DETAILED ACTION
All objections and rejections not mentioned below have been withdrawn.
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
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in parent Application No. PCT/EP2019/072843, filed on 8/27/2019.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 02/25/2022 is being considered by the examiner.
Claim Rejections - 35 USC § 103 -Modified Due to Amendments
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.
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) 1-3, 6, 8-10 and 11-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Raber (Raber et al., US 9732009 B2, 08/15/2017).
The reference Raber teaches “The present disclosure fulfills an unmet need by providing concentrated preparations of purified cannabinoids that do not contain solvent, and that were not prepared using any solvent”[0004] and “The present disclosure provides non-solvent lipid compositions for use as an extraction agent, for use as a carrier, or for use as both an extraction agent and as a carrier, for processing chemical constituents and for serving as a vehicle for dissolving said chemical constituents. The lipid composition can be, canola oil, peanut oil, sunflower oil, safflower oil, corn oil, soy oil, sesame oil, olive oil, avocado oil, grapeseed oil, annatto oil, almond oil, mustard oil, walnut oil, seed oil, nut oil, ground nut oil, a tree oil, jojoba oil, guayule oil, fish oil, cod liver oil, oil from a recombinant plant or from a recombinant microorganism, or any combination thereof, and the like. Also available, is an oil such as a wax oil, that is not a triglyceride oil. Moreover, the lipid composition can be a fat that is normally a solid at room temperature, and where extraction occurs at or above the melting temperature of the fat. The fat can be, for example, butter, margarine, lard, hydrogenated vegetable oil, partially hydrogenated vegetable oil, any combination thereof, and the like. Furthermore, the lipid composition can be a combination of an oil and a fat, such as a combination of canola oil and butter. What is encompassed is plant-derived oils, fungus-derived oils, animal-derived oils, microorganism-derived oils, oils manufactured by recombinant microorganisms or recombinant algae, and the like” [0106]. The reference Raber also teaches “Prior to use, the carrier lipid composition is subject to a purification scheme. Purification can be accomplished with distilling under vacuum (0.001 mbar) at higher temperatures (195 degrees C.)” [0107] and “Methods of the present disclosure can include one or more of the indicated series of steps. In some embodiments, the ordering of the steps is mandatory, while in other embodiments, the ordering of one or more of the steps can be reversed or changed”[0073]. Raber teaches “In a preferred embodiment, the final product of the present disclosure takes the form of a cannabinoid-rich resin. This cannabinoid-rich resin can optionally be redistilled to achieve higher purity. Redistillation is preferably at 165 degrees C …”[0114] and “…The cannabinoids can be dispersed into a non-solvent such as canola oil and then optionally subjected to further purification…”[0124] and “The high-THC canola oil is optionally subjected to distillation”[0125]. Additionally, Raber teaches “Systems and methods of the present disclosure are particularly useful for purifying chemicals such as tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), and cannabigerolic acid (CBGA); and decarboxylating them to tetrahydrocannabinol (THC), cannabidiol (CBD), and cannabigerol (CBG), respectively”[0007] and “The system and methods may use other materials, in place of a solvent, such as oil or an ionic liquid, for extracting plant material or for further extraction of a plant extract, followed by purification by distillation, optionally with heat-induced chemical transformation of natural products in the plant material. The heat-induced chemical transformation can include decarboxylation”[0002]. Additionally, the lipid extract containing cannabinoids acids shown in reference table 1 gives a 30% cannabinoid acids on total cannabinoids because 30%=100 x 1.105/(2.191+1.105+0.216+0.215). This helps to teach claims 1, 2, 3, 10 and 12.
Additionally, Raber teaches “These fractions may include a fraction that is greater than 70% THC…”[0090]. This helps to teach claims 6-9.
