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HRP20211467T1 - Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji - Google Patents

Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji Download PDF

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HRP20211467T1
HRP20211467T1 HRP20211467TT HRP20211467T HRP20211467T1 HR P20211467 T1 HRP20211467 T1 HR P20211467T1 HR P20211467T T HRP20211467T T HR P20211467TT HR P20211467 T HRP20211467 T HR P20211467T HR P20211467 T1 HRP20211467 T1 HR P20211467T1
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carboxylatomethyl
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Markus Berger
Jessica LOHRKE
Christoph-Stephan Hilger
Gregor Jost
Thomas Fenzel
Detlev Suelzle
Johannes Platzek
Olaf Panknin
Hubertus Pietsch
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Bayer Pharma Aktiengesellschaft
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
    • A61K49/103—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being acyclic, e.g. DTPA
    • A61K49/105—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being acyclic, e.g. DTPA the metal complex being Gd-DTPA
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
    • A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/08—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier
    • A61K49/10—Organic compounds
    • A61K49/101—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals
    • A61K49/106—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA
    • A61K49/108—Organic compounds the carrier being a complex-forming compound able to form MRI-active complexes with paramagnetic metals the complex-forming compound being cyclic, e.g. DOTA the metal complex being Gd-DOTA
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C07C229/16—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Animal Behavior & Ethology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Magnetic Resonance Imaging Apparatus (AREA)

Claims (13)

