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 .
Priority
This application filed on 06/12/2023, is a national phase application under 35 U.S.C. § 371 of International Application No. PCT/EP2021/086185, filed on 12/16/2021, which claims priority to grand Duchy of Luxembourg application No. LU102333, filed on 12/23/2020, and European patent application EP20215091.8, filed 12/17/2020.
Information Disclosure Statement
The information disclosure statement (IDS) filed on 10/13/2023, complies with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609. Accordingly, it has been placed in the application file and the information therein has been considered as to the merits, except where noted.
Status of claims
Applicant’s amendments and arguments filed on 05/26/2026 have been received and have been fully considered.
Claims 1, 12, 15 and 37 were amended, claims 19, 23 and claims 8-11, 13-14, 16-18, 20-22, 24-26, 28-29, and 33-35 were previously cancelled,
Claims 1-7, 12, 15, 27, 30-32, 36-42 are pending.
Election/Restriction
Applicant’s response filed on 01/20/2026 to Restriction/Election Requirement filed on 12/10/2025, is acknowledged. Applicant elected without traverse Group I drawn to a compound of Formula I and a pharmaceutical composition comprising a compound of Formula I or a pharmaceutically acceptable salt, racemate, diastereomer, enantiomer, ester, carbamate, sulphate, phosphate or prodrug thereof. Claims 1-7, 12, 15, 19, 23, 27, 30-32, 36, and 39-42 read on the elected Group. Claims 37 and 38 of Groups II and III are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Pursuant to the Election of Species Requirement, Applicant respectively elected without traverse, (S)-1-(2-(3,4-Dichloro-5-methyl-1 H-pyrrole-2-carboxamido)-5-(5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl) phenyl) pyrrolidin-3-aminium chloride depicted below for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable:
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Claims 1-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 read on the elected species. Applicant’s elected species was searched, and determined to be free of the art of record. Pursuant to MPEP § 803.02, the search and examination was extended to the non-elected species discussed below, which new search species falls within the scope of instant claims 1-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 (i.e., claims to proper Markush groupings that include both the new search species as well as the originally elected species. MPEP § 803.02(III)(C)(2)). The new search species underlies rejections of these claims pursuant to 35 U.S.C. § 102 and 103. As such, the election of species requirement is maintained as provisional, and claims 5, 19, 23, 37-38, and 40-41 are provisionally withdrawn from consideration pursuant to 37 CFR 1.142(b). See, MPEP § 803.02.
Thus, claims 1-7, 12, 15, 27, 30-32, 36-42 are pending with claims 5, 37-38, and 40-41 are withdrawn from further consideration, and claims 1-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 are under consideration.
Claim interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See MPEP § 2111. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. See MPEP § 2111.01. It is also appropriate to look to how the claim term is used in the prior art, which includes prior art patents, published applications, trade publications, and dictionaries. MPEP § 2111.01 (III). However, specific embodiments of the specification cannot be imported into the claims, particularly where the subject claim limitation is broader than the embodiment. MPEP § 2111.01(II).
