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 .
DETAIL ACTION
This office action is a response to an application filed 8/1/2023 claiming domestic priority to 63/393,984 filed 8/1/2022.
As filed, claims 1-17 are pending, wherein claim 1 is an independent claim.
Election/Restrictions
Applicant’s election without traverse of Group I – Claims 1-11 and 17 in the reply filed on 2/2/2026 is acknowledged.
Claims 12-16 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 2/2/2026.
Regarding the election of species requirement, Applicant elected the species of acetophenone for instantly claimed carbonyl compound; and TFAB-NEt3 for the instantly claimed TFAB-amine complex, which are found in paragraphs 0052 and 0007 of the instant specification, respectively. The Examiner finds the claims, which read on both elected species, are instant claims 1, 2, 4, and 6-11.
Claims 3, 5, and 17 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Examination will begin with the elected species. In accordance with the MPEP 803.02, if upon examination of the elected species, no prior art is found that would anticipate or render obvious the instant invention based on the elected species, the search of the Markush-type claim will be extended. If prior art is then found that anticipates or renders obvious the non-elected species, the Markush-type claim will be rejected. It should be noted that the prior art search will not be extended unnecessarily to cover all non-elected species . Should Applicant overcome the rejection by amending the claim, the amended claim will be reexamined. Id. The prior art search will be extended to the extent necessary to determine patentability of the Markush-type claim. Id. In the event prior art is found during reexamination that renders obvious or anticipates the amended Markush-type claim, the claim will be rejected and the action made final. Id.
As per MPEP 803.02, the Examiner will attempt to determine whether the entire scope of the claims is patentable. Applicants' elected species, as shown above, does makes a contribution over the prior art. Therefore, according to MPEP 803.02: should the elected species appear allowable, the search of the Markush-type claim will be extended. The search and examination should be continued until either (1) prior art is found that anticipates or renders obvious a species that falls within the scope of a proper Markush grouping that includes the elected species, or (2) it is determined that no prior art rejection of any species that falls within the scope of a proper Markush grouping that includes the elected species can be made. The Examiner need not extend the search beyond a proper Markush grouping.
Because the Markush-type claim (i.e. claim 1) is determined to be free of prior art, claims 3, 5, and 17 are rejoined and examined herein. Accordingly, the election of species requirement is hereby withdrawn.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 6/19/2024 has been considered by the Examiner.
Claim Rejections - 35 USC § 112(a)
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1 and 6-11 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 1 recites the limitation, “carbonyl compound”, in reference to the instantly claimed processes. Applicant has not described the claimed genus of “carbonyl compound” in a manner that would indicate they were in possession of the full scope of this genus, or even to describe what this genus is comprised of.
Regarding the requirement for adequate written description of chemical entities, Applicant's attention is directed to the MPEP §2163. In particular, Regents of the University of California v. Eli Lilly & Co., 119 F.3d 1559, 1568 (Fed. Cir. 1997), cert. denied, 523 U.S. 1089, 118 S. Ct. 1548 (1998), holds that an adequate written description requires a precise definition, such as by structure, formula, chemical name, or physical properties, "not a mere wish or plain for obtaining the claimed chemical invention." Eli Lilly, 119 F.3d at 1566. The Federal Circuit has adopted the standard set forth in the Patent and Trademark Office ("PTO") Guidelines for Examination of Patent Applications under the 35 U.S.C. 112.1 "Written Description" Requirement ("Guidelines"), 66 Fed. Reg. 1099 (Jan. 5, 2001), which state that the written description requirement can be met by "showing that an invention is complete by disclosure of sufficiently detailed, relevant identifying characteristics," including, inter aria, "functional characteristics when coupled with a known or disclosed correlation between function and structure..." Enzo Biochem, Inc. v. Gen-Probe Inc., 296 F.3d 316, 1324-25 (Fed. Cir. 2002) (quoting Guidelines, 66 Fed. Reg. at 1106 (emphasis added)). Moreover, although Eli Lilly and Enzo were decided within the factual context of DNA sequences, this does not preclude extending the reasoning of those cases to chemical structures in general. Univ. of Rochester v. G.D. Searle & Co., 249 Supp. 2d 216, 225 (W.D.N.Y. 2003).
