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, 2, 4 and 6-12 are pending in the instant invention. According to the Amendments to the Claims, filed June 23, 2025, claims 1, 2 and 6-12 were amended and claims 3 and 5 were cancelled.
Status of Priority
This invention is a Continuation (CON) of US Application No. 17/723,669, filed April 19, 2022 and now US 11,999,741, which is a Continuation (CON) of US Application No. 16/615,347, filed November 20, 2019 and now US 11,370,795, which is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/US2018/034566, filed May 25, 2018, which claims priority under 35 U.S.C. § 119(e) to US Provisional Application No. 62/511,367, filed May 26, 2017.
Restrictions / Election of Species
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The inventor’s or joint inventor’s provisional election of the following, with traverse, in the reply filed on June 23, 2025, is acknowledged: Group I - claims 1, 2, 4 and 6-10. Affirmation of this election must be made by the inventor or joint inventor in replying to this Office action.
Similarly, the inventor or joint inventor should further note that since supposed errors in the restriction requirement were not distinctly and specifically pointed out, the election has been treated as an election, without traverse. See MPEP § 818.03(a).
Likewise, the inventor or joint inventor should further note that the requirement is still deemed proper and is therefore made FINAL.
Moreover, the inventor or joint inventor should further note that claims 11 and 12 were withdrawn from further consideration, pursuant to 37 CFR 1.142(b), as being drawn to a nonelected or cancelled invention, there being no allowable generic or linking claim.
Thus, a first Office action and prosecution on the merits of claims 1, 2, 4 and 6-10 is contained within.
Specification Objection - Disclosure
The inventor or joint inventor is advised to format the specification according to 37 CFR 1.77(b) above and 37 CFR 1.77(c). Revisions should particularly include and/or address bold-type, underline, and/or upper case formatting. Appropriate correction may be required.
Specification Objection - Abstract
The inventor or joint inventor is reminded of the proper content of an abstract of the disclosure.
With regard particularly to chemical patents, for compounds or compositions, the general nature of the compound or composition should be given as well as the use thereof, e.g., The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics. Exemplification of a species could be illustrative of members of the class. For processes, the reactions, reagents and process conditions should be stated, generally illustrated by a single example, unless variations are necessary. See MPEP § 608.01(b), Section B.
The abstract of the disclosure is objected to because it fails to state the reactions, reagents and/or process conditions for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)-pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1). Correction is required. See MPEP § 608.01(b).
The examiner suggests incorporating the reactions, reagents and/or process conditions for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) into the abstract, to overcome this objection.
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 the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) of the following formula:
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P3.1
wherein the process comprises the following steps:
(a) reacting a compound of formula (S,S)-4:
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(S,S)-4
with a compound of formula 9:
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9
in the presence of potassium carbonate (K2CO3), followed by reacting with ammonium acetate (NH4OAc), to provide a compound of formula (S,S)-10:
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(S,S)-10;
(b) reacting the compound of formula (S,S)-10 above with hydrogen gas in the presence of a Pd/C catalyst, to provide a compound of formula (S,S)-11:
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(S,S)-11;
(c) reacting the compound of formula (S,S)-11 above with hydrochloric acid (HCl), to provide a compound of formula (S,S)-12:
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(S,S)-12; and
(d) reacting the compound of formula (S,S)-12 above with a compound of the following formula:
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,
in the presence of N,N-diisopropylethylamine (DIEA), to provide 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) above;
wherein the process is prepared with asymmetric enzymatic hydrolysis.
Appropriate correction is required. See MPEP § 2173.02.
