Cis- and trans-N-(2-aminocycloaliphatic)-2-arylacetamide derivative compounds of the formula [Figure] (1) e.g., N-[2-(N′, N′-dimethylamino)cyclohexyl]-N-methyl-2-(4-bromophenyl)acetamide and trans-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide, 2-(3,4-dichlorophenyl) and their pharmaceutically a
Cis- and trans-N-(2-aminocycloaliphatic)-2-arylacetamide derivative compounds of the formula [Figure] (1) e.g., N-[2-(N′, N′-dimethylamino)cyclohexyl]-N-methyl-2-(4-bromophenyl)acetamide and trans-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide, 2-(3,4-dichlorophenyl) and their pharmaceutically acceptable salts, have been found to have potent analgesic activity, and the preferred compounds have in addition only low to moderate apparent physical dependence liability, compared to morphine and methadone. As analgesics they would be useful also as antitussives. Processes for preparation of these compounds are also disclosed. This invention also includes compositions containing these compounds useful in pharmaceutical dosage unit form for alleviating pain in humans and animals, as well as methods for alleviating pain in animals and humans with these compositions.
대표청구항▼
A compound of the formula [Figure] (1) wherein the ＿at the 1-position of the cycloaliphatic ring denotes trans-stereoconfiguration of The 1-position substituent with respect to the substituent in position 2 of the same cycloaliphatic ring; R is C1 to C3-alkyl; R1 and R2, taken separately, are C1 to
A compound of the formula [Figure] (1) wherein the ＿at the 1-position of the cycloaliphatic ring denotes trans-stereoconfiguration of The 1-position substituent with respect to the substituent in position 2 of the same cycloaliphatic ring; R is C1 to C3-alkyl; R1 and R2, taken separately, are C1 to C3-alkyl, or when R1 is C1 to C3-alkyl, R2 is C1 to C6-alkyl, -CH2CF3, C3 to C6-(allylic)alkenyl, C2 to C5-hydroxyalkyl, C3 to C6-cycloalkyl, C3 to C4-cycloalkylmethyl, phenyl-C1 to C3-alkyl, or R1 and R2 taken together with the nitrogen to which they are bonded complete a saturated, monocyclic, mononitrogen heterocyclic ring containing only carbon and nitrogen ring atoms and containing from 3 to 4 carbon atoms; said saturated monocyclic nitrogen heterocyclic rings having 3 to 4 ring carbon atoms permissively being substituted in the 3-position of the ring with hydroxy, C1 to C3-alkyloxy, or C1 to C3-alkanoyloxy; or N-piperazinyl ring, permissively substituted on the N′-nitrogen with a C1 to C3-alkyl; R3 is hydrogen or methyl; R4 is hydrogen or methyl, or R3 and R4 can be taken together with the carbon to which they are bonded to complete a cyclopropylene ring; m is 1 to 4 and is 2 to 4 only when R3 and R4 are both hydrogen; n is 2 to 4; and Q is 1-naphthyl, 2-naphthyl or [Figure] wherein each of X, Y and Z is hydrogen, a halogen having an atomic number of from 9 to 35, trifluoromethyl, C2 to C3-alkyl, C1 to C3-alkyloxy, azido or phenyl, and at least one of X, Y and Z is a substituent other than hydrogen, and when one of X, Y and Z is azido, phenyl, C1 to C3-alkyloxy or trifluoromethyl, the remaining X, Y and Z moieties are hydrogen, and the pharmaceutically acceptable salts thereof. A composition useful in pharmaceutically effective dosage unit form for alleviating pain in warm-blooded mammals which comprises a compound of formula I in claim 1 in combination with a pharmaceutically acceptable carrier.
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