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 .
Election/Restriction
Applicant’s election without traverse of Group I, claims 1-14 in the reply filed on 08/03/2026 is acknowledged.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 1, 2, 4, 7, 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Massingill (US PG Pub 2019/0247769) in view of Popp (WO 2019/043259).
With respect to claim 1, Massingill teaches separations of substances including cannabinoids in fiber conduit contactors, a mobile phase flows between fibers, and in embodiments a constrained phase may be a liquid and flow along the fibers, and aqueous/polar constrained phase with an organic/non-polar mobile phase or vice versa (0001-0023, a method comprising: simultaneously introducing a immiscible with water composition and a first aqueous solution), in the example of figure 1 the mobile phase and constrained phase into inlets 16, 18, (0042, Fig. 1, into a first end of a first conduit reactor comprising a plurality of fibers disposed therein), the mobile phase flow from an outlet of the conduit to a receiver where any constrained phase carry over and the mobile phase are instantaneously separated (0037, 0042-0043, 001, 0055-0056, receiver chamber, collecting first reaction products in a first separator disposed opposite the first end, the separated constrained phase and mobile phase the first reaction products comprise a first organic phase, and a first aqueous phase), in some cases, a portion of the collected mobile phase can be recycled back to inlet port 18 and/or a portion or all of the constrained phase may be recycled back to inlet 16 (0043-0044, simultaneously introducing the first organic phase and a second aqueous solution into the first end of the first conduit reactor, wherein the second aqueous solution may be of the same kind or of a different kind than the first aqueous solution), Massingill teaches continuous operation (0040-0056, the portion of the collected mobile phase providing the first organic phase, and continuous operation providing collecting second reaction products in the first separator or in a second separator disposed opposite the first end of the second conduit reactor; wherein the second reaction products comprise a second organic phase comprising the cannabinoid and a second aqueous phase comprising the second aqueous solution and the second impurity; and separately removing the second organic phase), and concentration of impurities (0049-0050).
While Massingill does not explicitly teach the cannabinoid in the organic/non-polar phase, or impurities, as evidenced by Popp, Popp teaches cannabinoids are known separating and/or purifying acidic cannabinoids from cannabis plant extract, the method comprising a lighter phase acidified non-polar phase comprising the cannabinoid (p. 5, L17-25), providing evidence that Massingill’s taught method would provide the cannabinoid in the non-polar/organic phase, or would be obvious in view of.
Examiner notes Massingill teaches separation of cannabinoids, and concentration of impurities (0049-0050), absent clarification of differences over the prior art, the limitations with respect to the impurities are considered inherent, "Claim scope is not limited by claim language that suggests or makes optional but does not require steps to be performed. A “whereby clause in a method claim is not given weight when it simply expresses the intended result of a process step positively recited.” Id. (quoting Minton v. Nat’l Ass’n of Securities Dealers, Inc., 336 F.3d 1373, 1381, 67 USPQ2d 1614, 1620 (Fed. Cir. 2003); MPEP §2111.04). Where a reference discloses the terms of the recited method steps, and such steps necessarily result in the desired and recited effect, the fact that the reference does not describe the recited effect in haec verba is of no significance because the reference meets the claim under the doctrine of inherency."
With respect to claim 2, the method of claim 1, is taught above. Massingill teaches the organic phase and the second aqueous solution are simultaneously introduced into the first end of the first conduit reactor and recycling, as discussed above; the mobile phases require pH control, and pH of the mobile phase can be controlled by addition of a buffer (0023, 0049-0050,providing measuring a first pH of the first aqueous solution; measuring a second pH of the second aqueous solution); and teaches on-line monitoring of the effluent can be performed in various ways, e.g., pH, and pH-zone-refining which elutes highly concentrated rectangular peaks fused together with minimum overlapping while impurities are concentrated and eluted between the outside the major peaks and separation monitored by the pH of the effluent (0037, 0049), when the peak resolution is unsatisfactory, a measure of the constrained phase retention will serve as a guide for the next trial (0021), pH-zone-refining where proton transfer takes place at each zone boundary governed by the difference in pH between the neighboring zones, analytes elute as a train of rectangular peaks with sharp impurity peaks at their narrow boundaries, such that it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention recirculate the mobile phase, when the pH changes beyond a threshold, in order to collect a different fraction/peak. While Massingill does not explicitly teach a threshold of 0.5, the specific threshold would be a matter of design choice depending on the particular compound, and desired purity (comparing the first pH and second pH; if a difference between the first pH and second pH is greater than 0.5, reintroducing the second organic phase into the first end of the first conduit reactor with additional second aqueous solution).
With respect to claim 4, the method of claim 1, is taught above. Massingill teaches continuous operation where at least a portion of the mobile phase is recirculated as discussed above, as the first, second, and third impurities and aqueous solutions may be the same, Massingill’s method appears to satisfy the claim language.