Claim 2 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation:
The process of claim 1, wherein the process further comprises avoiding the use of a a chiral acid selected from the group consisting of (+)-2,3-dibenzoyl-D-tartaric acid, (+)-O,O-dibenzoyl-D-tartaric acid, dibenzoyl-L-tartaric acid, (-)-O,O’-di-p-toluoyl-L-tartaric acid, (+)-O,O’-di-p-toluoyl-D-tartaric acid, (+)-O,O’-di-pivaloyl-D-tartaric acid, (-)-O,O’-di-pivaloyl-D-tartaric acid, D-(-)-tartaric acid, L-(+)-tartaric acid, (4R)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide, L-(-)-malic acid, D-(+)-malic acid, (R)-(-)-mandelic acid, (S)-(+)-mandelic acid, (R)-(-)-a-methoxyphenylacetic acid, (S)-(+)-a-methoxyphenylacetic acid, (R)-(+)-a-methoxy-a- trifluoromethylphenylacetic acid, (S)-(-)-a-methoxy-a-(trifluoromethyl)phenylacetic acid, (R)-(-)-2-phenylpropionic acid, (S)-(+)-2-phenylpropionic acid, (R)-1,4-benzodioxane-2-carboxylic acid, (S)-1,4- benzodioxane-2-carboxylic acid, (R)-(-)-1,1’-binaphthyl-2,2’-diyl hydrogenphosphate, (S)-(+)-1,1’-binaphthyl-2,2’-diyl hydrogenphosphate, (1S)-(+)-3-bromocamphor-10-sulfonic acid hydrate, (1R)-(+)-camphanic acid, (1S)-(-)-camphanic acid, (1R,3S)-(+)-camphoric acid, (1S,3R)-(-)-camphoric acid, (1R)-(-)-10-camphorsulfonic acid, (1S)-(+)-10-camphorsulfonic acid, (R)-(-)-5-oxo-2-tetrahydrofurancarboxylic acid, (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid, and D-(-)-quinic acid.
Appropriate correction is required. See MPEP § 2173.02.
Claim 4 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 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 of claim 1, wherein the process further comprises preparing the compound of formula (S,S)-4 by the following steps:
(a1) reacting a compound of formula Rac-2:
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Rac-2
with human leukocyte elastase, to provide a mixture of a compound of formula (S,S)-2 and a by-product compound of formula (R,R)-acid:
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(S,S)-2 and
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(R,R)-acid;
(a2) extracting the by-product compound of formula (R,R)-acid above with a discarded aqueous phase, to provide a compound of formula (S,S)-2:
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(S,S)-2;
(a3) reacting the compound of formula (S,S)-2 above with di(tert-butyl) dicarbonate, followed by reacting with hydrogen gas in the presence of a Pd/C catalyst, to provide a compound of formula (S,S)-3:
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(S,S)-3; and
(a4) reacting the compound of formula (S,S)-3 above with a compound of the following formula:
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,
in the presence of triethylamine and tert-butylmagnesium chloride, to provide a compound of formula (S,S)-4:
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(S,S)-4.
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(a), 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 of claim 4, wherein the process further comprises preparing the compound of formula 9 by the following steps:
(a5) reacting a compound of formula 5:
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5
with diisobutylaluminum hydride (DIBAL-H), to provide a compound of formula 6:
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6;
(a6) reacting the compound of formula 6 above with a compound of the following formula:
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,
in the presence of aqueous ammonia, to provide a compound of formula 7:
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7;
(a7) reacting the compound of formula 7 above with sodium methoxide (NaOMe), to provide a compound of formula 8:
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8; and
(a8) reacting the compound of formula 8 above with N-bromosuccinimide (NBS), to provide a compound of formula 9:
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9.
Appropriate correction is required. See MPEP § 2173.02.
Claim 7 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 of claim 1, wherein the process further comprises synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) in a yield in the range of 50%-90%.
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 of claim 1, wherein the process further comprises synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) in a chiral purity in the range of 95.0%-99.9%.
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 of claim 1, wherein the process further comprises synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) in a purity in the range of 95.0%-99.9%.
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 of claim 1, wherein the process further comprises synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) where the total amount of all impurities is in the range of 0.1%-5%.
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, 2, 4 and 6-10 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 synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), as recited in claim 1, are the reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-10; (b) the synthesis of compound (S,S)-12; and (c) the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), respectively. The claim fails to explicitly recite any reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-10; (b) the synthesis of compound (S,S)-12; and (c) the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydro-pyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), respectively. Similarly, the specification fails to provide an adequate standard for ascertaining the requisite degree of any reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-10; (b) the synthesis of compound (S,S)-12; and (c) the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-yl-methyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), respectively. Consequently, one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), as recited in claim 1, since reagents for the essential manipulative steps which result: (a) the synthesis of compound (S,S)-10; (b) the synthesis of compound (S,S)-12; and (c) the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1), respectively, are omitted.
