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 .
Application Status
The claim set filed on 9/25/2023 is acknowledged. Claims 1-7 are currently pending and under consideration
Claim Objections
Claims 1 and 4 are objected to because of the following informalities: The spacing between some of the words within the claims seems to not be present. For example, in claim 1 “theprecipitation” or “nitricacid” and in claim 4 “conductedin”.
In view of the claim interpretation below, it is suggested that applicants provide a clear association between the claimed compound named in claim 1 and “MTX-1” as recited in claim 4. For example, amending claim 1 to remove “(tetrazole derivative”) and replace with “(MTX-1)”. Appropriate correction is required.
Claim Interpretation
The compound 1-[(2E)-3-(1H-tetrazol-5-yl)triaz-2-en-1-ylidene]methanediamine has the structure
PNG
media_image1.png
256
237
media_image1.png
Greyscale
, which is also referred to in the art as MTX-1. Accordingly, the examiner is interpreting the named compound to be synonymous with the structure above or MTX-1.
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, 3-4 and 6 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 limitation "the filtered solid". There is insufficient antecedent basis for this limitation in the claim since claim 1 does not previously recite “a filtered solid” or filtering the solid.
Claims 3 and 4, which depends from claim 1, recites the limitation "the aminoguanidine bicarbonate". There is insufficient antecedent basis for this limitation in the claim since claim 1 does not previously recite “aminoguanidine bicarbonate”.
Claim 4 further recites the limitations “a single operational step” when discussing the conversion of aminoguanidine nitrate to MTX-1. However, it is unclear what is encompassed by this language since the claims appear to require two steps, e.g. a treating step 1 and an additional adding step 2. Note: the specification does not appear to define what “a single operational step” encompasses. For prior art purposes, the examiner is interpreting a single opertation step as being that the reaction is a one-pot reaction not requiring any purification of the tetrazene prior to the addition of the nitric acid and sodium nitrite.
Claim 6 recites the limitation “a predetermined duration until the reaction is complete” when referring to the stirring of the reaction mixture. The phrase seems to contradict itself. For example, is the time the limiting factor in how long the reaction occurs or is it the completion of the reaction by using means such as TLC which shows consumption of the starting material.
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 2-5 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 2 recites that the starting material is aminoguanidine nitrate which does not appear to further limit Claim 1 which only recites aminoguanidine nitrate as the starting material.
Claims 3 and 4 recites that the starting material is aminoguanidine bicarbonate which broadens claim 1 in that claim 1 does not recite aminoguanidine bicarbonate.
Claim 5 recites that the in-situ Sandmeyer reaction conditions involve the addition of nitric acid and sodium nitrate which does not appear to further limit claim 1 because claim 1 already recites that the in situ Sandmeyer involves adding these two agents to the reaction mixture. 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 § 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(s) 1-3 and 5-6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Fronabarger and Williams (US8524019B2, 2013-11-03) in view of Patinkin et al. (J. Am. Chem. Soc. 1955; 77(3), 562-567) and Anderson, Neal (Practical Process Research and Development, San Diego, Academic Press, 2000).
Fronabarger and Williams teach that Tetrazene is widely used in ordinance systems as a sensitizer of primer mixes for use in both percussion and stab applications (column 1, lines 28-31). However, Fronabarger and Williams teach that Tetrazene suffers from a number of issues, most importantly low thermal and hydrolytic stabilities, wherein it has been demonstrated that Tetrazene readily decomposes at approximately 90C which is the temperature range that may be encountered during storage and some parts of the world (Column 2, lines 24-29). Accordingly, Fronabarger and Williams teach a possible alternative to Tetrazene referred to as MTX-1 which is conveniently prepared from Tetrazene in one step from an aqueous solution (Column 3, lines 63-67). For example, Fronabarger and Williams teach MTX-1 was prepared by suspending Tetrazene in HNO3 (Nitric acid) and adding NaNO2 (Sodium Nitrite) dissolved in 30mL of water to the suspension at room temperature, stirring the reaction for 4.5 hrs, filtering the white suspension, washing the white suspension with water and drying in a convection over at 60oC.
Fronabarger and Williams doe not specifically teach how tetrazene was produced or that MTX-1 was washed with water and isopropyl alcohol.
Patinkin et al. teach the reinvestigation of the structure of the primary explosive Tetracene (Abstract). Specifically, Patinkin et al. teach a method of making Tetracene comprising mixing aminoquanidinium nitrate in water with sodium nitrite at room temperate and reacting the mixture for 40 hrs until a solid had formed, washing with water, ethanol and water (page 566, 1st column, 1st full paragraph of Experimental).
