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
This application, filed 03/21/2024 is a National Stage entry of PCT/US2022/045677, International Filing Date: 10/04/2022. PCT/US2022/045677 Claims Priority from Provisional Application 63252921, filed 10/06/2021.
Status of Claims
Claims 1-15, 30-34, 36, and 38-39 are pending as of the response filed on 6/12/26. Claims 16-29, 35, 37, and 40-41 have been canceled.
Applicant’s election without traverse of the claims of invention I, 1-15 and 38-39; and the species shown below in the reply filed on 6/12/26 is acknowledged:
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.
Claims 30-34 and 36 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 6/12/26.
The elected species shown above has been found to be free of the prior art. Therefore, in accordance with MPEP 803.02, search and examination were extended to the additionally claimed species. The restriction between inventions I and II is maintained.
Claims 1-15 and 38-39 were examined and are rejected.
Claim Rejections-35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claims 1, 3-4, and 11-15 are rejected under 35 U.S.C. 101 because the claimed invention is directed to a judicial exception without significantly more. The claim(s) recite(s) compounds of formula (I) and (Ia). This judicial exception is not integrated into a practical application because formulas (I) and (Ia) encompass naturally occurring compounds, i.e., compounds present or isolated from natural plant products. For instance, a compound of formula (I) as shown below is present in Cannabis sativa:
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; see Radwan et. al., J. Nat. Prod., vol. 72(5), pp. 906-911, publ. 2009, specifically title and abstract, and p. 908, Fig. 1. The claim(s) does/do not include additional elements that are sufficient to amount to significantly more than the judicial exception because there is no evidence that the claims amount to more than the compounds as they are present in nature. Specifically, although claims 14-15 are drawn to a composition that includes a carrier, diluent, or excipient, the language is exceptionally broad and includes for example water as a carrier, and there is no evidence of the record that the properties of compound 5 as shown above would be altered as a result of any carrier, diluent, or excipient.
Claim Rejections-35 USC § 112
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 1-15 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.
Independent claim 1 recites “R2 is either a moiety of the formula (III-A), -(CH2)nCH3…” , “or a moiety of the formula (III-B), -(CH2)m(CH=CH)(CH2)pCH3”. This language renders the claim indefinite, since it is uncertain if formula (III-A) refers to -(CH2)nCH3 and if formula (III-B) refers -(CH2)m(CH=CH)(CH2)pCH3 , or if they represent alternative embodiments themselves, due to the presence of the commas between “formula (III-A)” and “formula (III-B)” and -(CH2)nCH3 and -(CH2)m(CH=CH)(CH2)pCH3, respectively. Dependent claims 2-15 are similarly rejected.
For the sake of compact prosecution, the claims were examined as if formula (III-A) referred specifically to -(CH2)nCH3 and formula (III-B) referred specifically to -(CH2)m(CH=CH)(CH2)pCH3. To overcome this rejection, it is suggested that references to “formula (III-A)” and “formula (III-B)” be removed from claim 1.
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(s) 1, 3-4, 9, and 11-14 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Radwan et. al., J. Nat. Prod., vol. 72(5), pp. 906-911, publ. 2009.
Radwan discloses biologically active cannabinoid compounds isolated from cannabis sativa (title & abstract). In particular, Radwan discloses compound 5 shown below (p. 908, Fig. 1):
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. This compound is included within formula (I) of the claims having X and Y each -OH; RA=H; R2=-(CH2)nCH3, wherein n=4; RB=-O(CO)CH3; and R1=
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, wherein each dashed bond represents a double bond. Radwan discloses compound 5 exhibited antileishmanial activity when evaluated in vitro (p. 909, Table 5); therefore, it would have been reasonably expected compound 5 would have been present with a pharmaceutically acceptable carrier as required by claim 14 for testing.
Regarding claim 11, “wherein the compound inhibits an activity selected from the group consisting of TNF, …”; claim 12, “wherein the compound has at least about 100-fold decreased toxicity ….”; and claim 13, “wherein the compound has at least about 2 fold selectivity for inhibiting the CB2 receptor over the CB1 receptor”, these limitations are drawn to properties of the claimed compound. A compound and its properties are inseparable. See MPEP 2141.02, In re Papesch, 315 F.2d 381, 391, 137 USPQ 43, 51 (CCPA 1963) ("From the standpoint of patent law, a compound and all its properties are inseparable."). As Radwan discloses the same compound as claimed, it would necessarily possess the characteristics recited by claims 11-13.
Radwan therefore anticipates the claims.
Claim(s) 1-2, 4, 6, 8, 11-13, and 38 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Metcalf, WO 2021041637 A1, publ. 3/4/2021, international filing date 8/27/2020, cited in the IDS.
