DETAILED ACTION
This office action is in response to the Applicant’s filing dated January 8th, 2026.
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 .
Status of Claims
Claims 1-20 are pending in the instant application.
Priority
This application is a 371 of PCT/CN2021/098707 filed on June 7th, 2021; and claims benefit of foreign priority of CN2021105834508 filed on May 27th, 2021. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Election/Restrictions
Applicant’s election without traverse of Group I in the reply filed on January 8th, 2026 is acknowledged.
Claims 8, 10 and 19-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected group, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on January 8th, 2026.
Applicant’s election of species without traverse of Compound IA-3 shown below in the reply filed on January 8th, 2026 is acknowledged.
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which is a compound of genus Formula (X1) wherein Z is absent; wherein X is O; wherein Y is NH; wherein R2 is an unsubstituted C1 alkyl (methyl), and Y and R2 are directly connected; and wherein R3 is an unsubstituted 6-member heteroaryl, specifically pyridine.
A prior art search was conducted for the elected species of Compound IA-3. This compound was found free of prior art. Therefore, the Examiner expanded search to encompass CAS RN: 2331256-29-0 shown below:
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Which is a species of genus Formula (X2) wherein Z is carbonyl; wherein X is O; wherein Y is
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; wherein R2 is an unsubstituted C1 alkyl (methyl), and Y and R2 are connected to form a ring; and wherein R3 is an unsubstituted hydroxyl.
This search retrieved prior art. In view of the teachings of the prior art, the Examiner further expanded search to encompass Compound IIA-27 shown below:
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which is a compound of genus Formula (X2) wherein Z is carbonyl; wherein X is O; wherein Y is NH; wherein R2 is an unsubstituted C1 alkyl (methyl), and Y and R2 are directly connected; and wherein R3 is an unsubstituted trihalomethyl, specifically CF3.
This search retrieved prior art. Therefore, the Examiner’s search will not be extended unnecessarily to additional species in/for/during this Office Action.
Claims 15-16 and 18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on January 8th, 2026. Claims 1-7, 9, 11-14 and 17 read on the elected species and will be examined herein.
Claim Objections
Claim 9 objected to because of the following informalities: In the first line, claim 9 recites “Pharmaceutical composition or pharmaceutical…”, but should read “A pharmaceutical composition or pharmaceutical…”. Appropriate correction is required.
Claim 13 is objected to as being dependent upon a rejected base claim.
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.
Claims 1-6, 9, 11-12 and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Colabuono (WO 2020/106695 A1), cited in the IDS filed on April 28th, 2023; as evidenced by Rowe et al (Dimethyl Sulfoxide. Handbook of Pharmaceutical Excipients. (2009), 6th Edition, Pharmaceutical Press, 238-240), cited for evidentiary purposes only.
Regarding claims 1-6, 9, 11-12 and 14, Colabuono teaches ARI-045 shown below (page 270, Example 134):
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which is a compound of instantly claimed Formula (X2) wherein Z is carbonyl; wherein X is O; wherein Y is
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; wherein R2 is an unsubstituted C1 alkyl (methyl), and Y and R2 are connected to form a ring; and wherein R3 is an unsubstituted hydroxyl. This is the compound initially expanded to by the Examiner. Colabuono further teaches ARI-045 in solution with a solvent, DMSO (page 91, Table 1, last row); which reads on a pharmaceutical excipient (carrier) as evidenced by Rowe, cited for evidentiary purposes only, in the Handbook of Pharmaceutical Excipients (page 238, section 7).
Thus, the teachings of Colabuono anticipate the compound and composition of instant claims 1-6, 9, 11-12 and 14.
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.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Colabuono (WO 2020/106695 A1), cited in the IDS filed on April 28th, 2023.
Regarding claim 17, Colabuono anticipates the compound of Formula (X2), ARI-045, as described in the above rejection.
Colabuono does not teach a compound wherein Y is
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; wherein R2 is an unsubstituted C2 alkyl (ethyl), and Y and R2 are connected to form a ring; thus forming
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as R2’.