1. Spoj opće formule (I), koji sadrži 4, 5 ili 6 skupina gadolinija [4,7,10-tris-(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il], u kojima: [image] predstavlja skupinu odabranu od: [image] [image] u kojoj skupine a i b predstavljaju cijeli broj 1; i , u kojoj skupine * označava točku vezanja navedene skupine sa R1; R1 predstavlja, međusobno neovisno, vodikov atom ili skupinu odabranu od: R3 [image] u kojoj skupine * označava točku vezanja navedene skupine sa A, pod uvjetom da samo jedan od supstituenata R1 može predstavljati vodikov atom; n predstavlja cijeli broj 3 ili 4; R2 predstavlja vodikov atom; R3 predstavlja skupinu odabranu od: [image] u kojoj skupine * označava točku vezanja navedene skupine s ostatkom molekule; R4 predstavlja vodikov atom; R5 predstavlja metilnu skupinu; ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
2. Spoj prema patentnom zahtjevu 1, naznačen time što: [image] predstavlja skupinu odabranu od: [image] [image] u kojoj skupine a i b predstavljaju cijeli broj 1; i, u kojoj skupine * označava točku vezanja navedene skupine sa R1; R1 predstavlja, međusobno neovisno, vodikov atom ili skupinu odabranu od: R3 [image] u kojoj skupine * označava točku vezanja navedene skupine sa A , pod uvjetom da samo jedan od supstituenata R1 može predstavljati vodikov atom; n predstavlja cijeli broj 3 ili 4; R2 predstavlja vodikov atom; R3 predstavlja skupinu odabranu od: [image] u kojoj skupine * označava točku vezanja navedene skupine s ostatkom molekule; R4 predstavlja vodikov atom; R5 predstavlja metilnu skupinu; ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
3. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time što: [image] predstavlja skupinu [image] , u kojoj skupini * označava točku vezanja navedene skupine sa R1, ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
4. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time što: [image] predstavlja skupinu [image] , u kojoj skupini * označava točku vezanja navedene skupine sa R1, ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
5. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time što: [image] predstavlja skupinu [image] , u kojoj skupini * označava točku vezanja navedene skupine sa R1, ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
6. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time što: [image] predstavlja skupinu [image] , u kojoj skupini * označava točku vezanja navedene skupine sa R1, ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
7. Spoj prema patentnim zahtjevima 1 ili 2, naznačen time što: [image] predstavlja skupinu [image] , u kojoj skupini * označava točku vezanja navedene skupine sa R1, ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
8. Spoj prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time što je odabran iz skupine koju čine: Pentagadolinijev [4,10-bis(karboksilatometil)-7-{3,6,10,18,22,25-heksaokso-26-[4,7,10-tris-(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il]-14-[({2-[4,7,10-tris(karboksilato-metil)-1,4,7,10-tetraazaciklododekan-1-il]propanoil}amino)acetil]-9,19-bis({[({2-[4,7,10-tris(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il]propanoil}amino)acetil]amino}-metil)-4,7,11,14,17,21,24-heptaazaheptakozan-2-il}-1,4,7,10-tetraazaciklododekan-1-il]-acetat, Heksagadolinijev [4,10-bis(karboksilatometil)-7-{3,6,10,15,19,22-heksaokso-23-[4,7,10-tris-(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il]-9,16-bis({[({12-[4,7,10-tris-(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il]propanoil}amino)acetil]amino}-metil)-11-(2-{[3-{[({2-[4,7,10-tris(karboksilatometil)-1,4,7,10-tetraazaciklododekan-1-il]-propanoil}amino)acetil]amino}-2-({[({2-[4,7,10-tris(karboksilatometil)-1,4,7,10-tetraaza-ciklododekan-1-il]propanoil}amino)acetil]amino}metil)propanoil]amino}etil)-4,7,11,14,18,21-heksaazatetrakozan-2-il}-1,4,7,10-tetraazaciklododekan-1-il]acetat , Pentagadolinijev [4-(1-{[2-(bis{2-[({1,4-bis[({2-[4,7,10-tris(karboksilatometil)-1,4,7,10-tetra-azaciklododekan-1-il]propanoil}amino)acetil]-1,4-diazepan-6-il}karbonil)amino]etil}-amino)-2-oksoetil]amino}-1-oksopropan-2-il)-7,10-bis(karboksilatometil)-1,4,7,10-tetra-azaciklododekan-1-il]acetat, Heksagadolinijev 2,2'2'',2''',2'''',2''''',2'''''',2'''''',2'''''''',2''''''''',2'''''''''',2''''''''''',2'''''''''''',2''''''''''''',2'''''''''''''', 