In the instant case, the claimed “carbonyl compound” encompasses any compound having any number of carbonyl groups (e.g. aldehyde, ketone, ketoacid, ester, amide, etc.). Applicants described a number of aldehydes, ketones, ketoacids, etc. as examples of “carbonyl compound” (Fig. 1; and paragraphs 0012, 0038, 0041-0043, and 0053-0066), which are not described adequately enough to allow one skilled in the art to ascertain that Applicant is in possession of the entire scope of that genus. Applicants have not described this genus in a manner that would allow one skilled in the art to immediately envisage the compounds contemplated for use.
The Examiner finds that one of ordinary skill in the art would recognize that chemical synthesis is unpredictable. Not all carbonyl compounds can be used in reductive amination, which is supported by the prior arts. The prior arts only demonstrated that reductive amination can be achieved through the use of aldehyde and ketone. See Lee et al., Highly Chemoselective Reductive Amination of Carbonyl Compounds Promoted by InCl3/Et3SiH/MeOH System. J. Org. Chem., 2008, 73, 8829-8837; and Sato et. al., One-Pot Reductive Amination of Aldehydes and Ketones with A-Picoline-Borane in Methanol, in Water, and in Neat Conditions. Tetrahedron, 2004, 60, 7899-7906. Both see IDS filed 6/19/2024.
As such, the claim lacks adequate written description for the claimed “carbonyl compound”.
Regarding claims 6-11, these claims are directly or indirectly dependent of claim 1, and they failed to correct the defective issue in claim 1, which rendered these claims improper.
Claim Rejections - 35 USC § 112(b)
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 4, 5, 7, and 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 4, the claim recites the phrase, “wherein the carbonyl compound is a ketone of formula (5)”, which has the following structure:.
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. Instant variables R3 and R4 include hydrogen. When R3 and R4 are hydrogen, formula (5) is drawn to an aldehyde, not a ketone, which introduced ambiguity into the metes and bounds of this claim. Accordingly, the claim is indefinite.
Regarding claim 5, the claim recites the phrase, “wherein the carbonyl compound is a ketoacid of formula (8)”, which has the following structure:.
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. Instant variable R2 includes hydrogen. When R2 is hydrogen, formula (5) is drawn to an aldehyde-acid, not a ketoacid, which introduced ambiguity into the metes and bounds of this claim. Accordingly, the claim is indefinite.
Regarding claim 7, the claim recites the phrase, “wherein the TFAB-amine complex is represented by formula (2)”, which has the following structure:
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. R3N includes piperidine, pyridine or 2-picoline. According to the guidance in the instant specification (paragraph 0091), the word, “amine”, does not include cyclic amine or aromatic amine, such as piperidine, pyridine or 2-picoline. Accordingly, the piperidine, pyridine or 2-picoline of R3N and the phrase, “TFAB-amine complex” contradict each other, which introduced ambiguity into the metes and bounds of this claim. Accordingly, the claim is indefinite.
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(paragraph 0091 of the instant specification)
Regarding claim 17, the claim is dependent of claim 5, and it failed to correct the indefiniteness issue of claim 5, which rendered the claim indefinite.
Claim Objections
Claims 1 and 17 are objected to because of the following informalities:
Regarding claim 1, the claim recites the phrase, “with an amine in the presence”. Such expression can be clarified by reciting -- with an amine in
Regarding claim 17, the claim recites the phrase, “wherein the keto acid undergo tandem reductive amination-cycloamidation”.
Such expression can be clarified by reciting -- wherein the keto acid further undergo tandem reductive amination-cycloamidation --.
Appropriate correction is required.
Allowable Subject Matter
Claims 2 and 3 are objected to as being dependent upon a rejected and an objected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims, and the objection of the base claim is corrected.
The instant claims are drawn to a process of direct reductive amination of a carbonyl compound in the presence of a trifluoroacetoxyborane-amine (TFAB-amine) complex; and the use of TFAB-amine complex in direct reductive amination do not appear to have been disclosed previously in the prior arts. For at least this reason, the instant claims are substantially differentiated from any prior art reference, such as “Highly Chemoselective Reductive Amination of Carbonyl Compounds Promoted by InCl3/Et3SiH/MeOH System”, hereinafter Lee (see IDS filed 6/19/2024). Furthermore, the prior art provide insufficient guidance or motivation that would have led a person having ordinary skill in the art to arrive at the instantly claimed process.
Conclusion
Claims 1, 4-11, and 17 are rejected.
Claims 2 and 3 are objected.
Claims 12-16 are withdrawn.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PO-CHIH CHEN whose telephone number is (571)270-7243. The examiner can normally be reached Monday - Friday 10:00 am to 6:00 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached at (571)270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/PO-CHIH CHEN/Primary Examiner, Art Unit 1621
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