Bruton's tyrosine kinase and mutant degrader, composition and application thereof

Abstract

Disclosed are a Bruton's tyrosine kinase and a mutant degrader thereof, or a stereoisomer thereof, or a stereoisomer mixture thereof or a pharmaceutically acceptable salt thereof, and an application thereof in the preparation of a drug for treating diseases, disorders or conditions that would benefit from the degradation of the Bruton's tyrosine kinase and the mutant thereof. The compound of the present invention can degrade BTK protein, can degrade BTKC481S protein, has an anti-proliferation inhibiting effect on tumor cell strains Mino and OCI-LY10, shows good anti-tumor activity in an OCI-LY10 subcutaneous transplantation tumor model, has an inhibiting effect on B cell activation, and can be applied to B cell or plasma cell proliferative diseases and autoimmune diseases. The compound of the present invention has good oral absorption properties, and can be applied to oral treatment of human or animal B cell or plasma cell proliferative diseases and autoimmune diseases.

Description

TECHNICAL FIELD The invention belongs to the technical field of pharmaceutical synthesis, and specifically 5 relates to a degrader of Bruton's tyrosine kinase and Bruton's tyrosine kinase mutant, and its composition and application thereof. BACKGROUND Bruton's tyrosine kinase (Btk), a member of the Tec family of non-receptor tyrosine kinases, is a key signaling enzyme expressed in all hematopoietic cell types except T 10 lymphocytes and natural killer cells. Btk plays a critical role in the B cell signaling pathway linking cell surface B-cell receptor (BCR) stimulation to downstream intracellular responses. Btk is a key regulator of B cell development, activation, signaling and survival. In addition, Bkt plays a role in numerous other hematopoietic cell signaling pathways, such as Toll like receptor (TLR) and cytokine receptor-mediated TNF-a production in macrophages, and immunoglobulin E 15 receptor (FcsR1) signaling in mast cells, inhibition of Fas / APO-1 cell apoptosis signaling and collagen-stimulated platelet aggregation in B-lineage lymphoid cells. See, for example, C.A. Jeffries et al., J. Bio. Chem. (2003) 278: 26258-26264, N. J. Horwood et al., J. Exp. Med. (2003) 197: 1603-1611. Research in recent years has shown that the Btk signaling pathway is a new hot spot in the clinical treatment research of non-Hodgkin lymphoma (NHL), especially chronic 20 lymphocytic leukemia (CLL), B-cell lymphoma and autoimmune diseases. By acting on the BCR signaling pathway, small molecule Btk inhibitors bind to Btk to inhibit Btk autophosphorylation, prevent Btk activation, and thereby block cell conduction and induce apoptosis. As BTK inhibition is used in the clinical setting, some CLL patients have developed 25 acquired resistance to covalent BTK drugs caused by BTK C481 mutations. A new generation of BTK drugs is urgently needed to solve this acquired resistance. In recent years, significant progress has been made in the targeted protein degradation technology (PROTAC), which achieves target protein degradation by inducing ubiquitination of target proteins. Drugs using this technology do not need to continuously occupy the target 30 proteins, and the catalytic concentration can achieve target degradation. Therefore, the 2022303441   30 Mar 2026 development of targeting degradation molecules for BTK is expected to solve the problem of acquired resistance to BTK. The reference to prior art in the background above is not and should not be taken as an acknowledgment or any form of suggestion that the referenced prior art forms part of the 5 common general knowledge in Australia or in any other country. SUMMARY The purpose of the present invention is to provide a novel, unreported BTK degradation molecule with excellent properties, its optical isomer or pharmaceutically acceptable salt thereof, having high degradation activity against BTK and position 481 cysteine mutation-type BTK, 10 having anti-proliferation inhibitory effect on Mino and OCI-LY10 tumor cell lines, showing good anti-tumor activity in OCI-LY10 subcutaneous transplanted tumor model, having inhibitory effect on B cell activation, and having excellent oral PK property. The present invention also provides a pharmaceutical composition comprising the above compound and its optical isomer or pharmaceutically acceptable salt thereof. The present 15 invention relates to a class of drugs or pharmaceutically acceptable salts that can degrade BTK or position 481 cysteine mutation-type BTK protein, and can be used as medicaments to treat hyperproliferative diseases, such as cancer and inflammation, as well as immune and autoimmune diseases. A first aspect of the present invention provides a compound as shown in the formula (I), 20 or its pharmaceutically acceptable salt thereof: BTKCJ-----L-----f E3CJ o (i) or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt thereof; where: 25          BTKcl represents a chemical ligand that can bind to BTK kinase. E3cl represents a chemical ligand that can bind to E3 ubiquitin ligase. L represents a class of chemical groups or chemical bonds that connect BTKcl and E3cl at the same time. As a preferred embodiment, E3cl is selected from: chemical fragments that bind to the E3 30 ubiquitin ligase CRBN. L has the following structure: 2022303441   30 Mar 2026 -X1-L1-X2-Cyc1-X3-L2-X4-Cyc2-X5-L3-X6-Cyc3-X7-L4-X8-wherein: X1, X2, X3, X4, X5, X6, X7 and X8 are each independently selected from: absent (or chemical bonds), -O-, -S-, or -N(Ra)-. 5          L1, L2, L3, and L4 are each independently selected from: absent, chemical bonds, C1-C4 alkyl, C2-C4 alkenyl, or C2-C4 alkynyl. The above-mentioned alkyl, alkenyl, and alkynyl can be substituted with oxo, alkyl, halogen, cyano, or haloalkyl. Cyc1, Cyc2, and Cyc3 are each independently selected from: absent, 3-12 membered heterocyclic ring, a 5-12 membered aromatic ring (such as benzene ring), a 5-12 membered 10 heteroaromatic ring, a 3-12 membered cycloalkane, a 4-12 membered cycloalkyne, a 3-12 membered cycloalkene, wherein the heterocyclic ring, aromatic ring, heteroaromatic ring, cycloalkane, cycloalkyne, and cycloalkene can be substituted with oxo, alkyl, halogen, cyano, haloalkyl. Ra is selected from: H, C1-C4 alkyl. 15 As a preferred embodiment, BTKcl is selected from the following structures: B  CD wherein: when BTKcl is selected from structure B, C, D: Rb is selected from: H, halogen, cyano, methyl, -CF3, C1-C3 alkoxy; 20 Rc can be one or more, each independently selected from: H, CN, halogen, C1-C4 alkyl, C1-C4 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 alkylamino; Rd is selected from: C1-C6 alkyl, C1-C6 haloalkyl, C3-C8 cycloalkyl, C3-C8 heterocyclyl; the C1-C6 alkyl, cycloalkyl, and heterocyclyl can be further substituted with one or more substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, 25 oxo, carboxyl, ester group, amido, hydroxyl; and p is selected from: an integer of 0-4. As a preferred embodiment, BTKcl is selected from the following structures: 2022303441   30 Mar 2026 Y1 is selected from: N, CR2; Y2 and Y3 are independently selected from: N, CH; ring A is selected from: 3-12 membered heterocyclic ring; 5 ring B is selected from: 5-6 membered heteroaromatic ring, a 5-10 membered heterocyclic ring, wherein the heteroaromatic ring and heterocyclic ring can be further substituted with one or more substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, amido, hydroxyl, wherein two substituents of ring B can be connected to form a bridged ring, a spiro ring, a fused ring; 10 D is selected from: chemical bonds, C1-C3 alkyl, -O-, -NH-, -S-; R1 can be one or more, each R1 is independently selected from: halogen, C1-C6 alkyl, C1-C6 haloalkyl, -CN, -COOH, -NH2; R2 is selected from: hydrogen, cyano, halogen, C1-C4 alkyl, C3-C8 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy; 15          R3 can be one or more, each R3 is independently selected from: 3-12 membered heterocyclyl, 5-12 membered heteroaryl, 5-12 membered aryl (such as phenyl), 3-12 membered cycloalkyl, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, amido, or hydroxyl, wherein the heterocyclyl, heteroaryl, and cycloalkyl can be further substituted with substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 20 alkoxy, cyano, oxo, carboxyl, ester group, amido, or hydroxyl. Wherein two R3s of ring A can be connected to form a spiro ring, a bridged ring, a fused ring; m is selected from: an integer of 0-3; n is selected from: an integer of 0-2; represents that the atom connected thereto is connected to L; 25 when Y1 is selected from CH, ring A is a monocyclic ring, and ring B is a benzene ring, a 5-6 membered heteroaromatic ring, a 4-6 membered alkane heterocyclic ring or an 8-10 membered spiro ring, R3 is not C1-C4 alkyl, C1-C4 haloalkyl. Further, a preferred compound of the present invention has the structure of the general formula II(b) 2022303441   30 Mar 2026 (IIb) or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt thereof; Further, a preferred compound of the present invention has the structure 5 of general formula III(a) or III(b): III(a)                                            III(b) or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceutically acceptable salt thereof; 10 ring B is not a bridged ring; R3 is selected from: C1-C4 alkyl, C1-C4 haloalkyl, 3-6 membered cycloalkyl, 3-6 membered heterocyclyl, 5-6 membered aryl (such as phenyl), 5-6 membered heteroaryl, wherein the cycloalkyl, heterocyclyl, aryl (phenyl), and the heteroaryl can be further substituted with one or more substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, 15 cyano, oxo, carboxyl, ester group, amide, hydroxyl, two substituents on the cycloalkyl, heterocyclyl, aryl (phenyl), and heteroaryl can be connected to form a fused ring, a bridged ring, or a spiro ring; when Y1 is selected from CH, R3 is not C1-C4 alkyl, C1-C4 haloalkyl. Still further, a preferred compound of the present invention has the structure of the 20 general formula IV(a), IV(b), IV(c), and IV(d): 2022303441   30 Mar 2026 or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt thereof; 5 wherein the fused ring or spiro ring structure composed of ring G and ring F is selected from: 10 The above-mentioned fused ring, spiro ring structure can be further substituted with one or more substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, amido, hydroxyl. 2022303441   30 Mar 2026 Further, a preferred compound of the present invention has the structure of the general formula V(a) or V(b): V(a)                               V(b) 5 or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt thereof; Z is selected from: -CH2-, -CH2CH2-, -O-. As a further preferred embodiment, in the general formulas III(a) and III(b) R3 is preferably selected from: C1-C4 alkyl, ring D; 10 ring D is selected from: / \ [jA r                  hn'a o"\ hn                         c V-- hn \-- r )--- । ?-- . , O , H , \= / ,    \— / ,            ,           , ring D can be further substituted with one or more substituents which can be on C atom or N atom and are selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, amide, hydroxyl. Two substituents on ring A can be connected to form a spiro ring, a bridged 15 ring or a fused ring; when Y1 is CH, R3 is selected from ring D. Further, a preferred compound of the present invention has the structure of the general formula VI: 20 the definition of “E3” in general formulas (IIb), III(a), III(b), IV(a), IV(b), IV(c), IV(d), V(a), V(b) and VI is the same as that of “E3cl” mentioned in the previous contents, that is, it represents a chemical ligand that can bind to E3 ubiquitin ligase, 2022303441   30 Mar 2026 or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt, prodrug thereof; where: L represents a chemical group or a chemical bond connecting benzene ring to E3; E3 represents a chemical ligand that can bind to E3 ubiquitin ligase; 5           Y1 is selected from: N, CR2; Y2 and Y3 are each independently selected from: N, CH; D is selected from: chemical bonds; one or more R1s are each selected from: H, halogen, C1-C6 alkyl, C1-C6 haloalkyl, -CN, -COOH, -NH2; 10           R2 is selected from: H, cyano, halogen, C1-C4 alkyl, C3-C8 cycloalkyl, C1-C4 haloalkyl, C1-C4 alkoxy; ring B is selected from: 5-6 membered heteroaryl, 5-10 membered heterocyclyl, wherein the heteroaryl and heterocyclyl can be further substituted with one or more substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, 15 amido, hydroxyl, wherein two substituents occurring silmutaneously on ring B can be connected to form a bridged ring, a spiro ring, a fused ring; R3 is selected from: C1-C4 alkyl, C1-C4 haloalkyl, 3-6 membered cycloalkyl, 3-6 membered heterocyclyl, 5-6 membered aryl, or 5-6 membered heteroaryl; wherein the cycloalkyl, the heterocyclyl, the aryl, and the heteroaryl can be further substituted with one or more 20 substituents selected from: halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, carboxyl, ester group, amide, hydroxyl, two substituents on the cycloalkyl, heterocyclyl, aryl and the heteroaryl can be connected to form a fused ring, a bridged ring or a spiro ring; n is selected from: an integer of 0-2; when Y1 is selected from CH, and ring B is a benzene ring, a 5-6 membered 25 heteroaromatic ring, a 4-6 membered heterocyclic ring or an 8-10 membered spiro ring, R3 is not C1-C4 alkyl, C1-C4 haloalkyl. As a further preferred embodiment, in the general formula VI, In some embodiments, ring B is preferably selected from: 30 still further, as a preferred embodiment: L is selected from: 'h 2022303441   30 Mar 2026 5 E3cl is selected from: , , , 10 Re is selected from: H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2, -S(O)2Rf, or -P(O)(Rf)2; Rd’ is selected from: H, Rf OCORg, RfOCOORg, ROCONRgRh, COORf, CONRfRg; Rf, Rg, and Rh are each independently selected from: H, C1-C8 alkyl, 3-8 membered cycloalkyl, 3-8 membered heterocyclyl, C1-C6 alkyl, 3-8 membered cycloalkyl, C1-C6 alkyl, 3-8 membered heterocyclyl; 2022303441   30 Mar 2026 or two adjacent Res on the benzene ring form a 7-10 membered benzo ring together with the benzene ring; the C atom on the benzo ring can be further substituted with one or more heteroatoms selected from N, O, S; the benzo ring is optionally substituted with H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2; 5          W1 and W2 are selected from: CH, N; q is selected from: 0, 1, 2, 3. Still further, E3 (i.e., E3cl) is selected from: 0 o          o 2022303441   30 Mar 2026 2022303441   30 Mar 2026 Preferably, the compound or the stereoisomer thereof, or the stereoisomer mixture thereof, 5   or the pharmaceutically acceptable salt thereof is selected from the following compounds: No. Structure No. Structure 001 O^Z'ysO / Mx ,— Z oj iz Wo o       —( z—. W 6 002 £ z r 9^0 b<H ZI 1? y Co 0^2-^0 b° o 003 9 o^b-o ZI r? ■Z.— / d qXWq y o 004 o b p y £J IZ OZ Z= /   --( 0=0 1 0 005 o y cwb^o \7 p :' IZ yOyw O 2= / X--( z—. o=y x z \ 006 o^nh2 1 H "Vn 0" bbo ° rb                 o o X Xb               VNH j,- M    Co w 007 nh2 bn \ / WN y^AJw\ N,          L , N, _ o 9 9            vb      p o b 1 J        ^NwW? Anh —n^jn                 |T^An—\_ / =° 0 008 y \7 p / ™ IZ W-o O 2=7 obbb z 1 009 l b<H ZI r? X £C yy oAho <r o 010 o^nh2 Jw M Mw, 1 1 ,&k         X . N _       „ 0 O        O^ P °* X X J        1-0^0 Vnh -o        XAnA>° A                     0 2022303441   30 Mar 2026 011 O^nh2 ZN.          L ,NX _ _ „ 0   < >        ' A      ,0 0 ^iXA° 0                ° 012 O^NH2 •oA c\xA 0 013 ZI r? / -• g° o 014 0^, nh2 Ao., An AAA^\ .N,„           L „N., _ Xy °1 jY                  FnH °an?                 1 T nA A° 0 015 o^nh2 A’n An GA^ 1    A o r P        A    p q . u 1 J            '-Nx / w'' Anh An^        OpNAP° 0 016 °ANH2 aS o°Af A a A   N'x Al AA O^AA0 017 °VNH2 A u nA ^vu V -    A"- 0 018 Oy,NH2 Ai A aNy A'0  AA aJ                     o 019 o^ nh2 1 H n\NY^ 11 II 9 Y ^Nj ,n.      GUa o rA       VA / \ X J                         o o P / —n            kA / A Anh UQ’A0 0 020 <Va fN  U, /             h / ° 0 rN\              °Y~t A -A J      A IZ-N             -p V / ' '                                    I—N / \ Ar° 021 °Ynh2 aa An / /    , / ^ALx 0   <-N.          / ^) / \ A A }       ^-Nx <An n^A ''— /                    ^N\^N n H oar H 022 9 po ArC ZI 1? A 9- / A l\^° >5 Q 023 O^NH2 A ^n UUy r-'A aA AY 024 <ANH2 "Vvx M lAu, 1                                                                    1 1 .N,         k ,N. _ o r           a^ c-A w. 0 Ao 025 o^nh2 ■A An AAA / \ 0 r i      A'N-y-l      0 0 -A o           ° 026 P Z>sO / A r / —z / A ™ IZ A A 2022303441   30 Mar 2026 027 o A o^A"X° <7 p r\ b IZ UA O Z= / X--( <A 028 nh2 AAf    h Mn O   o Yf X    v / —\ ,0^07 y /   AnX A o, )— /           ^-7 v# o ~^N XX^-N A 029 A,NH2 b'A               H o V" A      o 0 A o V V(j 030 0 hnA oV An O^NH2           AA^O | H                          I ¥ A AO r*! N mA n AA o o-V 031 0 HN— OA y-N nh2 r.Xj UJJj «o 032 1 z r o° bX ZI ■? : / b Ax°° yzA o LA 033 0 HnO oA y-N O^NH,           i / A AW-0 N 0  1^ oa 034 0 AnH2 nA / / ANH A / o >N A C 1 ii / —n        \ 7 A 0 o C"XX 0 035 0 Onh2 n'N VNH o A M u / aA AV 0 036 0 Anh2 AVnh o A ,V) -- o a. AA VvJ A oo 0 037 0 y-NH2 f-A / NH o rN V) o ‘OO 0 038 0 Anh2 XoA-nX 0 >N O - A        \= / XNOb O-\ M n   o o AA / A Anh AnA>° o 039 o. MNIX nA / / ANH / —। o XN X / \ 1 JI         \ / vA X\ 7n / ^.     o o ^'qAXx 0 040 0 Onh2 / / 1 ANH / A o >N A Xo % 2022303441   30 Mar 2026 041 C) 'Vnh2 / N-y-NH F o    M \7 A XNx x> x 'Tb- 042 0 V-NHj N— <? y™ o >n yyCN % 0 o iyy> 0 043 0 X-nh- / / 1 y-NH / ^o >N M rNs M / UyNAO    yo 0 0 7NH \_A° 0 044 o V-nh2 N-Z / / X— NH o    >=n ^5<i ^TX"^" 0 045 0 7nh2 nO / / 7 NH o An x CX % ^¢¢$^ 0 046 o^nh2 Ax jy                        0 0 yx v_yiyy 0 047 0^nh2 A"n n TTx JM           b.^N.. _         o o -cxx 0 048 0^, nh2 ¢7'Op 0 iy                 0 0 -y°   oxy 0 049 o^nh2 Xn n^n 0^7x7 ii-tu 0 050 o^nh2 Ax 0 0    0-7   0 ox x6 ci<y b 051 o^nh2 AVi n^n OO-x XI          \x-N'V-i        o o -XB XAiy 0 052 0 Vnh2 / / 1 7—NH / X 0 >N M a" / x Xx ""^xAx- 0 053 OpNH2 X -X- 054 o^nh2 x ^wOa° -XJ 2022303441   30 Mar 2026 055 O^NH2 1 H                                0 -^%^ 4pro )- -03^      " 056 O^NH2 x 'yjxrCcxyo AyJ 057 o^nh2 o v Xn^ 058 o^nh2 x ^oxx^y0 XyJ 059 yy^AJ 060 o^nh2 x ^XiXr^y0 c / A 061 O^NH2 X '^xcAA "A* xA° 062 0^,nh2 x yxuy^y* .0¼° 063 O^NH2 O X ryA"^ 064 (X,nh2 X yQuoA^P* cx‘A' 065 o^nh2 x ’x^xA4p’ dr^ 066 o^nh2 x yxcAA y ° xA 067 0^,nh2 . x ^xcA1^ N^ 068 o^nh2 x y:x:y:^y° XJ 069 o_nh2 x yJ 1 070 0^nh2 x y:x:>cyy” rX 071 0^, nh2 x xy 072 o^NH2 9. cyiNXS 2022303441   30 Mar 2026 073 OyNH2 x uo joX o-y3 074 OyNH2 X Aw AA cw 075 OyNH2 v -y- 076 A Wnh2        Ai I Xy A N^ / N W'^WY ANW^ o fl XnXJ 077 o^nh2 XYi NyN AXyy ,n                            o 'X       nXX / Xa 0 0 078 OyNH2 ^Oy rN> -A wbxy o o 079 OyNH2 ^Ur ° A Vw ? 0 0 080 o^nh2 Ao NVN WNv-\    O t j:"'j     uA oah 081 XVn Ay NyN M^N^Xj   0 ° / N. 0 C XN^ 082 OyNH2 Acv, Ay o A ynYy ° ° -W 083 O^,NH2 Xy NyN Awy-y N      YNy~X WJ b o 084 o^nh2 Xyx v X ^w° o fX ^w XCANb° 085 Oy NH2 / / ' . : y Y-u 086 OyNH2 y -• xx -W 087 o^nh2 Ah               ft .''. ■' "X y.o 088 0 hnX OyNH2             oAj 4Xw°A xA 2022303441   30 Mar 2026 089 % NyN XXy-y yN 090 o^,nh2 XBn NyN ^Ayy rN>                    o O-tN         NtK>-y>0 o o 091 o^,nh2 X!n, NyN N      AN s / \ 1    ~xx^° 0 0 092 o^nh2 ,vn, rN>                    o O^r0    CXHh 0 0 093 O^NH2 X’m nYn               o 094 NyN                   0 ° 04r° 095 ovnh2 | h                                       / ? . ft '‘W3^’ OX1-1 096 o^nh2 Asri NyN XAyy 0 0 097 O^NHj xx ?> A        JUCXl0 O 098 o^nh2 yayc4p” oXXJ 099 cy.NH2 Cy^X 100 o^nh2 ft 101 0 hnA 0¾^2           O»y CAn1J 102 %n° Nx / N \Ay yN o nXl xX 103 o^nh2 A-v, NyN XAyy yj      xA.^    0 nXX / ^1° 0 0 104 OyNH2 0 0 2022303441   30 Mar 2026 105 O^,nh2 ° A Lnw ,? -A       nxYnA° 0 0 106 o^nh2 XVo i A r“xXH>° 107 XX n A N^N A\Xw\J   0 ° w. o nA A 108 o^nh2 1 H                                         / 9 x jfNYX                 X° X AxX XX Xb'° 109 o^nh2 Xan N^N Aw'^ XX     'n-NvX -A 0 o 110 o^nh2 Xya "X ^Ax          / -a o x X^i XAnA>° 111 OyNH2 =y,, :• ;,-■ XX 112 o^nh2 J-! An-X> 'N\X 113 OyNH2 x    A Xn"° 114 o^nh2 X AlijX'AX’ X'° 115 ° z NH,               0 XX Aw XXnh » T YA      i VA ° NvN XX      \= / ° o A O rA A X) XNnj 116 v <x O^NH2          _XN X X\n nYn xa^ fN A-..     Xa X? o X x XN^ 117 OyNH2 X AaxXa -XXJ 118 O^NH2 o "x Aw AX aX 119 OyNH2 N^yNyX       XY^nX^Xo nVn       An^A Xnh o rX   XXO 0 0 wj 120 t n° O^NH2             _ / N  n 1 H           zAVA ° Ain   A ° NyN X<w  n An^ AX o X 2022303441   30 Mar 2026 121 V y o^,nh2            _An  u i h          rVA ° Ay  a^° NyN           rN o 122 o^nh2 o x Aw Aa -A ’ 123 o^nh2 v A?AofA AJ 124 t y 0^nh2               _ / N if 1 H         AVA 0 Ana a 0 NyN ^Yf rN -A 125 0^nh2 fl Nyy    AAaa NVN         r^N-^y ^NH o A               ° ° ,a 126 i y o^nh2              An Yf 1 H        nA 0 ArYA    F y= / 0 NyN AA^I rN o r 1 Ja J 127 °._ y cy,NH2                y-N y I h        aa o ANY^1     r^0 NyN AAy-y ^n o Ai         i ° 128 y canh2             Anz y i h          fa. ° ANYyF a 0 nyn yyw rN .n.    AaAa .A 129 o^nh2 y Aw .A 130 % y o^,NH2              An A 1 H        aA 0 Aya A ° NvN AA wf o a yyy AJ 131 A-ovnh2              An n 1 h          FVk ° AnyY nyn A-, r< N      ^N^A / 1 o O       ^<sA K JcjJ 132 y ~ canh2                 A i h          rvl ° Anatf   a ° yN An^ rN o y y        a*a 1 J 133 t c£ ovnh2              An y 1 H          fVA 0 NVyycl yA° A      n o y yy / AJ 134 o^nh2 nAn        An-^3 An" o A 33j  °0 -A' 2022303441   30 Mar 2026 135 o^nh2 Y UxkU-” U 136 Y -XH °ynhh      Xu V . ■ Y 137 O-yNH2 O V T JkJ ^NvX <Jo 138 O^,NH2 o V kxokY0 k JyJ 139 o^nh2 y 140 O^,NH2               TY Y 1 H        UA 0 UlY v 0 NyN ^\U X L „hL / kz 0 Y Y 141 o^nh2 o y AyU* FxkjN^ 142 <Xnh2 Y^Yi    fyYnO° nvn YYx       ^nh o A yYV ° ° ■Xr / Y^ 143 O^NH2 o y yAU UUk \— / o 144 o^,nh2 Y Ux UU $          ' >-a           o Yi oUa        ° k° 145 £AXh nyn       rAN ° o rY    Y-nJ—1 K AJ ~NvJ 146 Uyv rAUNH nvn YYn^ xnY-n 0 o A yAA x JA ^nX 147 o^nh2                XY° ^YVf     Yynynh y VYx x^^ ° o      AY—1 X A'J "NvJ 148 o^nh2 "YB'rV      « r'Y° 0 Y AyAX a Y J 149 0^, nh2 XKYYf     0 YY° v A^x YnYVy^ o rY   An J— ^0° « JX                    i 150 o^nh2 "YtY    ° r'V o Y A'JX'YlY" x kJ -nJ1 2022303441   30 Mar 2026 151 OyNH2 onxnh n            —1 o < >                ■ K X'J AO" 152 1 f2^0 z z"z / ° Ox H x-- / zO z ZI i? x X 0 X 153 X^xy pAX" NvN ^n'Y yAn ° N      ^nX--1 K JaX 154 Yhh          s o° Anty rAxr nyn XAn^ pNA,N   O L „hL . 1------1 0    0 >                   (s) 1 J -nJi 155 1 xx o^nh2               An if 1 H             x"\i 0 Xx F^v ° NyN X^y^ N ^hk      X^N^XX o <              ^(sr^ k MU ^n3 156 1 .(0 cVnh2            20 Y 1 H            / OVX 0 Ao f NyN        X X / N^ e X / \l XR; J 157 vO° O^NH2             AX 1 H          AXX 0 ifNyX'F    V^0 NyN          rN _N.       Xo^X\ / o   < >            ^(sr^ kU 158 1 0" °^nh2              / ~n Y 1 H          XvA 0 nXnyvf   yx° nYn        X ^N.        Xn. ..X / 159 q. y-z / \=° X~X / ° zX 0 0 .£ IZ yiXY O z-z z—. oXz3 \ 160 o 00° x X / NH o^nh2             An Y i h          rkx ° ANrrcl v 0 NYN XXNxy N / N.        X / N. .-XX o 0 >            w A JiA J 161 o Xnh2 N= / O A Xnh .A k XCF3 N-.             9 \Y     o o 162 o Xnh2 N=Y O X / Xnh f xnY? w~ f n~y               / ? YxXxx VJ     o o 163 0 Y 0° AZX X-0 fxK ty         0 X^xxXPx \_J      o o 164 ty,NH2 rXNO° NVN XXN^y y~NXJLy yNH o A xn3j ° ° xx 2022303441   30 Mar 2026 165 °yNH2 F r.XW» AA 166 0 Xnh2 n=A x J At NA r~ N    33 ^n3l> 3f Nx / -3 Vx JL Ln3^° ^NH VJ       0 167 °ya A ^33 168 O^nh2 nYAf     j3PnX~X° nyn 3a anAaY™ 0 A An3a 0 0 -3 169 A” cy,nh2                 n A i h          rVk ° 11 iAAX F yA° 3N       £N o rNA    AnAA ^A 170 o^nh2 / / .. : 1 A- 171 °ynhh                s xa° Aw rAVH NyN A<ny / nAn 0 o A   A«AA A A J 172 °Ynh2                o yy° AW rrWH nYn        YnAAf 0 0 a  AA 173 o^nh2 X-Aa" o X AAYhA 1JA            N HNXXo —nA                    3NH vJ                           o 174 o^nh2 Xari' N^N XAm / \ Y   —N X  YA / =Y o / 3        '-^-N. J^N A 0    1   1                          N-A \ / \ A J3 J                     HN \ Xo —XNH \3                           0 175 oya          ? a° Anttf 3ah nyn wny / AX ° o ana    AJJ 176 I vnA / 0 a 0 3 , AF A      Hr (3 M     XX Vn 3       ° H ° N* 'YH N=\ yNH2 o' 177 X3f °5Y^h N^N WNp / nAJ   0 „hL      X^^ / XX o r x X XxJ -n3 178 °ynhh         at 2 3° ynAf   XXhAnh Yn AAy a-A h 0 0 A   An^3 A / J 179 °ynhh          tt s Antyf yVAnh Y Yy     0 o A   An3a X J3 J -0^ 180 X3f 33 nyn 3a / ->3  0 0 A  AAA A AJ 'An 2022303441   30 Mar 2026 181 °YNH=              OMe 0 YY° bAry AW NyN A0.y pNA0 H o o K JA 'A 182 Xmaa yA1? NyN 0YN-y yAY H 0 o A   0N-0A ynA ^nA 183 °YnH2            yo o rrAF  AAV nyn A<Np rA ° o A k JaJ 184 °yNH2              F YY0 nAaa ANkNH NyN ANp pNA ° o A   AnAA -A 185 OyNH2              F Af° ^hyV    f / ¥nynh An ANp pNA o o a ^NAJ -A 186 °yNH2                0Y° A"AfF   FArVH nYn Ay rA ° o a AnAa -A 187 OyNH2               F FF yy^O iTYA     fYNYNH NyN A^p pNA ° o rN^    AnAA ~A 188 OyNH2                F..F Ay'yA    ANkNH NyN AAy pA ° o A   AnAA i A J 189 A 9 . 0 0 £ IZ Zy o=a । 190 '' . 0 0 N IZ yAq oYZ0 1 191 °yNH2                py° aAf Wynh NyN Ap Y~A^ ° o A ^Aj -A 192 °YNHh          ah a° Antaf nAynynh An A0p pNAJ o o A   AnAA -A 193 1 fzyo F-Z A    ft Oiyk ZI •? 0 0 ' b „ A “A 194 1 z 0AC ZI r? 0 0 b “0 195 1 z f A"0 A z AyC ZI t? 0 0 ' b 0 A 196 °yNH2                0A° kA YY     7 i Y An AAp pN00 ° o      AnAA -fAj1 2022303441   30 Mar 2026 197 °ynhh           ox / o rr° AtnAyf   "AAV" NyN A0^ yNA 0 o A   AnAa AJ 198 A -q A £- IZ ya o z-z '-- oZ3 i 199 o NH2          yy ya n^n^f     n1 I nynh nYn A<N / y y-NAJ ° o A   AnAa - / A 200 CL y-NH O^NH2          AN-\—A <fA y iTVt        / nyn ay     N o A  YnA x AJ "An 201 ox y~NH °^NH2         JN AA^ AyY 0 AN         n 0 A   YnYY X A J 'NAN 202 oynh2                       o nVtv rvYr nYn Aq pNAN YA0 o A  AA A"j 203 °vNH2                       o Avy  AY- nyn axn^        axo o A AnAj X ^nCjN 204 \ fzy° YyA ZI r? 0 Az ■ , V o 205 °VNH2                      O AW nVr NvN YAn^ rNMF AXO o A AnAa A J 206 c> y-NH °^NH2          jn \_A 1 H           Ay_ Aaaa  v nYn AY A r\ o A  YnA X yyJ "An 207 °vnh2                       o Avy  nn V          <A. o rY   YnJJ K AJ 'NX 208 fzy° yz AA ZI rj 0 / —Z T Z^ Ax-Ay o 209 'V'S            ro „ o Ayy ya nYn        pNYA AXO o rNY    YnJJ x AJ 'NX 210 °VNA            A° H 0 Axnyaf WAt nYn YA-y        XAO o A  XnA AJ 2022303441   30 Mar 2026 211 V";             „ « AAh NvN      A"^ 0A o A YnJY X 212 o IZ \ o7 Aa> ' ■ ,—z A -P IZ H0Q z—, oM b z \ 213 \ <ZY° z ZI r? 0 0 ■ 0 r o 214 °YV° CYNH2         ^nvT ya- y nyn Ay rN o A  YA -A 215 o q . 0 0 £ IZ Yo O z-z x—( z—. A \ 216 H O nA Ari' a NA         n o A -;A 217 \ rzy=° A )—\       p o^z ZI r? 0 0 ' A Maa \= /   1 ZI 218 Vz / AAa . 0 0 IZ Ra z—< o0z; \ 219 °AA X z^A^z z^ A q ,—Z 0J Avy O z-z Z—, oXM \ 220 0 HN0 0^0 <N [ x° o^nh2           ^ / 0 YA P" nyn ^a rN> 0 A  YA -A 221 0 HN0 oqp <N [ A° o^nh2              / A Ay a nYn ^A r\ o A   Yx / M A-- 222 -. 0 0 IZ May 0 z-z x O00 \ 2022303441   30 Mar 2026 223 O H^O O^NH2                        y J ASy yXI N N N pAXXO o         X-N^AX - N0) 225 0J 0J £ IZ O z-z z—, oXz; । 227 °^NH2                \  ° 0 1 H                nY 4 a?na T 1 II                             r n \ z^O nyn         £J ,N.           0 ,N. o r X AX 229 ■' ■ IZ X . 0 0 w IZ H>q z—. o0z; 231 O ..3^ nV-TY N ^N / N.       ( ) O                 N - nX^       n   n o A A O^ N ^O H 233 & Z Xa o^M a ^z X IZ O z-z z—. O0ZJ 1 235 OyNH2                0Y° A'yV    fYNYNH NyN UN-yO pNAU o o ("0      0'N'0^0 K A'J "00 237 OyNH?                XA° NXyN^^       XNYNH v Vy0 224 x° 000 ZI r? 0 0 " X iz o 0 226 o "0 O ZI °x 0)   /   \ 5 A? A . 0 0 IZ R00 O00 \ 228 \ 00° '"Z 000 ZI 1? 0 0 ' V A0-" ZI 230 o^nh2 1 H                                     0 V NH n JI 1X-, jy4N~Oo 1                         1       1                             A 0 0 0 232 °TNHh               ? 0Y° ANrrF n^m NyN 0AnY <^-000 ° o rY    0NJ0 yA 234 °YNH2                YA0 AyY    0ynynh nYn 00VY 0n"A 0 o A vja i A J ^Vjn 236 o^nh2                   AX^o mA^ N.^.          yAn NH 3001^ ,YJ0 O rN               N i A J - nQ3^ 238 / fzx° ^~z Xy z"z P x— /  z=( z ZI 1? ex Z— / b A 2022303441   30 Mar 2026 2022303441   30 Mar 2026 or its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceutically acceptable salt thereof. Preferably, the compound is the following compound: 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperi 5   din-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2- carboxamide 001 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2 -carboxamide 002 10           5-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperid in-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-ca rboxamide 003 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl)piperidin-15 1-yl)pyrazin-2-carboxamide 004 2022303441   30 Mar 2026 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(3-oxotetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)piperidin -1-yl)pyrazin-2-carboxamide 005 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi 5   peridin-4-yl)phenyl)amino)-5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1-yl )pyrazin-2-carboxamide 006 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-6-ethyl-5-(3-(3-(3-methyl-2-oxyimidazolin-1-yl)piperidin-1-yl)pyraz in-2-carboxamide 007 10 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxohexahydrocyclopenta[d]imidazol-1(2H)-yl)pip eridin-1-yl)pyrazin-2-carboxamide 008 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxooctahydro-1H-benzo[d]imidazol-1-yl)piperidin 15 -1-yl)pyrazin-2-carboxamide 009 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl)piperidin-1-yl)pyrazin-2-carboxamide 010 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi 20 peridin-4-yl)phenyl)amino)-5-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl)piperidin-1 -yl)pyrazin-2-carboxamide 011 3-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin] -4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carbox amide 012 25 3-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin]-4-y l)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxami de 013 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)azetidin-3-yl)-4-methylpiperi din-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-car 30 boxamide 014 3-((4-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperazin-1-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxa mide 015 2022303441   30 Mar 2026 3-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)methyl)pip erazin-1-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 016 3-((4-(9-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-3,9-diazaspirocyclo[5.5]un 5   dec-3-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-car boxamide 017 3-((4-(6-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-2,6-diazaspirocyclo[3.3]he ptan-2-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-ca rboxamide 018 10           3-((4-(2-(4-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperazin-1-yl)-7-azaspiro[3 .5]non-7-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 019 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindol-4-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-15 carboxamide 020 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(5-((2,6-dioxopiperidi n-3-yl)amino)pyridin-2-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carbox amide 021 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2,6-dioxopiperidin 20   -3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)azetidin-3-yl)-4-methylpiperidin-4 -yl)phenyl)amino)pyrazin-2-carboxamide 022 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperi din-3-yl)-1-oxo-1,2-dihydroisoquinolin-6-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino )pyrazin-2-carboxamide 023 25           5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperi din-3-yl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl) amino)pyrazin-2-carboxamide 024 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperi 30 din-1-yl)pyrazin-2-carboxamide 025 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)-4-methyl piperidin-4-yl)phenyl)amino)-5-(3-(3-oxoimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1-yl)pyrazin -2-carboxamide 026 2022303441   30 Mar 2026 5-(3-(3-cyclopentyl-2-oxyimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)pyrazin-2-carboxami de 027 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi 5   din-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperidin-4-formyl)phenyl)amino)pyraz in-2-carboxamide 028 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4-(3-(4-(2-(2,6-dioxopip eridin-3-yl)-1,3-dioxoisoindolin-5-yl)piperazin-1-yl)propan-1-yne-1-yl)piperidin-1-yl)phenyl)am ino)pyrazin-2-carboxamide 029 10           5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((2-((1-(2-(2,6-dioxopiperidi n-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino) pyrazin-2-carboxamide 030 3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2, 3,4-tetrahydroisoquinolin-6-yl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl 15 )pyrazin-2-carboxamide 031 3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)methyl)-1,2,3, 4-tetrahydroisoquinolin-6-yl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxyimidazolin-1-yl)piperidin-1-yl)p yrazin-2-carboxamide 032 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((2-((1-(2-(2,6-dioxopiperidi 20   n-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)p yrazin-2-carboxamide 033 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-4-methylpiperidin-4-yl)phenyl)amino )pyrazin-2-carboxamide 034 25           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )-4-methylpiperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 035 4-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )-4-methylpiperidin-4-yl)phenyl)amino)-2-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyr 30 imidin-5-carboxamide 036 2-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )-4-methylpiperidin-4-yl)phenyl)amino)-5-fluoro-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin -1-yl)nicotinamide 037 2022303441   30 Mar 2026 2-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )-4-methylpiperidin-4-yl)phenyl)amino)-5-methoxy-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperi din-1-yl)nicotinamide 038 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi 5   din-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)pyrazin- 2-carboxamide 039 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-4-fluoropiperidin-4-yl)phenyl)amino) pyrazin-2-carboxamide 040 10 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)-2-fluorophenyl)amino) pyrazin-2-carboxamide 041 3-((3-cyano-4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-y l)methyl)piperidin-4-yl)phenyl)amino)-5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl) 15 pyrazin-2-carboxamide 042 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-3-fluoropiperidin-4-yl)phenyl)amino) pyrazin-2-carboxamide 043 3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl 20 )piperidin-4-yl)phenyl)amino)-5-(3-(4-methyl-5-oxo-4,6-diazaspiro[2.4]cycloheptan-6-yl)piperid in-1-yl)pyrazin-2-carboxamide 044 3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)phenyl)amino)-5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1 -yl)pyrazin-2-carboxamide 045 25 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)pyraz in-2-carboxamide 046 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-5-(-6-(3-isopropyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)py 30 razin-2-carboxamide 047 2-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-6-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)nicot inamide 048 2022303441   30 Mar 2026 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2, 4-triazin-6-carboxamide 049 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)piperidin- 5 4-yl)phenyl)amino)-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2]octan-2-yl)pyrazi n-2-carboxamide 050 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)azetidin-3-yl)p iperidin-4-yl)phenyl)amino)-3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2 -yl)-1,2,4-triazin-6-carboxamide 051 10 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino) pyrazin-2-carboxamide 052 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-15 carboxamide 053 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoindol-5-yl)piperidin-4-yl)methyl)piper idin-4-yl)phenyl)amino)-3-(3-(3-ethyl-2-oxyimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carbo xamide 054 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi 20   peridin-4-yl)phenyl)amino)-3-(3-(3-isopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin- 6-carboxamide 055 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(trifluoromethyl)imidazolin-1-yl)piperidin-1-yl)-1,2,4 -triazin-6-carboxamide 056 25 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl)piperidin-1-yl)-1 ,2,4-triazin-6-carboxamide 057 3-(3-(3-cyclopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiper idin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-1,2,4-triaz 30 in-6-carboxamide 058 3-(3-(3-cyclobutyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-1,2,4-triazi n-6-carboxamide 059 2022303441   30 Mar 2026 3-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperi din-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-1,2,4-triazi n-6-carboxamide 060 3-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperi 5   din-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-1,2,4-triazi n-6-carboxamide 061 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-tria zin-6-carboxamide 062 10 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 063 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-15 carboxamide 064 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(3-(2-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 065 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi 20   peridin-4-yl)phenyl)amino)-3-(3-(3-(3-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4- triazin-6-carboxamide 066 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(pyridin-3-yl)imidazolin-1-yl)piperidin-1-yl)-1,2,4-tri azin-6-carboxamide 067 25 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 068 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl)piperidin-1 30 -yl)-1,2,4-triazin-6-carboxamide 069 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(3-(3-oxytrihydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)piperidin-1 -yl)-1,2,4-triazin-6-carboxamide 070 2022303441   30 Mar 2026 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-y l)-1,2,4-triazin-6-carboxamide 071 3-(6-(3-cyclopentyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-5-((4-(1-((1-( 5 2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl) amino)-1,2,4-triazin-6-carboxamide 072 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(6-(2-oxo-3-phenylimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-y l)-1,2,4-triazin-6-carboxamide 073 10 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(6-(3-oxotetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2-azabi cyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 074 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi peridin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2]octan-2-yl 15 )-1,2,4-triazin-6-carboxamide 075 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisooctyl-5-yl)pyrrolidin-3-yl)methyl)p iperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6 -carboxamide 076 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperidin-4- 20 yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxam ide 077 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin] -4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carbo xamide 078 25 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 079 5-((2-(1-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-1,2,3,4-tetrahydr oisoquinolin-6-yl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-ca 30 rboxamide 080 5-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2, 3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2, 4-triazin-6-carboxamide 081 2022303441   30 Mar 2026 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi