Court Opinion

ID: 4687784
Source: CourtListenerOpinion
Date Created: 2021-05-18 15:01:12.012634+00
Date Added: 2024-06-11T08:04:43.374388
License: Public Domain

Case: 20-1956    Document: 33    Page: 1   Filed: 05/18/2021

        NOTE: This disposition is nonprecedential.

   United States Court of Appeals
       for the Federal Circuit
                  ______________________

         IN RE: RAGHAVAN RAJAGOPALAN,
                       Appellant
                ______________________

                        2020-1956
                  ______________________

     Appeal from the United States Patent and Trademark
 Office, Patent Trial and Appeal Board in No. 14/499,191.
                   ______________________

                  Decided: May 18, 2021
                  ______________________

     ROBERT FRITZ GREEN, Green, Griffith & Borg-Breen
 LLP, Chicago, IL, argued for appellant Raghavan Ra-
 jagopalan.

    ROBERT MCBRIDE, Office of the Solicitor, United States
 Patent and Trademark Office, Alexandria, VA, argued for
 appellee Andrew Hirshfeld. Also represented by KAKOLI
 CAPRIHAN, THOMAS W. KRAUSE, AMY J. NELSON, FARHEENA
 YASMEEN RASHEED.
                ______________________

    Before TARANTO, BRYSON, and CHEN, Circuit Judges.
 TARANTO, Circuit Judge.
    Raghavan Rajagopalan is the named inventor on U.S.
 Patent Application No. 14/499,191, entitled “Prevention of
Case: 20-1956     Document: 33     Page: 2    Filed: 05/18/2021

 2                                         IN RE: RAJAGOPALAN

 Illicit Methamphetamine Manufacture from Pseudoephed-
 rine Using Food Flavor Excipients.” The Patent and Trade-
 mark Office’s Patent Trial and Appeal Board rejected
 claims 1–3 and 10 for obviousness based on two prior-art
 references and rejected claims 12 and 13 for obviousness
 based on those references together with a third. We affirm
 the Board.
                               I
                               A
     The ’191 application describes a composition that “pre-
 vent[s] [the] illicit manufacture of methamphetamine”
 from pseudoephedrine, a common pharmaceutical ingredi-
 ent in over-the-counter allergy medication. J.A. 22. The
 application explains the basic two steps in the manufacture
 of methamphetamine from such available medications.
 The first step is isolation, or extraction, of the
 pseudoephedrine from the available medications, which
 contain other components. The second step is a chemical
 “reduction” reaction, involving reducing agents that donate
 electrons to the pseudoephedrine to produce methamphet-
 amine. J.A. 23.
     The application discloses a pseudoephedrine composi-
 tion that impedes the second (reduction) step of that con-
 version process. Specifically, it discloses a combination of
 pseudoephedrine with a food-flavoring excipient (an addi-
 tive), J.A. 23, in which the “excipient may capture the elec-
 trons from the reducing agent . . . at a much higher rate
 than pseudoephedrine . . . thereby blocking the formation
 of methamphetamine,” J.A. 25. These food-flavoring excip-
 ients are referred to in the ’191 application as “organoleptic
 agents.” J.A. 23.
     Independent claim 1 is representative and recites:
     1. A pharmaceutically acceptable composition for
     deterring illicit manufacture of methamphetamine,
     said composition comprising:
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 IN RE: RAJAGOPALAN                                         3

