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 .
Continued Examination
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant’s submission filed on April 7th, 2026 has been entered.
Status of the Claims
Claims 1 and 6-14 are pending in this application. Claims 2-5 and 15-20 have been cancelled by applicant. Claims 1, 6, and 9-12 are under examination herein. Claims 7-8 and 13-14 are withdrawn from consideration.
Examiner Notes
In view of the unexpected results filed in the Oath/Declaration from 12/04/2025 – the compound below is allowable; however, unexpected results are not commensurate with the full scope of the claims, therefore, the rejections below still apply for embodiments rendered obvious by the prior art of record and not included in the Oath/Declaration.
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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.
Claim 1, 6, and 9-12 are rejected under 35 U.S.C. 103 as being unpatentable over Klenke et al. (WO 2013/110643 A1 – From IDS – previously cited) (“Klenke”).
Regarding claims 1 and 6, Klenke teaches the compounds of Formula I below as β-lactams for use as antibacterials, which is the same as the intended use of the instant invention (abstract). Klenke’s compounds render the instant compounds obvious when R1 and R2 (corresponding to instant R1 and R2) are methyl; R3 is -O-(CH2)o(SO2)OH wherein o can be 0 (corresponding to W being -O- and M being H, as shown in compounds 44A, 88, and 107, below, disclosed by Klenke in Table 3, starting on page 179); X can be CR4, wherein R4 is H or halogen (specifically showing Cl in compound 61 below); Z can be a C2-alkyl chain, substituted with one carboxyl group (carboxyl is defined as -COOH in [0024] and shown in compounds 44A, 88, and 107); Y is O; l can be 0; A represents an aryl, substituted with
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, wherein R1b, 2b can be H, and R3b (corresponding to R3) can be 4-7-membered heterocycle, or alkyl substituted with amino (pages 5-6) (as shown in compounds 44A, 88, and 107).
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(Klenke’s Formula I)
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(44A, page 179)
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(88, page 187)
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(107, page 191)
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(61, page 182)
While Klenke doesn’t show their preferred embodiment 44A, 88, and 107 wherein both R4 is Cl, Klenke discloses their X group can be CR4, wherein R4 can be a halogen (specifically showing Cl in their preferred embodiment 61 above). Thus, Klenke discloses a relatively broad genus of compounds, which encompasses the instantly claimed subgenus.
Therefore, regarding claims 1 and 6, one having ordinary skill in the art would have found the claimed compounds prima facie obvious, since they are generically embraced by Klenke’s disclosed formula and preferred embodiments; In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). See MPEP 2144.08. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of antibacterial compounds disclosed by Klenke. Accordingly, one having ordinary skill in the art would have been motivated to replace the H in the position corresponding to Klenke’s R4 in compounds 44A, 88, and 107 above for a Cl, as in their preferred embodiment 61, to arrive at the instant invention.
Further regarding claim 6, Klenke discloses their compounds for use in the treatment and/ or prophylaxis of diseases caused by bacteria, especially Gram-negative bacteria [0059].
Applicant is advised that a recitation of the intended use of the claimed invention, such as the use of the compounds of claim 1 for treating or preventing diseases caused by Gram-negative bacteria in the instant application, must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. Note: MPEP 2111.02.
Applicant is advised that a novel useful compound that is isomeric with the prior art compound is unpatentable unless it possesses some unobvious or unexpected beneficial property not possessed by the prior art compound. In re Norris, 179 F.2d. 970, 84 USPQ 458 (CCPA 1970). Therefore, it would have been obvious to one of ordinary skill to expect similar properties of structurally similar compounds since they are suggestive of one another. It has been held that a compound, which is structurally isomeric with a compound of the prior art, is prima facie obvious absent unexpected results. In re Finely, 81 USPQ 383 (CCPA 1949); 84 USPQ 458 (CCPA 1950).
Regarding claims 9 and 12, Klenke discloses medicaments comprising their compounds and further comprising at least one other active compound [0076].
