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 of Group I (e.g. claims 52-60) drawn to the compound having the formula M-L-D; and compound I5 as species A drawn to the compound having the formula M-L-D in the reply filed on December 24, 2025 is acknowledged.
Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
The Examiner further respectfully notes no prior art was found for the elected compound I5 nor the compounds recited within claim 68.
Therefore, the Examiner hereby modifies the elected species as discussed above where the compound having the formula M-L-D, wherein M is a mannose moiety, L is an oxime moiety, and D is dexamethasone.
The Examiner respectfully reiterates the modified elected species as discussed above reads on claims 52, 56-57, 59-60, and 68-71.
Drawings
The drawings are objected to because within Figure 2 the phrase "activated macrophage" is cut-off and thus the full phrase does not appear within the figure.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Information Disclosure Statement
The Information Disclosure Statements (IDS) filed on 12/11/2024 and 03/12/2026 have been considered by the Examiner inasmuch as foreign documents have been submitted into the file wrapper in English.
Claim Status
The claim set filed December 24, 2025 has been entered. Claims 1-51, 53-55, 58, and 61-67 are canceled. Thus, claims 52, 56-57, 59-60 and 68-71 as amended are examined on the merits herein.
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.
Claims 52, 56-57, and 59-60 are rejected under 35 U.S.C. 103 as being unpatentable over Friend et al. (Published 11 November 1993, WO-9322334-A1, IDS filed 12/11/2024) in view of Hu (Published Year 2005, Prodrug "Approaches to Drug Delivery", in: Wang et al., Drug Delivery: Principles and Applications (Hoboken, New Jersey, John Wiley & Sons, Inc, 2005), pp. 125-165, PTO-892).
Regarding claims 52, 56-57, and 59-60, Friend teaches a prodrug having the following structural formula depicted as,
PNG
media_image1.png
298
260
media_image1.png
Greyscale
, see pg. 28, claim #1, lines 5-10.
Friend teaches R is a sugar moiety; R1 is H; R2 is halogen; R3 is lower alkyl; R4 is OH; R5 is OH; R6 and R9 is lower alkyl; and α is an optional double bond, see pg. 28, claim #1, lines 15-33.
Friend defines the term “lower alkyl” as encompassing alkyl groups having and including 1 carbon atom, see pg. 7, lines 19-21.
Friend teaches R is selected from the group consisting of and including α-mannose and β-mannose (e.g. a mannose moiety, required in claim 52, lines 1-2), see pg. 28, claim #3.
Friend teaches the corticosteroid is dexamethasone (e.g. dexamethasone, required in claims 59-60), see pg. 29, claim #7.
The Examiner respectfully notes the linker which links the sugar moiety taught as mannose above and the corticosteroid taught as dexamethasone above contains a -CH2-CO- moiety, as discussed above. Therefore, in view of the teachings above, the Examiner respectfully notes the limitation “where L further comprises a C1 alkyl group” required within claim 57 is met.
Although, Friend does not teach the limitation where the mannose moiety is linked to the corticosteroid with a linker that comprises an oxime moiety, required in claims 52, 56-57 and 59-60.
However, in the same field of endeavor of prodrugs, Hu teaches within Table 8.1 reversible prodrug forms for various functional groups present in biologically active substances and exemplifies a carbonyl and an oxime are reversible prodrug forms present in biologically active substances, see pg. 138, Table 8.1.
Hu teaches oximes formed from ketones with hydroxylamines are chemically reversible under acidic or basic conditions and could be used as prodrugs of compounds containing carbonyl functionality, see pg. 149, section 8.8.4.1. Schiff Bases and Oximes, paragraph 1.
It would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have modified the prodrug of Friend which contains a carbonyl linking the mannose to dexamethasone by substituting said carbonyl of Friend for an oxime as taught by Hu above as within the scope of the artisan as combining prior art elements according to known compounds and methods to yield predictable results.
One of ordinary skill in the art would have been motivated to make the substitution as discussed above in order to create the prodrug of Friend as discussed above. One of ordinary skill in the art would have had a reasonable expectation of success to have made the modification as discussed above, because both Friend and Hu are drawn to prodrugs; Hu explicitly teaches a carbonyl and an oxime are reversible prodrug functional groups present in biologically active substances; and wherein Hu explicitly teaches oximes are formed from ketones with hydroxyl amines as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
Allowable Subject Matter
Claims 68-71 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.
The following is a statement of reasons for the indication of allowable subject matter: Nedelec et al. (Published 19 February 1980, US-4189477-A, PTO-892) teaches novel Δ4-pregnenes, see Col. 1, lines 20-25. Nedelec exemplifies the novel Δ4-pregnenes having the formula depicted as,
PNG
media_image2.png
228
429
media_image2.png
Greyscale
, see Col. 1, lines 25-35.
Nedelec teaches R1 is selected from the group consisting and including hydrogen; X2 is selected from the group consisting of and including -OH; R is selected from the group consisting of and including hydrogen and methyl; X1 is selected from the group consisting of a ketone or a hydroxyl; Y is selected from the group consisting of and including a halogen; Z is selected from the group consisting of and including alkoxy of 1 to 12 carbon atoms, see Col. 1, lines 25-55.
Nedelec teaches the dotted line in the A ring indicates the optional presence of a double bond in the 1(2)-position and A and B are both hydrogen, see Col. 2, lines 10-15.
The Examiner respectfully notes the teachings of Nedelec discussed above correspond to the compound as recited within claim 68, specifically wherein the drug is dexamethasone and the linker is an oxime moiety.
Although, the Examiner respectfully notes Nedelec does not teach where the alkoxy of Z is substituted with a mannose moiety as required within claim 68, which corresponds to M is a mannose moiety as recited in claim 52, lines 1-2; and thus, the teachings of Nedelec do not anticipate the compound as recited within claim 68.
Additionally, in view of the teachings of Nedelec as a whole as discussed above, it would not have been obvious to modify the C1-C12 alkoxy of Nedelec with a mannose moiety, wherein said alkoxy of Nedelec is linked to the oxime moiety specifically at the C3-position of dexamethasone as recited and required of the compounds of claim 68.
Thus, the teachings of Nedelec do not make obvious the compounds recited within claim 68. Claims 69-71 depend from the compounds of claim 68.
Conclusion
No claims are allowed in this action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JARET J CREWS whose telephone number is (571)270-0962. The examiner can normally be reached Monday-Friday: 9:00am-5:30pm 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, Renee Claytor can be reached at (571) 272-8394. 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.
/JARET J CREWS/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691