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 responsive to Applicant's Remarks and Amendment after Non-Final Rejection, filed Dec. 17, 2025. As filed claims 1-3, 5-12 are pending; of which claims 1, 10 are amended; claim 12 is newly added. Claim 4 is cancelled.
Response to Remarks
Applicant’s amendments have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
The rejection of claims 1-11 under 35 U.S.C. § 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph is withdrawn in view of claim amendments.
2.The rejection of claims 1-11 under 35 U.S.C. § 103 over Liu et al. Tetrahedron Letters 55 (2014) 3090–3092 and further in view of Byrne et al. Sustain Chem Process (2016) 4:7 is withdrawn in view of claim amendments.
3..The objection to claims has been addressed by amendments to claims.
The following are modified or new grounds of rejections necessitated by Applicants’ amendment, filed on 12/17/2025 wherein the limitations in pending claims as amended now have been changed. The limitations in the amended claims have been changed and the breadth and scope of those claims have been changed.
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.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
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 of carrying out his invention.
Claims 1-3, 5-12 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, 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 pre-AIA the inventor(s), at the time the application was filed, had possession of the claimed invention. This is a new matter rejection.
As currently amended, claim 1 introduces subject matter that was not described in the specification at the time the application was filed; i.e., “new matter.” In particular, the recitation “wherein the alcoholic hydroxyl group donor is a cyclohex(meth)anol substance”. The specification does not provide a basis or definition of cyclohex(meth)anol substance.
Examples 1 -4 of instant disclosure on [0040] -[0048] show 4'-propyl-[1,1'-bis(cyclohexane)]-4-yl) methanol; example 5-7 on [0054] show 4-(4-propylcyclohexyl)aniline or 4-(2',3'-difluoro-4'-methyl-[1,1 '-biphenyl]-4-yl)cyclohexanol- as alcoholic hydroxyl group donor substrate containing cyclohex(meth)anol structural feature.
However, the instant disclosure does not provide as definition of “cyclohex(meth)anol substance” as claimed.
Claim 12 recites “biscyclohexane methanol substance and a phenyl-cyclohexanol substance”. While examples 1 -4 of instant disclosure provide example of biscyclohexane methanol compound, however, the instant disclosure does not provide a basis or a definition of the “biscyclohexane methanol substance” or the “phenyl-cyclohexanol substance” as claimed. The support in the insta t disclosure as originally files for cyclohex(meth)anol substance and phenyl substance is limited to the specific compounds of preparative examples.
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.
Claims 1-3, 5-11 are rejected under 35 U.S.C. 103 as being unpatentable over US 2016/0161817 A1, Jun. 9, 2016 by Sasou (“the 817 publication”; cited in PTO-892 attached herewith) and further in view of Byrne et al. Sustain Chem Process (2016) 4:7 (cited in PTO-892 mailed 11/03/2025).
Instant claims are drawn to a method for performing Mitsunobu reaction between an alcoholic hydroxyl group donor and an active hydrogen donor, which specifically comprises the following steps: performing reaction of the alcoholic hydroxyl group donor, the active hydrogen donor, a trihydrocarbylphosphine reagent and an azodicarboxylate reagent in the presence of an organic solvent to obtain the product of dehydration condensation of the alcoholic hydroxyl group donor and the active hydrogen donor; wherein, the organic solvent is a C8-16 linear or branched alkane; wherein the alcoholic hydroxyl group donor is a cyclohex(meth)anol substance; and
wherein the active hydrogen donor is a phenyl substance containing an active hydrogen group selected from the group consisting of -OH, -SH, -COOH, -COSH, -NH2, and -CONH2.
The ‘817 publication teaches the Mitsunobu reaction of a cyclohex(meth)anol substance with phenol- phenyl substance containing -OH as an active hydrogen, in the presence of DIAD = diisopropyl azodicarboxylate, which corresponds the claimed azodicarboxylate reagent (instant claim 6), and PPh3 -triphenyl phosphine, the claimed trihydrocarbylphosphine reagent (instant claims 1, 5-6).
