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 .
Formal Matters
Applicants’ responses in the reply filed on 02 July 2026 are acknowledged and have been fully considered. Claims 1-4, 11-14, 16-17, 21, 25, 27-28, 41, 44-47, and 50 are pending. Claims 1-4, 11-14, 16-17, 21, 25, 27-28, 41, and 44-45 are under consideration in the instant office action. Claims 46-47 and 50 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and/or species, there being no allowable generic or linking claims. Claims 5-10, 15, 18-20, 22-24, 26, 29-40, 42-43, and 48-49 are canceled.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted on 02 July 2026 and 03 January 2025 are noted and the submissions follow the provisions of 37 CFR 1.97. Accordingly, the examiner has considered the references. Signed copies are attached herein.
Election/Restrictions
Applicant's election without traverse of Group I (claims 1-4, 11-14, 16-17, 21, 25, 27-28, 41, 44-45) in the reply filed on 02 July 2026 is acknowledged. Additionally, Applicant’s election the species depicted below for examination in the reply filed on 02 July 2026 is also acknowledged.
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Elected Species
The examiner indicates that the elected species is free of prior art. The examiner extended search and examination to two of the azide containing species depicted in claim 27.
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Claim Rejections - 35 USC § 102
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(s) 1-4, 11-14, 16-17, 21, 25, 27-28, and 44 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Müller et al. (Langmuir 2019, 35, 12439−12450).
Müller et al. disclose in the abstract as follows:
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Müller et al. disclose in Figure 1 as follows:
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The examiner notes that the two structures P15AzPdPC clearly read on the below species
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Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Note: The examiner indicates that the elected species is free of prior art. The examiner extended search and examination to two of the azide containing species depicted in claim 27.
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Claims 1-4, 11-14, 16-17, 21, 25, 27-28, and 44-45 are rejected under 35 U.S.C. 103 as being unpatentable over Gubbens et al. (Chemistry & Biology 16, 3–14, January 30, 2009) in view of Salic (US 2012/0028290) and Brito et al. (US 2016/0311759).
Applicants’ claims
Applicants claim a composition comprising a compound of formula I. Dependent claims thereof recite other further defining features.
Determination of the Scope and Content of the Prior Art
(MPEP 2141.01)
Gubbens et al. teach new lipid analogs mimicking the abundant membrane phospholipid phosphatidyl choline were developed to photocrosslink proteins interacting with phospholipid headgroups at the membrane interface. In addition to either a phenylazide or benzophenone photoactivatable moiety attached to the headgroup, the lipid analogs contained azides attached as baits to the acyl chains. After photocrosslinking in situ in the biomembrane, these baits were used for the attachment of a fluorescent tetramethyl rhodamine alkyne conjugate or a biotin-alkyne conjugate using click chemistry, allowing for the selective detection and purification of crosslink products, respectively. Proteins crosslinked to the lipid analogs in inner mitochondrial membranes from Saccharomyces cerevisiae were detected and subsequently identified by mass spectrometry. Established interaction partners of phosphatidylcholine were found, as well as known integral and peripheral inner membrane proteins, and proteins that were not previously considered mitochondrial inner membrane proteins (see summary). Gubbens et al. teach on Figure 3 the structure depicted below:
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Claimed structure as follows:
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The examiner notes that the above structure differs from the claimed structure below in claim 27 the number of the hydrophobic alkyl chains. According to MPEP 2144.08 (c) consider any teachings of a "typical," "preferred," or "optimum" species or subgenus within the disclosed genus. If such a prior art species or subgenus is structurally similar to that claimed, its disclosure may provide a reason for one of ordinary skill in the art to choose the claimed species or subgenus from the genus, based on the reasonable expectation that structurally similar species usually have similar properties. See, e.g., Dillon, 919 F.2d at 693, 696, 16 USPQ2d at 1901, 1904. See also In re Deuel, 51 F.3d 1552, 1558, 34 USPQ2d 1210, 1214 (Fed. Cir. 1995) ("Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homologs because homologs often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.").
