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, 8, 17-21, and 32-37 of H. Gulyás, US 17/999,197 (May 27, 2021) are pending. Claims 18-21, drawn to non-elected invention of Group (III), are withdrawn from consideration pursuant to 37 CFR 1.142(b). Claims 1, 8, 17, and 32-37 are under examination on the merits and are rejected.
Election/Restrictions
Applicant elected Groups (I)/(II)1, now claims 1, 8, 17, and 32-37, without traverse in the Reply to Restriction Requirement filed on December 1, 2025. New claims 32-37 are added to the elected Group. Claims 18-21, to the non-elected invention of Group (III), are maintained as withdrawn from consideration pursuant to 37 CFR 1.142(b). The restriction/election requirement is maintained as FINAL. Pursuant to the election of species requirement Applicant elected, without traverse, the species of:
PNG
media_image1.png
200
400
media_image1.png
Greyscale
for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable.
Claims 1, 8, 17, and 32-37 of elected Group (I)/(II) read on the elected species. The elected species was searched and determined to be obvious pursuant to § 103. The search/examination was not extended. MPEP § 803.02 (III)(C)(2). The provisional election of species requirement is maintained in effect and no claims are withdrawn from consideration as not reading on the elected species.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 as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. Claim interpretation is updated here, from the previous Office action, in view of the amendments.
Interpretation of “stability constant”
Claims 1 and 17 recite “stability constant” in the following context:
Claims 1 and 17 . . . wherein complexes of formula I having a stability constant in the range of from 5 L*mol-1 to 250,000 L *mol-1 when measured at 298 K and when the complex of formula I is dissolved in the solvent,
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
Claim 8 further narrows the claim 1 stability constant range.
The specification teaches that Schrock-type molybdenum or tungsten alkylidene olefin metathesis catalysts frequently lack air stability which makes them more difficult to handle and often restricts their usefulness or so air stable that the active catalyst must be released by exposure to a Lewis acid. Specification at pages 1-2, [0002]-[0004]. The specification further teaches that the Schrock-alkylidene complexes of formula I having a stability constant in the range of from 5 L *moI-1 to 250,000 L *mo1-1, are both air-stable and catalytically active in an olefinic metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid. Specification at page 4, [0013] (emphasis added).
The specification indicates that the stability constant is obtained by studying the equilibrium between the active 14-electron species and its 18-electron phenanthroline adduct, then fitting the data to equations (which equations are not disclosed in the instant specification) to solve for the formation constant (K):
[0010] . . . Thus, this finite stability constant K serves in a selected solvent for an equilibrium between the 18-electron complex comprising the bidentate ligand and which is not active in an olefinic metathesis reaction, and the 14-electron complex from which the bidentate ligand has been released by dissociation, wherein the 14-electron complex is catalytically active in an olefinic metathesis reaction.
Specification at pages 3-4, [0010] (emphasis added).
The specification teaches that the stability constant can be determined according to known methods employing the law of mass action.
[0044) The term "stability constant" is synonymously used with the term "association constant". It is the inverse of the dissociation constant. Terms such as "binding constant" and "formation constant" may also synonymously be used for the term "stability constant".
[0045] K can be determined according to known methods employing the law of mass action.
[0046] Suitable solvents preferably are organic aromatic solvents such as benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons such as dichloromethane or trichloromethane, or the substrate to be metathesized.
Specification at page 16, [0044].
In a representative working example, the specification (without giving the equations used, or showing the math) teaches the following stability constants K (at 298K in solvent d6-benzene using 1HNMR) regarding the equilibrium between claimed complexes 20-23 and compounds 16-19 disassociated from the 1,10-phenanthroline.
PNG
media_image2.png
200
400
media_image2.png
Greyscale
20 R = methyl, R' = H; K20, d6-benzene, 298K = 3281 M-1
21 R = ethyl, R' = H; K21, d6-benzene, 298K = 577 M-1
22 R = cyclopropyl, R' = CH3; K22, d6-benzene, 298K = 615 M-1
23 R = phenyl, R' = H; K23, d6-benzene, 298K = 255 M-1
Specification at page, [0098]. As can be seen, significant changes occur in the stability constant by changing variable R.
Similarly, and more generally, the art teaches that the stability constant is an experimental quantity, specific to the particular solvent, describing the thermodynamics of metal-ion binding with various (in)organic ligands, or biomolecules; that is, the equilibrium constant for the formation of a complex between the metal ion and ligand in solution. O. Gutten et al., 52 Inorganic Chemistry, 10347-10355 (2013) (“Gutten”), see Abstract; page 10437, col. 1.
In view of the foregoing, the claim 2 term “stability constant K” is reasonably interpreted, consistently with the specification, as the equilibrium constant between the claimed 18-electron complex of the formula I and the 14-electron complex that results from dissociation of the 1,10-phenanthroline ligand (claim 1 variable D), when equilibrated in a particular solvent at 298K. The solution ratios of complexes can be determined by art-known methods (e.g., 1HNMR as taught in the instant specification) and then the “stability constant K” may be obtained by plugging the concentration values into art-known equations.
Withdrawal Objections/Rejections
Any objection/rejection made in the previous Office action that is not specifically addressed, maintained or restated in modified form (in view of Applicant’s amendments) is withdrawn.
Withdrawal Claim Rejections - 35 USC § 102 (AIA )
Rejection of claims 1 and 8 under 35 U.S.C. 102(a)(1)/(2) as being anticipated by G. Frater et al, WO 2016/142849 (2016) (“Frater”) is withdrawn in view of Applicant’s amendments, for the following reasons.
Frater discloses complexes that fall within the scope of claimed formula I. For example, Frater discloses the following complexes III-VI. Frater at page 3.
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Frater at page 3. The above Frater complexes fall squarely within the claim 1, formula (I). However, Frater teaches that the active catalytic species is liberated from these compounds by de-complexing the 1,10-phenanthroline ligand with zinc chloride:
The catalysts are generated in situ from the compounds of Formula II by art-recognised methods, such as the addition of Lewis acids, typically zinc chloride.
Frater at page 4, lines 11-12 (emphasis added). Thus, Frater does not teach these species are themselves catalytically active and the Examiner has no means to determine whether Frater’s compounds meet the claim 1 functional limitation of:
Claims 1 . . . are . . . catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating . . .
Indeed, Frater’s compounds may have some modicum, however slight, of catalytic activity, for example, with a very reactive olefin substrate. However, as set forth in the § 112(a) rejection below, neither the art of record nor the specification provides a correlation between the structure of the claimed compounds of formula I and their olefin metathesis activity allowing the Examiner to make this determination, one way or another.
