DETAILED ACTION
This office action is in response to applicant’s filing dated April 17, 2026.
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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after allowance or after an Office action under Ex Parte Quayle, 25 USPQ 74, 453 O.G. 213 (Comm'r Pat. 1935). Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, prosecution in this application has been reopened pursuant to 37 CFR 1.114. Applicant's submission filed on April 17, 2026 has been entered.
Status of claims
Claims 1 – 16 and 22 - 26 are pending in the instant application. Claims 15, 16, 22 and 26 are withdrawn from consideration in the present office action, as being drawn to an unelected invention or species. Acknowledgment is made of Applicant’s amendments filed April 17, 2026.
Claims under consideration in the instant office action are claims 1 – 14 and 23 – 25.
Priority
The present application is a 371 of PCT/CA2020/050674, filed May 20, 2020, which claims the benefit of the filing dates of U.S. Provisional Application No.62/890,661, filed August 23, 2019 and U.S. Provisional Application No.62/851,837, filed May 23, 2019.
Claim interpretation
The claim language “the latter 6(2) groups” of claims 1, 2, 4, 5, 8 and 23 – 25 were interpreted as last 6(2) groups listed, e.g. in claim 1 latter 6 groups are: (C1-C20)-alkyl group, a (C2-C20)-alkenyl group, a (C2-C20)-alkynyl group, a (C3-C20)-cycloalkyl group, a (C6-C14)- aryl group, or a (C5-C14)-heteroaryl group.
Claim Objections
Claims 6, 7 and 12 – 14 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 23 – 25 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claims 23 – 25 recite hydrogen as one of the variants of R1, while claim 8, on which claims 23 – 25 are being dependent, does not recite hydrogen as possible variant of R1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
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.
Claims 1 – 5, 8 - 11 and 23 – 24 are rejected under 35 U.S.C. 103 as being unpatentable over Makriyannis et al (WO 2011/006099 A1, (reference of the record), hereinafter Makriyannis).
Instant claims are drawn to a compound of formula (I)
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103
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or a compound of formula (II)
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, where R1 is (C2-C20)-alkenyl group or a (C2-C20)- alkynyl group; R2 and R3 independently or simultaneously represent a (C1-C20)-alkyl group, acyl group -C(=O)-R', (C6-C14)- aryl group, or a (C5-C14)-heteroaryl group, wherein one or more of the carbon atoms in the alkyl, aryl, heteroaryl or acyl groups of R2 and/or R3 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P.
Makriyannis teaches a compound of formula (I)
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125
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, where Y is
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99
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where the dashed line represents a double bond, R7 is -Me and R8 is isopropenyl (page 6 [[0024], [0025]), R1 and R2 are -OH, -O-alkyl, -C(O)CH3, -C(O)CF3, -NH-alkyl, substituted or unsubstituted aromatic ring, a substituted or unsubstituted heteroaromatic ring (page 5 [0013]), R3 is -Z-alkyl-R6, where Z is -OSO2- and R6 is H, -CΞCH, -CH=CH2, and where R3 occupies position 5. Makriyannis defines “alkyl” as a linear or branched hydrocarbon radical which may be fully saturated, mono- or polyunsaturated and can include divalent radicals, having from 1 to about 15 carbon atoms.
Thus, since Makriyannis teaches compounds where all the structural elements are equivalent to instantly claimed, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the present invention to make various structural analogs of known compounds, by selecting known structural fragments and combining them with known core, to arrive at claimed compounds. The one of ordinary skills would be motivated to do so in search of an organic sulfonates with improved desired properties with the reasonable expectation of success.
Therefore, taking all together, taught by prior art, the invention as a whole is prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Response to Arguments
Applicant argues:
- The Office has not established a prima facie case of obviousness because, inter alia, the Office has not shown that the cited references (i.e., Makriyannis and MOC), taken individually or in combination, discloses or suggests the claimed invention. Additionally, the Office has not established that a person of ordinary skill in the art would have necessarily been led to the claimed invention in view of these cited references.
