HRP20221451T1 - Dimerna kontrastna sredstva - Google Patents
Dimerna kontrastna sredstva Download PDFInfo
- Publication number
- HRP20221451T1 HRP20221451T1 HRP20221451TT HRP20221451T HRP20221451T1 HR P20221451 T1 HRP20221451 T1 HR P20221451T1 HR P20221451T T HRP20221451T T HR P20221451TT HR P20221451 T HRP20221451 T HR P20221451T HR P20221451 T1 HRP20221451 T1 HR P20221451T1
- Authority
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- Croatia
- Prior art keywords
- compound according
- formula
- image
- groups
- alkyl chain
- Prior art date
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- 239000002872 contrast media Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- 229920005862 polyol Polymers 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 3
- -1 pentyl polyols Chemical class 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 229910021645 metal ion Inorganic materials 0.000 claims 2
- 230000005298 paramagnetic effect Effects 0.000 claims 2
- 150000003077 polyols Chemical class 0.000 claims 2
- CUGDYSSBTWBKII-LXGUWJNJSA-N (2r,3r,4r,5s)-6-(dimethylamino)hexane-1,2,3,4,5-pentol Chemical compound CN(C)C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO CUGDYSSBTWBKII-LXGUWJNJSA-N 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000002616 MRI contrast agent Substances 0.000 claims 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001342 alkaline earth metals Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 150000002678 macrocyclic compounds Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229960003104 ornithine Drugs 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
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- 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
- 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
-
- 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
- A61K49/12—Macromolecular 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
- A61K49/12—Macromolecular compounds
- A61K49/122—Macromolecular compounds dimers of complexes or complex-forming compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Radiology & Medical Imaging (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Claims (17)
1. Spoj s formulom (I)
[image]
gdje:
R je -CH(R1)-COOH, gdje:
R1 je H ili lanac C1-C3 alkil koji je po izboru supstituiran sa C1-C3 alkoksi skupinom ili C1-C3 hidroksialkoksi skupinom;
n je 1 ili 2;
R2 je odabran iz skupine koju čine: C1-C5 alkil supstituiran s jednom ili više C1-C8 hidroksialkoksi skupina, i C5-C12 hidroksialkil koji sadrži najmanje 2 hidroksilne skupine;
i
L je C1-C6 alkilen, po izboru prekinut s jednom ili više -N(R'2)- skupina, i po izboru supstituiranih s jednom ili više supstituentnih skupina odabranih od hidroksila, C1-C3 alkoksi i C1-C3 hidroksialkoksi, gdje
R'2 je, neovisno, kako je definirano za R2
kao i pojedinačni dijastereoizomeri i njihove racemične smjese, geometrijski izomeri i njihovi otopljeni enantiomeri, te njihova fiziološki prihvatljiva sol.
2. Spoj prema patentnom zahtjevu 1 naznačen time što R1 je H.
3. Spoj prema patentnim zahtjevima 1 ili 2 naznačen time što L je C1-C6 alkilen, koji ima slijedeću formulu (II)
[image]
u kojoj:
m je 1, 2, 3, 4, 5, ili 6; i
n i R2 su kako je definirano u patentnom zahtjevu 1.
4. Spoj prema patentnom zahtjevu 3 naznačen time što, u formuli (II), R2 je C5-C12 poliol.
5. Spoj prema patentnom zahtjevu 4 naznačen time što je poliol odabran iz skupine koju čine pentil-polioli koji sadrže od 2 do 4 hidroksilne skupine na C5 alkilnom lancu; heksil-polioli koji sadrže od 2 do 5 hidroksilnih skupina na C6 alkilnom lancu; i heptil-polioli koji sadrže od 3 do 6 hidroksilnih skupina na C7 alkilnom lancu.
6. Spoj prema patentnom zahtjevu 4 ili 5 naznačen time što poliol je odabran od pentil-tetraola s formulom
[image]
i heksil-pentaola s formulom
[image]
7. Spoj prema patentnom zahtjevu 3 naznačen time što, u formuli (II), R2 je C1-C5 alkil supstituiran s jednom ili dvije C1-C8 hidroksialkoksi skupine
8. Spoj prema patentnom zahtjevu 7 naznačen time što R2 je C2-C16 hidroksialkoksi-alkilen odabran iz skupina formule -CH2(OCH2CH2)sOCH2OH, -CH2(CH2OCH2)rCH2OH i -(CH2)r-O(CH2)rOH, gdje r je, neovisno, 1 ili 2, i s je 0, 1 ili 2.