Maintained Specification Objections
The specification is objectionable because the text of certain drawings/equations is too faint and/or pixilated to the extent that it will not be transcribable by the publication division in an issued patent. Applicant is required to provide clearer depictions of the following equations, such that all atoms, bonds, and text under/over the arrows as well as accompanying subtext can be clearly discerned: at page 23, [0092]; page 24, [0098]; page 25, [00102]; page 26, [00107]; page 34, [00149]; page 35, [00152]; and page 36, [00155]. For example, the subtext of the equation at page 24, [0098] was incorrectly transcribed in the published application, US 2023/0203072 (2023) at page 9. A larger font size for the subtext is recommended.
Applicant’s Arguments
Applicant argues that paragraphs 92, 98, 102, 107, 149, 152, and 155 have been amended and it is believed that the chemical formulas in these paragraphs are now more legible.
This argument is not persuasive because the amended specification pages still appear too faint and/or pixilated to the extent that they will not be transcribable by the publication division in an issued patent. If such cases are allowed, they are subsequently returned to the Examiner’s docket and present logistical difficulties in issuing the corresponding patent.
Maintained and New Rejections 35 U.S.C. 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION. — The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000). The meaning of every term used in a claim should be apparent from the prior art or from the specification and drawings at the time the application is filed. Claim language may not be ambiguous, vague, incoherent, opaque, or otherwise unclear in describing and defining the claimed invention. MPEP § 2173.05(a).
Unclear Claim term “stability constant K”
Claims 1, 8, 17, and 32-37 are rejected under 35 U.S.C. 112(b) as being indefinite because the numerical value of “stability constant” is manipulatable under the general recitations of independent claims 1 and 17; that is, it cannot be unambiguously determined for a particular formula I metal complex. MPEP § 2173.05(g).
A functional limitation must be evaluated and considered, just like any other limitation of the claim, for what it fairly conveys to a person of ordinary skill in the pertinent art in the context in which it is used. MPEP § 2173.05(g). The use of functional language in a claim may fail "to provide a clear-cut indication of the scope of the subject matter embraced by the claim" and thus be indefinite. MPEP § 2173.05(g).
Claims 1 and 17 have been amended to recite “stability constant” in the following functional context:
Claims 1 and 17 . . . wherein complexes of formula I having a stability constant in the range of from 5 L*mol-1 to 250,000 L *mol-1 when measured at 298 K and when the complex of formula I is dissolved in the solvent,
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
Claim 8 further narrows the claim 1 stability constant range.
Before discussing the central issue, the amendments raise additional 112(b) concerns. With respect to claim 1 (and its dependents), the above bolded claim 1 recitation of “the solvent” lacks antecedent basis because no earlier “a solvent” is recited or required in the claim 1 “composition”. MPEP § 2173.05(e). Furthermore, as bolded above, claim 1 recites that the solvent can be “the substrate to be metathesized” but there is no earlier recitation of any substrate in claim 1. MPEP § 2173.05(e). Moreover, it is unclear what the such “substrate to be metathesized” is since its identity will vary depending on what substrate the claim practitioner chooses (in the mind) to metathesize using the composition of claim 1 as a catalyst. 2 This reasoning does not apply to independent claim 17 because the composition of claim 17 requires “a solvent” and the solvent can be the “substrate to be metathesized”.
The primary § 112(b) issue is as follows. As discussed in Claim interpretation above, the numerical value of the stability constant for a particular composition depends upon the experimental conditions, particularly the solvent and concentration of the complex of formula I. The subject claims, however, leave open the concentration conditions and recite alternative solvents.
The claim term “stability constant” was interpreted above as the equilibrium constant between the claimed 18-electron complex of the formula I (which and the 14-electron complex that results from dissociation of the 1,10-phenanthroline ligand (claim 1 variable D), when equilibrated in a solvent at 298K. However, because the “stability constant” is an equilibrium constant, its numerical value depends upon the solvent as well as the initial concentration of the claimed 18-electron complex of the formula I. See Gutten at page 10349, col. 1 (indicating that the stability constant varies with concentration); see also, T. Djekic et al., 312 Applied Catalyst A: General, 144-152 (2006) at Abstract (“The ratios between different species are defined by the stability constants, which are influenced by different parameters such as the type of metal, ligand, counter ion or solvent”); Id at page 146, col. 1 (“The influence of metal, ligand, counter ion, solvent and concentration on the stability constant values is discussed”).
The instant specification itself teaches that concentration affects the stability constant. Specification at page 23, [0094]-[0095]. The instant specification itself also teaches that solvent identity affects the stability constant. Specification at page 25, [00102]-[00103]. For example, with respect to the instantly elected species (specification complex 25), the specification teaches that:
[00103] Complex 25 is autoactivating, and its stability constant heavily depends on the nature of the solvent. Under similar conditions, it dissociates considerably more readily in CDCl2 than in C5D5. In CDCl3 the dissociation is even more favored, below 0.01M concentration, at room temperature, the active MAP complex practically is completely liberated as shown by the stability constants in Scheme 3.
Specification at page 25, [00103] (emphasis added).
Here, one of ordinary skill, seeking to determine infringement of claims 1 and 17 (or their dependents) can arrive at different numerical values of “stability constant” by varying either the solvent, the concentration of the claimed 18-electron complex of the formula I, or both. This is because claims 1 and 17 permit a choice of solvent in the test and provides no limitation on concentration:
Claims 1 and 17 . . . wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
and do not specify the concentration of the formula (I) metal complex being tested. As such, infringement (or whether a prior art compound falls within the genus of claims 1 and 17) may not be unambiguously determined in some cases because claims 1 and 17 can have different numerical interpretations for the “stability constant”. MPEP § 2173.05(b).
Applicant’s Argument
Applicant argues that the rejection should be withdrawn because the condition and meaning of "stability constant" as now recited in amended independent claims 1 and 17 is clear and definite.
This argument is not persuasive because one of ordinary skill, seeking to determine infringement of claims 1 and 17 (or their dependents) can arrive at different numerical values of “stability constant” by varying either the solvent, the concentration of the claimed 18-electron complex of the formula I, or both.
This is because claims 1 and 17 permit a choice of solvent in the test:
Claims 1 and 17 . . . wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
and do not specify the concentration of the formula (I) metal complex being tested. As such, infringement (or whether a prior art compound falls within the genus of claims 1 and 17) may not be unambiguously determined in some cases because claims 1 and 17 can have different numerical interpretations for the “stability constant”. MPEP § 2173.05(b). Stated differently, a particular formula I metal complex’s stability constant may fall within the claimed range when the solvent is benzene but not fall within the claimed range using, for example, any of dichloromethane, carbon tetrachloride or perfluoronaphthalene (all chlorinated hydrocarbons). Thus, the claims may have mutually exclusive interpretations.
Unclear Claim term “air stable”
Claims 1, 8, 17, and 32-37 are rejected under 35 U.S.C. 112(b) as being indefinite because the meaning of “air stable” is unclear.
