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 .
Receipt is acknowledged of Applicant’s Argument filed on 07/17/2026.
Claims 1, 3-10 are pending in the instant application.
Claims 3-10 are withdrawn from further consideration.
Note, rejections and objections not reiterated from previous office actions are hereby withdrawn. The following rejections or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
Claim Rejections - 35 USC § 102/103
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 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.
Claim(s) 1 is/are rejected under 35 U.S.C. 102((a)(1)) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over KOVAC et al (3D QSAR study, synthesis, and in vitro evaluation of (+)-5-FBVM as potential PET radioligand for the vesicular acetylcholine transporter (VAChT). Bioorganic & Medicinal Chemistry 18 (2010) 7659–7667).
KOVAC teaches enantiomers of 5-fluoro-3-(4-phenyl-piperidin-1-yl)-1,2,3,4-tetrahydro-naphthalen-2-ol (5-FBVM) (see abstract; and Scheme 1 on pg. 7663, which is provided below):
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KOVAC further teaches that radionuclides, such as 18F, are well-known to be tracer compounds used in PET imaging and visualization of early neurodegenerative processes in Alzheimer’s disease, wherein KOVAC had previously synthesized several 18F-labeled benzovesamicol derivatives, such as [18F]FEOBV (see pg. 7659, under Introduction). In this publication, KOVAC developed the novel benzovesamicol analog 5-FBVM, as shown above, and discussed the potential as a PET radioligand (see title). Thus, it would have been obvious to incorporate 18F for PET imaging and visualization of early neurodegenerative processes in Alzheimer’s disease, which would read on Applicant’s formula (I).
Response to Arguments
Applicant argues that Kovac does not identicallv describe or depict the specific compound of formula (I), nor its uses, nor its method of preparation. Thus, Kovac does not anticipate the subject matter of claim 1. Similarly, the other radiolabelled enantiomer (II) is also not described. With respect to a 35 USC§ 103(a) rejection, Kovac describes the synthesis of the two enantiopure forms (-)-(R,R)- and (+)-(S,S)-5-FBVM and states that the two (non-radiolabelled) enantiomers exhibit similar affinity for VAChT (see p.7664, right-hand column, last paragraph), that both enantiomers are selective for VAChT at a 2 receptors and that only the (+)-(S,S)-5-FBVJ\,1 enantiomer is selective for the a 1 receptor. Regarding the comparison of the affinities of the two unlabelled forms, Kovac states: "5-FBVM presents very good affinity for VAChT and, surprisingly, the (+)-(S,S) enantiomer showed almost the same affinity as the (-)-(R,R) enantiomer (Ki(S,S)FBVM '" 6.95 nM and Ki(R,R)FBVM= 3. 68 nM)". In contrast, as shown in the present application, fluorine labelling results in surprising superior affinity of the (-)-(R,R) form and greater accumulation in the brain (see page 4 at lines 7-9 of the present application), properties that are not obvious based on Kovac.
The Examiner finds this argument unpersuasive, because KOVAC explicitly teaches the potential as a PET radioligand (see title), which would include incorporating 18F. Thus, it would have been obvious to incorporate 18F for PET imaging and visualization of early neurodegenerative processes in Alzheimer’s disease, which would read on Applicant’s formula (I).
Applicant argues that Kovac does not contain sufficient information to successfully prepare the compounds of the invention. Kovac merely mentions the preparation of radiolabeled compounds but contains no guidance on how to obtain said compounds. Sta1ting from Kovac, it was by no means obvious to a person skilled in the art to develop the two radiolabeled enantiomers, let alone to prepare a form that exhibits superior affinity for VAChT (the (-)-(R,R) form).
The Examiner finds this argument unpersuasive, because KOVAC provided references on previously synthesized compounds radiolabeled 18F (see pg. 7659, Introduction; and pg. 7666-7667, list of references) and provides sufficient method on synthesizing the compound (see pg. 7763), wherein one skilled in the art only have to use a radiolabeled 18F versus a non-radiolabeled F.
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.
Telephonic Inquiries
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JAKE MINH VU whose telephone number is (571)272-8148. The examiner can normally be reached Mon-Fri 9:00am-5:30pm.
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/JAKE M VU/Primary Examiner, Art Unit 1618
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