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 .
Response to Amendment
The office action is in response to Applicant’s amendment filed on 12/31/2025.
Claims 1 and 12-14 are amended.
Claims 3-6, 11, 21-22, and 29 are cancelled.
Claims 1-2, 4-10, 12-20, 23-28, and 30-35 are pending.
Claims 28 and 30-35 are withdrawn as being directed to a non-elected invention.
Response to Arguments
Applicant’s arguments, see pages 8-12, filed 12/31/2025, with respect to the rejection of claims 1-2, 7-10, 12-20, and 23-27 under 35 U.S.C. 112(a) have been fully considered and are not persuasive.
On pages 8-10, the Applicant argues the teachings in the instant specification are sufficient to allow a person of ordinary skill in the art to work within the claimed energy of binging range of -5.6 to -8 kcal/mol without undue burden or sufficient experimentation.
The Examiner respectfully disagrees.
First, the enablement rejection is regarding how one of ordinary skill in the art would not know what types of substituted cyclodextrins, the “one or more flavors”, as well as the additional requirements in the formulation would lead to the binding energy claimed without undue experimentation. While there are two examples of cyclodextrins provided in the specification within the claimed binding energy range, the claimed composition is not limited to only these two examples. There would be an undue amount of experimentation to recreate the claimed composition with any substituted cyclodextrin that would have a binding energy within the claimed range.
Further, the examples in the specification only show how substitutions can affect the binding energy of hydroxypropyl beta cyclodextrin. While the binding energies of hydroxypropyl beta cyclodextrin may be within the narrow range of -5.6 to -8, hydroxypropyl beta cyclodextrin is not claimed and therefore determining all the other types of substituted cyclodextrins that could be within the binding energy range would require undue experimentation.
Further substituted cyclodextrins are not narrow in scope and are instead a very broad category for types of cyclodextrins. There are alpha, beta, and gamma substituted cyclodextrins, various substitution sites, and cyclodextrins comprising different groups. Substituted cyclodextrins include many different constituents and one with ordinary skill in the art would not think hydroxypropyl groups are representative of all possible substitutions. There would be undue experimentation for one of ordinary skill in the art to find what suitable substituted alpha, beta, or gamma cyclodextrins would satisfy the claimed binding energy.
On pages 10-11, the Applicant argues that amended claim 1 overcomes the current rejection of claim 1, specifically arguing that none of the prior art documents relied on by the Examiner teach a formulation comprising an acid present in an amount from 0.2 to 6wt.% based on the aerosolizable formulation.
The Examiner finds the arguments persuasive, however newly found prior art teaches the amendment and is provided in detail below.
A modified rejection based on the amendments is provided below.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-2, 7-20, 23-28, and 30-35 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification does not reasonably provide enablement for an energy of binding of the one or more encapsulating materials with the one or more flavors to be encapsulated is from -5.6 kcal/mol to -8 kcal/mol as recited in claim 1. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make the invention commensurate in scope with these claims.
Further, in accordance with the In re Wands factors (see MPEP 2164.01(a)), the claims are not enabled in light of the following factors:
Breadth of the claims: the breadth of the claims are broader in scope than the specification. The breadth of the claims must be a reasonable enablement. The scope of enablement provided to one skilled in the art by the disclosure should commensurate with the scope of protection sought by the claims and when a range is claimed, there must be reasonable enablement of the scope of the range (MPEP 2164.06(b) and MPEP 2164.08). Claim 1 is not enabled by the claimed “wherein in the presence of water an energy of binding of the one or more encapsulating materials with the one or more flavors to be encapsulates is from -5.6 to -8 kcal/mol” because the number of working examples provided in the specification are very narrow compared to the wide breadth of the claims at issue. For example, the specification provides two working examples wherein Hydroxypropyl beta cyclodextrin substituted at 7 sites and Hydroxypropyl beta cyclodextrin substituted at 5 points result in a free energy of binding within the claimed range, which is -6 and -5.6 kcal/mol respectively. While two working examples are provided, one of ordinary skill in the art would not know what other substituted cyclodextrins and “the one or more flavors” are that could be used in a formulation that would result in the claimed energy of binding, and therefore would require an undue amount of experimentation to recreate the encapsulated materials with the energy of binding claimed. It is further noted that it is not clear how the endpoint of the range -8 kcal/mol was determined.
