Office Action Predictor
Last updated: April 15, 2026
Application No. 18/204,304

BICYCLIC INHIBITORS OF IRAK

Non-Final OA §101§102§103§112
Filed
May 31, 2023
Examiner
DAHLIN, HEATHER RAQUEL
Art Unit
1629
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Rigel Pharmaceuticals, INC.
OA Round
1 (Non-Final)
46%
Grant Probability
Moderate
1-2
OA Rounds
3y 3m
To Grant
71%
With Interview

Examiner Intelligence

Grants 46% of resolved cases
46%
Career Allow Rate
61 granted / 133 resolved
-14.1% vs TC avg
Strong +25% interview lift
Without
With
+25.4%
Interview Lift
resolved cases with interview
Typical timeline
3y 3m
Avg Prosecution
84 currently pending
Career history
217
Total Applications
across all art units

Statute-Specific Performance

§101
4.7%
-35.3% vs TC avg
§103
33.1%
-6.9% vs TC avg
§102
20.1%
-19.9% vs TC avg
§112
25.5%
-14.5% vs TC avg
Black line = Tech Center average estimate • Based on career data from 133 resolved cases

Office Action

§101 §102 §103 §112
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 claims priority benefit of U.S. Provisional Application No. 63/347,920, filed June 1, 2022. Information Disclosure Statement The information disclosure statement (IDS) submitted on May 3, 2024 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 1-28 are currently pending and subject to examination. Claim Rejections - 35 USC § 112(b) 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 9 and 20-27 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 claim 9, the phrase "such as" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d). Claim 20 is directed towards a method of treating a subject for a disease or condition wherein an IRAK inhibitor is indicated, comprising administering to the subject an effective amount of the compound of claim 1. One of ordinary skill in the art cannot determine the metes and bounds of the claim because it is unclear what patient population the claim is intended to treat because the claim does not recite that the subject is in need of treatment. The claim also recites administering to the subject an effective amount of the compound, but what is an effective amount of the compound for treating e.g. leukemia, in a subject that does not have leukemia? The specification states that the effective amount is “the amount of compound or composition sufficient to achieve a particular desired result.” (Specification, p. 9). In claim 20, the desired result is treating a disease or condition, but the subject does not necessarily have the disease or condition. Therefore, one of ordinary skill in the art would not know how to practice the method as claimed. Claim 27 is dependent from claim 20 and is directed towards the method of claim 23, wherein “the method further comprises identifying the subject having from the lymphoid neoplasm.” The phrase “having from the lymphoid neoplasm” is indefinite/ unclear, but is interpreted to mean having the lymphoid neoplasm. As such, it appears that the Applicant intended claim 20 to encompass administering the compound to any subject because otherwise the method of claim 27 would not be further limiting. Claims 24-26 depend from claim 20 and simply recite particular diseases or disorders and do not resolve this ambiguity and are therefore also indefinite. Appropriate correction is required. Claim Rejections - 35 USC § 101 35 U.S.C. 101 reads as follows: “Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.” Claims 18-19 are rejected under 35 U.S.C. 101 because the claimed invention is directed to a natural phenomenon without significantly more. The claim(s) recite(s) a method for inhibiting an IRAK enzyme, comprising contacting the enzyme with an effective amount of a compound of claim 1 (claim 18), wherein the contacting comprises administering the compound to a subject (claim 19). This judicial exception is not integrated into a practical application because the method does not require the treatment or prophylaxis of a medical condition. The claim(s) does/do not include additional elements that are sufficient to amount to significantly more than the judicial exception because the claim does not recite additional elements other than inhibiting IRAK by contacting it with the compound of claim 1. Step 1- The claims recite a process, so are one of the four categories of statutory subject matter. Step 2A, prong 1- The claims recite a natural phenomenon or physical phenomenon because they are directed towards contacting the compound and an enzyme, and merely observing the enzyme’s activity. Step 2A, prong 2- The claims do not recite additional elements that integrate the judicial exception into a practical application because a practical application must be more than the basic tools of scientific and technological work, such as a treatment for a specific medical condition. Observing the in vitro or in vivo activity of an enzyme after contacting the enzyme with a compound is a basic scientific observation, not a practical application within the bounds of 35 U.S.C. 101. Step 2B- The claims do not include additional elements that are sufficient to amount to significantly more than the judicial exception because the claim does not recite additional elements other than inhibiting IRAK. Furthermore, it is well known that compounds having the structure of formula I as in claim 1 inhibit IRAC. For example, Curran et al. (WO2017/025849 A1) teaches a species of falling within formula I, and that it is an IRAK inhibitor: PNG media_image1.png 144 158 media_image1.png Greyscale (Curran, Specification, p. 75, example 54); “In particular, novel bicyclic kinase enzyme inhibitor compounds of Formula la of the present invention possess a therapeutic role of inhibiting IRAK4 useful in the area of diseases and/or disorders that include, but are not limited to, cancers, allergic diseases…” (Curran, Specification, p. 4, lines 26-36). Claim Rejections - 35 USC § 112(d) 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.” Claims 26 and 28 are 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. Claims 26 and 28 fail to include all the limitation of claim 23 upon which it depends because claim 23 excludes myelodysplastic/ myeloproliferative lymphoid neoplasms (MDS/ MPN) but claims 26 and 28 require the lymphoid neoplasm to be an MDS/ MPN. 