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 .
Claim Status
Claims 1-9 are examined herein.
Claims 10-20 are withdrawn (see restriction/election below).
Priority
This application is filed 05/12/2023 and claims the benefit of domestic priority as below:
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Information Disclosure Statements
One IDS(s) received on 10/19/2023 have been considered unless marked with a strikethrough.
Election/Restrictions
Applicant elects Group I, claims 1-9, is drawn to a compound having a structure represented by Formula I, and salts and compositions thereof, with traverse in the reply field on 04/23/2026 is acknowledged. Claims 10-14 (Group II), and claims 15-20 (Group III) are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected a compound of formula (I) or (I'), or a pharmaceutically acceptable salt or composition thereof, and a nonelected method of treating, there being no allowable generic or linking claim.
The applicants argue that the restriction is improper because searching the groups together would not constitute a serious search and examination burden. This argument is not persuasive because searching the different inventions would require different fields of search , search queries and strategies. For example, elected claims 1-9 are directed to methods of synthesizing lysergic acid or derivatives thereof. These claims require searching synthetic steps, reagents, protecting groups, reducing agents, bases, annulating agents, Grignard reagents, and reaction sequences. In particular, limitations of claims 1-9 require a process oriented search focused on reaction chemistry, synthetic methodology, intermediates, reagents, and reaction conditions. By contrast, claims 10-14 are directed to compounds of Formula (I) or (I’) or pharmaceutically acceptable salts thereof, and pharmaceutical compositions comprising such a compounds or salts. These claims require a product oriented search focused on chemical structures, substituent patterns, Markush group coverage, salts, structural analogs, pharmaceutical compositions, and compound classification. Such a search is materially different from the search required for the synthetic methods of claims 1-9. Further, claims 15-20 are directed to method of treating neurodegenerative disease. These groups require a search focused on biological activity, therapeutic use, disease models, neurodegenerative disease indications, pharmacological effect, dosage, patient treatment, and clinical or preclinical disclosures. Additionally, the Examiner needs to search for and consider obviousness art for an invention related to 35 U.S.C. 103(a), this requires broader and more extensive search queries than those searches for anticipatory art. Therefore, Examination of all the different inventions, including the methods of making the compounds, the compounds and pharmaceutical compositions themselves, and the method of using the compounds for treatment, would impose a serious search and examination burden.
Accordingly, the restriction requirement is deemed proper and is made FINAL.
Applicant elects a compound of formula (A) of claim 1, wherein R1, R2, R3, R4, R5, and R6 are hydrogen, X is Br, and the protecting group is a tert-butyloxycarbonyl protecting group in claim 1 as the species, with traverse in the reply field on 04/23/2026 is acknowledged.
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The claims 1-9 read on the elected species.
If the elected specie is not identified in the prior arts, the elected specie would be allowable if
an independent claim were drafted with that specie alone. (see MPEP 802.03)
The elected specie was identified in the prior art. With respect to the elected species, the art is rejected under 35 USC 102 as well as on the ground of double patenting below.
Abstract
The abstract of the disclosure is objected to because the abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. Currently, the abstract has 33 words.
The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details. The current submitted abstract is the front pages of PCT application. Examiner requests to bring in narrative form to satisfy the abstract requirement.
Correction is required. See MPEP § 608.01(b).
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 9 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 9 recites the limitation "the method of claim 1, further comprising deacetylation to form a compound of formula (I)" in the first part of claim 9. There is insufficient antecedent basis for this limitation in the claim. Claim 9 depends from claim 1, which broadly recites ProtG as “a protecting group”, and recites removal of the protecting group, but does not require ProtG to be acetyl or otherwise require the presence of an acetyl containing group. Further, claim 3 recites that the protecting group is a tert-butyloxycarbonyl (i.e., Boc). Removal of a Boc protecting group is understood as a deprotection, not deacetylation. Accordingly, it is unclear what chemical transformation is required by the recited “deacetylation” step.
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.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-3 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Inoue et al. (Synthetic studies toward (+)-lysergic acid: construction of the tetracyclic ergoline skeleton, heterocycles, 79, 373-378, pub’d 1/16/2009).
Inoue discloses a method of synthesizing lysergic acid comprising contacting a compound of Formula A (i.e., compound 26) and Pd2(dba)3 to produce an annulated compound and removing the protecting group from the annulated compound (scheme 5).
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Compound 26 of Inoue corresponds to the compound of Formula (A) recited in claim 1 wherein ProtG is Boc, X is Br, and R1-R6 are independently selected from hydrogen that corresponds the elected species (scheme 5). Inoue further teaches contacting compound 26 with an annulating agent (i.e., Pd2(dba)3) to produce an annulated compound (scheme 5). Inoue also discloses subsequent removal of the Boc protecting group from the annulated compound in the synthetic sequence leading to (+)-lysergic acid (scheme 5).
The annulating agent, Pd2(dba)3CHCl3, disclosed by Inoue corresponds to claim 2, and Boc protected compound 26 of Inoue corresponds to the compound of Formula (A) corresponds to claim 3 (Scheme 5).
Double Patenting
A rejection based on double patenting of the “same invention” type finds its support in the language of 35 U.S.C. 101 which states that “whoever invents or discovers any new and useful process... may obtain a patent therefor...” (Emphasis added). Thus, the term “same invention,” in this context, means an invention drawn to identical subject matter. See Miller v. Eagle Mfg. Co., 151 U.S. 186 (1894); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Ockert, 245 F.2d 467, 114 USPQ 330 (CCPA 1957).
A statutory type (35 U.S.C. 101) double patenting rejection can be overcome by canceling or amending the claims that are directed to the same invention so they are no longer coextensive in scope. The filing of a terminal disclaimer cannot overcome a double patenting rejection based upon 35 U.S.C. 101.
Claims 1-9 are provisionally rejected under 35 U.S.C. 101 as claiming the same invention as that of claims 1-9 of copending Application No. 18/865,302 (reference application). This is a provisional statutory double patenting rejection since the claims directed to the same invention have not in fact been patented.
The instant claims 1-9 and claims 1-9 of ‘302 are completely identical.
Art of Record but not Applied
Liu et al. (Total Synthesis of (+)-Lysergic Acid, J. Org. Chem. 2013, 78, 21, 10885–10893, pub’d 10/10/2013) and Liu et al. (Total Synthesis of (+)-Lysergic Acid, Org Lett., 13(18), 4810-4813, pub’d 08/25/2011) demonstrate the process for the synthesis of (+)-Lysergic Acid. This prior study also describes the similar contents as the anticipated reference. However, these references form the ring via an intermolecular Heck reaction. This differs from the process recited in the instant claims, which requires different intermediates and method steps (e.g. claimed Grignard reagent and Grignard reaction for Formula (B)). Accordingly, the references do not provide a sufficient basis for a rejection under 35 USC 103.
Conclusion
Claims 1-9 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEONG JONG KIM whose telephone number is (571)272-6918. The examiner can normally be reached 7:00am-3:30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton A. Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SEONG JONG KIM/ Examiner, Art Unit 1621
/CLINTON A BROOKS/ Supervisory Patent Examiner, Art Unit 1621
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