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 of response and IDS dated 5/19/25 is acknowledged.
Claims 1-23 are pending. Claims 1-9 have been examined. Claims 10-23 have been withdrawn from examination.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 5/19/25 is being considered by the examiner.
In response to the persuasive arguments filed on 5/19/25, that Donsky reference fails to teach the claimed cannabinoid acids and the absence of surfactants, the previous rejection of record has been replaced with the following new rejection:
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-9 are rejected under 35 U.S.C. 103 as being unpatentable over US 8846409 to Flockhart et al in view of US 2016/0279073 to Donsky et al. (Donsky), Klossek et al (Klossek), CN 107951869 A to Zhang et al (Zhang) (translation attached) and US 2014/0274936 to Piccariello et al.
** It is noted that the previous action and PTO-892 inadvertently refers to Zhang reference as CN 10751869. However, a full translation of the document has been attached in the previous action.
Instant claims are directed to a solid, micellar composition, comprising micelles of one or more cannabinoid acids and a metal, wherein: the one or more cannabinoid acids are in a salt form, the salt form having a 5 monovalent counter ion; the micelles are free of added surfactants; and the micelles comprise an outer hydrophilic portion and an inner hydrophobic portion.
Flockhart teaches methods of preparing cannabinoids in substantially pure form starting from plant material, wherein the preparations include extracts enriched in cannabinoids and cannabinoid acids, with a purity of greater than 95% (abstract & fig. 1-2). Flockhart teaches that the cannabinoid components present in herbal cannabis are the cannabinoid acids Δ9 tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA), with small amounts of the corresponding neutral cannabinoids, respectively. Δ9 tetrahydrocannabinol (THC) and cannabidiol (CBD). Cannabidiol was formerly regarded as an inactive constituent, however there is emerging evidence that it has pharmacological activity, which is different from that of . Δ9 THC in several respects (col.1, l 39-48). The method of preparing the process cannabinoids and cannabinoid acids is described in col. 9, l 48-col. 2, l 53). For the instant claimed cannabinoid acids, Flockhart teaches THCA, CBDA (col. 8, l 29-52).
For claims 7-8, as explained above, Flockhart teaches cannabinoids in addition to cannabinoid acids.
Flockhart fails to teach the claimed metal salts of cannabinoid acids, a solid micellar composition and wherein the micelles are free of added surfactants.
Donsky teaches a liposome or micelle formulation comprising terpenes, hemp oil, cannabinoids, or mixtures of a cannabinoid and terpenes or hemp oil and cannabinoids, suitable for pharmaceutical and nutraceutical applications (abstract), and having a micelle in an average size of 50 nm to 1000 nm [0023]. Donsky teaches the method of preparation includes cannabinoid or cannabinoid analogues dissolved in ethanol or terpene to obtain terpene-cannabinoid liposomes [0033 & 0075]. The method of preparation does not include am surfactant and hence meets instant claimed surfactant. The composition is in the form of oral composition [0034-0035]. For the instant claimed solid composition, Donsky teaches formulations such as tablets, pills, capsules etc [0064].
Donsky additionally teaches incorporating additional components such as antibiotics [0061], vitamins [0062], and thus meets instant claim 9. Instant claim 6 requires that the additional lipid component is sequestered in the inner hydrophobic portion of the micelles.[0078] teaches the cannabinoid-terpene vehicles for delivery, and therefore one of an ordinary skill in the art would have expected that the use of the micelles for delivering of cannabinoid-terpene and further the additional agents such as antibiotics or vitamins.
With respect to the claimed salt and in particular metals such as calcium (instant claim 4 and 5), Donsky teaches preparing calcium alginate encapsulated liposomal suspensions [example 5], a film formation of liposomal suspensions by including calcium chloride. [0109] describes a film comprising calcium alginate added to a liposome formulation comprising terpenes, cannabinoids and sodium alginate.
Zhang teaches pharmaceutical compositions comprising cannabidiol in the form of a pharmaceutically acceptable salt (abstract), in particular salts formed with potassium, sodium, magnesium, aluminum, lithium etc.(page 4, 4th full para), and the composition in the form of a tablet, capsule, powder, etc (p 4, 5th full para).
Zhang does not teach reason for employing the salt forms of cannabinoids. However, Zhang teaches that the salt forms of both groups (instant claim 3 or claim 4) as being useful for treating depression.
