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
1. This application is a 371 of PCT/JP2021/025489 07/06/2021 FOREIGN APPLICATIONS, JAPAN 2020-122762 07/17/2020.
Claims 1-19 are pending.
Response to Restriction Election
2. Applicant’s election of group II and the species of Formula (3):
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in the reply filed on December 5, 2025 is acknowledged. The election was made without traverse. The examiner also acknowledges the election of the cobalt complex of Formula (1’) on page 4 of the reply, however this was not required for the election of group II. The action was ambiguous as to when the election of the cobalt complex was required but this was intended for the group I, which is drawn to the cobalt complexes. The examiner apologizes for the confusion. According to applicants’ representative claims 1-16 read on the elected species.
Objections
3. Claims 1-16 are objected to for the following informality: The claims use a parenthesis to set apart all the variable definitions in the claims, i.e. “(wherein….). Parenthesis is used as an explanation or afterthought into a passage that is grammatically complete without it, however in this case the material is required. This may be due to translation or an international filing artefact and a comma or some other mark may be used instead. Appropriate correction is required. Claims 2-9 are objected to for depending upon a rejected base claim.
Claim Rejections - 35 USC § 103
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, 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.
4. Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over Schotes WO 2019185541 A1 (cited on the IDS) AND Lu CN 110655456. 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:
Determination of the scope and content of the prior art
(MPEP 2141.01)
Schotes on pages 2-3 describes the process of the instant claims as shown below, with an iridium catalyst:
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The substrate II in a narrowest embodiment is 1-(2,2,4-trimethyl-1-quinolyl)ethenone, the elected species, l-[2,2,4-trimethyl-3,4-dihydroquinolin-1-yl]ethenone, in Examples 1-3, 6, 7-39 on page 35 ff.
Lu teaches an alternative to Iridium catalysts for the asymmetric hydrogenation of olefins on page 3 with the example of the compound of Formula IV:
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Lu explains on page 1 that, “The core of asymmetric hydrogenation of olefins is metal and chiral ligands. Among them, noble metals such as rhodium, ruthenium and iridium dominate the metal…..because precious metal reserves are scarce, they are often strategic resources and have certain toxicity. Therefore, it is of great significance to develop low-cost, metal-friendly catalytic systems with abundant reserves and environmental friendliness, especially in the fields of medicine and chiral materials. In 1998, Lu Zhan's research group at Zhejiang University successfully used a pyrimidine oxazoline chiral ligand (OIP) and cheap metal cobalt to achieve asymmetric hydrogenation…” Li on page 2 describes his method as “using the tri-substituted olefins represented by formula I as raw materials, and using atmospheric hydrogen as raw materials A hydrogen source, a CoBr2-IIP complex as a catalyst, and a silane compound as a cocatalyst. Under the action of a reducing agent, the reaction is performed for 24 to 48 hours to obtain a chiral alkyl compound…”
Ascertainment of the difference between the prior art and the claims
The prior art differs only in the type of catalyst used, iridium in the prior art of Schotes, while the instant claims substituted the known cobalt catalysts of Lu which had been used for the same purpose.
Finding of prima facie obviousness
Rationale and Motivation
(MPEP 2142-2143)
It would have been obvious to one of ordinary skill in the art at the time the claimed invention was made to substitute cobalt catalyst for iridium catalysts to produce the instant invention. The experienced organic chemist, would be motivated to undertake this substitution because cobalt is much cheaper than iridium, as Lu describes “cheap metal cobalt”. 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 forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. 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.
5. Claim(s) 1 is/are rejected under 35 U.S.C. 103 as being unpatentable over TAKAHASHI US 20170022162 A1 AND Chen “Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes.” Org. Lett. 2016, 18, 1594−1597. 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:
Determination of the scope and content of the prior art
(MPEP 2141.01)
Takahashi on pages 1 describes the process of the instant claims as shown below, with a catalyst ”wherein the transition metal catalyst having an optically active ligand is an iridium catalyst having an optically active ligand, a rhodium catalyst having an opti cally active ligand, or a ruthenium catalyst having an optically active ligand.”
