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 .
Final Rejection
The Status of Claims:
Claims 1, 3-18, and 20-22 are pending.
Claims 1, 4-14, 21-22 are rejected.
Claims 15-18 are allowable
Claims 3 and 20 are objected.
IDS
The IDS filed on 7/27/26 has been reviewed by the examiner.
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 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.
Claim Objections
Claims 3 and 20 are objected to because of the following informalities:
In claims 3 and 20, the phrases” the salt of claim 2” and “The process of claim 19” are recited. These expressions are improper because the claim 3 depends on the canceled claims 2 and 19. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
The rejection of Claims 3, 18-20 and 22 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, is withdrawn.
Claim Rejections - 35 USC § 102
2113 Product-by-Process Claims
PRODUCT-BY-PROCESS CLAIMS ARE NOT LIMITED TO THE MANIPULATION OF THE RECITED STEPS, ONLY THE STRUCTURE IMPLIED BY THE STEPS
“Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 77 F.2d 695,698,227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted) (Claim was directed to a novolac color developer. The process of making the developer was allowed. The difference between the inventive process and the prior art was the addition of metal oxide and carboxylic acid as separate ingredients instead of adding the more expensive prereacted metal carboxylate. The product-by-process claim was rejected because the end product, in both the prior art and the allowed process, ends up containing metal carboxylate. The fact that the metal carboxylate is not directly added, but is instead produced in-situ does not change the end product.).
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.
In view of the revised claim 1, the 102 rejection has been changed in the following>
The rejection of Claim(s)1, 4-14, 21-22 under 35 U.S.C. 102(a)(1) as being anticipated clearly by Zheng et al (WO 2021/062061 A1) has been changed to the rejection of Claim(s), 21-22 under 35 U.S.C. 102(a)(1) as being anticipated clearly by Zheng et al (WO 2021/062061 A1).
Claim Rejections - 35 USC § 103
Applicants’ argument filed 7/27/26 have been fully considered, and some are
persuasive. However, in view of the revised claims, another 103 rejection seems
necessary.
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.
I The rejection Claims 1-2, 15-19 under 35 U.S.C. 103 as being unpatentable over Zheng et al (WO 2021/062061 A1) in view of Wikipedia (.Methyl Isobutyl Ketone , Jan. 26, 2018, p.1-3) is withdrawn.
However, in view of the revised claims, the 103 rejection seems necessary in the followings:
:Claim(s) 1, 4-14, 21-22 are rejected under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Zheng et al (WO 2021/062061 A1).
Determination of the scope and content of the prior art
Zheng et al discloses an immediate release 50 mg granule formulation as in claim 14 of denatonium acetate monohydrate (DA) as in claims 21-22 as a free base as an immediate gastric release oral pharmaceutical formulation.(see page 15, example 8, table 9). It also teaches an oral pharmaceutical immediate gastric release pharmaceutical formulation as in claim 13 comprising granules which comprise a denatonium cation salt and a sour anion selected from the group consisting of acetate (DA), citrate (DC) tartrate (CT), maleate (DM) and combinations (see page 3 , line 15); furthermore, its pharmaceutical excipients comprise talc, as in claim 10, a cellulose as in claims 4-6 and a saccharide as in claim 7. Preferably, the oral formulation further comprises an organic acid selected from the group consisting of acetic acid, as in claims 11-12 and others (see page 3 , lines 19-21).
Further, it provides a sustained release oral formulation comprising DA
PNG
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230
992
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(see pages 5-6, table 1) and acetic acid powder in a sustained release cellulosic and mannitol excipient formulation as in claims 8-9(see page 3, lines 30-32).
Zheng et al discloses a granule formulation denatonium acetate monohydrate (DA) as in claim 1 (see page 15, example 8, Table 9).
Furthermore, it teaches the preparation of denatonium acetate from denatonium Hydroxide, thereby forming the crystallized denatonium acetate in the followings:
To a reflux apparatus 10 g of denatonium hydroxide (MW: 342.475 g/mol, 0.029 mol), 20 mL of acetone, and 2 g of acetic acid glacial (0.033 mol) dissolved in 15 mL of acetone is added, the mixture is stirred and heated to 35°C for 3 h. Then evaporated to dryness and recrystallized in hot acetone(see page 10, lines 3-7, example 5).
The current invention, however, differs from the prior art in that
the preparation of the claimed denatonium acetate monohydrate in a crystalline is unspecified in the prior art .
Ascertainment of the difference between the prior art and the claims
The difference between the current application and the applied Zheng et al art is that the Zheng et al does not expressly teach the claimed denatonium acetate monohydrate in a crystalline form.
