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 1-11 are pending in the instant invention. According to the Amendments to the Claims, filed July 18, 2023, claims 1-4, 7 and 9-11 were amended.
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.
Restrictions / Election of Species
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The forthcoming first Office action and prosecution on the merits includes claims 1-11, drawn to a process for the preparation of a compound of Formula (1), shown to the right.
Thus, a first Office action and prosecution on the merits of claims 1-11 is contained within.
Specification Objection - Disclosure
The inventor or joint inventor is advised to format the specification according to 37 CFR 1.77(c). Revisions should particularly address bold-type, underline, and/or upper case formatting. Appropriate correction may be required.
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.
Claim 2 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (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) further comprises evaporating the mixture comprising the compound of Formula (4) and toluene to an amount in the range of from 45% to 55% of the original volume.
Appropriate correction is required. See MPEP § 2173.02.
Claim 3 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (c), crystal Form I of the compound of Formula (4) is further characterized by an X-ray powder diffraction (XRPD) pattern comprising at least one additional characteristic peak at a diffraction angle (º2q) selected from the group consisting of 13.5º ± 0.2º, 15.7º ± 0.2º, and 21.3º ± 0.2º.
Appropriate correction is required. See MPEP § 2173.02.
Claim 4 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (a), reacting the compound of Formula (2) with a compound of Formula (3) is performed in the presence of AlCl3.
Appropriate correction is required. See MPEP § 2173.02.
Claim 5 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (d), the process further comprises reacting crystal Form 1 of the compound of Formula (4) provided in step (c) with an aqueous solution of ammonia.
Appropriate correction is required. See MPEP § 2173.02.
Claim 6 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (e), the process further comprises reacting the mixture comprising crystal Form 1 of the compound of Formula (4) and ammonia provided in step (d) with hydrazine hydrate.
Appropriate correction is required. See MPEP § 2173.02.
Claim 8 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein in step (f), the process further comprises reacting the compound of Formula (5) provided in step (e) with a compound of Formula (6) in the presence of 2-methyltetrahydrofuran.
Appropriate correction is required. See MPEP § 2173.02.
Claim 9 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 1, wherein providing the compound of formula (1) in step (h) further comprises the following steps:
(i) filtering the reaction mixture comprising 2-methyltetrahydrofuran;
(ii) adding hydrochloric acid to the filtrate; and
(iii) passing the filtrate over activated carbon using carbofiltration.
Appropriate correction is required. See MPEP § 2173.02.
Claim 10 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation:
The process according to claim 9, wherein in step (ii), the process further comprises adding hydrochloric acid to the filtrate such that the weight ratio of the hydrochloric acid to the compound of Formula (8) in the filtrate is in the range of from 1:63 to 1:69.
Appropriate correction is required. See MPEP § 2173.02.
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 1-11 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 claim 1, 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.
Similarly, 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 Claim Objections, to overcome this rejection.
Claims 1-11 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 the phrase, Lewis acid, in claim 1, with respect to step (a), is a relative phrase which renders the claim indefinite. The phrase, Lewis acid, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 4, uses open language, such as for example, to define the phrase, Lewis acid, as AlCl3, etc.; however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the preparation of a compound of Formula (1) has been rendered indefinite by the use of the phrase, Lewis acid, with respect to step (a).
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 Claim Objections, to overcome this rejection.
Claims 7-11 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 the phrase, amine protecting group, in claim 7, with respect to step (i), is a relative phrase which renders the claim indefinite. The phrase, amine protecting group, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 10, uses open language, such as preferably, to define the phrase, amine protecting group, as Boc (tert-butoxycarbonyl); however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the preparation of a compound of Formula (1) has been rendered indefinite by the use of the phrase, amine protecting group, with respect to step (i).
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 Claim Objections, to overcome this rejection.
Claims 7 and 9-11 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 the phrase, suitable solvent, in claim 7, with respect to step (i), is a relative phrase which renders the claim indefinite. The phrase, suitable solvent, is not defined by the claim, the specification does not provide an adequate standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the invention. The specification, on page 11, uses open language, such as such as, to define the phrase, suitable solvent, as 2-methyltetrahydrofuran, etc.; however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the preparation of a compound of Formula (1) has been rendered indefinite by the use of the phrase, suitable solvent, with respect to step (i).
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 Claim Objections, to overcome this rejection.
Allowable Subject Matter
No claims are allowed.
Conclusion
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