With respect to claim 7, the method of claim 1, is taught above. Massingil teaches separation of a variety of substances, such as but not limited to specialty organic chemicals, active pharmaceutical ingredients (API), API intermediates, amino acids, peptides, enzymes, proteins, antibiotics, lipids, phospholipids, agrochemicals, insecticides, vitamins, organic acids, amines, sugars and derivatives, medicinal plant extracts such as neutraceuticals, cannabinoids, flavonoids, catechins, alkaloids, anthraquinones, ligands, dyes and pigments, others, specific separation processes contemplated include but are not limited to separation of separation of hemp extract into CBD, CBDA, and other cannabinoids, separation of fatty acids from oils and/or fats, separation of phospholipids from oils or fats (0018),the first impurity comprises free fatty acids (FFAs), pesticides, gums, phospholipids, colorants or pigments, odor causing substances, acidic cannabinoids, sugars, cellulose, hemicellulose, chlorophyl, or combinations thereof.
With respect to claim 8, the method of claim 3, is taught above. Massingill teaches simultaneously introducing the first organic phase and the second aqueous solution comprises introducing into the first end of the first conduit reactor (Fig. 1).
Claim(s) 3, 5, 6, 9, 10, 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over Massingill (US PG Pub 2019/0247769) in view of Popp (WO 2019/043259), in view of Fisher (US PG Pub 2023/0271930) and Townsend (US PG Pub 2023/0173407).
With respect to claims 3-6, the method of claim 1, is taught above. Massingill teaches buffers (acids or bases) may be added to the mobile phase (0023), and examples of constrained phases include but are not limited to water, water solutions, water and co-solvents, water and polymers, water and salts, water and ionic liquids (0022), fibers may be used with an aqueous/polar constrained phase with an organic/non-polar mobile phase of vice versa (0023), providing aqueous acidic solution or basic aqueous solution, or water or brine.
While Massingill does not explicitly teach different solutions such that the first aqueous solution is an acidic solution or a basic solution and the second aqueous solution is water or brine. Fisher teaches sequential liquid liquid solvent extraction for obtaining highly purified THCa from cannabis (abstract, 0001-0025), comprising the steps of: preparing a mother liquor from Cannabis plant material extracted with a hydrocarbon solvent with acid, washing the mother liquor with an aqueous solution, extracting the treated mother liquor of with a basic solution, and washing and extracting (0043), and washing with water (0014), such that it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use a first aqueous acidic solution or basic solution and a second aqueous solution water or brine, depending on the desired product, and as the use of sequential separation of cannabinoids using different acids, bases and water/brine are known in the art as shown by Fisher.
Additionally, Massingill teaches preparatory separation with a fiber contactor, Townsend teaches a preparative chromatography system comprising a fiber contactor (0001-0004, 0116), arranged to execute a predetermined chromatography device sequence that defines the order of process liquids that are to be run through the chromatography device (0083), such that it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify Massingill’s taught method and system to perform sequential separation as taught by Fisher, as fiber contactors for sequential separations are known in the art and as according to Townsend the arrangement minimizes hold-up volume of the system (abstract).
With respect to claim 9, the method of claim 5, is taught above. Massingill teaches continuous operation and recycling as discussed above, Fisher teaches sequential separation, providing wherein simultaneously introducing the first organic phase and the second aqueous solution comprises introducing into the first end of the first conduit reactor and wherein simultaneously introducing the second organic phase and the third aqueous solution comprises introducing into the first end of the first conduit reactor. Additionally, Massingill teaches preparatory separation with a fiber contactor, Townsend teaches a preparative chromatography system comprising a fiber contactor (0001-0004, 0116), arranged to execute a predetermined chromatography device sequence that defines the order of process liquids that are to be run through the chromatography device (0083), such that it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify Massingill’s taught method and system to perform sequential separation as taught by Fisher, as fiber contactors for sequential separations are known in the art and as according to Townsend the arrangement minimizes hold-up volume of the system (abstract)
With respect to claims 10 and 11, the method of claims 3 and 5, is taught above. Massingill teaches a single contactor, however the use of multiple contactors/devices is known in the art as shown by Townsend, Townsend teaches in an embodiment a plurality of devices (Fig. 5, 0142-0148). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to include a plurality of conduits/devices as taught by Townsend in order to utilize a larger plurality of process liquids, for example a plurality of different wash (buffer) liquids (0095).
Claim(s) 1, 12-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Massingill (US PG Pub 2019/0247769), in view of Fisher (US PG Pub 2023/0271930) or alternatively Fisher in view of Massigill, in view of Tegan (US PG Pub 2020/0255389).
