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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 9/03/2026 has been entered.
Claims 1, 4 and 6 are currently pending and under consideration.
Claim Interpretation
Claim 1 has been amended to recite “…subjecting the solid directly to in-situ Sandmeyer reaction conditions without isolation, and adding nitric acid drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC to obtain a reaction mixture;….”. The claims do not specifically recite what the reaction conditions of the Sandmeyer reaction are. The claim 1 of the claim set filed on 5/12/2026 recite “… subjecting the solid to in-situ Sandmeyer reaction conditions by adding nitric acid and sodium nitrite to obtain a reaction mixture….”. The specification as originally filed teaches the following:
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Thus, in view of the previous claim set and specification, as originally filed, the Examiner is interpreting in-situ Sandmeyer conditions to be the addition of nitic acid and sodium nitrite which create the required conjugated double bonds in the molecule’s backbone.
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, 4 and 6 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. THIS IS A NEW MATTER REJECTION.
Claim 1 has been amended to recite “…b. cooling the solid to 10oC, and subjecting the solid directly to in-situ Sandmeyer reaction conditions without isolation, and adding nitric acid drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC to obtain a reaction mixture;….”. Thus, the claim appears to recite that the in-situ Sandmeyer reaction conditions are separate and/or independent of the addition of nitric acid drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC. However, the specification does not specifically teach these occurring as two different processes with the specificity required by the instant claims and Applicants have not specifically pointed to where in the specification or claims as originally filed support can be found. As noted above in the claim interpretation, the Examiner is interpreting in-situ Sandmeyer reaction conditions to encompass the addition of nitic acid and sodium nitrite. While the Examiner recognizes that the specification contemplates that the reaction may incorporate nitric acid and another batch of sodium nitrite (paragraph 0024), the specific reaction conditions for the addition of nitric acid and sodium nitrite only occur once in the two working examples and this appears to be directly related to in-situ Sandmeyer reaction conditions. In other words, there is no prior addition of nitric acid and sodium nitrite for the Sandmeyer reaction, followed by the addition of nitric acid drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC.
Rejections Maintained, but amended in view of Applicants amendments:
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, 4 and 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), Anderson, Neal (Practical Process Research and Development, San Diego, Academic Press, 2000) and Hayashi, Yujiro (Chem. Sci. 2016; 7: 866).
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 adding a solution of NaNO2 (Sodium Nitrite) in water over approximately 10 minutes, at a constant rate to maintain a temperature of 25oC, to a stirred suspension of tetrazene in 1N aq. HNO3 (Nitric acid) and 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 does not specifically teach how tetrazene was produced or that the reaction occurs as a one-pot synthesis which does not require purification of the Tetrazene. Moreover, Fronabarger and Williams does not explicitly teach the reaction condition as claimed 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 aminoguanidinium 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).
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).
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 the combination of Fronabarger and Williams and Patinkin et al. so as to optimize the reaction conditions and utilize 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 that efficiencies 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);
-Fronabarger and Williams recognize the importance the addition of the reactants at a constant rate to keep the reaction temperature at ambient temperature; and further
-Both Fronabarger and Williams and Patinkin et al. chemical reactions formed in the same solvent system (water) and both utilize sodium nitrite.
Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
See also MPEP 2144.04 (V)(E), In re Dilnot, 319 F.2d 188, 138 USPQ 248 (CCPA 1963) (Claim directed to a method of producing a cementitious structure wherein a stable air foam is introduced into a slurry of cementitious material differed from the prior art only in requiring the addition of the foam to be continuous. The court held the claimed continuous operation would have been obvious in light of the batch process of the prior art.).
Lastly, 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 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
While the rejection has been amended in view of Applicants amendments, the examiner would like to address Applicants arguments as they relate to the present rejection.
