DETAILED ACTION
Status of Claims
Receipt is acknowledged of the Applicants’ Amendments and Remarks, filed January 22, 2026.
Claims 1-25, 29, and 31-32 are pending and under consideration.
Claims 26-28 and 30 are/were previously cancelled by Applicant.
Claims 33-42 are new.
Claims 5, 18-19, 23-25, 29, and 31 remain withdrawn.
New claims 34-37, and 39-42 are withdrawn as explained below in the Election/Restriction section.
Claims 1-4, 6-17, 20-22, 32-33, and 38 are under consideration in the instant office action as explained below in the Election/Restriction section
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 .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-22 and 32, drawn to compounds and pharmaceutical compositions of Formula (I) in the reply filed on September 23, 2025 is acknowledged.
Applicant’s election of Group I, claims 1-22 and 32, drawn to compounds and pharmaceutical compositions of Formula (I) in the reply filed on September 23, 2025 is acknowledged.
Applicant’s election of the compound of claim 20 as a species of Formula (I) (shown below).
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Compound 20 reads on where X is O, Y1 and Y2 are N, R1 is an unsubstituted multi-ring carbon alicyclic group, R4 is methyl, z is 2, A is a carbocyclic aryl group, R is the same substituted alkyl group.
Therefore, compound 20 reads on claims 1-4, 6-17, 20-22, and 32.
Compound 20 does not read on claim 5 as Ring A is aryl; therefore, is aromatic and does not constitute a carbon alicyclic group, nor does compound 20 read on claims 18-19, which requires R1 to be multi-ring heteroalicyclic groups, thionorbonyl or oxonorbonyl, respectively.
In Applicant’s reply, Applicant argues search burden as a rationale for why they believe the restriction requirement to be improper. Applicant is reminded that the application under examination is a 371 of PCT/US2021/051375, and is not filed under 35 U.S.C. 111(a); therefore, “unity of invention” analysis, not “independent and distinct” analysis is applied. Please refer to MPEP § 1893.03 (d).
The requirement is still deemed proper and is therefore made FINAL.
For the purposes of compact prosecution, the search was expanded.
Claims 5, 18-19, 23-25, 29, and 31 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on September 23, 2025.
Claims 33-42 are new.
Claims 33 and 38 depends on claim 1, directed towards drawn to compounds and pharmaceutical compositions of Formula (I); therefore, are part of Group I and are elected.
Claims 34-36, 39-41 are directed towards a method for treating a subject suffering from or susceptible to a skin-related disorder or disease; therefore, are part of Group II and remain withdrawn.
Claims 37 and 42 are directed towards a method of increasing pigmentation in a tissue of a subject; therefore, are part of Group III and remain withdrawn.
Claims 1-4, 6-17, 20-22, 32, 33 and 38 are currently under examination and are the subject of this office action.
Information Disclosure Statement
One information disclosure statements (IDS) submitted on January 27, 2026 is acknowledged. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
WITHDRAWN OBJECTIONS
The examiner withdraws objections to the abstract and claims based on amendments made by Applicant.
WITHDRAWN REJECTIONS
The examiner withdraws rejections to Claims 1-4, 6-17, 20-22, and 32 under 35 U.S.C. 112(a) for written description based on claim amendments, interview discussion and further review with a training quality assurance specialist. Applicant is reminded that the rejection was made on the basis of written description not enablement.
The examiner withdraws rejections to Claims 1, 2-4, 6-7, 11-13, and 22 under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Fisher et al. (US PG-PUB 2020/0253981 A1) based on claim amendments made by Applicant, which have overcome the rejection.
The examiner withdraws rejections to Claims 1-3, 6-7, 11-12, and 22 under 35 U.S.C. 102(a)(1) and (a)(2) as being anticipated by Gray et al. (WO 2018/009544 A1) based on claim amendments made by Applicant, which have overcome the rejection.
MAINTAINED/MODIFIED REJECTIONS
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.
