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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 11/20/2025 has been entered.
Response to Amendment
The Examiner acknowledges Applicant’s response filed on 11/20/2025 containing
amendments and remarks to the claims.
Status of the Claims
Claims 1, 4, 6-7, 10-14, 17-20, 22-24, 27, 29-30, and 32 are pending and are subject to this Office Action. Claims 17-20, 22-24, 27, 29-30, and 32 have been withdrawn. Claim 1 has been amended.
Response to Arguments
Applicant’s arguments, see pages 6-7, filed 11/20/2025, with respect to the rejection(s) of claim(s) 1 under 35 USC 103 have been fully considered and are persuasive. The Applicant has amended claim 1 to recite wherein the evaporation step is performed in the absence of at least 90% of visible light, whereas previously this was not required. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of previously applied art and newly found art.
The following is a modified rejection made based on amendments made to the claims.
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.
Claim(s) 1, 4, 6-7, and 10-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Dull (US2015/0344456) in view of Etscorn (US 4,597,961) and Nathan (US2016/0089343).
Regarding claims 1 and 6, Dull teaches:
A method of making a nicotine material (abstract) comprising:
Providing a nicotine material-forming solution comprising nicotine, one or more coformer(s), and, optionally, one or more solvent(s) ([0107], a combination of nicotine and a coformer in a given solvent).
Wherein the nicotine is S-nicotine, R- nicotine, or a combination thereof ([0044], (L)-nicotine form, also known as (−)-nicotine or S-nicotine).
Evaporating at least a portion of the coformer(s), if the coformer(s) are a solvent or solvents, and/or solvent(s), if present, from the nicotine material-forming solution ([0112], the solvent can be removed (e.g., by evaporation)).
Optionally, rinsing the nicotine material ([0112], in some embodiments, the solid is washed).
Wherein the nicotine material is formed ([0107]).
Dull does not appear to explicitly disclose (I) optionally, drying the nicotine material and (II) wherein the evaporation step is performed in the absence of at least 90% of visible light.
In regard to (I), Dull further teaches:
Wherein the drying is carried out under vacuum and/or at a temperature below the melting and/or decomposition temperature of the nicotine material ([0194], the solid is…dried under vacuum at room temperature).
Although Dull does not appear to explicitly disclose drying the nicotine material after evaporation, the reference in general teaches drying after washing and thus it would be obvious to further dry the nicotine material under a vacuum after washing as Dull reasonably suggests to one of ordinary skill that drying a solid nicotine material is known in the art. Drying under vacuum at room temperature further reads on the claim 6 limitation of wherein the drying is carried out under vacuum and/or at a temperature below the melting and/or decomposition temperature of the nicotine material.
In regard to (II), Etscorn, directed to transcutaneous application of nicotine, teaches:
Liquid nicotine 16 provided in a cavity 14 (Col. 5, lines 15-20). As both Etscorn and Dull relate to nicotine materials, Etscorn is considered to be analogous art.
Nicotine 16 may breakdown a result of exposure to light (Col. 8, lines 5-10).
Further, Nathan, directed to formulations for delivery of therapeutically effective doses of curcumin, teaches:
The compositions described herein may further comprise nicotine or a salt thereof [0131]. As both Nathan and Dull relate to nicotine materials, Nathan is considered to be analogous art.
Preparation of the sample in the dark prevents its degradation [0141].
Therefore, before the effective filing date of the claimed invention, it would be obvious for one having ordinary skill in the art to modify the method of making the nicotine material of Dull by preparing the material in the dark as taught by Nathan, and thus including the evaporation step being performed in the dark, as Etscorn teaches nicotine may breakdown as a result of exposure to light and Nathan teaches preparation in the dark prevents degradation from exposure to light, both Etscorn, Nathan, and Dull are directed to nicotine materials, and this merely involves incorporating a known way to prepare nicotine materials (i.e. in the dark) to a similar nicotine material preparation to yield predictable results.