Resolving the level of ordinary skill in the pertinent art.
Regarding the Claims 1, 4-14, with respect to the lack of disclosing a definitive crystalline form of the claimed denatonium acetate monohydrate, the prior art does teach that the preparation of denatonium acetate from denatonium hydroxide, thereby forming the crystallized denatonium acetate in the followings:
To a reflux apparatus 10 g of denatonium hydroxide (MW: 342.475 g/mol, 0.029 mol), 20 mL of acetone, and 2 g of acetic acid glacial (0.033 mol) dissolved in 15 mL of acetone is added, the mixture is stirred and heated to 35°C for 3 h. Then evaporated to dryness and recrystallized in hot acetone(see page 10, lines 3-7, example 5).
From this example of producing the crystallized denatonium acetate, it can be naturally or inherently for the skilled artisan in the art to have assumed that the claimed denatonium acetate monohydrate can be in a crystalline form subsequently. Furthermore, regarding the presence of the term “ crystalline” in the claim, there is no patentable weight over the prior art compound since the prior art and the claimed compound are the same compound unless there are a set of x-ray diffraction data present in the claims.
So, if the skilled artisan in the art had desired to verify the crystalline form of the prior art denatonium acetate monohydrate , it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to perform X-ray crystallography on the compound.
This is because the skilled artisan in the art would expect such a manipulation to be within the purview of the skilled artisan in the art because the prior art does point out that the result of the prepared denatonium acetate is in a crystalline form as a guidance shown in the prior art. Therefore, the prior art is definitely and inherently related to the claimed invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
Zheng et al expressly discloses the granule formulation of denatonium acetate monohydrate (DA) and the preparation of denatonium acetate in a crystalline form after recrystallization using acetone.
Although Zheng et does not mention the crystalline denatonium acetate monohydrate literally, the prior art does teach indirectly that the crystallized denatonium acetate can be produced as a result of the preparation of denatonium acetate from denatonium hydroxide(see page 10, lines 3-7, example 5). Similarly, this means that it can be naturally or inherently for the skilled artisan in the art to have assumed that the prior art denatonium acetate monohydrate can be in a crystalline form subsequently.
So, it would have been obvious to the skilled artisan in the art before the effective filing date of the claimed invention to be motivated to have assumed that Zheng et al compound can have the crystalline denatonium acetate monohydrate naturally or inherently just like the claimed invention.
This is because the prior art does point out that the result of the prepared denatonium acetate is in a crystalline form as a guidance shown in the prior art.
Applicant’s arguments are in the followings:
More specifically, the Office alleges Zheng "discloses a granule formulation denatonium acetate monohydrate" and "teaches the preparation of denatonium acetate from denatonium hydroxide." Action at page 8. The Office acknowledges that "[t]he current invention...differs from the prior art in that the preparation of the claimed denatonium acetate monohydrate in a crystalline form by using methyl isobutyl ketone and a specific amount of water are unspecified in the prior art." Action at pages 8-9. The Office alleges "Wikipedia describes that unlike the other common ketone solvents, acetone and MEK, methyl isobutyl ketone has quite low solubility in water, making it useful for liquid-liquid extraction." Id. at page 9.
The Office acknowledges Zheng "does not expressly teach the claimed preparation of the denatonium acetate monohydrate in a crystalline form by using methyl isobutyl ketone and a specific amount of water," however, the Office alleges the "deficiencies of the Zheng...are partially cured by the Wikipedia." Action at page 9. The Office also acknowledges "Wikipedia does not expressly teach the claimed limitations of the preparation of the claimed denatonium acetate monohydrate in a crystalline form and a specific amount of water," however, the Office alleges the "deficiencies of the Wikipedia are partially cured by the Zheng." Id.
The Office acknowledges "the prior art is silent about the use of the specific amount of water," however the office alleges "it would have been obvious to the skilled artisan in the art to be motivated to control the optimum percentage range of water during the crystallization process." Action at page 10. The Office alleges Zheng and Wikipedia "are closely related to each other with respect to a crystallizing process and a solvent substitute." Action at page 11. The Office further alleges "it would have been obvious to the skilled artisan in the art...to be-8-
motivated to incorporate the teaching of the Wikipedia's methyl isobutyl ketone solvent into the Zheng's preparation in the absence of an unexpected result... [and] would expect such combined preparations to be feasible and success[ful] as shown in the prior art." Id.
Applicant respectfully disagrees and traverses.