MPEP § 2144.09(II) states:
“Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978).”
It would have been prima facie obvious to someone of ordinary skill in the art to perform a routine structural modification, adding an additional CH2 repeating unit at the R2 position, creating a homolog with a very similar structure to that of ARI-045, with a reasonable expectation of retaining similar chemical properties.
Taken together, all of this would result in a compound of Formula (IIA1) of instant claim 17 with a reasonable expectation of success.
Claims 1-7, 9, 11-12, 14 and 17 are rejected under 35 U.S.C. 103 as being unpatentable over Colabuono (WO 2020/106695 A1), cited in the IDS filed on April 28th, 2023; in view of Meanwell (Journal of Medicinal Chemistry; 2018, 61 (14), 5822-5880); as evidenced by Rowe et al (Dimethyl Sulfoxide. Handbook of Pharmaceutical Excipients. (2009), 6th Edition, Pharmaceutical Press, 238-240), cited for evidentiary purposes only.
Regarding claims 1-7, 9, 11-12, 14 and 17, Colabuono teaches Compound ARI-033 (page 191, Example 24) shown below:
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which is a compound that is structurally similar to the instantly claimed compound further expanded to by the Examiner, Compound IIA-27. The only difference between the compounds is the presence of CF3 at the instantly claimed R3 position of IIA-27, while CH3 is present at the R3 position of Colabuono’s compound ARI-033. Colabuono further teaches ARI-033 in solution with a solvent, DMSO (page 89, Table 1, first row); which reads on a pharmaceutical excipient (carrier) as evidenced by Rowe, cited for evidentiary purposes only, in the Handbook of Pharmaceutical Excipients (page 238, section 7).
Colabuono does not teach a compound wherein CF3 is present at the instantly claimed R3 position.
Meanwell teaches “Replacing hydrogen atoms with fluorine has been explored extensively in
drug design, most commonly to replace those bound to an aromatic ring or in the context of a CF3 for
CH3 where these substitutions can modulate potency or interfere with metabolic modification” (page 5823, left column, last paragraph). Meanwell further teaches, “Because the introduction of fluorine can lead to resistance toward oxidative metabolism, fluorination has developed into a popular approach to addressing poor pharmacokinetic performance of compounds in vitro and in vivo” (page 5824, left column, second paragraph).
MPEP 2144.09 states:
A prima facie case of obviousness may be made when chemical compounds have very
close structural similarities and similar utilities. "An obviousness rejection based on
similarity in chemical structure and function entails the motivation of one skilled in the
art to make a claimed compound, in the expectation that compounds similar in
structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245,
254 (CCPA 1979).
It would have been prima facie obvious to a person of ordinary skill in the art to modify ARI-033 of Colabuono by substituting the CH3 group at the R3 position with a CF3 group to arrive at the instantly claimed compound IIA-27. As taught by Meanwell, replacement of CH3 with CF3 is a well-established medicinal chemistry strategy used to modulate potency, improve metabolic stability and enhance pharmacokinetic properties. Given the close structural similarity between compounds, and thus their shared utility, one of ordinary skill in the art would have reasonably expected the modified compound to retain similar biological properties while potentially exhibiting improved performance. The instantly claimed compound IIA-27 thus represents a predictable variation of the prior art compound ARI-033, achieved through the routine substitution of one known substituent for another known bio-isosteric equivalent.
“[T]he rationale to support a conclusion that the claim would have been obvious is that all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination yielded nothing more than predictable results to one of ordinary skill in the art. KSR, 550 U.S. at 416, 82 USPQ2d at 1395.
Taken together, all of this would result in the compound and composition of instant claims 1-7, 9, 11-12, 14 and 17 with a reasonable expectation of success.
Conclusion
Claims 1-7, 9, 11-12, 14 and 17 are rejected.
Claims 9 and 13 are objected to.
No claim is allowed.
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/C.L.J./Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691