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 .
Claims 31-50, submitted on 16 August 2024, represent all claims currently under consideration.
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.
Priority
This application is a continuation of PCT/US2023/85277, filed 21 December 2023, which claims priority to provisional US 63/434,723, filed 22 December 2022. The effective filing date is 22 December 2022.
Information Disclosure Statement
Two Information Disclosure Statement (IDSs), submitted on 5 September 2024 and 17 August 2026, are acknowledged and have been considered.
Specification
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details. The currently submitted abstract is less than 50 words long.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
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 35 and 36 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. Claims 35 and 36 recite the limitation "wherein R2 and R3 are independently H or methyl" in lines 2-3. There is insufficient antecedent basis for this limitation in the claim as Claim 34, which Claims 35 and 36 depend on, state that variable R2 can only be C1-C6 alkyl.
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 35 and 36 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. Claims 35 and 36 recite the limitation "wherein R2 and R3 are independently H or methyl". These claims depend on Claim 34 and Claim 31, which do not state that variable R2 can be hydrogen, causing these claims to be broader than the claims which they depend on. 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 31-50 are rejected under 35 U.S.C. 103 as being unpatentable over Gray (US 2025/0186397; Publication Date: 12 June 2025; Priority to 2 March 2022) in view of Manda (Biomedical Chromatography, 2017: 31, e3815) and Rautio (Nature Reviews Drug Discovery, Vol. 7, March 2008).
Determining the Scope and Contents of the Prior Art:
Gray discloses the use of mesembrine alkaloids for use in the treatment of mood disorders. In particular, the invention provides compositions and methods for improving symptoms associated with anxiety and/or mood disorders, or a disorder where anxiety and/or depression are co-morbid (Abstract). Preferably, the mesembrine alkaloid is mesembrenol and/or mesembranol. In a further embodiment, the mesembrine alkaloid is mesembranol (Paragraph 0021). The diseases or conditions associated with anxiety and/or mood disorders is selected from the group consisting of generalized anxiety disorder, panic disorder, social anxiety disorder, phobia related disorder, major depressive disorder, clinical depression, bipolar I disorder, bipolar II disorder, cyclothymic disorder, and other disorders (Paragraph 0022). Preferably, the one or more mesembrine alkaloids is administered with one or more pharmaceutically acceptable excipients (Paragraph 0024). Mesembranol was shown to be effective in various models of animal stress (See Figures 3, 4, 7, and 9). Mesembranol has the structure
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and is the compound that forms following metabolism of the compounds of the examined application via hydrolysis. The compounds of the invention may be present or administered in the form of a prodrug of the active compound (Paragraph 0085).
Manda (See IDS, 5 September 2024) performed a study of the in vivo pharmacokinetics of mesembrenone and mesembrine, the two main pharmacologically active alkaloids present in Scletium tortuosum extracts. The i.v. plasma pharmacokinetics of mesembrine and mesembrenenone was performed in the mouse. However, the oral bioavailability of both alkaloids was poor and the plasma levels were below the detection limits. Figure 1 (Page 2) shows the structures of mesembrine and mesembrenone
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.
Rautio provides a review of prodrugs. Prodrugs are bio-reversible derivatives of drug molecules that undergo an enzymatic and/or chemical transformation in vivo to release the active parent drug, which can then exert the desired pharmacological effect. Prodrugs are an established tool for improving physicochemical, biopharmaceutical or pharmacokinetic properties of pharmacologically active agents (Abstract). A bio-precursor prodrug is a prodrug that does not contain a carrier or pro-moiety, but results from a molecular modification of the active agent itself. The modification (for example, oxidation or reduction) generates a new compound that can be transformed metabolically or chemically with the resulting compound being the active agent (it can also be referred to as an active metabolite) (Page 255). Figure 1 provides a representative illustration of the prodrug concept, demonstrating the common use of esters, phosphates, amides, carbonates, and carbamates. Esters are the most common prodrugs used, and are activated by enzymatic hydrolysis. Ester prodrugs are most often used to enhance lipophilicity of a parent compound. Once in the body, the ester bond is readily hydrolyzed by ubiquitous esterases found within the blood, liver, and other organs and tissues (Esters as prodrugs of carboxyl, hydroxyl, and thiol functionalities) (Page 256).