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 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 1-13, 15, 17-23 and 27 is/are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Li et al. (US 2022/0177446 A1, published June 9, 2022, filed Dec. 2, 2021) (of record, IDS U.S. cite no. 1). Claim 1 is directed towards a compound of Formula I: PNG media_image2.png 191 198 media_image2.png Greyscale , for example, PNG media_image3.png 227 288 media_image3.png Greyscale (Instant Specification, p. 118, Example 98). Li teaches the same compound as example 98: PNG media_image4.png 219 213 media_image4.png Greyscale (Li, Specification, p. 59). Therefore, claim 1 is anticipated. Claims 2, 4-6, 9-13, and 15 read on the compound example 98. Therefore, claims 2, 4-6, 9-13 and 15-16 are anticipated. Claim 3 is directed towards the compound of claim 1, wherein R5 is isopropyl. Claim 7 is directed towards the compound of claim 1, wherein R2 is PNG media_image5.png 40 94 media_image5.png Greyscale , R8 is C1-6 alkyl optionally substituted with OH. Claim 8 is directed towards the compound of claim 7, wherein R2 is PNG media_image6.png 58 114 media_image6.png Greyscale . Li teaches a compound of claim 1, wherein R5 is isopropyl and R2 is PNG media_image6.png 58 114 media_image6.png Greyscale : PNG media_image7.png 255 212 media_image7.png Greyscale (Li, Specification, p. 21, example 29). Therefore, claims 3, 7 and 8 are anticipated. Claim 17 is directed towards a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient. Li teaches a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient (Li, Specification, ¶ 0032). Therefore, claim 17 is anticipated. Claim 18 is directed towards a method for inhibiting an IRAK enzyme, comprising contacting the enzyme with an effective amount of a compound of claim 1. Claim 19 is directed towards the method of claim 18, wherein the contacting comprises administering the compound to a subject. Li teaches that the compound of claim 1 inhibit IRAK in subjects in need thereof: The present disclosure relates to a method of inhibiting IRAK protein kinase , comprising administering to a subject in need thereof a therapeutically effective amount of the compound of formula (1) , or a tautomer , mesomer , racemate , enantiomer , diastereomer , or mixture thereof , or a pharmaceutically acceptable salt thereof , or the pharmaceutical composition containing the same ; preferably the IRAK protein kinase is an IRAK - 4 protein kinase. Li, Specification, ¶ 0182. Li teaches specific in vitro examples where the compounds of formula (I) are incubated with purified IRAK4 enzyme to measure the inhibitory activity of the compounds (¶¶ 0457-0460). For example, the compound 29 has an IC50 of 26 nM and 100% IRAK4 inhibition (¶ 0460, Table 1). Therefore, claims 18-19 are anticipated. Claim 20 is directed towards a method of treating a subject for a disease or condition wherein an IRAK inhibitor is indicating, comprising administering to the subject an effective amount of the compound of claim 1. Li teaches this method: “The present disclosure relates to a method of preventing and/or treating IRAK-mediated disorder, disease, or condition, comprising a step of administering to a subject in need thereof a therapeutically effective amount of the compound of formula (I)” (Li, Specification, (¶ 0182). Therefore, claim 20 is anticipated. Claim 21 recites: The method of claim 20, where the disease or condition comprises an auto-immune disease, inflammatory disorder, cardiovascular disease, neurodegenerative disorder, allergic disorder, multi-organ failure, kidney disease, platelet aggregation, a hyperproliferative disorder, transplantation, sperm motility, erythrocyte deficiency, graft rejection, lung injury, respiratory disease, ischemic condition, bacterial infection, viral infection, immune regulatory disorder, sickle cell disease, chemical- or radiation- induced lung injury, hemorrhagic fever, or a combination thereof. Claim 21. Claim 22 recites: The method of claim 20, wherein the disease or condition is rheumatoid arthritis, systemic lupus erythematosus, Hashimoto's thyroiditis, multiple sclerosis, systemic sclerosis, myasthenia gravis, type I diabetes, uveitis, posterior uveitis, allergic encephalomyelitis, glomerulonephritis, postinfectious autoimmune diseases including rheumatic fever and post-infectious glomerulonephritis, inflammatory and hyperproliferative skin diseases, psoriasis, atopic dermatitis… Claim 22. Li teaches the compound of claim 1 for the treatment of such conditions: In another aspect, the present disclosure also relates to use of a compound of formula (I), or an isomer, pharmaceutically acceptable salt thereof, or a pharmaceutical composition containing the compound, in the manufacture of a medicament for treatment of a cancer, a neurodegenerative disorder, a viral disease, an autoimmune disease, an