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 .
Response to Amendment
Amendments to the specification and claims filed on 6 April 2026 are acknowledged. Claims 1-7, 9, 10, 13, 15, and 16 are amended, and claims 17-25 are newly added. Claims 1-7, 9, 10, 13, 15, and 16-25 are pending; claims 5-7, 9, 10, 13, 15, and 16 are withdrawn; and claims 1-4 and 17-25 are examined herein on the merits.
In response to the amendment filed on 6 April 2026, the objection to the specification is withdrawn; the objections to the claims are withdrawn; rejections under 35 U.S.C. 112(a) are added; the rejections under 35 U.S.C. 112(b) are partially withdrawn and modified; a rejection under 35 U.S.C. 112(d) is added; and the rejections over the prior art are withdrawn. Claims 4, 22, and 23 are directed to allowable subject matter.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
Claims 1, 3, 17, 21, 24 and 25 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, at the time the application was filed, had possession of the claimed invention.
The examiner respectfully reminds the Applicant that according to MPEP §2163:
"2163.02. Standard for Determining Compliance with Written Description Requirement:
The courts have described the essential question to be addressed in a description requirement issue in a variety of ways. An objective standard for determining compliance with the written description requirement is, “does the description clearly allow persons of ordinary skill in the art to recognize that he or she invented what is claimed.” In re Gosteli, 872 F.2d 1008, 1012, 10 USPQ2d 1614, 1618 (Fed. Cir. 1989). Under Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991), to satisfy the written description requirement, an applicant must convey with reasonable clarity to those skilled in the art that, as of the filing date sought, he or she was in possession of the invention, and that the invention, in that context, is whatever is now claimed. The test for sufficiency of support in a parent application is whether the disclosure of the application relied upon “reasonably conveys to the artisan that the inventor had possession at that time of the later claimed subject matter.” Ralston Purina Co. v. Far-Mar-Co., Inc., 772 F.2d 1570, 1575, 227 USPQ 177, 179 (Fed. Cir. 1985) (quoting In re Kaslow, 707 F.2d 1366, 1375, 217 USPQ 1089, 1096 (Fed. Cir. 1983)). Whenever the issue arises, the fundamental factual inquiry is whether the specification conveys with reasonable clarity to those skilled in the art that, as of the filing date sought, applicant was in possession of the invention as now claimed. See, e.g., Vas-Cath, Inc. v. Mahurkar, 935 F.2d 1555, 1563-64, 19 USPQ2d 1111, 1117 (Fed. Cir. 1991). An applicant shows possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention. Lockwood v. American Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997). Possession may be shown in a variety of ways including description of an actual reduction to practice, or by showing that the invention was “ready for patenting” such as by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the applicant was in possession of the claimed invention. See, e.g., Pfaff v. Wells Elecs., Inc., 525 U.S. 55, 68, 119 S.Ct. 304, 312, 48 USPQ2d 1641, 1647 (1998); Regents of the University of California v. Eli Lilly, 119 F.3d 1559, 1568, 43 USPQ2d 1398, 1406 (Fed. Cir. 1997); Amgen, Inc. v. Chugai Pharmaceutical, 927 F.2d 1200, 1206, 18 USPQ2d 1016, 1021 (Fed. Cir. 1991) (one must define a compound by “whatever characteristics sufficiently distinguish it”).
(I)
Independent claim 1 has been amended to recite the following limitations:
R3 is a C3-C25 hydrocarbon group, wherein the hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic…
R4 and R5 are independently selected from a C2-C6 hydrocarbon group substituted by at least one hydroxyl group, wherein the R4 and R5 hydrocarbon groups are independently linear or branched, saturated or unsaturated, cyclic or non-cyclic; or
R4 is a C3-C6 hydrocarbon group substituted by at least two hydroxyl groups, wherein the R4 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic, and R5 is an unsubstituted C1-C6 hydrocarbon group, wherein the R5 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic; or
R5 is a C3-C6 hydrocarbon group substituted by at least two hydroxyl groups, wherein the R5 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic, and R4 is an unsubstituted C1-C6 hydrocarbon group, wherein the R4 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic; and
R6 is selected from the group consisting of a hydrogen atom and a C1-C6 hydrocarbon group, which is linear or branched, saturated or unsaturated, cyclic or non-cyclic,
New dependent claim 21 recites related language.
New dependent claim 24 recites that R3 is a C7-C25 hydrocarbon group.
