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
The amendments received 12/23/2025 have been entered. Claims 1, 3, and 9-10 are pending. Any objection or rejection set forth in the Office Action mailed 09/23/2025 not maintained herein has been overcome and is withdrawn.
New grounds of rejection are set forth herein as necessitated by amendment.
Terminal Disclaimer
The terminal disclaimer filed on 12/18/2025 disclaiming the terminal portion of any patent granted on this application which would extend beyond the expiration date of application 18/210,068 and U.S. Patent 11618729 has been reviewed and is accepted. The terminal disclaimer has been recorded.
Specification
The disclosure is objected to because of the following informalities:
Examiner notes that the naming of formulas 3, 4, 9, 10, and 14 appears to be incorrect, first because “…sulfonyl group” is not a proper naming convention and second because the structures of the aforementioned formulas contain sulfinyl rather than sulfonyl groups;
Examiner recommends that applicant review the naming for all disclosed formulas and provide corrections where necessary; for example, formula 5 does not contain a porphyrin group (see paragraph [0038]) which is the naming convention used for all of formulas 3-7.
Appropriate correction is required.
Claim Objections
Claim 1 is objected to because of the following informalities: "in a presence of a catalyst" should read "in the presence of a catalyst". Appropriate correction is required.
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, and 9-10 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 recites the structures of formula 2 and formula 1, both of which are substituted by R. Claim 1 therefore contains two definitions for the same variable “R” that are not the same in scope, which causes confusion. Correction is required.
Claim 1 recites “wherein the heating reaction”. This limitation lacks antecedent basis.
Claim 3 sets forth the structures of formulas 3-6. However, formulas 3-4 are not within the scope of claim 1, as R1 and/or R2 cannot be p-toluenesulfinyl per claim 1.
Claim Rejections - 35 USC § 112(a)
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.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
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 of carrying out his invention.
Claims 1, 3, and 9 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, because the specification, while being enabling for a catalyst selected from pyridine, sodium ethoxide, or a mixture thereof, does not reasonably provide enablement for a catalyst generally. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims.
Claims 1-10 are directed toward a method of preparing biliverdin or a derivative thereof wherein the reaction takes place “in [the] presence of a catalyst”. Thus, the claims are incredibly broad. The working examples only demonstrate successfully preparing biliverdin or biliverdin dimethyl ester, wherein the compounds of formula 2 are dissolved in nitrobenzene, pyrrolidone, xylene, DMF, or THF and the resulting mixture was heated to 130-160⁰C. Additionally, the working examples only demonstrate successfully preparing biliverdin dimethyl ester wherein the catalyst is pyridine. Regarding predictability in the art, synthetic chemistry is generally regarded as unpredictable despite a high level of skill. See In Re Marzocchi and Horton, 169 USPQ at 367 paragraph 3:
“Most non-chemists would probably be horrified if they were to learn how
many attempted syntheses fail, and how inefficient research chemists are.
The ratio of successful to unsuccessful chemical experiments in a normal
research laboratory is far below unity, and synthetic research chemists, in
the same way as most scientists, spend most of their time working out
what went wrong, and why. Despite the many pitfalls lurking in organic
synthesis, most organic chemistry textbooks and research articles do give
the impression that organic reactions just proceed smoothly and that the
total synthesis of complex natural products, for instance, is maybe a labor-
intensive but otherwise undemanding task. In fact, most syntheses of
structurally complex natural products are the result of several years of
hard work by a team of chemists, with almost every step requiring careful
optimization. The final synthesis usually looks quite different from that
originally planned, because of unexpected difficulties encountered in the initially chosen synthetic sequence. Only the seasoned practitioner who
has experienced for himself the many failures and frustrations which the
development (sometimes even the repetition) of a synthesis usually
implies will be able to appraise such work ......Chemists tend not to publish
negative results, because these are, as opposed to positive results, never
definite (and far too copious) ...” Dorwald F. A. Side Reactions in Organic
Synthesis, 2005, Wiley: VCH, Weinheim pg. IX of Preface.
Given the limited guidance and breadth of the claims, in view of the level of unpredictability in the art, one of ordinary skill in the art would not be able to prepare biliverdin or a derivative thereof via the method of claims 1, 3, and 9 without undue experimentation.
Response to Arguments
Applicant's arguments filed 12/23/2025 have been fully considered but they are not persuasive.
Objections to Specification
Regarding Examiner’s objections to the specification, Applicant states, “Regarding the fourth issue of specification objections, it seems to Applicant that the ‘porphyrin’ is the core structure of the formula 3 to formula 7, so there is no clarity issue.” This is not persuasive. The core structure of the compounds within the scope of formula 2 (such as formula 3 and formula 7) is not porphyrin. As defined by PhysicsOpenLab (PhysicsOpenLab.org; 2016), porphyrins are defined as “a group of heterocyclic macrocycle organic compounds, composed of four modified pyrrole subunits interconnected at their α carbon atoms via methine bridges.” The compounds of the instant specification are not macrocyclic as the first and fourth pyrrole subunits are not connected via a methine bridge. Moreover, Applicant has provided no special definition that sets forth what “porphyrin” means in the scope of the invention such that one of ordinary skill in the art would interpret “porphyrin” in any way other than its broadest reasonable interpretation.
Applicant additionally states, “Regarding the third issue of specification objections, Applicant has amended the term "2-p-tolylene sulfonyl" to "p-toluenesulfonyl" recited throughout the specification (including the formulas 3, 4, 9, 10, and 14) to provide better clarity.” However, this amendment does not address Examiner’s additional objections regarding “…sulfonyl group” (emphasis added) not being a proper naming convention and that formulas 3, 4, 9, 10, and 14 contain sulfinyl groups, not sulfonyl groups (i.e., “p-toluenesulfinyl”).
35 U.S.C. 112(b)
Regarding the rejections under 35 U.S.C. 112(b), Applicant states, “Regarding the third issue of claim rejections under 35 U.S.C. 112(b), Applicant has limited the structure of biliverdin or a derivative thereof (formula 1) in claim 1, so the formulas 3-4 are within the scope of claim 1.” This is not persuasive, nor does this amendment resolve the issue addressed by Examiner.
Formula 1 sets forth the scope of “biliverdin or a derivative thereof” and is interpreted to be the product of the method, while formula 2 is interpreted to be the starting material. Claim 3, which recites formulas 3-4, further limits the scope of formula 2. Therefore, inserting formula 1 into claim 1 does not clarify the scope of formula 2 as it relates to formulas 3 and 4. Formulas 3 and 4 are substituted in the R1 and/or R2 positions by p-toluenesulfinyl, which is not within the scope of formula 2 as in claim 1. The rejection is maintained.
35 U.S.C. 112(a)
Regarding the rejection under 35 U.S.C. 112(a), Applicant states, “Namely, the amended claim 1 reasonably provide enablement for preparing the biliverdin or the derivative thereof, and one of ordinary skill in the art would be able to prepare the biliverdin or the derivative thereof via the method limited in the amended claim 1 without undue experimentation.” As Applicant does not provide specific arguments against Examiner’s rejection, Examiner points to the above rejection under 35 U.S.C. 112(a) regarding “catalyst” generally. For the reasons as set forth above, the rejection is maintained with regards to this limitation.
Conclusion
No claims are allowed.
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 MADELINE E BRAUN whose telephone number is (703)756-4533. The examiner can normally be reached M-F 8:30am-5:00pm ET.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/M.E.B./Examiner, Art Unit 1624 01/21/2026
/BRENDA L COLEMAN/Primary Examiner, Art Unit 1624
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