Moreover, 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)}.
The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claim 2 is 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, chiral acid, is a relative phrase which renders the claim indefinite. The phrase, chiral 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 37, uses open language, such as include, to define the phrase, chiral acid, as (+)-2,3-dibenzoyl-D-tartaric acid, dibenzoyl-L-tartaric acid, (-)-O,O’-di-p-toluoyl-L-tartaric acid, (+)-O,O’-di-p-toluoyl-D-tartaric acid, (+)-O,O’-di-pivaloyl-D-tartaric acid, (-)-O,O’-di-pivaloyl-D-tartaric acid, D-(-)-tartaric acid, L-(+)-tartaric acid, (4R)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide, L-(-)-malic acid, D-(+)-malic acid, (R)-(-)-mandelic acid, (S)-(+)-mandelic acid, (R)-(-)-a-methoxyphenylacetic acid, (S)-(+)-a-methoxy-phenylacetic acid, (R)-(+)-a-methoxy-a- trifluoromethylphenylacetic acid, (S)-(-)-a-methoxy-a-(trifluoromethyl)phenylacetic acid, (R)-(-)-2-phenylpropionic acid, (S)-(+)-2-phenylpropionic acid, (R)-1,4-benzodioxane-2-carboxylic acid, (S)-1,4- benzodioxane-2-carboxylic acid, (R)-(-)-1,1’-binaphthyl-2,2’-diyl hydrogenphosphate , (S)-(+)-1,1’-binaphthyl-2,2’-diyl hydrogen-phosphate, (1S)-(+)-3-bromocamphor-10-sulfonic acid hydrate, (1R)-(+)-camphanic acid, (1S)-(-)-camphanic acid, (1R,3S)-(+)-camphoric acid, (1S,3R)-(-)-camphoric acid, (1R)-(-)-10-camphorsulfonic acid, (1S)-(+)-10-camphorsulfonic acid, (R)-(-)-5-oxo-2-tetrahydrofurancarboxylic acid, (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid, and D-(-)-quinic acid; however, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) has been rendered indefinite by the use of the phrase, chiral acid.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claim 4 is further 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 preparing the compound of formula (S,S)-4, as recited in claim 4, are the reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-3; and (b) the synthesis of compound (S,S)-4, respectively. The claim fails to explicitly recite any reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-3; and (b) the synthesis of compound (S,S)-4, respectively. Similarly, the specification fails to provide an adequate standard for ascertaining the requisite degree of any reagents for manipulative steps which result in: (a) the synthesis of compound (S,S)-3; and (b) the synthesis of compound (S,S)-4, respectively. Consequently, one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the process for preparing the compound of formula (S,S)-4, as recited in claim 4, since reagents for the essential manipulative steps which result: (a) the synthesis of compound (S,S)-3; and (b) the synthesis of compound (S,S)-4, respectively, are omitted.
Moreover, 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)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claim 6 is further 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 preparing the compound of formula 9, as recited in claim 6, are the reagents for manipulative steps which result in: (a) the synthesis of compound 7; (b) the synthesis of compound 8; and (c) the synthesis of compound 9, respectively. The claim fails to explicitly recite any reagents for manipulative steps which result in: (a) the synthesis of compound 7; (b) the synthesis of compound 8; and (c) the synthesis of compound 9, respectively. Similarly, the specification fails to provide an adequate standard for ascertaining the requisite degree of any reagents for manipulative steps which result in: (a) the synthesis of compound 7; (b) the synthesis of compound 8; and (c) the synthesis of compound 9, respectively. Consequently, one of ordinary skill in the art would not be reasonably apprised of the metes and bounds of the process for preparing the compound of formula 9, as recited in claim 6, since reagents for the essential manipulative steps which result: (a) the synthesis of compound 7; (b) the synthesis of compound 8; and (c) the synthesis of compound 9, respectively, are omitted.
Moreover, 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)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this rejection.
