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Compound containing amide functional group of stable heavy isotope and application thereof

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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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

IUPAC recommends the name of the compound as ammonium acetate, but this and related formal names are rarely used in practice

Method used

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  • Compound containing amide functional group of stable heavy isotope and application thereof
  • Compound containing amide functional group of stable heavy isotope and application thereof
  • Compound containing amide functional group of stable heavy isotope and application thereof

Examples

Experimental program
Comparison scheme
Effect test

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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Application Information

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IPC IPC(8): C07C233/25C07C235/16C07C235/34C07C235/38C07C235/64C07C235/78C07C237/06C07C237/30C07D209/26C07D209/28C07D213/56C07D239/42C07D241/20C07D307/81C07D401/06C07D401/10C07D417/14C07H19/052C07K5/103C07K5/072A61P35/00A61P35/02A61K31/4439A61K31/4965A61K31/165A61K31/167A61K31/405A61K31/343A61K31/454A61K31/505A61K31/4402A61K31/166A61K31/7056A61K38/05A61K38/07
CPCC07D417/14C07D241/20C07D401/06C07D209/26C07D209/28C07D307/81C07D401/10C07D239/42C07D213/56C07H19/052C07C237/30C07C235/34C07C237/06C07C235/64C07C235/38C07C235/16C07C235/78C07C233/25C07K5/1013C07K5/06113A61P35/00A61P35/02C07B2200/05
Inventor 吕佳声顾家敏吉祥朱东青贺小林孔宪起
Owner 君实润佳(上海)医药科技有限公司
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