180272-31-5

Upstream product

• 3230-65-7 3,4-dihydroisoquinoline 
• 960-16-7 tributylphenylstannane 
• 541-41-3 chloroformic acid ethyl ester 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 180272-14-4 quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate 
• 180272-14-4 (1R)-quinuclidin-3'-yl 1-phenyl-1,2,3,4-tetrahydro-isoquinoline-2-carboxylate 
• 180272-14-4 (S,R)-((R)-quinuclidin-3-yl) 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 

Relevant academic research and scientific papers

Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: A multicomponent synthesis of α-substituted amides

A copper-catalyzed cross-coupling of organotin reagents with imines and acid chlorides is reported. The reaction proceeds efficiently with a range of vinyl-, alkyl-, aryl- and heteroaryl-substituted organostannanes as well as a diverse set of imines of non-enolizable aldehydes. Use of chloroformates also allows for the formation of N-protected α-substituted amines. This chemistry has been applied to the synthesis of isoquinoline alkaloid derivatives through the activation of cyclic imines.

3,4-DIHYDROISOQUINOLINE COMPOUNDS AS MUSCRINIC RECEPTOR ANTAGONISTS FOR THE TREATMENT OF RESPIRATORY, URINARY AND GASTROINTESTINAL DISEASES

The present invention generally relates to muscarinic receptor antagonists of formula (I), which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors. Formula (I) wherein Formula (II) represents a nitrogen-containing ring having from 5 to 9 carbon atoms is a bridging group selected from the group consisting of -(CH2)n-, -CH(Q)CH2-, -CH2CH(Q)CH2-, -CH2-O-CH2- or -CH2-NH-CH2-), where n is an integer selected from 0-3 (wherein when n is zero then T represents a direct bond); Y is alkylene, alkenylene, alkynylene or no atom; X is -NH or oxygen.

Synthesis and antimuscarinic properties of quinuclidin-3-yl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives as novel muscarinic receptor antagonists

In the course of continuing efforts to develop potent and bladder-selective muscarinic M3 receptor antagonists, quinuclidin-3-yl 1-aryl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate derivatives and related compounds were designed as conformationally restricted analogues of quinuclidin-3-yl benzhydrylcarbamate (8). Binding assays with rat muscarinic receptor subtypes revealed that the quinuclidin-3-yl 1-aryl-1,2,3,4- tetrahydroisoquinoline-2-carboxylate derivatives showed high affinities for the M3 receptor, and selectivity for the M3 receptor over the M2 receptor. Of these derivatives, (+)-(1S,3'R)-quinuclidin-3'-yl 1-phenyl-l,2,3,4-tetrahydroisoquinoline-2-carboxylate monohydrochloride (9b) exhibited almost the same inhibitory activity against bladder contraction to that of oxybutynin (1), and more than 10-fold selectivity for bladder contraction versus salivary secretion, demonstrating that 9b may be useful for the treatment of symptoms associated with overactive bladder without having side effects such as dry mouth.

Quinuclidine derivatives and medicinal composition thereof

PCT No. PCT/JP95/02713 Sec. 371 Date Aug. 28, 1997 Sec. 102(e) Date Aug. 28, 1997 PCT Filed Dec. 27, 1995 PCT Pub. No. WO96/20194 PCT Pub. Date Jul. 4, 1996Quinuclidine derivatives represented by general following general formula (I), salts, N-oxides or q

Application of the intermolecular α-amido-alkylation reaction for the synthesis of tertiary amides and 1-substituted 2-acyltetrahydroisoquinolines. Synthesis of (±)-carnegine

Adducts 4 of Schiff bases and 3,4-dihydroisoquinolines with acyl chlorides react with Grignard reagents 5 in an intermolecular α-amidoalkylation reaction to the corresponding tertiary amides or 1-substituted 2-acyltetrahydroisoquinolines.