DETAILED ACTION
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 the Claims
The amendment filed on 08/04/2026 has been entered. Claims 1-4, 6, 15, and 18-19 have been amended and claims 10-11 and 13-14 have been canceled. Thus claims 1-9, 12 and 15-20 are currently pending.
Election/Restrictions
The elected compound of formula IG is allowable. Pursuant to the procedures set forth in MPEP § 821.04(a), the restriction requirement among the species, as set forth in the Office action mailed on 04/06/2026, is hereby withdrawn and all withdrawn claims are hereby rejoined and fully examined for patentability under 37 CFR 1.104. In view of the withdrawal of the restriction requirement, applicant(s) are advised that if any claim presented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claim may be subject to provisional statutory and/or nonstatutory double patenting rejections over the claims of the instant application. Once the restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP § 804.01.
Withdrawn Objections and Rejections
The objections to the specification and claim 18 have been withdrawn in view of the amendment.
The compound of formula IG of claim 15 has been narrowed. Furthermore, compound 12 has been canceled from claim 19. Thus the 102(a)(1) rejections as being anticipated by Pap (Pap, L. et al. “Comparative evaluation of new synergists containing a butynyl-type synergophore group and piperonyl butoxide derivatives” Pest Manag. Sci. 57:186-190 (2001)) and Urakami (Urakami, T. et al. “Novel Amphiphilic Probes for [18F]-Radiolabeling Preformed Liposomes and Determination of Liposomal Trafficking by Positron Emission Tomography” J. Med. Chem. 2007, 50, 6454–6457), both set forth in the Office Action 05/21/2026 have been withdrawn.
Claim Objections
Claims 3 and 17 are 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.
Claim 4 is objected to because of the following informalities: compound of formula ID’ is a duplicate of the compound of formula IF. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claims 9 and 15-16 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 9 recites the limitation "the cyclic heteroaliphatic group". There is insufficient antecedent basis for this limitation in the claim. As such, the claim will not be examined for patentability.
Claim 15 recites the compounds of formulas IG, IJ and IK. There is insufficient antecedent basis for the -O-Aliphatic group in the compounds. In view of claim 1, the corresponding group -OR2 requires R2 to be C2-25 alkyl group, however, the aliphatic group of -O-Aliphatic of the compounds of formulas IG, IJ and IK encompasses any aliphatic group beyond claim 1’s C2-25 alkyl group.
For purpose of applying art, the aliphatic group of -O-Aliphatic in formulas IG, IJ and IK will be interpreted as in claim 1, i.e. C2-25alkyl group, wherein the C2-25alkyl group is linear, branched, cyclic, or a combination thereof.
Claim 16 recites the limitation “aliphatic group” that renders the claim vague and indefinite. Claim 15 has two versions of aliphatic group, one that refers to the -O-Aliphatic group and the other that refers to the TG group. Thus, it is unclear which aliphatic group of claim 15 the Applicant is intending to limit. If the intention is to limit the aliphatic group of -O-Aliphatic, please also see the 112(d) rejection set forth below.
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.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], 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 16 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, 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. The aliphatic group of claim 16 fails to further limit the R2 group of claim 1 as both claims are drawn to aliphatic groups C2-25alkyl group, wherein the C2-25alkyl group is linear, branched, cyclic, or a combination thereof. 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 § 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 1-2, 4-8 and 12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Patent number JP2008184412A (JP’412; cited in PTO-892 05/21/2025).
JP’412 teaches the following compounds and compositions comprising the compounds:
[0083] (CAS 1046052-61-2)
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341
485
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[0084] (CAS 1046052-63-4)
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235
503
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[0085] (CAS 1046052-66-7)
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138
506
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[0086] (CAS 1046052-70-3)
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348
501
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[0087] (CAS 1046052-74-7)
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227
656
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Regarding claims 1-2, 5-8, 12 and 20,
R1 is hydrophilic group (polyethylene oxide)
R2 is C8 or C12 linear alkyl group
X is O
p is 0 thus R3 is absent
R6 is OR4, wherein R4 is C8 or C12 linear alkyl group
m is 1
Regarding claim 4, the above compounds read on Formulas IC’, ID’ and IF.
Regarding claim 8, the compounds in [0085] and [0087] have 20 polyethylene oxide units, which is approximately 561.04 g/mol.
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.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Patent number JP2008184412A (JP’412; cited in PTO-892 05/21/2025).
JP’412 teaches the following generic compound of formula (X):
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187
564
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The above compound reads on the claimed compounds 92 (when n=7 and m=20), 98 (when n=9 and m=20) and 11 (when n=9 and m=9).
Thus, using the n and m integers as indicated above, a skilled artisan would reasonably arrive at the instantly claimed compounds 92, 98 and 11.
It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to obtain compounds 92, 98 and 11 as instantly claimed in view of the teachings of JP’412.
Claim 19 is rejected under 35 U.S.C. 103 as being unpatentable over Letellier (Letellier, P. et al. “The effect of hydrogen bonding, molecular shape, dipole moments, and chain length on the mesomorphism of some D-glucose and D-glucosamine derivatives” Liquid Crystals (1997), 22(5), 609-620; Abstract only; full NPL will be provided when becomes available).
Letellier teaches the following compound
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189
492
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The above compound and the claimed compound 85 are homologs as they differ by the successive addition of the same -CH2- group in the aliphatic group, and are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. MPEP § 2144.09.
It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to obtain compound 85 as instantly claimed in view of the teachings of Letellier.
Allowable Subject Matter
The subject matter of claims 3 and 15-17 is free of prior art and claim 18 is allowed.
Regarding claim 15, formula IG, Pap (Pap, L. et al. “Comparative evaluation of new synergists containing a butynyl-type synergophore group and piperonyl butoxide derivatives” Pest Manag. Sci. 57:186-190 (2001); cited in PTO-892 05/21/2025) teaches compound 12 (see below) and an insecticide composition comprising the compound thereof (Tables 1-2):
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152
443
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wherein in formula IG, aliphatic is C1 alkyl group and r = 2. The reference, however, fails to teach or suggest r = 3 to 20.
Regarding claims 15 and 18, formula IG, Patent number JP2008184412A (JP’412; cited in PTO-892 05/21/2025) teaches the compound of formula (XII) shown below ([38], pg. 24 of the original disclosure):
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180
527
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However, the reference fails to teach the methoxy group as instantly claimed.
Regarding claims 15 and 18, formula IK, Koike (Koike, Y. et al. “Novel phenolic glycosides, adenophorasides A–E, from Adenophora roots” J Nat Med (2010) 64:245–251) teaches the following compound 7
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693
1181
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Note: as indicated earlier, the aliphatic group in Aliphatic-O- group of claim 15 is interpreted as C2-25alkyl group, wherein the C2-25alkyl group is linear, branched, cyclic, or a combination thereof. The aliphatic group in compound 7 of Koike is C1 alkyl group but fails to teach or suggest C2-25alkyl group.
Furthermore, while one methoxy group of compound 7 reads on the claimed method of compound 39 (claim 18), the other methoxy group of compound 7 fails to read on the octyloxy group of compound 39.
Regarding claim 3 and claim 15, none of the above references teach or suggest R1 as claimed of claim 3 and formula IJ of claim 15.
Furthermore, a skilled artisan would not have been motivated in modifying the teachings of the above references to reasonably arrive at the compounds of claims 3, 15 and 18.
Conclusion
Claims 1-2, 4-9, 12, 15-16 and 19-20 are rejected and claim 18 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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