AU2018205019C1 - Inhibitors of transglutaminases - Google Patents

Inhibitors of transglutaminases Download PDF

Info

Publication number
AU2018205019C1
AU2018205019C1 AU2018205019A AU2018205019A AU2018205019C1 AU 2018205019 C1 AU2018205019 C1 AU 2018205019C1 AU 2018205019 A AU2018205019 A AU 2018205019A AU 2018205019 A AU2018205019 A AU 2018205019A AU 2018205019 C1 AU2018205019 C1 AU 2018205019C1
Authority
AU
Australia
Prior art keywords
methyl
cyclo
oxo
oxoethyl
dihydropyridin
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
AU2018205019A
Other languages
English (en)
Other versions
AU2018205019A1 (en
AU2018205019B2 (en
Inventor
Christian Büchold
Martin Hils
Ralf Pasternack
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.)
Zedira GmbH
Original Assignee
Zedira GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zedira GmbH filed Critical Zedira GmbH
Publication of AU2018205019A1 publication Critical patent/AU2018205019A1/en
Application granted granted Critical
Publication of AU2018205019B2 publication Critical patent/AU2018205019B2/en
Publication of AU2018205019C1 publication Critical patent/AU2018205019C1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07K5/1024—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
    • 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
    • A61K47/54—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
    • A61K47/548—Phosphates or phosphonates, e.g. bone-seeking
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • 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
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • 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
    • C07K5/0819—Tripeptides with the first amino acid being acidic
    • 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
    • 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
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1013—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing O or S as heteroatoms, e.g. Cys, Ser
    • 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
    • C07K5/1021—Tetrapeptides with the first amino acid being acidic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biochemistry (AREA)
  • Veterinary Medicine (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Enzymes And Modification Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
AU2018205019A 2016-12-27 2018-01-02 Inhibitors of transglutaminases Active AU2018205019C1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
EP16207029.6 2016-12-27
EP16207029.6A EP3342779A1 (en) 2016-12-27 2016-12-27 Inhibitors of transglutaminases
US201762499528P 2017-01-30 2017-01-30
US62/499,528 2017-01-30
PCT/EP2018/050085 WO2018122419A1 (en) 2016-12-27 2018-01-02 Inhibitors of transglutaminases

Publications (3)

Publication Number Publication Date
AU2018205019A1 AU2018205019A1 (en) 2019-05-30
AU2018205019B2 AU2018205019B2 (en) 2021-09-16
AU2018205019C1 true AU2018205019C1 (en) 2022-03-03

Family

ID=57777445

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2018205019A Active AU2018205019C1 (en) 2016-12-27 2018-01-02 Inhibitors of transglutaminases

Country Status (8)

Country Link
US (1) US11072634B2 (enExample)
EP (2) EP3342779A1 (enExample)
JP (1) JP7648339B2 (enExample)
CN (1) CN110088120A (enExample)
AU (1) AU2018205019C1 (enExample)
CA (1) CA3044487A1 (enExample)
ES (1) ES2949273T3 (enExample)
WO (1) WO2018122419A1 (enExample)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL3464336T3 (pl) 2016-06-01 2022-05-16 Athira Pharma, Inc. Związki
WO2019201432A1 (en) * 2018-04-17 2019-10-24 Zedira Gmbh Inhibitors of blood coagulation factor xiii
TWI825144B (zh) 2018-08-10 2023-12-11 美商思達利醫藥公司 第二型轉麩醯胺酸酶(tg2)抑制劑
WO2022022612A1 (en) * 2020-07-29 2022-02-03 Jacobio Pharmaceuticals Co., Ltd. Novel glutamine analogs
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds
WO2023110138A1 (en) * 2021-12-17 2023-06-22 Zedira Gmbh Inhibitors of transglutaminases
CN117561241B (zh) 2021-06-30 2025-10-28 策迪拉有限公司 转谷氨酰胺酶的抑制剂
HUE069300T2 (hu) 2021-06-30 2025-02-28 Zedira Gmbh Transzglutaminázok inhibitorai
AU2022303109A1 (en) * 2021-06-30 2023-12-14 Zedira Gmbh Inhibitors of transglutaminases
WO2025153465A1 (en) 2024-01-15 2025-07-24 UCB Biopharma SRL Method for the treatment of fibrotic-related disorder associated to ibd

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008144933A1 (en) * 2007-05-29 2008-12-04 Université de Montréal Cinnamoyl inhibitors of transglutaminase
US20110229568A1 (en) * 2006-11-08 2011-09-22 Kai Oertel Michael systems as transglutaminase inhibitors

