- Synthesis of Hindered α-Amino Carbonyls: Copper-Catalyzed Radical Addition with Nitroso Compounds
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The synthesis of sterically hindered anilines has been a significant challenge in organic chemistry. Here we report a Cu-catalyzed radical addition with in situ-generated nitroso compounds to prepare sterically hindered amines directly from readily available materials. The transformation is conducted at room temperature, uses abundant copper salts, and is tolerant of a range of functional groups.
- Fisher, David J.,Burnett, G. Leslie,Velasco, Rocío,Read De Alaniz, Javier
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supporting information
p. 11614 - 11617
(2015/09/28)
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- Synthesis of 4-anilinopiperidine methyl esters, intermediates in the production of carfentanil, sufentanil, and remifentanil
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Two spirodiaza intermediates have been made and employed in the synthesis of 4-anilinopiperidine methyl esters. These intermediates can be utilized in the production of commercial synthetic analgesics carfentanil, sufentanil, and remifentanil.
- Walz, Andrew J.,Hsu, Fu-Lian
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p. 501 - 502
(2014/01/06)
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- Synthesis of intermediate anilino methyl esters used in the production of synthetic opioid analgesics
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An improved process or method of synthesis of carfentanil and other potent opioid analgesics of the N-alkyl 4-substituted 4-piperidinylamide class which can be used as morphine substitutes.
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- Alternate Process for Remifentanil Preparation
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An alternate process for synthesizing opiate or opioid analgesics and anesthetics, and intermediates thereof is provided. In particular, a process of synthesizing synthetic opiate or opioid compounds such as, for example, remifentanil, carfentanil, sufentanil, fentanyl, and alfentanil are disclosed.
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Page/Page column 8
(2010/05/13)
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- SUBSTITUTED 4-AMINO-PIPERIDINES
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The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof
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Page/Page column 25
(2010/02/17)
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- IMPROVED METHOD OF MAKING SUFENTANIL
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The present invention relates to a process for the preparation of piperidine derivatives including sufentanil and its pharmaceutically acceptable salts, such as it citrate salt
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Page/Page column 3; 7
(2010/11/29)
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- Syntheses, biological evaluation, and molecular modeling of 18F-labeled 4-anilidopiperidines as μ-opioid receptor imaging agents
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The synthesis, evaluation, and molecular modeling of a series of 18F-labeled 4-anilidopiperidines with high affinities for the μ-opioid receptor (μ-OR) are reported. On the basis of the high brain uptake and selective retention in brain regions that contain a high concentration of the μ-OR, combined with a good metabolic stability, [ 18F]fluoro-pentyl carfentanil ([18F]4) and 2-(±)[18F]-fluoropropyl-sufentanil ([18F]6) were selected as the lead compounds for further evaluation. The binding affinity to the human μ-OR was 0.74 and 0.13 nM for [18F]4 and [ 18F]6, respectively. In vitro autoradiography of [18F] 4 and [18F] 6 on rat brain sections produced patterns in accordance with the known distribution of μ-OR expression. Structure-activity relationships of the fluorinated compounds are discussed with respect to the interaction with an activated-state model of the μ-OR. Taken together, the in vivo and in vitro data indicate that [18F] 4 and [18F] 6 hold promise for studying the μ-opioid receptor in humans by means of positron emission tomography.
- Henriksen, Gjermund,Platzer, Stefan,Marton, János,Hauser, Andrea,Berthele, Achim,Schwaiger, Markus,Marinelli, Luciana,Lavecchia, Antonio,Novellino, Ettore,Wester, Hans-Jürgen
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p. 7720 - 7732
(2007/10/03)
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- The conversion of amides to esters with Meerwein's reagent. Application to the synthesis of a carfentanil precursor
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An efficient two step transformation of 1°and 2°amides to methyl and ethyl esters has been developed using trimethyl- and triethyloxonium tetrafluoroborates, and dilute acid. This methodology was applied to 1-benzyl-4-phenylamino-4-piperidinecarboxamide, a precursor in the synthesis of carfentanil, to produce the methyl ester in 60% yield and the ethyl ester in 80% yield.
- Kiessling, Anthony J.,McClure, Cynthia K.
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p. 923 - 937
(2007/10/03)
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- N-(4-piperidinyl)-N-phenylamides
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Novel N-(4-piperidinyl)-N-phenylamides and -carbamates having very potent analgesic activity, methods of preparing same and useful intermediates therefor.
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- N-(4-piperidinyl)-N-phenylamides and -carbamates
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Novel N-(4-piperidinyl)-N-phenylamides and -carbamates having very potent analgesic activity, methods of preparing same and useful intermediates therefor.
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