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 is a 371 National Stage Entry of PCT/GB2022/051207 filed on May 12, 2022 which claims priority to foreign application No. GB2106787.1 filed on May 12, 2021.
Status of Claims
Acknowledgement is made of original (4, 8, 10, 12, 22-23, 28-29, 33, 37, 41), amended (1-3, 5-7, 9, 11, 20-21, 24-27, 30-32, 43, 47), and cancelled (13-19, 34-36, 38-40, 42, 44-46, 48), claims filed on June 3, 2024. Claims 1-12, 20-33, 37, 41, 43, 47 are pending in instant application.
Specification
The title of the invention is not descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed. The title refers to the instantly claimed compounds as “rescorcinols” which refers to a small moiety of the instantly claimed compounds (1,3-benzendiol). The more relevant classification that covers the core of compounds claimed is “6-hydroxy cannabidiols” or “6-hydroxy cannabidivarin” (see claims 1, 3). The utility should also be reflected in the title (e.g. epilepsy or seizure, see claims 20, 21). This may result in a slightly longer title, but the loss in brevity is offset by the gain in informative value for indexing, classifying, and searching (see MPEP § 606.01).
The following title is suggested: 6-HYDROXY CANNABIDIOL DERIVATIVES, METHODS FOR THEIR MANUFACTURE, AND TREATMENT OF SEIZURES.
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 22-33, 37, 41, 43 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.
Regarding claims 22-33, 37, 41, 43, Claim 22 recites the limitation "formula (I)" in line 1. There is insufficient antecedent basis for this limitation in the claim; the claim does not depend from claim 1 and thus does not include the structure or limitations of formula (I). Claims 23-27 depend from claim 22 and do not remedy this deficiency by defining formula (I).
Likewise, the same issue occurs for independent claims:
Claim 28, “formula (V)”, dependent claims 29-32 do not remedy.
Claim 33, “formula (VII)”, no dependent claims.
Claim 37, “formula (IX)”, no dependent claims.
Claim 41, “formula (X)”, no dependent claims.
Claim 43, “formula (Xa)”, no dependent claims. Notably no “formula Xa” in any other claims.
The Examiner recommends either amending dependency to establish antecedent basis or amending to include the reference structure and its structural limitations (notably required for claim 43).
Further regarding claim 31, claim 31 recites “the reagent” which should read “the triflation reagent” for proper antecedent basis.
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 30 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.
Independent claim 28 recites “R7 and R8 are independently H, Ac, or Piv.” The instant specification defines Ac as an acetyl group (-C(=O)CH3), and Piv as a pivaloyl group (-C(C=O)C(CH3)3) (see instant spec. at p. 26 ¶[0160]). Dependent claim 30 recites “wherein R7 and R8 are OH”. OH is excluded as a structural limitation in the independent claim.
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
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 7 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by VanLandingham et. al.1
VL teaches 6α-Hydroxycannabidiol (6-OH-CBD, CAS Registry No. 58940-28-6) is a metabolite of the anticonvulsant cannabidiol (CBD) (see VL at p. 1306 left col. ¶2; p. 1309 right col. ¶5; p. 1310 Table 6; p. 1310 right col. ¶1; p. 1311 left col. ¶1; p. 1312 left col. ¶4).
CAS# 58940-28-6
Formula III
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CAS# 58940-28-6 reads on Formula III when R1 is (CH2)4CH3, R2 is CH, and R3 is H.
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.
Claim(s) 1-4, 6, 8-10, 21 are rejected under 35 U.S.C. 103 as being unpatentable over VL as applied to claim 7.
Regarding claims 1-4, 6, 8-10 and a compound of Formula I or II or III or IV, Recall VL teaches 6α-Hydroxycannabidiol (6-OH-CBD, CAS Registry No. 58940-28-6) (see VL at p. 1310 Table 6).
CAS# 58940-28-6
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Formula I
Formula II
Formula III
Formula IV
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wherein
R1 is CH3 or CH2CH3
wherein
R1 is CH2CH2CH3,
R2 is CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3,
R2 is H or CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3
The prior art differs from the instant claims as follows: While VL teaches structurally similar CAS# 58940-28-6, VL does not specify i) wherein R1 is CH3 or CH2CH3 or CH2CH2CH3 or R2/R3 as CH3 ii) a method of administering CAS# 58940-28-6 to treat seizures.
