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WO2008095366A1 - Dérivés de porphyrine, leurs méthodes de préparation et leurs utilisations comme molécule antioxydante de petite taille - Google Patents

Dérivés de porphyrine, leurs méthodes de préparation et leurs utilisations comme molécule antioxydante de petite taille Download PDF

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Publication number
WO2008095366A1
WO2008095366A1 PCT/CN2007/002970 CN2007002970W WO2008095366A1 WO 2008095366 A1 WO2008095366 A1 WO 2008095366A1 CN 2007002970 W CN2007002970 W CN 2007002970W WO 2008095366 A1 WO2008095366 A1 WO 2008095366A1
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WO
WIPO (PCT)
Prior art keywords
porphyrin
porphyrin derivative
derivative according
acid
producing
Prior art date
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Ceased
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PCT/CN2007/002970
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English (en)
Chinese (zh)
Inventor
Xianchang Gong
Taiyou Hu
Changzhi Dong
Tianshun Guo
Caiyan Song
Zhiping Deng
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
JINAN SAIWEN PHARMTECHNOLOGY Inc
Original Assignee
JINAN SAIWEN PHARMTECHNOLOGY Inc
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Publication of WO2008095366A1 publication Critical patent/WO2008095366A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors

Definitions

  • the invention relates to a substituted porphyrin derivative, a preparation method thereof and application thereof as a small molecule antioxidant, in particular to a porphyrin derivative, a preparation method thereof and a small molecule antioxidant for regulating human cell or intracellular peroxidation Application in terms of concentration.
  • Peroxide is a product of normal physiological metabolism in the human body. Peroxides present in and between human cells include o 2 _, oir, ONcxr and 3 ⁇ 4o 2 . Since peroxides have high chemical activity, they can react with substances that make up human cells, such as cell membranes and chromosomes, leading to disease.
  • Oxygen is active and can participate in important metabolic processes that play an important role in sustaining life. But oxygen can also cause damage to living things. In the body, oxygen is converted into a variety of peroxides that can damage deoxynucleotides, proteins, and phospholipids. The accumulation of these reactions can impair the function of the cells and even cause disease. Studies have shown that peroxides in cerebral thrombosis, chronic bronchitis, asthma, rheumatoid arthritis, cancer, Alzheimer's disease, Parkinson's disease, shock caused by septicemia, diabetes, due to human exposure to radiotherapy It plays a role in various diseases such as sequelae, AIDS, aging and heart failure.
  • Free radicals are a class of high energy labile compounds containing unpaired electrons. Harmful peroxides in the human body include 0 2 _, OH -, ONOO- and 3 ⁇ 40 2 . Such peroxides are produced by physiological reactions in the body, such as the process of re-oxygenation and radiotherapy. ONOCT is the product of the action of 0 2 _ and NO_. Radon is a free radical that is often produced during the course of radiotherapy. This free radical is the most active free radical in chemistry. It reacts with chemicals in the body and causes a chain reaction. It can even react with groups on deoxynucleotides to disrupt the inheritance and replication of cells. The toxic effects of radiotherapy on the human body may begin with the production of free radicals.
  • Re-oxygenation of damaged tissue produces a large amount of peroxygen free radicals.
  • All of the above three anti-free radical enzymes are high molecular substances having a molecular weight of 10,000 or more, which are present in human cells or between human cells, but cannot pass through the cell membrane.
  • the amount of free radicals in the human body is low, these naturally occurring enzymes can effectively decompose these free radicals, thereby protecting the human body.
