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 .
Status of the Claims/Application
Claims 2, 4-7, 13-17 and 19-20 are canceled. Claims 1, 3, 10, 12, 18, 22 and 27 are currently amended. Claims 1, 3, 8-12, 18 and 21-28 are currently pending and are herein under examination of the merit.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 01/14/2026 is acknowledged and is in compliance with the provisions of 37 CFR 1.97. It has been considered by the examiner.
Withdrawn Rejections/Objections
Applicant’s canceled claims 2, 4-7, 13-17 and 19-20, see claims, filed on 01/14/2026, with respect to claims 2, 4-7, 13-17 and 19-20 have been canceled rendering the rejections moot. The objections of claims 19 and 20 and the rejections under 35 USC 103 of claims 2, 4-7, 13-17 and 19-20 have been withdrawn.
New Claim Objections
Claim 22 is objected to because of the following informalities: The claims recites “2.25 gm of sodium oxybat to 12 gm sodium oxybate”. Appropriate correction for the spelling of “oxybat” is required.
Furthermore, applicant is reminded as per MPEP 714C related to “status identifiers” for all amended claims. Claim 22 was amended as per claim set filed on 01/14/2026 but has a status identifier as “Original”.
New 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.
Claim 18 recites the limitation "the pharmaceutical composition of claim 1" in line 1. There is insufficient antecedent basis for this limitation in the claim.
Maintained Rejections
Applicant's arguments/remarks filed 01/14/2026 have been fully considered but they are not persuasive. Therefore, the rejections of claims 1, 3, 8-12, 18 and 21-28 under 35 USC 103 issued on 07/16/2025 are maintained as below.
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, 3, 10, 12 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over US 2020/01114015 A1, and further in view of US Patent No. 5324750, and Banerjee SS, Aher N, Patil R, Khandare J. Poly(ethylene glycol)-Prodrug Conjugates: Concept, Design, and Applications. J Drug Deliv. 2012 herein further referred to as US'4015, US'4750, and Banerjee.
Regarding claims 1 and 10, US'4015 teaches three oxybate prodrug formulars or pharmaceutical compositions, A, B and C (US'4015 pg. 3 col. 0020) as shown below.
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US'4015 further teaches X and Y are components that are covalently bound to GHB (oxybate) molecule through ester bonds. Formular C is a bis-series of GHB prodrug where X is bonded to the hydroxyl group of GHB through an ester bond and Y is chemically bonded to GHB through its carboxylic acid group through and ester or amide bond depending on the functionality of the group that is attached to the carboxylic group of GHB (US'4015 pg. 3 para. 0021 In 17-25).
US'4015 does not specifically teach of an oxybate polyethylene glycol (PEG) ester prodrug or
conjugate.
US'4750 teaches that cyclodextrin can be covalently bonded to a pharmaceutical agent that
have a functional group including carboxyl (-COOH) and hydroxyl (-OH) groups (US'4750 Col. 33 In 7-19). US'4750 further teaches that it is possible to esterify cyclodextrin at a desired hydroxyl group by reacting sodium salts of carboxylic acid with cyclodextrin substituted with a suitable leaving group to give an ester linkage (US'4750 Col. 30 In 29-39). Also, US'4750 teaches that ß cyclodextrin is commonly used in various complexes due to their nontoxic nature and all the primary hydroxyl groups situated at one end and all the secondary hydroxyl groups at the other end (US'4750 Col. 1 In 31-44). Beta Cyclodextrin have the ability to stabilize and increase the bioavailability of drugs especially where the drug has a short half-life (US'4750 col. 2 In 64-68 and col.3 In 1-16).
