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1. 发明公开

US20240115726A1 HYDRAZONE-BASED SAPONIN DERIVATIVES 审中-公开
公开(公告)号：US20240115726A1
公开(公告)日：2024-04-11
申请号：US18012791
申请日：2021-06-22
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Ruben POSTEL , Guy HERMANS
IPC分类号： A61K47/68 , A61K47/54
CPC分类号： A61K47/6851 , A61K47/542 , A61K47/545 , A61K47/549 , A61K47/6889
摘要： The invention relates to a saponin derivative The invention also relates to a first pharmaceutical composition comprising the saponin derivative of the invention. In addition, the invention relates to a pharmaceutical combination comprising the first pharmaceutical composition of the invention and a second pharmaceutical composition comprising for example an ADC or AOC. The invention also relates to the first pharmaceutical composition or the pharmaceutical combination of the invention, for use as a medicament, or use in the treatment or prophylaxis of a cancer or an auto-immune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell, comprising contacting said cell with the molecule and with a saponin derivative of the invention. The invention also relates to a saponin conjugate comprising a cell-surface molecule binding-molecule, capable of binding to a target cell, covalently bound to the saponin. The invention also relates to a pharmaceutical combination comprising a pharmaceutical composition comprising the saponin conjugate of the invention and a second pharmaceutical composition comprising an active pharmaceutical ingredient, or to a pharmaceutical composition comprising the saponin conjugate of the invention and an active pharmaceutical ingredient. In addition, the invention relates to said pharmaceutical combination of the invention or said pharmaceutical composition of the invention, for use as a medicament, or for use in the treatment or the prophylaxis of a cancer or an auto-immune disease.

2. 发明公开

US20230270872A1 CONJUGATE OF SAPONIN AND SINGLE-DOMAIN ANTIBODY, PHARMACEUTICAL COMPOSITION COMPRISING SAID CONJUGATE, THERAPEUTIC USE THEREOF 审中-公开
公开(公告)号：US20230270872A1
公开(公告)日：2023-08-31
申请号：US18012710
申请日：2020-07-09
申请人： SAPREME TECHNOLOGIES B.V. , CHARITÉ - UNIVERSITÄTSMEDIZIN BERLIN
发明人： Ruben POSTEL , Guy HERMANS , Hendrik FUCHS
IPC分类号： A61K47/68 , A61K45/06 , A61P35/00
CPC分类号： A61K47/6807 , A61K45/06 , A61K47/6855 , A61K47/6849 , A61P35/00
摘要： The invention relates to a conjugate for transferring a saponin of the monodesmosidic triterpene glycoside type or of the bidesmosidic triterpene glycoside type from outside a cell into said cell, the conjugate comprising a single-domain antibody, capable of binding to said cell, covalently bound to a saponin. The invention also relates to a pharmaceutical combination comprising a first pharmaceutical composition comprising the conjugate of the invention and a second pharmaceutical composition comprising an active pharmaceutical ingredient, or to a pharmaceutical composition comprising the conjugate of the invention and an active pharmaceutical ingredient. In addition, the invention relates to the pharmaceutical combination of the invention or the pharmaceutical composition of the invention, for use as a medicament, or for use in the treatment or the prophylaxis of a cancer, an auto-immune disease, an infection, an enzyme deficiency, a gene defect. Furthermore, the invention relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell, comprising the application of the conjugate of the invention. Finally, the invention relates to a kit of parts, comprising the pharmaceutical combination of the invention or the pharmaceutical composition of the invention, or the conjugate of the invention, and instructions for use thereof.

3. 发明公开

US20240115712A1 SEMICARBAZONE-BASED SAPONIN CONJUGATE 审中-公开
公开(公告)号：US20240115712A1
公开(公告)日：2024-04-11
申请号：US18262994
申请日：2022-01-26
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Guy HERMANS , Ruben POSTEL , Helmus VAN DE LANGEMHEEN , Mazdak ASADIAN BIRJAND
IPC分类号： A61K47/55 , A61K47/54
CPC分类号： A61K47/55 , A61K47/554
摘要： The invention relates to a saponin conjugate comprising a saponin derivative based on a saponin comprising a triterpene aglycone and at least one of a first saccharide chain and a second saccharide chain linked to the aglycone core structure, wherein the saponin derivative comprises an aglycone core structure comprising an aldehyde functional group which aldehyde functional group has been transformed to a semicarbazone functional group, the saponin conjugate further comprising a proteinaceous molecule capable of binding to a cell-surface molecule. The invention also relates to a composition comprising the saponin conjugate. In addition, the invention relates to a pharmaceutical combination comprising said composition comprising the saponin conjugate and a pharmaceutical composition comprising for example an ADC or an antibody-oligonucleotide conjugate (AOC). The invention also relates to a pharmaceutical composition comprising the saponin conjugate and comprising for example an ADC or an AOC. The invention also relates to the pharmaceutical combination or pharmaceutical composition, for use as a medicament. The invention also relates to the saponin conjugate comprising the saponin derivative, a proteinaceous molecule capable of binding to a cell surface molecule (endocytic receptor), and further comprising an effector moiety such as an oligonucleotide. The invention also relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell.

