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 .
Priority
The instant application was filed on 12/20/2023 and claims the benefit of priority to:
PNG
media_image1.png
192
1004
media_image1.png
Greyscale
See filing receipt dated 5/20/2024.
Claim Status
Claims 1-50 were filed on 12/20/2023. In a preliminary amendment filed on the same day, claims 4, 7, 13, 19, 23, 25, 30, 35, 37, 38, 40, 44, and 49 were amended and claims 3, 5, 6, 8, 9, 11, 12, 15-18, 20-22, 24, 26-29, 31, 32, 39, 41-43 and 45-48, and 50 were canceled. Claims 1, 2, 4, 7, 10, 13, 14, 19, 23, 25, 30, 33-38, 40, 44, and 49 are pending.
Claim Objections
Claims 1, 2, 10, 19, 23, 33, 34, 35, and 44 are objected to because of the following informalities:
In line 4 of the first wherein clause in claim 1, the phrase “wherein the later” should recite “wherein the latter”. The same issue occurs in line 5 of claim 2; line 5 of the wherein clause of claim 10; and line 5 of the wherein clause in claim 34.
In the definition of variable R12 in claims 19 and 34:
In line 3, a comma is missing between the 4th and 6th options;
In line 5, a comma is missing between the 1st and 2nd options;
In line 8, a comma is missing between the 1st and 2nd options;
In the wherein clause of claim 23, in line 4 a comma is missing between the penultimate and final options; and
In line 6 a comma is missing between the 2nd and 3rd options.
Claim 33 is objected to because it is missing a period at the end of the claim. See MPEP 608.01(m).
In line 3 of claim 35, the limitation “R1” should be deleted because it is not in structure (I-B), and the word “and” should be inserted between “R7” and “R8”.
In the penultimate line of claim 44, there is a comma missing between “chlorobenzene” and “acetonitrile”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(d)
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 19 and 23 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.
Regarding claim 19, the compound of formula (III-A) does not further limit the scope of compound (III) of claim 1, from which claim 19 depends. In the annotated drawing below, compound (III) has carbon atoms A (attached to R5 and B), B (attached to A and C and R6), and C (attached to B, R7, R8, and OH). However, in formula (III-A), carbon C is not attached to carbon B.
PNG
media_image2.png
280
575
media_image2.png
Greyscale
At first glance, variable R6 of formula (III-A) looks like it should be changed to R5 to overcome the issue. However, if that change is made, Formula (III-A) still fails to further limiting Formula (III) because of how R5, R6, R7, and R8 are defined in claim 1. Claim 1 recites that “any of R5 and R6, R5 and R7, or R7 and R8 are linked together to form an unsubstituted or substituted monocyclic or polycyclic ring system”. Therefore, if R6 is changed to R5, there is still an issue. To make a ring out of Formula (III), then two of the mentioned R groups must connect to form the ring. The claim does not recite that any of the carbon atoms A, B, or C attached to the R variables can be attached to an R group and still bear the R attachment. It must be an R group attached to an R group. Therefore “R6” would have to be deleted from the structure, wherein the ring would be formed by R5 connecting with R7.
Regarding claim claim 23, the definition of variable R13 includes the options “CN, NO2, COOH”. These options fall to further limit claim 1, from which claim 23 depends. When the structure of claim 23 is mapped to Formula (III) of claim 1, the ring is formed by joining R7 and R8, which can be substituted by the recited “one or more substituents independently selected from =O, …and C3-20heterocycloalkyl”. Therefore, these substituents must correspond to variable R13 in claim 23 as they are the substituents on the ring formed by joining R7 and R8. Claim 1 does not include “CN, NO2, COOH” in the list of acceptable substituents. Therefore, claim 23 fails to further limit claim 1.
