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 .
Election/Restrictions
Applicant's election with traverse of species (a-f) in the reply filed on August 25, 2025 is acknowledged. The traversal is based on species not being distinct and unrelated. Applicant further states there is no articulated reasoning provided that establishes a “serious” search or examination burden.
Applicant hereby elects the following species with traverse:
a. The polar aprotic solvent elected in steps (a) and (c) is ACETONE. Claims directed
to this elected species are claim 1, 3 and 25;
b. The organic acid elected in step (d) is OXALIC ACID. Claims directed to this elected
species are claims 1, 9 and 25;
c. The organic solvent elected in claim 10 is ACETONE. Claims directed to this elected
species are claims 7 and 11;
d. The Mitragynine salt precipitate formed in step (d) is elected as Mitragynine Oxalate
Salt precipitate. Claims directed to this elected species are claims 1, 16 and 25;
e. The polar aprotic solvent employed in step (f) is elected as ACETONE. Claims
directed to this elected species are claims 1, 18 and 25; and
f. The purified Mitragynine salt obtained in step (h) is elected as Purified Mitragynine
Oxalate salt. Claims directed to the elected species are claims 1, 21 and 25.
Claims 1-29 are pending. Applicant believes that claims 1, 3-7, 9, 11-14, 16, 18, 19 and 21-29 read on the elected species. The traversal is not found persuasive because the Mitragynine extract is highly dependent on the conditions and combinations of species of solvents/acids/salts used in the process. In addition, these species are not obvious variants of each other based on the current record. The traversal is not found persuasive because as stated in the election of species mailed on June 24, 2025 there is a serious search burden due to the species having separate statuses in the art due to their divergent subject matter. The species require different search queries. These require each of several different inventive concepts. The requirement is still deemed proper and is therefore made FINAL. Claims drawn to the elected species are currently under examination.
Priority
Applicant’s claim for the benefit of a prior-filed application no. IN202341010938 under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. The priority date is February 17, 2023.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on May 03, 2023 is being considered by the examiner. The signed IDS forms are attached with the instant office action.
Drawings
The drawings were received on May 03, 2023. These drawings are acceptable.
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 1-22, 24-26, and 28 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13, 19-22, 24, and 29 of copending Application No. 18/311,744 (reference application; US Patent Application Publication 2024/0287069 A1). Although the claims at issue are not identical, they are not patentably distinct from each other because the subject matter claimed in the instant application is fully disclosed in the referenced copending application and would be covered by any patent granted on that copending application since the referenced copending application and the instant application are claiming common subject matter, as follows: process for purification of Mitragynine from crude extract of Mytragynine comprising steps, solvents, acids, salts, filtering, and drying to form Mitragynine salt.
The claims of copending applications are drawn to a process for the purification of Mitragynine comprising the steps of: (a) adding crude extract of Mitragynine to a solvent in a reactor; (b) stirring the mixture obtained in step (a); (c) filtering the stirred solution obtained in step (b) to obtain filtered solution and spent; (d) optionally, adding solvent to the spent obtained in step (c), followed by stirring and filtering, to obtain filtered solution; (e) loading the filtered solution obtained in step (c) and/or step (d) into the reactor; (f) adding a mixture of an acid and solvent to the filtered solution in the reactor of step (e); (g) stirring the solution of step (f) until Mitragynine salt precipitate is formed; (h) filtering the precipitated salt as obtained in step (g) followed by washing with solvent; and (i) purifying the salt as obtained in step (h) with alcohol, followed by stirring, filtering and drying to form purified Mitragynine salt, In step (b) the stirring is carried out for 2 hours at 30-50 RPM, filtering is carried out through cleaned nutsche filter on 5 microns cloth, the acid in step (f) is organic or mineral acid. The mixture of organic or mineral acid and solvent in the step (f) process is prepared by dissolving the organic or mineral acid slowly into the solvent with continuous mixing followed by stirring at 30-50 RPM for 1 hour and filtering which is carried out through 100 mesh cloth. The organic or mineral acid employed in step (f) process is selected from a group comprising of hydrochloric acid, hydrobromic acid, perchloric acid, sulphuric acid, oxalic acid, tartaric acid, citric acid, formic acid, trifluoro acetic acid, trichloro acetic acid, or mixture thereof, preferably the organic or mineral acid is oxalic acid, the organic solvent selected from a group comprising of