Prosecution Insights
Last updated: April 19, 2026
Application No. 18/024,236

MEDIUM- OR MACRO-CYCLIC BENZYL-SUBSTITUTED HETEROCYCLE DERIVATIVES AND THEIR USES AS OREXIN-2 RECEPTOR AGONISTS

Non-Final OA §112
Filed
Mar 01, 2023
Examiner
WILLIS, DOUGLAS M
Art Unit
1624
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Centessa Pharmaceuticals (Uk) Limited
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 and 77-95 are pending in the instant invention. According to the Amendments to the Claims, filed October 31, 2025, claim 1 was amended, claims 2-76 were cancelled and claims 82-95 were added. Status of Priority This invention is a 35 U.S.C. § 371 National Stage Filing of International Application No. PCT/US2021/049003, filed September 3, 2021, which claims priority under 35 U.S.C. § 119(e) to US Provisional Application No. 63/074,220, filed September 3, 2020. Although the inventor’s or joint inventor’s claim for the benefit of a prior-filed invention under 35 U.S.C. § 119(e) is acknowledged, the inventor or joint inventor has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. § 119(e) as follows: The later-filed invention must be an invention for a patent, for an invention which is also disclosed in the prior-filed invention (the provisional invention). The disclosure of the invention in the prior-filed invention and in the later-filed invention must be sufficient to comply with the requirements of 35 U.S.C. § 112(a). {See Transco Products, Inc. v. Performance Contracting, Inc., 38 F.3d 551, 32 USPQ2d 1077 (Fed. Cir. 1994)}. The specification of the prior-filed invention, US Provisional Application No. 63/074,220, fails to provide adequate support or enablement in the manner provided by 35 U.S.C. § 112(a) for one or more claims of this invention for the following reason: the specification in the instant invention has been amended with respect to the scope of Formula (IIB’), which now discloses amended definitions for at least Ra and Rb, respectively, and is no longer coextensive with that of US Provisional Application No. 63/074,220. Consequently, since the specification of US Provisional Application No. 63/074,220 lacks adequate support or enablement for one or more claims of the elected invention of Group I, as defined below in Restrictions / Election of Species, and in the manner provided by 35 U.S.C. § 112(a), the first Office action on the merits of all relevant claims drawn to Group I will be prosecuted according to the earliest effective filing date afforded this invention, which is that of International Application No. PCT/US2021/049003, filed September 3, 2021. Restrictions / Election of Species PNG media_image1.png 200 400 media_image1.png Greyscale The inventor’s or joint inventor’s provisional election of the following, without traverse, in the reply filed on October 31, 2025, is acknowledged: a) Group I - claims 1, 77 and 82-95; and b) substituted macrocycle of Formula (IIB’) - p. 113, Table B1, Compound No. B1-1, shown to the right below, and hereafter referred to as N-((1R,16aR)-5-oxo-12-phenyl-2,3,5,6,7,8,9,10,16,16a-decahydro-1H-benzo[b]pyrrolo[2,1-e]-[1]oxa[6]azacyclododecin-1-yl)ethanesulfonamide, where n = 1; n1 = 1; R1 = -CH2CH3; Z = -NRZ-, wherein RZ = -H; Ra = -H; Rb = -H; X = -CH2(CH2)3CH2-; L = -absent-; Y = -O-; and RA1 = -Ar2, wherein Ar2 = -Ph. Claims 1, 77, 82-88, 90, 91, 93 and 95 read on the elected species. Affirmation of this election must be made by the inventor or joint inventor in replying to this Office action. PNG media_image2.png 200 400 media_image2.png Greyscale 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 78-81 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, 77 and 82-95 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. 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(a) and/or 35 U.S.C. § 112(b), the existing recitation should be replaced with the following recitation: A compound of Formula (IIB’): PNG media_image3.png 200 400 media_image3.png Greyscale (IIB’) or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: R1 is C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, NHC3-C10 cycloalkyl, NH(3- to 7-membered heterocycloalkyl), NHC6-C10 aryl, NH(5- to 10-membered heteroaryl), OH, OC1-C6 alkyl, OC3-C10 cycloalkyl, O(3- to 7-membered heterocycloalkyl), OC6-C10 aryl, O(5- to 10-membered heteroaryl), SH, SC1-C6 alkyl, SC6-C10 aryl, C3-C7 cycloalkyl, 3- to 7-membered heterocycloalkyl, C6-C10 aryl, or 5- to 10-membered heteroaryl; wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OC1-C6 alkyl, or SC1-C6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, SC1-C6 alkyl, S(O)2C1-C6 