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 .
Status of Application
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 07/13/2026 has been entered.
Receipt of Applicants’ Arguments, Remarks and amended claims filed on 07/13/2026 is acknowledged. Claims 1, 4-15 are pending. Claims 2-3 remains cancelled. Claim 1 have been amended.
Claims 1, 4-15 are pending and under examination in this application.
Priority
The current application filed on 05/09/2023 is a 371 of PCT/US2021/058843 filed 10/10/2021, which in turn claims priority to provisional patent application 63/112,32 filed on 11/09/2020.
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.
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 1, 4-15 are rejected under 35 U.S.C. 103 as being unpatentable over Zheng (WO 2019/144117 A1) in view of Nanoemulsion: Concepts, development and applications in drug delivery (hereinafter the referenced is referred as Singh) and further in view of Ulm et al. (US 2006/0148776 A1) (hereinafter the reference is referred as Ulm), both Singh and Ulm cited in IDS filed 05/09/2023.
Zheng teaches compositions that induce the degradation of the Bcl-2 family proteins and their method of use in the treatment of various cancers (¶ 0003) directed to compounds of anti-apoptosis Bcl-2 protein degraders comprising formula (I) in (¶ 0024-0037):
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in an embodiment, the below compound (¶ 0037) is explicitly displayed on page 37.
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Comprising a variety of vehicles are suitable for delivering a composition, for example, nanoparticles, liposomes, microemulsions, micelles, dendrimers and other phospholipid containing systems and methods of incorporating compositions into delivery vehicles are known in the art (¶ 0058).
Regarding claim 1, Zheng discloses delivery of the compound as a microemulsion comprising an aqueous solution, a surfactant, and an oil phase, wherein the structure may be micelles, which are like drops of oil in water, and the "oil" of microemulsions optimally comprises phospholipids (¶0066). Thus, the limitations of a compound of formula (I), a dispersed medium, a dispersing medium, and a nanoemulsion-type vehicle are taught or suggested by Zheng. Furthermore, Zheng discloses as will be appreciated by a skilled artisan, microemulsions can and will have a multitude of different microscopic structures including sphere, rod, or disc shaped aggregates, and in one embodiment, the structure may be micelles, which are the simplest microemulsion structures that are generally spherical or cylindrical objects, wherein micelles are like drops of oil in water, and reverse micelles are like drops of water in oil, and in an alternative embodiment, the microemulsion structure is the lamellae. It comprises consecutive layers of water and oil separated by layers of surfactant. The "oil" of microemulsions optimally comprises phospholipids (¶ 0066).
Regarding claims 4-7, Zheng teaches pharmaceutical compositions for effective administration are deliberately designed to be appropriate for the selected mode of administration, and pharmaceutically acceptable excipients, for example, compatible dispersing agents, buffers, surfactants, preservatives, solubilizing agents, isotonicity agents, stabilizing agents and the like are used as appropriate (¶ 0096), and preparation may be an aqueous or an oil-based solution comprising an antioxidant, for example ascorbic acid or sodium bisulfite (¶ 0055), a chelating agent ethylenediaminetetraacetic acid (EDTA); a buffer such as acetate, citrate, or phosphate; and/or an agent for the adjustment of tonicity such as sodium chloride, dextrose, or a polyalcohol such as mannitol or sorbitol, and the pH of the aqueous solution may be adjusted with acids or bases such as hydrochloric acid or sodium hydroxide, wherein Oil-based solutions or suspensions may further comprise sesame, peanut, olive oil, or mineral oil (¶ 0055), emulsifying and/or suspending agents (¶ 0054) and polyethylene glycol (PEG) (¶ 0049, 0062).
Regarding claim 8, Zheng teaches pH modifying agent may be sodium carbonate sodium bicarbonate, citric acid or phosphoric acid (¶ 0044).
Regarding claims 9 and 10, Zheng teaches oil-in-water or a water-in-oil base (¶ 0057), and the solvent may be an organic solvent or an inorganic solvent or a combinations thereof (¶ 0063), as well as diluents of ethanol, glycerin, and combinations thereof (¶ 0054). Furthermore, Zheng teaches parenteral administration (including subcutaneous, intradermal, intravenous, intramuscular, and intraperitoneal), the preparation may be an aqueous or an oil-based solution, and aqueous solutions may be include a sterile diluent such as water, saline solution, a pharmaceutically acceptable polyol such as glycerol, propylene glycol, or other synthetic solvents (¶ 0055). Thus the limitations of dispersed medium is a water miscible organic solvent and the dispersing medium is water, a water miscible solvent, or a mixture of two or more of water, a water miscible solvent are taught.
