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 .
Status of the Claims
Claims 1-2, 6-20, 24-25 and 27 are pending. Claims 12-14, 24-25 and 27 are withdrawn. Claims 16-19 are objected. Claims 1-2, 6-11, 15 and 20 are rejected.
Election/Restrictions
Applicant's election of Group I (claims 1-2 and 6-20) and of the elected species of claim 19,
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, without traverse in the reply filed on September 12, 2025 is
acknowledged.
Claims 1-2, 6-11 and 15-20 read on Applicant’s species election of formula I,
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, wherein R1 is F, R2 is H, R3 is CF3 (or R2 is CF3 and R3 is H), R4 is H, R5
and R6 are R9bOC(O)-, R7 and R8 are H, and R9b is methyl.
The elected invention was examined in accordance with the MPEP 803.02. The elected species is allowable in view of the prior art; therefore, examination of the Markush-type claim has been extended to the scope of formula I wherein:
R1, R2 and R3 are H, R4 is Cl or CF3, R5 and R6 are R9bOC(O)-, R7 and R8 are H, and R9b is methyl,
R1 is H, R2 is H, R3 is NO2 (or R2 is NO2 and R3 is H), R4 is H, R5 and R6 are R9bOC(O)-, R7 and R8 are methyl, and R9b is methyl,
and to the species of claims 16-19. Since art was found on nonelected species, subject matter not embraced by the elected embodiment or the above-identified non-elected species is therefore withdrawn from further consideration. Claims 12-14, 24-25 and 27 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Applicant is reminded that upon the cancellation of claims to a non-elected invention, the inventorship must be amended in compliance with 37 CFR 1.48(b) if one or more of the currently named inventors is no longer an inventor of at least one claim remaining in the application. Any amendment of inventorship must be accompanied by a request under 37 CFR 1.48(b) and by the fee required under 37 CFR 1.17(i).
Priority
This application is a 371 of PCT/SG2021/050734, filed on 11/30/2021, which claims foreign priority to application No. SG10202011877V, filed on 11/30/2020. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement(s) submitted on 9/4/2024, 11/6/2025, 11/7/2025, 2/3/2026,
5/22/2026, and 6/22/2026 are in compliance with the provisions of 37 CFR 1.97 and 37 CFR 1.98. Accordingly, the information disclosure statements have been considered by the examiner with the exception of the references that were not properly cited. These were references were striked-through to indicated that they were not considered. See, e.g., IDS filed 2/3/2026 NPL #10 and IDS filed 11/6/2025 NPL #6.
Drawings
The drawings are objected to because Figures 1A, 1B, 2A, 2B, 2C, and 3 have blurry structures and/or illegible text. Figures 5A and 5B and 6 have illegible text. Figure 7A misspells “H” and “I I” in the top two figures.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claims 1-2, 6-9, 11 and 15-20 are objected for the following grammatical informalities:
Claim 1 uses inconsistent formatting for Markush groupings (i.e., “selected from… and…” and “selected from…or…”). For consistency, replacing “selected from… and…” with “selected from…or…” is suggested as follows:
In the last line of the R5/R6 Markush group, “selected from halo, and NO2” may be replaced with “selected from halo or NO2”.
In the last line of the R7/R8 Markush group, “and C1 to C6 alkyl” may be replaced with “or C1 to C6 alkyl”.
In the first line of the R9a Markush group, “selected from H and” may be replaced with “selected from H or”.
Claim 1 contains the following typographical errors:
In the third line of the R7/R8 Markush group, “pair” should be “pairs”.
In the last line of the claim, “or pharmaceutically acceptable salts and/or solvates thereof” should be singular, since the claim is drawn to one compound in the alternative. (That is, “or a pharmaceutically acceptable salt and/or solvate thereof”.)
Claim 2, the last two lines, recite “selected from Cl, F, and NO2” instead of “selected from Cl, F or NO2.”
Claim 6, line 3, recites “selected from F and Cl” instead of “selected from F or Cl”; and the last line recites “and C1 to C6 alkyl” instead of “or C1 to C6 alkyl”.
Claim 6, line 4, recites “pair” instead of “pairs”.
Claim 7, line 3, recites “and Cl” instead of “or Cl”.
Claim 8, in the last three lines, recites “Cl and F” and “F and Cl”, instead of “Cl or F” and “F or Cl”, respectively.
Claim 9, last line, recites “H and CH3” instead of “H or CH3”.
Claim 11, line 2, recites “is” instead of “are”.
Claim 15, last line, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Claim 16, last line, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Claim 17, last line, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Claim 18, last line, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Claim 19, last line, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Claim 20, line 2, recites “or salts and solvates thereof”, which should be singular as “or a salt or solvate thereof”. The phrase “or a salt and/or solvate thereof” would also be acceptable (to encompass solvates of salts thereof).
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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.
Claims 8 and 9 are rejected under 35 U.S.C. 112(b) being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 8 recites five clauses that describe limitations on the compound of claim 1. There is a conjunction missing between the last two clauses (at the end of the R5/R6 clause); therefore, it is unclear whether claim 8 requires all of the five clauses to be met (if the conjunction were “and”), or whether only one of the clauses must be met (if the conjunction were “or”).
