13312371 (P.T.A.B. May. 11, 2018)

Ex Parte HORMANN et al

Patent Trial and Appeal BoardMay 11, 2018

13312371 (P.T.A.B. May. 11, 2018)

UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 13/312,371 12/06/2011 80011 7590 05/15/2018 Sterne, Kessler, Goldstein & Fox P.L.L.C. 1100 New York Avenue, N.W. Washington, DC 20005 FIRST NAMED INVENTOR Robert Eugene HORMANN 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. 2584.0010003/RWE/MFG 3405 EXAMINER POPA, ILEANA ART UNIT PAPER NUMBER 1633 NOTIFICATION DATE DELIVERY MODE 05/15/2018 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): dlucas@intrexon.com e-office@sternekessler.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte ROBERT EUGENE and BING LI Appeal2016-006661 Application 13/312,371 1 Technology Center 1600 Before RICHARD M. LEBOVITZ, RY ANH. FLAX, and DAVID COTTA, Administrative Patent Judges. LEBOVITZ, Administrative Patent Judge. DECISION ON APPEAL This appeal involves claims directed to enantiomerically enriched compounds of the general Formula III. The Examiner rejected the claims as obvious under 35 U.S.C. Â§ 103 and on the ground of non-statutory double- patenting. Appellants appeal the rejections pursuant to 35 U.S.C. Â§ 134. We have jurisdiction under 35 U.S.C. Â§ 6(b ). The rejections are affirmed. STATEMENT OF THE CASE An oral hearing was held on April 3, 2018. The transcript of the hearing will be entered into the record in due course. Claims 3, 17, 20, and 27 are appealed. Appeal Br. 4. 1 The Appeal Brief ("Appeal Br.") 4 lists Intrexon Corporation, as the real- party-in-interest. Appeal2016-006661 Application 13/312,371 The claims stand rejected by the Examiner, as indicated in the Examiner's Answer ("Ans."), as follows: 1. Claims 3, 20, and 57 on the ground of nonstatutory obviousness- type double-patenting as obvious over claims 1--4 of Hormann '161 (U.S. Pat. No. 7,304,161 B2, issued Dec. 4, 2007) in view of Hsu (U.S. Pat. No. 6,013,836, issued Jan. 11, 2000), Zhang (Drug Discovery Today, 10(8):571- 577, April 2005), and Chiral Technologies (Laboratory Products and Services for Chiral Analysis and Separation, 2006 Edition). 2 Ans. 3. 2. Claims 3, 17, 20, and 57 on the ground of nonstatutory obviousness-type double-patenting as obvious over claims 1 and 2 of Hormann '315 (U.S. Pat. No. 7,456,315 B2, issued Nov. 25, 2008) in view of Hsu, Zhang, and Chiral Technologies. Ans. 4. 3. Claims 3, 20, and 57 on the ground of nonstatutory obviousness- type double-patenting as obvious over claims 1 and 3-7 of Hormann '962 (U.S. Pat. No. 5,482,962, issued Jan 9, 1996) in view of Hsu, Zhang, and Chiral Technologies. Ans. 5. 4. Claims 3, 20, and 57 provisionally on the ground of nonstatutory obviousness-type double-patenting as obvious over claims 1, 2, and 15 of co-pending Application No. 13/603,965 in view of Hsu, Zhang, and Chiral Technologies. Ans. 7. 5. Claims 3, 17, 20, and 57 on the ground ofnonstatutory obviousness-type double-patenting as obvious over claims 1 and 2 of 2 There are two excerpts from Chiral Technologies: one excerpt had numbered pages, but the second excerpt did not. The second excerpt contained a list of LC columns available from Chiral Technologies. 2 Appeal2016-006661 Application 13/312,371 Hormann '948 (U.S. Pat. No. 8,524,948 B2, issued Sep. 3, 2013) in view of Hsu, Zhang, and Chiral Technologies. Ans. 8. 6. Claims 3, 17, 20, and 57 under pre-AIA 35 U.S.C. Â§ 103(a) as obvious over Hormann' 146 (U.S. Pat. Appl. Publ. 2006/0020146 Al, Jan. 26, 2006) in view of Hsu, Zhang, and Chiral Technologies. Ans. 10. 7. Claims 3, 17, 20, and 57 under pre-AIA 35 U.S.C. Â§ 103(a) as obvious over Berger (J. Am. Chem. Soc., 2003, 125: 9596-9597) in view of Hormann '146, Feringa (Stereoselectivity of Pesticides: Biological and Chemical Problems, 1988, Chapter 15, p. 453-499), Hsu, and Leighton (WO 03/074534 Al, publ. Sep. 12, 2003). Ans. 11. CLAIMS Claim 3, which is the only independent claim on appeal, is directed to an enantiomerically enriched compound of Formula III. The formula represents a genus of compounds and is reproduced in the Claim Appendix. Claim 17, which depends from claim 3, recites specifically named compounds which are species of the genus of compounds of claim 3. DOUBLE-PATENTING REJECTIONS There are five obvious-type double-patenting rejections listed in the Examiner's Answer. See Rejections 1-5 listed above. Appellants did not provide different arguments for any of the five pending double-patenting rejections together. Consequently, we have addressed them together. 