Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
This application is a continuation of U.S. Application No. 17/598,389 and is a U.S. National Phase application under 35 U.S.C. § 371 of PCT Application No. PCT/ US2020/026799, filed April 06, 2020 which claims priority under 35 U.S.C. § 119(e) from U.S. Provisional Application Serial No. 62/832125, filed on April 10, 2019.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on Aug. 20, 2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Status
Claims 1-13 are currently active and subject to examination.
Claim Objections
Claims 3 and 8 is objected to because of the following informalities: In claim 3, the word methyl appears as:
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. In claim 8, there is a comma missing after hydrogen.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
“A person shall be entitled to a patent unless -
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.”
Claims 1, 4 and 6-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by “N-(1H-indazol-7-yl)-1H-pyrazole-4-sulfonamide” (PubChem CID: 60911247, Published October 19, 2012; herein referred to as “PubChem A”) (of record IDS dated 08/20/2025, NPL cite no. 1).
Claim 1 is directed towards a compound of formula I:.
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PubChem A teaches the following compound of formula I of claim 1:
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(PubChem A, page 2). As in formula I of claim 1, X is N and R1-5 and 7 are hydrogen. Therefore, claim 1 is anticipated.
Claim 4 is directed towards the compound of claim 1 wherein R1 is hydrogen. Claim 6 is directed towards the compound of claim 1 wherein R3 is hydrogen. Claim 7 is directed towards the compound of claim 1 wherein R4 is hydrogen. Claim 8 is directed towards the compound of claim 1 wherein R5 is hydrogen. In the PubChem A compound, R1-5 are hydrogen. Therefore, claims 4 and 6-8 are anticipated.
Claims 1, 4 and 6-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by “N-(1H-indazol-7-yl)-1-methylpyrazole-4-sulfonamide” (PubChem CID: 47309930, Published November 26, 2010; of record IDS dated 08/20/2025, herein referred to as “PubChem B”) (of record, IDS dated 08/20/2025, NPL cite no 4).
Claim 1 is directed towards a compound of formula I:
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. PubChem B teaches the following compound of formula I of claim 1:
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(PubChem B, page 2). As in formula I of claim 1, X is N, R1-3, 5, and 7 are hydrogen, and R4 is methyl (C1-alkyl). Therefore, claim 1 is anticipated.
Claim 4 is directed towards the compound of claim 1 wherein R1 is hydrogen. Claim 6 is directed towards the compound of claim 1 wherein R3 is hydrogen. Claim 7 is directed towards the compound of claim 1 wherein R4 is methyl. Claim 8 is directed towards the compound of claim 1 wherein R5 is hydrogen. In the PubChem B compound, R1-3 and 5 are hydrogen and R4 is methyl. Therefore, claims 4-8 are anticipated.
Claims 1, 4 and 6-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by “1-tert-butyl-N-(1H-indazol-7-yl)-3,5-dimethylpyrazole-4-sulfonamide” (PubChem CID: 53609448, Published December 3, 2011; herein referred to as “PubChem C”) (of record, IDS dated 08/20/2025, NPL cite no. 3).
Claim 1 is directed towards a compound of formula I:
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. PubChem C teaches the following compound of formula I of claim 1:
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(PubChem C, page 2). ). As in formula I of claim 1, X is N, R1-2 and 7 are hydrogen, R3 and R5 are methyl (C1-alkyl), and R4 is tert-butyl (C4-alkyl). Therefore, claim 1 is anticipated.
Claim 4 is directed towards the compound of claim 1 wherein R1 is hydrogen. Claim 6 is directed towards the compound of claim 1 wherein R3 is methyl. Claim 7 is directed towards the compound of claim 1 wherein R4 is tert-butyl. Claim 8 is directed towards the compound of claim 1 wherein R5 is methyl. In the PubChem C compound, R1-2 are hydrogen, R3 and R5 are methyl, and R4 is tert-butyl (C4-alkyl). Therefore, claims 4 and 6-8 are anticipated.
Claims 1, 4 and 6-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by “N-(1H-indol-7-yl)-3,5-dimethyl-1H-pyrazole-4-sulfonamide” (PubChem CID: 110867609, Published January 18, 2016; herein referred to as “PubChem D”) (of record, IDS dated 08/20/2025, NPL cite no 5).
Claim 1 is directed towards a compound of formula I:
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. PubChem D teaches the following compound of formula I of claim 1:
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(PubChem D, page 2). ). As in formula I of claim 1, X is CR6, R1-2, 4, and 6-7 are hydrogen, and R3 and R5 are methyl (C1-alkyl). Therefore, claim 1 is anticipated.
