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
Applicant’s amendment and response, submitted on June 24, 2026, has been reviewed by the examiner and entered of record in the file.
Claims 1, 2, 4, 5, 7, 8, and 10-12 are amended. Claim 13 is canceled.
Claims 1-12 are under examination and are the subject of this office action.
Specification
5. The disclosure was previously objected to regarding the presence of the terms “new” and “novel.”
In view of Applicant’s amendment to the Specification to replace paragraph [002]; paragraph [005]; paragraph [0010], paragraph [0011], and paragraph [0012], the previous objection is withdrawn.
Withdrawn Claim Rejections - 35 USC § 112(b)
6. Claims 1-12 were previously 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.
7. Claim 1 was previously rejected as being unclear in the following aspects:
(a) In the preamble, the parenthetic expression “(bromo-oxime derivative)” is confusing and extraneous, because the claim has identified the compound being prepared: 4-amino-3-bromocarbohydroxymoyl-1,2,5-oxadiazole.
It is unclear whether parenthetical “bromo-oxime derivative” is part of the compound or if Applicant is further defining the compound.
In view of the deletion of “(bromo-oxime derivative)” from the claim, this aspect of the 35 USC 112(b) rejection has been overcome.
(b) In step (c), there is insufficient antecedent basis for the limitation of the term “the reaction mixture” in the claim because there is no prior mention of a reaction mixture.
In view of the addition of the text “to form a reaction mixture” into the first line of step (c), this aspect of the 35 USC 112(b) rejection has been overcome.
(c) In step (d), the term “cautiously” is a relative term which renders the claim indefinite.
In view of the deletion of the term “cautiously” from the first line of step (d), this aspect of the 35 USC 112(b) rejection has been overcome.
(d) Step (e), recites the term “the reaction” however there is insufficient antecedent basis for this limitation in the claim because there is no prior mention of a reaction.
In view of the addition of the text “to initiate a reaction” into the second line of step (d), this aspect of the 35 USC 112(b) rejection has been overcome.
(e) Step (f) recites the term “precipitated solid,” however there is insufficient antecedent basis for this limitation in the claim because there is no prior mention of a precipitated solid.
In view of the modification of the limitation “precipitated solid” in step (f) such that said limitation is now “solid precipitate,” which is consistent with the limitation if step (e), this aspect of the 35 USC 112(b) rejection has been overcome.
(f) (i) In claim 1, step (g) was rejected as being unclear regarding the term “obtained solid.”
In view of Applicant’s amendment to add the limitation of “and to obtain a solid” in step f), this aspect of the 35 USC 112(b) rejection has been overcome.
(ii) Step (g) recited the term “the desired product,” which lacks insufficient antecedent basis because there is no prior mention of a desired product.
In view of the deletion of the term “desired product” in step (g), this aspect of the 35 USC 112(b) rejection has been overcome.
(iii) In step (g), the phrase "subsequent chemical transformations or applications" rendered the claim indefinite.
In view of the deletion of the recitation of “ready for subsequent chemical transformations or applications” in step (g), this aspect of the 35 USC 112(b) rejection has been overcome.
8. Claim 2 was previously rejected as being unclear in the following aspects:
(a) Line 1 recited the term “the synthesis,” which lacked sufficient antecedent basis because there is no prior mention of “a synthesis of 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide.”
In view of the deletion of the term “the synthesis of …[language omitted] in line 1 of the claim, this aspect of the 35 USC 112(b) rejection has been overcome.
(b) In line 2, the parenthetic expression “(furoxan derivative)” was rejected as being confusing and extraneous, because the claim identified the compound being prepared: 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide. It was not clear whether parenthetical “furoxan derivative” is part of the compound or if Applicant is further defining the compound.
In view of the deletion of the term “(furoxan derivative)” in line 2 of the claim, this aspect of the 35 USC 112(b) rejection has been overcome.
(c) In lines 2-3, the limitation of “using the 4-amino-3-bromocarbohydroxy-moyl-1,2,5-oxadiazole,” is confusing, because it is not clear if the use recited in lines 2-3 is an additional step of if the use is referring to step (b), which is repetitive and redundant.
In view of the deletion of the recitation “using the 4-amino-3-bromocarbohydroxy-moyl-1,2,5-oxadiazole,” in line 2 of the claim, this aspect of the 35 USC 112(b) rejection has been overcome.
(d) Step (d) was rejected as being unclear in the following aspects:
(i) In line 1, it is not clear what solid “clean dimerization” is formed, and it is also not clear what is embraced by “analytic methods,” i.e., what analytics/ assays are being performed and does the term “analytic methods” refer to an additional method step(s) that are not yet recited?
In view of the deletion of the term “a clean” in the first line of step (d), and the deletion of the phrase, “is observed, as indicated by analytic methods,” this aspect of the 35 USC 112(b) rejection has been overcome.
(ii) And in step (d), line 1 recited the term “the reaction,” which lacks sufficient antecedent basis because there is no prior mention of a reaction.
In view of the addition of the text “to initiate a reaction” into the second line of step (c) of this claim, this aspect of the 35 USC 112(b) rejection has been overcome.
(e) In claim 2, step (e) was rejected as being unclear in the following aspects:
(i) Line 1 of step (e) recited the term “resultant,” which lacks sufficient antecedent basis because there is no prior mention of a resultant 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide.
In view of the deletion of the term “the” prior to the compound “3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide,” this aspect of the 35 USC 112(b) rejection has been overcome.
(ii) The term “other suitable separation methods” was rejected as being a relative term which renders the claim indefinite. The term “suitable separation methods” are 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.
In view of the deletion of the recitation “other suitable separation methods” in line 2 of step (e), this aspect of the 35 USC 112(b) rejection has been overcome.