Further regarding claim 12, Klenke discloses their invention for use in the treatment and/ or prophylaxis of diseases caused by bacteria, especially Gram-negative bacteria [0059].
Applicant is reminded that a recitation of the intended use of the claimed invention, such as the use of the medicaments of claim 9 for treating or preventing diseases caused by Gram-negative bacteria, in the instant application, must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Regarding claim 10, Klenke discloses that suitable “other active compounds” include β-lactamase inhibitors, including tazobactam and avibactam [0078].
Regarding claim 11, Klenke discloses medicaments comprising their compounds and pharmaceutically acceptable excipients [0075].
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 6, and 9-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-12 of U.S. Patent No. 9,782,390 B2 (US ‘390). Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claim 1, 6, and 9-12, US ‘390 claims a method of prophylactically treating a bacterial infection in a human comprising administration of an effective amount of the compounds of Formula I below, which render the instant compounds obvious when X is CR4, wherein R4 is halogen; R1-2 are C1 alkyl; R3 is -O-SO2-OH; Z can be a C2-alkyl chain, substituted with one carboxyl group; Y is O; l can be 0; and A can be
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, or
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(US ‘390’s claims 1 and 7). US ‘390 claims administration of their compound in a composition comprising at least one further active compound, wherein the compound is a β-lactamase inhibitor (specifically disclosing clavulanic acid, tazobactam, etc. (col. 21, para. 1), and with an inert, non-toxic, pharmaceutically acceptable excipient (US ‘390’s claims 9-11) – reading on instant claims 6, and 9-12.
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Applicant is reminded that a recitation of the intended use of the claimed invention, such as the use of the medicaments/compounds of instant claims 1 and 9 for treating or preventing diseases caused by Gram-negative bacteria, in the instant application, must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Claims 1, 6, and 9-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-17 of U.S. Patent No. 9,556,165 B2 (US ‘165). Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claim 1, 6, and 9-12, US ‘165 claims the compounds of Formula I below, which render the instant compounds obvious when X is CR4, wherein R4 is halogen; R1-2 are C1 alkyl; R3 is -O-SO2-OH; Z can be a C2-alkyl chain, substituted with one carboxyl group; Y is O; l can be 0; and A can be be
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, or
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(US ‘165’s claims 1 and 7). US ‘165 claims a composition comprising their compound and at least one further active compound, wherein the compound is an fl-lactamase inhibitor (Examiner believes this is a typo in US ‘165, and claim should read β-lactamase inhibitor) (specifically disclosing clavulanic acid, tazobactam, etc. (col. 21, para. 1), and with an inert, non-toxic, pharmaceutically acceptable excipient (US ‘165’s claims 12-17) – reading on instant claims 6, and 9-12.
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Applicant is reminded that a recitation of the intended use of the claimed invention, such as the use of the medicaments/compounds of instant claims 1 and 9 for treating or preventing diseases caused by Gram-negative bacteria, in the instant application, must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Claims 1, 6, and 9-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13 of US Patent No. 12,516,048 B2 (US ‘048); in view of Tang et al. (WO 2017/106064 A1 – From IDS – previously cited)
Regarding instant claim 1, US ‘048 claims the compounds of Formula I below, wherein M can be H; R1 and R2 can be H or C1 alkyl (methyl); W can be -O-; X can be methyl; and R3 can be 4 to 6-membered heterocycle.
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Regarding instant claims 6, and 12, US ‘048 claims their compounds for the treatment of bacterial infections caused by Gram-negative bacteria (US ‘048 claims 4-5).
Regarding instant claims 9-11, US ‘048 claims a pharmaceutical composition comprising another active compound, wherein the compound is a β-lactamase inhibitor (US ‘048 claims 6-8).
While US ‘048 does not teach their X (corresponding to instant R4) to be a halogen (instant claim 1); the teachings of Tang are relied upon for these disclosures.
