Ems 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 action is FINAL.
Status of Claims
Claims 1-14 and 16-22 are pending.
Claims 1-9, 11-13, 16-18, and 22 are examined herein.
Claims 10, 14 and 19-21 are withdrawn. (see Response to Arguments/Amendments)
Priority
PNG
media_image1.png
60
543
media_image1.png
Greyscale
This application is filed 07/13/2023 and claims the benefit of domestic priority as below:
Information Disclosure Statement
Two IDS(s) received on 10/17/2023, and 01/14/2024 have been considered unless marked with a strikethrough.
Response to Arguments/Amendments
In a non-final dated 03/18/2026, claims 7-9 and 17, and the drawing for Fig. 3A were objected to. Claims 1, 3-6, and 18 are rejected under 35 U.S.C. 102(a)(1). Claims 1, 2, 6, 11-13, and 16 are rejected under 35 U.S.C. 103.
Applicant's amendment filed 06/03/2026 is acknowledged. Claims 1, 7-9 and 17 are amended, claim 15 is canceled, and claim 22 is added. Claims 10, 14, and 19-21 are withdrawn. No new matter has been added. Accordingly, claims 1-14 and 16-22 are pending.
Applicant's arguments for the rejections under 35 USC § 102 and 35 USC § 103 filed 06/03/2026 have been fully considered but they are not persuasive.
The objection(s) for drawing is/are withdrawn, as the Applicant submitted the substitute abstract filed on 06/03/2026.
The objection(s) for claim 7-9 and 17 is/are withdrawn, as the amendments to claims 7-9, and 17 filed on 06/03/2026 have properly addressed the issues recited in the Non-Final office action.
Regarding the Claim Rejections under 35 USC § 102 for the claims 1, 3-6, and 18, Applicant's arguments filed on 06/03/2026 have been fully considered but they are not persuasive.
Applicant argues that “Claim 1 is amended to require that Rc and Rd of J1 are both
substituted (not either with H) when J1 is CRcRd. Therefore, Zhao does not anticipate Applicant's claims because Zhao does not teach each and every element of Applicant's claims.
Applicant’s arguments have been fully considered but are not persuasive. Amended claim 1 still encompasses embodiments in which Rc and Rd are each independently halogen, aryl, alkyl, cycloalkyl, or an ester containing substituent, provided that Rc and Rd are not both methyl. Thus, the amendment excludes embodiments in which either Rc or Rd is hydrogen, but it does not exclude terminal olefin embodiments in which both corresponding substituent positions are non-hydrogen substituents, including embodiments in which both positions are halogen.
Zhao discloses fusidic acid derivatives having the same core scaffold and a terminal olefin substituent pattern corresponding to the claimed Rc and Rd positions. Zhao defines R1 and R2 (i.e., Rc and Rd positions of instant Formula I) as hydrogen halogen, alkoxy, trifluoromethyl or alkyl (claim 1). Zhao further discloses preferred terminal olefin substitution patterns in which both corresponding substituent positions are non-hydrogen substituents, including R1 is trifluoromethyl, R2 is trifluoromethyl; R1 is a chlorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a bromine atom; and R1 is a chlorine atom, R2 is a bromine atom (claim 3).
Claims 3-6, and 18 depend from claim 1 and do not include additional limitations that patentably distinguish the claimed compounds form Zhao. Thus, Applicant’s argument with respect to amended claim 1 is also insufficient to overcome the previous rejection of dependent claims 3-6, and 18.
Accordingly, the rejection of claims 1, 3-6, and 18 under 35 USC 102(a)(1) is maintained.
Regarding the Claim Rejections under 35 USC § 103 for the claims 1, 2, 6, 11-13, and 16, Applicant's arguments filed on 06/03/2026 have been fully considered but they are not persuasive.
Applicant argues that “the Office Action has not established a prima facie case of
obviousness because Zhao's data led to a path that was divergent from Applicant's path of discovery.” Specifically, Zhao provides no data for terminally disubstituted olefins, meaning a person of ordinary skill in the art would lack data-driven guidance to pursue the Applicant’s divergent, highly active compounds.
Applicant’s arguments have been fully considered but are not persuasive. First, Zhao is relied upon as the primary reference because Zhao teaches antibacterial compounds sharing the same core structure as Formula I and identifies the terminal olefin position as a site suitable for substitution. Zhao does not merely disclose mono substituted terminal olefin compounds. Zhao discloses terminal olefin substitution patterns in which both terminal substituent positions are non-hydrogen substitutes, including embodiments such as R1 is trifluoromethyl, R2 is trifluoromethyl; R1 is a chlorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a bromine atom; and R1 is a chlorine atom, R2 is a bromine atom (claim 3). Thus, Zhao directly teaches that substitution at the terminal olefin position is contemplated within the same antibacterial compound scaffold.
