DETAILED ACTION
Claims 1-3 and 5-6 are currently pending in the instant application.
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 .
Response to Arguments
Applicant’s arguments in a response filed 04/13/2026 have been fully considered and entered into the application. Applicant has overcome
The 35 U.S.C. 103 rejection of claims 1-3 over Sharutin et al.
Regarding the 35 U.S.C. 103 rejection of claims 1-2 and 5-6 over Barton et al, Applicant argues that Barton tails to teach or suggest each and every element of the claims. However, the rejection was made under 35 U.S.C. 103 rather than 35 U.S.C. 102 so the prior art does not need to teach or suggest each and every element of the claims. Rather, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains, then the claim will be rejected under 35 U.S.C. 103.
Further Applicant argues that Barton teaches adding the Grignard reagent (nucleophile) to the diarylbismuth chloride (electrophile) rather than adding the electrophile (diarylbismuth chloride) to the nucleophile (organometal nucleophile). MPEP 2144, Section IV, C states that changes in sequence of adding ingredients would be considered an obvious modification. Ex parte Rubin, 128 USPQ 440 (Bd. App. 1959) (Prior art reference disclosing a process of making a laminated sheet wherein a base sheet is first coated with a metallic film and thereafter impregnated with a thermosetting material was held to render prima facie obvious claims directed to a process of making a laminated sheet by reversing the order of the prior art process steps.). See also In reBurhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) (selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results); In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930) (Selection of any order of mixing ingredients is prima facie obvious.).
Applicant further argues that the amount of nucleophile to bismuth compound has not been recognized as a result-effective variable for controlling dismutation in the synthesis of a heteroleptic triarylbismuthane. However, the instant claims are drawn to “a method of controlling dismutation”. Dismutation is defined in the Specification as “a chemical reaction where a molecule is transformed into two or more dissimilar products”. Cambridge dictionary (see https://dictionary.cambridge.org/dictionary/english/control#google_vignette) defines control as “decide or strongly influence the particular way in which something will happen or someone will behave”. In a chemical reaction, one would expect that varying the amount of starting materials would directly influence the amount of product as a basic chemical principle. Specifically, according to https://www.acs.org/middleschoolchemistry/lessonplans/chapter6/lesson2.html, changing the amount of reactants affects the amount of products produced in a chemical reaction. Thus varying the ratio of the reactants, in the instant case, the bismuth compound and nucleophile, would be expected to influence dismutation – transformation of a molecule into two or more dissimilar products (aka the chemical reaction). Thus, the prior art meets the limitations of influencing a chemical reaction where a molecule is transformed into two or more dissimilar products. As a result, the 35 U.S.C, 103 rejection of claims 1-2 and 5-6 in view of Barton have been maintained.
Regarding the 35 U.S.C. rejection of claims 1-3 over Barton in view of Sharutin, Applicant argues that tosylates unexpectedly provide a selective higher yield process over chlorides and cites Table 1 as evidence, in particular entries 6 and 16. Table 1 is reproduced below:
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284
360
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. As entries 2 and 13 show, having a toslyate rather than a chloride leaving group results in a lower not a higher yield. Thus, Applicant’s statement that toslyates unexpectedly provide a selective, high yield process over chlorides cannot be extrapolated over the entire breadth of the instant claims. MPEP 716.02(d) states whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). As applicant has not shown the unexpected results occur commensurate in scope with the instant claims, the 35 U.S.C. 103 rejection of claims 1-3 over Barton in view of Sharutin have been maintained.
Regarding the 35 U.S.C. 103 rejection of claims 1-2 and 5-6 over Gilman et al, Applicant utilizes the same arguments as applied to Barton et al as well as the 35 U.S.C. 103 rejection of Gilman in view of Sharutin. As these arguments have been addressed above, they have not been repeated for the sake of brevity. The rejections utilizing Gilman et al have been maintained.
Maintained 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 (i.e., changing from AIA to pre-AIA ) 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.
Claims 1-2 and 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Barton et al (see Tetrahedron, 1986, Vol 42, No. 12, p. 3111-3122, see IDS filed 06/24/2022).
Barton et al teach synthesis of di-p-tolylphenyl bismuth from di-p-tolylbismuth chloride (4.8 g = 11.2 mmol) and phenylmagnesium bromide from bromobenzene (1.76 g = 11.2 mmol) and magnesium (0.28 g = 11.5 mmol) - see p. 3119. Although Barton et al does not teach a substoichimetric amount of the arylbismuth precursor relative to the nucleophile, it would be obvious to vary the amount of bismuth compound to the nucleophile (i.e. phenylmagnesium bromide) to optimize the yield of the process. According to MPEP 2144.05, Section II, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. “[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 citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Claims 1-3 are rejected under 35 U.S.C. 103 as being unpatentable over Barton et al (see Tetrahedron, 1986, Vol 42, No. 12, p. 3111-3122, see IDS filed 06/24/2022) in view of Sharutin et al (see Russian Journal of General Chemistry, 2002, Vol. 72, No. 12, p. 1925-1926).
The teachings of Sharutin et al are described in the above 103 rejection. Regarding the use of R2 as a tosyl group, Barton et al teach a chloro group instead. However Sharutin et al teaches that reaction of a diarylbismuth precursor having a tosyl group as a leaving group with an organometal nucleophile is known. Thus, a chloro and tosyl group would be considered equivalents as they both function as leaving groups and it would have been prima facie obvious to substitute one for the other. See MPEP 2144.06.
Claims 1-2 and 5-6 are rejected under 35 U.S.C. 103 as being unpatentable over Gilman et al (see J. Am. Chem Soc, 1941, Vol. 63, No. 1, p. 207-211).
Gilman et al teach the reaction diphenylbismuth chloride (0.01 mol) with α-naphthylmagnesium bromide (0.01 mol) to give diphenyl-α-naphthylbismuth. Although Gilman et al et al does not teach a substoichimetric amount of the arylbismuth precursor relative to the nucleophile, it would be obvious to vary the amount of bismuth compound to the nucleophile (i.e. α-naphthylmagnesium bromide) to optimize the yield of the process. According to MPEP 2144.05, Section II, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. “[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 citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Claims 1-3 are rejected under 35 U.S.C. 103 as being unpatentable over Gilman et al (see J. Am. Chem Soc, 1941, Vol. 63, No. 1, p. 207-211) in view of Sharutin et al (see Russian Journal of General Chemistry, 2002, Vol. 72, No. 12, p. 1925-1926).
The teachings of Sharutin et al are described in the above 103 rejection. Regarding the use of R2 as a tosyl group, Gilman et al teach a chloro group instead. However Sharutin et al teaches that reaction of a diarylbismuth precursor having a tosyl group as a leaving group with an organometal nucleophile is known. Thus, a chloro and tosyl group would be considered equivalents as they both function as leaving groups and it would have been prima facie obvious to substitute one for the other. MPEP 2144.06.
Conclusion
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.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623
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