Claims 1 and 17 . . . wherein complexes of formula I . . .
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
The specification does not define “air stable”. The plain meaning of “air stable” is that a tested formula I complex undergoes no decomposition in air. MPEP § 2111. However, the specification teaches that even the elected species (specification compound 25) undergoes some decomposition in air, stating that “5-10 % decomposition was observed in 5 days”. Specification at page 26, [00104]. Thus, the gist of the specification is that complexing Schrock-type catalysts with 1,10-phenanthroline improves air stability over the noncomplexed species, it does not render the catalysts completely “air stable” per se. Thus, the claim term “air stable” is broadly and reasonably interpreted, consistently with the specification, as a subjective term. MPEP § 2173.05(a)(IV). Here, the term “air stable” is indefinite because the specification does not provide an objective standard for measuring the scope of this term. MPEP § 2173.05(a)(IV). The specification does not provide an objective boundary for measuring whether a particular complex, otherwise falling within the scope of claim 1, formula I is “air stable”. MPEP § 2173.05(a)(IV). Dependent claims 8, 17, and 32-37 do not cure the issue.
Maintained Claim Rejections 35 U.S.C. 112(a) – Written Description
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
For an originally filed claim, 35 U.S.C. 112(a) requires that the specification shall contain a written description of the invention demonstrate that the inventor was in possession of the invention that is claimed.3 MPEP § 2163(I); MPEP § 2163(II)(A)(3)(a). Possession may be shown by disclosure of drawings or structural chemical formulas that show that the invention was complete. MPEP § 2163(I).
The written description requirement for a claimed chemical genus may be satisfied through sufficient description of a representative number of species by actual reduction to practice, reduction to drawings, or by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the inventor was in possession of the claimed genus. MPEP § 2163(II)(A)(3)(a)(ii).
A "representative number of species" means that the species which are adequately described are representative of the entire genus. MPEP § 2163(II)(A)(3)(a)(ii). Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus. MPEP § 2163(II)(A)(3)(a)(ii) (citing AbbVie Deutschland GmbH & Co., KG v. Janssen Biotech, Inc., 759 F.3d 1285, 1300, 111 USPQ2d 1780, 1790 (Fed. Cir. 2014).
Disclosure of function and minimal structure may be sufficient when there is a well-established correlation between structure and function. MPEP § 2163(II)(A)(3)(a)(i). In contrast, without such a correlation, the capability to recognize or understand the structure from the mere recitation of function and minimal structure is highly unlikely. MPEP § 2163(II)(A)(3)(a)(i) (citing Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406). Accordingly, a “sufficient description . . . requires the disclosure of either a representative number of species falling within the scope of the genus or structural features common to the members of the genus so that one of skill in the art can ‘visualize or recognize’ the members of the genus.” Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010).
The § 112(a) rejection
Claims 1, 8, 34, and 35 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement because the application as filed does not disclose either sufficient species of the claim 1 complex of formula I that functions such that:
Claim 1. . . wherein complexes of formula I having a stability constant in the range of from 5 L*mol-1 to 250,000 L *mol-1 when measured at 298 K and when the complex of formula I is dissolved in the solvent,
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
nor is there a well-established structure-function correlation between formula I and stability constant, air stability, and catalytic activity in olefin metathesis such that one of skill can recognize which species of formula I will function as claimed
Claim Breadth
Claim breath is relevant to the instant § 112(a) written description rejection. The written description must lead a person of ordinary skill in the art to understand that the inventor possessed the entire scope of the claimed invention. MPEP § 2163(II)(A)(3)(a)(ii) (citing Juno Therapeutics, Inc. v. Kite Pharma, Inc., 10 F.4th 1330, 1337, 2021 USPQ2d 893 (Fed. Cir. 2021)).
Here, the claim 1 complexes of formula I permits mixing and matching of variables A-D and R3 and R4. The number of complexes falling within these genera genus is vast.
Guidance in the Specification and Art -- “stability constant”
It is first noted that what is conventional or well known to one of ordinary skill in the art need not be disclosed in detail. MPEP § (II)(A)(3)(a). Thus, the state of and predictability in the art is a relevant consideration in determining compliance with § 112(a), written description. MPEP § (II)(A)(3)(a) (citing Capon v. Eshhar, 418 F.3d 1349, 1357, 76 USPQ2d 1078, 1085 (Fed. Cir. 2005) ("The ‘written description’ requirement must be applied in the context of the particular invention and the state of the knowledge…. As each field evolves, the balance also evolves between what is known and what is added by each inventive contribution”).
The specification is directed to the air-stability and catalytic activity of Schrock-type alkylidene complexes (useful for olefin metathesis). Specification at page 2, [0004].
The specification discloses five species of the claimed complex of formula I (i.e., complexes 20-23 and 25) with stability constants with the claimed range, as depicted below
PNG
media_image4.png
200
400
media_image4.png
Greyscale
PNG
media_image5.png
200
400
media_image5.png
Greyscale
20 R = methyl, R' = H; K20, d6-benzene, 298K = 3281 M-1 25 K25, d-benzene = 1000 M-1
21 R = ethyl, R' = H; K21, d6-benzene, 298K = 577 M-1
22 R = cyclopropyl, R' = CH3; K22, d6-benzene, 298K = 615 M-1
23 R = phenyl, R' = H; K23, d6-benzene, 298K = 255 M-1
Specification at pages 24-25. All five disclosed species require a 1,10-phenanthroline ligand (at claim 1 variable D) and a pyrrole (at claim 1 variable B). The specification teaches only one species (i.e., 26PHEN) exhibits a Kd6-benzene at 298 K of 0 (falling outside of the claimed range). Specification at page 27, [00108]. However, it is not clear from the specification what the structure of 26PHEN is. As such, the specification provides essentially no guidance as to claimed complexes of formula I that do not exhibit the claimed function.
The art and specification teach that Schrock-type alkylidene complexes are very sensitive to air and moisture making their handling difficult. J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (page 7829, col. 1); specification at page 1, [0002]. The art and specification teach that the 1,10-phenanthroline complexed catalysts have increased stability, but an in-situ Lewis acid is required to release the active catalyst (1,10-phenanthroline decoordination), which results in side products and a more complicated workup. Specification at page 2, [0005]; Fürstner at page 7830, col. 2; G. Frater et al., US 2018/0022770 (2018) (page 3, [0026]). Thus, the chemistry of air-stable Schrock-type alkylidene complexes is complicated tradeoff because certain ligands (such as the Fürstner bipyridine complexes), while improving air-stability, unfortunately also require a Lewis acid to generate the active (decoordinated) complex in situ. Id.; see also, H. Ehrhorn e al., 25 Chemistry a European Journal, 3190-3208 (2019) (see page 3193, col. 2; page 3196-3197 (at 3197, col. 2 -- discussing two new multidentate trisilanol ligands (32, 33), intended to coordinate to molybdenum alkylidyne complexes where ligand exchange failed).
