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 Claims
The amendments to the claims filed April 7, 2026 are acknowledged and entered. Claims 1, 3-5, 7-10, 12 , 14, 16-20, 22 and 46-48 are pending.
Priority
This application is a 371 of PCT/CA2022/050311, filed March 4, 2022, which claims the benefit of 63/159,568, filed March 11, 2021.
Information Disclosure Statement
Acknowledgement is made of the Information Disclosure Statement filed on September 8, 2023. All references have been considered except where marked with a strikethrough.
Specification
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any of the errors of which applicant may become aware of in the specification.
Claim Objections
Claim 18 is objected to because of the following informalities:
Claim 18 is objected to for having improper format. The form of claims should be such that each claim begins with a capital letter and ends with a period. Periods may not be used elsewhere in the claims except for abbreviations. See MPEP 608.01(m). A claim thus should be one sentence. Examiner suggests deleting the second sentence corresponding to “In one embodiment, R2 represent…group.”
Election/Restriction
Applicant’s election without traverse of Group I (claims 1, 3-5, 7-10, 12, 14, 16-20 and 22, drawn to a compound of Formula (I)) and the species corresponding to 1-hydroxy-6,6,9-trimethyl-6H-benzo[c]chromen-3-yl trifluoromethanesulfonate (pictured below for convenience) in the reply filed on April 7, 2026 is acknowledged. Claims 46-48 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 April 7, 2026.
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The elected species corresponds to Formula (I) wherein:
R2 is H and LG is a sulphonate (triflate, -OTf)
The guidelines in MPEP § 803.02 provide that upon examination if prior art is found for the elected species, the examination will be limited to the elected species. The elected species was found in the prior art; however, the search was expanded to include the full scope of instant Formula (I).
Claim Rejections - 35 USC § 112a
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 3-5, 7-10, 12, 14 and 16-17 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for Formula (I) wherein R2 is independently hydrogen, unsubstituted C1-6 alkyl or a silyl group, and LG is a sulphonate does not reasonably provide enablement for the full scope of R2 or LG presently set forth in claim 1. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims.
The specification teaches Formula (I) is a cannabinol precursor that is useful for the preparation of cannabinol and its analogues and derivatives (pages 2-3, summary of disclosure). However, the only compounds of Formula (I) that have been shown to be useful are those embodiments disclosed in the Examples of the specification (see Examples 6-13, 18 and 23) and page 24, lines 10-15, which are included in the subgenus of formula (I) indicated above. This narrow scope of compounds does not give a reasonable assurance that all, or substantially all of the compounds within the scope of the claim are useful as precursors for the preparation of cannabinol and its analogues and derivatives . The claims are not drawn in terms of a recognized genus but are directed to a more or less artificial selection of compounds. There is no reason why a claim drawn in this way should not be limited to those compounds which are shown to be useful. An Applicant is not entitled to a claim for a large group of compounds merely on the basis of a showing that a selected few are useful and a general suggestion of a similar utility in the others. There is no statement of utility beyond that the claimed compounds are useful as precursors or synthetic intermediates for the preparation of cannabinol and its analogues and derivatives. Ex parte Lanham, 108 USPQ at 135 states “It was never intended that a patent be granted upon a product, or a process producing a product, unless such product be useful.”
The test of enablement is whether one skilled in the art could make and use the claimed invention from the disclosures in the application coupled with information known in the art without undue experimentation. (United States v. Teletronics Inc., 8 USPQ2d 1217 (Fed. Cir. 1988)). Whether undue experimentation is needed is not based on a single factor, but rather a conclusion reached by weighing many factors (See Ex parte Forman 230 USPQ 546 (Bd. Pat. App. & Inter. 1986) and In re Wands, 8 USPQ2d 1400 (Fed. Cir. 1988). These factors include the following:
1) The nature of the invention and predictability in the art. The nature of the invention is compounds which reportedly have use as precursors in the preparation of cannabinol and its analogues and derivatives (page 2 of specification, summary of disclosure). Regarding predictability in the art, chemistry is generally regarded as unpredictable. Dorwald F. A. (Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim pg. IX of Preface) teaches “Most non-chemists would probably be horrified if they were to learn how many attempted syntheses fail, and how inefficient research chemists are. The ratio of successful to unsuccessful chemical experiments in a normal research laboratory is far below unity, and synthetic research chemists, in the same way as most scientists, spend most of their time working out what went wrong, and why. Despite the many pitfalls lurking in organic synthesis, most organic chemistry textbooks and research articles do give the impression that organic reactions just proceed smoothly and that the total synthesis of complex natural products, for instance, is maybe a labor- intensive but otherwise undemanding task. In fact, most syntheses of structurally complex natural products are the result of several years of hard work by a team of chemists, with almost every step requiring careful optimization. The final synthesis usually looks quite different from that originally planned, because of unexpected difficulties encountered in the initially chosen synthetic sequence. Only the seasoned practitioner who has experienced for himself the many failures and frustrations which the development (sometimes even the repetition) of a synthesis usually implies will be able to appraise such work ......Chemists tend not to publish negative results, because these are, as opposed to positive results, never definite (and far too copious)...”
