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 .
Priority
This application claims benefit under 35 U.S.C. 119 or 365 (c), and is a National Stage entry from International Application No. PCT/KR2022/011915, filed Aug. 10, 2022, which claims priority to the benefit of Korean Patent Application Nos. 10-2021-0106107 filed on Aug. 11, 2021, and 10-2022-0099692 filed on Aug. 10, 2022 in the Korean Intellectual Property Office. The certified copies have been received and acknowledged.
Information Disclosure Statement
The information disclosure statements (IDSs) filed on 23 January 2024; 13 January 2025; and 21 March 2025 are acknowledged and have been considered.
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.
Claims 1-17 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 directed to a method of synthesizing bilirubin, but only provides a method of synthesizing a compound of Formula 3. Bilirubin is a compound, whereas Formula 3 is a genus of compounds. As such, the claim is indefinite because it is unclear if or how bilirubin is prepared from a reaction between the compounds of Formulae 1 and 2 to obtain Formula 3. The claim appears to be missing an essential step for how to prepare bilirubin. See MPEP § 2172.01. The omitted elements are: the intermediates and/or reagents necessary to prepare bilirubin from the compounds of Formula 3. Claims 2-17, which depend from claim 1 and therefore incorporate by reference the subject matter thereof, are indefinite because they fail to cure the indefiniteness issue in claim 1.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
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.
Claims 1, 4-5, and 12-17 are rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Brower, 2001 (#5 in IDS filed on 23 January 2024) and Leusen et al. (A New and Simple Synthesis of The Pyrrole Ring System from Michael Acceptors and Tosylmethylisocyanides, Tetrahedron, 52, 5337-5340. Published 1972).
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Brower, 2000 teaches a synthesis of symmetrical bilirubin derivatives (the vinyl groups are replaced by n-butyl groups) (Abstract). The synthesis involves coupling dipyrrolmethane dialdehyde 5 condensed with pyrrolinone 7 to give compound 2. Dimerization of compound 19 provided compound 18 which was further deprotected to give compound 5. Also taught is an oxidation of compound 13 to brominated tosyl pyrrole 11, which upon treatment with TFA provided pyrrolinone 9 (pp. 7869-7870, Synthesis, Scheme 1).
Brower, 2000 does not teach synthesis of a compound like bilirubin using a base (e.g., piperidine) or a compound of Formula 2 wherein R3 is a vinyl or acetyl group, or an ethyl group substituted with a hydroxyl group, carbamate, selenide or sulfide.
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Brower, 2001 teaches a synthesis of unsymmetrical bilirubin derivatives (the vinyl groups are replaced with phenyl groups) (Abstract). The synthesis involves coupling dipyrrolmethane dialdehyde 14 with pyrrolinone 6 in the presence of piperidine (0.28 mL), in 2-propanaol, at reflux overnight (Scheme 1; pp. 7824, 2nd column, 3rd ¶). Dimerization of compound 13 was synthesized the same way as the teachings of Brower, 2000 (¶ 15) then further acidified to give compound 14 (Brower, 2001, pp.7824, 2nd column, 2nd ¶). Also, taught is an oxidation of compound 11, which upon treatment with TFA provided pyrrolinone 9 (Scheme 1; pp. 7824, 2nd column, last ¶).
Brower, 2001 does not teach a compound of Formula 2 wherein R3 is a vinyl or acetyl group, or an ethyl group substituted with a hydroxyl group, carbamate, selenide or sulfide.
Leusen et al. teaches a method of making 3-acylpyrroles by reacting tosylmethylisocyanide (TosMIC) under basic conditions with α,β-unsaturated ketones, esters, etc. (p. 5337, 2nd ¶). Representative example IId is shown in the Table on p. 5338.
Brower, 2000 and Brower, 2001 (collectively “Browers”) are in the same field of coupling dipyrrolmethane dialdehyde compounds with pyrrolinone compounds to synthesize bilirubin. Leusen et al. is analogous art to Browers because it is teaches synthesis of a pyrrole, IId, through the Barton-Zard reaction which is taught in Browers to synthesize the pyrrole intermediates utilized in the synthesis of bilirubin.
Therefore, it would have been prima facie obvious to a person having ordinary skill in the art (PHOSITA), before the effective filing date of the invention, to combine the teachings of Browers and Leusen et al. to arrive at the method of making bilirubin as in instant claim 1. It would have been prima facie obvious to a PHOSITA to substitute intermediate IId taught by Leusen et al., for the pyrroles taught in Browers to make a pyrrolinone representative of Formula 2, because the reagents of the Barton-Zard reaction are equivalent in the tosylmethylisocyanide but can vary in the second reagent to give the desired pyrrole (MPEP §2144.06(II)). Accordingly, claims 1 and 12 are prima facie obvious.