Neither art cited by Applicant nor art identified in searches teaches a strong or well-established correlation between the structure of molybdenum or tungsten alkylidene complexes and their stability constant K (per Claim Interpretation above) air stability, or catalytic activity in olefin metathesis predictable of species throughout the vast breadth of claimed formula I that exhibit the claimed stability constant in the range of from 5 L*moI-1 to 250,000 L *moI-1, or air stability and catalytic activity in olefin metathesis such that one of skill in the art can ‘visualize or recognize’ the members of the claimed genus that perform the claimed function. Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010).
Claims 1, 8, 34, and 35 Lack an Adequate Supporting Written Description
Claims 1, 8, 34, and 35 lack adequate written description support because the application as filed does not disclose either sufficient species of claimed complex formula I nor is there a well-established structure-function correlation between formula I and “stability constant K” such that one of skill can recognize which species of formula I will function so as to exhibit a stability constant K in a “a range of from 5 L*moI-1 to 250,000 L *moI-1 when measured at 298 K when the complex of formula I is dissolved in the solvent”. Dependent claims 8, 34, and 35 do not sufficiently narrow in this respect.
Here, Applicant is not in possession of the full claim scope because neither the specification nor the art of record provides sufficient guidance allowing one of skill to correctly choose claim 1, formula I variables A-D, R3 and R4 such that one of skill would recognize Applicant’s possession of the full scope of those members encompassed by claim 1 formula 1 that exhibit the claimed stability constant, air stability, and catalytic activity in olefin metathesis.
In sum, the claims recite numerous possible structural combinations but neither the art nor the specification shows a well-established correlation between the claimed stability constant and mixing and matching the claim 1 variables such that one of skill can recognize which variable combinations perform the claimed function, particularly in view of the art’s complexity as discussed above. As stated above, the written description requirement may also be satisfied through disclosure of function and minimal structure when there is a well-established correlation between structure and function. MPEP § 2163(II)(A)(3)(a)(i). In contrast, without such a correlation, the capability to recognize or understand the structure from the mere recitation of function and minimal structure is highly unlikely. MPEP § 2163(II)(A)(3)(a)(i) (citing Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406).
Neither art cited by Applicant nor art identified in searches teaches a strong or well-established correlation between the structure of molybdenum or tungsten alkylidene complexes and their stability constant K (per Claim Interpretation above), air stability, and catalytic activity in olefin metathesis predictable of species throughout the vast breadth of claimed formula I that exhibit the claim 1 stability constant in the range of from 5 L*moI-1 to 250,000 L *moI-1, such that one of skill in the art can ‘visualize or recognize’ the members of the claimed genus that perform the claimed function. Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010).
As discussed above, the specification discloses that the structurally similar tungsten complexes 20-23 and 25 (no molybdenum species are disclosed) exhibit the claimed function respecting stability constant. Specification at pages 24-25. All five disclosed species require a 1,10-phenanthroline ligand (at claim 1 variable D) and a pyrrole (at claim 1 variable B). The specification also teaches that complex 26 does not exhibit the claimed function (K=0), however the structure of complex 26 cannot be determined by the Examiner. Specification at page 27, [00108]. As such, the specification provides essentially no guidance as to claimed complexes of formula I that do not exhibit the claimed function.
These six disclosed species do not amount to a strong correlation between specific structure and stability constant, air stability, and catalytic activity in olefin metathesis. It is true that claim 1 recites a complete structure, but it also leaves a large number of the formula I structural aspects undefined. For example, the variable A, B, and C aryl group is generic and all of formula I variables A-D, R3 and R4 may chosen from a number of different alternatives).
Further, the specification does not disclose a representative number of species because, as discussed above, only five species (having the same basic structure) are disclosed that perform the claimed function. These species are clearly not representative the full scope of formula I. A "representative number of species" means that the species which are adequately described are representative of the entire genus. MPEP § 2163(II)(A)(3)(a)(ii); see also, Idenix Pharms. LLC v. Gilead Scis. Inc., 941 F.3d 1149, 1164 (Fed. Cir. 2019) (“[a]s a result, a POSA is deprived of any meaningful guidance into what compounds beyond the examples and formulas, if any, would provide the same result”). Here the very structurally similar disclosed species are clearly not representative of the claimed genus.
The holding in Idenix Pharms. LLC v. Gilead Scis. Inc., 941 F.3d 1149, 1161 (Fed. Cir. 2019) is also relevant to the facts at issue. In Idenix, the claims recited a method of treating HCV by administering a nucleoside having a specific chemical and stereochemical structure. Idenix, 941 F.3d at 1154. Idenix argued that the key to its invention, and to treatment of HCV, is the use of 2'-methyl-up nucleosides. Id. The court adopted the lower court’s claim constructure that the functional claim language limits the scope of the claims to the use of some set of compounds that are effective for treatment of HCV. Idenix, 941 F.3d at 1155. In Idenix, the court found that the question in this case is whether the '597 patent demonstrates that the inventor was in possession of those 2'-methyl-up nucleosides that fall within the boundaries of the claim (i.e., are effective against HCV), but are not encompassed by the explicit formulas or examples provided in the specification. Idenix, 941 F.3d at 1163. The court held that the '597 patent is invalid for lack of written description, as it fails to provide sufficient blaze marks to direct an ordinary artisan to the specific subset of 2'-methyl-up nucleosides [within the claimed genus] that are effective in treating HCV. Idenix, 941 F.3d at 1164. The court noted that the specification provides no indication that any nucleosides outside of those disclosed in its formulas could be effective to treat HCV—much less any indication as to which of those undisclosed nucleosides would be effective. Idenix, 941 F.3d at 1164. The Idenix further noted that the written description requirement specifically defends against such attempts to "cover any compound later actually invented and determined to fall within the claim's functional boundaries. Idenix, 941 F.3d at 1165.
Applicant’s Argument
Applicant argues that claim 1 recites:
Claims 1. . . wherein complexes of formula I having a stability constant in the range of from 5 L*mol-1 to 250,000 L *mol-1 when measured at 298 K and when the complex of formula I is dissolved in the solvent,
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
Applicant argues that therefore, the structure-function correlation between formula I and stability condition and meaning of "stability constant" recited in independent claim 1 is well-established. Applicant further argues that amended claim 1 discloses sufficient details about A, B, C, and D such that one of skill can recognize which species of formula I exhibit the aforementioned feature recited in amended claim 1.