Claim interpretation for “optionally substituted”:
The claims recite optionally substituted alkyl, optionally substituted alkoxy, optionally substituted C3-6 cycloalkyl, etc. The term “optionally substituted” is defines by instant specification as:
Unless otherwise defined, the term "optionally substituted" or "optional substituent" as used herein refers to a group which may or may not be further substituted with 1, 2, 3, 4 or more groups, preferably 1, 2 or 3, more preferably 1 or 2 groups selected from the group consisting of C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, C3-8 cycloalkyl, hydroxyl, oxo, C1-6 alkoxy, aryloxy, C1-6 alkoxyaryl, halogen, C1-6 alkylhalogen (such as CF3 and CHF2), C1-6 alkoxyhalogen (such as OCF3 and OCHF2), carboxyl, alkoxycarbonyl, cyano, nitro, amino, mono substituted amino, disubstituted amino, acyl, amides, aminoacyl, substituted amides, disubstituted amides, carbamic acid, carbamates, thiol, alkylthio, thioxo, sulfates, sulfonates, sulfinyl, substituted sulfinyl, sulfonyl, substituted sulfonyl, sulfonylamides, substituted sulfonamides, disubstituted sulfonamides, phosphates, phosphonates, aryl, aryl-C1-6 alkyl, heterocyclyl, heteroaryl and spiro ring systems wherein each alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, heteroaryl and spiro ring system and groups containing them may be further optionally substituted. Unless otherwise defined, particularly preferred optional substituents in one case include 1, 2, 3 or 4, preferably 1 or 2 substituents each independently selected from the group consisting of C14 alkyl (particularly methyl), halogen (particularly F), halogeno-C1-3 alkyl (particularly CHF2 and CF3), OH, C1-4 alkoxyl (particularly OСН3), СООН, СООC1-4 alkyl (particularly COOCH3), NH2, NH-C1-4 alkyl (particularly NHCH3), N(C1-4 alkyl)2 (particularly N(CH3)2), NHC(=O)-C1-4 alkyl, NHC(=O)-4-6-membered heterocyclyl, OP(=O)(OR)2(where each R is independently H or C1-4 alkyl), P(=O)(OR)2(where each R is independently H or C1-4 alkyl), C3.6 cycloalkyl (particularly cyclopropyl, cyclobutyl, cyclopenyl and cyclohexyl), phenyl, 4-6-membered heterocylyl (particularly oxetanyl, azetidinyl, tetrahydrofuranyl, pyrrolidinyl, tetrahydropyranyl, morpholinyl, thiomorpholinyl, oxothiazinyl, dioxothiazinyl, thianyl (also known as tetrahydrothiopyranyl), oxothianyl, dioxothianyl, piperidinyl, and piperazinyl) and further where C1. 4alkyl either alone or as part of a substituent group includes methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-butyl, sec-butyl and tert-butyl and may be further optionally substituted. [Pg. 36, ln. 10-30].
Thus, the term “optionally substituted” is interpreted consistent with the specification as one of the above groups.
Claim interpretation for “heterocyclyl”:
The claims recite heterocyclyl. The term “heterocyclyl” is defines by instant specification as:
Heterocyclyl is a saturated, partially saturated or unsaturated, optionally substituted monocyclic or bicyclic 10 ring system containing 5 to 10 atoms of which 1, 2, 3 or 4 ring atoms are chosen from nitrogen, sulphur or oxygen, which may, unless otherwise specified, be carbon or nitrogen linked, wherein a -CH2- group can optionally be replaced by a -C(O)-, a ring sulphur atom may be optionally oxidised to form the S-oxide(s), and a ring nitrogen atom may be optionally oxidised to form the N-oxide. Examples and suitable values of the term heterocyclyl are morpholino, morpholinyl, piperidino, piperidyl, pyridyl, pyridyl-N-oxide, pyranyl, pyrrolyl, imidazolyl, thiazolyl, thienyl, 15 dioxolanyl, thiadiazolyl, piperazinyl, isothiazolidinyl, triazolyl, tetrazolyl, pyrrolidinyl, 2-oxazolidinonyl, 5- isoxazolonyl, thiomorpholino, pyrrolinyl, homopiperazinyl, 3,5-dioxapiperidinyl, 3-oxopyrazolin-5-yl, tetrahydropyranyl, tetrahydrothiopyranyl, 1-oxotetrahydrothiopyranyl, 1,1-dioxotetrahydrothiopyranyl, pyrimidyl, pyrazinyl, pyridazinyl, pyrazolyl, pyrazolinyl, isoxazolyl, 4-oxopydridyl, 2-oxopyrrolidyl, 4-oxothiazolidyl, furyl, thienyl, oxazolyl, oxadiazolyl, 20 2-[(5-oxo)-[oxa-3,4-diazolyl] and 3-[oxa-2,4-diazolyl]. [Pg. 30, ln. 9-20].