Zheng fails to specifically teach a nanoemulsion having a droplet size of 20-150 nm and lecithin as an emulsifying agent.
Singh teaches nanoemulsions are biphasic dispersions of two immiscible liquids stabilized by an amphiphilic surfactant, and discloses that the mean droplet diameter attained is usually less than 500 nm (p. 29, Introduction). Singh further teaches that the most important criterion in manufacturing a nanoemulsion is obtainment of a desired droplet size with monomodal distribution (p. 32, §3.4, Manufacturing nanoemulsions), and that droplet size is a variable directly controlled through known process parameters including applied shear, surfactant selection/concentration, and relative viscosity of the dispersed and continuous phases (p. 32, §§3.5.1-3.5.3), as well as through high-energy methods such as microfluidization, high-pressure homogenization, and ultrasonication, or low-energy methods such as spontaneous emulsification (pp. 32-34, §§3.6-4.1). Singh discloses that droplet size decreases with increasing sonication time and input power, confirming droplet size is a result-effective variable routinely controlled via known process conditions (p. 33, §3.7.3).
Singh further teaches that a common surfactant employed in nanoemulsions is lecithin (phosphatidylcholine), derived from egg yolk or soybean (p. 31, §3.2). Singh discloses that lecithin-based nanoemulsions have been used in marketed parenteral products including Intralipid®, Doxil®, Ambisome®, and Propofol® (p. 31, §3.2). Critically, Singh discloses numerous specific working nanoemulsion formulations with droplet sizes falling within or overlapping the claimed 20–150 nm range: Topical turmeric oil nanoemulsion, droplet size 20–200 nm (Table 4, p. 43; ref. [171]); Topical caffeine W/O nanoemulsion sized between 20 and 100 nm (p. 43, §9.3; ref. [159]); Oral nanoemulsions of paclitaxel (90–120 nm), ramipril (70–90 nm), silymarin (80–100 nm), piroxicam (30–100 nm), insulin (30–100 nm), and repaglinide (76.23 nm) (Table 3, p. 42; refs. [140], [143], [144], [149], [156], [152]); Ocular cationic nanoemulsion with droplet diameter of 95 ± 2 nm (p. 44, §9.4; ref. [176]); Parenteral vitamin E/paclitaxel nanoemulsion (TOCOSOL™) described as ultrafine (40–80 nm) (p. 41, §9.1; ref. [117]).
Therefore, the limitation of a nanoemulsion having droplet sizes of 20–150 nm is taught, or at minimum rendered obvious as an overlapping range achieved by routine optimization of a recognized result-effective variable using conventional manufacturing techniques. See MPEP 2144.05(I), (II)(A); In re Aller, 220 F.2d 454 (CCPA 1955).
Singh fails to specifically teach the dispersed medium is long chain triglyceride, a medium chain triglyceride, or a short chain triglyceride, and the specific percentages of compound 1.
Ulm teaches drug formulations having emulsifying agents and both medium- and long-chain triglycerides for improved parenteral administration of lipophilic drugs, specifically noting that ansamycins like many other lipophilic drugs are difficult to prepare for pharmaceutical applications, especially injectable intravenous formulations, and that prior attempts using lipid vesicles and oil-in-water emulsions required complicated processing steps, harsh or clinically unacceptable solvents, and/or resulted in formulation instability (¶0010). Ulm further teaches that its formulations have particular merit in rendering water-insoluble drugs suitable for intravenous administration (¶0034), and confirms that the active (17-AAG) is particularly soluble in the oil phase, necessitating the oil-in-water design (¶0055).
Regarding claim 1, Ulm teaches that emulsifying agents (synonymous with surfactants) include phospholipids such as lecithin, and that a common surfactant/emulsifying agent is soya lecithin (Phospholipon 90G), which has been used in parenteral nutritional products at concentrations of about 0.5–25% w/v, preferably 0.5–10% w/v, most preferably 1–8% w/v (¶0047).
Regarding claims 4-8, Ulm teaches emulsion (¶ 0055), the surfactant/emulsifying agent is lecithin (¶ 0047), osmotic agent glycerol, sugars, sugar alcohols (¶ 0052), EDTA disodium, dihydrate (¶ 0074, 0077), and to prevent or minimize oxidative degradation or lipid peroxidation, antioxidants, e.g., alpha-tocopherol and butylated hydroxytoluene, and preservatives, for example edentate may be included in addition to, or as an alternative to, oxygen deprivation (e.g., formulation in the presence of inert gases such as nitrogen and argon, and/or the use of light resistant containers) (¶ 0056). Furthermore, Ulm teaches buffer solution, for example Hank’s solution, Ringer’s solution, or physiological saline buffer, as each are well-known in the art (¶ 0067).
