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 11/14/2024, claims priority to U.S. Provisional Application No. 63/344,119, filed on May 20, 2022; U.S. Provisional Application No. 63/344,122, filed on May 20, 2022; U.S. Provisional Application No. 63/344,130, filed on May 20, 2022; U.S. Provisional Application No. 63/344,133, filed on May 20, 2022; U.S. Provisional Application No. 63/344,136, filed on May 20, 2022; U.S. Provisional Application No. 63/344,137, filed on May 20, 2022; U.S. Provisional Application No. 63/344,140, filed on May 20, 2022; U.S. Provisional Application No. 63/344,142, filed on May 20, 2022; U.S. Provisional Application No. 63/350,548, filed on June 9, 2022; U.S. Provisional Application No. 63/350,550, filed on June 9, 2022; and U.S. Provisional Application No. 63/350,577, filed on June 9, 2022
Information Disclosure Statement
The information disclosure statement (IDS) filed on 11/14/2024, 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
The premilitary amendment filed on 11/14/2024, that cancelled claims 1, and 4-73, is acknowledged.
Claims 2 and 3 are pending.
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 of crystalline form 1:
Claims 2 and 3recite “crystal form 1 of [2-(5-methoxy-1H-indol-3-yl)ethyl](propan-2-yl)propylazanium chloride, characterized by at least one of: a monoclinic crystal system at a temperature of about 297 K; a P21 space group at a temperature of about 297 K; unit cell dimensions a = 9.5054(9) A, b = 7.3960(7) A, c = 13.4481(12) A, a = 90°, B = 109.924(3)°, and y =90°; an X-ray powder diffraction pattern substantially similar to FIG. 25; or an X-ray powder diffraction pattern characterized by at least two peaks selected from 7.0, 10.0, and 21.1 °2[Symbol font/0x71]±0.2 °2[Symbol font/0x71].
Instant specification recites that the crystalline form 1 characterized by XRPD substantially similar to FIG. 25 [0014]. While the specification does not provide definition to the term substantially, the art teaches that compounds can exists in multiple crystalline forms, and the gold standard to distinguish these forms is through XRPD. The XRPD consider to be the fingerprint in determining and identifying the particular crystalline form. In view of the instant specification, the claimed crystalline form 1 is defined by XRPD peaks as shown in Figure 25, and in view of the art, crystalline form 1 is defined by Figure 25 and will be interpreted as the crystal form of Figure 25.
The claims are given their broadest reasonable interpretation in light of the specification. MPEP 2111. In particular, the reference to “Crystalline Form 1” in the instant specification and in the claims is always associated with the language “characterized by” regarding spectroscopic information i.e., XRPD peaks. Consistent with MPEP 2111.03, the claims are construed as being open-ended to allowing additional elements. In this case, the claims are construed as allowing other spectroscopic information as well as other solid forms “characterized” by additional information.
However, in view of the above interpretation, crystalline form 1 is not defined by the “open-ended” claim 3 the recited XRPD peaks, instead, the crystalline form A is defined by Figure 25.
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 2 and 3 are rejected under 35 U.S.C. 103 as being unpatentable over S. Banister et al. (US PG PUB 2025/0074873A1, 03/06/2025 (Effective Filing date 12/24/2021), “Banister” cited in the PTO-892) in view of W. Barth et al. (US Patent No. 4,432,987A, 02/21/1984, “Barth”, cited in the PTO-892) and S. Morissette, et al. Advanced Drug Delivery Reviews, Volume 56, Issue 3, 2004, Pages 275-300, “Morissette” cited in the PTO-892).
Prior Art Effect of Banister
The earliest possible effective filing date of the subject claims is that of priority document U.S. Provisional Application No. 63/344,122, filed on 05/20/2022. Banister is effective prior art under 35 USC § 102(a)(2) respecting the subject matter cited in this rejection as of the filing date of Banister priority document AU2021904274 (12/24/2021) because: (1) Banister is U.S. patent application publication; (2) names another inventor; and (3) the subject matter of Banister relied upon in this rejection is disclosed in Banister’s priority document AU2021904274 (12/24/2021). See MPEP § 2154.01; 35 USC § 102(d). Thus, the effective filing date of the subject matter relied upon in this rejection is 12/24/2021, which is before the claims’ earlies possible effective filing date of 05/20/2022. See MPEP § 2154.01; 35 USC § 102(d).
Banister teaches compound of formula (I) and teaches compound P-17 ([2-(5-methoxy-1H-indol-3-yl)ethyl](propan-2-yl)propylazanium) or a pharmaceutically acceptable salt, solvate, polymorph or prodrug thereof, as species of formula (I), [page 24, [0321], right col. 2nd comp.]:
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Banister teaches that salts of the compound of formula (I), i.e., P-17 may exist in different crystalline or polymorphic forms, all of which are intended to be within the scope of the present invention and specified formulae. [0424]. Banister teaches that all crystalline forms of a compound of Formula (I) including anhydrous crystalline forms, hydrates, solvates and mixed solvates. If any of these crystalline forms demonstrates polymorphism, all polymorphs are within the scope of this invention. [0425]
Banister teaches that basic nitrogen-containing groups may be quarternized with such agents as C1-6alkyl halide, such as methyl, ethyl, propyl, and butyl chlorides, bromides and iodides, [0429].
