Ex Parte Langstrom et alDownload PDFBoard of Patent Appeals and InterferencesJul 10, 201211386973 (B.P.A.I. Jul. 10, 2012) Copy Citation MOD PTOL-90A (Rev.06/08) APPLICATION NO./ CONTROL NO. FILING DATE FIRST NAMED INVENTOR / PATENT IN REEXAMINATION ATTORNEY DOCKET NO. 11/386,973 03/22/2006 Langstrom, Bengt EXAMINER Amersham Health, Inc. IP Department 101 Carnegie Center Princeton, NJ 08540 Schlientz, Leah ART UNIT PAPER NUMBER 1618 MAIL DATE DELIVERY MODE 07/11/2012 PAPER 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. UNITED STATES DEPARTMENT OF COMMERCE U.S. Patent and Trademark Office Address : COMMISSIONER FOR PATENTS P.O. Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov UNITED STATES PATENT AND TRADEMARK OFFICE _____________________________________________________________________________________ UNITED STATES PATENT AND TRADEMARK OFFICE __________ BEFORE THE BOARD OF PATENT APPEALS AND INTERFERENCES __________ Ex parte BENGT LANGSTROM, JULIEN BARLETTA, FARHAD KARIMI, and HISASHI DOI __________ Appeal 2011-006207 Application 11/386,973 Technology Center 1600 __________ Before FRANCISCO C. PRATS, MELANIE L. McCOLLUM and JEFFREY N. FREDMAN, Administrative Patent Judges. PRATS, Administrative Patent Judge. DECISION ON APPEAL This appeal under 35 U.S.C. § 134 involves claims to a method for synthesizing carbonylated diazo compounds labeled with a carbon isotope. The Examiner rejected the claims as obvious. We have jurisdiction under 35 U.S.C. § 6(b). We affirm. Appeal 2011-006207 Application 11/386,973 2 STATEMENT OF THE CASE Claims 1-7 and 19 stand rejected and appealed (App. Br. 2). Claim 1 is representative and reads as follows: 1. A method for labeling synthesis, comprising: (g) Providing a high pressure reaction chamber having a liquid inlet and a gas inlet in a bottom surface thereof, (h) providing an diazo solution to be labeled mixed with a transition metal complex and an appropriate reagent, wherein the appropriate reagent is selected from a list comprising: wherein R 2 , R 3 , R 4 and R 5 are independently linear or cyclic lower alkyl or substituted alkyl, hydrogen, aryl or substituted aryl, and may contain carbonyl, hydroxyl, thiol, halogen, nitrile, isonitrile, cyanate, isocyanate, thiocyanate, isothiocyanate functional groups. (i) introducing a carbon-isotope monoxide enriched gas-mixture into the reaction chamber via the gas inlet, (j) introducing at high pressure said diazo solution mixed with transition metal complex and said appropriate reagent into the reaction chamber via the liquid inlet, (k) waiting for a predetermined time while the labeling synthesis occur, and (l) collecting the labeled compound, wherein the labeled compound is selected from a list comprising: Appeal 2011-006207 Application 11/386,973 3 wherein R 1 is linear or cyclic lower alkyl or substituted alkyl, hydrogen, aryl or substituted aryl and may contain carbonyl, hydroxy, thiol, halogen, nitrile, isonitrile, cyanate, isocyanate, thiocyanate, isothiocyanate functional groups, R 2 , R 3 , R 4 and R 5 are independently linear or cyclic lower alkyl or substituted alkyl, hydrogen, aryl or substituted aryl, and may contain carbonyl, hydroxy, thiol, halogen, nitrile, isonitrile, cyanate, isocyanate, thiocyanate, isothiocyanate functional groups from the reaction chamber. The following grounds of rejection are before us for review: (1) Claims 1-6 and 19 under 35 U.S.C. § 103(a) as obvious over Tuba, 1 Kihlberg, 2 and Hernandez 3 (Ans. 4-6); and (2) Claims 1-7 and 19 under 35 U.S.C. § 103(a) as obvious over Tuba, Kihlberg, Hernandez, and Deydier 4 (Ans. 7). 1 Robert Tuba & Ferenc Ungváry, Octacarbonyl dicobalt-catalyzed selective transformation of ethyl diazoacetate into organic products containing the ethoxycarbonyl carbene building block, 203 J. MOL. CATALYSIS 59-67 (2003). 2 WO 02/102711 A1 (published Dec. 27, 2002). 3 L. Hernandez et al., Labelling with diethyl-[ 2- 14 C]-malonate in solvent- free conditions, 53 CZECH. J. PHYS. A751-A754 (Supp. 2003). 