Substituted xanthine derivatives

A compound and composition technology, applied in the field of substituted xanthine derivatives, can solve problems such as unpredictable effects on drug metabolism properties

Active Publication Date: 2012-05-30
CONCERT PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Even when the deuterium atom is bound at a known metabolic site, the effect of deuterium modification on the metabolic properties of the drug is unpredictable

Method used

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  • Substituted xanthine derivatives
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  • Substituted xanthine derivatives

Examples

Experimental program
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Effect test

other Embodiment approach

[0118] Other embodiments provide compounds of formula B, wherein Y 1 and Y 2 Together with the carbon they are attached to form C=O. On the one hand, R 5 is deuterium. On the other hand, Z 3 ,Z 4 and Z 5 each is hydrogen and R 5 is deuterium. On the other hand, Z 3 ,Z 4 and Z 5 Each is deuterium and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 . On the other hand, R 1 and R 2 Each is - CD 3 and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is deuterium and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is hydrogen. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 each is hydrogen and R 5 is deuterium.

other Embodiment approach

[0119] Other embodiments provide compounds of formula B, wherein Y 1 is OH and Y 2 is hydrogen or deuterium. On the one hand, R 5 is deuterium. On the other hand, Z 3 ,Z 4 and Z 5 each is hydrogen and R 5 is deuterium. On the other hand, Z 3 ,Z 4 and Z 5 Each is deuterium and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 . On the other hand, R 1 and R 2 Each is - CD 3 and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is deuterium and R 5 is deuterium. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 Each is hydrogen. On the other hand, R 1 and R 2 Each is - CD 3 , and Z 3 ,Z 4 and Z 5 each is hydrogen and R 5 is deuterium.

[0120] Another embodiment provides a compound of formula B, wherein R 5 is deuterium.

[0121] Another embodiment provides a compound ...

Embodiment 1

[0339] Example 1: 3-methyl-7-(methyl-d 3 )-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione (compound 100) synthesis

[0340] Route 13: Preparation of Compounds 100 and 409

[0341]

[0342] Step 1: 3-Methyl-7-(methyl-d 3 )-1H-purine-2,6(3H,7H)-dione (51). 3-Methylxanthine 50 (5.0g, 30.1mmol, 1 equivalent) and powdered K 2 CO 3 (5.0 g, 36.0 mmol, 1.2 equiv) in DMF (95 mL) was heated to 60 °C as a suspension and iodomethane-d was added via syringe 3 (Cambridge Isotopes, 99.5 atomic % D, 2.2 mL, 36.0 mmol, 1.2 equiv). The resulting mixture was heated at 80 °C for 5 hours (h). The reaction mixture was cooled to room temperature (rt) and DMF was evaporated under reduced pressure. The crude residue was dissolved in 5% aqueous NaOH (50 mL), forming a dark yellow solution. use CH 2 Cl 2 The aqueous solution was washed three times (total 500 mL). The aqueous layer was acidified to pH 5 with acetic acid (6 mL), forming a brown precipitate. The mixture was cooled in an ice-water...

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Abstract

This invention relates to novel compounds that are substituted xanthine derivatives and pharmaceutically acceptable salts thereof. For example, this invention relates to novel substituted xanthine derivatives that are derivatives of pentoxifylline. This invention also provides compositions comprising one or more compounds of this invention and a carrier and the use of the disclosed compounds and compositions in methods of treating diseases and conditions for which pentoxifylline and related compounds are beneficial.

Description

[0001] related application [0002] This application claims the benefit of priority to U.S. Patent Application No. 12 / 873,991, filed September 1, 2010, and U.S. Provisional Application No. 61 / 239,342, filed September 2, 2009, the entire teachings of which are incorporated herein by reference . Background technique [0003] Many current drugs have poor absorption, distribution, metabolism and / or excretion (ADME) properties, which prevent their widespread use. Poor ADME properties are also the main reason for failing to become drug candidates for clinical trials. Although in some cases formulation techniques and prodrug strategies can be used to improve certain ADME properties, these approaches fail to overcome the inherent ADME problems present with many drugs and drug candidates. One inherent problem is rapid metabolism, which allows many drugs that would otherwise be very effective in treating disease to be cleared from the body too quickly. A possible solution to rapid dr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90A61K31/522
CPCC07D473/04C07D473/10A61P1/00A61P1/04A61P1/16A61P1/18A61P13/00A61P13/02A61P13/12A61P17/04A61P19/06A61P25/02A61P27/02A61P3/00A61P3/04A61P31/18A61P3/06A61P37/02A61P39/00A61P43/00A61P5/50A61P7/02A61P7/06A61P9/10A61P9/12A61P3/10A61K31/522C07D473/06
Inventor R·D·童J·F·刘S·L·哈比森
Owner CONCERT PHARMA INC
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