perazin-1-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 082 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-[1,4'-bipiperidin]-4-yl)phe 5   nyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 083 5-((4-(4-(3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)propan-2-yn-1-yl)piperazin-1 -yl)piperidin-1-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-tria zin-6-carboxamide 084 10           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl)piperidin-4-yl) methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 085 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi din-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carb 15 oxamide 086 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi din-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxyimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carb oxamide 087 5-((4-(1-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imida 20 zol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 088 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)pyrrolidin-3-yl)methyl)p iperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6 -carboxamide 089 25 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxami de 090 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin] -4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carbox 30 amide 091 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 092 2022303441   30 Mar 2026 5-((2-(1-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-1,2,3,4-tetrahydr oisoquinolin-6-yl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-ca rboxamide 093 5-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2, 5 3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4 -triazin-6-carboxamide 094 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi perazin-1-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 095 10 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-[1,4'-bipiperidin]-4-yl)phe nyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 096 5-((4-(4-(3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoquinolin-5-yl)propan-2-yn-1-yl)piperazi n-1-yl)piperidin-1-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-t 15 riazin-6-carboxamide 097 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl)piperidin-4-yl) methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 098 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi 20   din-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carb oxamide 099 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi din-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carb oxamide 100 25 5-((4-(1-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imida zol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazol-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carboxamide 101 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)pyrrolidin-3-yl)methyl)p iperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-30 yl)-1,2,4-triazin-6-carboxamide 102 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-tr iazin-6-carboxamide 103 2022303441   30 Mar 2026 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin] -4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2, 4-triazin-6-carboxamide 104 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpi 5 peridin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-y l)-1,2,4-triazin-6-carboxamide 105 5-((2-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-1,2,3,4-tetrah ydroisoquinolin-6-yl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 106 10           5-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2, 3,4-tetrahydroisoquinolin-6-yl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-1,2,4-triazin-6-carboxamide 107 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi perazin-1-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-15 yl)-1,2,4-triazin-6-carboxamide 108 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-[1,4'-bipiperidin]-4-yl)phe nyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 109 5-((4-(4-(3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoquinolin-5-yl)propan-2-yn-1-yl)piperazi 20 n-1-yl)piperidin-1-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoisoimidazol-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-1,2,4-triazin-6-carboxamide 110 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl)piperidin-4-yl) methyl)piperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-1,2,4-triazin-6-carboxamide 111 25           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi din-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1 ,2,4-triazin-6-carboxamide 112 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)piperidin-4-yl)methyl)piperi din-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1 30 ,2,4-triazin-6-carboxamide 113 5-((4-(1-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imida zol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 114 2022303441   30 Mar 2026 4-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperazin-1-yl)phenyl)amino)-2-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrimidi n-5-carboxamide 115 4-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl 5 )piperidin-4-yl)phenyl)amino)-2-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrimidi n-5-carboxamide 116 4-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)phenyl)amino)-2-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrimidin -5-carboxamide 117 10           3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)phenyl)amino)-5-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2 -yl)pyrazin-2-carboxamide 118 5-((4-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperazin-1-yl)methyl) piperidin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-tria 15 zin-6-carboxamide 119 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)-3-methylpyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide 120 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)-3-fluoropyrrolidin-3- 20   yl)methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide 121 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)-4-fluoropiperidin-4-yl )methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 122 25           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-tria zin-6-carboxamide 123 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-tri 30 azin-6-carboxamide 124 5-((4-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperazin-1-y l)methyl)piperidin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 125 2022303441   30 Mar 2026 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide 126 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-carbonyl)p 5   iperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triaz in-6-carboxamide 127 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carboxamide 128 10           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 129 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl) 15 -1,2,4-triazin-6-carboxamide 130 5-((4-(4-(((3S)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)m ethyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 131 5-((4-(4-(((3R)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)m 20   ethyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin- 1-yl)-1,2,4-triazin-6-carboxamide 132 5-((3-chloro-4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperazin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide 133 25           5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 134 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)phenyl)amino)-3-((R)-3-(2,5-dioxopyrrolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-c 30 arboxamide 135 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)phenyl)amino)-3-((R)-3-(2,5-dioxopyrrolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 136 2022303441   30 Mar 2026 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)phenyl)amino)-3-((R)-3-(4-methyl-5,7-dioxo-4,6-diazaspiro[2.4]heptan-6-yl)pipe ridin-1-yl)-1,2,4-triazin-6-carboxamide 137 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) 5   piperidin-4-yl)phenyl)amino)-3-((R)-3-(4-methyl-5-oxo-4,6-diazaspiro[2.4]heptan-6-yl)piperidin -1-yl)-1,2,4-triazin-6-carboxamide 138 Methyl (3-(5-(3-((4-(4-((6-carbamoyl-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin -1-yl)-1,2,4-triazin-5-yl)amino)phenyl)piperidin-1-yl)methyl)pyrrolidin-1-yl)-1,3-dioxoisoindoli n-2-yl)-2,6-dioxopiperidin-1-yl)butyrate 139 10           5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperidin-4-yl)phenyl)amino)-3-((R)-3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 140 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) piperidin-4-yl)phenyl)amino)-3-((R)-3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl)piperidin-1 15 -yl)-1,2,4-triazin-6-carboxamide 141 5-((4-(4-((4-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperazin-1-y l)methyl)piperidin-1-yl)phenyl)amino)-3-((R)-3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl)p iperidin-1-yl)-1,2,4-triazin-6-carboxamide 142 3-(6-(1,3-dioxoisoindolin-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-5-((4-(1-((1-(2-(2,6-diox 20   opiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-1, 2,4-triazin-6-carboxamide 143 3-(6-(1,3-dioxoisoindolin-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-5-((4-(1-((1-(2-(2,6-diox opiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-1 ,2,4-triazin-6-carboxamide 144 25           5-((4-(4-((1-(6-(((S)-2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)pyrrolidin-3-yl)met hyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1 -yl)-1,2,4-triazin-6-carboxamide 145 5-((4-(4-((1-(6-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)piperidin-4-yl)methyl)p iperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1 30 ,2,4-triazin-6-carboxamide 146 5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)pyrrolidin-3-yl)methyl)pi perazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 147 2022303441   30 Mar 2026 5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-fluorobenzoyl)pyrrolidin-3-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidi n-1-yl)-1,2,4-triazin-6-carboxamide 148 5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methoxybenzoyl)pyrrolidin-3- 5 yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piper idin-1-yl)-1,2,4-triazin-6-carboxamide 149 5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methylbenzoyl)pyrrolidin-3-yl )methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperid in-1-yl)-1,2,4-triazin-6-carboxamide 150 10           5-((4-(4-(((R)-1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)pyrrolidin-3-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 151 5-((4-(4-(((S)-1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)pyrrolidin-3-yl)methy l)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl 15 )-1,2,4-triazin-6-carboxamide 152 5-((4-(4-(((R)-1-(6-(((S)-2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)pyrrolidin-3-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidi n-1-yl)-1,2,4-triazin-6-carboxamide 153 5-((4-(4-(((S)-1-(6-(((S)-2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)pyrrolidin-3-yl) 20   methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidi n-1-yl)-1,2,4-triazin-6-carboxamide 154 5-((4-(1-(((3S)-1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolidi n-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 155 25 5-((4-(1-(((3R)-1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolid in-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin -1-yl)-1,2,4-triazin-6-carboxamide 156 5-((4-(1-(((3S)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)m ethyl)piperidin-4-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-30 1-yl)-1,2,4-triazin-6-carboxamide 157 5-((4-(1-(((3R)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)m ethyl)piperidin-4-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 158 2022303441   30 Mar 2026 5-((3-chloro-4-(4-(((3S)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolid in-3-yl)methyl)piperazin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperid in-1-yl)-1,2,4-triazin-6-carboxamide 159 5-((3-chloro-4-(4-(((3R)-1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolid 5   in-3-yl)methyl)piperazin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperid in-1-yl)-1,2,4-triazin-6-carboxamide 160 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperazin-1-yl)-3-(trifluoromethyl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide 161 10           5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperazin-1-yl)-2,3-difluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin -1-yl)-1,2,4-triazin-6-carboxamide 162 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl )piperazin-1-yl)-2,5-difluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin 15 -1-yl)-1,2,4-triazin-6-carboxamide 163 5-((3-chloro-4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-y l)methyl)piperazin-1-yl)phenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-y l)-1,2,4-triazin-6-carboxamide 164 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl) 20   piperazin-1-yl)-2,3-difluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin- 1-yl)-1,2,4-triazin-6-carboxamide 165 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)pip erazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1 ,2,4-triazin-6-carboxamide 166 25           5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)piperidin-4-yl)methyl)pipe razin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 167 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindolin-5-yl)piperidin-4-yl)methyl)pipe razin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1, 30 2,4-triazin-6-carboxamide 168 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)pip eridin-1-yl)-1,2,4-triazin-6-carboxamide 169 2022303441   30 Mar 2026 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)piperidin-4-yl )methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piper idin-1-yl)-1,2,4-triazin-6-carboxamide 170 5-((4-(4-((1-(6-(((S)-2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)piperidin-4-yl)meth 5 yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 171 5-((4-(4-((1-(4-(((S)-2,6-dioxopiperidin-3-yl)carbamoyl)-3-fluorophenyl)piperidin-4-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperi din-1-yl)-1,2,4-triazin-6-carboxamide 172 10           5-((4-(4-((1-(6-(2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)pyrrolidin-3-yl)methyl)p iperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carboxamide 173 5-((4-(4-((1-(5-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-2-yl)pyrrolidin-3-yl)methyl) piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-y 15 l)-1,2,4-triazin-6-carboxamide 174 5-((4-(4-((1-(5-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-2-yl)piperidin-4-yl)methyl)p iperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carboxamide 175 5-((4-(4-((1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3]dioxacyclopent-4-yl)p 20 yrrolidin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazoli din-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 176 5-((4-(4-((1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3]dioxacyclopent-4-yl)pi peridin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino-3-((R)-3-(3-methyl-2-oxoimidazolidi n-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 177 25           4-(3-((4-(4-((6-carbamoyl-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-5-yl)amino)-2-fluorophenyl)piperazin-1-yl)methyl)pyrrolidin-1-yl)-N-(2,6-dioxopiperi din-3-yl)-1Hbenzimidazol-7-carboxamide 178 4-(4-((4-(4-((6-carbamoyl-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-5-yl)amino)-2-fluorophenyl)piperazin-1-yl)methyl)piperidin-1-yl)-N-(2,6-dioxopiperid 30 in-3-yl)-1Hbenzimidazol-7-carboxamide 179 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-methylphenyl)piperidin-4-yl)met hyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin -1-yl)-1,2,4-triazin-6-carboxamide 180 2022303441   30 Mar 2026 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-methoxyphenyl)piperidin-4-yl)me thyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin -1-yl)-1,2,4-triazin-6-carboxamide 181 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)carbamoyl)-2,3-difluorophenyl)piperidin-4-yl) 5   methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperi din-1-yl)-1,2,4-triazin-6-carboxamide 182 5-((4-(4-((1-(8-((2,6-dioxopiperidin-3-yl)carbamoyl)-2,3-dihydrobenzo[b][1,4]dioxan-5-yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidaz olidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 183 10           (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-fluorophenyl)piperidin-4- yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperid in-1-yl)-1,2,4-triazin-6-carboxamide 184 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-2,3-difluorophenyl)piperidi n-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)pip 15 eridin-1-yl)-1,2,4-triazin-6-carboxamide 185 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-2-fluorophenyl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperid in-1-yl)-1,2,4-triazin-6-carboxamide 186 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-(trifluoromethyl)phenyl)p 20   iperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 187 (R)-5-((4-(4-((1-(3-(difluoromethyl)-4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)pi peridin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 188 25           (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-isopropylphenyl)piperidin -4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)pipe ridin-1-yl)-1,2,4-triazin-6-carboxamide 189 (R)-5-((4-(4-((1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)benzo[d][1,3]dioxacyclopent -4-yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazo 30   lidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 190 (R)-5-((4-(4-((1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)benzo[d]oxazol-4-yl)piperidi n-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)pip eridin-1-yl)-1,2,4-triazin-6-carboxamide 191 2022303441   30 Mar 2026 (R)-5-((4-(4-((1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-1H-benzo[d]imidazol-4-yl)p iperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 192 (R)-5-((4-(4-((1-(8-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-2,3-dihydrobenzo[b][1,4]di 5 oxan-5-yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoim idazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 193 (R)-5-((4-(4-((1-(3-cyclopropyl-4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperi din-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)p iperidin-1-yl)-1,2,4-triazin-6-carboxamide 194 10           (R)-5-((4-(4-((1-(6-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)pyridin-3-yl)piperidin-4-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 195 (R)-5-((4-(4-((1-(5-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)pyridin-2-yl)piperidin-4-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin- 15 1-yl)-1,2,4-triazin-6-carboxamide 196 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-2-(methylsulfonyl)phenyl)pi peridin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 197 (R)-5-((4-(4-((1-(2-(dimethylphosphoryl)-4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phe 20 nyl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazoli din-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 198 (R)-5-((4-(4-((1-(5-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)quinolin-8-yl)piperidin-4-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 199 25           5-((4-(4-((1-(6-((2,6-dioxopiperidin-3-yl)amino)pyridin-3-yl)pyrrolidin-3-yl)methyl)pipe razin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 200 5-((4-(4-((1-(5-((2,6-dioxopiperidin-3-yl)amino)pyridin-2-yl)pyrrolidin-3-yl)methyl)pipe razin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1, 30 2,4-triazin-6-carboxamide 201 5-((4-(4-((1-(6-((2,6-dioxopiperidin-3-yl)amino)pyridin-3-yl)piperidin-4-yl)methyl)piper azin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-6-carboxamide 202 2022303441   30 Mar 2026 5-((4-(4-((1-(5-((2,6-dioxopiperidin-3-yl)amino)pyridin-2-yl)piperidin-4-yl)methyl)piper azin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-6-carboxamide 203 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)amino)-3-fluorophenyl)pyrrolidin-3-yl)methyl)p 5   iperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carboxamide 204 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)amino)-3-fluorophenyl)piperidin-4-yl)methyl)pi perazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 205 10           5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)amino)-3-methylphenyl)pyrrolidin-3-yl)methyl) piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-y l)-1,2,4-triazin-6-carboxamide 206 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)amino)-3-methylphenyl)piperidin-4-yl)methyl)p iperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl) 15 -1,2,4-triazin-6-carboxamide 207 5-((4-(4-((1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d][1,3]dioxacyclopent-4-yl)pyrrol idin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 208 5-((4-(4-((1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d][1,3]dioxacyclopent-4-yl)piperi 20 din-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 209 5-((4-(4-((1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d]oxazol-4-yl)piperidin-4-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1 -yl)-1,2,4-triazin-6-carboxamide 210 25 5-((4-(4-((1-(8-((2,6-dioxopiperidin-3-yl)amino)-2,3-dihydrobenzo[b][1,4]dioxan-5-yl)pi peridin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidi n-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 211 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-6-yl)pyrrolidin-3-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-30 1-yl)-1,2,4-triazin-6-carboxamide 212 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-6-yl)piperidin-4-yl)methyl )piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 213 2022303441   30 Mar 2026 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-pyrazolo[3,4-b]pyridin-6-yl)pyrrol idin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 214 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-pyrazolyl[3,4-b]pyridin-6-yl)piper 5   idin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 215 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-7-yl)pyrrolidin-3-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 216 10 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-7-yl)piperidin-4-yl)methyl )piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 217 5-((4-(4-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imida zol-5-yl)pyrrolidin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-ox 15   oimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 218 5-((4-(4-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imida zol-5-yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoi midazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 219 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxo-1,2,3,4-tetrahydropyrrolo[3,4-b]indol-6-y 20   l)pyrrolidin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidaz olidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 220 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxo-2,3-dihydro-1H-benzofuro[2,3-c]pyrrol-6 -yl)pyrrolidin-3-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimid azolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 221 25           5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxo-1,2,3,4-tetrahydropyrrolo[3,4-b]indol-6-y l)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazo lidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 222 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxo-2,3-dihydro-1H-benzofuro[2,3-c]pyrrol-6 -yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimida 30 zolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 223 5-((4-(4-(3-(6-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)propan-2-yn-1-yl)pipera zin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2, 4-triazin-6-carboxamide 224 2022303441   30 Mar 2026 5-((4-(4-((4-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-fluorophenyl)ethynyl)piperazin-1-yl) -3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 225 5-((4-(4-(3-(4-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-methylphenyl)propan-2-yn-1-yl)pi 5   perazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)- 1,2,4-triazin-6-carboxamide 226 5-((4-(4-(3-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidaz ol-5-yl)propan-2-yn-1-yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimida zolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 227 10 5-((4-(4-(3-(4-((2,6-dioxopiperidin-3-yl)amino)-3-fluorophenyl)propan-2-yn-1-yl)piperaz in-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4 -triazin-6-carboxamide 228 5-((4-(4-(3-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d]oxazol-4-yl)propan-2-yn-1-yl)pi perazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-15 1,2,4-triazin-6-carboxamide 229 5-((4-(4-(3-(5-((2,6-dioxopiperidin-3-yl)carbamoyl)thiophen-2-yl)propan-2-yn-1-yl)piper azin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-6-carboxamide 230 5-((3-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)-9- 20 fluoro-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin -1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 231 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxo-1,2-dihydroisoquinolin-6-yl)piperidin-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)pip eridin-1-yl)-1,2,4-triazin-6-carboxamide 232 25          (R)-5-((4-(4-((1-(3-carbamoyl-4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperidi n-4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)pip eridin-1-yl)-1,2,4-triazin-6-carboxamide 233 (R)-5-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperidin-4-yl)methyl )piperidin-4-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1, 30 2,4-triazin-6-carboxamide 234 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperidin-4-yl)methyl )-3-oxopiperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 235 2022303441   30 Mar 2026 (R)-5-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 -yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 236 (R)-5-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 5   -yl)methyl)piperidin-4-yl)-3-(hydroxymethyl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin- 1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 237 (R)-5-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 -yl)methyl)piperidin-4-yl)-2-(hydroxymethyl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 238 10 (R)-5-((4-(1-(2-(1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)azetidin-3-yl)acetyl)piperidin-4-yl)-2-(hydroxymethyl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 239 (R)-5-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperidin-4-yl)methyl )piperidin-4-yl)-3-(hydroxymethyl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperi 15 din-1-yl)-1,2,4-triazin-6-carboxamide 240 (R)-3-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 -yl)methyl)piperidin-4-yl)-3-fluorophenyl)amino)-6-fluoro-5-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 241 (R)-2-((4-(1-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 20 -yl)methyl)piperidin-4-yl)-3-fluorophenyl)amino)-3,5,6-trifluoro-4-(3-(3-methyl-2-oxoimidazoli din-1-yl)piperidin-1-yl)benzamide 242 5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)benzo[d]isoxazol-6-yl)piperidin-4-yl)methyl)pip erazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1 ,2,4-triazin-6-carboxamide 243 25           5-((4-(4-((1-(3-(2,6-dioxopiperidin-3-yl)imidazo[1,2-a]pyridin-7-yl)piperidin-4-yl)methy l)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 244 (R)-5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)imidazo[1,2-a]pyridin-7-yl)p iperidin-4-yl)methyl)piperazin-1-yl)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2, 30 4-triazin-6-carboxamide 245 (R)-5-((4-(4-(3-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)imidazo[1,2-a]pyridin-7-yl)pr opan-2-yn-1-yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide 246 2022303441   30 Mar 2026 5-((4-(4-((1-(1-(2,6-dioxopiperidin-3-yl)-2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)piperidin -4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carboxamide 247 5-((4-(4-(3-(1-(2,6-dioxopiperidin-3-yl)-2-oxo-1,2-dihydrobenzo[cd]indol-6-yl)propan-2- 5   yn-1-yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piper idin-1-yl)-1,2,4-triazin-6-carboxamide 248 5-((4-(4-((1-(5-((2,6-dioxopiperidin-3-yl)carbamoyl)naphthalen-1-yl)piperidin-4-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 249 10           4-(4-((4-(4-((6-carbamoyl-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2 ,4-triazin-5-yl)amino)-2-fluorophenyl)piperazin-1-yl)methyl)piperidin-1-yl)-N-(2,6-dioxopiperid in-3-yl)quinolin-8-carboxamide 250 5-((4-(4-((1-(4-(2,6-dioxopiperidin-3-yl)amino)-2-fluorophenyl)piperidin-4-yl)methyl)pi perazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-15 1,2,4-triazin-6-carboxamide 251 5-((4-(4-((1-(4-(2,6-dioxopiperidin-3-yl)amino)-2-(trifluoromethyl)phenyl)piperidin-4-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperi din-1-yl)-1,2,4-triazin-6-carboxamide 252 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)amino)phenyl)piperidin-4-yl)methyl)piperazin- 20    1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-tri azin-6-carboxamide 253 5-((4-(4-((1-(4-((2,6-dioxopiperidin-3-yl)carbamoyl)-3-fluorophenyl)piperidin-4-yl)meth yl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 254 25           (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)phenyl)piperidin-4-yl)methyl )piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl)-1 ,2,4-triazin-6-carboxamide 255 5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-fluorophenyl)pyrrolidin-3-yl) methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)piperi 30 din-1-yl)-1,2,4-triazin-6-carboxamide 256 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methylphenyl)piperidin-4 -yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperi din-1-yl)-1,2,4-triazin-6-carboxamide 257 2022303441   30 Mar 2026 5-((4-(4-((1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methoxyphenyl)pyrrolidin-3-y l)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-((R)-3-(3-methyl-2-oxoimidazolidin-1-yl)pipe ridin-1-yl)-1,2,4-triazin-6-carboxamide 258 (R)-5-((4-(4-((1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-methoxyphenyl)piperidin- 5 4-yl)methyl)piperazin-1-yl)-3-fluorophenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piper idin-1-yl)-1,2,4-triazin-6-carboxamide 259 Description of Terminology Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art. Unless otherwise specified, all 10 patent documents, publicly disclosed materials, etc. referred to in the present invention are incorporated herein in their entirety. If there are multiple definitions for the same term in the present invention, the definition in this section shall prevail. It should be understood that the foregoing general description and the following detailed description are merely exemplary and explanatory, and are not interpreted as limitations on any 15 claim. It should be noted that in the specification and the appended claims, singular references such as “a”, “an” and “the” include plural references unless the context specifies otherwise. It should also be noted that “or” means “and / or” unless specified otherwise. Furthermore, “comprise”, “include”, and similar terms are not limiting. “Substituted” means that a hydrogen atom is substituted with a substituent. It should be 20 noted that the substituent on a specific atom is constrained by its valence. In the definition part, “Ci-Cj” means a range including the starting point and the end point, where i and j are both integers, indicating the number of carbon atoms. For example, C1-C4, C1-C8, C3-C8, etc. C, H, O, S, N, F, Cl, Br, I, etc. involved in the groups and compounds of the present invention all include their isotopes. At the same time, C, H, O, S, N, F, Cl, Br, and I involved in 25 the groups and compounds of the present invention may be optionally substituted with one or more of their corresponding isotopes, including but not limited to isotopes of carbon 12C,13C, and 14C, isotopes of hydrogen protium (H), deuterium (D), and tritium (T), isotopes of oxygen 16O, 17O, and 18O, isotopes of sulfur 32S, 33S, 34S, and 36S, isotopes of nitrogen 14N and 15N, isotopes of fluorine 17F and 19F, isotopes of chlorine 35Cl and 37Cl, isotopes of bromine 79Br and 81Br, etc. 30 The term “alkyl” used in the present invention means a straight or branched saturated hydrocarbon group containing 1 to 8 carbon atoms, including but not limited to methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-amyl, isoamyl, neoamyl, tert-amyl, n-hexyl, isohexyl, neohexyl, heptyl, isoheptyl, neoheptyl, octyl, isooctyl, etc. The alkyl can be substituted with one or more substituents. When there are multiple substitutions occurring, the 2022303441   30 Mar 2026 substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8hydroxyalkyl, haloC1-C8 5 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. The term “alkenyl” used in the present invention means a straight or branched hydrocarbon chain group containing 1 to 8 carbon atoms and at least one C=C double bond, 10 including but not limited to vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 1-methyl-2-butenyl, 1-hexenyl, 2-hexenyl,    3-hexenyl,    4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 1-heptenyl, 2-heptenyl, 3-heptenyl, 1-methyl-2-hexenyl, 2-methyl-2-hexenyl, 2-methyl-3-hexenyl, 3,5-dimethyl-2-hexenyl, 3,3-dimethyl-1-pentenyl, 15 3-methyl-2-ethyl-1-butenyl, 1-octenyl, 2-octenyl, etc. The alkenyl can be substituted with one or more substituents. When there are multiple substitutions occurring, the substituents can be the same or different; the substituents are independently D, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, halohydroxyalkyl, alkylamino, haloalkylamino, cycloalkyl, halocycloalkyl, heterocyclyl, aryl, heteroaryl, hydroxyl, halogen, cyano, nitro, amino, aminoalkyl, carboxyl, 20 amido, sulfonamido. The term “alkynyl” used in the present invention means a straight or branched hydrocarbon chain group containing 1 to 8 carbon atoms and at least one C=C triple bond, including but not limited to ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 3-methyl-1-butynyl, 4-methyl-1-butynyl, 25 2-methyl-3-butynyl, 1-methyl-4-butynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl,    1-methyl-4-pentynyl,   2-methyl-3-pentynyl, 2,2-dimethyl-4-pentynyl, 1-heptynyl, 2-heptynyl,   3-heptynyl, 4-heptynyl, 5-heptynyl, 2-methyl-3-hexynyl, 3-methyl-1-hexynyl, 3,3-dimethyl-1-hexynyl, 4-methyl-1-hexynyl, etc. The alkynyl can be substituted with one or more substituents. When there are multiple substitutions 30 occurring, the substituents can be the same or different; the substituents are independently D, alkyl, haloalkyl, alkoxy, haloalkoxy, hydroxyalkyl, halohydroxyalkyl, alkylamino, haloalkylamino, cycloalkyl, halocycloalkyl, heterocyclyl, aryl, heteroaryl, hydroxyl, halogen, cyano, nitro, amino, aminoalkyl, carboxyl, amido, sulfonamido. 2022303441   30 Mar 2026 10 15 The term “alkylene” used in the present invention means a linear or branched divalent saturated hydrocarbon group containing 1 to 8 carbon atoms, including but not limited to methylene, ethylene, propylene, butylene, pentylene, etc. The alkylene can be substituted with one or more substituents. When there are multiple substitutions occurring, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. The term “halogen” used in the present invention means fluorine, chlorine, bromine and iodine, preferably, fluorine, chlorine and bromine. The term “cycloalkyl” used in the present invention means a monocyclic or polycyclic (two monocyclic rings connected by chemical bonds or bridged ring or spiro ring or fused ring) non-aromatic monovalent hydrocarbon group having 3 to 12 carbon atoms, and possibly one or more chemical bonds that are double or triple bonds. “Cycloalkyl” includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, 20 25 cyclodecyl, decalin, cyclopropyl-fused-cyclopropyl, cyclopropyl-fused-cyclopentyl, cyclobutyl-fused-cyclobutyl, cyclobutyl-fused-cycloheptyl, cyclopentyl-fused-cycloheptyl, cyclopropyl-spiro-cyclobutyl, cyclopropyl-spiro-cycloheptyl, cyclobutyl-spiro-cyclohexyl, cyclopentyl-spiro-cyclohexyl, cyclopropyl-fused-cyclohexyl, cyclobutyl-fused-cyclopentyl, cyclopentyl-fused-cyclopentyl, cyclohexyl-fused-cyclohexyl, cyclopropyl-spiro-cyclopentyl, cyclobutyl-spiro-cyclobutyl, cyclobutyl-spiro-cycloheptyl, cyclobutyl-spiro-cycloheptyl, cyclopropyl-fused-cyclobutyl, cyclopropyl-fused-cycloheptyl, cyclobutyl-fused-cyclohexyl, cyclopentyl-fused-cyclohexyl, cyclopropyl-spiro-cyclopropyl, cyclopropyl-spiro-cyclohexyl, cyclobutyl-spiro-cyclopentyl, cyclopentyl-spiro-cyclopentyl, cyclohexyl-spiro-cyclohexyl, 30 bicyclo[1.1.1]pentyl, bicyclo[4.1.1]octyl, bicyclo[4.2.1]nonyl, bicyclo[2.1.1]hexyl, bicyclo[3.2.1]octyl, bicyclo[4.3.1]nonyl, bicyclo[3.1.1]heptyl, bicyclo[3.2.1]octyl, bicyclo[3.2.2]nonyl, bicyclo[2.2.1]heptyl, bicyclo[5.1.1]nonyl, bicyclo[5.2.1]decyl, bicyclo[4.2.2]decyl, etc. The cycloalkyl can be substituted with one or more substituents. When there are multiple substitutions occurring, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, 2022303441   30 Mar 2026 alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. 