WO2024054089A1 - Nouveaux dérivés de camptothécine et conjugué véhicule-médicament les comprenant - Google Patents
Nouveaux dérivés de camptothécine et conjugué véhicule-médicament les comprenant Download PDFInfo
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- WO2024054089A1 WO2024054089A1 PCT/KR2023/013502 KR2023013502W WO2024054089A1 WO 2024054089 A1 WO2024054089 A1 WO 2024054089A1 KR 2023013502 W KR2023013502 W KR 2023013502W WO 2024054089 A1 WO2024054089 A1 WO 2024054089A1
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Images
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
- A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
- A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
- A61K47/68037—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a camptothecin [CPT] or derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
Definitions
- the present invention relates to a novel camptothecin derivative with excellent anticancer efficacy and safety, a carrier-drug conjugate containing the same, and its pharmaceutical use.
- Inhibitors of type 1 topoisomerase I an isomerization enzyme involved in DNA replication and recombination, are drugs with an anticancer mechanism with proven efficacy and safety, and have been clinically used to treat colon cancer, lung cancer, breast cancer, and ovarian cancer. Excellent anticancer efficacy has been proven in various intractable solid cancers, such as:
- Camptothecin (CPT) and its derivatives are known as representative type 1 topoisomerase inhibitors, but camptothecin has the problem of low water solubility and high toxicity.
- camptothecin derivatives with low toxicity and high water solubility
- drugs such as Irinotecan and Topotecan have been used to treat colon cancer, ovarian cancer, and lung cancer. It is licensed and commercially available.
- SN-38 is a potent topoisomerase-I inhibitor with IC50 values in the nanomolar range in several cell lines, and is the active form of irinotecan, a prodrug used to treat colorectal cancer. It is also active in lung cancer, breast cancer, and brain cancer.
- Trop-2-SN-38 Antibody-Drug Conjugate (ADC) is currently effective in many cancer types, including TNBC, bladder cancer, and stomach cancer, but the problem of SN-38 resistance still remains.
- DXd Daiichi Sankyo used DXd, a derivative of exatecan, a cytotoxic drug that is about 10 times more active in cancer cells than SN-38, in the development of Enhertu.
- DXd has good solubility, is relatively safe, and has a high killing effect on surrounding cells, making it advantageous for the treatment of heterogeneous tumors.
- it has the disadvantage of having a short half-life that can reduce off-target effects.
- camptothecin-based drugs developed to date are used as payloads in ADCs, they have lower cytotoxicity and still maintain safety compared to ADCs with existing ultra-toxic payloads such as MMAE or MMAF. Not only does it present a problem, but it also has the problem of reduced anti-cancer effectiveness due to the development of resistance due to overexpression of ABCG2 Drug Efflux Pump, etc.
- camptothecin derivatives that not only exhibit higher cytotoxicity but are also superior in safety and have significantly reduced resistance that causes reduced anticancer effectiveness, particularly camptothecin derivatives suitable as payloads and carrier-drug conjugates containing the same.
- the demand is urgent.
- the purpose of the present invention is to provide a novel camptothecin derivative that has a strong type 1 topoisomerase inhibitor effect, exhibits high cytotoxicity, and has excellent safety.
- Another object of the present invention is to provide a carrier-drug conjugate containing a camptothecin derivative according to the present invention, and a pharmaceutical composition containing a camptothecin derivative or a carrier-drug conjugate containing the same according to the present invention.
- the purpose of the present invention is to provide a method of treating cancer using a camptothecin derivative or a carrier-drug conjugate containing the same according to the present invention.
- a first aspect of the present invention provides a compound represented by any one of Formulas 1 to 8, an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a prodrug thereof.
- a second aspect of the present invention provides a pharmaceutical composition for preventing or treating cancer containing a compound represented by any one of Formulas 1 to 8, an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a prodrug thereof. .
- the present invention provides novel camptothecin derivatives having the structures of Formulas 1 to 8.
- Camptothecin derivatives represented by Formulas 1 to 8 or isomers thereof according to the present invention are hydrophobic small molecules that can permeate cell membranes, so they are delivered to cancer tissues by the EPR effect (enhanced permeability and retention effect) and penetrate deep into cancer tissues. It can accumulate at high concentrations, penetrate the cell membrane, exert cytotoxicity inside the cell, kill the cell, and then be released and subsequently penetrate the cell membrane and move into the cell to act on surrounding cells.
