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 .
DETAILED ACTION
Formal Matters
Claims 2-4, 7-9, 12-13, 15-17, 20-22, 24-29, 34-35, 39, 44, 46-49, and 51-53 are cancelled. Claims 1, 5, 6, 10-11, 14, 18, 19, 23, 30-33, 36-38, 40-43, 45, and 50 are pending and under examination.
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 3/2/2026 has been entered.
Priority
This application is a national stage entry of PCT/US2021/044564 filed on 8/4/2021, which claims priority from US provisional application 63/060,968 filed on 8/4/2020.
Information Disclosure Statement
The information disclosure statement filed on 12/05/2025 has been considered by the examiner.
Rejections Withdrawn
The rejection under USC 102(a)(1) over Veiseh is withdrawn per applicant’s amendments and arguments.
The rejection under USC 103 over Veiseh WO 2018067615A1 and Chemtips is withdrawn per applicant’s amendments and arguments.
Each of the previous rejections under non-statutory double patenting from the prior final rejection are withdrawn per applicant’s amendments to the claims to define the R1b group.
As these rejections are withdrawn, applicant’s arguments toward the rejections are moot. However, note a new rejection below.
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 42, 45 and 50 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 42 is indefinite for not reciting whether the % is in mass%, volume%, molar% or other type of %. It is unclear on how much less of a second compound can be present since different units will have different measurements. For the purpose of compact prosecution, it will be read in terms of weight %.
Claim 45 and 50 are indefinite for reciting the % values and then in parentheses reciting (w/w, w/v, v/v, or % by dry weight) as it is unclear if applicant is exemplifying the types of units that the % values can be read as and does not necessarily intend that any of those listed have to be chosen, or if applicant intends each of the options to be considered where the claim could be read under any one of those units to for consideration of the prior art. For the purpose of compact prosecution if the prior art teaches any one of those listed units to meet the limitation, then it will read on the claim.
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 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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, 5, 6, 10, 14, 18, 19, 23, 30, 31, 32, 33, 36, 37, 38, 40, 41, 42, 43, 45 and 50 are rejected under 35 U.S.C. 103 as being unpatentable over Veiseh WO 2018067615A1 and Baer WO1997041093A1.
Veiseh teaches a compound that has a structure of formula II-q -
PNG
media_image1.png
148
437
media_image1.png
Greyscale
that has definitions as in paragraph 309-310 that are like those of the applicant’s claims. The squiggle denote attachment to a device or material (paragraph 309). Veiseh teaches a compound of formula III-1 that has an RC group at the N position -
PNG
media_image2.png
147
270
media_image2.png
Greyscale
. RC can be hydrogen, alkyl, alkenyl, alkynyl, heteroalkyl, cycloalkyl, heterocyclyl, or heteroaryl (paragraph 343 group definitions). Veiseh teaches
PNG
media_image3.png
267
471
media_image3.png
Greyscale
. These compounds (3267-3270) have groups on the -NH- group that can be construed to protect the amine group while being attached to the compound via the -C-C-O- repeat group. Additionally, see compounds
PNG
media_image4.png
499
475
media_image4.png
Greyscale
(figure 6H). Compound 3260 in figure 6H has a Boc groups on the amine group. Veiseh teaches provides for use of protection group (paragraph 532). Veiseh also teaches
PNG
media_image5.png
198
495
media_image5.png
Greyscale
(page 222). Veiseh teaches
PNG
media_image6.png
101
476
media_image6.png
Greyscale
which is compound 100 in applicant’s table 1. Paragraphs 478 and 514-522 teaches a composition. Paragraphs 115 and 116 provide that various isomers, etc can be isolated by techniques known in the art, and thus, recognizes the compounds can be isolated to be pure as well as more than 75% by weight. Veiseh teaches single compounds, and thus, also envisions there isolated state without other compounds. Veiseh provides for salts of its compounds and treating disorders (pharmaceutical purpose) (Abstract). In regards to onset temperatures and maximum exothermic output, these are properties of the compound, but can be affected by reaction conditions and procedures used for calculation. These compounds of the prior art like compounds 3039, 3254, 3255, and 3270 have close structural similarities to compounds in applicant’s specification and will be expected to have similar onset temperatures and maximum exothermic outputs (see MPEP 2112). As Veiseh teaches compounds of the claims that have groups that can act as protecting groups on the amine group, these compounds would have such properties. They are also expected to be in liquid state based on the close structural relationship. The amide groups in compounds like 3255 would be acid or base labile under conditions (see Master Organic Chemistry, Carboxylic Acid Derivatives, Amide hydrolysis, 2025, https://www.masterorganicchemistry.com/2019/10/07/amide-hydrolysis/) for evidence of acid and base hydrolysis of amide groups.
Veiseh teaches the claims as discussed above. It is noted that Veiseh teaches broader structures of formula I and II with definitions of each group that allows for formation of more compounds including those encompassed by applicant’s genus structures (paragraphs 3-21). Figure 6H and other figures in Veiseh provide for compounds using other definitions of the groups for formula I or II. Compound 3260 in figure 6H has a Boc groups on the amine group. Veiseh provides for use of protection group (paragraph 532).
Veiseh does not teach a compound with one of the groups as in claim 11, it does not provide for BOC as the 1b group in a compound as claimed in claim 1, and does not provide a method of making a compound with the exact compounds provided in claim 43. Veiseh teaches a process for making a compound that involves reacting a compound with an azide and a alkyne (page 235, also page 226 and page 219).