chloroform, acetone, methanol, ethanol, n-butanol, isopropyl alcohol, ethyl acetate, diethyl ether, n-hexane, methylene dichloride, ethylene dichloride or mixture thereof, preferably the solvent is acetone. In step (g), the stirring is carried out for 2 hours at 30-50 RPM. The Mitragynine salt precipitate formed in step (g) is hydrochloride salt, hydrobromide salt, perchlorate salt, sulphate salt, oxalate salt, tartrate salt, citrate salt, formate salt, trifluoro acetate salt, or trichloro acetate salt. Preferably the Mitragynine salt precipitate formed in step (g) is Mitragynine oxalate salt precipitate, the salt product obtained after filtration is air dried for 5-6 hours followed by drying in Vacuum Tray Dryer at 45-50°C under 700mm of Hg. The purified Mitragynine salt obtained in step (i) is purified Mitragynine hydrochloride salt, purified Mitragynine hydrobromide salt, purified Mitragynine perchlorate salt, purified Mitragynine sulphate salt, purified Mitragynine oxalate salt, purified Mitragynine tartrate salt, purified Mitragynine citrate salt, purified Mitragynine formate salt, purified Mitragynine trifluoro acetate salt, or purified Mitragynine trichloro acetate salt, preferably the purified Mitragynine salt is purified Mitragynine oxalate salt. A process for the purification of Mitragynine, said process comprises the steps of: (a) adding crude extract of Mitragynine to acetone in the reactor; (b) stirring the mixture obtained in step (a) for 2 hours at 30-50 RPM; (c) filtering the stirred solution as obtained in step (b) to obtain filtered solution and spent; (d) optionally, adding acetone to the spent obtained in step (c), followed by stirring and filtering, to obtain filtered solution; (e) loading the filtered solution obtained in step (c) and/or step (d) into the reactor; (f) adding a mixture of oxalic acid and acetone to the filtered solution in the reactor of step (e); (g) stirring the solution of step (f) for 2 hours at 30-50 RPM, until Mitragynine oxalate salt precipitate is formed; (h) filtering the precipitated Mitragynine oxalate salt as obtained in step (g) followed by washing with acetone; and, purifying the Mitragynine oxalate salt as obtained in step (h) with 10% Methanol, followed by stirring for 1 hour at 30-50 RPM, filtering and drying to form purified Mitragynine oxalate salt. The mixture of oxalic acid and acetone in step (f) is prepared by slowly adding oxalic acid to the acetone with continuous mixing followed by stirring for 1 hour at 30-50 RPM and filtering through 100 mesh cloth. In step (i) of the above process, the salt product obtained after filtration is air dried for 5-6 hours followed by drying in Vacuum Tray Dryer at 45-50°C under 700mm of Hg. The obtained Mitragynine oxalate salt in the present process is in amorphous form. The process provides improved yield of Mitragynine oxalate salt (25%) with purity of 72-78% by HPLC (see claims 1-13, 19-22, 24, and 29).
Although the claims, particularly claims 1-22, 24-26, and 28 at issue are not identical, they are not patentably distinct from each other because polar aprotic solvent employed in instant case is acetone, and acetone is one of the solvents in the copending application. Additionally claims 23, 25-27 and 29 of instant case are not identical, they are not patentably distinct from each other because, the scope of the claims overlaps for purification of Mitragynine salt.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
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 1-28 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.
Claim 1 refers in the preamble to purification of Mitragynine from crude extract and the end step in the body of the claim refers to purification of a Mitragynine salt. It is unclear how the preamble coincides with the end step of the claimed process. Clarification is requested. Claims dependent on rejected claim 1 are rejected for failing to cure the indefiniteness.
Claims 2 contains the Markush limitation “is selected from the group comprising of”…followed by a list of alternative embodiments of solvents. However, the “comprising of” language renders the metes and bounds of claim 2 undefined (hence rendering claim 2 indefinite) since it is written as an open-ended list of alternative embodiments; rather, Markush limitations are supposed to be closed-ended alternative embodiments. As written, it is unclear what other alternatives are intended to be encompassed by the claim. A Markush grouping is a closed group of alternatives, i.e., the selection is made from a group "consisting of" (rather than "comprising" or "including") the alternative members. Abbott Labs., 334 F.3d at 1280, 67 USPQ2d at 1196. If a Markush grouping requires a material selected from an open list of alternatives (e.g., selected from the group "comprising" or "consisting essentially of" the recited alternatives), the claim should generally be rejected under 35 U.S.C. 112(b) as indefinite because it is unclear what other alternatives are intended to be encompassed by the claim. See In re Kiely, 2022 USPQ2d 532 at 2* (Fed. Cir. 2022). See MPEP 2173.05(h). Claim 3 is similarly rejected as indefinite since the claim refers back to rejected claim 2 but does not remedy the rationale underpinning the basis for this rejection.