4. 发明公开

US20230357310A1 Saponin derivatives with improved therapeutic window 审中-公开
公开(公告)号：US20230357310A1
公开(公告)日：2023-11-09
申请号：US17629796
申请日：2020-07-24
申请人： Sapreme Technologies B.V.
发明人： Ruben Postel , Guy Hermans , Hendrik Fuchs
IPC分类号： C07J63/00 , A61K45/06
CPC分类号： C07J63/008 , A61K45/06
摘要： The invention relates to a saponin derivative based on a saponin comprising a triterpene aglycone and a first saccharide chain and/or a second saccharide chain, and comprising: an aglycone core structure comprising an aldehyde group which has been derivatised; and/or the first saccharide chain wherein the first saccharide chain comprises a carboxyl group, which has been derivatised; and/or the second saccharide chain wherein the second saccharide chain comprises at least one acetoxy group which has been derivatised. The invention also relates to a first pharmaceutical composition comprising the saponin derivative of the invention. In addition, the invention relates to a pharmaceutical combination comprising the first pharmaceutical composition of the invention and a second pharmaceutical composition comprising any one or more of an antibody-toxin conjugate, a receptor-ligand—toxin conjugate, an antibody-drug conjugate, a receptor-ligand—drug conjugate, an antibody-oligonucleotide conjugate or a receptor-ligand—oligonucleotide conjugate. The invention also relates to the first pharmaceutical composition or the pharmaceutical combination of the invention, for use as a medicament, or use in the treatment or prophylaxis of a cancer, an infectious disease, viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, alpha-1 antitrypsin related liver disease, acute hepatic porphyria, transthyretin-mediated amyloidosis, or an auto-immune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell, comprising contacting said cell with the molecule and with a saponin derivative of the invention.

5. 发明申请

US20220023433A1 Saponin Conjugates 有权
公开(公告)号：US20220023433A1
公开(公告)日：2022-01-27
申请号：US17312104
申请日：2019-12-09
申请人： Sapreme Technologies B.V. , Charité - Universitätsmedizin Berlin
发明人： Ruben Postel , Hendrik Fuchs
IPC分类号： A61K47/64 , A61K47/68 , A61K47/54 , A61K47/59 , C12N15/113
摘要： The current invention relates to an effector moiety capable of inducing an intracellular effect when present inside a mammalian cell, the effector moiety comprising a payload conjugated with at least one saponin. The invention also relates to an antibody-drug conjugate comprising the effector moiety according to the invention, or a ligand-drug conjugate comprising the effector moiety of the invention, the effector moiety comprising covalently coupled saponin. The invention also relates to a therapeutic combination comprising: (a) the effector moiety of the invention, comprising at least one saponin, and optionally a pharmaceutically acceptable excipient; and (b) an antibody-drug conjugate or a ligand-drug conjugate, and optionally a pharmaceutically acceptable excipient. Further, the invention relates to a pharmaceutical composition comprising the effector moiety of the invention or the antibody-drug conjugate of the invention or the ligand-drug conjugate of the invention, comprising at least one saponin covalently linked to the effector molecule, and optionally a pharmaceutically acceptable excipient. The invention also relates to the effector moiety of the invention or the antibody-drug conjugate of the invention or the therapeutic combination of the invention or the ligand-drug conjugate of the invention or the pharmaceutical composition of the invention, for use as a medicament. Finally, the invention also relates to the effector moiety of the invention or the antibody-drug conjugate of the invention or the therapeutic combination of the invention or the ligand-drug conjugate of the invention or the pharmaceutical composition of the invention, for use in the treatment or prevention of a cancer or an autoimmune disease.

