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 1-16, 18, and 19 are pending.
Claims 1, 7, 8, 11, and 13-16 are currently amended.
Claim 24 is new.
Claim 17 was previously withdrawn.
Claims 20-23 were previously cancelled.
Election/Restrictions
As stated in the previous office action dated 09 September 2025 (hereinafter POA), applicant’s election without traverse of Group I claims 1-16, 18, and 19 with species election in the reply filed on 12 June 2025 was acknowledged and Group II claim 17 was withdrawn. As stated in the POA, the elected species specifically corresponding to Formula 5 as depicted below
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, appears to be free of prior art. In the POA, as per MPEP 803.02C.2., the search and examination was extended to the non-elected species or group of species that falls within the scope of a proper Markush grouping that includes the elected species of Formula 5.
Therefore, the claims 1-16, 18, 19, and 24 non-elected species or group of species that falls within the scope of a proper Markush grouping that includes the elected species of Formula 5 are examined on the merits herein and claim 17 remains withdrawn.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 06 February 2026 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement, except where lined through, has been considered by the examiner.
Non-Patent Literature Document (NPL) 1 to Cordes et al. and NPL 4 to Wang et al. are not attached in their entirety in view of the page numbers submitted in the IDS. Cordes et al. has only the supplemental information attached; however, the examiner found the full NPL 1 to Cordes et al. online and it has been considered in its entirety. The entirety of NPL 4 to Wang et al. could not be found online, it has not been considered in its entirety, and it is lined through on the IDS. The entirety of NPL 1 to Cordes et al. and NPL 4 to Wang et al. must be filed on the record.
Response to Amendments
Applicant’s amendments filed 09 December 2025 are acknowledged.
Claim Objections
Applicant’s amendments to claim 1 are sufficient to overcome the objections of the claim. The claim has been amended to remove the erroneous “Rα and Rβ are …” limitation associated with Formula 5 and to delete the typographical mistake of “6,;”. The objections are withdrawn.
Claim Rejections - 35 USC § 112
Applicant’s amendments to claim 1 are sufficient to overcome the rejection of claims 1-15, 18, and 19 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 1 has been amended to define the Z variable and to delete the R1 and R2 variables. The rejections are withdrawn.
Applicant’s amendment to claim 15 is sufficient to overcome the rejection of claim 15 under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention. Claim 15 has been amended to define a proper Markush grouping. The rejection is withdrawn.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claim 1 adding additional optional variable limitations and clarifying the “treating the first intermediate of formula 6” step to include steps (1), (2), and (3) “… followed by a Bronsted or second Lewis acid 13 or a base alone” are not sufficient to overcome the rejection of claims 1-6, 8, 10-16, 18, and 19 under 35 U.S.C. 103 as being unpatentable over Kavarana et al. (US20170283837, cited by applicants as WO2017175064 on 08 April 2022, hereinafter Kavarana) in view of Cordes et al. (“Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation−Aromatization Sequences”, 22 November 2011, The Journal of Organic Chemistry, Vol. 77, Pgs. 652-657, referenced by applications in instant specification Pg. 18, Lns. 14-16).
The rejection is maintained; however due solely to the amendments to claims and new claim 24, additional modified ground(s) of rejection is/are provided below.
Applicant’s amendments to claim 1 adding additional optional variable limitations and clarifying the “treating the first intermediate of formula 6” step to include steps (1), (2), and (3) “… followed by a Bronsted or second Lewis acid 13 or a base alone” are not sufficient to overcome the rejection of claims 7 and 9 under 35 U.S.C. 103 as being unpatentable over Kavarana et al. (US20170283837, cited by applicants as WO2017175064 on 08 April 2022, hereinafter Kavarana) in view of Cordes et al. (“Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation−Aromatization Sequences”, 22 November 2011, The Journal of Organic Chemistry, Vol. 77, Pgs. 652-657, referenced by applications in instant specification Pg. 18, Lns. 14-16), as applied to claims 1-6, 8, 10-16, 18, and 19 in the 35 USC 103 rejection above, in further view of Huffman et al. (“A Pyridone Analogue of Traditional Cannabinoids. A New Class of Selective Ligands for the CB2 Receptor”, 2001, Bioorganic & Medicinal Chemistry, Vol. 9, Pgs. 2863-2870, hereinafter Huffman).