Claim 23 is further rejected because “the latter 21 groups” mentioned with respect to variable R13 are not the same as those in claim 1. The list of substituents in claim 1 does not explicitly recite “SC1-10fluoroalkyl”, “S(O)C1-10fluoroalkyl”, or “SO2C1-10fluoroalkyl”, therefore the “latter 21 groups” in claim 1 is not the same as that of claim 23. The fluoroalkyl groups newly recited would have to correspond to a C1-20 alkyl group, substituted by halo in claim 1, wherein halo groups are not included in “the latter 21 groups” of substituents which can be further substituted by one or more substituents independently selected from OH, halo, C1-20alkyl, C1-20haloalkyl, C2-20alkenyl, C1-20alkyl and OC1-20haloalkyl. Thus, claim 1 does not recite that C1-20 alkyl groups substituted by halo can be further substituted with OH, halo, C1-6alkyl, C1-6haloalkyl, C2-6alkenyl, C1-6alkyl and OC1-6haloalkyl.
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 § 102
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 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.
(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.
Claim(s) 1, 2, 4, 10, 13, 33, 35, 37, 38, and 44 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Jentsch (“Synthesis of Cannabigerol Derivatives via Direct ortho-allylation of phenols” powerpoint presentation from National ACS Meeting and Exposition, August 27, 2019, of record in the IDS filed on 4/21/2026).
Jentsch teaches the following reaction:
PNG
media_image3.png
718
1196
media_image3.png
Greyscale
See slide 18. Phenol, a compound of instant formula (II) and claim 13 wherein R1, R2, R3, and R4 are H, is reacted with cinnamyl alcohol, a compound of instant formula (III) wherein R5 is phenyl (aryl) and R6, R7, and R8 are H, to produce compounds A, B, and C. Compounds A and B correspond to compounds of instant formula (I) wherein R1 to R4 are H (A) or wherein R2, R3, and R4 are H and R1 is a C3alkenyl substituted by aryl (B). Compound (A) corresponds to compound I-38 of claim 33. Compound B is also a compound of instant formula (I-B) in claim 35, wherein R2, R3, and R4 are H, R5 is phenyl (aryl), and R6, R7, and R8 are H. Jentsch teaches that the compounds are reacted in the presence of acidic alumina (alumina and an acid-claims 37 and 38) in DCE (1,2-dichloroethane, a non-protic solvent-claim 44). Also see slides 28-29 further regarding alumina.
Therefore, the reactions of Jentsch anticipate the reactions of claims 1, 2, 4, 13, 33, 35, 37, 38, and 44. Also see MPEP 2131. Slide 21 further teaches that the phenol is reacted with the corresponding compound of instant formula (III) to prepare compounds I-40 and I-41 of claim 33. Slide 22 teaches that cinnamyl alcohol is reacted with the corresponding compound of instant formula (II) to prepare compounds I-31 and I-32 of claim 33. Slide 22 also teaches the use of several of the phenols in claim 13. Further, slide 22 also teaches an example wherein cinnamyl alcohol is reacted with resorcinol, a compound of claims 10 and 13 wherein R2 is H.
Claim(s) 1, 2, 4, 7, 10, 13, 37, 38, and 44 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Baek (“Spectroscopic Methods for Distinguishing Primary and Secondary Alkylation Products” Bull. Korean Chem. Soc., 1993, p. 144, of record in the IDS filed on 4/21/2026).
Baek teaches the reaction between a cyclic allylic alkenol (1) and resorcinols (2) in the presence of BF3·etherate (a Lewis acid-claim 38), in the absence (a) and presence (b) of alumina (claim 37):
PNG
media_image4.png
432
600
media_image4.png
Greyscale
. See Scheme 2. In the presence of alumina, the reaction produces ortho-allylation products (3) and (6). The reaction with alumina (aluminum oxide) takes place in the presence of dichloromethane (DCM, a non-protic solvent-claim 44) and is referred to as “general procedure (A)” as discussed in col. 1 on p. 144:
PNG
media_image5.png
388
584
media_image5.png
Greyscale
The compound of formula (1) corresponds to a compound of instant formula (III) wherein R8 is methyl (C1 alkyl), R6 is H, and R5 and R7 are connected to form a monocyclic unsubstituted cyclohexene ring having 6 carbon atoms. Entry (26) in Table 1 also shows a one-carbon homolog, wherein the ring is 5 carbon atoms.