inflammatory disorder, a hereditary disorder, a hormone-related disease, a metabolic disorder, conditions associated with organ transplantation, immunodeficiency disorders, a destructive bone disorder, a proliferative disorder, an infectious disease, a condition associated with cell death, thrombin-induced platelet aggregation, liver disease, pathologic immune conditions involving T cell activation, a cardiovascular disorder, and a CNS disorder. Li, Specification, ¶ 0034; The “inflammatory disorder” refers to conditions of the eye such as ocular allergy, conjunctivitis, keratoconjunctivitis sicca, and vernal conjunctivitis; diseases affecting the nose including allergic rhinitis; and inflammatory disease in which autoimmune reactions are implicated or having an autoimmune component or etiology, including autoimmune hematological disorders (e.g. hemolytic anemia, aplastic anemia, pure red cell anemia and idiopathic thrombocytopenia), systemic lupus erythematosus, rheumatoid arthritis, polychondritis, scleroderma, Wegener granulamatosis, dermatomyositis, chronic active hepatitis, myasthenia gravis, Steven-Johnson syndrome, idiopathic sprue, autoimmune inflammatory bowel disease (e.g. ulcerative colitis and Crohn's disease), irritable bowel syndrome, celiac disease, periodontitis, hyaline membrane disease, kidney disease, glomerular disease, alcoholic liver disease, multiple sclerosis, endocrine opthalmopathy, Grave's disease, sarcoidosis, alveolitis, chronic hypersensitivity pneumonitis, multiple sclerosis, primary biliary cirrhosis, uveitis (anterior and posterior), Sjogren's syndrome… Li, Specification, ¶ 0195. Therefore, claims 21-22 are anticipated. Claim 23 recites: The method of claim 20, wherein the disease or condition comprises a lymphoid neoplasm selected from myeloproliferative neoplasms (MPN) excluding polycythemia vera, myeloid/lymphoid neoplasms with PDGFRA rearrangement, myeloid/lymphoid neoplasms with PDGFRB rearrangement, myeloid/lymphoid neoplasms with FGFR1 rearrangement, myeloid/lymphoid neoplasms with PCM1- JAK2, myelodysplastic/myeloproliferative neoplasms (MDS/MPN), myeloid sarcoma, myeloid proliferations related to Down syndrome, blastic plasmacytoid dendritic cell neoplasm, B-lymphoblastic leukemia/lymphoma; and/or T-lymphoblastic leukemia/lymphoma. Claim 23. Li teaches the treatment of lymphoid neoplasms selected from myeloproliferative neoplasms (MPN) including leukemia: The “cancer” or “proliferative disorder” mentioned includes… hematological malignancies (including leukemia, diffuse large B-cell lymphoma (DLBCL), ABCDLBCL, chronic lymphocytic leukemia (CLL), chronic lymphocytic lymphoma, primary effusion lymphoma, Burkitt lymphoma/leukemia, acute lymphocytic leukemia, B-cell prolymphocytic leukemia, lymphoplasmacytic lymphoma, Waldenstrom's macroglobulmemia (WM), splenic marginal zone lymphoma, multiple myeloma, plasmacytoma, and intravascular large B-cell lymphoma). Li, Specification, ¶ 0191. Therefore, claim 23 is anticipated. Claim 27 recites, “the method of claim 23, wherein the method further comprises identifying the subject having the lymphoid neoplasm.” The method of Li requires that the method of treating cancer comprises administering the drug to a subject be in need of treatment (Li, Specification, ¶ 0033), inherently showing that the patient has been identified as having the cancer (e.g. leukemia). Therefore, claim 27 is anticipated. Claims 1-3, 5-6, 9-12 and 15-16 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by “(S)-4-bromo-7-isopropoxy-1-((5-oxopyrrolidin-2-yl)methoxy)isoquinoline-6-carboxamide” (PubChem CID 126622165, published April 22, 2017, p. 1-9) (herein PubChem). Claim 1 is directed towards a compound of formula I: PNG media_image2.png 191 198 media_image2.png Greyscale , for example, I-1: (S)-4-bromo-7-isopropoxy-1-((5-oxopyrrolidin-2-yl)methoxy)isoquinoline- 6-carboxamide (claim 16), having the structure: PNG media_image8.png 207 184 media_image8.png Greyscale (Specification, p. 14). PubChem teaches (S)-4-bromo-7-isopropoxy-1-((5-oxopyrrolidin-2-yl)methoxy)isoquinoline-6-carboxamide: PNG media_image9.png 298 272 media_image9.png Greyscale (PubChem, p. 1-2). Therefore, claim 1 is anticipated. Claims 2-3, 5-6, 9-12 and 15-16 read on the compound I-1 and are therefore anticipated by PubChem for the reasons given in the rejection of claim 1. Claims 1-3, 5-6, 9-11, 14, 17-23 and 27 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Curran et al. (WO2017/025849 A1, Published Feb. 16, 2017) (of record, IDS foreign cite no. 2). Claim 1 is directed towards a compound of formula I: PNG media_image2.png 191 198 media_image2.png Greyscale , for example, PNG media_image10.png 146 170 media_image10.png Greyscale (Specification, p. 120, example 102). Curran teaches this compound: PNG media_image11.png 154 160 media_image11.png Greyscale (Curran, Specification, p. 75, example 54). Therefore, claim 1 is anticipated. Claims 2-3, 5-6, 9-11 and 14 read on the compound example 102 and are therefore anticipated by Curran for the reasons given in the rejection of claim 1. Curran also teaches the compound PNG media_image12.png 77 75 media_image12.png Greyscale (Curran, Specification, p. 66, example 37), which is a compound of formula I as in claim 1 and reads on claims 2-3, 5, 9-11 and 14. As such these claims are also anticipated by Curran example 37. Curran also teaches the compound PNG media_image13.png 169 172 media_image13.png Greyscale (Curran, Specification, p. 88, prep no. 5), which is a compound of formula I as in claim 1 and reads on claims 2-3, 5-6, 9-11 and 14. As