Detailed Action
The present office action is in response to the response filed on 02 Jun 2026.
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 .
Status
Claims 1, 4, 8-14, 42-44, and 58 of the pending application have been examined on the merits. Claims 2-3, 5-7, 15-18, 45-46, 53, and 56 are withdrawn (see “Response to Applicant Election” below). Acknowledgement is made of the amendments filed 11 Sep 2024. Acknowledgement is made of the cancellation of claims 19-41, 47-52, 54-55, 57, and 59-60.
Priority
Applicants identify the instant application, Serial #: 18/683,854, filed 15 Feb 2024, as a National Stage Entry of International Application #: PCT/CA2022/051265, filed 19 Aug 2022, which claims priority from Provisional Application #s: 63/347,845, filed 01 Jun 2022, 63/326,406, filed 01 Apr 2022, and 63/260,470, filed 20 Aug 2021.
Information Disclosure Statement
The information disclosure statement(s) (IDS) submitted on 11 Sep 2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Response to Applicant Election
Applicant’s election without traverse of Group I, claims 1-18, 42-44, and 58, in the reply filed on 02 Jun 2026 is acknowledged. Applicant has further elected Compound I-3 as the species of Formula I in the reply filed 02 Jun 2026:
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Prior art was returned after a search for the elected species.
Claims 2-3, 5-7, and 15-18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Claims 45-46, 53, and 56 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 02 Jun 2026.
Examiner notes that the relevant anticipation rejection below is based upon art which was found incidental to the search for the elected species. The additional art found is relevant to the claims addressing species where which contain an indole moiety attached to a nitrogen heterocycle at the 3-position. This is not indicative that the entire scope of the claims has been examined; however, the following art is being applied in an effort to promote compact prosecution of the case.
Claim Objections
Claim 1 is objected to because of the following informalities: The word “heteromoeities” should be “heteromoieties” in claim 1 on pg. 3, line 12 of the claims. Appropriate correction is required.
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, 4, 8, 9-14, 42-44, and 58 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Factors to be considered in making the determination as to whether one skilled in the art would recognize the applicant was in possession of the claimed invention as a whole at the time of filing include:
Actual reduction to practice;
Disclosure of drawings or structural chemical formulas;
Sufficient relevant identifying characteristics such as:
Complete structure,
Partial structure,
Physical and/or chemical properties, or
Functional characteristics when coupled with a known or disclosed correlation between function and structure;
Method of making the claimed invention;
Level of skill and knowledge in the art;
Predictability in the art.
While all these factors are considered, a sufficient number for a prima facie case are discussed below.
Regarding claims 1, 4, 8-9, and 42, here, the claims are drawn to "prodrug." Applicant provides no guidance as to prodrugs. The artisan understands that prodrug forms are generally determined a posteriori, and it is only through trial and error that prodrugs are identified. The artisan understands the concept of prodrugs, however the artisan does not per se understand what specifically describes a prodrug form. Han (AAPS Pharmsci, 2000, vol. 2, article 6), cited here for evidence, teaches there is no strict universal definition for a prodrug itself but that, in general, the prodrug is an inactivated form of the drug that activates in vivo to the active form (pg. 1, column 2). While some prodrugs are simply esters or salts, other prodrug forms are not chemically or structurally related to their active form, one example being glucose as the prodrug form of hydrogen peroxide (Table 1, pg. 5), as is hypoxanthine, thus posing a problem as to understanding what is the exact prodrug form of a compound, as hydrogen peroxide has two prodrug forms in the limited set of compounds exemplified in Han.
