DETAILED ACTION
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 .
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to a compound, and compound having the structure of:
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(referred to therein as “Compound-58”) as the elected species of compound in the reply filed on July 7, 2026 is acknowledged.
Please note the Examiner has reasonably construed that the elected compound-58 has a chemical name of “(R)-6-chloro-3-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl) ethyl) amino) picolinic acid” in view of the instant specification (see e.g., page 138, Ex. 58).
Claims 33, 49, 66-67, 69, 71-72, 76 and 78 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on July 7, 2026.
Expansion of Election of Species Requirement
A reasonable and comprehensive search of the elected species conducted by the Examiner discover a prior art by Wrona et al. that anticipates the claimed invention, wherein the prior art teaches compound 4 and compound 24 (see rejection below). Said prior art also renders obvious the compound, 2-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl) ethyl) amino) benzoic acid, and (R)-2-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl) ethyl) amino) benzoic acid instantly claimed. In light of this discovery, the search is expanded to the subject matter of the adenosine receptor antagonist to include compound 4 and compound 60 of Wrona et al. and the following compounds:
2-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl)ethyl)amino)benzoic acid; and
(R)-2-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl)ethyl)amino)benzoic acid
in addition to the elected compound species, such that it does not encompass the full scope of the claims.
Status of Claims
Acknowledgement is made of the receipt and entry of the amendment to the claims filed on May 8, 2024, wherein claims 1, 39, 42 and 64-67 are unchanged; claims 3-7, 9, 11-12, 15-16, 19-20, 22-28, 30-32, 35, 37-38, 40-41, 43-44, 47-48, 50, 52-56, 59-63, 70, 73-75, 77 and 79-80 are canceled; and claims 2, 8, 13-14, 17-18, 21, 29, 33, 34, 36, 45-46, 49, 51, 57-58, 68-69, 71-72, 76, and 78 are amended. Claims 1-2, 8, 10, 13-14, 17-18, 21, 29, 33-34, 36, 39, 42, 45-46, 49, 51, 57-58, 64-69, 71-72, 76 and 78 are pending.
Claims 33, 49, 66-67, 69, 71-72, 76 and 78 are withdrawn.
Claims 1-2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57-58, 64-65, and 68 are pending in accordance with the elected species along with the expanded species set forth in the Expansion of Election of Species Requirement section above.
Priority
The instant application 18/658,666 filed on May 8, 2024 claims priority to, and the benefits of U.S. Provisional Application No. 63/501,970 filed on May 12, 2023; U.S. Provisional Application No. 63/522,325 filed on June 21, 2023; and U.S. Provisional Application No. 63/578,523 filed on August 24, 2023.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 10/9/2024 and 11/15/2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Claim Objections
Claims 46 and 51 are objected to because of the following informalities:
Regarding claims 46 and 51, the recitation of “according to claim 42 wherein” is missing a comma between the claim number and the preposition that follows, and should read --according to claim 42, wherein--
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57-58 and 64-65 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claims 2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57, and 64-65, the recitation of “a” in the phrase of “[a] compound according to claim” renders the claim indefinite, because the claim uses the indefinite article “a” before the noun to introduce a subject matter that is not previously introduced. In other words, said recitation is ambiguous because it is not clear where applicant intends to (i) refer back to the compound set forth in the claim it depends upon or (ii) introduce another new compound of formula (I). To the extent that scenario (ii) applies, then it is not clear if applicant is claiming (i) more than one compound of formula (I) together such that it forms a mixture, or (ii) a singular compound of formula (I) that replaces the previously mentioned compound of formula (I). Therefore, one cannot reasonably determine the metes and bounds of the compound of formula (I), and cannot reasonably determine which interpretation applies.
Regarding claim 58, a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, the claim recites the broad recitation “compound of Formula (IV):
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…wherein R5 is C1-C2alkyl, cyclopropyl, bromo, chloro, fluoro, cyano, or trifluoromethyl”, and the claim also recites “compound of Formula (IV-A):
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“, “compound of Formula (IV-C):
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”, “compound of Formula (IV-D):
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”, “a compound of Formula (IV-E):
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”, respectively, which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 10 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Regarding claim 10, the limitation of “R2 is…5-7 membered heteroaryl” fails to further limit the R2 of formula (I) set forth in claim 1. Specifically, claim 1 recites “5-6 membered heteroaryl”; and that is a narrower limitation when compared to the limitation set forth in the dependent claim.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2, 8, 10, 13-14, 17-18, 29, 34, 36, 39, 42, 45-46, 51, 57 and 68 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Wrona et al. (WO 2024/026419 A1; cited in the IDS filed on October 9, 2024).