Claim 7 is 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 term, about, is a relative term which renders the claim indefinite. The term, about, 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 fails to adequately define the term, about. Similarly, the meaning of a term cannot depend on the unrestrained, subjective opinion of the inventor or joint inventor practicing the invention. Likewise, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) has been rendered indefinite by the use of the term, about. {See Ortho-McNeil Pharm., Inc. v. Caraco Pharm. Labs., Ltd., 476 F.3d 1321, 1326, 81 USPQ2d 1427, 1432 (Fed. Cir.2007); W. L. Gore & Associates, Inc. v. Garlock, Inc., 721 F.2d 1540, 220 USPQ 303 (Fed. Cir. 1983); Amgen, Inc. v. Chugai Pharmaceutical Co., 927 F.2d 1200, 18 USPQ2d 1016 (Fed. Cir. 1991); and MPEP § 2173.05(b)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Next, the inventor or joint inventor should further note that a broad limitation together with a narrow limitation that falls within the broad limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c), MPEP § 2173.05(h), and/or Eli Lilly & Co. v. Teva Parenteral Meds., 845 F.3d 1357, 1371, 121 USPQ2d 1277, 1287 (Fed. Cir. 2017).
Then, the inventor or joint inventor should further note that claim 7 recites the broad limitation, at least about 50%, and the claim also recites at least about 60%, at least about 70%, at least about 80%, and at least about 90%, respectively, which are the narrower statements of the limitation.
Moreover, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in Ex parte Wu, 10 USPQ2d 2031, 2033 (Bd. Pat. App. & Inter. 1989), pertaining to where broad language is followed by such as and then narrow language. The Board stated that this can render a claim indefinite by raising a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and consequently, not required, or (b) a required feature of the claim.
Also, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in the decisions of Ex parte Steigewald, 131 USPQ 74 (Bd. App. 1961); Ex parte Hall, 83 USPQ 38 (Bd. App. 1948); and Ex parte Hasche, 86 USPQ 481 (Bd. App. 1949).
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Claim 8 is 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 term, about, is a relative term which renders the claim indefinite. The term, about, 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 fails to adequately define the term, about. Similarly, the meaning of a term cannot depend on the unrestrained, subjective opinion of the inventor or joint inventor practicing the invention. Likewise, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) has been rendered indefinite by the use of the term, about. {See Ortho-McNeil Pharm., Inc. v. Caraco Pharm. Labs., Ltd., 476 F.3d 1321, 1326, 81 USPQ2d 1427, 1432 (Fed. Cir.2007); W. L. Gore & Associates, Inc. v. Garlock, Inc., 721 F.2d 1540, 220 USPQ 303 (Fed. Cir. 1983); Amgen, Inc. v. Chugai Pharmaceutical Co., 927 F.2d 1200, 18 USPQ2d 1016 (Fed. Cir. 1991); and MPEP § 2173.05(b)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Next, the inventor or joint inventor should further note that a broad limitation together with a narrow limitation that falls within the broad limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c), MPEP § 2173.05(h), and/or Eli Lilly & Co. v. Teva Parenteral Meds., 845 F.3d 1357, 1371, 121 USPQ2d 1277, 1287 (Fed. Cir. 2017).
Then, the inventor or joint inventor should further note that claim 8 recites the broad limitation, above about 95.0%, and the claim also recites above about 96.0%, above about 97.0%, above about 98.0%, above about 99.0%, above about 99.5%, above about 99.8%, and above about 99.9%, respectively, which are the narrower statements of the limitation.
Moreover, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in Ex parte Wu, 10 USPQ2d 2031, 2033 (Bd. Pat. App. & Inter. 1989), pertaining to where broad language is followed by such as and then narrow language. The Board stated that this can render a claim indefinite by raising a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and consequently, not required, or (b) a required feature of the claim.
Also, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in the decisions of Ex parte Steigewald, 131 USPQ 74 (Bd. App. 1961); Ex parte Hall, 83 USPQ 38 (Bd. App. 1948); and Ex parte Hasche, 86 USPQ 481 (Bd. App. 1949).
