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 Group I and species of fully specified R1 and R2 in the reply filed on January 28, 2026 is acknowledged. No prior art was found in the search for elected species. The search and examination was expanded to the full scope of claim 1.
The traversal is on the ground(s) that searching the groups together would not place upon the Examiner a serious search and examination burden, and the claims are directed to a reasonable number of species. This is not found persuasive because a serious search burden exists because the different groups have different classifications. The claims are not drawn to a reasonable number of species given the large breadth of R1 and R2. For example, R1 can be a hydrocarbyl group of any length substituted with amine and fluorine atoms and R2 can be any species comprising polyethylene glycol.
The requirement is still deemed proper and is therefore made FINAL.
Drawings
FIGs 1A, 1B, 1C, 2, 3, 4A, 4B, and 4C are objected to because the chemical bonds are shown as dashed lines in the structure. It is not clear what the short and long dashed lines mean. In the art, a dashed line indicates that the bond is below the plane of the drawing, a partial bond, delocalization, or a hydrogen bond (page 1904, ¶ 3; Brecher, Pure and Applied Chemistry, 2006; cited on PTO-892). The specification does not provide sufficient information or definition. Accordingly, the figures fail to provide a clear understanding of the claimed invention.
Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Appropriate correction is required.
Specification
The disclosure is objected to because of the following informalities:
The use of the terms Milli-Q®, SpectroSpin®, AVANCE™, PARAVISION® (PV), SigmaPlot® which are a trade name or a mark used in commerce, has been noted in this application. The term should be accompanied by the generic terminology; furthermore the term should be capitalized wherever it appears or, where appropriate, include a proper symbol indicating use in commerce such as ™, SM , or ® following the term.
Although the use of trade names and marks used in commerce (i.e., trademarks, service marks, certification marks, and collective marks) are permissible in patent applications, the proprietary nature of the marks should be respected and every effort made to prevent their use in any manner which might adversely affect their validity as commercial marks.
On pages 4, 8, 11, 16, and 19, the chemical structures contain chemical bonds with dotted line at both ends. It is not clear what the dotted lines mean.
Appropriate correction is required.
Claim Rejections - 35 USC § 112 Indefiniteness
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 1-11 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.
Regarding claims 1 and 9, the chemical structure of the formula contains chemical bonds with dashed lines at both ends. It is not clear what the dashed lines mean. In the art, a dashed line indicates that the bond is below the plane of the drawing, a partial bond, delocalization, or a hydrogen bond (page 1904, ¶ 3; Brecher, Pure and Applied Chemistry, 2006; cited on PTO-892). Neither the claims nor the specification defines which of these standard meanings applies, or if an alternative meaning is intended. Consequently, the specification fails to inform a person of ordinary skill in the art of the scope of the claimed invention with reasonable certainty. As the metes and bounds of the claimed invention cannot be reasonably ascertained, claims 1 and 9 are rejected as indefinite.
Regarding claims 1 and 9, the claims recites that a contrast agent has the formula shown in claim 1. In claim 1, the preamble recites a contrast agent, but the specific location, chemical nature, and isotopic identity of the contrast agent moiety are not clearly defined within the structural formula. Specifically, R1 is described as containing one or more fluorine atoms but it is not specified which isotopes are included. For example, naturally occurring fluorine-19 (19F) is typically used for a magnetic resonance imaging (MRI) agent and fluorine-18 (18F) is typically used for Positron Emission Tomography (PET) imaging agent. Furthermore, it remains unclear whether R2 comprises contrast agent moieties or isotopes, or if such moieties connect to the dashed lines, the meaning of such lines undefined as discussed above. Consequently, the body of the claim is appears to define the invention independently of the preamble. It is not clear how much weight should be afforded to the preamble as it fails to provide a distinct definition of the claimed limitations. .
When reading the preamble in the context of the entire claim, the recitation contrast agent is not limiting because the body of the claim describes a complete invention and the language recited solely in the preamble does not provide any distinct definition of any of the claimed invention' s limitations. Thus, the preamble of the claim(s) is not considered a limitation and is of no significance to claim construction. See Pitney Bowes, Inc. v. Hewlett-Packard Co., 182 F.3d 1298, 1305, 51 USPQ2d 1161, 1165 (Fed. Cir. 1999). See MPEP § 2111.02.