2''''''''''''''',2'''''''''''''''',2'''''''''''''''''-{etan-1,2-diilkarbamoil-1,4-diazepan-6,1,4-triiltris[(2-okso-etan-2,1-diil)imino(l-oksopropan-1,2-diil)-1,4,7,10-tetraazaciklododekan-10,1,4,7-tetrail]}oktadekaacetat , Heksagadolinijev 2,2'2'',2''',2'''',2''''',2'''''',2''''''',2'''''''',2''''''''',2'''''''''',2''''''''''',2'''''''''''',2''''''''''''',2'''''''''''''', 2''''''''''''''',2'''''''''''''''',2'''''''''''''''''-(1,4,7-triazonan-1,4,7-triiltris{karbonil-1,4-diazepan-6,1,4-triil-bis[(2-oksoetan-2,1-diil)imino(1-oksopropan-1,2-diil)-1,4,7,10-tetraazaciklododekan-10,1,4,7-tetrail]})oktadekaacetat , Tetragadolinijev2,2',2'',2''',2'''',2''''',2'''''',2''''''',2'''''''',2''''''''',2'''''''''',2'''''''''''-{1,4,7,10-tetraazaciklo-dodekan-1,4,7,10-tetrailtetrakis[(2-oksoetan-2,1-diil)imino(1-oksopropan-1,2-diil)-1,4,7,10-tetraazaciklododekan-10,1,4,7-tetrail]}dodekaacetat, Heksagadolinijev 2,2'2'',2''',2'''',2''''',2'''''',2''''''',2'''''''',2''''''''',2'''''''''',2''''''''''',2'''''''''''',2''''''''''''',2'''''''''''''', 2''''''''''''''',2'''''''''''''''',2'''''''''''''''''-{3,7,10-triazatriciklo[3.3.3.01,5]undekan-3,7,10-triiltris[karbonil-(3,6,11,14-tetraokso-4,7,10,13-tetraazaheksadekan-8,2,15-triil)di-1,4,7,10-tetraazaciklodo-dekan-10,1,4,7-tetrail]}oktadekaacetat , i Tetragadolinijev 2,2',2'',2''',2'''',2''''',2'''''',2''''''',2'''''''',2''''''''',2'''''''''',2'''''''''''-(3,7,9-triazabiciklo-[3.3.1]nonan-3,7-diilbis{karbonil-1,4-diazepan-6,1,4-triilbis[(2-oksoetan-2,1-diil)-1,4,7,10-tetraazaciklododekan-10,1,4,7-tetrail]})dodekaacetat , ili stereoizomer, tautomer, N-oksid, hidrat, solvat, ili njihova sol, ili njihova smjesa.
9. Spojevi prema bilo kojem od patentnih zahtjeva 1 do 8 za uporabu u magnetskoj rezonanciji (MRI).
10. Uporaba spojeva ili njihovih smjesa prema bilo kojem od patentnih zahtjeva 1 do 8, naznačena time što je za proizvodnju dijagnostičkih sredstava.
11. Uporaba spojeva ili njihovih smjesa prema bilo kojem od patentnih zahtjeva 1 do 8, za proizvodnju kontrastnih sredstava za snimanje magnetskom rezonancijom.
12. Postupak snimanja tjelesnog tkiva kod pacijenta, naznačen time što se sastoji od koraka davanja pacijentu učinkovite količine jednog ili više spojeva prema bilo kojem od zahtjeva 1 do 8 u farmaceutski prihvatljivom nosaču, te podvrgavanje pacijenta snimanju magnetskom rezonancijom.
13. Uporaba spoja opće formule (III): [image] u kojoj je R5 kao što je definiran za spojeve opće formule (I) prema bilo kojem od zahtjeva 1 do 8, i LG predstavlja aktivirajuću izlaznu skupinu, kao što je na primjer 4-nitrofenol za pripravu spoja opće formule (I) prema bilo kojem od zahtjeva 1 do 8.
HRP20211467TT 2015-06-04 2016-05-30 Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji HRP20211467T1 (hr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP15170658.7A EP3101012A1 (en) 2015-06-04 2015-06-04 New gadolinium chelate compounds for use in magnetic resonance imaging
EP19194723.3A EP3611169B1 (en) 2015-06-04 2016-05-30 New gadolinium chelate compounds for use in magnetic resonance imaging

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HRP20191631 HRP20191631T1 (hr) 2015-06-04 2016-05-30 Novi spojevi gadolinij kelata za uporabu kod snimanja magnetskom rezonancom
HRP20211467TT HRP20211467T1 (hr) 2015-06-04 2016-05-30 Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji

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US (5) US10137209B2 (hr)
EP (3) EP3101012A1 (hr)
JP (1) JP6703012B2 (hr)
KR (1) KR102162742B1 (hr)
CN (1) CN107667096B (hr)
AR (1) AR104897A1 (hr)
AU (1) AU2016272602B2 (hr)
CA (1) CA2987993C (hr)
CL (1) CL2017003083A1 (hr)
CO (1) CO2017012490A2 (hr)
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CY (2) CY1122323T1 (hr)
DK (2) DK3303307T3 (hr)
DO (1) DOP2017000282A (hr)
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HR (2) HRP20191631T1 (hr)
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IL (1) IL255945B (hr)
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LT (2) LT3611169T (hr)
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PT (2) PT3611169T (hr)
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UA (1) UA123313C2 (hr)
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EP4369353A1 (de) 2022-11-12 2024-05-15 Bayer Aktiengesellschaft Erzeugung von künstlichen kontrastmittelverstärkten radiologischen aufnahmen
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