DETAILED ACTION
Notice of Pre-AIA or AIA Status
The inventor or joint inventor should note that the instant invention, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 1-19 are pending in the instant invention. According to the Amendments to the Claims, filed June 15, 2026, claims 1-5 and 7-9 were amended and claims 12-19 were added.
Status of Priority
This invention is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/EP2022/051250, filed January 20, 2022, which claims priority under 35 U.S.C. § 119(a-d) to EP 21152830.2, filed January 21, 2021.
Status of Restrictions / Election of Species
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The forthcoming second Office action and prosecution on the merits includes (1) claims 1-11 and new claims 13-19, drawn to a process comprising the preparation of a solid form of a compound of Formula (4), shown to the left; and (2) claim 1 and new claim 12, drawn to a process for the preparation of a Compound of Formula (1), shown to the right above, respectively.
The inventor or joint inventor should note that the amended invention of claims 1-11 and new claims 13-19, directed to a process comprising the preparation of a solid form of a compound of Formula (4), shown to the left above, is independent or distinct from the originally presented invention of claims 1-11, filed July 18, 2023, and directed to a process for the preparation of Compound of Formula (1), shown to the right above, since (1) the inventions, as recited, are either incapable of use together or may have a materially different design, mode of operation, function, or effect; (2) the inventions do not overlap in scope, i.e., are mutually exclusive; and (3) the inventions, as recited, are not obvious variants. See MPEP § 806.05(j). In the instant case, the inventions, as recited, are either incapable of use together or may have a materially different design, mode of operation, function, or effect. For example, neither of the processes, as recited in claims 1 and 12, respectively, contains identical designs, steps for implementation, or modes of operation. Consequently, as recited, they are mutually exclusive and require materially different designs, modes of operation, and/or effects, respectively. Likewise, the inventions, as recited, do not encompass overlapping subject matter and there is nothing of record to show them to be obvious variants.
Next, the inventor or joint inventor should further note that since the inventor or joint inventor has received an action on the merits for the originally presented invention of claim 1 and new claim 12, filed July 18, 2023, directed to a process for the preparation of Compound of Formula (1), shown to the right above, this invention has been constructively elected by original presentation for prosecution on the merits.
Accordingly, the inventor or joint inventor should further note that the Amendments to the Claims, filed June 15, 2026, amending claims 1-11 and presenting new claims 13-19, directed to the invention of a process comprising the preparation of a solid form of a compound of Formula (4), shown to the left above, is non-responsive and has not been entered. See MPEP § 821.03.
Then, the inventor or joint inventor should further note that this invention contains claims 1-11 and 13-19, drawn to a nonelected invention, in the reply filed on June 15, 2026. A complete reply to the Final Rejection may include cancellation of nonelected claims or other appropriate action (37 CFR 1.144). See MPEP § 821.02.
Moreover, the inventor or joint inventor should further note that the sections of U.S.C. Title 35 that formed the basis of prior rejections formulated, as well as any references supporting said rejections, that are not included with this Office action, may be found in the Non-Final Rejection, mailed on March 13, 2026.
Also, the inventor or joint inventor should further note that any rejections and/or objections of record not explicitly addressed herein below, are hereby withdrawn, in light of the inventor’s or joint inventor’s arguments and/or the Amendments to the Claims, filed June 15, 2026.
Thus, a second Office action and prosecution on the merits of claims 1 and 12 is contained within.
New Claim Objections
Claim 1 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a) and/or 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation:
A process for preparing a compound of Formula (1):
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(1)
wherein the process comprises the following steps:
(a) reacting a compound of Formula (2):
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(2)
with a compound of Formula (3):
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(3)
in the presence of a Lewis acid selected from the group consisting of BF3∙Et2O, AlCl3, and FeCl3 and a solvent selected from the group consisting of dichloromethane, tetrahydrofuran, and 2-methyltetrahydrofuran, or a mixture thereof, to provide a compound of Formula (4):
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(4);
(b) contacting the compound of Formula (4) provided in step (a) above with toluene, to provide a mixture comprising crystal Form 1 of the compound of Formula (4) and toluene;
(c) isolating crystal Form 1 of the compound of Formula (4) from the mixture comprising crystal Form 1 of the compound of Formula (4) and toluene provided in step (b) above, wherein crystal Form 1 of the compound of Formula (4) is characterized by an X-ray powder diffraction (XRPD) pattern comprising characteristic peaks at diffraction angles (º2q) selected from the group consisting of 14.1º ± 0.2º, 17.2º ± 0.2º, 20.5º ± 0.2º, and 22.3º ± 0.2º;
(d) reacting crystal Form 1 of the compound of Formula (4) provided in step (c) above with gaseous ammonia or a solution of ammonia, optionally in the presence of a solvent selected from the group consisting of dioxane and toluene, to provide a mixture comprising the crystal Form 1 of the compound of Formula (4) and ammonia;
(e) reacting the mixture comprising crystal Form 1 of the compound of Formula (4) and ammonia provided in step (d) above with hydrazine of the following formula:
H2N-NH2,
or a salt or hydrate thereof,
optionally in the presence of a solvent, to provide a compound of Formula (5):
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(5);
(f) reacting the compound of Formula (5) provided in step (e) above with a compound of Formula (6):
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(6)
in the presence of triphenylphosphine, an azodicarboxylate compound selected from the group consisting of diisopropyl azodicarboxylate and dibenzyl azodicarboxylate, and a solvent selected from the group consisting of dimethyl formamide, tetrahydrofuran, 2-methyltetrahydrofuran, and toluene, or a combination thereof, to provide a compound of Formula (7):
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(7);
(g) deprotecting the compound of Formula (7) provided in step (d) above with (i) an acid selected from the group consisting of trifluoroacetic acid and hydrochloric acid or (2) hydrogen in the presence of a catalyst, to provide a compound of Formula (8):
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(8)
or a salt thereof; and
(h) reacting the compound of Formula (8) provided in step (e) above, or a salt thereof, with acryloyl chloride of the following formula:
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,
in the presence of 2-methyltetrahydrofuran and a base selected from the group consisting of diethylamine, diisopropylethylamine, triethylamine, and 1,8-diazabicyclo[5.4.0]undec-7-en (DBU), to provide the compound of Formula (1):
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(1).
