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. Claims 1-4, 10, 12, 14, 22, 24, 26, 28, 30, 32, 35-38, 54, 76 are pending in the current application.
2. This application has PRO 63/397,220 08/11/2022.
Response to Restriction Election
3. Applicant’s election of group I and the species
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, Example S-3 in the specification on page 24, in the reply filed on December 29, 2025 is acknowledged. The election was made without traverse. According to applicants’ representative claims 1-3, 14, 22, 30, 32 , 35-37, 76 read on the elected species. As best as can be understood the “solid support” in this species is a PVA/styrene/DVB polymer and “white spherical particles”. These appear to be “polymer beads” of claim 32, and the composition of claim 37, although the polymer does not appear to have been fully characterized and no mention of beads is given. As detailed in the following rejections, the generic claim encompassing the elected species was not found patentable. The search and examination was continued until prior art was found that anticipated or rendered obvious a non-elected species that falls within the scope of the generic Markush claim reading on the elected species. As per MPEP 803.02 II. C. “[T]he examiner must continue to search the species of the claim unless the claim has been found to be unpatentable over prior art.” The examiner “need not continue to search the claim if the claim is rejected over prior art”. [ibid. D.] Therefore, the search and examination is restricted to the claims reading on the elected species, and claims not reading on the elected species are held withdrawn. Accordingly, claims 4, 10, 12, 24, 26, 28 which do not read on the elected species are withdrawn.
Claim Rejections - 35 USC § 102
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.
4. Claim(s) 1-3, 14, 22, 30, 32 , 35-37, 76 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wang, Sibin; Zhelavskyi, Oleksii; Lee, Jeonghyo; Arguelles, Alonso J.; Khomutnyk, Yaroslav Ya.; Mensah, Enoch; Guo, Hao; Hourani, Rami; Zimmerman, Paul M.; Nagorny, Pavel “Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides.” Journal of the American Chemical Society, 2021, 143(44), 18592-18604 Published online 27 October 2021. Wang on page 28 of the supporting info discloses the elected species
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Further shown on page 65:
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According to the description, the solid support is a polymer made from polyvinyl alcohol, styrene, and divinyl benzene described as a “Polymeric product 3” the same as in the elected species. This is a compound of claim 1 having the definitions of the elected species, i.e. R1 is aryl substituted with R8 where R8 is C1haloalkyl (CF3), R2 is H, R3 is 4-alkylenephenylene, Z is the solid support.
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.
5. Claim(s) 1-3, 14, 22, 30, 32 , 35-37, 76 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lai, Junshan; “Development of Immobilized SPINOL-Derived Chiral Phosphoric Acids for Catalytic Continuous Flow Processes. Use in the Catalytic Desymmetrization of 3,3-Disubstituted Oxetanes.” ACS Catalysis, 2020, 10(24), 14971-14983 AND Rahman “Development and application of chiral spirocyclic phosphoric acids in asymmetric catalysis” Org. Biomol. Chem., 2018, 16, 4753–4777. 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)
Following their previous work on immobilized BINOL-derived chiral phosphoric acids (ref. 64-68, Lai page 14972 col 1-2), Lai expanded the concept to catalysts containing the configurationally more stable chiral SPINOL backbone. “We report in this manuscript the synthesis of a family of 3,3′-diphenyl-SPINOL bearing polymerizable substituents at either C4−C4′ or C6−C6′, their immobilization by copolymerization, the preparation of the corresponding CPAs (Cat b−Cat f), and the use of these catalytic species for the desymmetrization of 3-substituted oxetanes with benzothiazole thiols (up to 90% yield and >99% ee) in batch and in flow.” [ibid. col. 2]. The chiral phosphoric acid SPINOL precursor compounds contain vinyl moieties that copolymerize with styrene and divinylbenzene to form the supported catalyst. As discussed on page S3 and S4, the Cat b the solid support was synthesized with a suspension of polyvinyl alcohol (PV-OH) and a solution containing divinylbenzene (DVB), BINOL derivative and styrene described as “light-yellow beads”. This is the same solid support technique used to support the claimed compounds, such as the elected species, through 4,4’-alkyeneyl-phenylene linkers, cross linked polystyrene, which are those in Wang as discussed above. Solid support-immobilized catalysts simplify product isolation and facilitate the recovery and recyclability of the catalyst and allow reactions under flow conditions. As Lai discusses on page 14972, the most useful SPINOL analogs like the elected species have “bulky substituents at the 6,6′-positions on the SPINOL skeleton” which are ”essential for the achievement of optimal enantiocontrol.” According to Lai, on page 1497 col. 1:
This is not a trivial detail, since the introduction of such substituents always requires additional synthetic steps leading to increased production costs that could hamper large scale application This limitation, however, could be efficiently mitigated by immobilization of the catalyst onto solid supports. If correctly planned, this strategy could allow the easy recovery and recycling of the catalyst (thus extending its useful life span) and easy product isolation without paying a penalty in catalytic activity.37,38 Moreover, catalytic processes based on immobilized catalysts often present the remarkable advantage of allowing implementation in continuous-flow.39−56 As a consequence of these advantages, interest in the immobilization of homogeneous chiral catalysts onto diverse solid supports has spread in recent years,57−61 with chiral phosphoric acids clearly illustrating this tendency.
Rahman explains on Page 5755 col. 1, that besides 3,3′-diphenyl-SPINOL chiral phosphoric acids in Lai there are many others:
There is a large variety of structural variations of the SPA catalysts in the literature, with Fig. 3 showing the key family members of SPAs used in the majority of asymmetric reactions. It should be highlighted that most of these SPA catalysts are now commercially available from Strem Chemicals and Daicel Corporation. SPA 1 is the simplest catalyst, but most of the catalysts used in asymmetric reactions have some substitution at the 6,6′-positions since the steric bulkiness at this position usually plays an important role in obtaining a high enantioselectivity. The catalysts SPA (3–8) are commonly seen in this scenario. Catalysts SPA (9–13) have substitutions at the para position of a benzene ring, and these types of catalysts play a dual role in providing bulkiness as well as regulating the electronic properties of the catalysts for activation of the substrates. 3,5-Disubstituted SPA (14–17) and 2,4,6-trisubstituted SPA (18–21) on a benzene ring are the major classes of catalysts, which give dramatically increased steric bulkiness and varied acidity. SPA 19 is most commonly used catalyst in the literature, where it is often abbreviated to STRIP.
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The elected species is SPA 14 and the claims are drawn to all the compounds above affixed to solid support.
Ascertainment of the difference between the prior art and the claims
The prior art differs only in the choice of SPINOL chiral phosphoric acid immobilized on the solid support. Lai used 3,3′-diphenyl-SPINOL while the instant claims are drawn to immobilizing almost any other known chiral SPINOL phosphoric acids such as those taught in Rahman.
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 immobilize other SPAs on solid support using the same technique of Lai to produce the instant invention. Based upon Lai, additional SPAs taught in Rahman could be transformed into immobilized compounds with the same advantages. Rahman is reference 27 in Lai. One would be motivated to make the solid supported versions of the known catalyst in Rahman, to reduce production costs that could hamper large scale application, allow implementation in continuous-flow, easy recovery and recycling of the catalyst (thus extending its useful life span) and easy product isolation without paying a penalty in catalytic activity. This is an exemplary rationale as discussed in the MPEP 2143, “(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.” For these reasons the immobilized elected species and the additional SPAs in Rahman are obvious over Lai and Rahman.
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.
Conclusion
6. 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