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
Claims 1, 3, and 5 of K. Tamura, et al, US 17/058,221 (May 20, 2019) are pending, under examination on the merits and are rejected.
Election/Restrictions
Applicant previously elected Group (I), (claims 1-6) without traverse in the Reply to Restriction Requirement filed on March 7, 2024. Claims 7-18 to non-elected inventions of Groups (II) - (IV) are canceled by Applicant. The restriction/election requirement is maintained as FINAL.
Pursuant to the election of species requirement Applicant elected, without traverse, the species of:
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for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable. Claims 1, 3, and 5 read on the elected species. The elected species were searched and determined to be unpatentable as indicated in the § 103 rejection rejections below. The search/examination was not extended to additional species. MPEP § 803.02 (III)(C)(2). The provisional election of species requirement is given effect and no claims are withdrawn from consideration as not reading on the elected species. MPEP § 803.02(III)(A).
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution. See, MPEP § 2111.
Summary of the Claims
Independent claim 5 (which is narrower than independent claim 1) is summarized below.
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Where in the above scheme X is bromine. Note that in the above scheme, structures in brackets are undefined in the claims, but are drawn in by the Examiner based on the teachings of the specification, in order to better compare the claims to the prior art.
Interpretation of the Claim 1 and 5 Term “adding liquid B to liquid A”
The claim interpretation set forth in the previous Office action is repeated below for completeness, as the meaning “adding liquid B to liquid A” is a key issue.
Notably, independent claims 1 and 5 both require the limitation of “adding the liquid B to the liquid A”. The specification teaches that the step of “adding the liquid B to the liquid A” is advantageous. Specification at page 5, [0013]. The specification defines this phrase as follows:
Here, in the present invention, adding the liquid B to the liquid A refers to such an addition manner that the liquid B is little by little dividedly added to the total amount of the liquid A.
Specification at page 17, [0056]. In working Examples 1 and 2 (directed to the claimed addition method), the specification teaches that “liquid B was dropwise charged in the liquid A over 15 min at -80°C maintained” (Example 1, 84% yield) and “same operation as in Example 1, except for dropwise charging the liquid B to the liquid A at -10°C maintained” (Example 2, 70% yield). Specification at pages 67-70 (data in Table 1, page 73).
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Specification at pages 67-70 (data in Table 1, page 73).
In Comparative Examples 1 and 2, the same procedure was performed, “except for dropwise charging the liquid A to the liquid B” (the opposite of the claimed addition method) (Comparative Example 1, 65% yield; Comparative Example 2, 24% yield). Specification at pages 72(data in Table 1, page 73).
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Specification at pages 71 (data in Table 1, page 73).
The independent claim 1 and claim 5 phrase “adding liquid B to liquid A” is interpreted in accordance with the specification definition:
adding the liquid B to the liquid A refers to such an addition manner that the liquid B is little by little dividedly added to the total amount of the liquid A.
Specification at page 17, [0056].
In view of the foregoing, the claim limitation of “adding the liquid B to the liquid A” is broadly and reasonably interpreted, consistently with the specification, as requiring that portions (for example, pouring in or dropwise addition) of liquid B (which is the lithiated/deprotonated boranyl compound of claim 1 formula (2)) are added to a bulk liquid A (which is the compound of claim 1 formula (1)).
Maintained 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.
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 AIA 35 U.S.C. 103(a) 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, 3, and 5 and the elected species are rejected under 35 U.S.C. 103 as obvious over K. Tamura et al., 12 Organic Letters, 4400-4403 (2006) (“Tamura”) in view of W. Li et al., 67 Journal of Organic Chemistry, 5394-5397 (2002) (“Li”); N.G. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, “CHAPTER 5, Running the Reaction”, 113-143, (2000); and V. Gessner et al., 15 Chemistry, A European Journal, 3320-3334 (2009) (“Gessner”)
K. Tamura et al., 12 Organic Letters, 4400-4403 (2006) (“Tamura”)
Tamura teaches that chiral phosphine ligands have played an important role in transition metal-catalyzed asymmetric reactions, and numerous ligands have been designed and synthesized over the past four decades. Tamura at page 4400, col. 1.