2) Scope of the claims. The scope of the claims involves all of compounds of the following formula:
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479
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and
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275
955
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The claims are thus drawn to a broad scope of compounds which are diverse with regard to chemical structure and reactivity.
3) Amount of guidance provided by applicant and number of working examples. The Applicant has demonstrated the compounds of Formula (I) wherein R2 is independently hydrogen, unsubstituted C1-6 alkyl or a silyl group, and LG is a sulphonate are useful for preparing cannabinol and its analogues and derivatives (see Examples 6-13, 18 and 23). However, there is no evidence to show the full scope of Formula (I) has any use as a precursor for the preparation cannabinol and its analogues. Applicant has provided no working examples of wherein LG is a halide, boronate or MXn or wherein R2 is any group other than H, alkyl or silyl. The examples provided by Applicant are not representative of the entire scope of compounds (e.g. Formula (I) wherein LG is sulfonate is not representative of Formula (I) wherein LG is boronate or MXn at least for the reason that a sulfonate, boronate and organometallic represented by MXn have different chemical reactivities). The disclosure is therefore not sufficient to allow extrapolation of the limited examples to enable the scope of the compounds instantly claimed.
5) Level of skill in the art. The artisan using applicant' s invention would be a scientist with a Ph.D. degree and having several years of research experience.
6) Undue experimentation. MPEP §2164.01 (a) states, "A conclusion of lack of enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the application was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention without undue experimentation. In re Wright, 999 F.2d 1557,1562, 27 USPQ2d 1510, 1513 (Fed. Cir. 1993)."
The conclusion is clearly justified here that applicant is not enabled for making these compounds
Claim Rejections - 35 USC § 112b
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 7-10, 12, 14 and 16-20 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. The claims are indefinite for the reasons that follow:
Claim 8 recites the limitation "Rt " in line 1. There is insufficient antecedent basis for this limitation in the claim because claim 8 depends from claim 4 which does not recite the limitation Rt. Claim 9 depends from and includes the limitation of claim 8 and therefore is also indefinite. It is suggested the claims be amended to depend from an appropriate claim which provides support for Rt.
Claim 10 recites the limitation "Rc" in line 6; however, Rc is not recited as a possible group or substituent in claim 10 or claim 1 and so it is unclear which group is intended to correspond to Rc.
Regarding claims 7, 12, 14 and 19, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance the claims recite broad and narrow limitations as described below:
Claims 7, 12 and 19 recite the broad recitation “cyclic”, and the claims also recites “aryl” which is the narrower statement of the range/limitation (See claim 7, final line, “Rc is a hydrogen atom or a cyclic, linear or branched alkyl, aryl or alkenyl group”; see claim 12, line 9; see claim 19, final line). Claims 14 depends from and includes the limitation of claim 12 regarding Rc and therefore is also indefinite
Claim 18 recites the broad recitation “-Si[(C1-C6)-alkyl]3”, and the claim also recites “-Si[(C1-C3)-alkyl]3” which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Claims 16 and 17 recite “Rc…independently… (C2-C20)-alkynyl” and “Rc…independently… (C2-C6)-alkynyl”, respectively. There is insufficient antecedent basis for these limitations in the claims because claims 16 and 17 depend from claim 12 which limits Rc to a hydrogen atom, or a cyclic, linear or branched alkyl, or aryl or alkenyl group.
Claim 20 recites “Rc…independently… (C2-C20)-alkynyl”. There is insufficient antecedent basis for this limitation in the claim because claim 20 depends from claim 19 which limits Rc to a hydrogen atom, or a cyclic, linear or branched alkyl, or aryl or alkenyl group.
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.
Claims 1, 4, 7-9, 12, 14, 19-20 and 22 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Sammis et al. (WO2022/133332 A2, effectively filed December 17, 2020).
Sammis teaches compound 25 (see page 79; pictured below for convenience) which corresponds to instant formula (I) wherein LG is a sulfonate (triflate, -OTf) and R2 is H. Sammis teaches each and every claim limitation and therefore anticipates the invention.
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Allowable Subject Matter
Claim 18 would be allowable if rewritten to overcome the objection and the rejection(s) under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), 2nd paragraph, set forth in this Office action and to include all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
The closest reference to the instant claims is Sammis et al. which was discussed in the rejection herein. The difference between Sammis and the claimed invention is that the invention requires that R2 is a silyl group (-Si[(C1-C6)-alkyl]3). Sammis does not teach wherein the position corresponding to instant R2 is a silyl group as required by the claimed invention. There is no teaching which would have motivated a person of ordinary skill in the art before the effective filing date of the instant application to modify Sammis into the claimed invention with any reasonable expectation of success.
Conclusion
No claim is allowed.
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May 13, 2026
/KEVIN S MARTIN/Examiner, Art Unit 1624
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