Banerjee teaches that polyethylene glycol (PEG) can be conjugated to a biomolecule that has a functional group such as -COOH, -OH, -SH and -NH₂ (Banerjee et al pg. 2 sec. 2 In 6-14).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill in the art to modify the teachings of US'4015 in view of US’4750 and Banerjee with reasonable high degree of predictable success so as to obtain an oxybate-PEG, PEG-oxybate-ß-cylcodextrin prodrug or conjugate that has improved pharmacokinetic, pharmacological and physico-chemical properties than that of oxybate. It is known in the art that oxybate has low bioavailability, short half-life and is very susceptible for illicit use due to its fast dissolution in alcohols and common drinks with no taste, color or odor. As a result of the fast dissolution of oxybate, it can potentially lead to accidental or intentional overdose for prescription and over-the-counter drug (US'4015 pg. 2 para. 0010 In 1-6 and para. 0011). As indicated by US'4015, prodrug moieties that a generally recognized as safe can be covalently linked to oxybate to produce prodrugs (US'4015 pg. 2 para. 0017) according to Formular C, thereby altering the characteristics of oxybate to enhance it use for treatment of a condition. Polyethylene glycol (PEG) is a commonly used polymer for prodrug or conjugates in the art to improve therapeutic efficiency. Banerjee et al illustrates monomethoxy PEG (mPEG) (Banerjee et al pg. 2 Fig 2) that are used for prodrug modification by ester linkage between the gamma hydroxyl group of oxybate and the carboxylic acid group of the PEG acid as illustrated by Formular A (US'4015 pg. 3). PEG is also the only water soluble polymer that is widely accepted in therapeutics with market approval and has a decrease interactions with blood proteins and has a high biocompatibility. PEG can form chemical conjugates to drugs through a stable covalent bond (ester bond) with oxybate that remains stable until the prodrug reaches its target site (Banerjee et al. pg. 2 sec. 3 In 6-13). Therefore, one skilled in the art will have been motivated to use PEG as a suitable prodrug moiety to conjugate with oxybate to enhance its solubility and slow down it's dissolution. Also, US'4750 teaches that ß-cyclodextrin are commonly used in various complexes due to their nontoxic nature and all the primary hydroxyl groups situated at one end and all the secondary hydroxyl groups at the other end (US'4750 Col. 1 In 31-44). Cyclodextrins have the ability to stabilize and increase the bioavailability of drugs especially where the drug has a short half-life (US'4750 col. 2 In 64-68 and col.3 In 1-16). As such, it would have been obvious for one with ordinary skills to modify Formular C by using mPEG and ß-cyclodextrin to obtain an oxybate-PEG prodrug or conjugate that has better bioavailability and therapeutic outcomes and may be suitable for patients with low sodium intake.
Regarding claims 3 and 12, and incorporating the analysis of claims 1 and 10 above, US'4750 teaches that prodrugs can be made by reacting a pharmaceutical agent having a suitable functional group with a substituted or unsubstituted cyclodextrin (US'4750 col. 32 In 1-3). It also teaches that the pharmaceutical agents may contain functional group that may interfere with the desired reaction to the cyclodextrin and so it may be necessary to protect the interfering functional groups (US'4750 col. 32 In 64-68). US'4750 also teaches that the functional groups that the pharmaceutical agent may have for boding with cyclodextrin includes carboxyls (-COOH) and hydroxyl(-OH) (US'4750 col. 33 In 7-19). US'4750 further teaches that cyclodextrin can be esterified at the desired hydroxyl group (US'4750 col. 30 In 29-39). US'4750 Fig. 8 and Fig. 10 illustrates a diester and ester linked cyclodextrin (Col. 7 In 52-55).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill in the art to modify the teachings of US'4015 in view of US'4750 and Banerjee so as to obtain an ester prodrug conjugate that has improved pharmacokinetic and pharmacodynamic properties than oxybate. It is known in the art by one with ordinary skills, that polyethylene glycol and cyclodextrin can be used to
develop prodrugs which can help improve it bioavailability, reduce side effects, increase half-life
amongst others as indicated in the analysis of claim 1 above(US'4015 pg. 3 para. 0020) and (US'4750 col.
2 In 64-68 and col.3 In 1-16).
Regarding claim 28, and incorporating the analysis of claim 1, US'4015 teaches that oxybate can
be conjugate with generally recognized as safe (GRAS) prodrug components. US'4015 also teaches that
the prodrug formulation may prevent abuse by exhibiting stability under conditions that are likely to be
employed by one with ordinary skill in the art who may illicitly attempt to release the GHB compound
from its attached prodrug group (US'4015 pg. 3 para. 0020).
