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 .
Status of the Claims
A preliminary amendment has not been filed. Thus claims 1-12 filed on 03/12/2024 are currently pending and are under examination.
Claim Objections
Claims 1 and 10 are objected to because of the following informalities: DMC (line 2 in both claims) should be preceded by the full name to recite “double metal cyanide (DMC)”.
Claim 1 is objected to because of the following informalities: replace the period “.” sign in line 2 with a comma “,” sign.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 8 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 8:
The parenthetical limitation "(POE)" renders the claim indefinite because it is unclear whether “POE” is part of the claimed invention. See MPEP § 2173.05(d).
The acronym (POE) is not clear what it stands for and thus renders the claim vague and indefinite. For purpose of examination, (POE) is interpreted in view of the specification, i.e. polyoxyethylene.
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.
Claims 1-4 and 6-12 are rejected under 35 U.S.C. 103 as being unpatentable over Gerlach (Gerlach, C. D. et al. Patent application publication number US20220153670A1; effectively filed on Nov. 16, 2020) in view of McDaniel (McDaniel, K. G. et al. Patent application publication number US2008/0132728A1; cited in IDS 03/12/2024).
Regarding claims 1-4 and 10, Gerlach teaches that cannabinoids have very low water solubility and that an emulsifier system must be used to incorporate CBD into a water-based formulations, such as cosmetic formulations ([0005]). Gerlach thus teaches a method for preparing an alkoxylated cannabinoid (an emulsifier which is the poly(alkyleneoxide) ethers of cannabinoids) by the reaction of ethylene oxide (EO) or propylene oxide (PO) with a cannabinoid and particularly CBD ([0017]). The reference further teaches that more EO will make the resulting emulsifier more water soluble and adjust its emulsifying power and using CBD as the representative hydrophobe of the emulsifier ensures excellent compatibility with the native compound or free CBD oil ([0017]). Gerlach further teaches that the reaction of CBD isolate is conducted in the presence of KOH catalyst ([0046]).
Regarding claims 11-12, Gerlach is silent that the water solubility of the cannabinoid after alkoxylating is increased by at least about 5% or by at least about 100% as compared to the water solubility of the cannabinoid before alkoxylating. However, since Geralch teaches the same alkoxylated cannabinoid product as instant invention and that the solubility of alkoxylated cannabinoid in water is improved compared to cannabinoid before alkoxylation, the water solubility of the cannabinoid after alkoxylating in the reference is necessarily increased by at least about 5% or by at least about 100% as compared to the water solubility of the cannabinoid before alkoxylating.
Regarding claims 1 and 10, while Gerlach teaches the use of KOH catalyst, the reference fails to teach or suggest conducting the reaction in the presence of DMC isolate. The deficiency is however cured by McDaniel.
McDaniel teaches that alkyl and alkylaryl ethoxylates are produced via semi-batch processes utilizing base catalysis, typically potassium hydroxide (“KOH”) (same catalyst as Gerlach) ([0002]). The reference however discusses the disadvantages of using KOH:
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As such, McDaniel teaches an improved and continuous process for the production of alkylphenol ethoxylates in the presence of a double metal cyanide (“DMC”) catalyst ([0011]). The catalyst in the reactor has on-going activity and new catalyst is continually activated as the process proceeds ([0028]) and the conditions are established when the reactor temperature, ethylene oxide pressure, catalyst level, degree of catalyst activation, presence of oxyalkylatable compounds within the reactor, etc., are such that upon addition of unreacted ethylene oxide to the reactor, ethoxylation takes place ([0033]).
McDaniel teaches that the continuous processes also eliminate the nonproductive sequences required for the semi-batch process that uses KOH catalyst ([0028]). The reference further discusses in [0028] the advantages of using the continuous processes
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In view of the above advantages, a skilled artisan would have been motivated in using the process and DMC catalyst of McDaniel in the alkoxylation reaction of Gerlach’s cannabinoid and in place of KOH catalyst with a reasonable expectation of success in improving the productivity of alkoxylated cannabinoids.
Regarding claim 6, the catalyst concentration is preferably from 5 ppm to 1,000 ppm ([0032]).
Regarding claim 7, the preferred DMC catalyst used in McDaniel is zinc hexacyanocobaltate ([0031]).
Regarding claim 8, the instant specification describes POE as being equivalent to the molar ratio of ethylene oxide-to-cannabinoid (page 7, lines 27-29). McDaniel exemplifies the reaction of nonylphenol with ethylene oxide, in which 14.4 g/min of ethylene oxide and 15.2 g/min of nonylphenol have been charged to the reactor ([0041]). The amounts of ethylene oxide and nonylphenol are equivalent to 0.327 moles and 0.0690 moles, respectively, and thus the POE value is about 4.7 (calculated by 0.327moles/0.0690moles). It is noted here that nonylphenol has only one hydroxy group that is ethoxylated. However, most cannabinoids, and particularly CBD of Gerlach has two hydroxy groups and thus the ethylene oxide required would be twice the amount of that of McDaniel to obtain the ethoxylated CBD, i.e. a POE value of about 9.4 (4.7 x 2).
Regarding claim 9, the reaction is conducted at a temperature of 130° C ([0041]).
It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct
a process for preparing an alkoxylated cannabinoid comprising; (i) forming a mixture of a cannabinoid, an alkylene oxide and a DMC catalyst, and (ii) subjecting the mixture to conditions sufficient to activate the DMC catalyst and to alkoxylate the cannabinoid to form the alkoxylated cannabinoid; or
a method for increasing the water solubility of a cannabinoid comprising alkoxylating the cannabinoid in the presence of an alkylene oxide and a DMC catalyst
in view of the teachings of Gerlach and McDaniel.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Gerlach (Gerlach, C. D. et al. Patent application publication number US20220153670A1; effectively filed on Nov. 16, 2020) in view of McDaniel (McDaniel, K. G. et al. Patent application publication number US2008/0132728A1; cited in IDS 03/12/2024) as applied to claims 1-4 and 6-12 above, and further in view of Leanna Organics (Leanna Organics “Third Party Tested CBD” May 14, 2020; pages 1-7).
The teachings of Gerlach and McDaniel have been set forth above.
Regarding claim 5, Gerlach teaches the use of cannabinoid and in particular free CBD oil or CBD isolate ([0017] and [0046]), but fails to teach that the cannabinoid or the CBD isolate has a water content below about 1000 ppm. The deficiency is however cured by Leanna Organics as it teaches the commercial availability of CBD isolate at a purity of 99.99% before the effective filing date of the instant invention. Hence, if any water is present in the oil, the amount would be 100 ppm or less (calculated by [100%-99.99%] x 10,000). Accordingly, using the CBD isolate of Leanna Organics in the process of the combination of Gerlach and McDaniel would yield nothing more than the predictable alkoxylated CBD product.
It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a process for preparing an alkoxylated cannabinoid comprising; (i) forming a mixture of a cannabinoid, an alkylene oxide and a DMC catalyst, and (ii) subjecting the mixture to conditions sufficient to activate the DMC catalyst and to alkoxylate the cannabinoid to form the alkoxylated cannabinoid; wherein the cannabinoid has a water content below about 1000 ppm in view of the teachings of Gerlach, McDaniel and Leanna Organics.
Conclusion
Claims 1-12 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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