    (a) an active pharmaceutical ingredient, wherein
    the active pharmaceutical ingredient is ephedrine
    or pseudoephedrine; and
    (b) an effective amount of an organoleptic excipi-
    ent, wherein the organoleptic excipient is selected
    from the group consisting of pyrazines, pyrim-
    idines, thiazolines, thiazolidines, and thiazoles;
    wherein said organoleptic excipient inhibits the
    chemical reduction of said active pharmaceutical
    ingredient to methamphetamine with reducing
    agents; and wherein said reducing agents comprise
    alkali metals, zinc, or phosphorous.
 J.A. 455; see also Ex parte Rajagopalan, No. 2018-007283,
 2020 WL 2126720, at *4 (P.T.A.B. Apr. 29, 2020) (Board
 finding claim 1 representative).
                             B
     The examiner and the Board relied on three prior-art
 references—Giamalva, Adams, and Takakura—for reject-
 ing claims 1–3, 10, 12, and 13 of the ’191 application, in-
 voking the first two references for all claims and adding
 Takakura for claims 12 and 13.
     Giamalva is a published patent application, U.S. Pa-
 tent Application Publication No. 2007/0243140, entitled
 “Pharmaceutical Composition Containing Sympathomi-
 metic Amine Salt and Co-Distillable Additive.” Giamalva
 recognizes that over-the-counter medications containing
 pseudoephedrine (which is a sympathomimetic amine) may
 be used to illicitly manufacture methamphetamine. See
 Giamalva ¶¶ 3–4. And Giamalva notes that
    [i]t has thus been found desirable to formulate
    sympathomimetic amine-containing products in or-
    der to render isolation of the sympathomimetic
    amine more difficult or otherwise interfere with ef-
    forts to produce illegal drugs from common [over-
    the-counter] medications, e.g., by altering reactants
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 4                                         IN RE: RAJAGOPALAN

     used to convert sympathomimetic amine to meth-
     amphetamine.
Id. ¶ 5 (emphases added).
      The reference teaches including an additive in the com-
 pound to “inhibit[] reduction of the sympathomimetic
 amine and/or its derivatives.” Id. ¶ 17. The additive,
 Giamalva teaches, should have properties sufficiently sim-
 ilar to the pseudoephedrine to prevent separation of the
 two when distillation is used to isolate pseudoephedrine be-
 fore chemical reduction to methamphetamine. See id. ¶ 43.
 The additive may be an odorant, i.e., a compound that “ex-
 hibit[s] a characteristic odor, and in some cases, a charac-
 teristic flavor as well, particularly during purification
 and/or conversion of sympathomimetic amines in illegal
 drug synthesis, or in the product of the illegal synthesis it-
 self.” Id. ¶ 47. The odor can be unpleasant and, if released
 during preparation, “render such preparation distasteful
 and/or serve as a recognizable signal to law enforcement.”
Id. ¶ 48. Critically, inclusion of the additive can also “in-
 terfere[] with the reduction to methamphetamine by com-
 peting with pseudoephedrine for the reducing agent.” Id.
 ¶ 46.
     Giamalva elaborates on the odorant’s role at each of the
 two steps involved in the process of manufacturing meth-
 amphetamine. At the first step of the methamphetamine-
 production process, where the pseudoephedrine is isolated,
 “an odorant can deter misuse of commercially available
 sympathomimetic amines by imparting a very strong odor
 to a material, even after multiple attempts to isolate” it.
Id. ¶ 52. At the second step of the production process,
 where the pseudoephedrine is chemically converted into
 methamphetamine, “specific odorants” that are “present at
 sufficiently high levels” (higher than those required to
 simply create the odor) “can inhibit one or more of the re-
 actions, e.g., reduction, used to convert the sympathomi-
 metic amine to an illegal drug.” Id. (emphasis added).
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 IN RE: RAJAGOPALAN                                         5

 Giamalva further explains that a “specific odorant” may be
 a “standard flavorant.” Id. And it adds that embodiments
 include odorants that “contain nitrogen, e.g., as a volatile
 amine.” Id. ¶ 53.
     Adams is a journal article: T.B. Adams et al., The
 FEMA GRAS Assessment of Pyrazine Derivatives Used as
 Flavor Ingredients, 40 Food and Chemical Toxicology 429
 (2002). It teaches that pyrazines are nitrogen-containing
 compounds that are used as flavoring agents in foods. Id.
 at 430. It explains that acetylpyrazine is the most com-
 monly used pyrazine flavoring ingredient in the United
 States, and it discloses the structure of acetylpyrazine. Id.
 at 430, 434.
     Takakura is a published patent application, U.S. Pa-
 tent Application Publication No. 2012/0052177, entitled
 “Flavoring Material.” Takakura teaches that thiazoles are
 known organoleptic compounds. See Takakura ¶¶ 26, 30,
 45–48. Takakura further teaches that 5-acetyl-2,4-dime-
 thylthiazole “impart[s] a particularly favorable livestock
 meat stock flavor.” Id. ¶ 48.
                              C
      On September 29, 2017, the examiner issued a final re-
 jection of independent claim 1 and dependent claims 2, 3,
 10, 12, and 13 of the ’191 application. J.A. 403–28 (Final
 Rejection). On April 29, 2020, the Board affirmed the ex-
 aminer’s rejections of the claims as obvious in light of
 Giamalva combined with Adams or with Adams and
 Takakura. Rajagopalan, 2020 WL 2126720, at *4–7. Be-
 cause Mr. Rajagopalan has not argued that the Board
 adopted new grounds of rejection and denied him a re-
 quired opportunity to respond, we limit our description to
 the Board’s decision.
      The Board set forth the findings of fact that were key
 to its decision. It found that “Giamalva teaches the prepa-
 ration of a pharmaceutical composition comprising
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 6                                         IN RE: RAJAGOPALAN

