Synthesis of 3H and 14C labelled SCH 48461

Hesk, David; Bowlen, Christine; Hendershot, S.; Koharski, D.; McNamara, Paul E.; Rettig, D.; Saluja, S.

doi:10.1002/(sici)1099-1344(199611)38:11<1039::aid-jlcr920>3.0.co;2-g

Cited by 10 publications

(19 citation statements)

References 5 publications

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“…3 H nmr analysis showed that the expected meta and para positions were labelled along with a small amount of incorporation in the benzylic site. 6 Similar methodology was also used to prepare [ 3 H]Sch 40120 (6) and [ 3 H]Sch 40853 (7) ( Figure 1). 4,7 Although versatile, Pt-catalysed exchange does suffer a significant drawback.…”

Section: Synthesis and Analysis Of Tritium-labelled Compoundsmentioning

confidence: 99%

Synthesis of isotopically labelled compounds at Schering‐Plough, an historical perspective

Hesk¹,

McNamara²

2007

Labelled Comp Radiopharmac

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The use of isotopically labelled compounds at Schering-Plough (S-P) has substantially increased over the past 30 years. Since the formation of the S-P Radiochemistry section in the early 1970s, the group has expanded its role from supplying 14 C-and 3 H-labelled compounds for ADME studies for compounds in development, to providing 3 H-labelled compounds for drug discovery and also to provide stable isotope-labelled compounds that are used as LC/MS internal standards. Other isotopes used by the group have included 125 I and 35 S, which have been used to label both small molecules and proteins.

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Section: Synthesis and Analysis Of Tritium-labelled Compoundsmentioning

confidence: 99%

Synthesis of isotopically labelled compounds at Schering‐Plough, an historical perspective

Hesk¹,

McNamara²

2007

Labelled Comp Radiopharmac

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“…The extensive basic research on heterogeneous transition metal-catalyzed exchange of simple organic compounds with isotopic water pioneered by Garnett [40,41] has been successfully applied to pharmaceutical compounds using high activity tritiated water [42][43][44]. With the ability to comprehensively and carefully characterize the products of these exchange reactions, this approach should become more heavily employed.…”

Section: Heterogeneous Metal-catalyzed Exchange With Tritiated Watermentioning

confidence: 99%

Recent Developments in Tritium Incorporation for Radiotracer Studies

Saljoughian

Williams²

2000

CPD

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The essential nature of rapid radiotracer synthesis very early in drug discovery programs has driven the need for better and more varied tritium incorporation methods. This review presents a summary of recent advances for tritium introduction via tritiated water, tritium gas, complex tritides, and a range of recently improved tritiation reagents. Access to a wider range of tritiated reagents (for tritioacetylation, tritioformylation, methylation, etc.) and commercial manifolds for the transfer and use of tritium gas is also discussed.

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“…al., [119], also used an Evans approach for their synthesis of [ 14 C]SCH-48461. Acylation of (R)-4-benzyloxazolidinone with [ 14 C]5-phenylvalerolyl chloride (prepared from 4-phenylbutoxy tosylate and K 14 CN) gave (132).…”

Section: Asymmetric Syntheses Using Labelled Reagentsmentioning

confidence: 99%

Recent Advances in the Design and Synthesis of Carbon-14 Labelled Pharmaceuticals from Small Molecule Precursors

McCarthy

2000

CPD

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Over the past decade, the increased chemical complexity of new drug candidates has resulted in a parallel need to develop innovative syntheses of carbon-14 labelled pharmaceuticals. Faced with short time-lines and a limited number of labelled precursors, radiochemists have addressed this challenge by developing new reagents and adapting existing technology to labelled syntheses. Selected examples from the recent radiochemical literature illustrate some of the creative strategies used to rapidly solve these synthetic challenges. Examples describing the handling and use of common small molecule reagents, such as carbon-14 labelled carbon dioxide, methyl iodide, cyanide, acetic acids, sulfur and phosphorous stabilized ylides for the synthesis of labelled steroids, prostanoids, nucleosides, pyridines, quinolines, benzazepines and other heterocycles are presented. Several general strategies for radiolabelling are also discussed including the degradation strategy for accessing necessary intermediates and precursors, the radiolabelling of aromatic substrates, transition metal mediated cross-couplings, and the use of chiral auxiliaries for the enantioselective syntheses of radiolabelled pharmaceuticals.

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Synthesis of 3H and 14C labelled SCH 48461

Cited by 10 publications

References 5 publications

Synthesis of isotopically labelled compounds at Schering‐Plough, an historical perspective

Synthesis of isotopically labelled compounds at Schering‐Plough, an historical perspective

Recent Developments in Tritium Incorporation for Radiotracer Studies

Recent Advances in the Design and Synthesis of Carbon-14 Labelled Pharmaceuticals from Small Molecule Precursors

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