- camptothecin derivatives represented by the compounds of Formulas 1 to 8 or isomers thereof according to the present invention include not only the compounds of Formulas 1 to 8 or isomers thereof, but also pharmaceutically acceptable salts thereof, solvates thereof, and Includes prodrugs.
- salts refer to salts commonly used in the pharmaceutical industry, such as salts of inorganic ions including sodium, potassium, calcium, magnesium, lithium, copper, manganese, zinc, iron, etc., and hydrochloric acid. , phosphoric acid, and sulfuric acid, as well as salts of organic acids such as ascorbic acid, citric acid, tartaric acid, lactic acid, maleic acid, malonic acid, fumaric acid, glycolic acid, succinic acid, propionic acid, acetic acid, orotate acid, and acetylsalicylic acid.
- amino acids such as lysine, arginine, and guanidine.
- salts of organic ions such as tetramethyl ammonium, tetraethyl ammonium, tetrapropyl ammonium, tetrabutyl ammonium, benzyl trimethyl ammonium, and benzethonium that can be used in pharmaceutical reactions, purification, and separation processes, but are not limited to these.
- Prodrug means something that is used in the relevant technical field.
- an inactive compound is a drug that is converted to an active state through drug metabolism in the body.
- a physiologically active substance or a therapeutically active organic compound is chemically modified and the parent compound is liberated or released under enzymatic or other conditions in vivo. refers to a compound designed to A prodrug is converted into the target compound in vivo after administration.
- it is a useful drug it has unsuitable properties in terms of side effects, stability, solubility, absorption, and duration of action, and is chemically modified to enable clinical use.
- Solidvate refers to a compound represented by any one of Formulas 1 to 8, or an isomer thereof and a pharmaceutically acceptable salt thereof, further comprising a stoichiometric or non-stoichiometric amount of solvent bound by non-covalent intermolecular forces. it means.
- the solvent is water
- the solvate is a hydrate.
- the present invention provides a carrier-drug conjugate comprising a compound represented by any one of Formulas 1 to 8 according to the present invention, an isomer thereof, a pharmaceutically acceptable salt thereof, or a solvate thereof. provides.
- Carrier refers to a substance that has the ability to selectively and specifically deliver the camptothecin derivative according to the present invention to the target site, for example, cancer cells, and includes antibodies, peptides, liposomes, etc. It may be a body, and/or an aptamer, but is not limited thereto, and is preferably an antibody.
- Aptamer-Drug Conjugate is an aptamer introduced instead of an antibody in ADC.
- Aptamers are single-stranded nucleic acids with a three-dimensional structure. Aptamers are usually discovered through the SELEX (Systematic Evolution of Ligands by Exponential enrichment) process. Selex is a technology that obtains functional nucleic acids that bind to target protein molecules in a compound library. Aptamers can bind to targets very strongly and selectively, so they are also called chemical antibodies. Aptamers are about 20 kDa in size and are known to have excellent cell penetration and low immunogenicity compared to antibodies.
- aptamers can be chemically synthesized, precise design of the conjugation location and number of drugs is possible when manufacturing aptamer-drug conjugates.
- the production cost is lower than that of ADC.
- Aptamers are generally made of natural nucleic acids, so they are degraded by nucleic acid degrading enzymes in the body, making them less stable in vivo.
- nucleic acid degrading enzymes in the body, making them less stable in vivo.
- the limitations on the stability of modified aptamers can be overcome.
- PDC Peptide-Drug Conjugate
- ADC ADC in which peptides are introduced instead of antibodies.
- Peptides are composed of amino acids and have a size ranging from 500 to 5000 Da (Dalton). This is a very small size compared to antibodies of 150 kDa (kilodaltons) or more. Therefore, peptide-based PDC has superior cell penetration ability compared to ADC, and the possibility of immunogenicity is very low. Additionally, peptides can be chemically synthesized. For this reason, PDC not only has a very low production cost, but also allows precise control of the conjugation position and ratio of peptide and drug.
- peptides are easily degraded by proteolytic enzymes and therefore have a short biological half-life.
- strategies using modified peptides such as cyclic peptides and introduction of non-natural amino acids are being proposed.
