HRP20211467T1 - Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji - Google Patents
Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji Download PDFInfo
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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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- 150000001875 compounds Chemical class 0.000 title claims 16
- 238000002595 magnetic resonance imaging Methods 0.000 title claims 4
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 title claims 2
- 229910052688 Gadolinium Inorganic materials 0.000 title 1
- 239000013522 chelant Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 claims 10
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- -1 {2-[4,7,10-tris(carboxylato-methyl)-1,4,7,10-tetraazacyclododecan-1-yl]propanoyl}amino Chemical group 0.000 claims 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000002872 contrast media Substances 0.000 claims 1
- 239000000032 diagnostic agent Substances 0.000 claims 1
- 229940039227 diagnostic agent Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
Classifications
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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)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Radiology & Medical Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (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.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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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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HRP20211467T1 true HRP20211467T1 (hr) | 2021-12-24 |
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HRP20211467TT HRP20211467T1 (hr) | 2015-06-04 | 2016-05-30 | Novi spojevi gadolinijevih kelata za uporabu u magnetskoj rezonanciji |
HRP20191631 HRP20191631T1 (hr) | 2015-06-04 | 2019-09-11 | Novi spojevi gadolinij kelata za uporabu kod snimanja magnetskom rezonancom |
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EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
KR102464647B1 (ko) * | 2016-11-28 | 2022-11-08 | 바이엘 파마 악티엔게젤샤프트 | 자기 공명 영상화에 사용하기 위한 높은 이완도 가돌리늄 킬레이트 화합물 |
BR112021007707A2 (pt) * | 2018-11-23 | 2021-07-27 | Bayer Aktiengesellschaft | formulação de meios de contraste e processo de preparação da mesma |
CN110396122B (zh) * | 2019-08-13 | 2020-10-27 | 牡丹江医学院 | 一种核磁共振造影剂、制备方法及其用于肿瘤诊断中的用途 |
KR102386595B1 (ko) * | 2019-10-29 | 2022-04-14 | 경북대학교 산학협력단 | 신규한 가돌리늄계 화합물, 이의 제조 방법, 및 이를 함유하는 mri 조영제 |
CN111393544A (zh) * | 2020-03-02 | 2020-07-10 | 合肥工业大学 | 一种具有靶向核磁共振造影和荧光成像功能的聚合物、制备方法及应用 |
CN114181233B (zh) * | 2021-11-24 | 2023-10-31 | 复旦大学 | 一种钆基T1磁共振造影剂FD-Gd-123及其制备方法和应用 |
CN114276309B (zh) * | 2021-12-24 | 2023-08-11 | 南京科技职业学院 | 一类含乙氧基芳环的钆磁共振造影剂及其制备方法与应用 |
WO2024046833A1 (de) | 2022-08-30 | 2024-03-07 | Bayer Aktiengesellschaft | Erzeugen von synthetischen radiologischen aufnahmen |
WO2024046831A1 (de) | 2022-08-30 | 2024-03-07 | Bayer Aktiengesellschaft | Erzeugen von synthetischen radiologischen aufnahmen |
WO2024046832A1 (de) | 2022-08-30 | 2024-03-07 | Bayer Aktiengesellschaft | Erzeugen von synthetischen radiologischen aufnahmen |
WO2024052156A1 (de) | 2022-09-05 | 2024-03-14 | Bayer Aktiengesellschaft | Erzeugen von künstlichen kontrastverstärkten radiologischen aufnahmen |
EP4335461A1 (en) | 2022-09-09 | 2024-03-13 | Bayer AG | Combinations of contrast agents |
WO2024063529A1 (ko) * | 2022-09-20 | 2024-03-28 | 주식회사 테라노큐어 | 신규 화합물 및 이를 포함하는 염증성 질환과 암에 대한 진단 및 치료에 사용되는 mri 조영제 |
WO2024083466A1 (de) | 2022-10-17 | 2024-04-25 | Bayer Aktiengesellschaft | Automatisches analysieren von radiologischen aufnahmen |
EP4360660A1 (en) | 2022-10-24 | 2024-05-01 | Bayer AG | Process for the preparation of a gadolinium contrast agent |
EP4369353A1 (de) | 2022-11-12 | 2024-05-15 | Bayer Aktiengesellschaft | Erzeugung von künstlichen kontrastmittelverstärkten radiologischen aufnahmen |
EP4369285A1 (de) | 2022-11-12 | 2024-05-15 | Bayer AG | Erzeugung von künstlichen kontrastmittelverstärkten radiologischen aufnahmen |
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HUE056114T2 (hu) | 2016-12-12 | 2022-01-28 | Bracco Imaging Spa | Dimer kontrasztanyagok |
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