111555-53-4Relevant articles and documents
Solid-phase synthesis of naltrindole derivatives using Fischer indole synthesis based on one-pot release and cyclization methodology
Tanaka, Hiroshi,Ohno, Hiroshi,Kawamura, Kuniaki,Ohtake, Atsushi,Nagase, Hiroshi,Takahashi, Takashi
, p. 1159 - 1162 (2003)
(Matrix presented) We describe a new approach for the solid-phase synthesis of indoles 1 that involves a one-pot release and cyclization reaction of a solid-supported hydrazone through a Wang-type linker. Using this solid-phase methodology, we accomplishe
An updated synthesis of N1′-([11C]methyl)naltrindole for positron emission tomography imaging of the delta opioid receptor
Kaur, Tanpreet,Brooks, Allen F.,Hockley, Brian G.,Torres, Jovany,Henderson, Bradford D.,Scott, Peter J.H.,Shao, Xia
, p. 187 - 193 (2021)
A new method for the synthesis of the highly selective delta opioid receptor (DOR) antagonist radiotracer N1′-([11C]methyl)naltrindole ([11C]MeNTI) is described. The original synthesis required hydrogenation of a benzyl protecting group after 11C-labeling, which is challenging in modern radiochemistry laboratories that tend to be heavily automated and operate according to current good manufacturing practice. To address this challenge, we describe development of a novel MeNTI precursor bearing a methoxymethyl acetal (MOM) protecting group, which is easily removed with HCl, and employ it in an updated synthesis of [11C]MeNTI. The new synthesis is fully automated and validated for clinical use. The total synthesis time is 45 min and provides [11C]MeNTI in good activity yield (49 ± 8 mCi), molar activity (3,926 ± 326 Ci/mmol) and radiochemical purity (97% ± 2%).
Fischer indole synthesis in water: Simple, efficient preparation of naltrindole, naltriben and analogs
Duval, Romain A.,Lever, John R.
experimental part, p. 304 - 309 (2011/02/28)
Naltrindole, naltrindole analogs and the benzofuran congener naltriben have been prepared by Fischer syntheses using mildly acidic, purely aqueous conditions. The preparation of naltrindole and several analogs was accomplished under almost neutral conditions using just the hydrochloride salts of naltrexone and various electron-rich and electron-poor phenylhydrazines in boiling water. The products were obtained by simple filtration in good to excellent yields and with high purities in the majority of cases. The route is suited to gram-scale synthesis, does not require the use of organic solvents, minimizes the use of corrosive acids, and is simple, efficient and environmentally friendly. Naltriben was prepared efficiently from the hydrochloride salts of naltrexone and O-phenylhydroxylamine but more forcing conditions, 6.0 N HCl, were required. A limitation to the method is the failure of Fischer cyclization between naltrexone and nitro-substituted phenylhydrazines under aqueous conditions.
Solid-supported sulfonylhydroxylamine as an effective N-animating agent of anilines
Ohno, Hiroshi,Tanaka, Hiroshi,Takahashi, Takashi
, p. 1191 - 1194 (2007/10/03)
An effective method for the synthesis of aryl hydrazines by amination of anilines using the solid-supported phenylsulfonylhydroxylamine was described. Treatment of aniline with the solid-supported aminating agent, followed by removal of the resin, provided the corresponding hydrazine in 21% yield. The resulting hydrazines were directly adapted to the solid-phase synthesis of indoles, providing nine naltrindole derivatives varying the substituents on the aromatic rings.
Methods of o-demethylation and n-deprotection
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, (2008/06/13)
The present invention provides a method for N-deprotecting an opioid compound, a method for N-deprotecting and O-demethylating an opioid compound, a method for O-demethylating an opioid compound, and a method for O-demethylating a nonpeptidic delta agonist compound or an opioid compound having a tertiary amide with no significant reaction at amide groups.
L-Selectride as a general reagent for the O-demethylation and N- decarbomethoxylation of opium alkaloids and derivatives
Coop,Janetka,Lewis,Rice
, p. 4392 - 4396 (2007/10/03)
L-Selectride was shown to be an efficient and general O-demethylating agent for the opium alkaloids and their derivatives and also an efficient reagent for the cleavage of methyl carbamates, thus offering a convenient method for the N-demethylation of opioids. Further, it was shown that by choice of reaction conditions it is possible to achieve both N- decarbomethoxylation and O-demethylation in one pot, or only render N- decarbomethoxylation in high yield without accompanying O-demethylation.
IMMUNOSUPPRESSIVE AGENT AND PROCESS OF PRODUCING THE SAME
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, (2008/06/13)
An immunosuppressive agent which has low toxicity and which exhibits excellent effectiveness even if it is orally administered is presented. The immunosuppressive agent of the present invention is characterized in that it contains δ-opioid antagonist having high selectivity to . delta.-opioid receptor. The present invention also provides a process of producing a naltrindole derivative characterized by reacting naltrexone or a salt thereof with a phenylhydrazine derivative in a solvent in the presence of methanesulfonic acid.