PNG
media_image7.png
335
1105
media_image7.png
Greyscale
Veiseh does additionally teach other compounds similar to claimed compounds with a BOC group on the amine as provided above by Veiseh. Thus, Veiseh does allow provide this group for adding to the amine group of its compounds allowing one of ordinary skill in the art to utilize this group on the amine in each of its compounds. Furthermore, Veiseh provides for a compound with a group on the amine group that is similar in structure to a succinimide group (compound 3253). Thus, Veiseh does provide for such groups for its compounds at the amine position in its compounds.
Although Veiseh provides for use of a Boc group in compounds and use of protecting groups, it does not provide reasoning for doing so that might lead one to use in its other synthesis reactions.
Veiseh might not indicate a compound that is liquid, but these are known states of matter and based on the close structural similarity to applicant’s compounds, Veiseh would have provided compounds of both the liquid or solid states.
Veiseh provides for relative amounts of active ingredients where the composition can be 0.1% to 100% w/w of the active ingredient (paragraph 517). Veiseh provides for pharmaceutical compositions being prepared, packaged and/or sold in bulk, as a single unit or as a plurality of units (paragraph 516). Veiseh teaches 100 mg to 1000 mg of compound per dosage unit (paragraph 527). Veiseh teaches five, six… fourteen or more administrations which would allow for amounts of 500 to 5000 mg of the compound or more depending on the number of doses stored in a package (container).
Veiseh provides for purifying the compounds of its examples and providing pure enantiomeric compound (paragraph 116 and examples). Thus, substantially pure compounds would be a goal of Veiseh’s teachings.
Baer teaches synthesis of Fmoc protected amines (abstract and example 1). Baer teaches protecting groups with the following characteristics : (1) reacts selectively with the desired functionality in good yield to give a derivative that is stable to the projected reactions for which protection is desired; 2) can be selectively removed from the derivatized solid support to yield the desired functionality; and 3) is removable in good yield by reagents compatible with the other functional group(s) generated in such projected reactions (page 9). Baer teaches “Examples of protecting groups can be found in Greene et al. (1991) Protective Groups in Organic Synthesis. 2nd Ed. Qohn Wiley & Sons, Inc., New York). Preferred protecting groups include photolabile protecting groups (such as methylnitropiperonyloxycarbonyl (Menpoc), methylnitropiperonyl (Menp), nitroveratryl (Nv), nitroveratryloxycarbonyl (Nvoc), or nitroveratryloxymethyl ether (Nvom)); acid-labile protecting group (such as Boc or DMT); base-labile protecting groups (such as Fmoc, F , phosphonioethoxycarbonyl (Peoc, see Kunz (1976) Chem. Ber. 1Q9_:2670); groups which may be removed under neutral conditions (e.g., metal ion-assisted hydrolysis ), such as DBMB (see Chattopadhyaya et al. (1979) T.C.S. Chem. Comm. 987-990), allyl or alloc (see, e.g., Greene and Wuts, "Protective Groups in Organic Synthesis", 2nd Ed., John Wiley & Sons, Inc., New York, NY (1991), 2-haloethyl (see Kunz and Buchholz (1981) Angew. Chem. Int F.H Engl. 20:894), and groups which may be removed using fluoride ion, such as 2- (trimethylsilyl)ethoxymethyl (SEM), 2-(trimethylsilyl)ethyloxycarbonyl (Teoc) or 2- (trimethylsilyl)ethyl (Te) (see, e.g., Lipshutz et al. (1980) Tetrahedron I .P. Γ. ?ι -:v . 3346)); and groups which may be removed under mild reducing conditions (e.g., with sodium borohydride or hydrazine), such as Lev Id. at 30-31, 97, and 112” (pages 9-10). Baer teaches “Chemical protecting groups are used during synthesis reactions to temporarily protect certain functional groups on a compound against undesired reactions. When a reaction sequence is complete, and protection is no longer necessary, the protective group is removed to restore the protected functional group to its natural activity. Protective groups are removed by various procedures such as exposure to acidic or basic conditions or electromagnetic radiation (e.g., light of a prescribed wavelength).” (page 1). Page 2 provides for the structure of Fmoc reagent to be added to an amine group.
PNG
media_image8.png
119
118
media_image8.png
Greyscale
One of ordinary skill in the art before the time of filing would have added protecting groups to the amine used in the reactions taught by Veiseh by teachings of Baer to make its compounds with protecting groups on amine groups by known techniques of the prior art. For example, Compound 3037 of Veiseh, which also teaches protecting groups, when modified with an amine protecting group of Baer for protection of that amine group would reasonably provide compounds such as compound 107 of applicant’s claims. Baer teaches other options of protecting groups (e.g. alloc, Boc and others) that would allow for other “protected” compounds to be produced with the methods of Baer. This would produce compounds that have a protecting group on the amine (-NH2) group of compounds in Veiseh with a reasonable expectation of success . One of ordinary skill in the art based on Veiseh would also be to package the drug in containers and provide amounts based on the desired dose of drug and amount of dosages to be administered to the subject in a given period of time. As compounds of applicant’s claims are motivated by the combination of Veiseh with Baer, compounds with properties of applicant’s claims would have reasonably been produced (onset temperature and maximum exothermal output).
Response to Applicant’s Arguments
As each of the previous rejections was withdrawn, applicant’s arguments toward those rejections are now moot. The above prior art rejection is made in response to applicant’s amended claims after also considering their arguments.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MARK V STEVENS whose telephone number is (571)270-7080. The examiner can normally be reached on M-F 9:00 am to 6:00 pm 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, Brian-Yong Kwon can be reached on (571)272-0581. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/MARK V STEVENS/Primary Examiner, Art Unit 1613
Prosecution Insights