Ex Parte Chang et al

Patent Trial and Appeal BoardMay 3, 2017

13816620 (P.T.A.B. May. 3, 2017)

United States Patent and Trademark Office 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 APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 13/816,620 04/10/2013 Christopher J. Chang BERK-146 9050 84220 7590 05/05/2017 UC Berkeley - OTL Bozicevic, Field & Francis LLP 201 REDWOOD SHORES PARKWAY SUITE 200 REDWOOD CITY, CA 94065 EXAMINER PERREIRA, MELISSA JEAN ART UNIT PAPER NUMBER 1618 NOTIFICATION DATE DELIVERY MODE 05/05/2017 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): docket@bozpat.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte CHRISTOPHER J. CHANG and ALEXANDER R. LIPPERT1 Appeal 2016-006226 Application 13/816,620 Technology Center 1600 Before FRANCISCO C. PRATS, JOHN G. NEW, and JOHN E. SCHNEIDER, Administrative Patent Judges. SCHNEIDER, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35U.S.C. § 134 involving claims to compounds used for imaging hydrogen peroxide in vivo, which have been rejected as obvious. We have jurisdiction under 35 U.S.C. § 6(b). We affirm. STATEMENT OF THE CASE Reactive oxygen species such as hydrogen peroxide “are involved in various cell signaling pathways that are necessary for cell growth and survival.” Spec. 13. Various efforts to detect hydrogen peroxide have been 1 Appellants identify the Real Party in Interest as The Regents of the University of California. Appeal Br. 3. Appeal 2016-006226 Application 13/816,620 made to help understand the role of reactive oxygen species in health and disease. Spec. Tflf 3 and 4. The Specification describes compositions for imaging hydrogen peroxide in vivo. Spec. 7. Claims 1, 3—8, and 10-12 are on appeal.2 Claim 1 is the sole independent claim and reads as follows: 1. A compound of the formula: Q v) wherein Z is a [sic] aryl or a heteroaryl group, that includes one or more isotopically labeled atoms capable of being hyperpolarized by dynamic nuclear polarization. Claims 1, 3—8, and 10—12 stand rejected under 35 U.S.C. § 103(a) as unpatentable over Ropp3 in view of Larsen4 and Tang5, in further view of Sutherlin6 and Yu.7 2 Claims 1—24 are pending in the application but claims 2, 9, and 13—24 have been withdrawn from consideration. Final Act. 2. 3 Gus A. Ropp, Studies Involving Isotopically Labeled Formic Acid and its Derivatives. V. Studies of the Decarbonylation of Formic, Benzoylformic and Triphenylacetic Acids in Sulfuric Acid, 82 J. Am. Chem. Soc. 842—852 (1960) (“Ropp”). 4 Peder Olesen Larsen and Elzbieta Wieczorkowska, Syntheses of14C- Labeled Cinnamic, Mandelic, Phenylacetic, Phenylglyoxylic, and Phenylpyruvic Acids, 10 J. Labeled Comp. 287—296 (1974) (“Larsen”). 5 Tang et al., US 4,268,687, issued May, 19, 1981 (“Tang”). 6 Sutherlin, US 5,180,796, issued Jan. 19, 1993 (“Sutherlin”). 7 Yu et al., US 5,091,171, issued Feb. 25, 1992 (“Yu”). 2 Appeal 2016-006226 Application 13/816,620 DISCUSSION Issue The issue with respect to the rejection is whether a preponderance of evidence supports the Examiner’s finding that claims 1, 3—8, and 10—12 would have been obvious over Ropp combined with Larsen, Tang, Sutherlin and Yu under 35 U.S.C. § 103(a). The Examiner finds that Ropp teaches isotope fractionation studies using 14C labeled compounds. Ans. 3. The Examiner finds that Ropp teaches that the same general methods have been used to evaluate 13C and 15N isotopes. Id. The Examiner finds that Larsen teaches the labeled phenylglyoxylic acid can be produced from benzoyl chloride and cuprous cyanide. Id. The Examiner finds that Tang discloses the cyanation of benzoyl chloride to produce benzoyl cyanide which is in turn hydrolyzed to produce the corresponding keto acid. Id. The Examiner finds that Sutherlin teaches the use of benzoyl-carbonyl-13C-chloride. Ans. 6. The Examiner concludes that At the time of the invention it would have been obvious to one ordinarily skilled in the art to substitute the 13C for 14C and prepare a benzoylformic-l-13C from the known benzoyl- carbonyl-13C-chloride taught by Sutherlin as Larsen et al. teaches that labeled phenylglyoxylic acid has been produced from benzoyl chloride and cuprous cyanide via the nitrile and Tang et al. teaches the cyanation of benzoyl chloride produces benzoyl cyanide that can be hydrolyzed to produce the corresponding keto-acid. Therefore, at the time of the invention it would have been obvious and predictable to one ordinarily skilled in the art to prepare a 13C- benzoylformic acid via the known technique of producing labeled 14C-labeled phenylglyoxylic acid from benzoyl chloride and cuprous cyanide via the nitrile. 