KR102204781B1 - 혈전 용해, 항혈전 및 라디칼 소거능의 3가지 활성을 갖는 신규한 화합물, 및 이의 합성, 나노-구조 및 용도 - Google Patents

혈전 용해, 항혈전 및 라디칼 소거능의 3가지 활성을 갖는 신규한 화합물, 및 이의 합성, 나노-구조 및 용도 Download PDF

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KR102204781B1
KR102204781B1 KR1020157035673A KR20157035673A KR102204781B1 KR 102204781 B1 KR102204781 B1 KR 102204781B1 KR 1020157035673 A KR1020157035673 A KR 1020157035673A KR 20157035673 A KR20157035673 A KR 20157035673A KR 102204781 B1 KR102204781 B1 KR 102204781B1
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ala
pro
compound
lys
boc
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시치 펭
밍 쟈오
지안후이 우
유지 왕
치치 펭
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상하이 루모사 테라퓨틱스 여우시안공시
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
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    • A61K38/06—Tripeptides
    • 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
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    • 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
    • A61K47/54—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 organic compound
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    • 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
    • A61K47/54—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 organic compound
    • A61K47/55—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 organic compound the modifying agent being also a pharmacologically or therapeutically active agent, i.e. the entire conjugate being a codrug
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0215—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing natural amino acids, forming a peptide bond via their side chain functional group, e.g. epsilon-Lys, gamma-Glu
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • C07K5/06165—Dipeptides with the first amino acid being heterocyclic and Pro-amino acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1019—Tetrapeptides with the first amino acid being basic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Chemical & Material Sciences (AREA)
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  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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  • Veterinary Medicine (AREA)
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  • Molecular Biology (AREA)
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  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
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  • Hematology (AREA)
  • Diabetes (AREA)
  • Urology & Nephrology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
KR1020157035673A 2013-06-05 2014-06-03 혈전 용해, 항혈전 및 라디칼 소거능의 3가지 활성을 갖는 신규한 화합물, 및 이의 합성, 나노-구조 및 용도 Active KR102204781B1 (ko)

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CN201310225330 2013-06-05
CN201310225330.6 2013-06-05
PCT/CN2014/079098 WO2014194809A1 (zh) 2013-06-05 2014-06-03 具有溶栓、抗栓和自由基清除三重活性的新型化合物、其合成、纳米结构和应用

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KR102204781B1 true KR102204781B1 (ko) 2021-01-20

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CN (1) CN104231046B (https=)
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Families Citing this family (7)

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Publication number Priority date Publication date Assignee Title
CN106608905B (zh) * 2015-10-22 2020-10-16 彭莉 四氢异喹啉-3-甲酰-k(grpak)rgdv,其合成,活性及应用
CN106608902A (zh) * 2015-10-22 2017-05-03 彭莉 二羟基二甲基四氢异喹啉-3-甲酰-Lys(Lys),其合成,活性及应用
JP6663774B2 (ja) 2016-03-30 2020-03-13 東京エレクトロン株式会社 基板搬送方法及び基板処理システム
PT4034115T (pt) * 2019-09-25 2025-03-25 Lumosa Therapeutics Co Ltd Composição farmacêutica compreendendo conjugado péptido trombolítico-tetra-hidroisoquinolina
EP4149563A1 (en) * 2020-05-15 2023-03-22 Synhelix Peptidic scaffolds, processes for manufacturing the same, and uses thereof as soluble supports
JP2024510653A (ja) * 2021-03-22 2024-03-08 ルモサ セラピューティクス カンパニー， リミテッド 急性虚血性脳卒中を治療するｄｃ００９
CN115403653B (zh) * 2022-05-19 2024-08-06 首都医科大学 D(+)-β-(3,4-二羟基苯基)-乳酰-Pro-Ala-Lys,其合成及应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101190941A (zh) 2006-11-30 2008-06-04 首都医科大学 具有溶血栓活性的多肽、其制备方法及应用
CN101497651A (zh) 2008-01-30 2009-08-05 首都医科大学 具有溶血栓活性的化合物、其制备方法、其应用

