Prosecution Insights
Last updated: April 19, 2026
Application No. 18/257,027

COMPOUND CONTAINING 1,3-BENZODIOXOL STRUCTURE AND PREPARATION METHOD AND USE THEREOF

Non-Final OA §112
Filed
Jun 12, 2023
Examiner
WILLIS, DOUGLAS M
Art Unit
1624
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Xi'An Xintong Pharmaceutical Research Co. Ltd.
OA Round
1 (Non-Final)
83%
Grant Probability
Favorable
1-2
OA Rounds
2y 1m
To Grant
99%
With Interview

Examiner Intelligence

Grants 83% — above average
83%
Career Allow Rate
1472 granted / 1781 resolved
+22.7% vs TC avg
Strong +19% interview lift
Without
With
+19.4%
Interview Lift
resolved cases with interview
Fast prosecutor
2y 1m
Avg Prosecution
40 currently pending
Career history
1821
Total Applications
across all art units

Statute-Specific Performance

§101
0.9%
-39.1% vs TC avg
§103
7.8%
-32.2% vs TC avg
§102
16.7%
-23.3% vs TC avg
§112
50.5%
+10.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 1781 resolved cases

Office Action

§112
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 1-15 are pending in the instant invention. According to the Amendments to the Claims, filed June 12, 2023, claims 9 and 11-15 were amended. Status of Priority This invention is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/CN2022/082684, filed March 24, 2022, which claims priority under 35 U.S.C. § 119(a-d) to CN 202110357313.2, filed April 1, 2021. Restrictions / Election of Species PNG media_image1.png 200 400 media_image1.png Greyscale PNG media_image2.png 200 400 media_image2.png Greyscale The inventor’s or joint inventor’s provisional election of the following, without traverse, in the reply filed on November 24, 2025, is acknowledged: a) Group I - claims 1-9; and b) substituted benzo[d][1,3]dioxole of formula (I) - p. 4, compound I-11, shown to the right below, and hereafter referred to as (R)-N-(7-(1-(1-acryloylpiperidin-3-yl)-4-amino-1H-pyrazolo[3,4-d]-pyrimidin-3-yl)benzo[d][1,3]dioxol-4-yl)-4-(tert-butyl)benzamide, where m = 0; n = 1; A = -NHC(O)-; R1 is shown to the left, wherein p = 0, Y1 = CR5, where R5 = -H, Y2 = CR5, where R5 = -H, Y3 = CR5, where R5 = -H, Y4 = CR5, where R5 = -H, and R4 = -C(CH3)3; R3 = -H; and X = N. Claims 1, 3-7 and 9 read on the elected species. Affirmation of PNG media_image3.png 200 400 media_image3.png Greyscale this election must be made by the inventor or joint inventor in replying to this Office action. Similarly, the inventor or joint inventor should further note that the requirement is still deemed proper and is therefore made FINAL. Likewise, the inventor or joint inventor should further note that the elected species, shown to the right, was found to be free of the prior art. Thus, the examiner has expanded the forthcoming prosecution to include all claims relevant to the genus of Group I, for a first Office action and prosecution on the merits. Moreover, the inventor or joint inventor should further note that claims 10-15 were withdrawn from further consideration, pursuant to 37 CFR 1.142(b), as being drawn to a nonelected or cancelled invention, there being no allowable generic or linking claim. Thus, a first Office action and prosecution on the merits of claims 1-9 is contained within. Specification Objection - Disclosure The following guidelines illustrate the preferred layout for the specification of a utility application. These guidelines are suggested for the inventor’s or joint inventor’s use. Arrangement of the Specification As provided in 37 CFR 1.77(b), the specification of a utility invention should include the following sections in order. Each of the lettered items should appear in upper case, without underlining or bold type, as a section heading. If no text follows the section heading, the phrase Not Applicable should follow the section heading: (a) TITLE OF THE INVENTION. (b) CROSS-REFERENCE TO RELATED APPLICATIONS. (c) STATEMENT REGARDING FEDERALLY SPONSORED RESEARCH OR DEVELOPMENT. (d) THE NAMES OF THE PARTIES TO A JOINT RESEARCH AGREEMENT. (e) INCORPORATION-BY-REFERENCE OF MATERIAL SUBMITTED ON A COMPACT DISC. (f) BACKGROUND OF THE INVENTION. (1) Field of the Invention. (2) Description of Related