the nature of the invention: the invention is an aerosolizable formulation comprising water, one or more flavors to be encapsulated, one or more substituted cyclodextrins, and nicotine. A decent amount is known about the nature of formulating nicotine based aerosolizable formulations, but little is known about specific cyclodextrins used and energy of binding for the encapsulating materials used in these formulations. More detail would need to be provided in the specification. (MPEP 2164.03).
the state of the prior art: there are a few references that disclose substituted cyclodextrin in similar aerosolizable formulations.
the level of one of ordinary skill: one of ordinary skill in the art is considered to know an aerosolizable formulation comprising one or more flavors and an encapsulating material for encapsulating the flavors, however one of ordinary skill in the art would not know what encapsulating materials, specifically what kind of substituted cyclodextrins, can be used with the one or more flavors, water, and nicotine within the encapsulation would create an energy of binding in the presence of water from -5.6 to -8 kcal/mol.
The level of predictability in the art: the level of predictability in the art is lacking because one skilled in the art cannot readily anticipate the effect of a change within the subject matter to which the claimed invention pertains (MPEP 2164.03).
the amount of direction provided by the inventor: the amount of direction provided by the inventor is lacking in the scope of the specification because only two substituted cyclodextrins are provided that fit within the claimed binding energy range and the binding energy of these encapsulating cyclodextrins does not include the effects of the other materials in the formulation. Further, it is unclear if only the cited substituted cyclodextrins work or if the breadth of the claims is overreaching and includes more substituted cyclodextrins. In addition, it is unclear if any flavorings can be used or if there are specific flavors used to reach the energy of binding claimed.
The existence of working examples: there are only two working examples provided in the specification that fall within the claimed binding energy range and they do not include specific flavors, and thus one of ordinary skill in the art would not find it obvious to recreate what is claimed. Even if one of ordinary skill in the art could find one or more flavors that work, one would not know if other substituted cyclodextrins could be used in addition to the cited ones in the specification without undue experimentation.
The quantity of experimentation needed to make or use the invention based on the content of the disclosure: The Applicant provides embodiments in the specification with a narrower range to what is claimed that could potentially enable one of ordinary skill in the art to produce/recreate the invention. However, the scope of what is claimed is not enabled and would need an undue level of experimentation to produce the invention.
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.
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 1-2, 7-10, 12-4, 17-20, and 23-27 are rejected under 35 U.S.C. 103 as being unpatentable over Cameron et al. (US 2017/0325494 A1), in view of Kobal et al. (US-20250325614-A1), Kuntawala et al. (US 2016/0198759 A1, cited in the IDS dated 04/30/2021) and Demain (US-5144964-A).
In regards to claim 1, Cameron discloses a liquid composition for use with electronic vaporizing devices comprising:
water in an amount of about 70 wt.% to about 99 wt.% ([0010], [0015], and [0056]);
at least one flavoring agent ([0012] and [0061]);
nicotine ([0010], [0015], and [0058]); and
at least one acid ([0078]).
Cameron does not appear to explicitly disclose an acid present in an amount from 0.2 to 6w.% based on the aerosolizable formulation (I), one or more encapsulating materials comprising cyclodextrins (II), the cyclodextrins being substituted (III), that wherein in the presence of water an energy of binding of the one or more encapsulating materials with one or more flavors to be encapsulated is from -5.6 to -8 kcal/mol (IV), and the molar ratio of encapsulating material to flavor is from 5:1 to 1:5 (V).
(I)
Cameron discloses citric acid may be added to the composition ([0078]) but is silent to the weight percent of citric acid and therefore does not explicitly disclose a weight percent of acid from between 0.2 to 6 wt.%.
