Prosecution Insights
Last updated: October 25, 2026
Application No. 18/627,520

COMPOSITIONS COMPRISING ADAMANTYL ESTER-CONTAINING COMPOUNDS

Non-Final OA §103§112
Filed
Apr 05, 2024
Priority
Apr 07, 2023 — provisional 63/494,884
Examiner
WALKER, AJA ARYANNA
Art Unit
1761
Tech Center
1700 — Chemical & Materials Engineering
Assignee
The Procter & Gamble Company
OA Round
1 (Non-Final)
67%
Grant Probability
Favorable
1-2
OA Rounds
7m
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
48 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

§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 11 October 2024. The Examiner has considered the reference cited therein to the extent that each is a proper citation. Please see the attached USPTO Form. Election/Restrictions Applicant's election without traverse of Group I (claims 1-19) in the reply filed on 26 August 2026 is acknowledged. Claim 20 is cancelled and withdrawn from consideration from further consideration pursuant to 37 CFR 1.142(b), as being withdrawn to a non-elected invention, and non-elected species of the invention, there being no allowable generic or linking claims. Claims 1-19 are under examination and the requirement for restriction is made final. 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 10-12 and 16 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Regarding claims 10-12, the phrase "preferably" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d). A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 10 recites the broad recitation 100:0 to 25:75, and the claim also recites 100:0 to 50:50, 100:0 to 51:49, 100:0 to 75:25, 100:0 to 90:10, 100:0 to 95:5, and 100:0 to 99:1 which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 11 recites the broad recitation at least 0.001%, and the claim also recites at least 0.01%, 0.1%, 0.5%, and 1% which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 12 recites the broad recitation at least 0.001%, and the claim also recites at least 0.01%, 0.1%, 0.5%, and 1% which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. Claim 16 contains the trademark/trade name Neobee® caprylic/capric triglyceride. 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 caprylic/capric triglyceride and, accordingly, the identification/description is indefinite. 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. 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. Claims 1-6, 11, 13, 15, and 17-19 are rejected under 35 U.S.C. 103 as being unpatentable over Narula (US-4985403-A). With regard to claim 1-6 and 15, Narula teaches adamantane derivatives defined by the generic structure: PNG media_image1.png 189 191 media_image1.png Greyscale wherein R1 is hydrogen or acetyl; R2 is hydrogen or methyl; and R3 is hydrogen or methylene and the dashed line represents a carbon-hydrogen single bond or a carbon-methylene double bond. These compounds are utilized to augment or enhance the aroma of consumable materials, specifically selected from the group consisting of perfume compositions, colognes, and perfumed articles (col. 1, lines 7–28). Furthermore, when R1 is acetyl, R2 and R3 are hydrogen, n is 1, m is 0, the target compound specified in claim 6 (b) and formula 1 is obtained. Narula further teaches that the incorporation of a Tween 20 surfactant within the product (col. 26, line 46), which satisfies the "surfactant" limitation of the claimed treatment adjunct. Additionally, Narula teaches that the perfume compositions comprise at least one adamantane derivative prepared according to the disclosed processes, with the derivative present in an amount ranging from 0.005% (or 0.01%) to less than 50% (col. 14, lines 56–68; col. 15, lines 1–7). This disclosure inherently encompasses the claimed range. The Examiner provided a visual comparison between the presently claimed Compound 6b (left) and the prior art compound disclosed by Narula (right), noting that both representations correspond to the same chemical entity. PNG media_image2.png 367 871 media_image2.png Greyscale Narula does not teach the claimed consumer product to the degree of specificity as to be anticipatory. With regard to the structure, it would have been prima facie obvious to one of ordinary skill in the art at the time of Applicant's invention to modify the teachings of Narula by substituting the overlapping genus in the substituents to arrive at the claimed compounds of formula I. The reference teaches an identical core structure and overlapping various functional groups to modify. MPEP 2144.09 (I) states “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 rePayne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In rePapesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) and In reDillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990). Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art, as evidenced by the reference, especially in the absence of evidence to the contrary. With regard to claim 11, Narula teaches that the perfume compositions comprise at least one adamantane derivative prepared in accordance with the processes of the present invention, wherein the derivative is present in an amount ranging from as little as 0.005% (or 0.01%) to less than 50% (col. 14, lines 56–68 and col. 15, lines 1–7), which reads on the claimed range. With regard to claims 13 and 17-19, Narula teaches that the specified applications encompass soaps, cosmetics, colognes, perfumed polymers, and various detergent systems (including anionic, cationic, nonionic, or zwitterionic formulations), as well as fabric softener compositions and articles (col. 14, lines 56–68; col. 15, lines 1–7). This disclosure broadens the scope to encompass pro-fragrance materials and diverse product formats such as liquids, creams, sprays, and bars across multiple sectors, including beauty care, fabric care, home care, feminine care, and health care. Claims 7, 10 , 12, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Narula (US-4985403-A) as applied to claims 1-6, 11, 13, 15, and 17-19 above, and further in view of Gillaspey (US-5021184-A). The teachings of Narula is disclosed above. With regard to claim 7, Narula teaches a structural homolog of the claimed 7(b) and 6(b) with the following configuration: PNG media_image3.png 143 195 media_image3.png Greyscale Narula teaches that this specific compound is characterized by a piney, camphoraceous, balsamic, and woody aroma, complemented by camphoraceous armoise and animalic top notes (Table 1-continued, col. 14, lines 5-15). In the same field of endeavor, Gillaspey teaches an adamantane derivative of the following structure (Table A-continued, col 2, line 5): PNG media_image4.png 133 188 media_image4.png Greyscale This corresponds to the instant compound of claim 7(b), which is a homolog of the compound disclosed in Narula. Gillaspey teaches that this specific compound exhibits a woody, amber, vetiver, cedarwood, piney, and chrysanthemum-like aroma, characterized by woody, amber, and olibanum top notes (Table A-continued, col. 3, line 5). Furthermore, Gillaspey discloses that these adamantane derivatives are utilized to augment or enhance aromas in perfume compositions, perfumed articles, colognes, deodorizing articles, and malodor maskants (Abstract). The Examiner has carefully drawn the previously mentioned compound for visualization (homologs of claimed 7b) and 6b) compound of Narula on the left, and compound of Gillaspey and its differences). PNG media_image3.png 143 195 media_image3.png Greyscale PNG media_image5.png 111 146 media_image5.png Greyscale With regard to the overlapping genera, it would have been prima facie obvious to one of ordinary skill in the art at the time of Applicant's invention to modify the teachings of Narula by substituting a hydrogen for a methyl to arrive at the claimed compound of 7 b). The skilled artisan would predict that such a substitution of both hydrogen and methyl in the same positions lead to the same activity. MPEP 2144.09 (I) states “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities.”. With regard to the second fragrance, it would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention, to modify the fragrance composition of Narula. Specifically, to incorporate another adamantane derivative as established in Gillaspey. The references collectively teach similar fragrance compounds and scent notes for identical applications. One of ordinary skill in the art would achieve the predictable result of addition of adamantane derivatives for its augment aromas, as Narula explicitly teaches the use of adamantane derivatives. 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 enhanced aromas as established in Narula and Gillaspey. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art, as evidenced by the references, especially in the absence of evidence to the contrary. With regard to claim 10, Narula teaches that the perfume compositions comprise at least one adamantane derivative prepared in accordance with the processes of the present invention, wherein the derivative is present in an amount ranging from as little as 0.005% (or 0.01%) to less than 50% (col. 14, lines 56–68 and col. 15, lines 1–7). In the same field of endeavor, Gillaspey teaches that the effective concentration of the adamantane derivatives in perfume compositions depends on multiple variables, including the selection and concentration of other ingredients, as well as the desired olfactory effects. Notably, effective perfume compositions may contain as little as 0.5% of one or more of these adamantane derivatives. The concentration may range up to 50% or higher, determined by cost considerations, the nature of the end product, the specific fragrance profile sought, and the intended impact on the finished formulation (col. 59, lines 21-45). These combined teachings of Narula and Gillaspey overlap the specified weight ratios and the utilization of both structures. With regard to claim 12, Narula teaches that the perfume compositions comprise at least one adamantane derivative prepared in accordance with the processes of the present invention, wherein the derivative is present in an amount ranging from as little as 0.005% (or 0.01%) to less than 50% (col. 14, lines 56–68 and col. 15, lines 1–7), which reads on the claimed range. With regard to claim 14, Narula teaches that the specified applications encompass soaps, cosmetics, colognes, perfumed polymers, and various detergent systems (including anionic, cationic, nonionic, or zwitterionic formulations), as well as fabric softener compositions and articles (col. 14, lines 56–68; col. 15, lines 1–7). This disclosure broadens the scope to encompass pro-fragrance materials and diverse product formats such as liquids, creams, sprays, and bars across multiple sectors, including beauty care, fabric care, home care, feminine care, and health care. Claims 8-9 are rejected under 35 U.S.C. 103 as being unpatentable over Narula (US-4985403-A) and Gillaspey (US-5021184-A) as applied to claims 7, 10 , 12, and 14 above, and further in view of Science Direct et al. “Antioxidant” The teachings of Narula and Gillaspey are disclosed above. With regard to claims 8-9, Narula teaches a homolog structure adamantane derivatives defined by the generic structure: PNG media_image1.png 189 191 media_image1.png Greyscale wherein R1 is hydrogen or acetyl; R2 is hydrogen or methyl; and R3 is hydrogen or methylene and the dashed line represents a carbon-hydrogen single bond or a carbon-methylene double bond. These compounds are utilized to augment or enhance the aroma of consumable materials, specifically selected from the group consisting of perfume compositions, colognes, and perfumed articles (col. 1, lines 7–28). Furthermore, when R1 is acetyl, R2 and R3 are hydrogen, n is 1, m is 0, the target compound specified in claim 6 (b) and formula 1 is obtained. The Examiner has provided a drawing of the previously mentioned compounds. From left to right, this illustration depicts the homolog of claimed compound 6b, the prior art compound of Narula, and the claimed compound of formula 9, along with its structural differences. PNG media_image2.png 367 871 media_image2.png Greyscale PNG media_image6.png 321 366 media_image6.png Greyscale With regard to the overlapping genera, it would have been prima facie obvious to one of ordinary skill in the art at the time of Applicant's invention to modify the teachings of Narula by substituting a hydrogen for a methyl to arrive at the claimed compound of 7 b). The skilled artisan would predict that such a substitution of both hydrogen and methyl in the same positions lead to the same activity. MPEP 2144.09 (I) states “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities.”. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art, as evidenced by the references, especially in the absence of evidence to the contrary. Narula does not explicitly teach the use of an antioxidant. In the same field of endeavor, Science Direct et al. teaches antioxidants serve as formulation stabilizers that prevent the rancidity of fatty substances—such as natural oils, fats, and fragrances—in cosmetic products. Additionally, Science Direct et al. teaches that antioxidants function as skin-care actives to protect skin from oxidative stress by scavenging free radicals, thereby delaying signs of skin aging (7.4.8 Antioxidants, page 3). Furthermore, antioxidants are molecules capable of oxidizing themselves preferentially to protect adjacent molecules. They consist of compounds or systems that interact with free radicals to terminate chain reactions before vital cellular or formulation components are damaged. Consequently, the application of antioxidants is widely recognized across the food, cosmetic, beverage, pharmaceutical, and animal feed industries, where they are utilized either as health-promoting supplements and active ingredients, or as formulation stabilizers (2.1 Antioxidants, page 6). With regard to the antioxidant, it would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention, to modify the fragrance composition of Narula. Specifically, to incorporate an antioxidant as established in Science Direct et al. Science Direct et al. would guide one having ordinary skill in the art to employ antioxidant in cosmetic products to ensure formulation stability and provide oxidative stress benefits (7.4.8 Antioxidant). A person having ordinary skill in the art would be motivated to combine these known elements, with a reasonable expectation of success, to achieve enhanced formulation stabilization while maintaining desired cosmetic properties as taught by Science Direct et al. Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Narula (US-4985403-A) as applied to claims 1-6, 11, 13, 15, and 17-19 above, and further in view of Holland (US-20210032561-A1). The teaching of Narula is disclosed above. With regard to claim 16, Narula does not explicitly disclose the claimed specified carrier, the reference does teach that the fragrance composition may include a vehicle or carrier for the adamantane derivatives, specifically identifying glycols such as propylene glycol (col. 15, lines 37-44). In the same field of endeavor, Holland discloses a fragrance composition utilized in consumer products such as fabric care, air care, home care, and beauty care (Abstract). Holland further notes that, the formulation comprises a mixture of fragrance materials optionally combined with other ingredients, including perfume carriers. Holland defines a "perfume carrier" to include materials that are practically neutral from a perfumery perspective and do not significantly alter the organoleptic properties of the perfuming components. According to Holland, this carrier may consist of compatible liquid or solid fillers, diluents, and the like, where "compatible" indicates that the components can be combined with the primary actives—and with each other—without interactions that would substantially reduce the composition's efficacy under ordinary use. The specific carrier type depends on the desired product form and may include, but is not limited to, solutions, aerosols, emulsions (oil-in-water or water-in-oil), gels, and liposomes. Notably, Holland states that the carrier is preferably a liquid solvent, such as dipropylene glycol, isopropyl myristate, and triethyl citrate (para. [0162]), which reads on the limitations of the claimed carrier. With regard to the carrier, it would have been obvious to one of ordinary skill in the art before the effective filling date of the claimed invention, to modify the vehicle or carrier—such as the glycol—of Narula. Specifically, to a carrier established in Holland. Holland would guide one having ordinary skill in the art to employ a perfume carrier such as dipropylene glycol, noting its compatibility, miscible properties, and suitability from a perfumery standpoint, all while leaving the underlying perfumery components substantially unaltered (para [0162]). The person of ordinary skill in the art would have been motivated to make this modification in order to achieve the desired compatibility and arrive at the claimed invention. One of ordinary skill in the art would achieve the predictable result of substituting or utilizing a carrier like dipropylene glycol, as Narula explicitly teaches the use of a glycol-based carrier. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the before the effective filing date of the claimed invention, as evidenced by the references, especially in the absence of evidence to the contrary. 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 September 29, 2026
Read full office action

Prosecution Timeline

Apr 05, 2024
Application Filed
Oct 02, 2026
Non-Final Rejection mailed — §103, §112 (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 (~7m 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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