DETAILED ACTION
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 .
Election/Restrictions
Applicant’s election with traverse of species: (1) propylene oxide (PO) as the alkylene oxide,
encompassed by claims 1-15; (2) hexachlorobenzene oxide as the arene oxide, encompassed by claims 1-15; (3) pentafluoropyridine N-oxide as the pyridine N-oxide, encompassed by claims 1-15; (4) 2-chloropyrimidine N-oxide as the pyrimidine N-oxide, encompassed by claims 1-15; (5) propene as the alkene, encompassed by claims 1-15; (6) CrCl3 as the metal salt (A-2), encompassed by claims 1-15; and (7) silver as the metal (A-1), encompassed by claims 1-15, in the reply filed on 4/21/26 is acknowledged. The traversal is on the ground that the common technical feature is a special technical feature over Samsel et al. (Mechanism of the Chromium-Catalyzed Epoxidation of Olefins. Role of Oxochromium(V) Cations,” published 1985, cited by Examiner on 2/25/2026)(hereinafter, ‘Samsel’).
This is not found persuasive because Samsel teaches each and every aspect of the invention of
instant claim 1, which is directed to a process for producing an alkylene oxide comprising reacting an alkene with an arene oxide, pyridine N-oxide and/or pyrimidine N-oxide, in the presence of a catalyst. Samsel teaches that norbornene (an alkene) can be epoxidized using (salen)CrIII metal in the presence of pyridine N-oxide (see reference Table 1).
Thus, the species election requirement is still deemed proper and is therefore made FINAL.
In the Response to Restriction Requirements as filed on 4/21/2026, applicants have amended no claims; cancelled no claims; and added no new claims. Therefore, claims 1-15 are currently pending and claims 1-15 are under consideration.
Priority
The instant application is a 35 U.S.C. § 371 International Application PCT/EP2022/067640, filed on June 28, 2022, which claims priority to European Application No. 21182701.9, filed on June 30, 2021.
Information Disclosure Statement
The information disclosure statement (IDS) filed on 12/19/2023 is in compliance with the provisions of 37 CFR 1.97. All references have been considered except where marked with a strikethrough. A signed copy of Form 1449 is included with this Office Action.
Claim Interpretation
The specification provides no definition of an “alkene” so the Examiner has interpreted alkene to mean having a straight chain or branched hydrocarbon having at least 2 carbon atoms and at least one double bond.
Claim Objections
Claim 8 is objected to because of the following informality: there is a semi-colon inserted between “(+II); (+III)” when it should be a comma. Appropriate correction is required.
Claim Rejections - 35 USC § 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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 4 and 14 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 4, the phrase "preferably" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
Claim 14 recites the limitation "pyridine oxide". There is insufficient antecedent basis for this limitation in the claim.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 3, and 5-6 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 3, which depends on claim 1, is drawn to different species of alkenes. Claim 3 lists alkenes that broaden the scope of the definition of an alkene, as provided by the Examiner to mean straight or branched hydrocarbon chains having at least one double bond and at least two carbon atoms (see Claim Interpretation section of Office Action). For instance, the “allyl alcohol” of claim 3 does not fit within this definition and broadens the claim.
Claims 5 and 6, which are dependent on claim 1, are drawn to different species of substituted pyridine N-oxides and substituted pyrimidine N-oxides, respectively. Claim 1 is drawn to pyridine N-oxide and pyrimidine N-oxide, which are the discrete structures, shown below:
pyridine N-oxide: pyrimidine N-oxide:
PNG
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146
76
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Greyscale
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116
148
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Greyscale
Furthermore, Applicant does not provide any definitions in the specification to define pyridine N-oxide or pyrimidine N-oxide. Therefore, claims 5 and 6, which are drawn to substituted species of pyridine N-oxide and pyrimidine N-oxide, respectively, broaden the scope of claim 1.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 112(a)
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.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
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 of carrying out his invention.
Scope of Enablement – Process for Producing
Claims 1-15 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for the following:
A process for producing an alkylene oxide comprising reacting an alkene with an arene oxide, pyridine N-oxide and/or pyrimidine N-oxide, in the presence of a catalyst.
where the alkene is a hydrocarbon-based alkene only;
where the arene oxide is perfluorobenzene oxide or perchlorobenzene oxide only;
where the pyridine N-oxide is perfluoropyridine N-oxide only;
where a solvent is present
does not reasonably provide enablement for elements that are outside the scope of the enabling elements listed above. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make the invention commensurate in scope with these claims.
