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/EP2020/064743 05/27/2020; FOREIGN APPLICATIONS:EP 19176783.9 05/27/2019.
Claims 1, 3, 5-8, 10-13, 15-20, 22-23 are pending.
Request for Continued Examination
2. A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on November 7, 2025 has been entered.
Restriction/Election Maintained
3. Applicant’s election of group I and the species,
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without traverse in the reply filed on November 12, 2024 was previously acknowledged. As detailed in the following rejections, the elected species was not found patentable. The search and examination was continued until prior art was found that anticipated or rendered obvious the 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the claims reading on the elected species, and claims 3, 5-6, 10-11, 15-19 not reading on the elected species are held withdrawn.
Response to Amendments/Arguments
4. The rejection of claim(s) 1, 7-8, 20, 22-23 under 35 U.S.C. 103 as being unpatentable over Ondi WO ‘679 in view of Townsend is maintained. Applicant's arguments filed April 18, 2025 have been fully considered but they are not persuasive. Applicants’ representative argues that the feature “wherein LO- is racemic” distinguishes over the prior art. It is not clear if the stereochemistry shown in the compounds of Ondi above is absolute or relative. However, racemic compound contains both the isomers, a genus of two compounds. Assuming the configuration were absolute at least one of the two isomers of the claimed genus is disclosed in Ondi. According to Ondi page 15 lines 19-20, “The catalysts may be prepared according to known methods or methods e.g. known from US 2011/0077421 A1, US 6,121,473, US 2008/0119678 and US 2011/0015430.” As explained in Schrock US ‘421 page 4 the Binol ligands for example may be racemic or enantioenriched: “[0029] In some cases, an oxygen-containing ligand may be chiral and may be provided as a racemic mixture or a purified stereoisomer. In some embodiments, the chiral, oxygen-containing ligand may be present in at least 80% optical purity, i.e., the oxygen-containing ligand sample contains 90% of one enantiomer and 10% of the other. In some embodiments, the chiral, oxygen-containing ligand may be at least 90% optically pure, at least 95% optically pure, or, in some cases, at least 99% optically pure.” Therefore Ondi discloses both racemic and enantioenriched compounds.
According to the arguments, “Townsend neither teaches nor suggests providing the elected compound as solvate (acetonitrile) wherein LO- is racemic.” However it is not clear if the stereochemistry shown in the compounds of Townsend is absolute or relative. Assuming the configuration were absolute, the claimed racemic compound is drawn to both the isomers, a genus of two compounds. As explained in Schrock US ‘421, disclosed in Ondi as discussed above, these compounds were known ”and may be provided as a racemic mixture or a purified stereoisomer.”
According to the arguments, “the Application as filed discloses at page 10, para [0043] that compound 4 (on which nitrile adduct compound 1 is based) crystallizes very well provided LO- is racemic, in contrast to the compound when developed with (R) LO-. Accordingly, the presence of racemic bitet in the compounds defined in amended claim 1 further improves the tendency for crystallization additionally to the presence of a neutral ligand such as acetonitrile. This beneficial property can also not be ascertained from the cited prior art on file.” This is not the evidence in the specification as it relates to the claims. Compound 4 is not the subject of claim 1, and is the compound of Ondi cited in the rejection and would be rejected under anticipation, as such it is unclear what the argument is since compound 4 is not the subject of the rejected claim. Looking at page 39 which has the preparation of the claimed compound, compound 1, the R isomer was used, and it is not the racemic compound as argued. The (R) isomer ligand “(R)-3,3'-substituted-2'-(tert-butyldimethylsilyloxy)-5,5,6,6,7,7',8,8'-octahydro-1,1'-binaphthyl-2-ol”, was clearly used for the embodiment rejected over Ondi.
The alternative workup in Townsend who made acetonitrile solvent adducts led to crystals, but not without the acetonitrile adduct. 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.