Wrona et al. teaches Compound 4, 2-{[(1R)-1-[7-methyl-3-(morpbolin-4-yl)quinoxalin-5-yl]ethyl] amino}benzoic acid, having the structure of:
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is an exemplary compound of Formula (I) (see e.g., Table 2, Compound No. 4); and a pharmaceutical composition comprising the compound in combination with at least one pharmaceutically acceptable excipient or carrier (see e.g., [0064]).
Please note the Compound 4 of Wrona et al. is a compound of instant formula (I):
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, wherein R5 is hydrogen; R5A is
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; R6A is hydrogen; R6 is hydrogen; R4 is methyl; R3 is methyl; R1 is hydrogen; R2 is
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.
Therefore, the claimed invention is being anticipated by Wrona et al.
Claims 1-2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57, 58 and 68 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Wrona et al. (WO 2024/026419 A1; cited in the IDS filed on October 9, 2024).
Wrona et al. teaches Compound 25, 2-{[(1R)-1-[2,7-dimethyl-3-(morpholin-4-yl)quinoxalin-5-yl] ethyl]amino}benzoic acid, having the structure of:
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is an exemplary compound of Formula (I) (see e.g., Table 2, Compound No. 25); and a pharmaceutical composition comprising the compound in combination with at least one pharmaceutically acceptable excipient or carrier (see e.g., [0064]).
Please note the Compound 25 of Wrona et al. is a compound of instant formula (I):
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, wherein R5 is methyl; R5A is
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; R6A is hydrogen; R6 is hydrogen; R4 is methyl; R3 is methyl; R1 is hydrogen; R2 is
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.
Therefore, the claimed invention is being anticipated by Wrona et al.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57-58, 64-65, and 68 are rejected under 35 U.S.C. 103 as being unpatentable over Wrona et al. (WO 2024/026419 A1; cited in the IDS filed on October 9, 2024).
Wrona et al. teaches Compound 4, 2-{[(1R)-1-[7-methyl-3-(morpbolin-4-yl)quinoxalin-5-yl]ethyl] amino}benzoic acid, having the structure of:
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is an exemplary compound of Formula (I) useful for modulating PI3K[Symbol font/0x61] activity (see e.g., Table 2, Compound No. 4; Table B); and a pharmaceutical composition comprising the compound in combination with at least one pharmaceutically acceptable excipient or carrier (see e.g., [0064]). Wrona et al. further teaches the compounds may possess one or more asymmetric centers; such compounds can therefore be produced as individual (R)- or (S)-stereoisomers or as mixtures thereof (see e.g., [0292]). Wrona et al. further teaches a compound of formula (I):
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; an isomer thereof, or a pharmaceutically acceptable salt thereof, wherein R2 is, inter alia, H, cyano or C1-C6 alkyl(see e.g., [0096]).
In the present case, the difference between the Compound 4 of Wrona et al. and the claimed invention is that the prior art compound contains methyl (-CH3) at R2 rather than cyano (CN) shown below (see shaded):
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It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select the compound 4 of Wrona et al. and then modify said compound by replacing methyl with cyano at R2. One would have been motivated to do so, because Wrona et al. teaches a list of alternated R2, including hydrogen and cyano, that is contemplate for use to arrive at compound of formula (I) useful for modulating PI3K[Symbol font/0x61] activity. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that by modifying the compound 4 of Wrona et al. in accordance with the formula (I) as noted above would have successfully arrive at a compound of formula (I) useful for modulating PI3K[Symbol font/0x61] activity; and therefore, said compound can reasonably be combine with at least one pharmaceutically acceptable excipient or carrier to arrive at a pharmaceutical composition. The fact that Wrona et al. also teaches the compound 4 can be in the form of racemic mixture, it renders obvious the “2-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-
yl)ethyl)amino)benzoic acid” in claim 64 for the same logic.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Claims 1-2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57-58, 64-65, and 68 are rejected under 35 U.S.C. 103 as being unpatentable over Wrona et al. (WO 2024/026419 A1; cited in the IDS filed on October 9, 2024).