Ascertainment of the Difference Between Scope of the Prior Art and the Claims
(MPEP 2141.02)
Gubbens et al. do not specifically teach the inclusion of a therapeutic agent. These deficiencies are cured by the teachings of Salic.
Salic teaches a method to label phospholipids in vivo based on the metabolic incorporation of an alkynyl- or azido-labeled metabolic precursor into phospholipids. The resulting phospholipids have alkynyl or azido moieties, which, upon reaction with a labeled azide or alkyne, respectively, form labeled compounds that can be visualized using optical or electron microscopy with high sensitivity and spatial resolution in cells or tissue. The present method provides a valuable tool for imaging phospholipid synthesis, turnover and subcellular localization in cultured cells as well as in animals (see abstract). A method for visualizing phospholipids in living cells comprising: contacting the living cells with a precursor having an alkynyl or azido moiety under conditions sufficient to allow the phospholipids in the cells to incorporate the precursor, thereby forming an alkynyl-labeled or azido-labeled phospholipid; contacting the cells with a detectable label having an azide or alkyne group under conditions sufficient to allow the azide or alkyne group to react with the alkynyl or azido moiety, thereby forming phospholipids labeled with the detectable label; and visualizing the detectable label using optical or electron microscopy. The method of claim 13, wherein the detectable label having an azide group comprises biotin azide, TMR-azide, fluorescein azide or Alexa568-azide (claim 13). The examiner notes that these agents have therapeutic values.
Gubbens et al. and Salic do not specifically teach the composition in the form of a particle. These deficiencies are cured by the teachings of Brito et al.
Brito et al. teach a cationic lipid scaffold that demonstrates enhanced efficacy along with lower toxicity (improved therapeutic index) as a result of lower sustained lipid levels in the relavent tissues, and for local delivery applications (eye, ear, skin, lung); delivery to muscle (i.m.), fat, or subcutaneous cells (s.c. dosing) (see paragraph 0011). In a third aspect, this invention provides for a pharmaceutical composition (i.e. formulation) comprising a lipid composition of the invention and a pharmaceutically acceptable carrier or excipient. In one embodiment, the pharmaceutical composition comprises at least one other lipid component in the lipid composition. In another embodiment the lipid composition is in the form of a liposome. In another embodiment the lipid composition is in the form of a lipid nanoparticle (paragraph 0014).
Finding of Prima Facie Obviousness Rational and Motivation
(MPEP 2142-2143)
It would have been prima facie obvious to a person of ordinary skill in the art before the effective filing date of the instant invention to modify the teachings of Gubbens et al. by including a therapeutic agent because Salic teaches a method to label phospholipids in vivo based on the metabolic incorporation of an alkynyl- or azido-labeled metabolic precursor into phospholipids. The resulting phospholipids have alkynyl or azido moieties, which, upon reaction with a labeled azide or alkyne, respectively, form labeled compounds that can be visualized using optical or electron microscopy with high sensitivity and spatial resolution in cells or tissue. One of ordinary skill in the art would have been motivated to include therapeutic agents because Salic teaches that the present method provides a valuable tool for imaging phospholipid synthesis, turnover and subcellular localization in cultured cells as well as in animals (see abstract). A method for visualizing phospholipids in living cells comprising: contacting the living cells with a precursor having an alkynyl or azido moiety under conditions sufficient to allow the phospholipids in the cells to incorporate the precursor, thereby forming an alkynyl-labeled or azido-labeled phospholipid; contacting the cells with a detectable label having an azide or alkyne group under conditions sufficient to allow the azide or alkyne group to react with the alkynyl or azido moiety, thereby forming phospholipids labeled with the detectable label; and visualizing the detectable label using optical or electron microscopy. The method of claim 13, wherein the detectable label having an azide group comprises biotin azide, TMR-azide, fluorescein azide or Alexa568-azide (claim 13). The examiner notes that these agents have therapeutic values. One of ordinary skill in the art would have had a reasonable chance of success in combing the teachings of Gubbens et al. and Salic because both references are drawn to azide modified phosphatidylcholine for imaging purposes.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, as evidenced by the references, especially in the absence of evidence to the contrary.
