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HRP20191482T1 - 18f-označeni psma ciljani pet reagensi - Google Patents

18f-označeni psma ciljani pet reagensi Download PDF

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Publication number
HRP20191482T1
HRP20191482T1 HRP20191482T HRP20191482T1 HR P20191482 T1 HRP20191482 T1 HR P20191482T1 HR P20191482 T HRP20191482 T HR P20191482T HR P20191482 T1 HRP20191482 T1 HR P20191482T1
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HR
Croatia
Prior art keywords
group
formula
nitrobenzyl
benzyl
compound according
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English (en)
Inventor
Clifford Berkman
Svetlana A Stekhova
Original Assignee
Cancer Targeted Tech Llc
Univ Washington State
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Application filed by Cancer Targeted Tech Llc, Univ Washington State filed Critical Cancer Targeted Tech Llc
Publication of HRP20191482T1 publication Critical patent/HRP20191482T1/hr

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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/0489Phosphates or phosphonates, e.g. bone-seeking phosphonates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
    • A61K51/04Organic compounds
    • A61K51/0402Organic compounds carboxylic acid carriers, fatty acids
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/22Amides of acids of phosphorus
    • C07F9/24Esteramides
    • C07F9/2404Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/22Amides of acids of phosphorus
    • C07F9/24Esteramides
    • C07F9/2404Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2416Esteramides the ester moiety containing a substituent or a structure which is considered as characteristic of cycloaliphatic alcohols
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/06Phosphorus compounds without P—C bonds
    • C07F9/22Amides of acids of phosphorus
    • C07F9/24Esteramides
    • C07F9/2454Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07FACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02Phosphorus compounds
    • C07F9/547Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576Six-membered rings
    • C07F9/58Pyridine rings

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Optics & Photonics (AREA)
  • Physics & Mathematics (AREA)
  • Biophysics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Claims (15)