  • the free radical content in the human body is high, these naturally occurring enzymes can only effectively decompose part of the free radicals. The remaining free radicals that cannot be decomposed can cause greater damage to the human body.
  • Naturally occurring anti-free radical enzymes in the human body can catalyze the following reactions:
  • Antioxidant enzymes play an important role in protecting the body against free radicals.
  • the enzyme itself is a polymer which has a short half-life in the blood circulation and is inaccessible to the cells, which is costly, which limits its feasibility as a drug.
  • Another method is to add a small molecule antioxidant (catalyst) that is catalytically decomposed as soon as the peroxide is formed.
  • a small molecule catalyst catalytically decomposed as soon as the peroxide is formed.
  • An object of the present invention is to provide a porphyrin derivative which has good water solubility, thereby increasing the utility of using porphyrin as a medicament.
  • Another object of the present invention is to provide a process for producing a porphyrin derivative which is simple, high in yield and suitable for mass production.
  • a further object of the present invention is to provide a porphyrin derivative as a small molecule antioxidant for regulating the concentration of intercellular peroxide or intracellular peroxide in human cells.
  • the porphyrin derivative protects the human body from peroxy radicals and other peroxides derived from peroxy radicals, and is used to prevent and treat diseases caused by the presence of harmful peroxides.
  • M is one of the metal ions of the following metals: Fe, Mn , Co, Ni, Cu, Zn, Sn, Cr, Pd, Pt, V.
  • R is preferably -CH 3 or -CH 2 C3 ⁇ 4OC3 ⁇ 4, and M is preferably Fe(III) or ⁇ ( ⁇ ).
  • the present invention includes hydrochlorides, sulfates, acetates, phosphates and other salts which can be used medically as the metalloporphyrin derivatives of the formula I.
  • the different metals of the metalloporphyrin derivatives of the invention have different properties.
  • a complex of a porphyrin with iron or manganese is preferred.
  • the metalloporphyrin derivative of the present invention can be used as a small molecule antioxidant to achieve the purpose of treating diseases by reducing the content of 0 2 -radical, Off radical, ⁇ - and 3 ⁇ 40 2 in human cells or tissues.
  • the metalloporphyrin derivative of the invention can be used for reducing or preventing damage to the human brain due to the formation of cerebral thrombosis, thereby achieving the purpose of treating cerebral thrombosis.
  • the invention is equally applicable to the treatment of chronic bronchitis, asthma, rheumatoid arthritis, cancer, Alzheimer's disease, Parkinson's disease, shock caused by septicemia, diabetes, sequelae caused by radiotherapy of the human body, AIDS, Dry age-related macular degeneration, aging and heart failure diseases.
  • the metalloporphyrin derivative of the invention is capable of catalyzing the decomposition of harmful peroxides in the human body and And can penetrate the cell membrane into the human body cells.
  • the synthesis method of the metalloporphyrin derivative of the present invention is as follows:
  • MX is a metal salt
  • the preparation method of the porphyrin derivative of the invention comprises the following steps: firstly reacting benzaldehyde having a meta substituent with pyrrole under a catalytic action of an organic acid at a certain temperature for 1 hour to 3 days, after distilling off the acid, remaining The product is isolated and purified to obtain a porphyrin.
  • the molar ratio of benzaldehyde to pyrrole is 1:0.5-2
  • the organic acid herein is a monobasic acid such as acetic acid, propionic acid, butyric acid, isobutyric acid, trifluoroacetic acid, trichloroacetic acid or the like, preferably propionic acid.
  • the reaction temperature can be from room temperature to reflux depending on the acid.
