Process for the Synthesis of Chiral Propargylic Alcohols
US-2016326101-A1 · Nov 10, 2016 · US
US8946474B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-8946474-B2 |
| Application number | US-201113806391-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jun 24, 2011 |
| Priority date | Jun 30, 2010 |
| Publication date | Feb 3, 2015 |
| Grant date | Feb 3, 2015 |
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The present invention relates to the crystalline, polymorphic Form X of the calcimimetic compound {4-[(1R,3S)-3-((R)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-phenoxy}-acetic acid, to methods of preparation thereof, to methods of characterization thereof by single crystal X-Ray crystallography (XRC), X-Ray Powder diffractometry, attenuated total reflectance Fourier transform infrared (ATR-FTIR) spectroscopy, Solid State NMR spectroscopy and Differential Scanning Calorimetry (DSC), and to its use. The invention also relates to the preparation of Form X by crystallization from a saturated solution of {4-[(1R,3S)-3-((R)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-phenoxy}-acetic acid in a C 1 -C 6 alkyl alcohol, or alternatively by precipitation from a neutralized saponification reaction mixture following the alkaline hydrolysis of a C 1 -C 6 alkyl ester of {4-[(1R,3S)-3-((R)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-phenoxy}-acetic acid.
Opening claim text (preview).
The invention claimed is: 1. A crystalline form of {4-[(1R,3S)-3-((R)-1-Naphthalen-1-yl-ethylamino)-cyclopentyl]-phenoxy}-acetic acid which has an X-ray powder diffraction pattern that exhibits characteristic peaks expressed in 2θ at approximately 8.0, 11.3, 11.4, 15.0, 18.2 and 21.5. 2. The crystalline form according to claim 1 which belongs to the orthorhombic space group P2 1 2 1 2 1 having unit-cell parameters a=8.7299(17) Å, b=14.822(3) Å and c=16.353(3)…
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