such these claims are also anticipated by Curran prep no. 5. Claim 17 is directed towards a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient. Curran teaches a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient (Curran, Specification, p. 28, lines 20-26). Therefore, claim 17 is anticipated. Claim 18 is directed towards a method for inhibiting an IRAK enzyme, comprising contacting the enzyme with an effective amount of a compound of claim 1. Claim 19 is directed towards the method of claim 18, wherein the contacting comprises administering the compound to a subject. Curran teaches specific in vitro examples where the compounds of formula I are incubated with purified IRAK4 enzyme to measure the inhibitory activity of the compounds (Curran, Specification, pp. 105-108). For example, the compound 37 has an IC50 of 40 nM and 100% IRAK4 inhibition (p. 107, Table 1). Curran teaches administering the compound of claim 1 to treat IRAK mediated conditions in subjects in need thereof, wherein IRAK inherently would be inhibited: The compounds of the invention are also useful in treating and/or preventing a disease or condition mediated by or otherwise associated with an IRAK enzyme; the method comprising administering to a subject in need thereof an effective amount of a compound of the invention. Curran, Specification, p. 22, lines 5-7. Therefore, claims 18-19 are anticipated. Claim 20 is directed towards a method of treating a subject for a disease or condition wherein an IRAK inhibitor is indicating, comprising administering to the subject an effective amount of the compound of claim 1. As shown in the rejection of claims 18-19, Curran teaches Curran teaches administering the compound of claim 1 to treat IRAK mediated conditions in subjects in need thereof (Curran, Specification, p. 22). Therefore, claim 20 is anticipated. Claim 21 recites: The method of claim 20, where the disease or condition comprises an auto-immune disease, inflammatory disorder, cardiovascular disease, neurodegenerative disorder, allergic disorder, multi-organ failure, kidney disease, platelet aggregation, a hyperproliferative disorder, transplantation, sperm motility, erythrocyte deficiency, graft rejection, lung injury, respiratory disease, ischemic condition, bacterial infection, viral infection, immune regulatory disorder, sickle cell disease, chemical- or radiation- induced lung injury, hemorrhagic fever, or a combination thereof. Claim 21. Claim 22 recites: The method of claim 20, wherein the disease or condition is rheumatoid arthritis, systemic lupus erythematosus, Hashimoto's thyroiditis, multiple sclerosis, systemic sclerosis, myasthenia gravis, type I diabetes, uveitis, posterior uveitis, allergic encephalomyelitis, glomerulonephritis, postinfectious autoimmune diseases including rheumatic fever and post-infectious glomerulonephritis, inflammatory and hyperproliferative skin diseases, psoriasis, atopic dermatitis… Claim 22. Curran teaches the treatment of these IRAK mediated conditions: The disease may be, but not limited to, one of the following classes: auto-immune diseases, inflammatory diseases, allergic diseases, metabolic diseases, infection-based diseases, trauma or tissue-injury based diseases, fibrotic diseases, genetic diseases, diseases driven by over-activity of IL1 pathways, cardiovascular diseases, vascular diseases, heart diseases, neurological diseases, neurodegenerative diseases, respiratory diseases, pulmonary diseases, airways diseases, renal diseases, skin and/ or dermatological diseases, liver diseases, gastrointestinal diseases, oral diseases, pain and sensory diseases, hematopoietic diseases, joint diseases, muscle diseases, bone diseases, and ophthalmic and/or ocular diseases. Specific autoimmune diseases include, but are not limited to: rheumatoid arthritis, osteoarthritis, psoriasis, allergic dermatitis, systemic lupus erythematosus (and resulting complications), Sjogren's syndrome, multiple sclerosis, asthma, glomerular nephritis, irritable bowel syndrome, inflammatory bowel disease, Crohn's disease, ankylosing spondylitis, Behcet's disease, lupus nephritis, scleroderma, systemic scleroderma, type 1 or juvenile onset diabetes, alopecia universalis, acute disseminated encephalomyelitis, Addison's disease, antiphospholipid antibody syndrome, atrophic gastritis of pernicious anemia, autoimmune alopecia, autoimmune hemolytic anemia, autoimmune hepatitis… Curran, Specification, pp. 22-26. Claim 23 recites: The method of claim 20, wherein the disease or condition comprises a lymphoid neoplasm selected from myeloproliferative neoplasms (MPN) excluding polycythemia vera, myeloid/lymphoid neoplasms with PDGFRA rearrangement, myeloid/lymphoid neoplasms with PDGFRB rearrangement, myeloid/lymphoid neoplasms with FGFR1 rearrangement, myeloid/lymphoid neoplasms with PCM1- JAK2, myelodysplastic/myeloproliferative neoplasms (MDS/MPN), myeloid sarcoma, myeloid proliferations related to Down syndrome, blastic plasmacytoid dendritic cell neoplasm, B-lymphoblastic leukemia/lymphoma; and/or T-lymphoblastic leukemia/lymphoma. Claim 23. Curran teaches the treatment of lymphoid neoplasms selected from myeloproliferative neoplasms (MPN) including leukemia: Compounds of the current invention are also useful in the treatment of a proliferative disease selected from a hematological malignancies (including leukemia, diffuse large B-cell lymphoma (DLBCL), ABC DLBCL, chronic lymphocytic leukemia (CLL), chronic lymphocytic lymphoma, primary effusion lymphoma, Burkitt lymphoma/leukemia, acute lymphocytic leukemia, B-cell