Claims 1-4, 6-17, 20-22, 32-33, and 38 are rejected under 35 U.S.C. 103 as being unpatentable over Fisher (US20200253981A1) in view of Lovering et al. (Lovering, F., Bikker, J. and Humblet, C., 2009. Escape from flatland: increasing saturation as an approach to improving clinical success. Journal of medicinal chemistry, 52(21), pp.6752-6756)(“Lovering No.1”) and Lovering (Lovering, F., 2013. Escape from Flatland 2: complexity and promiscuity. Med. Chem. Comm., 4(3), pp.515-519)(“Lovering No. 2”) and further in view of Lamoureux et al. (Lamoureux, G. and Artavia, G., 2010. Use of the adamantane structure in medicinal chemistry. Current medicinal chemistry, 17(26), pp.2967-2978) and Liu et al. (Liu, Joe, Daniel Obando, Vivian Liao, Tulip Lifa, and Rachel Codd. "The many faces of the adamantyl group in drug design." European journal of medicinal chemistry 46, no. 6 (2011): 1949-1963).
Regarding claim 1, Fisher teaches similar pyrimidopyrimidinones as SIK inhibitors including compound YKL 06-062, which meets the limitations of claim 1 excepting limitations for R1 is as shown below (column 139, Table 1, compound YKL 06-062).
[AltContent: textbox (Y1 = Y2 = N,A= A is a carbocyclic aryl group,R = the same substituted alkyl group,z = 2)]
[AltContent: rect][AltContent: rect][AltContent: textbox (R4 = methyl)]
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Fisher’s compound YKL 06-062 also meets the limitations of claims 2-4, “wherein each R is the same substituted alkyl.”
Fisher’s compound YKL 06-062 also meets the limitations of claim 6-7, “wherein Ring A is a mono ring carbocyclic aryl group.”
Fisher’s compound YKL 06-062 also meets the limitations of claims 11-13 “wherein R2 and R3 are independently unsubstituted alkyl,” as Fisher incorporates the 1,3-xylene substituent as instant invention.
Fisher also teaches pharmaceutical compositions comprising compound YKL 06-062, meeting the limitations of claim 22 (column 124, paragraph [0434]).
Fisher does not teach compounds that explicitly contain R1 substituents that are multi-ring carbon alicyclic or heteroalicyclic as per claims 8-10, 14-16, and claim 33.
Fisher also does not teach compounds where R1 is “optionally substituted adamantyl, optionally substituted norbornyl, optionally substituted cyclo [2,2,2] octanyl or optionally substituted bicyclo [3,3,1] nonanyl,” as per claim 17.
Fisher also does not explicitly teach the compounds recited in claim 20-22, and pharmaceutical compositions comprising compound 20 as per claims 32 and 38
However, Fisher’s compound and elected species of claim 20 only differ based on the R1 substituent. Fisher’s R1 is a cyclohexyl group, whereas the elected species of claim 20 uses a bulkier, more rigid adamantane group that contains three fused cyclohexanes and increased sp3 character compared to cyclohexyl.
[AltContent: textbox (R1)][AltContent: rect][AltContent: rect][AltContent: textbox (Elected Species )][AltContent: textbox (Fisher)]
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[AltContent: textbox (R1)]
As per MPEP 2144.09: “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, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963).
Both Fisher and instant invention’s compounds are SIK inhibitors used in treating skin pigmentation diseases and disorders; therefore, it is reasonable that one would be motivated to modify Fisher to access instant invention to achieve similar properties based on routine SAR studies to develop libraries of similar compounds and to optimize properties.
Additionally, as per MPEP 2144.09, III: “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979).
At column 151, paragraph [0532], Fisher further teaches: “Since there are limitations to topical delivery of drugs into human skin epidermis, novel SIK inhibitors designed to enhance epidermal permeation by reducing the size and increasing the lipophilicity (c Log P) to develop second generation SIK inhibitors YKL 06-061 and YKL 06-062 were derived (FIG. 6) (Bos and Meinardi 2000; Hadgraft and Pugh 1998).
Consequently, Fisher teaches that increasing lipophilicity is a desirable property and specifically a key property to optimize in enabling topical delivery of drugs into human skin epidermis, and furthermore, that such property can be optimized via structure-activity modifications to the R1 position as illustrated below with the cyclobutyl and cyclohexyl substitution onto R1 (see column 139, Table 1, compounds shown below).
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Page 150, Table 7 furthermore demonstrates that increasing saturation (i.e: Fsp3 character) specifically by modifying the R1 substituent results in increasing lipophilicity as demonstrated by log P values (5.28 for cyclobutyl vs. 6.17 for cyclohexyl).