Regarding claim 4, Brower, 2000 teaches dimerization of compound 19 to give compound 18 which is deprotected to give compound 5. Although compound 19 has a protecting group with fewer carbons than the protecting group in the claimed compound, the carbamate protecting group of 18 does not affect the outcome of the dimerization reaction because it is not involved in the reaction. It would have been prima facie obvious to a PHOSITA to substitute the carbamate protecting group for a benzyl ester protecting group and arrive at the compound instantly claimed as they are both known for the same purpose (MPEP §2144.06(II)).
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Regarding claim 5, Brower, 2000 teaches a synthesis of derivatized pyrroles using the Barton-Zard reaction (Scheme 1, pp. 7871, 1st column, 1st ¶). Leusen et al. teaches synthesis of compound IId via the Barton-Zard reaction to give the same compound as in the instant claim. It would have been prima facie obvious to a PHOSITA to substitute the ester taught in Brower, 2000 (i.e., 15) for the one taught in Leusen et al. (see above citations) to arrive at the pyrrole compound of Formula 9 as both teachings use the Barton-Zard reaction to synthesize the derivatized pyrrole. Brower, 2000 further teaches subsequent oxidation of pyrrole 13 to give compound 11 which is further oxidized to give compound 9 (below). The structural differences between the compound of Formula 9 and the compounds in Brower, 2000 relate to the substituents at non-reactive positions on the pyrrole, however the teachings of Leusen et al. would have led a PHOSITA to synthesize the pyrrole of Formula 9 and oxidize it under the same conditions taught by Brower, 2000 with a reasonable expectation of success.
Regarding claims 13-17, Brower, 2001 teaches the synthesis of compound 2 was carried out by dissolving compound 6 (1.46 mmol) and compound 14 (0.341 mmol) in 2-propanol in the presence of 0.28 mL piperidine (ρ = .862 g/mL, 2.83 mmol) at reflux overnight (pp. 7824, 3rd ¶). A PHOSITA would have reasonably understood that reflux is the boiling point of 2-propanol (~80°C), overnight is at least 8 hours of reaction time, and to calculate and add molar excess of piperidine based on its density as it predominantly exists in liquid form. The reaction conditions overlap with the instant claims and therefore would have been prima facie obvious (MPEP §2144.05(I)).
Claims 2-3 are rejected 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Lee et al. (Bilirubin Nanoparticles as a Nanomedicine for Anti-inflammation Therapy, Angew. Chem. Int. Ed. 2016, 55, 7460 –7463. Published 4 May 2016).
The teachings of Brower, 2000 are discussed above (¶15) and are incorporated by reference herein.
Regarding claims 2 and 3, Brower, 2000 does not teach reacting a compound represented by Formula 3 or Formula 1 with polyethylene glycol (PEG).
Lee at al. teaches that bilirubin is an endogenous high potency anti-inflammatory compound, but its clinical translation has been hampered because of its insolubility in water (Abstract). Further taught is a method of PEGylating bilirubin with mPEG2000-NH2 to give PEGylated bilirubin to enhance solubility of bilirubin (Figure 1a).
Brower, 2000 and Lee et al. are in the same field of synthesizing bilirubin and derivatives thereof. Brower, 2000 further teaches that the intramolecular bonding of bilirubin reduces its polarity which makes it intrinsically unexcretable unless it’s converted to its glycosyl ester conjugate (p. 7869, Introduction). Therefore, it would have been prima facie obvious to a PHOSITA to combine the teachings of Brower, 2000 with the teachings of Lee et al. to arrive at the methods instantly claimed. A PHOSITA would have been motivated to combine the teachings of Browers and Lee et al. to synthesize PEGylated bilirubins for enhanced solubility. Furthermore, the timing of PEGylation would not change if a compound of Formula 1 was used instead of a compound of Formula 3 because the PEG functional group would react at similar sites of either molecule. Accordingly claims 2-3 are prima facie obvious.
Claims 6-7 are rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Olson et al. (#4 in IDS filed on 13 January 2025).
The teachings of Brower, 2000 are discussed above (¶ 15) and are incorporated by reference herein.
Regarding claims 6-7, Brower, 2000 does not teach a reduction of an acetyl group of a pyrrolinone compound or a dehydration of the resulting alcohol.
Olson et al. teaches reduction of the acetyl group of compound 40 to alcohol 46 and then dehydration of the alcohol to give the vinyl compound 29a (pp. 2759, Scheme 13).
