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Controlled release oral dosage forms of poorly soluble drugs and uses thereof

A technology for poorly soluble drugs and oral dosage, which is used in the treatment of various diseases and/or conditions, and can solve problems such as the need for alternative controlled-release dosage forms

Active Publication Date: 2013-12-11
AMGEN (EURO) GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there remains a need for alternative controlled release dosage forms for poorly water soluble drugs

Method used

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  • Controlled release oral dosage forms of poorly soluble drugs and uses thereof
  • Controlled release oral dosage forms of poorly soluble drugs and uses thereof
  • Controlled release oral dosage forms of poorly soluble drugs and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0146] 5.1 Example 1: 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-di Ketone synthesis

[0147] Mix 1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethylamide (1.0g, 3.7mmol) and 3-acetamidophthalic anhydride (751mg, 3.66mmol ) in acetic acid (20 mL) was heated at reflux for 15 h. The solvent was removed under vacuum to obtain an oil. The resulting oil was chromatographed to obtain the product as a yellow solid (1.0 g, 59% yield): mp, 144°C; 1 H NMR (CDCl 3 )δ:1.47(t,J=7.0Hz,3H,CH 3 ),2.26(s,3H,CH 3 ),2.88(s,3H,CH 3 ),3.75(dd,J=4.4,14.3Hz,1H,CH),3.85(s,3H,CH3),4.11(q,J=7Hz,2H,CH 2 ),5.87(dd,J=4.3,10.5Hz,1H,NCH),6.82-6.86(m,1H,Ar),7.09-7.11(m,2H,Ar),7.47(d,J=7Hz,1H, Ar),7.64(t,J=8Hz,1H,Ar),8.74(d,J=8Hz,1H,Ar),9.49(br s,1H,NH); 13 C NMR (CDCl 3 )δ:14.61,24.85,41.54,48.44,54.34,55.85,64.43,111.37,112.34,115.04,118.11,120.21,124.85,129.17,130.96,136.01,137.52,148.54,149.65,167.38,169.09,169.40;对C 22 h 24 NO 7 Anal. Calcd. for S: C, ...

Embodiment 2

[0148] 5.2 Example 2: (+) 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1, Synthesis of 3-diketones

[0149] Preparation of 3-aminophthalic acid

[0150] 10% Pd / C (2.5 g), 3-nitric acid (75.0 g, 355 mmol) and ethanol (1.5 L) were charged to a 2.5 L Parr hydrogenator under nitrogen atmosphere. Hydrogen was bubbled through the reaction vessel until 55 psi was reached. The hydrogen pressure was maintained between 50 and 55 psi and the mixture was shaken for 13 hours. The hydrogen was released and the mixture was purged 3 times with nitrogen. The suspension was filtered through a bed of celite and rinsed with methanol. The filtrate was concentrated in vacuo. The resulting solid was reslurried in ether and isolated by vacuum filtration. The solid was dried in vacuo to constant weight to afford 54 g (84% yield) of 3-aminophthalic acid as a yellow product. 1 H-NMR(DMSO-d6)δ:3.17(s,2H),6.67(d,1H),6.82(d,1H),7.17(t,1H),8-10(br,s,2H); 13 C-NMR (...

Embodiment 3

[0158] 5.3 Example 3: Cyclopropanecarboxylic acid {2-[(1S)-1-(3-ethoxy-4-methoxy-phenyl)-2-methane-sulfonyl-ethyl]-3-oxo Synthesis of -2,3-dihydro-1H-isoindol-4-yl}-amide

[0159]Preparation of methyl 2-methyl-6-nitrobenzoate

[0160] 2-Methyl-6-nitrobenzoic acid (300.0 g, 1.66 moles, obtained from Acros Organics, Morris Plains, NJ) and trimethyl orthoacetate (298.3 g, 2.48 moles of the mixture obtained from Aldrich Chemicals, Milwauke, WI) was charged to a 3 L three-necked flask. The reaction mixture was gradually heated, and low-boiling components generated during the reaction were distilled off to an internal temperature of 95-100°C. After 2 hours, the reaction mixture was cooled to 20-25°C over 1-2 hours. After adding heptane (1.50 L from aldrich Chemicals) to the reaction mixture over 1.0-1.5 hours, when it became cloudy, seed it with methyl 2-methyl-6-nitrobenzoate (0.5 g). into the reaction mixture. The suspension was cooled to 0-5°C within 0.5-1 hour and kept at 0...

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Abstract

Provided herein are controlled release oral dosage forms of poorly soluble drugs, methods of making the dosage forms, and methods of their use for the treatment of various diseases and / or disorders.

Description

[0001] This application claims priority to US Provisional Patent Application No. 61 / 424,003, filed December 16, 2010, the entire contents of which are incorporated herein by reference. 1. Technical field [0002] Provided herein are controlled release oral dosage forms of poorly soluble drugs, methods of making the dosage forms, and methods of using them to treat various diseases and / or conditions. 2. Background technology [0003] One goal in developing a drug is to provide a dosage form that enables the drug to maintain in a subject a certain amount or concentration of drug that will remain constant for hours. This is usually not achievable with conventional rapidly disintegrating tablets, which immediately release the active ingredient contained within. To this end, dosage forms have been developed which release the drug contained therein continuously in a controlled manner and over a sustained period of time. Oral controlled drug delivery is typically achieved through s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K9/22A61K31/4035A61K9/20A61K9/00
CPCA61K9/0065A61K9/2027A61K9/2031A61K9/205A61K9/2054A61K9/2086A61K9/209A61K31/4035A61P35/00A61P35/02A61P43/00A61K47/34A61K47/36A61K47/38
Inventor 陈明璋许浩华沈小乐
Owner AMGEN (EURO) GMBH
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