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Claim 9 is 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 term, about, is a relative term which renders the claim indefinite. The term, about, 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 fails to adequately define the term, about. Similarly, the meaning of a term cannot depend on the unrestrained, subjective opinion of the inventor or joint inventor practicing the invention. Likewise, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) has been rendered indefinite by the use of the term, about. {See Ortho-McNeil Pharm., Inc. v. Caraco Pharm. Labs., Ltd., 476 F.3d 1321, 1326, 81 USPQ2d 1427, 1432 (Fed. Cir.2007); W. L. Gore & Associates, Inc. v. Garlock, Inc., 721 F.2d 1540, 220 USPQ 303 (Fed. Cir. 1983); Amgen, Inc. v. Chugai Pharmaceutical Co., 927 F.2d 1200, 18 USPQ2d 1016 (Fed. Cir. 1991); and MPEP § 2173.05(b)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Next, the inventor or joint inventor should further note that a broad limitation together with a narrow limitation that falls within the broad limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c), MPEP § 2173.05(h), and/or Eli Lilly & Co. v. Teva Parenteral Meds., 845 F.3d 1357, 1371, 121 USPQ2d 1277, 1287 (Fed. Cir. 2017).
Then, the inventor or joint inventor should further note that claim 8 recites the broad limitation, above about 95.0%, and the claim also recites above about 96.0%, above about 97.0%, above about 98.0%, above about 99.0%, above about 99.5%, above about 99.8%, and above about 99.9%, respectively, which are the narrower statements of the limitation.
Moreover, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in Ex parte Wu, 10 USPQ2d 2031, 2033 (Bd. Pat. App. & Inter. 1989), pertaining to where broad language is followed by such as and then narrow language. The Board stated that this can render a claim indefinite by raising a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and consequently, not required, or (b) a required feature of the claim.
Also, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in the decisions of Ex parte Steigewald, 131 USPQ 74 (Bd. App. 1961); Ex parte Hall, 83 USPQ 38 (Bd. App. 1948); and Ex parte Hasche, 86 USPQ 481 (Bd. App. 1949).
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Claim 10 is 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 term, about, is a relative term which renders the claim indefinite. The term, about, 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 fails to adequately define the term, about. Similarly, the meaning of a term cannot depend on the unrestrained, subjective opinion of the inventor or joint inventor practicing the invention. Likewise, neither the specification, nor the claim, explicitly limits the invention to any specifically disclosed or recited embodiments. Consequently, the process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) has been rendered indefinite by the use of the term, about. {See Ortho-McNeil Pharm., Inc. v. Caraco Pharm. Labs., Ltd., 476 F.3d 1321, 1326, 81 USPQ2d 1427, 1432 (Fed. Cir.2007); W. L. Gore & Associates, Inc. v. Garlock, Inc., 721 F.2d 1540, 220 USPQ 303 (Fed. Cir. 1983); Amgen, Inc. v. Chugai Pharmaceutical Co., 927 F.2d 1200, 18 USPQ2d 1016 (Fed. Cir. 1991); and MPEP § 2173.05(b)}.
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Next, the inventor or joint inventor should further note that a broad limitation together with a narrow limitation that falls within the broad limitation (in the same claim) is considered indefinite, since the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c), MPEP § 2173.05(h), and/or Eli Lilly & Co. v. Teva Parenteral Meds., 845 F.3d 1357, 1371, 121 USPQ2d 1277, 1287 (Fed. Cir. 2017).
Then, the inventor or joint inventor should further note that claim 10 recites the broad limitation, less than about 5%, and the claim also recites less than about 2%, less than about 1%, less than about 0.5%, less than about 0.2%, and less than about 0.1%, respectively, which are the narrower statements of the limitation.
Moreover, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in Ex parte Wu, 10 USPQ2d 2031, 2033 (Bd. Pat. App. & Inter. 1989), pertaining to where broad language is followed by such as and then narrow language. The Board stated that this can render a claim indefinite by raising a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and consequently, not required, or (b) a required feature of the claim.
