Compound containing amide functional group of stable heavy isotope and application thereof
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A compound and functional group technology, applied to compounds containing stable heavy isotope amide functional groups and their application fields, can solve problems such as seldom use
Pending Publication Date: 2020-11-27
君实润佳(上海)医药科技有限公司
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IUPAC recommends the name of the compound as ammonium acetate,
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Embodiment 1
[0139] Example 1: N-(4-methyl-5-(2-(2,2,2-trifluoro-1,1-dimethylethyl)-4-pyridine)-2-thiazole)aminocarbonyl- L-proline- 18 O-amide (Compound 1 or Alpelisib- 18 o 1 ) preparation
[0140] Under nitrogen protection, (S)-1-N-Boc-2-pyrrolidinecarbonitrile (100mg, 0.51mmol), palladium acetate (12mg, 0.051mmol), 2,2-bipyridine (8mg, 0.051mmol) added to H 2 18 In O (98% oxygen-18 abundance, 0.5 mL), the reaction was stirred at 60° C. for 24 hours in a sealed tube. The reaction solution was cooled to room temperature and transferred to a flask, concentrated under vacuum, and the residue was purified by column chromatography (mobile phase, dichloromethane:methanol=100 / 0~50 / 1), and finally N-Boc-L- Proline- 18O-amide (48 mg; oxygen-18 abundance, 97.3%).
[0141] N-Boc-L-proline- 18 O-amide (48mg, 0.22mmol) was dissolved in dichloromethane (0.5mL), then hydrochloric acid / dioxane solution (4M, 0.5mL) was added, stirred and reacted at 25°C for 1 hour, and then the reaction solutio...
Embodiment 2
[0146] Example 2: N-(4-methyl-5-(2-(2,2,2-trifluoro-1,1-dimethylethyl)-4-pyridine)-2-thiazole)aminocarbonyl- L-proline- 17 O-amide (Compound 2 or Alpelisib- 17 o 1 ) preparation
[0147] In addition to using O 17 - water (H 2 17 O) to replace the H used in Example 1 2 18 Compound 2 was obtained in the same manner as in Example 1 except for O.
Embodiment 3
[0148] Example 3: N-(4-methyl-5-(2-(2,2,2-trifluoro-1,1-dimethylethyl)-4-pyridine)-2-thiazole)aminocarbonyl- L-proline- 13 C 1 -amide (Compound 4 or Alpelisib- 13 C 1 ) preparation
[0149] In addition to using proline- 13 C 1 Compound 4 was obtained in a similar manner to Example 1 except that -amide hydrochloride was used as the starting material.
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Abstract
The invention provides a compound containing a stable heavy isotope-enriched amide functional group. The compound is as shown in a formula (I) and is used for adjusting the pharmacokinetic characteristics, metabolic characteristics and/or delivery efficiency and treatment and prevention effects of a drug or a prodrug. The invention also relates to the application of the drug or prodrug containingisotope-enriched amide in the treatment or prevention of illness and symptoms of diseases.
Description
technical field [0001] The present invention relates to compounds containing stable heavy isotopically enriched amide functional groups and their use in modulating the pharmacokinetic properties, metabolic properties and / or delivery efficiency of compounds (e.g. drugs or prodrugs), as well as therapeutic and Preventive application. Background technique [0002] Amides, also known as acid amines, are compounds of the formula R m E(O) n NR 1 R 2 The compound, wherein, R, R 1 and R 2 is hydrogen (H) or an organic group. The most common amide is formamide (organic amide), where m is 1, E is carbon (C) and n is 1. Many other important classes of amides are known, including phosphoramides (e.g., where m is 1, E is phosphorus (P) and n is 2, and related compounds) and sulfonamides (e.g., where m is 1, E is sulfur (S) and n is 2, and related compounds) (see, see IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"), 1997). Another class of amides are the phos...
Claims
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