The rejection is maintained.
Response to Arguments
Applicant’s arguments filed 09 December 2025 have been fully considered but they are not persuasive.
Applicant’s argue that Kavarana, Cordes, and Huffman do not disclose the limitations as recited in newly amended claim 1. These arguments have been considered but are not persuasive for the reasons set forth in the new, maintained, and modified grounds of rejection below and the response to arguments below.
In response to applicant’s arguments throughout and specifically on pages 10-12 of the remarks filed on 09 December 2026 that are predominately drawn to Kavarana relating “to biosynthesis of cannabinoids, and more specifically relates to methods for using protein kinase synthase enzymes, which are responsible for the synthesis of cannabinoids in vivo in plants”; therefore, Kavarana is modified beyond its intended purpose.
Patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123. As stated in the previous office action dated 09 September 2025 (hereinafter POA) on page 9, “Kavarana teaches a variety of general synthetic methodologies for making Formula I compounds from precursor compounds and intermediate compounds, by using coupling reactions that couple, decouple, and replace the desired compounds amongst a variety of intermediate compounds, that are not all specifically depicted step by step in the Kavarana schemes, where the intermediate compounds are reacted with a Pd(dba)3 aka palladium(0) catalysts, THF, the halogen Br or I, a triethylamine base, propyne, and silica, then further subjected to hydrolysis, esterification, hydrogenation, and removal of the t-butyldimethylsilyl protecting groups, see Paras. [0082]-[0086], Schemes 1-3A;[0157]-[0163]”. To clarify, while Kavarana teaches embodiments drawn to the biosynthesis of cannabinoids of Formula I, see Paras. [0090]-[0092], Schemes 4 and 5, Kavarana also teaches a variety of general synthetic catalytic methodologies for making Formula I, see Paras. [0082]-[0086], Schemes 1-3A;[0157]-[0163]. Kavarana “does not criticize, discredit, or otherwise discourage” the synthesis of Formula 1 from chemical synthetic processes, see MPEP 2123. On the contrary, Kavarana specifically teaches “the invention provides synthetic methodologies for making Formula I compounds from precursor compounds”, where “Examples 6 and 7 illustrate synthetic methodologies”, see Paras. [0082];[0085]-[0086], Schemes 1-3A and Paras. [00150]-[0160]. Furthermore, the Formula I compound relied upon in the POA in Scheme 3 is made by a synthetic process, see Para. [0085] and below.
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For the reasons indicated above, applicants above arguments regarding Kavarana not teaching chemical synthesis and modification of Kavarana with a chemical synthesis process modifies Kavarana beyond its intended purpose are not persuasive.
In response to applicant’s arguments on pages 10-11 and 14 of the remarks filed on 09 December 2026 that a person of ordinary skill in the art would not “have been motivated to replace the process of Kavarana, with the chemistry in Cordes”, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, see In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007).
“A reference is analogous art to the claimed invention if: (1) the reference is from the same field of endeavor as the claimed invention (even if it addresses a different problem); or (2) the reference is reasonably pertinent to the problem faced by the inventor (even if it is not in the same field of endeavor as the claimed invention).”, see MPEP 2141.01(a).
As stated above, Kavarana specifically teaches “the invention provides synthetic methodologies for making Formula I compounds from precursor compounds”, where the Formula I compounds and precursor compounds are Pd catalytically synthesized cannabinoids, “Examples 6 and 7 illustrate synthetic methodologies” and the synthetic methodologies are not specifically depicted step by step in the Kavarana schemes, see Paras. [0082];[0085]-[0086], Schemes 1-3A and Paras. [00157]-[0160].
