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 .
Claims 1-19 are currently pending in this Application. Claims 15-19 are withdrawn from further consideration by the Examiner, 37 C.F.R. § 1.142(b), as being drawn to a non-elected invention. The withdrawn subject matter is patentably distinct from the elected subject matter as it differs in structure and element and would require separate search considerations.
Priority
CONTINUING DATA
This application is a 371 of PCT/US2021/030741 05/04/2021
PCT/US2021/030741 has PRO 63/019,812 05/04/2020
Information Disclosure Statement
Applicant’s Information Disclosure Statement, filed on November 04, 2022 has been considered. Please refer to Applicant’s copies of the 1449 submitted herewith.
Response to Restriction
Applicants’ election, without traverse, the invention of Group I, claims 1-14, drawn to Ru(II)-catalyzed enantioselective synthesis of a cyclic product, in response filed January 15, 2026 is acknowledged.
Therefore, the restriction requirement is considered proper and is maintained.
Applicant is reminded that upon the cancellation of claims to a non-elected invention, the inventorship must be amended in compliance with 37 CFR 1.48(b) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. Any amendment of inventorship must be accompanied by a petition under 37 CFR 1.48(b) and by the fee required under 37 CFR 1.17(i).
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.
The primary purpose of this requirement of definiteness of claim language is to ensure that the scope of the claims is clear so the public is informed of the boundaries of what constitutes infringement of the patent. A secondary purpose is to provide a clear measure of what applicants regard as the invention so that it can be determined whether the claimed invention meets all the criteria for patentability and whether the specification meets the criteria of 35 U.S.C. 112, first paragraph with respect to the claimed invention.", (see MPEP § 2173).
Claim 1-14 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.
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).
In the present instance:
Claim 1 recites the broad recitation “ …presence of co-catalysts”, and the claim also recites “including Ru(II) arene complex; and a chiral transient directing group” which is the narrower statement of the range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim. It is not clear what other co-catalysts are included or excluded.
Claim 2 recites the broad recitation “ …R1”, and the claim also recites “includes a branched or unbranched alkyl” which is the narrower statement of the range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim. It is not clear what other substituents are included or excluded.
Claim 8 recites the broad recitation “ …R1”, and the claim also recites “includes a branched or unbranched alkyl” which is the narrower statement of the range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim. It is not clear what other substituents are included or excluded.
It is recommended that Applicant remove the narrow limitations of the claims in all instances. Applicant can also add a new claim with the narrow limitations
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 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.
Claims 1-12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Li, Zhong-Yuan et al., Journal of the American Chemical Society, 2019, Vol. 141, pages 15730-15736.
The instant claim 1 is directed to a method of Ru(II)-catalyzed enantioselective synthesis of a cyclic compound, the method comprising: providing a precursor compound having an unfunctionalized C-H bond; and activating the unfunctionalized C-H bond by reacting the precursor compound in the presence of co-catalysts including: a Ru(II) arene complex; and a chiral transient directing group (CTDG).
Dependent claims 2-12 further limit the Ru(II) arene complex, CTDG and the precursor compound.
Li, Zhong-Yuan et al. discloses a method of enantioselective synthesis of compound 2aa,
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via catalytic C-H activation, the method comprising activating C-H bond by reacting compound laa,
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in the Ru3 presence of co-catalyst including [Ru(p-cymene)CI2]2,
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, and a chiral transient directing group (CTDG). Li, Zhong-Yuan et al. further discloses different Ru(II) arene complex, CTDG and the precursor compounds that anticipate the instant claims. (see abstract and table 1, table 2 and table 3). Therefore, claim 1-12 is anticipated by Li, Zhong-Yuan et al.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
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) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negatived 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(a) 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 1-14 are rejected under 35 U.S.C. 103(a) as being unpatentable over Li, Zhong-Yuan et al, Journal of the American Chemical Society, 2019, Vol. 141, pages 15730-15736 in view of LI, G. et al., Angewandte chemie international edition, 24 February 2020 (1st published 23 December 2019), Vol. 59, pages 3475-3479.
The instant claim 1 is directed to a method of Ru(II)-catalyzed enantioselective synthesis of a cyclic compound, the method comprising: providing a precursor compound having an unfunctionalized C-H bond; and activating the unfunctionalized C-H bond by reacting the precursor compound in the presence of co-catalysts including: a Ru(II) arene complex; and a chiral transient directing group (CTDG).
Dependent claims 2-12 further limit the Ru(II) arene complex, CTDG and the precursor compound.
Dependent claims 13 and 14 further limit the precursor compound to be
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.
Determining the Scope and Contents of the Prior Art
Claim 1-12 are anticipated by Li, Zhong-Yuan et al. (please see the 102 rejection explanation supra)
Claims 13 and 14 has a limitation of a precursor compound that is outside the scope of Li, Zhong-Yuan et al.
LI, G. et al. teach Ru(II)-catalyzed enantioselective synthesis of a cyclic product comprising reacting a precursor compound of Formula
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in the presence of cocatalyst of [Ru(p-cymene)Cl2]2 and a chiral transient director group.
Resolving the Level of Ordinary Skill in the Pertinent Art
“Factors that may be considered in determining level of ordinary skill in the art include: (1) the educational level of the inventor; (2) type of problems encountered in the art; (3) prior art solutions to those problems; (4) rapidity with which innovations are made; (5) sophistication of the technology; and (6) the education level of active workers in the field.” Envtl. Designs, Ltd. V. Union Oil Co., 713 F.2d 693, 696 (Fed. Cir. 1983) (citing Orthopedic Equip. Co. v. All Orthopedic Appliances, Inc., 707 F.3d 1376, 1381-82 (Fed. Cir. 1983)). The above factors are not exhaustive, but are a guide. Id.
In this case, the education level of the inventor and the education level of active workers in the field of organic chemistry, as well as the high degree of sophistication required to solve problems encountered in the art, a person of ordinary skill in the art would likely have at least a college degree in the field of organic chemistry, with industry experience, i.e., a masters or doctorate level of skill and knowledge in the laboratory. Thus, the level of skill in the art is relatively high.
Objective Evidence in the Application Indicating Obviousness or Nonobviousness
The Supreme Court in KSK International Co. v. Teleflex lnc.^ 550 U.S. 398, 127 S. Ct. 1727, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham. The key to supporting any rejection under 35 U.S.C. 103 is the clear articulation of the reason(s) why the claimed invention would have been obvious. The Supreme Court in KSK noted that the analysis supporting a rejection under 35 U.S.C. 103 should be made explicit.
Exemplary rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) “Obvious to try” — choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Note that the list of rationales provided is not intended to be an all-inclusive list. Other rationales to support a conclusion of obviousness may be relied upon by Office personnel. Here one or more of rationales (C) and (G) apply.
Prior to the filing of the instant application, a PHOSITA following the teachings of Li, Zhong-Yuan et al would have found it prima facie obvious to use the precursor compound of LI, G. et al. in the Ru(II)-catalyzed enantioselective synthesis of a cyclic compound of the instant claims because LI, G. et al. has identified the precursor compound in the preparing of Ru(II)-catalyzed enantioselective synthesis of a cyclic compound.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103(a). From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Accordingly, claims 1-14 are rendered obvious in view of the reference above. Applicant might consider providing evidence of unexpected results to overcome the rejection.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAMAL A SAEED whose telephone number is (571) 272-0705.
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, Adam C Milligan can be reached at (571)270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Kamal A Saeed/
Primary Examiner, Art Unit 1626
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