Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
This Office action is responsive to Applicant's Response to Election/Restriction, filed 04 September, 2025. As filed, Claims 1-48 are pending.
Priority
This application, 06/21/2022 is a National Stage entry of PCT/US21/12466 , International Filing Date: 01/07/2021; PCT/US21/12466 Claims Priority from Provisional Application 62960773 , filed 01/14/2020.
Election/Restrictions
Applicant's election without traverse of the species as shown below in the reply filed on 9/04/2025 is acknowledged:1) phenyl phosphine (PhPH2) as the primary phosphine;2) pentaphenylcyclophosphine(Ph5P5); (i.e., (Ph-P)n, with n = 5) as the corresponding compound of the formula(R-P)n;3) tris(pentaflurophenyl)borane (C18F15B; BCF) as the Lewis acid;and 4) for the starting materials of each of independent claims 1 and 17: Ph5P5 as the cyclophosphane having the general formula (R-P)n of the precursor, wherein R is Ph, P is phosphorous, and n = 5 and BCF as the Lewis acid .
Applicants indicated that the elected species reads on claims 1-8, 10-13, 17-22, and 24-27.
Applicants' elected species have been found not allowable due to the following rejections.Claims 9, 14-16, 23, 28-48 are withdrawn from further consideration as being drawn to a nonelected species. Claims 1-8, 10-13, 17-22, and 24-27 are examined on merits to the extend they read on elected species.
Information Disclosure Statement
Applicants' information disclosure statements (IDS) filed 6/21/2022 have been considered except where lined through. Please refer to Applicants' copy of the 1449 submitted herewith.
Claim Objections
1.Claims 2, 18, are objected to because of the following informalities: the recitation in parenthesis “(C18F15B) (BCF)” should be amended to delete the abbreviation “(BCF)” to address redundancy.
2. Claims 6, and 21 are objected to because of the following informalities: the recitation in parenthesis “(CH2Cl2) (DCM)” should be amended to delete the abbreviation“(DCM)” to address redundancy. Similar for “(C4H8O) (THF)”, “((C2H8)20) (DEE)”.
3.Claims 1, 8, 17 should be amended to delete the recitation “so as” to avoid potential indefiniteness issues.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claims 1-8, 10-13, 17-22, and 24-27 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.
Claims 1 and 17 recites “cyclophosphane with the general formula (R-P)n where R is any organic functional group”. However, a definition of variable “n” of the Markush structure of instant claim 1 is not provided, rendering said claims and their dependents indefinite.
Claim Rejections - 35 USC § 112
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.
Claims 1-8, 10-13, 17-22, and 24-27 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Applicants claims a method of preparing a primary phosphine product, comprising:
providing a precursor comprising a cyclophosphane with the general formula (R-P)n, where R is any organic functional group;
mixing a Lewis acid with the precursor to provide a mixture;
treating the mixture of the precursor and the Lewis acid with hydrogen under reaction conditions suitable for forming the primary phosphine product from the mixture;
and separating the Lewis acid from the primary phosphine product so as to isolate the primary phosphine product.
There is no chemical structure provided in the claims for the primary phosphine product and there is no core structure that is shared by all species within formula (R-P)n in which R is any organic functional group. In fact, (R-P)n is drawn to multiple core structures, as evidenced by the breadth in the definitions of the variable R “any organic functional group” to perform claimed function.
Regarding the cyclophosphane reactant, instant disclosure provide on [0013]:
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The specification definition uses the phrase “may include," which means that the examples are non-limiting and the definition is open-ended.
There is neither specific definition of variables R or n of the claimed Markus formula (R-P)n other than “R Is any organic functional group” nor a correlation between the disclosed function and the structure(s) responsible for the function of undergoing hydrogenation reaction mediated by Lewis acid under ”suitable reaction condition” and to obtain any “primary phosphine product”.
By contrast, the nature and scope of the invention described in the Specification limited to preparation of compounds phenylphosphine (PhPH2) starting with cylophenylphosphane as precursor (example on [0029) and preparation of methyl phosphine (MePH2)starting with cyclomethylphosphane as precursor (example on [0031];
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The species in the specification are not representative of the entire genus as claimed: preparation of any primary phosphine by reacting a precursor comprising cyclophosphane with the general formula (R-P)n, where R is any organic functional group under “suitable reaction conditions”.
The specification does not show any other examples of preparing a primary phosphine product by reacting a precursor comprising a cyclophosphane with the general formula (R-P)n, where R is any organic functional group with Lewis acid. As such a person skilled in the art would not recognize the written description of the invention as providing adequate support for the entire scope of the claimed invention.
Applicant has not described the claimed method of preparing a primary phosphine product by reacting a precursor comprising a cyclophosphane of formula (R-P)n in a manner that would indicate they were in possession of the full scope of the claimed genus, or even to describe what this genus is comprised of.
Regarding the requirement for adequate written description of chemical entities, Applicant's attention is directed to the MPEP §2163.
In the instant case, the claimed method of preparing a primary phosphine product, comprising a cyclophosphane with the general formula (R-P)n, where R is any organic functional group. The full scope of the claimed genus is far larger than the number of species exemplified by applicants- preparation of phenylphosphine from cyclophenylphosphane and preparation of methylphosphine from cyclomethyllphosphane.
In addition to lacking an adequate number of species, the disclosure fails to show a structural feature shared by all species of formula (R-P)n or primary phosphine and to define a genus whose members can be “visualize[d] or recognize[d]” by the skilled artisan.