Claim 4 is directed towards the compound of claim 1 wherein R1 is hydrogen. Claim 6 is directed towards the compound of claim 1 wherein R3 is methyl. Claim 7 is directed towards the compound of claim 1 wherein R4 is hydrogen. Claim 8 is directed towards the compound of claim 1 wherein R5 is methyl. In the PubChem D compound, R1-2 are hydrogen, R3 and R5 are methyl, and R4 is hydrogen. Therefore, claims 4 and 6-8 are anticipated.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
“A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.”
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshino et al. (US5767283A, Published June 16, 1998) (of record, IDS dated 08/20/2025, U.S. patent cite no. 3).
Claim 1 is directed towards a compound of formula I:
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(indole or indazole-pyrazole-sulfonamides).
For example, claim 1 reads on a compound having the following structure:
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(drawn by examiner).
Yoshino teaches the following compound is an antitumor agent with activity against colon cancer cells (Yoshino, Specification, column 11, Table 1-1):
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(Yoshino, Specification, column 38, lines 45-55). One of ordinary skill in the art would expect that the componds claimed by the Applicant would have the same properties as the compounds disclosed by Yoshino because Yoshino teaches compounds which differ from a species falling within the genus by only a single nitrogen atom (imidazole instead of pyrazole) and a genus which includes pyrazole.
Yoshino teaches a generic formula wherein imidazole in the above compound can be pyrazole:
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(Yoshino, Specification, column 1);
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(Yoshino, Specificaiton, column 2; see line 28 for pyrazole). As stated in the MPEP, such compounds are so similar that an ordinary artisan would expect similar properties:
Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979) (Claimed and prior art compounds were both directed to heterocyclic carbamoyloximino compounds having pesticidal activity. The only structural difference between the claimed and prior art compounds was that the ring structures of the claimed compounds had two carbon atoms between two sulfur atoms whereas the prior art ring structures had either one or three carbon atoms between two sulfur atoms. The court held that although the prior art compounds were not true homologs or isomers of the claimed compounds, the similarity between the chemical structures and properties is sufficiently close that one of ordinary skill in the art would have been motivated to make the claimed compounds in searching for new pesticides.).
MPEP § 2144.09 [R-07.2022].
Thus, claim 1 was prima facie obvious at the time of filing.
Claim 2 is directed towards a compound of claim 1 wherein R1 is C1-C4 alkyl or halo. While in compound 55 shown above R1 is hydrogen, one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R1 is C1-C4 alkyl or halo because Yoshino teaches examples wherein R1 is C1-C4 alkyl or halo. For example
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: (Yoshino, Specification, col. 24)
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(Yoshino, Specification, column 31);
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(Yoshino, Specification, column 33); Therefore, claim 2 was prima facie obvious at the time of filing.
Claim 3 is directed towards the compound of claim 1 wherein R1 is methyl, chloro, or fluoro. As shown above in the rejection of claim 2, both Yoshino teaches anticancer aryl sulfonamides wherein R1 is methyl or halogen (bromo and chloro are shown above). Therefore, one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R1 is methyl, fluoro, or chloro and claim 3 was prima facie obvious at the time of filing.
Claim 4 is directed towards the compound of claim 1 wherein R1 is hydrogen. As shown in the 103 rejection of claim 1, Yoshino teaches an indole-imidazole-sulfonamide wherein R1 is hydrogen. Therefore, one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R1 is hydrogen and claim 4 was prima facie obvious at the time of filing.
Claim 5 is directed towards the compound of claim 1 wherein R2 is chloro, fluoro, or cyano. Claim 9 is directed towards the compound of claim 1 wherein R2 is cyano. In the example compounds taught by Yoshino shown in the rejections of claims 1-2 above, R2 is cyano and chloro (fluoro is also halogen so would be expected to have similar properties). Therefore, one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R2 is chloro, fluoro, or cyano and claim 5 was prima facie obvious at the time of filing.
Claim 6 is directed towards the compound of claim 1 wherein R3 is hydrogen, methyl, fluoro, chloro, difluoromethyl, NH2 or C2H4OH. Claim 8 is directed towards the compound of claim 1 wherein R5 is hydrogen, methyl, fluoro, chloro, or NH2. While Yoshino does not teach these exact substituent locations on a pyrazole, one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R3 and R5 are as claimed because Yoshino teaches the claimed substituents in similar positions on similar rings.