Ascertaining the Differences Between the Prior Art and the Claims at Issue:
Gray does not directly disclose the use of pro-drugs of mesembranol.
Resolving the Level of Ordinary Skill in the Pertinent Art:
The artisan would be a medical practitioner with further expertise and training in the use of therapeutics, including pharmacokinetics and pharmacodynamics with respect to the administration of drugs for the treatment of disease.
Considering Objective Evidence Present in the Application Indicating Obviousness or Nonobviousness:
Gray, Manda, and Rautio are considered analogous to the claimed invention as all are involved drug development and pharmacology. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify mesembranol to form a pro-drug using the well-known techniques of forming esters as taught by Rautio, as Gray states directly that pro-drugs can be used to practice this invention, and Manda demonstrates that two similar alkaloids found within the same plant as mesembranol have poor oral bioavailability. The formation of pro-drugs of mesembranol in order to improve oral bioavailability is prima facie obvious use of a known technique to improve similar products in the same way (See MPEP 2143 I (C)); Gray demonstrates that mesembranol is a compound useful for the treatment of anxiety and depression; however, similar alkaloid compounds from the same plant possess poor oral bioavailability. Pro-drug formation, as taught by Rautio, is commonly employed in the pharmaceutical arts in order to enhance oral bioavailability, and the artisan would recognize this, and would be motivated to form ester pro-drugs of this compound in order to allow for enhanced oral delivery, as oral delivery is a preferred method of treatment due to ease for the patient.
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 31 and 44-48 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 17 and 20 of U.S. Patent No. 11,999,694 (Patent Date: 4 June 2024) (‘694).
Claim 17 of ‘694 (See IDS, 5 September 2024) is directed to a compound of the genus
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or a pharmaceutically acceptable salt thereof, wherein R3 is -OC(O)alkyl, optionally substituted with alkoxy, OH, halogen, or -O(CH2)pCH3, and p is 2, 3, or 4. Claim 20 is directed to several specific compounds such as
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. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘694 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘694 differ from those of the examined application by the presence of a single double bond. The specification of ‘694 demonstrates that these compounds are inhibitors of SERT (Table 14, Column 583), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
Claims 31, 44, and 47 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 17 of U.S. Patent No. 12,269,800 (Patent Date: 8 April 2025) (‘800).
Claim 17 of ‘800 is directed to a compound of genus
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or a pharmaceutically acceptable salt thereof, wherein
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. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘800 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘800 differ from those of the examined application by the presence of a single double bond. The specification of ‘800 demonstrates that these compounds are inhibitors of SERT (Table 14, Column 573), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
Claims 31 and 44-48 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 19/069,687 (Amended Claims of 4 March 2025) (‘687).
Claim 1 of ‘687 is directed to a compound of genus
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or a pharmaceutically acceptable salt thereof, wherein
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. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘687 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘687 differ from those of the examined application by the presence of a single double bond. The specification of ‘687 demonstrates that these compounds are inhibitors of SERT (Table 14, Page 384), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 31 and 44-48 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 135 and 138 of copending Application No. 18/705,647 (Amended Claims of 29 April 2024) (‘647).
Claim 135 of ‘647 is drawn to a compound of genus
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or a pharmaceutically acceptable salt thereof, wherein R1 is a C1-C7 alkyl or H;
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and
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. Claim 138 is drawn to a compound of Claim 135 wherein ring A is
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. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘647 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘647 differ from those of the examined application by the presence of a single double bond. The specification of ‘647 demonstrates that these compounds are inhibitors of SERT (Table 14, Page 365), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 31-50 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1, 31, and 32 of copending Application No. 18/799,146 (Amended Claims of 9 August 2024) (‘146) (reference application).
Claim 1 of ‘146 is drawn to a compound of the genus
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or a pharmaceutically acceptable salt thereof, wherein
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. Claim 31 of ‘146 is drawn to a pharmaceutical composition comprising a compund of Claim 1 and a pharmaceutically acceptable carrier. Claim 32 is drawn to a method of treating a mental health disorder comprising administering to a mammal in need thereof an effective amount of a compound of a compound of Claim 1. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘146 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘146 differ from those of the examined application by the presence of a single double bond. The specification of ‘146 demonstrates that these compounds are inhibitors of SERT (Table 8, Page 157), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 31-50 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 38, 56, and 57 of copending Application No. 18/995,408 (Amended Claims of 16 January 2025) (‘408).