5 The term “cycloalkenyl” used in the present invention means a monocyclic or polycyclic (two monocyclic rings connected by chemical bonds or bridged ring or spiro ring or fused ring) non-aromatic monovalent hydrocarbon group having 3 to 12 carbon atoms and at least one C=C double bond, including but not limited to cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cycloalkenyl, spiro[2.2]pent-1-enyl, spiro[2.2]pent-1,4-dienyl, 10 spiro[2.3]hex-1-enyl, spiro[2.3]hex-1,4-dienyl, spiro[3.3]hept-1-enyl, spiro[3.3]hept-1,5-dienyl, spiro[3.4]oct-1-enyl, spiro[3.4]oct-1,6-dienyl, spiro[3.4]oct-5-enyl, spiro[3.4]oct-6-enyl, spiro[3.4]oct-1-enyl, bicyclo[2.1.1]hex-1-enyl, bicyclo[2.1.1]hex-2-enyl, bicyclo[3.1.1]hept-1-enyl, bicyclo[3.1.1]hept-2-enyl, bicyclo[2.2.1]hept-1-enyl, bicyclo[2.2.1]hept-2-enyl, etc. The cycloalkene or cycloalkenyl can be substituted with one or more substituents. When there are 15 multiple substitutions occurring, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8 hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, 20 cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C12 heteroaryl, C3-C12 heterocyclyl. The term “heterocyclyl” used in the present invention means a monocyclic or polycyclic (two monocyclic rings connected by chemical bonds or bridged ring or spiro ring or fused ring) non-aromatic ring group having 3 to 12 ring atoms, one or more heteroatoms selected from N, O, 25 S, and possibly one or more chemical bonds that are double or triple bonds. Heterocyclyl, includes but are not limited to, pyranyl, piperidinyl, piperazinyl, morpholinyl, dioxanyl, oxacyclopropyl, oxacyclobutyl, oxacyclohexyl, oxacycloheptyl, oxacyclooctyl, azacyclopropyl, azacyclobutyl, azacyclopentyl, azacycloheptyl, azacyclooctyl, thiocyclobutyl, thiocyclopropyl, azacyclooctane group, oxazepinyl, diazepinyl, thiazepinyl, dihydrofuranyl, dihydrothienyl, 30 dihydropyranyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrothiazolyl, tetrahydroimidazolyl, hexahydropyridazinyl, hexahydropyrimidinyl, 1-azaspiro[2.2]pentyl, 1-azaspiro[2.3]hexyl, 4-azaspiro[2.3]hexyl, 5-azaspiro[2.3]hexyl, 2-azaspiro[3.3]heptyl, 2,6-diazaspiro[3.3]heptyl, 2-oxa-6-azaspiro[3.3]heptane, 1-azaspiro[2.5] octyl, 2-azaspiro[3.4]octyl, 6-azaspiro[3.4]octyl, 2,6-diazaspiro[3.4]octyl, 2-azaspiro[3.5]nonyl, 2022303441   30 Mar 2026 6-azaspiro[3.5]nonyl, 7-azaspiro[3.5]nonyl, 2,7-diazaspiro[3.5]nonyl, 2-oxa-7-azaspiro[3.5] nonyl, 1-azaspiro[4.4]nonyl, 2-azaspiro[4.4]nonyl, 8-azaspiro[4.5]decyl, 2,8-diazaspiro[4.5] decyl, 1-oxaspiro[2.2]pentyl, 1-oxaspiro[2.3]hexyl, 4-oxaspiro[2.3]hexyl, 5-oxaspiro[2.3]hexyl, 2-oxaspiro[3.3]heptyl, 2-oxaspiro[3.5]nonyl, 2-oxaspiro[4.4]nonyl, 1-oxaspiro[2.5]octyl, 6-oxaspiro[3.5]nonyl, 8-oxaspiro[4.5]decyl, 2-oxaspiro[3.4]octyl, 7-oxaspiro[3.5]nonyl, decahydroquinolyl, 6-oxaspiro[3.4]octyl, 1-oxaspiro[4.4]nonyl, decahydroisoquinolyl, 2-azabicyclo[1.1.1]pentyl, 2-oxabicyclo[1.1.1]pentyl, oxabicyclo[2.1.1]hexyl, azabicyclo[3.1.1]heptyl, azabicyclo[2.1.1]hexyl, oxabicyclo[3.1.1]heptyl, azabicyclo[2.2.1]heptyl, azabicyclo[4.1.1]octyl, azabicyclo[3.2.1]octyl, azabicyclo[3.2.1]octyl, 10 etc. The heterocyclyl can be substituted with one or more substituents. When there are multiple substitutions occurring, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, 15   haloC1-C8 hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. The term “aryl” used in the present invention means an all-carbon monocyclic or fused polycyclic aromatic ring group (in the case of fused polycyclic rings, one of the fused rings can 20 be partially saturated) having 6 to 12 carbon atoms, including but not limited to benzene ring, naphthalene ring, anthracene ring, indene ring, dihydroindenyl (indanyl), dihydronaphthalene ring, tetrahydronaphthalene ring, etc. Aryl can be unsubstituted or substituted, can be monosubstituted (such as ortho-, meta-, or para-substituted), can also be di-substituted or tri-substituted, etc. When there are multiple substitutions occurring, the substituents can be the 25 same or different; the substituents are independently D (deuterium), halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, acyl, amido, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8 hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 30 heteroaryl, C3-C12 heterocyclyl. The term “heteroaryl” used in the present invention means a monocyclic or fused polycyclic aromatic ring group (in the case of fused polycyclic rings, one of the fused rings can be partially saturated) having 5 to 14 ring atoms, which is equivalent to that one or more carbons in the above “aryl” are replaced by heteroatoms such as N, O, S, etc. Heteroaromatic rings can be 2022303441   30 Mar 2026 monocyclic ring or bicyclic ring, i.e., formed by the fusion of two rings. Heteroaryl includes, but are not limited to, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, isoxazolyl, isothiazolyl, pyrazolyl, thiazolyl, thienyl, furanyl, triazolyl, oxazolyl, imidazolyl, indazolyl, indolizinyl, indolyl, dihydroindolyl, isoindolinyl, quinolyl, isoquinolyl, quinoxalinyl, quinazolinyl, 5 dihydroquinolinyl, tetrahydroquinolinyl, dihydroisoquinolinyl, dihydroisoquinolinyl, tetrahydroisoquinolinyl, pteridinyl, purinyl, benzoimidazolyl, benzofuranyl, benzothienyl, benzothiazolyl, benzotriazolyl, benzotriazinyl, benzoxadiazolyl, benzoxazolyl, benzoisoxazolyl, imidazopyridyl, imidazothiazolyl, pyrrolopyridyl, thienopyrrolyl, thienothienyl, thienopyridyl, thienopyrimidinyl, pyrazolopyrimidinyl, pyrrolopyrrolyl, pyrrolopyrimidinyl, pyrrolopyridazinyl, 10 pyrrolopyrazinyl, imidazopyrimidinyl, imidazopyrazinyl, imidazopyridazinyl, pyrazolopyridyl, pyrazolopyridazinyl, pyrazolopyrazinyl, pyrimidopyridyl, pyrimidopyrazinyl, pyrimidopyridazinyl, pyrimidopyrimidinyl, pyridopyridyl, pyridopyrazinyl, pyridopyridazinyl, pyridazinopyridazinyl, pyridazinopyrazinyl, pyrazinopyrazinyl, etc. Heteroaryl can be unsubstituted or monosubstituted or polysubstituted. In the case of polysubstitution, the 15 substituents can be the same or different; the substituents are independently D (deuterium), halogen, cyano, nitro, amino, aminoalkyl, hydroxy, carboxyl, carboxylic ester group, acyl, amido, alkylamido, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 20 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl. The terms “spiro ring” and “spiro ring group” used in the present invention mean a polycyclic structure, in which at least two rings share one atom (usually a C atom). In this polycyclic structure, one or more chemical bonds can be double bonds or triple bonds, and one or more heteroatoms can be present. The spiro ring group can be unsubstituted or 25 monosubstituted or polysubstituted. In the case of polysubstitution, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 30 cycloalkyl, haloC3-C12 cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. The term “bridged ring group” used in the present invention means a polycyclic structure, in which at least two rings share two or more atoms. In this polycyclic structure, one or more 2022303441   30 Mar 2026 chemical bonds can be double bonds or triple bonds, and one or more heteroatoms can be present. The bridged ring group can be unsubstituted or monosubstituted or polysubstituted. In case of polysubstitution, the substituents can be the same or different; the substituents are independently D (deuterium), oxo, halogen, cyano, nitro, hydroxy, amino, aminoalkyl, alkenyl, alkynyl, 5 carboxyl, carboxylic ester group, acyl, amido, methylsulfuryl, alkylamido, C1-C8 alkyl, C1-C8 alkoxy, C1-C8 hydroxyalkyl, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 alkoxy, haloC1-C8hydroxyalkyl, haloC1-C8 alkylamino, C3-C12 cycloalkyl, haloC3-C12 cycloalkyl, cycloalkenyl, cycloalkynyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, hydroxyalkylamido, sulfonamido, C6-C12 aryl, C5-C14 heteroaryl, C3-C12 heterocyclyl. 10 The term “alkoxy” used in the present invention means alkyl-O-, in which the alkyl is as defined above. Examples of “alkoxy” used in the present invention include, but are not limited to, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, pentoxy, isopentyloxy, neopentyloxy, etc. “Alkoxy” also includes substituted alkoxy, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, 15   C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl. The term “hydroxyalkyl” used in the present invention means -alkyl-OH, in which the alkyl is as defined above. Examples of “hydroxyalkyl” used in the present invention include, but 20 are not limited to, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxyisopropyl, etc. “Hydroxyalkyl” also includes substituted hydroxyalkyl, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, 25    C5-C14 heteroaryl. The term “aminoalkyl” used in the present invention means -alkyl-NH2, in which the alkyl is as defined above. Examples of “aminoalkyl” used in the present invention include, but are not limited to, aminomethyl, aminoethyl, aminopropyl, aminoisopropyl, etc. “Aminoalkyl” also includes substituted aminoalkyl, the substituents of which may be D, halogen, oxo, amino, 30 hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl, and the substituents of which can be on alkyl or on N. 2022303441   30 Mar 2026 The term “alkylamino” used in the present invention means -NH-alkyl, in which the alkyl is as defined above. Examples of “alkylamino” used in the present invention include, but are not limited to, methylamino, ethylamino, propylamino, isopropylamino, etc. “Alkylamino” also includes substituted alkylamino, the substituents of which may be D, halogen, oxo, amino, 5 hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl, and the substituents of which can be on alkyl or on N. The term “alkylcarbonyl” used in the present invention means alkyl-C(O)-, in which the 10 alkyl is as defined above. “Alkylcarbonyl” also includes substituted alkylcarbonyl, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl. The “C(O)” represents C=O. 15 The term “alkoxycarbonyl” used in the present invention means alkyl-O-C(O)-, in which the alkyl is as defined above. “Alkoxycarbonyl” also includes substituted alkoxycarbonyl, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 20   heterocyclyl, C6-C12 aryl, and C5-C14 heteroaryl. The “C(O)” represents C=O. The term “heterocycloalkoxy” used in the present invention means heterocycloalkyl-O-, in which the heterocycloalkyl is as defined above. “Heterocycloalkoxy” also includes substituted heterocycloalkoxy, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 25 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl. The term “cycloalkoxy” used in the present invention means cycloalkyl-O-, in which the cycloalkyl is as defined above. “Cycloalkoxy” also includes substituted cycloalkoxy, the substituents of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, 30 sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, and C5-C14 heteroaryl. The term “cycloalkylamino” used in the present invention means cycloalkyl-NH-, in which the cycloalkyl is as defined above. “Cycloalkylamino” also includes substituted 2022303441   30 Mar 2026 cycloalkylamino, the substituent of which may be D, halogen, oxo, amino, hydroxy, cyano, nitro, carboxyl, amido, sulfonamido, C1-C8 alkyl, C1-C8 hydroxyalkyl, C1-C8 alkoxy, C1-C8 alkylamino, haloC1-C8 alkyl, haloC1-C8 hydroxyalkyl, haloC1-C8 alkoxy, haloC1-C8 alkylamino, C3-C12 cycloalkyl, C3-C12 heterocyclyl, C6-C12 aryl, C5-C14 heteroaryl. 5 The term “alkylthio” used in the present invention means alkyl-S-, in which the alkyl is as defined above. Alkylthio groups include, but are not limited to, methylthio, ethylthio, propylthio, butylthio, etc. The term “alkanoyl” used in the present invention means alkyl-C(O)-, in which the alkyl is as defined above. 10 The term “alkylsulfonyl” used in the present invention means alkyl-S(O)2-, in which the alkyl is as defined above. The term “haloalkyl” used in the present invention means a straight or branched alkyl group substituted with halogens (preferably fluorine, chlorine, bromine, iodine), in which the “alkyl” is as defined above. Examples of “haloalkyl” used in the present invention include, but 15 are not limited to, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, tetrafluoroethyl, pentafluoroethyl, 1,1,1-trifluoroprop-2-yl, etc. “Haloalkyl” can be substituted one or more times by halogens. The term “halohydroxyalkyl” used in the present invention means a hydroxyalkyl group 20 substituted with halogens (preferably fluorine, chlorine, bromine, iodine), in which the hydroxyalkyl is as defined above. “Halohydroxyalkyl” can be substituted one or more times by halogens. The term “haloalkoxy” used in the present invention means a hydroxyalkyl group substituted with halogens (preferably fluorine, chlorine, bromine, iodine), in which the alkoxy is 25 as defined above. “Haloalkoxy” can be substituted one or more times by halogens. The term “haloalkylamino” used in the present invention means an alkylamino group substituted with halogens (preferably fluorine, chlorine, bromine, iodine), in which the alkylamino is as defined above. “Haloalkylamino” can be substituted one or more times by halogens. 30 To avoid ambiguity, for example: when reference is made to alkyl, cycloalkyl, heterocyclyl, aryl and / or heteroaryl substitutions, it is intended that each of these groups is substituted individually, or that a combination of these groups is substituted. “Pharmaceutically acceptable salt” refers to a salt formed by the compound of the present invention with an acid or a base, and is suitable for use as a dug. Pharmaceutically acceptable 2022303441   30 Mar 2026 salts include inorganic salts and organic salts. One preferred class of salts are the salts formed by the compounds of the invention with acids. Suitable salt-forming acids include, but are not limited to: inorganic acids such as hydrochloric acid, hydrobromic acid, hydrofluoric acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid, organic acids such as 5 formic acid, acetic acid, trifluoroacetic acid, propionic acid, oxalic acid, malonic acid, succinic acid, fumaric acid, maleic acid, lactic acid, malic acid, tartaric acid, citric acid, picric acid, methanesulfonic acid, p-toluenesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, camphorsulfonic acid, 2-O-P-D-glucopyranosyl-L-ascorbic acid, isonicotinic acid, salicylic acid, ascorbic acid, gentisic acid, gluconic acid, pyruvic acid, naphthalenesulfonic acid, stearic acid, 10 phenylacetic acid, p-aminobenzenesulfonic acid, isethionic acid, pamoic acid, tannic acid; and acidic amino acids such as aspartic acid,glutamic acid. One preferred class of salts are the salts formed by the compounds of the invention with bases. Suitable salt-forming bases include, but are not limited to: inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, and sodium phosphate, and organic bases such as ammonia, 15   triethylamine, diethylamine, piperazine, guanidine, and diethanolamine. In this specification, the term “comprising” is intended to denote the inclusion of a stated integer or integers, but not necessarily the exclusion of any other integer, depending on the context in which that the term is used. This applies to variants of that term such as “comprising” or “comprises”. 20 The second aim of the present invention is to provide a pharmaceutical composition including one or more of the compounds described in any of the above technical solutions. The pharmaceutical composition of the present invention can be composed of one or more of the compounds described in any of the above technical solutions and other compounds, or composed of one or more of the compounds described in any of the above technical solutions. 25 The present invention provides a pharmaceutical preparation, which comprises at least one active component, and the active component is one or more of the compounds described in any of the above technical solutions. The pharmaceutical preparation comprises at least one active component and one or more pharmaceutically acceptable carriers or excipients. The active component can be any one or more of the BTK inhibitor compound of the present invention, an 30 optical isomer of the compound, a pharmaceutically acceptable salt of the compound or its optical isomer, a solvate of the compound or its optical isomer. The carriers include conventional diluents, excipients, fillers, binders, wetting agents, disintegrants, absorption accelerators, surfactants, adsorption carriers, lubricants, etc. in the pharmaceutical field, and when necessary, flavoring agents, sweeteners, etc. can also be added. 2022303441   30 Mar 2026 The drug of the present invention can be formulated into various forms such as tablets, powders, granules, capsules, oral liquids, and injections. The drugs in each of the above dosage forms can be formulated according to conventional methods in the pharmaceutical field. On the other hand, the present invention provides the use of the compound of the general 5 formula VI disclosed herein and its optical isomers or pharmaceutically acceptable salts or solvates thereof to inhibit Bruton's tyrosine kinase (Btk) activity, IKZF1 activity, or to treat diseases, disorders, or conditions that would benefit from the inhibition of Bruton's tyrosine kinase (Btk) activity, IKZF1 activity. In a further preferred embodiment, the present invention provides a method for inhibiting 10 the Bruton's tyrosine kinase activity in a subject in need by administering a composition containing a therapeutically effective amount of at least one compound to the subject, wherein the structural formula of the compound is set forth in the general formula VI. In some embodiments, the subject in need thereof suffers from an autoimmune disease, such as inflammatory bowel disease, arthritis, lupus, rheumatoid arthritis, psoriatic arthritis, 15 osteoarthritis, Still's disease, juvenile arthritis, diabetes, myasthenia gravis, Hashimoto's thyroiditis, Ord’s thyroiditis, Graves' disease, Sjogren’s syndrome, multiple sclerosis, Guillain-Barre syndrome, acute disseminated encephalomyelitis, Addison's disease, optic opsoclonus-myoclonus syndrome, ankylosing spondylitis, antiphospholipid antibody syndrome, aplastic anemia, autoimmune hepatitis, coeliac disease, Goodpasture’s syndrome, immune 20 thrombocytopenic purpura (ITP), optic neuritis, scleroderma, primary biliary cirrhosis, Reiter’s syndrome, Takayasu's arteritis, temporal arteritis, warm autoimmune hemolytic anemia, Wegener's granulomatosis, psoriasis, alopecia universalis, Behcet's disease, chronic fatigue, familial dysautonomia, endometriosis, interstitial cystitis, neuromyotonia, scleroderma or vulvodynia and chronic graft-versus-host disease (cGvHD). 25 In a further embodiment, the subject in need suffers from a cancer. In one embodiment, the cancer is a B cell or plasma cell proliferative disease, such as diffuse large B cell lymphoma, follicular lymphoma, small lymphocytic lymphoma, chronic lymphocytic leukemia, B cell prolymphocytic leukemia, lymphoplasmacytic lymphoma / Waldenstrom macroglobulinemia, splenic marginal zone lymphoma, plasma cell myeloma, plasmacytoma, extranodal marginal 30 zone B cell lymphoma, lymph node marginal zone B cell lymphoma, mantle cell lymphoma, mediastinum (thymus) large B cell lymphoma, intravascular large B cell lymphoma, primary effusion lymphoma, Burkitt lymphoma / leukemia, multiple myeloma, or lymphomatoid granulomatosis. 2022303441   30 Mar 2026 The present invention also provides the use of the compounds of the present invention or pharmaceutically acceptable salts thereof in the preparation of BTK inhibitors, especially their use in the treatment of cell proliferation diseases. The cell proliferative diseases include cancers. In other words, the invention also provides the use of the compound of the general formula VI, 5 its optical isomers or pharmaceutically acceptable salts or solvates thereof alone or in combination with other drugs in the treatment of proliferative diseases (such as cancers). Antitumor drugs that can be used in combination with the compounds provided by the present invention or their pharmaceutically acceptable salts thereof include, but are not limited to, at least one of the following types: mitotic inhibitors (such as vinblastine, vindesine, and 10 vinorelbine); tubulin breakdown inhibitors (such as Taxol)); alkylating reagents (such as cisplatin, carboplatin and cyclophosphamide); antimetabolites (such as 5-fluorouracil, tegafur, methotrexate, cytarabine, and hydroxyurea); antibiotics can be inserted (such as doxorubicin, mitomycin and bleomycin)); enzymes (such as aspartase); topoisomerase inhibitors (such as etoposide and camptothecin); biological response modifiers (such as interferons); immune 15 checkpoint inhibitors (such as PD-1 inhibitors, PD-L1 inhibitors, CTLA-4 inhibitors); CD20 monoclonal antibody; BCL2 inhibitors. The inventors of the present invention have confirmed through experiments that the compounds of the present invention can degrade BTK. The inventors of the present invention have confirmed through experiments that the 20 compounds of the present invention can degrade BTKC481S. The inventors of the present invention have confirmed through experiments that the compounds of the present invention have anti-proliferation inhibitory effects on Mino, OCI-LY10 tumor cell lines. The inventors of the present invention have confirmed through experiments that the 25 compounds of the present invention have good oral absorption properties in mice. The inventors of the present invention have confirmed through experiments that the compounds of the present invention have good oral absorption properties in dogs. The inventors of the present invention have confirmed through experiments that the compounds of the present invention have a strong effect on inhibiting tumor growth in vivo. 30 DETAILED DESCRIPTION OF EMBODIMENTS Intermediate 1. cyclopentyl-3-(piperidin-3-yl)imidazolin-2-one 2022303441   30 Mar 2026 Synthesis step 1. Tert-butyl 3-(3-(2-Chloroethyl)ureido)piperidin-1-carboxylate (1-1) N-Boc-3-aminopiperidine (25.0 g, 125 mmol) and triethylamine (25.3 g, 250 mmol) were dissolved in dichloromethane (250 mL), and chloroethyl isocyanate (15.8 g, 150 mmol) was slowly added dropwise. After 4 h of reaction, water was added, the organic layers were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate solution, the mixture was filtered, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain tert-butyl 3-(3-(2-chloroethyl)ureido)piperidine-1-carboxylate (1-1) as a solid. ESI-MS: m / z = 306 [M+H]+. Synthesis step 2. Tert-butyl 3-(2-Oxoimidazolin-1-yl)piperidin-1-carboxylate (1-2) Tert-butyl 3-(3-(2-chloroethyl)ureido)piperidine-1-carboxylate (4.03 g, 13.2 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL), and 60% sodium hydride (1.06 g, 26.4 mmol) was added in ice bath, and the mixture was reacted at room temperature overnight under stirring. 60% sodium hydride (0.57 g, 14.1 mmol) was added again, the mixture was reacted for 2 h, the reaction was quenched by adding water, extracted with dichloromethane. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound tert-butyl 3-(2-oxoimidazolin-1-yl)piperidine-1-carboxylate (1-2). ESI-MS: m / z = 270 [M+H]+. Synthesis step 3. Tert-butyl 3-(3-Cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1 -carboxylate (1-3) tert-butyl 3-(2-oxoimidazolin-1-yl)piperidine-1-carboxylate (3.38 g, 12.5 mmol) was dissolved in anhydrous tetrahydrofuran (40 mL), and 60% sodium hydride (1.01 g, 25.1 mmol) was added in ice bath, and after 5 min, the mixture was reacted at room temperature for 1 h under stirring. The mixture was placed back into the ice bath, iodocyclopentane (3.68 g, 18.8 mmol) was slowly added dropwise, and the resulting mixture was reacted at room temperature for 16 h under stirring, and then the reaction was quenched by adding water, and extracted with dichloromethane. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound tert-butyl 3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidine-1-carboxylate (1-3). ESI-MS: m / z = 67 2022303441   30 Mar 2026 338 [M+H]+. Synthesis step 4. 1-cyclopentyl-3-(piperidin-3-yl)imidazolin-2-one(Intermediate 1) tert-butyl 3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidine-1-carboxylate (3.38 g, 10 mmol) was dissolved in dioxane (35 mL), 4N HCl (31 mL) was slowly added dropwise and the 5 mixture was reacted at room temperature for 2 h under stirring. The solvent was removed from the reaction liquid under reduced pressure to obtain 1-cyclopentyl-3-(piperidin-3-yl)imidazolin-2-one (Intermediate 1). ESI-MS: m / z = 238 [M+H]+. Intermediate 2. 1-(oxetan-3-yl)-3-(piperidin-3-yl)imidazolin-2-one 10 The synthesis method was the same as that for Intermediate 1, except that the iodocyclopentane in synthesis step 3 was replaced with 3-iodooxetane to obtain Intermediate 2, ESI-MS: m / z = 226 [M+H]+. Intermediate 3. 1-cyclohexyl-3-(piperidin-3-yl)imidazolin-2-one 15 The synthesis method was the same as that for Intermediate 1, except that the iodocyclopentane in synthesis step 3 was replaced with iodocyclohexane to obtain Intermediate 3, ESI-MS: m / z = 252 [M+H]+. Intermediate 4. 1-(piperidin-3-yl)-3-(tetrahydro-2H-pyran-4-yl)imidazolin-2-one 20 The synthesis method was the same as that for Intermediate 1, except that the iodocyclopentane in synthesis step 3 was replaced with 4-iodotetrahydropyran to obtain Intermediate 4, ESI-MS: m / z = 254 [M+H]+. Intermediate 5. 1-methyl-3-(piperidin-3-yl)imidazolin-2-one 25 The synthesis method was the same as that for Intermediate 1, except that the iodocyclopentane in synthesis step 3 was replaced with methyl iodide to obtain Intermediate 5, 2022303441   30 Mar 2026 ESI-MS: m / z = 184 [M+H]+. Intermediate 6. 1-(-2-azabicyclo[2.2.1]heptan-6-yl)-3-methylimidazolin-2-one The synthesis method was the same as that for Intermediate 5, except that 5 N-Boc-3-aminopiperidine in   synthesis step 1 was   replaced   with tert-butyl 6-amino-2-azabicyclo[2.2.1]heptane-2-carboxylate to obtain the Intermediate 6: 1-(-2-azabicyclo[2.2.1]heptan-6-yl)-3-methylimidazolin-2-one, ESI-MS: m / z = 196 [M+H]+. Intermediate 7. 1-(-2-azabicyclo[2.2.1]heptan-6-yl)-3-isopropylimidazolin-2-one 10 The synthesis method was the same as that for Intermediate 6, except that methyl iodide in synthesis step 3 was replaced with 2-iodopropane to obtain Intermediate 7, ESI-MS: m / z = 224 [M+H]+. Intermediate 8. 1-(-2-azabicyclo[2.2.2]octan-6-yl)-3-methylimidazolin-2-one 15 The synthesis method was the same as that for Intermediate 5, except that N-Boc-3-aminopiperidine in synthesis step 1 was replaced with tert-butyl 6-amino-2-azabicyclo[2.2.2]octane-2-carboxylate to obtain the Intermediate 8. ESI-MS: m / z = 210 [M+H]+. Intermediate 9. 3-chloro-5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl) 20 pyrazin-2-carbonitrile The Intermediate 1, 1-cyclopentyl-3-(piperidin-3-yl)imidazolin-2-one (2.38 g, 10 mmol), and N,N-diisopropylethylamine (7 mL) were dissolved in DMF (20 mL) solution and the mixture was placed in an ice bath. 3,5-dichloropyrazine-2-carbonitrile (1.74 g, 10 mmol) was 25 added, the mixture was reacted for 15 min, then placed at room temperature and reacted for 2022303441   30 Mar 2026 another 16 h. The reaction was completed, water was added, and extracted with ethyl acetate. The organic layers were combined, washed twice with water, washed with saturated sodium chloride, dried with anhydrous sodium sulfate, and filtered with suction. The solvent was removed under reduced pressure, and purification was performed by column chromatography to 5 obtain compound 3-chloro-5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazine-2 -carbonitrile. ESI-MS: m / z = 375 [M+H]+. Intermediate 10. 3-chloro-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl) pyrazin-2-carbonitrile 10 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 2 to obtain Intermediate 10, ESI-MS: m / z = 363 [M+H]+. Intermediate 11. 3-chloro-5-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl) pyrazin-2-carbonitrile 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 3 to obtain Intermediate 11, ESI-MS: m / z = 389 [M+H]+. Intermediate 12. 3-chloro-5-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl) piperidin-1-yl)pyrazin-2-carbonitrile 20 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 4 to obtain Intermediate 12, ESI-MS: m / z = 391 [M+H]+. Intermediate 13. 3-chloro-5-(3-(3-oxotetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl) piperidin-1-yl)pyrazin-2-carbonitrile 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 2-(piperidin-3-yl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one to obtain Intermediate 13, ESI-MS: m / z = 347 [M+H]+. Intermediate 14. 3-chloro-5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3H)-yl) piperidin-1-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 2-(piperidin-3-yl)hexahydroimidazo[1,5-a]pyridin-3(2H)-one to obtain Intermediate 14, ESI-MS: m / z = 361 [M+H]+. Intermediate 15. 3-chloro-5-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl) pyrazin-2-carbonitrile Cl The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 5 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-6-ethylpyrazine-2-carbonitrile to obtain Intermediate 15, ESI-MS: m / z = 349 [M+H]+. Intermediate 16. 3-chloro-5-(3-(3-methyl-2-oxohexacyclopenta[d]imidazol-1(2H)-yl) piperidin-1-yl)pyrazin-2-carbonitrile CN Cl The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-methyl-3-(piperidin-3-yl)hexahydrocyclopenta[d]imidazol-2(1H)-one to obtain Intermediate 16, ESI-MS: m / z = 361 [M+H]+. Intermediate 17. 3-chloro-5-(3-(3-methyl-2-oxooctahydro-1H-benzo[d]imidazol-1-yl) piperidin-1-yl)pyrazin-2-carbonitrile CN 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-methyl-3-(piperidin-3-yl)octahydro-2H-benzo[d]imidazol-2-one to obtain Intermediate 17, ESI-MS: m / z = 375 [M+H]+. Intermediate 18. 3-chloro-5-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl) 5 piperidin-1-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with    4-methyl-6-(piperidin-3-yl)-4,6-diazaspirocyclo[2.4]heptan-5-one hydrochloride to obtain Intermediate 18, ESI-MS: m / z = 347 [M+H]+. 10 Intermediate 19. 3-chloro-5-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl) piperidin-1-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with    5-methyl-7-(piperidin-3-yl)-5,7-diazaspirocyclo[3.4]octane-6-one 15 hydrochloride to obtain Intermediate 19, ESI-MS: m / z = 361 [M+H]+. Intermediate 20. 3-chloro-5-(3-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 20 was replaced with   1-methyl-3-(piperidin-3-yl)-1,3-dihydro-2H-benzo[d]imidazol-2-one hydrochloride to obtain Intermediate 20, ESI-MS: m / z = 369 [M+H]+. Intermediate 21. 3-chloro-5-(3-(3-oxoimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1-yl) pyrazin-2-carbonitrile 25 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 2022303441   30 Mar 2026 was replaced with 2-(piperidin-3-yl)imidazo[1,5-a]pyridin-3(2H)-one to obtain Intermediate 21, ESI-MS: m / z = 355 [M+H]+. Intermediate 22. (-5-chloro-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)- 1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 5 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 22, ESI-MS: m / z = 322 [M+H]+. Intermediate 23. (-4-chloro-2-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl) 10 pyrimidin-5-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 5 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 2,4-dichloro-5-cyanopyrimidine to obtain Intermediate 23, ESI-MS: m / z = 321 [M+H]+. 15 Intermediate 24. 2-chloro-5-fluoro-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-cyanopyridine N^O F^_CN The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 5 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 20 3-cyano-2,6-dichloro-5-fluoropyridine to obtain Intermediate 24, ESI-MS: m / z = 338 [M+H]+. Intermediate 25. 2-chloro-5-methoxy-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin -1-yl)-3-cyanopyridine The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 25 was replaced with Intermediate 5 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 2022303441   30 Mar 2026 10 2,6-dichloro-5-methoxynicotinonitrile to obtain Intermediate 25, ESI-MS: m / z = 350 [M+H]+. Intermediate 26. 3-chloro-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 6 to obtain Intermediate 26, ESI-MS: m / z = 333 [M+H]+. Intermediate 27. 3-chloro-5-(-6-(3-isopropyl-2-oxoimidazolin-1-yl)-2-azabicyclo [2.2.1]heptan-2-yl)pyrazin-2-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 7 to obtain Intermediate 27, ESI-MS: m / z = 361 [M+H]+. Intermediate 28. 2-chloro-6-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)nicotinonitrile 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 6 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 2,6-dichloronicotinonitrile to obtain Intermediate 28, ESI-MS: m / z = 332 [M+H]+. Intermediate 29. 3-chloro-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2] octan-2-yl)pyrazin-2-carbonitrile 20 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 8 to obtain Intermediate 29, ESI-MS: m / z = 347 [M+H]+. Intermediate 30. 5-chloro-3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-1,2,4-triazin-6-carbonitrile 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 6 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 30, ESI-MS: m / z = 334 [M+H]+. 5 Intermediate 31. 5-chloro-3-(3-(3-ethyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-ethyl-3-(piperidin-3-yl)imidazolin-2-one and 10 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 31, ESI-MS: m / z = 336 [M+H]+. Intermediate 32. 5-chloro-3-(3-(3-isopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carbonitrile 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with     1-isopropyl-3-(piperidin-3-yl)imidazolin-2-one    and 3,5- dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 32, ESI-MS: m / z = 350 [M+H]+. Intermediate 33. 5-chloro-3-(3-(2-oxo-3-(trifluoromethyl)imidazolin-1-yl)piperidin-20 1-yl)-1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with     1-(piperidin-3-yl)-3-(trifluoromethyl)imidazolin-2-one     and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to 2022303441   30 Mar 2026 10 15 20 obtain Intermediate 33, ESI-MS: m / z = 376 [M+H]+. Intermediate 34. 5-chloro-3-(3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carbonitrile f3c^ The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with    1-(piperidin-3-yl)-3-(2,2,2-trifluoroethyl)imidazolin-2-one and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 34, ESI-MS: m / z = 390 [M+H]+. Intermediate 35. 5-chloro-3-(3-(3-cyclopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile Cl The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-cyclopropyl-3-(piperidin-3-yl)imidazolin-2-one and 3,5-dichloropyrazine -2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 35, ESI-MS: m / z = 348 [M+H]+. Intermediate 36. 5-chloro-3-(3-(3-cyclobutyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile ,CN N^° The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-cyclobutyl-3-(piperidin-3-yl)imidazolin-2-one and 3,5-dichloropyrazine -2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 36, ESI-MS: m / z = 362 [M+H]+. Intermediate 37. 5-chloro-3-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 9, except that 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 37, ESI-MS: m / z = 376 [M+H]+. Intermediate 38. 5-chloro-3-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile ci 10 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 3 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 38, ESI-MS: m / z = 390 [M+H]+. Intermediate 39. 5-chloro-3-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile CN 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 2 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 39, ESI-MS: m / z = 364 [M+H]+. Intermediate 40. 5-chloro-3-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carbonitrile ci 20 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 4 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 40, ESI-MS: m / z = 392 [M+H]+. Intermediate 41. 5-chloro-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile 2022303441   30 Mar 2026 CN The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-phenyl-3-(piperidin-3-yl)imidazolin-2-one and 3,5-dichloropyrazine -2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 41, ESI-MS: m / z = 384 [M+H]+. Intermediate 42. 5-chloro-3-(3-(2-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-(2-fluorophenyl)-3-(piperidin-3-yl)imidazolin-2-one and 3,5- dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 42, ESI-MS: m / z = 402 [M+H]+. Intermediate 43. 5-chloro-3-(3-(3-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile F              CN The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with    1-(3-fluorophenyl)-3-(piperidin-3-yl)imidazolin-2-one   and 3,5- dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 43, ESI-MS: m / z = 402 [M+H]+. Intermediate 44. 5-chloro-3-(3-(2-oxo-3-(pyridin-3-yl)imidazolin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-(piperidin-3-yl)-3-(pyridin-3-yl)imidazolin-2-one and 3,5-dichloropyrazine -2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 44, 2022303441   30 Mar 2026 ESI-MS: m / z = 385 [M+H]+. Intermediate 45. 5-chloro-3-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl) piperidin-1-yl)-1,2,4-triazin-6-carbonitrile N ^Cl n"VCN 10 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 4-methyl-6-(piperidin-3-yl)-4,6-diazaspirocyclo[2.4]heptan-5-one hydrochloride and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 45, ESI-MS: m / z = 348 [M+H]+. Intermediate 46. 5-chloro-3-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl) piperidin-1-yl)-1,2,4-triazin-6-carbonitrile Cl 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with    5-methyl-7-(piperidin-3-yl)-5,7-diazaspirocyclo[3.4]octane-6-one hydrochloride and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 46, ESI-MS: m / z = 362 [M+H]+. Intermediate 47. 5-chloro-3-(3-(3-oxotrihydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl) piperidin-1-yl)-1,2,4-triazin-6-carbonitrile Cl 20 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 2-(piperidin-3-yl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 47, ESI-MS: m / z = 348 [M+H]+. Intermediate 48. 5-chloro-3-(6-(3-cyclopentyl-2-oxoimidazolin-1-yl)-2-azabicyclo [2.2.1]heptan-2-yl)-1,2,4-triazin-6-carbonitrile Cl 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with 1-(2-azabicyclo[2.2.1]heptan-6-yl)-3-cyclopentylimidazolin-2-one and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 48, ESI-MS: m / z = 388 [M+H]+. 5 Intermediate 49. 5-chloro-3-(6-(2-oxo-3-phenylimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-1,2,4-triazin-6-carbonitrile CN The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with   1-(2-azabicyclo[2.2.1]heptan-6-yl)-3-phenylimidazolin-2-one   and 10 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 49, ESI-MS: m / z = 396 [M+H]+. Intermediate 50. 5-chloro-3-(6-(3-oxotrihydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl) -2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carbonitrile 15 The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with     2-(2-azabicyclo[2.2.1]heptan-6-yl)hexahydro-3H-pyrrole[1,2-c] imidazole-3-one and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 50, ESI-MS: m / z = 360 [M+H]+. Intermediate 51. 5-chloro-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2] 20 octan-2-yl)-1,2,4-triazin-6-carbonitrile The synthesis method was the same as that for Intermediate 9, except that Intermediate 1 was replaced with Intermediate 8 and 3,5-dichloropyrazine-2-carbonitrile was replaced with 3,5-dichloro-1,2,4-triazine-6-nitrile to obtain Intermediate 51, ESI-MS: m / z = 348 [M+H]+. 25 Intermediate 52. Tert-butyl 4-(4-aminophenyl)-4-methylpiperidin-1-carboxylate 2022303441   30 Mar 2026 Synthesis step 1. N-ethoxycarbonyl-4-hydroxyl-4-methylpiperidine (52-1) N-ethoxycarbonyl-4-piperidone (10.00 g, 58.41 mmol) was dissolved in diethyl ether solution and the mixture was cooled to -30°C. 3M methylmagnesium chloride (5.24 g, 70.1 5 mmol) in THF was added, and the mixture was placed at 0°C and reacted for 2 h under stirring. When the reaction was completed, saturated aqueous ammonium chloride solution was added, and the mixture was filtered to remove the white solid. The aqueous layer was extracted with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under reduced pressure, and purification was 10 performed by column chromatography to obtain the target compound N-ethoxycarbonyl-4-hydroxy-4-methylpiperidine (52-1). ESI-MS: m / z= 188 [M+H]+. Synthesis step 2. N-ethoxycarbonyl-4-(4-bromophenyl)-4-methylpiperidine(52-2) N-ethoxycarbonyl-4-hydroxy-4-methylpiperidine (3.08 g, 16.45 mmol) and 4-bromobenzene (25.83 g, 164.50 mmol) was placed in an ice bath at 0°C, and 15 trifluoromethanesulfonic acid (24.69 g, 164.50 mmol) was slowly add dropwise and the mixture was reacted at room temperature for 3 h. After the reaction was completed, the reactant was added to ice water, alkalized by adding 1N NaOH, and extracted with dichloromethane three times. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure 20 and purification was performed by column chromatography to obtain compound N-ethoxycarbonyl-4-(4-bromophenyl)-4-methylpiperidine (52-2). ESI-MS: m / z = 326 [M+H]+ . Synthesis step 3. 4-(4-bromophenyl)-4-methylpiperidine(52-3) N-ethoxycarbonyl-4-(4-bromophenyl)-4-methylpiperidine (7.00 g, 21.46 mmol) was dissolved in ethanol (20 mL), and potassium hydroxide (24.08 g, 429.14 mmol) was added and 25 the mixture was reacted at 80°C overnight. After the reaction was completed, the reaction liquid was distilled under reduced pressure to obtain a residue. The residue was dissolved in dichloromethane solution, washed with water, and extracted with dichloromethane. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under reduce pressure, and the 30 resulting product was used directly in the next reaction. ESI-MS: m / z = 254 [M+H]+ . Synthesis step 4. Tert-butyl 4-(4-Bromophenyl)-4-methylpiperidin-1-carboxylate (52-4) 2022303441   30 Mar 2026 Compound 4-(4-bromophenyl)-4-methylpiperidine (5.40 g, 21.25 mmol) was dissolved in dichloromethane (50 mL), and Boc anhydride (7.42 g, 33.99 mmol) was slowly added dropwise, and the mixture was reacted for 1 h at room temperature. After the reaction was completed, water was added, and dichloromethane was added for extraction. The organic layers were combined, 5 washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound tert-butyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate (52-4). ESI-MS: m / z = 354 [M+H]+ . Synthesis step 5. Tert-butyl 4-(4-aminophenyl)-4-methylpiperidin-1-carboxylate 10 (Intermediate 52) Under nitrogen protection, compounds N-Boc-4-(4-bromophenyl)-4-methylpiperidine (2.60 g, 7.34 mmol), 2-(dicyclohexylphosphino)biphenyl (65.00 mg, 0.19 mmol), tris(dibenzylideneacetone)dipalladium (68.00 mg, 0.07 mmol), and LiHMDS (14.70 mL) were dissolved in anhydrous THF (15 mL), and the mixture was reacted at 65°C overnight. After the 15 reaction was completed, dichloromethane was added for extraction. Then washed with water, washed with saturated sodium chloride, dried with anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound tert-butyl 4-(4-aminophenyl)-4-methylpiperidine-1-carboxylate (Intermediate 52). ESI-MS: m / z = 291 20 [M+H]+. Intermediate 53. Tert-butyl 4-(4-aminophenyl)piperazin-1-carboxylate Synthesis step 1. Tert-butyl 4-(4-nitrophenyl)piperazin-1-carboxylate (53-1) p-fluoronitrobenzene (1.41 g, 10 mmol), N,N-diisopropylethylamine (6.46 g, 50 mmol), 25 and 1-Boc-piperazine (1.86 g, 10 mmol) were dissolved in DMF (20 mL), the temperature was raised to 90°C for reaction overnight under stirring. Water was added, and extracted with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound tert-butyl 30 4-(4-nitrophenyl) piperazine-1-carboxylate (53-1). ESI-MS: m / z = 308 [M+H]+. Synthesis step 2. Tert-butyl 4-(4-aminophenyl)piperazin-1-carboxylate (Intermediate 53) Compound tert-butyl 4-(4-nitrophenyl)piperazine-1-carboxylate (1.54 g, 5 mmol) was 2022303441   30 Mar 2026 dissolved in ethanol (20 mL), Pd / C (154 mg) was added, and the mixture was reacted at room temperature for 2 h under H2. After the reaction was completed, the reaction liquid was filtered, and used ethyl acetate and methanol for the filter cake . The organic layers were combined, and the solvent was removed under reduced pressure to directly obtain the product tert-butyl 5   4-(4-aminophenyl)piperazine-1-carboxylate (Intermediate 53). ESI-MS: m / z = 278 [M+H]+. Intermediate 54. Tert-butyl 9-(4-aminophenyl)-3,9-diazaspirocyclo[5.5]undec-3-carboxylate N-Boc The synthesis method was the same as that for Intermediate 53, except that 10 1-Boc-piperazine in synthesis step 1 was replaced with tert-butyl 3,9-diazaspiro[5.5]undecane-3-carboxylate to obtain the Intermediate 54. ESI-MS: m / z = 346 [M+H]+. Intermediate 55. Tert-butyl 6-(4-aminophenyl)-2,6-diazaspirocyclo[3.3]heptan-2-carboxylate 15 20 25 N~Boc The synthesis method was the same as that for Intermediate 53, except that 1-Boc-piperazine in synthesis step 1 was replaced with tert-butyl 2,6-diazaspiro[3.3]heptane-2-carboxylate to obtain the Intermediate 55. ESI-MS: m / z = 290 [M+H]+. Intermediate 56. 7-(4-aminophenyl)-7-azaspiro[3.5]non-2-one The synthesis method was the same as that for Intermediate 53, except that 1-Boc-piperazine (1 mmol) in synthesis step 1 was replaced with 7-azaspiro[3.5]nonan-2-one to obtain Intermediate 56. ESI-MS: m / z = 231 [M+H]+. Intermediate 57. Tert-butyl 4-(4-aminobenzoyl)piperidin-1-carboxylate H2N O    —\ Synthesis step 1. Tert-butyl 4-(4-bromobenzoyl)piperidin-1-carboxylate (57-1) The compound bromobenzene (1.57 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL) solution, tert-butyl 4-(chlorocarbonyl)-piperidine-1-carboxylate (2.97 g, 12 mmol) was 2022303441   30 Mar 2026 10 added,aluminum trichloride (1.33 g, 10 mmol) was added, and the mixture was heated to 70°C, reacted for 10 h. After the reaction was completed, the reaction liquid was slowly added to a 3M HCl solution, extracted with ethyl acetate, washed with water, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound tert-butyl 4-(4-bromobenzoyl)piperidine-1-carboxylate (57-1). ESI-MS: m / z = 368 [M+H]+. Synthesis step 2. Tert-butyl 4-(4-aminobenzoyl)piperidin-1-carboxylate (Intermediate 57) The synthesis method was the same as that in synthesis step 5 of Intermediate 31, except that tert-butyl 4-(4-bromophenyl)-4-methylpiperidine-1-carboxylate was replaced with tert-butyl 4-(4-bromobenzoyl)piperidine-1-carboxylate to obtain Intermediate 57. ESI-MS: m / z = 305 [M+H]+. Intermediate 58. Tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate 15 H2N N—Boc 20 25 30 Synthesis step 1. Tert-butyl 4-(4-nitrophenyl)-3,6-dihydropyridin-1(2H)-carboxylate (58-1) 1-Bromo-4-nitrobenzene (2.02 g, 10 mmol), N-Boc-1,2,5,6-tetrahydropyridine-4-boronic acid pinacol ester (3.71 g, 12 mmol), [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloride (731.7 mg, 1 mmol), and potassium carbonate (4.15 g, 30 mmol) were dissolved in a solution of dioxane and water, and the mixture was refluxed and reacted for 2 h under nitrogen. After the reaction was completed, the reaction liquid was filtered, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (58-1). ESI-MS: m / z = 305 [M+H]+. Synthesis step 2. Tert-butyl 4-(4-aminophenyl)piperidin-1-carboxylate (Intermediate 58) Compound tert-butyl 4-(4-nitrophenyl)-3,6-dihydropyridine-1(2H)-carboxylate (3.05 g, 10 mmol) was dissolved in a mixture solvent of ethanol and DMF (volume ratio 1:1, 20 ml), 10% palladium on carbon (305 mg) was added, and the mixture was stirred at room temperature under hydrogen gas for 24 h. After the reaction was completed, the reaction liquid was filtered, and the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (Intermediate 58). ESI-MS: m / z = 277 [M+H]+. Intermediate 59. Tert-butyl 4-(4-aminophenyl)-4-fluoropiperidin-1-carboxylate 2022303441   30 Mar 2026 Synthesis step 1. Tert-butyl 4-(4-bromophenyl)-4-hydroxylpiperidin-1-carboxylate (59-1) Under nitrogen protection, p-bromoiodobenzene (2.83 g, 10 mmol) was dissolved in 5 anhydrous THF (20 mL), and the mixture was placed at -78°C, and a solution of n-butyllithium in THF (1.92 g, 30 mmol) was added dropwise. After reacting at -78°C for 2 h, a solution of N-tert-butoxycarbonyl-4-piperidone in THF (2.40 g, 12 mmol) was added dropwise, and the mixture was reacted at -78°C for 2 h. After the reaction was completed, the reaction was quenched by adding water, and extracted by adding ethyl acetate. The organic layers were 10 combined, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (59-1). ESI-MS: m / z = 356 [M+H]+. Synthesis step 2. Tert-butyl 4-(4-bromophenyl)-4-fluoropiperidin-1-carboxylate (59-2) Tert-butyl 4-(4-bromophenyl)-4-hydroxypiperidine-1-carboxylate (3.56 g, 10 mmol) was 15 dissolved in anhydrous dichloromethane (30 mL), and the mixture was placed at -78°C, and bis (2-methoxyethyl)aminosulfur trifluoride (11.06 g, 50 mmol) was added and the mixture was moved to room temperature and reacted for 72 h. After the reaction was completed, the reaction was quenched by adding saturated sodium bicarbonate solution, and extracted by adding dichloromethane. The organic phases were combined, the solvent was removed under reduced 20 pressure, and purification was performed by column chromatography to obtain compound (59-2). ESI-MS: m / z = 358 [M+H]+. Synthesis step 3. Tert-butyl 4-(4-aminophenyl)-4-fluoropiperidin-1-carboxylate (Intermediate 59) The synthesis method was the same as that for Intermediate 52, except that 25 N-Boc-4-(4-bromophenyl)-4-methylpiperidine in synthesis step 5 was replaced with compound 59-2 to obtain Intermediate 59. ESI-MS: m / z = 295 [M+H]+. Intermediate 60. Tert-butyl 4-(4-amino-3-fluorophenyl)piperidin-1-carboxylate The synthesis method was the same as that for Intermediate 58, except that 30 1-bromo-4-nitrobenzene in synthesis step 1 was replaced with 2-fluoro-4-bromonitrobenzene to obtain Intermediate 60. ESI-MS: m / z = 295 [M+H]+. 2022303441   30 Mar 2026 Intermediate 61. Tert-butyl 4-(4-amino-2-cyanophenyl)piperidin-1-carboxylate CN The synthesis method was the same as that for Intermediate 58, except that 1-bromo-4-nitrobenzene in synthesis step 1 was replaced with 2-bromo-5-nitrobenzonitrile to 5 obtain Intermediate 61. ESI-MS: m / z = 302 [M+H]+. Intermediate 62. Tert-butyl 4-(4-aminophenyl)-3-fluoropiperidin-1-carboxylate Synthesis step 1. Tert-butyl 3-hydroxyl-4-(4-nitrophenyl)piperidin-1-carboxylate (62-1) 10 Under nitrogen conditions, compound 58-1 (2.44 g, 8 mmol) was dissolved in anhydrous glycol dimethyl ether (12 mL), and the mixture was placed at 0°C; sodium borohydride (484.2 mg, 12.8 mmol) was added and the mixture was reacted for 5 min under stirring. Boron trifluoride ether (2.27 g, 16 mmol) was added dropwise, and the mixture was reacted at room temperature overnight under stirring. The reaction liquid was placed at 0°C, water was added 15 until boiling stopped, 10 M aqueous sodium hydroxide solution (5 mL) was added, hydrogen peroxide (5 mL) was added dropwise, and the reaction was warmed to room temperature and stirred for 2 h. The reaction was diluted with water, and then extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure, and purification was performed by column 20 chromatography to obtain compound (62-1). ESI-MS: m / z = 323 [M+H]+. Synthesis step 2. Tert-butyl 3-fluoro-4-(4-nitrophenyl)piperidin-1-carboxylate (62-2) Compound 62-1 (2.26 g, 7 mmol) was dissolved in 1,2-dichloroethane (15 mL), and the reaction liquid was placed at 0°C. Diethylaminosulphur trifluoride (5.64 g, 35 mmol) was added and the reaction liquid was stirred at room temperature overnight. After the reaction was 25 completed, saturated sodium bicarbonate solution was added, extraction was performed with dichloromethane, and the organic layers were combined. The organic layer was washed with water, dried over anhydrous sodium sulfate, and filtered. The solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (62-2). ESI-MS: m / z = 325 [M+H]+. 30 Synthesis step 3. Tert-butyl 4-(4-aminophenyl)-3-fluoropiperidin-1- carboxylate (Intermediate 62) 2022303441   30 Mar 2026 Compound 62-2 (1.95 g, 6 mmol) was dissolved in methanol (12 mL), 10% palladium on carbon (195 mg) was added, hydrogen was introduced, and the mixture was reacted overnight at a pressure of 3 atm. After the reaction was completed, the reaction liquid was filtered, and the solvent was removed under reduced pressure, and purification was performed by column 5 chromatography to obtain compound (Intermediate 62). ESI-MS: m / z = 295 [M+H]+. Intermediate 63. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4- methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide Synthesis step 1. Tert-butyl 4-(4-((3-cyano-6-(3-(3-cyclopentyl-2-oxoimidazolin 10   -1-yl)piperidin-1-yl)pyrazin-2-yl)amino)phenyl)-4-methylpiperidin-1-carboxylate (63-1) Intermediate 9 (3.75 g, 10 mmol), intermediate 52 (2.91 g, 10 mmol), cesium carbonate (9.78 g, 30 mmol), BINAP (622.69 mg, 1 mmol), and Pd2(bda)3(1.02 g, 1 mmol) were dissolved in dioxane (25 mL), and the mixture was reacted under reflux for 3 h while stirring. After the reaction was completed, the reaction liquid was filtered, and the solid was washed with 15 dichloromethane solution, the organic layers were combined, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (63-1). ESI-MS: m / z = 629 [M+H]+. Synthesis step 2. Tert-butyl 4-(4-((3-carbamoyl-6-(3-(3-cyclopentyl-2-oxoimidazolin -1-yl)piperidin-1-yl)pyrazin-2-yl)amino)phenyl)-4-methylpiperidin-1-carboxylate (63-2) 20 Tert-butyl 4-(4-((3-cyano-6-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl) pyrazin-2-yl) amino)phenyl)-4-methylpiperidine-1-carboxylate (6.29 g, 10 mmol) was dissolved in a mixed solvent of methanol and DMSO (1:1, 50 mL), and cesium carbonate (1.63 g, 5 mmol) was added, and 30% H2O2 (10 mL) was added, and the mixture was reacted at room temperature for 30 min under stirring. After the reaction was completed, acetonitrile solution was added and the mixture 25 was stirred for 5 min, and distilled under reduced pressure, the residue was dissolved in ethyl acetate solution, and washed with water three times. The organic layers were combined, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (63-2). ESI-MS: m / z = 647 [M+H]+. 30 Synthesis step 3. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4- 2022303441   30 Mar 2026 methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide (Intermediate 63) Tert-butyl 4-(4-((3-carbamoyl-6-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl) pyrazin-2-yl)amino)phenyl)-4-methylpiperidine-1-carboxylate (3.24 g, 5 mmol) was dissolved in dioxane (15 mL), and 4 N HCl (16 mL) was added dropwise in ice bath, and the mixture was 5 moved to room temperature and reacted for 30 min. After the reaction was completed, the reaction liquid was distilled under reduced pressure to obtain Intermediate 63. ESI-MS: m / z = 547 [M+H]+. Intermediate 64. 3-((4-(4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl) -2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 10 to obtain Intermediate 64. ESI-MS: m / z = 535 [M+H]+. Intermediate 65. 5-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4- 15 methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 11 to obtain Intermediate 65. ESI-MS: m / z = 561 [M+H]+. 20 Intermediate 66. 3-((4-(4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 12 to obtain Intermediate 66. ESI-MS: m / z = 2022303441   30 Mar 2026 563 [M+H]+. Intermediate 67. 3-((4-(4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxotetrahydro -1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 13 to obtain Intermediate 67. ESI-MS: m / z = 519 [M+H]+. Intermediate 68. 3-((4-(4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1-yl)pyrazin-2-carboxamide 10 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 14 to obtain Intermediate 68. ESI-MS: m / z = 533 [M+H]+. Intermediate 69. 5-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 15 to obtain Intermediate 69. ESI-MS: m / z = 521 [M+H]+. Intermediate 70. 5-(3-(3-methyl-2-oxohexahydrocyclopenta[d]imidazol-1(2H)-yl) piperidin-1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide) 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 16 to obtain Intermediate 70. ESI-MS: m / z = 533 [M+H]+. Intermediate 71. 5-(3-(3-methyl-2-oxooctahydro-1H-benzo[d]imidazol-1-yl) piperidin-1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 17 to obtain Intermediate 71. ESI-MS: m / z = 547 [M+H]+. Intermediate 72. 5-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl) piperidin-1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 18 to obtain Intermediate 72. ESI-MS: m / z = 519 [M+H]+. Intermediate 73. 5-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl)piperidin -1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 19 to obtain Intermediate 73. ESI-MS: m / z = 533 [M+H]+. 5          Intermediate 74. 5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4- (piperazin-1-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 64, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 53 to obtain Intermediate 74. ESI-MS: m / z 10 = 522 [M+H]+. Intermediate 75. 3-((4-(3,9-diazaspiro[5.5]undecan-3-yl)phenyl)amino)-5-(3-(3- (oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide o The synthesis method was the same as that for Intermediate 64, except that Intermediate 15 52 in synthesis step 1 was replaced with Intermediate 54 to obtain Intermediate 75. ESI-MS: m / z = 590 [M+H]+. Intermediate 76. 3-((4-(2,6-diazaspirocyclo[3.3]heptan-2-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 64, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 55 to obtain Intermediate 76. ESI-MS: m / z = 534 [M+H]+. Intermediate 77. 5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(2-oxo-7-azaspiro[3.5]non-7-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 64, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 56 and step 3 was omitted to obtain Intermediate 77. ESI-MS: m / z = 575 [M+H]+. Intermediate 78. 5-(3-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl) piperidin-1-yl)-3-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 20 to obtain Intermediate 78. ESI-MS: m / z = 541 [M+H]+. Intermediate 79. 3-((4-(4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxoimidazo [1,5-a]pyridin-2(3H)-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 21 to obtain Intermediate 79. ESI-MS: m / z = 527 [M+H]+. Intermediate 80. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 58 to obtain Intermediate 80. ESI-MS: m / z = 533 [M+H]+. Intermediate 81. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(piperidin-4-carbonyl)phenyl)amino)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 57 to obtain Intermediate 81. ESI-MS: m / z = 561 [M+H]+. Intermediate 82. Preparation of 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl) piperidin -1-yl)-3-((4-fluorophenyl)amino)pyrazin-2-carboxamide 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with 4-fluoroaniline and step 3 was omitted to obtain Intermediate 82. ESI-MS: m / z = 468 [M+H]+. Intermediate 83. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 2022303441   30 Mar 2026 52 in synthesis step 1 was replaced with tert-butyl 6-amino-3,4-dihydroisoquinoline-2 (1H)-carboxylate to obtain Intermediate 83. ESI-MS: m / z = 505 [M+H]+. Intermediate 84. 5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-3- ((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Intermediate 64, except that Intermediate 52 in synthesis step 1 was replaced with tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate to obtain Intermediate 84. ESI-MS: m / z = 493 [M+H]+. Intermediate 85. 3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(4-methylpiperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 22 to obtain Intermediate 85. ESI-MS: m / z = 494 [M+H]+. Intermediate 86. 2-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-4-((4-(4-methylpiperidin-4-yl)phenyl)amino)pyrimidin-5-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 23 to obtain Intermediate 86. ESI-MS: m / z = 493 [M+H]+. Intermediate 87. 5-fluoro-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-2-((4-(4-methylpiperidin-4-yl)phenyl)amino)nicotinamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 24 to obtain Intermediate 87. ESI-MS: m / z = 510 [M+H]+. Intermediate 88. 5-methoxy-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-2-((4-(4-methylpiperidin-4-yl)phenyl)amino)nicotinamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 25 to obtain Intermediate 88. ESI-MS: m / z = 522 [M+H]+. Intermediate 89. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4-fluoropiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 59 to obtain Intermediate 89. ESI-MS: m / z = 551 [M+H]+. Intermediate 90. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((2-fluoro-4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 2022303441   30 Mar 2026 52 in synthesis step 1 was replaced with Intermediate 60 to obtain Intermediate 90. ESI-MS: m / z = 551 [M+H]+. Intermediate 91. 3-((3-cyano-4-(piperidin-4-yl)phenyl)amino)-5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 61 to obtain Intermediate 91. ESI-MS: m / z = 558 [M+H]+. Intermediate 92. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(3-fluoropiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide o ■A 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 52 in synthesis step 1 was replaced with Intermediate 62 to obtain Intermediate 92. ESI-MS: m / z = 551 [M+H]+. Intermediate 93. 5-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl)piperidin -1-yl)-3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 18 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 93. ESI-MS: m / z = 505 [M+H]+. Intermediate 94. 5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3H)-yl)piperidin-1-yl) -3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 14 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 94. ESI-MS: m / z = 505 [M+H]+. 5 Intermediate 95. 5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 26 and Intermediate 52 was replaced with 10 Intermediate 58 to obtain Intermediate 95. ESI-MS: m / z = 491 [M+H]+. Intermediate 96. 5-(-6-(3-isopropyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan -2-yl)-3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 15 9 in synthesis step 1 was replaced with Intermediate 27 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 96. ESI-MS: m / z = 519 [M+H]+. Intermediate 97. 6-(-6-(3-methyl-2-oxyimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-2-((4-(piperidin-4-yl)phenyl)amino)nicotinamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 28 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 97. ESI-MS: m / z = 490 [M+H]+. Intermediate 98. 3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2- 5 yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 30 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 98. ESI-MS: m / z = 492 [M+H]+. 10 Intermediate 99. 5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2]octan-2-yl) -3-((4-(piperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 29 and Intermediate 52 was replaced with 15 Intermediate 58 to obtain Intermediate 99. ESI-MS: m / z = 505 [M+H]+. Intermediate 100. 3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 20 9 in synthesis step 1 was replaced with Intermediate 22 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 100, ESI-MS: m / z = 480 [M+H]+. Intermediate 101. 3-(3-(3-ethyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin -4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 31 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 101, ESI-MS: m / z = 494 [M+H]+. 5 Intermediate 102. 3-(3-(3-isopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4- (piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 32 and Intermediate 52 was replaced with 10 Intermediate 58 to obtain Intermediate 102, ESI-MS: m / z = 508 [M+H]+. Intermediate 103. 3-(3-(2-oxo-3-(trifluoromethyl)imidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 15 9 in synthesis step 1 was replaced with Intermediate 33 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 103, ESI-MS: m / z = 534 [M+H]+. Intermediate 104. 3-(3-(2-oxo-3-(2,2,2-trifluoroethyl)imidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 2022303441   30 Mar 2026 10 9 in synthesis step 1 was replaced with Intermediate 34 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 104, ESI-MS: m / z = 548 [M+H]+. Intermediate 105. 3-(3-(3-cyclopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 35 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 105, ESI-MS: m / z = 506 [M+H]+. Intermediate 106. 3-(3-(3-cyclobutyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide o An 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 36 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 106, ESI-MS: m / z = 520 [M+H]+. Intermediate 107. 3-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 37 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 107, ESI-MS: m / z = 534 [M+H]+. Intermediate 108. 3-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 38 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 108, ESI-MS: m / z = 548 [M+H]+. 5 Intermediate 109. 3-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 39 and Intermediate 52 was replaced with 10 Intermediate 58 to obtain Intermediate 109, ESI-MS: m / z = 522 [M+H]+. Intermediate 110. 3-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl) piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 15 9 in synthesis step 1 was replaced with Intermediate 40 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 110, ESI-MS: m / z = 550 [M+H]+. Intermediate 111. 3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 41 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 111, ESI-MS: m / z = 542 [M+H]+. Intermediate 112. 3-(3-(3-(2-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-5- 5 ((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 42 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 112, ESI-MS: m / z = 560 [M+H]+. 10 Intermediate 113. 3-(3-(3-fluorophenyl)-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 43 and Intermediate 52 was replaced with 15 Intermediate 58 to obtain Intermediate 113, ESI-MS: m / z = 560 [M+H]+. Intermediate 114. 3-(3-(2-oxo-3-(pyridin-3-yl)imidazolin-1-yl)piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 20 9 in synthesis step 1 was replaced with Intermediate 44 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 114, ESI-MS: m / z = 543 [M+H]+. Intermediate 115. 3-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]heptan-6-yl) piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 45 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 115, ESI-MS: m / z = 506 [M+H]+. 5 Intermediate 116. 3-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]octan-7-yl) piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 46 and Intermediate 52 was replaced with 10 Intermediate 58 to obtain Intermediate 116, ESI-MS: m / z = 520 [M+H]+. Intermediate 117. 3-(3-(3-oxotrihydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl) piperidin-1-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 15 9 in synthesis step 1 was replaced with Intermediate 47 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 117, ESI-MS: m / z = 506 [M+H]+. Intermediate 118. 3-(6-(3-cyclopentyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 48 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 118, ESI-MS: m / z = 546 [M+H]+. Intermediate 119. 3-(6-(2-oxo-3-phenylimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan 5 -2-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 49 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 119, ESI-MS: m / z = 554 [M+H]+. 10 Intermediate 120. 3-(6-(3-oxotrihydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2- azabicyclo[2.2.1]heptan-2-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 50 and Intermediate 52 was replaced with 15 Intermediate 58 to obtain Intermediate 120, ESI-MS: m / z = 518 [M+H]+. Intermediate 121. 3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.2] octan-2-yl)-5-((4-(piperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 20 9 in synthesis step 1 was replaced with Intermediate 51 and Intermediate 52 was replaced with Intermediate 58 to obtain Intermediate 121, ESI-MS: m / z = 506 [M+H]+. Intermediate 122. 3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 10 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 22 and Intermediate 52 was replaced with tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate to obtain Intermediate 122, ESI-MS: m / z = 452 [M+H]+. Intermediate 123. 3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperazin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 22 and Intermediate 52 was replaced with Intermediate 53 to obtain Intermediate 123, ESI-MS: m / z = 481 [M+H]+. Intermediate 124. 3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(4-oxopiperidin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 22 and Intermediate 52 was replaced with 1-(4-aminophenyl)piperidin-4-one to obtain Intermediate 124, ESI-MS: m / z = 494 [M+H]+. Intermediate 125. 5-((4-(4-methylpiperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 41 to obtain Intermediate 125, ESI-MS: m / z = 556 [M+H]+. Intermediate 126. 3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-5-((1,2,3,4- 5 tetrahydroisoquinolin-6-yl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 41 and Intermediate 52 was replaced with tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate to obtain Intermediate 126, 10 ESI-MS: m / z = 514 [M+H]+. Intermediate 127. 3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-5-((4-(piperazin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 15 9 in synthesis step 1 was replaced with Intermediate 41 and Intermediate 52 was replaced with Intermediate 53 to obtain Intermediate 127, ESI-MS: m / z = 543 [M+H]+. Intermediate 128. 3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-5-((4-(4-oxopiperidin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 41 and Intermediate 52 was replaced with 1-(4-aminophenyl)piperidin-4-one to obtain Intermediate 128, ESI-MS: m / z = 556 [M+H]+. Intermediate 129. 3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1] heptan-2-yl)-5-((4-(4-methylpiperidin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 10 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 30 to obtain Intermediate 129, ESI-MS: m / z = 506 [M+H]+. Intermediate 130. 3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2 -yl)-5-((1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 30 and Intermediate 52 was replaced with tert-butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate to obtain Intermediate 130, ESI-MS: m / z = 464 [M+H]+. Intermediate 131. 3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan -2-yl)-5-((4-(piperazin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 15 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 30 and Intermediate 52 was replaced with Intermediate 53 to obtain Intermediate 131, ESI-MS: m / z = 493 [M+H]+. Intermediate 132. 3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2 -yl)-5-((4-(4-oxopiperidin-1-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 63, except that Intermediate 9 in synthesis step 1 was replaced with Intermediate 30 and Intermediate 52 was replaced with 1-(4-aminophenyl)piperidin-4-one to obtain Intermediate 132, ESI-MS: m / z = 506 [M+H]+. 5 Intermediate 133. 2-(2,6-dioxopiperidin-3-yl)-5-(3-oxoazetidin-1-yl)isoindol-1,3-dione Synthesis step 1. Synthesis of 2-(2,6-dioxo-piperidm-3-yl)-5-fluoro-isomdoH,3-dione (133-1) 4-fluorophthalic anhydride (2.257 g, 13.59 mmol) was dissolved in 50 mL glacial acetic 10 acid, 3-aminopiperidine-2,6-dione hydrochloride (2.46 g, 14.95 mmol) and potassium acetate (4.14 g, 42.18 mmol) were added, the mixture was heated to 90°C, and reacted overnight. After the reaction was completed, the reaction liquid was cooled to room temperature, 120 mL of water was added, and kept in ice bath for 40 min. A large amount of white solid was precipitated. Filter-suction was performed. The solid was washed with methanol. The filter cake was dried to 15 obtain a crude product, which was purified by column chromatography to obtain a white solid (133-1) (3.05 g, yield 81.25%). ESI-MS: m / z = 277 [M+H]+ 1H NMR (500 MHz, DMSO-d6) 8 11.16 (s, 1H), 8.02 (dd, J = 8.3, 4.5 Hz, 1H), 7.86 (dd, J = 7.5, 2.3 Hz, 1H), 7.73 (ddd, J = 9.3, 8.2, 2.3 Hz, 1H), 5.18 (dd, J = 12.9, 5.4 Hz, 1H), 2.90 (ddd, J = 17.1, 13.9, 5.4 Hz, 1H), 2.70 -2.52 (m, 2H), 2.08 (dtd, J = 13.0, 5.4, 2.3 Hz, 1H). 20 Synthesis step 2. 2-(2,6-dioxopiperidin-3-yl)-5-(3-oxoazetidin-1-yl)isoindol-1,3-dione (Intermediate 133) 2-(2,6-dioxo-piperidin-3-yl)-5-fluoro-isoindole-1,3-dione (663 mg, 2.40 mmol) was dissolved in 10 mL of DMSO, azetidin-3-one hydrochloride (171 mg, 2.40 mmol) and 836 pl of DIPEA were added, and the mixture was reacted at 90°C overnight. After the reaction was 25 completed, 10 mL of water was added, and extraction was performed with ethyl acetate. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain Intermediate 79 as a yellow 2022303441   30 Mar 2026 solid (668 mg, yield 85.0%), thus Intermediate 133 was obtained. ESI-MS: m / z = 328 [M+H]+ . Intermediate 134 2-(2,6-dioxopiperidin-3-yl)-5-(4-oxopiperidin-1-yl)isoindol-1,3-dione o v The synthesis method was the same as that for Intermediate 133, except that 5 azetidin-3-one hydrochloride in synthesis step 1 was replaced with piperidin-4-one to obtain Intermediate 134. ESI-MS: m / z = 356[M+H]+. Intermediate 135. 3-(1-oxo-5-(4-oxopiperidin-1-yl)isoindol-2-yl)piperidin-2,6-dione Synthesis step 1. 5-(4-(dimethoxymethyl)piperidin-1-yl)isobenzofuran-1(3H)-one (135-1) 10 5-bromophthalide (1.0 g, 4.70 mmol), 4-(dimethoxymethyl)piperidine (1.20 g, 7.04mol), potassium phosphate (2.99 g, 14.09 mmol), and glycol dimethyl ether (15mL) were subjected to nitrogen replacement three times, and tris(dibenzylideneacetone)dipalladium (860 mg, 0.94 mmol) and (±)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthalene (535 mg, 0.94 mmol) were added to a 100 mL double-necked flask in sequence. The mixture was reacted at 80°C for 16 h. A 15 saturated aqueous sodium chloride (60 mL) solution was added, and extraction was performed with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by column chromatography to obtain the product (135-1). ESI-MS: m / z= 292[M+H]+. Synthesis step 2. 4-(4-(dimethoxymethyl)piperidin-1-yl)-2-(hydroxymethyl)benzoic 20 acid (135-2) 5-(4-(dimethoxymethyl)piperidin-1-yl)isobenzofuran-1(3H)-one (943 mg, 3.23 mmol) was added to a mixed solvent (3 mL of tetrahydrofuran, 3 mL of methanol, and 3 mL of water), and sodium hydroxide (387 mg, 9.68 mmol) was added in ice bath, and the mixture was stirred for 1 h at 25°C. After TLC monitoring showed that the reaction was completed, the reaction 25 liquid was adjusted to pH 4-5 with 1 M dilute hydrochloric acid, and extracted with ethyl acetate. The solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain the product (135-2). ESI-MS: m / z = 310[M+H]+. Synthesis step 3. Methyl 4-(4-(dimethoxymethyl)piperidin-1-yl)-2-(hydroxymethyl) benzoate (135-3) 2022303441   30 Mar 2026 4-(4-(dimethoxymethyl)piperidin-1-yl)-2-(hydroxymethyl)benzoic acid (738 mg, 2.38 mmol) was dissolved in a mixed solvent of 5 mL of methanol and 5 mL of ethyl acetate, and trimethylsilylated diazomethane (2 M, 3.58 ml) was added at -10°C, the reaction was stirred for 30 min at -10°C. After TLC monitoring showed that the reaction was completed, the reaction 5 was quenched with ice water (30 mL), extracted with ethyl acetate (10 ml*3), and purification was performed by column chromatography to obtain the product (135-3). ESI-MS: m / z = 324[M+H]+. Synthesis step 4. Methyl 2-(bromomethyl)-4-(4-(dimethoxymethyl)piperidin-1-yl) benzoate (135-4) 10 Methyl 4-(4-(dimethoxymethyl)piperidin-1-yl)-2-(hydroxymethyl)benzoate (693 mg, 2.14 mmol) was dissolved in 10 mL of tetrahydrofuran, and triphenylphosphine (842 mg, 3.21 mmol) and carbon tetrabromide (1.06 g, 3.21 mmol) were added in sequence. The mixture was stirred for 1 h at 25°C. After TLC monitoring showed that the reaction was completed, the reaction was quenched by adding 20 mL of ice water, and extracted with ethyl acetate. The 15 organic phases were combined, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain the product (135-4). ESI-MS: m / z = 386[M+H]+. Synthesis step 5. 3-(5-(4-(dimethoxymethyl)piperidin-1-yl)-1-oxoisoindol-2-yl) piperidin-2,6-dione (135-5) 20 Methyl 2-(bromomethyl)-4-(4-(dimethoxymethyl)piperidin-1-yl)benzoate (432 mg, 1.12 mmol) was dissolved in a solvent of 10 mL of acetonitrile, and then 3-aminopiperidine-2,6-dione hydrochloride (276 mg, 1.67 mmol) and N,N-diisopropylethylamine (585 pl, 3.36 mmol) were added in sequence. The mixture was reacted at 80°C for 16 h. After TLC monitoring showed that the reaction was completed, the reaction liquid was filtered with suction in ice bath and the solid 25 was washed with acetonitrile to obtain a crude product. ESI-MS:m / z= 402[M+H]+. Synthesis step 6. 3-(1-oxo-5-(4-oxopiperidin-1-yl)isoindol-2-yl)piperidin-2,6-dione(Intermediate 135) 3-(5-(4-(dimethoxymethyl)piperidin-1-yl)-1-oxoisoindol-2-yl)piperidine-2,6-dione (270 mg, 0.671 mmol) was dissolved in tetrahydrofuran (1 mL) and water (0.2 mL), pyridine 30 4-methylbenzenesulfonate (337 mg, 1.342 mmol) was added, and the mixture was stirred at 90°C, and concentrated under reduced pressure after the reaction was completed. Purification was performed by column chromatography to obtain (Intermediate 135). ESI-MS: m / z = 342[M+H]+. Intermediate 136. 3-(1-oxo-5-(3-oxoazetidin-1-yl)isoindol-2-yl)piperidin-2,6-dione 0 2022303441   30 Mar 2026 10 The synthesis method was the same as that for Intermediate 135, except that 4-(dimethoxymethyl)piperidine in synthesis step 1 was replaced with azetidin-3-ol to obtain Intermediate 136. ESI-MS: m / z = 314 [M+H]+ . Intermediate 137. 1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-carbaldehyde The synthesis method was the same as that for Intermediate 133, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with azetidin-3-carbaldehyde to obtain Intermediate 137. ESI-MS: m / z = 342 [M+H]+. Intermediate 138. 2-(2,6-dioxopiperidin-3-yl)-5-(piperazin-1-yl)isoindol-1,3-dione N O O o 15 The synthesis method was the same as that for Intermediate 133, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with piperazine to obtain Intermediate 138, ESI-MS: m / z = 343 [M+H]+. Intermediate 139. 2-(2,6-dioxopiperidin-3-yl)-4-(3-oxoaza-1-yl)isoindol-1,3-dione 20 The synthesis method was the same as that for Intermediate 133, except that 4-fluorophthalic anhydride in synthesis step 1 was replaced with 3-fluorophthalic anhydride to obtain Intermediate 139. ESI-MS: m / z = 328 [M+H]+. Intermediate 140. 1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-carbaldehyde 2022303441   30 Mar 2026 The synthesis method was the same as that for Intermediate 133, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with 4-formylpiperidine to obtain Intermediate 140, ESI-MS: m / z = 370 [M+H]+. Intermediate 141. 2-(2,6-dioxopiperidin-3-yl)-5-(4-(3-(piperidin-4-yl)propan-2-yn-1-yl)piperazin-1-yl)isoindol-1,3-dione HN. /          - Synthesis step 1. 2-(2,6-dioxopiperidin-3-yl)-5-(piperazin-1-yl)isoindol-1,3-dione(141-1) The synthesis method was the same as that for Intermediate 133, except that 10 azetidin-3-one hydrochloride in synthesis step 2 was replaced with piperazine to obtain Intermediate (141-1), ESI-MS: m / z = 343 [M+H]+. Synthesis step 2. 2-(2,6-dioxopiperidin-3-yl)-5-(4-(propan-2-yn-1-yl)piperazin-1-yl) isoindol-1,3-dione (141-2) Compound 2-(2,6-dioxopiperidin-3-yl)-5-(piperazin-1-yl)isoindole-1,3-dione (4.12 g, 12 15 mmol), 3-bromopropyne (2.86 g, 24 mmol) and potassium carbonate (8.30 g, 60 mmol) were dissolved in acetonitrile (430 mL), and the mixture was stirred at room temperature for 12 h. The solvent was removed under reduced pressure, the residue was dissolved in water, and extracted with ethyl acetate. The organic layers were combined, washed with saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate, and filtered with suction. The solvent 20 was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (141-2). ESI-MS: m / z = 381 [M+H]+. Synthesis step 3. Tert-butyl 4-(3-(4-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol -5-yl)piperazin-1-yl)propyn-1-yl)piperidin-1-carboxylate (141-3) Under nitrogen protection, compound 2-(2,6-dioxopiperidin-3-yl)-5-(4-(prop-2-yn-1-yl) 25 piperazin-1-yl)isoindole-1,3-dione (2.29 g, 6 mmol) was dissolved in anhydrous THF (30 mL), and the mixture was placed at -78°C. n-butyllithium (576 mg, 9 mmol) was added and the mixture was reacted for 0.5 h. A THF solution of 1-tert-butoxycarbonyl-4-iodopiperidine (2.8 g, 9 mmol) was added, and the mixture was moved to room temperature, raised to 50°C, and reacted for 24 h. The solvent was removed under reduced pressure, the residue was dissolved in 30 water, and extracted with ethyl acetate. The organic layers were combined, washed with 2022303441   30 Mar 2026 saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain compound (141-3). ESI-MS: m / z = 564 [M+H]+ . Synthesis step 4. 2-(2,6-dioxopiperidin-3-yl)-5-(4-(3-(piperidin-4-yl)propan-2-yn-1-yl) piperazin-1-yl)isoindol-1,3-dione(Intermediate 141) The synthesis steps are as described in synthesis step 3 of Intermediate 63, and compound 63-2 was replaced with compound 141-3 to obtain Intermediate 141. ESI-MS: m / z = 464 [M+H]+. Intermediate 142. 1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)pyrrolidin-3- 10 15 The synthesis method was the same as that for Intermediate 133, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with pyrrolidine-3-carbaldehyde. ESI-MS: m / z = 356[M+H]+. Intermediate 143. 2-(2,6-dioxopiperidin-3-yl)-5-fluoro-6-(3-oxoazetidin-1-yl) isoindolin-1,3-dione o o o 20 The synthesis method was the same as that for Intermediate 133, except that 4-fluorophthalic anhydride in synthesis step 1 was replaced with 4,5-difluorophthalic anhydride to obtain Intermediate 143. ESI-MS: m / z = 346[M+H]+. Intermediate 144.   1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl) pyrrolidin-3-carbaldehyde o 25 The synthesis method was the same as that for Intermediate 143, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with pyrrolidine-3-carbaldehyde. ESI-MS: m / z = 374[M+H]+. Intermediate 145. 3-(1-oxo-5-(3-(piperazin-1-yl)propan-1-yne-1-yl)isoindol-2-yl) 2022303441   30 Mar 2026 piperidin-2,6-dione Synthesis step 1. Methyl 4-bromo-2-bromomethyl benzoate (145-1) Methyl 4-bromo-2-methyl-benzoate (2 g) was dissolved in carbon tetrachloride solution 5 (25 mL), and N-bromosuccinimide (1.86 g) and dibenzoyl peroxide were added (437 mg), the mixture was refluxed and reacted for 5 h, and the reaction was monitored by TLC. After the reaction was completed, carbon tetrachloride was removed under reduced pressure, n-hexane was used for redissolution, filter-suction was performed, and the filter cake was washed with n-hexane three times, and then washed with a mixed solution of 1:4 (ethyl acetate:n-hexane). The 10 organic phases were combined, the solvent was removed under reduced pressure, and purification was performed by column chromatography to obtain compound (145-1). ESI-MS:m / z= 307[M+H]+. Synthesis step 2. 