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 45-51 are pending in the instant invention. According to the Amendments to the Claims, filed January 29, 2026, claim 45 was amended and claims 1-44 were cancelled.
Status of Priority Objection - Priority Date
This invention is a Continuation (CON) of abandoned US Application No. 17/324,674, filed May 19, 2021, which is a Continuation (CON) of US Application No. 16/708,340, filed December 9, 2019 and now US 11,040,980, which is a Continuation (CON) of US Application No. 15/978,041, filed May 11, 2018 and now US 10,533,013, which is a Continuation (CON) of US Application No. 14/997,330, filed January 15, 2016 and now US 9,994,576, which is a Continuation (CON) of US Application No. 14/374,788, filed July 25, 2014 and now US 9,266,896, which is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/US2013/058614, filed September 6, 2013, which claims priority under 35 U.S.C. § 119(e) to US Provisional Application No. 61/782,605, filed March 14, 2013.
Similarly, the inventor or joint inventor should further note that this invention’s claim to priority under 35 U.S.C. § 119(e) to US Provisional Application Nos.: a) 61/728,693, filed November 20, 2012; and b) 61/699,038, filed September 10, 2012, respectively, was objected to in the Non-Final Rejection, mailed on October 4, 2024. Consequently, the effective filing date, for examination and prosecution on the merits, is that of US Provisional Application No. 61/782,605, filed March 14, 2013.
Status of Restrictions / Election of Species
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The forthcoming fourth Office action and prosecution on the merits includes claims 45-51, drawn to a process for preparing a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA), shown to the right.
Likewise, the inventor or joint inventor should further note that the requirement was made FINAL in the Non-Final Rejection, mailed on October 4, 2024.
Next, 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 either the Non-Final Rejection, mailed on October 4, 2024, the Final Rejection, mailed on January 30, 2025, or the Non-Final Rejection, mailed on October 2, 2025.
Moreover, 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 January 29, 2026.
Thus, a fourth Office action and prosecution on the merits of claims 45-51 is contained within.
Status of Claim Rejections - Obviousness-type Double Patenting
The inventor’s or joint inventor’s arguments, on pages 6-8 of the Remarks, filed January 29, 2026, with respect to claims 45-51, have been fully considered, but are not persuasive. Consequently, the rejection of claims 45-51, made in the Final Rejection, mailed on January 30, 2025, is hereby maintained for the reasons of record.
The inventor or joint inventor primarily argues that the instantly recited claims are directed to a process for preparing a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA) and not a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA) alone. Similarly, the inventor or joint inventor further argues that (1) the instantly recited process for preparing a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA) requires either step (i) or step (ii), and that (2) the instantly recited claims and the reference claims of US 8,940,744, US 9,266,895, and US 9,994,576 are patentably distinct, respectively.
In response to the inventor’s or joint inventor’s arguments that (1) the instantly recited process for preparing a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA) requires either step (i) or step (ii), and that (2) the instantly recited claims and the reference claims of US 8,940,744, US 9,266,895, and US 9,994,576 are patentably distinct, respectively, the Examiner respectfully disagrees since 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)}.
Moreover, 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)}.
As a result of the Amendments to the Claims, filed January 29, 2026, and to clarify the record, the original rejection, made in the Non-Final Rejection, mailed on October 2, 2025, is included below, in the section entitled New Claim Rejections - Obviousness-type Double Patenting.