However,
Regarding i) The structural differences in the claimed Formulas and CAS# 58940-28-6 amount to differences in +/- CH2.
Regarding ii) VL teaches cannabidiol is an anti-seizure treatment (see VL at p. 1304 left col. ¶1). VL hypothesizes one of the abundant metabolites 7-OH-CBD (see VL at p. 1311 left col. ¶1) may contribute to the efficacy of CBD in seizure patients (see VL at p. 1312 left col. ¶3).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding i) and +/- CH2, per MPEP § 2144.09I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…homologs (compounds differing regularly by the successive addition of the same chemical group, e.g. by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (emphasis added, see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. In addition, per MPEP § 2144.08(II)(A)(4)(c), the closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. This includes H vs Me, In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring) (compare 6-OH-CBD’s -OH or -H, with Formula II/III’s R2 or R3 as CH3, Formula IV’s OMe). Here, the prior art teaches a highly similar structural homolog (6-OH-CBD) of the instantly claimed invention (Formulas I-IV).
Regarding ii) and treating seizures, per MPEP § 2143(I)(A), a prima facie case of obviousness exists for combining prior art elements according to known methods to yield predictable results. It would have been obvious to one skilled in the art to administer structurally similar compounds to CBD and its metabolite 6-OH-CBD with a reasonable expectation of success because the prior art teaches CBD is an anti-convulsant known to treat seizures, and suggests CBD metabolite effects could increase efficacy in seizure patients (see VL) (see also MPEP § 2143(I)(G)).
Furthermore, it is well-within the ordinary skill in art to:
incorporate one short-chain alkyl group (such as instantly claimed methyl, ethyl, or propyl) in lieu of another (such as the prior art pentyl), or incorporate a methyl group in lieu of a hydrogen.
administer a structurally similar drug to treat a known condition.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claim(s) 11-12 are rejected under 35 U.S.C. 103 as being unpatentable over VL as applied to claim 1-4, 6-10, 21 in view of Remington2.
The prior art differs from the instant claims as follows: While VL teaches an obvious compound of instant application, VL does not specify a composition further comprising additional ingredients or formulating.
However,
Remington teaches formulating active ingredients as suspensions (see Remington at p. 767), emulsions (see Remington at p. 759), syrups (see Remington at p. 754), mouthwashes (see Remington at p. 751), etc. Remington teaches additional components to achieve desired formulations and their respective advantages. For example, adding a flavoring agent to form a syrup to appeal to pediatrician prescribers (see Remington at p. 754 left col. ¶5-4).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
It would have been obvious to one skilled in the art to formulate an active ingredient such as a compound of instant claims as a composition with an expectation of success because the prior art teaches CBD or CBD metabolites have therapeutic properties (as taught by VL), and readily informs artisans how to formulate compositions comprising active agents with additional ingredients for various administration routes (as taught by Remington).
Furthermore, it is well-within the ordinary skill in art to formulate a compound with a therapeutic use as a composition.
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over VL as applied to claim 1-4, 6-10, 21 in view of Silva et. al.3
Regarding claim 20 and treating epilepsy, VL teaches CBD is an anticonvulsant, and sometimes used in combination with clobazam to treat seizures associated with Lennox-Gastaut syndrome or Dravet syndrome (see VL at p. 1304 left col. ¶1).
The prior art differs from the instant claims as follows: While VL teaches treating seizures, VL does not specify treating epilepsy.
However,
Silva teaches CBD has anti-epileptic efficacy (see Silva at p. 2 left col. ¶2).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Per MPEP § 2143(I)(A), a prima facie case of obviousness exists for combining prior art elements according to known methods to yield predictable results. It would have been obvious to one skilled in the art to administer structurally similar CBD compounds (as taught by VL) to treat epilepsy with a reasonable expectation of success because the prior art teaches CBD or CBD metabolites for treating seizures (as taught by VL) and epilepsy (as taught by Silva).
