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
Claims 23-24, 68-70, 73-74, and 76 are pending. Claim 68 is withdrawn. Claims 23-24, 69-70, 73-74 and 76 are rejected.
Response to Amendments/Arguments
Applicant’s amendments (particularly by adding the following to lines 2 and 3 of claim 69: “based on a molar quantity of the tetrahydrocannabidiol derivative of formula I”), filed 9/8/2026, with respect to the 112b rejection of claim 69 have been fully considered and are persuasive. The 112b rejection of claim 69 has been withdrawn. (The 112b rejection of claim 70 has been maintained because of the inclusion of “Raney nickel” in line 2).
Applicant's arguments and amendments, specifically regarding drawings filed 9/8/2026 have been fully considered but they are not persuasive. The drawings filing 9/8/2026 are still blurry and the objection is maintained below.
Applicant’s amendments and arguments (particularly the removal of the solvent “ethyl acetate”), filed 9/8/2026, with respect to the rejection(s) of claim(s) 23, 24, 69-71, 75 and 76 under 35 USC 103 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, as necessitated by amendment, a new ground(s) of rejection is made below. Arguments will be addressed here that are relevant to the 9/8/2026 amended claims.
On p. 6-7 of the response, Applicant argues that Lago-Fernandez does not render obvious the instant claims, particularly because Lago-Fernandez does not teach a solvent of the instant claims. This deficiency has been provided for below by Zhang in the amended 103 rejection.
On p. 7 of the response, Applicant argues that Zhou discloses formic acid/ammonium formate as a system used exclusively in an aqueous reaction medium. Examiner respectfully disagrees that this argument overcomes the findings of prima facie obviousness below. Because formic acid/ammonium formate was so successful and effective at generating hydrogen, a skilled artisan would have been motivate to explore its utility in a wide variety of systems, including organic solvents, with a reasonable expectation of success. Additionally, a combination of references is used below to render the claims obvious.
Drawings
The drawings submitted 9/8/2026 are objected to because they are blurry and difficult to read. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
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 70 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.
Claim 70 contains the trademark/trade name: “Raney nickel”. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a catalyst and, accordingly, the identification/description is indefinite. Examiner recommends removing trademark name.
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.
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.
Claim(s) 23-24, 69-70, 73-74 and 76 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lago-Fernandez et al. (Methods in Enzymology, 593, 2017, 237-257; disclosed on 11/5/2025 IDS), in view of Zhou et al. (International Journal of Hydrogen Energy, 41, 2016, 22059-22066), and further in view of Zhang et al. (J. Chem. Technol. Biotechnol. 1998, 72, 264-272).
Lago-Fernandez discloses the following on p. 241:
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The prior art compound 1 (CBD) is embraced by the instant claims Formula I:
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, wherein R = 5 (Applicant’s elected species is R = 3) and wherein the prior art pathway “ii” is applicable to that of the instant claims. Additionally, prior art compound 9 is embraced by instant claims Formula II:
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, wherein R = 5 (Applicant’s elected species is R = 3).
Lago-Fernandez fails to disclose a heating step, a hydrogen source specifically from ammonium formate and formic acid, and a solvent/catalyst combination of the instant claims. Zhou and Zhang provide for these deficiencies.
Zhou teaches the following: “The concentrated FA[formic acid]-AF[ammonium formate] mixture shows not only higher hydrogen evolution activity but also higher volumetric capacity than single FA, single AF….” (see conclusions, p. 22064).
Zhang explores catalysts and conditions used in the effective hydrogenation of cinnamaldehyde (see introduction, p. 265). “The Pd/C catalyst used can produce hydrocinnamaldehyde at a relatively high selectivity. A non-polar solvent, e.g. toluene was the better solvent while the polar solvent formed diacetals” (see conclusions, p. 272). The hydrogenation was performed at 273-343 K (equivalent to 0-70C) (see abstract, p. 264).
Regarding instant claims 23, 70, and 76, it would have been obvious to a skilled artisan to arrive at the instant process for the preparation of hexahydrocannabidiol derivative of the instant claims with a reasonable expectation of success, prior to the effective filing date. A skilled artisan would have been motivated to modify the prior art of Lago-Fernandez with the teachings of Zhou and Zhang for the following reasons:
Formic acid/ammonium formate mixture was shown to successfully and effectively generate H2 for various hydrogen needs (Zhou, conclusions, p. 22064);
A Pd/C catalyst system successfully demonstrated a hydrogenation process using toluene, at an overlapping heat range of the instant claims. “In the case where the claimed ranges ’overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists.” MPEP 2144.05(I).
Therefore, one of ordinary skill in the art would have had a reasonable expectation of success to arrive at the instantly claimed invention.
Regarding the elected species (R= propyl) and instant claim 24, a three-carbon vs. five-carbon difference, with all other chemical connectivity being identical between the instant claim and the prior art, would be considered obvious to a skilled artisan. “Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its
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homologs because
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homologs
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often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.” In re Deuel 34 USPQ2d 1210 at 1214. Furthermore MPEP 2144.09 (II) states: “Compounds which are […] homologs (…) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).” The properties of the homologs would have been similar as a result of their similar chemical structure.
Additionally, regarding instant claims 69, 73 and 74, a skilled artisan would have arrived within the claimed ranges of the catalyst, ammonium formate and formic acid as a result of routine experimentation. “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)”. See MPEP 2144.05(IIA). All three of these claims are drawn to “molar equivalents”, which would have been obvious a PHOSITA as a result of routine experimentation.
Conclusion
Applicant’s amendments necessitated the new ground(s) of rejection presented in this Office Action. Accordingly, 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 extension fee 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 MEGHAN C HEASLEY whose telephone number is (571)270-0785. The examiner can normally be reached Monday - Friday 8:30-4:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy Clark can be reached on 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MEGHAN C HEASLEY/Examiner, Art Unit 1626
/KAMAL A SAEED/Primary Examiner, Art Unit 1626
