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
Pursuant to the preliminary amendment dated 3/29/2024, claims 1-3, 7-12, 14 and 15 are amended and claims 16 and 17 are newly added.
Claims 1-17 are pending in the instant application and are examined on the merits herein.
Priority
This application is a National Stage Application of PCT/SG2022/050711, filed on 10/5/2022. The instant application claims foreign priority to SG 10202111103X filed on 10/5/2021. Acknowledgment is made of applicant's claim for foreign priority under 35 U.S.C. 119(a)-(d). The certified copy has been filed in the instant application on 3/29/2024.
Information Disclosure Statement
The information disclosure statements (IDS) dated 3/29/2024 comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, except where noted. Accordingly, the IDS documents have been placed in the application file and the information therein has been considered as to the merits.
Claim Rejections - 35 USC § 112—Second Paragraph
The following is a quotation of 35 U.S.C. 112(b):
(B) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 11 is rejected for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor, or for pre-AIA the applicant regards as the invention.
The compound at row 1, column 3 of claim 11 is associated with the phrase “and more particularly”. This phrase renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. Preferences, options and examples are properly set forth in the specification, but when included in the claims lead to confusion over the intended scope of the claim. See MPEP § 2173.05(d). For examination purposes, the broadest claim limitation(s) will be considered without taking into account preferences or examples.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1, 2, 5-10, 12, 13 and 15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cramer et al. (Chem. Eur. J., 2016, IDS).
Cramer et al. discloses a selective acylation of carbohydrates, exemplified by the following reaction, with particular note of entries 7-10 performed at 55°C: (Table 2)
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614
579
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In Table 2 of Cramer:
“3” =
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84
158
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, which is an oxidant;
“D” and “F” are N-heterocyclic carbene (NHC) precatalysts, as depicted among the following NHC options: (Figure 1)
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353
550
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; and
“DBU” =
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166
285
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, which is both a base and a coupling agent.
Cramer also discloses that excellent selectivity was observed for carbohydrate derivatives containing multiple free OH groups. Notably, this transformation is amenable to both cis/trans 2,3-diols of the glucose, mannose, and galactose series. (p. 7406, Col. 1)
Accordingly, the instant claims are anticipated by the prior art.
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 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 of this title, 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.
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.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
Claims 3, 4 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Cramer et al. (Chem. Eur. J., 2016, IDS).
The disclosure of Cramer is referenced as discussed above. Cramer does not exemplify the claimed polyols.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to expand upon the exemplified embodiment of Cramer to include other carbohydrates such as those of the glucose, mannose, and galactose series, because Cramer concludes that the synthetic approach disclosed is broadly applicable to these carbohydrates as well. In addition, one of ordinary skill in the art could envision deprotecting the 6 position, to cleave the TIPS group, of the exemplified compound 1 of Cramer, which would yield a carbohydrate starting material identical to the first two entries in the table of instant claim 4.
Accordingly, the instant claims are prima facie obvious over the teachings of the prior art.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Cramer et al. (Chem. Eur. J., 2016, IDS), in view of Ragano et al. (ACS Sust. Chem. Eng., June 2021, PTO-892).
The disclosure of Cramer is referenced as discussed above. Cramer does not teach the claimed acylating agents.
Ragano et al. discloses selective acylation of polyols using NHC chemistry where multiple acylation reagents were studied, as tabulated below: (Table 3)
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969
399
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It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to expand upon the exemplified embodiment of Cramer to employ other art recognized acylation reagents used in NHC chemistry of polyols, thereby arriving at the instant invention. One would look to Ragano, as analogous art, for guidance on the types of acylation reagents that would reasonably be art-recognized.
Accordingly, the instant claims are prima facie obvious over the teachings of the prior art.
Claims 14 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Cramer et al. (Chem. Eur. J., 2016, IDS), in view of DeSarkar et al. (Chem. Eur. J., 2013, PTO-892).
The disclosure of Cramer is referenced as discussed above. Cramer does not teach the use of a boronic acid.
DeSarkar et al. discloses that NHC chemistry can be modified with the inclusion of alkyl boronic acids, as oxidants, to generate a boronic acid-NHC adduct which can be used for esterification reactions. (Scheme 11)
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227
385
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It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the reaction of Cramer could be modified with the addition of a boronic acid, such as taught by DeSarkar, thereby arriving at the instant invention. One would look to DeSarkar, as analogous art, for guidance on art-recognized modifications to the oxidant in NHC chemistry which would be equivalent to the oxidant of Cramer.
Accordingly, the instant claims are prima facie obvious over the teachings of the prior art
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DALE R MILLER whose telephone number is (571) 272-6146. The examiner can normally be reached on M-F 7:00 AM – 3:30 PM EST.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached on (571) 270-5341. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DALE R MILLER/Primary Examiner, Art Unit 1693
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