Ex Parte Manners et alDownload PDFPatent Trial and Appeal BoardJul 8, 201611289240 (P.T.A.B. Jul. 8, 2016) Copy Citation UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE FIRST NAMED INVENTOR 111289,240 11129/2005 Gary D. Manners 25278 7590 07112/2016 USDA-ARS-OFFICE OF TECHNOLOGY TRANSFER PA TENT ADVISORS OFFICE GWCC - Rm 4-1188 5601 Sunnyside Avenue Beltsville, MD 20705 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. 0126.04 7635 EXAMINER GOON, SCARLETT Y ART UNIT PAPER NUMBER 1673 NOTIFICATION DATE DELIVERY MODE 07/12/2016 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): Claudia.Reynolds@ars.usda.gov Robin.McCormick@ars.usda.gov PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte GARY D. MANNERS and ANDREW P. BREKSA III Appeal2013-000987 Application 11/289,240 Technology Center 1600 Before DONALD E. ADAMS, LORA M. GREEN, and RICHARD M. LEBOVITZ, Administrative Patent Judges. LEBOVITZ, Administrative Patent Judge. DECISION ON APPEAL 1 This appeal involves claims directed to an analytically certified single component amorphous solid consisting essentially of a purified alkali metal salt of an individual species of isolated limonoid glycoside mono-carboxylic acid. Appellants appeal from the Examiner's final rejection of claims 17, 20, 39, and 40 as obvious under 35 U.S.C. § 103. We have jurisdiction under 35 U.S.C. § 134. The obviousness rejections are affirmed. 1 Appellants identify the real party in interest as "The United States of America, as represented by the Secretary of Agriculture" (Br. 3). Appeal2013-000987 Application 11/289,240 STATEMENT OF CASE Claims 17, 20, 39, and 40 are pending. The claims stand finally rejected by the Examiner as follows: 1. Claims 17 and 392 under 35 U.S.C. § 103(a) (pre-AIA) as obvious in view of Guthrie et al. (U.S. Patent 6,251,400, issued June 26, 2001) ("Guthrie"), Berge (Pharmaceutical Salts, 66 J. Pharmaceutical Sciences 1- 19 (1977)), and Lipinski ("Aqueous Solubility in Discovery, Chemistry, and Assay Changes" in Drug Bioavailability, Estimation of Solubility, Permeability, Absorption and Bioavailability, Han van de Waterbeemd et al. eds., pp. 215-231 (2003)). Final Rej. 4. 2. Claims 17, 20, 39, and 40 under 35 U.S.C. § 103(a) (pre-AIA) as obvious in view of Tian (Differential Inhibition of Human Cancer Cell Proliferation by Citrus Limonoids, 40 Nutrition and Cancer 180-184 (2001)), Guthrie, Berge, and Lipinski. Final Rej. 12. Claim 17 is representative and reads as follows: 17. An analytically certified single component amorphous solid consisting essentially of a purified alkali metal salt of an individual species of isolated limonoid glycoside mono- carboxylic acid made according to a production scale method compnsmg: (i) separating limonoid glycoside mono-carboxylic acids from limonoid glycoside di-carboxylic acids in an aqueous solution, wherein the separating comprises: (a) acidifying the aqueous solution to achieve a pH of less than 6.5; 2 We note that Appellants' Brief refers to claim 20 as rejected. However, both the Final Rejection and Answer states claims 17 and 39 are rejected. 2 Appeal2013-000987 Application 11/289,240 (b) applying the acidified aqueous solution from step (a) to a strong anion ion exchange resin; ( c) eluting the strong anion ion exchange resin with a linear gradient of an ionic solvent; and ( d) collecting eluate fractions that comprise separated limonoid glycoside mono-carboxylic acids and separated limonoid glycoside di-carboxylic acids; (ii) separating an individual species of limonoid glycoside mono-carboxylic acid from other species of limonoid glycoside mono-carboxylic acid in an aqueous solution, wherein the separating comprises: ( e) applying the collected eluate fractions comprising limonoid glycoside mono-carboxylic acids from step (i)( d) to an aromatic-selective chromatographic medium; (f) eluting the aromatic-selective chromatographic medium with a polar solvent; and (g) collecting eluate fractions comprising the separated individual species of limonoid glycoside mono- carboxylic acid, thereby separating the individual species of limonoid glycoside mono-carboxylic acid from the other species of limonoid glycoside mono-carboxylic acid in an aqueous