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 .
Status of the Claims
Claims 1-15 are pending and currently under examination.
Election/Restrictions
The restriction requirement between Group I, claims 1-14 and Group II, claim 15, as set forth in the Office Action mailed on 03/17/2026, has been reconsidered and is hereby withdrawn.
The election of species requirement for compound Y, as set forth in the Office Action mailed on 03/17/2026, has been reconsidered and is hereby withdrawn.
In view of the above noted withdrawal of the restriction requirement, Applicant is advised that if any of the claim represented in a divisional application is anticipated by, or includes all the limitations of, a claim that is allowable in the present application, such claims may be subject to provisional statutory and/or non-statutory double patenting rejections over the claims of the instant application.
Once a restriction requirement is withdrawn, the provisions of 35 U.S.C. 121 are no longer applicable. See In re Ziegler, 443 F.2d 1211, 1215, 170 USPQ 129, 131-32 (CCPA 1971). See also MPEP §804.01.
Claim Objections
Claim 1 is objected to because the phrase “Process comprising the process steps of” should read “A process comprising the process steps of”.
Claim 1 is further objected to because the phrase “wherein R1, R2, R3 are selected from -H, -(C1-C12)-alkyl, -O-(C1-C12)-alkyl, -CN, -NO2” should read “wherein R1, R2, and R3 are selected from -H, -(C1-C12)-alkyl, -O-(C1-C12)-alkyl, -CN, and -NO2”
Claims 2-14 are objected to because the phrase “Process according to” should read “The process according to” in each of these claims.
Claim 14 is objected to because the phrase “wherein the solvent is selected from: acetonitrile (ACN), toluene, xylene, THF, heptane” should read “wherein the solvent is selected from[[:]] acetonitrile (ACN), toluene, xylene, THF, and heptane”.
Claim 15 is objected to because the phrase “Compound according to” should read “A compound according to”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claims 1-14 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.
Claim 1 recites the process step of “initially charging a compound Y…”. It is unclear what is meant by the phrase "charging a compound." In a review of the specification, a definition of the phrase “charging a compound” was not identified. The term “charging” in the art is context-dependent and may refer to multiple things depending on the reaction being carried out, such as initiating with a catalyst or ionically charging a compound. Thus, the process step of “charging a compound” is indefinite. In the interest of compact prosecution and for the purposes of applying art, the phrase "charging a compound Y" is construed as replacing at least one carbon atom of the 5-membered ring with a nitrogen atom, since a nitrogen atom can hold an ionic charge. Claims 2-14, which depend on claim 1, inherit but fail to define this step and are similarly rejected.
Claim 14 recites the abbreviation THF. In a review of the specification, this abbreviation is not spelled out. For examination purposes, it is assumed that THF means tetrahydrofuran.
112(a) – Scope of Enablement
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 1-14 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 process of claim 1 comprising compounds Y and P(NX2)3 as described and compounds of formula (I) wherein R1, R2, R3 are selected from -H, -(C1-C12)-alkyl, and -O-(C1-C12)-alkyl, does not reasonably provide enablement for the full scope of compounds of formula (I), particularly when R1, R2, and R3 are aryl, -CN, or -NO2. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims. This is a scope of enablement rejection.
Pursuant to In re Wands, 858 F.2d 731, 737, 8 USPQ2d 1400, 1404 (Fed. Cir. 1988), one considers the following factors to determine whether undue experimentation is required: (1) The breadth of the claims, (2) The nature of the invention, (3) The state of the prior art, (4) The level of one of ordinary skill, (5) The level of predictability in the art, (6) The amount of direction provided by the inventor, (7) The existence of working examples and (8) The quantity of experimentation needed to make or use the invention based on the content of the disclosure.
Nature of the invention:
The invention is drawn to a process comprising initially charging a five-membered ring Y, adding P(NX2)3, then adding a compound according to the formula (I) depicted below, wherein R1, R2, and R3 are selected from -H, -(C1-C12)-alkyl, -O-(C1-C12)-alkyl, -CN, -NO2, and (C6-C10)-aryl.