The resorcinols (2) were varied, as shown in Table 1 on p. 145-146. These compounds correspond to compounds of instant formula (II) wherein R4 is OH, OCH3 (Z-C1alkyl, wherein Z is O), OC2H5 (Z-C2alkyl, wherein Z is O), or CH3 (C1alkyl); R1 and R3 are H; and R2 is H, methyl (C1alkyl), C5H11 (C5alkyl), 1,1DMH (defined as 5-(1,1-dimethylhepthyl) in col. 1 on p. 144, 4th paragraph, thus corresponding to a C7alkyl), or OCH3 (Z-C1alkyl, wherein Z is O).
The products of (1) and (2) of Baek correspond to compounds of instant formula (I) wherein all variables are as defined above. Thus, the reactions of Baek anticipate the reactions of claims 1, 2, 4, 7, 10, 13, 37, 38, and 44. Also see MPEP 2131.
Claim(s) 1, 2, 4, 7, 10, 13, 19, 33-35, 37, 38, and 44 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kim (“A Simple One-Step Synthesis of Alkylation Product from Cyclic Allylic Alcohol and Resorcinol” Arc. Pharm. Res, 1992, p. 304, of record in the IDS filed on 4/21/2026).
Kim teaches the reaction between a cyclic cycloalkene (1) or (6) with resorcinols (7) or (8) to produce compounds of formula (9) to (18):
PNG
media_image6.png
542
606
media_image6.png
Greyscale
. See p. 306.
When compound (1) is used, general procedure (A) was followed and when compound (6) is used, general procedure (B) was followed. See col. 1 on p. 305. General procedure (A) produces compounds of formula (9), (10), (12), (15), (16), (17), and (18). See p. 305, col. 2 to top of col. 2 on p. 306. General procedure (B) produces compounds of formula (11), (13), and (14). See col. 2 of p. 306 to col. 1 on p. 307. Both procedures teach that BF3·etherate (an acid-claim 38) is added to a stirred suspension of basic aluminum oxide (alumina-claim 37) in dichloromethane (a non-protic solvent, claim 44).
The compounds of formulas (1) and (6) correspond to compounds of instant formula (III) wherein R8 is methyl (C1 alkyl), R6 is H, and R5 and R7 are connected to form a monocyclic cyclohexene ring having 6 carbon atoms. In compound (6) the ring is substituted by a C3alkenyl group. Compound (6) is also a compound of instant formula (III-A) in claim 19 and (III-A) in claim 34, wherein R8 is methyl (C1alkyl), R6 is H, m is 2, n is 1, and R12 is C3alkenyl.
The compounds of formulas (7) and (8) correspond to compounds of instant formula (II) wherein R4 is OH (resorcinol-claims 10 and 13) or OCH3 (Z-C1alkyl, wherein Z is O); and R1, R2 and R3 are H. The products of (9), (10), and (11) of Kim correspond to compounds of instant formula (I) wherein all variables are as defined above. Compounds (12), (13), and (14) of Kim also correspond to compounds of formula (I) wherein the definitions of instant variables R2 and R4 are switched because compounds (12), (13), and (14) are regioisomers of compounds (9), (10), and (11). Compound (9) further corresponds to compound I-25 in claim 33.
Compound (15) corresponds to a compound of instant formula (I-B) in claim 35, wherein R4 is OH; R2 and R3 are H; R8 is methyl (C1 alkyl), R6 is H, and R5 and R7 are connected to form a monocyclic cyclohexene ring having 6 carbon atoms.