To be enabling, the specification of the patent application must teach those skilled in the art how to make and use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557, 1561 (Fd. Cir. 1993). Explaining what is meant by "undue experimentation," the Federal Circuit has stated that:
The test is not merely quantitative, since a considerable amount of experimentation is permissible, if it is merely routine, or if the specification in question provides a reasonable amount of guidance with respect to the direction in which experimentation should proceed to enable the determination of how to practice a desired embodiment of the claimed invention. PPG v. Guardian, 75 F.3d 1558, 1564 (Fed. Cir. 1996). As pointed out by the court in In re Angstadt, 537 F.2d 498 at 504 (CCPA 1976), the key word is "undue", not "experimentation".
The factors that may be considered in determining whether a disclosure would require undue experimentation are set forth In re Wands, 8 USPQ2d 1400 (CAFC 1988) at 1404 wherein, citing Ex parte Forman, 230 USPQ 546 (Bd. Apls. 1986) at 547 the court recited eight factors:
1- the quantity of experimentation necessary,
2- the amount of direction or guidance provided,
3- the presence or absence of working examples,
4- the nature of the invention,
5- the state of the prior art,
6- the relative skill of those in the art,
7- the predictability of the art, and
8- the breadth of the claims
These factors are always applied against the background understanding that scope of enablement varies inversely with the degree of unpredictability involved. In re Fisher, 57 CCPA 1099, 1108, 427 F.2d 833, 839, 166 USPQ 18, 24 (1970). Keeping that in mind, the Wands factors are relevant to the instant fact situation for the following reasons:
The nature of the invention:
The nature of the invention relates to compounds a process for producing an alkylene oxide
comprising reacting an alkene with an arene oxide, pyridine N-oxide and/or pyrimidine N-oxide, in the presence of a catalyst. Such compounds are useful for industrial applications.
Predictability of the art:
The hypothetical compounds produced in claim 1 through the instant method of claim 1 would be unpredictable in terms of one skilled in the art being able to synthesize every possible compound claimed in instant claim 1, using any arene oxide or any pyridine N-oxide or any alkene. It is well established that “the scope of enablement varies inversely with the degree of unpredictability of the factors involved,” and physiological activity is generally considered to be an unpredictable factor. See In re Fisher, 427 F.2d 833, 839, 166 USPQ 18, 24 (CCPA 1970).
Level of skill in the art:
An ordinary artisan in the area of small molecule synthesis would have experience in synthesizing chemical feedstocks for industrial purposes, such as a process chemist or chemical engineer. The level of skill in the art is considered high.
The breadth of the claims:
The scope of the claims involves a process for producing an alkylene oxide comprising reacting
an alkene with an arene oxide, pyridine N-oxide and/or pyrimidine N-oxide, in the presence of a catalyst. Such compounds are useful for industrial applications.
Claim 1 is very broad in the number of arene oxides, pyridine N-oxides, and alkenes that can be employed in the instant method. There is an extremely large amount of hypothetical starting materials.
The amount of direction provided, the presence or absence of working examples, and the quantity of experimentation necessary:
The specification only demonstrates the use of hexafluorobenzene oxide, hexachlorobenzene oxide, and pentafluoropyridine N-oxide as the oxygen transfer reagent in the epoxidation of alkenes (page 27-29, Examples 1-5). The specification does not demonstrate the use of substituted or unsubstituted pyrimidine N-oxide at all. Additionally, the specification provides computational data (page 26, Table 1) that shows the simulated activation energy (Ea) required for the oxygen transfer to occur, using hexafluorobenzene oxide, hexachlorobenzene oxide, and pentafluoropyridine N-oxide as the source of oxygen. It is presumed that the highly electron-withdrawing nature of these arene- and pyridine N-oxides is necessary for the reaction to occur at reduced Ea. The specification provides no data to suggest that the process of instant claim 1 would proceed with the proto versions of each of these species (e.g. benzene oxide, pyridine N-oxide). It would be expected that varying the substituents on the arene oxide or pyridine N-oxide would change the reactivity of the compounds, and therefore may require alternate reaction conditions to afford successful oxidation of alkene.
Additionally, the only alkene used in the reaction is propene to afford final product of propylene oxide (page 27-29, Examples 1-5). It would be assumed that the inventors are also enabled for all alkenes with hydrocarbon functionality only. However, inventors are not enabled for alkene substrates that include heteroatoms. It would be expected that heteroatoms would: alter the reactivity of the alkene double bond towards epoxidation; interfere or bind with the metal required in the catalytic cycle; and/or ring-open the arene oxide, to name a few possibilities.
Last, the specification does not provide any working examples where the process of claim 1 is done in the absence of solvent (see instant claim 11) – a so-called “neat” reaction. In all of the examples (page 27-29, Examples 1-5), only inert solvents (e.g. perfluorodecalin, hexafluorobenzene) are used.