Anderson teaches that there are two purposes in applying a wash to a product wet cake. (page 241). The most common is to displace impurities adsorbed as mother liquor to the surfaces of solids (page 241). The second reason for applying a wash to a wet cake is to displace the solvent with another solvent, usually a lower-boiling solvent to ease drying of the product. In this case it is essential that the solvent applied dissolve as little product as possible and temperature selection may be important (page 241). Anderson teaches guidelines for washing a product in Table 11.6. Anderson further provides a listing of common solvents such as ethanol and isopropyl alcohol and their respective boiling point 78oC and 81oC respectively (page 86, Table 4.3).
It would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention, to modify the method taught by Fronabarger and Williams to prepare Tetrazene by the method taught by Patinkin et al.. One of ordinary skill in the art would have been motivated to make such a modification, with a reasonable expectation of success, because:
- Fronabarger and Williams teaches that one of the disadvantages of Tetrazene is decomposition, specifically decomposition at storage temperatures. For example, Fronabarger and Williams teach that the decomposition of Tetrazene is complete after 1 week at 90oC and appears to be auto-catalytic (column 2, lines 53-55).
Moreover, it would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention, to modify the method taught by Fronabarger and Williams to include isopropyl alcohol in addition to water in the wash step in view of the teachings of Anderson. One of ordinary skill in the art would have been motivated to make such a modification, with a reasonable expectation of success, because:
- Anderson teaches that the second reason for applying a wash to a wet cake is to displace the solvent with another solvent, usually a lower-boiling solvent to ease drying of the product. In this case it is essential that the solvent applied dissolve as little product as possible and temperature selection may be important
Claim(s) 1-3 and 5-6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Fronabarger and Williams (US8524019B2, 2013-11-03) in view of Patinkin et al. (J. Am. Chem. Soc. 1955; 77(3), 562-567) and Anderson, Neal (Practical Process Research and Development, San Diego, Academic Press, 2000), as applied above to claims 1-3 and 5-6, in further view of Hayashi, Yujiro (Chem. Sci. 2016; 7: 866).
The teachings of the combination have been set forth above and incorporated herein. In short, the combination as set foth above teach a method of synthesizing MTX-1 by first producing Tetrazene by reacting aminoquanidinium nitrate in water with sodium nitrite at room temperate to form a solid, followed by producing MTX-1 by reacting Tetrazene in HNO3 (Nitric acid) with NaNO2 (Sodium Nitrite) dissolved in 30mL of water.
The combination does not specifically teach that the reaction occurs as a one-pot synthesis which does not require purification of the Tetrazene.
Hayashi teaches that the one-pot synthesis of a target molecule in the same reaction vessel is widely considered to be an efficient approach in synthetic organic chemistry because several synthetic transformations and bond forming steps can be carried out in a single pot which circumvents several purification procedures at the same time (Abstract and p 866 2nd column, paragraph bridging 1st column). Thus, Hayashi teaches that one-pot synthesis can thus minimize chemical waste, save time and simplify practical aspects (p 866 2nd column, paragraph bridging 1st column).
It would have been prima facie obvious to one of ordinary skill in the art, prior to the effective filing date of the instantly claimed invention, to modify the method taught by the combination to a one-pot synthesis in view of the teachings of Hayashi. One of ordinary skill in the art would have been motivated to make such a modification, with a reasonable expectation of success, because:
-Hayashi recognizes the efficiencies that can be gained by performing a series of steps in one-pot,
- Fronabarger and Williams teach the disadvantages of Tetrazene (the intermediate) include temperature stability, as well as, hydrolytic decomposition (column 2, lines 53-63); and further
-Both Fronabarger and Williams and Patinkin et al. chemical reactions formed in the same solvent system (water) and both utilize sodium nitrite.
Conclusion
Therefore, No claim is allowed.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
-Fronabarget et al. (Central European Journal of Energetic Materials, 2016; 13(1), 33-52).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BRANDON J FETTEROLF whose telephone number is (571)272-2919. The examiner can normally be reached M-F 6AM-4PM.
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, Jeffrey S Lundgren can be reached at 571-272-5541. 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.
BRANDON J. FETTEROLF, PHD
Primary Patent Examiner
Art Unit 1626
/BRANDON J FETTEROLF/Primary Examiner, Art Unit 1626