1. Spoj formule (I): ili njegova farmaceutski prihvatljiva sol, pri čemu je L veznik formule -NH-CH2CH2-(OCH2CH2-)y-C(O)- ili skupine formula pri čemu je u čemu y je 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12; m je 1, 2, 3 ili 4; svaki nje neovisno 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12; R1 je fenil ili piridil; pri čemu je fenil ili piridil supstituiran sa [F] - ili [18F] -fluoro skupinom i opcijski supstituirana s drugom skupinom koja je odabrana od halogena, cijano i nitro; svaki R2 je nezavisno vodik ili C1-C6 alkil; i svaki R je neovisno vodik ili zaštitna skupina odabrana iz skupine koja sadrži alkil, alkenil, haloalkil, benzil, trifenilmetil (trtil), difenilmetil, o-nitrobenzil, 2,4,6-trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4- (metilsulfinil) benzil, 4-sulfobenzil, 4-azidometoksibenzil, i piperonil, poželjno odabran iz skupine koja sadrži metil, etil, propil, izopropil, terc-butil, alil, trifluorometil, trifluoroetil, benzil, trifenilmetil (tritil), difenilmetil, o-nitrobenzil, 2,4,6- trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4- (metilsulfinil) benzil, 4-sulfobenzil, 4-azidometoksibenzil i piperonil; pod uvjetom da kada je L skupina formule m (n+2) je veće ili jednako 3 i manje ili jednako 21.
2. Spoj u skladu s patentnim zahtjevom 1, pri čemu je spoj formule (Ic); ili njegova farmaceutski prihvatljiva sol.
3. Spoj u skladu s patentnim zahtjevom 1 ili 2, pri čemu je svaki R vodik.
4. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-3, pri čemu je svaki R2 vodik.
5. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-4, pri čemu je m 1 ili 2.
6. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-5, pri čemu je spoj formule (Id): ili njegova farmaceutski prihvatljiva sol.
7. Spoj u skladu s bilo kojim od patentnih zahtjeva 1-6, pri čemu je R1: pri čemu je X vodik ili klor; i Y je N ili CH.
8. Spoj u skladu s patentnim zahtjevom 7, pri čemu je (i) X vodik i Y CH; (ii) X je vodik i Y je N; (iii) X je klor i Y je N; ili (iv) X je klor i Y je CH.
9. Spoj u skladu s patentnim zahtjevom 1 koji je:
ili njegova farmaceutski prihvatljiva sol.
10. Pripravak koji sadrži spoj bilo kojeg od patentnih zahtjeva 1-9, ili njegovu farmaceutski prihvatljivu sol, zajedno s farmaceutski prihvatljivim nosačem, ekscipijensom i/ili razrjeđivačem.
11. Spoj formule (II): ili njegova farmaceutski prihvatljiva sol, pri čemu je L veznik formule -NH-CH2CH2-(OCH2CH2-)y-C(O)- ili skupine formula pri čemu je y 1,2, 3, 4,5,6, 7, 8, 9, 10, 11 ili 12; m je 1, 2, 3, ili 4; svaki nje neovisno 1,2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12; svaki R2 je neovisno vodik ili C1-C6 alkil; i svaki R je neovisno vodik ili zaštitna skupina izabrana iz skupine koja sadrži alkil, alkenil, haloalkil, benzil, trifenilmetil (tritil), difenilmetil, o-nitrobenzil, 2,4,6-trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4-(metilsulfmil)benzil, 4-sulfobenzil, 4-azidometoksibenzil, i piperonil, preferabilno izabran iz skupine koja sadrži metil, etil, propil, isopropil, tert-butil, alil, trifluorometil, trifluoroetil, benzil, trifenilmetil (tritil), difenilmetil, o-nitrobenzil, 2,4,6-trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4-(metilsulfinil)benzil, 4-sulfobenzil, 4-azidometoksibenzil, i piperonil; pod uvjetom da kada je L skupina formule m (n+2) je veći ili jednak 3 i manji ili jednak 21.
12. Spoj u skladu s patentnim zahtjevom 11 koji je: ili njegova farmaceutski prihvatljiva sol.
13. Spoj formule (III): ili njegova farmaceutski prihvatljiva sol, pri čemu je L veznik formule -NH-CH2CH2-(OCH2CH2-)y-C(O)- ili skupina formule pri čemu je y 1,2, 3, 4,5,6, 7, 8, 9, 10, 11 ili 12; m je 1, 2, 3 ili 4; svaki nje neovisno 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 ili 12; R3 je fenil ili piridil; pri čemu je fenil ili piridil supstituiran odlazećom grupom i opcionalno supstituiran s drugom grupom izabranom između halogena, cijano i nitro; svaki R2 je neovisno vodik ili C1-C6 alkil; i svaki R je neovisno vodik ili zaštitna skupina izabrana iz grupe koja sadrži alkil, alkenil, haloalkil, benzil, trifenilmetil (tritil), difenilmetil, o-nitrobenzil, 2,4,6-trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4-(metilsulfinil)benzil, 4-sulfobenzil, 4-azidometoksibenzil, i piperonil, preferabilno izabran iz skupine koja sadrži metil, etil, propil, izopropil, tert-butil, alil, trifluorometil, trifluoroetil, benzil, trifenilmetil (tritil), difenilmetil, o-nitrobenzil, 2,4,6-trimetilbenzil, p-bromobenzil, p-nitrobenzil, p-metoksibenzil (PMB), 2,6-dimetoksibenzil, 4-(metilsulfinil) benzil, 4-sulfobenzil, 4-azidometoksibenzil i piperonil; pod uvjetom da kada je L skupina formule m (n+2) je veće ili jednako 3 i manje ili jednako 21.
14. Spoj u skladu s patentnim zahtjevom 13, pri čemu je R3 pri čemu R6 je odlazeća skupina.
15. Spoj u skladu s patentnim zahtjevima 13 ili 14, pri čemu su odlazeća skupina nitro, trimetilstanil, benzotriazol-1-iloksi, halogen, C1-C10alkilsulfonat, C1-C10haloalkilsulfonat, nonaflat, fenilsulfonat pri čemu je fenil opcionalno supstituiran s 1,2 ili 3 skupine koje su svaka neovisno halogene ili C1-C4 alkil ili sol amonijaka formule -[N(Rx)(Ry)(Rz)]+[X]-, pri čemu su Rx, Ry, and Rz neovisno vodik ili alkil i X je konjugirana baza jake kiseline, preferabilno je odlazeća skupina halogen ili trialkilamonijak.
HRP20191482 2013-03-15 2014-03-14 18f-označeni psma ciljani pet reagensi HRP20191482T1 (hr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361798108P 2013-03-15 2013-03-15
PCT/US2014/027820 WO2014143736A1 (en) 2013-03-15 2014-03-14 18f-labeled psma-targeted pet imaging agents
EP14721640.2A EP2970345B1 (en) 2013-03-15 2014-03-14 18f-labeled psma-targeted pet imaging agents

Publications (1)

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HRP20191482T1 true HRP20191482T1 (hr) 2019-11-15

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HRP20230109TT HRP20230109T1 (hr) 2013-03-15 2014-03-14 Postupci pripreme 18f-obilježenih psma-usmjerenih sredstava za pet snimanje i dijagnostički postupci sa njima
HRP20191482 HRP20191482T1 (hr) 2013-03-15 2014-03-14 18f-označeni psma ciljani pet reagensi

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Country Status (17)

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US (2) US11554183B2 (hr)
EP (3) EP3560937B1 (hr)
CN (2) CN108558939B (hr)
AU (2) AU2014228233B2 (hr)
CA (1) CA2903131C (hr)
DK (2) DK2970345T3 (hr)
ES (2) ES2743433T3 (hr)
FI (1) FI3560937T3 (hr)
HR (2) HRP20230109T1 (hr)
HU (2) HUE046194T2 (hr)
LT (2) LT3560937T (hr)
PL (2) PL2970345T3 (hr)
PT (2) PT3560937T (hr)
RS (1) RS64011B1 (hr)
SI (2) SI3560937T1 (hr)
SM (1) SMT202300035T1 (hr)
WO (1) WO2014143736A1 (hr)

