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
Claims 1-3, 5, 6, 9-11, 14, 15, 18-20, 22, 24, 25, 28-31, 34, 36-44, 49-53 and 60 are pending in the application. Claims 1-3, 5, 9, 14, 18-20, 24, 25, 29-31, 34, 36-39, 41 and 42 are rejected. Claim 40 is allowed. Claims 6, 10, 11, 15, 22, 28, 43, 44, 49-53 and 60 are withdrawn from further consideration.
Election/Restrictions
Applicant’s election without traverse of the species of Compound 34, having the structure:
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to prosecute the invention of Group I, claims 1-3, 5, 6, 9-11, 14, 15, 18-20, 22, 24, 25, 28-31, 34 and 36-42 in the reply filed on November 26th, 2025 is acknowledged.
As per MPEP 803.02, the examiner will determine whether the entire scope of the claims is patentable. Applicants' elected species appears allowable. Therefore, according to MPEP 803.02: should the elected species be found allowable, the examination of the Markush-type claim will be extended. If the examination is extended and a non-elected species found not allowable, the Markush-type claim shall be rejected and claims to the nonelected invention held withdrawn from further consideration. The examination of the Markush-type claims has been extended to include the scope of claims 2, 3, 5, 14, 18, 24, 29, 34 and 36-41, which are free of the prior art and further extended to the species cited under 35 USC 102 and to the scope of Formula (I) where R1 is -CHO, R2 is -OH, R3 is hydrogen, G1 and G2 are each CH, L is –(CH2)OC(O)NH-*, A1 is unsubstituted heteroaryl and A1 is substituted heterocyclyl, which are not allowable.
As a non-elected species has been found not allowable, the Markush-type claims have been rejected and claims to the nonelected invention held withdrawn from further consideration. Claims 1-3, 5, 9, 14, 18-20, 24, 25, 29-31, 34 and 36-42 embrace the elected species and are therefore under examination. Claims 1-3, 5, 9, 14, 18-20, 24, 25, 29-31, 34 and 36-42 have been examined to the extent that they are readable on the elected embodiment and the above identified nonelected species. Since the nonelected species has been found not allowable, subject matter not embraced by the elected embodiment or the above identified nonelected species is therefore withdrawn from further consideration.
Claims 6, 10, 11, 15, 22, 28, 43, 44, 49-53 and 60 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention or species.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement(s) filed on November 26th, 2025 and November 8th, 2023.
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 1-3, 5, 9, 14, 18-20, 24, 25, 29-31, 34, 36-39 and 42 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 1 is rejected as indefinite based on the exclusion of 5-[2-(3,4-diethoxyphenyl)-4-thiazolyl]-3-formyl-2-hydroxy-benzoic acid methyl ester. This compound does not otherwise fall within the scope of formula (I) since it would require that L is a bond. It is unclear if the definitions of formula (I) are incomplete or the exclusion is superfluous. Dependent claims 1-3, 5, 9, 14, 18-20, 24, 25, 29-31, 34 and 36-38 and 42 are rejected as indefinite for the same reason since they do not otherwise fully define the compounds embraced by the claims. For the purposes of examination, the Examiner has assumed the exclusion is superfluous.
Claim 37 is rejected as indefinite based on the preamble referring to a “compound of claim 1, or a tautomer thereof, or a pharmaceutically acceptable salt of any of the foregoing” where a “portion of the compound” can be the following options:
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The language refers to a definition of the compound but then lists structures that would correspond to salts. It is unclear whether claim 37 would embrace non-sodium salts of the first two options above and non-HCl salts of the third option above. Similarly, it is unclear if non-salt versions of the structures above are embraced by claim 37.
Claim 39 is rejected as indefinite since the preamble refers to a “compound , or a tautomer thereof, or a pharmaceutically acceptable salt of any of the foregoing wherein the compound is selected from” a list including the following structures:
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The language refers to a definition of the compound but then lists structures that would correspond to salts. It is unclear if claim 39 would embrace non-sodium salts of the first two options above and non-HCl salts of the third option above. Similarly, it is unclear if non-salt versions of the structures above are embraced by claim 39.
Claim 41 is rejected as indefinite since the preamble refers to a “compound of claim 40, or a tautomer thereof, or a pharmaceutically acceptable salt of any of the foregoing wherein the compound is selected from” a list including the following structures:
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The language refers to a definition of the compound but then lists structures that would correspond to salts. It is unclear if claim 41 would embrace non-sodium salts of the two options above. Similarly, it is unclear if non-salt versions of the structures above are embraced by claim 41.
Claim Rejections - 35 USC § 112(d)
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.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], 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 34 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 34 recites the following two options that only contain one ring system instead of the two required by -A1-A2:
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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.