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Brower, 2000 and Olson et al. are related art because they are both in the field of total synthesis having α,β-unsaturated pyrrolinones as key intermediates. Therefore, it would have been prima facie obvious to a PHOSITA, before the effective filing date of the claimed invention, to synthesize bilirubin following the teachings of Brower, 2000 and incorporate the teachings of Olson et al. to reduce a compound of Formula 10 and dehydrate a compound of Formula 11 to prepare a compound of Formula 2, as instantly claimed. The structural differences between the compounds of Formulae 10 and 11 and 40 and 46, respectively in Olson et al. relate to the substituents at non-reactive positions on the pyrrolinone. Despite the structural differences, compounds 40 and 46 are positional isomers of Formulae 10 and 11, respectively, and are therefore considered to possess similar properties (MPEP §2144.09(II)). A PHOSITA would have been motivated to apply the reaction conditions taught by Olson et al. to the pyrrolinones taught by Brower, 2000 to arrive at the method instantly claimed. Accordingly, claims 6-7 are prima facie obvious.
Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Bregoli et al. (#5 in IDS filed on 13 January 2025).
The teachings of Brower, 2000 are discussed above (¶15) and are incorporated by reference herein.
Regarding claim 8, Brower, 2000 does not teach a cyclization reaction to provide a pyrrolinone type compound.
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Bregoli et al. teaches cyclization of compound 1 in the presence of CuCl dissolved in ACN. The reaction conditions of compound 1f in Table 2 show that compound 2f was obtained in 93% yield (p. 1270, Scheme 6, Table 2, Entry 11). The subsequent elimination reaction was carried out in DMF at 100°C for 24 hours to give compound 5 in 46% yield (pp. 1271, Figure 1; pp. 1272, Table 3, Entry 13).
Brower, 2000 and Bregoli et al. are related art because they are both in the same field of synthesizing derivatized pyrrolinones. Compound 1f of Bregoli et al. corresponds to Formula 12 of the instant claim wherein R4 is a mesylate nitrogen protecting group and compound 5 of Bregoli et al. corresponds to instant Formula 2 wherein R4 is a mesylate nitrogen protecting group, R3 is a vinyl group, and R5 is a hydrogen. Therefore, it would have been prima facie obvious to a PHOSITA, before the effective filing date of the claimed invention, to synthesize bilirubin following the teachings of Brower, 2000 and incorporate the teachings of Bregoli et al. to cyclize a compound of Formula 12 to prepare a compound of Formula 2, as instantly claimed. A PHOSITA would have had a reasonable expectation of success combining the teachings of these prior art elements to arrive at the method instantly claimed as the prior art compounds are species of the genus of Formula 12 and 2. Accordingly, claim 8 is prima facie obvious.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Santander et al. (Preparation of pyrrolin-2-ones and 4,5-dihydrodipyrrin-1-ones by oxidation of α-formylpyrroles and α-formyldipyrromethanes with hydrogen peroxide, Tetrahedron, 41, 2825–2829, Published 26 June 2000), further in view of Fischer et al. (#6 in IDS filed on 13 January 2025).
The teachings of Brower, 2000 are discussed above (¶15) and are incorporated by reference herein.
Regarding claim 9, Brower, 2000 does not teach an oxidation or the carbamating of a pyrrole compound.
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Santander et al. teaches oxidation of pyrrole 1 to give pyrrolin-2-one 2. Entry 5 from Table 1 is a representative example of such an oxidation reaction (p. 2826).
Santander et al. does not teach carbamating the resulting pyrrolin-2-one.
Fischer et al. teaches carbamating pyrrole IV via reaction with hydrazine, subsequent treatment with nitrous acid, and then boiling in ethanol to give the carbamate VII (pp. 2 of applicant submitted machine translation).
Brower, 2000, Santander et al., and Fischer et al. are related art because they are in the same field of derivatizing and oxidizing pyrroles to prepare pyrrolinones. Therefore, it would have been prima facie obvious to a PHOSITA, before the effective filing date of the claimed invention, to synthesize bilirubin following the teachings of Brower, 2000 and incorporate the teachings of Santander et al., to first oxidize a pyrrole aldehyde compound like that of Formula 13, and the teachings of Fischer et al. to subsequently carbamate the resulting pyrrolinone ester of Formula 13. The prior art compounds are homologs of Formula 13 and the non-reactive positions are taught to be unaffected by the reaction conditions. The structural differences of 1 (Santander et al.) and IV (Fischer et al.) compared to compounds of Formula 13, relate to the substituents at non-reactive positions on the pyrrole. Therefore, the prior art compounds are generally of sufficiently close structural similarity and presumably possess similar properties to compounds of Formula 13 (MPEP §2144.09(III)). Accordingly, claim 9 is prima facie obvious.