Furthermore, it is well-within the ordinary skill in art to administer structurally similar compounds for the same purpose as taught by the prior art (treating epilepsy).
Therefore, an artisan would arrive at the same invention as presently claimed for reasons taught in the prior art.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-4, 6-10, 11-12, 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2, 4-5, 24-30 of copending Application No. 18/560,3164 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claims 1-4, 6-10, 21, App’316 claims a compound of Formula I (see App’316 claims 1-2) which corresponds with instant Formulas I-IV.
App’316 Formula I
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Formula I
Formula II
Formula III
Formula IV
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wherein
R1 is CH3 or CH2CH3
wherein
R1 is CH2CH2CH3,
R2 is CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3,
R2 is H or CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3
Regarding instant claims 11-12 and a composition, App’316 claims 4-5 correspond to instant 11-12.
Regarding instant claims 20-21 and a method of treating epilepsy or seizures, App’316 claims a method of treating epilepsy or generalized seizures, optionally in combination with other anti-seizure drugs (see App’316 at claim 24-30).
The copending claims differ from the instant claims as follows: While App’316 teaches structurally similar Formula I, App’316 does not specify wherein instant R1 is CH3 or CH2CH3 or CH2CH2CH3 or (CH2)4CH3 or R2/R3 as CH3.
However,
Regarding i) The structural differences in the claimed Formulas amount to differences in +/- CH2.
Therefore, it would have been obvious to one of ordinary skill in the art to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding +/- CH2, per MPEP § 2144.09I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…homologs (compounds differing regularly by the successive addition of the same chemical group, e.g. by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (emphasis added, see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. In addition, per MPEP § 2144.08(II)(A)(4)(c), the closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. This includes H vs Me, In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring) (compare App’316 Formula I -OH or -H, with Formula II/III’s R2 or R3 as CH3, Formula IV’s OMe). Here, the prior art teaches a highly similar structural homolog (App’316 Formula I) of the instantly claimed invention (Formulas I-IV).
Furthermore, it is well-within the skill in the art to incorporate one short-chain alkyl group (such as instantly claimed methyl, ethyl, or propyl) in lieu of another (such as the prior art pentyl), or incorporate a methyl group in lieu of a hydrogen.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 47 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-2 of copending Application No. 18/560,3465 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
App’346 claims Formula I (see App’346 claims 1-2) which reads on instant Formula V when R1 is H, R2 is H, R3 is H, and X1 is Br.
App’346 Formula I
Instant Formula V
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This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-4, 6-12, 20-21 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-10 of U.S. Patent No. 12,383,512 B26 in view of Remington and VL. Although the claims at issue are not identical, they are not patentably distinct from each other.
Regarding instant claim 7, US’512 claims a method of treating epilepsy in a subject with a composition comprising 6-hydroxy cannabidiol (6-OH CBD, CAS# 58940-28-6) (see US’512 claims 1-5, 7-10), which reads on instant Formula III when R1 is (CH2)4CH3, R2 is CH, and R3 is H.
US’512 6-OH CBD
CAS# 58940-28-6
Instant
Formula III
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Regarding instant claims 1-4, 6-10, 20, US’512 6-OH CBD is structurally similar to instant Formulas I-IV.
US’512 6-OH CBD
CAS# 58940-28-6
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Instant Formula I
Instant Formula II
Instant Formula III
Instant Formula IV
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wherein
R1 is CH3 or CH2CH3
wherein
R1 is CH2CH2CH3,
R2 is CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3,
R2 is H or CH3,
R3 is H or CH3
wherein
R1 is CH2CH2CH3
Regarding instant claim 11, US’512 claims wherein the pharmaceutically composition further comprises and excipient (see US’512 claim 6).
The prior art differs from the instant claims as follows: While US’512 claims structurally similar CAS# 58940-28-6, US’512 does not claim i) wherein R1 is CH3 or CH2CH3 or CH2CH2CH3 or R2/R3 as CH3, ii) a method of administering CAS# 58940-28-6 to treat seizures (instant claim 21), iii) formulation of the composition (instant claim 12).
