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 .
Information Disclosure Statement
Although the CN 105061407A reference was cited in the IDS filed on February 9th, 2023 (previously considered) a machine translation of the claims and the disclosure of this reference was used for the purposes of prior art rejections and cited in Form PTO-892.
Status of the Claims
Claims 2 and 4-10 are pending in this application. Claims 1 and 3 have been cancelled by Applicant.
Claim Rejections - 35 USC § 103
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.
Claims 2 and 4-10 are rejected under 35 U.S.C. 103 as being unpatentable over Feiyan et al. (CN 105061407 A – cited in the IDS); in view of SCENIHR (Scientific Committee on Emerging and Newly Identified Health Risks, Tobacco Additives I, 2016, 131 pages – previously cited).
Regarding instant claim 2, Feiyan discloses a method for preparing fragrance compounds for use in tobacco products (Feiyan’s claims 2 and 7). Feiyan discloses their method according to the scheme below, wherein X can be
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and R2-5 can be H (Feiyan’s claims 1-2), corresponding to the instant 2-acetylpyridine, and the lactone compound corresponds to the aroma compound to be released upon burning of the tobacco product (see page 2, para. 3, lines 3-6 of machine translation of the description). Feiyan discloses that acetylpyridines have a unique fragrance and are added to low-tar cigarettes to improve the quality of cigarettes and reduce irritation (page 1 of translated description, second to last para., last 2 lines). Feiyan teaches their coupled fragrance compound (resulting from the aldol between the lactone and the acetylpyridine) has the characteristics of high stability and can overcome the disadvantages of high volatility, small threshold value, heavy smell, and easy loss of processing during the process of the lactones alone; that the fragrance compound can be cracked and released at high temperature (puffing conditions) to release aroma substances such as the lactone and acylpyridine, which are used to improve the smoking quality of cigarettes (page 3 of translated description, para. 1).
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Feiyan discloses the following order of operations (reading on the instant claims): (i) dissolving their lactone compound in a solvent; (ii) adding a base at a temperature of -78 °C to 50 °C, stirring the reaction for more than 10 min; (iii) adding the acylpyridine to continue at -78 °C to 50 °C; (iv) stirred for 30 min or more under temperature conditions, followed by quenching the reaction; and (v) finally subjected to post-treatment separation and purification to obtain the target compound (see Feiyan’s claim 2 in machine translated document). Feiyan discloses their method wherein the solvent is methyl tert-butyl ether, tetrahydrofuran, dioxane, methyl-tetrahydrofuran, dichloromethane, dimethyl sulfoxide, and petroleum ether (see Feiyan’s claim 3 in machine translated document)
Regarding claim 4, Feiyan teaches their method wherein the base is BuLi, LDA, LiHMDS, NaNH2, NaH, NaOC(CH3)3, KOC(CH3)3, NaOEt, or KOEt (see Feiyan’s claim 4 in machine translated document)
Regarding claim 5, Feiyan teaches their method wherein the molar ratio of the lactone, the base, and the acylpyridine is 1: (1 to 2): (1 to 1.5) (see Feiyan’s claim 5 in machine translated document).
Regarding claim 6, Feiyan teaches their method wherein the quenching reaction and the post-treatment are carried out by quenching the reaction with water, separating the organic layer, washing with saturated brine, drying with anhydrous sodium sulfate, filtering, removing solvent under reduced pressure, and the obtained residue purified by silica gel column chromatography (see Feiyan’s claim 6 in machine translated document).
Regarding claim 7, Feiyan discloses their reaction at a temperature of -78 °C to 50 °C, stirring the reaction for more than 10 min; then adding the acylpyridine to continue at -78 °C to 50 °C and stirring for 30 min or more.
Regarding claims 8-9, Feiyan discloses a method of applying their fragrance compound by adding to a product which releases the fragrance in a combustion or heating process in an amount of from 0.00001% to 10% by weight. Feiyan discloses addition of their fragrance compound to the tobacco in an addition ratio of 0.00001% to 2% by weight of the tobacco (see Feiyan’s claims 7-8 in machine translated document).