9. Spoj prema patentnim zahtjevima 1 ili 2 naznačen time što u formuli (I), L je C1-C6 alkilenski lanac prekinut s jednom ili dvije -N(R'2)- skupine, koji ima formulu (III)
[image]
u kojoj:
svaki n, r i d je, neovisno, 1 ili 2; i
R2 i R'2, jednaki ili različiti, su kako je definirano u patentnom zahtjevu 1.
10. Spoj prema patentnim zahtjevima 9 naznačen time što:
d je 1; i
R'2 = R2,
koji ima formulu
[image]
11. Spoj prema patentnom zahtjevu 1 ili 2 s formulom:
[image]
[image]
12. Kelatirani kompleks spoja prema bilo kojem od patentnih zahtjeva 1- sa dva paramagnetska metalna iona odabrana iz skupine koja sadrži Fe2+, Fe3+, Cu2+, Cr3+, Gd3+, Eu3+, Dy3+, La3+, Yb3+ ili Mn2+, ili njegova fiziološki prihvatljiva sol.
13. Kelatirani kompleks prema patentnom zahtjevu 12, naznačen time što su paramagnetski metalni ioni Gd3+ ioni.
14. Spoj prema bilo kojem od patentnih zahtjeva 1-11 naznačen time što fiziološki prihvatljiva sol je s kationom (i) anorganske baze odabrane od alkalijskog ili zemno alkalijskog metala, (ii) organske baze odabrane od etanolamina, dietanolamina, morfolina, glukamina, N N-metilglukamina, N,N-dimetilglukamina ili (iii) aminokiselinom odabranom od lizina, arginina i ornitina.
15. Kelatirani kompleks kako je definiran u bilo kojem od patentnih zahtjeva 12-13 naznačen time što je za upotrebu kao MRI kontrastno sredstvo.
16. Farmaceutski pripravak naznačen time što sadrži kelatirani kompleks prema patentnim zahtjevima 12-13 u kombinaciji s jednim ili više farmaceutski prihvatljivih nosača, razrjeđivača ili pomoćnih sredstava.
17. Spoj prema bilo kojem od patentnih zahtjeva 1-11 naznačen time što je svaka od karboksilnih skupina R vezana na atome dušika u makrociklu u zaštićenom obliku kao tert-butil ester.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15199220 | 2015-12-10 | ||
| EP20187182.9A EP3753929B1 (en) | 2015-12-10 | 2016-12-12 | Dimeric contrast agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20221451T1 true HRP20221451T1 (hr) | 2023-02-17 |
Family
ID=55027251
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20221451TT HRP20221451T1 (hr) | 2015-12-10 | 2016-12-12 | Dimerna kontrastna sredstva |
| HRP20210061TT HRP20210061T1 (hr) | 2015-12-10 | 2021-01-13 | Dimerna kontrastna sredstva |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210061TT HRP20210061T1 (hr) | 2015-12-10 | 2021-01-13 | Dimerna kontrastna sredstva |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US10407412B2 (hr) |
| EP (2) | EP3753929B1 (hr) |
| JP (1) | JP6896733B2 (hr) |
| KR (1) | KR102703336B1 (hr) |
| CN (1) | CN108368067B (hr) |
| AU (1) | AU2016368545C1 (hr) |
| BR (1) | BR112018010815B1 (hr) |
| CA (1) | CA3002897C (hr) |
| DK (2) | DK3753929T3 (hr) |
| ES (2) | ES2843998T3 (hr) |
| FI (1) | FI3753929T3 (hr) |
| HR (2) | HRP20221451T1 (hr) |
| HU (2) | HUE060536T2 (hr) |
| IL (1) | IL259836B (hr) |
| LT (1) | LT3386954T (hr) |
| MX (1) | MX2018007043A (hr) |
| PL (2) | PL3753929T3 (hr) |
| PT (1) | PT3386954T (hr) |
| RU (1) | RU2739834C2 (hr) |
| SG (1) | SG11201804412SA (hr) |
| SI (2) | SI3753929T1 (hr) |