Tang teaches the related antibacterial compounds of Formula I below (pages 2-4), wherein Rx and Rz (corresponding to instant R1 and R2) can be H or Me; W can be -O-; Z can be C1-3 alkylene, substituted with -COOH; Y can be -O-; A1 can be a 6-membered aromatic ring; Q can be a bond; A2 can be -N(R3)2, wherein R3 can be H or alkyl; M can be cycloalkyl; and X (corresponding to instant X) can be N or CR1, wherein R1 can be C1-6 alkyl or a halogen.
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Therefore, it would have been prima facie obvious to one of ordinary skill in the art prior to the effective filing date of the instant application to replace the alkyl group (X) in US ‘048 (corresponding to instant R4) for a halogen. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of compounds disclosed by US ‘048, wherein X is limited to alkyl; in view of Tang’s functionally equivalent antibacterial compounds, wherein the position corresponding to instant R4 can be an alkyl or a halogen. Accordingly, one having ordinary skill in the art would have been motivated to prepare any of the compounds embraced by the US ‘048’s disclosed generic formula in view of Tang’s related compounds, including those encompassed by the claims.
Applicant is reminded that a recitation of the intended use of the claimed invention, such as the use of the medicaments/compounds of instant claims 1 and 9 for treating or preventing diseases caused by Gram-negative bacteria, in the instant application, must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim.
Response to Arguments
Claims
Claim amendments are acknowledged and have been entered. No new matter has been introduced.
Specification
Applicant’s arguments, see pages 6-7, filed 03/03/2026, with respect to the objection to the specification have been fully considered and are persuasive. The objection of the specification has been withdrawn.
Claim Rejections - 35 USC § 112(b)
Applicant’s arguments, see page 7, filed 03/03/2026, with respect to the 35 USC § 112(b) rejection of the claims have been fully considered and are persuasive. The 35 USC § 112(b) rejection of the claims has been withdrawn.
Claim Rejections - 35 USC § 103
Applicant's arguments filed 03/03/2026 have been fully considered but they are not persuasive.
Applicant is advised that MPEP 716.01(c) makes clear that “[t]he arguments of counsel cannot take the place of evidence in the record” (In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965)).
Applicant argues the claimed genus is not taught by the prior art of record and that Klenke’s single preferred embodiment with a Cl in the position corresponding to instant R4 does not show the instantly claimed R3 groups, and that SAR of β-lactams is highly sensitive to C2 substitution. Applicant states there’s no teaching in Klenke that would lead one of ordinary skill to the instant claims. Applicant argues Klenke’s generic teaching of “halogens” is insufficient to supply a predictable selection of chlorine with a reasonable expectation of success for R4, and that no rationale data is provided when R4 is Cl and R3 is aminoethyl, azetidine, pyrrolidine, or piperidine. Applicant cites the MIC data from Table 1 of the instant spec (see para. Bridging pages 10-11) ([0114]-[0116]) and states this data establishes a direct nexus that correlates the claimed structure with low MICs of Gram-negative pathogens, and that Cl at R4 creates a significant, non-obvious, unexpected improvement in potency. Applicant further argues the preparation of the instant compounds results in an increase in cost and structural complexity, and that one of ordinary skill would not undertake these additional synthetic steps and that the instant compounds are therefore, not obvious. Applicant also cites the Declaration filed 12/04/2025 to highlight “unexpected results” presented therein.
In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007).
In this case, Klenke teaches the compounds of Formula I below as β-lactams for use as antibacterials, which is the same as the intended use of the instant invention (abstract). Klenke’s compounds render the instant compounds obvious when R1 and R2 (corresponding to instant R1 and R2) are methyl; R3 is -O-(CH2)o(SO2)OH wherein o can be 0 (corresponding to W being -O- and M being H, as shown in compounds 44A, 88, and 107, below, disclosed by Klenke in Table 3, starting on page 179); X can be CR4, wherein R4 is H or halogen (specifically showing Cl in compound 61 below); Z can be a C2-alkyl chain, substituted with one carboxyl group (carboxyl is defined as -COOH in [0024] and shown in compounds 44A, 88, and 107); Y is O; l can be 0; A represents an aryl, substituted with
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, wherein R1b, 2b can be H, and R3b (corresponding to R3) can be 4-7-membered heterocycle, or alkyl substituted with amino (pages 5-6) (as shown in compounds 44A, 88, and 107).
