DETAILED ACTION
Applicant’s arguments, filed 20 February 2026, have been fully considered. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
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 .
Claims 46, 52, and 55-60 are pending; in accordance with Applicant’s election of 10/23/2025, claims 55-59 are withdrawn; claims 46, 52, and 60 are examined.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 46, 52, and 60 rejected under 35 U.S.C. 103 as being unpatentable over Rhee et al. (US 2007/0155798 A1, 07/05/2007) (hereinafter Rhee) in view of Zhou et al. (US 2005/0043317 A1, 02/24/2005) (hereinafter Zhou).
Rhee discloses derivatives of oxazolidinone with inhibitory activity against a broad spectrum of bacteria and lower toxicity, and compositions comprising the derivatives for use in an antibiotic (abs). The derivatives of oxazolidinone include Formula I below:
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,
wherein X is nitrogen; R1 is fluorine; R1’ is hydrogen; R2 is -OR7, wherein R7 is hydrogen; Het is a tetrazole ring; R3 and R4, which are the same or different, respectively refers to hydrogen or C1-4 alkyl group that is substituted or unsubstituted ([0013]). Rhee further discloses wherein locations of a tetrazole group’s substitution includes the 2’ position (Table 1, row 10).
Rhee differs from the instant claims insofar as not disclosing wherein the C1-4 alkyl group is substituted with amino.
However, Zhou discloses a family of biaryl heterocyclic compounds, comprising both a biaryl moiety and at least one heterocyclic moiety, that are useful as therapeutic agents in the field of anti-infective ([0002]). The heterocyclic moiety includes 5-membered monocyclic aromatic heterocyclic ring with one or more heteroatoms, e.g., 1-4 heteroatoms, that may be nitrogen. The nitrogen atom may be substituted ([0029]), e.g., forming a tetrazole([0031]). The heterocycle (“M”) may be substituted with a R5 group ([0052]), including an embodiment wherein R5 is R6, which may be a C1-6 alkyl group substituted with a R7 group. The R7 group includes NR8R8, which may each be a C1-6 alkyl group ([0043]-[0081]). Thus, the heterocyclic moiety includes the following structure:
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([0479]), wherein R5 is R6, R6 is C2 alkyl group substituted with a R7 group; R7 group is NR8R8, which is each a C1 alkyl group.
Accordingly, it would have been obvious to one of ordinary skill in the art to have formulated the derivative of Rhee with a dimethylaminoethyl group since it is a known and effective substituent suitable for tetrazole rings in the field of anti-infectives as taught by Zhou. One would have a reasonable expectation of success since Rhee discloses wherein Het is a tetrazole ring substitutable at the 2’ position.
Response to Arguments
Applicant mainly asserts Rhee does not teach or suggest compounds with an aminoalkyl substituent on the tetrazole ring at the 2’ position, and that Zhou does not remedy the deficiencies of Rhee since Zhou teaches a synthesis process with an intermediate alkylate thiol compound in the 1’ position. Thus Zhou does not teach or suggest compounds having a tetrazole ring substituted with an aminoalkyl on the 2’ position of the tetrazole ring as presently claimed with a reasonable expectation of success.
The Examiner does not find the argument persuasive. As this is a 103 obviousness rejection, no one piece of prior art is required to teach each and every claim limitation. See MPEP 2141(III). Thus, the test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981). As discussed in the rejection, Rhee teaches wherein a substitution may occur on the 2’ position of the tetrazole ring. Zhou teaches wherein a dimethylaminoethyl group is a known and effective substituent suitable for tetrazole rings in oxazolidinone derivatives used for inhibiting bacteria. As such, Applicant’s argument is unpersuasive.
Applicant further asserts neither Zhou nor Rhee, alone or in combination, provide a reasonable expectation that the claimed compounds demonstrated at least a 10-fold Selectivity Index (SI) for inhibitory activity against two Mycobacterium tuberculosis strains, as disclosed in Example 4 and Table 4 of the application as originally filed.
The Examiner does not find the Applicant’s assertion to be persuasive. It is noted that the features upon which applicant relies (i.e., at least a 10-fold selectivity index for inhibitory activity against two Mycobacterium tuberculosis strains) are not recited in the rejected claims. 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 asserts table 4 and para. [0234] shows that moving a dimethylaminoethyl group to position 1’ of the tetrazole ring (compound AKG-21 vs. AKG-28) unexpected resulted in dramatic loss of activity against Mycobacterium tuberculosis.
The Examiner appreciates the Applicant’s assertion but does not find the argument persuasive. Applicant has the burden of explaining the data in any declaration they proffer as evidence of non-obviousness. See MPEP § 716.02(b)(II). Applicant has explained that various statements referenced in the specification support their position, but these cannot take the place of evidence in the record. See MPEP § 716.01(c)(II). Moreover, any differences between the claimed invention and the prior art may be expected to result in some difference in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. The burden is on applicant to establish that the results are in fact really unexpected and of statistical and practical significance. Ex parte Gelles, 22 USPQ2d 1318 (Bd. Pat. App. & Inter. 1992). See also MPEP § 716.02. In this instance, it is noted that AKG-28 does not carry an OH group like AKG-21. Therefore, it is not clear to the examiner how AKG-28 demonstrates the effect of moving a dimethylaminoethyl group to position 1’ instead of 2’.
Finally, assuming purely arguendo that the unexpectedness of the results has been established, the probative value of the evidence as compared to the invention as claimed must then be determined, i.e., the claims must be “commensurate in scope” with the showing. MPEP § 716.02(d). See also MPEP § 2145. Table 4 employs specific substituents. Thus, even if Applicant were to show unexpected results, they would have been obtained, for example, not with the broad class of “aminoalkyl” substituent generally, but instead with specific species. Note for example, both paragraphs [0234] and [0224] of the instant Specification notes that the specific tetrazole substitution of a dimethylaminoethyl side chain at the 2’ position of the tetrazole being superior when compared to dimethylaminopropyl, aminoethyl or diethylaminoethyl analogs (AKG-16 vs AKG-24, AKG-28 vs AKG-29, AKG-30 vs AKG-31). Likewise, shorter dialkylaminoalkyl side chains (such as ethylene versus propylene) on the tetrazole ring showed greater activity (AKG-16 vs AKG-25, AKG-24 vs AKG-26, AKG-28 vs AKG-30). Analogs with substitutions on the 2′ position of the tetrazole were more active than those with substitutions at the 1′ position (AKG-16 vs AKG-21, AKG-23 vs AKG-22). Applicant would need to explain how the specific species is “reasonably representative” of the more broadly claimed subject matter of the claims.
Terminal Disclaimer
The Examiner appreciates the filing of the terminal disclaimer on 20 February 2026 and notes the terminal disclaimer has been recorded. Accordingly, the double patenting rejection is hereby withdrawn.
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 LUCY TIEN whose telephone number is (571)272-8267. The examiner can normally be reached Monday - Thursday 8:30 AM - 6:30 PM EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sahana Kaup can be reached at (571) 272-6897. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LUCY M TIEN/Examiner, Art Unit 1612
/SAHANA S KAUP/Supervisory Primary Examiner, Art Unit 1612
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