The reference Raber teaches “In yet another aspect, what is provided is the above method, wherein the non-solvent that is enriched in the chemical constituents comprises a first chemical constituent and a second constituent, and wherein the step of volatilizing results in a volatilized fraction, and also results in the separation of the first chemical constituent from the second chemical constituent, wherein the volatilized fraction is relatively enriched in the first chemical constituent and relatively depleted in the second chemical constituent, and wherein the non-solvent that is enriched in the chemical constituents contains heat-decarboxylatable chemical constituents, and wherein the step of volatilization results in heat-induced decarboxylation of less than about 10% of the heat-decarboxylatable chemical constituents” [0025]. This helps to teach claim 11.
The reference Raber does not explicitly teach distillation after lipid extraction (claim 1) or the high concentration of the acids in the concentrate (claims 8 and 9).
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber to achieve a method of lipid extraction then distillation because Raber states the steps in the method can be rearranged and states “In a preferred embodiment, the final product of the present disclosure takes the form of a cannabinoid-rich resin. This cannabinoid-rich resin can optionally be redistilled to achieve higher purity”[0114] as well as “…The cannabinoids can be dispersed into a non-solvent such as canola oil and then optionally subjected to further purification…”[0124] and since the decarboxylation is stated as optionally one would be motivated to distill after extraction for a higher purity acid product because distillation will remove some of the impurity that extraction would not remove since distillation function by boiling point not differential solubility. Additionally, it would have been obvious to achieve higher percentages of the acid forms since the decarboxylation is optional and it is stated that this method can be used to purify the acids [0007] and that distillation can provide an increased percentage of the chosen cannabinoid in a lipid [0090] so it would have been obvious to try distilling the acids in the lipids to achieve higher concentration and one would have been motivated to do so to achieve higher purity by distillation.
Claim(s) 1-3, 5-6, 8-9 and 11-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Raber (Raber et al., US 9732009 B2, 08/15/2017) in view of Farokhi (Farokhi et al., WO 2020028991 A1, effective filing date 08/08/2018).
The reference Raber has been discussed supra and does not explicitly teach distillation after lipid extraction (claim 1) or the high concentration of the acids in the concentrate (claims 8 and 9).
The reference Farokhi teaches “COLD EXTRACTION METHOD FOR CANNABINOIDS AND TERPENES FROM CANNABIS BY POLYUNSATURATED LIPID-BASED SOLVENTS” (title), “More specifically, the invention provides methods for extracting and isolating compounds such as pure cannabinoids, cannabinoid acids, terpenes, terpenoids, flavonoids or other bioactive molecules from cannabis plant material at low temperature by using polyunsaturated lipid solvents that have a melting point below 0°C”[00040] and “In some embodiments of the methods of the disclosure, the botanical extract is subject to one or more additional purification methods. In some embodiments, the one or more additional purification methods comprise molecular distillation…”[00018]. Farokhi also teaches “Purification of cannabis oil into cannabinoid distillates may be performed in one or more embodiments under vacuum about 0.001 mbar, by molecular distillation…”[00073] and “In some embodiments, distillation and/or sublimation can be used to further purify cannabis extracts of the instant disclosure. Distillation and sublimation have been used to separate components of plant medicines which have boiling points at or around the temperature at which water boils at atmospheric pressure (l00°C). Separation by distillation is a physical process widely used in the preparation of essential oils. For example, GB 635,121 describes a process for the preparation of extracts from aromatic plants by distillation with the help of a hot gas, preferably under high vacuum. As a further example, WO 99/11311 describes a vaporizer for inhalation and a method for the extraction of active ingredients from a crude natural product. This method utilizes an ascending stream of hot air, or a heated inert gas stream, to volatilize components from the natural product. The resultant vapor may then be inhaled by a user. As yet a