Metcalf discloses compositions comprising cannabinoids in anionic form dissolved in glycerol (title & abstract; p. 1, line 25-p. 2, line 7). In particular, Metcalf discloses the cannabinoid ion compound as 2-(3,7-dimethylocta-2,6-diene-1-yl)-5-propyl-1,4-benzoquinone-3-oxide (p. 11, lines 14-15; p. 20, line 13):
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. Metcalf further discloses preparing the cannabinoid anions from the protonated form, i.e., the -OH form by deprotonation with KOH (p. 12, lines 10-16 and lines 25-29; p. 13, lines 6-11 and 19-31). Therefore, it would have been expected that prior to preparation as the anion, 2-(3,7-dimethylocta-2,6-diene-1-yl)-5-propyl-1,4-benzoquinone-3-oxide would have necessarily been present as 2-(3,7-dimethylocta-2,6-diene-1-yl)-3-hydroxy-5-propyl-1,4-benzoquinone:
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. This compound is recited in claim 38, and further included within formula (Ia) having X and Y each =O; RA=H; R2=-(CH2)nCH3, wherein n=2; RB=-OH; and R1=
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, wherein two of the dashed lines represent double bonds and one of the dashed lines is a single bond. Regarding claim 11, “wherein the compound inhibits an activity selected from the group consisting of TNF, …”; claim 12, “wherein the compound has at least about 100-fold decreased toxicity ….”; and claim 13, “wherein the compound has at least about 2 fold selectivity for inhibiting the CB2 receptor over the CB1 receptor”, these limitations are drawn to properties of the claimed compound. A compound and its properties are inseparable. See MPEP 2141.02, In re Papesch, 315 F.2d 381, 391, 137 USPQ 43, 51 (CCPA 1963) ("From the standpoint of patent law, a compound and all its properties are inseparable."). As Metcalf discloses the same compound as claimed, it would necessarily possess the characteristics recited by claims 11-13. Metcalf thus anticipates the claims.
(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, and 9-15 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Meiri et. al., WO 2022144878 A1, publ. 7/7/2022, international filing date 12/27/2021, provisional application, 63/131075 filing date 12/28/2020. The provisional application provides support to the subject matter disclosed below.
Meiri discloses the following cannabinoid in a pharmaceutical composition (title & abstract; para [008], [010]):
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. The shown compound is included within formula (I) as claimed, having X= -OH; Y=-O(CO)CH3; RA=H; R2=-(CH2)nCH3, wherein n=4; RB=-OH; and R1=
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, wherein 2 dashed bonds represents a double bond, and one dashed bond represents a single bond. Meiri further discloses the pharmaceutical composition to additionally comprise an acceptable carrier (para [099], [0102]), and to be suitable for oral administration (para [0106]) and topical administration (para [0157]).
Regarding claim 11, “wherein the compound inhibits an activity selected from the group consisting of TNF, …”; claim 12, “wherein the compound has at least about 100-fold decreased toxicity ….”; and claim 13, “wherein the compound has at least about 2 fold selectivity for inhibiting the CB2 receptor over the CB1 receptor”, these limitations are drawn to properties of the claimed compound. A compound and its properties are inseparable. See MPEP 2141.02, In re Papesch, 315 F.2d 381, 391, 137 USPQ 43, 51 (CCPA 1963) ("From the standpoint of patent law, a compound and all its properties are inseparable."). As Meiri discloses the same compound as claimed, it would necessarily possess the characteristics recited by claims 11-13.
Meiri thus anticipates the claims.
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.
Claim(s) 1-2, 4, 6, 8, 14, and 38-39 is/are rejected under 35 U.S.C. 103 as being unpatentable over Blanco et. al., US 8772349 B2, patented 7/8/2014, cited in the IDS.
Blanco teaches cannabinoid quinone derivative compounds having activity as PPAR-γ agonists for treating diseases associated with impaired PPAR-γ function (title & abstract; col. 1, lines 15-20). Blanco teaches the cannabinoid quinone compounds to have the following structural formula (col. 4, lines 10-50):
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. Blanco exemplifies the cannabinoid quinone derivative CBG-Q shown below (col. 5, lines 26-35):
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. Blanco teaches the cannabinoid quinone compound in a pharmaceutical composition along with an excipient, wherein the pharmaceutical compositions are suitable for various routes of delivery including oral, nasal, pulmonary, or transdermal (col. 7, lines 4-46).
Blanco teaches the cannabinoid quinone derivative CBG-Q shown below as a PPAR-γ agonist for pharmaceutical compositions:
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. Although this compound is excluded by the proviso in instant claim 1, CBG-Q is structurally very similar to two compounds that are included within formula (Ia) and instant claim 38, shown below, differing only by the number of carbon atoms in the R2 position:
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. Formula X is included within formula (Ia) having X and Y both =O; RA=H; R2=-(CH2)nCH3, wherein n=3; RB=-OH; and R1=
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. Formula XI is included within formula (Ia) having X and Y both =O; RA=H; R2=-(CH2)nCH3, wherein n=5; RB=-OH; and R1=
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. Namely, the compound of formula X differs from CBG-Q by the loss of one -CH2- group from the –(CH2)nCH3 group for the position corresponding to R2, and the compound of formula XI differs from CBG-Q by the addition of one -CH2- group to the –(CH2)nCH3 group for the position corresponding to R2. As such, formula X and XI are homologs of CBG-Q, differing only by a -CH2- group. Homologs would be reasonably expected, due to their high degree of structural similarity to possess similar properties and characteristics, and as such would be prima facie obvious. See MPEP 2144.09(II): Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or 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. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
Therefore, it would have been prima facie obvious for one of ordinary skill in the art, before the effective filing date of the claims to have arrived at compounds of formulas X and XI as disclosed above in consideration of the teachings of Blanco, and have reasonably expected that these compounds and pharmaceutical compositions comprising these compounds would, similar to CBG-Q, have had pharmaceutical activity as PPAR-γ agonists in the absence of evidence to the contrary.
Information Disclosure Statement
The IDS filed on 4/4/24 has been considered.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SARAH PIHONAK whose telephone number is (571)270-7710. The examiner can normally be reached Monday-Friday 9:00-5:30 EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney Klinkel can be reached at 571-270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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SARAH . PIHONAK
Primary Examiner
Art Unit 1627
/SARAH PIHONAK/Primary Examiner, Art Unit 1627
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