Ex Parte Daeuwel et alDownload PDFPatent Trial and Appeal BoardMay 11, 201612158543 (P.T.A.B. May. 11, 2016) Copy Citation UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 12/158,543 06/20/2008 123223 7590 05/13/2016 Drinker Biddle & Reath LLP (WM) 222 Delaware A venue, Ste. 1410 Wilmington, DE 19801-1621 FIRST NAMED INVENTOR Juergen Daeuwel UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O. Box 1450 Alexandria, Virginia 22313-1450 www .uspto.gov ATTORNEY DOCKET NO. CONFIRMATION NO. 12810-00717-US 9151 EXAMINER KEYS,ROSALYNDANN ART UNIT PAPER NUMBER 1671 NOTIFICATION DATE DELIVERY MODE 05/13/2016 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address( es): IPDocketWM@dbr.com penelope.mongelluzzo@dbr.com DBRIPDocket@dbr.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte JUERGEN DAEUWEL, VOLKER RUEDIGER SPORYS, MARTIN VOELKERT, and HOLGER BUEHLER Appeal2013-007594 Application 12/158,543 Technology Center 1600 Before DONALD E. ADAMS, MELANIE L. McCOLLUM, and ULRIKE W. JENKS, Administrative Patent Judges. ADAMS, Administrative Patent Judge. DECISION ON APPEAL 1 This appeal under 35 U.S.C. § 134(a) involves claims 16-19, 21, 22, and 24-27 (App. Br. 2). Examiner entered a rejection under 35 U.S.C. § 103(a). We have jurisdiction under 35 U.S.C. § 6(b). We REVERSE. STATEMENT OF THE CASE Appellants' "invention relates to a process for preparing a specific a- chiral chloromethyl compound in pure or enriched form by distillative removal of the compound mentioned from substance mixtures which comprise this compound and higher-boiling impurities" (Spec. 1 ). 1 Appellants identify the Real Party in Interest as "BASF SE" (App. Br. 1 ). Appeal2013-007594 Application 12/158,543 Claim 16 is representative and reproduced in the Claims Appendix of Appellants' Brief. Claims 16-19, 21, 22, and 24-27 stand rejected under 35 U.S.C. § 103(a) as unpatentable over the combination of Herold,2 Zaitsev,3 Sandham, 4 and Rueger. 5 ISSUE Does the preponderance of evidence relied upon by Examiner support a conclusion of obviousness? FACTUAL FINDINGS (FF) FF 1. Herold discloses the "purification of a compound of [Appellants'] claimed formula (I), which is an intermediate [in] the [preparation] of 8- amino-y-hydroxy-W~ 1-alkanecarbox-amides (Ans. 6, citing Herold 17-18: Example Al). FF 2. Examiner finds that Herold fails to suggest the "purification of the crystallized product via a continuous distillation; [or] obtaining the optically active compound of formula (I) in 90 % to 99% by weight" (Ans. 6) FF 3. Examiner relies on Zaitsev to suggest "that in fractional crystallization the crystalline product is always contaminated by trapped inclusions of the mother melt" and that "[t]he distillation melting process 2 Herold et al., WO 02/08172 Al, published Jan. 31, 2002. 3 E.V. Zaitsev et al., Purification of substances by distillation crystallization and distillation melting, 810-816, translated from 5 VYSOKOCHISTYE VESHCHESTVA 101-108 (1989) (see Ans. 5). 4 David A. Sandham, et al., A convergent synthesis of the renin inhibitor CGP60536B, 41 TETRAHEDRON LETTERS 10091-10094 (2000). 5 Rueger et al., A convergent synthesis approach towards CGP60536B, a non-peptide orally potent renin inhibitor, via an enantiomerically pure keto lactone intermediate, 41 TETRAHEDRON LETTERS 10085-10089 (2000). 2 Appeal2013-007594 Application 12/158,543 allows one to increase the purity of the crystallized product thereby obtaining high-purity substances, up to 99.99%" (Ans. 7, citing Zaitsev 816; and 815: Table 2). FF 4. Examiner finds that the combination of Herold and Zaitsev fail to suggest the preparation of a compound having Appellants' "formula (I) by reacting an optically active alcohol of formula (II) with thionyl chloride and N,N-dimethylformamide" and relies on Sandham and Rueger to make up for this deficiency in the combination of Herold and Zaitsev (see Ans. 8). ANALYSIS Based on the combination of Herold, Zaitsev, Sandham, and Rueger, Examiner concludes that, at the time Appellants' invention was made, it would have been prima facie obvious to expect that a crystallized product [] of Herold [] contains at least some impurity, since Zaitsev [] teach that in fractional crystallization the crystalline product is always contaminated by trapped inclusions of the mother melt. [Thus,] [t]he skilled artisan would have [] found it obvious that the amount of the impurity and the yield of the crystallized product [] of Herold []. could be selected by modifying the crystallization conditions, as taught by Zaitsev et al. Th[erefore], based upon the teachings of Herold []. and Zaitsev [] obtaining a mixture comprising from 90-99% by weight of the optically active compound of [Appellants'] formula (la) would have been obvious to one having ordinary skill in the art. Further, the skilled artisan would have found it obvious that one could further increase the purity of the crystallized product (Al) of Herold[] to as high as 99.99% by utilizing the distillation melt technique, as disclosed by Zaitsev. (Ans. 7.) We are not persuaded. As Appellants explain, notwithstanding Examiner's assertion to the contrary "Zaitsev neither teaches nor suggests continuously feeding a liquid 3 Appeal2013-007594 Application 12/158,543 mixture into its process and continuously removing crystals and mother liquor as output streams," i.e. a continuous distillation (Reply Br. 2; cf Ans. 13 "Continuous distillation is an ongoing distillation in which a liquid mixture is continuously (without interruption) fed into the process and separated fractions are removed continuously as output streams as time passes during the operation."). Examiner recognizes, however, that Zaitsev teaches ... [that] the vapor is continuously drawn off, the fraction of the solid phase continually increases, and the fraction of the liquid phase decreases. The process is carried out until the liquid phase vanishes completely and the solid component, which is free of the mother liquid, remains in the condensed phase. (Ans. 13.) As Appellants explain, Examiner's reliance on Zaitsev, at best, suggests a "distillation crystallization process in a batch-type system ... where the separation of a single charge of a mixture of components is 'continuous' until complete" (Reply Br. 2, citing Zaitsev 813; cf Ans. 13")). In sum, Examiner failed to establish an evidentiary basis on this record to support a conclusion that the combination of Herold, Zaitsev, Sandham, and Rueger suggests the distillative removal of optically active compound of formula (I) by continuous distillation. Finally, we recognize Examiner's reliance on Fair6 to suggest that modifications could have been made to the method suggested by the combination of Herold, Zaitsev, Sandham, and Rueger (Ans. 18 ("the skilled artisan would find it obvious to adjust the distillation operating conditions based upon the substance being purified and the impurity being removed" and "make ... adjustments to allow one to operate the distillation 6 James R. Fair, Distillation, 8 KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY 739-785 (2001 ). 4 Appeal2013-007594 Application 12/158,543 continuously, such as taught by Fair ... most distillations conducted commercially operate continuously")). Examiner, however, fails to rely on Fair as part of the rejection before this panel for review. CONCLUSION OF LAW The preponderance of evidence relied upon by Examiner fails support a conclusion of obviousness. The rejection of claim 16-19, 21, 22, and 24- 27 under 35 U.S.C. § 103(a) as unpatentable over the combination of Herold, Zaitsev, Sandham, and Rueger is reversed. REVERSED 5 Copy with citationCopy as parenthetical citation