Claim(s) 41 is/are rejected under 35 U.S.C. 103 as being unpatentable over Gubbens et al. (Chemistry & Biology 16, 3–14, January 30, 2009) in view of Salic (US 2012/0028290) as applied to claim1-4, 11-14, 16-17, 21, 25, 27-28, and 44-45 above, and further in view of Brito et al. (US 2016/0311759).
Applicants’ claims
Applicants claim a composition comprising a compound of formula I. Dependent claims thereof recite other further defining features.
Determination of the Scope and Content of the Prior Art
(MPEP 2141.01)
The teachings of Gubbens et al. and Salic are described above in detail and are incorporated by reference herein.
Ascertainment of the Difference Between Scope of the Prior Art and the Claims
(MPEP 2141.02)
Gubbens et al. and Salic do not specifically teach the composition in the form of a particle. These deficiencies are cured by the teachings of Brito et al.
Brito et al. teach a cationic lipid scaffold that demonstrates enhanced efficacy along with lower toxicity (improved therapeutic index) as a result of lower sustained lipid levels in the relavent tissues, and for local delivery applications (eye, ear, skin, lung); delivery to muscle (i.m.), fat, or subcutaneous cells (s.c. dosing) (see paragraph 0011). In a third aspect, this invention provides for a pharmaceutical composition (i.e. formulation) comprising a lipid composition of the invention and a pharmaceutically acceptable carrier or excipient. In one embodiment, the pharmaceutical composition comprises at least one other lipid component in the lipid composition. In another embodiment the lipid composition is in the form of a liposome. In another embodiment the lipid composition is in the form of a lipid nanoparticle (paragraph 0014).
Finding of Prima Facie Obviousness Rational and Motivation
(MPEP 2142-2143)
It would have been prima facie obvious to a person of ordinary skill in the art before the effective filing date of the instant invention to modify the teachings of Gubbens et al. and Salic by preparing the composition in the form of particle because Brito et al. teach a cationic lipid scaffold that demonstrates enhanced efficacy along with lower toxicity (improved therapeutic index) as a result of lower sustained lipid levels in the relavent tissues, and for local delivery applications (eye, ear, skin, lung); delivery to muscle (i.m.), fat, or subcutaneous cells (s.c. dosing) (see paragraph 0011). One of ordinary skill in the art would have been motivated to do so because Brito et al. teach that in a third aspect, this invention provides for a pharmaceutical composition (i.e. formulation) comprising a lipid composition of the invention and a pharmaceutically acceptable carrier or excipient. In one embodiment, the pharmaceutical composition comprises at least one other lipid component in the lipid composition. In another embodiment the lipid composition is in the form of a liposome. In another embodiment the lipid composition is in the form of a lipid nanoparticle (paragraph 0014). This can achieve providing a cationic lipid scaffold that demonstrates enhanced efficacy along with lower toxicity (improved therapeutic index) as a result of lower sustained lipid levels in the relavent tissues, and for local delivery applications (eye, ear, skin, lung); delivery to muscle (i.m.), fat, or subcutaneous cells (s.c. dosing) (see paragraph 001). One of ordinary skill in the art would have had a reasonable chance of success in combing the teachings of Gubbens et al., Salic, and Brito et al. because all of the references are drawn to phospholipids for therapeutic use.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TIGABU KASSA whose telephone number is (571)270-5867. The examiner can normally be reached on 8 AM-5 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, David Blanchard can be reached on 571-272-0827. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/TIGABU KASSA/Primary Examiner, Art Unit 1619
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