Kobal, directed to a liquid aerosol formulation for use in an electronic smoking article, discloses the formulation comprising at least one active ingredient, one aerosol former, nicotine and at least one acid ([0006]).
Kobal further discloses the suitable acids are included in an amount ranging from about 0.1% weight to about 15% by weight of the formulation ([0079]). The range disclosed by the prior art overlaps the claimed range of an acid from between 0.2 to 6wt.%, and is therefore considered prima facie obvious.
Therefore, before the effective filing date of the claimed invention, it would be obvious for one having ordinary skill in the art to modify Cameron by making the acid of Cameron comprise a specific weight percentage, as taught by Kobal, because both are directed to aerosolizable liquid formulations, and this merely involves looking to a similar reference for a suitable range, especially when the prior art is silent to an amount, and applying a known amount of acid of a similar composition to yield predictable results.
Additionally, Kobal further discloses the amount of acid added to the liquid aerosol formulation may depend on the strength of the acid and the amount needed to adjust the pH of the liquid aerosol formulation to the desired range. If too much acid is added, essentially all of the available nicotine will be protonated and will enter the particle phase of the aerosol, leaving very little unprotonated nicotine in the gas phase of the aerosol. The resultant aerosol may not produce sufficient levels of sensory response in terms of throat harshness to meet preferences of a smoker of lit-end cigarettes. In contrast, if too little acid is added, a larger amount of nicotine will remain unprotonated and in the gas phase of the aerosol, such that the smoker will experience increased throat harshness. ([0080]).
Kobal teaches the amount of acid is a result effective variable and it would have been obvious to one of ordinary skill in the art at the time the invention was made to optimize the amount of acid within the aerosolizable formulation 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. In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). The burden is upon the Applicant to demonstrate that the claimed weight percentage of acid is critical and has unexpected results. In the present invention, one would have been motivated to optimize the amount of acid motivated by the desire to protonate the right amount of nicotine such that sufficient levels of sensory response in terms of throat harshness to meet the preferences of the user because too little acid increases throat harshness and too much acid lowers the sensory experience for the user ([0080]).
(II)
Kuntawala, directed to e-cigarette/vaping fluid, teaches improving vaping fluids by using cyclodextrin to enhance absorbability of active ingredients while suppressing any irritating tendency of the aerosol (Abstract, [0016], and [0017]). Cyclodextrins are disclosed by the Applicant as an encapsulating material (page 28 of Applicant’s specification).
Kuntawala further discloses cyclodextrins also promote aerosol formation with the heating elements of common e-cigarettes and the choice of cyclodextrin is affected by the active ingredient as well as the other ingredients in the e-liquid formula ([0016]-[0017]).
Kuntawala further discloses cyclodextrin molecules such as α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin ([0017]).
Therefore, before the effective filing date of the claimed invention, it would have been obvious for one having ordinary skill in the art to modify the liquid composition of Cameron to include encapsulating cyclodextrins, as taught by Kuntawala, because both Cameron and Kuntawala are directed to liquids for electronic cigarettes, Kuntawala teaches that cyclodextrins can improve absorbability of active ingredients such as nicotine and reduce the tendency toward irritation caused by the aerosol that is formed, as well as promote aerosol formulation ([0016]-[0017]), and this involves improving a similar e-liquid with cyclodextrin molecules to yield predictable results.
Kuntawala further teaches (V):
Cameron fails to explicitly disclose a molar ratio of encapsulating material to flavor is from 5:1 to 1:5 (V).
Kuntawala further discloses cyclodextrin complexes form best with a molar excess of cyclodextrin and that it has been found that a 2-3 fold molar excess works well although cyclodextrin is effective in the range of 0.5 to 5.0 molar ratio of cyclodextrin to active ingredient (i.e., flavors) ([0021]). The range disclosed by the prior art overlaps the claimed range of encapsulating material to flavor is from 5:1 to 1:5 and is therefore considered prima facie obvious.