alkyl, C3-C7 cycloalkyl, and 3- to 7-membered heterocycloalkyl; wherein the C1-C6 haloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, SC1-C6 alkyl, S(O)2C1-C6 alkyl, C3-C7 cycloalkyl, and 3- to 7-membered heterocycloalkyl; wherein the NHC3-C10 cycloalkyl, NH(3- to 7-membered heterocycloalkyl), OC3-C10 cycloalkyl, O(3- to 7-membered heterocycloalkyl), C3-C7 cycloalkyl, or 3- to 7-membered heterocycloalkyl is optionally substituted with one or more independently selected R1S substituents; and wherein the NHC6-C10 aryl, NH(5- to 10-membered heteroaryl), OC6-C10 aryl, O(5- to 10-membered heteroaryl), SC6-C10 aryl, C6-C10 aryl, or 5- to 10-membered heteroaryl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, SC1-C6 alkyl, S(O)2C1-C6 alkyl, C3-C7 cycloalkyl, and 3- to 7-membered heterocycloalkyl; each R1S is independently halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, =O, SC1-C6 alkyl, S(O)2C1-C6 alkyl, C3-C7 cycloalkyl, or 3- to 7-membered heterocycloalkyl; Z is -NRZ- or -O-; RZ is H or C1-C6 alkyl; Ra is H, halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, or OC1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NHC1-C6 alkyl, N(C1-C6 alkyl)2, or OC1-C6 alkyl is optionally substituted with one or more independently selected RS substituents; Rb is H, halogen, CN, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, or OC1-C6 alkyl, wherein the C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, NHC1-C6 alkyl, N(C1-C6 alkyl)2, or OC1-C6 alkyl is optionally substituted with one or more independently selected RS substituents; each RS is independently halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, or OC1-C6 alkyl; n is 1 or 2; X is -C1-C4 alkylene-, -NH-, -N(C1-C6 alkyl)-, or -O-, wherein the -C1-C4 alkylene- or -N(C1-C6 alkyl)- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, and OC1-C6 alkyl; L is absent, -C1-C2 alkylene-, or -C2-C6 alkenylene-, wherein the -C1-C2 alkylene- or -C2-C6 alkenylene- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, and OH; Y is -C1-C4 alkylene- or -O-, wherein the -C1-C4 alkylene is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, and OC1-C6 alkyl; each RA1 is independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, OC1-C6 haloalkyl, or Ar2; n1 is 0, 1, 2, 3, or 4; each Ar2 is independently C6-C10 aryl or 5- to 10-membered heteroaryl, wherein each C6-C10 aryl and 5- to 10-membered heteroaryl is optionally and independently substituted with one or more independently selected RA2 substituents; and each RA2 is independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, or OC1-C6 haloalkyl. Appropriate correction is required. See MPEP § 2173.02. Claim 77 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 pharmaceutical composition comprising a pharmaceutically acceptable diluent or carrier and the compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof. Appropriate correction is required. See MPEP § 2173.02. Claim 82 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein n is 1. Appropriate correction is required. See MPEP § 2173.02. Claim 83 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: Z is -NRZ-; and RZ is H. Appropriate correction is required. See MPEP § 2173.02. Claim 84 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R1 is C1-C6 alkyl, wherein the C1-C6 alkyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, OC1-C6 alkyl, SC1-C6 alkyl, S(O)2C1-C6 alkyl, C3-C7 cycloalkyl, and 3- to 7-membered heterocycloalkyl, and further wherein at least one substituent is halogen. Appropriate correction is required. See MPEP § 2173.02. Claim 85 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein R1 is CH3 or CH2CH3. Appropriate correction is required. See MPEP § 2173.02. Claim 86 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein: Ra is H or halogen; and Rb is H or halogen. Appropriate correction is required. See MPEP § 2173.02. Claim 87 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein at least one RA1 is Ar2. Appropriate correction is required. See MPEP § 2173.02. Claim 88 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein at least one Ar2 is C6-C10 aryl, wherein the C6-C10 aryl is optionally substituted with one or more independently selected RA2 substituents. Appropriate correction is required. See MPEP § 2173.02. Claim 89 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein X is -NH-, -N(C1-C6 alkyl)-, or -O-, wherein the -N(C1-C6 alkyl)- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, and OC1-C6 alkyl. Appropriate correction is required. See MPEP § 2173.02. Claim 90 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein X is -C1-C4 alkylene-, wherein the -C1-C4 alkylene- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, and OC1-C6 alkyl. Appropriate correction is required. See MPEP § 2173.02. Claim 91 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Y is -O-. Appropriate correction is required. See MPEP § 2173.02. Claim 92 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein Y is -C1-C4 alkylene-, wherein the -C1-C4 alkylene- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, OH, and OC1-C6 alkyl. Appropriate correction is required. See MPEP § 2173.02. Claim 93 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein L is absent. Appropriate correction is required. See MPEP § 2173.02. Claim 94 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: The compound of claim 1, or a pharmaceutically acceptable salt or stereoisomer thereof, wherein L is -C1-C2 alkylene- or -C2-C6 alkenylene-, wherein the -C1-C2 alkylene- or -C2-C6 alkenylene- is optionally substituted with one or more substituents independently selected from the group consisting of halogen, CN, NH2, NHC1-C6 alkyl, N(C1-C6 alkyl)2, and OH. Appropriate correction is required. See MPEP § 2173.02. Claim 95 is objected to because of the following informalities: for clarity, precision and to avoid issues under 35 U.S.C. § 112(a), 35 U.S.C. § 112(b) and/or 35 U.S.C. § 112(d), the existing recitation should be replaced with the following recitation(s): 95. The compound of claim 1, or a stereoisomer thereof, wherein the compound, or stereoisomer thereof, is selected from the group consisting of: PNG media_image4.png 200 400 media_image4.png Greyscale , 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 , PNG media_image12.png 200 400 media_image12.png Greyscale , PNG media_image13.png 200 400 media_image13.png Greyscale , 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 , PNG media_image21.png 200 400 media_image21.png Greyscale , PNG media_image22.png 200 400 media_image22.png Greyscale , PNG media_image23.png 200 400 media_image23.png Greyscale , PNG media_image24.png 200 400 media_image24.png Greyscale , PNG media_image25.png 200 400 media_image25.png Greyscale , PNG media_image26.png 200 400 media_image26.png Greyscale , PNG media_image27.png 200 400 media_image27.png Greyscale , PNG media_image28.png 200 400 media_image28.png Greyscale , PNG media_image29.png 200 400 media_image29.png Greyscale , PNG media_image30.png 200 400 media_image30.png Greyscale , PNG media_image31.png 200 400 media_image31.png Greyscale , PNG media_image32.png 200 400 media_image32.png Greyscale , PNG media_image33.png 200 400 media_image33.png Greyscale , PNG media_image34.png 200 400 media_image34.png Greyscale , PNG media_image35.png 200 400 media_image35.png Greyscale , PNG media_image36.png 200 400 media_image36.png Greyscale , PNG media_image37.png 200 400 media_image37.png Greyscale , PNG media_image38.png 200 400 media_image38.png Greyscale , PNG media_image39.png 200 400 media_image39.png Greyscale , PNG media_image40.png 200 400 media_image40.png Greyscale , and PNG media_image41.png 200 400 media_image41.png Greyscale , or a pharmaceutically acceptable salt thereof. 96. A compound: PNG media_image42.png 200 400 media_image42.png Greyscale , or a pharmaceutically acceptable salt or stereoisomer thereof. Appropriate correction is required. See MPEP § 2173.02. Claim Rejections - 35 U.S.C. § 112(a) The following is a quotation of the first paragraph of 35 U.S.C. § 112: (a) IN GENERAL. The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention. Substituted macrocycles of the Formula (IIB’) Claims 1, 77 and 82-95 are rejected under 35 U.S.C. § 112(a) because the specification, while being enabling for substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are as presented herein in the section above entitled Claim Objections, does not reasonably provide enablement for substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections. The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention commensurate in scope with these claims. Substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections, as recited in claims 1, 77 and 95, respectively, have not been adequately enabled in the specification to allow any person having ordinary skill in the art, at the time this invention was made, to make and/or use substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections. There are many factors to be considered when determining whether there is sufficient evidence to support a determination that a disclosure does not satisfy the enablement requirement and whether any necessary experimentation is undue. These factors include, but are not limited to: (a) breadth of the claims; (b) nature of the invention; (c) state of the prior art; (d) level of one of ordinary skill in the art; (e) level of predictability in the art; (f) amount of direction provided by the inventor or joint inventor; (g) existence of working examples; and (h) quantity of experimentation needed to make or use the invention based on the content of the disclosure. {See Ex parte Forman 230 USPQ 546 (Bd. Pat. App. & Inter. 