- Repebody is a type of artificial antibody that does not have an antibody skeleton but has the function of recognizing antigens like an antibody. Lipibodies specific to target proteins can be discovered through phage display technology.
- Phage display is a technology that expresses desired proteins on the surface of bacteriophage.
- Lipibody is about 30kDa in size, which is 20% of an antibody drug. Therefore, it is known to have relatively low immunogenicity and improved cell penetration compared to antibodies.
- lipibodies are expected to increase structural stability by controlling thermal and pH stability. Compared to antibodies, production costs are also assessed to be relatively low. Because of these advantages of lipibodies, interest in developing lipibody-drug conjugates (Repebody-DC) as a strategy to replace antibodies with lipibodies is also increasing.
- Repebody-DC lipibody-drug conjugates
- antigens include, but are not limited to, antigens selectively distributed on the surface of cancer, such as Her2, FolR, and PSMA, and antigens overexpressed in cancer cells, such as Trop2, which are distributed in small numbers in normal tissues.
- Exemplary cancer cell target antigens include 5T4, ABL, ABCF1, ACVR1, ACVR1B, ACVR2, ACVR2B, ACVRL1, ADORA2A, AFP, Aggrecan, AGR2, AICDA, AIF1, AIGI, AKAP1, AKAP2, ALCAM, ALK, AMH, AMHR2, ANGPT1.
- Non-limiting examples of antibodies in the present invention include Urelumab, Utomilumab, Bebtelovimab, Aducanumab, Bapinezumab, and Crenezumab. , Donanemab, Gantenerumab, Lecanemab, Solanezumab, Nesvacumab, Evinacumab, Enoblituzumab, Ombur Omburtamab, Belimumab, Ianalumab, Tabalumab, Bertilimumab, Mogamulizumab, Leronlimab, Cipilizumab ( Siplizumab), Foralumab, Muromonab-CD3, Otelixizumab, Teplizumab, Ibalizumab, Tregalizumab, Zanolimumab, Itolizumab, Efalizumab, Inebilizumab, Tafasitamab, Tositumomab, O
- the carrier and the drug are conjugated through a linker.
- the linker in the present invention should be stable in the bloodstream, preventing the drug from being separated from carriers such as antibodies, maintaining its structure until it reaches the target such as antigen, and minimizing damage to normal tissues.
- the antibody-drug conjugate is stable when circulating throughout the body, it is cleaved in the target cells to appropriately release the cytotoxic drug and safely deliver the drug to the target, thereby ensuring that the antibody-drug conjugate has both efficacy and safety.
- the carrier-drug conjugate according to the present invention may be characterized in that the carrier is conjugated to the drug, that is, the compound of Formula 1 to Formula 8 through a linker, but is not limited thereto.
- the compounds of Formulas 1 to 8 can be linked to a linker at an appropriate site as long as their anticancer activity and other properties do not change. Accordingly, the present invention provides compounds of Formulas 1 to 8.
- a drug-linker in which the compound of 8 and the linker are connected is provided.
- the drug-linker according to the present invention may have the structure of Formula 1a to Formula 8a, but is not limited thereto.
- L refers to a linker.
- the linker may be in a form that is cleavable in a specific intracellular environment and/or condition, that is, a drug may be released from the antibody through cleavage of the linker in the intracellular environment.
- the linker may be cleaved by a cleaving agent present in the intracellular environment, such as a lysosome or endosome, and may be a peptide that may be cleaved by an intracellular peptidase or protease enzyme, such as a lysosomal or endosomal protease. It may be a linker. Typically, peptide linkers are at least two amino acids long.
- the cleavage agent may include cathepsin B, cathepsin D, and plasmin, and hydrolyzes the peptide to release the drug into the target cell.
- the peptide linker can be cleaved by the thiol-dependent protease cathepsin-B, which is highly expressed in cancer tissues, for example, Gly-Gly-Phe-Gly (GGFG), Gly-Gly-Tyr-Gly (GGYG) , Phe-Leu or Gly-Phe-Leu-Gly linkers may be used, but are not limited thereto. Additionally, the peptide linker can be cleaved by, for example, an intracellular protease and may be a Val-Cit linker or a Phe-Lys linker.
- the cleavable linker is pH sensitive and may be sensitive to hydrolysis at a specific pH value.
- pH sensitive linkers indicate that they can be hydrolyzed under acidic conditions.