Claims 10 is rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Jacobi et al. (#7 in IDS filed on 13 January 2025).
The teachings of Brower, 2000 are discussed above (¶15) and are incorporated by reference herein.
Regarding claim 10, Brower, 2000 does not teach a cyclization of a compound represented by Formula 14 containing a selenide moiety.
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Jacobi et al. teaches cyclization of compound 15 in the presence of potassium tert-butoxide to give compound 16 (pp. 8480, Scheme 2).
Brower, 2000 and Jacobi et al. are related art because they are in the same field of synthesizing derivatized pyrrolinones. Therefore, it would have been prima facie obvious to a PHOSITA, before the effective filing date of the claimed invention, to synthesize bilirubin following the teachings of Brower, 2000 and incorporate the teachings of Jacobi et al. to cyclize a compound of Formula 14 to prepare a compound of Formula 2, as instantly claimed. The structural differences between the compounds of Jacobi et al. and that of Formula 14 relate to the substituents at non-reactive positions. Despite the structural differences, compounds 15 and 16 of Jacobi et al. are positional isomers of Formula 14 and Formula 2, respectively, and are therefore considered to possess similar properties (MPEP §2144.09(II)). A PHOSITA would have been motivated to apply the reaction conditions taught by Jacobi et al. to synthesize a compound of Formula 2 and synthesize bilirubin through the teachings of Brower, 2000 and would have had a reasonable expectation of success. Accordingly, claim 10 is prima facie obvious.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Brower, 2000 (#4 in IDS filed on 23 January 2024) in view of Kakiuchi et al. (#8 in IDS filed on 13 January 2025).
The teachings of Brower, 2000 are discussed above (¶15) and are incorporated by reference herein.
Regarding claim 11, Brower, 2000 does not teach oxidizing a bromo pyrrole type compound with a sulfide moiety.
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Kakiuchi et al. teaches oxidation of the bromo pyrrole 9 to give pyrrolinone 10 wherein both compounds contain a sulfide moiety (pp. 902, Scheme 2).
Brower, 2000 and Kakiuchi et al. are related art because they are in the same field of oxidizing pyrroles to pyrrolinones. Therefore, it would have been prima facie obvious to a PHOSITA, before the effective filing date of the claimed invention, to synthesize bilirubin following the teachings of Brower, 2000 and incorporate the teachings of Kakiuchi to oxidize a compound of Formula 15 to prepare a compound of Formula 2, as instantly claimed. Compound 9 of Kakiuchi et al. corresponds to Formula 15 wherein R4 is a hydrogen, R5 is a tosylate, and Z is a sulfide. Compound 10 of Kakiuchi corresponds to Formula 2 wherein R4 is a hydrogen, R5 is a tosylate, and Z is a sulfide. A PHOSITA would have had a reasonable expectation of success combining the teachings of these prior art elements to arrive at the method instantly claimed as the prior art compounds are species of the genus of Formula 15 and 2. Accordingly, claim 11 is prima facie obvious.
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.
Claims 1-17 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 1-15 of copending Application No. 18/291,336 (‘336). Although the claims at issue are not identical, they are not patentably distinct from each other because instant claims 1-17 are obvious over claims 1-15 of ‘336, as explained below.
52, This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
53. Claims 1-4 and 10-15 of ‘336 recite related subject matter as instant claims 1-4 and 12-17 with differences that are obvious variants: claim 1 of ‘336 recites R3 can be a hydrogen but not an ethyl group substituted with a carbamate, whereas instant claim 1 excludes hydrogen but includes an ethyl group substituted with carbamate. Compounds of Formulae 2 and 3 represented in claim 1 of ‘336´are positional isomers of instant claim 1 and therefore have a presumed expectation of possessing similar properties and therefore would have been prima facie obvious to a PHOSITA to arrive at the method instantly claimed (MPEP §2144.09(II)).
54. Claims 6-9 of ‘336 recite methods of making a compound of Formula 2 in a similar fashion to instant claims 6-7 and 10-11. The differences are the positional isomers of Formula 2 in claim 1 of ‘336 and the instant claims. Positional isomers have a presumed expectation of possessing similar properties and therefore would have been prima facie obvious for a PHOSITA to arrive at the method instantly claimed (MPEP 2144.05(II)).
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAHIL CHANDER AGGARWAL whose telephone number is (571)272-7755. The examiner can normally be reached 7am-5pm.
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/SAHIL CHANDER AGGARWAL/Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623
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