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 .
DETAILED ACTION
Claims 1-20 are pending in the application. Claims 6, 14 and 17-20 are rejected. Claims 7 and 15 are objected to. Claims 1-5, 8-13 and 16 are allowed.
Claim Rejections - 35 USC § 112(b)
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 17-20 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.
(1 of 3) Claim 17 is rejected as indefinite since the preamble of claim 17 recites a “method for synthesizing cannabinol (CBN) or cannabinovarin (CBNV)” but where step (c) only refers to heating “to form CBN”. While the formulae 1 and 2 are generic to precursors for CBNV, it is unclear if the claims embrace the alternative preparation of CBNV or if, for instance, CBN is generated in all embodiments but CBNV may or may not be generated. Dependent claims 18-20 are rejected as indefinite for the same reason since they do not obviate the issue.
(2 of 3) Claim 17 recites the limitation "the mixture of step (b)" in the tenth line of the claim (in step (c)). There is insufficient antecedent basis for this limitation in the claim. The preceding step (b) recites “heating the resulting first mixture from (a) to form a compound according to Formula 2…”. Step (b) only refers to forming “a compound” as opposed to a mixture. The specification in various examples (such as Example 6) directly adds an oxidant (iodine) to a mixture containing CBD or CBNV, an acid and a solvent. Limitations from the specification, however, are not imported to the claims. In this situation, it is unclear if Applicant is attempting to have step (b) encompass possible removal of the additional components of the first mixture prior to proceeding to step (c). Applicant could argue that the reference to “mixture” in step (c) implies otherwise; however, a person of ordinary skill in the art would recognize that acid-catalyzed treatment of CBD or CBNV can result in a mixture of products. For instance, WO 2020/248062 A1 by Adair et al. teaches the treatment of CBD with an acid can result in the mixture of Δ9-THC and Δ8-THC (see Table 2, page 47). For these reasons, it is unclear what set of components constitute “the mixture of step (b)”. Dependent claims 18-20 are rejected as indefinite for the same reason since they do not obviate the issue.
The two issues above could be resolved by amending claim 17 (and dependent claim 19 to maintain consistency with the change to claim 17) as follows:
Claim 17: A method for synthesizing cannabinol (CBN) or cannabinovarin (CBNV), comprising:
contacting a compound of Formula 1 with a solvent and an acid to form a first mixture;
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heating the resulting first mixture from (a) to form a second mixture comprising a compound according to Formula 2; and
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contacting an oxidant with the second mixture of step (b) and heating the resultant third mixture to form CBN or CBNV;
wherein,
R1 in Formula 1 and Formula 2 is —H and R2 in Formula 1 and Formula 2 is propyl or pentyl.
Claim 19: The method of claim 17, wherein the third mixture is heated to 110° C.
(3 of 3) Claim 20 contains the trademark/trade name (in several instances) Amberlyst. Where a trademark or trade name is used in a claim as a limitation to identify or describe a particular material or product, the claim does not comply with the requirements of 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph. See Ex parte Simpson, 218 USPQ 1020 (Bd. App. 1982). The claim scope is uncertain since the trademark or trade name cannot be used properly to identify any particular material or product. A trademark or trade name is used to identify a source of goods, and not the goods themselves. Thus, a trademark or trade name does not identify or describe the goods associated with the trademark or trade name. In the present case, the trademark/trade name is used to identify/describe a particular acid and, accordingly, the identification/description is indefinite.
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.
Claim 6 is 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. Parent claim 1 recites the use of a base and dependent claim 6 recites two exhaustive categories of bases, i.e. organic or inorganic. Accordingly, every embodiment of parent claim 1 is embraced by dependent claim 6. 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 14 is 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. Parent claim 9 recites the use of a base and dependent claim 14 recites two exhaustive categories of bases, i.e. organic or inorganic. Accordingly, every embodiment of parent claim 9 is embraced by dependent claim 14. 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
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.
Claim(s) 17, 18 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over U.S. Patent PGPub No. 2022/0002261 A1 by D’Spain et al. in view of U.S. Patent PGPub No. 2022/0033373 A1 by Loewinger et al., which claims support to U.S. Provisional Application No. 63/060,183 filed August 3rd, 2020 and in further view of WO 2020/248062 A1 by Adair et al.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
D’Spain et al. generally teach that CBD can be converted to CBN in a two-step procedure as follows on page 1:
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The prior art teaches an initial acid-catalyzed conversion to tetrahydrocannabinols followed by aromatization with halogen (an oxidation procedure).
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The general procedure of D’Spain et al. overlaps with the instant claims where CBD (a compound of Formula 1 where R1 is -H and R2 is pentyl) is reacted with an acid to form a compound of Formula 2 (which is tetrahydrocannabinol, Δ8-THC) followed by oxidation to form CBN. The additional embodiments of D’Spain et al., however, are directed to different conditions and manipulations.
