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
Claim Status
Claims 1-9, and 11-17 are pending. Claims 9, 11, and 17 are withdrawn. Claims 1-8 and 12-16 are under examination in their entirety. Claims 1-8 and 12-16 are rejected. No claims allowed.
Election/Restrictions
Claims 9, 11, and 17 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 05/22/2026.
Filing Receipt
PNG
media_image1.png
94
939
media_image1.png
Greyscale
PNG
media_image2.png
46
939
media_image2.png
Greyscale
PNG
media_image3.png
46
937
media_image3.png
Greyscale
PNG
media_image4.png
84
940
media_image4.png
Greyscale
PNG
media_image5.png
66
935
media_image5.png
Greyscale
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 1-8 and 12-16 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 1 and 8 and all dependent claims are indefinite because of the redundancy of compounds (III) and (III’). The difference of (III’) and (III) is not understood. When all variables in (III) and (III’) are identical as can be the case in claim 1 and 8, there is no difference in (III’) and (III). Claims 1 and 8 do not require a difference between (III) and (III’).
When variables n, p, n’, p’ are identical as can be the case in claim 1, R and R’ would be identical and the Grignard reagents (III) and (III’) would be identical. Clarification is needed to define the variables.
This argument is being applied to compounds (I) and (I’). Upon achieving (I) and without a requirement for R and R’ being different, (I’) is also achieved.
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.
Claim(s) 1-6, 8 and 12-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Miyake et al. (USPGPub 2013/0245313, Published 09-2013), Protective Groups (pp. 1-3, Published 01-2021), Shiono et al. (JP5988437, Published 05-1984. Translation attached.) and Protective Groups (pp. 1-3, Published 01/2021).
Scope of the Prior Art
Miyake et al. teach a process to prepare the current pheromone (par. 5, 54 and
Examples 1 to 3-3) see immediately below compound (6) and (E3,Z8,Z11)-3,8,11-tetradecatrienyl acetate. The R group being 3,6-nonadienyl (par. 37 and 68).
PNG
media_image6.png
145
509
media_image6.png
Greyscale
PNG
media_image7.png
337
313
media_image7.png
Greyscale
(E3,Z8,Z11)-3,8,11-tetradecatrienyl acetate
Miyake et al. teach a process to prepare the current pheromone utilizing the intermediate compound (3) immediately below, and the current Grignard reagent RMgX (R=3,6-nonadienyl) accompanied with additional steps (par. 33). X being Cl or Br (par. 35).
PNG
media_image8.png
176
492
media_image8.png
Greyscale
Wherein, the only difference from current compound (II) from compound (3) immediately above is the 2nd acetate (O-acetyl) hydroxyl protecting group is missing.
Note: Compound (3) of Miyake et al. immediately above has two hydroxyl protecting groups acetate (claimed) and methoxymethyl ether.
A replacement of the methoxymethyl ether with the claimed acetic acid ester is accomplished in a later step in Miyake et al. (par. 46-60).
PNG
media_image9.png
143
496
media_image9.png
Greyscale
PNG
media_image10.png
129
496
media_image10.png
Greyscale
Concerning claim 2-3, Miyake et al. teach Copper halide catalysts with triphenylphosphine and triethylphpsphite (par. 39-42).
Concerning claim 4, Miyake et al. teach tetrahydrofuran (par. 44).
Concerning claim 5, 14 and 6, Miyake et al. teach Cupric chloride (par. 39) and
copper chloride (II) (Example 2).
Concerning claim 8, when the variables n, p, n’, p’ are identical as in claim 1, R and R’ are identical. Thus, a ratio of 1 would exist. This ratio overlaps the current ratio of 1:1 (III) to (III’). Alternatively, with both R and R’ being identical, a 1 to 1 ratio would be envisaged when dividing the amount if the claimed compound in half by weight. For example, the two halves of (III) would equate to a 1:1 ratio of (III) to (III’). Thus 1:1 exists.
Ascertain the Differences
Miyake et al. does not teach the reaction of the current diacetate compound (II) with the current RMgX to prepare the current pheromone. Miyake et al. does not teach the 25C of the reaction of the diacetate and the Grignard reagent.
Secondary References
Protective Groups teach methoxymethyl ether and acetic acid ester being hydroxyl protecting groups (p. 2 of 3).
Shiono et al. teach a successful alkylation of a allylic acetate end (position 1, allylic position, Specification p. 3) of a bisacetate, using a bromine Grignard reagent in the presence of a copper-based catalyst (example 1). The homoallylic position (Specification p. 3) of the bisacetate is unphased/untouched during the Grignard reaction taught by Shiono et al. See immediately below.
PNG
media_image11.png
166
595
media_image11.png
Greyscale
Shiono et al. is silent to alkylation of the beta carbon of the acetate in the homoallylic position. The alkylation of the beta carbon of the acetate in the homoallylic position leads to current compounds (VI) and/or (VI’) of current claim 9 (Claim 9 is not being examined at this time). This overlaps the less than 2% by weight of the composition in claim 9.
Shiono et al. teach overlapping temperatures of those taught by Miyake et al. and to the current temperature in claim 7 step. d. when reacting the Grignard reagent and the substrate -78 to 70 to -20 to 30C (p. 251, right column).
Shiono et al. has overlapping catalysts and solvents as taught by Miyake et al.
See page 251 right column and examples.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have replaced the methoxymethyl ether in compound (3) of Miyake et al. with the acetic acid ester taught by Protective Groups with a reasonable expectation of success and arrive at the diacetate compound (II) in current claim 1. Next it would have been obvious for the ordinary artisan to have tried to react the arrived at diacetate compound (II) in the Grignard reaction taught by Miyake et al. to arrive at the current invention.