For example, Yoshino teaches compounds wherein substituents on similar rings are hydrogen, NH2, halo, and methyl. For example:
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(Yoshino, Specification, column 44);
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Yoshino, Specification, column 42);
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(Yoshino, Specification, column 28);
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(Yoshino, Specification, column 36).
Thus, claims 6 and 8 were prima facie obvious at the time of filing.
Claim 7 is directed towards the compound of claim 1 wherein R4 is hydrogen, methyl… one of ordinary skill in the art would have a reasonable expectation of success to generate a compound of formula I of claim 1 wherein R4 is methyl because Yoshino teaches a similar compound wherein methyl is conjugated to nitrogen:
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(Yoshino, Specification, column 42). Yoshino, Specification, column 2, lines 35+ teaches additional substituents as in claim 7). Thus, claim 7 was prima facie obvious at the time of filing.
Claim 10 is directed towards a compound of claim 1, for example, N-(3-cyano-1H-indol-7-yl)-1-methyl-pyrazole-4-sulfonamide. This is a preferred compound according to the specification and has the following structure:
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(Specification, page 73). As shown above, Yoshino teaches the following compound:
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Yoshino, Specification, column 42).
These compounds are so similar that they can be reasonably expected to have similar properties as explained in the rejection of claim 1.
For example, the claimed compound differs from N-(3-cyano-4-methyl-1H-indol-7-yl)-1-methyl-pyrazole-4-sulfonamide, in that the sulfur is bonded to pyrazole instead of imidazole. However, as stated in the rejection of claim 1, Yoshino teaches both pyrazole and imidazole at this site, and pyrazole and imidazole are so similar they can be expected to have similar properties.
Furthermore, Yoshino does teach that compound 55 has in vitro antitumor activity against colon cancer cells that outperforms the control (IC50 of 0.59 for the test compound vs. 2.0 for the control CQs) (Yoshino, Specification, columns 11-12). This activity is typical of species within the disclosed genus, structurally similar to that claimed, providing a reason for one of ordinary skill in the art to choose the claimed species from the genus, based on the reasonable expectation that structurally similar species usually have similar properties. See, e.g., Dillon, 919 F.2d at 693, 696, 16 USPQ2d at 1901, 1904. See also In re Deuel, 51 F.3d 1552, 1558, 34 USPQ2d 1210, 1214 (Fed. Cir. 1995) ("Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homologs because homologs often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.").
Thus, claim 10 was prima facie obvious at the time of filing.
Claim 11 is directed towards a pharmaceutical composition comprising a compound of claim 1. One of ordinary skill in the art would have a reasonable expectation of success to arrive at a pharmaceutical composition comprising a compound of claim 1 because similar compositions are commonly known in the art. For example, Yoshino teaches pharmaceutical compositions:
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(Yoshino, Specification, column 2). Thus, claim 11 was prima facie obvious at the time of filing.
Claim 12 is directed towards a method of treating cancer comprising administering a therapeutically effective amount of a compound of claim 1 to a subject. One of ordinary skill in the art would have a reasonable expectation of success to treat cancer with the compound of claim 1 because similar compound are known in the art for the treatment of cancer. For example, Yoshino teaches that the compounds of their invention are effective to treat cancer:
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(Yoshino, Specification, column 2); Thus, claim 12 was prima facie obvious at the time of filing.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Yoshino et al. (US5767283A, Published June 16, 1998), as applied to claims 1-12 above, and further in view of Gray et al. (US 11,807,606 B2, Published November 7, 2023, Priority Date January 25, 2018) (of record, IDS dated 08/20/2025, U.S. patent cite no. 4).
The rejection of claims 1-12 as unpatentable over Yoshino is incorporated by reference.
Claim 13 is directed towards a process of preparing a compound of formula I:
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with an intermediate of formula B:
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in the presence of a base to give a compound of formula I.
Yoshino teaches the following synthesis scheme for compounds of formula I:
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(Yoshino, Specificaiton, column 4).
While the method of Yoshino differs from the synthesis scheme of claim 16 in that the sulfone of intermediate A is bonded to hydrogen in Yoshino and chlorine in claim 16, one of ordinary skill in the art would have a reasonable expectation of success to make this modification because Gray teaches a similar synthesis scheme wherein the sulfone is bonded to chlorine:
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(Gray, Specification, column 35). Thus, claim 13 was prima facie obvious at the time of filing.
