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 .
Status of Claims
Claims 1, 12, and 15-17 are pending. Claims 16-17 are withdrawn.
Priority
Instant application 18/038,001, filed 05/19/2023 claims priority as follows:
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Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
All references from IDS(s) received 05/19/2023 and 02/14/2025 have been considered unless marked with a strikethrough.
Response to Amendment
The amendment filed 02/02/2026 has been entered. Applicant has amended claims 1 and 12. Claims 2-11, 13-14, and 18-19 have been cancelled.
Claims 1-2, 4-10, 12, and 15 were previously rejected under 35 U.S.C. 102 over Bebernitz (WO 2011048112 A1), Choi (WO 2012165914 A1), Kim (WO 2015174695 A1), or Bebernitz (WO 2012140596 A1). In view of the amendments to claims 1 and 12, applicant has overcome these rejections. Therefore, all previous rejections under 35 U.S.C. 102 are withdrawn.
Claim Rejections - 35 USC § 103 - Maintained
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, 12, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Bebernitz et al. (WO 2012140596 A1; previously cited).
The teachings of Bebernitz are disclosed previously and at least those teachings are incorporated herein by reference. Bebernitz is drawn to glycoside derivatives as SGLT-2 inhibitors useful for treating diabetes (title, abstract).
Bebernitz fails to anticipate instant formula I or disclose Applicant’s elected species compound 2:
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However, Bebernitz represents the closest prior art to the claimed formula and elected species, and discloses the compound No. 1-1 (page 59, top):
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The Bebernitz compound is a homolog of Applicant’s elected species. MPEP 2144.09, second paragraph, states, “Compounds which are position isomers or 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). The homolog is expected to be preparable by the same method and to have generally the same properties. This expectation is then deemed the motivation for preparing the homolog. This circumstance has arisen many times. See In re Schechter and LaForge, 98 USPQ 144, 150, which states “a novel useful chemical compound which is homologous or isomeric with compounds of the prior art is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compounds.” See In re Wilder, 166 USPQ 545, 548. Note also In re Deuel 34 USPQ2d 1210, 1214 which states, “Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds … a known compound may suggest its analogs or isomers, either geometric isomers (cis v. trans) or position isomers (e.g., ortho v. para).”
Please also note that Bebernitz teaches that R3 in the general formula:
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can be a C1-6 alkyl (page 79, embodiment 1 and embodiment 10), which includes methyl. Accordingly, compounds which are homologs of 1-1 would have been expected by the skilled artisan to possess similar properties, particularly SGLT-2 inhibitory activity.
Accordingly, Applicant’s elected species reading on instant claims 1 and 12 having similar structure and the same utility as the compound in Bebernitz, would have been prima facie obvious before the effective filing date of the instant application. A skilled artisan would have been motivated to prepare a homolog of the compound disclosed by Bebernitz with a reasonable expectation of success to obtain a compound with the same utility.
With respect to claim 15, Bebernitz teaches pharmaceutical compositions comprising the glycoside derivatives above and a pharmaceutically acceptable carrier (page 88 and claim 25).
It would have therefore been prima facie obvious to prepare a pharmaceutical composition comprising the aforementioned compound and a pharmaceutically acceptable carrier.
Response to Arguments
In the Remarks filed 02/02/2026 responding to the rejection, applicant argues that “one cannot simply assume that a structurally modified compound will retain the same pharmacological effects” (Remarks, page 11).
Applicants’ arguments have been fully considered but are not found persuasive.
With respect to the argument that “once cannot simply assume that a structurally modified compound will retain the same pharmacological effects” please note that MPEP 2144.09, second paragraph, states, “Compounds which are position isomers or 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). The homolog is expected to be preparable by the same method and to have generally the same properties. This expectation is then deemed the motivation for preparing the homolog. This circumstance has arisen many times. See In re Schechter and LaForge, 98 USPQ 144, 150, which states “a novel useful chemical compound which is homologous or isomeric with compounds of the prior art is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compounds.” See In re Wilder, 166 USPQ 545, 548. Note also In re Deuel 34 USPQ2d 1210, 1214 which states, “Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds … a known compound may suggest its analogs or isomers, either geometric isomers (cis v. trans) or position isomers (e.g., ortho v. para).”