3-(5-bromo-1-oxoisoindol-2-yl)piperidin-2,6-dione(145-2) 3-aminopiperidine-2,6-dione hydrochloride (2.41 g) was dissolved in acetonitrile (50 mL), 15 triethylamine (3.24 mL) was added and the mixture was stirred for ten minutes, and then methyl 4-bromo-2-bromomethyl benzoate (2 g) was added dropwise, and the resulting mixture was refluxed and reacted for 5 h, and the reaction was monitored by TLC. After the reaction was completed, the solvent was removed under reduced pressure, 30 ml of methanol was added, refluxed for 30 min, and filtered with suction to obtain compound (145-2). ESI-MS:m / z= 20   323[M+H]+. Synthesis step 3. Tert-butyl 4-(propan-2-yn-1-yl)piperazin-1-carboxylate (145-3) 1-tert-butoxycarbonylpiperazine (5 g, 26.84 mmol) was dissolved in tetrahydrofuran (100 mL), potassium carbonate (5.57 g, 40.26 mmol) and 3-bromopropyne (3.19 g, 26.84 mmol) were added in ice bath and the mixture was reacted at room temperature for 3 h. After the reaction was 25 completed, the reaction liquid was extracted with ethyl acetate and washed with saturated sodium chloride. The organic phases were combined, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and column chromatography was performed to obtain compound (145-3), ESI-MS: m / z= 225[M+H]+. Synthesis step 4. Tert-butyl 4-(3-(2-(2-2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl) 30 propan-2-yn-1-yl)piperazin-1-carboxylate (145-4) 3-(5-bromo-1-oxoisoindol-2-yl)piperidine-2,6-dione (500 mg), copper iodide (59 mg), and triethylamine (430 ul) were added to a 25 mL double-neck flask, DMF (12mL) was added, 2022303441   30 Mar 2026 and nitrogen replacement was performed. Tert-butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate (347 mg) and Pd2(pph3)2Cl2 (109 mg) were added, then nitrogen replacement was performed, the mixture was reacted at 90°C overnight, and the reaction was monitored by TLC until the reaction was completed. A large amount of water was added, and the resulting reaction liquid was 5 extracted with ethyl acetate, washed with saturated sodium chloride, and dried over anhydrous sodium sulfate, and purification was performed by column chromatography to obtain compound (145-4). ESI-MS: m / z = 467[M+H]+. Synthesis step 5. 3-(1-oxo-5-(3-(piperazin-1-yl)propan-1-yne-1-yl)isoindol-2-yl) piperidin-2,6-dione(145) 10 The synthesis method was the same as that in synthesis step 3 of Intermediate 63 to obtain Intermediate 145, ESI-MS:m / z= 367[M+H]+. Intermediate 146. 1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindol-5-yl)piperidin-4-carbaldehyde 15 The synthesis method was the same as that for Intermediate 135, except that 4-(dimethoxymethyl)piperidine in synthesis step 1 was replaced with ethyl 4-piperidinecarboxylate, and 5-bromophthalide was replaced with 6-bromophthalide. The reaction conditions in synthesis step 6 were replaced to the following: the compound (3 mmol) was dissolved in dichloromethane (10 mL), diisobutylaluminum hydride (7.5 mmol) was added, 20 and the mixture was stirred at room temperature overnight; and after the reaction was completed, the reaction liquid was extracted with ethyl acetate, washed with saturated sodium chloride, and dried with anhydrous sodium sulfate, and purification was performed by column chromatography to obtain Intermediate 146. ESI-MS: m / z = 356[M+H]+. Intermediate 147. 1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisooctanol-5-yl) 25 piperidin-4-carboxylic acid o The synthesis method was the same as that for Intermediate 143, except that azetidin-3-one hydrochloride in synthesis step 2 was replaced with piperidine-4-aminocarbaldehyde. ESI-MS: m / z = 388[M+H]+. 2022303441   30 Mar 2026 10 Intermediate 148. 1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl) piperidin-4-carbaldehyde o 0 The synthesis method was the same as that for Intermediate 146, except that 6-bromophthalide was replaced with 5-bromophthalide. ESI-MS: m / z = 356 [M+H]+ Intermediate 149. 1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl) pyrrolidin-3-carbaldehyde o The synthesis method was the same as that for Intermediate 148, except that 4-(dimethoxymethyl)piperidine was replaced with 3-(dimethoxymethyl)pyrrolidine. ESI-MS: m / z = 342 [M+H]+. Referring to the synthetic route and method for Intermediate 133, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 150 o ft ft) ft 370.1 151 o 1 N \ / ^° / ftNH ftftft       o o o 374.1 152 I Z—. -n ft o 361.1 153 o o £IH> / r~NH ft..J         O O 356.1 2022303441   30 Mar 2026 154 _^O Q qA^Aq X o 356.1 155 o O. z I A° x O 372.1 Intermediate 156: Tert-butyl 4-(4-amino-2-fluorophenyl)piperazin-1-carboxylate Synthesis step 1: Tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazm-1-carboxylate 5 3,4-difluoronitrobenzene (796 mg, 5.0 mmol) was dissolved in 20 mL of DMF, and triethylamine (1.01 g, 10.0 mmol) and tert-butyl piperazine-1-carboxylate (1.03 g, 5.5 mmol) were added to the system in sequence. The mixture was stirred, heated to 60°C and reacted for 3 h. TLC detected that the reaction was completed. Water was added. The system was cooled to room temperature, filtered, dried over anhydrous sodium sulfate, and concentrate under reduced 10 pressure to obtain tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate (1.5 g, yield 92%). ESI-MS: m / z = 326.1 [M+H]+. Synthesis step 2: Tert-butyl 4-(4-amino-2-fluorophenyl)piperazin-1-carboxylate Tert-butyl 4-(2-fluoro-4-nitrophenyl)piperazine-1-carboxylate (1.5 g, 4.6 mmol) was dissolved in 10 mL of ethanol, then 10 mL of water, ammonium chloride (394 mg, 7.36 mmol) 15 and iron powder (219 mg, 3.9 mmol) were added to the system and the mixture was reacted at 50°C for 1 h. After the reaction was completed, the reaction liquid was filtered over Celite to remove iron powder and extracted three times with DCM. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate 20 (1.23 g, yield 91%). ESI-MS: m / z = 296.2 [M+H]+. Referring to the synthetic route and method for Intermediate 156, the following intermediates were synthesized: Intermedia te No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 2022303441   30 Mar 2026 157 h2n Cl N-Boc 312.1 158 H2N- F -0- v O N-Boc 310.2 159 h2n- F F vTX / N—Boc 314.2 160 h2n- F F ^N-Boc 314.2 161 h2n- ,CF3 nC N-Boc 346.2 Referring to the synthetic route and method for Intermediate 58, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 162 F H2N^^)— / N-Boc 295.2 163 HO H2N^—( \|-Boc 307.2 164 OH H2N^— / N~Boc 307.2 Intermediate 165: (R)-tert-butyl 4-(4-((6-carbamoyl-3-(3-(3-methyl-2-oxoimidazolin -1-yl)piperidin-1-yl)-1,2,4-triazin-5-yl)amino)-2-fluorophenyl)piperazin-1-carboxylate 2022303441   30 Mar 2026 Synthesis step 1: (R)-tert-butyl 3-(2-oxoimidazolidin-1-yl)piperidin-1-carboxylate (R)-tert-butyl 3-aminopiperidine-1-carboxylate (2 g, 10 mmol) was dissolved in 20 mL of tetrahydrofuran, the system was cooled to 0°C, and 2-chloro ethyl isocyanate (1.17 g, 11 mmol) 5 was slowly added and the mixture was reacted at 20°C for 1 h under stirring, then the system was cooled to 0°C, potassium tert-butoxide (1.68 g, 15 mmol) was slowly added, and the temperature was raised to room temperature for reaction for 2 h. TLC detected that the reaction was completed, water was added to quench the reaction, the system was adjusted to weak acidity, extract three times with water and DCM, and the organic phases were combined, dried over 10 anhydrous sodium sulfate, concentrate under reduced pressure, and subjected to column chromatography to obtain tert-butyl (R)-3-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (1.13 g, yield 42%). ESI-MS: m / z = 270.2 [M+H]+. Synthesis step 2: (R)-tert-butyl 3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-carboxylate 15 (R)-tert-butyl 3-(2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (1.13 g, 4.2 mmol) was dissolved in 10 mL of tetrahydrofuran, and the system was cooled to 10°C. Potassium tert-butoxide (941 mg, 8.4 mmol) and dimethyl sulfate (635 mg, 5.04 mmol) were added in sequence. The mixture was reacted at room temperature for 3 h under stirring. After the reaction was completed, the reaction was quenched by adding water, and extracted three times with DCM, 20 and the organic layers were combined, dried over anhydrous sodium sulfate, and concentrate under reduced pressure, and purification was performed by column chromatography to obtain (R)-tert-butyl 3-(3-methyl-2-oxoimidazolidine-1-yl)piperidine-1-carboxylate (1.13 g, yield 95%). ESI-MS: m / z = 284.2 [M+H]+. Synthesis step 3: (R)-1-methyl-3-(piperidin-3-yl)imidazolin-2-one 25 (R)-tert-butyl 3-(3-methyl-2-oxoimidazolidin-1-yl)piperidine-1-carboxylate (1.13 g, 4.0 mmol) was dissolved in 8 mL of DCM, and 2 mL of TFA was added and the mixture was reacted at room temperature for 1 h. After the reaction was completed, the reaction liquid was extracted three times with DCM, dried over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain crude product (R)-1-methyl-3-(piperidin-3-yl)imidazolin-2-one, which was 30 directly used in the next reaction step. ESI-MS: m / z = 184.1 [M+H]+. 2022303441   30 Mar 2026 Synthesis step 4: Tert-butyl 4-(4-((6-carbamoyl-3-(methylthio)-1,2,4-triazin-5-yl) amino)-2-fluorophenyl)piperazin-1-carboxylate Ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (700 mg, 3.00 mmol) was dissolved in 10 mL of acetonitrile, and DIPEA (1.7 g , 12.84 mmol) and tert-butyl 5 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate (885 mg, 3.00 mmol) were added to the system. After reacting at room temperature for 30 min, ammonia-methanol solution (7 moL / L, 30 mL) was added, the system became turbid within 10 min, and the reaction was continued for 2 h at room temperature. After the reaction was completed, the reaction liquid was concentrated under reduced pressure, slurried with petroleum ether, and filtered to obtain tert-butyl 10 4-(4-((6-carbamoyl-3-(methylthio)-1,2,4-triazine-5-yl)amino)-2-fluorophenyl)piperazine-1-carbo xylate as a yellow solid (1.3 g, yield 93%). ESI-MS: m / z = 464 [M+H]+. Synthesis step 5: (R)-tert-butyl 4-(4-((6-carbamoyl-3-(3-(3-methyl-2-oxoimidazolin -1-yl)piperidin-1-yl)-1,2,4-triazin-5-yl)amino)-2-fluorophenyl)piperazin-1-carboxylate (R)-1-methyl-3-(piperidin-3-yl)imidazolidin-2-one (1.3 g, 2.78 mmol) was dissolved in 15 20 mL of NMP, and mCPBA (85%, 2.4 g, 13.99 mmol) was added, and the mixture was stirred at room temperature for 2 h. After the reaction was completed, DIPEA (2 mL, 11.00 mmol) and (R)-1-methyl-3-(piperidin-3-yl)imidazolin-2-one (661 mg, 3.61 mmol) were added to the system in sequence. The mixture was reacted at 80°C for 2 h. After the reaction was completed, a solid was precipitated after adding water, and filtration was performed to obtain a yellow solid. The 20 yellow solid was dissolved by adding DCM, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain            (R)-tert-butyl            4-(4-((6-carbamoyl-3-(3-(3-methyl-2-oxoimidazolin -1-yl)piperidin-1-yl)-1,2,4-triazin-5-yl)amino)-2-fluorophenyl)piperazine-1-carboxylate   as a yellow solid (300 mg, yield 16%). ESI-MS: m / z = 599.3 [M+H]+. 25 Referring to the synthetic route and method for Intermediate 165, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 166 o^,nh2 1 H mXzNvZk / CFs Y Y YY NyN Yn- .N.         k / N. 0  ||           Boc K .YY .--Yj 649.3 2022303441   30 Mar 2026 167 o. ,nh2 1 H YY YY NyN Yn-- ,N. 0  ||           Boc K Hy 615.3 168 o^nh2 AyV nYn / N. O |     ]                     Boc K YY 'nCjn 617.3 169 o,nh2 1 H m<Y- n^-^f N Y Y । NyN       N , N        Yn,. O ||           Boc 1 Jr J N 617.3 170 o,nh2 YyV N^N Y          N k / N. 0  ||           Boc K YY 613.3 171 i z Y y=o z MH ZI i? Y CD O o 580.3 172 O^NH 1 H m-A^ N. / YX. / F YY YY N^N o A        NB XN >y -- N^j 598.3 173 0-:-.,,-NH2 1 H N„ N if          OH n^n ^yYi 0 A         NB.c xN ^R^ N\_J 610.3 2022303441   30 Mar 2026 174 0,nh2   oh *711^ ,N           L 0   <                 boc w J 610.3 175 Q O CO \ / £■ IZ k / -=Q u.      Z—, °Y \ 615.3 176 0 co ^z □_   )—' \7 £ IZ   Ll_ LL.     ll        z—, Y \ 649.3 177 OY IZ y / vo O z-z Z— Y \ 552.3 178 o^nh2 1 H nA / Nv^zF n Y ¥ | nYn .rk      M\ / O 570.3 179 Y° ZI 1? C ^z 'Z.—f CD Q O 580.3 180 O NH2 XHr, N<yN _ xN^              N „ O r >               Boc ■ NO 579.3 2022303441   30 Mar 2026 Intermediate 185: 1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-fluorophenyl) pyrrolidin-3-carbaldehyde 5 Synthesis step 1: 3-((5-bromo-2-fluorophenyl)amino)propanoic acid 5-bromo-2-fluoroaniline (2 g, 10.58 mmol) was dissolved in 20 mL of toluene, acrylic acid (787 mg, 12.69 mmol) was added to the system, and the mixture was reacted at 100°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated 10 under reduced pressure to obtain 3-((5-bromo-2-fluorophenyl)amino)propionic acid (2.5 g, yield 90%). ESI-MS(M+H)+=262.0. Synthesis step 2: 1-(5-bromo-2-fluorophenyl)dihydropyrimidin-2,4(1H, 3H)-dione 3-((5-bromo-2-fluorophenyl)amino)propionic acid (2.5 g, 9.54 mmol) was dissolved in 2022303441   30 Mar 2026 30 mL of acetic acid, and urea (1.2 g, 19.08 mmol) was added to the system, and the mixture was reacted at 120°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure and subjected to column chromatography (eluted with DCM / MeOH) to obtain 1-(5-bromo-2-fluorophenyl)dihydropyrimidin-2,4(1H,3H)-dione as a brown solid (2 g, yield 73%). ESI-MS(M+H)+=287.0. Synthesis step 3: 1-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2-fluorophenyl) dihydropyrimidin-2,4(1H, 3H)-dione 1-(5-bromo-2-fluorophenyl)dihydropyrimidin-2,4(1H,3H)-dione (500 mg, 1.74 mmol) was dissolved in 10 mL of DMSO, and 3-(1,3-dioxolan-2-yl)pyrrolidine (325 mg, 2.27 mmol), t-BuONa (511 mg, 5.22 mmol), Pd2(dba)3 (155 mg, 0.17 mmol), and X-Phos (201 mg, 0.34 mmol) were added and the mixture was reacted at 80°C for 3h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain 1-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2-fluorophenyl)dihydropyrimidin-2,4(1H,3H)-dione as a brown solid (100 mg, yield 16%). ESI-MS(M+H)+=350.1. Synthesis step 4: 1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-fluorophenyl) pyrrolidin-3-carbaldehyde 1-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2-fluorophenyl)dihydropyrimidin-2,4(1H,3H) -dione (100 mg, 0.28 mmol) was dissolved in 2 mL of TFA and the mixture was reacted at 80°C for 1 h, then 0.1 mL of concentrated hydrochloric acid was added to the system, and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was adjusted to alkalinity by adding saturated aqueous sodium carbonate solution, extracted with DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrate under reduced pressure, and subjected to column chromatography to obtain 1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-fluorophenyl)pyrrolidin-3-carbaldehyde (80 mg, yield 93%). ESI-MS(M+H)+=306.1. Intermediate 186: 1-(3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methoxyphenyl) pyrrolidin -3-carbaldehyde 2022303441   30 Mar 2026 Referring to the synthetic route and method for Intermediate 185, and 5-bromo-2-fluoroaniline in synthesis step 1 was replaced with 5-bromo-2-methoxyaniline, ESI-MS(M+H)+=318.1. Intermediate 187: 3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methylbenzoic acid 10 15 20 H Synthesis step 1: 3-((2-carboxyethyl)amino)-4-methylbenzoic acid 3-amino-4-methylbenzoic acid (10.0 g, 66.2 mmol) was dissolved in 30 mL of toluene, and acrylic acid (18 mL, 264.6 mmol) was added to the system and the mixture was reacted at 110°C for 4 h. After the reaction was completed, DCM was added and a solid was precipitated. Filtration was performed under reduced pressure to obtain 3-((2-carboxyethyl) amino)-4-methylbenzoic acid as a white solid (14.5 g, yield 98%). ESI-MS: m / z = 224 [M+H]+. Synthesis step 2: 3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-4-methylbenzoic acid 3-((2-carboxyethyl)amino)-4-methylbenzoic acid (14.5 g, 65.0 mmol) was dissolved in 30 mL of acetic acid, urea (9.8 g, 162.5 mmol) was added to the system, and the mixture was reacted at 120°C for 12 h. After the reaction was completed, water was added, and a solid was precipitated in the system. The obtained system was filtered, slurried with water, then slurried with acetonitrile, and filtered to obtain 3-(2,4-dioxotetrahydropyrimidin-1(2H)-yl) -4-methylbenzoic acid as a white solid (11.5 g, yield 71%). ESI-MS: m / z = 249 [M+H]+. Referring to the synthetic route and method for Intermediate 187, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 188 H o °yny° 265.1 189 H o °yny° HoJ'Yy 253.1 Intermediate 190: 1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-fluorophenyl) 2022303441   30 Mar 2026 piperidin-4-carbaldehyde Synthesis step 1: 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-nitroaniline 5-fluoro-2-nitroaniline (1 g, 6.41 mmol) was dissolved in 10 mL of DMF, and 4-(1,3-dioxolan-2-yl)piperidine (1.2 g, 7.69 mmol) and cesium carbonate (6.2 g, 19.23 mmol) were added to the system in sequence. The mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 5-(4-(1,3-dioxolan-2-yl)piperdin-1-yl)-2-nitroaniline (1.5 g, yield 79%), ESI-MS (M+H)+=294.1. Synthesis step 2: 4-(1,3-dioxolan-2-yl)-1-(3-fluoro-4-nitrophenyl)piperidine 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-nitroaniline (1.5 g, 5.11 mmol) was dissolved in 15 mL of concentrated hydrochloric acid. HF (70%, 30 mL) was added to the system at 0°C, and the mixture was reacted at room temperature until the reactants were completely dissolved. NaNO2 (423 mg, 6.13 mmol) was added to the system at -78°C, and the mixture was reacted at 0°C for 30 min. Then the temperature was raised to 60°C for reaction for 15-30 min. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 4-(1,3-dioxolan-2-yl)-1-(3-fluoro-4-nitrophenyl)piperidine (1 g, yield 66%). ESI-MS(M+H)+ =297.1. Synthesis step 3: 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluoroaniline 4-(1,3-dioxolan-2-yl)-1-(3-fluoro-4-nitrophenyl)piperidine (1 g, 3.37 mmol) was dissolved in 10 mL of tetrahydrofuran, and ammonium chloride (2 g, 33.78 mmol), water (10 mL), and iron powder (1.9 g, 33.78 mmol) were added to the system in sequence. The mixture was reacted at 70°C for 12 h. After the reaction was completed, the iron powder was removed by filtration with diatomaceous earth. The filtrate was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to purification by column chromatography (eluted with EA / PE) to obtain 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluoroaniline (750 mg, yield 83%). ESI-MS(M+H)+ =267.1. Synthesis step 4: 3-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorophenyl) amino) 126 2022303441   30 Mar 2026 propionic acid 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluoroaniline (750 mg, 2.81 mmol) was dissolved in 10 mL of toluene, acrylic acid (243 mg, 3.38 mmol) was added to the system, and the mixture was reacted at 100°C for 12 h, and the reaction was completed. The reaction liquid 5 was extracted five times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 3-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorophenyl)amino) propionic acid as a yellow liquid (860 mg, yield 90%). ESI-MS(M+H)+=339.2. Synthesis step 5: 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorophenyl) 10 dihydropyrimidin-2,4(1H, 3H)-dione 3-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorophenyl)amino)propionic acid (860 mg, 2.54 mmol) was dissolved in 10 mL of acetic acid, and urea (315 mg, 5.08 mmol) was added to the system, and the mixture was reacted at 120°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times. The organic phases were combined, dried 15 over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl) -2-fluorophenyl)dihydropyrimidin-2,4(1H,3H)-dione as a brown solid (540 mg, yield 58%). ESI-MS(M+H)+=364.2. Synthesis step 6: 1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-fluorophenyl) 20 piperidin-4-carbaldehyde 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorophenyl)dihydropyrimidin-2,4(1H,3H)-dione (540 mg, 1.68 mmol) was dissolved in 6 mL of TFA and the mixture was reacted at 80°C for 1 h, then 0.5 mL of concentrated hydrochloric acid was added to the system, and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was adjusted to 25 alkalinity by adding saturated aqueous sodium carbonate solution, extracted with MeOH / DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrate under reduced pressure, and subjected to column chromatography to obtain 1-(4-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)-3-fluorophenyl)piperidin-4-carbaldehyde as a yellow solid (490 mg, yield 91%). ESI-MS(M+H)+=320.1. 30 Referring to the synthetic route and method for Intermediate 190, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 2022303441   30 Mar 2026 191 0 302.1 192 Vn / =( ^”v —( N—<\ / / -N / =0 o 316.2 193 ^ / / / ^^ / ° 0           ° 288.1 194 £ N “C # N / ° / =nh o           ° 288.1 195 O=--®o 6 / o 288.1 196 / / : “0 o 338.1 197 F. O / —\        / —\ x—(       / Vn x— /       Vmh o 320.1 198 cf3 o 370.1 199 / o^z V o 352.1 200 o / —\   / = / / —\ —(   N / / >—N   ) O o 344.2 201 °\ / —\ / ^N   / —\ —( N— / / Vn / =O o 303.1 2022303441   30 Mar 2026 202 V / N=\ 303.1 \ / NY / Y\ Y° YNH O 203 v / nY   N / =0 ^N{r o 342.2 204 o^, o / 9          1 l S.      ,N. NH ° 380.1 205 o^ ,° r T _N. ,NH y ° 378.2 206 (        Z>— N  >O 0 353.2 207 O^ O^NH2 / \^O X. . N. ,NH r T o N^^^ 345.2 208 HO- / —Yn Y Yn Yo o           o 318.1 272 v \ o a nY Yn Yo o 332.2 Intermediate 209: (S)-N-(2,6-dioxopiperidin-3-yl)-2-fluoro-4-(4-formylpiperidin-1-yl) benzamide Synthesis step 1: Methyl 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluoro benzoate 2022303441   30 Mar 2026 Methyl 4-bromo-2-fluorobenzoate (2.5 g, 10.73 mmol) was dissolved in 20 mL of DMF, and 4-(1,3-dioxolan-2-yl)piperidine (2.0 g, 12.87 mmol), cesium carbonate (8.7 g, 26.82 mmol), Sphos (880 mg, 2.15 mmol), and palladium acetate (240 mg, 1.07 mmol) were added, and the mixture was reacted at 50°C for 2 h under introduced nitrogen protection. After the reaction was 5 completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain methyl 4-(4-(1,3-dioxacyclo-2-yl)piperidin-1-yl)-2-fluorobenzoate as a yellow solid (800 mg, yield 24%). ESI-MS(M+H)+=310.1. 10 Synthesis step 2: 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorobenzoic acid Methyl 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorobenzoate (240 mg, 0.78 mmol) was dissolved in 10 mL of tetrahydrofuran. Lithium hydroxide (90 mg, 3.88 mmol), water (2 mL), and methanol (4 mL) were added to the system in sequence. The mixture was reacted at room temperature for 1 h. After the reaction was completed, the reaction liquid was concentrated 15 under reduced pressure, extracted with DCM, slurried, filtered, and concentrated under reduced pressure to obtain 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorobenzoic acid as a white solid (190 mg, yield 82%). ESI-MS(M-H)+=296.1. Synthesis step 3: (S)-4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin-3-yl)-2-fluorobenzamide 20 (S)-tert-butyl (2,6-dioxopiperidin-3-yl)carbamate (93 mg, 0.73 mmol) was dissolved in 5 mL of DCM, and TFA (1 mL) was added to the system. The mixture was reacted at room temperature for 1 h. After the reaction was completed, the reaction liquid was concentrated under reduced pressure. 5 mL of DMF, 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-2-fluorobenzoic acid (180 mg, 0.61 mmol), HATU (30 mg, 0.79 mmol) and TEA (0.5 mL, 1.22 mol) were added in 25 sequence to the above product. The mixture was reacted at room temperature for 1 h and the reaction was completed. The reaction liquid was extracted three times with DCM, the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain (S)-4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin-3-yl)-2-fluorobenzamide as a 30 white solid (200 mg, yield 80%). ESI-MS(M+H)+=406.2. Synthesis step 4: (S)-N-(2,6-dioxopiperidin-3-yl)-2-fluoro-4-(4-formylpiperidin-1-yl) benzamide (S)-4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin-3-yl)-2-fluorobenzami de (200 mg, 0.49 mmol) was dissolved in 2 mL of TFA and the mixture was reacted at 80°C for 1 2022303441   30 Mar 2026 h. Then 1 mL of concentrated hydrochloric acid was added to the system and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the system was adjusted to be alkaline by adding saturated aqueous sodium carbonate solution, extracted with DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrate under reduced 5 pressure, and subjected to column chromatography to obtain (S)-N-(2,6-dioxopiperidin-3-yl) -2-fluoro-4-(4-formylpiperidin-1-yl)benzamide as a white solid (146 mg, yield 83%). ESI-MS(M+H)+=362.1. Intermediate 210: N-(2,6-dioxopiperidin-3-yl)-5-(4-formylpiperidin-1-yl)pyridine carboxamide 10 Synthesis step 1: Methyl 5-(4-(1, 3-dioxolan-2-yl)piperidin-1-yl)picolinate Methyl 5-fluoropicolinate (2.2 g, 14.18 mmol) was dissolved in 20 mL of DMF, and 4-(1,3-dioxolan-2-yl)piperidine (2.7 g, 17.02 mmol) and potassium carbonate (5.8 g, 42.54 mmol) was added to the system and the mixture was reacted at 90°C for 2 h. After the reaction was 15 completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain methyl 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)picolinate as a yellow solid (3.2 g, yield 78%). ESI-MS(M+H)+=293.1. 20 Synthesis step 2: 5-(4-(1, 3-dioxolan-2-yl)piperidin-1-yl)picolinic acid methyl 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)picolinate (1.5 g, 5.13 mmol) was dissolved in 20 mL of tetrahydrofuran, and lithium hydroxide (615 mg, 25.67 mmol) and water (7.5 mL) were added to the system. The mixture was reacted at room temperature for 2 h. After the reaction was completed, the reaction liquid was concentrated to no solvent, slurried with 25 DCM, and filtered, and the filtrate was concentrated to obtain 5-(4-(1,3-dioxolan-2-yl) piperidin-1-yl)picolinic acid as a white solid (1.3 g, yield 93%). ESI-MS(M+H)+ =279.1. Synthesis step 3: 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin -3-yl)pyridine carboxamide 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)picolinic acid (500 mg, 1.08 mmol) was dissolved 30 in 10 mL of DMF, and 3-aminopiperidin-2,6-dione (255 mg, 1.97 mmol), HATU (752 mg, 1.97 mmol) and triethylamine (0.75 mL, 5.39 mmol) were added to the system in sequence. The 2022303441   30 Mar 2026 mixture was reacted at room temperature for 1 h. After the reaction was completed, the reaction liquid was extracted with DCM three times, and the organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain 5 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin-3-yl)pyridinecarboxamide as a gray solid (350 g, yield 51%). ESI-MS(M+H)+=389.2. Synthesis step 4: N-(2,6-dioxopiperidin-3-yl)-5-(4-formylpiperidin-1-yl)pyridine carboxamide 5-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-N-(2,6-dioxopiperidin-3-yl)pyridinecarboxamide 10 (100 mg, 0.26 mmol) was dissolved in 2 mL of TFA and the mixture was reacted at 80°C for 1 h. Then 1 mL of concentrated hydrochloric acid was added to the system and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the system was adjusted to be alkaline by adding saturated aqueous sodium carbonate solution, extracted with DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrate under 15 reduced pressure to obtain N-(2,6-dioxopiperidin-3-yl)-5-(4-formylpiperidin-1-yl) pyridinecarboxamide as a yellow solid (75 mg, yield 84%). ESI-MS(M+H)+ =345.2. Referring to the synthetic route and method for Intermediates 209 and 210, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 211 H 0 °ynY° . U Ls; 1 II 1 H 362.1 212 H O^N^O 358.2 213 H O^N^O o o V Y 1 ■= 374.2 2022303441   30 Mar 2026 214 H F 00^ 380.1 215 rvr n 11 H 11 0 331.1 216 331.1 217 • J-A r>                          11 H 11 331.1 218 A ZI O 331.1 219 9 fx° ^ZNXNH X J H o | N N o'=X~-X 345.2 220 X O ZT / =\ CM o 394.2 221 6 ^Z )=o IZ o 395.2 Intermediate 222: 1-(6-((2,6-dioxopiperidin-3-yl)amino)pyridin-3-yl) pyrrolidin-3-carbaldehyde 2022303441   30 Mar 2026 Synthesis step 1: Synthesis of 5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2- nitropyridine 5-fluoro-2-nitropyridine (1.5 g, 10.56 mmol) was dissolved in 20 mL of DMF, and 5 3-(1,3-dioxolan-2-yl)pyrrolidine (1.8 g, 12.67 mmol) and cesium carbonate (10 g, 31.68 mmol) were added to the system and the mixture was reacted at 80°C for 2 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 10   5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2-nitropyridine as a yellow liquid (2.2 g, yield 75%). ESI-MS(M+H)+=266.1. Synthesis step 2: 5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridin-2-amine 5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-2-nitropyridine (2.1 g, 7.92 mmol) was dissolved in 25 mL of tetrahydrofuran, and ammonium chloride (4.6 g, 79.24 mmol), water (5 mL), and 15 iron powder (4.6 g, 79.24 mmol) were added to the system in sequence. The mixture was reacted at 70°C for 12 h. After the reaction was completed, a large amount of iron powder was filtered out while hot, and the resulting reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 20   5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridine-2-amine as a yellow solid (1.7 g, yield 93%). ESI-MS(M+H)+=236.1. Synthesis step 3: 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridin-2-yl)amino) piperidin-2,6-dione 5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridin-2-amine (1.7 g, 7.23 mmol) was 25 dissolved in 20 mL of DMF, and 3-bromopiperidin-2,6-dione (2 g, 10.84 mmol), Pd(dppf)Cl2(526 mg, 0.72 mmol) and Na2CO3(2.6 g, 21.69 mmol) were added to the system in sequence. The mixture was reacted at 100°C for 3 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced 30 pressure, and subjected to column chromatography to obtain 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridin-2-yl)amino)piperidin-2,6-dione (2 g, yield 80%). ESI-MS(M+H)+=347.2. 2022303441   30 Mar 2026 Synthesis step 4: 1-(6-((2,6-dioxopiperidin-3-yl)amino)pyridin-3-yl)pyrrolidin-3-carbaldehyde 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)pyridin-2-yl)amino)piperidin-2,6-dione (2 g , 5.78 mmol) was dissolved in 10 mL of TFA and the mixture was reacted at 80°C for 1 h. Then 2 5 mL of concentrated hydrochloric acid was added to the system and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was adjusted to alkalinity by adding saturated aqueous sodium carbonate solution, extracted with DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 1-(6-((2,6-dioxopiperidin-3-yl)amino)pyridin-3-yl)pyrrolidin-3- 10 carbaldehyde as a yellow solid (1.5 g, yield 85%). ESI-MS(M+H)+ =303.1. Referring to the synthetic route and method for Intermediate 222, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 223 "b b b 303.1 224 O NA pNN   ; -; 317.2 225 b H o 317.2 226 •b b H o 316.2 227 •b IZ ~b 316.2 2022303441   30 Mar 2026 228 F N O 320.1 229 o 0 o ZI X 330.2 230 AnA 334.2 231 H 1 XrA 334.2 232 H O Nh rnXJ La O^^\^ 384.2 Intermediate 233: methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3] dioxolan-4-yl)piperidin-4-yl)4-methylbenzenesulfonate Synthesis step 1: 7-aminobenzo[d][1,3]dioxolan-4-carboxylic acid 7-nitrobenzo[d][1,3]dioxolan-4-carboxylic acid (1 g, 5.52 mmol) was dissolved in 10 mL 10 of THF, and ammonium chloride (2.9 g, 55.20 mmol), water (3 mL) and iron powder (3 g, 55.20 mmol) were added to the system and the mixture was reacted at 70°C for 12 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with EA / PE) to obtain 7-aminobenzo[d][1,3]dioxolan-4-carboxylic acid (729 mg, yield 85%). ESI-MS(M+H)+ =182.0. Synthesis step 2: Synthesis of 7-fluorobenzo[d][1,3]dioxolan-4-carboxylic acid 7-aminobenzo[d][1,3]dioxolan-4-carboxylic acid (729 mg, 4.02 mmol) was dissolved in 10 mL of concentrated hydrochloric acid, and the mixture was cooled to 0°C. HF (70%, 20 mL) 2022303441   30 Mar 2026 was added to the system at 0°C, and the resulting mixture was reacted at room temperature until the reactants were completely dissolved. NaNO2 (305 mg, 4.42 mmol) was added to the system at -78°C, and the mixture was reacted at 0°C for 30 min. Then the temperature was raised to 60°C for further reaction for 15-30 min. After the reaction was completed, the reaction liquid 5 was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 7-fluorobenzo[d][1,3]dioxolan-4-carboxylic acid (628 mg, yield 85%). ESI-MS(M+H)+=185.0. Synthesis step 3: 7-(4-(hydroxymethyl)piperidin-1-yl)benzo[d][1,3] dioxolan-410 carboxylic acid 7-fluorobenzo[d][1,3]dioxolan-4-carboxylic acid (628 mg, 3.41 mmol) was dissolved in 10 mL of DMF, and piperidin-4-ylmethanol ( 588 mg, 5.11 mmol) and cesium carbonate (3.3 g, 10.23 mmol) were added to the system in sequence. The mixture was reacted at 80°C for 12 h. After the reaction was completed, the reaction liquid was quenched by adding water, and 15 extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 7-(4-(hydroxymethyl)piperidin-1-yl)benzo[d][1,3]dioxolan-4-carboxylic acid (761 mg, yield 80%). ESI-MS(M+H)+=280.1. Synthesis step 4: N-(2,6-dioxopiperidin-3-yl)-7-(4-(hydroxymethyl)piperidin-1-yl) 20 benzo[d][1,3]dioxolan-4-carboxamide 7-(4-(hydroxymethyl)piperidin-1-yl)benzo[d][1,3]dioxolan-4-carboxylic acid (761 mg, 2.72 mmol) was dissolved in 10 mL of DMF, and 3-aminopiperidin-2,6-dione (452 mg, 3.53 mmol), DIPEA (1.0 g, 8.16 mmol) and HATU (1.3 g, 3.53 mmol) were added to the system in sequence. The mixture was reacted at room temperature for 2 h. After the reaction was 25 completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with MeOH / DCM) to obtain   N-(2,6-dioxopiperidin-3-yl)-7-(4-(hydroxymethyl)piperidin-1-yl)benzo[d][1,3]dioxolan -4-carboxamide (793 mg, yield 75%), ESI -MS(M+H)+= 390.2. 30 Synthesis step 5: methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3] dioxolan-4-yl)piperidin-4-yl)4-methylbenzenesulfonate N-(2,6-dioxopiperidin-3-yl)-7-(4-(hydroxymethyl)piperidin-1-yl)benzo[d][1,3]dioxolan-4 -carboxamide (793 mg, 2.03 mmol) was dissolved in 10 mL of DCM, and TsCl (580 mg, 3.05 mmol) and TEA (615 mg, 6.09 mmol) were added to the system in sequence. The mixture was 2022303441   30 Mar 2026 reacted at room temperature for 2 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3]dioxolan-4-yl)piperidin 5 -4-yl)4-methylbenzenesulfonate (992 mg, yield 90%). ESI-MS(M+H)+ =544.2. Intermediate 234: methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)benzo[d][1,3] dioxolan-4-yl)pyrrolidin-3-yl)4-methylbenzenesulfonate Referring to the synthetic route and method for Intermediate 233, and 10 piperidin-4-ylmethanol in synthesis step 3 was replaced with pyrrolidin-3-ylmethanol to obtain methyl (1-(7-((2,6-dioxopipperidin-3-yl)carbamoyl)benzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl) 4-methylbenzenesulfonate, ESI-MS ( M+H)+=530.2. Intermediate 235: methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)-1H-benzo[d] imidazol-4-yl)piperidin-4-yl)4-methylbenzenesulfonate N^NH / —(  n—c 2—\ / —\ TsO              HN—<   / =0 V MH 15                                  O Referring to the synthetic route and method in synthesis steps 3, 4, and 5 of Intermediate 233, and 7-fluorobenzo[d][1,3]dioxolan-4-carboxylic acid in synthesis step 3 was replaced with 4-fluoro -1H-benzo[d]imidazol-7-carboxylic acid to obtain methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)-1H-benzo[d]imidazol-4-yl)piperidin-4-yl)4-methylbe 20 nzenesulfonate, ESI-MS (M+H)+=540.2. Intermediate 236: methyl (1-(7-((2,6-dioxopiperidin-3-yl)carbamoyl)-1H-benzo[d] imidazol-4-yl)pyrrolidin-3-yl)4-methylbenzenesulfonate Referring to the synthetic route and method for Intermediate 235, and 25 pyrrolidin-3-ylmethanol was replaced with piperidin-4-ylmethanol to obtain methyl (1-(7-((2,6-dioxopiperidin-3-yl )carbamoyl)-1H-benzo[d]imidazol-4-yl)pyrrolidin-3-yl)4-methyl benzenesulfonate, ESI-MS (M+H)+=526.5. 2022303441   30 Mar 2026 Intermediate 237: methyl (1-(8-((2,6-dioxopiperidin-3-yl)carbamoyl)-2,3- dihydrobenzo[b][1,4]dioxin-5-yl)piperidin-4-yl)4-methylbenzenesulfonate Referring to the synthetic route and method for Intermediate 233, and 7-nitrobenzo[d][1,3]dioxolan-4-carboxylic acid in synthesis step 1 was replaced with 8-nitro-2,3-dihydrobenzo[b][1,4]dioxin-5-carboxylic acid to obtain methyl (1-(8-((2,6-dioxopiperidin-3-yl)carbamoyl)-2,3-dihydrobenzo[b][1,4]dioxin-5-yl)piperidin-4-yl) 4-methylbenzenesulfonate, ESI-MS(M+H)+=558.2. Intermediate 238: 1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)benzo[d]oxazol-4-yl) piperidin-4-carbaldehyde Nx O Synthesis step 1: 4-fluoro-7-nitrobenzoxazole 5-fluoro-2-nitrobenzamide (1 g, 5.43 mmol) was dissolved in 15 mL of water, and cesium carbonate (5.3 g, 16.29 mmol) was added to the system, and the mixture was reacted for 10 min under microwave at 120W. After the reaction was completed, the reaction liquid was extracted with DCM three times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4-fluoro-7-nitrobenzoxazole (750 mg, yield 75%). ESI-MS(M+H)+=183.1. Synthesis step 2: 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)-7-nitrobenzoxazole 4-fluoro-7-nitrobenzoxazole (750 mg, 4.12 mmol) was dissolved in 10 mL of DMF, and 4-(1,3-dioxolan-2-yl)piperidine (776 mg, 4.94 mmol) and cesium carbonate (4 g, 12.36 mmol) were added to the system in sequence. The mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 4-(4-(1,3-dioxolan-2-yl)piperdin-1-yl)-7-nitrobenzoxazole (900 mg, yield 68%), ESI-MS (M+H)+=320.1. Synthesis step 3: 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-amine 4-(4-(1,3-dioxolan-2-yl)piperdin-1-yl)-7-nitrobenzoxazole (900 mg, 2.82 mmol) was dissolved in 10 mL of tetrahydrofuran, and ammonium chloride (1.6 g, 28.21 mmol), water (10 139 2022303441   30 Mar 2026 mL), and iron powder (1.6 g, 28.21 mmol) were added to the system in sequence. The mixture was reacted at 70°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 5 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-amine (500 mg, yield 61%). ESI-MS(M+H)+=290.1. Synthesis step 4: 3-((4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl) amino)propionic acid 4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-amine (500 mg, 1.73 mmol) 10 was dissolved in 10 mL of toluene, and acrylic acid (128 mg, 2.07 mmol) was added to the system, and the mixture was reacted at 100°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 3-((4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl)amino)propionic acid as a yellow 15 liquid (580 mg, yield 94%). ESI-MS(M+H)+=362.2. Synthesis step 5: 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl) dihydropyrimidin-2,4(1H, 3H)-dione 3-((4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl)amino)propionic acid (580 mg, 1.60 mmol) was dissolved in 10 mL of acetic acid, and urea (200 mg, 3.20 mmol) was 20 added to the system, and the mixture was reacted at 120°C for 12 h. After the reaction was completed, the reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography (eluted with DCM / MeOH) to obtain 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl)dihydropyrimidin-2,4(1H,3H)-dio 25 ne as a brown solid (380 mg, yield 58%). ESI-MS(M+H)+=387.2. Synthesis step 6: 1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)benzo[d]oxazol-4-yl) piperidin-4-carbaldehyde 1-(4-(4-(1,3-dioxolan-2-yl)piperidin-1-yl)benzo[d]oxazol-7-yl)dihydropyrimidin-2,4(1H, 3H)-dione (380 mg, 0.98 mmol) was dissolved in 3 mL of TFA and the mixture was reacted at 30 80°C for 1 h, then 0.2 mL of concentrated hydrochloric acid was added to the system, and the mixture was reacted at 80°C for 3 h. After the reaction was completed, the reaction liquid was adjusted to alkalinity by adding saturated aqueous sodium carbonate solution, extracted with MeOH / DCM five times, and the organic phases were combined, dried over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain 2022303441   30 Mar 2026 1-(7-(2,4-dioxotetrahydropyrimidin-1(2H)-yl)benzo[d]oxazol-4-yl)piperidin-4-carbaldehyde as a yellow solid (310 mg, yield 92%). ESI-MS(M+H)+=343.1. Referring to the synthetic route and method for Intermediate 238, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 239 % t Xi' X- o 342.2 240 0   3 N—(\   / ^N    / =0 0 360.2 5 Intermediate 241: methyl (1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d][1,3] dioxolan-4-yl)pyrrolidin-3-yl)4-methylbenzenesulfonate Synthesis step 1: (1-(7-nitrobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol 10          4-fluoro-7-nitrobenzo[d][1,3]dioxolane (3 g, 16.22 mmol) was dissolved in 20 mL of DMF, and pyrrolidin-3-ylmethanol ( 2 g, 19.46 mmol) and cesium carbonate (15.81 g, 48.64 mmol) were added to the system in sequence. The mixture was reacted at 90°C for 2 h. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, 15 concentrated under reduced pressure, and subjected to column chromatography to obtain (1-(7-nitrobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol as a yellow solid (3.6 g, yield 85%). ESI-MS(M+H)+=267.1. Synthesis step 2: (1-(7-aminobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol (1-(7-nitrobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol (2 g, 8.47 mmol) was 20 dissolved in 30 mL of tetrahydrofuran, and ammonium chloride (7.5 g, 147.26 mmol), water (7.5 mL), and iron powder (8 g, 147.26 mmol) were added to the system in sequence. The mixture was reacted at 70°C for 12 h. After the reaction was completed, a large amount of iron powder was filtered out while hot, and the resulting reaction liquid was extracted with DCM three times. 2022303441   30 Mar 2026 The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain (1-(7-aminobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol as a yellow solid (1.2 g, yield 60%). ESI-MS(M+H)+=237.1. 5 Synthesis step 3: 3-((7-(3-(hydroxymethyl)pyrrolidin-1-yl)benzo[d][1,3]dioxolan-4-yl) amino)piperidin-2,6-dione (1-(7-aminobenzo[d][1,3]dioxolan-4-yl)pyrrolidin-3-yl)methanol (1.2 g, 5.08 mmol) was dissolved in 10 mL of DMF, and 3-bromopiperidin-2,6-dione (1.3 g, 6.61 mmol) and sodium bicarbonate (1.28 g, 15.27 mmol) were added to the system and the mixture was reacted at 70°C 10 for 1 h, and the reaction was completed. the reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 3-((7-(3-(hydroxymethyl)pyrrolidin-1-yl)benzo[d][1,3]dioxolan-4-yl)amino)piperidin-2,6-dione as a yellow solid (1.3 g, yield 75%). ESI-MS(M+H)+=348.2. 15 Synthesis step 4: methyl (1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d][1,3]dioxolan -4-yl)pyrrolidin-3-yl)4-methylbenzenesulfonate 3-((7-(3-(hydroxymethyl)pyrrolidin-1-yl)benzo[d][1,3]dioxolan-4-yl)amino)piperidin-2,6 -dione (1 g, 2.88 mmol) was dissolved in 10 mL of DCM, and p-toluenesulfonyl chloride (820 mg, 4.32 mmol) and 3.5 mL of DIPEA were added to the system in sequence. The mixture was 20 reacted at room temperature for 2 h. After the reaction was completed, the reaction liquid was extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrate under reduced pressure, and subjected to column chromatography to obtain methyl (1-(7-((2,6-dioxopiperidin-3-yl)amino)benzo[d][1,3]dioxolan-4-yl)pyrrolidin -3-yl)4-methylbenzenesulfonate as a yellow solid (1.2 g, yield 85%). ESI-MS(M+H)+ =502.2. 25 Referring to the synthetic route and method for Intermediate 241, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 242 o 'NH 516.2 2022303441   30 Mar 2026 Intermediate 245: 1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-6-yl) pyrrolidin-3-carbaldehyde 5 Synthesis step 1: 3-(2,6-bis(benzyloxy)pyridin-3-yl)-6-bromo-1-methyl-1H-indazole 6-bromo-3-iodo-1-methyl-1H-indazole (2 g, 5.97 mmol) was dissolved in 20 mL of THF, and 2,6-bis(benzyloxy)-3-(4,4,5,5-tetramethyl-1,3,2-dioxobenzaldehyde-2-yl)pyridine (3.7 g, 8.96 mmol), DPPF palladium dichloride (432 mg, 0.60 mmol), and cesium carbonate (5.8 g, 17.91 mmol) were added to the system in sequence. The mixture was reacted at room 10 temperature for 12 h under introduced nitrogen protection. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 3-(2,6-bis(benzyloxy)pyridin-3-yl)-6-bromo-1-methyl-1H-indazole as a yellow solid (1.4 g, yield 15   49%). ESI-MS(M+H)+=500.1. Synthesis step 2: 6-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-3-(2,6-bis(benzyloxy) pyridin-3-yl)-1-methyl-1H-indazole 3-(2,6-bis(benzyloxy)pyridin-3-yl)-6-bromo-1-methyl-1H-indazole (1.4 g, 2.81 mmol) was dissolved in 20 mL of 1,4-dioxane, and 3-(1,3-dioxolan-2-yl)pyrrolidine (485 mg, 3.37 20 mmol), Pd2(dba)3(257 mg, 0.28 mmol), XPhos (267 mg, 0.56 mmol), and cesium carbonate (1.8 g, 5.62 mmol) were added to the system in sequence. The mixture was reacted at 160°C for 12 h under introduced nitrogen protection. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and 25 subjected to column chromatography to obtain 6-(3-(1,3-dioxolan-2-yl)pyrrolidin-1 2022303441   30 Mar 2026 -yl)-3-(2,6-bis(benzyloxy)pyridin-3-yl)-1-methyl-1H-indazole as a yellow solid (860 mg, yield 50%). ESI-MS(M+H)+=563.3. Synthesis step 3: 3-(6-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-1-methyl-1H-indazol -3-yl)piperidin-2,6-dione 5 6-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-3-(2,6-bis(benzyloxy)pyridin-3-yl)-1-methyl-1H -indazole (860 mg, 1.53 mmol) was dissolved in 10 mL of 1,4-dioxane, and palladium hydroxide (21 mg, 0.15 mmol) was added to the system, and the mixture was reacted at room temperature for 12 h under introduced hydrogen. After the reaction was completed, the reaction liquid was filtered and concentrated under reduced pressure to obtain 3-(6-(3-(1,3-dioxolan-2-yl) 10 pyrrolidin-1-yl)-1-methyl-1H-indazol-3-yl)piperidin-2,6-dione as a white solid (500 mg, yield 85%). ESI-MS(M+H)+=385.2 Synthesis step 4: 1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-6-yl) pyrrolidin-3-carbaldehyde 3-(6-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-1-methyl-1H-indazol-3-yl)piperidin-2,6-dione 15 (500 mg, 1.30 mmol) was dissolved in 5 mL of TFA and the mixture was reacted at 80°C for 1 h. 1 mL of concentrated hydrochloric acid was added dropwise and the mixture was reacted at 80°C for 2 h. The reaction liquid was quenched with aqueous sodium bicarbonate solution, extracted with DCM 5 times, and concentrated under reduced pressure to obtain 1-(3-(2,6-dioxopiperidin-3-yl)-1-methyl-1H-indazol-6-yl)pyrrolidin-3-carbaldehyde as a white 20 solid (400 mg, yield 90%). ESI-MS(M+H)+=341.2. Referring to the synthetic route and method for Intermediate 246, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 247 o.^ 0 I rz / \=O z / / i O 355.2 248 0 \-N a. mah 342.2 249 ox \-N  0 N^yAxx^NH 356.2 2022303441   30 Mar 2026 250 < 1    N—N 9 341.2 251 J \= /  1 \^z / \^° X^-Z / / 1 o 355.2 252 0 HN-\ 341.2 253 H o o^n-y O ,-- / => 9 J \^N VN 342.1 254 o b o 392.2 Intermediate 255: 1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)pyrrolidin-3-carbaldehyde Synthesis step 1: 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-3-methyl-2-oxo-2,3- 10 dihydro-1H-benzo[d]imidazol-1-yl)piperidin-2,6-dione 3-(5-bromo-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-2,6-dione (1 g , 2.97 mmol) was dissolved in 20 mL of DMF, and 3-(1,3-dioxolan-2-yl)pyrrolidine (3.6 g, 3.56 mmol), Pd2(dba)3 (280 mg, 0.30 mmol), XPhos (285 mg, 0.59 mmol), and cesium carbonate (1.8 g, 5.62 mmol) were added to the system in sequence. The mixture was reacted at 160°C for 12 h under introduced nitrogen protection. After the reaction was completed, the reaction liquid was quenched by adding water, and extracted with DCM three times. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl) 2022303441   30 Mar 2026 -3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-2,6-dione as a yellow solid (530 mg, yield 45%). ESI-MS(M+H)+=401.2. Synthesis step 2: 1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)pyrrolidin-3-carbaldehyde 5 3-(5-(3-(1,3-dioxolan-2-yl)pyrrolidin-1-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imi dazol-1-yl)piperidin-2,6-dione (530 mg, 1.33 mmol) was dissolved in 5 mL of TFA and the mixture was reacted at 80°C for 1 h. 1 mL of concentrated hydrochloric acid was added dropwise and the mixture was reacted at 80°C for 2 h. After the reaction was completed, the system was adjusted to be alkaline by adding saturated aqueous sodium bicarbonate solution, extracted with 10 DCM 5 times, concentrated under reduced pressure, and subjected to column chromatography to obtain 1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl) pyrrolidin-3-carbaldehyde as a white solid (450 mg, yield 95%). ESI-MS(M+H)+ =357.2. Referring to the synthetic route and method for Intermediate 256, the following intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 257 0 HN-A r l >° 371.2 258 o 6 368.2 259 o H o       / . rv — /      N   o H    u 381.2 260 O H yv° cr 0 382.1 261 A ozjT / ° ■■ o 396.2 2022303441   30 Mar 2026 262 0. H Y y° 395.2 N 0 Intermediate 263: 3-(6-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)propan-2-yn-1-ylmesylate 5 Synthesis step 1: 5-(3-hydroxylpropan-1-yne-1-yl)picolinic acid 5-bromopicolinic acid (2 g, 10.00 mmol) was dissolved in 20 mL of glycol dimethyl ether, and propargyl alcohol (675 mg, 12.00 mmol), tetrakis(triphenylphosphine)palladium (570 mg, 0.50 mmol), copper iodide (380 mg, 2.00 mmol), and DIPEA (4 mL, 30.00 mmol) were added to the system in sequence. The mixture was reacted at 120°C for 20 min. After the reaction was 10 completed, the reaction liquid was filtered, concentrated under reduced pressure, dissolved in DCM, and subjected to column chromatography to obtain 5-(3-hydroxyprop-1-yn-1-yl)picolinic acid as a yellow liquid (750 mg, yield 40%). ESI-MS(M+H)+=178.0. Synthesis step 2: 5-(3-((methylsulfonyl)oxy)propan-1-yne-1-yl)picolinic acid 5-(3-hydroxyprop-1-yn-1-yl)picolinic acid (750 mg, 4.23 mmol) was dissolved in 15 mL 15 of DCM, and methanesulfonyl chloride (724 mg, 6.35 mmol) and TEA ( 855 mg, 8.47 mmol) were added in sequence. The mixture was reacted at room temperature for 3 h. After the reaction was completed, water was added and a solid was precipitated. The resulting system was extracted by adding DCM, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 20   5-(3-((methylsulfonyl)oxy)prop-1-yn-1-yl)picolinic acid as a white solid (700 mg, yield 70%). ESI-MS(M+H)+=256.0. Synthesis step 3: 3-(6-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)propan-2-yn -1-ylmesylate 5-(3-((methylsulfonyl)oxy)prop-1-yn-1-yl)picolinic acid (700 mg, 2.73 mmol) was 25 dissolved in 15 mL of DMF, and 3-aminopiperdine-2,6-dione (418 mg, 3.27 mmol), HATU (1.2 g, 3.27 mmol), and DIPEA (827 mg, 8.19 mmol) were added to the system in sequence. The mixture was reacted at room temperature for 2 h. After the reaction was completed, water was added and a solid was precipitated. The resulting system was extracted by adding DCM, dried 2022303441   30 Mar 2026 over anhydrous sodium sulfate, concentrated under reduced pressure, and subjected to column chromatography to obtain 3-(6-((2,6-dioxopiperidin-3-yl)carbamoyl)pyridin-3-yl)prop-2-yn-1-yl methanesulfonate as a white solid (740 mg, yield 75%). ESI-MS(M+H)+ =366.1. Referring to the synthetic route and method for Intermediate 263, the following 5 intermediates were synthesized: Intermediate No. Intermediate structure LC-MS (ESI-MS) m / z [M+H]+ 264 o zi o=\ A o tn 5 379.1 265 H F O °^N^° MsO^" 369.1 266 ^NH s HN—( Wn \ / u 371.0 267 O HN \ oX J) 363.1 268 O 0 NH 11 MsO.. / ^ 413.1 269 O A o w 5 392.1 270 F u ° ......„O..... 355.1 2022303441   30 Mar 2026 10 15 Example 1. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)ph enyl)amino)pyrazin-2-carboxamide o o Intermediate 63 (5.47 g, 10 mmol) and Intermediate 133 (3.28 g, 10 mmol) were dissolved in a solution of triethylamine (101 mg, 1 mmol) in dichloroethane (40 mL), and the mixture was reacted at room temperature for 5 min under stirring. Sodium triacetoxyborohydride (10.60 g, 50 mmol) was added, and the mixture was reacted at room temperature for 5 h under stirring. After the reaction was completed, the reaction liquid was extracted by adding ethyl acetate and water solution. The organic layers were combined, washed with saturated sodium chloride, dried over anhydrous sodium sulfate, and filtered with suction. The solvent was removed under pressure and purification was performed by column chromatography to obtain Compound 001. ESI-MS: m / z = 858 [M+H]+. Example 2. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidine -3-yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)pip eridin-1-yl)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 64 to obtain Compound 002. ESI-MS: m / z = 846 [M+H]+. Example 3. 5-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)pheny l)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 65 to obtain Compound 003, ESI-MS: m / z = 872 [M+H]+. Example 4. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidine 5 -3-yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imid azolin-1-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 66 to obtain Compound 004, ESI-MS: m / z = 874 [M+H]+. 10 Example 5. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxotetrahydro-1H-pyrrolo[1,2-c]imidazo l-2(3H)-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 15 was replaced with Intermediate 67 to obtain Compound 005, ESI-MS: m / z = 830 [M+H]+. Example 6. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxohexahydroimidazo[1,5-a]pyridin-2(3 H)-yl)piperidin-1-yl)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 68 to obtain Compound 006, ESI-MS: m / z = 844 [M+H]+. 2022303441   30 Mar 2026 Example 7. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-6-ethyl-5-(3-(3-(3-methyl-2-oxyimidazolin-1-yl)p iperidin-1-yl)pyrazin-2-carboxamide —N The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 69 to obtain Compound 007, ESI-MS: m / z = 832 [M+H]+. Example 8. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxohexahydrocyclopenta[d]imi dazol-1(2H)-yl)piperidin-1-yl)pyrazin-2-carboxamide 10 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 70 to obtain Compound 008, ESI-MS: m / z = 844 [M+H]+. Example 9. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxooctahydro-1H-benzo[d]imi dazol-1-yl)piperidin-1-yl)pyrazin-2-carboxamide O 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 71 to obtain Compound 009. ESI-MS: m / z = 858 [M+H]+. Example 10. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(4-methyl-5-oxo-4,6-diazaspirocyclo[2.4]he ptan-6-yl)piperidin-1-yl)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 72 to obtain Compound 010. ESI-MS: m / z = 830 [M+H]+. Example 11. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 5 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(5-methyl-6-oxo-5,7-diazaspirocyclo[3.4]oct an-7-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 73 to obtain Compound 011. ESI-MS: m / z = 844 [M+H]+. 10 Example 12. 3-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin]-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1 -yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 2, except that Intermediate 133 15 was replaced with Intermediate 134 to obtain Compound 012. ESI-MS: m / z = 874 [M+H]+. Example 13. 3-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin]-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1 -yl)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Example 2, except that Intermediate 133 2022303441   30 Mar 2026 was replaced with Intermediate 135 to obtain Compound 013. ESI-MS: m / z = 860 [M+H]+. Example 14. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)azetidin-3-yl) -4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin -1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 2, except that Intermediate 133 was replaced with Intermediate 136 to obtain Compound 014. ESI-MS: m / z = 832 [M+H]+. Example 15. 3-((4-(4-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)piperazin-1-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piperidin-1-yl) 10 pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 74 to obtain Compound 015. ESI-MS: m / z = 833 [M+H]+. Example 16. 3-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidine 15 -3-yl)methyl)piperazin-1-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)piper idin-1-yl)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Example 15, except that Intermediate 133 was replaced with Intermediate 137 to obtain Compound 016. ESI-MS: m / z = 847 [M+H]+. Example 17. 3-((4-(9-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-3,9- diazaspirocyclo[5.5]undec-3-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)pi peridin-1-yl)pyrazin-2-carboxamide 2022303441   30 Mar 2026 0 0 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 75, and Intermediate 1339 was replaced with Compound 133-1 to obtain Compound 017. ESI-MS: m / z = 846 [M+H]+. Example 18. 3-((4-(6-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-2,6-diazaspirocyclo[3.3]heptan-2-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)p iperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 17, except that Intermediate 75 was replaced with Intermediate 76 to obtain Compound 018. ESI-MS: m / z = 790 [M+H]+. Example 19. 3-((4-(2-(4-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperazin -1-yl)-7-azaspiro[3.5]non-7-yl)phenyl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1-yl)pip eridin-1-yl)pyrazin-2-carboxamide o^,nh2 I o 0 •N                NH M \ )=° O The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 77, and Intermediate 133 was replaced with Intermediate 138 to obtain Compound 019. ESI-MS: m / z = 901 [M+H]+. Example 20. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-4-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)pheny l)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with Intermediate 139 to obtain Compound 020. ESI-MS: m / z = 858 [M+H]+. Example 21. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(5-((2,6-dioxopiperidin-3-yl)amino)pyridin-2-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)a mino)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with 3-((6-(3-oxoazetidin-1-yl)pyridin-3-yl)amino)piperidin-2,6-dione to obtain Compound 021. ESI-MS: m / z = 805 [M+H]+. Example 22. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1- (2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-4-yl)azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)pyrazin-2-carboxamide 15 The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with 3-(3-methyl-2-oxo-4-(3-oxoazetidin-1-yl)-2,3-dihydro-1H-benzo[d] imidazol-1-yl)piperidin-2,6-dione to obtain Compound 022. ESI-MS: m / z = 859 [M+H]+. Example 23. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1-oxo-1,2-dihydroisoquinolin-6-yl)azetidin-3-yl)-4-methylpiperidi n-4-yl)phenyl)amino)pyrazin-2-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with 3-(1-oxo-6-(3-oxoazetidin-1-yl)isoquinolin-2(1H)-yl)piperidin-2,6-dione to obtain Compound 023. ESI-MS: m / z = 856 [M+H]+. Example 24. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2- 2022303441   30 Mar 2026 (2,6-dioxopiperidin-3-yl)-1-oxo-1,2,3,4-tetrahydroisoquinolin-6-yl)azetidin-3-yl)-4-methylpi peridin-4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with 3-(1-oxo-6-(3-oxoazetidin-1-yl)-3,4-dihydroisoquinolin-2 (1H)-yl)piperidin -2,6-dione to obtain Compound 023. ESI-MS: m / z = 858 [M+H]+. Example 25. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 10 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 78 to obtain Compound 025. ESI-MS: m / z = 852 [M+H]+. Example 26. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)-4-methylpiperidin-4-yl)phenyl)amino)-5-(3-(3-oxoimidazo[1,5-a]pyridin-2(3H )-yl)piperidin-1-yl)pyrazin-2-carboxamide o 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 79 to obtain Compound 026. ESI-MS: m / z = 838 [M+H]+. Example 27. 5-(3-(3-cyclopentyl-2-oxyimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)piperidin-4-yl)phenyl)amino) pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 80 to obtain Compound 027. ESI-MS: m / z = 844 [M+H]+. Example 28. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-5   (2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperidin-4-yl)methyl)piperidin-4-formyl )phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 81, and Intermediate 133 was replaced with Intermediate 140 to 10 obtain Compound 028. ESI-MS: m / z = 914 [M+H]+. Example 29. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(4-(3-(4-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)piperazin-1-yl)propan-1-yne-1-yl)pi peridin-1-yl)phenyl)amino)pyrazin-2-carboxamide 15 The synthesis step was the same as synthesis step 1 of Intermediate 63, except that compound Intermediate 9 was replaced with Intermediate 82 and Intermediate 52 was replaced with Intermediate 141 to obtain Compound 029. ESI-MS: m / z = 911 [M+H]+. Example 30. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2,3,4-tetrahydrois 20 oquinolin-6-yl)amino)pyrazin-2-carboxamide O^NH2 N 2022303441   30 Mar 2026 10 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 83, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 030. ESI-MS: m / z = 858 [M+H]+. Example 31. 3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxoimidazoli n-1-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 84, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 031. ESI-MS: m / z = 846 [M+H]+. Example 32. 3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidine -3-yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-5-(3-(3-(oxetan-3-yl)-2-oxyimidazol in-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 15 The synthesis method was the same as that for Example 31, except that Intermediate 140 was replaced with Intermediate 137 to obtain Compound 032. ESI-MS: m / z = 818 [M+H]+. Example 33. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl)methyl)-1,2,3,4-tetrahydroiso quinolin-6-yl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 83, and Intermediate 133 was replaced with Intermediate 137 to obtain Compound 033. ESI-MS: m / z = 830 [M+H]+. Example 34. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-4-methylpiperi din-4-yl)phenyl)amino)pyrazin-2-carboxamide 10 The synthesis method was the same as that for Example 1, except that Intermediate 133 was replaced with Intermediate 142 to obtain Compound 034. ESI-MS: m / z = 886 [M+H]+. Example 35. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) pyrrolidin-3-yl)methyl)-4-methylpiperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidaz olin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 15 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 85 to obtain Compound 035. ESI-MS: m / z = 833 [M+H]+. Example 36. 4-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) pyrrolidin-3-yl)methyl)-4-methylpiperidin-4-yl)phenyl)amino)-2-(3-(3-methyl-2-oxoimidaz olin-1-yl)piperidin-1-yl)pyrimidin-5-carboxamide 2022303441   30 Mar 2026 0 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 86 to obtain the compound. ESI-MS: m / z = 832 [M+H]+. Example 37. 2-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) 5 pyrrolidin-3-yl)methyl)-4-methylpiperidin-4-yl)phenyl)amino)-5-fluoro-6-(3-(3-methyl-2-ox oimidazolin-1-yl)piperidin-1-yl)nicotinamide 0 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 87 to obtain Compound 037. ESI-MS: m / z = 849 [M+H]+. 10 Example 38. 2-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) pyrrolidin-3-yl)methyl)-4-methylpiperidin-4-yl)phenyl)amino)-5-methoxy-6-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)nicotinamide 0 The synthesis method was the same as that for Example 34, except that Intermediate 63 15 was replaced with Intermediate 88 to obtain Compound 038. ESI-MS: m / z = 861 [M+H]+. Example 39. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phe nyl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 80 to obtain Compound 039. ESI-MS: m / z = 872 [M+H]+. Example 40. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2- 5   (2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-4-fluoropiperidin -4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 89 to obtain Compound 040. ESI-MS: m / z = 890 [M+H]+. 10 Example 41. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)-2-f luorophenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Example 34, except that Intermediate 63 15 was replaced with Intermediate 90 to obtain Compound 041. ESI-MS: m / z = 890 [M+H]+. Example 42. 3-((3-cyano-4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5 -yl)pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-5-(3-(3-cyclopentyl-2-oxoimidazoli n-1-yl)piperidin-1-yl)pyrazin-2-carboxamide 2022303441   30 Mar 2026 0 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 91 to obtain Compound 042. ESI-MS: m / z = 897 [M+H]+. Example 43. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2- 5   (2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)-3-fluoropiperidin -4-yl)phenyl)amino)pyrazin-2-carboxamide The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 92 to obtain Compound 043. ESI-MS: m / z = 890 [M+H]+. 10 Example 44. 3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-5-(3-(4-methyl-5-oxo-4,6-diazaspiro[2. 4]cycloheptan-6-yl)piperidin-1-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 34, except that Intermediate 63 15 was replaced with Intermediate 93 to obtain Compound 044. ESI-MS: m / z = 844 [M+H]+. Example 45. 3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-5-(3-(3-oxohexahydroimidazo[1,5-a]p yridin-2(3H)-yl)piperidin-1-yl)pyrazin-2-carboxamide 2022303441   30 Mar 2026 0 The synthesis method was the same as that for Example 34, except that Intermediate 63 was replaced with Intermediate 94 to obtain Compound 045, ESI-MS: m / z = 858 [M+H]+. Example 46. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) 5 azetidin-3-yl)piperidin-4-yl)phenyl)amino)-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicy clo[2.2.1]heptan-2-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 95 to obtain Compound 046, ESI-MS: m / z = 802 [M+H]+. 10 Example 47. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-5-(-6-(3-isopropyl-2-oxoimidazolin-1-yl)-2-azabi cyclo[2.2.1]heptan-2-yl)pyrazin-2-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 15 was replaced with Intermediate 96 to obtain Compound 047, ESI-MS: m / z = 830 [M+H]+. Example 48. 2-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-6-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicy clo[2.2.1]heptan-2-yl)nicotinamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 2022303441   30 Mar 2026 10 was replaced with Intermediate 97 to obtain Compound 048, ESI-MS: m / z = 801 [M+H]+. Example 49. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicy clo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide —N 0 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 98 to obtain Compound 049, ESI-MS: m / z = 803 [M+H]+. Example 50. 3-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-5-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicy clo[2.2.2]octan-2-yl)pyrazin-2-carboxamide 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 99 to obtain Compound 050, ESI-MS: m / z = 816 [M+H]+. Example 51. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(-6-(3-methyl-2-oxoimidazolin-1-yl)-2-azabicy clo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide —N o 20 The synthesis method was the same as that for Example 49, except that Intermediate 133 was replaced with Intermediate 143 to obtain Compound 051, ESI-MS: m / z = 821 [M+H]+. Example 52. 5-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-3-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindolin-5-yl)pyrrolidin-3-yl)methyl)piperidin -4-yl)phenyl)amino)pyrazin-2-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 80, and Intermediate 133 was replaced with Intermediate 144 to obtain Compound 052, ESI-MS: m / z =890 [M+H]+. 5 Example 53. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 10 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 053, ESI-MS: m / z =833 [M+H]+. Example 54. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisooctyl-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-ethyl-2-oxyimidazolin-1-yl)pipe ridin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 101, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 054, ESI-MS: m / z =847 [M+H]+. Example 55. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 20 piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-isopropyl-2-oxoimidazolin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 2022303441   30 Mar 2026 10 was replaced with Intermediate 102, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 055, ESI-MS: m / z =861 [M+H]+. Example 56. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(trifluoromethyl)imidazo lin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide N—(  )=0 )=NH ) o7 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 103, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 056, ESI-MS: m / z =887 [M+H]+. Example 57. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(2,2,2-trifluoroethyl)imid azolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide N \  )=0 ) 0 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 104, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 057, ESI-MS: m / z =901 [M+H]+. Example 58. 3-(3-(3-cyclopropyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl )amino)-1,2,4-triazin-6-carboxamide 20 )=o Vnh ) o7 25 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 105, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 058, ESI-MS: m / z =859 [M+H]+. Example 59. 3-(3-(3-cyclobutyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl )amino)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 106, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 059, ESI-MS: m / z =873 [M+H]+. 5 Example 60. 3-(3-(3-cyclopentyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl )amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 10 was replaced with Intermediate 107, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 060, ESI-MS: m / z =887 [M+H]+. Example 61. 3-(3-(3-cyclohexyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl )amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 108, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 061, ESI-MS: m / z =901 [M+H]+. Example 62. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 20 piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-(oxetan-3-yl)-2-oxoimidazolin-1 -yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 109, and Intermediate 133 was replaced with Intermediate 140 to 2022303441   30 Mar 2026 obtain Compound 062, ESI-MS: m / z =875 [M+H]+. Example 63. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(tetrahydro-2H-pyran-4-yl)imidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 110, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 063, ESI-MS: m / z =903 [M+H]+. Example 64. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 10   piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 111, and Intermediate 133 was replaced with Intermediate 140 to 15 obtain Compound 064, ESI-MS: m / z =895 [M+H]+. Example 65. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-(2-fluorophenyl)-2-oxoimidazol in-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 112, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 065, ESI-MS: m / z =913 [M+H]+. Example 66. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-(3-fluorophenyl)-2-oxoimidazol 25 in-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 113, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 066, ESI-MS: m / z =913 [M+H]+. 5 Example 67. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-(pyridin-3-yl)imidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 10 was replaced with Intermediate 114, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 067, ESI-MS: m / z =896 [M+H]+. Example 68. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(4-methyl-5-oxo-4,6-diazaspirocyc lo[2.4]heptan-6-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 115, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 068, ESI-MS: m / z =859 [M+H]+. Example 69. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 20 piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(5-methyl-6-oxo-5,7-diazaspirocyc lo[3.4]octan-7-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 116, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 069, ESI-MS: m / z =873 [M+H]+. Example 70. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 5   piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-oxytrihydro-1H-pyrrolo[1,2-c]i midazol-2(3H)-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 117, and Intermediate 133 was replaced with Intermediate 140 to 10 obtain Compound 070, ESI-MS: m / z =859 [M+H]+. Example 71. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2 -azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 98, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 071, ESI-MS: m / z =845 [M+H]+. Example 72. 3-(6-(3-cyclopentyl-2-oxoimidazolin-1-yl)-2-azabicyclo[2.2.1]heptan-2 -yl)-5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4-yl)methyl)pi 20 peridin-4-yl)phenyl)amino)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 118, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 072, ESI-MS: m / z =899 [M+H]+. 25          Example 73. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(6-(2-oxo-3-phenylimidazolin-1-yl)-2- 2022303441   30 Mar 2026 azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 119, and Intermediate 133 was replaced with Intermediate 140 to 5 obtain Compound 073, ESI-MS: m / z =907 [M+H]+. Example 74. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(6-(3-oxotetrahydro-1H-pyrrolo[1,2-c]imidazol-2(3H)-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-1,2,4-triazin-6-carboxamide 10 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 120, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 074, ESI-MS: m / z =871 [M+H]+. Example 75. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(6-(3-methyl-2-oxoimidazolin-1-yl)-2 15 -azabicyclo[2.2.2]octan-2-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 121, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 075, ESI-MS: m / z =859 [M+H]+. 20 Example 76. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisooctyl-5-yl) pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)p iperidin-1-yl)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 10 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 142 to obtain Compound 076, ESI-MS: m / z =819 [M+H]+. Example 77. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) azetidin-3-yl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1 -yl)-1,2,4-triazin-6-carboxamide —N o o The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100 to obtain Compound 077, ESI-MS: m / z = 791 [M+H]+. Example 78. 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin]-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolidin-1-yl)piperidin-1-yl) -1,2,4-triazin-6-carboxamide —N o o 15 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 85, and Intermediate 133 was replaced with Intermediate 134 to obtain Compound 078, ESI-MS: m / z =833 [M+H]+. Example 79. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 -yl)-4-methylpiperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1 -yl)-1,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 85 to obtain Compound 079, ESI-MS: m / z = 805 [M+H]+. Example 80. 5-((2-(1-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl) -1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1 5 -yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 122 to obtain Compound 080, ESI-MS: m / z = 763 [M+H]+. Example 81. 5-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4 10 -yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carboxamide o The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 122, and Intermediate 133 was replaced with Intermediate 140 to 15 obtain Compound 081, ESI-MS: m / z =805 [M+H]+. Example 82. 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperazin-1-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 123, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 082, ESI-MS: m / z =834 [M+H]+. Example 83. 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)- [1,4'-bipiperidin]-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1 25 ,2,4-triazin-6-carboxamide 2022303441   30 Mar 2026 —N O o o The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 134 to obtain Compound 083, ESI-MS: m / z =819 [M+H]+. Example 84. 5-((4-(4-(3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindol-5-yl)propan-2-yn -1-yl)piperazin-1-yl)piperidin-1-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)pipe ridin-1-yl)-1,2,4-triazin-6-carboxamide o^nh2 nyn o r । 0 N^\ / =o Vnh o 10 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 124, and Intermediate 133 was replaced with Intermediate 145 to obtain Compound 084, ESI-MS: m / z =844 [M+H]+. Example 85. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-6-fluoro-1,3-dioxoisoindol-5-yl) piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide 15 o 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 147 to obtain Compound 085, ESI-MS: m / z =851 [M+H]+. Example 86. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-3-oxoisoindol-5-yl)piperidin-4 -yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxoimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 2022303441   30 Mar 2026 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 146 to obtain Compound 086, ESI-MS: m / z =819 [M+H]+. Example 87. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisooctyl-5-yl)piperidin-4 -yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-methyl-2-oxyimidazolin-1-yl)piperidin-1-yl )-1,2,4-triazin-6-carboxamide 0 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100, and Intermediate 133 was replaced with Intermediate 148 to obtain Compound 087, ESI-MS: m / z =819 [M+H]+. Example 88. 5-((4-(1-((1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2-oxo-2,3-dihydro -1H-benzo[d]imidazol-5-yl)piperidin-4-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(3-met hyl-2-oxoimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide O.NH2 NV N^N / N-. O - O HnV O^J N CT > o N-'^'^N The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 100, and Intermediate 133 was replaced with 1-(1-(2,6-dioxopiperidin-3-yl)-3-methyl-2 -oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)piperidin -4-aminocarbaldehyde to obtain Compound 088, ESI-MS: m / z =834 [M+H]+. Example 89. 5-((4-(1-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) pyrrolidin-3-yl)methyl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)p iperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 111, and Intermediate 133 was replaced with Intermediate 142 to obtain Compound 089, ESI-MS: m / z =881 [M+H]+. Example 90. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3 2022303441   30 Mar 2026 -yl)piperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-t riazin-6-carboxamide 0 O 0 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 111 to obtain Compound 090, ESI-MS: m / z = 853 [M+H]+. Example 91. 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)-4-methyl-[1,4'-bipiperidin]-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 10 15 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 125, and Intermediate 133 was replaced with Intermediate 134 to obtain Compound 091, ESI-MS: m / z =895 [M+H]+. Example 92. 5-((4-(1-(1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidine -3-yl)-4-methylpiperidin-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide o o 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 125 to obtain Compound 092, ESI-MS: m / z = 867 [M+H]+. Example 93. 5-((2-(1-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)azetidin-3-yl) -1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1,2,4-triazin-6-carboxamide o^.NH2 I H N^N o r > Va o V-N          / —\ N \ / =° ^NH o oz The synthesis method was the same as that for Example 1, except that Intermediate 63 2022303441   30 Mar 2026 was replaced with Intermediate 126 to obtain Compound 093, ESI-MS: m / z = 825 [M+H]+. Example 94. 5-((2-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)piperidin-4 -yl)methyl)-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl) piperidin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 126, and Intermediate 133 was replaced with Intermediate 140 to obtain Compound 094, ESI-MS: m / z =867 [M+H]+. Example 95. 5-((4-(4-((1-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl) 10 piperidin-4-yl)methyl)piperazin-1-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)pi peridin-1-yl)-1,2,4-triazin-6-carboxamide The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 127, and Intermediate 133 was replaced with Intermediate 140 to 15 obtain Compound 095, ESI-MS: m / z =896 [M+H]+. Example 96. 5-((4-(1'-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindol-5-yl)- [1,4'-bipiperidin]-4-yl)phenyl)amino)-3-(3-(2-oxo-3-phenylimidazolin-1-yl)piperidin-1-yl)-1, 2,4-triazin-6-carboxamide 20 The synthesis method was the same as that for Example 1, except that Intermediate 63 was replaced with Intermediate 111, and Intermediate 133 was replaced with Intermediate 134 to obtain Compound 096, ESI-MS: m / z =881 [M+H]+. Example 97. 5-((4-(4-(3-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoquinolin-5-yl) propan-2-yn-1-yl)piperazi...