Art (including information disclosed under 37 CFR 1.97 and 1.98). (g) BRIEF SUMMARY OF THE INVENTION. (h) BRIEF DESCRIPTION OF THE SEVERAL VIEWS OF THE DRAWING(S). (i) DETAILED DESCRIPTION OF THE INVENTION. (j) CLAIM OR CLAIMS (commencing on a separate sheet). (k) ABSTRACT OF THE DISCLOSURE (commencing on a separate sheet). (l) SEQUENCE LISTING (See MPEP § 2424 and 37 CFR 1.821-1.825). The inventor or joint inventor is advised to format the specification according to 37 CFR 1.77(b) above and 37 CFR 1.77(c). Revisions should particularly include and/or address: a) section headings (b-i), where applicable; and b) bold-type, underline, and/or upper case formatting. Appropriate correction may be required. Specification Objection - Title The inventor or joint inventor is reminded of the proper content of the title of the invention. The title of the invention should be brief, but technically accurate and descriptive and should contain fewer than 500 characters. See 37 CFR 1.72(a) and MPEP § 606. The title of the invention is not technically accurate and descriptive. A new title is required that is clearly indicative of the invention to which the claims are directed. In the revised title, the examiner suggests additionally identifying a particular utility for the substituted benzo[d][1,3]-dioxoles of the formula (I). The following title is suggested: SUBSTITUTED BENZO[d][1,3]DIOXOLES AS BTK AND/OR JAK3 KINASE INHIBITORS. Appropriate correction is required. Specification Objection - Abstract The inventor or joint inventor is reminded of the proper content of an abstract of the disclosure. With regard particularly to chemical patents, for compounds or compositions, the general nature of the compound or composition should be given as well as the use thereof, e.g., The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics. Exemplification of a species could be illustrative of members of the class. For processes, the reactions, reagents and process conditions should be stated, generally illustrated by a single example, unless variations are necessary. See MPEP § 608.01(b), Section B. The abstract of the disclosure is objected to because it fails to exemplify any clear members or formulae illustrative of its class. Correction is required. See MPEP § 608.01(b). The examiner suggests incorporating a clear structure of formula (I) into the abstract, to overcome this objection. Claim Objections Claim 1 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation: A compound of formula (I): PNG media_image4.png 200 400 media_image4.png Greyscale (I) or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: A represents -NHC(O)-, -NHC(O)CH2-, -NHS(O)2-, -O-, or -S-; R1 represents: PNG media_image5.png 200 400 media_image5.png Greyscale , PNG media_image6.png 200 400 media_image6.png Greyscale , PNG media_image7.png 200 400 media_image7.png Greyscale , PNG media_image8.png 200 400 media_image8.png Greyscale , PNG media_image9.png 200 400 media_image9.png Greyscale , PNG media_image10.png 200 400 media_image10.png Greyscale , PNG media_image11.png 200 400 media_image11.png Greyscale , or PNG media_image12.png 200 400 media_image12.png Greyscale ; Y1 represents CR5 or N; Y2 represents CR5 or N; Y3 represents CR5 or N; Y4 represents CR5 or N; each R5 independently represents H, F, Cl, Br, I, CN, CH3, CF3, OH, OCH3, or OCF3; Z represents -NR6-, -O-, or -S-; R6 represents H, CH3, CH2CH3, or cyclopropyl; each R4 independently represents H, F, Cl, Br, I, CN, NO2, C1-C6 alkyl, CF3, C(O)NH2, C(O)NHCH3, C(O)NHCH2CF3, NH2, NHC1-C6 alkyl, NHC(O)CH3, N(CH3)2, N(CH2CH3)2, OH, OC1-C6 alkyl, OCF3, OCH2CH2OCH3, pyrrolidin-1-yl, piperazin-1-yl, 4-methylpiperazin-1-yl, morpholin-4-yl, or phenyl; X represents CH or N; m represents 0 or 1; n represents 0 or 1; R2 represents H, Cl, Br, or CN; and R3 represents H, C1-C6 alkyl, or C2-C6 heterocycloalkyl; wherein the C2-C6 heterocycloalkyl is a saturated 4-, 5-, or 6-membered ring containing one, two, or three heteroatoms or heteroatomic groups independently selected from the group consisting of N, NH, O, and S; and wherein the C1-C6 alkyl or C2-C6 heterocycloalkyl is substituted with one