Thus, the reactions of Kim anticipate the reactions of claims 1, 2, 4, 7, 10, 13, 19, 33-35, 37, 38, and 44. Also see MPEP 2131.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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) 1, 2, 4, 10, 13, 25, 30, 33, 40, 44, and 49 is/are rejected under 35 U.S.C. 103 as being unpatentable over Brand (WO 2020/249184 A1, published on 12/17/2020).
Applicant claims:
PNG
media_image7.png
634
830
media_image7.png
Greyscale
Brand teaches:
PNG
media_image8.png
448
670
media_image8.png
Greyscale
See claims.
Brand teaches the following example on p. 31:
PNG
media_image9.png
600
680
media_image9.png
Greyscale
. Olivetol (2) is reacted with linalool (4) to produce cannabigerol (CBG, 1) in the presence of a para-toluene sulphonic acid (p-TsOH) acid catalyst and toluene (non-protic solvent-claim 44). See p. 31-32.
Olivetol (2), specifically recited in instant claim 13, is a compound of instant formula (II) wherein R4 is OH, R2 is n-pentyl (C5alkyl), and R1 and R3 are H. Linalool, specifically recited in instant claim 30, is a compound of instant formula (III) of claims 1 and 25 wherein R5 and R6 are H, one of R7 and R8 is methyl (C1alkyl), and the other is a C6alkenyl. CBG (1) is a compound of instant formula (I), compound I-3 of claim 33, wherein all of the variables are as defined above. Thus, the reaction meets the limitations of instant formulas (I), (II), and (III) in claims 1, 2, 4, 10, 13, 25, 30, and 33.
Brand exemplifies p-TsOH as a catalyst, but also teaches that other acidic or Lewis catalysts can be used, including aluminium isopropoxide (an aluminum alkoxide-claim 40):
PNG
media_image10.png
144
658
media_image10.png
Greyscale
. See claim 8.
Brand does not explicitly teach an anticipatory example wherein the catalyst for the reaction is alumina or an aluminum alkoxide.
It would have been prima facie obvious to arrive at the instantly claimed process based on the teachings of Brand with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute an aluminum alkoxide, specifically aluminum isopropoxide, for the p-TsOH exemplified by Brand, because Brand explicitly teaches such. Brand teaches a limited genus of ninenteen acceptable and predictable catalysts, one of them being aluminum isopropoxide. Therefore replacing one known catalyst with another as directed to obtain predictable results is not inventive.
Regarding claim 49, Brand teaches that the molar ratio of olivetol (a compound of instant formula II) to linalool/geraniol (allylic alcohol compounds of instant formula III) falls within the range of 1:1 to 1:2 (claim 2) or 1:0.5 to 1:1.2 (claim 4). See claims 2 and 4, wherien the range in claim 4 includes the option of the use of a 0.20 molar excess of the olivetol. Brand does not explicitly teach that the olivetol is used in a 2 to 4 molar amount excess with respect to the allylic alcohol. Brand teaches that it is known that the reaction produces a mixture of products, including regioisomers and polyalkylation products, which can be difficult to separate fro the desired product. See p. 3, line 32-p. 4, line 14. The method of Brand is directed toward the use of polyalkylation as a tool to functionalize the undesirable regioisomer to simplify purification. See p.5, line 25-p. 8, line 6. Brand teaches that the polyalkylation can take place using the same allylic alcohol as the primary reaction (claim 2, molar ratio of 1:1-2 olivetol:allylic alcohol) or by carrying out a second reaction with a sterically hindered alcohol (claim 4, molar ratio of 1:0.5-1.2 of olivetol:first allylic alcohol followed by molar ratio of 0.21:1 of steric allylic acohol:olivetol) to further enhance the separation. Preferred steric alcohols are described on p. 10, line 5 to p. 11, line 10 and p. 14, line 15-p. 16, line 19.