1986); and In re Wands, 8 USPQ2d 1400 (Fed. Cir. 1988)}. The above factors, regarding the instant invention, are summarized as follows: PNG media_image1.png 200 400 media_image1.png Greyscale (a) Breadth of the claims - the breadth of the claims includes substituted macrocycles of the Formula (IIB’), shown to the right; (b) Nature of the invention - the nature of the invention is evaluation of substituted macrocycles of the Formula (IIB’), shown to the right above, and the pharmacokinetic behavior of these substances as orexin-2 receptor agonists; (c) State of the prior art - Nature Reviews: Drug Discovery offers a snapshot of the state of the drug development art. Herein, drug development is stated to follow the widely accepted Ehrlich model which includes: (1) development of a broad synthetic organic chemistry program; (2) subsequent testing of compounds in an appropriate laboratory model for the disease to be treated; and (3) screening of compounds with low toxicity in prospective clinical trials (Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205). Moreover, WO 22/051583, as provided in the file and cited on the IDS, illustrates a synthesis of the instantly recited substituted macrocycles of the Formula (IIB’) {Lefker, et al. WO 22/051583, 2022}; (d) Level of one of ordinary skill in the art - the artisans synthesizing the inventor’s or joint inventor’s substituted macrocycles of the Formula (IIB’) would be a collaborative team of synthetic chemists and/or health practitioners, possessing commensurate degree level and/or skill in the art, as well as several years of professional experience; (e) Level of predictability in the art - Synthetic organic chemistry is quite unpredictable (See In re Marzocchi and Horton 169 USPQ at 367 ¶3). Similarly, it is unclear based on the combination of Examples, on pages 184-319 of the instant specification, and Lefker, et al. in WO 22/051583, as provided in the file and cited on the IDS, whether the instantly recited substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections, are enabled. Moreover, the following excerpt is taken from Dörwald, which has relevance to the synthesis of substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections (Dörwald, F. Zaragoza. Side Reactions in Organic Synthesis: A Guide to Successful Synthesis Design, Weinheim: WILEY-VCH Verlag GmbH & Co. KGaA, 2005, Preface): Most non-chemists would probably be horrified if they were to learn how many attempted syntheses fail, and how inefficient research chemists are. The ratio of successful to unsuccessful chemical experiments in a normal research laboratory is far below unity, and synthetic research chemists, in the same way as most scientists, spend most of their time working out what went wrong, and why. Despite the many pitfalls lurking in organic synthesis, most organic chemistry textbooks and research articles do give the impression that organic reactions just proceed smoothly and that the total synthesis of complex natural products, for instance, is maybe a labor-intensive but otherwise undemanding task. In fact, most syntheses of structurally complex natural products are the result of several years of hard work by a team of chemists, with almost every step requiring careful optimization. The final synthesis usually looks quite different from that originally planned, because of unexpected difficulties encountered in the initially chosen synthetic sequence. Only the seasoned practitioner who has experienced for himself the many failures and frustrations which the development (sometimes even the repetition) of a synthesis usually implies will be able to appraise such work. Chemists tend not to publish negative results, because these are, as opposed to positive results, never definite (and far too copious). (f) Amount of direction provided by the inventor - the invention lacks direction with respect to making and/or using substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections; (g) Existence of working examples - the inventor or joint inventor has provided sufficient guidance to make and/or use substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are