or more substituents independently selected from the group consisting of NH2, NHCH3, NHC(O)CH3, OH, and OCH3. Appropriate correction is required. See MPEP § 2173.02. Claim 2 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: A represents -NHC(O)-, or -NHS(O)2-; m represents 1; n represents 0; R2 represents H; and R3 represents H. Appropriate correction is required. See MPEP § 2173.02. Claim 3 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: A represents -NHC(O)-, or -NHS(O)2-; m represents 0; n represents 1; R2 represents H; and R3 represents H. Appropriate correction is required. See MPEP § 2173.02. Claim 4 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: The compound according to claim 1, wherein the compound is of formula (II): PNG media_image13.png 200 400 media_image13.png Greyscale (II) or a pharmaceutically acceptable salt thereof. Appropriate correction is required. See MPEP § 2173.02. Claim 5 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation: The compound according to claim 4, or a pharmaceutically acceptable salt thereof, wherein R1 represents: PNG media_image14.png 200 400 media_image14.png Greyscale , PNG media_image15.png 200 400 media_image15.png Greyscale , PNG media_image16.png 200 400 media_image16.png Greyscale , PNG media_image17.png 200 400 media_image17.png Greyscale , PNG media_image18.png 200 400 media_image18.png Greyscale , PNG media_image19.png 200 400 media_image19.png Greyscale , PNG media_image20.png 200 400 media_image20.png Greyscale , or PNG media_image21.png 200 400 media_image21.png Greyscale ; R8 represents H, Cl, or CH3; and each R7 independently represents H, F, Cl, Br, CN, CH3, C(CH3)3, CF3, C(O)NH2, C(O)NHCH3, C(O)NHCH2CF3, NH2, NHC(O)CH3, N(CH3)2, N(CH2CH3)2, OH, OCH3, OCF3, pyrrolidin-1-yl, 4-methylpiperazin-1-yl, morpholin-4-yl, or phenyl. Appropriate correction is required. See MPEP § 2173.02. Claim 6 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: The compound according to claim 5, or a pharmaceutically acceptable salt thereof, wherein: R8 represents Cl; and each R7 independently represents H, Cl, CH3, C(CH3)3, CF3, C(O)NHCH2CF3, N(CH3)2, N(CH2CH3)2, or OCH3. Appropriate correction is required. See MPEP § 2173.02. Claim 7 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation: A compound selected from the group consisting of: PNG media_image22.png 200 400 media_image22.png Greyscale I-1, PNG media_image23.png 200 400 media_image23.png Greyscale I-2, PNG media_image24.png 200 400 media_image24.png Greyscale I-3, PNG media_image25.png 200 400 media_image25.png Greyscale I-4, PNG media_image26.png 200 400 media_image26.png Greyscale I-5, PNG media_image27.png 200 400 media_image27.png Greyscale I-6, PNG media_image28.png 200 400 media_image28.png Greyscale I-7, PNG media_image29.png 200 400 media_image29.png Greyscale I-8, PNG media_image30.png 200 400 media_image30.png Greyscale I-9, PNG media_image31.png 200 400 media_image31.png Greyscale I-10, PNG media_image32.png 200 400 media_image32.png Greyscale I-11, PNG media_image33.png 200 400 media_image33.png Greyscale I-12, PNG media_image34.png 200 400 media_image34.png Greyscale I-13, PNG media_image35.png 200 400 media_image35.png Greyscale I-14, PNG media_image36.png 200 400 media_image36.png Greyscale I-15, PNG media_image37.png 200 400 media_image37.png Greyscale I-16, PNG media_image38.png 200 400 media_image38.png Greyscale I-17, PNG media_image39.png 200 400 media_image39.png Greyscale I-18, PNG media_image40.png 200 400 media_image40.png Greyscale I-19, PNG media_image41.png 200 400 media_image41.png Greyscale I-20, PNG media_image42.png 200 400 media_image42.png Greyscale I-21, PNG media_image43.png 200 400 media_image43.png Greyscale I-22, PNG media_image44.png 200 400 media_image44.png Greyscale I-23, PNG media_image45.png 200 400 media_image45.png Greyscale I-24, PNG media_image46.png 200 400 media_image46.png Greyscale I-25, PNG media_image47.png 200 400 media_image47.png Greyscale I-26, PNG media_image48.png 200 400 media_image48.png Greyscale I-27, PNG media_image49.png 200 400 media_image49.png Greyscale I-28, PNG media_image50.png 200 400 media_image50.png