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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 05/05/2026 has been entered.
Response to Amendment
The office action is in response to Applicant’s amendment filed on 04/06/2026.
Claims 1-2, 7-10, 12-20, 23-28, and 30-35 are pending.
Claims 1, 23, 28, 32, and 34-35 are amended.
Claims 3-6, 11, 21-22, and 29 are cancelled.
Claims 28 and 30-35 are withdrawn as being directed to a non-elected invention.
Response to Arguments
Applicant’s arguments, see pages 9-11, filed 04/06/2026, 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 persuasive. The Applicant has provided new amendments that overcome the 112(a) enablement rejection.
On pages 11-12, the Applicant further argues that the newly presented amendments of the molar ratio of acid to nicotine is from 5:1 to 1:1 because none of the cited prior art teaches the claimed range.
The Examiner respectfully disagrees. At least one of the cited prior arts teaches a value that overlaps the claimed range. Kobal discloses the nicotine is included in the liquid aerosol formulation in an amount ranging from about 1% by weight to about 10% by weight ([0081]) and the acid, preferably citric acid, is included in the liquid aerosol formulation in an amount ranging from about 0.1 to about 15% by weight ([0079]). The ranges disclosed by Kobal overlap the disclosed ranges of nicotine and acid in the Applicant’s Specification and are therefore considered prima facie obvious that similar ranges of the same components would result in a molar ratio of the components that at the very least overlap the claimed range.
Furthermore, nicotine and citric acid have similar molar masses (nicotine: 162.23 g/mol; citric acid: 192.12 g/mol) and for example purposes only, assuming the nicotine and the citric acid are on the upper end of the preferable ranges (10% nicotine and 15% acid) would result in a molar ratio of about 1.27:1 which overlaps the claimed range of a molar ratio of acid to nicotine from 5:1 to 1:1, and is therefore considered prima facie obvious.
Furthermore, the previously cited prior art “Rabinowitz” does in fact teach the claimed molar ratio as detailed in claims 15-16 of the Final rejection dated 02/06/2026.
On page 12, the Applicant further argues that the Applicant has identified that by ensuring the molar ratio of acid to nicotine is from 5:1 to 1:1, the nicotine of the formulation is protonated which allows the flavor to out-compete the nicotine for encapsulation by the core of the cyclodextrin.
The Examiner respectfully does not find the arguments persuasive. There is no citation provided and nowhere stated that the claimed molar ratio is from 5:1 to 1:1 to ensure the nicotine is protonated and further allows the flavor to out-compete the nicotine for encapsulation.
Furthermore, Kobal teaches it is preferable to have protonated nicotine in the formulation before aerosolization ([0084]) and there is no requirement in the claims to teach nicotine protonation.
On page 12, the Applicant further argues that Kuntawala does not actually teach the molar ratio of 0.5 to 5 M of cyclodextrin to active ingredient because Kuntawala teaches flavors are not active ingredients and therefore cannot teach the claimed molar ratio of cyclodextrin to flavor.
The Examiner respectfully does not find the arguments persuasive. Kuntawala teaches the active ingredient can be chamomile, which is a flavor in accordance with Applicant’s instant specification (page 20). There is no reason a compound cannot act as both a flavor and an active ingredient and therefore the arguments are not persuasive.
Furthermore, Kuntawala discloses embodiments wherein the flavor is present in “trace amounts” and the cyclodextrin is from 0.05 to 0.2 Molar ([0027]-[0033]). Therefore, it would be obvious to one of ordinary skill in the art that a trace amount of flavor to cyclodextrin would likely result in a molar ratio with the cyclodextrin much greater than the flavor such as cyclodextrin to flavor having a molar ratio of 5:1 as claimed, and is therefore considered a prima facie obvious limitation.
A modified rejection based on the amendments is provided below.
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, 12-20, 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), Demain (US-5144964-A), DeKock (Development of a Sensitive and Accurate Method for the Qualitative Analysis of Encapsin TM HPB. | Springer Nature Link) and alternatively in view of Kuntawala et al. (US 2016/0198759 A1, cited in the IDS dated 04/30/2021) and/or Rabinowitz et al. (US 2014/0345635 A1).
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 explicitly disclose an acid present in an amount from 0.2 to 6w.% based on the aerosolizable formulation (I), wherein the molar ratio of acid to nicotine is from 5:1 to 1:1 (II), one or more encapsulating materials comprising hydroxy-propyl substituted cyclodextrins (III), that 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)
Cameron does not explicitly disclose the molar ratio of acid to nicotine is from 5:1 to 1:1.