Claim 9, line 3, recites “R2 is selected from CF3” and “more particularly, H or F”. The phrase “more particularly” denotes a preference for the selection of R2 being made from H or F. It is unclear whether R2 can be selected from any of CF3, H or F, or whether R2 must be selected from H or F as a presiding preference. Since the scope of compounds encompassed is unclear, the claim is indefinite.
Claim 9, lines 6-7, provides a broad definition for R5 and R6 and then, in parentheticals, an example where “R5 and R6 are both CH3OC(O)-”. It is unclear whether R5 and R6 can be selected from the broader definition or whether R5 and R6 must be both CH3OC(O), based on the example. Since the scope of compounds encompassed is unclear, the claim is indefinite.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(1 of 2) Claims 1-2, 6-11 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bennasar et al. Tetrahedron 2002, 58, 8099-8106, as evidenced by Wikipedia contributors. (16 May 2005). Chloroform In Wikipedia, The Free Encyclopedia. Retrieved 4 November 2023, from https://en.wikipedia.org/w/index.php?title=Chloroform&oldid=14090628.
Bennasar teaches compounds 10b and 10c, of the formula
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, wherein R1 is 2-CF3 (10b) or 2-Cl (10c). See Table 2 entries 1 and 2. Bennasar provides NMR data for these compounds in CDCl3 solution. See Sections 3.1, 3.7.1 and 3.7.2.
Bennasar’s compounds 10b and 10c have the same structure as the claimed compounds of formula I,
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, wherein R1, R2 and R3 are H, R4 is Cl or CF3, R5 and R6 are
R9bOC(O)-, R7 and R8 are H, and R9b is methyl; thereby anticipating claim 1. The following dependent claims read on compounds 10b and 10c as outlined below:
Claim 2, R1 is H, R2 and R3 are H, R4 is Cl or CF3, and R5 and R6 are R9bOC(O)-,
Claim 6, wherein R7 and R8 are H.
Claim 7, wherein R9b is methyl.
Claim 8, wherein R1, R2 and R3 are H, R4 is Cl or CF3, R5 and R6 are R9bOC(O)-, and R7 and R8 are H.
Claim 9, wherein R1, R2 and R3 are H, R5 and R6 are CH3OC(O)-, and R7 and R8 are H.
Claims 10 and 11, wherein R7 and R8 are H.
Claim 20 reads on the CDCl3 solutions comprising compound 10b or 10c, because chloroform is inherently a pharmaceutically acceptable carrier or vehicle in such small amounts, as evidenced by Wikipedia. For example, Wikipedia teaches that chloroform has anesthetic properties. Since anesthetic properties are pharmaceutical properties, chloroform qualifies as a pharmaceutically acceptable carrier/vehicle.
(2 of 2) Claims 1-2, 6-9, 15 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bossert et al. Med. Res. Rev. 1989, 9, 291-324.
Bossert teaches compound 42 of the structure
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, wherein R is -CH3 and R1 is 3-NO2. The compound was administered intravenously at dosages of 0.01, 0.1 and 0.2 mg/kg to “anesthetized, cardiac-catheterized dogs.” See p. 297 and Table VI (p. 305).
Bossert’s compound 42 has the same structure as the claimed compound of formula I,
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, wherein R1 is H, R2 is H, R3 is NO2 (or R2 is NO2 and R3 is H), R4 is H, R5
and R6 are R9bOC(O)-, R7 and R8 are methyl, and R9b is methyl; thereby anticipating claim 1.
The following dependent claims read on compound 42 as outlined below:
Claim 2, R1 is H, R2 and R3 are H or NO2, R4 is H, and R5 and R6 are R9bOC(O)-,
Claim 6, wherein R7 and R8 are methyl.
Claim 7, wherein R9b is methyl.
Claim 8, wherein R1 is H, R2 and R3 are H or CF3, R4 is H, R5 and R6 are R9bOC(O)-, and R7 and R8 are methyl.
Claim 9, wherein R1 is H, R2 is H, R3 is CF3 (or R2 is CF3 and R3 is H), R4 is H, R5 and R6 are CH3OC(O)-, and R7 and R8 are CH3.
Claim 15 depicts the compound
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, which is identical to Bossert’s compound 42.
Claim 20 reads on the IV solutions comprising compound 42, because a pharmaceutically acceptable carrier or vehicle must have been inherent to administer the various dosages of compound 42 to the anesthetized and cardiac-catheterized dogs. Without a pharmaceutically acceptable carrier or vehicle, a PHOSITA would not have been able to modify the amount of compound administered, because dilution of a solution requires a liquid carrier or vehicle.
Allowable Subject Matter
Claims 16-19 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. The closest prior art is Bennasar et al., which was discussed above.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMANDA L AGUIRRE whose telephone number is (571)272-5592. The examiner can normally be reached 10 am-6 pm MST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, JEFFREY H. MURRAY can be reached on 571-272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMANDA L. AGUIRRE/ Primary Examiner, Art Unit 1626
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