further example, WOOO/25127 is concerned with a method of preparing tetrahydrocannabinol using extraction of plant material with a non-polar solvent followed by vacuum distillation and collection of a constant boiling fraction. Additional distillation steps and chromatographic steps, including HPLC, reverse phase HPLC and flash chromatography, may be performed. In some embodiments, molecular distillation can be used to further purify cannabis extracts of the instant disclosure. Molecular distillation, sometimes called short path distillation, is a separation technique that separates compounds through a process of slow thermal heating. The compounds in cannabis extracts, such as cannabinoids, terpenes and flavonoids, have different vapor pressure points (boiling points). Through precise temperature control of the distillation process, molecular distillation can separate a cannabis extract into one or more high-purity fractions. In exemplary embodiments, the final materials produced through short path distillation include one or more cannabinoids, one or more terpenes, and optionally, any leftover waxes, sugars, and heavy residues. In some embodiments, the molecular distillation comprises more than one round of molecular distillation” [000114-000115]. This helps to teach claims 1 and 5.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber to achieve a method of lipid extraction then distillation because Farokhi teaches purification of cannabinoid acids by first lipid extraction and then short path distillation and since the decarboxylation is stated as optionally one would be motivated to distill after extraction for a higher purity acid product because distillation will remove some of the impurity that extraction would not remove since distillation function by boiling point not differential solubility. Additionally, it would have been obvious to achieve higher percentages of the acid forms since the decarboxylation is optional and it is stated that this method can be used to purify the acids [0007] and that distillation can provide an increased percentage of the chosen cannabinoid in a lipid [0090] so it would have been obvious to try distilling the acids in the lipids to achieve higher concentration and one would have been motivated to do so to achieve higher purity by distillation.
Claim(s) 1, 4, 14-26 and 28-29 is/are rejected under 35 U.S.C. 103 as being unpatentable over Raber (Raber et al., US 9732009 B2, 08/15/2017) in view of Farokhi (Farokhi et al., WO 2020028991 A1, effective filing date 08/08/2018) further in view of VENTURINI DEL GRECO (VENTURINI DEL GRECO et al., WO 2018130682 A1, 07/19/2018).
The reference Raber and Farokhi have been discussed supra and does not disclose lipid extract has a content of cannabinoids of at least 2 % by weight (claim 4) or the methods of claims 14-26 and 28-29.
The reference VENTURINI DEL GRECO teaches “In another aspect, provided herein, is a lipid-soluble extract obtainable from the process according to the invention, wherein the extract has a total phyto-cannabinoid content of at least 2, 3, 4 or 5 weight percent” (page 7, lines 10-20). This helps to teach claim 4.
The reference VENTURINI DEL GRECO also teaches “A process for producing a lipid-soluble extract from plant material containing phyto- cannabinoids and/or terpenoids and/or terpenes, comprising the steps of:
a. comminuting the plant material;
b. mixing the comminuted plant material with enzymes to form a mixture to which water and lipids are optionally added;
c. agitating the mixture at a temperature range of 1 to 80 °C; and
d. separating the mixture into a lipid phase, an aqueous phase, and a solid phase;
wherein the lipid phase comprises the lipid-soluble extract” ( reference claim 1). This helps to teach claims 14 and 15.
The reference VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 5, wherein said plant material derives from the Cannabis genus of plants, that encompasses the species C sativa, C indica and C. ruderalis” (reference claim 6) and “The process according to anyone of claims 1 to 4, wherein said plant material containing phyto-cannabinoids or terpenoids is chosen from the group consisting of hemp, cannabis, hops, echinacea, salvia dinivorum, chrysanthemum, helichrysum and hypericum biomass and wherein said plants are pure, hybrids or genetically modified variants thereof”(reference claim 5). This helps to teach claims 16-18.
VENTURINI DEL GRECO teaches “The process according to anyone of claims 1 to 8, wherein the plant material has a moisture content of at least 20% of the plant material weight” (reference claim 9). This helps to teach claim 19.
