Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claim Status
Claims 1-17 are pending. Claims 1-17 are under examination. Claims 1-17 are rejected. No claims allowed.
Filing Receipt
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Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-2, 4, 6, and 8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ibert et al. (Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid, Carbohydrate Research 337 pp. 1059–1063, Published 2002).
Ibert et al. disclose the following bridging pages 1062-1063 left column.
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The product disclosed by Ibert et al. contains the claimed glucaric acid because substantially identical processes result in substantially identical products. The claimed process is disclosed by the prior art. Therefore, the product obtained by practicing the methods of the prior art would have the claimed glucaric acid.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
The TEMPO being the nitroxide radical-mediated organocatalyst (claim 2), the sodium bromide being the co-catalyst (claim 4) and the oxidizing agent bleach being sodium hypochlorite (NaClO) (claim 6), the water being the solvent (claim 8).
Claim(s) 1-8 12, and 15 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Merbouh et al. (Facile nitroxide-mediated oxidations of D-glucose to D-glucaric acid, Carbohydrate Research 336 pp. 75–78, Published 2001. Cited in the IDS filed 08/13/2025).
Merbouh et al. disclose the following page 77 left column.
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Concerning claim 4 and 7, Merbouh et al. disclose the following bridging pages 77-78.
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The 4-acetamido-TEMPO being the nitroxide radical-mediated organocatalyst (claim 2-3), the sodium bromide and potassium bromide being the co-catalyst (claim 4-5, 12) and the oxidizing agent and bleach being sodium hypochlorite (NaClO) and KClO (claim 6-7, 12), the water being the solvent (claim 8). The HCl being the acid in claim 12 and 15.
Concerning claim 12 step (a) and the preparing of an aqueous solution containing glucaric acid or a potassium salt thereof, substantially identical methods yield substantially identical products. The claimed process is disclosed by the prior art. Therefore, the product obtained by practicing the methods of the prior art would have the claimed glucaric acid.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Concerning claim 12 and current step (b) and adding an acid to change the aqueous solution to an acidic one would necessarily have occurred when Merbouh et al. taught “At the end of the reaction, the mixture ( 130 mL) was partially acidified with one equivalent of concd HCl to give a final pH of 3.8. The precipitated product, after drying under vacuum at 40 °C was identical to the one obtained above and amounted to 2.4 g (55%)” (p. 78).
The above precipitated product disclosed by Merbouh et al. refers to monopotassium glucarate (Merbouh et al., page 77, left column).
The precipitated product disclosed by Merbouh et al. is the current mixture in step (b) of claim 12.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1-2, 4, 6, and 8-11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ibert et al. (Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid, Carbohydrate Research 337 pp. 1059–1063, Published 2002).
Scope of the Prior Art
The disclosure of Ibert et al. is in the above 102 rejection and incorporated by reference.
Additional teachings of Ibert et al. are as follows.
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page 1059 left column.
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page 1059 right column.
Concerning claim 10 the pH and other process parameters, Ibert et al. teach
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page 1059 right column.
Additionally, concerning the pH and the importance of process parameters, Ibert et al. teach
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page 1059 right column.
Concerning claims 9 and 11 and the temperature, and oxidizing agent to glucose (m2/ml), Ibert et al. teach 0C and 5C, and 2.2 (m2/ml) respectively (page 1062 left column). The temps. and m2/ml taught by Ibert et al. overlap the numerical ranges in current claims 9 and 11. Concerning claim 10 and the pH, Ibert et al. teach “At pH 11.7, 1H NMR-spectroscopic yields close to 90% of sodium glucarate can be obtained (p. 1060, right column). This pH overlaps the current range in claim 10.
Ascertain the Differences
Ibert et al. does not explicitly teach the current pH ranges of claim 10 in the working example cited in the above 102 rejection on pages 1062-1063. of Ibert et al. However, Ibert et al. does teach pH in another location within the reference that overlaps in stope of the current ranges. Thus a combination of teachings is warranted.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared and isolated glucaric acid due to the potential of a number of industrially relevant applications in polymer, food, and medicinal chemistry.
The ordinary artisan would have next chosen a system involving the current reaction of glucose in a solvent through an oxidation reaction using a nitroxide radical-mediated organocatalyst, a co-catalyst, and an oxidizing agent with a reasonable expectation of success because Ibert et al. teach glucaric acid, isolated as its monopotassium or disodium salt, can be made under carefully controlled pH and temperature conditions from glucose in yields approaching 90%, within the context of a TEMPO–NaBr–NaOCl system. Ibert et al. then goes on to teach a specific oxidation of glucose on page 1062 and which is detailed in the above 102 which is incorporated by reference.