prolymphocytic leukemia, lymphoplasmacytic lymphoma, Waldenstrom's macroglobulinemia (WM), splenic marginal zone lymphoma, multiple myeloma, plasmacytoma, intravascular large B-cell lymphoma) Curran, Specification, p. 25, lines 9-25. Therefore, claim 23 is anticipated. Claim 27 recites, “the method of claim 23, wherein the method further comprises identifying the subject having from the lymphoid neoplasm.” The method of Curran requires that the method of treating the condition comprises administering the drug to a subject be in need of treatment (Curran, Specification, p. 22, lines 5-7), inherently showing that the patient has been identified as having the condition (e.g. leukemia). Therefore, claim 27 is anticipated. Claims 1-2, 4, 7-13, 15, 17-25 and 27 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mainolfi et al. (WO 2020/264490 A1, Published Dec. 30, 2020) (of record, IDS foreign cite no. 4). Claim 1 is directed towards a compound of formula I: PNG media_image2.png 191 198 media_image2.png Greyscale , for example, PNG media_image14.png 96 192 media_image14.png Greyscale (Specification, p. 15, example I-17) and PNG media_image15.png 109 184 media_image15.png Greyscale (example I-15). Mainolfi teaches similar compounds, still falling within the genus of claim 1: PNG media_image16.png 128 212 media_image16.png Greyscale and PNG media_image17.png 140 225 media_image17.png Greyscale (Mainolfi, Specification, ¶ 001046). Therefore, claim 1 is anticipated. Claims 2, 4, 7-13 and 15 read on the compounds of Mainolfi and are also anticipated for the reasons given in the rejection of claim 1. Claim 17 is directed towards a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient. Mainolfi teaches a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable carrier, adjuvant, or vehicle (Mainolfi, Specification, ¶ 00517). Therefore, claim 17 is anticipated. Claim 18 is directed towards a method for inhibiting an IRAK enzyme, comprising contacting the enzyme with an effective amount of a compound of claim 1. Claim 19 is directed towards the method of claim 18, wherein the contacting comprises administering the compound to a subject. Mainolfi teaches that the compounds inhibit IRAK in a biological sample or in a patient, and can be administered to such a patient in need thereof, thus inherently teaching the method of inhibiting IRAK by contacting IRAK with the compound, such as by administering the compound to the subject The amount of compound in compositions of this invention is such that is effective to measurably degrade and/or inhibit an IRAK protein kinase, or a mutant thereof, in a biological sample or in a patient. In certain embodiments, the amount of compound in compositions of this invention is such that is effective to measurably degrade and/or inhibit an IRAK protein kinase, or a mutant thereof, in a biological sample or in a patient. In certain embodiments, a composition of this invention is formulated for administration to a patient in need of such composition. Mainolfi, Specification, ¶ 00517. Therefore, claims 18-19 are anticipated. Claim 20 is directed towards a method of treating a subject for a disease or condition wherein an IRAK inhibitor is indicating, comprising administering to the subject an effective amount of the compound of claim 1. Mainolgi teaches administering the compound of claim 1 to treat IRAK mediated conditions in subjects in need thereof: In other embodiments, the present invention provides a method for treating a disorder mediated by one or more of IRAK-1, IRAK-2, and/or IRAK-4, or a mutant thereof, in a patient in need thereof, comprising the step of administering to said patient a compound according to the present invention or pharmaceutically acceptable composition thereof. Mainolfi, Specification, ¶ 00668. Therefore, claim 20 is anticipated. Claim 21 recites: The method of claim 20, where the disease or condition comprises an auto-immune disease, inflammatory disorder, cardiovascular disease, neurodegenerative disorder, allergic disorder, multi-organ failure, kidney disease, platelet aggregation, a hyperproliferative disorder, transplantation, sperm motility, erythrocyte deficiency, graft rejection, lung injury, respiratory disease, ischemic condition, bacterial infection, viral infection, immune regulatory disorder, sickle cell disease, chemical- or radiation- induced lung injury, hemorrhagic fever, or a combination thereof. Claim 21. Claim 22 recites: The method of claim 20, wherein the disease or condition is rheumatoid arthritis, systemic lupus erythematosus, Hashimoto's thyroiditis, multiple sclerosis, systemic sclerosis, myasthenia gravis, type I diabetes, uveitis, posterior uveitis, allergic encephalomyelitis, glomerulonephritis, postinfectious autoimmune diseases including rheumatic fever and post-infectious glomerulonephritis, inflammatory and hyperproliferative skin diseases, psoriasis, atopic dermatitis… Claim 22. Mainolfi teaches the treatment of these IRAK mediated conditions: In some embodiments, the present invention provides a method for treating one or more disorders, diseases, and/or conditions wherein the disorder, disease, or condition is a cancer, a neurodegenative disorder, a viral disease, an autoimmune disease, an inflammatory disorder, a hereditary disorder, a hormone-related disease, a metabolic disorder, conditions associated with organ transplantation, immunodeficiency disorders, a destructive bone disorder, a proliferative disorder, an infectious disease, a condition associated with cell death, thrombin-induced platelet aggregation, liver