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5222632B2 (https=) * 1972-08-22 1977-06-18
WO2002059117A1 (en) 2001-01-23 2002-08-01 Eli Lilly And Company Piperazine- and piperidine-derivatives as melanocortin receptor agonists
WO2003061660A1 (en) 2002-01-23 2003-07-31 Eli Lilly And Company Melanocortin receptor agonists
EP1578786A2 (en) * 2002-12-23 2005-09-28 Janssen Pharmaceutica N.V. Heteroaryl peptidomimetics as thrombin receptor antagonists
CN101190895B (zh) 2006-11-30 2010-05-26 首都医科大学 N-[(3s)-1,2,3,4-四氢异喹啉-3-甲酰基]氨基酸、其制备方法及应用
CN101200493B (zh) 2006-12-11 2011-11-09 首都医科大学 （3s）-n-（l-氨基酰）-1，2，3，4-四氢异喹啉-3-羧酸、其制备方法及应用
CN102241740B (zh) * 2008-01-30 2014-02-19 首都医科大学 具有溶血栓活性的化合物、其制备方法、其应用
CN101899084B (zh) 2009-05-26 2012-09-05 首都医科大学 (3s)-1,2,3,4-四氢异喹啉-3-羧酸三肽缀合物及其制备方法和应用
CN102120727B (zh) 2010-01-07 2013-08-28 首都医科大学 N-[(3s)-n-氨基酰-1,2,3,4-四氢异喹啉-3-甲酰基]氨基酸及其合成方法和应用
CN102127097A (zh) 2010-01-15 2011-07-20 首都医科大学 N-（3s-1,2,3,4-四氢异喹啉-3-甲酰基）氨基酸铜络合物及其制备方法和应用
CN102477068B (zh) 2010-11-30 2013-07-24 首都医科大学 用于制备溶血栓药物的氨基酸衍生物及其制备方法和应用
KR101937514B1 (ko) * 2011-10-14 2019-01-10 브리스톨-마이어스 스큅 컴퍼니 인자 xia 억제제로서의 치환된 테트라히드로이소퀴놀린 화합물
CN103145797B (zh) 2011-12-07 2015-05-20 首都医科大学 [(3s)-1,2,3,4-四氢异喹啉-3-甲酰基]-Lys修饰的RGD四肽,其合成和在医学中的应用
CN103450338B (zh) 2012-05-29 2016-08-24 首都医科大学 杂环羧酸修饰的胸腺五肽，其制备，抗肿瘤作用和应用
CN103450330B (zh) * 2012-06-01 2016-05-25 首都医科大学 二羟基四氢异喹啉-3-甲酰氨基酸、其合成、抗血栓作用和应用
CN103665107B (zh) * 2012-09-05 2017-07-14 上海晟顺生物科技有限公司 同时具溶血栓、清除自由基和血栓靶向功能的新颖化合物及其制备方法和用途
CN102887941A (zh) * 2012-09-05 2013-01-23 永光制药有限公司 Pak/咪唑啉/rgd三元缀合物及其制备方法和用途

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101190941A (zh) 2006-11-30 2008-06-04 首都医科大学 具有溶血栓活性的多肽、其制备方法及应用
CN101497651A (zh) 2008-01-30 2009-08-05 首都医科大学 具有溶血栓活性的化合物、其制备方法、其应用

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EP3006454A1 (en) 2016-04-13
US20230312644A1 (en) 2023-10-05
US10351594B2 (en) 2019-07-16
US20180134748A1 (en) 2018-05-17
HUE053351T2 (hu) 2021-06-28
HRP20210566T1 (hr) 2021-06-25
ZA201507237B (en) 2019-11-27
CA2914004A1 (en) 2014-12-11
PH12015502684B1 (en) 2019-07-03
EP3006454A4 (en) 2016-11-30
LT3006454T (lt) 2021-04-12
US20200055895A1 (en) 2020-02-20
WO2014194809A1 (zh) 2014-12-11
PH12015502684A1 (en) 2016-03-07
US20210355163A1 (en) 2021-11-18
TWI633889B (zh) 2018-09-01
BR112015027164B1 (pt) 2023-03-21
CN104231046B (zh) 2017-05-03
PL3006454T3 (pl) 2021-06-28
MX2015015924A (es) 2016-04-06
KR20160016863A (ko) 2016-02-15
CA2914004C (en) 2022-01-25
TW201521759A (zh) 2015-06-16
MX362902B (es) 2019-02-22
US20160083423A1 (en) 2016-03-24
RU2660901C2 (ru) 2018-07-11
RU2015147247A (ru) 2017-05-05
JP2016521696A (ja) 2016-07-25
BR112015027164A2 (pt) 2017-07-25
CN104231046A (zh) 2014-12-24
RS61606B1 (sr) 2021-04-29
US9890193B2 (en) 2018-02-13
AU2014277416A1 (en) 2015-12-24
SI3006454T1 (sl) 2021-04-30
AU2014277416B2 (en) 2018-02-22
JP6510500B2 (ja) 2019-05-08
PT3006454T (pt) 2021-01-29
CY1123976T1 (el) 2022-05-27
EP3006454B1 (en) 2021-01-13
SMT202100108T1 (it) 2021-03-15
ES2847934T3 (es) 2021-08-04

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