HRP20230261T1 - Peptidi za ciljanje mitohondrija - Google Patents

Peptidi za ciljanje mitohondrija Download PDF

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HRP20230261T1
HRP20230261T1 HRP20230261TT HRP20230261T HRP20230261T1 HR P20230261 T1 HRP20230261 T1 HR P20230261T1 HR P20230261T T HRP20230261T T HR P20230261TT HR P20230261 T HRP20230261 T HR P20230261T HR P20230261 T1 HRP20230261 T1 HR P20230261T1
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dmt
oxadiazole
arg
image
diaminopent
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HRP20230261TT
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Guozhu ZHENG
Mark J. BAMBERGER
Inese Smukste
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Stealth Biotherapeutics Inc.
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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
    • C07K5/021—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)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
    • 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
    • A61K38/07—Tetrapeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • 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
    • C07K5/1016—Tetrapeptides with the first amino acid being neutral and aromatic or cycloaliphatic

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
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  • Proteomics, Peptides & Aminoacids (AREA)
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  • Crystallography & Structural Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Epidemiology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (17)

1. Spoj s formulom (I): [image] naznačen time što AA1 je odabran od [image] , i [image] AA2 je odabran od [image] R1 je odabran od [image] [image] [image] R2a je odabran od [image] [image] R2b je H ili Me; R3 i R4 su neovisno odabrani od H i (C1-C6)alkila; R5 i R6 su neovisno H, metil, etil, propil, ciklopropil, ili ciklobutil; ili R5 i R6 zajedno s atomom N na koji su oni vezani tvore 4-6-člani heterociklil; R7 je odabran od H, (C1-C6)alkila, cikloalkila, i arila; R8 i R9 su neovisno odabrani od H, (C1-C6)alkila, cikloalkila, i arila; ili R8 i R9 zajedno s atomom N na koji su oni vezani tvore 4-6-člani heterociklil; n je 1, 2, ili 3; X je odabran od [image] [image] i * označava točku spajanja X na R1.
2. Spoj prema zahtjevu 1, naznačen time što R1 je odabran od [image] [image] ili je odabran od [image] [image] ili je odabran od [image] ili je odabran od [image] ili pri čemu R1 je [image]
3. Spoj prema zahtjevu 1 ili zahtjevu 2, naznačen time što je R2a odabran od [image] po izboru pri čemu R8 i R9 su neovisno odabrani od H i metila; ili pri čemu R8 i R9 zajedno s atomom N na koji su oni vezani tvore 4-6-člani heterociklil; po izboru pri čemu heterociklil je azetidinil, pirolidinil, ili piperidinil.
4. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što je R2a odabran od [image] [image] i [image]
5. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što je AA2 odabran od [image] [image] po izboru pri čemu je R7 odabran od H, metila, etila, izopropila, ili n-propila.
6. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što je AA1 odabran od [image] ili AA1 je odabran od [image]
7. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što R2b je H ili Me.
8. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što R5 je H ili Me.
9. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što R6 je H ili Me.
10. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time što R5 i R6 zajedno s atomom N na koji su oni vezani tvore 4-6-člani heterociklil; po izboru pri čemu heterociklil je azetidinil, pirolidinil, ili piperidinil.
11. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što je X odabran od [image] ili [image] ili X je odabran od [image] ili X je [image] ili X je odabran od [image] ili X je odabran od [image]
12. Spoj prema bilo kojem prethodnom zahtjevu, naznačen time što su R3 i R4 odabrani od H i (C1-C6)alkila; po izboru pri čemu R3 i R4 su neovisno metil, ili etil; dalje po izboru pri čemu R3 i R4 su metil ili pri čemu R3 i R4 su etil.
13. Spoj prema zahtjevu 1, naznačen time što je spoj odabran iz niza koji sadrži D-Arg-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((R)-1', 5'-diaminopent-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-2',6'-diaminoheks-2'-il)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-5'-dimetilamino-1'-aminopent-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((R)-1',5'-diaminopent-1'-il)-3-(2',3',4',5',6'-pentafluorobenzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-(4-tert-butilbenzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((R)-1',5'-diaminopent-1'-il)-3-(4-tert-butilbenzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-(4'-trifluorometilbenzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-(4-fenilbenzil))-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-(4'-cikloheksilbenzil))-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-fenetil))-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-cikloheptilmathil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-biciklo [2,2,2]pentanilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1', 