Regarding claim 10, Feiyan discloses their fragrance compound being dissolved in water or alcohol and being sprayed or injected onto the tobacco; wherein the tobacco is a mixed or flue-cured type (see Feiyan’s claims 9-10 in machine translated document).
Regarding the instantly claimed ranges of: (i) temperatures of -78 °C to 0 °C or -70 °C to 0 °C; (ii) molar ratios of 1: (4 to 6): (1-1.5) between the lactone, the alkali, and acetylpyridine; (iii) time ranges of 30 min to 12 h; (iv) amount of aroma compound added of 0.00001% to 10% weight of the product; or (v) the amount of aroma compound added of 0.00001% to 2% weight of the tobacco; as recited in instant claims 2, 5, and 7-9, as discussed above, and in view of Feiyan’s disclosure, it is noted that the courts have stated where the claimed ranges overlap or lie inside the ranges disclosed by the prior art and even when the claimed ranges and prior art ranges do not overlap but are close enough that one skilled in the art would have expected them to have similar properties, a prima facie case of obviousness exists. See In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); Titanium Metals Corp. of America v. Banner, 778 F2d 775. 227 USPQ 773 (Fed. Cir. 1985) (see MPEP 2144.05.01). The courts have also found 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. See In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05-II.
Therefore, the claimed ranges merely represent an obvious variant and/or routine optimization of the values of the cited prior art.
While Feiyan does not specifically teach ɣ-caprolactone as the flavoring/ aroma portion of these tobacco additives. The teachings of SCENIHR are relied upon for these disclosures.
SCENIHR discloses ɣ-caprolactone (a.k.a. gamma-hexalactone) (page 23, compound 2) as a flavor and aroma constituent in tobacco products.
Therefore, it would have been prima facie obvious to one of ordinary skill prior to the effective filing date of the instant application to prepare the instantly claimed ɣ-caprolactone precursor-aroma compound from 2-acetylpyridine and ɣ-caprolactone in view of Feiyan and the cited report from SCENIHR. One of ordinary skill would have been motivated to prepare this compound with a reasonable expectation of success in view of Feiyan’s teachings of related compounds as additives for tobacco products to release flavoring/ aroma components, which are synthesized from 2-acylpyridine and a lactone aroma compound; that their coupled fragrance compound has the benefit of high stability and can overcome the disadvantages of high volatility, small threshold value, heavy smell, and easy loss of processing during the process of the lactone compounds alone; and that the fragrance compound can be cracked at high temperature to release aroma substances such as the lactone and acylpyridine, which improves the smoking quality and reduces irritation. One would have been further motivated with a reasonable expectation of success in view of SCENIHR’s disclosure that ɣ-caprolactone is a known lactone additive for tobacco products, known to have “sweet, creamy, vanilla-like with powdery green lactonic nuances,” which may appeal to tobacco consumers.
Response to Arguments
Claim Status
Amendments to the claims is acknowledged. No new matter has been introduced.
Interview Summary
Summary of the Interview held on August 14th, 2025 is acknowledged.
Drawings
Applicant’s arguments, see page 5-6, filed September 12th, 2025, with respect to the objection to the drawings submitted on 10/25/2022 have been fully considered and are persuasive. The new drawings, submitted on September 12th, 2025, are accepted. Thus, the objection of the drawings has been withdrawn.
Claim Objections
Applicant’s arguments, see pages 6, filed September 12th, 2025, with respect to the objection to claim 2 have been fully considered and are persuasive. The objection of claim 2 has been withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s arguments with respect to claims 2 and 4-10, regarding Houminer et al., have been considered but are moot because the new ground of rejection does not rely on Houminer et al., applied in the prior rejection of record, for any teaching or matter specifically challenged in the argument.
Claim 1 has been cancelled, thus 35 USC § 103 rejections of claim 1 are moot.
