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
2. This Office Action is responsive to Applicant’s Amendment and Remarks, filed October 13, 2025. The amendment, filed October 13, 2025, is entered, wherein claim 3 is amended, claims 21 – 23 are new, and claims 10 – 12 and 18 – 20 are canceled.
Claims 1 – 9, 13 – 17, and 21 – 23 are pending in this application and are currently examined.
Priority
This application is a national stage application of PCT/KR2019/016668, filed November 29, 2019, which claims benefit of foreign priority document KR10-2018-0152876, filed November 30, 2018; this foreign priority document is not in English.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Failure to provide a certified translation may result in no benefit being accorded for the non-English application is only pertinent when interference arises.
The followings are maintained / modified / new grounds of rejection necessitated by Applicant’s Amendment and Remarks, filed October 13, 2025, wherein claim 3 is amended, claims 21 – 23 are new, and claims 10 – 12 and 18 – 20 are canceled. Previously and newly cited references have been used to establish the maintained / modified / new grounds of rejection.
Maintained / Modified / New Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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:
i. Determining the scope and contents of the prior art.
ii. Ascertaining the differences between the prior art and the claims at issue.
iii. Resolving the level of ordinary skill in the pertinent art.
iv. 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.
Claims 3 – 5, 8 – 9, 13 – 17, and 21 – 23 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US8524888B2) in view of Muller (Anti-solvent crystallization of sucrose, 2016, Reference included with PTO-892) and Giulietti (InTech EBooks, 2012, cited in the previous Office Action).
Regarding claims 3 – 5, 8 – 9, 13 – 17, and 21 – 23, Lee et al. teach a method of producing purified D-psicose crystals, including removing impurities from a D-psicose solution to obtain a purified D-psicose solution, concentrating the purified D-psicose solution, and crystallizing D-psicose from the concentrated D-psicose solution in a supersaturated state under a metastable zone (Col. 2, lines 57 – 64). In one embodiment, the D-psicose solution (containing about 2,780 g of D-psicose) is purified, concentrated to about 85% (g/g solution), and put into a crystallizer (Col. 8, lines 51 – 59). In other embodiment, the concentrated D-psicose solution used in the crystallization is D-psicose solution of about 70% (g/g) or more (claim 4). The crystallizer is controlled to maintain the temperature at about 50 ⁰C. The seeds are put into a mortar and mixed with ethanol to prepare a D-psicose ethanol solution. The D-psicose ethanol solution is introduced as a seed to the concentrated D-psicose solution in the crystallizer (Col. 8, lines 51 – 59). In general, the D-psicose seeds are in an amount of D-psicose is about 0.01% to about 1% (g/g) based on the total amount of D-psicose dissolved in the concentrated D-psicose solution (Col. 6, lines 4 – 7). The final supernatant is cooled down until the concentration reached about 74% (g/g solution) (Col. 9, lines 5 – 28). The results show that the amount of D-psicose crystals after the drying is about 1408 g, which is about 50% recovery (Col. 9, lines 28 – 31). The D-psicose crystals recovered after the dehydration is transferred to a fluidizer bed dryer or a vacuum dryer for drying (Col. 9, lines 26 – 28). In an embodiment, the purified D-psicose crystals have a size of about 0.1 mm to 0.2 mm (Col. 5, lines 47 – 49).
However, Lee et al. do not explicitly teach the use of anti-solvent crystallization for obtaining D-psicose, the ratio of water to ethanol is 1:0.5 or more, and the final temperature .
Muller discloses crystallization of sugar, wherein anti-solvent crystallization is discussed (Abstract). Anti-solvent crystallization involves adding an additional substance, called the anti-solvent, which induces crystallization. Anti-solvent crystallization achieves supersaturation by exposing a solution of the product to another solvent in which the product is poorly soluble. The anti-solvent must be miscible with the solvent and must change the solubility of the solute in the solvent. For example, if the solvent is ethanol, the anti-solvent might be water (page 12, para. 1). Pharmaceutical and fine chemical makers frequently rely on anti-solvent crystallization to generate a solid from a solution in which the produce has high solubility (page 12, para. 2). Anti-solvent crystallization is represented as:
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wherein the solution is mixed with anti-solvent and the antisolvent is recovered and reused. It is obvious that the use of an anti-solvent yields a crystal product without needing to evaporate the solvent, but still requires a separation step. Solvent (water) and anti-solvent (ethanol) can be separated by simply inducing liquid-liquid phrase separation. The most common way of separating ethanol from water is by distillation (page 12, para. 3). Moreover, seeding may help avoid excessive nucleation. The seed can be added as a powder or in slurry form with the anti-solvent. Adding seed with the anti-solvent offers an advantage over the traditional method of putting seed in at a single time which poses the risk of adding too soon (seeds dissolve) or too late (nucleation has already occurred) (page 13, para. 2). Therefore, seeding techniques can help produce the desired outcome (page 13, para. 3).