Cordes is in the known prior art filed of the synthetic synthesis of Pd catalytically synthesized cannabinoids, see Abstract, Pg. 652, Introduction, Pg. 653, Scheme 2 and Col. 1, First Para., and Pg. 654, Scheme 3, and is applied to teach the same.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Kavarana and Cordes teach synthetic synthesis of Pd catalytically synthesized cannabinoids in the chemical synthesis pharmaceutical industry, a person of ordinary skill in the art has good reason to modify Kavarana to synthesize Formula I by relying upon Cordes step by step intermediate process compound scheme before the effective filing date of the claimed invention for knowledge generally available within the synthetic synthesis of Pd catalytically synthesized cannabinoids art regarding the intermediate compounds produced within a reaction scheme leading to the final desired compound of Formula I, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the reaction scheme of intermediate compounds in a Pd catalytically synthesized cannabinoids synthesis, see MPEP 2141.
For the reasons indicated above, applicants above arguments regarding a person of ordinary skill in the art would not “have been motivated to replace the process of Kavarana, with the chemistry in Cordes” are not persuasive.
In response to applicant’s arguments on pages 12-14 of the remarks filed on 09 December 2026 that “Kavarana simply fails to teach, disclose or suggest any of the critical aspects of the process of independent claim 1, regardless of any similarity between the compounds” and “Kavarana is clearly not effective prior to support a prima facie case of obviousness against the pending claims”. The test for obviousness is not whether the features of a secondary reference may be bodily incorporated into the structure of the primary reference; nor is it that the claimed invention must be expressly suggested in any one or all of the references. Rather, the test is what the combined teachings of the references would have suggested to those of ordinary skill in the art, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981) and MPEP 2145.
As stated above and in the POA on page 9, Kavarana teaches synthetic methodologies for Pd catalytically synthesized cannabinoids; however, the synthetic methodologies are not specifically depicted step by step in the schemes, see Paras. [0082];[0085]-[0086], Schemes 1-3A and Paras. [00150]-[0160]. To clarify, Kavarana is not applied to teach the step by step intermediate compound scheme. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
As stated in the POA pages 9-11, Kavarana is combined with Cordes to teach the step by step intermediate process compound scheme, see Cordes, Abstract, Pg. 652, Introduction, Pg. 653, Scheme 2 and Col. 1, First Para., and Pg. 654, Scheme 3.
As stated above, since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Kavarana and Cordes teach synthetic synthesis of Pd catalytically synthesized cannabinoids in the chemical synthesis pharmaceutical industry, a person of ordinary skill in the art has good reason to modify Kavarana to synthesize Formula I by relying upon Cordes step by step intermediate process compound scheme before the effective filing date of the claimed invention for knowledge generally available within the synthetic synthesis of Pd catalytically synthesized cannabinoids art regarding the intermediate compounds produced within a reaction scheme leading to the final desired compound of Formula I, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the reaction scheme of intermediate compounds in a Pd catalytically synthesized cannabinoids synthesis, see MPEP 2141.
For the reasons indicated above, applicants above arguments regarding Kavarana not teaching the specific step by step process and Kavarana is not effective prior art are not persuasive.
In response to applicant’s arguments on pages 14-15 of the remarks filed on 09 December 2026 that Cordes does not teach Formula 5 as instantly claimed. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references, see In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
As stated above and in the POA on page 8, Kavarana is applied to teach Formula 5, see Paras. [0082];[0085]-[0086], Schemes 1-3A and Paras. [00157]-[0160].
As stated above and in the POA pages 9-11, Kavarana is combined with Cordes to teach the step by step intermediate process compound scheme, see Cordes, Abstract, Pg. 652, Introduction, Pg. 653, Scheme 2 and Col. 1, First Para., and Pg. 654, Scheme 3. To clarify, Cordes is not applied to teach Formula 5.