solution; (iii) combining eluate fractions from step (ii)(g) which comprise the same individual species of limonoid glycoside mono-carboxylic acid to provide combined fractions; (iv) adding an aqueous alkali metal base to the combined fractions to make the combined fractions alkaline; (v) applying the alkaline combined fractions from step (iv) to a styrene divinylbenzene resin; (vi) washing the styrene divinylbenzene resin with water to remove excess alkali; (vii) eluting the styrene divinylbenzene resin with a polar solvent; (viii) collecting eluate fractions comprising the individual species of limonoid glycoside mono-carboxylic acid; and (ix) evaporating the polar solvent present in the collected fractions, thereby yielding an analytically certified single component amorphous solid consisting essentially of a purified 3 Appeal2013-000987 Application 11/289,240 alkali metal salt of the individual species of isolated limonoid glycoside mono-carboxylic acid. Product-by-process claims Independent claim 17 is directed to an "analytically certified single component amorphous solid consisting essentially of a purified alkali metal salt of an individual species of isolated limonoid glycoside mono-carboxylic acid." The claim is a "product-by-process" because it claims the salt product by the process by which it is made. With respect to product-by-process claims, it is "'well settled that the presence of process limitations in product claims, which product does not otherwise patentably distinguish over the prior art, cannot impart patentability to that product.'" SmithKline Beecham Corp. v. Apotex Corp., 439 F.3d 1312, 1318 (Fed. Cir. 2006) (quoting In re Stephens, 345 F.2d 1020, 1023 (CCPA 1965). "[E]ven thoughproduct-by- process claims are limited by and defined by the process, determination of patentability is based on the product itself." Jn re Thorpe, 777 F.2d 695, 697 (Fed. Cir. 1985). Process steps are relevant to the extent they change a structure or characteristic of the product which distinguishes it from products made by other processes. See In re Garnero, 412 F.2d 276, 279 (CCPA 1979). Independent claims 20, 39, and 40 are also product-by- process claims. Obviousness Rejections Rejections The Examiner found that Guthrie describes the claimed "limonoid glycoside mono-carboxylic acid" as a therapeutic agent to treat cancer and other diseases. Final Rej. 4--5. However, the Examiner found that Guthrie does not describe the limonoid in the form of an alkali metal salt or as an 4 Appeal2013-000987 Application 11/289,240 amorphous solid as required by the claim. Id. The Examiner found that Berge describes the advantages of an alkali metal salt for pharmaceutical compositions. Id. at 5-6. Furthermore, the Examiner found that Lipinski teaches that compounds frequently exist in the amorphous form and such form is advantageous because it is more soluble in all solvents. Id. at 6. Based on these teachings, the Examiner determined it would have been obvious to one of ordinary skill in the art to convert Guthrie's limonoid to an alkali metal salt in amorphous form for the advantages described by Berge and Lipinski. Id. at 6-7. The rejection based on Tian uses the same rationale as the one for Guthrie, Berge, and Lipinski, but relies on Tian for the claimed "limonoid glycoside mono-carboxylic acid." Id. at 12-13. Citing the Bennett3 and Moodley4 publications, Appellants contend that it was known in the art that the addition of an alkali metal base will convert the structure of the liminoid compound to another form and produce a mixture of liminoid compounds. Br. 16-18. For this reason, Appellants contend that the claimed "amorphous solid consisting essentially of a purified alkali metal salt of an individual species of isolated limonoid glycoside mono-carboxylic acid" is not possible and there would have been no reasonable expectation of success. Id. at 18, 22. Appellants also argue the cited publications do not teach the process steps recited in the claims nor how to overcome the problem of making the alkali metal salt. Id. at 22. 3 Bennett et al., Limonoid Glucosides in Citrus Aurantium, 30 Phytochemistry 3803-3805 (1991) ("Bennett"). 