3 Appeal2016-006661 Application 13/312,371 Rejections The Examiner found that each of the cited patents and patent applications are directed to the same compounds which are claimed, but differ in not requiring an "enantiomeric enriched compound" where "the compound has an enantiomeric excess of at least 95%" as recited in independent claim 3. To meet this limitation, the Examiner cited Hsu, Zhang, and Chiral Technologies as evidence of a reason to separate enantiomers, the technology to do so, and of a reasonable expectation of success. Final Action ("Final Act.") 3--4. Findings of Fact ("FF") FPL Molecular chirality is a fundamental consideration in drug discovery, one necessary to understand and describe biological targets as well as to design effective pharmaceutical agents. Enantioselective chromatography has played an increasing role not only as an analytical tool for chiral analyses, but also as a preparative technique to obtain pure enantiomers from racemates quickly from a wide diversity of chemical structures. Different enantioselective chromatography techniques are reviewed here, with particular emphasis on the most widespread high performance liquid chromatography (HPLC) and the rapidly emerging supercritical fluid chromatography (SFC) techniques. This review focuses on the dramatic advances in the chiral stationary phases (CSPs) that have made HPLC and SFC indispensable techniques for drug discovery today. Zhang 571 (abstract) FF2. It is not uncommon for one enantiomer to be active while the other is toxic in biological systems. Thus, the FDA has required evaluation of each enantiomer in developing stereoisomeric 4 Appeal2016-006661 Application 13/312,371 drugs. .As a result, the pharmaceutical industry has raised its emphasis on the generation of enantiomerically pure compounds before undertaking phan11acokinetic, metabolic, physiological and toxicological evaluation in the search for drugs with greater therapeutic benefits and low toxicity. According to the recently survey by Israel Agranat, the distribution of worldwide approved dn1gs from 1983-2002 and FDA-approved drugs from 1991- 2002 indicate that single-enantiomers surpassed achirals whereas racemic dn1gs represented the rninority category. Zhang 571. FF3. Although a large number of approaches have been used to isolate single enantiomers, enantioselective chromatography using HPLC and SFC on chiral stationary phases (CSPs) has become the most widely utilized technique in the context of obtaining limited quantities (from mg to multi-grams) of pure enantiomers quickly5 particularly in dn1g discovery. The impetus for reliance on chromatography has been fueled by recent advances in CSPs that allow reliable, robust and efficient resolution of mg to gram quantities of chiral molecules in a matter of hours. Zhang 571. FF4. It is estimated that 1300 CSPs have been prepared, and over 200 CSPs have been commercialized. Thus, understanding and classi{ying the different CSPs is important for selecting the most suitable CSP to solve a particular problem Zhang 573. FF5. Strategies for fast enantioselective method development in drug discovery Enantioselective chromatography has advanced dramatically in the past two decades, led by the development of new CSPs. 5 Appeal2016-006661 Application 13/312,371 However, the demand for faster preparative and analytical chiral resolutions for a wide variety of new chemical entities continues to push the frontiers of current technologies. As there is no universal CSP, elucidation of the chiral recognition mechanisms operating at the molecular level is essential for further development in the field. Zhang 575 . .. __ , FF6. Currently, prediction of enantioselectivity for almost any CSPs is, practically speaking, still not feasible. In addition, small changes in solute structure and/or chromatographic environment often have great impact on the chiral resolution ability of many CSPs. Consequently, 'trial-and-error' screening of a set ofCSPs that offers a broad-spectrum of enantioselectivity in simple rnobile phase systems has been the most popular approach to chiral method development in drug discovery. Zhang 575. FF7. To facilitate this approach, three automated column screening strategies have been reported. Zhang 575 . ._, FF8. Very recently, a multi-column paraIIel screening approach with a circular dichroism signal poo Hng technique was reported. Five CSPs were screened sinmltaneously in parallel using a simple customized HPLC system with five lJ V detectors and one circular dichroism detector. An injected sample was carried by the mobile phase through an on-line pre-filter, then divided into five columns and UV detectors with even flow distribution accomplished via individually adjusted backpressures. . . . As shown in Figure 2, the enantioselectivity of sulconazole was screened on five CSPs in parallel resulting in a fivefold increase in throughput 6 Appeal2016-006661 Application 13/312,371 Zt' , <:.;75 ,11ang _ .. FF9. Figure 2 in Zhang is reproduced below: 2{1 30 40 50 min: Parallel chil!'al c"Olumn sueÂ·ening t1:hrornatograms of SukonazoleÂ· with CD signiil poollng... Mobffe pha-se: I 5% eth.ancl in 1'1-he~a:ne from 0-30 m~n and 25% ethana~ in n-hexan-e from 30-.55 min.FhwÂ· rate: 1 ml/min fur each cdumn. UV ~Â·ta:1''e'length: 225nm,CDviavcl-e~h235 rsm.(The\o;,.