However,
Regarding i) and +/- CH2, the structural differences in the claimed Formulas and CAS# 58940-28-6 amount to differences in +/- CH2.
Regarding ii) and seizure, VL teaches 6α-Hydroxycannabidiol (6-OH-CBD, CAS Registry No. 58940-28-6) is a metabolite of the anticonvulsant cannabidiol (CBD) (see VL at p. 1306 left col. ¶2; p. 1309 right col. ¶5; p. 1310 Table 6; p. 1310 right col. ¶1; p. 1311 left col. ¶1; p. 1312 left col. ¶4). VL teaches cannabidiol is an anti-seizure treatment (see VL at p. 1304 left col. ¶1). VL hypothesizes one of the abundant metabolites 7-OH-CBD (see VL at p. 1311 left col. ¶1) may contribute to the efficacy of CBD in seizure patients (see VL at p. 1312 left col. ¶3).
Regarding iii) and formulation, Remington teaches formulating active ingredients as suspensions (see Remington at p. 767), emulsions (see Remington at p. 759), syrups (see Remington at p. 754), mouthwashes (see Remington at p. 751), etc. Remington teaches additional components to achieve desired formulations and their respective advantages. For example, adding a flavoring agent to form a syrup to appeal to pediatrician prescribers (see Remington at p. 754 left col. ¶5-4).
Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to arrive at the instantly claimed invention with a reasonable expectation of success in view of the prior art for at least the following reason(s):
Regarding i) +/- CH2, per MPEP § 2144.09I)-(II), “[a] prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities” because “[c]ompounds which are…homologs (compounds differing regularly by the successive addition of the same chemical group, e.g. by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties” (emphasis added, see, e.g., MPEP § 2144.09(I)-(II)), and the Court has stated that “[i]f a person of ordinary skill can implement a predictable variation, § 103 likely bars its patentability.” KSR, 127 S.Ct. at 1740. In addition, per MPEP § 2144.08(II)(A)(4)(c), the closer the physical and/or chemical similarities between the claimed species or subgenus and any exemplary species or subgenus disclosed in the prior art, the greater the expectation that the claimed subject matter will function in an equivalent manner to the genus. This includes H vs Me, In re Druey, 319 F.2d 237, 240, 138 USPQ 39, 41 (CCPA 1963) (omission of methyl group from pyrazole ring) (compare 6-OH-CBD’s -OH or -H, with Formula II/III’s R2 or R3 as CH3, Formula IV’s OMe). Here, the patent claims a highly similar structural homolog (6-OH-CBD) of the instantly claimed invention (Formulas I-IV).
Regarding ii) seizures, per MPEP § 2143(I)(A), a prima facie case of obviousness exists for combining prior art elements according to known methods to yield predictable results. It would have been obvious to one skilled in the art to administer a known epileptic treatment to treat seizures with a reasonable expectation of success because the prior art teaches the known compound (claimed by US’512) as an anti-convulsant seizure treatment (as taught by VL).
Regarding iii) formulation, per MPEP § 2143(I)(D), a prima facie case of obviousness exists for applying a known technique to a known method or product ready for improvement to yield predictable results. It would have been obvious to one skilled in the art to formulate a known composition with a therapeutic use because the prior art readily informs artisans how to formulate advantageous compositions comprising active agents with additional ingredients for various administration routes (as taught by Remington).
Furthermore, it is well-within the ordinary skill in art to:
incorporate one short-chain alkyl group (such as instantly claimed methyl, ethyl, or propyl) in lieu of another (such as the prior art pentyl), or incorporate a methyl group in lieu of a hydrogen.
apply a known epileptic treatment to treat seizures.
formulate a known composition.
Therefore, an artisan would arrive at the same invention as presently claimed.
Allowable Subject Matter
Claim 5 is 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.
Regarding claim 47, if a terminal disclaimer is filed over App’346, instant claim 47 will be allowable over the prior art. The closest prior art to formula IX is Anagnostaki et. al.7 Anagnostaki teaches anti-carveol Compound 10 which differs from instant Formula IX in double bond placement and lack of OH. No reasonable suggestion or motivation was found to alter compound 10 to arrive at a compound of instant formula IX.