The ordinary artisan would have done so to effectively prepare the pheromone
compound (compound (6)) of Miyake et al. via a different method. See MPEP 2141 III
(B) and/or (E).
More discussion of the reasonable expectation of success is warranted. The
ordinary artisan would have had a reasonable expectation of success in substituting the protecting groups as argued above because both methoxymethyl ether and the current acetic acid ester are hydroxyl protecting groups. This is on full display in Protective Groups and Miyake et al. Moreover, a replacement of the methoxymethyl ether with the claimed acetic acid ester is accomplished in a later step in Miyake et al.
The ordinary artisan would have had a reasonable expectation of success in
alkylating the allylic acetate end (position 1, allylic position, Specification p. 3) of diacetate compound (II), using Grignard reagents and reaction parameters including the copper-based catalysts in Miyake et al. because Shiono et al. teach overlapping catalysts and solvents and a successful alkylation of a allylic acetate end (position 1, allylic position, Specification p. 3) of a bisacetate using a bromine Grignard reagent in the presence of a copper-based catalyst (example 1). Shiono et al. is silent to alkylation of the beta carbon of the acetate in the homoallylic position. Thus, there is no evidence that the compounds (VI) and/or (VI’) of current claim 9 would have been made.
MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning the current temperature in claim 7 step. d., MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning the currently claimed order of steps, Selection of any order of
performing process steps is prima facie obvious in the absence of new or unexpected
results In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and Selection of any order of mixing ingredients is prima facie obvious. In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930). See MPEP 2144.04 IV C.
Claim(s) 7 and 15-16 is/are rejected under 35 U.S.C. 103 as being
unpatentable over Miyake et al. (USPGPub 2013/0245313, Published 09-2013),
Protective Groups (pp. 1-3, Published 01-2021), Shiono et al. (JP5988437, Published 05-1984) as applied to claims 1-6, 8 and 12-14 and in further view of Kuethe et al. (USPGPub 2007/0015923, Published 01-2007).
Scope of the Prior Art
The teachings of Miyake et al., Protective Groups, and Shiono et al. are in the above 103 rejection and are incorporated by reference. Additional teachings are as followed.
Concerning claim 7
Step a. see Miyake et al. immediately below par.69
PNG
media_image12.png
67
512
media_image12.png
Greyscale
Step b. see Miyake et al. immediately below par.69
PNG
media_image13.png
47
503
media_image13.png
Greyscale
PNG
media_image14.png
19
503
media_image14.png
Greyscale
Miyake et al. adds the catalyst first and next adds the substrate, the opposite of
current step b.
Step c. see Miyake et al. immediately below par.68
PNG
media_image15.png
136
497
media_image15.png
Greyscale
Step d. see Miyake et al. immediately below par.69
PNG
media_image16.png
140
508
media_image16.png
Greyscale
From the above, the Grignard reagent is added to a Cu catalyst-substrate mixture as in current step d at a temperature of 0 to 5C not 25C as currently claimed.
Step e. and f. see Miyake et al. immediately below par. 70
PNG
media_image17.png
117
498
media_image17.png
Greyscale
PNG
media_image18.png
125
493
media_image18.png
Greyscale
Shiono et al. teach the extraction of the product of a reaction of a Grignard reagent and an allylic acetate (p. 252, left column).
Shiono et al. teach overlapping temperatures of those taught by Miyake et al. and to the current temperature in claim 7 step. d. when reacting the Grignard reagent and the substrate -78 to 70 to -20 to 30C (p. 251, right column).
Shiono et al. has overlapping catalysts and solvents as taught by Miyake et al.
See page 251 right column and examples.
Concerning termination of the reaction, neutralization thereof and extraction in current steps e.-f. Shiono et al. teach pouring a Grignard reaction into ice-cold ammonium chloride and extracted with diethyl ether.
Ascertain the Differences
From the above, the reaction was neutralized and terminated simultaneously by adding ammonium chloride/HCl, not the claimed two step process of steps e. and f.
For current procedures for stopping and neutralizing the reaction see page 7 of the specification wherein acetic anhydride and ammonium chloride are used.
Secondary References
Kuethe et al. teach the use of the aqueous NH4Cl quench taught by Miyake et al. See Kuethe et al. paragraph 35 immediately below. Kuethe et al. goes on to teach the use of acetic anhydride initially and the subsequent use of NH4Cl. See Kuethe et al. paragraph 35 immediately below.
PNG
media_image19.png
90
502
media_image19.png
Greyscale
PNG
media_image20.png
110
497
media_image20.png
Greyscale
PNG
media_image21.png
87
498
media_image21.png
Greyscale
The 1.5 equivalences overlaps the range in claim 16.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried an alternative quenching method of the Grignard reaction. The alternative method being the addition of the acetic anhydride taught by Kuethe et al. and next the addition of the ammonium chloride taught by Kuethe et al. and Miyake et al. MPEP 2141 III. (B) and/or (E).
The ordinary artisan would have looked to Kuethe et al. because both Kuethe et al. and Miyake et al. teach the use of ammonium chloride when stopping a Grignard reaction. The reasonable expectation of success coming from the fact that acetic anhydride can be used to stop a Grignard reaction.
Concerning the order of steps in claim 7, Selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and Selection of any order of mixing ingredients is prima facie obvious. In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930). See MPEP 2144.04 IV C.
Concerning claim 16, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Conclusion
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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, 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.
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.
/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
Prosecution Insights