Tamura teaches that that enantiopure 1,2-bis(tert-butylmethylphosphino)benzene (named BenzP*) (1) would exhibit excellent enantioselectivities high catalytic activities. Tamura at page 4400-4401, col. 2.
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Tamura demonstrates significant utility for, and motivates one of ordinary skill to explore methods of synthesizing BenzP*, because Tamura teaches that the optically active rhodium complex 4 derived from BenzP* is useful in asymmetric hydrogenations of prochiral substrates. Tamura at page 4402, Table 1.
Tamura teaches the following synthesis of above BenzP*.
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Tamura at page 4401, col. 1, Scheme 1; Experimental at pages S2-S4. Tamura Scheme 1 meets each and every limitation of claims 1 and 5 (and the elected species) regarding chemical structure and reagents employed. The first part of Tamura Scheme 1 meets each and every reagent/product limitation of claim 1 as well as the first part of claim 5 (“reaction step (A) of claim 5). The second part of Tamura Scheme 1 meets alternative reaction (B1) of claim 5.
The claim 1 and claim 5 concentration amendment of “the first mole larger than the second mole”:
Claims 1 and 5 . . . obtaining liquid B comprising a first mole of n-butyllithium and a second mole of an optically active phosphine borane compound obtained by deprotonating, the first mole larger than the second mole, an optically active hydrogen-phosphine borane compound . . .
is met by Tamura because Tamura employs 11 mmol of n-butyllithium and 10 mmol of (S)-tert-butylmethylphosphine–borane. Tamura at page S2.
Tamura further meets the claimed “optically active” limitations because (per the Scheme above, Tamura starts with enantiopure 2, isolates compound 3 in 99.8 %, and designates each chiral center as “R”.
Differences between Tamura and Claim 1 and 5
Tamura does not meet the claim 1 and claim 5 addition order and temperature-range limitations of:
Claims 1 and 5 . . . adding the liquid B to the liquid A at -20°C to 0°C . . .
because Tamura adds liquid A to liquid B (reverse of the claim 1 and claim 5 order) at -80 °C. See Tamura at page S2 “Preparation of (R)-2-(boranato-tert-butylmethylphosphino)bromobenzene (3)”. In sum, the sequence of reagent addition as well as the addition temperature (claimed -20 °C to 0 °C versus -80 °C) in the following step are the only differences between Tamura and claims 1 and 5:
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W. Li et al., 67 Journal of Organic Chemistry, 5394-5397 (2002) (“Li”)
Li teaches a study towards optimizing the synthesis of 3-pyridylboronic acid (3) based on the addition order of reactants 3-bromopyridine (1), triisopropyl borate (2) and n-butyl lithium, per Scheme 1. Li at page 5394, col. 2.
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Li at page 5395, Scheme 1. Li teaches that “the order of addition of the reagents was the key to a successful preparation”. Li at page 5394, col. 2.
Li teaches that when 3-bromopyridine was treated with n-butyllithium at -78 °C followed by triisopropyl borate (2), the product was isolated in poor yield (20-30%). Li at page 5394, col. 2.
Li teaches that the “reverse” addition procedure, in which 3-bromopyridine was added to a solution of n-butyllithium followed by addition of triisopropyl borate, gave better yields, but the reaction must be run at low temperatures (below -70 °C) in order to get consistent results, making it inconvenient for largescale preparation. Li at page 5394, col. 2.
In the experiment most relevant to the instant facts, Li teaches that adding n-butyllithium to a solution of 3-bromopyridine and triisopropyl borate followed by an acid quench was superior in that not only did it consistently afford good yields but it also proved to be temperature tolerant, giving the best yields (90-95%) at -40 °C and a respectable 80% yield even at 0 °C. Li at page 5394, col. 2.
This was probably because the lithium-halogen exchange on 3-bromopyridine is much faster than the reaction between n-butyllithium and triisopropyl borate. The 3-lithiopyridine intermediate thus generated reacts rapidly with the borate in the reaction mixture, thereby minimizing the chance for 3-lithiopyridine to undergo undesired side reactions.
Li at paragraph bridging page 5394 and 5395 (emphasis added).