As noted below in the rejections under 35 USC 112(b), the meaning of a cyclic C1 or C2 hydrocarbon group is completely unclear. Likewise, the meaning of an unsaturated C1 hydrocarbon group is completely unclear. The original disclosure provides no support for a cyclic C1 or C2 hydrocarbon group. The original disclosure provides no support for an unsaturated C1 hydrocarbon group. This is new matter.
Moreover, the original disclosure does not provide sufficient written description support for the choice of R group(s) being an unsaturated, cyclic hydrocarbon group for the claimed ranges of a C3-C25 hydrocarbon group, a C2-C6 hydrocarbon group, a C1-C6 hydrocarbon group. More broadly, the original disclosure does not provide sufficient written description support for the choice of R group(s) being a hydrocarbon group for the claimed ranges of a C3-C25 hydrocarbon group or a C7-C25 hydrocarbon group.
The original disclosure does not use the term "hydrocarbon." Instead, the specification broadly uses the term "alkyl," without a special definition, to encompass examples of hydrocarbon groups and non-hydrocarbon groups. The specification teaches that examples of alkyl groups include radicals derived from heteroaryl groups (e.g., "- purinyl," page 4, lines 34-35), which are non-hydrocarbon groups. Accordingly, the specification's broad disclosure of the category of "alkyl" cannot be interpreted as synonymous with the claimed term of "hydrocarbon." Consequently, the disclosure of a C25 "alkyl" does not support a C25 hydrocarbon group.
The original disclosure provides specific examples of the choice of R group that are hydrocarbon groups (as well as some non-hydrocarbon examples). Regarding whether the disclosed specific examples of R groups provide sufficient support for the broader claimed subject matter of (unsaturated, cyclic) hydrocarbon groups of a particular carbon number, a portion of MPEP 2163.05, I. B is reproduced below, with added bolding:
The written description requirement for a claimed genus may be satisfied through sufficient description of a representative number of species. A "representative number of species" means that the species which are adequately described are representative of the entire genus. Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus. See AbbVie Deutschland GmbH & Co., KG v. Janssen Biotech, Inc., 759 F.3d 1285, 1300, 111 USPQ2d 1780, 1790 (Fed. Cir. 2014) (Claims directed to a functionally defined genus of antibodies were not supported by a disclosure that "only describe[d] one type of structurally similar antibodies" that "are not representative of the full variety or scope of the genus."). The disclosure of only one species encompassed within a genus adequately describes a claim directed to that genus only if the disclosure "indicates that the patentee has invented species sufficient to constitute the gen[us]." See Enzo Biochem, 323 F.3d at 966, 63 USPQ2d at 1615.
Regarding the choice of R group(s) being an unsaturated, cyclic hydrocarbon group for the claimed ranges of a C3-C25 hydrocarbon group, a C2-C6 hydrocarbon group, a C1-C6 hydrocarbon group, the specification provides examples of saturated, cyclic hydrocarbon groups that are C3, C4, and C5 (cyclopropyl, cyclobutyl, cyclopentyl) and an example of an unsaturated, cyclic hydrocarbon groups that is C5 (cyclopentenyl). However, no examples are provided for unsaturated, cyclic hydrocarbon groups that are C3 or C4.
Regarding the broader recitation of the choice of R group(s) being a hydrocarbon group (regardless of subtype) for the claimed ranges of a C3-C25 hydrocarbon group or a C7-C25 hydrocarbon group, the original disclosure does not appear to provide any examples of a C25 hydrocarbon group.
Dependent claims 17, 21, and 24 are rejected for inheriting this deficiency of independent claim 1.
(II)
Independent claim 1 has been amended to recite the choice of "O-CO-R6" for R1.
Claim 1 previously recited the choice of "O2CR6" for R1.
The originally disclosed choice of "O2CR6" would be interpreted by one of ordinary skill as "-O2CR6," with oxygen having an open valence position and its atom order of connectivity being read from left to right. One of ordinary skill in the art would not recognize the disclosed choice of "O2CR6" as referring to a functional group that satisfies normal atom valencies. One of ordinary skill in the art would not recognize the disclosed choice of "O2CR6" as being synonymous with the amended choice of "O-CO-R6."
It would not be reasonable to disregard the listed atom order of the originally disclosed choice of "O2CR6" for R1. While it is true that element-order does not matter for a molecular formula, a molecular formula does not contain a variable group such as R6. Moreover, according to convention in a molecular formula, oxygen would not be listed before carbon. Accordingly, it is not reasonable to interpret the originally disclosed "O2CR6" moiety as a molecular formula and accordingly disregard the convention that links listed atom order to atom connectivity.