As previously noted above, solely to advance prosecution, claim 1 is amended to
incorporate certain elements of claim 2. Zheng mentions a granule formulation of denatonium acetate monohydrate (see, e.g., page 15, lines 1-2 of Zheng). Zheng does not indicate whether the granules are crystalline or amorphous. In contrast, independent claim 1 recites a crystalline denatonium acetate monohydrate salt. Independent claim 15 is directed to a process for preparing a denatonium acetate salt, comprising the steps of (1) contacting an equivalent of anhydrous denatonium acetate with methyl isobutyl ketone and water such that the water concentration is above 10 weight percent, (2) recovering a resultant solid phase, and (3) removing the solid phase therefrom.
Zheng does not teach or suggest a crystalline denatonium acetate monohydrate salt, and as acknowledged by the Office, Zheng does not teach or suggest the claimed preparation of the denatonium acetate monohydrate. Zheng also does not provide any reason to seek or obtain crystalline denatonium acetate monohydrate. Zheng also does not teach or suggest a method of preparing the crystalline form and as acknowledged by the Office, Zheng "does not describe the use of methyl isobutyl ketone and water in the crystallization process." Action at page 11.
One of ordinary skill in the art would not have had any motivation from Zheng to prepare denatonium acetate monohydrate so as to obtain a crystalline form of the monohydrate. Thus, one of ordinary skill would not have looked to Wikipedia or combined it with Zheng. In any event, Wikipedia does not cure the deficiencies of Zheng. Wikipedia is a summary of methyl isobutyl ketone. Wikipedia is silent to methyl isobutyl ketone being used in preparing a crystalline form of any material, let alone crystalline denatonium acetate monohydrate. Wikipedia discloses methyl isobutyl ketone "has quite low solubility in water, making it useful for liquid-liquid extraction." (see, e.g., 1st paragraph of "Solvent and niche applications" section of Wikipedia). Liquid-liquid extraction does not suggest crystallization, and the statement that methyl isobutyl ketone has quite low solubility in water does not suggest that it would be useful for isolating and crystallizing a monohydrate, in which a water molecule is retained, let alone crystalline monohydrate of denatonium acetate in particular. Indeed, there is no teaching or suggestion in either cited document to use methyl isobutyl ketone as a solvent to generate crystalline material. Nothing in Wikipedia teaches or suggests the claimed crystalline denatonium acetate monohydrate and the preparation of the denatonium acetate monohydrate.
Therefore, a person of ordinary skill in the art would not reasonably expect from Zheng and Wikipedia, either alone or in combination, that any solvent, let alone methyl isobutyl ketone, can be used to obtain a new crystalline form, nor would they be led to Applicant's claimed crystalline denatonium acetate monohydrate and the preparation of the denatonium acetate monohydrate.
In contrast, the results in the present application provide a crystalline denatonium acetate monohydrate and a method of obtaining the claimed crystalline form of denatonium acetate monohydrate that is not taught or suggested in Zheng and/or Wikipedia. See, e.g., pages 4-5, paragraphs [0017]-[0018] and Example 1 in the Specification as filed.
As such, Wikipedia would not have led a person of skill in the art to modify the teachings Zheng to obtain Applicant's claimed crystalline denatonium acetate monohydrate salt and Applicant's claimed process for preparing a denatonium acetate salt, comprising the steps of (1) contacting an equivalent of anhydrous denatonium acetate with methyl isobutyl ketone and water such that the water concentration is above 10 weight percent, (2) recovering a resultant solid phase, and (3) removing the solid phase therefrom. Accordingly, Applicant respectfully submits that the present claims would not have been obvious to one skilled in the art, and respectfully requests that the rejection be withdrawn.
Applicants’ arguments have been noted. However, as indicated in the above,
in view of the revised claims, the rejection Claims 1-2, 15-19 under 35 U.S.C. 103 as being unpatentable over Zheng et al (WO 2021/062061 A1) in view of Wikipedia (.Methyl Isobutyl Ketone , Jan. 26, 2018, p.1-3) has been changed to the rejection of Claim(s) 1, 4-14, 21-22 under 35 U.S.C. 102(a)(1) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Zheng et al (WO 2021/062061 A1). Therefore, Applicants’ arguments will be responded in the next communication.
Conclusion
Claims 1, 4-14, 21-22 are rejected.
Claims 15-18 are allowable.
Claims 3 and 20 are objected.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TAYLOR V OH whose telephone number is (571)272-0689. The examiner can normally be reached on 8:00-5:00.
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/TAYLOR V OH/Primary Examiner, Art Unit 1625 10/07/2026