According to Ettamayer et al. (J Med Chem, 2004, 47:2393-2404), cited here for evidence, prodrugs are often accidental discoveries (pg. 2393, column 2). Furthermore, Testa et al. (Biochem Pharm, 2004, 68:2097-2106), cited here for evidence, teaches:
[A] number of challenges await medicinal chemists and biochemists carrying out prodrug research, such as the additional work involved in synthesis, physiochemical profiling, pharmacokinetic profiling and toxicological assessment. Two of these challenges are introduced here, namely biological variability and toxicity potential. The challenge of biological variety results principally but not only from the huge number and evolutionary diversity of enzymes involved in xenobiotic metabolism. Inter- and intra-species differences in the nature of these enzymes, as well as many other differences such as the nature and level of transporters, may render prodrug optimization difficult to predict and achieve. (pg. 2098, column 2)
Methods of making compounds, in general, are known to the artisan. However, the methods of making any specific prodrug are complex and poorly understood, requiring an undue amount of experimentation to determine if a compound is actually a prodrug, and the instant specification fails to provide guidance to overcome the complexity and difficulties known to the artisan, as discussed above.
Thus, the artisan would have increased difficulty in determining how to convert the claimed compounds into prodrugs.
Regarding claims 10-14, 43-44, and 58, these claims are similarly rejected as these claims refer back to claim 1, but do not remedy the rationale underpinning the basis for rejecting claim 1.
The description requirement of the patent statute requires a description of an invention, not an indication of a result that one might achieve if one made that invention. See In re Wilder, 736, F2d 1516, 1521, 222 USPQ 369, 372-73 (Fed. Cir. 1984) (affirming rejection because the specification does "little more than outlin[e] goals appellants hope the claimed invention achieves and the problems the invention will hopefully ameliorate.") Accordingly, it is deemed that the specification fails to provide adequate written description for the genus of the claims and does not reasonably convey to one skilled in the relevant art that the inventor(s), at the time the application was filed, had possession of the entire scope of the claimed invention.
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 4, 8-9, and 58 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.
Regarding claims 4 and 8-9, the claims recite the limitation:
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However, the variable R20’ is only associated with the Q2’ moiety and claims 4 and 8-9 limit Q to being Q2. The person having ordinary skill in the art would be unclear how R20’ would be incorporated into the compound of the claims. Applicant may overcome this rejection by pointing out where in the claims R20’ would be present or cancelling R20’ from the claims.
Regarding claim 58, the claim recites the limitation: “A pharmaceutical composition comprising a compound of claim 1 and an additional therapeutic agent.” The phrase “additional therapeutic agent” is very broad in its scope and encompasses any agent which may have therapeutic effect. While the specification provides examples of “additional therapeutic agents” (paragraphs [00217]-[00230]) there is no limiting definition provided. The therapeutic agents of the claim could therefore be anything with some therapeutic effect resulting in an unlimited number of choices. The lack of boundaries regarding what counts as a therapeutic agent results in claim 58 being indefinite.
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.
Examiner notes that the following anticipation rejections below are based upon art which was found incidental to the search for the elected species. This is not indicative that the entire scope of the claims has been examined; however, the following art is being applied in an effort to promote compact prosecution of the case.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by U.S. Patent No. 6,133,287, hereinafter ‘287.
Instant claim 1 is directed towards compounds of general Formula I:
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‘287 teaches compounds of reference Formula (I):
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Compounds of the reference Formula I are all species of instant Formula I and so the reference anticipates the instant claims.
Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by U.S. Patent No. 5,998,438, hereinafter ‘438.
‘438 teaches Compounds 18a, 19, and 23 which anticipate the instant claims (Columns 29-30 and 45-46):
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Claim(s) 1 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by U.S. Patent No. 5,856,510, hereinafter ‘510.
‘510 teaches Compound 7d which has the following structure (Columns 15-16):
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Compound 7d anticipates the instant claims.
Claim Rejections - 35 USC § 103
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 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.