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Gray et al. (US 11,807,606 B2, Published November 7, 2023, Priority Date January 25, 2018) (of record, IDS dated 08/20/2025, U.S. patent cite no. 4) in view of Liang et al. (Bioorganic & Medicinal Chemistry Letters, Vol. 26, Issue 16, 15 August 2016, p. 4036-4041) (of record, IDS dated 08/20/2025, NPL cite no. 2).
Claim 1 is directed towards a compound of formula I:
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(indole or indazole-pyrazole-sulfonamides). For example, compounds of formula I include
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(Specification, p. 79) and
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(Specification, p. 75).
Grey teaches RBM39 degrading compounds with anticancer activity of general formula (I) and (Ia):
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Formula (I) (Grey, Specification, col. 2) and
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Formula (Ia) (Grey Specification, col. 5).
For example, Grey teaches the RBM39 degrading compound
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(Grey, Specification, col. 58).
While Grey’s compound differs from the instantly claimed compounds in that the sulfonamide is linked to chlorophenyl instead of 2-cyanoethyl-pyrazole or ethyl-pyrazole, one of ordinary skill in the art would have a reasonable expectation of success to substitute 2-cyanoethyl-pyrazole or ethyl-pyrazole because these groups are known in the art to have similar properties to chlorophenyl.
For example, see Liang who teaches that these substituents produce compounds with similar activities:
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Liang, p. 4038;
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Liang, p. 4039.
Therefore, claim 1 was prima facie obvious at the time of filing.
Claims 2-3 and 5-10 read on the compounds shown above and were thus prima facie obvious at the time of filing.
Claim 4 is directed towards a compound of claim 1, wherein R1 is hydrogen. One of ordinary skill in the art would have a reasonable expectation of success to generate an RBM39 degrader wherein R1 is hydrogen because Grey teaches that R1 may be hydrogen. For example,
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(Grey, Specification, col. 54, compound 31).
Therefore, claim 4 was prima facie obvious at the time of filing.
Claim 11 is directed towards a pharmaceutical composition comprising a compound of claim 1. One of ordinary skill in the art would have a reasonable expectation of success to arrive at a pharmaceutical composition comprising a compound of claim 1 because similar compositions are commonly known in the art. For example, Grey teaches pharmaceutical compositions: “In certain embodiments, disclosed herein are pharmaceutical compositions comprising a compound of Formula (І), Formula (II), or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.” (Grey, Specification, col. 3, lines 29-33). Therefore, claim 11 was prima facie obvious at the time of filing.
Claim 12 is directed towards a method of treating cancer comprising administering a therapeutically effective amount of a compound of claim 1 to a subject. One of ordinary skill in the art would have a reasonable expectation of success to treat cancer with the compound of claim 1 because similar compound are known in the art for the treatment of cancer. For example, Grey teaches that the compounds of their invention are effective to treat cancer:
In certain embodiments, disclosed herein are compounds of Formula (I) or Formula (II) that act as degraders of RRM proteins. These compounds are therapeutic agents for the treatment of diseases such as cancer and metastasis, and other RRM protein mediated diseases.
Grey, Specification, col. 3, lines 24-29;
In certain embodiments the disclosure relates to a method of treating or preventing cancer, comprising administering to a subject in need thereof of a compound of Formula (I), Formula (II), or a pharmaceutically acceptable salt thereof.
Grey, Specification, col. 19, lines 45-48.
Therefore, claim 12 was prima facie obvious at the time of filing.
Claim 13 is directed towards a process of preparing a compound of formula I:
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with an intermediate of formula B:
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in the presence of a base to give a compound of formula I.
One of ordinary skill in the art would have a reasonable expectation of success to prepare a compound of formula I by this method because Gray teaches a comparable synthesis scheme:
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(Gray, Specification, column 35). Thus, claim 13 was prima facie obvious at the time of filing.
Given the above teachings, the invention as a whole was prima facie obvious at the time of filing.
Nonstatutory Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-13 provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6, 9-11, and 14-16 of copending Application No. 17/598,339 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the copending application claims a subgenus of compounds and overlapping species with the present application. Both applications claim pharmaceutical compositions of the compounds, methods of treating cancer with the compounds, and the same synthesis method for the compound. As the copending application claims a subgenus of compounds and overlapping species to the instant application, the instant claims are anticipated by the claims of the copending application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claim is found to be allowable.
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/HEATHER DAHLIN/Examiner, Art Unit 1629