US'4750 teaches cyclodextrin as a suitable GRAS for the formulation of prodrugs (US'4750 col.
33 In 8-19).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015 in view of US'4750 and Banerjee with reasonable degree of predictable success to improve the abuse-resistance of oxybate by formulating an oxybate cyclodextrin ester as in claim 1 so as to enable the use of oxybate without abusing the drug.
Claims 8-9 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over US’4015, US’4750 and Banerjee as applied to claims 1 and 10 above, and further in view WO2017049470A1, herein further referred to as WO'9470.
Regarding claims 8, 9 and 11, and incorporating the analysis of claim 1 and 10 above, Banerjee further teaches that polyethylene glycol (PEG) can be conjugated to a biomolecule that has a functional group such as -COOH, -OH, -SH and -NH₂ (Banerjee et al pg. 2 sec. 2 In 6-14). Banerjee et al. also suggested that methyl polyethylene glycol (mPEG) is one of the most useful for polypeptide modification and that successful conjugation of PEG with biomolecules depends on the chemical structure, molecular weight, steric hindrance and the reactivity to the molecule.
WO'9470 teaches an ester prodrug having a chemical structure as shown below, where R² can be -(CH₂) and R³ can be C1-6 alkoxyl.
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WO'9470 does not specifically teach of an oxybate-PEG ester prodrug or conjugate having the structure PEG-O-CH2-COO-CH₂CH₂-COOH (WO'9470 pg. 6 para. 19).
Banerjee teaches that polyethylene glycol (PEG) can be conjugated to a biomolecule that has a functional group such as -COOH, -OH, -SH and -NH₂ (Banerjee et al pg. 2 sec. 2 In 6-14). Banerjee also suggested that methyl polyethylene glycol (mPEG) is one of the most useful PEG for polypeptide modification and that successful conjugation of PEG with biomolecules depends on the chemical structure, molecular weight, steric hindrance and the reactivity to the molecule (Banerjee pg. 2 sec 2).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill in the art to modify the teachings of US’4015, US,4750 and Banerjee in view of WO’9470 with reasonable degree of predictable success so as to PEGylate oxybate with an alkoxy-PEG that will form an ester bond between the alkoxyl PEG and Oxybate to obtain an oxybate-PEG ester prodrug which has an improved pharmacokinetic and pharmacodynamic properties than oxybate. Also, as suggested by Banerjee et al., one skill in the art will choose mPEG for the formulation of the prodrug or conjugate due to its size and other properties that makes it less likely to cause steric hindrance with the other functional groups in the prodrug or conjugate.
Claims 18 and 21-27 are rejected under 35 U.S.C. 103 as being unpatentable over US’4015, US,4750 and Banerjee as applied to claim 10 above, and further in view of US Patent No. 10398662 B, herein after referred to as US’8662.
Regarding claim 18, and incorporating the analysis of claim 1 above, US'8662 teaches of a pharmaceutical composition (Col. 12 In 37-60) where a drug-anion exchange resin contained within a matrix (US'8662 col. 12 In 29-36) and an anionic hydrophobic agent can be loaded on the resin (US'8662 col. 2 In 11-16) as well as a GHB-containing resonates matrix can be coated with a diffusion rate controlling coating (US'8662 col. 17 In 49-52). US'8662 further teaches that the formulation of the GHB-resin matrix complex can be an immediate or modified release composition (US'8662 col. 4 In 40-55). US'8662 teaches drug-resin complex can be formulated to address some pharmacokinetic limitations of oxybate (US'8662 col. 6 In 7-11). US'8662 further teaches a suitable ion-exchange resin includes anion exchange resin that are well suited for use with acidic drugs including GHB as well as prodrugs, salts and solvates thereof (US'8662 Col. 8 In 17-27). It also teaches an example of anion exchange resin with a polystyrene matrix and quaternary ammonium functional group that can be used in the drug-resin complex (US'8662 Col. 8 In 30-34) and the complex can be a polymeric beads which can optionally be coated (US'8662 Col.2 In 45-51). US'8662 also teaches that the drug-resin complex can address some of the solubility challenges of oxybate as long as oxybate remain bounded to the resin (US'8662 col. 6 In 7-14).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with reasonable level of predictable success to obtain a pharmaceutical composition of PEG-Oxybate-anion exchange resin complex that has been coated with a rate controlling agent in an anion exchange matrix comprising a hydrophobic agent so as to enable the controlled release of oxybate and increase the half-life of oxybate and potentially reduce the frequency of administration during night time.