Moreover, even if the "O2C" moiety were to be interpreted as a divalent molecular formula, where atom order is not given weight when interpreting atom connectivity, a broadly disclosed divalent molecular formula genus containing two oxygens and one carbon would encompass plural species, including -C(O)-O-R6. Accordingly, the narrow species of -O-C(O)-R6 is not supported by a broader genus.
Dependent claims 3, 24 and 25 are rejected for inheriting this deficiency of independent claim 1.
Therefore, the Applicants did not show possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention, by description of an actual reduction to practice, or by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the applicant was in possession of the claimed invention.
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.
Claims 1-4 and 17-25 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 1 recites the limitations "wherein the hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic," "wherein the R4 and R5 hydrocarbon groups are independently linear or branched, saturated or unsaturated, cyclic or non-cyclic," "wherein the R5 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic," "the R4 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic," and "a C1-C6 hydrocarbon group, which is linear or branched, saturated or unsaturated, cyclic or non-cyclic." Claim 21 recites similar limitations. It is unclear what is meant by a linear cyclic hydrocarbon. It is unclear what is meant by a branched cyclic hydrocarbon.
Claim 1 recites the limitations "a C2-C6 hydrocarbon group substituted by at least one hydroxyl group, wherein the R4 and R5 hydrocarbon groups are independently linear or branched, saturated or unsaturated, cyclic or non-cyclic," "R5 is an unsubstituted C1-C6 hydrocarbon group, wherein the R5 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic," "R4 is an unsubstituted C1-C6 hydrocarbon group, wherein the R4 hydrocarbon group is linear or branched, saturated or unsaturated, cyclic or non-cyclic," and "a C1-C6 hydrocarbon group, which is linear or branched, saturated or unsaturated, cyclic or non-cyclic." Claims 18 and 21 recite at least some similar limitations. The meaning of a cyclic C1 or C2 hydrocarbon group is completely unclear. The meaning of an unsaturated C1 hydrocarbon group is completely unclear. It is also unclear what is meant by a "branched" C1 or C2 hydrocarbon group.
Claim 1 recites the limitation "or a salt or solvate thereof" immediately after the definition of R6. It is unclear what is modified by this definition. Although the grammar suggests that this limitation modifies the previous phrase ("R6 is selected from the group consisting of a hydrogen atom and a C1-C6 hydrocarbon group, which is linear or branched, saturated or unsaturated, cyclic or non-cyclic"), this interpretation does not make sense.
Claims 2-4 and 17-25 are rejected for depending from rejected independent claim 1.
Claim 2 recites the limitation "R4 and R5 are independently selected from a C2-C6 saturated linear alkyl group substituted by at least one hydroxyl group," and other similar limitations. It is unclear what is meant by a saturated alkyl. The instant specification does not set forth a special definition of "alkyl," while the accepted meaning is a univalent group -CnH2n+1 derived from an alkane by removal of a hydrogen atom from any carbon atom. Accordingly, the conventional meaning of an alkyl group already requires the group to be saturated. The term "alkyl" is indefinite because the specification does not clearly redefine the term to encompass something that can be unsaturated. Moreover, the specification provides numerous examples of the "C3-C25 alkyl, linear or branched, saturated or not, cyclic or not" (page 4, line 6 to page 6, line 7), including radicals derived from heterocyclic groups (e.g., "-1,2,3,4-tetrahydroquinolinyl," page 5, line 1), which are not hydrocarbon groups as required by claim 1. Because the specification uses the term "alkyl" to refer to both hydrocarbon and non-hydrocarbon groups, it is unclear whether dependent claim 2 requires all of the limitations of independent claim 1. Where applicant acts as his or her own lexicographer to specifically define a term of a claim contrary to its ordinary meaning, the written description must clearly redefine the claim term and set forth the uncommon definition so as to put one reasonably skilled in the art on notice that the applicant intended to so redefine that claim term. Process Control Corp. v. HydReclaim Corp., 190 F.3d 1350, 1357, 52 USPQ2d 1029, 1033 (Fed. Cir. 1999).
Claim 2 recites the limitation "an unsubstituted C1-C6 saturated linear or branched alkyl group" twice. It is unclear what is meant by a "branched" C1 or C2 alkyl group.
Claim 4 recites the limitation "The fluorescent compound according to claim 1 of the following formula." There is insufficient antecedent basis for this limitation in the claim.
Claim 4 recites the limitation "of the following formula:…" However, what follows this limitation is plural formulae (or formulas).