disease, pathologic immune conditions involving T cell activation, a cardiovascular disorder, or a CNS disorder. Mainolfi, Specification, ¶ 00546; In some embodiments the inflammatory disease which can be treated according to the methods of this invention is an disease of the skin. In some embodiments, the inflammatory disease of the skin is selected from contact dermatitits, atopic dermatitis, alopecia areata, erythema multiforma… In some embodiments the inflammatory disease which can be treated according to the methods of this invention is selected from acute and chronic gout, chronic gouty arthritis, psoriasis, psoriatic arthritis, rheumatoid arthritis, Juvenile rheumatoid arthritis, Systemic juvenile idiopathic arthritis (SJIA), Cryopyrin Associated Periodic Syndrome (CAPS), and osteoarthritis. Mainolfi, Specification, ¶¶ 00559-00560. (See also ¶¶ 547-558 and 561-572). Claim 23 recites: The method of claim 20, wherein the disease or condition comprises a lymphoid neoplasm selected from myeloproliferative neoplasms (MPN) excluding polycythemia vera, myeloid/lymphoid neoplasms with PDGFRA rearrangement, myeloid/lymphoid neoplasms with PDGFRB rearrangement, myeloid/lymphoid neoplasms with FGFR1 rearrangement, myeloid/lymphoid neoplasms with PCM1- JAK2, myelodysplastic/myeloproliferative neoplasms (MDS/MPN), myeloid sarcoma, myeloid proliferations related to Down syndrome, blastic plasmacytoid dendritic cell neoplasm, B-lymphoblastic leukemia/lymphoma; and/or T-lymphoblastic leukemia/lymphoma. Claim 23. Claims 24 recites: The method of claim 23, wherein the lymphoid neoplasm is a myeloproliferative neoplasm selected from chronic myeloid leukemia (CML), chronic neutrophilic leukemia (CNL), primary myelofibrosis (PMF), essential thrombocythemia, chronic eosinophilic leukemia, or a combination thereof. Claim 24. Claim 25 limits the MPN to chronic myeloid leukemia (CML). Mainolfi teaches the treatment of lymphoid neoplasms selected from myeloproliferative neoplasms (MPN) including chronic myeloid leukemia (CML) (Mainolfi, Specification, ¶00649). Therefore, claims 23-25 are anticipated. Claim 27 recites, “the method of claim 23, wherein the method further comprises identifying the subject having from the lymphoid neoplasm.” The method of Mainolfi requires that the method of treating the condition comprises administering the drug to a subject be in need of treatment (Mainolfi, Specification, ¶ 00668), inherently showing that the patient has been identified as having the condition (e.g. leukemia). Therefore, claim 27 is anticipated. Claims 1-3, 7, 9-11, 15, 17-23 and 27 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lee et al. (WO 2017/033093 A1, Published March 2, 2017) (of record, IDS foreign cite no. 3). Claim 1 is directed towards a compound of formula I: PNG media_image2.png 191 198 media_image2.png Greyscale . Lee teaches a compound of formula I as in claim 1, PNG media_image18.png 215 159 media_image18.png Greyscale (Lee, Specification, p. 69, example 5). As in formula I, each of R1, R3 and R6 are H, R2 is heteroaryl, R4 is C(O)NH2, R5 is isopropyl, R7 is CH2-heterocycloaliphatic and n is 1. Therefore, claim 1 is anticipated. Claims 2, 3, 7, 9-12, and 15 read on the example 5 compound and are therefore also anticipated for the reasons given for claim 1. Claim 17 is directed towards a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable excipient. Lee teaches a pharmaceutical composition comprising a compound according to claim 1, and a pharmaceutically acceptable carrier (Lee, Specification, p. 27, lines 8-14). Therefore, claim 17 is anticipated. Claim 18 is directed towards a method for inhibiting an IRAK enzyme, comprising contacting the enzyme with an effective amount of a compound of claim 1. Claim 19 is directed towards the method of claim 18, wherein the contacting comprises administering the compound to a subject. Lee teaches specific in vitro examples where the compounds of formula I are incubated with purified IRAK4 enzyme to measure the inhibitory activity of the compounds (Lee, Specification, pp. 125-129). For example, example 5 has an IC50 of 1.1-3.7 nM (p. 127, Table 1). Curran teaches administering the compound of claim 1 to treat IRAK mediated conditions in subjects in need thereof, wherein IRAK inherently would be inhibited: The compounds of the invention are also useful in treating and/or preventing a disease or condition mediated by or otherwise associated with an IRAK enzyme; the method comprising administering to a subject in need thereof an effective amount of a compound of the invention. Lee, Specification, p. 20, lines 28-30. Therefore, claims 18-19 are anticipated. Claim 20 is directed towards a method of treating a subject for a disease or condition wherein an IRAK inhibitor is indicating, comprising administering to the subject an effective amount of the compound of claim 1. As shown in the rejection of claims 18-19, Lee teaches administering the compound of claim 1 to treat IRAK mediated conditions in subjects in need thereof (Lee, Specification, p. 20). Therefore, claim 20 is anticipated. Claim 21 recites: The method of claim 20, where the disease or condition comprises an auto-immune disease, inflammatory disorder, cardiovascular disease, neurodegenerative disorder, allergic disorder, multi-organ failure, kidney disease, platelet aggregation, a hyperproliferative disorder, transplantation, sperm motility, erythrocyte deficiency, graft rejection, lung injury, respiratory disease, ischemic condition, bacterial infection, viral infection, immune regulatory disorder, sickle cell