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 .
Detailed Action
Filing Receipt and Priority
The filing receipt mailed 08/17/2023 states the instant application is a 371 of PCT/US2021/052844, filed 09/30/2021, which claims benefit of provisional application 63/086,653, filed 10/02/2020.
The instant applications find support in the provisional application. Therefore, the effective filing date is 10/02/2020.
Response to Amendments
The amendments made to the claims have been entered.
Claims 12 and 13, which were withdrawn in the prior office action have been canceled.
In view of the amendments made to the claims, the objection and 112(b) rejection made in the prior office have been withdrawn.
Status of claims
Claims under examination are claims 1-11 and 18.
Response to Arguments
In view of the arguments made in the remarks submitted 02/18/2026, the 112(a) scope of enablement rejection and written description rejections have been withdrawn.
Applicant has persuasively shown that the claimed electrochemical process relies on iodine to convert the cycloalkene ring system to aromatic ring system as shown in Jagtap (cited in prior office action) and the iodine is then regenerated electrochemically.
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.
KSR Rationales
The MPEP in section 2143, subsection I gives examples of Rationales for supporting a conclusion of obviousness. These rationales are non-exhaustive and include (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; (D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results; (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success; (F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art; (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.
Claim(s) 1-3 is/are rejected under 35 U.S.C. 103 as being unpatentable over Berkowitz (WO2020/041321, international filing date 08/20/2019) in view of Jagtap (WO2020/031179, published 02/13/2020, of the record) and Liu (Org. Biomol. Chem., 2018, 16, 2375-2387).
Claim 1 is drawn to a process of preparation of product compound 5 comprised of i) providing a first intermediate 8, treating the first intermediate 8 with iodine in an inert solvent to provide aromatized intermediate 9, then hydrolyzing aromatized intermediate 9 to provide compound 5 or, ii) alternatively, hydrolyzing the first intermediate of formula 8 to provide a second intermediate of formula 10, then treating the second intermediate of formula 10 with iodine in inert solvent to provide compound 5. Compounds are shown below.
Compounds of claim 1
PNG
media_image1.png
130
126
media_image1.png
Greyscale
,
PNG
media_image2.png
130
138
media_image2.png
Greyscale
PNG
media_image3.png
130
128
media_image3.png
Greyscale
,
PNG
media_image4.png
128
118
media_image4.png
Greyscale
.
Dependent claims 2-3 are drawn to embodiments of claim 1 wherein the step of treating the first intermediate is carried out using iodine in toluene at reflux.
Berkowitz on p. 41 teaches Scheme 1 which shows a synthetic route to compound 7 (tetrahydrocannabinol, THC).
Berkowitz, Scheme 1
PNG
media_image5.png
352
590
media_image5.png
Greyscale
Berkowitz on p. 49 states “The synthetic methods in Schemes 1, 2, 3, 4, and 5 are suitable for use on a large scale and for manufacturing purposes particularly since the key cyclization reactions in the invention do not give rise to unwanted isomeric side product. Examples of known cannabinoids that are available using the synthetic routes are cannabidiol (11), cannabidivarin (12), Δ9-tetrahydrocannabinol (7) tetrahydrocannabivarin (9) and compounds related to Nabilone (16).”
Compound 27 of Berkowitz above embraces instant intermediate 8.
Additionally, Berkowitz in its specification contemplates similar molecules. Berkowitz on p. 12-13 states “The synthetic methods are also suitable for synthesis of other know and novel cannabinoids and these compounds are also part of the invention. The cannabinoids 1 below, which are novel analogs of cannabidiol (11) and cannabidivarin (12) are also available by the synthetic routes herein described and are part of the invention.” The full compounds are represented by the formula 1 (above):
This listing of possible substituents matches those of the instant claims.
Berkowitz on p. 68-69, Example 4 also teaches hydrolyzation and decarboxylation of a protected cannabidiol to unprotected and decarboxylated cannabidiol.
PNG
media_image6.png
192
426
media_image6.png
Greyscale
Berkowitz does not teach a step of refluxing a compound with iodine in an inert solvent. This is addressed by the combination of Jagtap.
Jagtap on p. 35, teaches Scheme 7 shown below which shows a step of converting cannabidiol to CBN.
Jagtap, Scheme 7
PNG
media_image7.png
368
558
media_image7.png
Greyscale
.
Jagtap on p. 32, Example 4 teaches that the conversion of CBD to CBN (above) was carried out in toluene and with the addition of iodine.
Berkowitz teaches compounds 27. Jagtap teaches the step of converting CBD to CBN (represented by instant formula 5) via refluxing CBD with iodine in toluene. While the scheme in Jagtap is applied to compounds that are different from those in Berkowitz, the critical bond formation and aromatization are taught by Jagtap. The final steps to reach product 5 are taught by Berkowitz in example 4, shown above. The combination of Berkowitz with Jagtap amounts to applying a known method to a known product to yield a predictable result.
Therefore, the instant claims would have been prima facie obvious to one of ordinary skill in the art at the time of the effective filing date. One of ordinary skill would find motivation to make the combination as Jagtap disclose a method that would yield a predictable product from compounds and methods of Berkowitz.
Response to Arguments
Applicant’s remarks state that the claims have been amended to “remove aromatization reactions of intermediate 10 (RA is H, CO2H) using iodine alone.” These amendments do not address where Berkowitz and Jagtap in combination make obvious the conversion of intermediate 8 to intermediate 9.
New Rejections
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 1-11 and 18 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 refers to the following compound 10 as both “first intermediate” and “second intermediate” where it states “providing a first intermediate of formula 10 or its diastereoisomer or enantiomer; wherein RA is H, CO2H or its diastereoisomer or enantiomer, and treating the second intermediate of formula 10…” As claims 2-11 and 18 are dependent on claim 1 they are also rejected.
This new rejection has been necessitated by amendments made to the claim.
Conclusion
No claims allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
Applicant's amendment necessitated a new ground(s) of rejection presented in this Office action.
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 LUISALBERTO GONZALEZ whose telephone number is (571)272-1154. The examiner can normally be reached M-F 8:30-5:30.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/L.G./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
Prosecution Insights