- acid labile linkers that can be hydrolyzed in lysosomes such as hydrazone, semicarbazone, thiosemicarbazone, cis-aconitic amide, orthoester, acetal, It may be ketal, etc.
- the linker may be cleaved under reducing conditions, for example, a disulfide linker may correspond to this.
- SATA Nsuccinimidyl-S-acetylthioacetate
- SPDP N-succinimidyl-3- (2-pyridyldithio)propionate
- SPDB Nsuccinimidyl-3- (2-pyridyldithio)butyrate
- SMPT N-succinimidyl-oxycarbonyl-alpha-methyl
- a variety of disulfide bonds can be formed using -alpha-(2-pyridyl-dithio)toluene).
- the linker may include a beta-glucuronide linker that is recognized and hydrolyzed by beta-glucuronidase, which exists in large numbers in lysosomes or is overexpressed in some tumor cells.
- a beta-glucuronide linker disclosed in Korean Patent Publication No. 2015-0137015 for example, a beta-glucuronide linker containing a self-immolative group, may be used.
- linker may be, for example, a non-cleavable linker, and the drug is released through an antibody hydrolysis step, producing, for example, an amino acid-linker-drug complex.
- This type of linker can be a thioether group or maleimidocaproyl group and can maintain stability in the blood.
- the linker according to the present invention is characterized by containing GGFG or GGYG, and in the case of the linker containing GGYG, the hydrogen atom of the hydroxyl group of the tyrosine (Y, Tyrosin) side chain is separated under specific conditions. May be substituted with a possible hydrophilic functional group.
- the hydrophilic functional group is preferably a monovalent hydrophilic functional group, such as beta-glucuronide or PEG (PEG) having 3 to 100 ethylene glycol repeating units. Examples may include esters or carbonates having a polyethylene glycol (Polyethylene Glycol) group, but are not limited thereto.
- the linker may have the structure of Formula 11 or Formula 12, but is not limited thereto.
- n may be an integer of 3 to 10.
- the drug and/or drug-linker which is the compound of Formula 1 to Formula 8, or the compound of Formula 1a to Formula 8a, is randomly selected through lysine in the antibody. It can be conjugated with or through the cysteine exposed when the disulfide bond chain is reduced.
- a drug-linker may be bound through a genetically engineered tag, for example, lysine or cysteine present in a peptide or protein.
- the present invention provides a method for preventing or treating cancer, including a compound represented by any one of Formulas 1 to 8 according to the present invention, an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a carrier-drug conjugate containing the same.
- a pharmaceutical composition for use including a compound represented by any one of Formulas 1 to 8 according to the present invention, an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a carrier-drug conjugate containing the same.
- a therapeutically effective amount of the compound represented by Formula 1 to Formula 8 or an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a carrier-drug conjugate containing the same is used.
- a method for treating or preventing cancer comprising administering to a subject in need thereof.
- the subject may be a mammal, including humans.
- the cancer is caused by inhibition of topoisomerase I, and/or one or more cancer-related survival genes selected from the group consisting of survivin, Mcl-1, XIAP, and cIAP2. It includes all cancers that can be treated by inhibiting genes, and may be solid cancer or blood cancer. For example, pseudomyxoma, intrahepatic biliary tract cancer, hepatoblastoma, liver cancer, thyroid cancer, colon cancer, testicular cancer, myelodysplastic syndrome, glioblastoma, oral cancer, oral cavity cancer, mycosis fungoides, acute myeloid leukemia, acute lymphocytic leukemia, basal cell carcinoma, ovary.
- cancer-related survival genes selected from the group consisting of survivin, Mcl-1, XIAP, and cIAP2.
- Epithelial cancer ovarian germ cell cancer, male breast cancer, brain cancer, pituitary adenoma, multiple myeloma, gallbladder cancer, biliary tract cancer, colon cancer, chronic myeloid leukemia, chronic lymphocytic leukemia, retinoblastoma, choroidal melanoma, ampulla of Vater cancer, bladder cancer, peritoneal cancer, Parathyroid cancer, adrenal cancer, sinonasal cancer, non-small cell lung cancer, tongue cancer, astrocytoma, small cell lung cancer, pediatric brain cancer, pediatric lymphoma, childhood leukemia, small intestine cancer, meningioma, esophageal cancer, glioma, renal pelvis cancer, kidney cancer, heart cancer, duodenum Cancer, malignant soft tissue cancer, malignant bone cancer, malignant lymphoma, malignant mesothelioma, malignant melanoma, eye cancer, vulvar cancer, ureteral cancer, ure
- patient refers to animals, such as mammals.