4 Eric Deydier et al., Wolff rearrangement in a transition-metal diazoalkane complex. Synthesis of the first η 1 -ketenyl rhodium complex Appeal 2011-006207 Application 11/386,973 4 DISCUSSION In rejecting claims 1-6 and 19 as obvious over Tuba, Kihlberg, and Hernandez, the Examiner cited Tuba as teaching that, “in the presence of 1 mol% octacarbonyl dicobalt, ethyl diazoacetate can be transformed at room temperature and carbon monoxide pressure in the presence of an alcohol (methanol, ethanol, t-butanol, phenol) or diethylamine into the corresponding malonic acid derivatives in high yields” (Ans. 4). In particular, the Examiner noted that Tuba described optimizing the yield of diethyl malonate (id. at 5). The Examiner conceded, however, that Tuba’s process differed from the claimed process in that Tuba did “not teach using isotopically enriched carbon monoxide” (id.). To address that deficiency, the Examiner cited Kihlberg as describing a procedure for synthesizing carbon-isotope monoxide (id.). Finally, the Examiner found that Hernandez taught the suitability of using diethyl malonate, radiolabeled with a carbon isotope, either 14 C or 11 C, as a precursor for producing radiolabeled methyl fatty acids “which are frequently used as biochemical tracers and radiopharmaceuticals” (id. at 6). Based on the references’ teachings, the Examiner concluded that an ordinary artisan would have considered it obvious “to perform isotopic labeling of malonic acid derivatives by performing carbonylation reactions using a diazo compound and reagent such as alcohol using isotopically labeled carbon monoxide in an automated reactor, when the teaching of Tuba is taken in view of Kihlberg” (id.). The Examiner reasoned that the [Rh{C(CO)SiMe3}(CO)(PEt3)2], 458 J. ORGANOMETALLIC CHEM. 225-228 (1993) (abstract only). Appeal 2011-006207 Application 11/386,973 5 artisan would have been prompted to “to prepare labeled diethyl malonate because Hernandez teaches that diethyl-[2- 14 C]-malonate is a useful precursor in labeling synthesis, such as for preparation of various 2-[11, 14C]-methyl fatty acids, which are frequently used as biochemical tracers and radiopharmaceuticals” (id.). As stated in In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992): [T]he examiner bears the initial burden . . . of presenting a prima facie case of unpatentability. . . . After evidence or argument is submitted by the applicant in response, patentability is determined on the totality of the record, by a preponderance of evidence with due consideration to persuasiveness of argument. As Appellants do not argue the claims subject to this ground of rejection separately, we select claim 1 as representative of the rejected claims. See 37 C.F.R. § 41.37(c)(1)(vii). Appellants’ arguments do not persuade us that a preponderance of the evidence fails to support the Examiner’s prima facie case of obviousness as to claim 1. Claim 1 recites a method for synthesizing carbon-isotope labeled compounds by reacting a mixture containing a diazo compound, a transition metal complex, and an appropriate reagent – which among other compounds may be an alcohol – with carbon-isotope monoxide at high pressure. The Examiner has advanced evidence, in the form of Tuba, that, except for the isotope-labeled carbon monoxide, it was known in the art to prepare a number of compounds using that procedure, diethyl malonate being among those compounds (see Tuba 59-60). The Examiner has also advance evidence, in the form of Hernandez, that 14 C-labeled diethyl malonate was itself useful for preparing labeled methyl fatty acids “which Appeal 2011-006207 Application 11/386,973 6 are frequently used as biochemical tracers and radiopharmaceuticals” (Hernandez A751). Given these teachings, we agree with the Examiner that an ordinary artisan seeking to prepare carbon-isotope labeled diethyl malonate, as taught by Hernandez, would have considered it obvious to use a known process of preparing that compound, such as that taught by Tuba, and in doing so would have used isotope-labeled carbon monoxide, such as that taught by Kihlberg. Appellants argue that “Tuba, Kihlberg, or Hernandez do not disclose, teach, or suggest using the appropriate reagents disclosed in the current invention for a carbon-isotope labeling synthesis method. This is an essential feature of the present