Also, the inventor or joint inventor should further note the explanation given by the Board of Patent Appeals and Interferences in the decisions of Ex parte Steigewald, 131 USPQ 74 (Bd. App. 1961); Ex parte Hall, 83 USPQ 38 (Bd. App. 1948); and Ex parte Hasche, 86 USPQ 481 (Bd. App. 1949).
The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this section of the rejection.
Claim Rejections - Obviousness-type 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 obviousness-type double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined invention claim is not patentably distinct from the reference claims because the examined invention claim is either anticipated by, or would have been obvious over, the reference claims. {See 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); and In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969)}.
US Patent No. 11,999,741
Consequently, at least claims 1, 4 and 6-10 are rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over at least claims 1, 4 and 7-10 of US Patent No. 11,999,741. Although the conflicting claims are not identical, they are not patentably distinct from each other because claim 1 in US 11,999,741 recites a process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one of formula P3.1), which provides overlapping subject matter with respect to the instantly recited process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1).
The inventor or joint inventor should note that MPEP § 2141.02 states that [I]n determining the differences between the prior art and the claims, the question under 35 U.S.C. 103 is not whether the differences themselves would have been obvious, but whether the claimed invention as a whole would have been obvious. {See Stratoflex, Inc. v. Aeroquip Corp., 713 F.2d 1530, 218 USPQ 871 (Fed. Cir. 1983); Schenck v. Nortron Corp., 713 F.2d 782, 218 USPQ 698 (Fed. Cir. 1983); and In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976)}.
Similarly, the inventor or joint inventor should further note that MPEP § 2112.01-I states that [W]here the claimed and prior art products are… produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness is established. {See In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)}.
Likewise, in the instant case, the inventor or joint inventor should further note that the specification of US 11,999,741 discloses a method of synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) {column 27, line 15 – column 32, line 38}.
US Patent No. 11,370,795
At least claims 1, 4 and 6-10 are further rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over at least claims 1-4 and 6-9 of US Patent No. 11,370,795. Although the conflicting claims are not identical, they are not patentably distinct from each other because claim 1 in US 11,370,795 recites a process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]-pyrazin-8-one of formula P3.1), which provides overlapping subject matter with respect to the instantly recited process for the synthesis of 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)-pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1).
The inventor or joint inventor should note that MPEP § 2141.02 states that [I]n determining the differences between the prior art and the claims, the question under 35 U.S.C. 103 is not whether the differences themselves would have been obvious, but whether the claimed invention as a whole would have been obvious. {See Stratoflex, Inc. v. Aeroquip Corp., 713 F.2d 1530, 218 USPQ 871 (Fed. Cir. 1983); Schenck v. Nortron Corp., 713 F.2d 782, 218 USPQ 698 (Fed. Cir. 1983); and In re Hirao, 535 F.2d 67, 190 USPQ 15 (CCPA 1976)}.
Similarly, the inventor or joint inventor should further note that MPEP § 2112.01-I states that [W]here the claimed and prior art products are… produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness is established. {See In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)}.
Likewise, in the instant case, the inventor or joint inventor should further note that the specification of US 11,370,795 discloses a method of synthesizing 6-((3S,4S)-4-methyl-1-(pyrimidin-2-ylmethyl)pyrrolidin-3-yl)-3-(tetrahydropyran-4-yl-7H-imidazo[1,5-a]pyrazin-8-one (Compound P3.1) {column 26, line 37 – column 45, line 37}.
Next, the inventor or joint inventor should further note that a timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 37 CFR 1.321(d) may be used to overcome an actual or provisional rejection based on a nonstatutory double patenting ground, provided the conflicting invention or patent either is shown to be commonly owned with this invention, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement.
Then, the inventor or joint inventor should further note that the USPTO internet Web site contains terminal disclaimer forms which may be used, and the inventor or joint inventor is encouraged to visit http://www.uspto.gov/forms/, where (i) the filing date of the invention will determine what form should be used, and (ii) a web-based eTerminal Disclaimer may be filled out completely online using web-screens, respectively.
Moreover, the inventor or joint inventor should further note that an eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission.
Finally, for more information about eTerminal Disclaimers, the inventor or joint inventor should refer to http://www.uspto.gov/patents/process/file/efs/guidance/eTD-info-I.jsp.
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