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Amide derivatives of aniline-related compound and composition of amide derivatives of aniline-related compound

A compound and solvate technology, applied in the field of amide derivatives, can solve the problems of limited bioavailability and low water solubility of aniline-related compounds

Inactive Publication Date: 2015-10-14
C & C BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the aqueous solubility of aniline-related compounds is often low, which limits their bioavailability

Method used

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  • Amide derivatives of aniline-related compound and composition of amide derivatives of aniline-related compound
  • Amide derivatives of aniline-related compound and composition of amide derivatives of aniline-related compound
  • Amide derivatives of aniline-related compound and composition of amide derivatives of aniline-related compound

Examples

Experimental program
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preparation example Construction

[0109] Preparation of Amide Derivatives Disclosed herein.

[0110] Amide derivatives of aniline-related compounds can be prepared by conventional organic synthesis. For example, amide derivatives can be prepared by reacting an aniline related compound with a suitable acid, where the other reactive group of the acid is protected by a protecting group (e.g. amino group via tert-butoxycarbonyl (BOC), trityl (Trt) or 2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-ylsulfonyl (Pbf) protected; hydroxyl by tert-butoxy (tBu); carboxyl by tert-butyl carboxylate (OtBU) protection) to avoid undesired reactions. In certain embodiments, a coupling agent such as HBTU (O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and It is carried out under the condition of base (such as DIEA (N,N-diisopropylethylamine)).

[0111] The prepared amide derivatives, if provided with protecting groups ("protected amide derivatives"), can be further converted into unprotected amide deri...

Embodiment 1

[0130] Example 1: Preparation of amide derivatives of aniline-related compounds disclosed herein.

[0131] Several amide derivatives of several aniline-related compounds were prepared from the reaction of the corresponding aniline-related compounds and acids in DMF and in the presence of HBTU and DIEA. Other active groups on the acid that should not participate in the reaction have been protected (such as the amino group through tert-butoxycarbonyl (BOC), trityl (TrtRT protection) or 2,2,4,6,7-pentamethyl -2,3-dihydrobenzofuran-5-ylsulfonyl (Pbf) protected; hydroxyl protected by tert-butoxy (tBu); carboxyl protected by tert-butyl carboxylate (OtBU)).

[0132] I. Preparation of MS-275 Amide Derivatives.

[0133] To a solution of the acid in DMF (20 mL) was added HBTU and DIEA. The reaction mixture was stirred at 10°C for 10 minutes, and MS-275 was added to the reaction solution. After the reaction mixture was stirred at room temperature for 12 hours, 50 ml of water was added...

Embodiment 2

[0218] Example 2. Solubility of several amide derivatives.

[0219] Solubility (mg / ml) of a compound in water was measured by adding the compound to a known amount (eg, 1 mL) of water until saturation, and measuring the amount of the compound added (Table 9).

[0220] Table 9. Solubility of several amide derivatives.

[0221] Structural formula PR

[0222] Structural formula PR-4

[0223] Structural formula PR-3

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Abstract

Amide derivatives of aniline-related compounds are disclosed, including salts thereof, and compositions, preparations and uses thereof. In certain embodiments, the amide derivatives and / or salts thereof show higher solubility in water compared to the corresponding parent aniline-related compounds.

Description

technical field [0001] The present application relates to amide derivatives of aniline-related compounds, including salts thereof, compositions thereof, preparations thereof and uses thereof. Background technique [0002] Compounds containing aniline structures (aniline-related compounds) are promising drug candidates for the treatment of various diseases. However, the aqueous solubility of aniline-related compounds is often low, which limits their bioavailability. Therefore, it is necessary to synthesize new derivatives of these compounds to have higher water solubility. Contents of the invention [0003] One aspect of the present invention pertains to amide derivatives of aniline related compounds with enhanced solubility. [0004] Another aspect of the invention pertains to compositions of the amide derivatives disclosed herein. [0005] Another aspect of the invention relates to the use of the amide derivatives disclosed herein. Description of drawings [0006] ...

Claims

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Application Information

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IPC IPC(8): C07D213/30C07D401/04C07C271/22C07C237/04C07D307/79C07D233/64C07D207/16C07C279/14A61K31/4406A61K31/506A61K31/27A61K31/167A61K31/343A61K31/4164A61K31/401A61P35/00
CPCC07D401/04C07C235/74C07D213/56C07C237/04C07C271/22C07C279/14C07D207/16C07D213/30C07D233/64C07D307/79A61P35/00
Inventor 陈林武永庆盖大海陈小江
Owner C & C BIOPHARMA
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