93744-18-4

Upstream product

• 611-20-1 salicylonitrile 
• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 70987-78-9 (S)-Glycidyl tosylate 
• 51594-55-9 (R)-(-)-epichlorohydrin 
• 1054487-80-7 (R)-3-(2-cyanophenoxy)-1-bromo-2-propanol 
• 93744-27-5 (R)-(-)-4-(2-cyanophenoxy)methyl-2,2-dimethyl-1,3-dioxolane 
• 56715-37-8 (2S)-1-(2-cyanophenoxy)-2,3-propanediol 
• 97960-34-4 2-(prop-2'-enyloxy)benzonitrile 
• 850427-88-2 (R)-4-(2-cyanophenoxymethyl)-1,3,2-dioxathiolane-2-oxide 
• 850427-94-0 (R)-4-(2-cyanophenoxymethyl)-1,3,2-dioxathiolane-2,2-dioxide 
• 93744-28-6 (R)-(-)-2-acetyloxy-1-bromo-3-(2-cyanophenoxy)propane 

Downstream Products

• 915287-89-7 (S)-N-[4-(2-bromo-ethoxy)-phenyl]-N'-[2-[3-(2-cyanophenoxy)-2-hydroxy-propylamino]-ethyl]-urea 
• 1037411-43-0 (S)-3-(2-cyanophenoxy)-N-(2-(2-fluorophenoxy)ethyl)-2-hydroxypropan-1-aminium trifluoroacetate 
• 1037411-57-6 (S)-3-(2-cyanophenoxy)-N-(2-(2-(4-fluorophenyl)acetamido)ethyl)-2-hydroxypropan-1-aminium trifluoroacetate 
• 1037411-67-8 (S)-1-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-3-(4-(3-fluoropropoxy) phenyl)urea 
• 1037411-56-5 (S)-1-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-2-(4-fluorophenyl)acetamide 
• 46905-83-3 (S)-1-(2-cyanophenoxy)-2-hydroxy-3-tert-butylamino-propane 
• 131769-21-6 (S)-(-)-1-<2-<3-(2-cyanophenoxy)-2-hydroxypropyl>aminoethyl>-2,4-dioxo-3-phenyl-1H,3H-imidazolidine 
• 46905-83-3 (R)-1-(2-cyanophenoxy)-2-hydroxy-3-tert-butylamino-propane 
• 1323276-32-9 C₂₀H₂₁FN₄O₅ 
• 1323276-85-2 (S)-1-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-3-(3-benzyloxyphenyl) urea 
• 1323276-56-7 (S)-N-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-2-fluorobenzenesulfonamide 
• 1323276-55-6 (S)-N-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-6-fluoronicotinamide 
• 1323276-52-3 (S)-4-(3-(2-cyanophenoxy)-2-hydroxypropylamino)-N-(6-fluoropyridin-3-yl)butanamide 
• 1323276-48-7 (S)-1-(2-(3-(2-cyanophenoxy)-2-hydroxypropylamino)ethyl)-3-(1-(2-fluoroethyl)piperidin-4-yl)urea 

Relevant academic research and scientific papers

Efficient chemoenzymatic synthesis of (RS)-, (R)-, and (S)-bunitrolol

A new chemical and the first chemoenzymatic synthesis of β-adrenergic receptor blocking agent bunitrolol is reported in racemic (RS) and enantioenriched forms (R and S). The intermediates (R)- and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates were synthesized from the corresponding racemic alcohol through enzymatic kinetic resolution. The commercial available lipases PS-C and CCL exhibited complementary enantioselectivity during transesterification of the racemic alcohol with vinyl acetate affording the (R)-alcohol along with (S)-acetate and the (S)-alcohol along with (R)-acetate, respectively, and represent an example of enzymatic switch for reversal of enantioselectivity. The effects of various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium, on the activity and enantioselectivity were optimized. The (R)- and (S)-alcohols were converted into (S)-and and (R)-bunitrolol, respectively, by treatment with tert-butylamine. The (R)- and (S)-acetates, obtained enzymatically were deacetylated to the corresponding alcohol by chemical hydrolysis and further converted into (S)-and and (R)-bunitrolol by chemical means. This is the first chemoenzymatic synthesis of both of the enantiomers of the drug. (RS)-, (R)-, and (S)-Bunitrolol were also synthesized following the 'all chemical' routes from (RS)-, (R)-, and (S)-epichlorohydrin via the corresponding (RS)-, (S)-, and (R)-2-cyanoglycidyl ether and the (RS)-, (R)-, and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates with improved overall yields and better enantiomeric excesses compared to the reported processes.