(iii) In step (e), the phrase "other suitable separation methods" rendered the claim indefinite because the claim includes elements not actually disclosed, i.e., those encompassed by "or other … methods," thereby rendering the scope of the claim(s) unascertainable.
In view of the deletion of the recitation “other suitable separation methods” in line 2 of step (e), this aspect of the 35 USC 112(b) rejection has been overcome.
9. Claim 5 was previously rejected regarding the term “ the solid,” which renders the claim indefinite. In view of the amendment to add the term “precipitate” after “solid” in line 1 of claim 5, the previous indefiniteness rejection is withdrawn.
10. Claim 10 was previously rejected for reciting the limitation "wherein the temperature of the biphasic reaction medium… [language omitted]," wherein there is insufficient antecedent basis for the limitation of “the temperature” in the claim.
In view of Applicant’s amendment to claim 10 to delete the recitation of “the temperature” in line 1, and to add the recitation of “at a temperature” after the term “maintained” in line 2, the previous indefiniteness rejection is withdrawn.
11. Claim 11 was previously rejected for reciting the term “the resultant.” There is insufficient antecedent basis for this limitation in the claim because there is no prior mention of a resultant 3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide.
In view of Applicant’s amendment to claim 11 to delete the recitation of “the resultant” in line 1, the previous indefiniteness rejection is withdrawn.
12. Claim 12 was previously rejected as being unclear in the following aspects:
(a) Claim 12 was previously rejected regarding the term “the isolated… [language omitted]” in line 1, as lacking sufficient antecedent basis.
In view of Applicant’s amendment to delete the term “the isolated” prior to “3,4-bis(4-amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazole-N-oxide” in lines 1-2, this aspect of the previous indefiniteness rejection is overcome and the rejection is withdrawn.
(b) Claim 12 was previously rejected regarding the recitation of "such as" which renders the claim indefinite because it is unclear whether the limitations following the phrase, i.e., crystallization or column chromatography, are exemplary or are part of the claimed invention.
In view of Applicant’s amendment to delete the phrase “such as” and replace it with “including”, this aspect of the previous indefiniteness rejection is overcome and the rejection is withdrawn.
14. Claim 13 was previously rejected as being unclear regarding the recitation of “said compound being a bromo-oxime derivative” in the preamble, as well as the claim being drawn to the compound characterized by the recited formula.
In view of the cancellation of claim 13, the previous indefiniteness rejection is withdrawn.
Maintained Claim Rejections - 35 USC § 112(b)
15. The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
16. Claims 2 and 4 remain 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.
17. Claim 2 remains rejected as being indefinite regarding the labeling of the further method steps (a)-(e) recited. Claim 2 depends from claim 1, which recites a method of synthesis comprising steps (a)-(g). However, claim 2 then adds additional steps, i.e., “further comprising” steps (a)-(e), which is confusing because they are labeled the same as the initial steps in claim 1, such that there are duplicate “a)”s, “b)”s, etc. Thus is not clear if steps (a)-(e) are performed subsequent to the steps recited in claim 1, or if each of steps (a)-(e) of claim 2 occurs sequentially with steps (a)-(e) of claim 1. For purposes of clarification, it is recommended that the additional steps of claim 2 are labeled as i), ii), iii) etc.
18. Claim 4 remains rejected as being indefinite regarding the limitation "the sequential treatment with an aqueous solution of hydrobromic acid, cuprous bromide, and sodium nitrite,” as lacking sufficient antecedent basis.
Applicant amended the claim to delete the recitation of “sequential treatment with an aqueous solution of,” in lines 1-2.
However, as amended, claim 4 remains rejected regarding the limitations: “the addition of hydrobromic acid,” “the introduction of cuprous bromide,” and “the introduction of sodium nitrite,” as lacking antecedent basis because there is no prior recitation of each of said limitations in claim 1. That is, claim 1 recites “…adding an aqueous solution of hydrobromic acid” [emphasis added], not “the addition of hydrobromic acid.” And, claim 1 recites “…introducing cuprous bromide in divided portions,” not “the introduction of cuprous bromide.” And, claim 1 recites “…introducing an aqueous solution of sodium nitrite,” [emphasis added], not “introduction of sodium nitrite.”
Clarification is requested.
Previous Claim Rejections - 35 USC § 112(a)
19. Claims 1-13 were previously 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, regarding the full scope of “bromo oxime derivative(s)” embraced by the claims.
20. In view of Applicant’s amendment to delete the term “bromo-oxime derivative” from claim 1, the previous written description rejection of claim 1 and dependent claims 2-13 is withdrawn.
21. Claims 11 and 12 were previously 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, regarding the step of “ensuring a purity of above 90%” (claim 11) or “achieving a purity of 98% or higher” (claim 12).
22. In view of Applicant’s amendments to delete the limitation of “ensuring a purity of above 90%” in claim 11, and to delete the limitation of “achieving a purity of 98% or higher” in claim 12, the previous written description rejection under 35 USC 112(a) is withdrawn.
Previous Claim Rejections - 35 USC § 102
23. Claim 13 was previously rejected under 35 U.S.C. 102(a)(1) as being anticipated by Andrianov and Eremeev, Chemistry of Heterocyclic Compounds (1994).
24. In view of the deletion of claim 13, the previous anticipation rejection is withdrawn.
Conclusion
24. Claims 1-12 are pending in the application, and all claims are rejected. No claim is presently allowed.
25. THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
26. Any inquiry concerning this communication or earlier communications from the examiner should be directed to JANET L COPPINS whose telephone number is (571)272-0680. The examiner can normally be reached Monday-Friday 8:30AM-5PM EST.
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.
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/JANET L COPPINS/Examiner, Art Unit 1628
/AMY L CLARK/Supervisory Patent Examiner, Art Unit 1628