To the extent that the claims are drawn to the elected compound species, i.e., Compound-58, then the following rejection applies.
Wrona et al. teaches Compound 25, 2-{[(1R)-1-[2,7-dimethyl-3-(morpholin-4-yl)quinoxalin-5-yl] ethyl]amino}benzoic acid, having the structure of:
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is an exemplary compound of Formula (I) useful for modulating PI3K[Symbol font/0x61] activity (see e.g., Example 18 and Example 19; Table 2, Compound No. 25; Table B); and a pharmaceutical composition comprising the compound in combination with at least one pharmaceutically acceptable excipient or carrier (see e.g., [0064]). Wrona et al. further teaches the racemic mixture of 2-[1-(2,7-dimethyl-3-morpholino-quinoxalin-5-yl)ethylamino]benzoic acid having the structure of:
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(see e.g., p. 112, Example 18 and Example 19). Wrona et al. further teaches a compound of formula (I):
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; an isomer thereof, or a pharmaceutically acceptable salt thereof, wherein R2 is, inter alia, cyano or C1-C6 alkyl; A is C6-C10 aryl or 5-to 10-membered heteroaryl, wherein the C6-C10aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more RA; each RA independently is, inter alia, halogen or -(C=O)OH (see e.g., [0096]). Wrona et al. further teaches the term “halogen” refers to fluoro, chloro, bromo and iodo (see e.g., [0046]); and examples of heteroaryl groups include, inter alia, pyridine (see e.g., [0039]).
In the present case, the difference between the Compound 25 of Wrona et al. and the claimed invention is that the prior art compound contains methyl (-CH3) at R2 rather than cyano (CN); contains phenyl as A rather pyridinyl; contains one RA that is -(C=O)OH rather than a total of 2 RA (-(C=O)OH and chloro) shown below (see shaded):
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.
It would have been prima facie obvious to one of ordinary skill in the art at the time the application was filed to select the compound 25 of Wrona et al. and then modify said compound by replacing methyl with cyano at R2, replacing phenyl with pyridine as A, and substituting said A with additional RA that is a chloro. One would have been motivated to do so, because Wrona et al. teaches a list of alternated R2, including cyano and C1-C6 alkyl; a list of alternated A, including C6-C10aryl, or 5- to 10-membered heteroaryl such as pyridine; and a list of one or more RA that can optionally substituted on A, including -(C=O)OH or halogen such as chloro, that are contemplate for use to arrive at compound of formula (I) useful for modulating PI3K[Symbol font/0x61] activity. One would have a reasonable expectation of success to arrive at the claimed invention, because one would have reasonably expected that by modifying the compound 25 of Wrona et al. in accordance with the formula (I) as noted above would have successfully arrive at a compound of formula (I) useful for modulating PI3K[Symbol font/0x61] activity; and therefore, said compound can reasonably be combine with at least one pharmaceutically acceptable excipient or carrier to arrive at a pharmaceutical composition. The fact that Wrona et al. also teaches the compound 25 can be in the form of racemic mixture, it renders obvious the “6-chloro-3-(( 1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl)ethyl)amino) picolinic acid” in claim 64 for the same logic.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
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 1-2, 8, 10, 13-14, 17-18, 21, 29, 34, 36, 39, 42, 45-46, 51, 57-58, 64-65, and 68 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 of copending Application No. 19/047,751 (reference application).
Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of reference application is drawn to a crystalline form of (R)-6-chloro-3-((1-(2-cyano-7-methyl-3-morpholinoquinoxalin-5-yl)ethyl)amino)picolinic acid having a powder X-ray diffraction (PXRD) pattern; and a pharmaceutical composition comprising the crystalline form and a pharmaceutically acceptable carrier.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Chihyi Lee whose telephone number is (571)270-0663. The examiner can normally be reached Monday - Friday 8:30 am - 5:00 pm EST.
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/CHIHYI LEE/Examiner, Art Unit 1628
/JEAN P CORNET/Primary Examiner, Art Unit 1628
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