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 .
Election/Restrictions
Applicant's election with traverse of Group I, drawn to claims 1-13, in the reply filed on 05/02/2026 is acknowledged. The traversal is on the grounds that (a) no evidence, citation. Or technical explanation showing that an alternative synthesis route to the claimed product is possible and (b) that a serious search/examination has not been demonstrated. This is not found persuasive because Group I, the product, can be made by a materially different process than the claimed process is, as demonstrated in U.S. Patent No. 2,784,199. Therein, a compound which reads to the instantly claimed product of claim 1 is made via addition of a substituted amine to the bridged species 3,6-endoxyhexahydropthalic anhydride (which could conceivably be made first via hydrogenation of the Diels-Alder product of furan and maleic anhydride), wherein the anhydride is cleaved, and the reaction is heated to recyclized the compound to a compound matching Formula I wherein n = 0. This process is materially different from that which is claimed, wherein an N-substituted maleimide and a furan-containing compound undergo a Diels-Alder reaction followed by hydrogenation. Furthermore, a serious search burden was properly established in the previous restriction requirement because the two inventions have separate classifications and when classifiable together would have a separate status.
The requirement is still deemed proper and is therefore made FINAL.
Claims 14-26 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being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. Applicant timely
traversed the restriction requirement in the reply filed on 05/02/2026.
Priority
Acknowledgment is made of applicant’s claim domestic benefit from U.S. Provisional Application No. 63/408,513 filed 21 September 2022.
Information Disclosure Statement
The Information Disclosure Statement (IDS) filed on 19 February 2026 has been reviewed and considered by the examiner.
Drawings
Color photographs and color drawings are not accepted in utility applications unless a petition filed under 37 CFR 1.84(a)(2) is granted. Any such petition must be accompanied by the appropriate fee set forth in 37 CFR 1.17(h), one set of color drawings or color photographs, as appropriate, if submitted via the USPTO patent electronic filing system or three sets of color drawings or color photographs, as appropriate, if not submitted via the via USPTO patent electronic filing system, and, unless already present, an amendment to include the following language as the first paragraph of the brief description of the drawings section of the specification:
The patent or application file contains at least one drawing executed in color (Fig. 11A, Fig. 11B, and Fig. 14). Copies of this patent or patent application publication with color drawing(s) will be provided by the Office upon request and payment of the necessary fee.
Color photographs will be accepted if the conditions for accepting color drawings and black and white photographs have been satisfied. See 37 CFR 1.84(b)(2).
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.
Claims 1-4 and 8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Grogan & Rice (J. Med. Chem., 1963, 6(6), pp. 802-805).
With regard to claim 1, Grogan & Rice disclose various substituted 7-oxabicyclo[2,2,1]heptane-2,3-dicarboximides (see Table I, pp. 803) which share the parent structure of instantly claimed Formula I wherein n = 0. Furthermore, Grogan & Rice disclose compounds sharing Formula I wherein R1 (i.e. X) is hydrogen (line 1, Table I), an alkyl (lines 2-4, Table I), or a carboxyl (line 26, Table I) and R2/R3 (i.e. R/R’) are hydrogen or an alkyl (lines 1-26, Table I). As n = 0 in the prior art, a linker (R4) is not present.
With regard to claim 2, Grogan & Rice disclose a compound sharing Formula I and wherein R1 is 4-carboxy-phenyl (line 26, Table I, pp. 803). Carboxyl groups are a well-known functional group capable of catalyzing chemical reactions through their acidic moiety, and thus the compound is capable of catalyzing a chemical reaction.
With regard to claim 3, Grogan & Rice disclose a compound with Formula I wherein R1 is a substituted aryl (4-carboxy-phenyl, line 26, Table I, pp. 803).
With regard to claims 4 and 8, the process limitations are noted. However, when the examiner has found the same or substantially similar product as in the applied prior art, the burden of proof is shifted to applicant to establish that their product is patentably distinct and not the examiner to show the same process of making. In re Brown, 173 USPQ 685 and In re Fessmann, 180 USPQ 324.
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 9 is rejected under 35 U.S.C. 103 as being unpatentable over Grogan & Rice as applied to claim 1 above, and further in view of Haj & Ahmed (Molecules, 2020, 25(8), 1937).
Grogan & Rice does not teach that R2 and R3 of the structure of claim 1 may be hydroxy-C1-C6-alkyl. However, Haj & Ahmed teach that the functionalization of small organic molecules via the addition of hydroxyl groups is commonplace in natural systems and as a means to alter a molecule’s chemical properties/activity (pp. 1, Abstract). Specifically, inclusion of a hydroxyl group can lead to increased steric hinderance around a specific site of the molecule or a change to the molecule’s hydrophobicity (pp. 18, Section 3).