5'-diaminopent-1'-il)-3-biciklo[2,2,2]oktanilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((1S)-(5-(1',5'-diaminopent-1'-il-3-adamant-1'-il)-1,2,4-oksadiazol; D-Arg-DMT-(5-((1R)-(5-(1',5'-diaminopent-1'-il-3-adamant-1'-il)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-admantilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-fenil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-fenetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-ciklopentilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-t-metilhistamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-p-metilhistamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-cikloheptilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-biciklo[2,2,2]pentanilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-biciklo[2,2,2]oktanilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-admantil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-(S)-histamin)-3-admantilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((S)-(2-(1H-indol-3-il)-1-aminoetil)-3-benzil)-1,2,4-oksadiazol; D-Arg-DMT-(5-((1S)-2-(piridin-4-il)-1-aminoetil-3-admantilmetil)-1,2,4-oksadiazol; D-Agb-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Agb-DMT-(5-((S)-1',4'-diaminobut-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Agb-DMT-(5-((S)-4'-dimetilamino-1'-aminobut-1'-il)-3-benzil)-1,2,4-oksadiazol; D-Agb-DMT-(5-(2'-(S)-4-histamin)-3-admantilmetil)-1,2,4-oksadiazol; (N,N-diMe)-D-Agb-DMT-(5-(2'-(S)-4-histamin)-3-admantil)-1,2,4-oksadiazol; D-Agb-DMT-(5-((S)-(2-(1H-indol-3-il)-1-aminoetil)-3-benzil)-1,2,4-oksadiazol; D-Agb-DMT-(5-((S)-(2-(1H-indol-3-il)-1-aminoetil)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-1',4'-diaminopropan-1'-il)-3-benzil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-1',4'-diaminobut-1'-il)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-1',4'-diaminobut-1'-il)-3-admantil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-1',4'-diaminobut-1'-il)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((R)-1',4'-diaminobut-1'-il)-3-admantilmetil)-1,2,4-oksadiazol; D-(6-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((R)-1',4'-diaminobut-1'-il)-3-(biciklo[2.2.2]oktanilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5 -((S)-4'-dimetilamino-1'-aminobut-1'-il)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((S)-5'-dimetilamino-1'-aminopent-1'-il)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(6-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-benzil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-(4-fenilbenzil))-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-ciklopentilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-cikloheptilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-t-metilhistamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-cikloheksilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-histamin)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-(α-(S)-t-metilhistamin)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((1S)-(2-(1H-indol-3-il)-1-aminoetil)-3-(4-fenilbenzil))-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((1S)-(2-(1-metil-indol-3-il)-1-aminoetil)-3-(4-fenilbenzil))-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((1S)-(2-(1H-indol-3-il)etil)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((1S)-(2-(6-fluoro-1H-indol-3-il)etil)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-DMT-(5-((1S)-(2-(1-metil-indol-3-il)-1-aminoetil)-3-admantilmetil)-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-(O-Me)-DMT-(5-(α-histimin)-3-(4-fenilbenzil))-1,2,4-oksadiazol; D-(δ-2-amino-1H-imidazol-1-il)-Nva-(O-Me)-DMT-(5-(α-(S)-t-metilhistamin)-3-(4-fenilbenzil))-1,2,4-oksadiazol (Karbamimidoil)-D-Dab-DMT-(5-((S)-1',5'-diaminopent-1'-il)-3-benzil)-1,2,4-oksadiazol; (Karbamimidoil)-D-Dab-DMT-(5-((S)-1',5'-diaminobutan-1'-il)-3-benzil)-1,2,4-oksadiazol; (Karbamimidoil)-D-Dab-DMT-(5-(2'-(S)-4-histamin)-3-admantilmetil)-1,2,4-oksadiazol; D-Arg-DMT-(5-(α-histimin))-3-benzil)-1,3,4-oksadiazol; D-Arg-DMT-(2-((S)-1', 5'-diaminopent-1'-il)-4-benzil)-1,3-oksazol; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-5-benzil)-1,3-oksazol; D-Arg-DMT-(2-((S)-1', 5'-diaminopent-1'-il)-4-benzil)-1,3-tiazol; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-5-benzil)-1,3-tiazol; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-4-benzil)-furan; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-5-benzil)-furan; D-Arg-DMT-(1-((S)-1', 5'-diaminopent-1'-il)-3-fenoksi)-benzen; D-Arg-DMT-(1-((S)-1', 5'-diaminopent-1'-il)-4-fenoksi)-benzen; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-4-fenoksi)-piridin; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-5-fenoksi)-piridin; D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-6-benzil)-piridin; i D-Arg-DMT-(2-((S)-1',5'-diaminopent-1'-il)-4-benzil)-pirimidin.
14. Spoj prema zahtjevu 1, naznačen time što spoj ima sljedeću strukturu: [image] ili njegova farmaceutski prihvatljiva sol.
15. Spoj prema bilo kojem prethodnom zahtjevu za uporabu u liječenju ili prevenciji ishemijsko-reperfuzijske ozljede; po izboru pri čemu je ishemijsko-reperfuzijska ozljeda srčana ishemijsko-reperfuzijska ozljeda; i/ili za uporabu u liječenju ili prevenciji infarkta miokarda; i/ili za uporabu u liječenju ili prevenciji ishemije stražnjih udova ili kritične ishemije udova.
16. Spoj za uporabu prema zahtjevu 15, naznačen time što se spoj primjenjuje oralno, lokalno, sistemski, intravenski, potkožno, intraperitonealno ili intramuskularno.
17. Farmaceutski pripravak, naznačen time što sadrži spoj prema bilo kojem od zahtjeva 1 do 14, te farmaceutski prihvatljiv nosač.
HRP20230261TT 2017-12-15 2018-12-14 Peptidi za ciljanje mitohondrija HRP20230261T1 (hr)

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US201762599175P 2017-12-15 2017-12-15
EP18888579.2A EP3723783B1 (en) 2017-12-15 2018-12-14 Mitochondria-targeting peptides
PCT/US2018/065755 WO2019118878A1 (en) 2017-12-15 2018-12-14 Mitochondria-targeting peptides

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KR20220078644A (ko) 2019-10-04 2022-06-10 스텔스 바이오테라퓨틱스 인코포레이티드 미토콘드리아 질환 치료를 위한 바티퀴논의 퀴논-, 히드로퀴논- 및 나프토퀴논-유사체
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US20230227499A1 (en) * 2020-06-22 2023-07-20 Stealth Biotherapeutics Inc. Prodrugs of mitochondria-targeting oligopeptides
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