- the patient is a human.
- the patient is a non-human animal, such as a dog, cat, domestic animal (e.g., horse, pig, or donkey), chimpanzee, or monkey.
- therapeutically effective amount refers to a compound represented by any one of Formulas 1 to 8 that is effective in treating or preventing cancer, or an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or It indicates the amount of carrier-drug conjugate containing it.
- therapeutically effective amount means an amount sufficient to treat the disease with a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level is determined by the type and severity of the individual, age, gender, type of disease, It can be determined based on factors including the activity of the drug, sensitivity to the drug, time of administration, route of administration and excretion rate, duration of treatment, drugs used simultaneously, and other factors well known in the medical field.
- the pharmaceutical composition of the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with commercially available therapeutic agents. And it can be administered single or multiple times. Considering all of the above factors, it is important to administer an amount that can obtain the maximum effect with the minimum amount without side effects, and the compound represented by any of Formulas 1 to 8 of the present invention, or an isomer thereof, or a pharmaceutically acceptable salt thereof , or a carrier-drug conjugate containing it exhibits a dose-dependent effect, so the administered dose can be easily determined by a person skilled in the art depending on various factors such as the patient's condition, age, gender, and complications. Since the active ingredient of the pharmaceutical composition of the present invention has excellent safety, it can be used at a dose exceeding the determined dosage.
- the present invention provides a compound represented by any of Formulas 1 to 8, or an isomer thereof, for use in the production of a medicament for use in the treatment or prevention of cancer.
- a pharmaceutically acceptable salt, a solvate thereof, or a carrier-drug conjugate comprising the same.
- the compound represented by any one of Formulas 1 to 8, or an isomer thereof, a pharmaceutically acceptable salt thereof, a solvate thereof, or a carrier-drug conjugate containing the same is used as a pharmaceutically acceptable auxiliary, diluent, or carrier. etc. can be mixed, and can be prepared as a composite preparation with other active agents to have a synergistic effect of the active ingredients.
- the anticancer effect or therapeutic effect of an anticancer agent refers to the action of reducing the severity of cancer, reducing the size of a tumor, or delaying or slowing the progression of cancer that occurs while a patient is suffering from a specific cancer. It can be referred to.
- the anticancer effect caused by an anticancer drug may be the Cell Viability (change in the degree of cytotoxicity or number of cells) of cancer cells after treating cancer cells with an anticancer drug in-vitro and/or in-vivo.
- Cell Viability change in the degree of cytotoxicity or number of cells
- cancer patients can directly confirm the anticancer effect of anticancer drugs, derive related data, and use it as a database.
- animal model PK parameters and/or toxicity profiles can be considered in parallel.
- the anticancer effect of an anticancer drug can be inferred from in-vitro data, such as the % maximum effect of the anticancer drug, such as IC 50 , IC 60 , IC 70 , IC 80 , and IC 90 , and the highest blood concentration of the drug. It can also be confirmed in non-clinical animal models and clinical cancer patients through in-vivo data such as concentration (Cmax) and/or area under the blood drug concentration-time curve (AUC).
- Cmax concentration
- AUC blood drug concentration-time curve
- the reactivity of an anticancer drug refers to clinical sensitivity in terms of anticancer effect.
- “Sensitivity” and “sensitive” when referring to treatment with anticancer agents are relative terms that refer to the degree of effectiveness of a compound in alleviating or reducing the progression of the tumor or disease being treated.
- Effective patient anti-cancer effect/response refers to, e.g., 5%, 10%, 15%, 20% of patient response, as measured by any suitable means such as gene expression, cell counting, assay results, etc. , 25%, 30%, 40%, 50%, 60%, 70%, 80%, 90%, 100%, 200%, or more.
- the administered dose is the dose expected to have medicinal effect.
- the medicinal effect may be an anti-cancer effect.
- the reactivity (anti-cancer effect) of an anti-cancer drug is the degree of response, including the % maximum effect of the anti-cancer drug, such as IC 50 , IC 60 , IC 70 , IC 80 , and IC 90 , and the value of toxicity to normal cells (LC 50 ). It can be.