This argument is not persuasive because the cited amendment does not provide a strong or well-established correlation between the structure of molybdenum or tungsten alkylidene complexes and their stability constant (per Claim Interpretation above), or air stability, and catalytic activity in olefin metathesis predictable of species throughout the vast breadth of claimed formula I that exhibit the claim 1 stability constant in the range of from 5 L*moI-1 to 250,000 L *moI-1, such that one of skill can ‘visualize or recognize’ the members of the claimed genus that perform the claimed function. Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349 (Fed. Cir. 2010). Stated differently, the issue is which particular species of formula I meets the stability-constant functional language. In order to correctly choose the particular species from within the formula I genus, one of skill requires knowledge of how the structure of formula I affects the stability constant. Without such knowledge, one of skill is not able to correctly choose particular combinations of claim 1 variables A-D, R3 and R4, such that a stability constant within the claimed range is achieved. Here the neither the art nor the specification provides guidance regarding how the structure of formula I affects the stability constant. As such, one of skill must first obtain a particular complex of formula I, and then test it to see if it exhibits a conforming stability constant. Such testing requirement does not meet the standard of § 112(a) because the invention is not complete/possessed by Applicant. MPEP § 2163(II)(3)(a)(ii). Rather Applicant has proffered a claimed genus, narrowed by functional language, where it is left to the claim practitioner to figure out which species, literally falling within formula I, are claimed and which are not. In the absence of a teaching in the art or specification regarding how the formula I chemical structure affects the stability constant, and without performing physical tests, one of skill cannot determine which species, literally falling within formula I, are claimed and which are not. For practical purposes, in the absence of such structure-function teachings, the Examiner does not have access to laboratory resources to determine whether a particular compound, otherwise meeting the variable definition of formula I, also falls within the scope of claim 1’s functional language.
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, 8, 17, and 32-37 are rejected under AIA 35 U.S.C. 103 as being unpatentable over F. Toth et al., US 2017/0037069 (2017) (“Toth”) and J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (“Fürstner”) in further view of G. Frater et al, WO 2016/142849 (2016) (“Frater”).
F. Toth et al., US 2017/037069 (2017) (“Toth”)
Toth discloses compounds of Formula (I):
PNG
media_image6.png
200
400
media_image6.png
Greyscale
where M is a Group 6 metal atom, are suitable for use as catalyst compounds, e.g., catalysts for olefin metathesis reactions. Toth at page 7, [0091].
In working Example 1, Toth discloses compound 2 (a species of Formula I) having the following structure.
PNG
media_image7.png
200
400
media_image7.png
Greyscale
Toth compound 2
Toth at page 19, Table 2; Id. at page 26, [0250] (Example 1, synthesis of compound 2).
Toth teaches that compound 2 is air sensitive and was completely decomposed over a period of 24 hours air exposure. Toth at page 32, [0284] (data Table 10).
Toth teaches that the disclosed metathesis catalysts are dissolved in solvent prior to conducting the metathesis reaction.
[0213] In certain embodiments, the metathesis catalyst (such as the compounds disclosed herein) is dissolved in a solvent prior to conducting the metathesis reaction. In certain such embodiments, the solvent chosen may be selected to be substantially inert with respect to the metathesis catalyst.
Toth at page 23, [0213].
In a working example, Toth discloses that compound 2 was an active catalyst in the ring-closing metathesis of diethyl diallylmalonate (giving 93% conversion at loading of 200 ppm). Toth at page 31, [0280].
Differences between Toth and the Elected Species
Toth complex 2 differs from the claims and the elected species in that it lacks the stabilizing 1,10-phenanthroline ligand.
J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (“Fürstner”)
Fürstner discloses tetracoordinate molybdenum alkylidenes developed by Schrock, such as complex 1, are powerful alkene metathesis catalysts. Fürstner at page 7829, col. 1. Fürstner teaches, however, that complex 1 and relatives, are very sensitive to air and moisture, their handling is clearly more demanding than that of the competing ruthenium carbenes introduced by Grubbs. Fürstner at page 7829, col. 1.
Fürstner teaches
To overcome this disadvantage, we now present a simple way of rendering prototype Schrock alkylidenes largely air-stable, which facilitates their handling and may hence encourage more widespread use of these able catalysts in preparative laboratories.
Fürstner at page 7829, col. 1 (emphasis added).
To exemplify, Fürstner teaches that solutions of 1 in toluene were reacted at room temperature with equimolar amounts of 1,10-phenanthroline and the resulting crystalline adducts 2 (complexed with the 1,10-phenanthroline) turned out to be surprisingly robust in the solid state as well as in solution. Fürstner at page 7829, col. 1.
PNG
media_image8.png
200
400
media_image8.png
Greyscale
Fürstner at page 7829, col. 1: Id. at Scheme 1. Fürstner teaches that while complex 2 is devoid of catalytic activity in prototype ring closing metathesis (RCM) the bidentate 1,10-phenanthroline ligand can be readily pulled off upon treatment with one equivalent of anhydrous ZnCl2 in toluene at [Symbol font/0xA3]100 °C, thus releasing the structurally intact and catalytically competent parent complex 1. Fürstner at page 7829, col. 2. Fürstner teaches that complex 1’s excellent reactivity was found uncompromised by the presence of the precipitated yellow phenanthroline·ZnCl2 that need not be filtered off. Fürstner at page 7829, col. 2; see reaction yield data using pre-catalyst 2 in ring closing metatheses in Fürstner Table 1 at page 7831.
G. Frater et al, WO 2016/142849 (2016) (“Frater”)
As discussed above, Frater discloses complexes that fall within the scope of claimed formula I. For example, Frater discloses the following complexes III-VI. Frater at page 3.
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Frater at page 3. In working Examples 1-4 Frater teaches synthesis of catalysts III, IV, V, and VI by treating the active catalyst with 1,10-phenantroline using a similar procedure to that of Fürstner above. Frater at pages 5-8. For Example, Frater teaches that the compound of formula III is made by the following scheme, which involves addition of a 1,10-phenantroline ligand.
PNG
media_image9.png
200
400
media_image9.png
Greyscale
Frater at page 3. Frater prepares complexes III-V as solvent compositions that do not contain a Lewis acid (per instant claims 34-37). Frater at pages 5-8 (synthesis Examples 1-4); See e.g., Example 1 where the solid filtered product III was washed with pentane, which results in a composition of III and pentane. Frater at page 5, lines 30-32.
Frater teaches:
The catalysts are generated in situ from the compounds of Formula 11 by art-recognised methods, such as the addition of Lewis acids, typically zinc chloride.
Frater at page 4, lines 11-12 (emphasis added).