Anagnostaki Compound 10
Instant Formula IX
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The closest prior art to formula V is US 2012/0172339 A1 to Makriyannis et. al.8 Makriyannis teaches compound 311 (CAS# 1260669-33-7, see Makriyannis at p. 12 Table 1 left col.) which differs from instant formula V by a missing -OR1. No suggestion or motivation was found to modify compound 311 to include an -OR1 at the 6-position core.
Makriyannis Compound 311
Instant Formula V
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Claims 22-33, 37, 41 and 43 presently have 112(b) issues, which if resolved, would be allowable over the prior art.
Regarding claims 22-27, the closest prior art to claims 22-27 is CN 112592260 A to Li et. al.9 Li teaches the following similar synthesis (see Li at p. 8 ¶[0026]) comprising reacting compound 1 with pentyl boric acid and tetra-triphenyl phosphine palladium and potassium phosphate:
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The synthesis in Li differs from the instant claims in: i) the lack of the 6 position hydroxyl in the starting material and product (cannabidiol), ii) instant Y of Formula VI is not met by pentyl boric acid, iii) Li compound 1 halogen is Cl not Br or I, iv) the base is potassium phosphate and not a reagent listed in claim 26. While any one of these changes might be obvious to an artisan, no reasonable suggestion or motivation was found to make all such changes.
Regarding claims 28-32, 33, 37, 41, 43, the closest prior art appears to be Lander et. al.10 Lander teaches the synthesis of cannabidiol metabolites including 6-OH CBD (see Lander at p. 9 right col. Formula Via and at p. 14 left col. “6a- (VIa) and 6P-HydroxycannabidioZ (VIIa)”). Lander differs from the instant claims in that 6-OH CBD is an obvious compound of instant product claims, but Lander does not teach the synthetic steps or strategy instantly claimed to arrive at 6-OH CBD. No reasonable suggestion or motivation was found to make all such changes to Lander’s synthetic strategy to arrive at the methods instantly claimed.
Conclusion
The specification is objected to.
Claims 1-4, 6-12, 20-33, 37, 41, 43, 47 are rejected.
Claim 5 is objected to.
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/S.R./Examiner, Art Unit 1627
/JENNIFER A BERRIOS/ Primary Examiner, Art Unit 1613
1 VanLandingham et. al. "A Phase 2, Double-Blind, Placebo-Controlled Trial to Investigate Potential Drug-Drug Interactions Between Cannabidiol and Clobazam" Journal of Clinical Pharmacology, 2020, 60, 10, 1304-1313. Hereinafter VL.
2 Remington's Pharmaceutical Sciences (21st Ed) New York, NY: Lippincott Williams and Wilkins 2005. Select Pages. Hereinafter Remington.
3 Silva et. al. "Cannabidiol in the Treatment of Epilepsy: A Focused Review of Evidence and Gaps" Front. Neurol. 2020, 11, 531939, 1-6. DOI: 10.3389/fneur.2020.531939. Hereinafter Silva.
4 Cite No. 267 in the IDS filed 5/31/24. Effective filing date May 12, 2021. Hereinafter App’316.
5 Cite No. 269 in the IDS filed 5/31/24. Effective filing date of 5/12/21. Hereinafter App’346.
6 Patented August 12, 2025. Hereinafter US’512.
7 Cite No. 169 in the IDS filed 5/31/24. Anagnostaki et. al. "Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes" Organic Letters, 2013, 15, 1, 152-155. DOI: 10.1021/ol3031999. Hereinafter Anagnostaki.
8 Published July 5, 2012. Hereinafter Makriyannis.
9 Filed November 30, 2020. Published April 2, 2021. Cite No. 159 in the IDS 5/31/24. Hereinafter Li.
10 Lander et. al. "Total syntheses of cannabidiol and Δ1-tetrahydrocannabinol metabolites" J. Chem. Soc. Perkin Trans. 1, 1976, 8-16. DOI: 10.1039/p19760000008. Cite No. 183 in the IDS filed 5/31/24. Hereinafter Lander.