Lovering No. 1 teaches that “More highly complex molecules, as measured by saturation, have the capacity to access greater chemical space. This results in greater potential to identify compounds that better complement the spatial subtleties of target proteins. Importantly, the three-dimensionality that saturation imparts may also result in greater selectivity, resulting in fewer off-target effects… As compounds are prepared in the drug discovery setting and transition from discovery through clinical trials to drugs, those that are more highly saturated are more likely to succeed in these transitions. Saturation also increased the likelihood of higher solubility and lower melting points. Compounds are much more likely to succeed as drugs if they have appropriate values for these properties.”
Lovering No. 2 teaches that “ Previously we reported that complexity, as measured by saturation and the presence of chiral centers, impacts success in the clinic. Physical properties that were found to play a role included melting point and solubility…Previously we reported that complexity, as measured by Fsp3 and the presence of chiral centers, impacts the probability of success in the clinic. It was noted that Fsp3 positively impacts melting point and solubility… Compounds with greater specificity and selectivity are expected to show less toxicity due to off target effects…. We found that both Fsp3 and the presence of chiral centers does impact promiscuity as measured by a Cerep panel as well as by a set of cyp isozymes. Promiscuity decreases 60% for non-aminergic compounds and 89% for aminergic compounds as a function of Fsp3.”
Consequently, Lovering teaches that increasing saturation as measured through increasing Fsp3 (i.e.: escaping flatland towards more 3D drug candidates) improves clinical success through improved physical properties, specificity, selectivity and decreased promiscuity.
Lamoureux teaches that adamantane “exhibits remarkable structural, physical and chemical properties. The molecule is rigid, yet almost unstrained due to the 4 cyclohexyl chairs contained within…. Since the molecule only contains aliphatic carbons and hydrogen atoms, it is unusually inert. The hydrogens are tertiary and secondary (no primary or methyl) which restricts the level of reactivity (e.g. oxidation).”
Lamoureux additional teaches that “It is a well-known fact that the addition of an adamantane group as an auxiliary confers higher lipophilicity/hydrophobicity to the entire molecule. For the design of drugs based on a lead molecule, this change can entirely affect the ADME properties.”
Liu teaches that “The value of the adamantyl group in drug design is multidimensional. The hydrophobic substituent constant for the adamantyl group has been estimated from the calculated partition coefficients (clogP values) of 31 adamantyl-bearing compounds in the clinic or in development as πadamantyl = 3.1, which indicates that the logP value of a compound with high water solubility (logP < < 0) could be moved with an adamantyl-based modification to a region that is more clinically useful. The steric bulk of the adamantyl group can: (i) restrict or modulate intramolecular reactivity; and (ii) impede the access of hydrolytic enzymes, thereby increasing drug stability and plasma half-life.”
Liu further teaches that “In almost all cases, an adamantyl-bearing compound will be more lipophilic than the des-adamantyl analogue. Beyond increasing partition coefficients, the adamantyl group positively modulates the therapeutic index of many experimental compounds, through a variety of mechanisms.”
Liu further teaches that “ In many cases, the adamantyl group has been found to increase drug-like qualities of a lead compound, without increasing toxicity.”
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to modify Fisher’s compound by replacing the cyclohexyl motif with an adamantane motif to access the elected species because Fisher teaches compound YKL 06-062 which is identical to instant invention excepting the R1 substituent. Fisher furthermore teaches that increasing lipophilicity is a desirable property in enabling drug delivery for topical applications, teaches that the R1 position can be modified, and that increasing saturation results in increased lipophilicity. Fisher’s compounds are also SIK inhibitors used to treat skin pigmentation disorders and Fisher teaches that the nitrogen is a modifiable position without loss of activity (i.e.: R1 substituent). Furthermore, Lovering teaches that increasing saturation and using more 3D molecules (i.e.: increasing Fsp3 and “escaping flatland”) can improve clinical success through improved physical properties, specificity, selectivity and decreased promiscuity, Lamoureux teaches that adamantane offers unique properties in terms of rigidity, stability, and increased lipophilicity and Liu teaches that adamantane can increase drug-like qualities of a lead compound without increasing toxicity.
