DETAILED ACTION
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 .
Status
This is in response to January 18, 2024 New Application filing with corresponding documents.
Claims 1-20 Care pending and are under examination in the above-identified application.
Priority
The present application U.S. Appln. Ser. No.:18/580,519, Filed: 01/18/2024 is a 371 Nat.’l Stage entry of WO 2023/001088 A1 (i.e., PCT/CN2022/106174, Intern.’ l Filing Date: 07/18/2022), which claims foreign priority to either CN113563242A (i.e., CN2021/ 10813487.5) and CN113548994A (CN 2021/10814726.9), each respectively, filed on 07/19/2021.
However, to overcome art rejections, while certified foreign documents were filed in the Chinese language, NO corresponding certified ENGLISH translation were filed for either of those Chinese language documents; i.e., therefore the earliest priority or effective filing date (EFD) for prior art consideration is 07/19/2022.
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.
Claims 1 to 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 1-10, 12, 14 and 17-18, respectively lacks clarity for reasons discussed below:
In particular, claims 1 and 5 are unclear for incorrectly naming the intermediate product at the end of step (a) in those claims, which then subsequently reappears in step (b) as the intermediate compound that is further reacted upon; i.e.,
in step (a) reaction of N-benzylpyrrolidone with trifluoroacetic anhydride cannot result in the incorrect compound name 3-(1-chloro-2, 2, 2- trifluoroethylidene)-N-benzylpyrrole, instead the correct compound intermediate formed should be named:
“3-(1-chloro-2, 2, 2- trifluoroethylidene) -N-benzylpyrrolidone”,
which correctly corresponds to chemical structure is shown in Fig. 1 and described written description of Example 3 (i.e., see paras. [0087]-[0095], esp. [0089]-[0091]):
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likewise in step (b) of claims 1 and 5, respectively,
in claim 1, the subsequent step (b) of the first compound reacted therein occurs by:
“dissolving 3-(1-chloro-2, 2, 2- trifluoroethylidene) -N-benzylpyrrolidone . . .”,
In claim 5. “wherein in the step (b), the mass ratio of 3-(1-chloro-2, 2, 2- trifluoroethylidene) -N-benzylpyrrolidone”,
not incorrect compound
3-(1-chloro-2, 2, 2- trifluoroethylidene)-N-benzylpyrrole,
Claim 1 also is indefinite, vague, ambiguous and lacks clarity for recitation such that the metes and bounds of the claimed invention are rendered indeterminate, because:
[a] Steps (a) and (d) each recite presence of “a catalyst and hydrogen”, with each recitation of “a catalyst” reacting on a different intermediate substrate, without any differentiation (i.e., without knowing more, it is the same catalyst or a different catalyst or an additional amount of the same catalyst?). It is recommended that claim 1 be amended to indicate that there are two different applications of what appears from the reaction scheme is the same catalyst used in this reaction sequence. Clarification is required.
For consistency, it is suggested that step (a) be amended to recite
reacting N-benzylpyrrolidone with trifluoroacetic anhydride to obtain 3-(1-chloro-2, 2, 2- trifluoroethylidene)-N-benzylpyrrolidone” to form a reaction mixture”.
Claims 2, 7, 8, 12, 17,18 are rejected under 35 U.S.C. § 112(b) for indefiniteness and ambiguity for failure to particularly point out and distinctly claim the subject matter regarded as the invention, due to recitation of the terms “preferably” ” (i.e., in claims 6, 8, 16, 18), or “specifically comprising” (i.e., in claims 2, 7, 8, 12, 17,18)” in each of the various method steps in preparation enders the aforementioned claim ambiguous.
In particular,
The term "preferably" introduces ambiguity as it suggests flexibility in scope—i.e., preparation method or process might further comprise an additional step in order to effectuate a certain chemical reaction transformation to yield and obtained the specifically desired compound, such that application of the term preferably done to perform an action fails to make a specific desired molecule.
Claims 4 and 14, respectively lack clarity, is ambiguous and has antecedent basis issues, for the following reasons:
Recitation of the term “PE”, especially when or no previous identification for the aforementioned phrase (i.e., ethyl acetate).
Based on aforementioned suggested claim 1 amendments, a proposed amendment to claim 4 as shown and likewise to claim 14 be made:
“The preparation method according to claim 2, wherein the step (a) further comprises subjecting a mixture obtained after the reaction in this step to extraction and column chromatography, wherein a solvent used for the extraction is ethyl acetate (EA), and developing agents used for column chromatography are in a solution of petroleum ether (PE) and EA in a volume ratio of 10:1.”
Clarification for each of the above is requested accordingly.
Closest Prior Art
The prior art made of record and not relied upon is considered pertinent to Applicant's disclosure are exemplified by these references that teach methods for making compounds of the instant claimed invention with different chemical preparation routes:
[1] U.S. Pat. 9,067,930 B2 (Filed: April 8, 2014; Issued: June 30, 2015) discloses the preparation method of 3-(2,2,2-trifluoroethyl)-pyrrolidine hydrochloride (see col. 27, lines 1-35).
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Bugeram, J. Org. Chem., 2019, vol. 84, No. 24, pp. 16105-16115, discloses a preparation method of 3-(2,2,2-trifluoroethyl)-pyrrolidine hydrochloride via a different chemical reaction sequence (i.e., different reaction steps) than that disclosed in the claimed invention (i.e., see Scheme 6 and description col. 2, at page 16108 shown below):
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CONCLUSION
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to GRACE C HSU whose telephone number is (571) 270-1689. The Examiner can normally be reached Monday-Friday 7:30 am - 6 pm.
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/G.C.H./Examiner, Art Unit 1627
/Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627
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