It would require one skilled in the art, such as a chemist, to perform thousands of reactions to determine which alkylene oxides can be produced using any arene oxide, any pyridine N-oxide, and any alkene, additionally in the absence of a solvent, and would likely require synthesis methods other than those provided in the specification. This is undue experimentation given the limited guidance and direction provided by Applicants.
Accordingly, the instant claims do not comply with the enablement requirement of 35 U.S.C. 112(a), since to practice the claimed invention a person of ordinary skill in the art would have to engage in undue experimentation, with no assurance of success.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1, 8, 10, 12-13 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Samsel.
Regarding claims 1, 8, 10: Samsel teaches that norbornene (an alkene) can be epoxidized using (salen)CrIII metal using in the presence of pyridine N-oxide in acetonitrile solvent under argon (see reference Table 1; see page 7616, “Procedure for the Catalytic Epoxidation with Salenchromium(III)”).
Regarding claims 12-13: The specification, specifically Examples 1-5 on pages 27-29, does not provide any rationale as to why metering in the alkene and arene oxide, pyridine N-oxide, and/or pyrimidine N-oxide continuously or stepwise would matter, or why withdrawing the alkylene oxide continuously or stepwise, would matter. Therefore, any method of adding the reagents or removing the product may be treated the same, unless there is evidence to the contrary. As such, this limitation in the methods of instant claims 12-13 has not been given any weight.
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 for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim 11-15 are rejected under 35 U.S.C. 103 as being unpatentable over Samsel.
The previous 102 rejection is incorporated herein.
Regarding claim 11: Claim 11 is drawn to the process of claim 1, wherein the production of the alkylene oxide is effected in the absence of a solvent. Use of one of the reactants as a solvent is standard procedure and is not a patentable modification. In re Dunn, 146 USPQ 479. In the instant case, claim 1 is drawn to an alkene, which includes 1-octene, which is a liquid at room temperature, and therefore, one of the reactants (e.g. 1-octene) can be used as a solvent.
Regarding claim 12-13: Regarding reagent addition, Samsel teaches, on page 7616, “Procedure for the Catalytic Epoxidation with Salenchromium(III)”):
A typical procedure for the catalytic epoxidation of olefins was carried out with 12 mg (0.055 mmol) of iodosylbenzene suspended in a solution consisting of 1.1-1.3 mmol of olefin, 0.011 mmol of salenchromium(III) complex lb, 0.006 mmol of pyridine N-oxide (added as 5 μ of a 1.2 M solution in CH3CN), and an internal standard (either chlorobenzene or n-decane) in 1 mL of acetonitrile which was sealed under argon.
It is well established that batch and continuous processes are not patentably distinct. See, In re Dilnot, 319 F.2d 188, 138 U.S.P.Q. 248 (C.C.P.A. 1963). Continuous addition of a component instead of all at once addition is prima facie obvious. In re Lincoln and Burke 530 USPQ 40.
Regarding claim 14-15: Samsel performs the reaction as a “one-pot” procedure. Applicant is claiming a “two-pot” procedure, wherein the “arene oxide, pyridine oxide and/or the pyrimidine N-oxide” are produced in a separate reactor. Performing a “one-pot” procedure as a “two-pot” procedure is not a patentable modification because it can be logically assumed that the prior art set forth the least number of steps thought necessary. In re Freed, 425 F.2d 785, 165 U.S.P.Q. 519 (C.C. P.A. 1970); see also, Fromson v. Advance Offset Plate Inc., 775 F.2d 1549, 225 (J.S.P.Q. 26 (Fed. Cir. 1985).
Claim 15, which depends on claim 14, is drawn to the addition of reagents, specifically metering in the arene oxide, pyridine N-oxide, and/or pyrimidine N-oxide continuously or stepwise. The specification, specifically Examples 1-5 on pages 27-29, does not provide any rationale as to why metering in these reagents continuously or stepwise would matter. Therefore, any method of adding the reagents may be treated the same, unless there is evidence to the contrary. As such, this limitation in the methods of instant claims 15 have not been given any weight.
Furthermore, it is well established that batch and continuous processes are not patentably distinct. See, In re Dilnot, 319 F.2d 188, 138 U.S.P.Q. 248 (C.C.P.A. 1963). Continuous addition of a component instead of all at once addition is prima facie obvious. In re Lincoln and Burke 530 USPQ 40.
Conclusion
All claims are rejected.
No claims are allowed.
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/L.A.B./Examiner, Art Unit 1624
/SUSANNA MOORE/Primary Examiner, Art Unit 1624
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