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The substrate in a narrowest embodiment is 1-(2,2,4-trimethyl-1-quinolyl)ethenone, the elected species, l-[2,2,4-trimethyl-3,4-dihydroquinolin-1-yl]ethenone, in examples on page 10-11 at paragraph [0053] Formula I-11 and Formula 2-11.
Chen teaches an alternative to Iridium catalysts for the asymmetric hydrogenation of olefins on page 1594 with the examples in the abstract
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Chen explains on page 1594 column 1 that, “Although precious metal catalysts including rhodium, iridium, and ruthenium have been used for hydrogenation of 1,1-disubstituted alkenes to achieve high enantioselectivities,6 the high cost of removing trace amounts of precious metals for pharmaceutical utility and potential depletion of precious metals make the development of green, sustainable base-metal catalysts for hydrogenation highly desirable. Furthermore, the distinct electronic structures and unique redox ability of basemetals provide numerous opportunities for exploring new reactivity. Because of the lower costs and toxicity of cobalt catalysts, rapid progress has been made in cobalt-mediated or -catalyzed transformations during the last two decades.7”
Ascertainment of the difference between the prior art and the claims
The prior art differs only in the type of catalyst used, iridium in the prior art of Takahashi, while the instant claims substituted the known cobalt catalysts of Chen used for the same purpose.
Finding of prima facie obviousness
Rationale and Motivation
(MPEP 2142-2143)
It would have been obvious to one of ordinary skill in the art at the time the claimed invention was made to substitute cobalt catalyst for iridium catalysts to produce the instant invention. The experienced organic chemist, would be motivated to undertake this substitution because cobalt is much cheaper than rhodium, iridium, and ruthenium, and as Chen discusses there is trouble removing rhodium, iridium, and ruthenium. 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 forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. 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.
6. Claim(s) 10-11, is/are rejected under 35 U.S.C. 103 as being unpatentable over Schotes AND Lu as applied to claim 1 above, and further in view of Bellandi WO 2017178868 A1. Claim 10-11 have the additional step of an acid catalyzed rearrangement/hydrolysis of the dihydroquinoline (DQ), which is not taught by Schotes. Bellandi on page 5 has the additional claimed steps:
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It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
7. Claim(s) 10-11, is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi AND Chen as applied to claim 1 above, and further in view of Bellandi WO 2017178868 A1. Claim 10-11 have the additional step of an acid catalyzed rearrangement of the DQ, which is not taught by Takahashi. Bellandi on page 5 has the additional claimed steps. It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
8. Claim(s) 12-16, is/are rejected under 35 U.S.C. 103 as being unpatentable over Takahashi, Chen and Bellandi as applied to claims 1, 10-11 above, and further in view of Ujita US 9,227,911 B2. The resolution of the resulting indane in claims 12-15 with tartaric acid, is not discussed in Bellandi however it is known in the art as disclosed in Ujita (whole document). Regarding the coupling in claim 16, this is also disclosed in Bellandi on Page 3,
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It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
9. Claim(s) 12-16, is/are rejected under 35 U.S.C. 103 as being unpatentable over Schotes, Lu and Bellandi as applied to claims 1, 10-11 above, and further in view of Ujita US 9,227,911 B2. The resolution of the resulting indane in claims 12-15 with tartaric acid is not discussed in Bellandi, however it is known in the art as disclosed in Ujita (whole document). Regarding the coupling in claim 16, this is also disclosed in Bellandi on Page 3. It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the claims at issue are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground provided the reference application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The USPTO internet Web site contains terminal disclaimer forms which may be used. Please visit http://www.uspto.gov/forms/. The filing date of the application will determine what form should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
10. Claim 1 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of U.S. Patent No. 9,796,678 (cited on the IDS) in view of Chen “Cobalt-Catalyzed Asymmetric Hydrogenation of 1,1-Diarylethenes.” Org. Lett. 2016, 18, 1594−1597. Although the claims at issue are not identical, they are not patentably distinct from each other because the patented claims are drawn to any transition metal catalyst, while claim 1 is drawn to a cobalt catalyst at least where R1 is acetyl in the patent claims. As discussed above Chen teaches the claimed cobalt catalysts for hydrogenation. The prior claims therefore differ only in the type of catalyst used, claim 4 in the prior patent claim is drawn to iridium rhodium, and ruthenium catalysts, while the instant claims substitute the known cobalt catalysts of Chen used for the same purpose.