VENTURINI DEL GRECO also teaches “The process of claim 1 to 9, wherein said plant material is newly harvested and has a moisture content of at least 30%, preferably at least 40%.” (reference claim 10). This helps to teach claim 20.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 10, wherein the plant material has a total phyto-cannabinoid content greater than 0,2% of the plant material weight” (reference claim 11). This helps to teach claim 21.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 11, wherein the plant material is industrial hemp comprising less than 0.2-0.6% THC, or wherein the plant material is cannabis comprising more than 0.2-0.6% THC, or hybrids and genetically modified variants thereof. 13. The process according to anyone of claims 1 to 12, wherein the plant material has a seeds content lesser than 98% of the plant material weight”(reference claim 12). This helps to teach claims 22-23.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 14, wherein the plant material different from seeds is greater than 2% of the plant material weight” (reference claim 15). This helps to teach claim 24.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 21, wherein the enzyme is one or more enzymes independently selected from the group consisting of cellulase, hemicellulase, xylanase, glucanase, beta-glucanase, pectinase, amylase, alpha-amylase, phospholipase, arabanase, galacto-, beta-mannanase, protease and phytase; wherein the amount of enzyme is 0.5% to 10% of the weight of plant material; and the pH of the mixture is 3-10”(reference claim 22). This helps to teach claims 25.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 31, wherein steps a. and b. are inverted” (reference claim 32). This helps to teach claim 26.
VENTURINI DEL GRECO also teaches “The process according to anyone of claims 1 to 38, wherein less than 10%, preferably less than 5%, more preferably less than 2%, of cannabinoids are decarboxylated during the process”(reference claim 39). This helps to teach claim 28.
VENTURINI DEL GRECO also teaches “The solid phase according to claim 56, wherein the phyto-cannabinoid content of the plant material is reduced by at least 80 weight percent”(reference claim 57). This helps to teach claim 29.
VENTURINI DEL GRECO also teaches “In another embodiment, the aqueous phase and the lipid-soluble extract are used in the production of pharmaceutical, nutraceutical products, cosmetics, food or feed products, antimicrobial, antibacterial, insecticidal, or biocidal products.” (page 18, lines 15-20).
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber and Farokhi previously discussed to be obvious for the lipid extraction before distillation with the initial lipid extract provided by the steps of VENTURINI DEL GRECO because Raber uses a lipid extract of cannabinoids and VENTURINI DEL GRECO provides a lipid extract of cannabinoids and one would be motivated to do so because the steps are being used for the same purpose of purifying cannabinoids without solvents.
Claim(s) 1 and 5 are rejected under 35 U.S.C. 103 as being unpatentable over Raber (Raber et al., US 9732009 B2, 08/15/2017) in view of Norberk (Norberk et al., “Distillation for Pharmaceutical Production”, Pharmaceutical Technology Europe(Vol. 12, Issue 12), Intellisphere, LLC, Dec. 2000).
The Raber has been discussed supra and does not disclose wherein said vacuum distillation is carried out in at least one equipment selected from the group consisting of: short path equipment, wiped film and thin-film equipment of claim 5.
The reference Norberk teaches “The distillation of pharmaceuticals requires a method that prevents contamination or decomposition of the product during processing. To avoid damage to heat-sensitive products, thin film and short path distillation plants can be operated with short residence times (down to a few seconds) and, by reducing the pressure to 0.001 mbar, the evaporation temperature can be lowered by 100-200[degrees]C. Distillation plants can also be designed for ease of cleaning and sterilization, thus providing good quality control of the production process”(Full Text Section). This helps to teach claim 5.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber previously discussed to be obvious for the lipid extraction before distillation with the distillation equipment of Norberk because Norberk teaches that thin film and short path distillation plants are beneficial for avoiding degradation of heat-sensitive products, from Raber we know high heat can lead to decarboxylation and Raber can be used for purifying the acid versions, one would have been motivated to use one of these equipments to avoid degrading the acids.
Claim(s) 1, 13 and 27 are rejected under 35 U.S.C. 103 as being unpatentable over Raber (Raber et al., US 9732009 B2, 08/15/2017) in view of Farokhi (Farokhi et al., WO 2020028991 A1, effective filing date 08/08/2018) further in view of VENTURINI DEL GRECO (VENTURINI DEL GRECO et al., WO 2018130682 A1, 07/19/2018) and further in view of Zereshki (Zereshki et al., “Application of edible paraffin oil for cationic dye removal from water using emulsion liquid membrane”, Volume 356, 15 August 2018, Pages 1-8).
