Appeal 2007-0711
Reexamination 90/006,706
selector, which is also useful in achieving the enantiomeric separation of
amines, alcohol derivatives, epoxides and sulfoxides” (Pirkle, Abstract).
Pirkle’s separation process does not employ a simulated moving bed system.
Like Negawa, however, Pirkle’s process is designed to separate optically
active isomers of medicinals, e.g., anti-inflammatory agents (Pirkle, col. 7,
ll. 17-29; col. 8, ll. 17-40), such as ibuprofen (Pirkle, col. 8, l. 23). Pirkle
teaches the separation of optically active medicinals using a chiral stationary
phase and an achiral mobile phase which contains a chiral selector (Pirkle,
col. 21, l. 21, to col. 22, l. 68). Pirkle teaches (Pirkle, col. 22, ll. 43-51):
Two mobile phases were separately utilized: Mobile Phase A,
which comprised 5% 2-propanol and 0.1% acetic acid in hexane, and
Mobile Phase B, which comprised 20% 2-propanol, 0.1% acetic acid
and 0.1% triethylamine in hexane.
Chromatographic data for naproxen and nine other α-aryl acetic
acid compounds were obtained using the (R,R) configuration of CS-
10 of the invention. The results are presented … in Table 9.
Table 9 reports the “Separation of Underderivatized naproxen and other
arylacetic acid compounds on CSP-10” (Pirkle, col. 22, Table 9). The
enantiomeric medicinal mixtures to be separated into their chiral isomers
include naproxen, ibuprofen, ketoprofen, flurbiprofen, pirprofen, fenoprofen,
cicloprofen, carprofen, tiaprofenic acid, and etodolac (Pirkle, col. 22, Table
9). Table 9 is said to report the capacity factor (k’1) and chromatographic
separation factor (α) for the first isomer of each enantiomeric mixture to be
separated employing first Mobile Phase A and then employing Mobile Phase
B. The data reported in Pirkle’s Table 9 indicates that isomers of certain
enantiomeric medicinal mixtures, e.g., ibuprofen, flurbiprofen, and etodolac,
were separated using a Mobile Phase A having low k’1 (capacity factor)
10
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