Concerning claim 10 and the current pH, the ordinary artisan in need of a pH
would have looked to Ibert et al. on page 1060, right column and found 11.7 pH.
Concerning the limitations of claims 9, 10 and 11, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Claim(s) 1-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Merbouh et al. (Facile nitroxide-mediated oxidations of D-glucose to D-glucaric acid, Carbohydrate Research 336 pp. 75–78, Published 2001. Cited in the IDS filed 08/13/2025) and Ibert et al. (Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid, Carbohydrate Research 337 pp. 1059–1063, Published 2002).
Scope of the Prior Art
The disclosure and/or teachings of Merbouh et al. and Ibert et al. are in the above 102 and/or 103 rejections and are incorporated by reference.
Additional teachings of Merbouh et al. are as follows. Concerning claim 9,
Merbouh et al. teach 0-5C (page 77, left column). This range overlaps the current range. Concerning claim 10, Merbouh et al. teach a pH of 11.5 (page 77, left column). This range overlaps the current range. Concerning claim 11 and the ratio of m2/ml, Merbouh et al. teach 3.3 equiv. (page 77, left column). This range overlaps the current range. Concerning claim 13, Merbouh et al. teach a pH of 11.4-11.6 (page 77, left column). This range overlaps the current range. Concerning claim 14, Merbouh et al. teach a pH of 3.8 (page 78, left column). This range overlaps the current range.
Ascertain the Differences
Merbouh et al. teach preparing the sodium and/or potassium salts of glucaric acid at specific parameters wherein the claimed parameters are in ranges. Thus, an obviousness rejection is warranted.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared and isolated glucaric acid due to the potential of a number of industrially relevant applications in polymer, food, and medicinal chemistry.
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have chosen to prepare the monopotassium glucaric acid with a reasonable expectation of success from the limited options presented. MPEP 2141 (E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success. In doing so, the ordinary artisan would have arrived at the inventions of claims 1 and 16.
Concerning the claimed ranges, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Claim(s) 16-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Merbouh et al. (Facile nitroxide-mediated oxidations of D-glucose to D-glucaric acid, Carbohydrate Research 336 pp. 75–78, Published 2001. Cited in the IDS filed 08/13/2025) and Ibert et al. (Determination of the side-products formed during the nitroxide-mediated bleach oxidation of glucose to glucaric acid, Carbohydrate Research 337 pp. 1059–1063, Published 2002) as applied to claims 1-15 and in further view of LibreTexts (3 pages, Published 06-2023).
Scope of the Prior Art
The combinational teachings and disclosure of Merbouh et al. and or Ibert et al. are in the above 103 and 102 rejections and are incorporated by reference.
Additional teachings of Merbouh et al. are as follows. Merbouh et al. teach the monopotassium salt is slightly soluble (p. 76, lower right column). Concerning the second precipitation was conducted as follows.
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page 78, left column.
Concerning step (b) in claim 16, Merbouh et al. teach in the immediately above, precipitation, drying of product, filtrate, and white crystalline product.
Ascertain the Differences
Merbouh et al. does not teach reducing a temperature of the mixture to further precipitate the glucaric acid monopotassium salt.
Secondary References
LibreTexts teach precipitation can happen for various reasons, such as that you cooled a solution, or remove some solvent by evaporation or both (page 1).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have lowered the temperature after adjusting the pH. The ordinary artisan being taught by Merbouh et al. that the product, glucaric acid is slightly soluble and that product remains in solution immediately following the precipitation of the product would have alternatively tried lowering the temperature of the precipitated mixture to achieve similar results.
The ordinary artisan would have done so with a reasonable expectation of success because LibreTexts teach precipitation can happen for various reasons, such as that you cooled a solution, or remove some solvent by evaporation or both (page 1).
MPEP 2141 (E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success. Additionally, see MPEP 2141 III (B).
Concerning the current temperatures of 1 to 10C, the ordinary artisan knowing that lowering the temperature can necessarily cause precipitation would have experimented via routine experimentation to ensure the correct temperatures were used to cause the claimed precipitation. In doing so the ordinary artisan would have arrived at the current temperatures.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Concerning step (b) in claim 16, Merbouh et al. teach precipitation, drying of product, filtrate, and white crystalline product. From this the ordinary artisan would have inferred from the teachings the isolation of any and all precipitate via filtration and drying to obtained a crystalline white product of glucaric acid.
Additional References Pertinent to the Invention
Thaburet et a. (TEMPO-mediated oxidation of maltodextrins and D-glucose:
effect of pH on the selectivity and sequestering ability of the resulting polycarboxylates, Carbohydrate Research 330 pp. 21–29, Published 2001).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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