The methods of Raber, Farokhi and VENTURINI DEL GRECO and has been discussed supra and does not disclose liquid paraffin of claim 13 and 27.
The reference Zereshki teaches “Application of edible paraffin oil for cationic dye removal from water using emulsion liquid membrane”(title) and “Liquid-liquid extraction was proposed by Muthuraman to remove the astacryl golden yellow and astacryl blue BG dyes from aqueous solutions [11]. Supported liquid membrane (SLM) and bulk liquid membrane (BLM) are also studied for separation and removal of dyes [12–16]. One of the interesting and high potential methods for separation of dyes is using emulsion liquid membranes (ELM)...So far, in the ELM process, oil derivatives such as hexane [20,21], kerosene [5,8,18] and heptane [22] have been used as solvents. The solubility of hexane, heptane and kerosene in water are in the range of 10 mg/L. While, according to the world health organization (WHO) the permitted amount of hydrocarbons in water is less than 0.05 mg/L [23]. These chemicals are volatile, flammable and nonrenewable causing environmental issues [24]. Furthermore, the environmental impact is even more serious, due to the poor membrane stability [25]. Using edible solvents instead of toxic organic solvents, which are commonly used in liquid membranes, is proposed as a suitable solution to overcome this issue. Vegetable oils such as palm, soybean, sunflower, and sesame are used as solvents in emulsion liquid membrane to remove phenol [26], Cd [25], succinic acid [27] and Cr [28]. In this work, we have used edible oils for dye removal which is not studied before to the best of the authors' knowledge”(page 2, second paragraph). This helps to teach claims 13 and 27.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber and Farokhi previously discussed to be obvious for the lipid extraction before distillation with the initial lipid extract provided by the steps of VENTURINI DEL GRECO because Raber uses a lipid extract of cannabinoids and VENTURINI DEL GRECO provides a lipid extract of cannabinoids and one would be motivated to do so because the steps are being used for the same purpose of purifying cannabinoids without solvents. Additionally, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified Raber and VENTURINI DEL GRECO methods with a liquid paraffin as taught in Zereshki because liquid paraffin is a lipid oil that has previously also been used for extraction for the same purpose of avoiding traditional nonedible solvents. One would have been motivated to use liquid paraffin since it is non-toxic.
Claim(s) 33-38 are rejected under 35 U.S.C. 103 as being unpatentable over Black (Black et al., US 20190231737 A1, 08/01/2019) in view of VENTURINI DEL GRECO (VENTURINI DEL GRECO et al., WO 2018130682 A1, 07/19/2018) further in view of NADAL ROURA (NADAL ROURA et al., US 2019134532 A1, 05/09/2019).
The methods VENTURINI DEL GRECO has been discussed supra and does not disclose the methods of claims 33-38.
The reference Black teaches “One aspect of the technology is directed to a tetrahydrocannabinol concentrate composition comprising about 0.3 to about 20 wt. %, about 0.5 to about 20 wt. %, about 1 to about 20 wt. %, or about 1 to about 15 wt. % tetrahydrocannabinol. The composition may further comprise about 5 to about 25 wt. %, or about 10 to about 20 wt. % fatty acids and terpenes and/or about 10 to about 95 wt. % cannabinoids selected from the group comprising cannabidiol, Cannabigerol, Cannabichromene, Cannabicyclol, Cannabinol, Cannabivarin, delta-9 Tetrahydrocannabinolic acid, Tetrahydrocannabivarin, Cannabidiolic acid, Cannabigerolic acid, Cannabidivarin, Cannabichromevarin, Cannabigerovarin, Cannabigerol Monomethyl Ether and combination thereof. The concentrate may be an oil or a powder.”[0032]. Since the weight % can add to 100% and no solvent is stated less than 1ppm is also covered. This helps to teach claims 33.
The reference Black does not teach the specific percentages of the instant claims 33, however, they are included in the stated ranges.