New Claim Objections
Claim 45 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 (IA):
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(IA)
or a pharmaceutically acceptable salt or stereoisomer thereof,
wherein:
Z is
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or
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;
Rc is:
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,
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,
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, or
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;
R4 is H, alkyl, haloalkyl, alkyl-O(alkyl), C(O)R, C(O)O(alkyl), S(O)2alkyl, or oxetan-3-yl;
R is alkyl;
Ra is H, alkyl, haloalkyl, alkyl-O(alkyl), or oxetan-3-yl;
Rb is H, alkyl, or cycloalkyl; and
Rd is:
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,
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,
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, or
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;
with the provisos that:
(1) the piperazinylene of Rc is optionally substituted with one or two independently selected alkyl substituents; and
(2) Rd is optionally substituted with one or two substituents independently selected from the group consisting of halo, alkyl, and haloalkyl;
wherein the process comprises the following steps:
(i) reacting a compound of formula (1):
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(1)
wherein:
Z is
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or
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;
with a compound of the following formula:
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wherein:
Rc is:
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,
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,
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,
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, or
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;
R4 is H, alkyl, haloalkyl, alkyl-O(alkyl), C(O)R, C(O)O(alkyl), S(O)2alkyl, or oxetan-3-yl;
R is alkyl;
Ra is H, alkyl, haloalkyl, alkyl-O(alkyl), or oxetan-3-yl;
Rb is H, alkyl, or cycloalkyl; and
Rd is:
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,
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,
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,
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, or
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;
with the provisos that:
(1) the piperazinylene of Rc is optionally substituted with one or two independently selected alkyl substituents; and
(2) Rd is optionally substituted with one or two substituents independently selected from the group consisting of halo, alkyl, and haloalkyl;
to provide the compound of Formula (IA) above; or
(ii) reacting a compound of formula (2):
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(2)
wherein:
Z is
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or
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;
with a compound of the following formula:
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or
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,
wherein:
X is halogen;
Rc is:
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,
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,
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, or
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;
R4 is H, alkyl, haloalkyl, alkyl-O(alkyl), C(O)R, C(O)O(alkyl), S(O)2alkyl, or oxetan-3-yl;
R is alkyl;
Ra is H, alkyl, haloalkyl, alkyl-O(alkyl), or oxetan-3-yl;
Rb is H, alkyl, or cycloalkyl; and
Rd is:
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,
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, or
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;
with the provisos that:
(1) the piperazinylene of Rc is optionally substituted with one or two independently selected alkyl substituents; and
(2) Rd is optionally substituted with one or two substituents independently selected from the group consisting of halo, alkyl, and haloalkyl;
to provide the compound of Formula (IA) above; and
(iii) optionally reacting the compound of Formula (IA) provided in step (i) or step (ii) above with a pharmaceutically acceptable acid, to provide a pharmaceutically acceptable acid addition salt of the compound of Formula (IA); or
(iv) optionally reacting the compound of Formula (IA) provided in step (i) or step (ii) above, or the pharmaceutically acceptable acid addition salt of the compound of Formula (IA) provided in step (iii) above, with a base, to provide a free base of the compound of Formula (IA); or
(v) optionally separating the compound of Formula (IA) provided in step (i) or step (ii) above, the pharmaceutically acceptable acid addition salt of the compound of Formula (IA) provided in step (iii) above, or the free base of the compound of Formula (IA) provided in step (iv) above into one or more stereoisomers of the compound of Formula (IA); or
(vi) optionally separating the compound of Formula (IA) provided in step (i) or step (ii) above, the pharmaceutically acceptable acid addition salt of the compound of Formula (IA) provided in step (iii) above, the free base of the compound of Formula (IA) provided in step (iv) above, or the one or more stereoisomers of the compound of Formula (IA) provided in step (v) above into an (E) or (Z) diastereomer of the compound of Formula (IA).
Appropriate correction is required. See MPEP § 2173.02.
Claim 46 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein:
Z is
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or
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; and
Rc is
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 47 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein:
Z is
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or
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; and
Rc is
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 48 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein:
Z is
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or
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; and
Rc is
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 49 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein:
Z is
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or
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; and
Rc is
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 50 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein:
Z is
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or
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; and
Rc is
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.
Appropriate correction is required. See MPEP § 2173.02.
Claim 51 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation:
The process of claim 45, wherein Rc is:
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,
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,
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,
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, or
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.
Appropriate correction is required. See MPEP § 2173.02.