Claim(s) 1, 4, 8-14, 42-44, and 58 is/are rejected under 35 U.S.C. 103 as being unpatentable over Taylor et al. (Mol Pharmacol, 1988, 34:42-53), hereinafter Taylor, further in view of Atzrodt et al. (Angew Chem Int Ed, 2018, 57:1758-1784), hereinafter Atzrodt, Winnicka et al. (J Radioanal Nucl Chem, 2009, 279:675-678), hereinafter Winnicka, Bhattacharyya et al. (2006, CRC Press, “Excipient development for pharmaceutical, biotechnology, and drug delivery systems,” Ch. 1), hereinafter Bhattacharyya, and U.S. Patent No. 5,834,493, hereinafter ‘493.
The instant claims are directed to compounds of Formula I (claim 1):
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In the reply filed 02 Jun 2026 applicant elected Compound I-3 as the species of Formula I:
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Compound I-3 reads on claims 1, 4, 8-14, 42-44 and 58. Claims 43 and 44 claim a composition comprising a compound of claim 1 and a carrier (claim 43) or pharmaceutically acceptable carrier (claim 44). Claim 58 claims a composition comprising a compound of claim 1 and an additional therapeutic agent. It is noted that the instant specification defines “pharmaceutically acceptable carrier” as a non-toxic solvent, dispersant, excipient, adjuvant or other material mixed with the active ingredient to permit formation of a pharmaceutical composition (paragraph [0079]).
Regarding claims 1, 4, 8-14, and 42-44, Taylor teaches the synthesis of 27 analogs of RU24969 to perform a quantitative structure-activity relationship in order to determine structural features which optimize binding potency for the 5-HT1A and 5-HT2 receptors (Abstract). One of the analogs taught by Taylor is Structure 2a (pg. 43, Table 1):
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Structure 2a has an apparent Ki of 19.3 nM for the 5-HT2 receptor which the reference describes as exceptional potency (pg. 43, Table 1; and pg. 51, column 1). However, Taylor does not teach deuterating the unsubstituted carbons of the indole ring, a composition of Structure 2a and a pharmaceutically acceptable carrier, or a composition of Structure 2a and an additional therapeutic compound.
Atzrodt teaches that isotopes of hydrogen have been known for their utility in mechanistic, spectroscopic, and tracer studies and that in medicinal chemistry, replacement of a hydrogen by a deuterium atom has recently received attention as a way to alter ADME properties of drug candidates (pg. 1759, column 1). One of these isotopes is deuterium which is stable and can be handled under standard laboratory conditions without special permissions, handling licenses, or radiation safety measures, which is not the case for the other hydrogen isotope, tritium (pg. 1759, column 2). Atzrodt teaches that deuterating drugs may result in potential beneficial properties such as reduced systemic clearance and higher systemic exposure as well as reduced formation of toxic or reactive metabolites while retaining the potency of the original drug (pg. 1763, column 1).
Winnicka teaches the synthesis of L-tryptophan labeled with hydrogen isotopes in the indole ring including the synthesis of an indole ring fully labeled with deuterium (pg. 677, column 1).
Bhattacharyya teaches that almost all therapeutic products include excipients (pg. 1, paragraph 1). It is further taught that excipients have defined functional roles in pharmaceutical dosage forms including enhancing stability of the active ingredients in finished dosage forms (pg. 1, paragraph 2).
MPEP § 2144.09 states, “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities.”
Based on the teachings of Taylor, Atzrodt, and Winnicka, it would be prima facie obvious to the person of ordinary skill in the art that deuterating the indole of Structure 2a taught by Taylor would result in a compound with similar structure and utility with potential for increased beneficial properties such as reduced systemic clearance and higher systemic exposure as well as reduced formation of toxic or reactive metabolites while retaining the potency of the original drug, specifically against 5-HT2, as taught by Atzrodt. The artisan would have a reasonable expectation of success in modifying the indole of Structure 2a with deuterium to arrive at instant Compound I-3.
Based on the teachings of Taylor, Atzrodt, Winnicka, and Bhattacharyya, the artisan would further combine the compound taught by Taylor, Atzrodt, and Winnicka with an excipient taught by Bhattacharyya to arrive at the composition of the instant claims. The artisan would be motivated to form this composition between the compound and an excipient to enhance stability of the active ingredients in finished dosage forms.
