DETAILED ACTION
It appears the inventor(s) filed the current application pro se (i.e., without the benefit of representation by a registered patent practitioner). While inventors named as applicants in a patent application may prosecute the application pro se, lack of familiarity with patent examination practice and procedure may result in missed opportunities in obtaining optimal protection for the invention disclosed. The inventor(s) may wish to secure the services of a registered patent practitioner to prosecute the application, because the value of a patent is largely dependent upon skilled preparation and prosecution. The Office cannot aid in selecting a patent practitioner.
A listing of registered patent practitioners is available at https://oedci.uspto.gov/OEDCI/. Applicants may also obtain a list of registered patent practitioners located in their area by writing to Mail Stop OED, Director of the U.S. Patent and Trademark Office, P.O. Box 1450, Alexandria, VA 22313-1450. Claims 1-10 filed on 09/29/2023 are pending and are currently examined.
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 .
Claim Objections
Claims 1 and 2 are objected to because of the following informalities: In claim 1, the recitation of “the solid precursor compound” (line 8) should be changed to “the precursor compound” to comply with the preceding recitation of “a precursor compound” and subsequent recitation “the precursor compound”. Additionally, it is recommended that the applicant insert the missing phrase “containing a sodium cation” immediately before the recitation of “with methanolic” (line 11) to comply with the subsequent “the sodium cation” (line 12). It is also recommended that the applicant insert the missing word “to” immediately before the recitation “generate” (line 12) and delete the excessive recitation “The synthesis involves” (line 16). In claim 2, it is recommended that the applicant change the incorrect recitation “facilitating a one-step” (line 3) to “and to facilitate a one-step” to refer to the preceding “specific ratio”; and delete the redundant recitation “in one step” (at the end of the claim). 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 1-10 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 2, 3, 6, 9, and 10 depend from claim 1.
Claims 1b, 1f, and 8 lack antecedent basis which renders the claims indefinite. In 1b for “the reaction mixture” lacks antecedent basis. It is recommended that the applicant change the phrase to “a reaction mixture. In 1f there is no “a penultimate” phrase in the preceding clause therefore 1f lacks antecedent basis. The applicant should amend the recitation “forming the penultimate intermediate compound” in 1f to “to form a penultimate intermediate compound”. Additionally, “the resulting filtrate” in 1f lacks antecedent basis which can be overcome by changing the recitation “reaction between sodium azide” in 1a of claim 1 to “reaction in a reaction mixture containing sodium azide” and inserting the phrase “to obtain a filtrate” immediately after the recitation “the sodium chloride” in line 1 of step 1f, respectively. Claim 8 recites the limitation "the precipitation of sodium chloride" to completion in line 3. There is insufficient antecedent basis for this limitation because “the” should refer back to the preceding limitation.
In the present instance of claim 1g and 7, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). Claim 1g and 7 recite the broad recitation potassium alkoxide, and the claims also recites preferably potassium tert-butoxide which is the narrower statement of the range/limitation. The claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. To advance the prosecution, the “potassium alkoxide” will be examined as the broadest reasonable interpretation.
The term “good” in claim 1gis a relative term which renders the claim indefinite. The term “good” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Yield and purity are therefore rendered indefinite. To advance the prosecution, “good” is interpreted as any.
Claim 4 and 5 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being incomplete for omitting essential structural cooperative relationships of elements, such omission amounting to a gap between the necessary structural connections. See MPEP § 2172.01. The omitted structural cooperative relationships are: The recitation “in subsequent steps without isolation or purification” in lines 2 to 3 of claim 4 contradicts the “to precipitate the precursor compound” in claim 1a, “filtration” in claim 1c, “air-drying” in claim 1d, and so on. To advance the prosecution, the limitation “without isolation or purification” was excluded to meet the broadest reasonable interpretation.
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 (i.e., changing from AIA to pre-AIA ) 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, 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 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Caruana et al. (Published 06 January 2015, US 8927734 B1) in view of Srinivas et al. (2014, New Journal of Chemistry, 38(8), 3699–3707), Gitis et al. (1960, Zhurnal Obshchei Khimi, 30, 3807-10) and Urbański (1965, Chemistry and Technology of Explosives, Pergamon Press).