Thus, the term “heterocyclyl” is interpreted consistent with the specification.
Withdrawn Abstract Objections
Objection to the Abstract for not having proper language and format, is withdrawn in view of Applicant’s amendment to the Abstract filed on 05/26/2026.
Withdrawn Claim Objections
Objection to claim 1 for reciting the parenthetical phrase (independently at each occurrence), is withdrawn in view of Applicant’s amendment filed on 05/26/2026 that deleted parenthetical phrase.
Withdrawn Claim Rejections - 35 USC § 112(a)
Objection to claims 1-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement for reciting “or prodrug thereof”, is withdrawn in view of Applicant’s amendment filed on 05/26/2026 that amended claim 1 by deleting “or prodrug thereof”.
Withdrawn Claim Rejections - 35 USC § 102
Rejection to claims 1-4, 6-7, 12, 36, and 39 under 35 U.S.C. 102(a)(1) as being anticipated by Z. Skok et al. Bioorg Chem. 2020 Sep; 102:104049), is withdrawn in view of Applicant’s amendment filed on 05/26/2026 that amended R6 of Formula I, see amended claim 1.
Rejection New
Rejections 35 U.S.C. 112(b)
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.
Claims 1-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 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.
Pursuant to 35 U.S.C. 112(b), the claim must apprise one of ordinary skill in the art of its scope so as to provide clear warning to others as to what constitutes infringement. MPEP 2173.02(II); Solomon v. Kimberly-Clark Corp., 216 F.3d 1372, 1379, 55 USPQ2d 1279, 1283 (Fed. Cir. 2000).
Claim 1 recites “R6 is an optionally substituted 5-membered heterocyclyl”. However, the body of claim 1 recites “R6' and R6" are independently at each occurrence selected from H and optionally substituted C1-6 alkyl or C1-6 acyl; or R6' and R6" may together with the nitrogen to which they are attached form a 5 or 6-membered heterocyclic ring, optionally substituted with 1 or 2 substituents independently selected from C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, hydroxyl, C1-6 alkoxy, halogen, cyano, nitro, carboxyl, …”. R6 is defined as an optionally substituted 5-membered heterocyclyl. The definition of R6 in the amended claim 1 does not include R6' and R6". None of the R1, R2, R3, R4, OR R5 comprises R6' and R6". Thus, R6' and R6" renders claim 1 indefinite. A claim limitation which is considered indefinite cannot be disregarded. MPEP § 2143.03(I).
It appears that Applicant deleted R6 is CONR6'R6" without deleting R6' and R6" definitions. Applicant can overcome this rejection by amending claim 1 to remove R6' and R6" definition from the claim.
Dependent claims 2-4, 6-7, 12, 15, 27, 30-32, 36, 39 and 42 are indefinite due to their dependence on a rejected claim and lacking any limitations that cure the ambiguities resulting from the parent claim(s).
Rejection Maintained
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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, 6-7, 12, 15, 27, 30-31, 36, 39 and 42 remain rejected under 35 U.S.C. 103 as being obvious over B. Tiz et al. Eur. J. Med. Chem. 2019 Apr 1; 167:269-290. doi: 10.1016/j.ejmech.2019.02.004, “Tiz” cited in the IDS dated 10/13/2023).
Tiz teaches DNA gyrase and topoisomerase inhibitors. Tiz teaches construction of the compound as depicted below, [Abstract]:
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In studies on the inhibitory activity against DNA gyrase and topoisomerase IV, Tiz listed compound 9d as the potent inhibitor with an IC50 of 6.9±0.5 nM, [Table 1]:
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Tiz’s compound 9d and 10a only differs in Y of the genus
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, wherein Y of compound 9d (6.9±0.5 nM) is COOH, and Y of compound 10b (48±4 nM) is COOMe. This difference in Y resulted in more than an 8 times decrease in potency.