In sum, Li teaches that having the electrophile present as the n-BuLi was added enabled high yields and the reaction to be run at a higher temperature than is normally used for a lithium-halogen exchange.
T. Rathman et al., 13 Organic Process Research & Development, 144-151 (2009) (“Rathman”)
In a review of optimization of organolithium reactions, Rathman teaches that order of addition organolithium reagents to an electrophile is an optimizable parameter. Rathman at pages 146-147 (“Order of Addition”)
N. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, “CHAPTER 5, Running the Reaction”, 113-143, (2000) (“Anderson”).
Anderson teaches that determining the optimal addition sequence of reagents is important. N.G. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, “CHAPTER 5, Running the Reaction”, 113-143, (2000) (see Anderson at page 114, Table 5.2; Id. at page 122 (“[t]he sequence of adding starting materials, reagents, and solvents usually must be optimized for each reaction”); Id. at page 128-129. Anderson teaches that the addition sequence may determine the primary reaction course or influence impurity formation. Anderson at page 128.
In one example, Anderson teaches that in the preparation of amide 42, a precursor to saquinavir (Figure 5.15), two addition sequences were investigated. Anderson at page 128. Anderson teaches that the preferred procedure was to add pivaloyl chloride (PivCl) to a solution of carboxylic acid 39 in EtOAc, followed by the addition of Et3N. Anderson at page 128. Anderson teaches that this cleanly generated the mixed anhydride 40, which reacted with L-asparagine (41) to afford 42 in 90% yield. When pivaloyl chloride was added to a solution of 39 and Et3N, some of the symmetrical anhydride 44 was generated, and coupling with 41 led to lower yields of 42 since only half of 44 can form the desired amide. The gist of Anderson is that, in some cases, the addition sequence is expected to affect the reaction parameters.
Anderson further teaches that reaction temperatures and reagent addition rates are important optimizable parameters. Anderson at pages 124-128.
V. Gessner et al., 15 Chemistry, A European Journal, 3320-3334 (2009) (“Gessner”).
Gessner teaches that due to the strongly polarized lithium–carbon bond, organolithium compounds are used as highly reactive nucleophiles and strong bases. Gessner at page 3321, col. 1.
Obviousness Rationale
Claims 1 3, and 5 and the elected species are obvious in view of Tamura for the following reasons.
The Claimed Addition Order “adding the liquid B to the liquid A” Is Obvious over the Cited Art
The claim 1 and 5 order-of-addition limitation “adding the liquid B to the liquid A at -20°C to 0°C” is obvious for the following reasons.
It is first noted that the case of obviousness is very strong because one of ordinary skill can readily envisage the claimed reaction addition order simply as the inverse of Tamura’s addition. MPEP § 2131.03(III) (citing Kennametal, Inc. v. Ingersoll Cutting Tool Co., 780 F.3d 1376, 1381, 114 USPQ2d 1250, 1254 (Fed. Cir. 2015) (quoting In re Petering, 301 F.2d 676, 681(CCPA 1962))). And one of ordinary skill is apprised that sequence of reagent addition is an optimizable, result-effective parameter. See Li, Rathman and Anderson as discussed above.