Consequently, an ordinarily skilled artisan would be motivated to optimize Fisher’s compounds to access libraries of similar compounds with desirable properties for topical drug delivery arriving at instant invention as a highly predictable result with a reasonable expectation of success through standard SAR optimization as is common the art of medicinal chemistry and as an obvious modification based on Fisher’s prior work in R1 substitution patterns and changing ring sizes and shapes, and what is known in terms of additional benefits to drug properties from increasing saturation and use of adamantyl group as taught by Lovering, Lamoureux and Liu.
It would have been further prima facie obvious to access the pharmaceutical compositions containing the elected species as a highly predictable result with a reasonable expectation of success.
Therefore, claims 1-4, 6-17, 20-22, 32-33, and 38 are rejected as being obvious based on the beneficial teachings of Fisher, Lovering, Lamoreux and Liu.
Response to Arguments
The Remarks of January 22, 2026 have been fully considered but are not fully persuasive for the reasons below.
35 USC 103
Applicant’s Arguments:
“The rejection is traversed. The rejection requires, inter alia, that a particular adamantyl group be considered prima facie obvious based on a cyclohexyl group of Fisher et al. Such a structural difference, however, has been clearly recognized as NOT presenting a prima facie case under Section 103. Thus, as set forth in MPEP 2144.09, much greater structural similarity is required to establish a prima facie Section 103 case. In this regard, attention is directed In re Grabiak, 769 F.2d 729, 226 USPQ 871 (Fed. Cir 1985) - cited in MPEP 2144.09 - where the Federal Circuit held that substitution of a thioester group for an ester group in an herbicidal safener compound was not suggested by the prior art. The secondary citations of Lovering et al., Lovering, Lamoureux and Liu do not somehow substantiate the instant rejection. None of those documents pertain in any respect to compounds reported in Fisher et al. The skilled worker would have had no incentive to seek out Lovering et al., Lovering, Lamoureux and Liu and then for some reason modify Fisher et al. compounds based on those reports.”
Examiner’s Response:
The Examiner respectfully disagrees. As communicated during the interview on January 27, 2026, the Examiner disagrees with the interpretation of Grabiak. Applicant claims the Federal Circuit held that the substitution was not suggested by the prior art; however, what was actually critical in Grabiak was lack of evidence as the key piece for disfavoring structural similarity between the thioester and ester group.
Such lack of evidence does not apply to the present case. The Examiner has provided evidence from Fisher, Lovering, Lamoureux and Liu to establish a highly reasonable prima facie obvious case for structural similarity and furthermore, motivation for why a person of ordinary skill in the art would make such a modification of Fisher as aforementioned.
As explained to the Attorney of Record, Lovering and the concept of increasing saturation (i.e.: “escaping flatland”) is a fundamental teaching and cannon for an ordinarily-skilled artisan in the pharmaceutical arts and would be highly obvious, furthermore supported by Fisher’s teachings and SAR studies regarding highly similar structures directed towards identical targets and importance of lipophilicity in topical drug delivery and bolstered by the known benefits of adamantyl groups emphasized by Lamoureux and Liu in increasing lipophilicity and improving drug-like properties.
Applicant is further reminded as per MPEP 2145. IV: “One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., Inc., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Where a rejection of a claim is based on two or more references, a reply that is limited to what a subset of the applied references teaches or fails to teach, or that fails to address the combined teaching of the applied references may be considered to be an argument that attacks the reference(s) individually. Where an applicant’s reply establishes that each of the applied references fails to teach a limitation and addresses the combined teachings and/or suggestions of the applied prior art, the reply as a whole does not attack the references individually as the phrase is used in Keller and reliance on Keller would not be appropriate. This is because "[T]he test for obviousness is what the combined teachings of the references would have suggested to [a PHOSITA]." In re Mouttet, 686 F.3d 1322, 1333, 103 USPQ2d 1219, 1226 (Fed. Cir. 2012).
As aforementioned, Fisher provides sufficient teachings and motivations to guide an ordinarily-skilled artisan to modify the R1 position, Lovering and Liu bolster such motivations based on what is common knowledge in medicinal chemistry regarding the benefits of increasing saturation, and Lamoreux further supports selection of adamantyl based on benefits in increasing lipophilicity, which is a property Fisher teaches is desirable to optimize for and can be optimized for via modification of the R1 position. Such teachings and strategies are well-known to an ordinarily skilled practitioner in the art of medicinal chemistry and drug design.