 pseudoephedrine and a volatile amine odorant.” Id. at *3
 (citing Giamalva Abstract). It found, too, that Giamalva
 teaches what Giamalva paragraph 5 expressly states—the
 desirability of formulating a product containing a sympa-
 thomimetic amine such as pseudoephedrine so as to “‘inter-
 fere with efforts to produce illegal drugs from common
 [over-the-counter] medications, e.g., by altering reactants
 used to convert sympathomimetic amine to methampheta-
 mine.’” Id. (quoting Giamalva ¶ 5). The Board further
 found that Giamalva teaches what Giamalva paragraph 47
 states—use of odorants as codistillable additives “‘that in-
 terfere with subsequent chemical reactions for converting
 sympathomimetic amine compounds to illegal drugs.’” Id.
 (quoting Giamalva ¶ 47). The Board added that Adams
 teaches aroma-producing pyrazine-based flavoring ingredi-
 ents, including acetylpyrazine, which is among the struc-
 tures covered by claim 1, as made explicit in Formula I of
 the ’191 application’s specification. Id. at *3 (citing Adams
 429–30).
      The Board also “adopt[ed] the [e]xaminer’s findings as
 [its] own, including with regard to the scope and content of,
 and motivation to modify or combine, the prior art.” Id. at
 *3. One of the examiner’s findings was that “‘[i]t would
 have been obvious to one of ordinary skill in the art to com-
 bine the teachings of Giamalva . . . with the organoleptic
 agents disclosed by Adams’” and that, with that combina-
 tion, “‘conversion of any pure pseudoephedrine to metham-
 phetamine [would be] hindered with a reasonable
 expectation of success.’” Id. at *2 (quoting J.A. 420–21).
 That finding, as the examiner made explicit to the Board,
 is a finding of “motivation to combine . . . with a reasonable
 expectation of success.” J.A. 497 (examiner’s answer).
     The Board summarized: “Giamalva teaches a composi-
 tion comprising pseudoephedrine and an amine[-]based
 odorant which interferes with the conversion of
 pseudoephedrine. Adams teaches that pyrazines[,] includ-
 ing those having a chemical structure meeting the
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 IN RE: RAJAGOPALAN                                        7

 requirements of [F]ormula I in the Specification, exhibit
 aromas. We agree with the [e]xaminer that it would have
 been obvious to substitute the pyrazines of Adams for the
 odorants of Giamalva.” Rajagopalan, 2020 WL 2126720, at
 *5 (citations omitted).
     The Board considered and rejected Mr. Rajagopalan’s
 arguments against the examiner’s obviousness rejections.
Id. at *4–7. The Board first rejected the contention that
 the invention claimed in the ’191 application satisfies a
 long-felt need—a contention, the Board concluded, that
 was only attorney argument, unsupported by any “objec-
 tive evidence . . . that there was a long-felt need and that
 the present invention satisfied that need.” Id. at *4. The
 Board next rejected Mr. Rajagopalan’s argument that the
 prior art taught away from the combination that the Board
 found the art actually taught. Id. Mr. Rajagopalan also
 contended that the cited prior art “does not enable the
 claimed composition” because “the compositions taught by
 Giamalva do not inhibit the chemical conversion of
 pseudoephedrine to methamphetamine,” id. at *5, but the
 Board concluded otherwise. The Board reasoned that be-
 cause “the composition resulting from the combination of
 Giamalva and Adams matches the claimed composition,”
 Mr. Rajagopalan had the burden to show that the
 Giamalva-Adams combination composition “would not pos-
 sess the same property” as the claimed composition, but
 Mr. Rajagopalan had “not offered any persuasive evidence”
 to make that showing. Id. Similarly, the Board concluded,
 Mr. Rajagopalan had “not offered any evidence of unex-
 pected results.” Id. at *6.
     Mr. Rajagopalan did not make separate arguments as
 to the examiner’s rejection of claims 12 and 13 for obvious-
 ness based on the combination of Giamalva, Adams, and
 Takakura, so the Board likewise affirmed that rejection.
 See id. at *4, *7.
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 8                                         IN RE: RAJAGOPALAN