One of ordinary skill seeking 1,2-bis(tert-butylmethylphosphino)benzene (named BenzP*) (1), in view of its catalytic utility in asymmetric synthesis as taught by Tamura, is motivated to modify/investigate the method of Tamura by reversing the order of addition; i.e., by adding the THF solution of deprotonated (S)-tert-butylmethylphosphine–borane to the THF solution of o-dibromobenzene thereby arriving at optically active (6). One of ordinary skill is so motivated because such modification represents suitable alternative order of addition of regents. MPEP § 2144.04 (IV)(C).1 Alternatively, one of ordinary skill is motivated to optimize Tamura by investigating the sequence of addition as taught by Li, Rathman, and Anderson. MPEP § 2144.05(II). For example, one of ordinary skill (apprised of the high reactivity of lithiated organics by Gessner and Li) is motivated to investigate reversing the order of addition (as taught Li, Rathman, and Anderson) and slowly add cooled reactive lithiated compound (2) (liquid B) (for example dropwise addition) to the dibromobenzene (liquid A) so that cooled, reactive lithiated 2 is consumed as it is added (rather than Tamura’s addition order where the bulk of unreacted lithiated intermediate is present in the reaction mixture). Based on the teachings of Li and Gessner, one of ordinary skill would reasonably postulate that in this manner, the concentration of the highly reactive lithiated anion (i.e., compound (2)/liquid B) within the reaction mixture would be lower over time than in the Tamura addition order. One of ordinary skill could reasonably expect that under such reverse-order conditions, a lower reaction-mixture concentration of the reactive lithiated intermediate may lead to fewer side products and/or higher yield similar to the teachings of Li. MPEP § 2144.05(II) citing In re Williams, 36 F.2d 436, 438 (CCPA 1929); In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). When making a determination of obviousness should be on what a person of ordinary skill in the pertinent art would have known at the relevant time, and on what such a person would have reasonably expected to have been able to do in view of that knowledge; regardless of whether the source of that knowledge and ability was documentary prior art, general knowledge in the art, or common sense. MPEP § 2141(II) (discussing the flexible approach of KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007)). Here, one of ordinary skill would reasonably consider the concentration of the reactive lithiated intermediate in the reaction mixture.
The Claimed Addition Temperature Range “-20°C to 0°C” Is Obvious Over the Cited Art
The claim 1 and 5 addition-temperature limitation “adding the liquid B to the liquid A at -20°C to 0°C” is obvious for the following reasons.
Tamura effectively teaches reaction temperature range of -80 °C to 0 °C, which overlaps with the claimed temperature range of “-20°C to 0°C”. That is, Tamura’s addition temperature and subsequent temperature elevation is shown by the following paragraph in Tamura:
Preparation of (R)-2-(boranato-tert-butylmethylphosphino)bromobenzene (3)
To a solution of (S)-tert-butylmethylphosphine–borane (1.18 g, 10 mmol) in THF (10 mL) was added n-butyllithium (7.0 mL of 1.57 M hexane solution, 11 mmol) at –80 °C under argon. To the resulting solution was added a solution of o-dibromobenzene (3.54 g, 15 mmol) in THF (5 mL) during 15 min. The bath temperature was gradually elevated to 0 °C during 2 h . . .
Tamura at page S2 (emphasis added).2 Generally, 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. MPEP § 2144.05(II)(A) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.)). Here, one of ordinary skill in the art is motivated to develop workable or optimum ranges for addition temperature, where Applicant can rebut a prima facie case of obviousness by showing the criticality (unexpected result) of the range. MPEP § 2144.05; see also, In re Boesch, 617 F.2d 272,276 (CCPA 1980); In re Aller, 220 F.2d 454, 456 (CCPA 1955). Here, respecting the highly reactive lithiated intermediate (liquid B), addition temperature is clearly a result-effective variable as taught by Li. One of skill in the art it motivated to balance the costs benefit of lower addition temperatures versus higher (perhaps at the cost of selectivity). For example, while one of ordinary skill may reasonably expect a lower yield at the claimed addition temperature of -20 °C, such may be offset by the costs (equipment availability/costs and power costs) of maintaining Tamura’s -80 °C addition temperature. One the other hand, one of ordinary skill may reasonably expect to mitigate yield losses by slower addition of one cooled reagent to the other.
Further, one of ordinary skill is motivated to investigate reaction-mixture temperature with respect to a change in addition order because Li teaches that having the electrophile present as the n-BuLi was added enabled high yields and the reaction to be run at a higher temperature than is normally used for a lithium-halogen exchange. Li at page 5394, col. 2. Li teaches that the “reverse” addition procedure, in which 3-bromopyridine was added to a solution of n-butyllithium followed by addition of triisopropyl borate, must be run at low temperatures (below -70 °C) in order to get consistent results, making it inconvenient for largescale preparation. Li at page 5394, col. 2.
The point is that one of ordinary skill apprised by Tamura of the general reaction is free to develop workable temperature and addition protocols.