- oral dosage forms can be formulated using various formulation techniques known in the art.
- it may include a biodegradable (hydrolyzable) polymeric carrier used to adhere to the oral mucosa. It is manufactured to erode slowly over a predetermined period of time, where drug delivery is provided essentially holistically.
- Drug delivery in oral dosage forms avoids the weaknesses encountered with oral drug administration, such as slow absorption, degradation of the active agent by fluids present in the gastrointestinal tract, and/or first-pass inactivation in the liver.
- biodegradable (hydrolyzable) polymeric carriers virtually any such carrier can be used as long as the desired drug release profile is not impaired, and the carrier is compatible with any of the other ingredients present in the oral dosage unit.
- polymeric carriers include hydrophilic (water-soluble and water-swellable) polymers that adhere to the wet surface of the oral mucosa.
- Examples of polymeric carriers useful herein include acrylic acid polymers (eg, carbomers).
- non-limiting examples of other ingredients that can be incorporated into oral dosage forms include disintegrants, diluents, binders, lubricants, flavoring agents, colorants, preservatives, etc. In some embodiments, it may be in the form of tablets, lozenges, or gels, formulated in a conventional manner for oral or sublingual administration.
- administration of the compound is continued at the discretion of the physician if the patient's condition improves;
- the dose of drug to be administered may be temporarily reduced or temporarily suspended for any length of time (i.e., a “dose washout”).
- the length of the washout can vary between 2 days and 1 year, by way of example only: 2 days, 3 days, 4 days, 5 days, 6 days, 7 days, 10 days, 12 days, 15 days, 20 days, 28 days. days, 35 days, 50 days, 70 days, 100 days, 120 days, 150 days, 180 days, 200 days, 250 days, 280 days, 300 days, 320 days, 350 days, or 365 days.
- the dose reduction during washout is 10%-100%, and by way of example only, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55 %, 60%, 65%, 70%, 75%, 80%, 85%, 90%, 95%, or 100%.
- the amount of a given agent that will correspond to such amount will vary depending on factors such as the particular compound, the severity of the disease, and the identity (e.g., body weight) of the subject in need of treatment, but will nevertheless vary, including, for example, the formulation to be administered, the administration Depending on the route, and the particular circumstances surrounding the subject to be treated, this can be routinely determined in a manner known in the art. In general, however, doses used for treatment of adult humans will typically range from 0.02-5000 mg/day, or about 1-1500 mg/day.
- a single dosage herein may be given as a single dose or in divided doses administered simultaneously, for example, as 2, 3, 4 or more sub-doses.
- the oral dosage form is in unit dosage form suitable for single administration of precise doses.
- the formulation is divided into unit doses containing appropriate amounts of one or more compounds.
- the unit dose is in the form of a packet containing discrete amounts of dosage form.
- Non-limiting examples are packaged tablets or capsules, and powders in vials or in ampoules.
- Aqueous suspension compositions can be packaged in single-dose, non-reclosable containers. Alternatively, multi-dose reclosable containers can be used, in which case it is typical to include a preservative in the composition.
- formulations for parenteral injection are provided in unit dosage form, including but not limited to ampoules, or in multi-dose containers, with an added preservative.
- parenteral administration i.e., bolus, intravenous, and intratumoral injection
- a pharmaceutically acceptable parenteral vehicle i.e., bolus, intravenous, and intratumoral injection
- parenteral vehicle i.e., bolus, intravenous, and intratumoral injection
- a pharmaceutically acceptable parenteral vehicle i.e., bolus, intravenous, and intratumoral injection
- It is optionally mixed in the form of a lyophilized preparation or aqueous solution with pharmaceutically acceptable diluents, carriers, excipients or stabilizers (Remington's Pharmaceutical Sciences (1980) 16th edition, Osol, A. Ed.).
- camptothecin derivatives represented by Formulas 1 to 8 according to the present invention have more desirable properties than existing camptothecin derivatives in terms of efficacy, toxicity, selectivity, action time, administration, handling, stability and/or production potential, etc. It has the advantage of maximizing the efficacy of main drug target modulation through an additional mechanism of action that (i) simultaneously inhibits the Bcl family, such as the resistance protein Survivin, and/or (ii) inhibits the action of the efflux pump. .