Applicant additionally points to the specification Table 2, which compares compounds 2 and 3 with the known compound Dapagliflozin, and argues that the substitution of CH2 with O for drug activity is not a conventional technical means in the art, and its technical effects cannot be anticipated (Remarks, page 13).
Applicants’ arguments have been fully considered but are not found persuasive.
With respect to the reference to Table 2 of the specification, please note that Table 2 represents a comparison to Dapagliflozin, which is not the closest prior art compound. Also, while compound 3 has structural differences to Dapagliflozin, and those structural differences appear to result in a different activity value (6.745 nM for compound 3 versus 0.147 nM for Dapagliflozin), both compounds still have inhibitory activity for SGLT2 (i.e., the compounds possess similar properties). Thus, the example provided in Table 2 supports the examiner’s position that compounds which are position isomers or homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.
Applicant further argues that compound 1-1 in Bebernitz can be regarded as one of the closest prior art compounds to the compounds in the present application, and relies on evidence in a Declaration under 37 CFR 1.132 to assert that compound 2 of the instant application has an activity advantage of more than one order of magnitude in the IC50 of in vitro inhibitory activity against human SGLT2 compared with compound 1-1 of Bebernitz.
Applicants’ arguments have been fully considered but are not found persuasive.
The Declaration under 37 CFR 1.132 filed 02/02/2026 has been considered but is insufficient to overcome the rejection as set forth in the last Office action because:
The comparative IC50 data is not consistent with the prior art disclosure. Applicant submits comparative IC50 data purporting to show unexpected results for the claimed compound relative to the prior art compound 1-1 of Bebernitz. However, the IC50 value reported in the Declaration for the prior art compound is 0.932, whereas Bebernitz discloses an IC50 of 0.36 (Bebernitz, page 43, Table 1, Example Number 1-1). This is a material, unexplained deviation between Applicant’s comparative testing and the disclosure of the closest prior art.
Pursuant to MPEP 716.02(e), “[w]here the comparison is not identical with the reference disclosure, deviations therefrom should be noted and evaluated, and if significant, explanation should be required. In re Armstrong, 280 F.2d 132, 126 USPQ 281 (CCPA 1960).” The deviation here is significant because applicant’s reported value places the prior art compound’s potency in a different order of magnitude than applicant’s claimed compound, materially affecting the alleged magnitude of unexpected improvement.
Further, the burden of explaining proffered data rests with Applicant. See MPEP 716.02(b) "[A]ppellants have the burden of explaining the data in any declaration they proffer as evidence of non-obviousness." Ex parte Ishizaka, 24 USPQ2d 1621, 1624 (Bd. Pat. App. & Inter. 1992). Likewise, MPEP 716.01(c) requires that objective evidence be supported by actual proof, and notes that “unexpected results must be established by factual evidence” (citing In re De Blauwe, 736 F.2d 699, 705, 222 USPQ 191, 196 (Fed. Cir. 1984)). Argument alone cannot substitute for evidence reconciling the discrepancy. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965).
Until the deviation is explained, the showing cannot be credited as a comparison with the closest prior art as required by MPEP 716.02(e) and In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979).
Applicant is required to explain the deviation between the IC50 value reported in the declaration for the prior art compound 1-1 and the value disclosed in Bebernitz. The value disclosed by Bebernitz (0.36 nmol/L) is equivalent to the IC50 value for instant compound 8 (0.356 nmol/L) which applicant states (Remarks, page 15) is “comparable to compound 2 …indicating both exhibit excellent efficacy”.
In view of the foregoing, when all of the evidence is considered, the totality of the rebuttal evidence of nonobviousness fails to outweigh the evidence of obviousness. Therefore, the rejection under 35 U.S.C. 103 is maintained.
Conclusion
Claims 1, 12, and 15 are rejected. Claims 16-17 are withdrawn.
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 Kyle Nottingham whose telephone number is (571)270-0640. The examiner can normally be reached M-F from 10:00 am - 6:00 pm.
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, Clinton Brooks can be reached at (571) 270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/K.N./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
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