Greyscale I-29, PNG media_image51.png 200 400 media_image51.png Greyscale I-30, PNG media_image52.png 200 400 media_image52.png Greyscale I-31, PNG media_image53.png 200 400 media_image53.png Greyscale I-32, PNG media_image54.png 200 400 media_image54.png Greyscale I-33, and PNG media_image55.png 200 400 media_image55.png Greyscale I-34, or a pharmaceutically acceptable salt thereof. Appropriate correction is required. See MPEP § 2173.02. Claim 8 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: The compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein the pharmaceutically acceptable salt is an acid addition salt selected from the group consisting of an acetic acid addition salt, a benzenesulfonic acid addition salt, a carbonic acid addition salt, a citric acid addition salt, a ferulic acid addition salt, a hydrobromic acid addition salt, a hydrochloric acid addition salt, a lactic acid addition salt, a maleic acid addition salt, a methanesulfonic acid addition salt, an oxalic acid addition salt, a phosphoric acid addition salt, a pyruvic acid addition salt, a succinic acid addition salt, a sulfuric acid addition salt, a tartaric acid addition salt, and a p-toluenesulfonic acid addition salt. Appropriate correction is required. See MPEP § 2173.02. Claim 9 is objected to because of the following informalities: for clarity and precision, the existing recitation should be replaced with the following recitation: A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound according to claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof. Appropriate correction is required. See MPEP § 2173.02. Claim Rejections - 35 U.S.C. § 112(b) The following is a quotation of the second paragraph of 35 U.S.C. § 112: (b) CONCLUSION. The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or joint inventor regards as the invention. Claims 5 and 6 are rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention. The inventor or joint inventor should note that claim 5 recites the limitation, The compound… according to claim 4, wherein R1 represents… 1,2,3,4-tetrahydronaphthalen-5-yl-R7, in lines 1-4 of the claim. There is insufficient antecedent basis, in claim 4, for this limitation, with respect to the substituted benzo[d][1,3]dioxoles of the formula (II). According to claim 1, R1 is not recited as 1,2,3,4-tetrahydronaphthalen-5-yl, with respect to the substituted benzo[d][1,3]-dioxoles of the formula (I). Moreover, the inventor or joint inventor should further note that [C]laims which depend from indefinite claims are also indefinite. {See Ex parte Cordova, 10 USPQ 2d 1949, 1952 (PTO Bd. App. 1989)}. The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection. Claim 7 is rejected under 35 U.S.C. § 112(b) as being indefinite for failing to set forth the subject matter which the inventor or joint inventor regards as the invention. The inventor or joint inventor should note that claim 5 recites the limitation, The compound… according to claim 1, wherein the compound is… I-8, I-20, I-27, I-33, and I-34, in lines 1-4 of the claim. There is insufficient antecedent basis, in claim 1, for this limitation, with respect to the substituted benzo[d][1,3]dioxoles of the formula (I). According to claim 1, the aforementioned species are not recited as substituted benzo[d][1,3]dioxoles of the formula (I), particularly with regard to the following: I-8 (R5), I-20 (R1), I-27 (R3), I-33 (R5), and I-34 (R5), respectively. The examiner suggests amending the claim, particularly as stated in the section above entitled Claim Objections, to overcome this rejection. Allowable Subject Matter No claims are allowed. Conclusion 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
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Prosecution Timeline

Jun 12, 2023
Application Filed
Jan 25, 2026
Non-Final Rejection — §112 (current)

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
83%
Grant Probability
99%
With Interview (+19.4%)
2y 1m
Median Time to Grant
Low
PTA Risk
Based on 1781 resolved cases by this examiner. Grant probability derived from career allow rate.

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