6. 发明公开

US20240279684A1 CYTOSOLIC DELIVERY OF GENOME EDITING TOOLS 审中-公开
公开(公告)号：US20240279684A1
公开(公告)日：2024-08-22
申请号：US18564885
申请日：2022-05-19
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Ruben POSTEL , Alexander WENG , Matthias Friedrich MELZIG , Simko SAMA
IPC分类号： C12N15/87 , C12N9/22 , C12N15/11 , C12N15/88 , C12N15/90
CPC分类号： C12N15/87 , C12N9/22 , C12N15/11 , C12N15/88 , C12N15/907 , C12N2310/20 , C12N2800/80
摘要： A first aspect of the invention relates to the use of a saponin in the in vitro delivery of a nucleic acid into a cell. Typically, the nucleic acid is plasmid DNA, e.g. with a relatively large size of at least 5.5 kbp. In embodiments, the nucleic acid is transfected into cells in the presence of saponin GE1741 and/or saponin SO1861. A second aspect of the invention relates to a method for delivering a nucleic acid encoding for a CRISPR/Cas construct into a cell in vitro. Typically, the nucleic acid is plasmid DNA, e.g. with a relatively large size of at least 5.5 kbp. In embodiments, the nucleic acid is transfected into cells in the presence of saponin GE1741 and/or saponin SO1861. In embodiments, the nucleic acid is combined with poly-lysine, forming nanoplexes for transfection of the nucleic acid into a In cell. A third aspect of the invention relates to a kit of parts for delivering a nucleic acid encoding for a CRISPR/Cas construct into a cell in vitro. In addition, the invention also relates to a nanoparticle suitable for in vitro delivery of a nucleic acid into a cell, the nanoparticle comprising or consisting of a nucleic acid encoding for a CRISPR/Cas construct, a poly-lysine peptide and optionally a saponin.

7. 发明公开

US20230365617A1 SAPONIN DERIVATIVES FOR USE IN MEDICINE 审中-公开
公开(公告)号：US20230365617A1
公开(公告)日：2023-11-16
申请号：US18012698
申请日：2021-06-23
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Ruben POSTEL , Guy HERMANS , Hendrik FUCHS
IPC分类号： A61K47/54 , A61K47/68 , A61P35/00 , C07J17/00 , A61K36/48
CPC分类号： C07J17/005 , A61K36/48 , A61K47/549 , A61K47/6807 , A61K47/6819 , A61P35/00
摘要： The invention relates to a Quillaja saponaria saponin derivative based on a saponin comprising a triterpene aglycone and a first saccharide chain and/or a second saccharide chain, and comprising: an aglycone core structure comprising an aldehyde group which has been derivatised; and/or the first saccharide chain wherein the first saccharide chain comprises a carboxyl group, which has been derivatised; and/or the second saccharide chain wherein the second saccharide chain comprises at least one acetoxy group which has been derivatised. The invention also relates to a first pharmaceutical composition comprising the saponin derivative of the invention. In addition, the invention relates to a pharmaceutical combination comprising the first pharmaceutical composition of the invention and a second pharmaceutical composition comprising any one or more of an antibody-toxin conjugate, a receptor-ligand - toxin conjugate, an antibody-drug conjugate, a receptor-ligand - drug conjugate, an antibody-oligonucleotide conjugate or a receptor-ligand - oligonucleotide conjugate. The invention also relates to the first pharmaceutical composition or the pharmaceutical combination of the invention, for use as a medicament, or use in the treatment or prophylaxis of a cancer, an infectious disease, viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, alpha-1 antitrypsin related liver disease, acute hepatic porphyria, transthyretin-mediated amyloidosis, or an autoimmune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell, comprising contacting said cell with the molecule and with a saponin derivative of the invention.

8. 发明公开

US20230302140A1 CONJUGATE OF A SINGLE DOMAIN ANTIBODY, A SAPONIN AND AN EFFECTOR MOLECULE, PHARMACEUTICAL COMPOSITION COMPRISING THE SAME, THERAPEUTIC USE OF SAID PHARMACEUTICAL COMPOSITION 审中-公开
公开(公告)号：US20230302140A1
公开(公告)日：2023-09-28
申请号：US18012729
申请日：2021-06-22
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Ruben POSTEL , Guy HERMANS , Hendrik FUCHS
IPC分类号： A61K47/54 , A61K47/64 , A61K47/68
CPC分类号： A61K47/549 , A61K47/6415 , A61K47/6807 , A61K47/6855
摘要： The invention relates to a conjugate for transferring an effector molecule from outside a cell into said cell, the conjugate comprising at least one effector molecule to be transferred into the cell, at least one saponin of the mono-desmosidic triterpene glycoside type or the bi-desmosidic triterpene glycoside type, and at least one single-domain antibody (sdAb), covalently bound to each other, wherein the sdAb is capable of binding to a cell-surface molecule of said cell. The invention also relates to a pharmaceutical composition comprising the conjugate of the invention. Furthermore, the invention relates to a pharmaceutical composition of the invention, for use as a medicament. In addition, the invention relates to a pharmaceutical composition of the invention, for use in the treatment or the prophylaxis of any one or more of: a cancer, an auto-immune disease such as rheumatoid arthritis, an enzyme deficiency, a disease related to an enzyme deficiency, a gene defect, a disease relating to a gene defect, an infection such as a viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, alpha-1 antitrypsin related liver disease, acute hepatic porphyria, an amyloidosis and transthyretin- mediated amyloidosis. The invention also relates to an in vitro or ex vivo method for transferring the conjugate from outside a cell to inside said cell or for transferring the effector molecule comprised by the conjugate of the invention from outside a cell to inside said cell, preferably to the cytosol of said cell.

