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 .
DETAILED ACTION
This office action is response to communication filed on 04/16//2026.
Election/Restriction
Applicant elected Group I invention and compound species recited in claim 4 having structure shown below on 04/16/2026.
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Applicant identified claims 1, 2, 4 and 13-15 read on the elected invention and species. 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)).
Claims 16-26 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention.
Claims 3 and 5-12 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
The elected species disclosed in instant spec as Q-NA (See Fig. 7 ), is a compound of Formula I wherein X is NO2, Y is H, m=7, n=8; or Y=CH3, m=7, n= 7.
The elected species (CAS# 2839679-59-1, entered STN database on October 14, 2022), is rejected under following 103 rejection.
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Other non-elected species are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to non-elected species, there being no allowable generic or linking claim.
Status of Claims
Claims 1-26 are pending in the instant application.
Claim 3, 5-12 and 16-26 are withdrawn.
Claims 1, 2, 4 and 13-15 are under examination in this office action.
Priority
The instant application 18/282,099 filed on 09/14/2023, is a 371 of PCT/US2022/021714 filed on 03/24/2022, which claims priority benefit of US provisional application No. 63/166,058 filed on 03/25/2021.
Information Disclosure Statement
The information disclosure statement dated 10/19/2023 is in compliance with the provisions of 37 CFR 1.97. The reference listed in IDS are being considered by the Examiner.
Claim Objections
Claims 1 and 2 are objected to because of the following informalities:
m, n in the Formula I, II, III, IV, XV, XVI are not drawn properly adjacent to the parenthesis.
Specification
The disclosure is objected to because the structure of “Q-NA” is confusing. Instant specification recites variety of Q-NA and activity thereof (See Figs 1-9; page 30, line 33-37; page 31, and Results from page 33 ). The structure of Q-NA in Fig. 1 and Fig. 7 are not the same. It’s not clear the position of NO2 in the structure of Q-NA. It’s not clear which Q-NA exhibit the activity as recited in Results.
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Drawings
The drawings are objected to because Fig.1, Fig. 3, Fig. 8 and Fig. 9 are blurry . It’s not clear if the Q-NA in Fig. 1 and Fig.3 should be the same as Q-NA in Fig. 7 and Fig. 9.
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.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claim 1 and 13-15 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
The MPEP states that for a generic claim the genus can be adequately described if the disclosure presents a sufficient number of representative species that encompass the genus. If the genus has a substantial variance, the disclosure must describe a sufficient variety of species to reflect the variation within that genus. See MPEP § 2163. Although the MPEP does not define what constitute a sufficient number of representative species, the courts have indicated what do not constitute a representative number of species to adequately describe a broad genus. In Gostelli, the courts
determined that the disclosure of two chemical compounds within a subgenus did not describe that subgenus. In re Gostelli, 872, F.2d at 1012, 10 USPQ2d at 1618.
Claim 1 recites compound of formula I, II, III, IV comprising X, and Y moiety, wherein X is an electron withdrawing group, Y is a terminal group that inhibits enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached. Instant specification (See [0161]) discloses: the term “electron-withdrawing group” is recognized in the art and denotes the tendency of a substituent to attract valence electrons from neighboring atoms, i.e., the substituent is electronegative with respect to neighboring atoms. Embodiments encompass any known electron-withdrawing group...”. Instant specification discloses working example wherein X is NO2. Instant specification does not disclose working example comprising other electron-withdrawing groups, e.g. COOH, COOR, CN, sulfoxide, sulfonyl, etc. as recited in claim 13. Instant specification discloses embodiments wherein Y is H or methyl. Instant specification does not disclose working example wherein Y is cyclopropyl, or alkynyl. Instant specification does not disclose/define what terminal group that inhibit enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached. In absence of sufficient working example of other groups as Y, an ordinary skilled in the art would not know whether the Applicant, at the time the application was filed, had possession of instant claimed compound genus comprising X electron-withdrawing moiety genus and Y moiety genus that inhibit enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached.
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.
Claims 1, and 13-15 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.
Claim 1 recites compound of formula I, II, III, IV comprising X, and Y moiety, wherein X is an electron withdrawing group, Y is a terminal group that inhibits enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached. The definition of X , Y by property of the group or intended result is indefinite. An ordinary skilled in the art would not be appraised the scope of X, Y moiety, especially Y moiety. The lack of clear definition of X, Y moiety in the formula(s) renders the claims indefinite since the resulting claims do not clearly set forth the metes and bounds of the patent protection desired.