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(Klenke’s Formula I)
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(44A, page 179)
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(88, page 187)
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(107, page 191)
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(61, page 182)
While Klenke doesn’t show their preferred embodiment 44A, 88, and 107 wherein both R4 is Cl, Klenke discloses their X group can be CR4, wherein R4 can be a halogen (specifically showing Cl in their preferred embodiment 61 above). Thus, Klenke discloses a relatively broad genus of compounds, which encompasses the instantly claimed subgenus.
Therefore, one having ordinary skill in the art would have found the claimed compounds prima facie obvious, since they are generically embraced by Klenke’s disclosed formula and preferred embodiments. The requisite motivation for arriving at the claimed compounds stems from the fact that they fall within the generic class of antibacterial compounds disclosed by Klenke. Accordingly, one having ordinary skill in the art would have been motivated to replace the H in the position corresponding to Klenke’s R4 in compounds 44A, 88, and 107 above for a Cl, as in their preferred embodiment 61, to arrive at the instant invention.
Regarding Applicant’s arguments that SAR of these β-lactams is highly sensitive to C2 substitution, Klenke discloses the MIC for their compounds 44A, 88, and 107 for 21 different strains of bacteria (see pages 247-254). This data shows that compounds with H in the position corresponding to R4 had significantly superior activity relative to compound 61 (with Cl in R4) when it came to strains 1-5, 8, 10, 12, 16, 17-18, and 19-21; however, compound 61 had similar MICs against strains 6-7, 9, 11, and 15; and better MICs against strains 13-14. Therefore, one of ordinary skill would have been motivated to replace the H in position R4 of Klenke’s compounds 44A, 88, and 107 for a Cl (as in compound 61) to combine the SAR efficacies of these compounds against different strains of bacteria, and arrive at the instant inventions.
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The relevant MIC values (for compounds encompassed by the instant claims) from instant Table 1 (starting on page 53 of the spec.) are included herein for convenience:
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While the strains of bacteria tested may not be the same among the two sets of data shown above, it can be seen that Klenke’s compounds (with H instead of Cl in the position corresponding to their R4) are generally more potent against the strains of bacteria they tested.
In response to Applicant’s arguments that the instant compounds are more difficult to synthesize…the methods for the preparation of the instant compounds are reported by Klenke, and one of ordinary skill in the art would easily be able to modify Klenke’s syntheses to arrive at their compounds of interest. Applicant is advised that "A person of ordinary skill in the art is also a person of ordinary creativity, not an automaton." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 421, 82 USPQ2d 1385, 1397 (2007). "[I]n many cases a person of ordinary skill will be able to fit the teachings of multiple patents together like pieces of a puzzle." Id. at 420, 82 USPQ2d 1397.
In the Oath/Declaration filed 12/04/2025 – Applicant cites unexpected beneficial properties of the instant compound 10 when compared to Klenke’s compound 96 (shown below for convenience):
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(cmpd. 10)
Applicant discloses the following:
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These results render instant compound 10 allowable and non-obvious over the prior art. However, unexpected results do not encompass the full scope of claim 1, and therefore, claims stand rejected over Klenke et al.
Double Patenting
Applicant states a terminal disclaimer will be submitted once claims are in condition of allowance.
This is not persuasive. Claims stand rejected over non-statutory double patenting (NSDP) rejections of record. Two additional NSDP rejections have been introduced herein over US ‘390 and US ‘165. The oath/declaration of 12/04/2025 is not enough to overcome NSDP rejections of record. Claims stand rejected over NSDP rejections of record.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JACKSON J HERNANDEZ whose telephone number is (571)272-5382. The examiner can normally be reached Mon - Thurs 7:30 to 5.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney L. Klinkel can be reached at (571) 270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/JACKSON J HERNANDEZ/Examiner, Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627
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