The reference NADAL ROURA teaches “In order to decarboxylate CBGA to CBG, 150 g of Cannabis sativa L. of the Carma variety, with CBGA as predominant, was decarboxylated by heating at 120° C. for two hours. A subsequent maceration was carried out in 750 mL of hexane for one hour (X3). The plant material was filtered, the hexane evaporated down to a volume of 100 mL, and then incubated 4° C. for 24 hours in order to crystallize the CBG “raw” material. The CBG “raw” material was vacuum filtered and the collected mother liquors evaporated to a volume of 30 mL to 50 mL and then incubated at 4° C. for 24 hours in order to crystalize the CBG. The amount of CBG obtained in this two-step process depends on the concentration of CBG in the starting plant material. The CBG obtained was recrystallized with 5 mL of hexane per gram of CBG two or three more times to obtain CBG with a purity between 95% and 98%”[0329] and “In one embodiment, the cannabinoid is THCA or THC. In another embodiment, the cannabinoid is CBDA or CBD. In another embodiment, the cannabinoid is CBGA or CBG” [0045]. This helps to teach claims 33, 34 and 36-37.
The reference NADAL ROURA also teaches “Another way to selectively manage or eliminate THC using a series of fractionating columns. Diverse chromatographic techniques have been used purify cannabinoid compounds from the plant Cannabis sativa. For example, Flash chromatography on silica gel, C8 or C18 ...”[0007]. This helps to teach claim 35.
The reference NADAL ROURA also teaches “Liquid formulations include suspensions, solutions, syrups and elixirs. Such formulations may be employed as fillers in soft or hard capsules and typically comprise a carrier, for example, water, ethanol, polyethylene glycol, propylene glycol, methylcellulose, or a suitable oil, and one or more emulsifying agents and/or suspending agents” [0118]. This helps to teach claim 38.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have taken the composition from Black and further purified it by the recrystallization procedure taught by NADAL ROURA this would have been obvious to do because Black teaches CBGA as part of the composition and NADAL ROURA teaches purification of CBGA. One would have been motivated to do so because increased purity caused by crystallization can remove potentially dangerous impurities. It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have used the purified product as suggested by VENTURINI DEL GRECO for the preparation of pharmaceutical or nutraceutical products, cosmetics, antimicrobial, antibacterial, insecticidal or biopesticides (instant claim 38) because the reference teaches that the cannabinoid extract can be used for such purposes and one would be motivated to use it as such because a purer composition is less likely to have unforeseen complication due to impurities.
Response to Arguments
Applicant's arguments filed 08/27/2025 have been fully considered but they are not persuasive.
The applicant argues the following:
“Raber fails to provide any guidance that would allow a person of ordinary skill in the art to have selected conditions suitable for carrying out the disclosed processes without significant decarboxylation of extracted carboxylic acids.” The applicant also argues: “What is clear, therefore, is that Raber fails to explain what conditions can be used to achieve decarboxylation and what conditions can be used while avoiding (or at least minimizing) decarboxylation. As such, the various statements in Raber are no more than the expression of objectives with no real teaching about how to achieve those objectives.”
This argument was not found to be persuasive because Raber teaches decarboxylation is an optional step in the process done in a vacuum oven separate from the distillation processes. Raber teaches “ Optionally, heating in the vacuum oven is conducted under conditions of temperature and timing that can lead to decarboxylation of THC-acid to THC” [0068] and “Following vacuum oven treatment, the oil is then subject to distillation under a vacuum” [0070]. Thus it would be obvious to one of ordinary skill in the art to skip decarboxylation (oven step) to avoid decarboxylation. This is supported because Raber teaches distillation does not lead to significant decarboxylation despite high temperatures: “Also provided is the above method, wherein the non-solvent that is enriched in the chemical constituents comprises a first chemical constituent and a second constituent, wherein the step of volatilizing results in a volatilized fraction, and also results in the separation of the first chemical constituent from the second chemical constituent, wherein the volatilized fraction is relatively enriched in the first chemical constituent and relatively depleted in the second chemical constituent, and wherein the non-solvent that is enriched in the chemical constituents contains heat-decarboxylatable chemical constituents, and wherein the step of volatilization results in heat-induced decarboxylation of less than about 5% of the heat-decarboxylatable chemical constituents” [0024]. Thus this argument was not found persuasive.
