DETAILED ACTION
Notice of 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 without traverse of Group I in the reply filed on 3/16/2026 is acknowledged. The requirement is still deemed proper and is therefore made FINAL.
Claims 18-21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Applicant’s election without traverse of a single species in the reply filed on 3/16/2026 is also acknowledged.
The elected species read upon claims 2-7, 10-11 and 16.
Claim Rejections - 35 USC § 102
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 2-7, 10-11 and 16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Donovan et al (WO 2017/205534; of record).
Claim 2 is drawn to a crystalline form of (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-((methylamino)methyl)piperidine-1-carboxylate hydrochloride, wherein the crystalline form is Form 1 having an XRPD pattern with characteristic peaks at about 4.4o 2-Theta, 7.6o 2-Theta, 8.8o 2-Theta, 11.6o 2-Theta, 18.5o 2-Theta, 20.1o 2-Theta, and 22.3o 2-Theta (more specifically, wherein the crystalline form is obtained from ethyl acetate (claim 11)).
Donovan et al teach “(E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-((methylamino)methyl)piperidine-1-carboxylate hydrochloride” (Paragraph 0003) as well as “crystalline forms” thereof (Paragraph 0137). Specifically, Donovan et al teach the preparation of a crystalline form of Compound 1 comprising the steps of:
(A) “[s]ynthesis of (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-((methylamino)methyl)piperidine-1-carboxylate hydrochloride (Compound 1)” as follows:
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(B) purification “via crystallization in EtOAc” (Paragraph 0184).
It is asserted, absent evidence to the contrary, that the crystalline form of Compound 1 taught by Donovan et al would necessarily have an XRPD pattern with characteristic peaks at about 4.4o 2-Theta, 7.6o 2-Theta, 8.8o 2-Theta, 11.6o 2-Theta, 18.5o 2-Theta, 20.1o 2-Theta, and 22.3o 2-Theta for the following reasons:
The instant Specification teaches the preparation of “Crystalline Compound , Form 1” comprising the identical step (A) taught by Donovan et al to provide to provide (E)-2-methoxy-4-((8-methylnon-6-enamido)methyl)phenyl 2-((methylamino)methyl)piperidine-1-carboxylate hydrochloride (Compound 1) (Page 23, Paragraph 0080 to Page 25, Paragraph 0085), which was then (B) “dissolved in EtOAc... to afford crystalline Compound 1, Form 1” (Page 25, Paragraph 0086, Example 2), as similarly taught by Donovan et al.
As stated in In re Best, Bolton, and Shaw, “[w]here… the claimed and prior art products are identical or substantially identical, or are produced by identical or substantially identical processes, the PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his claimed product" 562 F2d 1252 (CCPA 1977). In the instant case, as discussed above, the identical claimed and prior art products are produced by substantially identical processes. As such, absent evidence to the contrary, it is asserted that that the crystalline form of Compound 1 taught by Donovan et al would necessarily have an XRPD pattern with characteristic peaks at about 4.4o 2-Theta, 7.6o 2-Theta, 8.8o 2-Theta, 11.6o 2-Theta, 18.5o 2-Theta, 20.1o 2-Theta, and 22.3o 2-Theta. (see also In re Fitzgerald 619 F2d 67 (CCPA 1980): the burden is shifted to the applicants to "prove that subject matter shown to be in the prior art does not possess characteristic relied on”).
Accordingly, claims 2 and 11 are anticipated.
Claims 3-7 and 10 are drawn to the crystalline form of claim 2, wherein the crystalline is characterized by additional properties.
For the same reasons as discussed above regarding the XRPD pattern, it is further asserted that the substantially identical crystalline form of Compound 1 taught by Donovan et al produced by a substantially identical process would necessarily possess the instantly claimed properties of claims 3-7 and 10.
Accordingly, claims 3-7 and 10 are also anticipated.
Claim 16 is drawn to a pharmaceutical composition comprising the crystalline form of claim 2, and at least one inactive ingredient selected from pharmaceutically acceptable carriers, diluents, and excipients.
Donovan et al further teach “a pharmaceutical composition... wherein the pharmaceutical composition comprises an effective dose of... Compound 1” (Paragraph 0021), wherein “[t]he term ‘pharmaceutical composition’ refers to a mixture of a compound described herein with other chemical components, such as carriers... diluents... and/or excipients” (Paragraph 0065).
Accordingly, claim 16 is also anticipated.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CRAIG D RICCI whose telephone number is (571) 270-5864. The examiner can normally be reached on Monday through Thursday, and every other Friday, 7:30 am - 5:00 pm ET. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Bethany Barham can be reached on (571) 272-6175. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CRAIG D RICCI/Primary Examiner, Art Unit 1611
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