MPEP 2143 explains that an invention is considered prima facie obvious if it combines prior art elements using a known technique to yield predictable results, or if a person of ordinary skill could easily swap known elements or choose from a finite set of predictable options with a reasonable expectation of success. In this case, Zhao discloses the same antibacterial scaffold, identifies the same terminal olefin position, and expressly teaches terminal olefin substitution. Zhao also teaches halogen containing disubstituted embodiments. Therefore, selecting bromo or iodine as halogen substituents at the disclosed terminal olefin position would have been a selection among known substituent options for the same disclosed purpose of preparing antibacterial analogs.
Second, regarding Applicant’s argument that Zhao lacks biological data for the particular terminally disubstituted olefins, the prior art does not need to explicitly provide a working example or biological test data for every species to establish a prima facie case of obviousness. Instead, the art simply needs to provide a reasonable expectation of success or a motivation to make the claimed compounds. (see MPEP 2143.02) Zhao teaches the same antibacterial scaffold, identifies the terminal olefin position for substitution, and specifically discloses disubstituted terminal olefin embodiments. Therefore, the absence of Zhao test data for every possible terminally disubstituted olefin does not negate the reason to modify Zhao or the reasonable expectation that the resulting analogs would retain antibacterial activity.
Third, regarding Applicant’s argument that there was no “data driven obviousness” because Zhao has not constructed a complete structure activity relationship for terminally disubstituted olefin. Obviousness does not require that the prior art provide a complete structure activity relationship or conclusive proof of efficacy for the exact claimed compounds. Under MPEP 2143 and 2143.02, the issue is whether the prior art would have provided a reason to make the claimed modification with a reasonable expectation of success. Zhao’s teaching of the same core antibacterial compounds, the same terminal olefin substitution site, halogen containing disubstituted embodiments, and the same antibacterial purpose provides such a reason.
Fourth, regarding Applicant’s argument that Zhao led to “a divergent path”. Applicant has not identified any disclosure in Zhao that criticizes, discredits, or otherwise discourages terminal dihalogen substitution. The mere absence of an example or preference for the exact dibromo or diiodo embodiment does not establish that Zhao teaches away the claimed modification. (see MPEP 2145) In this case, Zhao discloses terminally disubstituted olefin and includes halogen containing disubstituted embodiments. Therefore, Zhao does not lead away from the claimed modification, rather, Zhao directs one of ordinary skill in the art to the same terminal olefin position, and the same class of substituent modifications.
Fifth, regarding Applicant’s argument that MIC data are insufficient to establish unexpected results, Applicant relies on MIC values in the present specification for selected unsubstituted, difluoro, dibromo, diiodo, and cyclic olefin compounds, and asserts a trend of improved MIC as the size of substituents on the terminal olefin increases. However, MPEP 716.02(d) states that objective evidence of unexpected results must be commensurate in scope with the claims, requiring data to extend across the entire claimed range or show a consistent trend, and MPEP 716.02(e) states that evidence of unexpected results is most persuasive when it includes a comparison with the closest prior art. In this case, Applicant has not established that the alleged substituent size trend reasonably extends across the full scope of the pending claims. The pending claims are not limited solely to the specific dibromo, diiodo, or cyclic substituted compounds for which Applicant identifies MIC data, but instead encompass a broader genus of terminally substituted compounds. Applicant has not provided sufficient comparatives data across the breadth of the claimed genus to show that the asserted improvement occurs throughout the full claim scope. Accordingly, the asserted MIC data are not commensurate in scope with the claims. Moreover, Applicant relies on MIC values from the present specification and compares them generally with Zhao’s EC50 activity range. MIC and EC50 are different biological measurements, and Applicant has not shown that values are directly comparable or that they are obtained under the same testing conditions. Also, Applicant has not provided comparative testing between the claimed compounds and Zhao’s closest compound under the same assay conditions or otherwise explained a reliable correlation between the reported MIC and EC50 data. Therefore, the alleged absence of Zhao data for the exact terminally disubstituted olefins, the assertion that Zhao led to a divergent path, and the asserted MIC trend in Applicant’s specification are insufficient to overcome the prima facie case of obviousness.
Accordingly, the rejection of claims 1, 2, 6, 11-13, and 16 under 35 USC 103 is maintained.
NEW/MAINTAINED REJECTION
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.
Claim(s) 1, 3-6, and 18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhao et. al (CN 105924488 A, English Machine Translation attached, pub’d 07/09/2016).