As stated above, since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Kavarana and Cordes teach synthetic synthesis of Pd catalytically synthesized cannabinoids in the chemical synthesis pharmaceutical industry, a person of ordinary skill in the art has good reason to modify Kavarana to synthesize Formula I by relying upon Cordes step by step intermediate process compound scheme before the effective filing date of the claimed invention for knowledge generally available within the synthetic synthesis of Pd catalytically synthesized cannabinoids art regarding the intermediate compounds produced within a reaction scheme leading to the final desired compound of Formula I, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the reaction scheme of intermediate compounds in a Pd catalytically synthesized cannabinoids synthesis, see MPEP 2141.
For the reasons indicated above, applicants above arguments regarding Cordes does not teach Formula 5 are not persuasive.
In response to applicant’s arguments on page 15 of the remarks filed on 09 December 2026 that Cordes “has substantial limitations regarding scalability in that the key step in the synthesis of the crucial Cordes intermediate 21 in the concurrent formation of the chloride 22 unless the chlorine scavenger amylene in used” and “[o]ne of ordinary skill in the art would not have been able to arrive at this synthetic scheme without undue experimentation”. Prior art references are part of the literature of the prior art relevant for all they contain, see MPEP 2123.
In this case Cordes teaches compound 21 is obtained at 23% without amylene and at 52% with amylene,
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, see Pg. 654, Scheme 3; Pg. 655, Col. 1, (E)-3,7-Dimethyl-2,6-octadien-1-yl 4-(2,2-dimethyl-4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate (21) – Col. 2, (E)-7-Chloro-3,7-dimethyloct-2-enyl 4-(2,2-Dimethyl 4-oxo-4H-1,3-dioxin-6-yl)-3-oxobutanoate (22). Therefore, in Scheme 3 of Cordes compound 21 is produced with or without amylene leading to zero undue experimentation. For the reasons indicated above, applicants above arguments regarding scalability and amylene are not persuasive.
New, Maintained, and Modified Rejections Based on Amendments to the Claims in the reply filed on 09 December 2025
In the Spirit of Compact Prosecution
Throughout prosecution the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
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)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 16 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kavarana et al. (US20170283837, published 05 October 2017, hereinafter Kavarana).
Regarding instant application claim 16, Kavarana discloses a compound of Formula I having the structure of instantly claimed formula 5 with the exception that the compound is not CBG 1, CBGA 2, CBGV 3, CBGVA 4,
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, where in Formula I, RA is CO2RC, RC is C1 alkyl, and RB is linear C3 alkyl, see above and Para. [0085], Scheme 3; see also Paras. [0137]-[0149], meeting:
Formula 5 in instant application claim 16 with the exception.
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.
Claims 1-6, 8, 10-16, 18, and 19 stand rejected in modified form and claim 24 is newly rejected under 35 U.S.C. 103 as being unpatentable over Kavarana et al. (US20170283837, published 05 October 2017, hereinafter Kavarana) in view of Cordes et al. (“Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation−Aromatization Sequences”, published 22 November 2011, The Journal of Organic Chemistry, Vol. 77, Pgs. 652-657).
For clarity between the new, maintained, and modified rejection, the specific new and modified rejections are in italics.
Kavarana teaches the claims 1, 11, 16, 18, and 19 limitations of a process for preparing the terpenophenolic compounds cannabigerolic acid, CBGA, cannabigerovarin acid, CBGVA, and Formula I, see Paras. [0003];[0022];[0027];[0085], Scheme 3;[0137]-[0149] and below,
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, where in Formula I above, RA is CO2RC, RC is C1 alkyl, RB is linear C3 alkyl, meeting:
Formula 5 in instant application claim 1 and in instant application claim 16;
The specific formula 5 acids of instant application claim 18 and instant application claim 19; and,
Kavarana teaches a variety of general synthetic methodologies for making Formula I compounds from precursor compounds and intermediate compounds, by using coupling reactions that couple, decouple, and replace the desired compounds amongst a variety of intermediate compounds, that are not all specifically depicted step by step in the Kavarana schemes, where the intermediate compounds are reacted with a Pd(dba)3 aka palladium(0) catalysts, THF, the halogen Br or I, a triethylamine base, propyne, and silica, then further subjected to hydrolysis, esterification, hydrogenation, and removal of the t-butyldimethylsilyl protecting groups, see Paras. [0082]-[0086], Schemes 1-3A;[0157]-[0163], meeting the specific Pd catalyst in instant application claim 11.
