DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 10/08/2025 has been entered.
AIA Status of the Claims
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Response to Arguments
Applicant’s arguments, filed 9/25/2025, have been fully considered.
As argued by Applicant, “the Applicants have now narrowed the scope of protection to the process comprising only step (b2)” and, “[w]ith reference to Section 6 of the present Office Action, the Examiner acknowledged that the subject matter of claim 25 with regards to the combination of step (a) with step (b2) is patentable” (Applicant Arguments, Page 9).
The argument is unclear. It is unclear what is meant by “Section 6 of the present Office Action” and nowhere has it been indicated that “the subject matter of claim 25 with regards to the combination of step (a) with step (b2) is patentable” as argued by Applicant.
In an effort to understand Applicant’s arguments, Applicant’s attorney, Alan Miller, was contacted by telephone to discuss, who indicated that since only the combination of step (a) with step (b1) was rejected, it was understood that the combination of step (a) with step (b2) would be patentable.
The argument is not found persuasive. In Applicant’s Response to Restriction/Election dated 11/03/2023, Applicant elected a single method of making the compound
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comprising the combination of step (a) with step (b2).
Since the elected method of making the elected compound was found to be free of the art, the search was expanded as called for under current Office Markush practice to include a single additional species (M.P.E.P. § 803.02). That species was a method of preparing the following compound species
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comprising the combination of step (a) with step (b2), which was rejected in the Action mailed on 11/20/2023.
In Applicant’s response filed 2/06/02024, Applicant amended the claims to exclude the above non-elected compound of formula (I).
Accordingly, in the Action mailed on 5/02/2024, the search was again expanded as called for under current Office Markush practice to include a single additional species (M.P.E.P. § 803.02). That species was the preparation of the following compound species
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comprising the combination of step (a) with step (b1), which was MAINTAINED rejected in the Actions mailed on 11/22/2024 and 6/11/2025.
Since Applicant has amended the claims to exclude step (b1), the search is again expanded as called for under current Office Markush practice to include a single additional species (M.P.E.P. § 803.02). That species was the preparation of the following compound species
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comprising the combination of step (a) with step (b2).
Claim Rejections - 35 USC § 103
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.
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 25 is NEWLY rejected under 35 U.S.C. 103(a) as being unpatentable over Quellet et al (GB 2 528 480 published 1/27/2016 – provided in Applicant’s IDS submitted 6/01/2022; of record) in view of Ishida et al (US 2009/0171124; of record) and Wadsworth et al (J American Chem Soc 83:1733-1738, 1961).
As amended claim 25 is drawn to a process for the preparation of a compound of formula (I), which embraces the following compound species
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wherein R1 is C1 alkyl; R2 is C6 alkyl; R3-R7 are H; and X is CH2OH; the method comprising:
(a) coupling a compound of formula A with a compound of formula B, thereby obtaining a compound of formula C, wherein:
the compound of formula A is:
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the compound of formula B is:
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the compound of formula C is:
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(b) contacting the compound of formula C with a phosphonate derivative F thereby obtaining a compound of formula (I), wherein:
the phosphonate derivative F is:
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Quellet et al teaches the instantly claimed compound of formula (I) (i.e., (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol (Page 4, Line 16)).
However, Quellet et al does not teach methods for preparing said compound.
Yet, it would have been obvious to prepare the compound of Quellet et al as claimed based further on Ishida et al and Wadsworth et al as follows:
FIRST, Ishida et al teach step (a) of coupling a compound of formula A with a compound of formula B, thereby obtaining a compound of formula C. In particular, Ishida et al teach coupling the compound R1-CHO (Formula I) with R2-CHO (Formula II) – wherein R1 and R2 can be “a linear or branched alkyl group having 1 to 20 carbon atoms… [and] an aromatic ring structure-containing group having 6 to 20 carbon atoms” (Paragraph 0021) and which read on instant formulas A and B – to provide
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(Formula III-b) (Paragraph 0021) which reads on instant formula C.
Even more specifically, Ishida et al teach:
coupling the compound
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(Paragraphs 0045 and 0048, formula (6), i.e., a compound of Formula I as defined by Ishida et al which reads on a compound of formula A as instantly claimed (see also Paragraph 0027: “[e]xamples of the aldehyde compounds I and II used as the raw aldehyde compound in the present invention include… benzaldehyde” – i.e.,
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))
with the compound
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(Paragraph 0045, formula (2) i.e., a compound of Formula II as defined by Ishida et al which reads on a compound of formula B as instantly claimed) to provide
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(Paragraph 0045, formula (7) which reads on a compound of formula C as instantly claimed (see also Paragraph 0050: “[e]xamples of the α,β-unsaturated aldehyde compounds produced by the condensation reaction II… include… α-methyl cinnamaldehyde” – i.e.,
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– as well as “a-hexyl cinnamaldehyde” – i.e.,
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).
And it is evident from Ishida et al that utilizing
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(i.e., in place of
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would provide
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(see, e.g., Paragraphs 0021 and 0048-0050, formulas (8), (9) and (10), i.e., “a-hexyl cinnamaldehyde”).
And SECOND, Wadsworth et al teach step (b2) of contacting a compound of formula C with a phosphonate derivative F, thereby obtaining a compound of instant formula (I). In particular, Wadsworth et al teach contacting a compound
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(i.e., a compound of formula C as instantly claimed) with a compound having the following structure
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(i.e., a phosphonate derivative F as instantly claimed) results in a compound having the following structure
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(i.e., a compound of formula (I) as instantly claimed) via Honer-Wadsworth-Emmons (HWE) reaction (Page 1733, Column 1).
As such, an ordinarily skilled artisan, desiring to synthesize the compound
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taught by Quellet et al (Page 4, Line 16), would have found it obvious to contact
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– the compound of formula C which also entails a compound having the general structure
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– with
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– the compound
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which also entails a phosphonate derivative F – to provide said title compound
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via Honer-Wadsworth-Emmons (HWE) reaction, based further on Wadsworth et al.
In view of all of the foregoing, claim 25 is rejected as prima facie obvious.
Claim Objections
Claim 32 is MAINTAINED rejected as depending from a rejected base claim.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CRAIG D RICCI whose telephone number is (571) 270-5864. The examiner can normally be reached on Monday through Thursday, and every other Friday, 7:30 am - 5:00 pm ET.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Bethany Barham can be reached on (571) 272-6175. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CRAIG D RICCI/Primary Examiner, Art Unit 1611