IP Library › Granted Patent US 12,508,320
Granted Patent B2
US 12,508,320 · App. 18/679,403 · Granted Dec 30, 2025

Drug conjugate, pharmaceutical composition and method of treating hepatitis

Inventors: Wuu-Jyh Lin (Kaohsiung, TW); Min-Ching Chung (Kaohsiung, TW); Chi-Shiang Ke (Kaohsiung, TW); Ya-Chen Tseng (Kaohsiung, TW); Chin-Yu Liang (Kaohsiung, TW); Yen-Chun Lee (Kaohsiung, TW); Hsin-Jou Li (Kaohsiung, TW); Tai-Yun Huang (Kaohsiung, TW); Nai-Chen Hsueh (Kaohsiung, TW); Yan-Feng Jiang (Kaohsiung, TW)
Assignee: SeeCure Taiwan Co., Ltd.
A61K47/549A61P31/20
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Quick Facts
Patent No.
US 12,508,320
App. No.
18/679,403
Granted
Dec 30, 2025
Kind
B2
Abstract

A drug conjugate includes a structure shown by the following formula: Z-(linker-[R] m ) n . In the formula, Z is a drug compound, R is a sugar, and m and n are independently an integer from 1 to 6. The drug compound Z is a hepatitis virus targeting drug, a hepatitis B virus (HBV) drug, an inhibitor of apoptosis protein (IAP) antagonist, a multidrug resistance (MDR) inhibitor, or analogues, precursors, prodrugs, derivatives thereof.

Claims (31)

1 . A drug conjugate having the structure shown in formula (I):

Z-(linker-[R] m ) n   (I)

wherein, in formula (I), Z is a drug compound, R is a sugar, and m and n are independently an integer from 1 to 6, wherein the drug compound Z is selected from the group consisting of Entecavir, Birinapant, Tenofovir, LCL161 and Adefovir, and the sugar R is selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide, a tetrasaccharide, an oligosaccharide, and a polysaccharide, and

wherein in the drug conjugate, the drug compound Z is conjugated to the linker to form a carbamate linkage.

2 . The drug conjugate according to claim 1 , wherein the linker includes L 1 (L 2 ) p groups, wherein the L 1 group is linked to the drug compound Z to form the carbamate linkage, and the L 2 group links the L 1 group to the sugar R, wherein p is an integer from 1 to 4, the L 2 group is selected from the group consisting of a single bond, an alkyl having 1 to 50 carbons, alkoxy having 1 to 50 carbons, alkenyl having 2 to 50 carbons, and alkenyloxy having 2 to 50 carbons, and wherein, the alkyl, alkoxy, alkenyl, alkenyloxy is linear or branched, at least one —CH 2 — is optionally replaced by —CO—, —COO—, —OCO—, —S—, —O—, or —NH—, at least one —CH 2 CH 2 — is optionally replaced by —CH═CH— or —C≡C—, and at least one hydrogen in —CH 2 —, —CH═ or —NH— described above is optionally replaced by a halogen, trifluoromethyl, alkyl having 1 to 20 carbons, alkoxy having 1 to 20 carbons, or alkanoyl having 1 to 20 carbons, and at least one —O— above is optionally replaced with a phosphate, phosphonate, phosphinate, phosphine oxide, phosphoramide, phosphoramidate, phosphite, phosphonite, phosphine, aminophosphine, phosphoramidite, phosphonamidite, phosphonamide, phosphinamide or phosphorodiamidite group.

3 . The drug conjugate according to claim 1 , wherein the linker is selected from any one of formula (LX1), formula (LX2), formula (LX7) to formula (LX11), and formula (LX20):

wherein, in formula (LX1), formula (LX2), formula (LX7) to formula (LX11), and formula (LX20), Z is the drug compound, and R is the sugar.

4 . The drug conjugate according to claim 1 , wherein the linker comprises a triazole.

5 . The drug conjugate according to claim 1 , wherein the structure shown in b formula (I) is formula (II):

Z-(linker-[R] m ) 2   formula (II)

wherein, in formula (II), Z is the drug compound, R is the sugar, and m is independently an integer from 1 to 3.

6 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IA1) gr formula (IA2):

7 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IB3), formula (IB4), formula (IB5), formula (IB10) gr formula (IB11):

8 . The drug conjugate according to claim 1 ,

wherein the structure shown in formula (I) comprises formula (IC1), formula (IC2), formula (IC3), formula (IC4), formula (IC5), formula (IC6), formula (IC7), formula (IC8), formula (IC9), formula (IC10) or formula (IC11):

9 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (ID2), formula (ID3) or formula (ID4):

10 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IE1):

11 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IF1) or formula (IF2):

12 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IG1):

13 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IH3):

14 . The drug conjugate according to claim 1 , wherein the structure shown in formula (I) comprises formula (IJ2):

15 . A pharmaceutical composition, comprising:

an active ingredient, wherein the active ingredient comprises a drug conjugate having the structure shown in formula (I):

Z-(linker-[R] m ) n   formula(I)

wherein, in formula (I), Z is a drug compound, R is a sugar, and m and n are independently an integer from 1 to 6, the drug compound Z is selected from the group consisting of Entecavir, Birinapant Tenofovir, LCL161 and Adefovir, and the sugar R is selected from the group consisting of a monosaccharide, a disaccharide, a trisaccharide, a tetrasaccharide, an oligosaccharide, and a polysaccharide, and wherein in the drug conjugate, the drug compound Z is conjugated to the linker to form a carbamate linkage; and

at least one or more pharmaceutically acceptable excipients.

16 . The pharmaceutical composition according to claim 15 , wherein the drug conjugate of formula (I) comprises a first drug conjugate that is selected from the group consisting of formula (IA1), formula (IA2), formula (IC1), formula (IC2), formula (IC3), formula (IC4), formula (IC5), formula (IC6), formula (IC7, formula (IC8), formula (IC9), formula (IC10), formula (IC11), formula (IE1), formula (IF1), formula (IF2), and formula (IG1):

17 . The pharmaceutical composition according to claim 16 , wherein the drug conjugate of by formula (I) further comprises a second drug conjugate that is selected from the group consisting of formula (IB3), formula (IB4), formula (IB5), formula (IB10), formula (IB11), formula (ID2), formula (ID3), formula (ID4), formula (IH3), and formula (IJ2):

18 . The pharmaceutical composition according to claim 15 , wherein the pharmaceutical composition is prepared into tablets, capsules, granules, powders, solutions, syrups, spray, injections or inhalations, and the at least one or more pharmaceutically acceptable excipients is selected from the group consisting of fillers, extenders, binders, blending agents, surfactants, emulsifiers, dispersing agents, defoamers, lubricants, nonstick agents, blenders, coating materials, glidants, anti-sticking agents, diluents, dyes, pigments, dispersants, wetting agents, and combinations distinct excipients thereof.

19 . A method of treating hepatitis, comprising:

administering a therapeutically effective amount of the drug conjugate according to claim 1 , or a pharmaceutical composition comprising the drug conjugate of claim 1 to a patient having hepatitis.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 6, 2024
From: LIN, WUU-JYH; CHUNG, MIN-CHING; KE, CHI-SHIANG; TSENG, YA-CHEN; LIANG, CHIN-YU; LEE, YEN-CHUN; LI, HSIN-JOU; HUANG, TAI-YUN; HSUEH, NAI-CHEN; JIANG, YAN-FENG
To: SEECURE TAIWAN CO., LTD.
Reel/Frame 067635/0671 →
Continuity (2)
Provisional Application 63524210 · Jun 29, 2023
Related Publication 20250032621A1 · Jan 30, 2025
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