     Mr. Rajagopalan timely appealed under 35 U.S.C.
 § 141(a). We have jurisdiction. See 28 U.S.C. § 1295(a)(4).
                               II
     Obviousness is a question of law that we review de
 novo, with underlying factual determinations reviewed for
 substantial evidence. PersonalWeb Techs., LLC v. Apple,
 Inc., 917 F.3d 1376, 1381 (Fed. Cir. 2019). Factual findings
 include “the scope and content of the prior art, the differ-
 ences between the prior art and the claimed invention, the
 level of ordinary skill in the art, the presence or absence of
 a motivation to combine or modify with a reasonable expec-
 tation of success, and objective indicia of non-obviousness.”
 Ariosa Diagnostics v. Verinata Health, Inc., 805 F.3d 1359,
 1364 (Fed. Cir. 2015). On substantial-evidence review, we
 ask “‘whether a reasonable fact finder could have arrived
 at the agency’s decision’ and require[] examination of the
 ‘record as a whole, taking into account evidence that both
 justifies and detracts from an agency’s decision.’” Intelli-
 gent Bio-Systems, Inc. v. Illumina Cambridge Ltd., 821
F.3d 1359, 1366 (Fed. Cir. 2016) (quoting In re Gartside,
 203 F.3d 1305, 1312 (Fed. Cir. 2000)).
      In this case, obviousness follows readily from the
 Board’s key factual findings if those findings are supported
 by substantial evidence. As described above, the Board, in
 its expressly stated findings and in its adoption of the ex-
 aminer’s findings, found that Giamalva teaches using an
 amine-based odorant to interfere with the chemical conver-
 sion of pseudoephedrine to methamphetamine; that Adams
 discloses particular odorants, namely, pyrazines, which
 come within claim 1 of the ’191 application and its specifi-
 cation; and that a relevant artisan had a motivation to use
 the Adams-disclosed compositions as odorants in the
 Giamalva composition with a reasonable expectation of
 success of hindering the chemical conversion. Those find-
 ings are supported by substantial evidence.
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 IN RE: RAJAGOPALAN                                          9

      Some of the support is found in evidence the Board ex-
 pressly quoted or cited. See, e.g., Giamalva ¶ 5 (“It has thus
 been found desirable to formulate sympathomimetic
 amine-containing products [like pseudoephedrine] in order
 to render isolation of the sympathomimetic amine more dif-
 ficult or otherwise interfere with efforts to produce illegal
 drugs from common [over-the-counter] medications . . . .”),
 ¶ 47 (teaching codistillable additives “that interfere with
 subsequent chemical reactions for converting sympathomi-
 metic amine compounds to illegal drugs”); see also Adams
 429–30. Additional supporting evidence is found on the
 face of Giamalva at paragraphs 17, 43, 46, 48, 52, and 53
 (all quoted above). Those paragraphs, among other things,
 disclose the motive to inhibit the reduction reaction, the
 use of odorants to achieve that inhibition, the inclusion of
 “standard flavorants” among the “specific odorants” de-
 scribed as inhibiting reduction, and the use of nitrogen-con-
 taining odorants like volatile amines. See id. Adams, for
 its part, adds that pyrazines are commonly used amine (ni-
 trogen-containing) odorants and that one type of pyrazine
 (acetylpyrazine) is the most commonly used pyrazine fla-
 vorant in the United States. Adams 430. The ’191 appli-
 cation itself makes clear that acetylpyrazine falls within
 the group of amine odorants recited in the claims because
 acetylpyrazine has the structure of Formula I set forth in
 the application. Compare J.A. 20 (Formula I), with Adams
 434 (acetylpyrazine).
     This is sufficient evidence of a motivation to use the
 Adams pyrazine, a standard flavorant amine, as an odor-
 ant in the Giamalva formulation, creating a composition
 that, as a prima facie matter, Giamalva indicates would be
 reasonably expected to have the claimed inhibition-of-re-
 duction property. In this circumstance, “the burden shifts
 to the patentee to provide evidence” to rebut the examiner’s
 prima facie case—here, specifically, to show that the
 claimed inhibition of reduction would not result. See In re
 Brandt, 886 F.3d 1171, 1176 (Fed. Cir. 2018); ACCO
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 10                                      IN RE: RAJAGOPALAN