The specification, then, is considered absent of sufficiently detailed, relevant, identifying characteristics demonstrating that Applicant was in possession of the genus now claimed, i.e., additional complete or partial structures, other physical and/or chemical properties, functional characteristics coupled with a known or disclosed correlation between function and structure, demonstrating possession of the entirety of the claimed genus.
Instant claims do not comply with the written description requirement because the disclosure does not provide a representative number of species falling within the scope of the genus compound of formula (R-P)n or the primary phosphine products of the method as recited in the claim. As such, the claims lack adequate written description for the claimed method for preparing a primary phosphine product.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102 of this title, 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 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.
Graham v. John Deere Co., 383 U.S. 1, 17 (1966); MPEP § 2141(11).
Claims 1-8, 10-13, 17-22, and 24-27 are rejected under 35 U.S.C. 103 as being unpatentable over US 2008/0071115, March 2008 by Sommerlade et al. (hereinafter “the ‘115 publication”; cited in by Applicants in IDS) in view of Geier, Transition metal complexes and main group frustrated Lewis pairs for stoichiometric and catalytic P-P and H-H bond activation, University of Toronto, Ph.D., Thesis, 2010, 40-63 (cited by Applicants in IDS).
The Graham factors are addressed in tum below.
Determining the scope and content of the prior art
The ‘115 publication discloses a method of preparing a primary phosphine product,
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(see claim 1 of the ‘115 publication). The ‘115 publication teaches in-situ formation of the cyclophosphane precursor intermediate on [0066] while the preparation of pentaphenyl-pentaphospholane (PhP)5 - which corresponds to the cyclophane precursor of disclosed formula where R is any organic functional group – i.e. phenyl and the elected species- which is upon treatment with hydrogen under reaction conditions suitable for forming the primary phosphine product. Disclosed on [0057] of the ‘115 publication is that the reaction products can be isolated and purified by conventional processing methods known to the skilled person; the phenylphosphanes are obtained in high yield and with high selectivity (instant claims 1, 8,10-13; 17, 20, 24-27).
Example 2 on [0068] illustrated preparation of phenylphosphane (PhPH2)- the elected species- the method comprising: treating dichlorophenylphosphane - which corresponds to the claimed precursor comprising a cyclophosphane - with hydrogen at 20 bar ant 150⁰C:
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Regarding the limitation of solvent of instant claims, the ‘115 publication teaches reaction conducted in toluene under argon atmosphere; [0022]; [0068]; instant claims 5-6, 20-21).
Ascertaining the differences between the prior art and the claims at issue
The method of the present application differs from the method described in the 15 publication in that prior art does not teach Lewis acid catalyst for formation of the same product -a primary phosphine by treatment of a cyclophosphahe precursor under hydrogenation conditions.
It is noted that conducting the reaction under Lewis acid catalysis as alternative catalyst for the reaction of primary phosphine formation, is a known option in the prior art as discussed in the article by Geier.
Geier teaches activation of phosphorus-hydrogen or phosphorus-phosphorus bonds allows for the facile synthesis of new phosphorus-containing compounds by metal-free small molecule activation, containing a bulky Lewis acid and Lewis base which are unable to bond directly due to steric repulsion - "frustrated Lewis pair" (FLP) ;the concept expanded to bulky P-P bound species, pyridines and P-O bound Lewis bases as partners for B(C6F5)3 – which corresponds to the Lewis acid elected species (abstract). Disclosed on page 45 of the prior art by Geier is aspects of hydrogenation of P5Ph5 ( which corresponds to the elected species of precursor comprising cyclophosphane) by mixing a Lewis acid B(C6F5)3 with the precursor P5Ph5 (22 mg, 0.041 mmol) in toluene treating the mixture of the precursor and the Lewis acid with hydrogen under reaction conditions suitable for forming the product from the mixture.
Furthermore, Geier teaches that the Lewis acid can be separated from the primary phosphine product; at elevated temperatures, these can dissociate in solution, generating free phosphine and borane; page 40-41, Figure 3.1; page 59, Figure 3.12 reproduced below:
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(instant claims 2-8, 18-22). Geier teaches that functionalization of polyphosphines via FLP reactivity by Lewis acid activation is a metal-free hydrogenation methodology alternative in preparing organophosphines, making the process more cost·effective and eliminating the usage of toxic raw materials (page 42).
The question of obviousness
Based on the above factors, it would have been obvious for a person having ordinary skill in the art prior to the filing of the instant application to combine and modify the disclosures of the ‘115 publication and to utilize the Lewis acid activation hydrogenation synthetic strategy as taught by Geier to arrive at the claimed invention.
When considered as a whole, the cited references establish one of ordinary skill in the art would have been motivated to modify or combine the cited references to provide functionalization of polyphosphines by Lewis acid activation and a metal-free hydrogenation methodology which is more cost·effective and environmentally friendly.
There would have been a reasonable expectation of success at arriving at the claimed invention because the use of Lewis acid activation in the synthesis of organophosphines was known at the time of filing of the instant application.
The rationale to support a conclusion that the claim would have been obvious is that teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. KSR, 550 U.S. at_, 82 USPQ2d at 1395.
Thus, the claimed invention as a whole is prima facie obvious over the combined teachings of the prior art.
Conclusion
Claims 1-8, 10-13, 17-22, and 24-27 are rejected. Claims 9, 14-16, 23, 28-48 are withdrawn from further consideration.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692