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 .
Priority
This application is a 371 of PCT/FR2021/052105 (11/26/2021)
and claims foreign priority to FRANCE 2013614 (12/18/2020).
Drawings
The drawings filed 6/20/23 are objected to for not conforming to the requirements of 37 CFR 1.84(u)(1) (“View numbers must be preceded by the abbreviation “FIG.” Where only a single view is used in an application to illustrate the claimed invention, it must not be numbered and the abbreviation “FIG.” must not appear.”). MPEP 608.02.
In addition, Figure 1 has illegible text and bond orders – a higher resolution version 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 11-18 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 11 uses the language “the diazidoglyoxime” which lacks an antecedent basis. Claim 11 has the following language: “a cyclization by reaction of the diazidoglyoxime obtained with an acetyl halide so as to obtain 1,1'-diacetyl-5,5'-bistetrazole, a temperature greater than or equal to 30°C and less than the boiling temperature of the acetyl halide being imposed during the cyclization,” which is unclear with respect to how “a temperature” is limiting the claim and whether the reaction is required to be performed at the temperature. Claim 11 has the language “less than the boiling temperature of the acetyl halide” which one of skill in the art would find ambiguous as the boiling temperature can change depending on the conditions of the reaction (and could be below 30C), particularly pressure.
Claim 11 has the following language: “a solvent allowing to dissolve the reagents and reaction intermediates being used during the synthesis, the reaction intermediates remaining in solution and no isolation of the latter being carried out, the azidization, the cyclization, the hydrolysis and the ion exchange being carried out in a common solvent comprising at least dimethylformamide, acetone or acetonitrile” which lacks antecedent basis for “the reagents and reaction intermediates”; is not clear how the “a solvent allowing …” is incorporated into the claims given a lack of “and” or “or” preceding; is unclear with respect to the scope of “a solvent” vs. “a common solvent” and whether the “common solvent” allows for common elements or requires the solvent to be actually the same; and is unclear with respect to what is being referred to with “no isolation of the latter”.
Thus, the claim and those that depend therefrom are rejected as indefinite.
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.
Claim 18 is 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 18 is to A method for the manufacture of an energetic composition, comprising at least: implementing a method according to claim 11 so as to obtain TKX-50, and obtaining the energy composition from the TKX-50 thus obtained, which does not clearly further limit the method of claim 11 because there are no additional steps or limitations required to be performed. 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
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.
Claims 11-16 and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Klapotke et al. (US9296664) in view of Golenko et al. (Chin. J. Chem. 2017, 35, p. 98-102, supp 6-15) and Damavarapu et al. (US9643937).
Klapotke teaches a method of synthesizing dihydroxylammonium salt of 5,5’-bistetrazole-1,1’-diolate (aka TKX-50) (col 2):
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Klapotke teaches “8. The process as disclosed in item 3, wherein the promoting of the isomerization takes place by acylation, more particularly by means of acetyl chloride” (col 2, line 60). Klapotke teaches “9. The process as disclosed in item 3 or 8, wherein the diazidoglyoxime is produced by reaction of dichloroglyoxime with an azide, the dichloroglyoxime being produced more particularly by reaction of glyoxime with chlorine, the glyoxime being produced more particularly by reaction of glyoxal with hydroxylamine.
10. The process as disclosed in item 9, wherein the reaction of the dichloroglyoxime with the azide takes place in a nonaqueous solvent, more particularly dimethylformamide (DMF) or N-methyl-2-pyrrolidone (NMP), the solvent with the result ant diazidoglyoxime being subsequently mixed with the …” (col 2, line 65, to col 3, line 9).
