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.
Restriction Election Maintained
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is restricted to the claims reading on the elected species, and claims not reading on the elected species are held withdrawn. Accordingly, claims 4, 10, 12, 24, 26, 28 which do not read on the elected species are withdrawn.
Claim Rejections/Objections Withdrawn
4. The rejection of 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 Journal of the American Chemical Society, 2021, 143(44), 18592-18604 Published online 27 October 2021 is withdrawn in view of the attribution affidavit of inventor Nagorny under 1.130(a) on July 2, 2026. Wang was published on 7 October 2021 which is within the grace period, the one year before the priority date of 11 August, 2022. The rejection is withdrawn based upon the 102(b)(1) exception. As per MPEP 2155.01:
AIA 35 U.S.C. 102(b)(1)(A) provides that a grace period disclosure shall not be prior art to a claimed invention under AIA 35 U.S.C. 102(a)(1) if the disclosure was made by the inventor or a joint inventor. An applicant may show that a disclosure was made by the inventor or a joint inventor by way of an affidavit or declaration under 37 CFR 1.130(a) (an affidavit or declaration of attribution). See In re Katz, 687 F.2d 450, 455, 215 USPQ 14, 18 (CCPA 1982) and MPEP § 718. Where the authorship of the prior art disclosure includes the inventor or a joint inventor named in the application, an "unequivocal" statement from the inventor or a joint inventor that the inventor or joint inventor (or some specific combination of named inventors) invented the subject matter of the disclosure, accompanied by a reasonable explanation of the presence of additional authors, may be acceptable in the absence of evidence to the contrary.
Claim Rejections/Objections Maintained/ New Grounds of Rejection
5. The rejection of claims 1-3, 14, 22, 30, 32, 35-37, 76 under 35 U.S.C. 103 as being unpatentable over Lai AND Rahman is maintained. Applicant's arguments filed July 2, 2026 have been fully considered but they are not persuasive. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Applicant argues that the motivation is ”removing the 3,3'-diphenyl substituents from the immobilized SPA's of Lai”, however the rejection explains that one of ordinary skill would not remove phenyl groups from the Lai compounds, but rather immobilize other known SPAs such as those disclosed in Rahman in the same manner as done by Lai which lack the phenyl groups. One would be motivated to make the solid supported versions of the known catalysts 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.”
With respect to the arguments on page 12 and the declaration under 1.132 of inventor Nagorny, the method of making the Lai immobilized phosphoric acid compounds is different. According to the arguments, the steps of preparing the compounds is reversed. It is noted that the features upon which applicant relies (i.e., the process of making the compounds) are not recited in the rejected claim(s). Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). While no product by process limitations are present if they were, patentability is based on the product itself, not the method by which it is made. See MPEP 2113 for a discussion of Product by Process claims: "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process."
According to the arguments and declaration using this alternative sequence, installing phosphoric acid groups after polymerization, to prepare the immobilized compounds results in increased conversion. This is quite interesting, however the comparison is unrelated to the claimed compounds. The compounds in the Wang dissertation1 discussed on pages 4-5 are some BINOL compounds, not the SPINOL compounds. If Wang is prior art and the alternative sequence was known to give superior results, the artisan would simply use this method to attach the known phosphoric acids to the same Lai resins.
According to paragraph 12, the supported catalyst (S)-3 was better than the unsupported catalyst (S)-16. According to the arguments, “immobilized catalyst (S)-3 generally had a comparable or higher yield and selectivity than its unsupported counter part”, however this is an argument that supported versus non-supported is better and has nothing to do with the alternative sequence of immobilization discussed in the Wang dissertation. The characterization immobilization “generally had a comparable or higher yield and selectivity” does not meet the requirement of unexpected results. There is no actual value of any yield and/or selectivity improvement only vague statements. As per MPEP 716.02(b) "The evidence relied > upon < should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance." Ex parte Gelles, 22 USPQ2d 1318, 1319 (Bd. Pat. App. & Inter. 1992) (Mere conclusions in appellants' brief that the claimed polymer had an unexpectedly increased impact strength "are not entitled to the weight of conclusions accompanying the evidence, either in the specification or in a declaration."); Ex parte C, 27 USPQ2d 1492 (Bd. Pat. App. & Inter. 1992) (Applicant alleged unexpected results with regard to the claimed soybean plant, however there was no basis for judging the practical significance of data with regard to maturity date, flowering date, flower color, or height of the plant.). See also In re Nolan, 553 F.2d 1261, 1267, 193 USPQ 641, 645 (CCPA 1977) and In re Eli Lilly, 902 F.2d 943, 14 USPQ2d 1741 (Fed. Cir. 1990) as discussed in MPEP § 716.02(c)." "[A]ppellants have the burden of explaining the data in any declaration they proffer as evidence of non-obviousness." Ex parte Ishizaka, 24 USPQ2d 1621, 1624 (Bd. Pat. App. & Inter. 1992). Assuming the immobilization resulted in a yield that is unexpected which has not been shown, the evidence of unexpected results "must be reasonably commensurate with the scope of the claims," although every claimed embodiment need not be tested. In re Huai-Hung Kao, 639 F.3d 1057, 1068 (Fed. Cir. 2011); see also Allergan, Inc. v. Apotex, Inc., 754 F.3d 952, 965 (Fed. Cir. 2014). "Appellant bears the burden of establishing a nexus between the full scope of the claimed invention and the proffered evidence of nonobviousness." Demaco Corp. v. F. Von Langsdorff Licensing Ltd., 851 F.2d 1387, 1392 (Fed. Cir. 1988). Unexpected results must be “commensurate in scope with the degree of protection sought by the claimed subject matter.” In re Harris, 409 F.3d 1339, 1344 (Fed. Cir. 2005). The claims are drawn to immobilizing all known SPINOLs on any known substrate, however S-3 is just one SPINOL immobilized in one way on one substrate. Lai remarks on page 14976, “From the point of view of yield, it is important to remark that all the studied desymmetrization reactions are very clean, no significant byproducts being detected. Thus, although lower than optimal yields detected in some cases (>65%), it should be possible to increase them by simply adjusting flow rate in those particular examples.” Lai also explains on page 14980, “Cat f exhibits unlimited recyclability (to the extent of the attempted reuses) in batch and flow, providing the target desymmetrized products in high yield (up to 92%) and enantioselectivity and (upto>99%ee), high productivity being recorded under both types of experimental conditions.” Expected beneficial results are evidence of obviousness of a claimed invention, just as unexpected results are evidence of unobviousness thereof." In re Gershon, 372 F.2d 535, 538, 152 USPQ 602, 604 (CCPA 1967) (resultant decrease of dental enamel solubility accomplished by adding an acidic buffering agent to a fluoride containing dentifrice was expected based on the teaching of the prior art); Ex parte Blanc, 13 USPQ2d 1383 (Bd. Pat. App. & Inter. 1989).
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.
6. 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
7. THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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 According to the declaration, Wang is a University of Michigan Dissertation from 2021 written by one of the co-inventors. Wang may be prior art, although the publication month and day has not been cited and has not been supplied to the examiner. It could be useful to disclose this document in full with an exact publication date to the examiner and cite it on an IDS.
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