitatory function and their preparation method
HK04107530A HK1064664A1 (en) 2001-09-30 2004-09-30 Novel phenylethanolamine compounds having beta2-acceptor excitatory function and their preparation method

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CN100497296C (zh) * 2006-07-07 2009-06-10 沈阳药科大学 旋光活性的苯乙醇胺类化合物及其制法
CN100431535C (zh) * 2006-09-18 2008-11-12 锦州九泰药业有限责任公司 一种盐酸川丁特罗气雾剂
EP1969929A1 (de) 2007-03-12 2008-09-17 Bayer CropScience AG Substituierte Phenylamidine und deren Verwendung als Fungizide
CN102477000B (zh) * 2010-11-24 2013-11-06 沈阳药科大学 一种苯乙醇胺类化合物的合成方法
WO2014108449A1 (en) 2013-01-08 2014-07-17 Atrogi Ab A screening method, a kit, a method of treatment and a compound for use in a method of treatment
CN106279018B (zh) * 2015-06-26 2019-01-29 沈阳药科大学 β2-受体兴奋剂及其制备方法和应用
GB201714734D0 (en) 2017-09-13 2017-10-25 Atrogi Ab New compounds and uses
GB201714736D0 (en) 2017-09-13 2017-10-25 Atrogi Ab New compounds and uses
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GB201714740D0 (en) 2017-09-13 2017-10-25 Atrogi Ab New compounds and uses
GB202205895D0 (en) 2022-04-22 2022-06-08 Atrogi Ab New medical uses
WO2024153813A1 (en) 2023-01-20 2024-07-25 Atrogi Ab Beta 2-adrenergic receptor agonists for treatment or prevention of muscle wasting
GB202302225D0 (en) 2023-02-16 2023-04-05 Atrogi Ab New medical uses
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CN1237574A (zh) * 1998-05-29 1999-12-08 中国科学院成都有机化学研究所 合成苯乙醇胺类化合物的方法

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DK1439164T3 (da) 2007-08-20
HK1064664A1 (en) 2005-02-04
EP1439164A4 (en) 2005-12-21
JP3990399B2 (ja) 2007-10-10
RU2264382C1 (ru) 2005-11-20
CN1408703A (zh) 2003-04-09
JP2005519989A (ja) 2005-07-07
DE60219500D1 (de) 2007-05-24
US7098364B2 (en) 2006-08-29
AU2002338124A8 (en) 2003-11-17
ES2284926T3 (es) 2007-11-16
WO2003093219A1 (fr) 2003-11-13
ATE359261T1 (de) 2007-05-15
RU2004112212A (ru) 2005-09-10

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