Giulietti teaches the ethanol to water ratio used in the crystallization of sugar may be 1 : 1 (page 390, para. 1). In other embodiments, the ethanol to water ratio may be 1 : 1.5, 1 : 4.0, 1 : 6.0, and 1 : 9.0 (page 389, table 3). Giulietti also teaches the good choice of antisolvent must be done carefully with preliminary experiments that can allow to obtain high yields and easiness of solvent recovery (page 395, para. 4). Giulietti also teaches that final temperature for all experiments is 30 ⁰C. The crystals yield is more than 93% of the available fructose quantity for all experiments (page 389, lines 12 – 13).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to combine the method of producing purified D-psicose crystals, including removing impurities from a D-psicose solution to obtain a purified D-psicose solution, concentrating the purified D-psicose solution, and crystallizing D-psicose from the concentrated D-psicose solution in a supersaturated state under a metastable zone as taught by Lee et al. with anti-solvent crystallization using water and ethanol in view of Muller because Muller teaches that anti-solvent crystallization has been used to generate a product that has high solubility and a crystal product is yield without the need of evaporating the solvent. One would have been motivated to combine the method as taught by Lee et al. with anti-solvent crystallization using water and ethanol in view of Muller because Muller teaches that anti-solvent crystallization is suitable for product with high solubility and it is known in the art that D-psicose is highly soluble. One would have been motivated to combine the method as taught by Lee et al. with anti-solvent crystallization using water and ethanol in view of Muller because Muller teaches that evaporating is not needed in the process, and is, therefore, more energy efficient.
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to combine the method as taught by Lee et al. and Muller with the ethanol to water ratio used in the anti-solvent crystallization of sugar in view of Giulietti because Giulietti teaches that the crystals yield would be 93% or more based on the method. One would have been motivated to combine the method as taught by Lee et al. and Muller with the ethanol to water ratio used in the anti-solvent crystallization of sugar in view of Giulietti because of the improved crystal yield. For the final temperature, one would have performed a routine experimentation to discover the best final temperature for the optimal D-psicose production. Therefore, one of the ordinary skill in the art would have had a reasonable expectation of success to combine the method of producing purified D-psicose crystals, including removing impurities from a D-psicose solution to obtain a purified D-psicose solution, concentrating the purified D-psicose solution, and crystallizing D-psicose from the concentrated D-psicose solution in a supersaturated state under a metastable zone as taught by Lee et al. with anti-solvent crystallization using water and ethanol and the ethanol to water ratio used in the anti-solvent crystallization of sugar in view of Muller and Giulietti as Lee et al. teach a method for producing D-psicose crystals, Muller teaches the benefits of anti-solvent crystallization and Giulietti teaches water-to-ethanol ratio used in anti-solvent crystallization for producing sugar crystals, thereby, the combination will yield predictable results.
Claims 1 – 2 and 6 – 7 are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (US8524888B2) in view of Muller (Anti-solvent crystallization of sucrose, 2016, Reference included with PTO-892) and Giulietti (InTech EBooks, 2012, cited in the previous Office Action) as applied to claims 3 – 5, 8 – 9, 13 – 17, and 21 – 23 above, and further in view of Kim et al. (EP3210478A1) and ICH (ICH Harmonised Guideline, 2016, Reference included with PTO-892).
Regarding claims 1 – 2 and 6 – 7, Lee et al., Muller, and Giulietti teach the limitations discussed above. Muller further discloses that cooling is probably the most common way of creating supersaturation and controlled cooling crystallization perhaps in combination with seeding, can be used to keep the process in metastable region (page 11, para. 2). An advantage of cooling crystallization is the low energy consumption (page 11, para. 4). Giulietti also discloses that the combination of cooling crystallization and antisolvent crystallization for crystallizing sugar has already been studied (page 388, para. 2).
However, these references do not teach the cooling rate and the time for performing crystallization to obtain D-psicose crystals.
Kim et al. teach a method for producing high purity D-psicose. The D-psicose crystals having a purity of 98% (w/w) or more and a grain size of MA200 or more (Abstract). The full-scale D-psicose crystallization is conducted for 80 hours (Col. 9, para. [0039]). The D-psicose solution having a purity of 95% (w/w) in the crystallization device is cooled to 50 ⁰C to 35 ⁰C at a rate of 0.31 ⁰C per hour for 48 hours to perform crystallization (Col. 10, para. [0042]).
