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 .
Claims 1-20 are currently pending.
Priority
The instant application claims priority as follows:
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Species Election requirement
Applicants’ election on July 10, 2025, without traverse, of “an acid reagent”, is acknowledged. The examiner contacted Applicant to request a complete reply to the species requirement, which would include the selection of a specific acid reagent and the claims readable on the elected acid reagent. On August 25, Applicant’s representative informed the examiner that Applicant would like to elect the species of acid PSSA (polystyrene sulfonic acid).
According to the specification at paragraph [0036], polymers such as PSSA are sterically hindered and insoluble in CBD. Thus, it appears that the elected species reads on claims 1-5, 7-10, 14-17 and 20.
Claims 6, 11-13, 18, 19 and subject matter outside of the examined scope are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on July 10, 2025.
Examination will begin with the elected species. In accordance with MPEP 803.02, if upon examination of the elected species, no prior art is found that would anticipate or render obvious the instant invention based on the elected species, the search of the Markush-type claim will be extended. If prior art is then found that anticipates or renders obvious the non-elected species, the Markush-type claim will be rejected. It should be noted that the prior art search will not be extended unnecessarily to cover all non-elected species. Should Applicant overcome the rejection by amending the claim, the amended claim will be examined again. The prior art search will be extended to the extent necessary to determine patentability of the Markush-type claim. In the event prior art is found during further examination that renders obvious or anticipates the amended Markush-type claim, the claim will be rejected and the action made final.
The elected species was searched in a conversion of CBD into THC and applicable art was identified. Therefore, the entire scope of claims 1-5, 7-10, 14-17 and 20 has not yet been examined in accordance with Markush search practice. See MPEP 803.02. Examination included the elected species PS-SO3 and sulfonic acid resins known as Amberlyst 15 and silica-sulfonic acids, found in the same reference.
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.
Claims 4, 14 and 15 are 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 pre-AIA the applicant regards as the invention.
In claim 4, the term “substantially pure” is indefinite. The specification discloses that “substantially” means “that differences between compared features or characteristics is less than 25% of the respective values/magnitudes in which the compared features or characteristics are measured and/or defined.” One cannot distinguish from things which are not substantially pure.
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“A sulfonation product of an aromatic ring” makes claim 14 ambiguous. One of ordinary skill in the art would not know the full range of products and structures included in the claim.
In claim 15, the elevated temperature is a relative term and is ambiguous. It could mean an elevated temperature from the generally considered standard room temperature between the range of 20°C to 23 °C. Or elevated from that of a laboratory temperature which could be between 15-25°C.
Claim 15 should also be corrected for the phrase “starting material starting material”.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1-2, 4-5, 7-10, 14 and 20 are rejected under 35 U.S.C. 102(a)(2) as being clearly anticipated by Nivorozhkin (US Patent 11,098,024 -effectively filed on Jan. 11, 2019).
The prior art teaches a method for producing THC from CBD in a manner that affords tunability to select the ratio of THC-8 to THC-9. See abstract. The method comprises introducing CBD to acidicly enriched solid support particles in a solvent-free environment, wherein the catalytic solid support particles that are acidicly enriched are selected from Amberlyst-15 resin beads, silica-sulfonic acid resins and others (at least column 5, lines 53-60, column 7, and claims). Amberlyst-15 is a polystyrene-supported sulfonic acid resin (column 9, lines 13-26). The reaction temperature is 100°C. The prior art further teaches that the THC produced may have a THC-8 bias of greater than 50%, or than 60% or than 90%, etc., and both THC-8 and THC-9 are produced. See the catalytic conversion of CBD to THC and THC-9 to THC-8 represented in Schemes 1 and 2. Seemingly, pure CBD can be used for these types of reaction (> 99% purity-Example 1) as well as isolates containing other cannabis compounds (column 15, lines 32-37). For Amberlyst-15 resin see Example 1: “A full catalytic conversion of CBD to THC-8 (78%) also took place by heating a commercial CBD isolate containing minor quantities of other cannabinoids and terpenes for 10h at 100°C.” (Col. 15) The prior art teaches that particular catalysts, longer reaction times and high temperature reactions favor production of THC-8 over THC-9. See all tables. A 5-minutes solvent free reaction catalyzed by Si-Sulfonic acids resins at 100°C favored THC-8 to THC-9 in a ratio of 21.3 to 1. See at least Table 2.