4 Moodley et al., Micellar electrokinetic capillary chromatography of limonoid glucosides from citrus seeds, 718 J. Chromatogr. A 187-193 (1995) ("Moodley"). 5 Appeal2013-000987 Application 11/289,240 Appellants make the same arguments for the rejection based on Tian. Id. at 23-31. Discussion Appellants' principal argument is that the alkali conditions required to make the claimed limonoid alkali metal salt would convert the structure of the limonoid to another form, producing a mixture of limonoids in contrast to the claim which requires a "single component" that "consists essentially" of the limonoid alkali metal salt. The evidence to support this argument is based on the Bennett and Moodley publications. Bennett teaches the alkaline conversion of ichangin 17-Beta-D-glucopyranoside to 19- hydroxydeacetylnomilinic acid 17-beta-D-glucopyranoside. Bennett 3805. Moodley teaches the alkaline conversion of nomilin glycoside to obacunone glucoside at a pH greater than 7.5. Moodley 189. Based on these two teachings for alkaline conversion of two specific limonoid compounds into other structures, Appellants state that alkaline conditions are undesirable for limonoids and must be avoided. Br. 17. Appellants' argument is not supported by a preponderance of the evidence. First, as found by the Examiner, neither of the two starting compounds described in Bennett and Moodley correspond to those compounds in the Guthrie and Tian publications relied upon by the Examiner. Answer 15. Appellants have not provided evidence that one of ordinary skill in the art would have generalized the teachings for these specific compounds to other limonoid compounds. Id. at 16-17. As indicated by the Examiner, there are structural differences between the compounds claimed and described in Guthrie and Tian and those said by 6 Appeal2013-000987 Application 11/289,240 Bennett and Moodley to be unstable under alkaline conditions. Id. Thus, the Examiner had scientific basis to find Appellants' alkaline instability argument unpersuasive. Appellants acknowledged the Examiner's argument (Br. 27, 30), but did not identify an error in it. Furthermore, the Examiner found that the skilled worker would have inferred that obacunone glucoside, a monocarboxylic acid limonoid disclosed by Tian and encompassed by the claims, is stable under alkaline conditions. Answer 20. Specifically, Moodley teaches that, at a pH greater than 7.5, nomilin glucoside is converted to obacunone glucoside, indicating that the obacunone glucoside is a stable product of the alkaline reaction. Answer 20; Moodley 189. Appellants did not rebut the Examiner's scientific reasoning, which we find to be fact-based and credible. Appellants also argue that the cited publications do not teach the process steps recited in the claims. Br. 22. As discussed above, all the independent claims are "product-by-process" claims and are not limited by the process by which the purified alkali metal salt of the isolated limonoid glycoside mono-carboxylic acid made, unless the process limitations change the structure of the recited product. Thorpe, 777 F.2d at 697; Garnero, 412 F.2d at 279. Appellants have not provided evidence that the process by which the claimed limonoid is made makes it different from the same limonoids described in Guthrie and Tian. Consequently, Appellants' argument are unavailing. Appellants also argue that the prior art teaches that there were known problems with obtaining the claimed "analytically certified single component amorphous solid consisting essentially of a purified alkali metal salt of the individual species of isolated limonoid glycoside mono-carboxylic 7 Appeal2013-000987 Application 11/289,240 acid," such as the structural conversion associated with alkaline conditions. Br. 22, 29. However, Appellants do not explain how they solved the problem nor how their solution is any different from conventional methods for preparing alkali salts. For the foregoing reasons, we affirm the obviousness rejections of claim 17. Claims 20, 39, and 40 were not argued separately and fall with claim 17. 37 C.F.R. § 41.37(c)(iv). TIME PERIOD No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a)(l )(iv). AFFIRMED 8 Copy with citationCopy as parenthetical citation