Regarding claim 21, and incorporating the analysis of claim 10 above, US'8662 teaches a formulation of oxybate comprising oxybate salts such as sodium, potassium etc. (US'8662 col. 4 In 51-56).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with reasonable degree of predictable success to formulate a pharmaceutical composition as described in claim 10 that has an acceptable oxybate salt such as sodium as a component of the formulation, whereby the oxybate salt will enable an immediate release component of oxybate.
Regarding claim 22, US'8662 teaches that the pharmaceutical composition can be formulated
in such a way that has oxybate equivalent in such a way that will enable immediate and controlled
release of oxybate, by having a composition that has two or more distinct bead populations of oxybate
distinguished by their release characteristics (US'8662 col. 20 In 47-67). Also, US'8662 teaches that
about 12-13 gm of sodium oxybate would be required for a sustained release formulation to be
equivalent to the 6-9 gm of Xyrem that is normally administered.
Therefore, it would have been obvious before the effective filing date for one with skill in the art
to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with reasonable degree of predictable success to obtain a pharmaceutical composition comprising an amount of oxybate equivalent of 2.25 gm oxybate HCL to 12 gm sodium oxybate so as to enable the design of a composition that has more than one population of oxybate prodrug, where each population can be release at different time intervals such as immediate release and extended release and will still provide the an effect amount of oxybate required for the desired therapeutic outcome.
Regarding claims 23, 24 and 25, and incorporating the analysis of claim 10, US'4015 teaches the
GHB prodrugs can prevent abuse when administered via parenteral routes, particularly by intravenous,
intranasal, or inhalation routes (US'4015 pg. 3 para. 0018 In 4-8).
US'4015 does not specifically teach of a composition as in claim 10, wherein the pharmaceutical
composition is a powder-for-suspension or powder-for-solution or wherein the pharmaceutical
composition is in an aqueous suspension or solution formulated for injection or oral dosing.
US'8662 teaches a formulation where the immediate release component may be provided as a
dry powder formulation, an immediate release tablet, an encapsulated formulation or a liquid solution
or suspension (US'8662 col. 4 In 46-49). US'8662 also teaches that the any of the compositions as
described in the patent document can be presented in hydrated form as part of an aqueous suspension,
or maybe provided as dried beads for mixing with water immediately prior to ingestion or to be taken
without water (e.g., as a powder, tablet, capsule etc.) (US'8662 col. 18 In 11-17).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with a reasonable high degree of predictable success to formulate the pharmaceutical composition of claim 10 as a powder-for-solution, powder-for-suspension, solution for injection, solution for oral dosing or an aqueous suspension so as to obtain compositions of various forms that is suitable for administering to different patient populations in order to improve therapeutic outcomes, compliance and tackle other problems related to the current formulation of sodium oxybate (available in solution as XYREM).
Regarding claim 26, and incorporating the analysis of claim 10, US'8662 teaches that gamma
hydroxybutyrate (GHB) which is a sodium-free form of sodium oxybate, is used to formulate the anion
exchange resin complex of the prior invention (US'8662 col. 2 In 7-15 and In 45-57).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with reasonable degree of predictable success to obtain a sodium free pharmaceutical composition so as to obtain a formulation that is suitable for individuals who have a sodium intake restriction.
Regarding claim 27, and incorporating the analysis of claim 10, US'8662 teaches of a pharmaceutical composition comprising GHB prodrug that can be formulated as a controlled or
extended release, accompanied by a component of an immediate release formulation of GHB (US'8662
col. 4 In 9-15 and col. 19 In 8-21).
