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
This Office Action is responsive to the response to Election/Restriction and Amendment, filed 08/05/2026, wherein claims 12 and 51 were cancelled.
Claims 1-11, 13-16, 18, 21, and 50 are pending.
Priority
This application claims the following priority:
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Election/Restrictions
Applicant’s election without traverse of Group I, and the following species:
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, as the compounds of Formula I and 10, respectively, in the reply filed on 08/05/2026, is acknowledged.
The instantly claimed process utilizing the species:
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, is allowable over the prior art. The examination of the Markush claim has been extended. If a Markush grouping as set forth in a claim is proper and election of species has been required, the examiner must continue to search the species of the claim unless the claim has been found to be unpatentable over prior art. MPEP 803.02.
As detailed in the following prior art rejections, the generic claim encompassing the elected species was not found patentable. Therefore, the provisional election of species is given effect, the examination is restricted to the elected species only, and claims not reading on the elected species are held withdrawn. MPEP 803.02; Ex parte Ohsaka, 2 USPQ2d 1460, 1461 (Bd. Pat. App. lnt. 1987).
Should applicant, in response to this rejection of the Markush-type claim, overcome the rejection through amendment, the amended Markush-type claim will be reexamined to the extent necessary to determine patentability of the Markush-type claim. See MPEP 803.02.
Claims 2-3, 5-8, 15-16, 18, 21, and 50 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and subject matter, there being no allowable generic or linking claim.
Claims 1, 4, 9-11, and 13-14 are pending and examined on the merits herein.
Note: Though claims 7, 15 and 16 are withdrawn from consideration, in view of compact prosecution, it is noted that the claims do not properly narrow R1 and R2, as defined in instant claim 1; when R1 and R2 form a ring, claim 1 does not further recite R1 and R2as substituted, though it does define R1 and R2 as optionally substituted when R1 and R2 do not form a ring. However the ring formed by R1 and R2 in claims 7, 15, and 16, is substituted.
Claim Interpretation
The term “ring” in the definition of R1 and R2 in claims 1 and 4 is interpreted as a carbocyclic ring or a heterocyclic ring, wherein these rings are either aromatic or aliphatic.
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, 4, and 9-10, are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Brown-Wensley (Cp2TiCH2 Complexes in Synthetic Applications, published 1983, IDS of 12/05/2024).
Brown-Wensley teaches:
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(pg. 1736), wherein
in Formula I, X is the halogen Br, and R1 and R2are alkyl; in Formula 10, Y is CH2, and R1 and R2 are alkyl; and M is Br.
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.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 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.
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.
Claims 1, 4, and 9-11 are rejected under 35 U.S.C. 103 as being unpatentable over Brown-Wensley (Cp2TiCH2 Complexes in Synthetic Applications, published 1983, IDS of 12/05/2024).
Brown-Wensley is applied to claims 1, 4, and 9-10, as discussed above and incorporated herein.
While Brown-Wensley teaches the process of instant claim 1, it differs from that of instant claims 11 and 13, in that it does not specify a solvent.
Brown-Wensley teaches:
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as performed in the basic solvent, pyridine (pg. 1734).
Thus, it would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention, to select pyridine as the solvent in the reaction of Brown-Wensley, to arrive at instant claim 11. One of ordinary skill in the art would have been motivated to make such a selection, with a reasonable expectation of success, because Brown-Wensley teaches similar reactions that require a basic solvent as performed in pyridine.
As such, an ordinary skilled artisan would have reasonably expected pyridine, a basic solvent, to be used in the methods of Brown-Wensley to arrive at instant Formula I.
Claims 13-14 are rejected under 35 U.S.C. 103 as being unpatentable over Brown-Wensley (Cp2TiCH2 Complexes in Synthetic Applications, published 1983, IDS of 12/05/2024) as applied to claims 1, 4, and 9-11 above, and further in view of Law (Site Specifica Alkene Hydromethylation via Protonolysis of Titanacyclobutanes, published 2021, IDS of 12/05/2024).
Brown-Wensley is applied as discussed above and incorporated herein.
While Brown-Wensley teaches the method of instant claim 1, it differs from that of instants 13 and 14 in that it does not teach one the solvents of instant claim 13 or the treating step as performed at 0°C of instant claim 14.
Brown-Wensley teaches a treating step of the instant intermediate as performed at 0°C:
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(pg. 1739).
Law teaches a metathesis reaction between the titanium methylidene unveiled from Cp2Ti(µ-Cl)µ-CH2)AlMe2 (Tebbe’s reagent) and inactivated alkenes, wherein Cp2Ti(µ-Cl)µ-CH2)AlMe2 is a hydromethylation reagent (abstract; pg. 14360, 1st paragraph).
Law exemplifies the following hydromethylation reaction:
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(pg. 14360, Fig. 1);
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(pg. 14361, Table 1); and
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(pg. 14362, Scheme 3). See also Scheme 4, pg. 14363.
Thus, it would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention, to modify the method of Brown-Wensley, to select THF as the basic solvent and 0°C as the temperature of the treating step, to arrive at instant claims 13-14. One of ordinary skill in the art would have been motivated to make such selections, with a reasonable expectation of success, because:
-Brown-Wensley and Law are both directed toward hydromethylation of inactivated alkenes by combining an alkene with Cp2Ti(µ-Cl)µ-CH2)AlMe2 (Tebbe’s reagent),
-Brown-Wensley teaches a treating step of the instant intermediate performed at 0°C, and
- "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." MPEP 2144.05(II)
As such, an ordinary skilled artisan would have been motivated to make such selections, to predictably arrive at a method optimized to produce the first intermediate, and ultimately, Formula I:
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.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LAUREN WELLS whose telephone number is (571)272-7316. The examiner can normally be reached M-F 7:00-4:30.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, James (Jim) Alstrum-Acevedo can be reached on 571-272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LAUREN WELLS/Examiner, Art Unit 1622
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