In working Examples 5-8, Frater teaches treating the above catalysts with zinc chloride to disassociate the 1,10-phenantroline thereby generating the active catalyst in situ (and release 1,10-phenanthroline-zinc) and performing a ring-opening polymerization. Frater at pages 8-10. Frater’s synthetic method involves first forming a composition comprising the catalyst and a solvent before adding the zinc chloride. Frater at page 8, lines 20-24 (Example 5, composition of catalyst III and toluene, without ZnCl2); Frater at page 9, lines 5-8 (Example 6, composition of catalyst IV and toluene, without ZnCl2); Frater at page 9, lines 29-31 (Example 7, composition of catalyst V and toluene, without ZnCl2). Thus again, Frater teaches complexes III-V as solvent compositions that do not contain a Lewis acid (per instant claims 34-37).
Frater therefore teaches one of ordinary skill that 1,10-phenanthroline complexes with 14-electron tungsten alkylidene catalysts to give the 18-electron tungsten alkylidene pre-catalysts and that such 18-electron tungsten pre-catalysts can be efficiently and readily restored, in situ, by decomplexation with ZnCl2 in situ.
Obviousness Rationale
Obviousness of a claimed compound can be shown where there is initial motivation to select a prior art compound and thereafter still further motivation to make the specific structural modifications thereto so as to arrive at a claimed compound. See MPEP § 2143(B) (discussing “lead compound cases” in Examples 9-11 with respect to pharmaceutical applications).4
The elected species and composition claims 1, 8, 17, 32, and 33 are obvious over the cited art because one of ordinary skill is motivated to complex Toth catalyst 2 with 1,10-phenanthroline so as to arrive at the elected species and further motivated to prepare a composition of the resulting complexed catalyst in a solvent thereby meeting each and every limitation of claims 1 and 17. One of ordinary skill is motivated to prepare Toth catalyst 2 as a composition in solvent (as per claim 17) because, as discussed above, Frater teaches that such 1,10-phenanthroline complexed catalysts are prepared and used as solvent compositions.
One of ordinary skill is motivated to select and explore Toth’s 14-electron tungsten alkylidene compound 2 because Toth teaches that it is an active olefin metathesis catalyst. One of ordinary skill is further motivated to stabilize Toth compound 2 against air/moisture by complexing it with 1,10-phenanthroline so as to arrive at the elected species. One of ordinary skill is so motivated because Fürstner teaches that such Schrock-type catalysts are very sensitive to air and moisture making their handling demanding and that complexing the molybdenum catalysts with 1,10-phenanthroline stabilizes these catalysts. Further, Toth specifically teaches that compound 2 is air sensitive and was completely decomposed over a period of 24 hours air exposure. Toth at page 32, [0284] (data Table 10). For example, one of ordinary skill seeking extended storage or shipping of Toth catalyst 2 is motivated to first complex it with 1,10-phenanthroline.
Frater and Fürstner teach that the catalytic activity of the 1,10-phenanthroline complexes (Frater teaches W; Fürstner teaches Mo) can be efficiently and readily restored, in situ, by decomplexation of the 1,10-phenanthroline ligand with ZnCl2. One of ordinary skill has a reasonable expectation that tungsten catalysts (as in Toth compound 2 and the elected species) will complex/decomplex with 1,10-phenanthroline, because Frater teaches complexing such 14-electron tungsten catalysts with 1,10-phenanthroline and further de-complexing in situ with zinc chloride to perform a metatheses reaction. MPEP § 2143.02(I) (where there is a reason to modify or combine the prior art to achieve the claimed invention, the claims may be rejected as prima facie obvious provided there is also a reasonable expectation of success).
All limitations of composition claims 1, 8, 17, 32, and 33 are therefore met because the above obviousness rationale generates the elected species in solvent composition, and the instant specification teaches the elected species exhibits the claimed stability constant.
Claims 34-37 are obvious because Frater motivates one of ordinary skill to prepare the above proposed Toth compound 2 complexed with 1,10-phenanthroline as solvent composition, without any Lewis acid. One of ordinary skill is so motivated because Frater teaches that preparation of structurally similar 1,10-phenanthroline complexes III-V involves simple addition of 1,10-phenanthroline to the active catalyst in a solvent, where the product is thus obtained as a solvent composition that does not contain a Lewis acid (per instant claims 34-37). Frater at pages 5-8 (synthesis Examples 1-4); See e.g., Example 1 where the solid filtered 1,10-phenanthroline-product III was washed with pentane, which results in a composition of III and pentane and no Lewis acid. Frater at page 5, lines 30-32. In sum, one of ordinary skill is motivated to synthesize above-proposed Toth compound 2 complexed with 1,10-phenanthroline in solvent, without a Lewis acid, as suggested by Frater thereby arriving at each and every limitation of claims 34-37.
Alternatively, one of ordinary skill is motivated to provide the above-proposed Toth compound 2/phenanthroline complex in solvent, without any Lewis acid (thereby arriving at each and every limitation of claims 34-37), and then subsequently add the Lewis acid, zinc chloride, to the solvent composition. In this regard, in working Examples 5-8, Frater’s synthetic method involves preparing a solvent composition of similar 1,10-phenanthroline-complexed catalysts before adding the zinc chloride. Frater at page 8, lines 20-24 (Example 5, composition of catalyst III and toluene, without ZnCl2); Frater at page 9, lines 5-8 (Example 6, composition of catalyst IV and toluene, without ZnCl2); Frater at page 9, lines 29-31 (Example 7, composition of catalyst V and toluene, without ZnCl2). Thus, Frater teaches catalytic-use of structurally similar complexes III-V as solvent compositions that do not contain a Lewis acid (per instant claims 34-37).
Applicant’s Argument
Applicant argues that the § 103 rationale does not teach the claim 1 and 17 limitation of:
Claims 1 and 17 . . . wherein complexes of formula I having a stability constant in the range of from 5 L*mol-1 to 250,000 L *mol-1 when measured at 298 K and when the complex of formula I is dissolved in the solvent,
are air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid and hence unnecessarily forming corresponding by-products, i.e., such complexes are autoactivating; and
wherein the solvent is selected from benzene, toluene, xylene or chlorobenzene, chlorinated hydrocarbons, or the substrate to be metathesized.
Reply at page 18. Applicant argues that none of the cited references provides any incentive or motivation for a person skilled in the art to determine the stability constant to assess whether a compound is autoactivating (dissociative) or not. Reply at page 19. Applicant argues that none of the cited references provides any incentive or motivation for a person skilled in the art to determine the stability constant to assess whether a compound is autoactivating (dissociative) or not. Reply at page 19.
This argument is not persuasive because the § 103 rationale is based on the elected species and the specification teaches that the elected species (specification compound 25) exhibits the instantly claimed stability constant.5 The specification teaches the following stability constant data for the elected species.