11. Claims 10-11 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of U.S. Patent No. 9,796,678 in view of Chen as applied to claim 1 above, and further in view of Bellandi. Claim 10-11 have the additional step of an acid catalyzed rearrangement of the DQ, which is not taught by the patent claims. Bellandi on page 5 has the additional claimed steps. It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
12. Claims 12-16 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of U.S. Patent No. 9,796,678 in view of Chen and Bellandi as applied to claims 1, 10-11 above, and further in view of Ujita US 9,227,911 B2. The resolution of the resulting indane in claims 12-15 with tartaric acid, is not discussed in Bellandi however it is known in the art as disclosed in Ujita (whole document). Regarding the coupling in claim 16, this is also disclosed in Bellandi on Page 3. It would be obvious to conduct the additional steps since they lead to the known end product pesticides.
Allowable Subject Matter
13. The following is a statement of reasons for the indication of allowable subject matter: Claims 2-9 are only objected to for depending upon a rejected base claim and having some issues with parenthesis but would be allowable if those issues were corrected and the limitations of claim 2 moved into the base claim 1. The cobalt complexes of claim 2 are known and Lavoie US 6,281,303 B1 discusses uses these same complexes for olefin polymerization. They are also known for hydroboration1, hydrosilation2, and as cited previously Guo3 teaches that cobalt Py-Box complexes catalyze 1,3-butadiene polymerization. Guo also mentions a number of other reactions, “Pybox ligand have been widely applied in asymmetric catalysis reactions, such as aldol addition [48,49], cyclopropanation [50-52], and aziridination reactions [53]” [Guo page 124-125]. However after an exhaustive search by the examiner finds no evidence that the compounds of claim 2 have been used in asymmetric hydrogenation. Alig4 is the most comprehensive review on the technology claimed conducted before the filing date of the instant claims. Alig describes the complex of Chen, which is distinguished from the claim 2 complex by having only one oxazoline. “The same group [Chen] developed an NNN-pincer ligand that combines the PDI and the chiral Pybox frameworks (Figure 23).381 This ligand has been applied to manganese-, iron-, and cobalt-catalyzed asymmetric hydrogenation, hydroboration, and hydrosilylation.382−386” [Alig Page 2694 col. 2].
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It is not surprising that the claim 2 cobalt complexes would also function as hydrogenation catalysts, however if one were to look at the process of Schotes WO 2019185541 and look for cheaper catalysts, one would choose catalysts already proven to catalyze hydrogenation, not the catalysts of claim 2 which had not been used for this purpose.
Conclusion
14. Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 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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/DAVID K O'DELL/Primary Examiner, Art Unit 1621
1 Zuo “Synthesis of 1,1-diboronate esters by cobalt-catalyzed sequential hydroboration of terminal alkynes.” Organic Chemistry Frontiers, 2016, 3(4), 434-438. (cited on the IDS)
2 Schuster, “Bench-Stable, Substrate-Activated Cobalt Carboxylate Pre-Catalysts for Alkene Hydrosilylation with Tertiary Silanes.” ACS Catalysis, 2016, 6(4), 2632-2636.
3 Guo “Synthesis, characterization and 1,3-butadiene polymerization studies of cobalt dichloride complexes bearing pyridine bisoxazoline ligands” Polymer 2015, 59, 124-132. (cited on the IDS)
4 Alig “First-Row Transition Metal (De)Hydrogenation Catalysis Based On Functional Pincer Ligands” Chem. Rev. 2019, 119, 2681−2751.