Appropriate correction is required. See MPEP § 2173.02.
New Claim Rejections - 35 U.S.C. § 112(b)
The following is a quotation of the second paragraph of 35 U.S.C. § 112:
(b) CONCLUSION. The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or joint inventor regards as the invention.
Claims 1 and 12 are rejected under 35 U.S.C. § 112(b) as being incomplete for omitting an essential procedural step, such omission resulting in an indefinite process. See MPEP § 2172.01.
The inventor or joint inventor should note that the omitted essential procedural steps in the process for the preparation of a compound of Formula (1), or a salt thereof, as recited in claims 1 and 12, respectively, are the manipulative steps which result in the preparation of a compound of Formula (1), or a salt thereof. The claim fails to explicitly recite manipulative steps which result in the preparation of a compound of Formula (1), or a salt thereof. Similarly, the specification fails to provide an adequate standard for ascertaining the requisite degree of any manipulative steps which result in the preparation of a compound of Formula (1), or a salt thereof. Consequently, one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the process for the preparation of a compound of Formula (1), or a salt thereof, as recited in claim 1, since the essential manipulative steps which result in the preparation of a compound of Formula (1), or a salt thereof, are omitted.
Likewise, the inventor or joint inventor should further note that [A] claim which omits matter disclosed to be essential to the invention, as described in the specification or in other statements of record, may also be rejected under 35 U.S.C. § 112(a) as not enabling. {See In re Mayhew, 527 F.2d 1229, 188 USPQ 356 (CCPA 1976); and MPEP § 2164.08(c)}.
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled New Claim Objections, to overcome this rejection.
Claims 1 and 12 are further rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention.
The inventor or joint inventor should note that claim 1 recites the limitation, …wherein said solvent comprises dichloromethane, in step (a) of the claim.
Similarly, the inventor or joint inventor should further note that MPEP § 2111.03 states the transitional term, comprising, which is synonymous with including, containing, or characterized by, is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. {See Mars Inc. v. H.J. Heinz Co., 377 F.3d 1369, 1376, 71 USPQ2d 1837, 1843 (Fed. Cir. 2004); Invitrogen Corp. v. Biocrest Mfg., L.P., 327 F.3d 1364, 1368, 66 USPQ2d 1631, 1634 (Fed. Cir. 2003); Genentech, Inc. v. Chiron Corp., 112 F.3d 495, 501, 42 USPQ2d 1608, 1613 (Fed. Cir. 1997); Moleculon Research Corp. v. CBS, Inc., 793 F.2d 1261, 229 USPQ 805 (Fed. Cir. 1986); In re Baxter, 656 F.2d 679, 686, 210 USPQ 795, 803 (CCPA 1981); Ex parte Davis, 80 USPQ 448, 450 (Bd. App. 1948); and Gillette Co. v. Energizer Holdings Inc., 405 F.3d 1367, 1371-73, 74 USPQ2d 1586, 1589-91 (Fed. Cir. 2005)}.
Likewise, the inventor or joint inventor should further note that [A] Markush group must be definite and complete as to its membership. A Markush group is indefinite, and claims are rejected, where the Markush group is defined as comprising. {See Ex parte Morrell, 100 USPQ 317 (Bd. Pat. App. & Int. 1953)}.
Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled New Claim Objections, to overcome this rejection.
Allowable Subject Matter
No claims are allowed.
Conclusion
The inventor’s or joint inventor’s arguments and/or the Amendments to the Claims, filed June 15, 2026, necessitated the new grounds of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). The inventor or joint inventor 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 extension fee 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to DOUGLAS M. WILLIS, whose telephone number is 571-270-5757. The Examiner may normally be reached on Monday thru Thursday from 8:00-6:00 EST. The Examiner is also available on alternate Fridays.
If attempts to reach the Examiner by telephone are unsuccessful, the Examiner’s supervisor, Mr. Jeffrey Murray, may be reached on 571-272-9023. The fax phone number for the organization where this invention or proceeding is assigned is 571-273-8300.
Information regarding the status of an invention may be obtained from Patent Center. For more information about Patent Center, see https://www.uspto.gov/patents/apply/patent-center. Should you have questions on access to Patent Center, contact the Patent Electronic Business Center (PEBC) at 866-217-9197 (toll-free) or ebc@uspto.gov.
/DOUGLAS M WILLIS/
Primary Examiner, Art Unit 1624
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