The applicant also argues that the rejections fails to suggest "subjecting said lipid extract to a vacuum distillation, wherein said vacuum distillation is carried out at a temperature in the range from 120 'C to 260 'C and at a pressure below 0.04 mbar" as recited in claim 1, where the lipid extract contains "cannabinoid acids in an amount of at least 20% by weight on total cannabinoids weight".
This argument was not found persuasive because Raber teaches distillation under a vacuum with temperatures in this range [0070] and pressure in this range [0069, 1 atm ~ 1 bar conversion]. It would have been obvious to one of ordinary skill in the art that one could achieve "cannabinoid acids in an amount of at least 20% by weight on total cannabinoids weight" since the refence teaches starting extract of 30% cannabinoid acids and wherein the step of volatilization results in heat-induced decarboxylation of less than about 5% of the heat-decarboxylatable chemical constituents [0024].
The applicant also argues that Raber teaches away from the instant invention because:
Indeed, Raber explicitly teaches away from the recited process of claim 1. Raber explicitly asserts:
[I]t is preferred to perform heat-induced decarboxylation on the non-solvent
extract, because the extract has a smaller volume than the plant matter, and
also because the presence of plant matter is expected to generate off-flavors or
off-odors. Heat-induced decarboxylation is preferably conducted before
distillation (or other process step involving pressure and heating), because
any decarboxylation that occurs inside a distillation apparatus could disrupt
the vacuum, resulting in inefficient distillation, for example, taking the form
of bumping.
This argument was not found persuasive because Raber from context also states “Heat-induced decarboxylation can be performed on non-extracted plant matter”[0113] and so is not arguing against using the decarboxylation step as suggested by the applicant but simply arguing that if the decarboxylation step is to occur it is preferred to occur on the smaller volume of plant matter because it will be easier and smell better and should occur before distillation to avoid some additional bumping by the small amount that could be generated in the distillation setup.
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The applicant also argues:
This was not found to be persuasive because it is not unexpected with the teaches of Raber. This argument was not found to be persuasive because Raber teaches decarboxylation is an optional step in the process done in a vacuum oven separate from the distillation processes. Raber teaches “ Optionally, heating in the vacuum oven is conducted under conditions of temperature and timing that can lead to decarboxylation of THC-acid to THC” [0068] and “Following vacuum oven treatment, the oil is then subject to distillation under a vacuum” [0070]. Thus it would be obvious to one of ordinary skill in the art to skip decarboxylation (oven step) to avoid decarboxylation. This is supported because Raber teaches distillation does not lead to significant decarboxylation despite high temperatures: “Also provided is the above method, wherein the non-solvent that is enriched in the chemical constituents comprises a first chemical constituent and a second constituent, wherein the step of volatilizing results in a volatilized fraction, and also results in the separation of the first chemical constituent from the second chemical constituent, wherein the volatilized fraction is relatively enriched in the first chemical constituent and relatively depleted in the second chemical constituent, and wherein the non-solvent that is enriched in the chemical constituents contains heat-decarboxylatable chemical constituents, and wherein the step of volatilization results in heat-induced decarboxylation of less than about 5% of the heat-decarboxylatable chemical constituents” [0024]. Thus this argument was not found persuasive.
Applicant submits that a person of ordinary skill in the art would have lacked a rational basis for combining Raber and Farokhi, and certainly would have lacked a reasonable expectation of success given the incompatibility of the Raber and Farokhi processes... In other words, Raber requires that the lipid used for extraction of chemicals from plants be a non-solvent for the chemical constituents, while Farokhi requires that the fatty acid be a solvent.