Claims

2022303441   18 Jun 20261. A compound, wherein, the compound has a structure shown in general formula III(a) orIII(b):R3NDOIII(a)                                            III(b),or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceutically acceptable salt thereof;wherein:Y1 is selected from: N, CR2;Y2 and Y3 are each independently selected from: N, CH;ring B is selected from:awD is chemical bond;one or more R1s are each independently selected from: H, halogen, C1-C6 haloalkyl, -CN;R2 is selected from: hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy;R3 is selected from: 3-6 membered heterocyclyl, 5-6 membered heteroaryl, 5-6 membered aryl, 3-6 membered cycloalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, wherein the heterocyclyl, heteroaryl, aryl and cycloalkyl can be further substituted with halogen;n is selected from: an integer of 0-2;represents that the atom connected thereto is connected to L;when Y1 is CH, then R3 is not C1-C4 alkyl, C1-C4 haloalkyl;E3CL represents a chemical ligand that can bind to E3 ubiquitin ligase, and is selected from2022303441   18 Jun 2026Reisselectedfrom: H, F, Cl, -CH3, -OMe,-CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2, -S(O)2Rf, -P(O)(Rf)2;Rf is selected from: H, C1-C3 alkyl; or two adjacent Res on the benzene ring form a 7-10 membered benzo ring together with the benzene ring; one or more C atoms in the benzo ring can be replaced by heteroatoms selected from N, O, S; the benzo ring is optionally substituted with H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2;W1 and W2 are selected from: CH, N;q is selected from: 0, 1, 2, 3;and L represents a chemical group or a chemical bond connecting the BTKcl to the E3CL, in case L represents a chemical group, L has the following structure:-X1-L1-X2-Cyc1-X3-L2-X4-Cyc2-X5-L3-X6-Cyc3-X7-L4-X8-wherein:2022303441   18 Jun 2026X1, X2, X3, X4, X5, X6, X7 and X8 are absent;L1 is selected from: absent, C1-C4 alkyl, wherein the C1-C4 alkyl can be substituted with oxo;L4 is absent;L2 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl, wherein the C1-C4 alkyl can be substituted with oxo;L3 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl; wherein the C1-C4 alkyl can be substituted with oxo;Cyc1 is selected from: 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with oxo, C1-C8 alkyl, halogen;Cyc2 is selected from: absent, 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with C1-C8 alkyl, halogen;Cyc3 is absent.

