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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 3 is objected to because of the following informalities: On the last line of claim 3, the full meaning for the abbreviation “DIPEA” should be recited. Appropriate correction is required.
Claim Rejections - 35 USC § 112
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.
Claim 6 is 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.
On line 5 of claim 6, the phrase “the resulting reaction mixture” lacks antecedent basis.
Inventorship
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.
Claim Rejections - 35 USC § 102
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 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) 1-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lee et al (article from ACS Omega, vol. 5, pages 32507-32514, December 9, 2020, submitted in the IDS filed on June 13, 2023).
With regards to claim 1, Lee et al teach of a probe known as KF-DNBS for the detection of hydrogen sulfide in a serum sample. The probe has the formula depicted in Scheme 1 b) on page 32508 of Lee et al, which is:
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This formula is the same as chemical formula 1 for KF-DNBS recited in instant claim 1. Lee et al teach that the probe KF-DNBS serves to detect hydrogen sulfide in a serum sample since hydrogen sulfide causes the 2,4-dinitrobenzene sulfonyl (DNBS) group in the probe to be cleaved from the probe by thiolysis followed by the formation of a fluorescent fluorophore KF-albumin complex. See the abstract and Scheme 1(b) on pages 32507-32508 of Lee et al.
With regards to claim 2, Lee et al teach of a method for manufacturing the probe for hydrogen sulfide detection using the same steps as recited in claim 2. See “Scheme 2. Synthetic Route for KF-DNBS” on page 32508 of Lee et al, which depicts the same manufacturing steps for the probe for hydrogen sulfide detection as set forth in paragraph 44 in the instant specification. Specifically, Lee et al teach that the method for manufacturing the probe for hydrogen sulfide detection comprises the steps of: preparing a first intermediate (5-(4-(diethylamino) phenyl) -N-methylthiophen-3-amine); obtaining a second intermediate (2-(4- (diethylamino) phenyl)-7- (4-methoxyphenyl)-4-methyl-6, 7-dihydrothieno [3,2-b]pyridin-5(4H) -one) by quenching the first intermediate with water and extraction; obtaining a third intermediate (6-bromo-2- (4-(diethylamino)phenyl)-7-(4-methoxypheny-4-methylthieno[3,2-b]pyridin- 5(4H)-one) by quenching the second intermediate with water and extraction; obtaining a fourth intermediate (2-(4-(Diethylamino)phenyl)-7-(4-methoxypheny1)-4-methylthieno[3, 2-b] pyridin-5 (4H)-one) by quenching the third intermediate with water and extraction; obtaining KF (2-(4- (diethylamino) phenyl)-7-(4- hydroxyphenyl)-4-methylthieno [3,2-b]pyridin-5(4H)-one) by quenching the fourth intermediate with water and extraction; and obtaining KF-DNBS (4-(2-(4-diethylamino) phenyl)-4-methyl-5-oxo-4,5-dihydrothieno[3,2-b]pyridin-7-yl)phenyl 2, 4-dinitrobenzenesulfonate) by quenching the KF with water and extraction. See “Scheme 2. Synthetic Route for KF-DNBS” on page 32508 of Lee et al. Also, see the right-hand column on page 32511 and the left-hand column on page 32512 of Lee et al under the heading “Synthesis of the Probe”.
With regards to claim 3, Lee et al teach that the step of obtaining the second intermediate comprises reacting the first intermediate with 4-methoxycinnamic acid, benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (BOP) and DIPEA. See the paragraph in the right-hand column of page 32511 of Lee et al where it states:
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With regards to claim 4, Lee et al teach that the step of obtaining the third intermediate comprises the step of mixing and reacting the second intermediate with N-bromosuccinimide. See the paragraph in the right-hand column of page 32511 of Lee et al where it states:
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With regards to claim 5, Lee et al teach that the step of obtaining the fourth intermediate comprises the step of quenching the third intermediate, followed by reaction with n-butyllithium solution. See the paragraph in the left-hand column of page 32512 of Lee et al where it states:
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With regards to claim 6, Lee et al teach that the step of obtaining KF comprises quenching the fourth intermediate followed by reaction with boron tribromide to form a reaction mixture; and quenching the reaction mixture with water followed by neutralization. See the paragraph in the left-hand column of page 32512 of Lee et al where it states:
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With regards to claim 7, Lee et al teach that the step of obtaining KF-DNBS comprising mixing and reacting KF with 2,4-dinitrobenzenesulfonyl chloride and triethylamine. See the paragraph in the left-hand column of page 32512 of Lee et al where it states:
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With regards to claim 8, Lee et al teach of a composition for detecting hydrogen sulfide in a serum sample comprising a probe known as KF-DNBS having the formula depicted in Scheme 1 b) on page 32508 of Lee et al, which is:
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and 2-formyl benzene boronic acid (2-FBBA) as a masking agent for masking the reactivity of Cys and Hcy in a serum sample to the dinitrobenzenesulfonyl (DNBS) portion of the KF-DNBS probe. See the abstract and the following paragraph in the right-hand column on page 32509 of Lee et al where it states:
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It is noted that the article to Lee et al qualifies as prior art under 35 USC 102(a)(1) against the instant claims since it was published on December 9, 2020, which is prior to both the filing date of the PCT application (PCT/KR2021/016446, filed on November 11, 2021) and the foreign application (KR 10-2020-0175242, filed on December 15, 2020) upon which the instant application claims priority to. It is noted that a translation of the foreign priority document has also not been filed.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Please make note of: Ahn et al (US 2016/0274123) who teach of a fluorescent probe for sensing hydrogen sulfide, and a manufacturing method thereof; Xian et al (US 2018/0074068) who teach of fluorescent probes for detecting hydrogen sulfide; Wang et al (CN112745340A) who teach of a fluorescent probe for selectively detecting hydrogen sulfide based on a BODIPY dye; and Tong et al (article from RSC Advances, vol. 12, June 16, 2022, pages 17846-17852) who teach of a fluorescent probe for visualizing hydrogen sulfide in living cells.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MAUREEN M WALLENHORST whose telephone number is (571)272-1266. The examiner can normally be reached on Monday-Thursday from 6:30 AM to 4:30 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Lyle Alexander, can be reached at telephone number 571-272-1254. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MAUREEN WALLENHORST/Primary Examiner, Art Unit 1797 July 21, 2026
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