Thus, Klapotke’s “10” corresponds to claim 11’s azidization step; Klapotke’s “9” corresponds to claim 11’s cyclization step. Regarding claim 11’s hydrolysis and ion exchange steps, Klapotke teaches (Col 8, line 32):
In the case of DMF as solvent, a mixture of dimethylammonium 5,5'-bistetrazole-1,1'-diolate and a 5,5'-bistetrazole-1, 1'-diolate which comprises at least one counterion of the azide serving for the chlorine/azide exchange, and, in the case of NMP as solvent, a residue comprising 5,5'-bistetrazole-1, 1'-diol, are obtained. The stated mixture can be dissolved in H2O, with subsequent addition of a hydroxylammonium salt, more particularly hydroxylammonium chloride, and so the dihydroxylammonium salt of 5,5'-bistetrazole-1,1'-diol is obtained as the precipitate.
wherein dissolving the mixture in water corresponds to hydrolysis and “subsequent addition of a hydroxylammonium salt” corresponds to ion exchange. Regarding claim 11’s last paragraph, the solvent and common solvent are DMF and no isolation is carried as taught by Klapotke above.
Klapotke does not specifically teach claim 11’s “a temperature greater than or equal to 30°C and less than the boiling temperature of the acetyl halide being imposed during the cyclization”
Golenko teaches optimization of the synthesis of TKX-50, including one-pot procedures (title, abstract). Golenko teaches that temperature of the reaction to synthesize TKX-50 is a results effective variable with respect to yield (p. 101: “We have found out that the reaction temperature significantly affects the TKX-50 yield”, “… the acetyl chloride promoted cyclization required high temperature.”). Golenko also teaches use of acetyl chloride (AcCl) in the synthesis of TKX-50 including Scheme 4, Table 5 (p. 101):
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Golenko also teaches successful synthesis with solvents including benzene, toluene, and DMF (p. 100-102).
Damavarapu teaches one-pot process for the synthesis of TKX-50 as illustrated in Scheme 1, including the use of N-chlorosuccinimide in DMF to prepare dichologlyoxime (cols 2-3; claims 1-3).
One of ordinary skill in the art following the teaching of Klapotke would have considered known techniques for synthesizing the same compound, in this case TKX-50, in the course of optimization of a one-pot synthesis. Both Golenko and Damavarapu teach how to optimize one-pot synthesis of the compound, including through the optimization of temperature of reaction and use of solvent. One of ordinary skill in the art routinely optimizes such well-known results effective variables in order to improve yield of synthetic processes and the application of the same techniques was well within the technical grasp of one of ordinary skill art.
Thus, the prior art reasonably suggests the method of claims 11-16 and 18. With each of the claims, the level of skill in the art is very high such that one of ordinary skill in the art would consider routine the combination of elements from the teaching of the art. One of ordinary skill in the art would have recognized that the results of the combination would be predictable due to the well-known nature and optimizations routinely performed in the art. Thus, one of ordinary skill in the art would have arrived at the invention as claimed before the effective filing date with a reasonable expectation of success.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Klapotke et al. (US9296664) in view of Golenko et al. (Chin. J. Chem. 2017, 35, p. 98-102, supp 6-15) and Damavarapu et al. (US9643937) as applied to claims 11-16 and 18 above and further in view of KR10-1964988 (‘988).
Regarding claim 17, the combined teaching of Klapotke, Golenko and Damavarapu teach the synthetic method, but not the use of diaminoglyoxime as an intermediate.
‘988 teaches synthesis of TKX-50 using a diaminolyoxime intermediate via azidation (Abstract: “a process for preparing dihydroxyammonium 5,5'-bistetrazole-1,1'-diolate using a diaminoglyoxime intermediate”). One of ordinary skill in the art following the combined teaching would have considered using known successful synthetic techniques for the same compound with a reasonable expectation of success. Thus, claim 17 is also rendered obvious.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 11-18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-20 of U.S. Patent No. 9296664 in view of Golenko et al. (Chin. J. Chem. 2017, 35, p. 98-102, supp 6-15), Damavarapu et al. (US9643937), and KR10-1964988. Although the claims at issue are not identical, they are not patentably distinct from each other because the patent (the same as in the 35 USC 103 rejection supra) claims the same compound and a process for preparation such that as detailed in the 35 USC 103 rejection supra and incorporated herein renders the instant claims obvious.
Conclusion
No claims allowed.
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/ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626