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 .
Election/Restrictions
Applicant’s election without traverse of R = alkyl in the reply filed on 02/04/2026 is acknowledged.
In accordance with the MPEP, 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 and the claims drawn to the elected species are allowable, the search of the Markush-type claim will be extended (see MPEP 803.02). 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 reexamined. Id. The prior art search will be extended to the extent necessary to determine patentability of the Markush-type claim. Id. In the event prior art is found during reexamination that renders obvious or anticipates the amended Markush-type claim, the claim will be rejected and the action made final. Id.
Applicants' elected species of R = alkyl does not appear allowable, therefore the search and examination of the claims has not been extended beyond the elected species (see the following 35 USC 103(a) rejection).
Priority
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Information Disclosure Statement
The information disclosure statement filed 02/06/2024 fails to comply with 37 CFR 1.98(a)(2), which requires a legible copy of each cited foreign patent document; each non-patent literature publication or that portion which caused it to be listed; and all other information or that portion which caused it to be listed. Specifically, a copy of the non-patent literature publication has not been provided. Thus, the has been placed in the application file, but the non-patent literature publication referred to therein has not been considered.
Claim Objections
Claims 1-20 are not in proper Markush format. See MPEP 2173.05 (h) which states that Markush type claim recites alternatives in a format such as “selected from the group consisting of A, B and C.” See Ex parte Markush, 1925 C.D. 126 (Comm’r Pat. 1925), MPEP 803.02. The claims do not contain the phrase “or” between the final two species, or recite “selected from the group consisting of” in the preamble of the claim. Appropriate correction is required.
Claim 1 recites R comprises an alkyl group, a phenyl group, etc. The transitional term “comprising”, which is synonymous with “including,” “containing,” or “characterized by,” is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. See, e.g., Mars Inc. v. H.J. Heinz Co., 377 F.3d 1369, 1376, 71 USPQ2d 1837, 1843 (Fed. Cir. 2004) (“like the term ‘comprising,’ the terms ‘containing’ and ‘mixture’ are open-ended.”). Invitrogen Corp. v. Biocrest Manufacturing, L.P., 327 F.3d 1364, 1368, 66 USPQ2d 1631, 1634 (Fed. Cir. 2003) (“The transition ‘comprising’ in a method claim indicates that the claim is open-ended and allows for additional steps.”); Genentech, Inc. v. Chiron Corp., 112 F.3d 495, 501, 42 USPQ2d 1608, 1613 (Fed. Cir. 1997). The definition for R implies that there can be numerous other substituents beyond what is found in R. However, it appears applicants intend for the claim to state that R is an alkyl group, a phenyl group, a benzyl group, etc. Further, claim 17 recites “wherein the terpene comprises (1S, 4R)-1-methyl-4-(prop-1-en-2-yl)cyclone-2-enol and/or cis-Verbenol. However the Specification only shows that (1S, 4R)-1-methyl-4-(prop-1-en-2-yl)cyclone-2-enol and cis-Verbenol are converted to a cannabidivarin.
Additionally, claim 8 recites that the Lewis base comprises 4-dimethylamino pyridine, imidazole, pyrrole etc. Claim 9 recites “wherein the alkyl amine comprises N, N-diisopropylethylamine, tert-butylamine, etc”. Claim 10 recites “wherein a protecting group comprises acetyl, 2-nosyl, 3-nosyl, 4-nosyl, etc”. Claim 11 recites “wherein the alcohol comprises methanol, ethanol, isopropyl alcohol, etc”. Claim 18 recites “wherein the acid comprises a Bronsted acid or a Lewis acid”. Claim 19 recites “wherein the acid comprises p-toluenesulfonic acid, hydrochloric acid, etc”. Claim 20 recites “wherein the cannabinol derivative comprises cannabivarin”.
The Examiner recommends amending the claims to recite “is selected from the group consisting of” in place of “comprises” to overcome the objections. Since claims 2-7 and 11-16 do not resolve the issue, so they are included in the objection.
Further claim 9 recites that the alkyl amine comprises methyl, pyridine. However neither methyl or pyridine is an alkyl amine. Appropriate correction is required.
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 1-20 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 applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 1 recites the limitation “A process for the preparation of cannabinol or derivative thereof” as well as “tetrahydrocannabinol or a derivative thereof”. Claim 2 recites “tetrahydrocannabinol derivative”. Claim 16 recites “contacting divarin or derivative thereof” as well as “to generate the tetrahydrocannabivarin or a derivative thereof”. Claim 20 recites “wherein the cannabinol derivative comprises cannabivarin”. However, the specification fails to limit or clearly delineate what can be considered a "derivative." According to Hackh's chemical dictionary, "derivative" is defined as a compound, usually organic obtained from another compound by a simple chemical process or an organic compound containing a structural radical similar to that from which it is derived (Hackh's chemical dictionary, 1972). Multiple derivatives of a cannabinol, tetrahydrocannabinol or divarin compound having various functional groups and chemical reactivity are encompassed by the instant claims. The “derivatives” of cannabinol, tetrahydrocannabinol, or divarin compound are not defined by a structural formula so as to know the metes and bounds of the claims. Such language fails to clearly define the subject matter being claimed.
The rejection over claim 1 could be overcome by inserting “A process for the preparation of cannabinol of formula I” with the structural formula in claim 1 and deleting the other instances of the term “derivative” in claim 1. The rejection over claims 2, 16 and 20 could be overcome by deleting the terms “derivative” found in the claims. As claim 3-15 and 17-19 do not fix the issue, they have been rejected as well.
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
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
US 2023/0002341, filed 06/14/2022 also teach conversion of tetrahydrocannabinol to cannabidiol using sulfur.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan can be reached at 571-270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623