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 .
Detailed Action
Response to Amendments
The amendments made to the claims 01/26/2026 has been entered.
Restriction/Species Election
Applicant elected the following.
Group I, claims 1-16 and 19.
Compound of claims 1-3.
The election was made without traverse.
Claims 4-18 and 20 are hereby withdrawn as being drawn to non-elected inventions and species.
Status of Claims
Claims pending are claims 1, 3-14, and 16-20.
Claims withdrawn from further prosecution are claims 4-14, 16-18, and 20.
Claims under examination are claims 1, 3 and 19.
Information Disclosure Statements
The information disclosure statement (IDS) submitted 01/26/2026 has been considered.
Modified Rejections
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.
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.
Claim(s) 1, 3 and 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sherwood (Synthesis, 2020, 52, 688-694) in view of Yu (Advanced Drug Delivery Reviews 48, 2001, 27-42), Hancock (Pharm. Res. 17(4) 397 (2000)) and Sharma (US20070129385).
Regarding claim 19, Sherwood on p. 691 teaches reaction conditions of the reaction in scheme 5 (below). Protected psilocybin was provided in the form of compound 9. The psilocybin was deprotected via hydrogenolysis reaction. The reaction solvent was methanol (MeOH).
Scheme 5
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Further discussion of this reaction is found p. 693, section Psilocybin (1). Here, Sherwood states “The flask was degassed, refilled with N2 and the suspension was filtered through a pad of Celite via Büchner funnel. The filter pad was washed with CH3OH (500 mL) and the purple-colored filtrate was concentrated and dried overnight under vacuum to give 10.7 g of crude 1 (106%).”
Regarding claims 1-3, Sherwood on p. 691 states “Precipitation of 1 from the aqueous reaction mixture using acetone typically provided a semi-crystalline solid in about 90% recovery and 97-98% purity.”
Sherwood does not explicitly discuss an amorphous psilocybin. This is addressed by the combination of Yu.
Yu is drawn to amorphous pharmaceutical solids and their preparation (title). Yu in its abstract states “The importance of amorphous pharmaceutical solids lie in their useful properties, common occurrence, and physio-chemical instability relative to corresponding crystals.” Yu continues by stating “Amorphous solids can be produced by common pharmaceutical processes, including melt quenching, freeze- and spray-drying, milling, wet granulation, and drying of solvated crystals.”
Yu on p. 31, sec. 3.1.1 states “Grinding or milling of crystals can remove all traces of crystallinity according to XRD.” Yu on p. 28 provides motivation to mill a crystalline compound to achieve an amorphous form where it states “Useful properties. Amorphous solids have higher solubility, higher dissolution rate, and sometimes better compression characteristics than corresponding crystals.”
Additional references to support the motivation to create an amorphous form are found in Hancock and Sharma.
The primary reference shows applicants’ compounds in a semi-crystalline form; the rejected claims are drawn to the amorphous. The motivation to prepare an amorphous form rather than a semi-crystalline form is provided by the secondary references.
The amorphous form is an obvious variation which one is motivated to obtain because of the expected advantage. Note this from the conclusion of Hancock “Amorphous pharmaceuticals are markedly more soluble than their crystalline counterparts… Based on a comparison with polymorphic crystal forms of drug compounds the clinical relevance of solubility increases for amorphous drug forms is likely to be significant, even in systems which are only partially amorphous.”
Sharma para. [0009] teaches that for valganciclovir hydrochloride, the “amorphous form was found to have a superior stability profile to the existing crystalline form.
Sherwood teaches a synthetic psilocybin compound and Yu teaches methods of generating an amorphous solid from crystalline compound. Motivation to make the amorphous form is found in Hancock and Sharma.
Therefore, it would have been prima facie obvious at the time of the effective filing date for one of ordinary skill in the art to have taken the semi-crystalline compound of Sherwood and then create the amorphous form a reasonable assumption of success.
One of ordinary skill in the art would have found motivation to combine the teachings in order to increase the solubility of the semi-crystalline compound and the increased stability profile as discussed in Yu, Hancock, and Sharma.
Response to Arguments
The affidavit and remarks submitted 01/26/2026 have been considered. While the applicant and affidavit indicate an advantage over the art, it is not persuasive since the argued advantage is a property that is well known for amorphous forms.
The affidavit points to the differences between Sherwood and the instant claims in that the instant claims “replaced hot filtration and crystallization steps with a liquid-liquid extraction method” that forgoes the need for crystallization to achieve purity. Instead, the claimed product is purified via liquid-liquid extraction methods, which are techniques well known within the art, to purify the compound.
Additionally, the affidavit points to instant paragraphs [0237]-[0238]. Para. [0238] specifically states “following 1 week of storage at [room temperature], the lack of sharp reflexes indicated (that in the absence of sugars or polymer) the psilocybin lyophilizate long an short scan samples surprisingly maintained a non-crystalline/amorphous phase. The results of the measurement indicates the absence of long-range ordering (i.e. crystallinity), of the psilocybin lyophilizate samples.”
This is addressed above by Sharma, where the amorphous form of a crystalline compound had better stability.
Examiner’s Comments
The instant application is a divisional application of co-pending application 18/764,635 (parent application). The instant application was filed after a restriction requirement/species election made in the parent application.
Conclusion
No claims allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/L.G./Examiner, Art Unit 1624
/SUSANNA MOORE/Primary Examiner, Art Unit 1624
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