It would be obvious to one or ordinary skill in the art that drying in the dark would have the absence of visible light near zero and therefore falling within the claimed range of in the absence of at least 90% of visible light.
Regarding claim 4, Dull further teaches:
Wherein the nicotine material is rinsed with a solvent chosen from hydrocarbon solvents, alcohols, ketone solvents, ester solvents, halogenated solvents, and combinations thereof ([0112], in some embodiments, the solid is washed, e.g., with THF, heptane, and/or EtOAc).
Regarding claim 7, Dull further teaches:
Wherein the solvent of the nicotine material-forming solution is chosen from organic solvents, water, and combinations thereof, and the organic solvents are chosen from alcohols, cyclic ethers, polar protic solvents, polar aprotic solvents, halogenated alkanes, halogenated aryl solvents, and combinations thereof ([0108]).
Regarding claims 10 and 13, Dull does not appear to explicitly disclose wherein the nicotine is present in the nicotine material-forming solution at its solubility limit in the solvent(s) or at 90% or more of its solubility limit in the solvent(s) or at a concentration of at least 0.01 M, and wherein the coformer(s) is/are present in the nicotine material-forming solution at 0.01 to 2 M. However, Dull further discloses:
The stoichiometry of the salts, co-crystals, and salt co-crystals described herein can vary. For example, in certain embodiments, where two components (i.e., nicotine and one coformer) are present, the nicotine: coformer stoichiometry can range in certain embodiments from about 5:1 to about 1:5 nicotine: coformer ([0049]).
The amount of a given nicotine salt, co-crystal, or salt co-crystal to be incorporated within a product will depend on the desired nicotine content of that product, and can be calculated based on the mass of the coformer and the stoichiometry of the salt, co-crystal, or salt co-crystal ([0130]).
As such, Dull is reasonably considered to teach that the amount of nicotine and the amount of coformer in the nicotine material-forming solution can be controlled by varying the nicotine: coformer stoichiometry. Therein, the nicotine: coformer stoichiometry is considered a result effective variable with affects the molar concentration of the nicotine and the coformer in the nicotine material-forming solution.
One of ordinary skill would recognize that the nicotine: coformer stoichiometry would affect the amount of nicotine and coformer present in the nicotine material-forming solution and thus affect the molar concentration of nicotine and coformer present in the nicotine material-forming solution. As such, it would be obvious for one having ordinary skill in the art to optimize the molar concentration of nicotine and coformer present in the solution since it has been held that, where 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. One of ordinary skill would be motivated to optimize the molar concentration of nicotine and coformer present in the solution by the desire to achieve the desired nicotine content of a specified product. As such this may include cases wherein the nicotine is present in the nicotine material-forming solution at its solubility limit in the solvent(s) or at 90% or more of its solubility limit in the solvent(s) or at a concentration of at least 0.01 M, as recited in claim 10, and wherein the coformer(s) is/are present in the nicotine material-forming solution at 0.01 to 2 M, as recited in claim 13. The burden is shifted upon the Applicant to demonstrate that the claimed concentrations are critical and have unexpected results.
Regarding claim 11, Dull further teaches:
Wherein the coformer(s) is/are chosen from organic compounds, mineral acids, and combinations thereof ([0092]).
Regarding claim 12, Dull further teaches:
Wherein the organic compounds are chosen from carboxylic acids, hydroxycarboxylic acids, alcohols, polyacids, sweetening agents, amino acids, and combinations thereof ([0092]).
Regarding claim 14, Dull further teaches:
Wherein the nicotine material is amorphous, polycrystalline, single crystalline, or a combination thereof ([0017], a pharmaceutical product comprising a nicotine salt or crystalline polymorphic form).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Nicole A Szumigalski whose telephone number is (703)756-1212. The examiner can normally be reached Monday - Friday: 8:00 - 4:30 EST.
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/N.A.S./Examiner, Art Unit 1755 /PHILIP Y LOUIE/Supervisory Patent Examiner, Art Unit 1755