This same issue as claim 2, makes claims 8, 10, and 17 indefinite (for containing “comprising of” followed by a Markush list of alternative embodiments).
How to render moot these open-ended list of alternatives’ rejections: Please replace “comprising of” with -- consisting of -- in all rejected claims 2, 8, 10, and 17, above.
Claim 22 recites the limitation "the Mitragynine oxalate salt" of claim 1. There is insufficient antecedent basis for this limitation in the claim.
As drafted, "the Mitragynine oxalate salt" renders the metes and bounds of claim 22 undefined (hence rendering claim 22 indefinite) since the artisan does not know where antecedent basis is first found for "the Mitragynine oxalate salt" within claim 1. Examiner recommends making claim 22 depend from claim 21 to render moot this rejection as claim 21 does contain antecedent basis to "Mitragynine oxalate salt". Claim 23 is indefinite for the same rationale.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim 29 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by: ACS (American Chemical Society. Chemical Abstract Service. RN 11047-41-9. Entered into STN: 16 November 1984).
The prior art reference ACS teaches the Mitragynine oxalate compound:
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(see enclosed ACS reference).
Furthermore, the limitation “having 62-68% HPLC purity” of the rejected claim 29 is interpreted as an inherent property/function. When the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent. Thus, “having 62%-88% HPLC purity” is also anticipated by the ACS prior art reference. See MPEP 2112.01(I) and (II). This anticipates instant claim 29.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The 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.
Claims 1-29 are rejected under 35 U.S.C. 103 as being unpatentable over Goh Teik Beng et.al., “A SIMPLE AND COST EFFECTIVE ISOLATION AND PURIFICATION PROTOCOL OF MITRAGYNINE FROM MITRAGYNA SPECIOSA KORTH (KETUM) LEAVES (The Malasian Journal of Analytical Sciences, Vol 15 No 1 (2011): 54-60), and Karimov R et. al. (WO-2016176657-A1),Cravotto G (WO-202208955-A1), in view of Amrianto et. al., “Mitragynine: a review of it’s extraction, identification, and purification methods”, Current Research on Bioscience and Biotechnology 3 (1) 2021 165 171.
In instant claims recite, process for purification of Mitragynine from crude extract of Mitragynine comprising the steps of:(a) mixing crude extract of Mitragynine with polar aprotic solvent (Acetone) in a reactor followed by stirring; (b) filtering the stirred solution obtained in step (a) to obtain filtered solution and spent; (c) optionally, adding polar aprotic solvent to the spent obtained in step (b), followed by stirring and filtering, to obtain filtered solution; (d) mixing the filtered solution obtained in step (b) and/or step (c) and an acid solution (Oxalic acid) in the reactor followed by stirring until Mitragynine salt precipitate is formed; (e) filtering the precipitated salt as obtained in step (d); (f) washing the filtered precipitated salt of step (e) with polar aprotic solvent (Acetone) to obtain the salt product; (g) optionally, performing step (f) multiple times to obtain the salt product; and (h) drying the salt product obtained in step (f) and/or step (g) to form purified Mitragynine salt.
Regarding claims 1 and 25, Beng et. al. teaches, “Approximately 0.80 g of the isolated crude mitragynine was dissolved in minimum quantity of methanol and this solution was added to a 5 mL saturated methanolic picric acid solution. Side of test tube was scratched and this solution was kept in refrigerator for 20 minutes to obtain orange colored mitragynine picrate crystals. These crystals were filtered, washed with methanol followed by acetone and the melting point of these crystals was determined (Experimental paragraph - Purification of mitragynine by crystallization)”. Furthermore, regarding claims 24, and 28, Beng et. al. teaches, “Fresh Mitragyna speciosa to obtain crude mitragynine (Experimental paragraph - Extraction and isolation of mitragynine).”
Claims 1, 5, 12, and 25 differs from Beng et. al. in that polar aprotic solvent used to purify Mitragynine, however, Karimov et.al. ‘657 teaches, employing methanol which is also polar aprotic solvent, “Kratom powder (450 g) was extracted by refluxing with MeOH (5 x 500 mL) for 40 min. The suspension was filtered after each extraction and the solvent evaporated. The residue was resuspended in 20% acetic acid solution; The combined organic layers were dried over sodium sulfate and filtered (Detailed Description of certain embodiments [para. 00291]).” Although, reference does not explicitly teach what type of filtration system used to filter the extract, for example, the instant claims teach using micron cloth for filtering the crude extract of Mitragynine. However, one skilled in the art is knowledge to perform filtration of product dependent of what contaminants are to be removed to make the end result in pure form, and because it is known in the art to the use of micron filters serves as physical separation tool for purifying Mitragynine rather than isolating the alkaloids by chemical.
