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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 without traverse of 58-71 in the reply filed on 3/20/2026 is acknowledged.
Applicant's election with traverse of the species of claim 71 in the reply filed on 3/20/2026 is acknowledged. Claim 71 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. Therefore, the election of species requirement of claim 71 is withdrawn.
Information Disclosure Statement
The reference Schroder, et al. was not provided. The reference Germano et al. was also not provided.
Claim Objections
Claim 61, 62-64, 68, and 70-72 are objected to under 37 CFR 1.75(c) as being in improper form because a multiple dependent claim should refer to other claims in the alternative only and multiple dependent claims cannot depend from any other multiple dependent claim. See MPEP 608.01(n). For the purpose of examination on the merits, all improper multiple dependent claims will be interpreted as depending from the lowest numbered claim which they refer back to.
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 59 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.
Claim 59 recites the limitation "the thiol.” There is insufficient antecedent basis for this limitation in the claim. There is no indication the chemical entity of claim 58 has the a thiol present.
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.
Claims 58-60, 64, 68, and 70 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Frost US 20150247005A1.
Regarding claim 58, 60-61 and 64, Frost teaches a compound formed from the formula below (Abstract)
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is a thiolactone that reads on the claimed compound B where A is an alkyl group, n= 0, m=1, and R1 and R2 are C1 alkyl groups. The polymer
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reads on the claimed moiety comprising one or more amine groups and the claimed “polymer.” This also reads on the claimed Formula (X) where E is NH2 p is an integer of at least 1 and D is the rest of the polymer.
Regarding claim 59, Frost also teaches that the resulting polymer is further reacted to form
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(Abstract) which comprises a nitrosothiol group. This reads on the limitations of claim 59.
Regarding claim 70, Frost teaches R is a polyalkylsiloxane moiety substituted with a primary amine group
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(Abstract). This reads on the limitations of claim 70.
Regarding claims 58-60, 64-65, 68 Frost teaches a reaction between a thiolactone and a polymer containing a primary amine (Paragraph [0103]). Frost also teaches that the thiolactone is
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(Paragraph [0107]).
This reads on the claimed compound B where A is an alkyl group, n= 0, m=1, and R1 and R2 are C1 alkyl groups. The polymer containing a primary amine reads on the claimed moiety comprising one or more amine groups and the claimed “polymer”. This also reads on the claimed compound of formula X, where E is NH2, and D is a core moiety.
Regarding claims 58, 60, and 64-65, Frost teaches the polymer can be
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(Paragraph [0119], Scheme 2). This reads on the limitations of claim 65 where the monomer groups comprising the polymer comprise pendant amine groups. It would have been obvious to select the polymer of scheme 2 because it is prima facie obvious to select a known material based on its suitability for its intended use. See MPEP 2144.07.
Claims 58, 67, and 69 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Espeel, P., et al., (One-Pot Multistep Reactions Based on Thiolactones: Extending the Realm of Thiol-Ene Chemistry in Polymer Synthesis) Journal of the American Chemical Society 2011 133 (6), 1678-1681) as evidenced by Huntsman JEFFAMINE(R) Amine Brochure 2017.
Regarding claims 58 and 67, Espeel teaches a compound (5) that reads on the claimed component (D) where m =1, n =1, O is the linker and A is the propene group, and R1 and R2 are each a hydrogen. This reads on the claimed B. Espeel teaches this compound reacts with (7) (Scheme 4). This reads on the claimed compound comprising at least one primary amine. This reads on the limitations of claim 58. Espeel teaches that the primary amine can be Jeffamine D series 10. Jeffamine D series 10 is a polyether amine polymer (Huntsman, Page 3). This reads on the claimed polymer comprising amine groups at each terminus of the polymer chain.
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Regarding claim 69, Espeel reads on the limitations of claim 68. The Jeffamine (D) polymers comprise C2 alkylene oxide units. This reads on the limitation of claim 69.
Claims 58, 64, and 66 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhou, Y., et al., (Synthesis and nitric oxide releasing properties of novel fluoro S-nitrosothiols. Chem. Commun., 2019, 55, 401).
Regarding claims 58, 64, and 66, Zhou teaches a method of producing nitrosothiols beginning from gemdimethyl thiolactone (Figure 1). Gemdimethyl thiolactone reads on the claimed structure of component B where the core moiety A is a methyl group, n= 0, m =1, and C is the fluoroamine. Zhou teaches the reaction
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(Scheme 1). Zhou teaches the R group is 2 fluorophenyl. (Scheme 1). This reads on the limitation of 2-fluorobenzylamine.This reads on the limitations of claims 58, 64, and 66.
Allowable Subject Matter
Claims 62, 63, and 71 are objected to as being dependent upon a rejected base claim, and for being in improper multiple dependent form, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Regarding claim 62, Frost, Zhou, and Espeel are silent on the value of m being greater than 1.
Regarding claim 63, Frost, Zhou and Espeel are silent on a chemical entity where component B is any of the structures of claim 63.
Regarding claim 71, Frost, Zhou and Espeel are silent on the chemical entity having the structure of compound 20.
Relevant Prior art
Espeel, P. et al., (Double modular modification of thiolactone-containing polymers: towards polythiols and derived structures, Polym. Chem., 2012, 3, 1007) teaches a thiolactone polymer
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(Scheme 3). This is similar to the limitations of claim 58 where A is the rest of the polymer, L is the sulfate linker, This polymer comprises thiolactone repeat units. Espeel teaches the number of thiolactone units is 25 mol% of the total composition and number of styrene units is therefore 75%. (Espeel, Table 1 Example 4). Espeel teaches the number average molecular weight of the polymer is 12,500. The molecular weight of the repeat unit of styrene is 104.14. The molecular weight of the repeat unit of the St-TLa block is 283. The number of repeat units of St-TLA is therefore 23. Espeel also teaches the polymer undergoes aminolysis (Scheme 1). However, the structure comprises a sulfate group instead of a carbonyl group therefore Espeel does not read on the limitations of claim 58.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LILY K SLOAN whose telephone number is (703)756-5875. The examiner can normally be reached Monday-Friday 9:00-5:30 ET.
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/LILY K SLOAN/ Examiner, Art Unit 1762
/ROBERT S JONES JR/ Supervisory Patent Examiner, Art Unit 1762
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