Regarding claims 9 and 11, Ulm teaches pharmaceutical composition comprising a pharmacologically active compound, e.g., an ansamycin such as 17-AAG, in combi- nation with an emulsifying agent (e.g., phospholipids such as found in lecithin) and oil, wherein the oil may contain long chain triglycerides and the composition can also contain medium chain triglycerides, and the emulsifying agent and oil together constitute a lipid phase (¶ 0013).
Regarding claim 10, Ulm teaches the surfactant/emulsifying agent is typically present in a concentration of about 0.5-25% w/v based on the amount of the water and/or other components into which the surfactant is dissolved (¶ 0047). Furthermore, Ulm teaches ethanol is added in an amount approximately 50x the drug weight and the solution sonicated in a water bath to disperse the drug (¶ 0075; Example 4), and the pharmaceutical composition of claim 1 that is an oil in water emulsion having a lipid phase and an aqueous phase, and wherein said lipid phase comprises 5-30% by weight of the total (claims 6, 8).
Regarding claim 12, Ulm teaches formulation of 17-allylamino-geldanamycin (17-AAG) is a synthetic analog of geldanamycin (GDM), wherein both molecules belong to a broad class of antibiotic molecules known as ansamycins (¶ 0004) and (17-AAG) are thought to exert anti-cancerous effects by tight binding of the N-terminus ATP-binding pocket of HSP90 (¶ 0006). Furthermore, Ulm teaches in some embodiments, the compound (17-AAG) drug in an amount of 0.5mg/ml to 4 mg/ml or 0.05 % w/w to 0.4% w/w relative to the total formulation weight (¶ 0021), particularly, in one embodiment, comprises components of 2 mg/ml (17-AAG), 6.6 % lecithin, 7.5 % sucrose, and water (¶ 0022). This example differs from instant formulation as it does not contain instant formula of compound (I), however the limitations of percentages of components of the amounts of the compound, lecithin and sugar overlaps with instant ranges and the long chain and medium chain triglyceride can be 0 % as recited in the claim. A person having ordinary skill in the art would have been able to convert w/w to w/v relative to the total formulation volume used.
Regarding claims 13-15, Ulm teaches variation of processes comprising of adding long chain triglycerides for the compound (17-AAG) at 1 % w/w, a source of long chain triglycerides (soya oil) 16 % w/w, mixed with Miglyol 812N (a source of medium chain triglycerides) at 50.0 % w/w, and an emulsifying agent (Phospholipon 90G (PL90G)) at 33.03 % w/w, and 9.375 % w/w sucrose, and EDTA 0.0063 % w/w (¶ 0084, Example 6). Furthermore, Ulm discloses formulation 1 and formulation 2 with different amounts of (17-AAG), a source of long chain triglycerides (soya oil), Miglyol 812N (a source of medium chain triglycerides), lecithin, sucrose, sodium edetate, and water (¶ 0085) and further exemplary examples 1-9 are representative of various aspects of embodiments and one skilled in the art would have been able to adapt, carry out or modify the objects and obtain the ends and advantages within the spirit and scope of the invention (¶ 0096). Therefore, it would have been obvious to a person having ordinary skill in the art to optimize the percentages of the components in order to prevent or minimize oxidative degradation with proper amount of antioxidant (e.g., inert gases, EDTA) and achieve desired emulsification of the emulsion with surfactant/emulsifying agent (e.g., lecithin, PEG), osmotic agent (e.g., a sugar, glycerol), and stability with pH modifying agent (e.g., citric acid, phosphoric acid or a buffer solution).