Kavarana does not teach:
The instant application claim 1 said process comprising the step by step intermediate compound limitations;
The presence of the specific phosphine in instant application claim 11; and,
The limitations of instant application claims 2-6, 8, 10, 12, 13, 15, and 24.
Cordes relating to the palladium catalyzed synthesis of terpenoids by coupling reactions that couple, decouple, and replace the desired compounds amongst a variety of intermediate compounds, that are mostly specifically depicted step by step in the schemes of Cordes, where the intermediate compounds are reacted with a palladium(0) catalysts, THF, the halogen Cl, a pyridine base, toluene, MgCl2, silica, hydrogen, and the protecting group TIPSO aka triisopropylsilane, see Abstract, Pg. 652, Introduction, Pg. 653, Scheme 2 and Col. 1, First Para., and Pg. 654, Scheme 3. Cordes teaches a reaction synthesis of intermediate compound 21,
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, where Rα and Rβ are both independently C1 alkyl aka methyl, see Pg. 652, Introduction and Pg. 654, Scheme 3, meeting:
The first intermediate 6 in instant application claim 1;
The limitations in instant application claim 3;
Compound 21 is treated with MgCl2, CH2Cl2, pyridine, and the compound 23,
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, where in compound 23 RB is AcO-CH2 and Z is Cl, see Pg. 654, Scheme 3, meeting:
The treating the first intermediate of the formula 6 with an electrophilic acylating reagent RBCOZ, Z is Cl, the first base 8 is pyridine, the first Lewis acid 9 is MgCl2 in instant application claim 1, in instant application claim 2, in instant application claim 4, in instant application claim 5, in instant application claim 6, and in instant application claim 24;
RB is AcO-CH2 and does not contain hydroxyl groups; therefore the optional protecting groups are not present, meeting the limitations in instant application claim 1, in instant application claim 14, and in instant application claim 15;
The reaction continues in the presence of a Pd(PPH3)4 catalysts aka palladium(0) triphenylphosphine and THF to synthesis intermediate compound 25 followed by silica gel and stepwise addition of 51% THF aka a Lewis base to synthesize intermediate compound 26,
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, where in compound 26 RB is AcO-CH2 and Rα and Rβ are both independently C1 alkyl aka methyl, see Abstract and Pg. 654, Scheme 3, meeting:
The palladium(0) complex in the presence of/containing triphenylphosphine in instant application claim 1, in instant application claim 8, in instant application claim 10, and in instant application claim 11;
The second intermediate 7 in instant application claim 1;
The reaction with silica in instant application claim 1 rendering the reaction with a second base 12 optional, meeting the limitations in instant application claim 12,
The reaction with silica in the presence of and followed by the base THF in instant application claim 1 rendering the reaction followed by a Bronsted or second Lewis acid 13 optional, meeting the limitations in instant application claim 13; and,
Product compounds are obtained by decarboxylation and hydrolyzation to prepare the desired compounds, see Pg. 652, Introduction and Pg. 654, Conclusion; Scheme 3, meeting providing a product compound in instant application claim 1.