Though Brand teaches that the second embodiment (of claim 4, containing the use of a second step employing a steric allylic compound) can employ an excess of olivetol : allylic alcohol, it is not as significant as that claimed (1.2 : 1 vs. the claimed 2:1). However, based on the reasoning behind the method of Brand, it would have been prima facie obvious to further increase the quantity of olivetol relative to the first allylic alcohol (geraniol/linalool). The skilled artisan would have been motivated to make this modification because doing so will decrease the risk of polyalkylation to produce more of the desired CBG product in the first step, while producing an easier to separate polyalkylation product in the second step using the steric allylic alcohol. Though there may be a decrease in the amount of CBG produced, there would also be a decrease in the amount of polyalkylated product that is more difficult to separate from CBG. Also see MPEP 2144.05.
Claim(s) 1, 2, 4, 10, 13, 33, 35, 37, 38, 44, and 49 is/ rejected under 35 U.S.C. 103 as being unpatentable over Jentsch (“Synthesis of Cannabigerol Derivatives via Direct ortho-allylation of phenols” powerpoint presentation from National ACS Meeting and Exposition, August 27, 2019, of record in the IDS filed on 4/21/2026).
The teachings of Jentsch were discussed in a rejection in the preceding rejection and are incorporated by reference herein.
Regarding claim 49, on slide 16, Jentsch teaches a molar ratio of olivetol (compound of instant formula II) : geraniol (compound analogous to those of instant formula III) of 1.5:1 for the optimized reaction, which is presumably carried through the reactions on slides 18-22. This falls outside of the claimed range of 2-4:1. It would have been prima facie obvious to arrive at the instantly claimed invention based on the teachings of Jentsch with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to increase the molar ratio of the compound of formula (II) : the compound of formula (III) to fall within the claimed range because increasing the concentration of the compound of formula (II) relative to the compound of formula (III) will predictably lower the risk of obtaining any polyalkylated side products, such as compound B on slide 18. Also see MPEP 2144.05.
Claim(s) 14 is/ rejected under 35 U.S.C. 103 as being unpatentable over Jentsch (“Synthesis of Cannabigerol Derivatives via Direct ortho-allylation of phenols” powerpoint presentation from National ACS Meeting and Exposition, August 27, 2019, of record in the IDS filed on 4/21/2026), as applied to claims 1, 2, 4, 10, 13, 33, 35, 37, 38, 44, and 49 above, and further in view of Mignani (US 4594460, published on 6/10/1986) and Brand (WO 2020/249184 A1, published on 17/17/2020).
Jentsch does not explicitly teach the use of compounds of instant formula (II) wherein at least one of R1 and R2, R2 and R3, and/or R3 and R4 are linked together to form a polycyclic ring system having 10 or more atoms.
Mignani teaches the production of compounds of formula (I):
PNG
media_image11.png
320
392
media_image11.png
Greyscale
by reacting a butadiene of formula (II) with a phenol of formula (III) in the presence of a rhodium-based catalyst. See claims. Miganani teaches the compounds of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides. See abstract. Example 7 of Mignani teaches the reaction between 2-naphthol with isoprene to produce 1-(3-methyl-3-butenyl)-2-naphthol and 1-(3-methyl-2-butenyl)naphthol. The first compound is a compound I-10 in claim 33, and corresponds to a compound of instant formula (I) wherein R3 and R4 are joined together to form a ten membered unsubstituted polycyclic ring system (naphthalenyl), R1, R2, R5, and R6 are H, and R7 and R8 are methyl (C1alkyl). Likewise, 2-napthol is a compound of instant formula (II) wherein the variables are as defined above. Therefore, Mignani provides motivation to synthesize compounds of claim 14.
Neither Mignani nor Jentsch teach reacting 2-naphthol with a compound of instant formula (III) to produce the compounds of Mignani. Jentsch teaches an analogous reaction system on slide 16, wherein olivetol is reacted with geraniol to produce CBG. However, geraniol does not meet the limitations of instant formula (III) because it corresponds to a compound of said formula wherein the carbon attached to R5 is not attached to a hydrogen atom. Geraniol is analogous to the compounds of formula (III) which would be required to produce the naphthol compounds of Mignani based on the teachings of Jentsch, which would also fail to meet the limitations of instant formula (III).