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to formulate the Bcl-2 protein degrader of Zheng as a nanoemulsion as taught by Singh, and to select a droplet size within the claimed 20-150 nm range using the known, result-effective manufacturing parameters taught by Singh, including shear rate, surfactant concentration, homogenization pressure/cycles, sonication amplitude/time (pp. 32-34), and to further optimize the composition using the lecithin-based lipid system and weight percentages taught by Ulm, with a reasonable expectation of success. Such motivation exists because (1) Singh’s own review catalogs numerous distinct actives successfully formulated as nanoemulsions within this precise size range across parenteral, oral, ocular, and topical routes (Tables 2–5, pp. 41–45), demonstrating this is a routinely achievable and predictable result; (2) Ulm already demonstrates that a structurally analogous formulation challenge — rendering a water-insoluble, solvent-sensitive lipophilic drug (17-AAG) suitable for injectable administration via a lecithin/triglyceride/sucrose emulsion system — was successfully solved using the same class of excipients and manufacturing approach recited in the instant claims (¶¶0010, 0034, 0055, 0074–0076, 0085); and (3) combining Zheng's compound with the optimized nanoemulsion platform of Singh and Ulm would predictably improve drug delivery, stability, and bioavailability. Please see MPEP 2141(III)(A)–(G) and MPEP §§2144–2144.09.
One would have been motivated to do so because the combined teachings of Zheng, Singh and Ulm discloses compounds directed to instant formula (I), the combination references are drawn to the identical instant molecular structure of compound (I), and the variations and components involved in nanoemulsion formulations for drug delivery. One of ordinary skill in the art would have found it obvious to apply the different amounts and percentages of surfactant, emulsifying agent, osmotic adjusting agent, an antioxidant, a stabilizer, a pH modification agent, an inorganic salt or a buffering agent in order to improve the desired nanoemulsion formulation and use as taught by Zheng in view of Singh and further in view of Ulm.
From the combined 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.
Response to Arguments
Applicant's arguments filed 07/13/2026 have been fully considered but they are not persuasive for the following reasons.
I. The Cited References Teach the Claimed Droplet Size Range
Applicant argues (Section I of the Remarks) that none of the cited references teaches or suggests a nanoemulsion comprising the specific combination of 0.5–2.0% w/v of Compound 1 and 20–150 nm droplet sizes.
Examiner respectfully disagrees. Singh, already of record and cited in the Final Office Action for its nanoemulsion teachings, expressly discloses that droplet size is the most important criterion in nanoemulsion manufacturing and a variable directly and predictably controlled through well-understood process parameters (p. 32, §3.4). Singh further discloses numerous specific working nanoemulsions with droplet sizes falling within or overlapping the claimed 20–150 nm range across a variety of actives and administration routes, including droplet sizes of 20–100 nm (topical caffeine NE, §9.3), 20–200 nm (turmeric oil NE, Table 4), 30–100 nm (piroxicam and insulin NEs, Table 3), 40–80 nm (parenteral TOCOSOL™, §9.1), 70–90 nm (ramipril, Table 3), 80–100 nm (silymarin, Table 3), and 95 ± 2 nm (ocular DOTAP NE, §9.4). The claimed range of 20–150 nm is therefore taught, or at minimum obvious as an overlapping range achieved through routine optimization. The 0.5–2.0% w/v drug loading range remains taught by Ulm's overlapping 0.05–0.4% w/w (equivalent to approximately 0.05–0.4% w/v) range for the analogous ansamycin formulation (¶0021).
II. Applicant's Comparative Data Does Not Establish Unexpected Results
Applicant argues (Sections II–V of the Remarks) that comparative data in the specification demonstrates a critical and unexpected relationship between the claimed 20–150 nm droplet size range and sterile filterability, colloidal stability, and formulation appearance.
Examiner respectfully disagrees that this data is sufficient to rebut the prima facie case of obviousness. A showing of unexpected results must compare the claimed subject matter against the closest prior art, not merely against the applicant's own internal formulations. See MPEP 716.02(e); In re Baxter Travenol Labs., 952 F.2d 388, 392 (Fed. Cir. 1991). The comparative data presented by Applicant (e.g., Example 1 vs. Examples 6–15; Example 5 vs. Example 6) is drawn entirely from Applicant's own formulations and is not compared against the closest prior art nanoemulsion embodiments of record — specifically the working examples in Ulm (¶¶0074–0076, ¶0085, Formulations 1 and 2, Example 6) or the specific droplet-size embodiments disclosed in Singh. Absent a comparison against the closest prior art, the alleged criticality of the 20–150 nm boundary has not been established.
Additionally, the correlation between droplet size and sterile filterability through a 0.2 µm filter is a well-recognized and predictable property of colloidal dispersions generally. Ulm itself teaches that filtration through a 0.45 µm followed by a 0.2 µm filter is a standard step in nanoemulsion processing (¶0058, ¶0079), and Singh teaches that small droplet size inherently imparts kinetic stability and resistance to destabilization phenomena such as creaming, sedimentation, and coalescence (p. 29, Introduction; pp. 36–37, §§7.1–7.3). The observed transition from cloudy/filtration-failing formulations above 150 nm to semi-transparent/filterable formulations within the claimed range is thus an inherent and predictable consequence of reducing droplet size below the filter pore threshold — not an unexpected result. Applicant has not shown this correlation to be surprising relative to the closest prior art.
