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/Amendment after Non-Final Rejection, supplemental amendment filed April 16, 2026. As filed, claims 1, 3-17, 19-20 are pending of which claims 1, 3, 4-17 are amended; claims 19-20 newly added. Claims 2, 18 are cancelled.
Rejections Withdrawn
Applicants’ amendment, have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
1. The rejection of claims 1, 3-4, and 7-17 under 35 U.S.C. § 112(b) is maintained. Applicants’ argument that “the structure of crossed bonds
PNG
media_image1.png
200
400
media_image1.png
Greyscale
represents a commonly used nomenclature for a carbon-carbon double bond whose configuration is not fixed, that is, it can be any configuration/stereochemistry” (remarks page 7) was carefully reviewed and not found persuasive.
Contrary to Applicants assertions, a crossed double bond is not considered acceptable for general use. See GRAPHICAL REPRESENTATION OF STEREOCHEMICAL CONFIGURATION (IUPAC Recommendations 2006) Pure Appl. Chem., Vol. 78, No. 10, pp. 1897–1970, 2006 (cited in the PTO892 attached herewith) states that: The most common convention for depicting double bonds with unspecified configuration in molecules of all sizes uses a wavy bond.
This rejection is still deemed proper, and is therefore maintained.
2. The rejection of claims 1, 3, 4, 7-9, 12-17 under 35 U.S.C. § 102(a)(1) and 102(a)(2) as being anticipated by US20100240729, May 2009 by Shigeyuki is withdrawn in view of claim amendments to define variables R1 as C1-6 alkyl and C1-6 haloalkyl and R2 is H.
3. The rejection of claims 1, 3, 4, 7-17, under 35 U.S.C. § 103 over US20100240729, May 2009 by Shigeyuki is maintained/modified. Applicants’ argument that “instant method is associated with unexpected technical results not disclosed or taught by the '729 publication, notably, a superior yield of the resulting product. As seen in the table at 1 [0127] of the specification (reproduced below), a reaction utilizing the compounds encompassed by formulas (II) and (III) of claim 1 results in a significantly high yield of product (formula(I)) (Remarks page 7) was carefully reviewed and not found persuasive.
It is noted that regarding unexpected results commensurate in scope with claimed invention- the examples on Table 1 correspond to reaction of substrate of formula II in which variable X is S, R4 is phenyl or tolyl.
As noted before and reiterated herein, the prior art teaches reaction of phenol mediated by base with the methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate which corresponds to claimed formula III as discussed above differs from the instant claimed elected species by a hydrogen instead of methyl at the same loci (i.e. variables R1 and R2 in formula (II) and a methyl instead of ethyl for variable R3 of claimed formula II. Absent clear, convincing, side-by-side data demonstrating unobviousness vis-a-vis the prior art commensurate with the scope of protection sought, the claims are considered prima facie obvious.
Please note that if Applicant intends to rely on unexpected or unforeseen results, attention is invited to MPEP 716.02. This rejection is still deemed proper, and is therefore maintained.
4.The objection to claims has been addressed by amendment.
The following are modified or new grounds of rejections necessitated by Applicants’ amendment, filed on 4/16/2026 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 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, 3-4, and 7-17, 19, 20 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 pre-AIA the applicant regards as the invention.
In claim 1 the chemical drawing of formula II and formula I shows incorrect chemical bonding between carbon atoms further bonded to R1 or R2, rendering claim 1 and its dependents indefinite.
PNG
media_image2.png
200
400
media_image2.png
Greyscale
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Claim Rejections - 35 USC § 112
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 11 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.Claim 11 dependent upon Claim 1. The subject matter in Claim 1 is method of preparing a compound of general formula (I) in which variable R2 as amended is H. The subject matter in Claim 11 is the method of claim 1, wherein R2 is H. Therefore, the claim fails to further limit the subject matter thereof, and fails to comply with the formal requirements set forth in the fourth paragraph of 35 U.S.C. § 112.
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 § 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 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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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, 4, 7-17, 19, 20 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as anticipated by US20100240729, May 2009 by Shigeyuki (“the ‘729 publication”; cited in PTO892 attached herewith).
Determining the Scope and Content of the Prior Art
The ‘729 publication teaches the synthesis of (E)-methyl 2-methyl-3-phenoxy-2-propenoate by reacting phenol with methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate, shown below is the reaction as displayed in registry data base:
PNG
media_image4.png
177
456
media_image4.png
Greyscale
The ‘729 publication teaches on example 11 on [1716] the synthesis of the compound (E)-methyl 2-methyl-3-phenoxy-2-propenoate which corresponds to claimed formula I in which R1 is H, R2 is CH3, R3 is methyl (instant claim 12); R4 is ring A is phenyl; by reacting phenol which corresponds to claimed formula III in which ring A is C6 aryl (phenyl) and R is H, n is 5 (instant claims 7-9); with methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate - which corresponds to claimed formula II in which R1 is H, R2 is methyl, R3 is methyl; R4 is C6 aryl substituted with m’R” groups in which m’ is 1 R” is methyl (4-methylphenyl; instant claims 3, 4); the reaction is conducted in DMF as solvent (instant claim 14) the presence of base cesium carbonate (instant claims 1 and 13, 19, 20); at room temperature (instant claim 15).
PNG
media_image5.png
200
400
media_image5.png
Greyscale
Regarding instant claim 16 the ‘729 publication teaches reactants in 25.8 mmol 28.3 mmol which corresponds to 1:09 ratio which is within the claimed ratio of 1: 0.7-3.
Regarding instant claim 17 the ‘729 publication teaches reactant 25.8 mmol to 30.6 mmol base which corresponds to 1: 1.18 ratio which is within the claimed ratio of 1: 1-5.
Ascertainment of the Difference Between Scope of the Prior Art and the Claims
Regarding instant claims 10 and 11, the prior art teaches reaction of phenol mediated by base with the methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate which corresponds to claimed formula III as discussed above differs from the instant claimed elected species by a hydrogen instead of methyl at the same loci (i.e. variables R1 and R2 in formula (II) and a methyl instead of ethyl for variable R3 of claimed formula II. It is noted that replacement of methyl for hydrogen on a known compound was considered prima face obvious based on the homologous and close structural relationship to the known compound. Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds.
Finding of Prima Facie Obviousness Rationale and Motivation
It would have been prima facie obvious to one of ordinary skill in the art to utilize the method disclosed by the ‘ 729 publication to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to make the structural modification of the reactants and substitute with claimed elected species in the process of ‘729 publication. There would be a reasonable expectation of success of producing the corresponding product of claimed formula (I) because of the significantly close structural similarity between the substrates undergoing the same reaction and the claimed elected species, by the same method steps, in the presence of cesium carbonate as a base as disclosed by the cited prior art.
Thus, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
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).
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 an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see https://ppair-my.uspto.gov/pair/PrivatePair. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/ANA Z MURESAN/Primary Examiner, Art Unit 1692
Prosecution Insights