Prosecution Insights
Last updated: October 27, 2026
Application No. 18/832,528

COMPOSITIONS COMPRISING 4-ISOPROPYL-1-METHYL-7-OXABICYCLO[2.2.1]HEPTAN-2-OL OR ESTERS OR ETHERS THEREOF AND THEIR USE AS AROMA CHEMICALS

Non-Final OA §101§102§103§112
Filed
Jul 24, 2024
Priority
Jan 26, 2022 — EU 22153455.5 +1 more
Examiner
WALKER, AJA ARYANNA
Art Unit
1761
Tech Center
1700 — Chemical & Materials Engineering
Assignee
BASF SE
OA Round
1 (Non-Final)
67%
Grant Probability
Favorable
1-2
OA Rounds
10m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 67% — above average
67%
Career Allowance Rate
6 granted / 9 resolved
+1.7% vs TC avg
Strong +43% interview lift
Without
With
+42.9%
Interview Lift
resolved cases with interview
Typical timeline
3y 1m
Avg Prosecution
47 currently pending
Career history
53
Total Applications
across all art units

Statute-Specific Performance

§101
2.6%
-37.4% vs TC avg
§103
57.0%
+17.0% vs TC avg
§102
13.2%
-26.8% vs TC avg
§112
16.7%
-23.3% vs TC avg
Black line = Tech Center average estimate • Based on career data from 9 resolved cases