- Makriyannis does not teach or suggest all the limitations of independent claims 1 and 8. The Office Action suggests that starting from Makriyannis, it would be obvious to select one of the numerous compounds disclosed in the claimed invention and modify it to sulfonates to arrive at the claimed subject matter. We respectfully disagree. The mere fact that the prior art could be so modified would not have made the modification obvious unless the prior art suggested the desirability of the modification. In re Gordon, 733 F.2d 900 (Fed. Cir. 1984). Simply being capable of modifying is not enough. In re Mills, 916 F. 2d 680, 682 (Fed. Cir. 1990). The claimed invention aims to solve a long-standing problem in the art of challenging development of synthesis routes towards pure, single component cannabinoids.
- Dr. Abdur-Rashid (see the Declaration under 37 CFR1.132, filed April 17, 2026) opines that the present application aims to solve a long-standing problem in the art. The Office Action's conclusion of obviousness does not explain how Makriyannis and MOC would have suggested a solution to that problem. There would not be any reason for a skilled person in the art to consider modification of Makriyannis and expect the invention as an identifiable, predictable solution to the technical problem known in the art.
- Makriyannis is directed to new compounds with specific receptors selectivity, to provide desirable pharmacological properties. Accordingly, relying on Makriyannis as the closest prior art is improper and strictly relies on impermissible hindsight, i.e., the obviousness conclusion is merely using Applicant's disclosure as a roadmap to select sulfonylation chemistry from MOC and retrofit it onto the Makriyannis compounds without any teaching or suggestion in the cited art.
- It is clear that there is no obvious motivation or guidance for a person skilled in the art to select the lead compound from Makriyannis (i.e. the single compound of Formula (I) with variable selections as identified at pages 5-6 of the Office Action) as a starting point to solve the identified technical problem. The Office Action arguments relies on impermissible hindsight bias.
Examiner’s response:
Applicant's arguments and a Declaration of Dr. Abdur-Rashid have been fully considered but they are not persuasive because: as set forth above, Makriyannis teaches not a lead compound, that can be modified, but compounds where all the structural elements are equivalent to instantly claimed, thus Makriyannis teaches all the limitations of rejected claims (see the rejection section above). MOC reference was not applied in the present office action.
With respect to the argument that disclosure of Makriyannis requires numerous arbitrary selections, this is not found persuasive because: “It is well settled that it is a matter of obviousness for one of ordinary skill in the art to select a particular component from among many disclosed by the prior art as long as it is taught that the selection will result in the disclosed effect, even when the possible selections number 1200 or in the thousands.” Merck & Co., Inc. v. Biocraft Labs., Inc., 874 F.2d 804, 807 (Fed. Cir. 1989); In re Corkill, 771 F.2d 1496, 1500 (Fed. Cir. 1985). As stated above, a positive recitation cannot be seen as a negative teaching merely because there are additional utilities.
Regarding the argument that the compounds disclosed in Makriyannis were developed for pharmaceutical uses, while the instantly claimed compounds are needed for synthetic purposes is not found persuasive, because, as set forth above, Makriyannis teaches compounds of the same or similar structure as instantly claimed compounds. Thus, since compounds of the same structure are taught by prior art, their properties are obviously present even if these properties are not disclosed by prior art, i.e. if prior art teaches that the compounds can be used as a pharmaceutical product since they express certain pharmacological activity, does not preclude that compounds of the same structure can be used as a reactant in further synthetic pathways. MPEP 2112.01 states: "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). A chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. Id. (Applicant argued that the claimed composition was a pressure sensitive adhesive containing a tacky polymer while the product of the reference was hard and abrasion resistant. "The Board correctly found that the virtual identity of monomers and procedures sufficed to support a prima facie case of unpatentability of Spada’s polymer latexes for lack of novelty.").
In response to Applicant's argument about challenging development of synthesis routes towards pure, single component cannabinoids, it is not persuasive, because rejected claims are drawn to the compounds of Formula (I) and (II) and do not recite their method of making. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971).
Therefore, Applicant’s arguments are not persuasive and the rejection of claims 1 – 5, 8 - 11 and 23 – 24 as obvious over teachings of Makriyannis is maintained.
Conclusion
Claims 1 – 5, 8 - 11 and 23 – 25 are rejected.
Claims 6, 7 and 12 – 14 are objected to. No claim is allowed.
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/E.V.V./Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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