  • porphyrin and the metal salt are heated and reacted in a polar solvent for 1 to 24 hours, and after distilling off the solvent, the residue is separated and purified to obtain a porphyrin derivative (i.e., a metal-porphyrin complex).
  • a porphyrin derivative i.e., a metal-porphyrin complex.
  • the molar ratio of porphyrin to metal salt is 1:1-10; the metal salt is any salt of any form of Fe, Mn, Co, M, Cu, Zn, Sn, Cr, Pt, V described above, preferably hydrochloride.
  • the solvent can be selected from hydrazine, hydrazine dimethylformamide, methanol, ethanol, acetonitrile, 1,4-dioxane, dimethyl sulfoxide, etc.; reaction temperature can be 30 ⁇ depending on the reactants. To the reflux temperature.
  • Cerebral thrombosis refers to the blockage of blood flow in the brain. Re-opening the bloodstream after surgery can cause further damage to the brain. This is called damage caused by re-oxygenation. Many scientists believe that at least some of the damage caused by cerebral thrombosis and reoxygenation is caused by free radicals.
  • the porphyrin derivative of the present invention can be used as a small molecule antioxidant for treating cerebral thrombosis, and can reduce brain cell death and re-oxygenation damage caused by cerebral thrombosis, and the dosage is 0.5-100 g / kg body weight.
  • Acute myocardial infarction commonly referred to as heart failure. It is due to the crown of the heart blood supply Caused by blockage of blood flow in the arteries leading to death of heart tissue. Long-term or permanent blood flow is blocked, causing partial myocardial hypoxia, which ultimately leads to the death of cardiomyocytes. If intervened by natural or medical means, blood flow is quickly cleared, and damage caused by infarction may be removed or reduced. However, the recanalization of blood flow can also cause damage to cardiomyocytes and their adjacent tissue cells. This type of injury is called ischemic re-oxygenation damage. Studies have shown that free radicals play an important role in the damage caused by blocked blood flow and the damage caused by ischemic re-oxygenation. Therefore, the porphyrin derivative of the present invention as a small molecule antioxidant can reduce tissue damage and benefit patients suffering from heart failure.
  • the porphyrin derivative of the present invention can be used as a small molecule antioxidant to treat sequelae caused by radiotherapy in the human body and to act as an adjuvant therapy.
  • the porphyrin derivatives of the present invention can also be used as a small molecule antioxidant to treat these diseases.
  • the small molecule antioxidant of the metalloporphyrin derivative of the present invention can be classified into two types, oral and injection.
  • As an oral solution it may be formed into a tablet or a capsule, and the ratio of the active component may be between 0.1 and 80%.
  • As the injection a mixture of polyethylene glycol-400, anhydrous ethanol and water for injection is usually used as a solvent. The amount of the drug used is between 0.01 and 200 mg/kg/day. It is used as a small molecule antioxidant to treat diseases such as cerebral thrombosis and heart failure.
  • Porphyrin hydrochloride 20.5mg Polyethylene glycol-400 (PEG-400) (50%) 1.0ml Anhydrous ethanol (30%) 0.6ml Sodium deoxycholate O.lg Water for injection (20%) 0.4ml iOml / support process:
  • dosing separately take the prescription amount of polyethylene glycol-400 and anhydrous ethanol mixed evenly, add the prescription amount of sodium deoxycholate, stir and dissolve; then add the prescription of the main drug, stir, ultrasonic dissolution, adjust pH, add water for injection to the full amount.
  • the above solution is finely filtered with a 0.22 um-0.45 um microporous membrane, and the liquid is checked for visible foreign matter.
  • Sterilization leak detection steam sterilization at 100 ° C for 30 minutes.
  • Example 16 Main pharmacodynamic study of iron(III)-5,10,15,20-tetrakis[3-(2-methoxyethoxy)phenyl]porphyrin hydrochloride (SW100-7) Test