Tiz also teaches compound 50 as the most anti-bacterial and DNA gyrase and topoisomerase IV inhibitor, [Table 2], with minimum inhibitory concentration of 3.13 µM, [Table 6]:
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Tiz’s compounds 46b and 50 only differs in the R2 groups of the genus
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, [Table 2]. R2 of compound 46b (7700 ± 900 nM) is
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, and R2 of compound 50 (77 ± 10 nM) is
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. This difference in the R2 resulted in hundreds times decrease in potency.
One of ordinary skill in the art having access to Tiz studies and looking to prepare a potent anti-bacterial agent, would have been motivated at the time of the invention to modify Tiz’s compound 9d by incorporating the R2 of compound 50 to arrive at the compound below:
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One of ordinary skill in the art would have been motivated to select 1,4-dihydro- tetrazol-5-one as Y, and piperidine as X with reasonable expectation of success because:
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Tiz studies directed to finding potent anti-bacterial agents;
Tiz teaches three different groups as Y and compound 50 with Y as 1,4-dihydro- tetrazol-5-one shows high anti-bacterial potency;
Tiz’s compound 9d with X as piperidine shows higher anti-bacterial inhibition; and
The comparison discussed above between 9d/10b, and 50/46b shows that positions X and Y are crucial in the genus above, and the variables piperidine and 1,4-dihydro- tetrazol-5-one demonstrate high anti-bacterial potency. Thus, one of ordinary skill in the art would reasonably predict to increase the potency with preforming the modification of Tiz compound 9d.
The modified compound
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reads on instant claim 1 wherein:
Skok’s compound 18 anticipates instant claim 1 wherein:
R1 is CH3;
R2 is chloro;
R3 is Chloro;
R4 is H;
R5 is (CH2)mO(CH2)m-5-10-membered heterocycle, wherein m is 0, and the 6-membered heterocycle is piperidine; and
R6 is 5-membered heterocyclyl, 1,4-dihydro- tetrazol-5-one.
Claims 2, 3, and 4 are met because R1 is CH3, R2 is chloro, and R3 is Chloro.
Claim 6 is met because R4 is H.
Claim 7 is met because R5 is O-piperidine.
Claim 12 is met because R6 is 1,4-dihydro- tetrazol-5-one.
Claims 15, 27, 30, and 31 are met because R1 is CH3; R2 is chloro; R3 is Chloro; R4 is H; R5 is O-piperidine; and R6 is 1,4-dihydro- tetrazol-5-one.
Claims 39 and 42 are met because R2 and R3 are Chloro.
With regard to claim 36, Tiz teaches that water solubility of the compound i.e., compound 50 was performed. [Pg. 279, col. 2, last para.]. Water reads on pharmaceutically acceptable excipient.
Response to Arguments
Applicant argues:
The Office's assertion of obviousness is the result of impermissible picking and choosing among different compounds within Tiz to assertedly arrive at the claimed invention. In fact, the Office is picking substituents from entirely different compound structures (referenced as compound types) described in Tiz. Tiz teaches three difference structural types (see Figure 2) with modifications among the three different types in the central part and right-hand sides of the molecules. See Tiz at Section 2.1 Design. Tiz teaches that these compounds are of distinct structural types and as such the skilled person would not consider properties of the different types and selection of moieties from among different types as the Office has done in making a modification. That is, the skilled person would not look to the moiety of compound 50, a type II compound, and arrive at any reasonable conclusion as to how a particular moiety from that compound would affect properties in the entirely distinct structural type I compound of compound 9d. Tiz even states that type II inhibitors were less potent than type I compounds. Tiz at 275. Thus, in looking to improve potency of a type I compound, the skilled person would not reasonably look to the type II compounds.
