DETAILED ACTION
Claims 1-20 are currently pending in the instant application.
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 .
Information Disclosure Statement
Applicant's Information Disclosure Statement filed on 04/16/2026 has been considered. Please refer to Applicant's copies of the 1449 submitted herewith.
Response to Amendment/Arguments
Applicant's amendments and arguments in a response filed 07/24/2026 have been fully considered and entered into the application. Applicant has overcome
The objection to claims 1-20.
The 35 U.S.C. 112(b) rejection of claims 1-20 in view of Applicant’s amendments.
Regarding the 35 U.S.C. 103 rejections, Applicant argues that Duchek does not contact a crude cannabinol product with a protecting group compound to generate a protected cannabinol which is then deprotected and Duchek begins with a pure cannabinol starting material and cites the abstract which states aryl sulfonic THC esters (protected cannabinols) are highly crystalline. Applicant states that Duchek teaches purification of protected cannabinol products by recrystallization and does not disclose or suggest protecting/deprotection as means for protecting cannabinol products. However, on p. 4, Duchek specifically teaches that impure cannabinoids can be treated with at least one aryl sulfonyl halide in the presence of at least one base to cause reaction at the phenol hydroxy group thereby producing aryl sulfonates. Thus contrary to Applicant’s allegation, Duchek teaches contacting impure cannabinoids with aryl sulfonyl halide to protect said cannabinoid. Further on p. 6, reaction 2 of Duchek cited in the original reaction teaches deprotection of the arylsulfonyl halide to give the pure cannabinoid. Although Duchek teaches recrystallization of the protected cannabinols, Duchek also teaches protecting/deprotection of cannabinol, contrary to Applicant’s allegation as described in the original rejection.
Further Applicant argues that the goal of Siegel’s teachings is to produce ∆9-tetrahydrocannabinol although CBN is produced and thus Siegel teaches away from the production of CBN. However, MPEP 2123, Section I states “The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned. They are part of the literature of the art, relevant for all they contain.” In re Heck, 699 F.2d 1331, 1332-33, 216 USPQ 1038, 1039 (Fed. Cir. 1983) (quoting In re Lemelson, 397 F.2d 1006, 1009, 158 USPQ 275, 277 (CCPA 1968)). A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Merck & Co. v.Biocraft Labs., Inc. 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989), cert. denied, 493 U.S. 975 (1989). See also Upsher-Smith Labs. v. Pamlab, LLC, 412 F.3d 1319, 1323, 75 USPQ2d 1213, 1215 (Fed. Cir. 2005). Further MPEP 2123, Section II states that Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments. In re Susi, 440 F.2d 442, 169 USPQ 423 (CCPA 1971). “A known or obvious composition does not become patentable simply because it has been described as somewhat inferior to some other product for the same use.” In re Gurley, 27 F.3d 551, 554, 31 USPQ2d 1130, 1132 (Fed. Cir. 1994). Thus, since Siegel teaches limitations that read on the instant claims, the rejections have been maintained.
Maintained 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.
Claims 1-15 are rejected under 35 U.S.C. 103 as being unpatentable over SIEGEL (see US Pat. No. 10,894,780, issued 01/19/2021) as applied to claims 1-15 above, and further in view of DUCHEK (see WO 2004/043946, pub. 05/27/2004, reference cited in IDS filed 02/06/2024).
SIEGEL teaches conversion of tetrahydrocannabinol to cannabidiol
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- see drawing occurs in the presence of a catalyst, which is taught to be sulfur – see col. 3, line 17. SIEGEL teaches adding sulfur to tetrahydrocannabinol at a ratio of least 2 mol - 0.001 mol sulfur to THC (see claim 6) and heating the reaction above 130 ºC (see col. 2, lines 7-12) and specifically between 125 to 300 ºC (see claim 10). The crude product is taught to be purified using distillation (see col 6, Example 5). SIEGEL does not teach contacting the crude cannabinol product with a protecting group and then contacting the protected-cannabinol with a metal hydroxide and alcohol to generate a cannabinol of formula I.
