DETAILED ACTION
This office action is in response to the Applicant’s filing dated February 2nd, 2026.
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 .
Status of Claims
Claims 1-20 are pending in the instant application. Acknowledgement is made of Applicant’s remarks and amendments filed on February 2nd, 2026. Acknowledgement is made of the Applicant’s amendment of claim 1. Claims 11-20 remain withdrawn.
Priority
This application is a 371 of PCT/US2021/051072 filed on September 20th, 2021; and has a PRO 63/080,708 filed on September 19th, 2020.
Objections and/or Rejections and Response to Arguments
Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated (Maintained Objections and/or Rejections) or newly applied (New Objections and/or Rejections, Necessitated by Amendment or New Objections and/or Rejections, NOT Necessitated by Amendment). They constitute the complete set presently being applied to the instant application.
New Objections and/or Rejections
Necessitated by Claim Amendment
Claim Objections
Claim 8 is 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, recite only the elected species, and to remove the currently non-elected subject matter.
Maintained Objections and/or Rejections
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:
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 1, 3-7 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over Rauniyar et al. (US 2014/0350253 A1); in view of Meanwell (Journal of Medicinal Chemistry. (2011), 54, 2529-2591); as evidenced by Rowe et al. (Isopropyl Alcohol. Handbook of Pharmaceutical Excipients. (2009), 6th Edition, Pharmaceutical Press, 346-348), cited for evidentiary purposes only.
Regarding claims 1, 3-7 and 9, Rauniyar teaches compound (5b) shown below (page 36, paragraph [0227]):
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Which is a bioisostere of the compound initially expanded to by the Examiner overlapping at the following points: wherein a double bond is present between R3 and R7; wherein X is N; wherein R1 and R2 are both aryl; wherein R3 and R7 are both H; and wherein n is 1.
The only difference between Compound (5b) of Rauniyar and the compound initially expanded to by the Examiner is the presence of CF, instead of CH, at the Y position of instantly claimed Formula (I).
Meanwell teaches that fluorine is a bioisostere of hydrogen, and this replacement tactic is used by medicinal chemists to modulate a range of compound properties of interest (page 2531, left column, last paragraph); such as increased metabolic stability (page 2532, left column, first paragraph) and increased compound potency (page 2534, left column, last paragraph).
The motivation to substitute a fluorine for hydrogen in a compound is the establishment in the art that substitution of hydrogen by fluorine results in a bioisostere with similar activity with potential for increased metabolic stability and increased compound potency. As such, Compound (5b) of Rauniyar is a known bioisostere of the instantly claimed compound initially expanded to by the Examiner.
Regarding claim 10, Rauniyar teaches a mixture comprising Compound (5b) and isopropanol (page 35, paragraph [0228], last 3 lines). Isopropanol reads on a pharmaceutical excipient (carrier/vehicle in topical formulations) as evidenced by Rowe, cited for evidentiary purposes only, in the Handbook of Pharmaceutical Excipients (page 346, section 7). Although the presence of hexane is noted, given the comprising language of the instantly claimed invention, the examiner notes that other ingredients are not precluded.
Taken together the teachings of Rauniyar and Meanwell would result in the compound and composition of instant claims 1, 3-7 and 9-10.
Allowable Subject Matter
The following is a statement of reasons for the indication of allowable subject matter:
In a search of the claimed compound of Formula (II) of claim 2, the compound of Formula (II) was found to be free of prior art.
As allowable subject matter has been indicated, applicant's reply must either comply with all formal requirements or specifically traverse each requirement not complied with. See 37 CFR 1.111(b) and MPEP § 707.07(a).
Response to Arguments
Applicant argues:
Applicant contends that one would not modify the compounds of Rauniyar to replace the fluorine atom with hydrogen in view of the teachings in Rauniyar.
Examiner's response:
The above argument has been carefully considered and has not been found persuasive.
One of ordinary skill in the art would be motivated to modify the compound of Rauniyar in view of the teachings from Meanwell as discussed in the above rejection. Specifically, Meanwell’s teaching that fluorine is a bioisostere of hydrogen, and the substitution will result in a compound of similar activity with adjusted the potency and metabolic stability. Absent evidence of unexpected results, these changes constitute predictable optimizations within the skill of an ordinary artisan.
MPEP § 2144.09(III) states:
“Claimed and prior art compounds used in a method would have been expected to have similar activity because the structural difference between the compounds involved a known bioisosteric replacement” In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990).
Conclusion
Claims 1, 3-7 and 9-10 are rejected.
Claim 8 is objected to.
Claim 2 is allowed.
THIS ACTION IS MADE FINAL. 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 CHRISTOPHER L JOHNSON whose telephone number is (571)272-1672. The examiner can normally be reached Monday - Friday 08:00AM - 5:00PM EST with Flex on Fridays.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/C.L.J./Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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