9. 发明公开

US20230293708A1 CONJUGATE OF SAPONIN AND SINGLE-DOMAIN ANTIBODY, PHARMACEUTICAL COMPOSITION COMPRISING SAID CONJUGATE, THERAPEUTIC USE THEREOF 审中-公开
公开(公告)号：US20230293708A1
公开(公告)日：2023-09-21
申请号：US18012715
申请日：2021-06-22
申请人： SAPREME TECHNOLOGIES B.V. , CHARITÉ - UNIVERSITÄTSMEDIZIN BERLIN
发明人： Ruben POSTEL , Guy HERMANS , Hendrik FUCHS
IPC分类号： A61K47/68 , A61K45/06 , A61P35/00
CPC分类号： A61K47/6809 , A61K47/6889 , A61K47/6851 , A61K47/6849 , A61K45/06 , A61P35/00
摘要： The invention relates to a conjugate for transferring a saponin of the monodesmosidic triterpene glycoside type or of the bidesmosidic triterpene glycoside type from outside a cell into said cell, the conjugate comprising a single-domain antibody, capable of binding to said cell, covalently bound to a saponin. The invention also relates to a pharmaceutical combination comprising a first pharmaceutical composition comprising the conjugate of the invention and a second pharmaceutical composition comprising an active pharmaceutical ingredient, or to a pharmaceutical composition comprising the conjugate of the invention and an active pharmaceutical ingredient. In addition, the invention relates to the pharmaceutical combination of the invention or the pharmaceutical composition of the invention, for use as a medicament, or for use in the treatment or the prophylaxis of a cancer, an auto-immune disease, an infection, an enzyme deficiency, a gene defect. Furthermore, the invention relates to an in vitro or ex vivo method for transferring a molecule from outside a cell to inside said cell, comprising the application of the conjugate of the invention. Finally, the invention relates to a kit of parts, comprising the pharmaceutical combination of the invention or the pharmaceutical composition of the invention, or the conjugate of the invention, and instructions for use thereof.

10. 发明公开

US20230293562A1 THERAPEUTIC COMBINATION OF GALNAC-OLIGONUCLEOTIDE CONJUGATE AND SAPONIN, AND USES THEREOF 审中-公开
公开(公告)号：US20230293562A1
公开(公告)日：2023-09-21
申请号：US18012778
申请日：2021-06-23
申请人： SAPREME TECHNOLOGIES B.V.
发明人： Ruben POSTEL , Guy HERMANS
IPC分类号： A61K31/704 , A61K47/54
CPC分类号： A61K31/704 , A61K47/549
摘要： The invention relates to a pharmaceutical combination comprising: a conjugate of an effector molecule and a ligand for ASGPR, wherein the ligand for ASGPR comprises at least one GalNAc moiety; and a saponin of the monodesmosidic or bidesmosidic triterpene glycoside type. The invention also relates to a pharmaceutical composition comprising the conjugate and the saponin. In addition, the invention relates to a pharmaceutical combination or composition of the invention, for use as a medicament, or for use in the treatment or prophylaxis of a disease or health problem in which an expression product is involved of any one or more of genes: apoB, TTR, PCSK9, ALAS 1, ATS, GO, CCS, X gene of HBV, S gene of HBV, AAT and LDH, and/or for use in the treatment or prophylaxis of a cancer, an infectious disease, a viral infection, hypercholesterolemia, primary hyperoxaluria, haemophilia A, haemophilia B, AAT related liver disease, acute hepatic porphyria, TTR-mediated amyloidosis, hereditary TTR amyloidosis (hATTR), complement-mediated disease, hepatitis B infection, or an auto-immune disease. Furthermore, the invention relates to an in vitro or ex vivo method for transferring an effector molecule of the invention from outside a cell to inside said cell, preferably into the cytosol of said cell. The invention also relates to an in vitro or ex vivo method for transferring the conjugate of the invention from outside a cell to inside said cell.

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