Banister teaches that the compound of formula (I) i.e., activate 5-HT2A, 5-HT2B and 5-HT2C. Out of the 5-HT activators of Banister, P-17 is the most potent and selective agonist that actives all three receptors, with activity on 5-HT2A, 5-HT2B and 5-HT2C receptors of EC50 13.82 nM, EC50 137.9 nM and EC50 184.9 nM, respectively, [[0580], Table 1, P-17].
However, Banister does not specifically teach the chloride salt of P-17 or the crystalline form 1 of P-17 or the spectroscopic characterization.
In the same art area, namely pharmaceutical preparations and their use in treating disease, Barth teaches the following:
“[c]rystalline forms of compounds are ordinarily preferable to the non-crystalline forms thereof. The crystalline materials have superior stability, appearance and handling characteristics when compared to their amorphous counterparts. For pharmaceutical use crystalline compounds are especially advantageous in manufacturing procedures and in formation and use of acceptable dosage forms such as solutions, suspensions, elixirs, tablets, capsules and various pharmaceutically elegant preparations required by the medical and pharmaceutical professions.” [Pg. 2, col. 1, ln. 60- col. 2, ln. 2].
Morissette teaches an automated high-throughput crystallization to form polymorphs, salts, co-crystals and solvate forms of pharmaceuticals [Title, abstract]. The prior art describes the successful application of the automated high-throughput technique to several known pharmaceuticals and details how thousands of crystallization conditions can be performed in parallel, computer analyzed and then used to produce the polymorphic forms of a given pharmaceutical [Pg. 296, para. 2].
At the time of invention, one of ordinary skill in the art practicing the Banister’s pharmaceutical compound P-17 would form a crystalline form in accordance with the specific teaching of Banister.
One of ordinary skill in the art would have been motivated to specifically prepare the chloride salt of P-17 because: Barth teaches that crystalline forms are preferable for pharmaceutical compounds, crystalline forms are more stable, preferred in formulation of dosage forms, and advantageous in manufacturing procedures, which motivate skilled artisan to prepare crystalline form of the potent Banister P-17; Banister teaches preparation of P-17 in Ex. 20, wherein the compound isolated as N-isopropyl-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)propan-1-amine, as an oil [0536]; the oil of P-17 converted to salt by treating the resulting oil product with HCl as exemplified by compounds P-19- P-22, [0539]- [0546]; Banister teaches that the salts of the compound i.e., P-17 form crystalline forms [0424]; Banister teaches the P-17 is the most potent agonist. Thus, one of ordinary skill in the art would have been motivated to prepare the crystalline form of the chloride salt of the potent P-17 in view of Barth teachings of the advantageous of crystalline form in pharmaceutical.
Utilizing the routine “High-throughput salt selection” taught by Morissette [Pg. 285-287] one of ordinary skill in the art would arrive at the claimed invention. Specifically, because Banister teaches that the compounds e.g., P-17 from crystalline forms, and teaches that all P-17 crystalline forms are within the scope of this invention, [0425], and P-17 salts (chloride, bromide or iodide) which exist in crystalline or polymorphic forms, are intended to be within the scope of the present invention [0424]. Thus, one of ordinary skill in the art would have a reasonable expectation of success in arriving at the claimed invention.
In the instant case one of ordinary skill in the art would have a reasonable expectation of success in following the teaching of Banister and utilizing the well-known and routine automated high-throughput screening described by Morissette arrive at the claimed invention because such acts are conventional and routine in the art. One of ordinary skill in the art would be expected to apply methods within their technical grasp (such as automated high-throughput screening) to improve that which is already known in the art. The Supreme Court stated in KSR “if a technique has been used to improve one device, and a person of ordinary skill in the art would recognize that it would improve similar devices in the same way, using the technique is obvious unless its actual application is beyond that person's skill.” KSR Intern. Co. v. Teleflex Inc., 127 S.Ct. 1727, 1731 (2007). Here, the use of an automated system to screen a pharmaceutical salt for crystallization is well known and specifically taught by Morissette. Therefore, the method is within the technical grasp of those of ordinary skill in the art and it would be obvious to one of ordinary skill in the art to use the same method and apply it to the Banister’s compound P-17.
Regarding the spectroscopic characterization of the obvious product, such properties are inherent in the product (MPEP 2112.02: "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. Id.). In this case, one of ordinary skill in the art would have reasonably considered producing the crystalline salt form which would inherently show the same spectroscopic parameters as are in the claim. "[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his [or her] claimed product. Whether the rejection is based on ‘inherency’ under 35 U.S.C. 102, or ‘prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same." In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977).
Thus, claims 2 and 3 are rejected as prima facie obvious.
Conclusion
Claims 2 and 3 are rejected. No claim is allowed.
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/M.M.A./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622