Both Grogan & Rice and Haj & Ahmed are written in regards to small organic molecule pharmaceuticals, and thus a person of ordinary skill in the art would reasonably have access to and understand the teachings of both pieces of prior art. As such, the alteration of the R2 and R3 positions of Grogan & Rice to comprise a C1-C6 hydroxy moiety, as taught by Haj & Ahmed, would have been obvious to one of ordinary skill in the art at the relevant time because such is a recognized technique for the control of a molecule’s hydrophobicity.
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Grogan & Rice as applied to claim 1 above, and further in view of Minakata & Komatsu (Chem. Rev., 2009, 109(2), pp. 711-724).
Grogan & Rice does not teach that the chemical structures disclosed are immobilized on a support. However, Minakata & Komatsu teach that immobilized catalysts on inorganic supports, specifically silica, are advantageous because of their easy recovery from reaction mixtures and reuse. Furthermore, catalysts can be immobilized via covalent or non-covalent attachment and effectively used in aqueous media (pp. 1, right column, lines 12-16). Grogan & Rice teach that the chemical structures disclosed are intended for under normal physiological conditions and have varying degrees of pharmacological activity in aqueous environments (pp. 802, left column, lines 1-17). Modifying the teachings of Grogan & Rice to immobilize the disclosed small organic molecules onto an inorganic support as suggested by Minakata & Komatsu could then yield a catalytic organic molecule which can more easily be recovered from aqueous media after reactions. Therefore, it would have been obvious to one of ordinary skill to modify the taught chemical structures of Grogan & Rice to be immobilized on a support as taught by Minakata & Komatsu in order to improve recoverability.
Claims 5-7 are rejected under 35 U.S.C. 103 as being unpatentable over Grogan & Rice as applied to claim 4 above, and further in view of Galehban et al. (RCS Adv., 2022, 12, pp. 16454-16478).
With regard to claims 5-7, Grogan & Rice do not teach that a molecule with Formula I has an R1 substituent which is an amino acid or one of the amino acids subsequently claimed in claims 6 and 7.
However, Galehban et al. teaches a glutamic-acid modified chitosan immobilized on a support for use in trapping metal particles and catalysis in aqueous solutions (pp. 16454, Abstract). In the material, L-glutamic acid is substituted onto the ring system of chitosan as both a cross-linking additive and to provide complexation sites for metal nanoparticles (pp. 16455, right column lines 8-12; pp. 16456, right column, lines 2-6). Galehban et al. demonstrates the affinity of the oxygen moieties of L-glutamic acid for complexing with metal ions, which is a desirable quality for small organic molecules intended for use in and/or around pharmacological active sites, which are often metal ions. Galehban et al. even discloses that such a catalytic system may be attractive in the fields of biomedicine or drug delivery (pp. 16455, left column, lines 50-57). Given the relevance of Galehban’s adapted chitosan to biomedicine, the targeted use of the compounds taught by Grogan & Rice, a person of ordinary skill in the art would have thought to apply the teachings of Galehban et al. to Grogan & Rice with a reasonable expectation of success in yielding useful compounds.
Therefore, it would have been obvious to one of ordinary skill in the art at the relevant time, to have modified the chemical structure of Grogan & Rice to include L-glutamic acid as a substituent in order to increase the small molecule’s affinity for metal complexation in an aqueous environment, as suggested by Galehban et al., and to yield a L-glutamic acid substituted compound which reads to the limitations of claims 5-7.
Allowable Subject Matter
Claims 10-12 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
With respect to claims 10-12, the claims are indicated as containing allowable subject matter because the structure of Formula I wherein n is greater than 0 have not previously been reported in the art. There is no precedent in the prior art which would motivate one of ordinary skill to design a molecule with the structure of claims 10-12 (wherein n ≥ 1), or to modify the reported structures of Grogan & Rice, the closest identified prior art, in such a way as to result in the instantly claimed structures, without use of improper hindsight based on the present disclosure.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MORDECAI M LEAVITT whose telephone number is (571)272-6637. The examiner can normally be reached Monday-Friday 8AM-5PM.
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, CHRISTINA JOHNSON can be reached at (571) 272-1176. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/MORDECAI M LEAVITT/Examiner, Art Unit 1742 /CHRISTINA A JOHNSON/Supervisory Patent Examiner, Art Unit 1742
Prosecution Insights