DETAILED ACTION
Notice of 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 amendments filed 7/15/2026 have been entered.
Response to Arguments
Applicant’s arguments, filed 7/15/2026, have been fully considered.
Applicant traverses the rejection of claims 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; of record).
Applicant first argues that “it is already questionable that a person of ordinary skill in the art would select”
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(i.e., (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol) from Quellet et al to prepare said compound (Applicant Arguments, Page 9).
However, Applicant provides no reasoning as to this argument. As such, it is maintained that one of ordinary skill in the art desiring to practice the invention of Quellet et al would have found it obvious to prepare the compounds disclosed therein, including (2E,4Z)-4-benzylidene-2-methyldec-2-en-1-ol.
Next, noting that “the rejection relies on a reconstruction of the Applicant’s process using disclosures selected from the separate references (namely Ishida and Wadsworth)”, Applicant argues that “such a reconstruction requires more than a showing that the individual reaction types were known in the art. Rather, it must be shown that a person of ordinary skill in the art would have been motivated to select the particular intermediate of formula C and the particular phosphonate derivative F recited in the claim, and would have had a reasonable expectation of success in obtaining the desired product by the claimed sequence of reactions” (Applicant Arguments, Page 10).
The argument is not found persuasive. As discussed in the basis of the rejection, Ishida et al teach step (a) of coupling a compound of formula A with a compound of formula B to obtain a compound of formula C, specifically wherein the compound of formula C is “α-hexyl cinnamaldehyde” -
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(see Paragraphs 0021 and 0048-0050, formulas (8), (9) and (10), i.e., “α-hexyl cinnamaldehyde”).
Applicant, however, further argues that, although “Ishida... identifies α-hexyl cinnamaldehyde as one example... even if Ishida was considered to render obvious the preparation of the claimed aldehyde intermediate of formula C, this disclosure does not establish obviousness of the presently claimed process as a whole” and “[t]o address this problem, the Examiner relies on Wadsworth” (Applicant Arguments, Pages 10-11). Yet, as argued by Applicant, “Wadsworth merely discloses the general concept that phosphonate carbanions may react with aldehydes and ketones to form olefins... Wadsworth does not disclose an aldehyde intermediate of formula C, nor does it disclose a compound of formula (I)” (Applicant Arguments, Page 11). And, pointing to page 1734, left column, line 18, Applicant argues that “while Wadsworth discloses the use of cinnamaldehyde as a substrate in the disclosed olefination chemistry... the cinnamaldehyde employed therein bears a hydrogen atom in the α-position” as opposed to the “larger α-substituents” of instantly claimed formula C which “are significantly longer, more sterically hindered, and bulkier than... hydrogen” (Applicant Arguments, Page 11).
Applicant’s arguments require one of ordinary skill in the art to limit the Horner-Wadsworth-Emmons reaction taught by Wadsworth et al solely to the exact compounds disclosed in the examples therein, which cannot be found persuasive. As indicated by the Court in KSR v. Teleflex (127 S,Ct. 1727 (2007)), the analysis under 35 USC 103 “need not seek out precise teachings directed to the specific subject matter of the challenged claim [but, instead] can take account of the inferences and creative steps that a person of ordinary skill in the art would employ”, emphasizing that “[a] person of ordinary skill is… a person of ordinary creativity, not an automaton”.
Applicant additionally argues that “a person of ordinary skill, reading the cited references in their entirety, would not be motivated to modify Ishida in view of Wadsworth with a reasonable expectation of success and without undue experimentation” (Applicant Arguments, Page 12). In particular, Applicant argues that “[n]either Ishida nor Wadsworth provides a teaching that the specific α-substituted aldehydes of formula C would behave in the same manner as the unsubstituted cinnamaldehyde exemplified in Wadsworth, or that the claimed Horner-Wadsworth-Emmons reaction would proceed successfully to provide compounds of formula (I)” (Applicant Arguments, Page 12).
The argument is not found persuasive. Again, it is not found persuasive that one of ordinary skill in the art would limit the limit the Horner-Wadsworth-Emmons reaction taught by Wadsworth et al solely to the exact compounds disclosed in the examples therein. Additionally, obviousness does not require absolute predictability, only a reasonable expectation of success of obtaining similar properties. In re O'Farrell, 853 F.2d 894 (Fed. Cir. 1988).
Lastly, Applicant argues that “the present rejection relies upon first identifying the target compounds of the present application and then reconstructing a synthetic route thereto by selecting the specific aldehyde intermediate from Ishida and combining it with the generally disclosed chemistry of Wadsworth. The proposed combination is therefore not derived from the teachings of the prior art itself, but only becomes apparent with knowledge of the Applicants' invention and is thus based on hindsight” (Applicant Arguments, Page 12).
In response to Applicant’s argument that the examiner’s conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the Applicant’s disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392 (CCPA 1971). In the instant case, the rejection of claims takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the Applicant’s disclosure. As such, Applicant’s argument is not found persuasive.
For all the foregoing reasons, Applicant’s arguments are not found persuasive. The rejection of claim 25 is MAINTAINED.
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 MAINTAINED 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; of record).
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 said
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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
No new ground(s) of rejection are 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 extension fee 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 date of this final action.
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
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