 Brands Corp. v. Fellowes, Inc., 813 F.3d 1361, 1365–66
 (Fed. Cir. 2016); In re Best, 562 F.2d 1252, 1255 (CCPA
 1977). Mr. Rajagopalan has not undermined the Board’s
 determination that he did not rebut the prima facie case.
     Mr. Rajagopalan argues that the prior-art references
 do not teach using the organoleptic excipient in an “effec-
 tive amount,” which the ’191 application defines as an
 amount that sufficiently inhibits the formation of metham-
 phetamine to be “less than about 25%” of the formed com-
 position. J.A. 26; Rajagopalan Opening Br. at 11–12, 32.
 But the Board adopted the examiner’s findings, which in-
 clude a finding that the claimed “effective amount” in the
 ’191 application is taught in Giamalva’s disclosure of the
 most preferred amount of odorant to add. See J.A. 410.
 Giamalva supports that finding. It teaches that the ratio
 of additive to pseudoephedrine should “preferably” be
 “from about 10:1 to about 1:10,” “[m]ore preferably” “from
 about 3:1 to about 1:3,” and “[m]ost preferably” “from about
 2:1 to about 1:2.” Giamalva ¶ 56. The ’191 application
 teaches that if the ratio of the excipient Formula I to
 pseudoephedrine is roughly 1:1, which is within the range
 of Giamalva’s most preferred ratios, then the amount will
 be effective, in that methamphetamine will be no more
 than 6% of the product of the reduction process. See J.A.
 30–31.
     With respect to claims 12 and 13, which depend on
 claim 1 but specify particular excipients, Mr. Rajagopalan
 made no separate arguments before the Board that the
 combination of Giamalva, Adams, and Takakura failed to
 establish that the claims are unpatentable for obviousness.
 See J.A. 433–62 (Rajagopalan Appeal Brief), 516–27 (Ra-
 jagopalan Reply Brief). Such arguments have accordingly
 been forfeited. See In re Google Tech. Holdings LLC, 980
F.3d 858, 863 (Fed. Cir. 2020). In any event, we note that
 Takakura discloses 5-acetyl-2,4-dimethylthiazole, which,
 as Mr. Rajagopalan does not dispute, is a thiazole described
 by the structure of Formula III recited in claims 12 and 13.
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 IN RE: RAJAGOPALAN                                        11

 Compare J.A. 20 (Formula III), with Takakura ¶¶ 47–48;
 see also Rajagopalan Opening Br. at 28–30. Takakura fur-
 ther discloses that 5-acetyl-2,4-dimethylthiazole is a fla-
 vorant that “impart[s] a particularly favorable livestock
 meat stock flavor.” Takakura ¶ 48; see also J.A. 424 (Final
 Office Action). Thus, for reasons similar to those stated
 above, substantial evidence supports the finding that a rel-
 evant artisan would have been motivated to substitute the
 flavorant from Takakura for the odorants in Giamalva’s
 teachings. See J.A. 424; cf. Rajagopalan, 2020 WL
2126720, at *4–5 (explaining why a relevant artisan would
 combine Giamalva and Adams).
                             III
     We have considered Mr. Rajagopalan’s remaining ar-
 guments and find them unpersuasive. For the foregoing
 reasons, we affirm the Board’s determination that claims
 1–3, 10, 12, and 13 of the ’191 application are unpatentable
 for obviousness.
     The parties shall bear their own costs.
                        AFFIRMED