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“Surprisingly, the transformation is significantly accelerated when conducted in the melt, without any solvent. See column 18, lines 39-41.
Claim Rejections - 35 USC § 103
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.
Claim(s) 1-5, 7-10, 14-17 and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Nivorozhkin (US Patent 11,098,024- as above), in view of Zhang et al. (Nat Commun 5, 3170 (2014)), Kiss et al. (Ind. Eng. Chem. Res. 2019, 58, 5909-5918) and Adair (US 2022/0220090A1).
Determining the scope and content of the Prior art (MPEP §2141.012)
Teachings of Nivorozhkin (US Patent 11,098,024-as above)
Nivorozhkin teaches a method for producing THC from CBD in a manner that affords tunability to select the ratio of THC-8 to THC-9. The method comprises introducing CBD to acidicly enriched solid support particles in a solvent-free environment (see at least the abstract and columns 12-14).
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The catalytic solid support particles that are acidicly enriched are selected from Amberlyst-15 resin beads and others (at least column 5, lines 53-60, column 9, lines 13-26, and Table 1).
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Amberlyst-15 is a polystyrene-supported sulfonic acid resin.
The reaction temperature may be 100°C. The prior art further teaches that the THC produced may have a THC-8 bias of greater than 50%, or than 60% or than 90%, etc., and both THC-8 and THC-9 are produced. See the catalytic conversion of CBD to both THC isomers and THC-9 to THC-8 represented in Schemes 1 and 2. Seemingly, pure CBD can be used for these types of reaction (> 99% purity-Example 1) as well as isolates containing other cannabis compounds (column 15, lines 32-37). For Amberlyst-15 resin see Example 1: CBD is converted to THC-8 in 85% yield using Amberlyst-15 resin in heptane solvent (Example 1). “A full catalytic conversion of CBD to THC-8 (78%) also took place by heating a commercial CBD isolate containing minor quantities of other cannabinoids and terpenes for 10h at 100°C.” (Col. 15) The prior art teaches that particular catalysts, longer reaction times and high temperature reactions increase the production of THC-8 over THC-9. The use of Amberlyst-15 catalyst (polystyrene-based sulfonic acid) favors the production of THC-8 from CBD and converts THC-9 into THC-8. The use of silica-sulfonic acid resins at elevated temperatures favors THC-8 formation. A solvent-free reaction catalyzed by Si-Sulfonic acids resins at 100°C favored THC-8 to THC-9 in a ratio of 21.3 to 1, even if run for only 5 minutes.
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Clearly, high temperatures and prolonged reaction times favor production of THC-8 over THC-9. See all tables. “Surprisingly, the transformation is significantly accelerated when conducted in the melt, without any solvent. Using aluminosilicates helps to stabilize THC-9 vs. THC-8.” See column 18, lines 39-44.
Teachings of Adair (US2022/0220090)
The prior art reports that the ability to convert CBD into primarily Δ9-THC and/or compositions of various Δ9-THC:Δ8-THC ratios greater than 1.0:1.0 is associated with the utilization of Lewis-acidic heterogeneous reagents under aprotic or neat reaction conditions in which reaction temperature and reaction time parameters are carefully selected and controlled. In particular, the examples of the prior art disclosure “indicate that for either neat reaction conditions or reactions in aprotic-solvent systems, mild reaction temperatures and short reaction times favor the formation of Δ9-THC over Δ8-THC and that the properties of the Lewis-acidic heterogeneous reagent affect the selection of such reaction conditions.” See paragraph [0024].
Example 1 (E11) shows that the use of catalyst ZSM-5 at 60°C for 18 hours gives THC-9 as the major product, however, ZSM-5 at 80°C for 18 hours gives THC-8 as the major product (Example CE1). Moreover, Amberlyst-15 (a styrene-divinylbenzene sulfonic acid resin) provides mostly THC-8 even at a lower temperature (60°C) and short reaction time (only 2 hours) (Example CE2). Neat reaction conditions using ZSM at 100°C gives THC-9 as the major product only if it’s a 30 minutes reaction (Example E2); and an 18-hour reaction provided THC-8 in much higher amounts (Example CE3). See the trend in Table 2.