Regarding claims 1 and 9, the claims recites that R1 is a hydrocarbyl that is substituted with an amine and comprises one or more carbon atoms substituted with one or more fluorine atoms. The specification discloses that the term “hydrocarbyl” generally refers to aliphatic, aryl, or arylalkyl groups, including substituted derivatives thereof (¶ 76 of PGPub). The use of the phrase “generally refers to” is ambiguous as it fails to provide a fixed, exclusive definition. Furthermore, it is unclear how far the scope of “substituted derivatives” extends. The specification provides examples of substituted C4 hydrocarbyl as being a diethyl ether moiety or N,N-dimethylacetamide moiety (¶ 77 of PGPub). These examples do not comport with what one of ordinary skill in the art would consider a C4 hydrocarbyl to be. Generally, to one of ordinary skill in the art, “hydrocarbyl” groups mean univalent groups formed by removing a hydrogen atom from a hydrocarbon and hydrocarbons mean compounds consisting of carbon and hydrogen only (page 1341; Moss et al., Pure and Applied Chemistry, 1995; cited on PTO-892). For example, dependent claim 2 recites the R1 structure containing oxygen atoms. The “hydrocarbyl” in its ordinary meaning should not contain an oxygen atom, but the “hydrocarbyl” defined in the specification may or may not contain an oxygen atom. While applicants may act as their own lexicographers, the specialized definition must be sufficiently clear and unambiguous to provide notice of what the claim covers. Because the term “hydrocarbyl” of the instant application is contrary to the ordinary meaning and is not clearly redefined, the metes and bounds of the invention are not understandable to one of ordinary skill in the art, rendering the claims indefinite. See MPEP §§ 2111.01 and 2173.05(a). The dependent claims fall therewith.
Clarification and/or amendment is required.
For the purposes of applying art below, the term “hydrocarbyl” is being interpreted to include substituted derivatives such as those with oxygen substitutions.
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.
Claims 1-11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Du et al. (Bioconjugate Chemistry, April 21, 2022; cited on IDS filed June 10, 2024).
Regarding claims 1-8, Du 2022 discloses a contrast agent for 19F-based MRI comprising polyethylene glycol (PEG), poly(isobutylene-alt-maleic anhydride) (PIMA), and fluorine atoms (ABSTRACT). Du 2022 discloses the structure of PEG-OMe-PIMA-CF3 (page 883, Figure 1), which reads on the structure of a contrast agent of instant claims 1, 2, 4, 5, 7, and 8. The PEG-OMe component corresponds to R2 (wherein v is 15) shown in instant claims 2 and 8, and the PIMA-CF3 component corresponds to R1 shown in instant claims 2 and 5.
PNG
media_image1.png
260
236
media_image1.png
Greyscale
Du 2022 also discloses the structure the PEG-OMe-PIMA-PEG600-CF3 (page 885, Figure 2), which reads on the structure of a contrast agent of instant claims 1, 2, 4, and 6-8. The PEG-OMe component corresponds to R2 (wherein v is 15) shown in instant claims 2 and 8, and the PIMA- PEG600-CF3 component corresponds to R1 (wherein z is 12) shown in instant claims 2 and 6.
PNG
media_image2.png
414
227
media_image2.png
Greyscale
Du 2022 discloses that the molar ratio x (PEG-OMe) : y (PIMA-CF3) can be 70:30 (page 884, col. 1, ¶ 1), which reads on the x:y ratio of instant claims 1 and 3.
Regarding claims 9-11, Du 2022 discloses that the contrast agent can be dissolved in phosphate buffer (reads on aqueous liquid of instant claim 11) at varying concentrations such as 200 mg/mL (page 887, col. 2, ¶ 1; page 887, Figure 4), which reads on a composition comprising the contrast agent having a solubility of at least 1 mg/ml (instant claim 9) or 10 mg/ml (instant claim 10) .
Claims 1-11 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Liang Du (Florida State University, 2020; cited on PTO-892).
Regarding claims 1-8, Du 2020 discloses a set of 19F-containing polymers as contrast agents (page 74, ¶ 2). Du 2020 discloses the structure of PEGOMe-PIMA-CF3 (page 79, Figure 4.1), which reads on the structure of a contrast agent of instant claims 1, 2, 4, 5, 7, and 8. The PEGOMe component corresponds to R2 (wherein v is 15) shown in instant claims 2 and 8, and the PIMA-CF3 component corresponds to R1 shown in instant claims 2 and 5.
PNG
media_image1.png
260
236
media_image1.png
Greyscale
Du 2020 also discloses the structure the PEGOMe-PIMA-PEGCF3 (page 82, Figure 4.4), which reads on the structure of a contrast agent of instant claims 1, 2, 4, and 6-8. The PEGOMe component corresponds to R2 (wherein v is 15) shown in instant claims 2 and 8, and the PIMA- PEGCF3 component corresponds to R1 (wherein z is 12) shown in instant claims 2 and 6.
PNG
media_image2.png
414
227
media_image2.png
Greyscale
Du 2020 discloses that the molar ratio x (PEG-OMe) : y (PIMA-CF3) can be 70:30 (page 78, ¶ 2), which reads on the x:y ratio of instant claims 1 and 3.
Regarding claims 9-11, Du 2020 discloses that the contrast agent can be well solubilized in water at a concentration of up to 50 mg/ml (page 85, ¶ 1), which reads a composition comprising the contrast agent having a solubility of at least 1 mg/ml (instant claim 9) or 10 mg/ml (instant claim 10) in an aqueous liquid (instant claim 11).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JONG HWAN BAEK whose telephone number is (571)272-0670. The examiner can normally be reached Mon - Thu, 9 am - 3 pm ET.
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, Michael G Hartley can be reached at 571-272-0616. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/JONG HWAN BAEK/Examiner, Art Unit 1618
/Nissa M Westerberg/Primary Examiner, Art Unit 1618
Prosecution Insights