112217-73-9

Upstream product

• 13156-95-1 2-chloro-N-phenethylacetamide 
• 127606-02-4 1-(chloromethyl)-3,4-dihydroisoquinoline hydrochloride 
• 921213-09-4 1-(pyrrolidine-1-methyl)-3,4-dihydroisoquinoline 
• 64-04-0 phenethylamine 
• 112217-71-7 1-(pyrrolidin-1-yl)methyl-1,2,3,4-tetrahydroisoquinoline 
• 6831-55-6 2-(3,4-dichlorophenyl)acetyl chloride 
• 5807-30-7 3,4-dichlorophenyl acetic acid 

Downstream Products

• 112217-73-9 2-(3,4-Dichloro-phenyl)-1-(1-pyrrolidin-1-ylmethyl-3,4-dihydro-1H-isoquinolin-2-yl)-ethanone 

Relevant academic research and scientific papers

Method for the treatment of a hyponatremic disease

Compounds of formula (Ia), or pharmaceutically acceptable salts or solvates thereof, STR1 in which A, together with the nitrogen atom, represents --(CH2)p--, where p is an integer from 3 to 6, or an optionally substituted tetrahydroisoquinoline ring system; each of R1 and R2 are independently hydrogen, C1-6 alkyl, C2-6 alkenyl C3-6 cycloalkyl or C4-12 cycloalkylalkyl, or together form a C2-6 polymethylene or C2-6 alkenylene group, optionally substituted with a hetero-atom, Rx is hydrogen, C1-6 alkyl or phenyl, or together with R1 forms a --(CH2)3 -- or --(CH2)4 -- group; and R comprises a substituted or unsubstituted carbocyclic or heterocyclic aromatic group; and compounds of formula (Ib) STR2 in which: R, R1, R2 and X are as defined in formula (Ia) Ra is C1-6 alkyl or phenyl; Rb is hydrogen or together with Ra forms a --(CH2)n -- group in which n=1, 2 or 3; and `Het` is an optionally substituted single or fused ring heterocyclic group containing from 5 to 12 ring atoms and comprising up to four hetero-atoms in the or each ring, selected from oxygen, nitrogen and sulphur, are useful as diuretic agents.

(1S)-1-(Aminomethyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinoline and heterocycle-condensed tetrahydropyridine derivatives: Members of a novel class of very potent κ opioid analgesics

The synthesis and structure-activity relationship (SAR) of a novel class of κ opioid analgesics, 1-(amino-methyl)-2-(arylacetyl)-1,2,3,4-tetrahydroisoquinolines and (aminomethyl)-N-(arylacetyl)-4,5,6,7-tetrahydrothienopyridines, are described. These compounds, formally derived by the condensation of a benzene or thiophene ring on the piperidine nucleus of the recently described compounds 1, are from 3 to 7 times more potent as antinociceptive agents and with a longer duration of action than the original lead compounds. A similar N2-C1-C9-N10 pharmacophore torsional angle of approximately 60° was also found for this class of compounds by using X-ray and 1H NMR analyses. The same absolute configuration (S) at the chiral center of the active (-) enantiomers was determined by X-ray crystallographic analysis. A varied degree of κ receptor selectivity was a feature of this novel class of antinociceptive agents (μ/κ ratio from 44 to 950 according to the nature of the basic moiety). A SAR analysis indicated that the presence of electron-withdrawing and lipophilic substituents in para and/or meta positions in the arylacetic moiety and the pyrrolidino or dimethylamino basic groups are required to optimize biological activity. The lead compounds 28, 30, and 48 are among the most potent antinociceptive agents (ED50 ca. 0.020 μM/kg sc) and κ ligands (K(i)(κ) ca. 0.20 nM) identified so far.