DETAILED ACTION
A non-final Office action was mailed 31 October 2025 (“Office Action”).
Applicant’s reply to the Office Action was received 30 January 2026 (“Reply”).
Status of the Claims
The listing of claims filed with the Reply has been examined.
Claims 1–3, 5, 6, 9, 10, 12, 23, 24, 27, 28, 32, 34, 42, 44, 47, 48, and 57–62 are pending.
Claims 1, 3, 5, 10, 42, 47, and 62 are amended.
Claims 47, 48, and 62 are withdrawn.
Claims 4, 7, 8, 11, 13–22, 25, 26, 29–31, 33, 35–41, 43, 45, 46, and 49–56 are canceled.
Status of Rejections and Objections
Unless repeated herein, any objection or rejection in the Office Action is withdrawn.
Claim Rejections - 35 U.S.C. § 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.
Graham v. John Deere Co., 383 U.S. 1, 17 (1966); MPEP § 2141(II).
Claims 1–3, 10, 12, 32, 34, 60, and 61 are rejected under 35 U.S.C. § 103 as being unpatentable over US 9,248,187 (“Bylock”).
The Graham factors are addressed in turn below.
Determining the scope and contents of the prior art
Bylock discloses a method of synthesizing the compounds of formula (I) comprising the reaction of a compound of formula II with a boronic acid or boronic ester; or comprising the reaction of a compound of formula II with a diborane to obtain a compound of formula III and subsequent coupling of the compound of formula III with a compound R3X. (Bylock, 154:38–155:10) (col:line). X is chloro, bromo, iodo, or triflate. (Id., 155:10). R3 is a heteroaryl. (Id., 3:30–37). R1 and R2 can be, e.g., H or alkyl. R5 can be, e.g., heteroaryl. (Id., 3:39–43).
The synthetic methods are shown below.
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Compound I-52 (below) is an example of a Bylock intermediate of formula (II). The compound corresponds to instant formula (I) as follows: R1 = C6-10 aryl substituted by halogen; Z1 = C1-2 alkylene substituted by one or more C1-3 alkyl; Z2 = 1,2,4-oxadiazole; X1 = N; X2 = CR2; R2 = N(R5)2; R5 = H; and there is a double bond between X1 and X2. (Id., col.177).
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Ascertaining the differences between the prior art and the claims at issue
Bylock formula (I) is a genus directed to subject matter that overlaps with the instant formula (I) (e.g., X = chloro); however, there is no specific example in Bylock that anticipates instant formula (I). Compound I-52 is a related example of Bylock intermediate formula (II) in which the phenyl is substituted by bromo, which the claims do not include as a substituent.
Resolving the level of ordinary skill in the pertinent art
The level of one of ordinary skill may be found by inquiring into: (i) the type of problems encountered in the art; (ii) prior art solutions to those problems; (iii) the rapidity with which innovations are made; (iv) the sophistication of the technology; and (v) the education level of active workers in the field. Custom Accessories, Inc. v. Jeffrey-Allan Industries, Inc., 807 F.2d 855, 962 (Fed. Cir. 1986). All of the factors may not be present in every case, and one or more of them may predominate. Envtl. Designs, Ltd. v. Union Oil Co., 713 F.2d 693, 696 (Fed. Cir. 1983). Based on the typically high education level of workers in the pharmaceutical art and the high degree of sophistication required to solve problems encountered in the art, Examiner finds a person having ordinary skill in the art would have at least a college degree in chemistry, biology, biochemistry, pharmacology, or a related field, and several years of experience.
Considering objective evidence present in the application indicating obviousness or nonobviousness
There is no data in the specification relevant to an unexpected property based on the halogen substituted on the R1 phenyl.
The question of obviousness
Based on the above factors, it would have been prima facie obvious, prior to the filing of the instant application, for a person having ordinary skill in the art to modify Compound I-52 by substituting the bromo with chloro. The substitution of one halogen for another would have been obvious because Bylock presents them as alternatives for the synthetic reactions. One of ordinary skill in the art would have been motivated to modify Bylock to ascertain which option provides the best result. There would have been a reasonable expectation of success at arriving at the claimed invention because each of the X options are commonly used for such reactions.
The specification has been considered for any evidence of non-obviousness, including unexpected results, but there is nothing relevant.
Allowable Subject Matter
Claims 5, 6, 9, 12, 23, 24, 27, 28, 42, 44, and 57–59 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
Applicant’s amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 C.F.R. § 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 nonprovisional extension fee (37 C.F.R. § 1.17(a)) pursuant to 37 C.F.R. § 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 mailing date of this final action.
Communication
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jason Nolan at (571) 272-2480. The examiner can normally be reached Monday through Friday between 9:00–5:00.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to submit an Automated Interview Request: http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan, can be reached on 571-270-7674.
/J.M.N./Patent Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623
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