DETAILED ACTION
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 .
CONTINUING DATA
This application is a 371 of PCT/US22/20849 03/18/2022
PCT/US22/20849 has PRO 63/163,668 03/19/2021
Applicant’s election without traverse of Group I, claims 1-9 and 52, in the reply filed on May 12, 2026 is acknowledged.
Claims 10, 13, 20, 22, 32, 38, and 48-51 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on May 12, 2026.
Drawings
Figures 5A-9B are objected to because the figures are pixelated and difficult to read.
Specification
The disclosure is objected to because of the following informalities: the chemical structures in paragraph [0036] are pixelated and difficult to read.
Appropriate correction is required.
Claim Interpretation
The claims recite a reactive moiety. “Reactive moiety” is not defined in the specification, so the ordinary definition of the term is the broadest reasonable interpretation. “Reactive moiety” is interpreted to include any moiety which can react with a chemical compound under any conditions.
Claim Rejections - 35 USC § 112
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 4 and 9 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 4 recites the broad recitation “1-20,”, and the claim also recites “preferably 2 to 10 or 2 to 4,” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
The chemical structures in claim 9 are pixelated and difficult to read, so it is unclear what is being claimed. Additionally, claim 9 is incomplete because it lacks a period at the end.
Claim Rejections - 35 USC § 102
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 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) 1-6 and 8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Nitz (J. Org. Chem., cited on IDS).
Nitz teaches the following compounds on page 8415:
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341
395
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486
656
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531
623
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In compound 29, the reactive group is allyl. In compound 32, the reactive group is NH2 and the linker is –(CH2)3-S-(CH2)2-. In compound 43, the reactive group is a squarate group.
Claim(s) 1-6 and 8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Qiao (Tetrahedron 81 (2021) 131920, published online January 7, 2021).
Qiao teaches the following compound in Table 1:
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169
462
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The reactive group is amino and the linker is an alkyl linker.
Claim(s) 1, 5-6, and 52 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Belz (Carbohydrate Research 429 (2016) 38-47).
Belz teaches the following compounds on page 41.
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420
759
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Compound 22 is a tetrasaccharide and the reactive group is SAc. Compound 11 is a hexasaccharide and the reactive group is SAc.
Belz teaches that S-linked glycoconjugates typically do not undergo enzymatic transformation, so they are useful as oligosaccharide mimics. See first paragraph of Introduction.
Claim(s) 1-2 and 6-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ding (Eur. J. Org. Chem. 1999, 1143-1152).
Ding teaches the following compounds on page 1144:
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473
511
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The reactive group in compound 11 is OAc. The reactive group in compound 12 is OH. The compound is a hexasaccharide composed of glucose moieties. Ding also teaches the following compounds on page 1145:
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465
587
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The reactive group in compound 23 is Br. The reactive group in compound 24 is SC(=NH)NH2. The reactive group in compound 25 is thiol.
S-linked thio analogs of oligosaccharides might be expected to be less prone to enzymatic inactivation as compared to their O-linked natural counterpart. See Introduction.
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.
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) 1-9 and 52 is/are rejected under 35 U.S.C. 103 as being unpatentable over Krauss (US 2013/0116417 A1, May 9, 2013) in view of Ding (Eur. J. Org. Chem. 1999, 1143-1152), Belz (Carbohydrate Research 429 (2016) 38-47), Nguyen (ACS Cent. Sci. 2019, 5, 237-249) and Bruxelle (Scientific Reports (2020) 10:7582).
Krauss teaches oligosaccharides useful for preparing vaccines. See abstract. Paragraph [0124[ illustrates compounds which are similar to the compounds of current claim 9 except they are not S-linked. The reactive group in Krauss’s compounds is N3, and it is attached through an alkyl linker.
Ding teaches methods for preparing S-linked oligosaccharides, as set forth above. S-linked thio analogs of oligosaccharides might be expected to be less prone to enzymatic inactivation as compared to their O-linked natural counterpart. See Introduction.
Belz teaches as set forth above, the synthesis of S-linked mannooligosaccharides. Belz teaches that S-linked glycoconjugates typically do not undergo enzymatic transformation, so they are useful as oligosaccharide mimics. See first paragraph of Introduction.
Nguyen teaches oligomannose compounds for targeting antibodies. See title. The oligomannose compounds are illustrated on page 243. Nguyen observed significant trimming of the glycoconjugates (page 244, last paragraph). Mannosides trimming of the vaccine glycans may affect the glycan microspecificity of vaccine-elicited antibodies. Page 245. Trimming occurs at the glycan “tips.” See Conclusion.
Bruxelle teaches that serum mannosidase trimming of oligosaccharides in vivo lessens the likelihood of eliciting antibodies with capacity to bind full-sized oligomannose (see abstract). Bruxelle confirmed that Nguyen’s hypothesis of glycoside trimming does occur in vivo. See page 2, first paragraph. Bruxelle suggests preparing mannosidase-resistant glycosides. Page 5, end of Discussion section.
It would have been obvious to one of ordinary skill in the art at the time the application was filed to prepare S-linked analogs of Krauss’s compounds because oligomannosides undergo trimming in vivo, which causes vaccines made from the oligomannosides to be less effective. Ding and Belz teach that S-linked oligosaccharides are less likely to undergo enzymatic inactivation, so the skilled artisan would have prepared S-linked analogs to overcome the problem of glycoside trimming. Ding and Belz teach methods for preparing S-linked oligosaccharides, so the skilled artisan would have had a reasonable expectation of success. The skilled artisan would have prepared compounds which are S-linked at the non-reducing end because trimming occurs at the “tips,” as taught by Nguyen.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LAYLA D BERRY whose telephone number is (571)272-9572. The examiner can normally be reached 7:00-3:00 CST, M-F.
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/LAYLA D BERRY/ Primary Examiner, Art Unit 1693
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