Claim 41 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 41 recites the following compounds that are not embraced by formula (I) since they require L be a bond:
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Claim 41 further recites the following compound that is not embraced by Formula (I) of claim 40 since R2A1A does not embrace an aryl group:
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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.
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, 9, 19, 20, 25, 30, 31 and 42 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry No. 2419399-22-5, which entered STN on June 5th, 2020.
CAS Registry No. 2419399-22-5 is drawn to N-(3,4-dihydro-3-methyl-2-oxo-2H-1,3-benzoxazin-6-yl)-2-(2-methoxyphenyl)-5-thiazolecarboxamide, which has the following structure:
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The compound is embraced by Formula (I) where R1 and R2 together form an optionally substituted ring of the formula:
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G1 and G2 are CH, R3 is hydrogen, L is -NHC(O)-*, A1 is unsubstituted heteroaryl and A2 is substituted aryl. The compound is embraced by instant claims 1, 9, 19 (third option), 20 (thiazolyl), 25, 30 (substituted phenyl) and 31. Regarding instant claim 42, this claim only requires the presence of the compound itself and the preamble of “pharmaceutical” is considered a non-limiting intended use.
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.
Claim(s) 1, 9 and 42 is/are rejected under 35 U.S.C. 103 as being unpatentable over WO 2018/133859 A1 by Yang et al. in view of Monsees et al. Analytical Biochemistry 1994, 221, 329-334.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Yang et al. teach compounds of the following formulae (I)-(III) for detection of hydrogen peroxide (abstract and page 1):
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In Formula (II), the prior art teaches (page 5) that X1 is a monovalent pro-fluorophore or pro-luminophore moiety. As an example, the prior art teaches the following species on page 8:
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where (page 9) R is H or CF3.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The compound of the prior art where R is H is excluded by provision at the end of claim 1. The instant claims, however, encompass a compound where the carbamate moiety is located at the 6-position of the benzothiazole ring instead of the 5-position.
The instantly claimed compound is embraced by Formula I where R1 is -CHO, R2 is -OH, R3 is hydrogen, G1 and G2 are each CH, L is –(CH2)OC(O)NH-*, A1 is unsubstituted heteroaryl and A1 is substituted heterocyclyl. The instantly claimed compound is embraced by instant claims 1 and 9. Regarding instant claim 42, this claim only requires the presence of the compound itself and the preamble of “pharmaceutical” is considered a non-limiting intended use.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
The prior art teaches the following mechanism in Figure 1:
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The prior art teaches release at the carbamate nitrogen. Accordingly, a person having ordinary skill in the art would have been motivated to use structures that would (upon cleavage of the carbamate) result in fluorescent or luminescent moieties.
Monsees et al. teach the following bioluminescence scheme on page 330:
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Monsees et al. teach generation of D-aminoluciferin having the following structure (page 331):
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The structure above contains a nitrogen moiety at the 6-position of the benzothiazole ring. At least since Monsees et al. demonstrate a successful luminescence system using release of the 6-position substituted structure, a person having ordinary skill in the art would have reasonably expected that the instantly claimed compound differing by the position of the nitrogen-moiety would similarly be useful in the utilities of Yang et al. Furthermore, MPEP 2144.09(II) states: “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).”
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claim 39 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-8 of U.S. Patent No. 11,299,487 in view of Patani et al. Chem. Rev. 1996, 96, 3147-3176 and in further view of Sheridan, R.P. J. Chem. Inf. Comput. Sci. 2002, 42, 103-108. The claims of the patent embrace compounds of the following general formula:
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where R4 has the following structure:
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As a species, claim 7 of the patent recites the following structure (column 336):
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Instant claim 39 recites the following species:
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The instantly claimed compound differs from the species of the patent based on the replacement of a -CH- group with an -N= group (corresponding to the G4 or G6 position in the patent structure). Claim 1 of the patent, however, recites both carbon and nitrogen as options for the corresponding positions. Furthermore, this type of modification is well recognized to be a bioisosteric replacement. For instance, Patani et al. teach the following on page 3156:
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As an additional example, Sheridan reports a study that analyzes compounds with similar biological properties as follows (abstract):
We have written a method that extracts one-to-one replacements of chemical groups in pairs of drug-like molecules with the same biological activity and counts the frequency of the replacements in a large collection of such molecules. […]
Regarding one method of analysis, the replacement of –CH= with –N= was returned as the most frequent replacement to result in compounds with similar activity (Figure 5, page 106):
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Accordingly, a person having ordinary skill in the art would have been familiar with the common replacement of –CH= with –N= and would have reasonably expected that such a replacement on the species of the patent would result in a compound with similar properties and utility.
Allowable Subject Matter
Claim 40 is allowed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Renee Claytor can be reached at 571-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626