Piccariello teaches stable coordinated complexes having a metal and a biologically active agent, and useful for pharmaceutical and nutraceutical application [0010]. Piccariello teaches that the biologically active agent is cannabinoid, and the metal can be a s-block, d-block or a p-block metal (see claims 7 & 10 of the reference). Piccariello teaches that the metal salts of biologically active agents improve solubilities of the poorly soluble actives [0006]. For the metal salts, the reference teaches metals such as calcium, magnesium, nickel etc [0010], and that the chelation with s-block, d-block or a p-block metals provide a critical component in the stabilization [0029-0032]. Further the complexes are described in [0084]-[0085].
Therefore, it would have been obvious for one of an ordinary skill in the art before the effective filing date of the instant invention to modify the composition of Flockhart, comprising the claimed cannabinoid acid as well as cannabinoid, to prepare metal salts of the cannabinoid acids, and further employ the said metal salts in the preparing solid micelles of instant claims. One of an ordinary skill in the art would have been motivated to modify because while Flockhart only teaches preparing substantially pure cannabinoid acids the reference does not suggest methods of administering the said compounds, and in this regard, Donsky suggests pharmaceutical and nutraceutical compositions employing micelle formulations for effectively delivering the desired amounts of cannabinoid acid and cannabinoid compounds, via several routes. One of an ordinary skill in the art would have further prepared complexes of salt forms of cannabinoid acids and cannabinoids by employing metals such as potassium, sodium, magnesium, aluminum, lithium (taught by Zhang), calcium, magnesium or strontium (taught by Piccariello) because while Zhang teaches salt forms of cannabinoids are useful to treat depression, Piccariello teaches coordination complexes of cannabinoids (claimed cannabinoids) with metals improve the solubility of cannabinoids and thus improving the biovailability at physiological pH. Hence, one of an ordinary skill in the art would have expected that the composition of Flockhart modified by Donsky, Zhang and Piccariello provides effective pharmaceutical compositions with increased solubility and bioavailability.
Flockhart does not teach employing any surfactants in preparing cannabinoids or cannabinoid acids, and hence meet instant surfactant-free limitations.
However, microemulsions that are free of surfactants are known in the art as described by Klossek. Klossek teaches that microemulsions (also termed as micelles) are transparent, macroscopically homogenous, low-viscous one-phase system consisting of a surfactant component in the form of a molecular film. However, Klossek teaches that the drawback of microemulsions is that they include very high amounts of surfactant (paragraph 1, page 4116). Klossek teaches that well defined domains of two fluids of clearly different composition can exist in surfactant-free ternary mixtures. Further, Klossek teaches that the inner core of the microemulsions containing hydrophobic groups and are comparable to the surfactant containing emulsions (fig. 3), and yet provide thermodynamically stable emulsions (col. 1, p 4118).
Thus, it would have been obvious for one of an ordinary skill in the art before the effective filing date of the instant invention to prepare the micelle composition of Flockhart (modified by Donsky, Zhang and Piccariello) without including surfactants (surfactant-free micelle) because Klossek teaches conventional microemulsions include high amounts of surfactants for solubilizing whereas one can prepare surfactant-free and yet thermodynamically stable micelles that are comparable to those prepared by including high amounts of surfactants. Therefore, even though Donsky teaches employing surfactant in preparing the cannabinoid acid micelles, one of an ordinary skill in the art would have expected that the surfactant-free micelles provide thermodynamically stability.
Response to Arguments
Applicant's arguments filed 5/19/25 have been fully considered. As explained above, Applicants’ arguments that Donsky reference fails to teach the claimed cannabinoid acids and the absence of surfactants, have been found persuasive. However, upon further search, the previous rejection of record has been replaced with a new rejection. The present rejection relies on new references, Flockhart et al., and Klossek et al., in combination with the previously cited Donsky, Zhang and Piccariello references. The newly cited Flockhart references teach the instant claimed cannabinoid acids as well as cannabinoids, and Klossek has been relied on for the teaching of a surfactant-free micelle. The argument that the claimed micelles are formed in-situ is not persuasive because instant examined claims are directed to a composition and not a process of producing micelles. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). Therefore, the argument is not persuasive.
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/LAKSHMI S CHANNAVAJJALA/Primary Examiner, Art Unit 1611
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