PNG
media_image10.png
200
400
media_image10.png
Greyscale
Specification at page 25, [00102], Scheme 3. The specification teaches that complex 25 is autoactivating. Specification at page 25, [00103]. The specification teaches that complex 25 is “air-stable and catalytically active in an olefin metathesis reaction without the necessity of removing the bidentate ligand by means of a Lewis acid”. Specification at page 26, [00105]. It is appropriate to look to the instant specification for evidence that a claimed feature is inherent in the prior art. See, MPEP § 2112.02(I) (discussing Ex parte Novitski, 26 USPQ2d 1389 (Bd. Pat. App. & Inter. 1993).6 Here, although the prior art itself does not teach the asserted functional characteristics, they are nonetheless inherent in the prior art.
Applicant’s argument that none of the cited references provides any incentive or motivation for a person skilled in the art to determine the stability constant to assess whether a compound is autoactivating (dissociative) or not is duly noted. Reply at page 19. However, one of ordinary skill is motivated to complex Toth compound 2 with 1,10-phenanthroline so as to arrive at the elected species in order to improve is handling in air. The reason or motivation to modify the reference may often suggest what the inventor has done, but for a different purpose or to solve a different problem. It is not necessary that the prior art suggest the combination to achieve the same advantage or result discovered by applicant. MPEP § 2144(IV).
Non-Statutory Double Patenting
The non-statutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A non-statutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
Provisional Non-Statutory Double Patenting Rejection over L. Ondi et al., US 17/595,761 (claimed filed on 11/07/2025), published as US 2022/0227797 (2022)
Instant claims 1, 8, 34, and 35 are provisionally rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claim 11 of L. Ondi et al., US 17/595,761 (claimed filed on 11/07/2025), published as US 2022/0227797 (2022) in view of J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (“Fürstner”) and G. Frater et al, WO 2016/142849 (2016) (“Frater”). The rejection is provisional because the conflicting claims have not been patented.
Conflicting claim 11 discloses olefin catalyst species; for example, the following species:
PNG
media_image11.png
200
400
media_image11.png
Greyscale
The species of conflicting claim 11 differ from product claims 1, 8, 34, and 35 in that they lack the instant 1,10-phenanthroline ligand.
As discussed in detail above, Fürstner teaches that solutions of 1 in toluene were reacted at room temperature with equimolar amounts of 1,10-phenanthroline and the resulting crystalline adducts 2 (complexed with the 1,10-phenanthroline) turned out to be surprisingly robust in the solid state as well as in solution. Fürstner at page 7829, col. 1.
PNG
media_image8.png
200
400
media_image8.png
Greyscale
Fürstner at page 7829, col. 1: Id. at Scheme 1. Fürstner teaches that while complex 2 is devoid of catalytic activity in prototype ring closing metathesis (RCM) the bidentate 1,10-phenanthroline ligand can be readily pulled off upon treatment with one equivalent of anhydrous ZnCl2 in toluene at [Symbol font/0xA3]100 °C, thus releasing the structurally intact and catalytically competent parent complex 1. Fürstner at page 7829, col. 2. Fürstner teaches that complex 1’s excellent reactivity was found uncompromised by the presence of the precipitated yellow phenanthroline·ZnCl2 that need not be filtered off. Fürstner at page 7829, col. 2; see reaction yield data using pre-catalyst 2 in ring closing metatheses in Fürstner Table 1 at page 7831.
Also as discussed above, Frater discloses complexes that fall within the scope of claimed formula I. For example, Frater discloses the following complexes III-VI. Frater at page 3.
PNG
media_image3.png
200
400
media_image3.png
Greyscale
Frater at page 3. In working Examples 1-4 Frater teaches synthesis of catalysts III, IV, V, and VI by treating the base catalyst with 1, 10-phenantroline using a similar procedure to that of Fürstner above. Frater at pages 5-8. In working Examples 5-8, Frater teaches treating the above catalysts with zinc chloride to release 1,10-phenanthroline-zinc and perform a ring-opening polymerization. Frater at pages 8-10.
Frater therefore teaches one of ordinary skill that 1,10-phenanthroline complexes with 14-electron tungsten alkylidene catalysts to give the 18-electron tungsten alkylidene pre-catalysts and that such 18-electron tungsten pre-catalysts can be efficiently and readily restored, in situ, by decomplexation with ZnCl2 in situ.
Rationale
Instant claims 1, 8, 34 and 35 are patentably indistinct from conflicting claim 11 in view of the cited secondary art for the following reasons. One of ordinary skill is motivated to select and explore the species of conflicting claim 11 because these compounds are taught to be useful for olefin metathesis. See US 2022/0227797 at page 1, [0013].7 One of ordinary skill is further motivated to stabilize the conflicting claim 11 species against air/moisture by complexing it with 1,10-phenanthroline so as to arrive at compounds falling within the instantly claimed genera. One of ordinary skill is so motivated because Fürstner teaches that such Schrock-type catalysts are very sensitive to air and moisture making their handling demanding and that complexing the molybdenum catalysts with 1,10-phenanthroline stabilizes these catalysts. And Fürstner further teaches that the catalytic activity of the 1,10-phenanthroline complex can be efficiently and readily restored, in situ, by decomplexation with ZnCl2. One of ordinary skill has a reasonable expectation that conflicting tungsten catalysts will complex/decomplex with 1,10-phenanthroline, as taught by Fürstner for the molybdenum analogs, because Frater teaches complexing such 14-electron tungsten catalysts with 1,10-phenanthroline and further decomplexing in situ with zinc chloride to perform a metatheses reaction. MPEP § 2143.02(I) (where there is a reason to modify or combine the prior art to achieve the claimed invention, the claims may be rejected as prima facie obvious provided there is also a reasonable expectation of success). In sum, the instant composition claims are patentably indistinct from the species of the conflicting claims because one of ordinary skill is motivated to stabilize the conflicting species against air/moisture by complexing it with 1,10-phenanthroline so as to arrive at compositions falling within the instantly claimed genera under the same rational given above in the § 103 rejection.
In view of the § 112(b) rejection above regarding the meaning of “stability constant” and “air stable”, and the teachings of the instant specification, the proposed complexes are asserted to inherently meet the claimed stability-constant, catalysis, and air stability functional characteristics. Specification at pages 25-27, [00101-[00107] (teaching that structurally similar compounds to the conflicting species meet the claimed functional characteristics when complexed to 1,10-phenanthroline).
Non-Statutory Double Patenting Rejection over H. Gulyas et al., US 11,702,438 (2023)
Instant claims 1, 8, 34 and 35 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 12 or 13 of H. Gulyas et al., US 11,702,438 (2023) in view of J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (“Fürstner”) and G. Frater et al, WO 2016/142849 (2016) (“Frater”).
Conflicting claim 13 discloses the following catalyst species
PNG
media_image12.png
200
400
media_image12.png
Greyscale
The species of conflicting claims 12 and 13 differ from product claims 1, 8, 34 and 35 in that they lack the instant 1,10-phenanthroline ligand. The conflicting specification teaches that the conflicting claim 12 and 13 species is useful for olefin metathesis. See US 11,702,436 at col. 7, lines 48-67.