Therefore, before the effective filing date of the claimed invention, it would have been obvious for one having ordinary skill in the art to further modify the liquid composition of Cameron to include encapsulating cyclodextrins in a range that is effective with the flavors of Cameron, as taught by Kuntawala, because both Cameron and Kuntawala are directed to liquids for electronic cigarettes, Kuntawala teaches that cyclodextrins can improve absorbability of active ingredients such as nicotine and are effective in a range of 0.5 to 5.0 molar ratio of cyclodextrin to flavor ([0016] and [0021]), and this involves improving a similar e-liquid with cyclodextrin molecules to yield predictable results.
(III)
Cameron in view of Kuntawala discloses the use of different types of cyclodextrins (Kuntawala [0016]-[0017]) but fails to explicitly disclose the use of substituted cyclodextrins.
Demain, directed to a smoking composition containing a flavorant-release additive, discloses a water-soluble molecular inclusion complex contains a lipophilic organic flavorant compound as an essential constituent (column 2, lines 41-44).
Demain further discloses the water-soluble molecular inclusion complex is a substituted beta-cyclodextrin for encapsulating the constituent (i.e., flavorant) (column 2, lines 61-68 and column 3, lines 8-24).
Demain further discloses beta-cyclodextrin that is substituted with hydroxyalkyl groups is used over unsubstituted cyclodextrin derivatives, so that it has an increased solubility in water (column 2, lines 61-68).
Demain further discloses it is known in the art to encapsulate a flavorant with a substituted cyclodextrin (column 3, lines 41-55).
Demain further discloses flavorant-release additive, which is the filler/flavorant encapsulated by a substituted cyclodextrin, can be incorporated into the tobacco or tobacco substitute in accordance with methods known and used in the art (column 3, lines 52-55).
Therefore, before the effective filing date of the claimed invention, it would be obvious to one of ordinary skill to modify the cyclodextrin molecule of Cameron, in view of Kuntawala, to be a substituted cyclodextrin, as taught by Demain, because Demain teaches that use of substituted cyclodextrin is preferable over un-substituted cyclodextrin because substituted cyclodextrin has improved water solubility to form water soluble inclusion complexes that carry the flavorant (column 2, lines 61-68).
(IV)
Cameron, in view of Kuntawala and Demain, discloses the same encapsulating materials, substituted cyclodextrins, and flavorings (Cameron, [0061] and Demain column 2, lines 61-68) as claimed and disclosed by the Applicant, as discussed above.
Therefore, it follows that with the same encapsulating material and flavorings that the prior art liquid composition would have a similar energy of binding in the presence of water of the one or more encapsulating materials with the one or more flavors to be encapsulated as claimed. As such, one of ordinary skill in the art would reasonably conclude that the liquid composition of Cameron, in view of Kuntawala and Demain, would have an energy of binding from -5.6 to -8 kcal/mol similarly as claimed, absent evidence to the contrary.
Regarding claims 2, 25 and 26, Cameron, in view of Kuntawala and Demain, discloses a water-soluble encapsulating material (Demain column 2, lines 27-30), but does not appear to explicitly disclose that the encapsulating materials have a solubility in water of at least 50%, at least 70%, or at least 90% of the solubility in water of the one or more flavors.
However, Cameron, in view of Kuntawala and Demain, discloses the same encapsulating materials, cyclodextrins, and flavorings (Cameron, [0061] and Demain column 2, lines 27-30) as claimed and disclosed by the Applicant. Therefore, it follows that with the same encapsulating material and flavorings that the encapsulating materials of Cameron, in view of Kuntawala and Demain, would have solubilities in water of at least 50%, at least 70%, and at least 90% of the solubility in water of the one or more flavors similarly as claimed, absent evidence to the contrary.
Regarding claims 7 and 8, Cameron discloses water in an amount of about 70 wt.% to about 99 wt.% ([0010], [0015], and [0056]). The range disclosed by the prior art overlaps the claimed ranges of water in an amount of at least 75wt% and at least 90wt%, respectively and is therefore considered prima facie obvious.