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10054687A1 (de) * 2000-11-03 2002-05-16 N Zyme Biotec Gmbh Inhibitoren von Transglutaminasen
WO2006018164A2 (de) 2004-08-11 2006-02-23 N-Zyme Biotec Gmbh Fluoreszenzbasierende kinetische bestimmung der aktivität von transglutaminasen
EP2885400A1 (en) * 2012-08-17 2015-06-24 Celexion, LLC Biological synthesis of difunctional hexanes and pentanes from carbohydrate feedstocks

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110229568A1 (en) * 2006-11-08 2011-09-22 Kai Oertel Michael systems as transglutaminase inhibitors
WO2008144933A1 (en) * 2007-05-29 2008-12-04 Université de Montréal Cinnamoyl inhibitors of transglutaminase

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
COX, R. J. et al., "Synthesis and in vitro enzyme activity of peptide derivatives of bacterial cell wall biosynthesis inhibitors", J. Chem. Soc., Perkin Trans. 1, 2000, vol. 1, no. 13, pages 2023-2036 *
SIEGEL, M. et al., "Structure-based design of [alpha]-amido aldehyde containing gluten peptide analogues as modulators of HLA-DQ2 and transglutaminase 2", Bioorg. Med. Chem., 2007, vol. 15, no. 18, pages 6253-6261 *

Also Published As

Publication number Publication date
EP3405477C0 (en) 2023-06-07
EP3405477A1 (en) 2018-11-28
JP7648339B2 (ja) 2025-03-18
US20190322700A1 (en) 2019-10-24
JP2020514283A (ja) 2020-05-21
ES2949273T3 (es) 2023-09-27
EP3342779A1 (en) 2018-07-04
WO2018122419A1 (en) 2018-07-05
CN110088120A (zh) 2019-08-02
CA3044487A1 (en) 2018-07-05
AU2018205019A1 (en) 2019-05-30
US11072634B2 (en) 2021-07-27
EP3405477B1 (en) 2023-06-07
AU2018205019B2 (en) 2021-09-16

Similar Documents

Publication Publication Date Title
AU2018205019C1 (en) Inhibitors of transglutaminases
US12497460B2 (en) Anti-MSR1 antibodies and methods of use thereof
JP4312718B2 (ja) Ｃ型肝炎ウイルス阻害剤
KR102362277B1 (ko) 면역조절제로서 1,2,4-옥사디아졸 유도체
EA005740B1 (ru) Карбаматные ингибиторы каспазы и их использование
JPH11503455A (ja) トロンビン阻害剤
BRPI0617751A2 (pt) compostos de ligação do domìnio iap bir
JP2002521386A (ja) ウロキナーゼおよび血管形成のインヒビター
US20160031935A1 (en) Small molecule modulators of pcsk9 and methods of use thereof
SK63498A3 (en) Novel macrocyclic compounds as metalloprotease inhibitors
CA2387002A1 (en) Non-covalent inhibitors of urokinase and blood vessel formation
JPH08503217A (ja) 血小板糖タンパク質▲ＩＩ▼ｂ／▲ＩＩＩ▼ａの阻害剤として有用な複素環式環により結合された環状化合物
JPH02300199A (ja) レトロウイルスプロテアーゼ阻害剤
KR20060129069A (ko) 카스파제 억제제 및 이의 용도
JP2021512867A (ja) Ｉｒａｋ阻害剤としてのキノリン化合物及びその使用
AU6655798A (en) Beta-sheet mimetics and methods relating to the use thereof
US11203602B2 (en) Thioester prodrugs of macrocycles as inhibitors of histone deacetylases
KR20020062312A (ko) １,３,４-옥사디아졸린 유도체 및 이들을 유효 성분으로하는 약제
JP2024097099A (ja) Ｍｍｐ７阻害作用を有するペプチドコンジュゲート
JP2879280B2 (ja) ２−ピペラジノン誘導体およびその用途
JP3125212B2 (ja) ２−ピペラジノン誘導体およびその用途
AU9583998A (en) Thrombin inhibitors
RU2172321C2 (ru) Ингибиторы сериновых протеаз
JPH11503450A (ja) Ｃ−末端アミネルジックな側鎖アミノ酸残基を含む血小板凝集抑制物質

Legal Events

Date Code Title Description
DA2 Applications for amendment section 104

Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 22 NOV 2021

DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 22 NOV 2021

FGA Letters patent sealed or granted (standard patent)