Therefore, it would have been obvious before the effective filing date for one with ordinary skill
in the art to modify the teachings of US'4015, US’4750 and Banerjee in view of US'8662 with a reasonable degree of predictable success to make a pharmaceutical composition as that in claim 10 so as to improve the therapeutic effects that GHB (oxybate) may have on the individual taking it.
Response to Arguments
Applicant's arguments/remarks filed 01/14/2026 have been fully considered but they are not persuasive.
Regarding the applicants remarks on page 1 para 6 filed on 01/14/2026, applicants remarks that US’4015 does not teach oxybate polyethylene glycol (PEG) ester prodrug or conjugate or suggest PEG diester and that US’4015 requires a covalent attachment of a chemical moiety derived from alpha-hydroxy carboxylic acid which changes one or more GHB’s properties and/or a variety of different ligands. Firstly as indicated in US’4015 of 892 submitted on 07/16/2025, the prodrug with Formular C is a bis-series GHB prodrug wherein the prodrug moieties X and Y are chemically or covalently attached to the hydroxyl and carboxylic groups of GHB via ester bonds respectively (US’4015 para 0021), therefore US’4015 teaches this limitation. Regarding Applicant remarks that US’4015 requires a chemical moiety derived from alpha-hydroxy carboxylic acid, US’4015 teaches that chemical moieties derived from alpha-hydroxy carboxylic acids are exemplary generally recognize as safe (GRAS) monomers and recites that other GRAS monomers can be used for the same (US’4015 para 0022-0023). Furthermore, it is common in the arts to use PEG in formulating prodrugs conjugates in order to improve various pharmacodynamic and pharmacokinetic properties of the drug such as prolong circulation time, minimize nonspecific uptake, and enhance permeability and retention effect as indicated by Banerjee (Banerjee Abstract).
Regarding the applicants remarks on page 1 para 7 filed on 01/14/2026, applicants remarks that US’4750 generally describes cyclodextrin complexes and the processes for making the same and that it does not teach or suggest oxybate or any oxybate prodrug. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Furthermore, as indicated by US’4015 of 892 submitted on 07/16/2025, other GRAS can be used to make the prodrug. Furthermore beta-cyclodextrin are GRAS (Braga pg. 2 Section 1.2) that are commonly used in the food and pharmaceutical industries. Also, as indicated by US’4750 benefits of cyclodextrins include the ability to stabilize and increase bioavailability of drugs due to their ability to strongly include a drug molecule to render it inactive by hydrolysis in an acidic environment like the stomach as well as improves the drug half-life (US’4015 col 2 ln 64-68 and col 3 ln 1-16). Therefore, a skilled artisan would have been motivated to determine which cyclodextrin to use as the Y chemical moiety that can form ester bond on the carboxylic end of GHB (oxybate) based on its ability to improve the drugs pharmacodynamics and pharmacokinetics properties given cyclodextrin are known GRAS that are commonly used for said purposes.
Regarding the applicants remarks on page 2 filed on 01/14/2026, applicants remarks that neither WO’9470 or U’662 does not teach prodrugs of GHB nor does it suggest oxybate-PEG ester prodrug or conjugate, and that Banerjee not teach or suggest oxybate, oxybate prodrugs or Peg oxybate prodrugs in combination with a PEG bi- ester. In response to applicant's arguments against the references individually, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). As indicated in the rejection issued on 07/16/2025 it would have been obvious for a skill artisan to use PEG and cyclodextrin that are commonly used GRAS where the PEG prodrug moiety can form an ester linkage with the hydroxyl terminal of GHB and beta-cyclodextrin can form an ester linkage with the carboxyl terminal of GHB as indicated by US’4015 to obtain the PEG bi-ester prodrug as claimed in the instant claims.
Conclusion
No claims allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to EMMANUEL LED YOUTCHOM PENDIE whose telephone number is (571)272-6313. The examiner can normally be reached Mon - Fri: 8AM - 5PM CST.
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/EMMANUEL LED YOUTCHOM PENDIE/ Examiner, Art Unit 1647
/JOANNE HAMA/ Supervisory Patent Examiner, Art Unit 1647