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New beta-agonists, processes for preparing them and their use as pharmaceutical compositions

a technology of beta-agonists and processes, applied in the field of new beta-agonists, processes for preparing them and their use as pharmaceutical compositions, can solve the problem of rarely successful methods in the longer term

Inactive Publication Date: 2004-07-01
BOEHRINGER INGELHEIM PHARM KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods are rarely successful in the longer term.

Method used

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  • New beta-agonists, processes for preparing them and their use as pharmaceutical compositions
  • New beta-agonists, processes for preparing them and their use as pharmaceutical compositions
  • New beta-agonists, processes for preparing them and their use as pharmaceutical compositions

Examples

Experimental program
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Effect test

example 5

[0173] a) Enantiomerically Pure Synthesis of (R)-1-(4-benzyloxy-3-nitrophe-nyl)-2-[1,1-dimethyl-3-(4-phenylimidazol-1-yl)-propylamino]-ethanol

[0174] 0.90 g (3.1 mmol) of 3-chloro-1,1-dimethylpropylamine-hydrochloride were added to 10 mL sodium hydroxide solution (1 M) at 0.degree. C. with vigorous stirring. The reaction mixture was stirred for 30 min at 0.degree. C. and then combined with 20 mL methylene chloride. The phases were separated and the aqueous phase was extracted twice with 20 mL methylene chloride. The combined organic phases were dried over magnesium sulphate and the solvent was eliminated. The residue was dissolved in 5.0 mL methylene chloride and at ambient temperature combined with 0.70 g (2.6 mmol) (R)-2-(4-benzyloxy-3-nitrophenyl)-oxirane and 0.20 g (0.26 mmol) ytterbium (III) trifluoromethanesulphonate with stirring. The reaction mixture was stirred for 3 d at ambient temperature and then combined with 30 mL water / methylene chloride (1:1). The phases were separat...

example 12

[0193] a) Racemic Synthesis of N-(2-benzyloxy-5-{2-[1,1-dimethyl-3-(4-phen-yl-imidazol-1-yl)-propylamino]-1-hydroxy-ethyl}-phenyl)methanesulphonamide

[0194] 21.1 g (33.0 mmol) of N-[2-benzyloxy-5-(2-ethoxy-2-hydroxy-acetyl)--phenyl]-methanesulphonamide and 7.00 g (30.0 mmol) of 1,1-dimethyl-3-(4-phenyl-imidazol-1-yl)-propylamine in 150 mL ethanol were refluxed for 18 h. The reaction mixture was cooled to 0.degree. C. and then combined with 3 g (77.0 mmol) sodium borohydride. It was stirred for a further 3 h at ambient temperature and then combined with glacial acetic acid. The solvent was removed using the rotary evaporator and the residue was dissolved in 300 mL ethyl acetate / water (1:2). The aqueous phase was made alkaline with conc. ammonia and separated from the organic phase. The organic phase was washed twice with 200 mL water and once with 200 mL of saturated, aqueous sodium chloride solution, dried over sodium sulphate and freed from solvent using the rotary evaporator. The r...

example 27

[0199] a) Racemic Synthesis of N-(2-benzyloxy-5-{1-hydroxy-2-[3-(4-iodimid-azol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-phenylsulphonamide

[0200] 2.1 g (7.7 mmol) of 3-(4-iodimidazol-1-yl)-1,1-dimethyl-propylamine and 3.4 g (7.7 mmol) of N-[2-benzyloxy-5-(2-ethoxy-1,2-dihydroxy-ethyl)-p-henyl]-phenylsulphonamide in 25 mL ethanol were refluxed for 18 h. The reaction mixture was cooled to 0.degree. C. and then combined with 0.3 g (7.7 mmol) sodium borohydride. The mixture was stirred for a further 3 h at ambient temperature and then combined with glacial acetic acid. The solvent was removed using the rotary evaporator and the residue was dissolved in 300 mL ethyl acetate / water (1:2). The aqueous phase was made alkaline with conc. ammonia and separated from the organic phase. The organic phase was washed twice with 100 mL water and once with 100 mL of saturated aqueous sodium chloride solution, dried over sodium sulphate and freed from solvent using the rotary evaporator. The res...

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Abstract

The present invention relates to new beta-agonists of general formula 1: wherein the groups R<1 >to R<12 >have the meanings given in the claims and specification, the isomers thereof, processes for preparing these compounds and their use as pharmaceutical compositions.

Description

[0001] The present invention relates to new beta-agonists of general formula 1: 2[0002] wherein the groups R.sup.1 to R.sup.12 have the meanings given in the claims and specification, the isomers thereof, processes for preparing these compounds and their use as pharmaceutical compositions.BACKGROUND TO THE INVENTION[0003] The treatment of type II diabetes and obesity is based primarily on reducing calorie intake and increasing physical activity. These methods are rarely successful in the longer term.[0004] It is known that beta-3 receptor agonists have a significant effect on lipolysis, thermogenesis and the serum glucose level in animal models of type II diabetes (Arch JR. beta(3)-Adrenoceptor agonists: potential, pitfalls and progress, Eur J Pharmacol. 2002 Apr. 12;440(2-3):99-107).[0005] Compounds which are structurally similar to the compounds according to the invention and their broncholytic, spasmolytic and antiallergic activities were disclosed in DE 2833140, for example.[000...

Claims

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Application Information

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IPC IPC(8): C07D233/54C07D233/84C07D249/08C07D401/12C07D403/12C07D405/04C07D405/12C07D409/04C07D409/12C07D409/14C07D413/12
CPCC07D233/64C07D233/84C07D249/08C07D401/12C07D403/12C07D413/12C07D405/12C07D409/04C07D409/12C07D409/14C07D405/04
Inventor TRIESELMANN, THOMASHAMILTON, BRADFORD S.STENKAMP, DIRKMUELLER, STEPHAN GEORG
Owner BOEHRINGER INGELHEIM PHARM KG
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