With regard to steps (a) to (d) of claim 1, Caruana et al. teaches a method of potassium 5,7-dinitro-[2,1,3] -benzoxadiazol-4-olate-3-oxide (KDNP) synthesis using starting reactants of an azide and a heteroaromatic compound (Figure 1 and Column 2, lines 20 -25). They specifically suggest that sodium or potassium azide could be used as a reactant (Column 2, lines 23-25). Caruana et al. also teaches synthesis using a temperature of 90° C and high-boiling organic solvent and water (Column 2, lines 32 – 53). The reaction can be actively cooled using an ice bath (0° – 5° C) and the product is precipitated (Column 2, lines 56 and 57; Column 3, lines 1 and 2). Caruana et al. then teaches filtration and isolation of KDNP (Column 3 lines 3-6, Column 4 lines 2-7).
PNG
media_image1.png
232
554
media_image1.png
Greyscale
Caruana et al. differs from the instantly claimed invention in (A) the specific starting reactant of 3-chloro-2,4,6-trinitrophenol, the solvent system of methanol, the use of HCl, the precursor compound sodium 5,7-dinitro-[2, 1,3]benzoxadiazol-4-olate-3-oxide, and the penultimate intermediate compound 5,7-dinitro[2, 1,3 ]-benzoxadiazol-4-ol-3-oxide, required by step (a), (e), and (f) of claim 1, and claims 2-9, and (B) the potassium alkoxide or potassium tert-butoxide used, required by step (g) of claim 1 and claims 7 and 10.
With regard to the limitation (A) above, Srinivas et al. teaches the starting reactant of 3-chloro-2,4,6-trinitrophenol reacting with sodium azide in methanol to produce the energetic salt, 3-azido-2,4,6-trinitrophenol (3-AzPA) (Scheme 2).
PNG
media_image2.png
142
486
media_image2.png
Greyscale
Srinivas et al. notes the “displacement” of the chlorine of 3-chloro-2,4,6-trinitrophenol by azide occurred to yield 3-azido-2,4,6-trinitrophenol (pg. 3700, right col., paragraph 2). The use of HCl for washing after nitration, precipitation, and filtration in the energetic salt synthesis is also disclosed in Srinivas et al. (pg. 3704, right col., paragraph 5).
Furthermore, with regard to the limitation (B) above, Gitis et al. teaches and suggests claims 7 and 10 through the disclosure of potassium tert-butoxide to produce the potassium salt of the nitrated heteroaromatic compound 2,4,6-(NO2)3C6H2OMe. The abstract from Gitis et al. states:
PNG
media_image3.png
255
1144
media_image3.png
Greyscale
In addition, Gitis et al. (1960, Zhurnal Obshchei Khimi, 30, 3807-10) discloses the following structure containing the potassium tert-butoxy group:
PNG
media_image4.png
231
357
media_image4.png
Greyscale
Moreover, Urbański disclosed that potassium ethoxylate and potassium methoxylate reactants, which are potassium alkoxides, produce the potassium salts of a trinitrophenol compound with further presence of potassium hydroxide.
PNG
media_image5.png
200
400
media_image5.png
Greyscale
(19)
PNG
media_image6.png
200
400
media_image6.png
Greyscale
(20a) (pg. 202, scheme 19 and pg. 203, scheme 20a).
Accordingly, it would have been prima facie obvious to one of ordinary skill in the art at the time the invention was filed to combine the 3-chloro-2,4,6-trinitrophenol and sodium azide reactants of Srinivas et al. with the conditions and steps of Caruana et al. to yield a sodium salt of 5,7-dinitro-[2, 1,3]benzoxadiazol-4-olate-3-oxide, followed by HCl wash to obtain 5,7-dinitro[2, 1,3 ]-benzoxadiazol-4-ol-3-oxide, and subsequent treatment with potassium alkoxide, including the potassium tert-butoxide or potassium ethoxylate with potassium hydroxide step in view of Gitis et al. and Urbański to obtain KDNP because the references teach structurally and functionally similar reactants and compatible reaction conditions employed for energetic salt synthesis. Thus, one of skill in the art would have a reasonable expectation of success by combining the reactants as taught by Srinivas et al. with the steps of Caruana et al. and alkoxide of Gitis et al. and Urbański, to achieve Applicant's claims 1-10.
Conclusion
No claims are allowed in this action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RAJESH JAIPRASHAD whose telephone number is (571)272-1049. The examiner can normally be reached Monday-Friday 8AM-5PM.
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, Renee Claytor can be reached at 571-272-8394. 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.
/RAJESH JAIPRASHAD/Examiner, Art Unit 1691
/YIH-HORNG SHIAO/Primary Examiner, Art Unit 1691