Examiner response:
Applicant's arguments have been fully considered but they are not persuasive for the following reasons. First, in response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). Tiz presented an optimization studies for finding a potent inhibitors for DNA gyrase, same utility of instant application (compounds of formula I are claimed to inhibit DAN gyrase). Tiz’s Graphical Abstract alone would provide the requisite motivation to one of ordinary skill in the art to reach a compound falling within claimed formula I, for example the modified
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above because there is only three groups for each of Y and X:
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Second, one of ordinary skill in the art would have been motivated to optimize Y and X of the genus because Tiz studies directed to finding potent anti-bacterial agents; Tiz teaches three different groups as Y and compound 50 with Y as 1,4-dihydro- tetrazol-5-one shows high anti-bacterial potency; Tiz’s compound 9d with X as piperidine shows higher anti-bacterial inhibition; and positions X and Y are crucial in the genus above. Thus, one of ordinary skill in the art would reasonably predict to increase the potency with preforming the modification of Tiz compound 9d. As discussed in MPEP 2143.02, obviousness does not require absolute predictability, but a reasonable expectation of success.
Applicant argues that “the skilled person would not look to the moiety of compound 50, a type II compound, and arrive at any reasonable conclusion as to how a particular moiety from that compound would affect properties in the entirely distinct structural type I compound of compound 9d, and Tiz even states that type II inhibitors were less potent than type I compounds”. However, type I and type II are combined in the Graphical Abstract, are subgenus of the same genus presented in the Graphical Abstract, type I and II are the main points of Tiz’s optimization studies, and one having ordinary skill in the art would be motivated by Tiz to optimization studies of type I (Table 1) and type II (Table II) and pick the best X of the substituents of Table 1, piperidine, and the best Y of the substituents of Table 2,
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, and reasonable expectation of success to arrive at the modified structure above. Tiz teaches that “overall, type II inhibitors were less potent than type I compounds, which is probably due to the absence of substituents at the ortho position to the amino group on the benzene ring”, which provide motivation to modify type II of Tiz compounds and incorporate ortho substituent as described in Tiz’s compound 9d and incorporate the active substituent
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from compound 50 because this substituent is the best substituent presented in table 2 (77 ± 10 nM).
Objection to Claims
Claim 32 objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Allowable Subject Matter
Claim 32 is allowable.
The following is an examiner’s statement of reasons for allowance:
The closest prior art is considered to be Z. Skok et al. Bioorg. Chem. 2020 Sep; 102:104049, “Skok” cited in the IDS dated 10/13/2023).
Skok discloses bacterial topoisomerase inhibitors [Abstract]. Skok discloses compound 18 below, [Table 1]:
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Skok’s compound 18 reads on compounds of claim 32, i.e., 4-(2-(3,4-Dichloro-5-methyl-1 H-pyrrole-2-carboxamido)-5-(5-oxo-4,5-dihydro-1,3,4- oxadiazol-2-yl)phenoxy)piperidin-1-ium chloride (depicted in the Table below), wherein (in claim 32 and Skok’s compound 18): R1 is CH3; R2 is chloro; R3 is Chloro; R4 is H; and R5 is O-piperidine; and differs from the instantly claimed compound of claim 32 in the highlighted circle as depicted in the below table:
[Skok’s compound 18]
[Claim 32 compound]
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In order to arrive at a compound falling within the instantly claimed compounds of claim 32, for example, the compound above, one of ordinary skill in the art would have to modify Skok’s above compound by replacing the highlighted CONHCH(CH3)-COOH group with 1,2,4-oxadiazol-5-one, tetrazole, 1,3,4-oxadiazol-2-one or 1,4-dihydro- tetrazol-5-one, e.g., 1,4-dihydro- tetrazol-5-one above, to arrive at a compound of claim 32. However, Skok’s disclosure does not provide sufficient guidance and motivation to one of ordinary skill in the art to perform the functional modifications to arrive at the instantly claimed compounds of claim 32. Therefore, Skok does not anticipate or render instantly claimed compounds obvious.
Conclusion
Claims 1-4, 6-7, 12, 15, 27, 30-31, 36, 39 and 42 are rejected. Claim 32 is objected to.
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 MANAHIL MIRGHANI ALI ABDALHAMEED whose telephone number is (571)272-1242. The examiner can normally be reached M-F 7:30 am - 5:00 pm.
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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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/M.M.A./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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