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AssigneeMiles Laboratories, Inc.
InventorsRobert N. Schut, Edgar O. Snoke, John W. Van Dyke, Jr.
Estimating the term…
Disclosed are novel isoquinoline propionamides and their acid salts represented by the structural formula: ##STR1## wherein R is alkyl of 1 to 6 carbon atoms, methylcycloalkyl of 4 to 7 carbon atoms or alkaryl of 7 to 8 carbon atoms; R' is H or OCH.sub.3 ; A is N or CH; X is H, Cl or CH.sub.3 ; n is 0 or 1; Y is a pharmacologically acceptable, non-toxic acid and p and q are 0 or 1. These compounds exhibit analgesic properties.
N-[(1,2,3,4-Tetr ahydro-2-methyl-1-isoquinolyl)methyl]N-(4-chlorophenyl)propionamide having the structural formula:
Dependencies are inferred from the claim text.
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With radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring: other than aralkyl radicals
Heterocyclic compounds
Term ended 18 Oct 1998 (estimated)
USPTO file history isn’t available for this patent, so only indexed dates are shown.
1. Field of the Invention
This invention involves isoquinoline propionamides and a method for their preparation. The novel compounds of this invention have been found to exhibit potent analgesic activity in in vivo tests.
2. Prior Art
The method of practicing the invention is further illustrated by the following examples in which all temperatures are in .degree.C.
Title Compound I, in which R=CH.sub.3 ; R'=H, A=CH; pY=HCl and q and n=0, was prepared by first refluxing 5.0 g. (0.02 mole) of N-phenylisoquinaldamide with 30 ml. of methyl iodide for 48 hours. The excess methyl iodide was distilled and the resulting brown solution cooled to yield 4.66 g. (60% of theory) of the methiodide (melting range 204.degree.-5.degree. from nitromethane).
Anal. Calcd. for C.sub.17 H.sub.18 IN.sub.2 O: C, 52.32; H, 3.87; N, 7.18. Found: C, 52.39; H, 3.88; N, 7.00.