3 Appeal 2016-006226 Application 13/816,620 Ans. 6 Appellants contend that Ropp actually teachess away from the invention, that is, Ropp cites to Grovenstein,8 * * *which teaches that 13C measurements are rarely feasible unless the product labled with 13C is carbon dioxide or another gas such as methane. Appeal Br. 5—6. Appellants argue that the remaining references do not provide any guidance as to the use of 13C in light of the teachings of Ropp. Appeal Br. 7—8. Analysis We adopt the Examiner’s findings of fact, reasoning on scope and content of the prior art, and conclusions as set out in the Final Action and the Examiner’s Answer regarding this rejection. We find the Examiner has established that claim 1 would have been obvious over Ropp combined with Larsen, Tang, Sutherlin, and Yu. Appellants have not produced evidence showing, or persuasively argued, that the Examiner’s determinations underlying the obviousness conclusion are incorrect. Only those arguments made by Appellants in the Briefs have been considered in this Decision. Arguments not presented in the Briefs are waived. See 37 C.F.R. § 41.37(c)(l)(iv) (2015). We address Appellants’ arguments below. Appellants contend that Ropp, by citing to Grovenstein, teaches away from using 13C except in limited circumstances such as labeling carbon dioxide or other gases. Appeal Br. 5—6. We are unpersuaded. Although Grovenstein teaches that the use of 13C may be limited, as the Examiner 8 Erling Grovenstein, Jr. and Gus A. Ropp, Carbon-13 Isotope Fractionation as a Criterion of the Mechanism of Bromodecarboxylation of 3,5-Dibromo- 4-hydroxybenzoic Acid, 78 J. Am. Chem. Soc. 2560—2562 (1955) (“Grovenstein”). 4 Appeal 2016-006226 Application 13/816,620 points out, Ropp teaches that the same methods used in Ropp have been used to evaluate 13C isotopes. Ans. 5; see also Ropp 844. The Examiner also points out that Grovenstein teaches that 13C yields superior precision over14C . Ans. 7; see also Grovenstein 2561, n.8. As the Examiner also notes (Ans. 7), Ropp teaches that carbon monoxide is released as part of the decarbonylation of benzoylformic -1-14C acid and that the carbon monoxide contains the label. Ropp 847. The use of 13C would fall within one of the specific exceptions recited in Grovenstein. See Grovenstein 2561, n.8 (carbon-13 useful where label-containing product “is carbon dioxide or some other gas”). Finally, as the Examiner finds (Ans. 8), Sutherlin teaches the use of 13C-labeling in compounds other than gases and similar to those recited in the instant claims. Sutherlin, col. 6,11. 8—15. We agree with the Examiner that it would have been obvious to one ordinarily skilled in the art to substitute one known isotope for another natural and stable isotope chosen from a finite list of isotopes to yield predictable results. Ans. 7. We are also not persuaded by Appellants’ argument that the remaining references do not provide sufficient guidance to make the proposed combination. Appeal Br. 7. As discussed above, Sutherlin teaches that the use of 13C as a label for other than gases was known in the art. Moreover, the teachings of Ropp and Grovenstein do not teach way from the proposed combination. Conclusion of Law We conclude that the Examiner has established by a preponderance of the evidence that claim 1 would have been obvious over Ropp combined with Larsen, Tang, Sutherlin, and Yu under 35 U.S.C. § 103(a) 5 Appeal 2016-006226 Application 13/816,620 Claims 3—8, and 10—12 have not been argued separately and therefore fall with claim 1. 37 C.F.R. § 41.37(c)(l)(iv). SUMMARY We affirm the rejection under 35 U.S.C. § 103(a). TIME PERIOD FOR RESPONSE No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a). AFFIRMED 6