Applicant is again reminded that the test for obviousness is based on what the combined teachings would have suggest to a person of ordinary skill in the art, not simply via reading the individual references.
Applicant’s Arguments:
“Still further, the results set forth in the Examples at page 42-53 of the application demonstrate activity of the present compounds, including the SLT-008 compound which is recited in inter alia claims 20, 32 and 34-37. Thus, among others: Example 5 (Salt Kinase Inhibition) at pages 42-43 of the application demonstrates that the compound SLT-008 is an effective agent capable of inducing cutaneous pigmentation. Examples 6-10 (in vitro and ex vivo skin tissue models) of the application show pigmentation efficacy of SLT-008. Example 6 shows topical application of SLT-008 induces melanin pigmentation. Example 7 shows SLT-008 pigmentation activity on human living skin explants. Example 11 demonstrates DNA protection provided by SLT-008. Example 12 shows good DNA protection activity provided by SLT-008 as demonstrated with living human skin explants. In view thereof, withdrawal of the rejections is requested.”
Examiner’s Response:
As aforementioned, Fisher also teaches similar compounds with similar properties that can be predicted based on R1 substitution. Consequently, upon weighing the data provided by Applicant against Fisher and the prima facie obvious case, the Examiner concludes such results are not unexpected.
Applicant is reminded that the burden is on Applicant to establish that results are unexpected and significant. As per MPEP 716.02(b), “The evidence relied upon should establish "that the differences in results are in fact unexpected and unobvious and of both statistical and practical significance." Ex parte Gelles, 22 USPQ2d 1318, 1319 (Bd. Pat. App. & Inter. 1992).”
As per MPEP 716.02, Applicant is further reminded that “Any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).”
Additionally, as per MPEP 716.02(c). I: “Where the unexpected properties of a claimed invention are not shown to have a significance equal to or greater than the expected properties, the evidence of unexpected properties may not be sufficient to rebut the evidence of obviousness. In re Nolan, 553 F.2d 1261, 1267, 193 USPQ 641, 645 (CCPA 1977).”
Furthermore, MPEP 716.02(c).II: “"Expected beneficial results are evidence of obviousness of a claimed invention, just as unexpected results are evidence of unobviousness thereof." In re Gershon, 372 F.2d 535, 538, 152 USPQ 602, 604 (CCPA 1967).”
As aforementioned, Fisher has provided guidance regarding SAR onto a similar structure including data regarding activity and drug-like properties. When taken into context of Fisher’s disclosure, the results of instant invention as expected and predictable. Again, absolute predictability is more required. Applicant has failed to demonstrate or explain how the data provided is unexpected in this context.
Furthermore, Applicant is reminded as per MPEP 716.02(d) that unexpected results must be commensurate in scope with claimed invention: “Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the "objective evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support." In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980).”
Applicant has only provided data for SLT-008.
Applicant is encouraged to respond and further explain how the claimed invention results in unexpected results in the context of Fisher, Lovering, Lamoureux, Liu and the claimed scope of invention and/or provide additional data to rebut the prima facie obvious case.
Applicant is additionally reminded of Claims 5,18-19,23-25,29,31,34-37 and 39-42 which remain withdrawn.
Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Katamreddy et al. (WO 2020/140055 A1) reports compounds with a similar structural features, pharmaceutical compositions and methods of treatment, particularly the use of 3D bulky substituents onto R1 nitrogen (see Example-123, page 276 by example only).
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Sennhenn et al. (US PG-PUB 2023/0192701 A1) also reports SIK inhibitors with structural similarities, pharmaceutical compositions and methods of treatment similar to instant invention (see page 146, Table 1, second compound by example only).
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Conclusion
Claims 1-4, 6-17, 20-22, 32-33, and 38 are under consideration and are rejected.
No claims are allowed.
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 CAROLYN L. LADD whose telephone number is (703)756-5313. The examiner can normally be reached M-Th, 7:00 am to 5:30 pm EST.
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, James H. Alstrum-Acevedo can be reached at 571-272-5548. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/C.L.L./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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