Claim 2, claim has been amended to exclude diethyl ether as one of the claimed solvents, limiting the claim to MTBE, THF, dioxane, MTHF, DCM, 1,2-DCE, DMSO, and petroleum ether. Applicant argues that the SCENIHR reference fails to disclose the claimed solvents. Applicant further argues that SCENIHR provides a toxicological review of zinc oxide and titanium dioxide nanoparticles, it is not directed to synthetic chemistry, does not disclose chemical reactions, and does not disclose any teaching related to the claimed aroma compound or its preparation. Applicant further argues that the specific compound is not shown or suggested. Applicant argues their sub-zero alkaline conditions involving enolate chemistry and precise control of temperature and timing to ensure the desired product is formed, and that SCENIHR does not contain any mention of such a reaction. Applicant argues that the purpose of SCENHIR is regulatory, not synthetic. Applicant further argues that the reaction shown in the claim is regio- and stereo- selective aldol-type addition.
In response to applicant's argument that SCENIHR is nonanalogous art, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992).
In this case, SCENIHR (previously cited), discloses ɣ-caprolactone (a.k.a. gamma-hexalactone) (page 23, compound 2) as a flavor and aroma constituent in tobacco products, which is the same use cited in the instant claims.
In response to applicant's arguments against the SCENIHR reference individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to applicant's argument that the references fail to show certain features of the invention, it is noted that the features upon which applicant relies (i.e., the stereo- and regioselectivity of the aldol-type reaction) are not recited in the rejected claims or in the specification. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Applicant argues that the specification explicitly states that the inventors identify specific limitations of known lactone and acylpyridine compounds, namely high volatility, low threshold, strong odor, and tendency to be lost during processing. Applicant states their innovation addresses the volatility and loss issues and expands the functional scope of lactone fragrances.
In response to applicant's argument that the prior art does not address the volatility or stability of their aroma precursor compounds, the fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious. See Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985).
Applicant has submitted an affidavit, filed September 12th, 2025, signed by the inventor, in which they declare that deviation from the claimed temperature and time ranges (Temp: -78 °C – 0 °C; and Time: 30 min to 12 h) would result in the formation of by-products, loss of selectivity, and/or degradation of the desired compound, compromising yield and purity and forming a compound that lacks the intended aroma properties or decomposes.
While the Applicant asserts that the claimed temperature and time ranges are crucial for the performance of the reaction claimed, no factual evidence is disclosed to support this. The presently cited art discloses a similar aldol reaction with 2-acetylpyridine and a lactone (see 103 rejections in this office action). The cited art conducts a similar aldol at a temperature ranging from -78 °C to 50 °C, and stirring for 30 min or more. Feiyan’s conditions have a substantial overlap with the instantly claimed conditions, and as discussed above, Feiyan teaches their coupled fragrance compound (resulting from the aldol between the lactone and the acetylpyridine) has the characteristics of high stability and can overcome the disadvantages of high volatility, small threshold value, heavy smell, and easy loss of processing during the process of the lactones alone; that the fragrance compound can be cracked and released at high temperature (puffing conditions) to release aroma substances such as the lactone and acylpyridine, which improve the smoking quality of cigarettes (page 3 of translated description, para. 1).
Arguments presented by the applicant cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965) and In re De Blauwe, 736 F.2d 699, 705, 222 USPQ 191, 196 (Fed. Cir. 1984).
Claim 4, Applicant states SCENHIR does not address bases used in the claimed reaction.
Claim 5, Applicant states SCENHIR is irrelevant, and that the use of extraction and/or chromatography for the stated product is not disclosed in the references.
Claim 6, Applicant states SCENHIR doesn’t disclose their purity values.
Claims 7-8, Applicant states SCENHIR doesn’t disclose the claimed compound or its use in flavoring.
Claim 9, Applicant states SCENHIR doesn’t disclose chemical transformations.
Regarding arguments to claims 4-9 above, Applicant is reminded that one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references.
Claim 10, Applicant states the conversion of ɣ-caprolactone is triggered by enzymatic hydrolysis in the oral cavity, and that the physiological context of this transformation is not disclosed by the art.
In response to applicant's argument that the references fail to show certain features of the invention, applicant is reminded that the features upon which applicant relies (i.e., hydrolysis of ɣ-caprolactone in the oral cavity) are not recited in the rejected claim. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims.
Conclusion
THIS ACTION IS MADE FINAL. 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 JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
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/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627
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