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 .
Claims 2-10, 12, 14, 16-18 and 39 are presented for examination.
The amendments and remarks filed on 02/05/2026 have been received and entered.
Claim(s) 2-10, 12, 14, 16-18 and 39 is/are rejected under 35 U.S.C. 103 as being unpatentable over
Freeman (US 20150246059) in view of Szente et al. (Fatty Acid-Cyclodextrin Complexes: Properties and
Applications) and further in view of Kadri et al. (submitted by the applicant).
Freeman teaches the nitrated lipids and methods of making and using the nitrated lipids. See the
abstract. The claimed compounds are taught in Para [0071]-[0087]. Freeman teaches that Parenteral
administration of the composition, if used, is generally characterized by injection. Injectables can be
prepared in conventional forms, either as liquid solutions or suspensions, solid forms suitable for
solution of suspension in liquid prior to injection, or as emulsions. See Para [0107]. Freeman teaches
that formulations for topical administration may include ointments, lotions, creams, gels, drops,
suppositories, sprays, liquids and powders. Conventional pharmaceutical carriers, aqueous, powder or
oily bases, thickeners and the like may be necessary or desirable. See Para [0114]. Freeman teaches
that compositions for oral administration include powders or granules, suspensions or solutions in water
or non-aqueous media, capsules, sachets, or tablets. Thickeners, flavorings, diluents, emulsifiers,
dispersing aids or binders may be desirable See Para [0115]. Freeman teaches that in one aspect, the
unsaturated lipid comprises oleic acid, linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic
acid, or docosahexanoic acid. See Para [0098]. The use of 10-nitro-9-octadecenic acid (oleic acid) is
taught in claim 83.
Freeman differs from the claimed invention in the presence of cyclodextrin. Szente et al. teach that
complexation of fatty acids (both saturated and unsaturated with various cyclodextrins and cyclodextrin
derivatives greatly modifies their properties. Inclusion complex formation depending upon the type of
host cyclodextrin may result in protection against the environment, in improved water solubility and bioavailability. Thus lipid complexation enables the preparation of more reliable diagnostic reagents,
better chromatographic separations and higher yields in biotechnological processes. See the abstract.
The use of beta-cyclodextrin is taught in the experiments, on page 4. Kadri et al. teach the increases stability of 2-chloroethylnitrososulfamides by addition of beta-cyclodextrin. See the abstract and conclusion.
It would have been obvious to a person skilled in the art to add cyclodextrin to the composition of
Freeman, motivated by the teachings of Szente, which teaches the inclusion of beta-cyclodextrin may result in protection against the environment, in improved water solubility and bioavailability of fatty acids. Kadri teaches the increased stability of compounds having a nitro group by addition of beta-cyclodextrin.
Double Patenting
Claims 2-10, 12, 14, 16-18 and 39 rejected on the ground of nonstatutory double patenting as being unpatentable over claim1-4 of U.S. Patent No. 10,869,850, claims 4-32 of U.S. Patent No.
10,751,310, claims 1-5 of the U.S. Patent No. 10,765,652, claims 17-20 of the U.S. Patent 8,309,526,
claims 1-2 of the U.S. Patent 10,258,589 and claims 1-9 of U.S. Patent 8,735,449 in view of Szente et al. and Kadri et al.
Szente et al. teach that complexation of fatty acids (both saturated and unsaturated with various cyclodextrins and cyclodextrin derivatives greatly modifies their properties. Inclusion complex formation depending upon the type of host cyclodextrin may result in protection against the environment, in improved water solubility and bioavailability. Thus lipid complexation enables the preparation of more reliable diagnostic reagents, better chromatographic separations and higher yields in biotechnological processes. See the abstract. The use of beta-cyclodextrin is taught in the experiments, on page 4. Kadri et al. teach the increased stability of compounds having a nitro group with beta-cyclodextrin.
Response to Arguments
Applicant’s arguments have been noted. Applicant in his response argues that “Nitro-containing compounds, particularly nitrated fatty acids (NO2-FAs), are extremely unstable
in aqueous environments. NO2-FAs are fundamentally different from conventional fatty acids or drugs
previously complexed with cyclodextrins. NO2-FAs contain a highly reactive nitroalkene moiety, which
imparts distinctive chemical reactivity and extreme instability in aqueous environments. Unlike typical
solubilization challenges addressed by prior art, the nitroalkene group undergoes rapid Michael addition
with nucleophiles (e.g., thiols, amines), reversible covalent adduction to proteins, and water and pH-
dependent hydration processes. These reactions result in degradation and inactivation, rendering NO2-FAs unsuitable for pharmaceutical applications unless stabilized.” The examiner has relied on Kadri to show the increased stability of nitro compounds by the addition of beta-cyclodextrin. Therefore, the advantage applicant refers to in Figs 7A-7C is the expected property of Kadri et al.
Applicant's submission of an information disclosure statement under 37 CFR 1.97(c) with the timing fee set forth in 37 CFR 1.17(p) on 02/05/2026 prompted the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 609.04(b). 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ZOHREH A FAY whose telephone number is (703)756-1800. The examiner can normally be reached Monday-Friday 9:30AM-6:00.
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/ZOHREH A FAY/Primary Examiner, Art Unit 1617
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