Regarding claims 9-10, Cameron discloses nicotine in an amount of from about 0.01 wt.% to about 10 wt.% ([0058]). The range disclosed by the prior art overlaps the claimed ranges of nicotine present in an amount no greater than 1% and nicotine present in an amount from 0.01 to 0.6wt%, respectively and is therefore considered prima facie obvious.
Regarding claims 12-14, Cameron discloses that the liquid composition may further comprise one or more additives including an acid, such as citric acid ([0078]).
Regarding claims 17 and 18, Cameron discloses that the liquid composition may comprise menthol ([0078] and [0117]).
Regarding claims 19 and 20, Cameron discloses that the flavoring agent can be present in about 1 wt.% to about 30 wt.% ([0062]). The claimed ranges of no greater than 2 wt.% and from 0.01 to 1 wt.% overlap the range taught by the prior art and are therefore considered prima facie obvious.
Regarding claim 23, Demain discloses substituted β-cyclodextrin (column 2, lines 61-68).
Regarding claim 24, Kuntawala discloses a molar ratio of cyclodextrin to active ingredient in the range of 0.5 to 5.0 ([0021]). Given the molar ratio and disclosed amount of nicotine of Cameron ([0058]), which may be considered an active ingredient, one of ordinary skill in the art would reasonably conclude that the cyclodextrin would be present in a range that overlaps the claimed range of no greater than 12 wt.%.
Regarding claim 27, Cameron discloses that the flavoring agent may be any flavoring comprising any component that is known to provide a pleasant taste to the user ([0061]). Therefore, given that Cameron may comprise any flavor, it is reasonable for one having ordinary skill in the art to reasonably conclude that the liquid composition of Cameron, in view of Kuntawala and Demain, would include embodiments wherein the composition contains no flavors that can be encapsulated by cyclodextrins. Alternatively, Cameron does not disclose that the flavoring is encapsulated and therefore may comprise embodiments wherein no flavoring is encapsulated by the cyclodextrins.
Claims 15 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Cameron et al. (US 2017/0325494 A1) in view of Kobal et al. (US-20250325614-A1), and Kuntawala et al. (US 2016/0198759 A1) and Demain (US-5144964-A), as applied to claim 1 above, and further in view of Rabinowitz et al. (US 2014/0345635 A1).
Regarding claims 15 and 16, Cameron discloses additives including acids ([0078]).
Cameron does not appear to explicitly disclose that the total content of acid present in the composition is no greater than 1.0 mole equivalents based on the nicotine, or no less than 0.1 mole equivalents based on the nicotine.
However, Rabinowitz, directed to compositions for nicotine aerosol delivery, teaches that compositions use ion pairing agents such as acids in compositions comprising nicotine to provide for control over, or otherwise affect, deposition of the nicotine in the body ([0035]). Rabinowitz discloses examples of ion pairing agents include similar acid additives disclosed by Cameron ([0048]). Rabinowitz discloses that the molar ratio of ion pairing agent to nicotine may range from 1:3 to about 3:1 ([0050]). The claimed contents of acid to nicotine overlaps the range taught by Rabinowitz and are therefore considered prima facie obvious.
Therefore, before the effective filing date of the claimed invention, it would have been obvious for one having ordinary skill in the art to modify the liquid composition of Modified Cameron, to have an acid to nicotine molar ratio of 1:3 to about 3:1 as taught by Rabinowitz because both are directed to liquid compositions comprising nicotine and acids for aerosol generation, Cameron is silent in regards to the amount of acid to nicotine should be used, one of ordinary skill would look to a similar reference for known molar ratio ranges of acid to nicotine such as Rabinowitz, and this merely involves applying a known teaching to a similar composition to yield predictable results.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/MADELEINE P DELACRUZ/Examiner, Art Unit 1755 /PHILIP Y LOUIE/Supervisory Patent Examiner, Art Unit 1755