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 Response to Election/Restriction, filed Sept 29, 2025. As filed, claims 1, 3-17 are pending. Claims 2 and 18 are canceled.
Priority
This application 02 /24/2023 is a National Stage entry of PCT/CN2021/114070, International Filing Date: 08/23/2021 claims foreign priority to 202010856857.9, filed 08/24/2020.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed on 5/19/2023, 7/01/2024, 12/09/2024, 7/01/2025 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Election/Restrictions
Applicant’s election of Group I, claims 1, 3-17, drawn to a method for preparing compounds of formula I in the reply filed on 9/29/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.03(a)).
Applicant’s elect the species of the example 1 on [00137] of the specification
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The elected species correspond to claimed formula II in which X is S; R1: methyl; R2 is H; R3-= is ethyl; R4 is 4-methylphenyl; in formula III, ring A is phenyl, R is Cl; and n is 1. The Applicants indicated claims 1, 3-4, and 7-17 read on the elected species.
Applicants' elected species have been found not allowable due to the following rejections.
Claims 5, 6 are withdrawn from consideration as pertaining to non-elected
Claims 1, 3-4, and 7-17 will be examined on the merits herein to the extend they read on the elected species.
Claim Objections
Claims 1, 4, 9, 10, 13, 14 are objected for reciting improper Markush language: the recitation in claim 1 for definition of variables R1-R4 of Markush formula II, variable R of claimed formula III and variable R, R1, R2 of claimed formula I “selected from” - should be changed to “selected from the group consisting of”.
Similarly, the recitation in claims 4, 9, 10,13, 14 “selected from” and “is” in claim 5 and 6, 8, 12 should be changed to “selected from the group consisting of”. See MPEP 803.02. “A Markush-type claim recites alternatives in a format such as "selected from the group consisting of A, B and C." 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 1, 3-4, and 7-17 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.
1. 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.
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2.In claims 4, 7-9, 12-13, 15-17 the recitation “alternatively”; “yet alternatively “ rendering said claims indefinite. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c).
3. In claims 10, 13,14 the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
4.In claim 13, the phrase "for example" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
5.Claim 15, which depend from claim 1, recites the limitation "the reaction temperature”. There is insufficient antecedent basis for this limitation in the claim 1.
6.Claim 16, 17, which depend from claim 1, recite the limitation "the molar ratio”. There is insufficient antecedent basis for this limitation in the claim 1.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 3, 4, 7-9, 12-17 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).
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:
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The ‘729 publication teaches on example 11 on [1716] the synthesis of the compound (E)-methyl 2-methyl-3-phenoxy-2-propenoate of formula
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-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) at room temperature (instant claim 15). Regarding instant claims 10-11, the methyl 2-methyl-3-(p-toluenesulfonyloxy)-2-propenoate which is structurally similar to elected species, is noted that R1: methyl; R2 is H
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.
Therefore, the prior art teaches the limitations of instant claims.
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, 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:
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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); at room temperature (instant claim 15).
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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
Claims 1, 3, 4 7-17 are rejected. Claims 5, 6 are withdraw from consideration.
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).
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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.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692