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Teachings of Zhang et al.
Zhang disclosed the preparation of polystyrene sulphonic acid resins (PS-SO3H) with enhanced acid strength to be used in acid-catalyzed reactions. This solid catalyst exhibits much higher activity than Amberlyst-15, and in some cases even higher than H2SO4, under similar reaction conditions. It is safer and more environmentally friendly than corrosive mineral acids. See at least page 2.
Teachings of Kiss et al.
Reactive distillation was developed since the early 1920s, and “is considered an established industrial unit operation”. The process is also known as catalytic distillation when a solid catalyst is used. Some of the many advantages of this technology are reduced capital investment and significant energy savings, as it can simplify complex processes, increase product selectivity, and improve separation efficiency. See the abstract and introduction.
Ascertainment of the Difference Between the Prior Art and the Claims
(MPEP §2141.012)
The difference between the teachings of Nivorozhkin and instant claim 3 is that Nivorozhkin did not mention “reactive distillation”.
The difference between the teachings of Nivorozhkin and instant claims 15-16 is that Nivorozhkin did not mention polystyrene sulfonic acid (PSSA) resins as the catalyst.
The difference between the teachings of Nivorozhkin and instant claim 17 is that Nivorozhkin did not mention polystyrene sulfonic acid (PSSA) resins and the ratio of THC-8 to THC-9 of between 50:1 and 1000:1.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
A person of ordinary skill in the art is a chemist practitioner with the level of skill of the authors of the above references. The ordinary skilled artisan would have been motivated to perform the reactions of Nivorozhkin as a reactive distillation process because of the many advantages of the very well-known technology, as taught by Kiss et al.
Regarding claims 15-17, the ordinary skilled artisan would have recognized that the polystyrene sulfonic acid (PSSA) resins of Zhang, the silica-sulfonic acid resins of Nivorozhkin and Amberlyst-15 resin have similar properties, are used in the same type of reactions, and are replaceable for one another. The starting materials, acid-catalyst resins, and products were all known. The claimed reaction has been previously disclosed. The instant application takes a known reaction and replaces its sulfonic acid catalyst resin, or styrene-based sulfonic acid catalyst (Amberlyst-15), for another styrene-based sulfonic acid catalyst (PSSA). Thus, one of ordinary skill would have been motivated to perform the reactions taught by Nivorozhkin, that is, in the melt to significantly accelerate the transformation, and at 100°C, with the catalyst polystyrene sulfonic acid (PSSA) resin of Zhang, with the expectation of obtaining high conversion of CBD into THC-8 and the benefits of using PSSA. Further motivation arises from that Zhang disclosed that PSSA exhibits much higher activity than Amberlyst-15.
Regarding the ratio of THC-8 to THC-9 of between 50:1 and 1000:1 of claim 17, the artisan would have known from the references that longer reaction times necessarily favor THC-8. Nivorozhkin disclosed that a solvent-free reaction catalyzed by silica-sulfonic acid resin at 100°C for only 5 minutes gave a THC-8 to THC-9 ratio of 21.3 to 1. Artisans interested in obtaining mostly THC-8 would have been motivated to use the catalyst polystyrene sulfonic acid (PSSA) resin of Zhang, which exhibits much higher activity, under Nivorozhkin reaction conditions and to allow the reaction to proceed for 1h, 1.5 h, 10h or 18h (per Nivorozhkin and Adair), and until the ratio of THC-8 to THC-9 would reach the desired ratio. This would consequently afford a ratio of 50:1 or larger.
Pursuant to the Supreme Court rationales in KSR International Co. v. Teleflex Inc., 550 U.S. 398, 127 S. Ct. 1727, 82 USPQ2d 1385, 1395-97 (2007), at least exemplary rationales (A), (B), (C) and (G) apply in this case:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Note to Applicants
Claims 1-5, 7-10, 14-17 and 20 are rejected.
Not every piece of prior art found in the search has been applied against the instant claims. See MPEP 904.03.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to VALERIE RODRIGUEZ-GARCIA whose telephone number is (571)270-5865. The examiner can normally be reached Monday-Friday 9:30am-4:30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Curtis Mayes can be reached at 571-272-1234. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/VALERIE RODRIGUEZ-GARCIA/Primary Examiner, Art Unit 1759 09/02/2025