invention” (App. Br. 5). Appellants do not, however, explain with any specificity why an ordinary artisan would have considered the reagents described in the prior art cited by the Examiner to be inappropriate for generating an isotopically labeled carbon compound as recited in claim 1. In the absence of some fact- based explanation as to some error in the Examiner’s reasoning, we do not find this argument persuasive. Appellants argue: [I]t is impermissible within the framework of 35 U.S.C. § 103 to pick and choose from any one reference only so much of it as will support a given position to the exclusion of other parts necessary to the full appreciation of what such reference fairly suggests to one skilled in the art. (App. Br. 5 (citing Bausch & Lomb, Inc. v. Barnes-Hind/Hydrocurve, Inc., 796 F.2d 443 (Fed. Cir. 1986))). Appeal 2011-006207 Application 11/386,973 7 We are not persuaded. Appellants do not point, with any specificity, to any portion of any of the cited references that the Examiner might have ignored so as to fail to fully appreciate the references’ teachings. Appellants similarly argue that “it is well settled in the law that a reference must be considered not just for what it expressly teaches, but also for what it fairly suggests to one who is unaware of the claimed invention” (App. Br. 5 (citing In re Baird, 16 F.3d 380 (Fed. Cir. 1994). Appellants do not, however, direct us to anything in the record suggesting that the Examiner somehow misapprehended what the cited references would have fairly suggested to an ordinary artisan unaware of the claimed invention. In sum, as Appellants’ arguments do not persuade us that the Examiner erred in concluding that claim 1 would have been obvious to an ordinary artisan, we affirm the Examiner’s rejection of that claim over Tuba, Kihlberg, and Hernandez. As they were not argued separately, claims 2-6 and 19 fall with claim 1. See 37 C.F.R. § 41.37(c)(1)(vii). The Examiner also rejected claims 1-7 and 19 as obvious over Tuba, Kihlberg, Hernandez, and Deydier (Ans. 7). The Examiner relied on Tuba, Kihlberg, and Hernandez for the teachings discussed above, and cited Deydier as evidence that it was known in the art to use a rhodium complex, as recited in claim 7, in a “functionally equivalent reaction” to that described by Tuba (id.). The Examiner reasoned that an ordinary artisan would have therefore considered it obvious “to substitute a rhodium catalyst for the cobalt catalyst employed by Tuba” (id.). We again select claim 1 as representative of the rejected claims. See 37 C.F.R. § 41.37(c)(1)(vii). Appeal 2011-006207 Application 11/386,973 8 As to this rejection, Appellants’ sole argument is that “Tuba, Kihlberg, Hernandez, or Deydier do not disclose, teach, or suggest using the appropriate reagents disclosed in the current invention for a carbon-isotope labeling synthesis method. This is an essential feature of the present invention” (App. Br. 6). As discussed above, however, we are not persuaded that the Examiner erred in concluding that claim 1 would have been obvious in view Tuba, Kihlberg, and Hernandez, and each of those references is applied against claim 1 in this rejection as well. Moreover, Appellants do not point, with any specificity, to any error in the Examiner’s characterization of Deydier, or to any error in the Examiner’s rationale for combining Tuba, Kihlberg, and Hernandez with Deydier. Thus, as Appellants’ arguments do not persuade us that the Examiner erred in concluding that claim 1 would have been obvious to an ordinary artisan in view Tuba, Kihlberg, Hernandez, and Deydier, we affirm the Examiner’s rejection of that claim over those references. As they were not argued separately, claims 2-7 and 19 fall with claim 1. See 37 C.F.R. § 41.37(c)(1)(vii). SUMMARY We affirm the Examiner’s obviousness rejection of claims 1-6 and 19 under over Tuba, Kihlberg, and Hernandez. We also affirm the Examiner’s obviousness rejection of claims 1-7 and 19 over Tuba, Kihlberg, Hernandez, and Deydier. Appeal 2011-006207 Application 11/386,973 9 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). AFFIRMED alw Copy with citationCopy as parenthetical citation