82716-88-9Relevant academic research and scientific papers
Decahydroisoquinoline carboxylic acids
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, (2008/06/13)
What are disclosed are aminoacid compounds of the formula STR1 wherein n is 0 or 1, and salts thereof, said compounds and salts having hypotensive properties; methods for making the compounds; pharmaceutical compositions containing the compounds or salts;
(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
Vecchietti,Clarke,Colle,Giardina,Petrone,Sbacchi
, p. 2624 - 2633 (2007/10/02)
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.
Bicyclic α-iminocarboxylic acid compounds having hypotensive activity
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, (2008/06/13)
What are disclosed are indole, quinoline and isoquinoline compounds of the formula STR1 in which n denotes 0 or 1, m denotes 1 or 2, but (n+m)≤2, A together with the bridgehead carbon atoms denotes a benzene or a cyclohexane ring, Y1 denotes hy
Substituted derivatives of octahydroindole-2-carboxylic acids
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, (2008/06/13)
Compounds of the formula I STR1 in which n denotes 0-3, R1 and R1' are the same or different and denote hydrogen, alkyl or alkenyl, phenyl or benzyl, each substituted as desired; R2 denotes hydrogen, alkyl or alkenyl; R3 denotes hydrogen, alkyl, hydroxyalkyl, alkoxyalkyl or aminoalkyl, alkanoylaminoalkyl, guanidinoalkyl, imidazolylalkyl, indolylalkyl, mercaptoalkyl or alkylthioalkyl, phenylalkyl, hydroxyphenylalkyl, phenoxyalkyl or phenylthioalkyl, or R2 and R3, together with the C and N atoms carrying them, denote a saturated or unsaturated 4- to 8-membered monocyclic or 8- to 10-membered bicyclic isocycle or heterocycle, optionally monosubstituted or disubstituted by hydroxyl, alkoxy having 1 to 3 C atoms or alkyl, R4 denotes hydrogen, alkyl, alkenyl, alkadienyl, alkinyl, alkeninyl or alkadiinyl, cycloalkyl, phenyl, benzyl, phenethyl or phenylpropyl, each of which can be optionally monosubstituted or disubstituted; R5 denotes hydrogen or alkyl, hydroxyl or alkoxy and R6 denotes hydrogen, optionally substituted alkyl, cycloalkyl, alkenyl, optionally monosubstituted or disubstituted phenyl or naphthyl, their salts, a process for their preparation and their use as medicaments.