APPLICANT’S ARGUMENT
(I) Applicant’s Argument Respecting Addition Temperature
Applicant argues that with respect to amended claims 1 and 5 in this Response, the Examiner's previous reasons to maintain the rejections are not applicable. Reply at page 8. Applicant argues that Tamura expressly teaches that a solution of o-dibromobenzene (i.e., liquid A) is added at -80 °C to a solution of (S)-tertbutylmethylphosphine-borane (1.18 g, 10 mmol) and n-butyllithium (i.e., liquid B). Id.
Applicant presents the following Table comparing the claimed temperature/addition order versus the prior art (Tamura) addition order of comparative Examples 1 and 2.
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Reply at page 9. Applicant notes that in Examples 2 and 5 and Comparative Example 2, the addition temperature was at -10°C. Applicant further notes that in comparing these examples, it was found that Examples 2 and 5 showed about the improvements in the yield by about three times (70-72% vs. 24%). Applicant argues that the yields of 70-72% (Examples 2 and 5 at -10 °C) are well acceptable for one skilled in the art in exchange of adopting a higher temperature of -10°C. Applicant argues that the addition condition of a temperature of -10°C is significantly easily handled compared with maintaining a temperature of -80°C.
Applicant argues that there is no reasonable basis for one skilled in the art to raise the addition temperature taught by Tamura (i.e., -80 °C) to within the claimed range of -20 °C to 0 °C since one of ordinary skill would expect a significant yield decrease; and that it is common knowledge in the relevant art that yield and/or optical purity would decrease if increasing a reaction temperature. Reply at page 10.
Examiner Response Respecting Addition Temperature
This argument is not persuasive for the following reasons. Applicant has not cited any evidence (e.g., prior art) supporting the proposition one of ordinary skill would expect a significant yield decrease upon raising Tamura’s addition temperature from -80 °C to within the claimed range of -20 °C to 0 °C. MPEP § 2145(I) (citing In re Geisler, 116 F.3d 1465, 43 USPQ2d 1362 (Fed. Cir. 1997) “[a]n assertion of what seems to follow from common experience is just attorney argument and not the kind of factual evidence that is required to rebut a prima facie case of obviousness”). Here, Applicant’s specification results, as summarized in the above table, are not available to one of ordinary skill seeking to optimize Tamura.
Further, one of ordinary skill is motivated to investigate reaction-mixture temperature with respect to a change in addition order because Li teaches that having the electrophile present as the n-BuLi was added enabled high yields and the reaction to be run at a higher temperature than is normally used for a lithium-halogen exchange. Li at page 5394, col. 2. Li teaches that the “reverse” addition procedure, in which 3-bromopyridine was added to a solution of n-butyllithium followed by addition of triisopropyl borate, must be run at low temperatures (below -70 °C) in order to get consistent results, making it inconvenient for largescale preparation. Li at page 5394, col. 2.
Examiner Response -- Applicant’s Proffered Results do not Overcome the § 103 Rejection
The results of the above Table were previously argued by Applicant as unexpected. Reply filed June 9, 2025.
(i) Applicant Has not Met Its Burden of Demonstrating that the Proffered Results are Unexpected
The proffered results are not persuasive to overcome the § 103 rejection for the following reasons. Applicant’s proffered results show that claimed addition order clearly results in a higher yield of desired product (3) at both -80 °C and -10 °C, with the result being more striking at lower temperatures (i.e., -10 °C). However, any differences between the claimed invention and the prior art may be expected to result in some differences in properties. MPEP § 716.02. The issue is whether the properties differ to such an extent that the difference is really unexpected. MPEP § 716.02 (citing In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) (differences in sedative and anticholinergic effects between prior art and claimed antidepressants were not unexpected)).
Here, the differences in percent yields between the claimed invention and the prior art is one of degree, where one of ordinary skill would expect different addition sequences to give a different percent yield. Differences of degree are not as persuasive as a difference in kind – i.e., if the range produces ‘a new property dissimilar to the known property,’ rather than producing a predictable result but to an unexpected extent. MPEP § 716.02 (citing UCB, Inc. v. Actavis Labs, UT, Inc., 65 F.4th 679, 693, 2023 USPQ2d 448 (Fed. Cir. 2023)).