Claims 18 and 21 recite the limitation "or a salt or solvate thereof" immediately after the definition of R4. It is unclear what is modified by this definition. Although the grammar suggests that this limitation modifies the previous phrase ("wherein the R4 hydrocarbon group is linear or branched, saturated or unsaturated […]"), this interpretation does not make sense.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 19 is rejected under 35 U.S.C. 112(d) as being of improper dependent form for failing to include all the limitations of the claim upon which it depends.
Dependent claim 19 recites the limitation "R4 and R5 are saturated hydrocarbon groups."
Claim 19 does not require all of the limitations of claims 1 and 18, which require either (i) each of R4 and R5 are a hydrocarbon group substituted by at least one hydroxyl group, or (ii), one of R4 and R5 is a hydrocarbon group and the other of R4 and R5 is a hydrocarbon group substituted by at least two hydroxyl groups. If R4 is "a hydrocarbon group substituted by at least one hydroxyl group," then R4 is not a hydrocarbon because R4 comprises an oxygen atom.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Allowable Subject Matter
Claims 4, 22, and 23 would be allowable if rewritten to overcome the rejections under 35 U.S.C. 112(b) set forth in this Office action. If put in independent form, the claims must not include redundant or broader limitations recited in claim 1.
The prior art of record does not disclose a fluorescent compound selected from the formulae of claim 4, 22, or 23, or a salt or a solvate thereof.
Newly made of record are the following prior art:
Mao (CN 109280017 A) discloses the following localization agent:
PNG
media_image1.png
250
591
media_image1.png
Greyscale
Shi (CN 101544584 A) discloses the following imaging agent (claim 1):
PNG
media_image2.png
137
342
media_image2.png
Greyscale
PNG
media_image3.png
50
211
media_image3.png
Greyscale
Ahn (US 2017/0327509) discloses fluorophores, including the following (page 6):
PNG
media_image4.png
183
417
media_image4.png
Greyscale
Cho (US 2009/0155837) discloses florescent probes, including the following ([0040]):
PNG
media_image5.png
210
523
media_image5.png
Greyscale
Chang (WO 2016/114722) discloses numerous specific examples of a probe of structural formula (A) that comprises at a primary amine (pages 20-33), where R4 is an acetyl group.
Response to Arguments
Applicant's arguments filed on 6 April 2026 have been considered and are not fully persuasive.
Regarding support for the amendment to claim 1, Applicant argues the following (page 18; bolding added):
Just as, in R1, the "CO2R6" in NHCO2R6 would be understood to be an ester, by symmetry, the "O2CR6" definition would be understood by a person of ordinary skill in the art (POSITA) to mean "O-CO-R6," which is the only chemically sensible interpretation.
This argument is clearly unpersuasive. The moiety "CO2R6" is understood to mean "-C(O)-O-R6" because "CO2R6" properly follows the convention of atom order being read from left-to-right when interpreting atom connectivity.
Applicant's argument appears to imply that the "O2CR6" moiety should be understood as a molecular formula, where the listed order of elements reflects a convention that is independent of the atom connectivity of the molecule. However, a molecular formula does not contain a variable group such as R6. Moreover, according to molecular formula convention, oxygen is not listed before carbon. Accordingly, it is unreasonable to interpret the originally-disclosed "O2CR6" moiety as a molecular formula and disregard the convention of listed atom order.
Moreover, even if the "O2C" moiety were to be interpreted as a divalent molecular formula, where atom order is not given weight when interpreting atom connectivity, a broadly disclosed divalent molecular formula genus containing two oxygens and one carbon would encompass plural species, including -C(O)-O-R6. Accordingly, "O-CO-R6" is not "the only chemically sensible interpretation" when disregarding atom order when interpreting atom connectivity. A narrow species is not supported by a broader genus.
Applicant's arguments with respect to the previous rejection for anticipation by Barrio (US 2002/0022002) are persuasively consistent with the guidance and case law discussed in MPEP 2131.02, III. Claimed species of fluorescent compound cannot be "at once envisioned" from the disclosure of Barrio. Accordingly, the rejections for anticipation by Barrio have been withdrawn.
The amendments to the claims have overcome the rejections based upon Petric ("Dicyanovinylnaphthalenes for neuroimaging of amyloids and relationships of electronic structures and geometries to binding affinities," Proc. Natl. Acad. Sci. U.S.A. 2012).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 MICHELLE ADAMS whose telephone number is (571)270-5043. The examiner can normally be reached M, T, Th, and F, 12-4 P.M.
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, Lyle Alexander can be reached at (571) 272-1254. 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.
/MICHELLE ADAMS/ Examiner, Art Unit 1797
/JENNIFER WECKER/ Primary Examiner, Art Unit 1797
Prosecution Insights