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 .
Election/Restrictions
Applicant’s election of Group (I) in the reply filed on 12/08/2024 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Applicant’s election of
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species in the reply filed on 12/08/2024 is acknowledged and maintained. This compound reads on the following substituents of the compound of formula (I):
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Expansion of Election of Species Requirement
A reasonable and comprehensive search conducted by the Examiner determined that the prior art at the time of the present invention was such that it did not anticipate or render obvious the elected species
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. In light of this discovery, the search is expanded to the subject matter of the subgenus of the elected species, i.e., the compound of the formula (I)
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where:
Het is an unsubstituted aryl;
R1 and R2 are each a hydrogen atom;
n is 0;
R3 is hydrogen;
R4 is and hydrogen atom; and
R5 is –(C(O)R6 where R6 is an unsubstituted aryl.
Claims Status
Acknowledgement is made of the receipt and entry of the amendment to the claims filed on August 21, 2025. Claims 1-5, 9, 12, 14-21, 27-31 are pending. Claims 6-8, 10-11, 13, 22-26, and 32-33 are canceled. Claims 15, 17, 30-31 are withdrawn. Claims 1-5, 9, 12, 14, 16, 18-21, and 27-29 are examined in accordance to the expanded compound species.
Priority
This application is the US national phase under 35 U.S.C. § 371 of International Application No. PCT/US2020/014636, filed January 22, 2020, which claims priority to U.S. Provisional Application No. 62/795,549, filed January 22, 2019 and U.S. Provisional Application No. 62/871,951, filed July 9, 2019.
Action Summary
The objection to claims 1, 9, and 21 are withdrawn in light of the claim amendment.
Claims 1, 2, 4, 5, 9, 12, 14, 16, 18, 19, 21, and 28-29 rejected under 35 U.S.C. 102(a)(1) as being anticipated by Leibeschuetz et al (WO1999011657A1), are withdrawn in light of the claim amendment.
Claims 1, 2, 4, 5, 9, 12, 14, 16, 18-21, and 27-29 rejected under 35 U.S.C. 103 as being unpatentable over Leibeschuetz et al (WO1999011657A1) as applied to claims 1, 2, 4, 5, 9, 12, 14, 16, 18, 19, 21, and 28-29 set forth in the above rejection, are also withdrawn in light of the claim amendment.
Response to Arguments
Acknowledgement is made of the receipt and entry of Applicant’s argument, filed on August 21, 2025. Applicant’s arguments with respect to claim(s) 1, 4-5, 9, 12, 14, 16, 18-21, and 27-29 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 2, 9, 12, 14, 16, and 18, 19-21 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zymalkowski et al (STN ACCESSION NUMBER: 1966:404153).
Zymalkowski teaches nornicotine derivatives comprising
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and
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. (See Abstract.) These compounds read on the claimed compound of the formula (I)
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where:
Het is an unsubstituted aryl;
R1 and R2 are each a hydrogen atom;
n is 0;
R3 is hydrogen;
R4 is and hydrogen atom; and
R5 is –(C(O)R6 where R6 is an unsubstituted aryl. With respect to the limitation of “wherein Rg, Rh and Ri are independently selected from alkyl, alkoxy, halo, haloalkyl, haloalkoxy, cyano, hydroxy, amino, acylamino,preferably, methyl, ethyl, methoxy, ethoxy, chloro, fluoro, trifluoromethyl, trifluoromethoxy, hydroxy, acetylamino, butanoylamino, and pentanoylamino” of claims 14 and 19, which both depend from claim 1; the fact that Rg, Rh and Ri are optional substituents of aryl or heteroaryl or R6, then claim 2 is interpret to encompass compounds in which Rg, Rh and Ri are absent.
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, 2, 4, 5, 9, 12, 14, 16, 18-21, and 27-29 are rejected under 35 U.S.C. 103 as being unpatentable over Zymalkowski et al (STN ACCESSION NUMBER: 1966:404153) as applied to claims 1, 2, 9, 12, 14, 16, 18-21, and 27 set forth in the above rejection in view of Holtman et al (US8,710,069 B2).
The teachings of Zymalkowski have been discussed in the above rejection.
However, Zymalkowski does not teach the pyridine is pyridyl-3yl as recited in claims 27- 28 and a pharmaceutically acceptable carrier in claim 29. Moreover, Zymalkowski does not teach a compound of the formula (I) wherein n is 1 (i.e. piperidine) as recited in claims 4 and 5.
Holtman teaches a pharmaceutical composition comprising an analgesically effective amount of a nornicotine compound and at least one pharmaceutically acceptable excipient. (See claims 21.) Moreover, Holtman teaches nornicotine
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, the primary metabolite of nicotine, binds to nicotinic receptors which are located in the brain, spinal cord and periphery (autonomic ganglia and Smooth muscle). It has recently been appreciated that nicotinic receptor binding can also modulate pain signals to the brain suggesting their poten tial use in the treatment of pain (acute, chronic, cancer-re lated). (See column 1, lines 38-44.) Please note that nornicotine has the same core structure as the claimed compound of formula (I).
It would have been prima facie obvious to one of ordinary skill in the art at the time the invention was filed to use the compounds taught by Zymalkowski in combination with a pharmaceutically acceptable for treating pain. One would have been motivated by the fact the nornicotine as having nicotinic receptor binding activity for treating pain taught by Holtman, has the same or similar core structure as the compound taught by Zymalkowski. Based on the fact that both, the compound taught by Zymalkowski and the compound taught by Holtman have structurally similarity or similar core structure, one would reasonably expect the compound taught by Zymalkowski to possess similar activity and said compound can be formulated with a pharmaceutically acceptable carrier for treating successfully pain.
Furthermore, in the absence of showing unobvious results, it would have been obvious to one of ordinary skill in the art at the time of the invention when faced with Zymalkowski
to make the instantly claimed derivatives of a known product. The instantly claimed compounds and prior art compounds are common derivatives known as isomers. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) 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). See MPEP 2144.09(11).
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). The only structural differences between the claimed and prior art compounds and the claimed compounds are the absence of the (S) and the (R) in the compound of Zymalkowski and also the presence of the piperidine ring (when n is 1) in the claimed compound
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, whereas the prior art compound has a pyrrolidine ring
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. The court held that although the prior art compounds were not true homologs or isomers of the claimed compounds, the similarity between the chemical structures and properties is sufficiently close that one of ordinary skill in the art would have been motivated to make the claimed compounds in searching for new pesticides.). See MPEP 2144.09 (111).
Guided by the teaching of Zymalkowski, one skilled in the art would be able to make similar compounds by making isomers of the known compound. The motivation would be to prepare similar compounds that are pharmacologically active compounds that treat paitn. The instant obviousness rejection is based on the close structural similarity of the instantly claimed compounds to the prior art compounds and the common utility shared among the compounds. There is an expectation among those of ordinary skill in the art that similar structural compounds will have similar properties and that modification of a known structure is mere experimentation within the means of a skilled artisan. See MPEP 2144.09(I). Therefore, claims 4-5 and 27-29 are rejected as obvious over the prior art.
Claim Objection
Claim 3 is 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.
Conclusion
Claims 1, 2, 4-5, 9, 12, 14, 16, 18-21, and 27-29 are not allowed.
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 JEAN P CORNET whose telephone number is (571)270-7669. The examiner can normally be reached Monday-Thursday from 7.00am-5.30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached on 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/JEAN P CORNET/Primary Examiner, Art Unit 1628