The sequence of reagent addition is a result-effective, optimizable parameter that may affect reaction yield. Li at page 5394, col. 2; N.G. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, “CHAPTER 5, Running the Reaction”, 113-143, (2000) (see Anderson at page 114, Table 5.2; Id. at page 122 (“[t]he sequence of adding starting materials, reagents, and solvents usually must be optimized for each reaction”). One of ordinary skill would expect that reagent addition order can affect the reaction’s percent yield. For example, under the instant facts, one of ordinary skill (apprised of the high reactivity of lithiated organics by Gessner) has an expectation that handling of such highly reactive intermediate (including addition order) may be important. For instance, considering reversing the order of addition (as taught generally by Anderson) and slowly add reactive lithiated compound (2) (liquid B) (for example dropwise addition) to the dibromobenzene (liquid A) so that lithiated 2 is consumed as it is added. One of ordinary skill would reasonably postulate that in this manner, the concentration of the highly reactive lithiated anion (i.e., compound (2)/liquid B) within the reaction mixture would be lower over time than in the Tamura addition order. One of ordinary skill could reasonably postulate that under such reverse-order conditions, a lower reaction-mixture concentration of the reactive lithiated intermediate may lead to fewer side products and/or higher yield.
Further, the facts established by rebuttal evidence must be evaluated along with the facts on which the conclusion of a prima facie case was reached, not against the conclusion itself. MPEP § 716.01(d) (citing In re Eli Lilly, 902 F.2d 943, 14 USPQ2d 1741 (Fed. Cir. 1990)). In other words, each piece of rebuttal evidence should not be evaluated for its ability to knockdown the prima facie case. MPEP § 716.01(d). All of the competent rebuttal evidence taken as a whole should be weighed against the evidence supporting the prima facie case. MPEP § 716.01(d). Although the record may establish evidence of secondary considerations which are indicia of nonobviousness, the record may also establish such a strong case of obviousness that the objective evidence of nonobviousness is not sufficient to outweigh the evidence of obviousness. MPEP § 716.01(d) (citing Newell Cos. v. Kenney Mfg. Co., 864 F.2d 757, 769, 9 USPQ2d 1417, 1427 (Fed. Cir. 1988)).
Here, the case of obviousness is very strong because one of ordinary skill can readily envisage the claimed reaction addition order.
Here, weighing/balancing: (1) the strong case of; (2) the strong motivation to improve the synthesis of the subject compound; (3) the highly reactive nature of the lithiated reactant/intermediate involved, which provides a focus point to one of ordinary skill; (4) the expectation that reagent order addition may affect the yield; and (5) the limited choices available with respect to reagent order addition, versus the degree of respective yield improvements at -80 °C and -10 °C, the conclusion is that the evidence of obviousness outweighs the objective evidence proffered. MPEP § 716.01(d). Although the record may establish evidence of secondary considerations which are indicia of nonobviousness, the record may also establish such a strong case of obviousness that the objective evidence of nonobviousness is not sufficient to outweigh the evidence of obviousness. MPEP § 716.01(d) (citing Newell Cos. v. Kenney Mfg. Co., 864 F.2d 757, 769, 9 USPQ2d 1417, 1427 (Fed. Cir. 1988)).
(ii) Applicant Has not Met Its Burden of Demonstrating that the Proffered Results are Commensurate with Claim Scope
The proffered results do not facially appear commensurate in scope with the claims. The claims are directed to reaction of the genus of formula (1) with the genus of deprotonated formula (2) (where the deprotonation does not limit the cation counterion of formula (2)). However, the proffered results are directed to a single species of each claimed formula, in a single solvent, where lithium is the counter cation to the species of formula (2). The claimed subject matter is considerably broader in scope than the proffered species. The burden is on Applicant to establish unexpected results. MPEP § 716. Here, it is not readily apparent, nor has Applicant offered and explanation of how the proffered results (directed to a single species) and single claimed temperature of -10 °C are reasonably expected by one of ordinary skill to occur over the entire claimed range of compounds, solvents and counter cations and claimed temperature range of -20 °C to 0 °C. MPEP § 716.02(d).
Conclusion
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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 MPEP § 2144.04 (IV)(C) (citing 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 re Burhans, 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.).
2 In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I) (citing In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976)).