5. Claim(s) 1, 7-8, 20, 22-23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Ondi WO 2014139679 in view of Townsend “High Oxidation State Molybdenum Imido Heteroatom-Substituted Alkylidene Complexes.” Organometallics 2013, 32, 4612−4617. 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)
Ondi teaches compounds that are desolvated analogs of the compounds of the instant case that have the same utility. For instance the specific compounds on pages 44-46 shown below:
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The complexes were made as disclosed on page 114 by adding the phenol to the tungsten complex. The workup consisted of “volatiles were removed under reduced pressure and the resulting orange solid was triturated with n-pentane (15ml) to afford a yellow precipitate. The flask was sealed and allowed to cool to -38 °C (glovebox freezer) for 12 h. The orange precipitate was collected by vacuum filtration and washed with cold pentane (~5ml) to afford the titled compound as an orange powder”. Compositions of claim 20 are disclosed on page 128 where “Purification of allylbenzene by a chemical purification step: Reaction of by-products with trioctyl aluminum” and is the subject of claim 30 vis a vis claims 9-12.
An alternative workup is described in Townsend for these same type of complexes where besides pentane, acetonitrile can be used. Crystals were isolated with the acetonitrile adduct, but not without. “The reaction between 1b and CH2 =CHPPh2 yields Mo(NAr)(CHPPh2)(Me2Pyr)(OTPP) (2e) as a red solid in 63% yield. Crystals were isolated as an orange acetonitrile adduct of 2e (2e′) in 79% yield.” [Townsend page 4614 col. 1]. “Mo(NAr)(CHPPh2)(Me2Pyr)(OTPP) (2e) and MeCN Adduct” “Pentane was again added (10 mL), and the red slurry was stirred and filtered to obtain 92 mg of red product (63% yield). The acetonitrile adduct of 2e can be obtained as an orange powder in 79% yield by adding acetonitrile in place of pentane in the workup.” [Townsend page 4617 col. 1].
Ascertainment of the difference between the prior art and the claims
Compound 207 of Ondi differs from the elected species only by the presence of the neutral ligand acetonitrile, or as a solvent adduct.
Elected Species
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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 make a solvent adduct of the compounds of Ondi to produce the instant invention. Typically neutral solvent adducts are easier to crystallize and manipulate. They can also be more air stable which requires less strict conditions in handling. According to Townsend, “The 1H NMR spectrum of 2e′ (in toluene-d8 or C6D6; Figure 8) at 20 °C is virtually the same as the corresponding 1H NMR spectrum of 2e (Figure 7), consistent with acetonitrile not being bound strongly to the metal in solution at room temperature under these conditions.” Such labile adducts are expected to provide very similar catalytic performance to that of the parent complexes. The prior art Ondi complexes are electron deficient 14 electron species. Adding the acetonitrile adduct electrons would help this metal center achieve a more noble gas-like electron configuration increasing stability. Being crystalline also makes the adducts more stable than the amorphous solids when exposed to air. This is because the highly ordered, packed structure of crystalline solids provides greater resistance to interactions with atmospheric components like moisture and oxygen.
With respect to the limitation “LO- is racemic”, it is not clear if the stereochemistry shown in the compounds of Ondi above is absolute or relative. However, racemic ligand contains both the isomers, a genus of two compounds. Assuming the configuration were absolute at least one of the two isomers of the genus is disclosed in Ondi.
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. All claims are identical to or patentably indistinct from, or have unity of invention with claims in the application prior to the entry of the submission under 37 CFR 1.114 (that is, restriction (including a lack of unity of invention) would not be proper) and all claims could have been finally rejected on the grounds and art of record in the next Office action if they had been entered in the application prior to entry under 37 CFR 1.114. Accordingly, THIS ACTION IS MADE FINAL even though it is a first action after the filing of a request for continued examination and the submission under 37 CFR 1.114. See MPEP § 706.07(b). 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
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