Brand, as discussed in a previous rejection, teaches that linalool (4) is an acceptable substitute for geraniol (3) in analogous reactions catalyzed by Lewis acids, including aluminum alkoxides:
PNG
media_image12.png
250
224
media_image12.png
Greyscale
. See p. 4. Also as discussed above, linalool does meet the limitations of instant formula (III).
It would have been prima facie obvious to combine the teachings of Jentsch, Mignani, and Brand to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to produce compounds of claim 14 based on the teachings of Mignani, which indicate that said compounds are important synthetic intermediates. A person of ordinary skill would be motivated to produce the naphthol compounds of Mignani by using compounds of instant formula (III) in the reaction of Jentsch because Brand teaches that tertiary terpene alcohols of instant formula (III) are predictable substitutes for the corresponding primary terpene alcohols of Jentsch in the claimed process. Further, expanding the scope of a known predictable process is always desirable to increase access to a wider variety of compounds for a variety of uses. Therefore, preparing a desirable compound using a predictable reaction is not inventive. Also see MPEP 2143(I)(B).
Claim(s) 23 is/ rejected under 35 U.S.C. 103 as being unpatentable over Jentsch (“Synthesis of Cannabigerol Derivatives via Direct ortho-allylation of phenols” powerpoint presentation from National ACS Meeting and Exposition, August 27, 2019, of record in the IDS filed on 4/21/2026), as applied to claims 1, 2, 4, 10, 13, 33, 35, 37, 38, 44, and 49 above, and further in view of Kakhniashvili (“Alkylation of o-cresol by 1-vinylcyclopentan-1-ol”, Trudy Tbilisskogo Universiteta / Tr. Tbilis. Gos. Univ., 1976).
Jentsch does not explicitly teach the use of compounds of instant formula (III) of claim 23. Though as discussed in preceding rejections, the scope of the Jentsch reaction is broad. See slides 21-22.
Kakhniashvili teaches the following process to produce a compound of instant formula (I) (compound III in the Scheme):
PNG
media_image13.png
470
758
media_image13.png
Greyscale
. See p. 77. Compound (III) is a compound of instant formula (I) wherein R1 is methyl (C1alkyl) and R2, R3, R4, R5, and R6 are H and R7 and R8 are joined to form an unsubstituted monocyclic ring system having five atoms. This compound corresponds to compound I-46 in claim 33. Kakhniashvili teaches that the compound is formed from a mixture of the allylic compounds above reacted with ortho-methyl phenol in the presence of a strong acid (H3PO4). The tertiary alcohol isomer of the allylic alcohol (the compound on the left in the first reversible reaction) corresponds to a compound of instant formula (III) wherein the variables are as defined above, and a compound of claim 23 wherein R5 and R6 are H, p is 1, and q is 0. Ortho-methyl phenol is a compound of instant formula (II) wherein the variables are as defined above.
It would have been prima facie obvious to combine the teachings of Jentsch and Kakhniashvili to arrive at the instantly claimed compounds with a reasonable expectation of success before the effective filing date of the instant invention. A person of ordinary skill would have been motivated to prepare the compounds of Kakhniashvili using the process of Jentsch because Jentsch teaches milder process conditions than those claimed (alumina vs. H3PO4), which should make the product easier to separate because the alumina is heterogeneous and can be filtered from the reaction. Further, expanding the scope of a known predictable process is always desirable to increase access to a wider variety of compounds for a variety of uses. Using known process conditions to predictably produce known compounds is not inventive. Also see MPEP 2143(I)(B).
Subject Matter free from the Art
The subject matter of claim 36 appears to be free from the prior art. The prior art does not teach or suggest the claimed compounds, therefore there is no motivation to produce said compounds using the claimed process. The closest prior art is Jentsch and Kim, as discussed in the 35 USC 102 rejections above.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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, Scarlett Goon can be reached at 571-270-5241. 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.
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
Prosecution Insights