Office Action

§101 §102 §103 §112
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 Receipt is acknowledged of the Information Disclosure Statement filed 16 August 2024. The Examiner has considered the reference cited therein to the extent that each is a proper citation. Please see the attached USPTO Form. 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. Claims 23-30 and 40-43 are indefinite because the claim merely recites a use without any active, positive steps delimiting how this use is actually practiced. See MPEP 2173.05(q) Claims 40-41 and 43 contains the trademark/trade name Ferula jaeschkeana. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a rhizome and, accordingly, the identification/description is indefinite. Claim Rejections - 35 USC § 101 35 U.S.C. 101 reads as follows: Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title. Claims 23-30 and 40-43 is rejected under 35 U.S.C. 101 because the claimed invention is directed to non-statutory subject matter. Claims 23-30 and 40-43 are use claims. The claim does not fall within at least one of the four categories of patent eligible subject matter because a “use” claim does not purport to claim a process, machine, manufacture, or composition of matter. See MPEP 2173.05(q). Claim Rejections - 35 USC § 102 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. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claim 31 is rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Bledsoe (US-4853089-A, located in Information Disclosure Statement). With regard to claim 31, Bledsoe teaches a composition comprising 75.6 wt. % exo-2-hydroxy-1,4-cineole and 10.3 wt. % carvenone (Example 6, col. 6, line 65-66). This disclosure anticipates a composition comprising (a) a compound of formula (I) wherein R1 represents H, and (b) a compound of formula (II). Claims 35-36 are rejected under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Barton et al. “Herbicidal Activity of Cineole Derivatives” (located in Information Disclosure Statement). With regard to claim 35-36, Barton et al. teaches the compound 2-exo-butoxy-1,4-cineole in combination with a hexane solvent (Table 6, Figures 2 and 11b), which meets the limitation of the compound of formula (I) wherein R1 is a C3-alkylcarbonyl group in combination with a solvent. Furthermore, the instant specification defines the "non-aroma carrier" as comprising one or more solvents and further lists hexane as a suitable solvent (page 21, lines 28–29; page 9, lines 20–23). Thus, the disclosure satisfies the claimed non-aroma carrier and overall composition. 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. This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention. Claim 33 is rejected under 35 U.S.C. 103 as being unpatentable over Bledsoe (US-4853089-A, located in Information Disclosure Statement) as applied to claim 31 above. The teaching of Bledsoe is disclosed above. With regard to claim 33, Bledsoe fails to teach that the claimed compound of the formula (I) R1 is not hydrogen. However, Example 6 (col. 6, line 65-66) of Bledsoe discloses a composition comprising 75.6 wt. % exo-2-hydroxy-1,4-cineole and 10.3 wt. % carvenone, which corresponds to a molar ratio of 6.56:1 and falls into the claimed ratio. With regard to the compound, exo-2-hydroxy-1,4-cineole is a homolog of a chain comprising C1-C4 alkyl-compounds differing regularly by the successive addition of the same chemical groups, in the present instance, a -CH3-group. Homologs “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”. In re Wilder, 563 F.2D 457, 195 USPQ 426 (CCPA 1977). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 245 (CCPA 1979); MPEP 2144.09. It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Bledsoe’s composition to a derivative of 1,4-cineole. Specifically, to modify to a straight chain comprising C1-C4 alkyl-compounds as homolog of exo-2-hydroxy-1,4-cineol, as exo-2-hydroxy-1,4-cineole is expected to possess similar properties and have similar utility relative to the claimed compounds. Claims 23-24, 26, 28-34, 37-44 are rejected under 35 U.S.C. 103 as being unpatentable over Miyawaki (JPH-01261327-A, located in Information Disclosure Statement) in view of Kropp (US-3686097-A). With regard to claims 23-24, 31, Miyawaki teaches a perfume composition comprising 2-hydroxy-1,4-cineole (Abstract), which reads on the compound of formula I, wherein R1 is hydrogen. Miyawaki further teaches that utilizing 2-hydroxy-1,4-cineole as a fragrance material enhances the cooling sensation of menthol, improves its longevity, and provides an enhanced flavor and aroma profile (page 2, lines 20-27 and page 3, lines 1-9). Miyawaki fails to teach the compound of the formula (II). However, Miyawaki does teach that this composition is suitably employed in body care products, such as bath additives, as well as other fragrance formulations (page 3, lines 44-45). In the same field of endeavor, Kropp teaches novel perfume compositions comprising para-menth-3-en-2-one (i.e., carvenone) and mixtures thereof (Abstract). Kropp teaches that these reaction products—namely 4-caranone and para-menth-3-en-one, either individually or in admixture—exhibit desirable odor characteristics and are particularly valuable as fragrance components (col 4, lines 11-26). With regard to the composition, it would have been obvious to a person of ordinary skill in the art before the effective filling date of the claimed invention to modify the composition of Miyawaki. Specifically, to incorporate carvenone as established in Kropp. Miyawaki would guide one having ordinary skill in the art to employ the composition within other fragrance formulations (page 3, lines 44-45). Kropp would guide one having ordinary skill in the art to employ carvenone for its desirable odor characteristics (col 4, lines 11-26). The references collectively teach fragrance composition comprising fragrance components. Therefore, a person having ordinary skill in the art would expect to modify the composition of Miyawaki to achieve the recognition properties as established in Kropp. With regard to claims 26, 36, 42, and 44, Miyawaki teaches a composition comprising 2-hydroxy-1,4-cineole (Abstract), which is a homolog of R1 as C1-C4 alkyl. With regard to the structure, exo-2-hydroxy-1,4-cineole is a homolog of a chain comprising C1-C4 alkyl-compounds differing regularly by the successive addition of the same chemical groups, in the present instance, a -CH3-group. Homologs “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”. In re Wilder, 563 F.2D 457, 195 USPQ 426 (CCPA 1977). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. “An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties.” In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 245 (CCPA 1979); MPEP 2144.09. It would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention to modify Miyawaki’s composition to a derivative of 1,4-cineole. Specifically, to modify to a straight chain comprising C1-C4 alkyl-compounds as homolog of exo-2-hydroxy-1,4-cineol, as exo-2-hydroxy-1,4-cineole is expected to possess similar properties and have similar utility relative to the claimed compounds. With regard to claims 28 and 32-33, Miyawaki teaches that the weight ratio of 2-hydroxy-1,8-cineole and 2- hydroxy-1,4-cineole is 0.0001:1 to 1:1 (Abstract). Miyawaki fails to teach the utilization compound of formula (II). In the same field of endeavor, Kropp teaches novel perfume compositions comprising para-menth-3-en-2-one (i.e., carvenone) and mixtures thereof (Abstract). Kropp teaches that these reaction products—namely 4-caranone and para-menth-3-en-2-one, either individually or in admixture—exhibit desirable odor characteristics and are particularly valuable as fragrance components. Kropp further notes that these products can be isolated via distillation or utilized as a mixture, and explicitly teaches incorporating these compounds into perfume compositions in an odoriferously effective amount ranging from 0.0001% to 50% (col 4, lines 11-26). Thus, combining a 1 wt. % concentration of 2-hydroxy-1,4-cineole (per Miyawaki) with the minimum and maximum (0.0001 to 50 wt.%) carvenone concentration taught by Kropp yields a calculated molar ratio of 0.0179:1 to 8941:1, which overlaps the claimed molar ratio. As stated above, the combined teachings of Miyawaki and Kropp teach the inclusion of carvenone. With regard to claims 29-30, Miyawaki teaches that the utilization of 2-hydroxy-1,4-cineole as fragrance materials enhances the cooling sensation of menthol used, and improves its sustainability, and has improved flavor and aroma (page 2, lines 20-27 and page 3, lines 1-9), which reads as a fragrance, and for modifying and/or enhancing the aroma of the composition. With regard to claims 34 and 37-38, Miyawaki teaches that this composition is suitably employed in body care products, such as bath additives, as well as other fragrance formulations (page 3, lines 44-45). Miyawaki exemplifies this by incorporating coumarin, ionone, carvone, and propylene glycol (Examples 4-5, page 5-6) which corresponds to the claimed aroma chemicals distinct from compounds (I) and (II), alongside the specified non-aroma chemical carriers. With regard to claim 39, Miyawaki teaches that the relevant fragrance composition can be incorporated into a wide variety of consumer products. Specifically, Miyawaki discloses use in oral hygiene products (e.g., toothpastes and mouth rinses), food and beverages (e.g., chewing gum, candies, and drinks), and hair or body care products (e.g., shampoos and hair tonics) (page 3, lines 40-44). This disclosure reads on the claimed body care, oral/dental hygiene, food, and food supplement compositions. With regard to claims 40-41 and 43, Miyawaki does not teach that the use encompass the use of exo-2-hydroxy-1,4-cineole as an aroma chemical/or modifying the aroma is derived from the rhizomes of Ferula jaeschkeana. Thus, it can be interpreted that it reads on the use of the compounds. Claims 25 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Miyawaki (JPH-01261327-A, located in Information Disclosure Statement) and Kropp (US-3686097-A) as applied to claims 23-24, 26, 28-34, 37-44 above, and further in view of Barton et al. “Herbicidal Activity of Cineole Derivatives” (located in Information Disclosure Statement). The teachings of Miyawaki and Kropp are disclosed above. With regard to claim 25, Miyawaki and Kropp do not teach the claimed compound of the formula (I) R1 is formyl or C1-C3-alkylcarbonyl. In the same field of endeavor, Barton et al. teaches the herbicidal activity of a composition comprising 1,4-cineole (i.e., 2-exo-hydroxy-1,4-cineole 10, Figure 2) derivatives and eucalyptus oils (Abstract). Barton et al. further teaches common 1,4-cineole derivatives are 2-exo-acetoxy-1,4-cineole 11a, and 2-exo-butoxy-1,4-cineole 11b (Table 6, Figure 2), which reads on the claimed compound of the formula (I) wherein R1 is hydrogen, C1-alkylcarbonyl, C3-alkylcarbonyl. Furthermore, Barton et al. teaches that Of the 1,4-cineole derivatives, the most effective germination inhibitor was 2-exo-acetoxy-1,4-cineole. Although 2-exo-benzoxy-1,4-cineole only inhibited germination, it suppressed ryegrass root and shoot growth at a lower concentration than any of the cineole derivatives (Figure 4). Generally, all evaluated substances were more effective at suppressing ryegrass root and shoot growth than suppressing germination (Table 7) (Results and Discussion, page 6, col 2). With regard to the structure, it would have been obvious to a person of ordinary skill in the art before the effective filling date of the claimed invention to modify the 2- hydroxy-1,4-cineole of Miyawaki. Specifically, to a 1,4-cineole derivative established in Barton et al. For doing so, Barton et al. would guide one having ordinary skill in the art to 1,4-cineole derivatives for gemination inhibition, ryegrass root, and shoot growth suppression. These effects refers to a bioherbicidal activity of the aroma ingredients rather than the sensory profile. The references collectively teach fragrance components. Therefore, a person having ordinary skill in the art would be motivated to combine these known elements, with a reasonable expectation of success, to achieve the modification as Miyawaki can be provided with 1,4-cineole derivatives. With regard to claim 27, Miyawaki and Kropp fail to teach the group -OR1 is bound in exo-position. In the same field of endeavor, Barton et al. teaches the herbicidal activity of a composition comprising 1,4-cineole (i.e., 2-exo-hydroxy-1,4-cineole 10, Figure 2) derivatives and eucalyptus oils (Abstract), which reads on the exo-position. As stated above, the combined teachings of Miyawaki and Barton et al. make it obvious to modify the structure of the 1,4-cineole. Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to Aja A Walker whose telephone number is (571)272-0037. The examiner can normally be reached Monday - Friday 7-5. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Angela Brown-Pettigrew can be reached at 571-272-2817. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /A.A.W./Examiner, Art Unit 1761 /TANISHA DIGGS/Primary Examiner, Art Unit 1761 October 14, 2026
Read full office action

Prosecution Timeline

Jul 24, 2024
Application Filed
Oct 16, 2026
Non-Final Rejection mailed — §101, §102, §103 (current)

Precedent Cases

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Study what changed to get past this examiner. Based on 3 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
67%
Grant Probability
99%
With Interview (+42.9%)
3y 1m (~10m remaining)
Median Time to Grant
Low
PTA Risk
Based on 9 resolved cases by this examiner. Grant probability derived from career allowance rate.

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