As discussed above under rejection (2 of 3) under 35 USC 112(b), instant claims 17-20 are considered indefinite. At least one interpretation is that step (b) does not require the mixture of step (a) to be carried through the overall process. The instant rejection is premised on the broader interpretation that step (b) embraces separation of the compound of Formula 2 (along with additional cannabinoids) from the remainder of the first mixture.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
A person having ordinary skill in the art would have recognized that the transformations of D’Spain et al. are not strictly limited to the embodiments disclosed in the primary reference. For instance, Loewinger et al. teach methods of aromatizing cannabinoids and provide the following description on page 3 (support can be found in paragraph [0034] and Figure 2 of the ‘183 priority document):
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Figure 2 provides the following depiction:
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Loewinger et al. similarly teach an acid-catalyzed step followed by an aromatization step. At least in the interest of determining which known conditions for performing the individual transformations would provide optimum results, a person having ordinary skill in the art would have been motivated to test known conditions or approaches for the individual transformations.
As an example of known approaches corresponding to conversion of CBD to a tetrahydrocannabinol, Adair et al. teach cannabinoid isomerizations including the following example on page 42:
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The prior art teaches contacting CBD with a solvent (heptane) and an acid (Amberlyst-15, recited in instant claim 20 as Amberlyst A-15) corresponding to instant step (a) where R2 is pentyl. The prior art further teaches heating the mixture to 60°C and forming Δ8-THC corresponding to instant step (b) where R2 is pentyl. Regarding instant claim 18, Adair et al. teach the following on page 28:
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“[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05.
Regarding the instant step (c), Loewinger et al. teach aromatization as noted above. The authors teach that Δ8-THC (the majority product of Adair et al.) can be converted to CBN, for example, in paragraphs [0067] and [0068]. While the particular example appears to have been performed at room temperature, Loewinger et al. teach the following range on page 6:
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“[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP 2144.05. Applying a range above room temperature would entail contacting the product of Adair et al. (a mixture) with an oxidant (the ortho-quinone of Loewinger et al.) and heating to above room temperature to form CBN.
Claim(s) 19 is/are rejected under 35 U.S.C. 103 as being unpatentable over U.S. Patent PGPub No. 2022/0002261 A1 by D’Spain et al. in view of U.S. Patent PGPub No. 2022/0033373 A1 by Loewinger et al., which claims support to U.S. Provisional Application No. 63/060,183 filed August 3rd, 2020 and in further view of WO 2020/248062 A1 by Adair et al., as applied to claims 17, 18 and 20 above, and in further view of Pollastro et al. J. Nat. Prod. 2018, 81, 630-633.
The rationale above discusses conversion of CBD to a majority Δ8-THC product (taught by Adair et al.) and then conversion to CBN. A person having ordinary skill in the art, however, would have similarly been familiar with conversions of CBD to a majority Δ9-THC product where Adair et al. teach Example 7 on pages 43 and 44 using Amberlyst-15 and where Example 7 still results in a minor portion of Δ8-THC as required by instant step (b). Furthermore, Pollastro et al. teach a method of converting Δ9-THC to CBN on page 631:
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Pollastro et al. teach the use of reflux in toluene (corresponding to a temperature of 110 °C) with iodine (an oxidant) on page 632. Accordingly, a person having ordinary skill seeking to determine which permutation of known transformations would provide an optimum conversion of CBD to CBN would have been motivated to test the combination of the acid-catalyzed step of Adair et al. with the aromatization step of Pollastro et al., which conditions would be embraced by instant claim 19.
Additional Closest Prior Art
Regarding instant claims 1 and 9, these claims involve a first step of contacting CBD or CBDV with a solvent and a base. A first step in the conversion of CBD or CBDV (ultimately to CBN or CBNV) would typically be carried out using an acid. For instance, D’Spain et al. (U.S. Patent PGPub No. 2022/0002261 A1) teach on page 1:
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The prior art teaches an initial acid-catalyzed step followed by treating with a halogen (an oxidant). Regardless, claims 1 and 9 additionally require a step of contacting an oxidant with a solvent, heating the oxidant mixture and then adding the heated mixture to a separately heated mixture (containing CBD/CBDV and a base). Even if a person having ordinary skill in the art were to include a base (instead of an acid), separately heating an oxidant is not a common practice for oxidizing cannabinoids and the Examiner finds insufficient guidance in the prior art regarding why this approach should be taken. For instance, Pollastro (J. Nat. Prod. 2018, 81, 630-633) teach aromatization procedures on page 632 where to a solution “was added iodine” or that “iodine (200 mg) was added.” Absent some reason why it would be necessary or desirable to perform the reaction in the instantly claimed way, the Examiner finds that the prior art does not reasonably suggest the methods of instant claims 1 and 9.
Allowable Subject Matter
Claims 1-5, 8-13 and 16 are allowed.
Claims 7 and 15 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.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached at 571-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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