2. A compound, wherein, the compound has a structure shown in general formula IV(a) orIV(c):or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceuticallyacceptable salt thereof;wherein:2022303441   18 Jun 2026Y1 is selected from: N, CR2;Y2 and Y3 are each independently selected from: N, CH;one or more R1s are each independently selected from: H, halogen, C1-C6 haloalkyl, -CN;R2 is selected from: hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy;n is selected from: an integer of 0-2;represents that the atom connected thereto is connected to L;E3CL represents a chemical ligand that can bind to E3 ubiquitin ligase, and is selected fromR eisselectedfrom: H, F, Cl, -CH3, -OMe,-CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2, -S(O)2Rf, -P(O)(Rf)2;Rf is selected from: H, C1-C3 alkyl; or two adjacent Res on the benzene ring form a 7-10 membered benzo ring together with the benzene ring; one or more C atoms in the benzo ring can2022303441   18 Jun 2026be replaced by heteroatoms selected from N, O, S; the benzo ring is optionally substituted with H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2;W1 and W2 are selected from: CH, N;q is selected from: 0, 1, 2, 3;and L represents a chemical group or a chemical bond connecting the BTKcl to the E3CL, in case L represents a chemical group, L has the following structure:-X1-L1-X2-Cyc1-X3-L2-X4-Cyc2-X5-L3-X6-Cyc3-X7-L4-X8-wherein:X1, X2, X3, X4, X5, X6, X7 and X8 are absent;L1 is selected from: absent, C1-C4 alkyl, wherein the C1-C4 alkyl can be substituted with oxo;L4 is absent;L2 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl, wherein the C1-C4 alkyl can be substituted with oxo;L3 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl; wherein the C1-C4 alkyl can be substituted with oxo;Cyc1 is selected from: 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with oxo, C1-C8 alkyl, halogen;Cyc2 is selected from: absent, 3-12 membered heterocyclic ring, wherein the heterocyclicring can be substituted with C1-C8 alkyl, halogen;Cyc3 is absent;the fused ring or spiro ring structure composed of ring G and ring F is selected from:

3. A compound, wherein, the compound has a structure shown in general formula V(a) orV(b):2022303441   18 Jun 2026acceptable salt thereof;Y1 is selected from: N, CR2;R2 is selected from: hydrogen, halogen, C1-C4 alkyl, C1-C4 alkoxy;Y2 and Y3 are each independently selected from: N, CH;one or more R1s are each independently selected from: H, halogen, C1-C6 haloalkyl, -CN;n is selected from: an integer of 0-2;ring A is selected from: imidazolidinyl, isoindolinyl, hexahydro-pyrrolo[1,2-c]imidazolyl;one or more R3s are selected from: 3-6 membered heterocyclyl, 5-6 membered heteroaryl, 5-6 membered aryl, 3-6 membered cycloalkyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, cyano, oxo, wherein the heterocyclyl, heteroaryl, aryl and cycloalkyl can be further substituted with halogen; or two R3s on ring A can be connected to form a spiro ring, a bridged ring, a fusedring;m is selected from: an integer of 1-3;when Y1 is CH, and ring A is a monocyclic ring, then R3 is not C1-C4 alkyl, C1-C4 haloalkyl;represents that the atom connected thereto is connected to L;E3CL represents a chemical ligand that can bind to E3 ubiquitin ligase, and is selected from,2022303441   18 Jun 20260Reisselectedfrom: H, F, Cl, -CH3, -OMe,-CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2, -S(O)2Rf, -P(O)(Rf)2;Rf is selected from: H, C1-C3 alkyl; or two adjacent Res on the benzene ring form a 7-10 membered benzo ring together with the benzene ring; one or more C atoms in the benzo ring can be replaced by heteroatoms selected from N, O, S; the benzo ring is optionally substituted with H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2;W1 and W2 are selected from: CH, N;q is selected from: 0, 1, 2, 3;and L represents a chemical group or a chemical bond connecting the BTKCL to the E3CL, in case L represents a chemical group, L has the following structure:-X1-L1-X2-Cyc1-X3-L2-X4-Cyc2-X5-L3-X6-Cyc3-X7-L4-X8-wherein:X1, X2, X3, X4, X5, X6, X7 and X8 are absent;L1 is selected from: absent, C1-C4 alkyl, wherein the C1-C4 alkyl can be substituted withoxo;L4 is absent;L2 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl, wherein the C1-C4 alkyl can be substituted with oxo;L3 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl; wherein the C1-C4 alkyl can be substituted with oxo;2022303441   18 Jun 2026Cyc1 is selected from: 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with oxo, C1-C8 alkyl, halogen;Cyc2 is selected from: absent, 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with C1-C8 alkyl, halogen;Cyc3 is absent;Z is selected from: -CH2-, -CH2CH2-.

4. The compound of claim 1, wherein:R3 is selected from: C1-C4 alkyl, or ring D;ring D is selected from:, ring D can be further substituted with one ormore substituents which can beon C atom or N atom and are selected from: halogen;when Y1 is CH, then R3 is selected from ring D.

5. A compound, wherein, the compound has a structure shown in general formula (VI):(VI)or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceutically acceptable salt thereof, or a prodrug thereof;wherein:Y1, Y2 and Y3 are each independently selected from: N, or CH;D is a chemical bond;one or more R1s are each selected from: H, halogen, C1-C6 haloalkyl or -CN;ring B is selected from:2022303441   18 Jun 2026R3 is selected from: C1-C4 alkyl, C1-C4 haloalkyl, 3-6 membered cycloalkyl, 3-6 memberedheterocyclyl, 5-6 membered aryl, or 5-6 membered heteroaryl, in which the cycloalkyl, theheterocyclyl, the aryl, and the heteroaryl can be further substituted with one or more substituentsselected from: halogen;n is selected from: an integer from 0 to 2;when Y1 is selected from CH, and ring B is selected from, then R3 is not C1-C4 alkyl or C1-C4 haloalkyl;,represents that the atom connected thereto is connected to L;E3CL represents a chemical ligand that can bind to E3 ubiquitin ligase, and is selected from2022303441   18 Jun 2026Re is selected from: H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2, -S(O)2Rf, -P(O)(Rf)2;Rf is selected from: H, C1-C3 alkyl; or two adjacent Res on the benzene ring form a 7-10 membered benzo ring together with the benzene ring; one or more C atoms in the benzo ring can be replaced by heteroatoms selected from N, O, S; the benzo ring is optionally substituted with H, F, Cl, -CH3, -OMe, -CN, -CF3, -CHF2, -CH(CH3)2, -cyclopropyl, -C(O)NH2;W1 and W2 are selected from: CH, N;q is selected from: 0, 1, 2, 3;and L represents a chemical group or a chemical bond connecting the BTKcl to the E3CL, in case L represents a chemical group, L has the following structure:-X1-L1-X2-Cyc1-X3-L2-X4-Cyc2-X5-L3-X6-Cyc3-X7-L4-X8-wherein:X1, X2, X3, X4, X5, X6, X7 and X8 are absent;L1 is selected from: absent, C1-C4 alkyl, wherein the C1-C4 alkyl can be substituted with oxo;L4 is absent;L2 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl, wherein the C1-C4 alkyl can be substituted with oxo;L3 is selected from: absent, C1-C4 alkyl, C2-C4 alkynyl; wherein the C1-C4 alkyl can be substituted with oxo;Cyc1 is selected from: 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with oxo, C1-C8 alkyl, halogen;Cyc2 is selected from: absent, 3-12 membered heterocyclic ring, wherein the heterocyclic ring can be substituted with C1-C8 alkyl, halogen;Cyc3 is absent.

6. The compound of any one of claims 1 to 5, wherein,L is selected from:2022303441   18 Jun 2026,7. The compound of any one of claims 1 to 6, wherein,E3CL is selected from:2022303441   18 Jun 2026G-HN / N. „Y° Yyy y 0         ,                 0         ,0^-YH■■H P              O^Nto00 0 ,H,' N Xo H,,X^H I ,N. ,NH Y 0 \,,Yy° / ¾ ,N. NH fY YAY ° ,TY yAY 0, / O, o0<N^°0 o ,rr° rr,,A FH A / N^NH fl Y o,>° F_F Yl°H , / / ,N ,NH (T Y YY 0,                                                 ,r^°o o ,Y? Y? Y? Y?°,,,,,J™ o o'o Yr° YY",f yt°_X,N NH F.T T itAY °   \, i^Y^0,N. ,N. ,NHI Y Y <Y °Y j-                             , ~                                ,,yy "YA ,H                  Ho °^nya° q °y / ny^°p^"           zJWO                       ,                              ,H                     HD^.N^D      n AY,. X1 .C^1,H                     H0 °yny° y 0 °Yn'YY" . / 0^",N NH n o0II,H o°YN Ay'nZ-yU H ,H0 °yN y°Y^n'^YH,N ,NH\ Y0,o0Y       / NHY YY-Y 0 , H0 °Y Y,;O,rr'' n'''^Y-U H ,HCK ,N. X)O '?Y^Y I H, 'HO .N / O) o y Y y~nht"’1 -C,H f o°yny° y ° ^N^ °^Y1 H                         II 1, ., / 0O;HO;'N' H, H ,NH 0^ / N^.O0 I I n'Yx><n'xY-> II J H XYY ,                                                           ,H o °yN y° p.Y, r°, ,gr Yth Yth^zwv                        _rv{ / v                        ."Av2022303441   18 Jun 2026°' ,,N. ,NH n Y-Y ° ,                                                   ,_ F _i TN NH N 1Y ¥°  Y-,YY° ^NH ¥Y° ¥° xx°.N NH N¥vNyNH O^Yn NH nYLYnH Y Y Y Y ¥Y Y YY y o       ° YY ° YY °,                                                  ,                                                  ,xx, x ». Yx.H                         H .                  H .,, ,,Yx Yx. Y / x Yc. Yx. H ,                  H ,                  H ,                  H ,                  HH                 I H                 | H                        H                  \|--N   9,H oo^YYNX■"X)H N^OH ,                 H ,                 H ,H nO;:YnYs n            \       n                      a. YN-N Y            N-N \\                / -N,      Y1^0H n             H nYnY Y^Y ¥"Y YYJ YY"^0 NT          X b 0            .                  .,  ,  ,,,° oxH O          YNxHoyy Yyn¥ Y°Y^N HO%,HO VYHo ,                                 .

8. The compound of any one of claims 1 to 7, wherein, Y1, Y2 and Y3 are each N.2022303441   18 Jun 2026005 o^nh2 An 1 T ’ A0 An 006 ovnh2 Aa> Aoc{k> 007 A, \AAN A^AAa ° A            l 1 1 J                 VNH _NvJN            IXa ^0 0 008 o^nh2 A'CA 0 A              ° o -Ny       AXn^° 009 o^nh2 .a v A o A A ,° A^   ^tAnATo 6    A 010 Oy NH2 y XAl^ 0 a              0 0 -n°    An-a A                    o 011 OyNH2 A XAa o rA     An-^    0 0 -A An o                ° 012 o^nh2 Ari, Aa AA\A\ T          T 1 q r         Al    00 ^OaAa 0 013 o^nh2 1 H w Ud / \ i             T । 90      T 1     2\ oA AAA       AA / a^. Anh °vA_J               1^C / N~( A0 o 014 Y z r a° nz A“\ Az ° CHA. / A A o 015 o^nh2 A kN An^ A A^b- 0 016 °yNH2 nA    °aA ^an \ /             ° oA J? an>                J^nv n \AJ    (     AAAa La        ^A_ / aA^A 0 017 °VNH2 Aa 'Al..° - a-a 0 018 o^.nh2 An <^0 %P> ^A                     Q 019 Oy ,nh2 , V^A 0 020 Anh2 J H / ANv^\ kN \A /          h / ° 0 rN\      71     °=¥ \ / \ AMk )     An o >A N^\>          y~! 4 ' '                                1—N / V Ca° 021 a, An A^n [1 J o   r-NK / \ a a y      ^-n <An nA>      y^ —1                 '"A A n H njy H 022 o A A-A A p - W IZ LAq z—. oX^J 62022303441   18 Jun 2026023 9 z r x0 z )—\    / =2 o ZI 1? cf b . r- 024 o^nh2 1 H nx Xn XXLy X X___ CbXJ Xj A i NH 0 xo 025 o^nh2 )¾. Xn XXLy 6          ° 026 o^nh2 1 H X bX CX Xx-X 027 o^nh2 y LX X "v"'Cd<>" 0 028 nh2 ____ 0XNXX° vb x 0 bY „ b X-X X N ax 029 °yNH2 ( / V"                X w / /           °Y 3 ex W " Cl X X Xn-AA Xy 030 0 hnX o°A Xn yH.        Y>0 AtoxA o b b C-bA 031 9 X° by 6 b Ay° ° ?x 032 8 £■ IZ xbVzX O z= / X z—, oX 8 z 3 033 z b yQ by ZI r? L \J Xf°° yX o I X 034 ox XnH2 n-8 / / yNH x °     ?A < 1  11 r-N     X / XX y V-\ / X    0 0 ' VNY'X; XNH bXN vX° 0 035 0 Xnh2 nn y™ o 9N X 9 rA X / yO X X y oo txX 0 036 0 XNH2 XyNH o y by A / 'Nx   X / Xbb by 0 037 0 yry fJtnh o A M . JJ / ~N XX by ^N\ / X    0 0 ' XyX. XnH Xx vX 0 038 0 yNH2 bXb™ o >n by Obb by ^“N\ / X     o o 02022303441   18 Jun 20262022303441   18 Jun 20262022303441   18 Jun 2026075 o^nh2 Y MixM A*3 077 O^NH2 Asri Ny^N ,n                            o ^Nx        "XI / XX 0 0 079 o^nh2 ^Mm ° A LM NXXNX^° 0 0 081 o XM NyN                  O O ,N. o A A 083 o^nh2 Av, N<yN XMvyV n.      ^na / A -a Ma o o 085 o^nh2 Th               / ? = / - . : :- jv 087 (X,nh2 X MuMM jv 089 °« XM °VH2        A, A Mo0 M Mv a O fl Ml XN-^ / M / nM 091 0^,nh2 Av, N^N MMMy N       ^ny / x> VV M$Qr 0 oz076 o^.nh2           Vi 1 Av A n^n MM^v\   N ,N. O fl 078 cv,nh2 ^Xlv ana    ^"M A'    ~Xr^° o o 080 o^nh2 Avr, N<y.N LXA^-Nv^,      O M W 082 ck,nh2 1 H                                 p V'CV VjAv o A vnUv ° ° -V' 084 (X,nh2 MM A"          j - v M Mn M MnXJ              0 086 O^,NH2 JMxAA mm 088 0 hnA °yNH2             oAJ xAJ 090 o^nh2 Av Ny,N MMyVy ana                    o oAJ   “AVr- 0 0 092 OvNH2 Av Ny,N MMAy rM        ’''^N'V\      o oa "VHv 0 02022303441   18 Jun 2026093 o^nh2 Arn nYN AAv,-Nyy     0 Wr 094 AoA" Ny Ax-Axy   0 0 ,N, oy / j 095 o^.nh2 Th                II V~O.Np pNXXfTT o A AAy ° ° OKA 096 o-.nh2 Ay N<^N A\ / \| yny      ^Ny / Xo oA "YYpr 0 0 097 o-.nh2 1 H Y Y1--         ,? ,-yO 098 OyNH2 KiAx O-nAA 099 ck,nh2 Y "OoY3^ oYr-1 100 0^,nh2 KyA- 101 0 hnY OyNH,             oYj Aaxxn coy 102 in- °-,NH2           Y^1 Y Xsyy- A NyN           yN X    La^ / L / o KI knK ~~NvJ 103 0-, nh2 A NyN TAy^ x             0 ^NtN         nxx}at 0 0 104 O-.NH2 AA    ^nYA ■A AAor 0 0 105 O^,NH2 ° A           ? 0 0 106 0-, NH2 XYp N;yN AaA / '^'y^      0 JX KA 107 0 XU N^N                  0 0 N o nA 108 0<_nh2 1 H                                         / 9 NV1       jfX^NAf^>0 NVN XYNp YN-XYp Anh o YS   vJj 0 0 pX 109 o^nh2 Xy NyN AA -y -A A4u O 0 110 o^nh2 AK v Ay a1 _ o a       AAnAnV° - / A           0 111 OyN^ = / ..- Y- jy 112 o^,nh2 xAxAA yd2022303441   18 Jun 2026113 0^nh2 Y XfX JA 115 o^nhj             9, XY° xx™ f X YX     9 VA ° NvN (A      \= / ° o r\    O on; A Z J -rYYX> 117 o^nh2 Y YaoX^0 ^O-A 119 cx,nh2 n if xx       Xt^nX^xo nvn X-na          Xnh o A xXO ° ° . / A 121 ^,o X X / nh °vnh2           _Xn n 1 H                  / TA J. 0 AN~n   v ° NyN        a o A ^fX 123 o^nh2 V YaYX° A"X 125 0^nh2 9 Xnap    FTfXFF° nvn ^nY An"^A y™ o A                ° ° yA 127 % A 0^nh2          _Xn Y 1 H         Fvk ° Anti   y ° n^n XAyy rN L ., A XX o f >              n -fX    ° 129 Oy,AH2 1 H                                 O N^XO  " - ■■          ”114 O^,NH2 X YxAX YX 116 t A" 0^nh2             2Y X Xan     ’ NyN Xy^ y off 118 o^nh2 v yA 120 ^x~ o^nh2                   X 1 H        OX ° ifnix NyN XXyy  N f^l'kXX o < f XnXJ 122 o^nh2 A na^x:Yy yA    ’ 124 i X O^N^          _XN B 1 H          Zvi 0 XyX V ° NyN               Nz Xn.. XX -A 126 %n- ck,nh2            AY Y 1 H         Al 0 XNXA FX° NyN XXxy X off Z X J -Njl 128 % o’ o^nh2            X^N n Xx- pY- NyN XX / y nZ / N.     XnaXX A" 130 19J~ o^NH2            An Y 1 h         XxA ° Xyv X* nYn Fy r\ o A   OnJy -PA2022303441   18 Jun 2026131 A o^nh2              An n 1 H          AVA ° AnyY 0*° nYn         r< o rN> PNkA .A 132 A ovnh2             2A A 1 h          rvk O AVf v ° nyn Ay A _hk O <              w 1 A J "NCi 133 o oO A k-NH o / h            / "n X 1 H          rVk O nVyy  y^O NYN     N    Ny O r%        N ' N N' 134 ^Y NHz i1 if NrvF     YpAfA nyn ^-A-y         Anh o A OUx ° ° 135 o^,nh2 Y Y^ OX" 136 y xy n NH                                    ft °YYNH2               ztA I O i h             / / V% Aft NY^1 NyxN             rN M-Jp o [] A 137 o v A.x AP° 'Nx <1  0 138 O^,NH2 o x AoA1 / A° 139 o^nh2 JOxxyAAy A. 140 v Y^ O^NHa               _ / N if 1 H                                     0 ANn >Ao nYn ^Ay rN k^N. A-? o r 141 o^nh2 0 Y F3C PmAP 3 ^Ny1 142 o^nh2 AyY    fAAn^C^° nyn ^-ny ynJA Ynh o A        J ° ° y / y 143 o^nh2 o x AAP Ax' 144 o^nh2 X AxoYY Kx f            St^y^y ^AVa        O J 1 AO      ° K° 145 XKxy yA^ NyN       pXN  0 o X    X«X-1 4 Y'J ~Yj 146 °Ynhh             ? o° nVyV   xAAnh nyn “Ay yn^n ° o X   XnXX xnA "Xo 147 OyNH2                  r^Y° AkYYf    ANyNH nYn ’Ay       ° o rNx           —1 » X J 148 o^nh2 XYt'     “   l'~T° o X Wcr A JaJ -n32022303441   18 Jun 20262022303441   18 Jun 20262022303441   18 Jun 2026183 NyN 00N^ yNY0   0 o A YnUo r JrJ 'An 184 °yNH2                  F ^-=y0 n0Aoyf      / ynynh NyN O-N-y pNAb ° 0 O   kNJ0 O;J 185 1 Yyo O-z b^ ZZ i? a 0 ■ 7 °b 186 Oy NH2                YY° nAkyY    fyOnynh nYn 00,-y         0 o rO   O-bO YrJ 187 OyNH2            FyF yyO ■AhyV     AfYNH NyN 00-0        ° O O k b'J -07 188 O^NHj             F.Y |^y° ObYV    0YnYnh nYn OVy pNA0 o 0 O   kN0J K bb -00 189 1 <zy) bHH ZI r? a ,—z -n z— / b <Hy Ab Ao 190 b^i ZZ 1? 0 Oz "H z—' A bi 191 °ynhh           r° rr° AnyOf    Aynynh NyN YAn^ pNAJ o o 07    0n0J y / j 192 °TNHh         O bV° yVyV    bvNYNH NyN 0Yn^ pNA0 ° O O   0N0J y / J 193 1 <0o z biH ZZ r? 0 0 " b» 0b 194 bAb 0 7--Z 0 vH<0 O z-z b—( O00 1 195 OyNH2                yyO fbV" NyN YA'Y        ° O r0   0N0J yo 196 °yNH2                0Y° „Onxzx,F        m«=^-N..NH 0 Y Y Y     YI Y NyN YYNy pNYY ° 0 O   0N0J yO 197 A b z—, »■' o . o 0 ZZ 001 O z-z '— z—, A 1 198 yH2        °   y^O AynYOf    "iYYnYnh NyN YAN=y pNO0 ° 0      0N00 ~N00 199 1 Yy 7z bo ZZ i? 0 0 ' b . HA A 200 ox y-NH o^nh2            0 / N"Y—0° Yy 0” NyN OkN^ N o O Obbb A "NvJ2022303441   18 Jun 2026201 ox Anh n hh              HN0 0° A- 0 N^N A.p p o A  0nA 4 A J 202 °VNH2                       o AW Air A Up a^n o A aA "nA 203 b q . 0 0 £ IZ Avq O z-z z—. oXz; \ 204 o ! ■ z A £i IZ KA z—, °=A \ 205 °yNH^                      0 Arr jA NyN YANp yNMF <A0 0 A   KnJK K bb 'nA 206 ox y~NH O^NH,          pH-A0 A’ A nyn rxNp rNf o A   KnAA "nCjn 207 °yNH2                       o Al rM o A ^NvJ 208 c\ y~NH o_nh2       AP Ary A nyn rxNp     ° o A  ^NA -A 209 °YNHh              a0 h ° Ary  °AA NYN KkNp p-N-A1 o A A "NvJN 210 °YNH^              r° H ° jprA nAnA nYn 00n^ pN0J kA 0 A   kN00 AJ 211 °Y,hJ           r° „ - A' aa nYn ANp pNA 0Ao o A ^nA> -AJ 212 \ z f Y° Az \ z-z O Oth ZI r? r 0 ’ ^A AKA o \ ZI o 213 vi    kA Anayf    / Yaa nyn Ay pNA o ry   KnAa -A 214 H °yNxpO ,nyAA> °VNH2         ^N\T 1 H             YA n if YY NyN         r< o A   KnA? -A 215 °YNk          Vn 1 nA A    / (A0 nyn     fA o A  KA 216 °A IZ / y^vzx ° a • . 0 0 £ IZ A^y O z-z x—( z—, °A2022303441   18 Jun 20262022303441   18 Jun 20262022303441   18 Jun 2026or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceuticallyacceptable salt thereof.

10. A compound selected from the following compounds:No. Structure No. Structure 119 o 3 v) Z—\ ^Z d 0 IZ AxV o z-z x oZ) \ 126 o^nh2                       if 1 h                                   0 ANn F^v 0 NyN 00y0 rN ,N.                    N .    / z' 0  <        v X 050 128 1 50 o^nh2             _An id 1 H         fvk ° vNYYF n^n            n ,N_,       LzNxzV odd 130 i rC 0^nh2           _An B 1 H        AA 0 AnyV V / N,          AA odd X0J "NvJ 131 ox V-z / \=o —( o z \ . 0 0 IZ >Y 0ZV O z-z V / z—. Y \ 132 i O" o^nh2                 / ^n B I h        rO o Avy v 0 NyN V-0 fN k.x-N. vAy odd      w \i A J2022303441   18 Jun 2026133 yQ° o^nh2            An X T H         AVA 0 Aw1 v 0 nYn L .n. AA Ob0 135 y 'o o Y x-O b IZ 00-3 O Z-Z A zo ZA oAv A° yNH 136 ° bX °vnH2       A ° €A a n  3 N^N XAyy yN X   AnAA o fl < 140 K 0^nh2                  n Vr, V NyN Ay^ A Anx AA 0       |      | -aa v° 0NH 0 143 0 cy2-^ W 9 / —Z Cl £ IZ V, z 1 oXX u 145 ZI b . o 0 -N IZ 0-YJ- O Z-Z z~. o=<0 1 A° 0 146 °X      3 X ANrrF AAnh nYn          <"rA"N 0 ,N-     AnA\J orb kA 147 b b . 0 b IZ 0-VY O Z-Z z—. o0z; i ynh 0 150 A X b / —z A ^IZ Wl 0 z-z Z—. 30 1 254 O^NH2                   n | H                                       n N VaA    Aan" An IA     XA H y          N । i N       F / N.                  J o   r >                \z K AJ ''xNH o 255 X b a . 0 0 IZ w Z—. oXz; । 257 b . 0 0 IZ 300 z—. °A । 3NH 0 259 । <zy° z bv ZI r? a 0 ' b A11. A compound, wherein, the compound isor its stereoisomer thereof, or its stereoisomer mixture thereof, or its pharmaceuticallyacceptable salt thereof.

12. The compound according to claim 11, wherein the compound is2022303441   18 Jun 2026or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceuticallyacceptable salt thereof.

14. A pharmaceutical composition, wherein, the pharmaceutical composition comprises one or more of the compounds of any one of claims 1 to 13.

15. Use of the compound of any one of claims 1 to 13 in the preparation of a drug for treating a disease, a disorder or a condition that would benefit from the inhibition or degradation of Bruton's tyrosine kinase activity alone or in combination with other drugs.

16. The use of claim 15, wherein, the disease, the disorder or the condition is one that would benefit from the inhibition or degradation of mutant Bruton's tyrosine kinase.2022303441   18 Jun 202617. The use of claim 15, wherein, the disease is selected from one or more of a B cell or plasma cell proliferative disease and an autoimmune disease.

18. The use of claim 17, wherein, the B cell or plasma cell proliferative disease includes diffuse large B cell lymphoma, follicular lymphoma, chronic lymphocytic leukemia, small lymphocytic lymphoma, B cell prolymphocytic leukemia, lymphoplasmacytic lymphoma / Waldenstrom macroglobulinemia, splenic marginal zone lymphoma, plasma cell myeloma, plasmacytoma, extranodal marginal zone B cell lymphoma, lymph node marginal zone B cell lymphoma, mantle cell lymphoma, mediastinum (thymus) large B cell lymphoma, intravascular large B cell lymphoma, primary effusion lymphoma, Burkitt lymphoma / leukemia or lymphomatoid granulomatosis, and multiple myeloma;the autoimmune disease includes inflammatory bowel disease, arthritis, lupus, rheumatoid arthritis, psoriatic arthritis, osteoarthritis, Still's disease, juvenile arthritis, diabetes, myasthenia gravis, Hashimoto's thyroiditis, Ord’s thyroiditis, Graves' disease, Sjogren’s syndrome, multiple sclerosis, Guillain-Barre syndrome, acute disseminated encephalomyelitis, Addison's disease, optic opsoclonus-myoclonus syndrome, ankylosing spondylitis, antiphospholipid antibody syndrome, aplastic anemia, autoimmune hepatitis, coeliac disease, Goodpasture’s syndrome, immune thrombocytopenic purpura, optic neuritis, scleroderma, primary biliary cirrhosis, Reiter’s syndrome, Takayasu's arteritis, temporal arteritis, warm antibody type autoimmune hemolytic anemia, Wegener's granulomatosis, psoriasis, alopeciauniversalis, Behcet's disease, chronic fatigue, familial dysautonomia, endometriosis, interstitial cystitis, neuromyotonia, scleroderma or vulvodynia and chronic graft versus host.

19. The compound of any one of claims 1 to 13 for use as a medicament.

20. A method for treating a disease, a disorder or a condition that would benefit from the inhibition or degradation of Bruton's tyrosine kinase activity, wherein, the method comprising administrating to a subject in need thereof a therapeutically effective amount of the compounds of any one of claims 1 to 13, or the pharmaceutical composition according to claim 14.2022303441   18 Jun 202621. The method of claim 20, wherein, the disease is selected from one or more of a B cell or plasma cell proliferative disease and an autoimmune disease.

22. The method of claim 21, wherein, the B cell or plasma cell proliferative disease includes diffuse large B cell lymphoma, follicular lymphoma, chronic lymphocytic leukemia, small lymphocytic lymphoma, B cell prolymphocytic leukemia, lymphoplasmacytic lymphoma / Waldenstrom macroglobulinemia, splenic marginal zone lymphoma, plasma cell myeloma, plasmacytoma, extranodal marginal zone B cell lymphoma, lymph node marginal zone B cell lymphoma, mantle cell lymphoma, mediastinum (thymus) large B cell lymphoma, intravascular large B cell lymphoma, primary effusion lymphoma, Burkitt lymphoma / leukemia or lymphomatoid granulomatosis, and multiple myeloma;the autoimmune disease includes inflammatory bowel disease, arthritis, lupus, rheumatoid arthritis, psoriatic arthritis, osteoarthritis, Still's disease, juvenile arthritis, diabetes, myasthenia gravis, Hashimoto's thyroiditis, Ord’s thyroiditis, Graves' disease, Sjogren’s syndrome, multiple sclerosis, Guillain-Barre syndrome, acute disseminated encephalomyelitis, Addison's disease, optic opsoclonus-myoclonus syndrome, ankylosing spondylitis, antiphospholipid antibody syndrome, aplastic anemia, autoimmune hepatitis, coeliac disease, Goodpasture’s syndrome, immune thrombocytopenic purpura, optic neuritis, scleroderma, primary biliary cirrhosis, Reiter’s syndrome, Takayasu's arteritis, temporal arteritis, warm antibody type autoimmune hemolytic anemia, Wegener's granulomatosis, psoriasis, alopeciauniversalis, Behcet's disease, chronic fatigue, familial dysautonomia, endometriosis, interstitial cystitis, neuromyotonia, scleroderma or vulvodynia and chronic graft versus host.