  • White blood cell dilution 1 ml of glacial acetic acid and 1 ml of gentian violet 1 ml, add distilled water to 100 ml, and mix well.
  • mice Sixty healthy mice were randomly divided into 6 groups, 10 in each group, half male and half female.
  • the first group was normal control group, intraperitoneal injection of normal saline, no irradiation; the second group was irradiated control group, intraperitoneal injection of normal saline and irradiation; the third group was positive control group, intraperitoneal injection of amifostine and irradiation;
  • the fourth group was the high-dose group, intraperitoneal injection of l100/ml SW100-7 and irradiation;
  • the fifth group was the middle dose group, intraperitoneal injection of 0.2mg/ml SW100-7 and irradiation;
  • the sixth group was low dose group , SW100-7 was injected intraperitoneally with O.lmg/ml and given irradiation.
  • mice were weighed (m), and immediately after intraperitoneal injection according to the dose of 0.005 m ml, a whole body irradiation was performed with 60 ⁇ > ⁇ ray, and the absorbed dose rate was 0.175 Gy/min, and the total absorbed dose was 7.20 Gy.
  • the total number of white blood cells was counted on the fourth day after irradiation, and the results are shown in Table 1.
  • Table 1 List of white blood cell counts (unit: unit / liter)
  • SW100-7 has a certain cytoprotective effect. From test data not The dose-response relationship of SW100-7 was found. The number of white blood cells in the male and female mice in the positive control group was lower than that in the irradiated control group, which may be caused by the experimental error.
  • the invention provides a porphyrin derivative, a preparation method thereof and application thereof as a small molecule antioxidant, and the porphyrin derivative of the invention has good water solubility and can treat sequelae caused by human body receiving radiotherapy, To the role of adjuvant therapy; and to protect the body from peroxygen free radicals and other peroxides derived from peroxy radicals by regulating the concentration of intercellular or intracellular peroxides, preventing and treating harmful peroxidation A disease caused by the presence of a substance.
  • the porphyrin derivative can also be used for reducing or preventing damage to the human brain due to the formation of cerebral thrombosis, thereby achieving the purpose of treating cerebral thrombosis.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Diabetes (AREA)
  • Virology (AREA)
  • Hematology (AREA)
  • Biochemistry (AREA)
  • Biomedical Technology (AREA)
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  • Toxicology (AREA)
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  • Endocrinology (AREA)
  • Obesity (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
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  • Psychology (AREA)
  • Communicable Diseases (AREA)
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  • Orthopedic Medicine & Surgery (AREA)
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  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne un dérivé de porphyrine, son sel de qualité pharmaceutique et sa méthode de préparation. Ce dérivé de porphyrine est une M-5, 10, 15, 20-tétra[3-éthylène polyol monométhyle éther-substituée-phényle]porphyrine, dans lequel M désigne un des ions métalliques suivants: Fe, Mn, Co, Ni, Cu, Zn, Sn, Cr, V et Pt. Ce dérivé de porphyrine peut être utilisé comme molécule antioxydante de petite taille pour réguler la concentration de peroxyde entre les cellules du corps humainou dans une cellule, afin de protéger le corps contre les dommages provoqués par les radicaux peroxy ou d'autres peroxydes dérivés du radical peroxy, et également afin de prévenir ou de traiter les maladies dues au peroxyde.
PCT/CN2007/002970 2007-02-02 2007-10-17 Dérivés de porphyrine, leurs méthodes de préparation et leurs utilisations comme molécule antioxydante de petite taille Ceased WO2008095366A1 (fr)