METHODS AND COMPOSITIONS INVOLVING (S)-BUCINDOLOL

Disclosed is bucindolol substantially free of its R-stereoisomer. Also disclosed are pharmaceutical compositions that include bucindolol substantially free of its R-stereoisomer or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier. Also disclosed are methods of treating a patient that involve administering to the patient a therapeutically effective amount of a composition of the present invention. Formula (I).

Spontaneous resolution amongst chiral ortho-cyanophenyl glycerol derivatives: an effective preferential crystallization approach to a single enantiomer of the β-adrenoblocker bunitrolol

The β-adrenoblocker bunitrolol 1 as well as intermediate cyclic sulfate 6 and glycidyl ether 8 have been prepared in enantiopure form by starting from enantiopure o-cyanophenyl glycerol ether 2 by an entrainment resolution procedure. Thermal investigations reveal that 1·HCl forms a moderately stable racemic compound, whereas 2, 6 and 8 are conglomerate forming substances potentially capable of entrainment resolution. Some chemical and chiroptical characteristics for bunitrolol and possible intermediates in its synthesis were corrected, and configurations were verified with the configuration of 1·HCl.

LIGANDS FOR CARDIAC BETA1 ADRENOCEPTOR FOR IMAGING CONGESTIVE HEART FAILURE

Novel β1 adrenoreceptor ligands that find use as imaging agents within nuclear medicine applications (e.g., PET imaging and SPECT imaging) are provided. Methods of imaging, including methods of imaging congestive heart failure, are also provide

NOVEL 1 -BENZYL-4-PIPERIDINAMINES THAT ARE USEFUL IN THE TREATMENT OF COPD AND ASTHMA

The invention provides 1 -benzyl- 4 -piperidinamines of the general formula (I), processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds are useful in the treatment of respiratory diseses such a

Synthesis of an 18F-labelled high affinity β1- adrenoceptor PET radioligand based on ICI 89,406

To date, some non-selective β-adrenoceptor (β-AR) positron emission tomography (PET) radioligands are in clinical use, but no PET radioligand for the selective imaging of cardiac β1-ARs is clinically available. Therefore, the aim of this study

Synthesis of (R)- and (S)-[O-methyl-11C]N-[2-[3-(2-cyano- phenoxy) -2-hydroxy-propylamino]-ethyl]-N′-(4-methoxy-phenyl)-urea as candidate high affinity β1-adrenoceptor PET radioligands

Molecular imaging and quantification of myocardial β1- adrenoceptor (AR) rather than total β-AR density is of great clinical interest since cardiac biopsy studies suggest that myocardial β1-AR density is reduced in patients with chro

Asymmetric synthesis of aryloxypropanolamines via OsO4-catalyzed asymmetric dihydroxylation

A simple and effective procedure for the enantioselective synthesis of several β-adrenergic blocking agents incorporating the first asymmetric synthesis of celiprolol, is described. The key steps are (i) sharpless asymmetric dihydroxylation of aryl allyl ethers to introduce chirality into the molecules and (ii) conversion of cyclic sulfates into the corresponding epoxides using a three-step procedure.

A FACILE ENANTIOSELECTIVE SYNTHESIS OF AN ARYLOXYPROPANOLAMINE β-BLOCKER THROUGH A TWO-STEP CONVERSION OF 1,3-DIOXOLANES INTO EPOXIDES

A facile and convenient synthesis of the two enantiomers of P-0160, an aryloxypropanolamine β-blocker, is presented.The key step is the reaction of a chiral isopropylideneglycerol derivative with hydrobromic acid in acetic acid to afford a 2-acetoxy-1-bro