disease, chemical- or radiation- induced lung injury, hemorrhagic fever, or a combination thereof. Claim 21. Claim 22 recites: The method of claim 20, wherein the disease or condition is rheumatoid arthritis, systemic lupus erythematosus, Hashimoto's thyroiditis, multiple sclerosis, systemic sclerosis, myasthenia gravis, type I diabetes, uveitis, posterior uveitis, allergic encephalomyelitis, glomerulonephritis, postinfectious autoimmune diseases including rheumatic fever and post-infectious glomerulonephritis, inflammatory and hyperproliferative skin diseases, psoriasis, atopic dermatitis… Claim 22. Lee teaches the treatment of these IRAK mediated conditions: The disease may be, but not limited to, one of the following classes: auto-immune diseases, inflammatory diseases, allergic diseases, metabolic diseases, infection-based diseases, trauma or tissue-injury based diseases, fibrotic diseases, genetic diseases, diseases driven by over-activity of IL1 pathways, cardiovascular diseases, vascular diseases, heart diseases, neurological diseases, neurodegenerative diseases, respiratory diseases, pulmonary diseases, airways diseases, renal diseases, skin and/ or dermatological diseases, liver diseases, gastrointestinal diseases, oral diseases, pain and sensory diseases, hematopoietic diseases, joint diseases, muscle diseases, bone diseases, and ophthalmic and/or ocular diseases. Specific autoimmune diseases include, but are not limited to: rheumatoid arthritis, osteoarthritis, psoriasis, allergic dermatitis, systemic lupus erythematosus (and resulting complications), Sjogren's syndrome, multiple sclerosis, asthma, glomerular nephritis, irritable bowel syndrome, inflammatory bowel disease, Crohn's disease, ankylosing spondylitis, Behcet's disease, lupus nephritis, scleroderma,.. Curran, Specification, pp. 20-21. Claim 23 recites: The method of claim 20, wherein the disease or condition comprises a lymphoid neoplasm selected from myeloproliferative neoplasms (MPN) excluding polycythemia vera, myeloid/lymphoid neoplasms with PDGFRA rearrangement, myeloid/lymphoid neoplasms with PDGFRB rearrangement, myeloid/lymphoid neoplasms with FGFR1 rearrangement, myeloid/lymphoid neoplasms with PCM1- JAK2, myelodysplastic/myeloproliferative neoplasms (MDS/MPN), myeloid sarcoma, myeloid proliferations related to Down syndrome, blastic plasmacytoid dendritic cell neoplasm, B-lymphoblastic leukemia/lymphoma; and/or T-lymphoblastic leukemia/lymphoma. Claim 23. Lee teaches the treatment of lymphoid neoplasms selected from myeloproliferative neoplasms (MPN) including leukemia: Compounds of the current invention are also useful in the treatment of a proliferative disease selected from… hematological malignancies (including leukemia, diffuse large B-cell lymphoma (DLBCL), ABC DLBCL, chronic lymphocytic leukemia (CLL), chronic lymphocytic lymphoma, primary effusion lymphoma, Burkitt lymphoma/leukemia, acute lymphocytic leukemia, B-cell prolymphocytic leukemia, lymphoplasmacytic lymphoma, Waldenstrom's macroglobulinemia (WM), splenic marginal zone lymphoma, multiple myeloma, plasmacytoma, intravascular large B-cell lymphoma) Lee, Specification, p. 23-24. Therefore, claim 23 is anticipated. Claim 27 recites, “the method of claim 23, wherein the method further comprises identifying the subject having from the lymphoid neoplasm.” The method of Lee requires that the method of treating the condition comprises administering the drug to a subject be in need of treatment (Lee, Specification, p. 20), inherently showing that the patient has been identified as having the condition (e.g. leukemia). Therefore, claim 27 is 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. 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. Claim(s) 1-13, 15-23 and 27 is/are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (US 2022/0177446 A1, published June 9, 2022, filed Dec. 2, 2021), as applied to claims 1-13, 15, 17-23 and 27 above, in view of Lee et al. (WO 2017/033093 A1, Published March 2, 2017), as applied to claims 1-3, 7, 9-11, 15, 17-23 and 27 above. The rejection of claims 1-13, 15, 17-23 and 27 as anticipated by Li above is incorporated herein by reference. The rejection of claims 1-3, 7, 9-11, 15, 17-23 and 27 as anticipated by Lee is incorporated herein by reference. Accordingly, these claims were prima facie obvious at the time of filing. Claim 16 is directed towards the compound of claim 1, I-3, having the structure, PNG media_image19.png 133 181 media_image19.png Greyscale (Specification, p. 14). Li teaches a largely similar compound, except that R7 is substituted: PNG media_image7.png 255 212 media_image7.png Greyscale (Li, Specification, p. 21, example 29). The claimed and prior art compounds possess a sufficiently close relationship to create a reasonable expectation, in light of the totality of the prior art, that the new compound will have similar properties to the old because Li teaches that these substituents are optional (Li, Specification, ¶ 61) and compounds with the same activity but lacking the fluorine and ethyl group are commonly known in the art. For example, Lee teaches a compound of formula I as in claim 1 wherein R7 is unsubstituted, PNG media_image18.png 215 159 media_image18.png Greyscale (Lee, Specification, p. 69, example 5). Therefore, claim 16 was prima facie obvious at the time of filing. Claim(s) 1-13, 15-25 and 27 is/are rejected under 35 U.S.C. 103 as being unpatentable over Mainolfi et al. (WO 2020/264490 A1, Published Dec. 30, 2020), as applied to claims 1-2, 4, 7-13, 15, 17-25 and 27 above, and further in view of