196195-38-7

Upstream product

• 100-44-7 benzyl chloride 
• 99481-03-5 (5-acetyl-2-hydroxy-phenyl)-acetic acid methyl ester 
• 100-39-0 benzyl bromide 
• 99-93-4 4-Hydroxyacetophenone 
• 81720-89-0 (5-acetyl-2-hydroxyphenyl)acetic acid 
• 65236-06-8 5-acetyl-2-hydroxyphenylacetonitrile 
• 24085-05-0 1-(3-chloromethyl-4-hydroxyphenyl)ethanone 

Downstream Products

• 371783-91-4 2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-tert-butyldimethylsilyloxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide 
• 371783-92-5 2-{[(2S)-2-({(2R)-2-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-hydroxyethyl}amino)-1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide 
• 371783-90-3 (1R)-1-[4-benzyloxy-3-(2-tert-butyldimethylsilyloxyethyl)phenyl]-2-bromoethan-1-tert-butyldimethylsilyloxyethane 
• 371783-87-8 (1R)-1-[4-benzyloxy-3-(2-hydroxyethyl)phenyl]-2-bromoethan-1-ol 
• 371783-86-7 methyl (2-benzyloxy-5-bromoacetylphenyl)acetate 

Relevant academic research and scientific papers

The practical synthesis of a uterine relaxant, Bis( 2-{[(2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3-(2-hydroxyethyl) -phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-yl]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246)

The synthetic route for a uterine relaxant, bis(2-{[ (2S)-2-({(2R)-2-hydroxy-2-[4-hydroxy-3- (2-hydroxyethyl)-phenyl]ethyl}amino) -1,2,3,4-tetrahydronaphthalen-7-y1]oxy}-N,N-dimethylacetamide) sulfate (KUR-1246), was established by the coupling of optically active components, the bromohydrin 14 and the amine 24. We now describe the practical synthesis of these two optically active components. Bromohydrin 14 was obtained by the asymmetric borane reduction of the prochiral phenacyl bromide 13 using a catalyst prepared from aluminum triethoxide and a chiral amino alcohol. The other optically active component 24 was prepared from (S)-AMT.

3,4-disubstituted phenylethanolaminotetralincarboxylic acid derivatives

PCT No. PCT/JP97/01008 Sec. 371 Date Mar. 8, 1999 Sec. 102(e) Date Mar. 8, 1999 PCT Filed Mar. 26, 1997 PCT Pub. No. WO97/35835 PCT Pub. Date Oct. 2, 1997The present invention relates to 3,4-disubstituted phenylethanolaminotetralincarboxylic acid derivatives represented by the general formula: [wherein Q represents a vinylene group or a group represented by the general formula: -A-(CH2)m-(wherein A represents an oxygen atom or a methylene group; and m is an integer of from 1 to 6); R represents a hydrogen atom or a lower alkyl group; n is an integer of 1 or 2; the carbon atom marked with * represents a carbon atom in R configuration, S configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in S configuration] and pharmaceutically acceptable salts thereof, which have a selective beta 2-adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator and an agent for pain remission and promoting stone removal in urolithiasis.

3,4-disubstituted phenylethanolaminotetralincarboxamide derivatives

The present invention relates to 3,4-disubstituted phenylethanolaminotetralincarboxamide derivatives represented by the general formula: STR1 (wherein A represents a lower alkylene group; B represents an amino group, a di(lower alkyl)amino group or a 3 to 7-membered alicyclic amino group which may contain an oxygen atom in the ring; n is an integer of 1 or 2; the carbon atom marked with * represents a carbon atom in R configuration, S configuration or a mixture thereof; and the carbon atom marked with (S) represents a carbon atom in S configuration) and pharmaceutically acceptable salts thereof, which have a selective β 2 -adrenergic receptor stimulating effect with relieved burdens on the heart such as tachycardia and are useful as an agent for the prevention of threatened abortion and premature labor, a bronchodilator and an agent for pain remission and stone removal in urolithiasis.