New 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. 8,940,744
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Consequently, at least claims 45-48, 50 and 51 are rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over at least claims 1-5, 10-12 and 30 of US Patent No. 8,940,744. Although the conflicting claims are not identical, they are not patentably distinct from each other because at least claim 30 in US 8,940,744 recites a process of preparing (R)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile of the Formula (IA), shown to the right above, wherein the process comprises: (a) reacting (R)-3-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]-pyrimidin-1-yl)piperidin-1-yl)-3-oxopropanenitrile of the formula (1), wherein Z is shown to the left above, with 2-methyl-2-(4-methylpiperazin-1-yl)propanal of the formula, RcC(O)H, wherein Rc is shown to the right, where R4 = -CH3, which provides overlapping subject matter with respect to the instantly recited process for preparing (R)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-piperidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile of the Formula (IA), shown to the right above, wherein the process comprises: (a) reacting (R)-3-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-3-oxopropanenitrile of the formula (1), wherein Z is shown to the left above, with 2-methyl-2-(4-methylpiperazin-1-yl)propanal of the formula, RcC(O)H, wherein Rc is shown to the right above, where R4 = -CH3.
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)}.
Moreover, in the instant case, the inventor or joint inventor should further note that the specification of US 8,940,744 discloses a process of preparing (R)-2-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carbonyl)-4-methyl-4-(4-methylpiperazin-1-yl)pent-2-enenitrile, wherein the process comprises: (a) reacting (R)-3-(3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-3-oxopropanenitrile with 2-methyl-2-(4-methylpiperazin-1-yl)propanal (Example 4, column 48, line 18 - column 49, line 26).
US Patent No. 9,266,895
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Claims 45-51 are rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over at least claims 1-8 of US Patent No. 9,266,895. Although the conflicting claims are not identical, they are not patentably distinct from each other because claim 1 in US 9,266,895 recites a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA), where Z is shown to the left, and Rc is shown to the right, wherein R4 = -alkyl, respectively, which are produced by the instantly recited process for preparing a substituted pyrazolo[3,4-d]pyrimidine of the Formula (IA), wherein the process comprises: (a) reacting a substituted pyrazolo[3,4-d]pyrimidine of the formula (1), wherein Z is shown to the left above, with an aldehyde of the formula, RcC(O)H, wherein Rc is shown to the right above, where R4 = -alkyl.
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)}.
Moreover, in the instant case, the inventor or joint inventor should further note that the specification of US 9,266,895 discloses a process of preparing a compound of formula (IA), wherein the process comprises the following steps: (i) reacting a compound of formula (I) with an aldehyde of formula RcCHO, to provide the compound of Formula (IA) {column 21, line 4 - column 24, line 28}.
US Patent No. 9,994,576
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Claims 45-51 are further rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over at least claims 1-3, 7-9, 15 and 19 of US Patent No. 9,994,576. Although the conflicting claims are not identical, they are not patentably distinct from each other because claim 1 in US 9,994,576 recites a substituted pyrazolo[3,4-d]pyrimidine of the Formula (II), where R1 = -H; R2 = -H; R3 = -halo; Z is shown to the left; and Rc is shown to the right, wherein R5 = -alkyl, respectively, which are produced by the instantly recited process for preparing a substituted pyrazolo[3,4-d]-pyrimidine of the Formula (IA), wherein the process comprises: (a) reacting a substituted pyrazolo[3,4-d]pyrimidine of the formula (1), wherein Z is shown to the left above, with an aldehyde of the formula, RcC(O)H, wherein Rc is shown to the left, where R4 = -alkyl.
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 9,994,576 discloses a process of preparing a compound of formula (IA), wherein the process comprises the following steps: (i) reacting a compound of formula (I) with an aldehyde of formula RcCHO, to provide the compound of Formula (IA) {column 21, line 4 - column 24, line 42}.
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
The inventor’s or joint inventor’s arguments and/or the Amendments to the Claims, filed January 29, 2026, necessitated the new ground 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