With respect to claims 1, 3-6, and 18, Zhao disclose antibacterial compounds including WU-FA-10 (paragraph [0061-[0076]), and Zhao further discloses preferred terminal olefin substitution patterns of R1 and R2 (i.e., Rc and Rd positions, wherein J is CRc Rd , and G2 is H in instant Formula I) in which both corresponding substituent positions are halogen, including R1 is a chlorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a chlorine atom; R1 is a fluorine atom, R2 is a bromine atom; and R1 is a chlorine atom, R2 is a bromine atom (claim 3). These compounds fall within the scope of the instant claimed compounds, for example, R1 is OC(=)CH3, R2, R3, and G1 are hydroxy, G2 is H, and J is CRc Rd, wherein Rc and Rd are each independently halo. Zhao further teaches these compounds are useful as antibiotic agents.
PNG
media_image2.png
275
280
media_image2.png
Greyscale
PNG
media_image3.png
282
308
media_image3.png
Greyscale
PNG
media_image4.png
249
237
media_image4.png
Greyscale
Zhao’s Formula I
Zhao further teaches that such compounds can be prepared in the form of powders, tablets, capsules, suspensions, liquids, emulsions, oral preparations, granules, sprays, ointments, eye drops, disinfectants, etc. (paragraph [0043]). Preparations for the such forms are understood in the pharmaceutic field as formulated compositions produced though compounding. Accordingly, this disclosure reasonably convey that the active compound is combined with additional components in such preparations, thereby forming pharmaceutical compositions.
Claim 18 recites that “a pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.” The specification does not disclosure a specific information of a pharmaceutically acceptable excipient, thus this interpretation is consistent with the broadest reasonable interpretation standard applied during patent examination (see MPEP 2111). Accordingly, in the view the specification’s disclosure of Zhao that the compounds should prepare through drug compounding into preparation such as spray, ointments, tablets and eye drops, the disclosure reasonably encompasses pharmaceutical compositions comprising the compound of claim 1 together with pharmaceutically acceptable excipients as recited in claim 18.
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, 2, 6, 11-13, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et. al (CN 105924488A1, WIPO English Machine Translation, pub’d 07/09/2016, cited in IDS).
Claims 1, 3-6, 11 and 18 are rejected under 35 USC § 102(a)(1) as anticipated by Zhao. These 103 rejections are expanded additional limitations for claims 2, 11-13, and 16 that would have been obvious, but not directly disclosed by Zhao.
With respect to claim 1, 2, 6, 11-13, and 16, Zhao teaches compounds sharing the core structure with Formula I as set forth above, including WU-FA-13 that is a compound of formula I wherein G1 is ORx wherein Rx is H; G2 is H; J1 is CRcRd (i.e., Rc and Rd are each independently Halo), R1 is -OC(=O)(C1-C6)alkyl, R2 and R3 are hydroxy, as required in claims 1, 3-6, and 11 explained above.
PNG
media_image3.png
282
308
media_image3.png
Greyscale
PNG
media_image2.png
275
280
media_image2.png
Greyscale
PNG
media_image4.png
249
237
media_image4.png
Greyscale
Zhao’s Formula I
Zhao fails to teach a structural example wherein both Rc and Rd are both bromo or iodine substituents at position J1.
However, Zhao does teach in the generic disclosure that the terminal olefin may be substitute with halogen (i.e., bromine, chlorine, and fluorine), methoxy, trifluoromethyl group or mixture on both Rc and Rd position (claims 1-3). For examples, Zhao cites that “R1 is a chlorine atom, R2 is a chlorine atom”, and “R1 is a fluorine atom, R2 is a bromine atom”. R1 is the same position as Rc, and R2 is the same position as Rd (claim 1 and 3). Thus, Zhao teaches that the substitution at the terminal olefin position is permitted and encompasses both halogens as bromine or iodine within the genus, as required in the instant claims 2, 12-13, and 16. Zhao further teaches the compounds for use in antibiotics (paragraph [0011]).
The MPEP states that compounds with structural similarity are expected to have similar properties. 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 rePayne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In rePapesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) (discussed in more detail below) and In reDillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990). See MPEP 2144.09(I).
The references is directed to the same field of endeavor and address related to the application. The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham.
Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Applying KSR example rationale (E), it would have been prima facie obvious to extract the structure and substitute different halogens or dichloro- on the J position in Formular I taught by Zhao. Zhao does not restrict substitution at that position and expressly contemplates halogen substitution, thereby providing a reason to pursue such modification with a reasonable expectation of success. Therefore, claims 1, 2, 6, 11-13, and 16 would be obvious to a person skilled in the art at the time.
Conclusion
Claims 7-9, 17, and 22 are allowed.
Claims 1-6, 11-13, 16, and 18 are rejected.
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 SEONG JONG KIM whose telephone number is (571)272-6918. The examiner can normally be reached 7:00am-3:30pm.
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, Clinton A. Brooks can be reached at 571-270-7682. 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.
/SEONG JONG KIM/Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
Prosecution Insights