The instant claims are patentably indistinct from the species of the conflicting claims because one of ordinary skill is motivated to stabilize the conflicting species against air/moisture by complexing it with 1,10-phenanthroline so as to arrive at compositions falling within the instantly claimed genera under the same rational given above in the § 103 rejection.
In view of the § 112(b) rejection above regarding the meaning of “stability constant” and “air stable”, and the teachings of the instant specification, the proposed complexes are asserted to inherently meet the claimed stability-constant, catalysis, and air stability functional characteristics. Specification at pages 25-27, [00101-[00107] (teaching that structurally similar compounds to the conflicting species meet the claimed functional characteristics when complexed to 1,10-phenanthroline).
Non-Statutory Double Patenting Rejection over G. Frater et al., US 11,420,926 (2022)
Instant claims 1, 8, 17, and 32-37 are rejected on the ground of non-statutory double patenting as being unpatentable over conflicting claims 1 and 11 of G. Frater et al., US 11,420,926 (2022) in view of J. Fürstner et al., 50 Angew. Chem. Int. Ed. 7829-7832 (2011) (“Fürstner”) and G. Frater et al, WO 2016/142849 (2016) (“Frater”).
Conflicting claim 11 discloses the following catalyst species, which is the instantly elected species
PNG
media_image13.png
200
400
media_image13.png
Greyscale
The species of conflicting claim 11 differs from product claims 1, 8, 17, and 32-37 (and the elected species) in that it lacks the instant 1,10-phenanthroline ligand. Conflicting claim 1 teaches that the conflicting claim 11 species is useful for olefin metathesis. See US 11,702,436 at col. 7, lines 48-67.
The instant claims are patentably indistinct from conflicting claim 11 because one of ordinary skill is motivated to stabilize the conflicting species against air/moisture by complexing it with 1,10-phenanthroline so as to arrive at the elected species falling within the instantly claimed genera for the same reasons given in the § 103 rejection above.
Applicant’s Argument
Applicant argues that it is requested the rejection of the claims under obviousness-type double patenting be held in abeyance until all other claim objections and rejections are resolved. Applicant argues that independent claims 1 and 17 have been amended and the Examiner has not shown that the currently pending claims are not patentably indistinct from the alleged conflicting claims in view of the amendments presented herein. Accordingly, Applicant requests that the rejections be held in abeyance until such time as all claims are found otherwise allowable
The argument is not persuasive to overcome the double patenting rejection because the amendments have been taken into account in the above rationale.
Terminal Disclaimer
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a non-statutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 ALEXANDER R PAGANO whose telephone number is (571)270-3764. The examiner can normally be reached 8:00 AM through 5:00 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 In the previous Office action, Group (I) was rejoined with elected Group (II).
2 The idea of “substrate to be metathesized” is not functionally related to the claim 1 structure because claim 1 is directed to a composition of matter. MPEP § 2111.05; (citing In re Ngai, 367 F.3d 1336, 1339 (Fed. Cir. 2004). The structure of the claim 1 composition remains unchanged regardless of which “substrate to be metathesized” is selected. Also, the claim 1 steps/instructions of determining the stability constant do not lead to selection of any particular “substrate to be metathesized” as the solvent.
3 While there is a presumption that an adequate written description of the claimed invention is present in the specification as filed, a question as to whether a specification provides an adequate written description may arise in the context of an original claim. MPEP § 2163.03 (V) (citing In re Wertheim, 541 F.2d 257, 262, 191 USPQ 90, 96 (CCPA 1976)). An original claim may lack written description support when (1) the claim defines the invention in functional language specifying a desired result but the disclosure fails to sufficiently identify how the function is performed or the result is achieved or (2) a broad genus claim is presented but the disclosure only describes a narrow species with no evidence that the genus is contemplated. MPEP § 2163.03 (V) (citing Ariad Pharms., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1349-50 (Fed. Cir. 2010) ("[e]ven if a claim is supported by the specification, the language of the specification, to the extent possible, must describe the claimed invention so that one skilled in the art can recognize what is claimed”).
4 The MPEP warns against applying the lead compound analysis rigidly in view of the flexible approach stated in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) see also, MPEP § 2143(B), Example 11 (citing Altana Pharma AG v. Teva Pharm. USA, Inc., 566 F.3d 999, 91 USPQ2d 1018 (Fed. Cir. 2009) a ‘restrictive view of the lead compound test would present a rigid test similar to the teaching-suggestion-motivation test that the Supreme Court explicitly rejected in KSR’).
5 Where the claimed and prior art products are identical or substantially identical in composition to a claimed composition, a prima facie case of either anticipation or obviousness has been established subject to Applicant’s rebuttal. MPEP § 2112.01(I) (citing In re Ludtke, 441 F.2d 660, 169 USPQ 563 (CCPA 1971) (holding that a prior art structure anticipated a claimed structure even though a claimed functional recitation was not specifically taught in the prior art reference because applicant had failed to show that the prior art did not possess the functional characteristics of the claims)); see also, MPEP § 2112(V) (citing In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
6 In Ex parte Novitski the Board rejected a claim directed to a method for protecting a plant from plant pathogenic nematodes by inoculating the plant with a nematode inhibiting strain of P. cepacia. A U.S. patent to Dart disclosed inoculation using P. cepacia type Wisconsin 526 bacteria for protecting the plant from fungal disease. Dart was silent as to nematode inhibition but the Board concluded that nematode inhibition was an inherent property of the bacteria. The Board noted that applicant had stated in the specification that Wisconsin 526 possesses an 18% nematode inhibition rating).
7 A reference specification may be reviewed to construe the conflicting claims. MPEP § 804(II)(B)(1). Further, those portions of the specification which provide support for the conflicting claims may also be examined and considered when addressing the issue of whether a claim in the application defines an obvious variation of an invention claimed in the reference patent or application. MPEP § 804(II)(B)(1) (citing In re Vogel, 422 F.2d 438, 441-42, 164 USPQ 619, 622 (CCPA 1970)). The court in Vogel recognized ‘that it is most difficult, if not meaningless, to try to say what is or is not an obvious variation of a claim,’ but that one can judge whether or not the invention claimed in an application is an obvious variation of an embodiment disclosed in the patent or application which provides support for the claim. MPEP § 804(II)(B)(1). In this regard, it is also proper to look at the disclosed utility in the reference disclosure to determine the overall question of obviousness in a non-statutory double patenting context. MPEP § 804(II)(B)(1) (citing Sun Pharm. Indus., Ltd. v. Eli Lilly & Co., 611 F.3d 1381, 95 USPQ2d 1797 (Fed. Cir. 2010).
Prosecution Insights