III. Applicant's Stability Data Does Not Overcome the Rejection
Applicant argues (Section III) that stability data in Table 9 (¶¶0057–0058) corroborates the criticality of the claimed range, as formulations stored at 2–8°C maintained droplet sizes within 20–150 nm while formulations stored at −20°C and 25°C exhibited droplet growth beyond 150 nm.
This argument is not persuasive for two reasons. First, the comparison again is between Applicant's own formulations stored under different conditions — not against the closest prior art. See MPEP 716.02(e). Second, Ulm itself discloses stability data for its 17-AAG lyophilized nanoemulsion showing droplet sizes of 0.187–0.200 µm (187–200 nm) maintained over 10 weeks at 2–8°C (¶0087, Example 7 stability table), and further discloses that its formulations are stable at −20°C, 2–8°C, and room temperature for periods in excess of two months (¶0082). The concept that emulsion droplet size should be controlled and maintained within a target range for stability is thus well-recognized in the art, and Applicant's data does not establish that maintaining droplet sizes within 20–150 nm specifically — as opposed to the adjacent ranges taught by Ulm — produces unexpectedly superior stability results.
IV. The Physicochemical Complexity of Compound 1 Does Not Defeat Reasonable Expectation of Success
Applicant argues (Section IV) that Compound 1 presents inherently unpredictable formulation challenges due to its conflicting physicochemical properties — hydrophobic character, polar functional groups, poor water solubility, and incompatibility with pharmaceutically acceptable organic solvents — such that nanoemulsion formulation of Compound 1 was far from routine.
Examiner respectfully disagrees. Ulm expressly recognizes that ansamycins, like many other lipophilic drugs, are difficult to prepare for pharmaceutical injectable formulations, and that prior attempts required complicated processing steps, harsh or clinically unacceptable solvents, and/or resulted in formulation instability (¶0010). Ulm's invention is directed precisely to solving this class of challenge — rendering water-insoluble, solvent-sensitive lipophilic drugs suitable for intravenous administration via a lecithin/triglyceride/sucrose emulsion system (¶0034). Ulm's Example 4 further demonstrates that 17-AAG — which like Compound 1 requires a transient organic solvent (ethanol) to facilitate dissolution into the oil phase before the solvent is removed — was successfully incorporated into a stable parenteral nanoemulsion using this approach (¶¶0074–0076). The successful formulation of 17-AAG under these conditions directly demonstrates that the class of physicochemical challenges Applicant describes for Compound 1 was not an obstacle to successful nanoemulsion development using the Ulm platform. Applicant has not identified any property of Compound 1 that would have been expected to prevent successful nanoemulsion formulation using the Zheng/Singh/Ulm combined approach.
V. The Examiner's Prima Facie Case Establishes Reasonable Expectation of Success
Applicant argues (Section VI) that the Examiner's prima facie case does not establish a reasonable expectation of success because the cited references provide no guidance on achieving the specific 20–150 nm droplet size for a compound with Compound 1's particular physicochemical challenges.
Examiner respectfully disagrees. As set forth above, Singh discloses that droplet size in a nanoemulsion is a result-effective variable directly controlled by known, well-understood manufacturing parameters including shear rate, surfactant selection and concentration, homogenization pressure/cycles, and sonication parameters (pp. 32–34). Singh's review further documents that these techniques routinely produce nanoemulsions across a wide variety of actives with droplet sizes within the 20–150 nm window, confirming that achieving droplet sizes in this range is an expected, not exceptional, outcome of conventional nanoemulsion manufacturing. Moreover, motivation alone is not required to establish a reasonable expectation of success when, as here, the result-effective variables are well-characterized and the techniques for controlling them are fully described in the prior art. See In re Dow Chemical Co., 837 F.2d 469, 473 (Fed. Cir. 1988). The prior art combination as a whole provides a person of ordinary skill with a reasonable expectation of success in achieving the claimed formulation.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANDRE MACH whose telephone number is (571)272-2755. The examiner can normally be reached 0800 - 1700 M-F.
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/ANDRE MACH/Examiner, Art Unit 1615
/Robert A Wax/Supervisory Patent Examiner, Art Unit 1615
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