as presented herein in the section above entitled Claim Objections; however, the disclosure is insufficient to allow extrapolation of the limited examples to enable the instantly recited substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections. The specification lacks working examples of substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections. Within the specification, [A]t least one specific operative embodiment or example of the invention must be set forth. The example(s) and description should be of sufficient scope as to justify the scope of the claims. Markush claims must be provided with support in the disclosure for each member of the Markush group. Where the constitution and formula of a chemical compound is stated only as a probability or speculation, the disclosure is not sufficient to support claims identifying the compound by such composition or formula. See MPEP § 608.01(p) and MPEP § 2173.05. PNG media_image43.png 200 400 media_image43.png Greyscale (h) Quantity of experimentation needed to make or use the invention based on the content of the disclosure - predicting whether a recited compound is in fact one that produces a desired physiological effect at a therapeutic concentration and with useful kinetics, is filled with experimental uncertainty, and without proper guidance, would involve a substantial amount of experimentation (Jordan, V. C. Nature Reviews: Drug Discovery, 2, 2003, 205-213). Similarly, the specification, as originally filed, including any references incorporated therein, fails to provide the necessary support required by 35 U.S.C. § 112(a) to enable the instantly recited substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections. Thus, it is unclear, based on the guidance provided by the specification, whether a substituted macrocycle of the Formula (IIB’), such as N-((7R,16R,16aR)-7-cyano-5-methyl-10-oxo-4-phenyl-5,7,8,9,10,12,13,14,-15,16,16a,17-dodecahydro-6H-6,9-methanoazepino[1,2-a]benzo[d][1,6]diazacyclo-undecin-16-yl)methanesulfonamide, shown to the left above, is either synthetically feasible or possesses utility as an orexin-2 receptor agonist. A conclusion of lack of enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the invention was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention without undue experimentation. {See In re Wright, 999 F.2d 1557, 1562, 27 USPQ2d 1510, 1513 (Fed. Cir. 1993)}. The determination that undue experimentation would have been needed to make and use the claimed invention is not a single, simple factual determination. Rather, it is a conclusion reached by weighing all the above noted factual considerations. (See In re Wands, 858 F.2d at 737, 8 USPQ2d at 1404). These factual considerations are discussed comprehensively in MPEP § 2164.08 (scope or breadth of the claims), § 2164.05(a) (nature of the invention and state of the prior art), § 2164.05(b) (level of one of ordinary skill), § 2164.03 (level of predictability in the art and amount of direction provided by the inventor or joint inventor), § 2164.02 (the existence of working examples) and § 2164.06 (quantity of experimentation needed to make or use the invention based on the content of the disclosure). Based on a preponderance of the evidence presented herein, the conclusion that the inventor or joint inventor is insufficiently enabled for making and/or using substituted macrocycles of the Formula (IIB’), wherein the substituted macrocycles of the Formula (IIB’) are not as presented herein in the section above entitled Claim Objections, is clearly justified. The examiner suggests amending the claims, particularly as stated in the section above entitled Claim Objections, to overcome this rejection. 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. Claim 95 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. PNG media_image44.png 200 400 media_image44.png Greyscale The inventor or joint inventor should note that claim 95 recites the limitation, The compound or salt of claim 1, wherein the compound is… (shown to the right), in line 1 of the claim. There is insufficient antecedent basis, in claim 1, for this limitation, with respect to the aforementioned substituted macrocycle. According to claim 1, the aforementioned substituted macrocycle (i.e. X = -CH2-, L = -OCH2CH2O-, and Y = -CH2-) is not recited as a substituted macrocycle of the Formula (IIB’), particularly with respect to L. 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

Mar 01, 2023
Application Filed
Dec 28, 2025
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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