PNG
media_image1.png
147
135
media_image1.png
Greyscale
Breadth of the invention:
The scope of the claimed invention is broad, as the compounds of formula (I) can have a number of substituents including alkyl, alkoxy, NO2, CN, and aryl. Furthermore, 0-3 of these substituents may be present.
State of the prior art and predictability in the art:
An ordinary artisan in the area of organic chemistry would understand that different substituents offer different electronic and steric effects that must be considered when planning and conducting a reaction. In the instant case, the effects of different substituents on the phenol compound of formula (I) must be considered in predicting how these compounds will react with the intermediate formed after step b) of the reaction of claim 1.
With regard to electronic effects, Ashenhurst 2017 (“Activating and Deactivating Groups In Electrophilic Aromatic Substitution”) teaches that CN and NO-2 are pi-acceptors and remove electron density from the aromatic ring (p. 8, under header “Pi-acceptor groups are strongly deactivating”). On the other hand, alkyl groups (p. 5, under header ““Sigma” donors and acceptors”) and alkoxy groups are both electron-donating.
In addition, Ashenhurst 2012 (“What Makes A Good Nucleophile?”) teaches that as electron density increases, so does nucleophilicity (p. 2, section “The Role of Charge”). In addition the bulkier a given nucleophile is, the lower its nucleophilicity (p. 4, section “Steric hindrance”). Bulkier groups such as tert-butyl and aryl will sterically hinder reactions, whereas more compact groups such as CN will not.
These competing factors illustrate that the effect of substituents, including CN, NO2, and aryl, must be weighed when determining if a desired reaction will take place.
Level of ordinary skill in the art:
One of ordinary skill in the art would have experience dealing with homologs in reactions and treating these classes similarly (e.g., treating methyl and ethyl substituents the same or treating halogens the same). In addition, the skilled artisan would understand that factors such as solvent choice and reaction temperature are routine variables to modify and optimize for reaction schemes. However, for compounds with different classes of substituents, such as a compound of formula (1) substituted with alkyl vs. aryl vs. CN, the electronic and steric effects mentioned above mean that one cannot always predict from first principles how a given reaction will take place.
The amount of direction provided and working examples:
The specification provides the following reaction as an example (p. 4, line 1), where compound Y is tetrazole, P(NX2)3 has X = C1 alkyl (methyl), and the compound of formula (I) has R-1 = H and R-2 and R3 both tert-butyl.
PNG
media_image2.png
384
1027
media_image2.png
Greyscale
Depending on the exact mechanism of the reaction of the phenol compound of formula (I) with the phosphorous tris-azole intermediate, different substituents will affect the reaction in competing and unpredictable ways. Although aryl and alkoxy substituents will likely function similarly to the given example with tert-butyl substituents, the use of CN, NO2, or aryl would be less clear. This unpredictability would require undue experimentation to determine what substituents for compounds of formula (I) can or cannot be used in the reaction.
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.
Claim 15 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shimadzu (Nucleic Acids Research. 1984. Vol. 12, No. 7, Pages 3257-3270, cited in the IDS filed 01/31/2024).
Shimadzu teaches phosphorus tris-azoles prepared according to the following reaction scheme (p. 3259):
PNG
media_image3.png
364
543
media_image3.png
Greyscale
When Az is tetrazole (letter h), (Az)3P is the compound depicted below, which is the same compound as formula (3) of instant claim 15.
PNG
media_image4.png
524
575
media_image4.png
Greyscale
Thus, the reference anticipates the instantly claimed invention.
ConclusionNo claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to OLIVER D. HEES whose telephone number is (571)272-9840. The examiner can normally be reached Monday - Friday 8:00 am - 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, AMY L. CLARK can be reached at (571) 272-1310. 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.
/O.D.H./Examiner, Art Unit 1628
/AMY L CLARK/Supervisory Patent Examiner, Art Unit 1628
Prosecution Insights