With respect to claims 1 and 12, 13, Massingill teaches separations of substances including cannabinoids in fiber conduit contactors, a mobile phase flows between fibers, and in embodiments a constrained phase may be a liquid and flow along the fibers, and aqueous/polar constrained phase with an organic/non-polar mobile phase or vice versa (0001-0023, a method comprising: simultaneously introducing a immiscible with water composition and a first aqueous solution), in the example of figure 1 the mobile phase and constrained phase into inlets 16, 18, (0042, Fig. 1, into a first end of a first conduit reactor comprising a plurality of fibers disposed therein), the mobile phase flow from an outlet of the conduit to a receiver where any constrained phase carry over and the mobile phase are instantaneously separated (0037, 0042-0043, 001, 0055-0056, receiver chamber, collecting first reaction products in a first separator disposed opposite the first end, the separated constrained phase and mobile phase the first reaction products comprise a first organic phase, and a first aqueous phase), in some cases, a portion of the collected mobile phase can be recycled back to inlet port 18 and/or a portion or all of the constrained phase may be recycled back to inlet 16 (0043-0044, simultaneously introducing the first organic phase and a second aqueous solution into the first end of the first conduit reactor, wherein the second aqueous solution may be of the same kind or of a different kind than the first aqueous solution), Massingill teaches continuous operation (0040-0056, the portion of the collected mobile phase providing the first organic phase, and continuous operation providing collecting second reaction products in the first separator or in a second separator disposed opposite the first end of the second conduit reactor; wherein the second reaction products comprise a second organic phase comprising the cannabinoid and a second aqueous phase comprising the second aqueous solution and the second impurity; and separately removing the second organic phase), and concentration of impurities (0049-0050), proton transfer takes place at each zone boundary governed by the difference in pH and pH-zone-refining which elutes highly concentrated rectangular peaks fused together with minimum overlapping while impurities are concentrated and eluted between the outside the major peaks and separation monitored by the pH of the effluent (0037, 0049-0050), but is silent as to the specific compounds separated.
Fisher teaches isolating, in high purity, THCa cannabinoid from plant material comprising cannabinoids, terpenes, lignins, waxes and other impurities (abstract, 0001-0025, wherein the cannabinoid containing composition comprises a first cannabinoid or a terpene), CBD (0098), comprising the steps of: preparing a mother liquor from Cannabis plant material extracted with a hydrocarbon solvent with acid, washing the mother liquor with an aqueous solution, extracting the treated mother liquor of with a basic solution, and washing and extracting of phases (0043), and washing with water (0014), and an aqueous phase is adjusted to a basic pH, for example to a pH of 12.65-13, providing a basic solution of THCa carboxylate (0059, wherein the first aqueous solution has a pH of less than 2 or greater than 13), acid-base extraction is typically used to separate organic compounds from each other based on their acid-base properties; most organic compounds are more soluble in organic solvents than they are in water, some organic compounds can be converted into a water soluble salt, in this case THCa is converted to THC (0056, 0096-0102), wherein the cannabinoid containing composition or the first aqueous solution is capable of converting the first cannabinoid or the terpene into a second cannabinoid that is different than the first cannabinoid and the terpene.
Fisher teaches countercurrent liquid-liquid centrifugal contacting, settling, and/or liquid membrane extraction (0045), Massingill teaches the methods do not require centrifugation and can be scaled up readily for large scale industrial separations at relatively modest cost (0040-0052).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify Fisher’s taught method to use Massingill’s conduit separation method as according to Massingill the methods do not require centrifugation and can be scaled up readily for large scale industrial separations at relatively modest cost (0040-0052); or alternatively to modify Massingill’s taught method for use in Fisher’s taught method as when a primary reference is silent as to a certain detail, one of ordinary skill would be motivated to consult a secondary reference which satisfies the deficiencies of the primary reference.
While the taught combination does not explicitly teach a catalyst, the taught combination provides acidic phases achieved by buffers and acidification, Tegen teaches processes for purifying THCs, cannabinoids, or terpenes from sources comprising a cannabidiol (CBD) (abstract), and adding a catalyst to a first extract comprising the plurality of cannabinoids or terpenes and a first solvent, the catalyst converts Δ8-THC to Δ9-THC (0029-0030), catalysts are or comprise acids.
If Fisher’s taught conversion is not adequate to address the claim language it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to include a catalyst as taught by Tegen depending on the starting composition or desired product.
With respect to claim 14, the method of claim 1 is taught above. Tegen teaches solvents can comprise oxalic acid, see instant specification 0023 examples of catalysts include oxalic acid.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Goodwin US20050049298
Ito US 5332504
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/JEANNIE MCDERMOTT/Examiner, Art Unit 1776
/BRADLEY R SPIES/Primary Examiner, Art Unit 1776
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