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Disclosed on example of [0229] (reproduced below) is the Mitsunobu reaction of 4-trans-n-pentylcyclohexanemethanol which corresponds to the claimed alcoholic hydroxyl group donor a cyclohex(meth)anol substance with 2,3-difluorophenol which corresponds to the claimed active hydrogen donor, with DIAD = diisopropyl azodicarboxylate, which corresponds the claimed azodicarboxylate reagent (instant claim 6), and PPh3 (triphenyl phosphine instant claim 5) which corresponds the claimed trihydrocarbylphosphine reagent (instant claims 1, 5-6).
Regarding instant claims 7-11, the ‘817 publication teaches the molar ratio of the alcoholic hydroxyl group donor and the active hydrogen donor is 1:1-1.2, stirring reaction mixture for 2h at ice-cool temperature, under nitrogen atmosphere, ant stirring at room temperature for 12h.
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The difference between the instantly claimed process and that taught by the ‘817 publication is that the prior art does not teach C8-16 linear or branched alkane as solvent for the reaction, instead it used THF as reaction solvent.
However, regarding the influence on reaction of the solvent, and
consideration for solvent selection is known in the prior art as discussed by the review article by Byrne. The article by Byrne teach that dodecane and undecane are listed as solvent of choice for green chemistry (page 19) and as a choice for conventional solvents.
Conclusion – the process taught in the instant application fails to set forth a patentable inventive step. In view of the high level of skill in the art, the optimization of a known processes has been herein shown to be prima facie obvious because the specification fails to produce evidence of unexpected results, a long-felt industrial need, or other secondary considerations to overcome the lack of an inventive step. As such, one skilled in the art would thus be motivated to optimize the processes as taught by the publication by Liu and utilize sustainable solvents such as dodecane and undecane, to arrive at the instant claimed process with the expectation of success, because the prior art specifically teach optimization of the reaction conditions by selection of solvents to minimize the by-product formation and by utilizing alternative solvents with low toxicity, minimal safety concerns and little impact on the environment as routine in chemical art. "Exemplary rationales that may support a conclusion of obviousness include: (A) Combining prior art elements according to known methods to yield predictable results ". See MPEP § 2143. Thus, the instant claims are obvious over the combined teachings of prior art.
Relevant Prior Art
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AN 161:724606 CASREACT Full-text
TI A novel thiazolidinedione derivative TD118 showing selective algicidal
effects for red tide control
AU Wu, Ying; Lee, Yew; Jung, Seul-Gi; Kim, Minju; Eom, Chi-Yong; Kim, Si
Wouk; Cho, Hoon; Jin, Eon Seon
CS Department of Polymer Science and Engineering, Chosun University, Kwangju,
501-759, S. Korea
SO World Journal of Microbiology & Biotechnology (2014), 30(5), 1603-1614
CODEN: WJMBEY; ISSN: 0959-3993
PB Springer
DT Journal; (online computer file)
LA English
AB Thiazolidinedione (TD) derivs. have been found to have an algicidal effect
on harmful algal bloom microalgae. In this study, 75 TD derivs. were
synthesized and analyzed for algicidal activity. Among these synthetic
TDs, 18 TD derivs. showed specific algicidal activity on two strains
belonging to the classes Raphidophyceae (Chattonella marina and
Heterosigma akashiwo) and Dinophyceae (Cochlodinium polykrikoides). Two
strains belonging to Bacillariophyceae (Navicula pelliculosa and
Phaeodactylum EPV), one strain belonging to Dinophyceae (Amphidinium sp.),
and a Eustigmatophycean microalga (Nannochloropsis oculata) showed less
sensitivity to the TD derivs. than the other two phyla. The most reactive
TD deriv., compd. 2 (TD118), was selected and tested for morphol. and
physiol. changes. TD118 effectively damaged the cell membrane of C.
marina, H. akashiwo and C. polykrikoides. The O2 evolution and
photosystem II efficiency (Fv/Fm) of C. marina, H. akashiwo and C.
polykrikoides were also severely reduced by TD118 treatment. Amphidinium
sp., N. pelliculosa, Phaeodactylum EPV and N. oculata showed less redn. of
O2 evolution and the Fv/Fm by TD118.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692