Regarding claim 58, ‘493 teaches compounds of formula (I) which have utility as 5-HT2 receptor inhibitors (Abstract):
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‘493 teaches Compound 9 as a species of formula (I) with a Ki of 15 nM for the 5-HT2 receptor (Column 9, lines 25-35; and Column 15, lines 4-30):
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Based on the teachings of Taylor, Atzrodt, Winnicka, and ‘493 it would be prima facie obvious to one having ordinary skill in the art to combine the composition of instant Compound I-3, taught by Taylor, Atzrodt, and Winnicka (see above), with the composition of Compound 9, taught by ‘493, to create a third composition to modulate the 5-HT2 receptor with a reasonable expectation of success. See In re Kerkhoven, 626 F.2d 846, 850, 205 USPQ 1069, 1072 (CCPA 1980).
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
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 1, 8, 10-13, and 43-44 rejected on the ground of anticipatory-type nonstatutory double patenting as being unpatentable over claims 1-22 of U.S. Patent No. 5,856,510. Although the claims at issue are not identical, they are not patentably distinct from each other.
The instant claims 1 and 10-13 are directed to compounds of Formula I:
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Claim 8 is directed to compounds of Formula I-E’:
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Instant claims 43-44 are directed to a composition of a compound of claim 1 and a carrier (claim 43) or pharmaceutically acceptable carrier (claim 44).
The reference teaches compounds of Formula I:
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The compounds of reference Formula I anticipate the compounds of the instant claims when reference variable R2 is Formula II. Reference claim 20 is directed to a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of reference claim 1 in an amount effective to stimulate a 5-HT1D-like receptor.
Claims 1, 4, 8-13, and 43-44 are rejected on the ground of anticipatory-type nonstatutory double patenting as being unpatentable over claim 1-35 of U.S. Patent No. 5,998,438. Although the claims at issue are not identical, they are not patentably distinct from each other.
The reference claims compounds of Formula I (claim 1):
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The compounds of Formula I anticipate the instantly claimed compounds when reference variable R2 is Formula II or IV. Reference claim 34 is directed to a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of Formula V:
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Ring A, R1, R3, and R2 are defined as in reference claim 1. Therefore, the reference anticipates the instant claims.
Claims 1 and 43-44 rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 and 16 of U.S. Patent No. 6,133,287. Although the claims at issue are not identical, they are not patentably distinct from each other.
The reference claims compounds of formula I:
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The reference formula I is a species of instant Formula I. The reference also claims a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound of reference formula I.
Claims 1, 10, 43-44, and 58 are provisionally rejected on the ground of anticipatory-type nonstatutory double patenting as being unpatentable over claims 1-25 and 41 of copending Application No. 18/683,846 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
Reference claim 1 is directed to a compound of Formula I:
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Where Q is selected from:
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Reference Formula I is a species of the instant Formula I when Q is Q1, Q2, or Q2’. The reference also claims a composition comprising one or more compounds of reference Formula I and a carrier (claim 25) and further claims a pharmaceutical composition comprising a compound of reference Formula I and an additional therapeutic agent. The reference therefore anticipates the instant claims.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 4, 8-14, and 58 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-25 of copending Application No. 18/683,842 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
The reference application is directed to compounds of reference Formula I (claim 1):
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Where Q is selected from:
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The compounds of reference Formula I species of the instant formula I when Q is Q1, Q2, or Q2’. Reference claim 25 is directed to a pharmaceutical composition of a compound of reference Formula I and a pharmaceutically acceptable carrier. The instant claims are therefore anticipated by the reference claims.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claim is allowed.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jonathan D. Mahlum whose telephone number is (703)756-4691. The examiner can normally be reached 8:30 AM - 5:00 PM ET, M-F.
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/J.D.M./Examiner, Art Unit 1625
/Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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