- Enantiomers of Diastereomeric cis-N--N-phenylpropanamides: Synthesis, X-ray Analysis, and Biological Activities
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(+/-)-cis-N--N-phenylpropanamide (1) is a mixture of four stereoisomers , which together constitute two diastereoisomeric pairs of optical i
- Brine, George A.,Stark, Peter A.,Liu, Young,Carrol, F. Ivy,Singh, P.,et al.
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p. 1547 - 1557
(2007/10/02)
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- CARBOSTYRIL DERIVATIVES
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Novel carbostyril derivatives of the formula: STR1 wherein R 1 is H, NO 2, alkoxy, alkoxycarbonyl, alkyl, halogen, optionally substituted amino, OH, CN, COOH, alkanoyloxy, hydrazinocarbonyl; q is 1 to 3, and R is a group of the formula STR2 [wherein R 2 i
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- Synthesis and Pharmacological Evaluation of a Series of New 3-Methyl-1,4-disubstituted-piperidine Analgesics
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The synthesis and intravenous analgesic activity of a series of 3-methyl-4-(N-phenyl amido)piperidines, entries 34-79, is described.The methoxyacetamide pharmacophore produced a series of compounds with optimal analgesic potency and short duration of action. cis-42 was 13 036 times more potent than morphine and 29 times more potent than fentanyl; however, the corresponding diastereomer 43 was only 2778 and 6 times more potent, respectively.Compounds 40, 43, 47, and 57 are extremely short acting; all had durations of action of about 2 min, which was about 1/5 of that of fentanyl in the mouse hot-plate test at a dose equivalent to 2 times the ED50 analgesic dose.Among the many compounds that displayed exceptional analgesic activity, duration of action was one of the main factors for choosing a candidate for further pharmacological investigation.At present, cis-1--3-methyl-4-2-fluorophenyl)methoxyacetamido>piperidine hydrochloride (40) (Anaquest, A-3331.HCl, Brifentanil) is in clinical evaluation.Opiate analgesics that possess short duration of action are excellent candidates for short surgical procedures in an outpatient setting where a rapid recovery is required.
- Lalinde, Nhora,Moliterni, John,Wright, Denny,Spencer, H. Kenneth,Ossipov, Michael H.,et al.
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p. 2876 - 2882
(2007/10/02)
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- Fentanyl analogues 3. 2-(1,2,3,4-tetrahydro)-naphthyl substituted 4-anilidopiperidines
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The synthesis and analgetic properties of 2-(1,2,3,4-tetrahydro)-naphthyl analogues of fentanyl and 3-methylfentanyl are reported. The relation of the N-phenethyl group to the piperidine ring is discussed.
- Fifer,Davis,Borne
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p. 519 - 524
(2007/10/02)
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