ICH discloses a guideline for recommended use of less toxic solvents and the levels considered to be toxicologically acceptable for some residual solvents (page 1, para. 1). Ethanol is classified as Class 3 solvent (page 11) and Class 3 solvents below 0.5% need not be reported (page 4, 3.5 Reporting levels of residual solvents).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to combine the method as taught by Lee et al., Muller, and Giulietti with the particular cooling rate and duration of crystallization for D-psicose crystals in view of Kim et al. because Kim et al. teach the high purity D-psicose crystals using the specified cooling rate and duration. One would have been motivated to combine the methods because of the D-psicose crystals with the improved purity. It would also have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to adjust the amount of ethanol in the D-psicose crystal in view of the ICH guideline because ICH teaches that ethanol level of less than 0.5% is toxicologically acceptable. One would have performed routine experimentation to discover the best ethanol content for the optimal product characteristics based on the ICH guideline. Therefore, one of the skills in the art would have had a reasonable expectation of success to combine the method as taught by Lee et al., Muller, and Giulietti with the particular cooling rate and duration of crystallization for D-psicose crystals in view of Kim et al. because Lee et al. teach a method for producing D-psicose crystals, Muller teaches the benefit of using cooling crystallization, Giulietti teaches a method for producing sugar crystals, which incorporates both anti-solvent and cooling crystallization, and Kim et al. teach the cooling rate and the duration for the cooling crystallization of D-psicose, wherein the combination will lead to an improved product.
Response to Applicant’s Remarks:
Applicant’s Remarks, filed April 30, 2025, have been fully considered and are found to be not persuasive.
Regarding Lee et al., Applicant argues that Lee et al. fail to disclose mixing ethanol to the D-psicose solution to be crystallized and Lee et al. teach away from using ethanol with a D-psicose solution. Therefore, one of ordinary skill in the art would have no reason to modify Lee et al. by adding ethanol to D-psicose solution to be crystallized. The examiner acknowledged Applicant’s arguments. However, the new rejection is based on Lee et al. in view of Muller and Giulietti for achieving the claimed method for preparing a D-psicose crystal. Lee et al. teach a method of preparing D-psicose crystals using crystallization. In combination with Muller and Giulietti, the deficiencies of the claimed steps and the water-to-ethanol ratio are cured. The benefits of incorporating anti-solvent crystallization for crystallizing sugars with the appropriate water-to-ethanol ratio provided by Muller and Giulietti are the motivation for one to combine or modify.
Applicant argues that Lee et al. uses a D-psicose ethanol solution as a seed at only 0.3% (g/g) relative to D-psicose, which not only is a very small amount but it used solely as a seed. Therefore, Lee et al. do not disclose the D-psicose crystal as set forth in the claims. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Regarding the unexpected results, Applicant clarifies that the maximum amount of ethanol allowable in the composition without human taste (i.e., 0.05%) was surprisingly found and claimed. One of ordinary skill in the art will not expect the criticality of such a range prior to the present application. Applicant states that a prima facie obviousness can be rebutted simply based on the overlapping ranges by showing the criticality of the claimed range and unexpectedness is not required. However, Applicant does not provide sufficient evidence to establish that this specific concentration is critical to achieving any functional or distinctive property in the claimed product. The data cited by Applicant indicates that samples containing 0%, 0.03%, and 0.05% of ethanol exhibit no meaningful difference in taste, which suggests the claimed range does not result in a significant improvement or effect. Furthermore, the mere fact that 0.05% is below a known human detection threshold does not make it inherently critical or unexpected. This result is consistent with what would be reasonably anticipated, which is reducing ethanol content lowers its sensory detectability. Without evidence showing that the claimed ethanol concentration produces a distinct or superior result compared to closely related values, the assertions do not support a finding of criticality.
Regarding ICH, Applicant argues that the concept of ICH is distinct from the ethanol content of the present claim. The ICH calculation method and limits are directed to safety and not to organoleptic properties such as taste. The examiner acknowledged that ICH guideline primarily addresses acceptable levels of residual solvents from a safety and toxicological standpoint. However, the reference was not cited to establish a safety threshold, but rather to provide technical context and illustrate that low concentrations of solvents, such as ethanol, are commonly present in final compositions and are typically negligible or incidental. This supports the position that ethanol at or below the claimed concentration is not functionally significant in the final product. Furthermore, the cited art demonstrates that the presence of minor amounts of ethanol is known and routine. Therefore, the claimed ethanol concentration does not confer any unexpected property or non-obvious effect.
Conclusion
No claim is found to be allowable.
Applicant's amendment necessitated the maintained / modified / new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to HOI YAN LEE whose telephone number is 571-270-0265. The examiner can normally be reached Monday - Thursday 7:30 - 17:30.
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/H.Y.L./Examiner, Art Unit 1693
/SCARLETT Y GOON/Supervisory Patent Examiner, Art Unit 1693