Cordes further teaches the reactions take place in the presence of Cs2CO3, K2CO3, see Pg. 654, Scheme 3, and the protecting group TIPSO aka triisopropylsilane, see Pg. 653, Scheme 2 and Col. 1, First Para.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the generally depicted terpenophenolic cannabinoid coupling reaction synthesis of Kavarana to synthesize the terpenophenolic cannabinoids using the specifically depicted step by step terpenoid compounds coupling reaction synthesis process as taught by Cordes with a reasonable predictability of success for the purpose of efficiently producing terpenoid compounds by coupling, decoupling, and replacing the desired compounds in a palladium catalyzed five-step or lower synthesis that is high yielding, see Cordes, Abstract, Pg. 652, Introduction and Pg. 654, Conclusion.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and both Kavarana and Cordes teach synthetic synthesis of Pd catalytically synthesized cannabinoids in the chemical synthesis pharmaceutical industry, a person of ordinary skill in the art has good reason to modify Kavarana to synthesize Formula I by relying upon Cordes step by step intermediate process compound scheme before the effective filing date of the claimed invention for knowledge generally available within the synthetic synthesis of Pd catalytically synthesized cannabinoids art regarding the intermediate compounds produced within a reaction scheme leading to the final desired compound of Formula I, see MPEP 2143 B & G and 2141, for the benefit of efficiently controlling the reaction scheme of intermediate compounds in a Pd catalytically synthesized cannabinoids synthesis and efficiently producing terpenoid compounds by coupling, decoupling, and replacing the desired compounds in a palladium catalyzed five-step or lower synthesis that is high yielding, see Cordes, Abstract, Pg. 652, Introduction and Pg. 654, Conclusion, see MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means,” such as the specifically depicted process steps taught by Cordes, “is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions.” In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929), see MPEP 2144.05.
Selection of a known material, such as the type of palladium catalyst and reactants, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Claims 7 and 9 stand rejected under 35 U.S.C. 103 as being unpatentable over Kavarana et al. (US20170283837, cited by applicants as WO2017175064 on 08 April 2022, hereinafter Kavarana) in view of Cordes et al. (“Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation−Aromatization Sequences”, 22 November 2011, The Journal of Organic Chemistry, Vol. 77, Pgs. 652-657, referenced by applications in instant specification Pg. 18, Lns. 14-16), as applied to claims 1-6, 8, 10-16, 18, and 19; and new claim 24 in the 35 USC 103 rejection above, in further view of Huffman et al. (“A Pyridone Analogue of Traditional Cannabinoids. A New Class of Selective Ligands for the CB2 Receptor”, 2001, Bioorganic & Medicinal Chemistry, Vol. 9, Pgs. 2863-2870, hereinafter Huffman).
Kavarana in view of Cordes do not teach the limitations of instant application claims 7 and 9.
Huffman relating to the synthesis of analogues, such as compound 5, of traditional cannabinoids, such as compound 6, by palladium catalyzed coupling, see Abstract; Pg. 2864, Col. 2, First Para., and below
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.
Huffman teaches palladium catalyzed coupling through use of the phosphine ligand associated palladium (II) catalysts dichlorobis(triphenylphosphine)
palladium (II), see Pg. 2865, Scheme 2-3 and Pg. 2867, Col. 1, 2-Methoxy-6-(1-pentynyl)pyridine (11), meeting the specific palladium catalysts and ligand limitations in instant application claim 7 and in instant application claim 9.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Kavarana to synthesize the cannabinoids using the palladium catalyst as taught by Huffman with a reasonable predictability of success for the purpose of efficiently producing cannabinoids, analogs thereof, and derivatives thereof in an efficient palladium catalyzed synthesis that is high yielding, see Huffman, Pg. 2864, Col. 2, Last Para.-Pg. 2865, Col. 1, First Full Para.
By applying “routine optimization” and “predictable results” to select the optimal palladium catalyzed process, one of ordinary skill in the art would have been motivated to make these modifications because Huffman provides a finite number of identified, predictable solutions. A person of ordinary skill in the art has good reason to synthesize cannabinoids, analogs thereof, and derivatives thereof by pursuing the known options within their technical grasp for the benefit of efficiently producing cannabinoids, analogs thereof, and derivatives thereof in a palladium catalyzed synthesis that is high yielding, see Huffman, Pg. 2864, Col. 2, Last Para.-Pg. 2865, Col. 1, First Full Para. and MPEP 2141.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as the type of palladium catalyst and reactants, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 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.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699