Claim 38 of ‘408 is drawn to a compound of genus
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or a pharmaceutically acceptable salt thereof, wherein:
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. Claim 56 of ‘408 is drawn to a pharmaceutical composition comprising a compound of Claim 38 and a pharmaceutically acceptable excipient. Claim 57 of ‘408 claims a method for treating a mental health disorder comprising administering to a mammal in need thereof an effective amount of a compound of Claim 38 wherein the mental health disorder is anxiety, stress, or depression. These compounds differ from the compounds of the examined application by the presence of a double bond, but otherwise meet the limitations of what is claimed.
The claims at issue are not identical, but are not patentably distinct because the compounds of ‘408 and of the examined application are of similar structure, and would not be expected to have significantly different properties due to this close chemical structure (See MPEP § 2144.09 I). The compounds of ‘408 differ from those of the examined application by the presence of a single double bond. The specification of ‘408 demonstrates that these compounds are inhibitors of SERT (Table 8, Page 157), which is the same mechanism of the compounds of the examined application. The artisan would not expect the insertion of a double bond to significantly impact the activity of these compounds towards the 5-HT transporter.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 31-50 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1 of copending Application No. 18/807,015 (Amended Claims of 16 August 2024) (‘015) in view of Manda (Biomedical Chromatography, 2017: 31, e3815) and Rautio (Nature Reviews Drug Discovery, Vol. 7, March 2008).
Determining the Scope and Contents of the Prior Art:
Claim 1 of ‘015 claims a method of treating anxiety or depression, comprising orally administering to a subject in need thereof a therapeutically effective amount of a pharmaceutical composition comprising Compound 019
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or a pharmaceutically acceptable salt thereof. This is the compound that forms following metabolism of the compounds of the examined application via hydrolysis.
The teachings of Manda and Rautio are previously described and are fully incorporated into this rejection.
Ascertaining the Differences Between the Prior Art and the Claims at Issue:
‘015 does not disclose the use of pro-drugs of compound 019.
Resolving the Level of Ordinary Skill in the Pertinent Art:
The artisan would be a medical practitioner with further expertise and training in the use of therapeutics, including pharmacokinetics and pharmacodynamics with respect to the administration of drugs for the treatment of disease.
Considering Objective Evidence Present in the Application Indicating Obviousness or Nonobviousness:
‘015, Manda, and Rautio are considered analogous to the claimed invention as all are involved drug development and pharmacology. Therefore, it would have been prima facie obvious to one of ordinary skill in the art the time of the effective filing date of the instant application to modify mesembrano (Compound 019) l to form a pro-drug using the well-known techniques of forming esters as taught by Rautio, and Manda demonstrates that two similar alkaloids found within the same plant as mesembranol have poor oral bioavailability. The formation of pro-drugs of mesembranol in order to improve oral bioavailability is prima facie obvious use of a known technique to improve similar products in the same way (See MPEP 2143 I (C)); ‘015 claims the use of Compound 019 for the treatment of anxiety and depression; however, similar alkaloid compounds from the same plant possess poor oral bioavailability. Pro-drug formation, as taught by Rautio, is commonly employed in the pharmaceutical arts in order to enhance oral bioavailibity, and the artisan would recognize this, and would be motivated to form ester pro-drugs of this compound in order to allow for enhanced oral delivery, as oral delivery is a preferred method of treatment due to ease for the patient.
This is a provisional nonstatutory double patenting rejection.
Conclusion
Claims 31-50 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PHILLIP MATTHEW RZECZYCKI whose telephone number is (703)756-5326. The examiner can normally be reached Monday Thru Friday 730AM-5PM EST.
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, Andrew Kosar can be reached at 571-272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/P.M.R./Examiner, Art Unit 1625
/JOHN S KENYON/Primary Patent Examiner, Art Unit 1625
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