| WO (1) | WO2017098044A1 (hr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3101012A1 (en) | 2015-06-04 | 2016-12-07 | Bayer Pharma Aktiengesellschaft | New gadolinium chelate compounds for use in magnetic resonance imaging |
| SI3753929T1 (sl) * | 2015-12-10 | 2023-01-31 | Bracco Imaging Spa | Dimerna kontrastna sredstva |
| CN110035996B (zh) | 2016-11-28 | 2022-08-09 | 拜耳医药股份公司 | 用于磁共振成像的新型高弛豫性钆螯合物 |
| WO2018108780A1 (en) * | 2016-12-12 | 2018-06-21 | Bracco Imaging Spa | Dimeric contrast agents |
| KR20210095168A (ko) | 2018-11-23 | 2021-07-30 | 바이엘 악티엔게젤샤프트 | 조영 매체의 제형 및 그의 제조 방법 |
| AU2020399182A1 (en) | 2019-12-13 | 2022-06-09 | Bracco Imaging Spa | Manufacturing of protected DO3A |
| US20230303592A1 (en) | 2020-07-27 | 2023-09-28 | Bracco Imaging S.P.A. | Manufacturing of dimeric contrast agents |
| KR20230116805A (ko) * | 2020-12-04 | 2023-08-04 | 브라코 이미징 에스.피.에이. | 가도테리돌 제조를 위한 제조 방법 |
| AU2022317221A1 (en) * | 2021-07-27 | 2023-11-16 | Bracco Imaging Spa | Manufacturing of dimeric contrast agents |
| KR20240038926A (ko) | 2021-07-27 | 2024-03-26 | 브라코 이미징 에스.피.에이. | 가돌리늄 착물 용액의 제조 과정 |
| WO2023110863A1 (en) | 2021-12-14 | 2023-06-22 | Bracco Imaging Spa | Process for manufacturing a mixture comprising a dimeric macrocycle intermediate of a gadolinium complex |
| EP4448499A1 (en) | 2021-12-14 | 2024-10-23 | Bracco Imaging SPA | Manufacturing of dimeric contrast agent |
| WO2024074648A1 (en) | 2022-10-07 | 2024-04-11 | Bracco Imaging Spa | Precipitation and isolation of gadolinium complex |
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| US4647447A (en) | 1981-07-24 | 1987-03-03 | Schering Aktiengesellschaft | Diagnostic media |
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| IT1213029B (it) | 1986-01-30 | 1989-12-07 | Bracco Ind Chimica Spa | Chelati di ioni metallici paramagnetici. |
| DE3625417C2 (de) * | 1986-07-28 | 1998-10-08 | Schering Ag | Tetraazacyclododecan-Derivate |
| US5132409A (en) | 1987-01-12 | 1992-07-21 | Bracco Industria Chimica S.P.A. | Macrocyclic chelating agents and chelates thereof |
| GB9320277D0 (en) * | 1993-10-01 | 1993-11-17 | Nycomed Salutar Inc | Chelants |
| DE4009119A1 (de) | 1990-03-19 | 1991-09-26 | Schering Ag | 1,4,7,10-tetraazacyclododecan-butyltriole, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
| DE4035760A1 (de) | 1990-11-08 | 1992-05-14 | Schering Ag | Mono-n-substituierte 1,4,7,10-tetraazacyclododecan-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mittel |
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| DE4318369C1 (de) * | 1993-05-28 | 1995-02-09 | Schering Ag | Verwendung von makrocyclischen Metallkomplexen als Temperatursonden |
| GB9318550D0 (en) * | 1993-09-07 | 1993-10-20 | Nycomed Salutar Inc | Chelants |
| IT1291624B1 (it) | 1997-04-18 | 1999-01-11 | Bracco Spa | Chelati complessi di metalli paramagnetici a bassa tossicita' |
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| IT1292128B1 (it) | 1997-06-11 | 1999-01-25 | Bracco Spa | Processo per la preparazione di chelanti macrociclici e loro chelati con ioni metallici paramagnetici |
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