Kobal discloses the nicotine is included in the liquid aerosol formulation in an amount ranging from about 1% by weight to about 10% by weight ([0081]) and the acid, preferably citric acid, is included in the liquid aerosol formulation in an amount ranging from about 0.1 to about 15% by weight ([0079]). The ranges disclosed by Kobal overlap the disclosed ranges of nicotine and acid in the Applicant’s Specification and it would be obvious that similar ranges of the same components would result in a molar ratio of the components that at the very least overlap the claimed range.
Furthermore, nicotine and citric acid have similar molar masses (nicotine: 162.23 g/mol; citric acid: 192.12 g/mol) and for example purposes only, assuming the nicotine and the citric acid are on the upper end of the preferable ranges (10% nicotine and 15% acid) would result in a molar ratio of about 1.27:1 which overlaps the claimed range of a molar ratio of acid to nicotine from 5:1 to 1:1, 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 further modify Cameron by making the composition further comprise a specific weight percentage of nicotine and thus a molar ratio of 1.27:1, 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.
(III)
Cameron does not explicitly disclose the use of hydroxyl-propyl 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 an example of the hydroxyalkyl group used is Molecusol HPB and Encapsin HPB, which are hydroxy-propyl beta cyclodextrins, and comprise about seven substitutions (col. 2, line 68 to col. 3, line 2).
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 further modify Modified Cameron by applying hydroxy-propyl substituted cyclodextrin as an encapsulating material to the liquid formulation of Cameron, as taught by Demain, because both are directed to aerosolizable compositions, Demain teaches that use of hydroxy-propyl substituted cyclodextrins are known encapsulating materials in the art (col. 3, lines 41-55) and substituted cyclodextrins are 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), and this merely involves applying a known technique of using a type of encapsulating material of a similar composition to yield predictable results.
(IV)
Modified Cameron discloses the same encapsulating materials, substituted cyclodextrins, and flavorings (Cameron, [0061] and Demain col. 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 Modified Cameron, would have an energy of binding from -5.6 to -8 kcal/mol similarly as claimed, absent evidence to the contrary.
Additionally, DeKock, directed to a qualitative analysis of encapsin HPB (hydroxypropyl beta cyclodextrins), discloses a range of recorded substitutions usually around 5 (Conclusion). Since Demain and DeKock both disclose HPB’s such as encapsin with substitutions of about 5 and 7, it would be obvious to one of ordinary skill in the art that a hydroxypropyl beta cyclodextrin with the same substitutions as the two provided examples in the Applicant’s Specification would also have similar binding energies to those claimed, and therefore the claimed binding energy is considered a prima facie obvious limitation.
(V)
Modified Cameron discloses HPB (Demain col. 2, lines 61-68), but Cameron does not explicitly disclose the molar ratio of encapsulating material to flavor is from 5:1 to 1:5.
Demain discloses example 1 comprising 100 mg Vanilla mixed with 2 mL of a 45% w/w aqueous solution of Encapsin HPB (i.e., hydroxypropyl beta substituted cyclodextrin) (col.2 lines 61-68 to col. 3, line 1), which results in about a 4.92:1 molar ratio of encapsulating material to flavor. 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.
Alternatively (V)
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]).
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, such as chamomile which in line with the Applicant’s Specification’s definition of 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 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.
The Examiner further notes that while Kobal makes obvious (II), additionally Rabinowitz also makes obvious the claimed ratio of acid to nicotine.
Alternatively (II)
Cameron discloses additives including acids ([0078]).
Rabinowitz, directed to compositions for nicotine aerosol delivery, teaches that compositions use ion pairing agents such as acids in compositions comprising nicotine to provide control over/affect the deposition of the nicotine in the body ([0035]).
Rabinowitz further discloses examples of ion pairing agents include similar acid additives as those disclosed by Cameron ([0048]). Rabinowitz discloses that the molar ratio of ion pairing agent (i.e., acid) 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, Rabinowitz teaches acid to nicotine molar ratios control the deposition of nicotine in the body ([0035]), one of ordinary skill would look to a similar reference for known molar ratio ranges of acid to nicotine such as Rabinowitz, especially when the prior art is silent to one, and this merely involves applying a known teaching to a similar composition to yield predictable results.
Regarding claims 2, 25 and 26, Modified Cameron, 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, Modified Cameron, discloses the same specific encapsulating material and flavorings (Cameron, [0061] and Demain column 2, lines 27-30) as claimed and disclosed by the Applicant. Therefore, it follows the same encapsulating material and flavorings would have the same claimed 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, 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 15-16, Kobal discloses the composition comprising at least 0.1 to 1 mole acid equivalents based on nicotine, as discussed above ([0079]-[0081]).
Alternatively, Rabinowitz, as discussed above teaches the molar ratio of ion pairing agent (i.e., acid) 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.
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 an HPB 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.
Conclusion
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/MADELEINE P DELACRUZ/Examiner, Art Unit 1755 /PHILIP Y LOUIE/Supervisory Patent Examiner, Art Unit 1755
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