Applications Claiming Priority (2)

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CN200710006441.2 2007-02-02
CNA2007100064412A CN101235036A (zh) 2007-02-02 2007-02-02 一类卟啉衍生物及其作为小分子抗氧化剂的应用

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011034183A1 (fr) * 2009-09-17 2011-03-24 国立大学法人九州大学 Composé porphyrine
JP2020515630A (ja) * 2017-04-04 2020-05-28 バイオミメティックス ジェイブイ，エルエルシー 放射線及び／又は化学療法の曝露に関連付けられる副作用を処置及び／又は防止する為の方法、組成物及びキット
US11344574B2 (en) 2017-09-29 2022-05-31 Duke University Fluoro substituted porphyrin compounds, pharmaceutical compositions comprising the same, and methods of preparing and using the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109912607B (zh) * 2018-12-11 2021-01-22 南华大学 一类卟啉-白杨素复合物及其抗肿瘤活性
CN111607100A (zh) * 2020-06-10 2020-09-01 苏州大学 基于铁基卟啉配体的结晶材料及其制备和应用
CN119700724A (zh) * 2024-12-31 2025-03-28 中国医学科学院生物医学工程研究所 一种用于治疗慢性阻塞性肺病和哮喘的雾化吸入制剂及其制备方法

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WO1995031219A1 (fr) * 1994-05-11 1995-11-23 Schering Aktiengesellschaft Utilisation de composes a base d'un complexe de porphyrine ou d'un complexe de porphyrine etendue comme preparation diagnostique pour la localisation d'un infarctus
EP1279676A1 (fr) * 2001-07-19 2003-01-29 Institut Curie Dérivés de porphyrines pour la thérapie photodynamique
CN1450066A (zh) * 2002-04-08 2003-10-22 巩宪昌 带有大取代基的卟啉衍生物、其制备方法及其作为小分子抗氧化剂的应用

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Publication number Priority date Publication date Assignee Title
WO1995031219A1 (fr) * 1994-05-11 1995-11-23 Schering Aktiengesellschaft Utilisation de composes a base d'un complexe de porphyrine ou d'un complexe de porphyrine etendue comme preparation diagnostique pour la localisation d'un infarctus
EP1279676A1 (fr) * 2001-07-19 2003-01-29 Institut Curie Dérivés de porphyrines pour la thérapie photodynamique
CN1450066A (zh) * 2002-04-08 2003-10-22 巩宪昌 带有大取代基的卟啉衍生物、其制备方法及其作为小分子抗氧化剂的应用

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Title
BANERJEE S. ET AL.: "A novel 186/188Re]-labelled porphyrin for targeted radiotherapy", NUCLEAR MEDICINE COMMUNICATIONS, vol. 22, no. 10, 2001, pages 1101 - 1107 *
SESSLER J.L. ET AL.: "Water soluble sapphyrins: potential fluorescent phosphate anion sensors", ORGANIC & BIOMOLECULAR CHEMISTRY, vol. 1, no. 22, 2003, pages 4113 - 4123 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011034183A1 (fr) * 2009-09-17 2011-03-24 国立大学法人九州大学 Composé porphyrine
JP5745415B2 (ja) * 2009-09-17 2015-07-08 国立大学法人九州大学 ポルフィリン化合物
JP2020515630A (ja) * 2017-04-04 2020-05-28 バイオミメティックス ジェイブイ，エルエルシー 放射線及び／又は化学療法の曝露に関連付けられる副作用を処置及び／又は防止する為の方法、組成物及びキット
EP3606614A4 (fr) * 2017-04-04 2020-10-28 Biomimetix JV LLC Méthodes, compositions et kits pour traiter et/ou prévenir un effet secondaire associé à une exposition à un rayonnement et/ou à une chimiothérapie
US11285162B2 (en) 2017-04-04 2022-03-29 Biomimetix Jv, Llc Methods, compositions, and kits for treating and/or preventing a side effect associated with radiation and/or chemotherapy exposure
JP7333560B2 (ja) 2017-04-04 2023-08-25 バイオミメティックス ジェイブイ，エルエルシー 放射線及び／又は化学療法の曝露に関連付けられる副作用を処置及び／又は防止する剤、組成物及びキット
US12171769B2 (en) 2017-04-04 2024-12-24 Biomimetix Jv, Llc Methods, compositions, and kits for treating and/or preventing a side effect associated with radiation and/or chemotherapy exposure
EP4603096A1 (fr) * 2017-04-04 2025-08-20 Biomimetix JV LLC Méthodes, compositions et kits pour traiter et/ou prévenir un effet secondaire associé à une exposition à un rayonnement et/ou à une chimiothérapie
US11344574B2 (en) 2017-09-29 2022-05-31 Duke University Fluoro substituted porphyrin compounds, pharmaceutical compositions comprising the same, and methods of preparing and using the same

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