Li et al. (US 2022/0177446 A1, published June 9, 2022, filed Dec. 2, 2021) and Lee et al. (WO 2017/033093 A1, Published March 2, 2017) as applied to claims 1-13, 15-23 and 27 above. The rejection of claims 1-2, 4, 7-13 and 15 as anticipated by Mainolfi is incorporated herein by reference. As such, these claims were prima facie obvious at the time of filing. The rejection of claims 1-13, 15-23 and 27 above is incorporated herein by reference. Claim 16 is directed towards a compound of claim 1, I-17 PNG media_image14.png 96 192 media_image14.png Greyscale (Specification, p. 15, example I-17) and I-15 PNG media_image15.png 109 184 media_image15.png Greyscale (example I-15). Mainolfi teaches largely similar IRAK binding compounds, falling within the genus of claim 1: PNG media_image16.png 128 212 media_image16.png Greyscale and PNG media_image17.png 140 225 media_image17.png Greyscale (Mainolfi, Specification, ¶ 001046). While these compounds differ in that R7 is substituted and R5 is methyl instead of isopropyl, the claimed and prior art compounds possess a sufficiently close relationship to create a reasonable expectation, in light of the totality of the prior art, that the new compound will have similar properties to the old because it is well known in the art that IRAK inhibitors with the same core structure can have unsubstituted R7 and R5 isopropyl. For example, Li teaches a similar compounds wherein R5 is isopropyl: PNG media_image20.png 278 213 media_image20.png Greyscale and that R7 substituents are optional (Li, Specification, ¶ 61) (Li, Specification, p. 24) and Lee teaches IRAK inhibitor wherein R5 is isopropyl and R7 is unsubstituted, PNG media_image18.png 215 159 media_image18.png Greyscale (Lee, Specification, p. 69, example 5). Therefore, claim 16 was prima facie obvious at the time of filing. Claims 1-3, 7, 9-11, 15-23 and 27 is/are rejected under 35 U.S.C. 103 as being unpatentable over Lee et al. (WO 2017/033093 A1, Published March 2, 2017). The rejection of claims 1-3, 7, 9-11, 15, 17-23 and 27 as anticipated by Lee is incorporated herein by reference. Accordingly, these claims were prima facie obvious at the time of filing. Claim 16 is directed towards a compound of claim 1, I-47, PNG media_image21.png 137 177 media_image21.png Greyscale (Specification, p. 17, example I-47). Lee teaches a largely similar compound , PNG media_image18.png 215 159 media_image18.png Greyscale (Lee, Specification, p. 69, example 5). While in example 5, the pyrazole is substituted with methyl and in the instantly claimed compound the pyrazole is unsubstituted, the claimed and prior art compounds possess a sufficiently close relationship to create a reasonable expectation, in light of the totality of the prior art, that the new compound will have similar properties to the old because Lee teaches that the pyrazole is optionally substituted (Lee, Specification, p. 20, lines 9-10). Therefore, claim 16 was prima facie obvious at the time of filing. Claims 1-25 and 27 is/are rejected under 35 U.S.C. 103 as obvious over Curran et al. (WO2017/025849 A1, Published Feb. 16, 2017), as applied to claims 1-3, 5-6, 9-11, 14, 17-23 and 27 above and further in view of Mainolfi et al. (WO 2020/264490 A1, Published Dec. 30, 2020), as applied to claims 1-2, 4, 7-13, 15, 17-25 and 27 above, and Li et al. (US 2022/0177446 A1, published June 9, 2022, filed Dec. 2, 2021), as applied to claims 1-13, 15, 17-23 and 27 above. The rejection of claims 1-3, 5-6, 9-11, 14, 17-23 and 27 above as anticipated by Curran is incorporated herein by reference. The rejection of claims 1-2, 4, 7-13, 15, 17-25 and 27 above as anticipated by Mainolfi is incorporated herein by reference. The rejection of claims 1-13, 15, 17-23 and 27 as anticipated by Li above is incorporated herein by reference. As such these claims were prima facie obvious at the time of filing. Claim 16 is directed towards the compound of claim 1, I-95, PNG media_image22.png 114 185 media_image22.png Greyscale (Specification, p. 19, example I-95) and I-96 PNG media_image23.png 116 183 media_image23.png Greyscale (Specification, p. 19, example I-96). Curran teaches the compound PNG media_image12.png 77 75 media_image12.png Greyscale (Curran, Specification, p. 66, example 37). While this compound differs by the R2 substituent and has a halogen instead of substituted alkynyl, the claimed and prior art compounds possess a sufficiently close relationship to create a reasonable expectation, in light of the totality of the prior art, that the new compound will have similar properties to the old because it is commonly known in the art that IRAK inhibitors can be substituted either with substituted alkynyl or halogen and have similar IRAK inhibiting activities. For example, Mainolfi teaches largely similar IRAK binding compounds, which have the same R2 substituent as instantly claimed: PNG media_image16.png 128 212 media_image16.png Greyscale and PNG media_image17.png 140 225 media_image17.png Greyscale (Mainolfi, Specification, ¶ 001046). Li teaches both alkynyl and halogen for the R2 substituent: PNG media_image24.png 114 200 media_image24.png Greyscale PNG media_image24.png
Read full office action

Prosecution Timeline

May 31, 2023
Application Filed
Sep 08, 2025
Non-Final Rejection — §101, §102, §103
Mar 20, 2026
Response Filed

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Prosecution Projections

1-2
Expected OA Rounds
46%
Grant Probability
71%
With Interview (+25.4%)
3y 3m
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Low
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