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US11078166B2 (en) 2015-08-13 2021-08-03 The Johns Hopkins University Triazole conjugated ureas, thioureas, carbamates, and reversed carbamates for PSMA-targeted imaging agents and uses thereof
MX392700B (es) * 2016-08-10 2025-03-11 Cancer Targeted Tech Llc Inhibidores de antígeno de la membrana específico para la próstata (psma) quelados.
CN110418604B (zh) 2017-03-22 2023-04-18 赛佛欧普手术有限公司 用于检测电生理诱发电位变化的医疗系统和方法
WO2018233798A1 (en) 2017-06-20 2018-12-27 ITM Isotopen Technologien München AG NOVEL PSMA BINDING AGENTS AND USE THEREOF
KR20200009091A (ko) 2017-05-24 2020-01-29 아이티엠 이소토펜 테크놀로지엔 뮌헨 아게 신규 psma-결합제 및 이의 용도
WO2020108753A1 (en) 2018-11-28 2020-06-04 ITM Isotopen Technologien München AG Novel tumor antigen binding agents and uses thereof
WO2020224780A1 (en) 2019-05-08 2020-11-12 ITM Isotopen Technologien München AG Para-aminohippuric acid (pah) as a renal protective substance
WO2021046233A1 (en) 2019-09-03 2021-03-11 Cancer Targeted Technology Llc Chelate-containing psma inhibitors
WO2022096103A1 (en) 2020-11-05 2022-05-12 ITM Isotopen Technologien München AG Combination of para-aminohippuric acid (pah) and radiolabeled complexes for treating cancer
WO2022111800A1 (en) 2020-11-25 2022-06-02 Itm Solucin Gmbh Stable formulations for radionuclide complexes
JP2024514293A (ja) 2021-04-02 2024-04-01 ノバルティス アーゲー 前立腺がんの診断方法
WO2025038752A1 (en) 2023-08-14 2025-02-20 Cancer Targeted Technology Llc Psma binding ligand-linker conjugates and methods for use thereof

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US7696185B2 (en) * 2006-03-14 2010-04-13 Cancer Targered Technology LLC Peptidomimetic inhibitors of PSMA, compounds comprising them, and methods of use
BRPI0716554A2 (pt) * 2006-09-08 2013-09-24 Bayer Schering Pharma Ag compostos de mÉtodos para agentes rotulados de 18f
RU2494096C2 (ru) * 2008-08-01 2013-09-27 Дзе Джонс Хопкинс Юниверсити Агенты, связывающиеся с psma, и их применение
US9328129B2 (en) * 2010-11-12 2016-05-03 Washington State University Peptidomimetic inhibitors of PSMA
CN107325127B (zh) * 2011-06-15 2020-09-01 癌靶技术有限责任公司 螯合的psma抑制剂
CN102757296B (zh) * 2012-04-10 2014-11-19 中国科学院上海应用物理研究所 一种对化合物进行[18f]标记的方法
WO2013173630A1 (en) * 2012-05-16 2013-11-21 Cancer Targeted Technology, Llc Formulation of radiopharmaceuticals containing multiple acidic groups
WO2013173583A1 (en) * 2012-05-16 2013-11-21 Cancer Targeted Technology, Llc Psma inhibitors

Also Published As

Publication number Publication date
AU2014228233B2 (en) 2019-02-28
US20230144322A1 (en) 2023-05-11
ES2743433T3 (es) 2020-02-19
DK2970345T3 (da) 2019-08-26
SI3560937T1 (sl) 2023-04-28
HRP20230109T1 (hr) 2023-04-28
ES2937955T3 (es) 2023-04-03
AU2019203610A1 (en) 2019-06-13
FI3560937T3 (fi) 2023-02-28
EP4180438A1 (en) 2023-05-17
AU2019203610B2 (en) 2021-02-04
PL3560937T3 (pl) 2023-03-27
HUE061402T2 (hu) 2023-06-28
SMT202300035T1 (it) 2023-05-12
PT2970345T (pt) 2019-09-06
RS64011B1 (sr) 2023-03-31
LT3560937T (lt) 2023-03-27
US20160030605A1 (en) 2016-02-04
PL2970345T3 (pl) 2019-12-31
US11554183B2 (en) 2023-01-17
EP3560937B1 (en) 2022-12-28
EP3560937A1 (en) 2019-10-30
HUE046194T2 (hu) 2020-02-28
AU2014228233A1 (en) 2015-09-17
CA2903131A1 (en) 2014-09-18
CN105308056A (zh) 2016-02-03
DK3560937T3 (da) 2023-02-13
SI2970345T1 (sl) 2019-11-29
EP2970345B1 (en) 2019-06-19
LT2970345T (lt) 2019-09-25
EP2970345A1 (en) 2016-01-20
PT3560937T (pt) 2023-02-13
CN108558939A (zh) 2018-09-21
CN108558939B (zh) 2021-08-24
CA2903131C (en) 2021-11-23
CN105308056B (zh) 2018-03-20
WO2014143736A1 (en) 2014-09-18

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