DUCHEK teaches purification of cannabinoids by contacting a cannabinoid with an aryl sulfonyl halide in the presence of a base, specifically a tertiary amine (see p. 4) at room temperature -
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(see p. 3) wherein Y is an aryl. Further the aryl is taught to be benzene, alkyl substituted benzene, nitrobenzene, substituted and unsubstituted naphthyl compounds (see claim 21, p. 17). This product can then be crystallized (see p. 5, 1st paragraph) and then hydrolyzed with base comprising a metal salt of an alkyl oxide in an alkyl alcohol -
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(see p. 6). DUCHEK names potassium t-butoxide in t-butanol, which reads on claims 11 and 14. Regarding claims 7-9, DUCHEK teaches that the base is needed to cause reaction at the phenol hydroxy group, thereby producing the aryl sulfonate and any suitable base that does not interfere with the esterification reaction may be used (see p. 4, lines 1-5). DUCHEK teaches the tertiary amine is represented by formula R5R6R7 wherein R5, R6, and R7 are alkyl groups. DUCHEK teaches hydrolysis of the protected cannabinoid at 40 ºC rather than room temperature. According to MPEP 2144.05, Section II, Part A, generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382 ("The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages."); In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969). Therefore, the adjustment of particular conventional working conditions (e.g. determining result effective amounts of the ingredients beneficially taught by the cited references), as well as adjustment of reaction temperature, reaction time and use of solvents, rearranging steps in a reaction sequence, is deemed merely a matter of judicious selection and routine optimization which is well within the purview of the skilled artisan (See In re Mostovych, Weber, Mitchell and Aulbach, 144 USPQ 38).
Thus, it would be obvious to apply the teachings of DUCHEK to SIEGEL in order to improve the purity of the product of SIEGEL. DUCHEK teaches esterification of a cannabinoid followed by deprotection as an improved method for purifying cannabinols that also allows for increased ease in handling and stable storage ability. One would be motivated to subject the product of SIEGEL to improved purification methods as taught for DUCHEK in order to improve purification and/or for improved storage of the cannabinoid compounds.
Claims 1 and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over SIEGEL (see US Pat. No. 10,894,780, issued 01/19/2021) and DUCHEK (see WO 2004/043946, pub. 05/27/2004, reference cited in IDS filed 02/06/2024) as applied to claim 1 above, and further in view of OHLER (see WO 2021/163042, pub. 08/19/2021) and Bloemendal et al (see Org. Biomol. Chem., 2020, Vol. 18, p. 3203-3215).
The limitations of claim 1 are taught as discussed above.
OHLER teaches that reaction of an aromatic polyketide with a terpene provides a cannabinoid (see p. 27). Specifically the cannabinoid may be cannabidivarin (CBNV, see p. 18-19) and the aromatic polyketide is divarin (see p. 28). The reaction may be catalyzed by a Bronstead or Lewis acid such as p-toluene sulfonic acid or BF3 etherate (see p. 18). OHLER does not teach verbenol as the terpene. Bloemendal et al teaches that several terpenoid may be used to synthesize tetrahydrocannabinol (see FIG. 1, p, 3205) and exemplifies olivetol may be reacted with verbenol in presence of p-TSA or boron trifluoride to provide tetrahydrocannabinol
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(see p. 3205). Thus, one of ordinary skill in the art would have been motivated to substitute the appropriate aromatic polyketide, such as divarin, which has a propyl rather than a pentyl alkyl side chain could be reacted with a terpene such as verbenol in the presence of acid in order to provide the desired cannabidivarin or tetrahydrocannabivarin as taught by OHLER.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAREN CHENG whose telephone number is (703)756-4699. The examiner can normally be reached M-F, 9AM-6PM PST.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ANAND U DESAI/Supervisory Patent Examiner, Art Unit 1655
