DETAILED ACTION
This office action is in response to the Applicant’s filing dated November 17th, 2025.
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.
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.
Election/Restrictions
Applicant's election with traverse of Group I in the reply filed on November 17th, 2025 is acknowledged. The traversal is on the grounds that Salvati et al., cited in the previous Office Action, teaches a compound that does not contain a CH2, O, S, or NH attached to the bridged ring via a double bond at the Z variable of instantly claimed Formula (I); and a methylene group is not present between the Y and R2 variables of instantly claimed Formula (I). This is not found persuasive because these aforementioned variables are not part of the Applicant’s instantly claimed core structure as defined by MPEP § 1850(III)(B)(1).
The requirement is still deemed proper and is therefore made FINAL.
Claims 11-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 November 17th, 2025.
Applicant’s election of species without traverse of the compound of Formula (II), shown below, in the reply filed on November 17th, 2025 is acknowledged.
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Which is a species of genus Formula (I) wherein a double bond is present between R3 and R7; wherein X and Y are both N; wherein Z is O; wherein R1 and R2 are both aryl; wherein R3 is CN; wherein R7 is H; and wherein n is 1. This compound can be found in claim 2.
This compound was found free of prior art.
Therefore, the Examiner expanded search to the compound shown below:
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Which is a species of genus Formula (I) wherein a double bond is present between R3 and R7; wherein X is N; wherein Y is CH; wherein Z is O; wherein R1 and R2 are both aryl; wherein R3 and R7 are both H; and wherein n is 1.
In light of the teachings of the prior art, the Examiner further expanded search to CAS RN: 71947-32-5 shown below:
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Which is a species of genus Formula (I) wherein a double bond is present between R3 and R7; wherein X and Y are both N; wherein Z is O; wherein R1 is aryl; wherein R2 is CN; wherein R3 and R7 are both H; and wherein n is 2.
This search retrieved prior art. Therefore, the Examiner’s search will not be extended unnecessarily to additional species of genus Formula (I) in/for/during this Office Action. Claims 1 and 3-10 read on the elected species and will be examined herein.
Claim Rejections - 35 USC § 112(b)
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.
Claim 1 is 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.
Regarding claim 1, In lines 9 spanning into 10 and lines 13 spanning into 14, when listing out potential substituents for R1 and R2 the applicant recites “- -CHO”, which renders the metes and bounds of the claim unclear; because it is not clear whether or not another atom is intended to be present between the two indicated bonds (e.g, “- -“).
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.
Claims 1, 3 and 5-9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Somekawa et al. (Nippon Kagaku Kaishi, (1979), 8, 1071-1078).
Regarding claims 1, 3 and 5-9, Somekawa teaches Compound [5md] shown below (page 1075, left column, Fig. 2):
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Which is a species of instantly claimed genus Formula (I) wherein a double bond is present between R3 and R7; wherein X and Y are both N; wherein Z is O; wherein R1 is aryl; wherein R2 is CN; wherein R3 and R7 are both H; and wherein n is 2. Compound [5md] of Somekawa is the compound further expanded to by the examiner.
Thus, the teachings of Somekawa anticipate the compound of instant claims 1, 3 and 5-9.
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).
Conclusion
Claims 1 and 3-10 are rejected.
Claim 2 is allowed.
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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/C.L.J./Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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