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Polymorphic forms of nateglinide

A technology of nateglinide and crystal form, applied in the field of solid-state chemistry, can solve the problems of unstable and easy-to-change B-type crystals

Inactive Publication Date: 2006-01-18
TEVA PHARMA IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] According to U.S. Patent No. 5,463,116, DSC shows that the B-type crystals are unstable and prone to change when milled

Method used

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  • Polymorphic forms of nateglinide
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  • Polymorphic forms of nateglinide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0193] Example 1 - This example illustrates the preparation of various nateglinide crystal forms from solution

[0194] Nateglinide (5g) was placed in an Erlenmeyer flask and heated to a specific temperature. The solvent was added in 1 ml portions (in some cases in 5 ml portions) until a clear solution formed. If a clear solution did not result after addition of 150 ml of the solvent, the hot mixture was filtered.

[0195] The clear solution crystallized at room temperature. If no or very few crystals appeared, the solution was frozen at 3°C. The precipitate was filtered off (at room temperature or 5°C, depending on the crystallization temperature), weighed and divided into two equal portions. One portion was dried at 50°C under reduced pressure (20-30mmHg) for about 3-10 hours to constant weight (±0.01g). Details are listed in Table IV.

[0196] solvent

L / S,

ml / g

T，

℃

time

RT, h

time

3°C, h

crystal form

wet

...

Embodiment 2

[0200] Example 2 - This example illustrates the milling of Form H and U nateglinide in various solvents

[0201] Nateglinide (5g) was placed in an Erlenmeyer flask. The solvent was added in 1 ml portions to prepare a stirrable mixture. The bottle was stirred at room temperature with a magnetic stirrer. The solid was filtered off at room temperature, weighed, and divided into 2 equal portions. One portion was dried at 55°C under a pressure of 20-30mm / Hg to constant weight (±0.01g).

[0202] Details are listed in Tables V and VI.

[0203] start

[0204] start

Embodiment 3

[0205] Example 3 - This example illustrates the absorption of nateglinide to solvent vapor

[0206] Nateglinide (3.50 g) was added to a polypropylene jar and weighed. The jars were introduced into a larger polypropylene container containing solvent and stored at room temperature. The jar was removed from the container and weighed (Wfinal). The can contents are divided into 2 parts. One portion was dried to constant weight (±0.01 g) at 55°C under 20-30 mmHg pressure. Details are listed in Table VII.

[0207] NTGW,

[0208] Legend: Brutto - start weight of tank with NTG; Wfinal - final weight of tank with NTG after exposure; Δ - excess weight

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PUM

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Abstract

Provided are crystalline forms of nateglinide, labeled forms A, C, D, F, G, I, J, K, L, M, N, O, P, Q, T, U, V, Y, alpha, beta, gamma, delta, epsilon, sigma, theta and omega, processes for their preparation and processes for preparation of other crystalline forms of nateglinide. Also provided are their pharmaceutical formulations and methods of administration.

Description

[0001] Cross References to Related Applications [0002] This application claims U.S. Provisional Application Serial Nos. 60 / 396,904 (filed July 18, 2002), 60 / 413,622 (filed September 25, 2002), 60 / 414,199 (filed September 26, 2002), 60 / 423,750 ( 5 November 2002), 60 / 432,093 (filed 10 December 2002), 60 / 432,962 (filed 12 December 2002), 60 / 442,109 (filed 23 January 2003), 60 / 449,791 (filed February 24, 2003), 60 / 479,016 (filed June 16, 2003), and 10 / ____ (filed July 3, 2003, attorney docket 1662 / 60606), which The entire content of is incorporated herein by reference. field of invention [0003] The present invention relates to the solid state chemistry of nateglinide. Background of the invention [0004] Nateglinide, known as (-)-N-(trans-4-isopropylcyclohexanecarbonyl)-D-phenylalanine, has the following structure and properties: [0005] [0006] Molecular formula C 19 h 27 NO 3 [0007] Molecular weight 317.42 [0008] Exact mass 317.199093 [0009] Composition...

Claims

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Application Information

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IPC IPC(8): C07C231/24C07C233/63A61K31/16A61P3/00
Inventor R·亚哈罗米E·夏皮罗B·-Z·多利茨基I·戈兹兰B·戈姆S·维策尔
Owner TEVA PHARMA IND LTD
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