Claims 13-15 are also rejected due to dependency on claim 1.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 15 is rejected under 35 U.S.C. 112(d), as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 15 depends on claim 1 and recites Y is H, dimethyl, trimethyl, cyclopropyl, or alkynyl. Claim 1 recites Y is a terminal group that inhibits enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached. It’s not clear how the group of H, dimethyl, trimethyl, cyclopropyl, or alkynyl inhibits enzymatic omega-end hydroxylation, oxidation and shortening of the alkyl chain to which Y is attached. Thus, claim 15 fails to include all the limitations of the claim upon which it depends.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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 non-obviousness.
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, 2, 4 and 13-15 are rejected under 35 U.S.C. 103 as being unpatentable over Wan et al. (US 3974187A ) in view of Batthyány et al. (US20180297973A1).
Wan teaches 6-alkyl derivatives of 2,3-dimethoxy-5-methyl-1,4-benzoquinone as analogs of Coenzyme Q, that have coenzyme activity as naturally occurring coenzyme (e.g. coenzyme Q10) (See abstract; Col. 2, line 28-38; Examples; Table I, II, claims 1-8).
Wan teaches the structure of naturally occurring coenzyme Q6 to Q10 (See Col. 1) and 6-alkyl derivatives of 1 ,4-benzoquinone comprising both saturated and unsaturated straight carbon chains that reads on the core structure of instantly claimed compounds (See Table 1, Examples).
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Wan explicitly teaches compound, 2,3- dimethoxy-5-methyl-6-(8 '-heptadecenyl)-1,4-benzoquinone and activity thereof(See Col. 4, line 15- 37; Table 1) that’s very similar to instant elected species except the NO2 group.
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Batthyány teaches anti-inflammatory, antioxidant nitroalkene and methods of use thereof in the treatment and prevention of inflammation related conditions(See abstract, [0011], [0013], claim 1-20).
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Batthyány teaches the benefit/advantage of endogenous electrophilic nitrated unsaturated fatty acids, including nitro-linoleic acid (LNO2) and nitro-oleic acid (OA-NO2), that mediate anti-inflammatory and pro-survival signaling reactions, wherein the presence of the nitro group on the double bond turns the β-carbon adjacent to the nitroalkene strongly electrophilic and reacts covalently with nucleophiles both in proteins (thiols and histidine residues) and low molecular weight molecules via Michael addition reactions (See [0002]-[0003], [0006], [0011]). Batthyány also teaches Nrf2 ( nuclear factor erythroid 2-related factor 2) pathway and NAD (P) H: quinone oxidoreductase-1 (NQO1), which also reduces antioxidants coenzyme Q10 to their active form(See [0003]-[0004]). Batthyány also teaches rationale for non-endogenous nitroalkenes conjugate derivatives, e.g. wide range of anti-inflammatory , anti-proliferative activity by modifying major signaling pathways, not as susceptible to beta oxidation or
metabolism via the classical desaturation pathway, etc. (See [0009]-[0011]).
Batthyány teaches variety of compound species comprising nitroalkene / vinyl nitro conjugate(See [0018]-[0024], claim 18), general synthetic procedures and Examples (See [0090]- [0091]).
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According to M.P.E.P. § 2144.09, a prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).
Wan discloses coenzyme Q10 analogs that’s very similar to instant elected species except NO2 group. It would have been prima facie obvious to one of ordinary skilled in the art before the effective filing date of instant application to modify the coenzyme Q10 derivative taught by Wan, with the teaching of nitroalkene/ nitrated double bond taught by Batthyány, together with experimentation/optimization based on general knowledge of structure similarity and bioisosteric modification, and arrive at instantly claimed invention with reasonable expectation of success. A skilled artisan would have been motivated to further explore nitrated derivative of coenzyme Q10 and reasonably expected the nitrated derivative of coenzyme Q10 would exhibit coenzyme activity associated with redox homeostasis and antioxidant/anti-inflammation associated with NRF-2 and other pathway, since Batthyány teaches the nitro group on the double bond turns the β-carbon adjacent to the nitroalkene strongly electrophilic and reacts covalently with nucleophiles which might be beneficial for anti-inflammatory signaling.
One of ordinary skill in the art would have had reasonable expectation of success in producing the claimed invention base on the combined teachings of prior art and further exploration/optimization based on general knowledge of structure similarity and bioisosteric modification. For example, compound 2,3- dimethoxy-5-methyl-6-(8 '-heptadecenyl)-1,4-benzoquinone taught by Wan, could have been modified to instant elected species by introducing NO2 at the double bond as taught by Batthyány.
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Therefore, the invention as a whole is prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LIYUAN MOU whose telephone number is (571)270-1791. The examiner can normally be reached Mon-Fri 9:00-5:30.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached on (571)272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LIYUAN MOU/Examiner, Art Unit 1628
/JARED BARSKY/Primary Examiner, Art Unit 1628
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