Additionally, regarding claims 1, 2, 3, 10-11, 17, 18, and 25, Karimov et. al. ‘657 teaches, “A solvent can be used in the coupling reaction. Any solvent not interfering with the reaction can be included. In some embodiments, the solvent is a polar aprotic solvent. Exemplary solvents suitable for the coupling reaction include, but are not limited to, dichloromethane, tetrahydrofuran (THF), ethyl acetate, acetonitrile, dimethylformamide (DMF), dimethyl sulfoxide (DMSO), acetone, and hexamethylphosphoric triamde (HMPT) (Detailed Description of certain embodiments [para.00198].”
Regarding Claims 6, 8, 9, 13, and 15, Karimov et. al. ‘657 teaches, “Examples of pharmaceutically acceptable, nontoxic acid addition salts are salts of an amino group formed with inorganic acids such as hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, and perchloric acid or with organic acids such as acetic acid, oxalic acid, maleic acid, tartaric acid, citric acid, succinic acid, or malonic acid; Exemplary chelating agents include ethylenediaminetetraacetic acid (EDTA) and salts and hydrates thereof (e.g., sodium edetate, disodium edetate, trisodium edetate, calcium disodium edetate, dipotassium edetate, and the like), citric acid and salts and hydrates thereof (e.g., citric acid monohydrate), fumaric acid and salts and hydrates thereof, malic acid and salts and hydrates thereof, phosphoric acid and salts and hydrates thereof, and tartaric acid and salts and hydrates thereof (Detailed Description of certain embodiments [para. 00211]).”
Therefore, a person having ordinary skill in the art would have been motivated and likely to succeed in purifying Mitragynine salts from Mitragyna speciosa using the claimed solvents and salts, because both Beng et al. and Karimov et al. disclose such a purification.
Beng et. al. and Karimov et. al. does not explicitly teach stirring, filtering, and drying, as in instant claims 4, 5, 7 12, 14, 19, and 26 however, Carvoto ‘955 teaches, “plant material was placed in round bottom flask, 500mL of MeOH/H2O 1:1 mixture was added, and the suspension was kept under magnetic stirring. The suspension was filtered on a filter paper and MeOH was evaporated under vacuum (Example 2 [para. 0054, and 560057]).” From the teachings of Beng, Karimov, and Carvoto, one of ordinary skilled in the art would be able to modify the steps of purification of Mitragynine by mixing polar aprotic solvent as methanol or acetone, mixing, stirring, filtering, and drying to obtain a purified Mitragynine salt. A person of ordinary skilled in the art would have understood to modify steps to process purification of Mitragynine by incorporating the steps taught by Beng, Karimov, and Carvoto and optimize process to achieve a success for purifying Mitragynine as the end result would be similar. It is obvious to the person having ordinary skill in the art to purify a Mitragynine salt from a crude extract, because the prior art has shown the same process steps to purify Mitragynine salts.
Regarding claims 23 and 27, Karimov et. al. teache, “ Analysis of mitragynine has been carried out using High-Performance Liquid Chromatography (HPLC) instruments. The use of the HPLC method was found to be suitable for the detection of alkaloid compounds such as mitragynine (Identification and purification methods of mitrgynine [para. 0002]).”
One would have had a reasonable expectation of success to achieve the purification process of Mitragynine from crude extract of Mitragynine because the cited references teach using similar solvents, salts, and process steps as currently claimed. It would have obvious to combine known method steps to yield a predictable result of obtaining a purified Mitgagynine salt. The process of purification of Mitragynine in the instant invention is not an inventive process because merely combining known purification techniques in the art and the routine purification of a product to separate alkaloids and impurities, and filtering to obtain soluble and insoluble fractions are the inherent and predictable consequence of purification technique.
The incorporation of the teachings from the references above, it is deemed merely a matter of judicious selection and routine optimization of adjusting process and selection of solvents and acids which is well within the purview of the skilled artisan.
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was effectively filled. As evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
No Claims are presently allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Alpa Amin whose telephone number is (571)272-0562. The examiner can normally be reached 8:30am - 6:00pm.
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/ALPA NILESH AMIN/Examiner, Art Unit 1655
/ANAND U DESAI/Supervisory Patent Examiner, Art Unit 1655
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