In response to the previous rejections, Applicants contend that neither Fronabarger and Williams nor Patinkin teaches nor suggests subjecting the solid directly to in -situ Sanmeyer reaction conditions without isolation and adding nitric drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC to obtain a reaction mixture. Moreover, Applicants contend that adding sodium nitrite to the salt at 10oC initiates an in situ Sandmeyer reaction, resulting in assembling the desired molecular architecture. Applicants further assert that the addition of nitric acid drop by drop over a period of 1 hour and sodium nitrite drop by drop over a period of 0.5 hour at 10oC eliminates the undesired amine functionality from the assembled molecule to furnish MTX-1. Thus, Applicants contend that the desired structural modification to prepare MTX-1, by incorporating reaction conditions that create the required conjugated double bonds in the molecule’s backbone, is achieved by carefully controlling the addition of nitric acid and sodium nitrite and maintaining the reaction at ambient temperature (see paragraph 0017 of the present disclosure). Lastly, Applicants contend that the innovative aspect of the application lies in the fact that the Sandmeyer protocol can be successfully conducted on a nitrate salt without using any acid, wherein the nitrate part serves as the acid, and therefore avoids any acid in the reaction, rendering the reaction clean and leading to a highly pure MTX-1.
These arguments have been carefully considered, but are not found persuasive.
First, Applicants are reminded that the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). As discussed above, both the synthesis of MTX-1 and tetrazene are known in the art, wherein MTX-1 is made using tetrazene as the starting material. However, as noted in the prior art and acknowledged by Applicants, tetrazene suffers from a number of issues such as being both thermally and hydrolytically unstable. As such, it view of the teachings of Hayashi, it would be prima facia obvious to combine the two steps into a one-pot synthesis. Secondly, the Examiner is confused by Applicants arguments regarding the reactants and what they are used for. In particular, Applicants appear to contradict themselves. For example, Applicants argue that the addition of sodium nitrite to the salt initiates an in situ Sandmeyer reaction resulting in assembling the desired molecular architecture. However, Applicants also appear to argue that the required conjugated double bonds in the molecule’s backbone (interpreting as the same as the desired molecular architecture) is achieved by the addition of nitric oxide AND sodium nitrate. Thus, it is confusing because at one-point Applicants appear to argue that it is the addition of sodium nitrite to the salt which forms the “backbone”, but also contends it is the combination of nitric acid AND sodium nitrite. It is important to note that the second interpretation seems to be a more accurate picture of the reaction conditions (see Examiners claim interpretation above). Moreover, the claims do not require a step of adding sodium nitrite to the salt and the specification does not teach or suggest that sodium nitrite alone is responsible for the in situ Sandmeyer reaction. Additionally, Fronabarger and Williams recognize the importance of the addition of the reactants at a constant rate to keep the reaction temperature at ambient temperature (as noted above). Lastly, regarding Applicants arguments pertaining to the innovative aspect of the application, the examiner has reviewed the specification and there is no teaching that the Sandmeyer protocol can be successfully conducted on a nitrate salt without using any acid. In contrast, both the examples of the specification use nitric acid. Moreover, the claims require nitric acid. As such, the Examiner is again confused about how there is no acid in the reaction.
Applicants further argue that the HPLC profile submitted in the previous filed declaration is unambiguous evidence that the disclosure provides MTX-1 is quantitatively pure, wherein the DSC profile, a single peak, reinforces purity.
In response to these arguments, the Examiner has previously responded to the declaration in the Final Office action and incorporated herein. In particular, the declarant has not provided any comparative data to show that MTX-1 obtained, for example, by the method of the prior art will result in a purity that is substantially or unexpectedly different. In the instant case, Fronabarger and Williams provides a DCS profile for MTX-1 (Figure 9) showing only one peak, which according to Applicants, reinforces the purity of the MTX-1 produced by Fronabarger and Williams.
Conclusion
Therefore, No claim is allowed.
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.
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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.
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BRANDON J. FETTEROLF, PHD
Primary Patent Examiner
Art Unit 1626
/BRANDON J FETTEROLF/Primary Examiner, Art Unit 1626