This argument was not found to be persuasive because both references teach lipids for the same purpose of extracting cannabinoid from plants and so one of ordinary skill in the art would just see these as alternative for the same purpose. Farokhi was used to teach distillation after lipid extraction (claim 1) and the high concentration of the acids in the concentrate (claims 8 and 9) and Raber teaches distillation after lipid extraction as well as further purification [0124] and so one would have a reasonable expectation of success.
The applicant argues that: In making this rejection, the PTO asserts at pages 21-22 of the Office Action that "[i]t would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the steps in Raber and Farokhi previously discussed to be obvious for the lipid extraction before distillation with the initial lipid extract provided by the steps of Venturini del Greco because Raber uses a lipid extract of cannabinoids and Venturini del Greco provides a lipid extract of cannabinoids and one would be motivated to do so because the steps are being used for the same purpose of purifying cannabinoids without solvents." As discussed above with respect to the preceding rejection, the latter statement is false because Farokhi explicitly recites the use of a fatty acid solvent. Thus, the solvents of each of Raber, Farokhi, and Venturini are incompatible with one another. Therefore, a person or ordinary skill in the art would have lacked any rational basis to combine the teachings of Raber, Farokhi, and Venturini.
This argument was not found persuasive because the non-solvent method was used as a motivation as to why one would want to combine the references not as the reason one would find it obvious to combine the methods. The reason one would be motivated to do so need not come form all the references to be true. The reason one would combine the references was given as they are all provide a lipid extract of cannabinoids.
The applicant argues: While Nadal Roura teaches methods of purifying one or more cannabinoids from a plant material, as acknowledged by the PTO at page 24 of the Office Action, Nadal Roura teaches a method that involves decarboxylation. Because such a teaching is contrary to the claimed subject matter, a person of ordinary skill in the art would have lacked a rational basis to combine Nadal Roura with Black and Venturini, which describe different systems for extraction.
This argument was not found persuasive because the reason for combining these references was not based on the fact that Nadal Roura teaches a method that involves decarboxylation instead all of these references teach cannabinoid compounds and so it would have been obvious to combine the references for the purification steps for cannabinoid compounds as taught by Nadal Roura. Nadal Roura teaches both the acid and the non-acid as embodiments of cannabinoids [0045] and their recrystallization [0014]. Thus one of ordinary skill in the art would also understand that the crystallization taught methods could also be done on acid cannabinoids.
Moreover, Applicant respectfully submits that the combination of Black, Venturini and Nadal Roura-even if such combination is proper (which Applicant does not admit)-fails to teach or suggest the steps of providing, mixing, adjusting, and separating as recited in claims 33 as well as the steps of providing and compounding as recited in claim 38.
This argument was not found persuasive because Nadal Roura provides both the acid and the non-acid as embodiments of cannabinoids [0045] and their recrystallization and concentrates [0014] and teaches an example which would be obvious to try for the acid version of the cannabinoids as well “A subsequent maceration was carried out in 750 mL of hexane [mixing] for one hour (X3). The plant material was filtered, the hexane evaporated down to a volume of 100 mL, and then incubated 4° C. for 24 hours [adjusting] in order to crystallize the CBG “raw” material. The CBG “raw” material was vacuum filtered and the collected mother liquors evaporated [separating] to a volume of 30 mL to 50 mL and then incubated at 4° C. for 24 hours in order to crystalize the CBG. The amount of CBG obtained in this two-step process depends on the concentration of CBG in the starting plant material. The CBG obtained was recrystallized with 5 mL of hexane per gram of CBG two or three more times to obtain CBG with a purity between 95% and 98%”[0329]. This helps to teach claim 33. As for claim 38, Nadal Roura provides both the acid and the non-acid as embodiments of cannabinoids [0045] and their recrystallization and concentrates [0014] and adding a pharmaceutically acceptable carrier [0118].
Conclusion
Claims 1-6, 8-29, and 33-38 are rejected.
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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/A.A.S./ Examiner, Art Unit 1627 /Kortney L. Klinkel/Supervisory Patent Examiner, Art Unit 1627