- the carrier-drug conjugate containing a camptothecin derivative represented by any one of Formulas 1 to 8 according to the present invention has the advantage of minimizing toxicity, providing high safety, and at the same time showing high therapeutic efficacy.
- Figure 1 shows structural formulas of various camptothecin-based anticancer drugs (SN-38, Exatecan, Dxd, FL118).
- Figure 2 is a diagram showing the results of in vitro cytotoxicity assay of the compound of Formula 2 in FaDu cell line.
- the analysis conditions for the compounds according to the present invention are as follows.
- the physicochemical properties, such as LogP, cLogP, and tPSA (topological polar surface area) values, of the compounds of Formulas 1 to 8 according to the present invention are shown in Table 1.
- 3000 FaDu cell lines per well were seeded in a 96 well plate and incubated at constant temperature (37°C, 5% CO 2 ). After 24 hours, 100 ⁇ l of drugs at 9 concentrations (serial dilution of 1/5 from 1000 nM) were treated with the cells. At this time, 7MAD-MD-CPT (lactic acid), a compound of Formula 2, and a control group were treated, respectively.
- Compounds of Formulas 1 to 8 according to the present invention are conjugated with Trastuzumab, Cetuximab, Nimotuzumab or Sacituzumab through the linker of Formula 11.
- Antibody-drug conjugates containing the compounds according to the invention are prepared and their anticancer efficacy is tested.
- the preparation of the antibody-drug conjugate is carried out as follows.
- the drug-to-antibody ratio is about 8.
- excess drug-linker was removed using a PD-10 desalting column, and the final antibody-drug conjugate was obtained.
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Abstract
La présente invention concerne de nouveaux dérivés de camptothécine ayant les structures de formules chimiques 1 à 8 et des conjugués véhicule-médicament les comprenant, les dérivés possédant des propriétés plus souhaitables par rapport aux dérivés de camptothécine existants en termes d'efficacité, de toxicité, de sélectivité, de temps d'action, d'administration, de manipulation, de stabilité et/ou d'aptitude à la production et bénéficiant de l'avantage d'augmenter au maximum l'efficacité de la modulation cible de médicament principale par (i) inhibition simultanée de la famille Bcl telle que la protéine de résistance survivine, etc. et/ou (ii) le mécanisme supplémentaire d'inhibition de l'activité de pompe d'efflux. Les nouveaux dérivés de camptothécine et les conjugués véhicule-médicament selon la présente invention ont une excellente efficacité anticancéreuse et une excellente sécurité et peuvent ainsi être utilisés dans le traitement de divers cancers.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5342947A (en) * | 1992-10-09 | 1994-08-30 | Glaxo Inc. | Preparation of water soluble camptothecin derivatives |
KR20210006362A (ko) * | 2018-04-06 | 2021-01-18 | 시애틀 지네틱스, 인크. | 캄토테신 펩타이드 접합체들 |
WO2021067861A1 (fr) * | 2019-10-04 | 2021-04-08 | Seagen Inc. | Conjugués peptidiques de camptothécine |
KR20220027828A (ko) * | 2019-04-26 | 2022-03-08 | 이뮤노젠 아이엔씨 | 캄프토테신 유도체 |
WO2022170971A1 (fr) * | 2021-02-09 | 2022-08-18 | 苏州宜联生物医药有限公司 | Conjugué à substance bioactive, son procédé de préparation et son utilisation |
-
2023
- 2023-09-08 KR KR1020230119533A patent/KR20240035370A/ko unknown
- 2023-09-08 WO PCT/KR2023/013502 patent/WO2024054089A1/fr unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5342947A (en) * | 1992-10-09 | 1994-08-30 | Glaxo Inc. | Preparation of water soluble camptothecin derivatives |
KR20210006362A (ko) * | 2018-04-06 | 2021-01-18 | 시애틀 지네틱스, 인크. | 캄토테신 펩타이드 접합체들 |
KR20220027828A (ko) * | 2019-04-26 | 2022-03-08 | 이뮤노젠 아이엔씨 | 캄프토테신 유도체 |
WO2021067861A1 (fr) * | 2019-10-04 | 2021-04-08 | Seagen Inc. | Conjugués peptidiques de camptothécine |
WO2022170971A1 (fr) * | 2021-02-09 | 2022-08-18 | 苏州宜联生物医药有限公司 | Conjugué à substance bioactive, son procédé de préparation et son utilisation |
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