AR055200A1 - METALLIC COMPLEXES WITH CONTENT OF PERFLUOR OR RENT PROCEDURES FOR THEIR PREPARATION, AS WELL AS THEIR USE - Google Patents

METALLIC COMPLEXES WITH CONTENT OF PERFLUOR OR RENT PROCEDURES FOR THEIR PREPARATION, AS WELL AS THEIR USE

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Publication number
AR055200A1
AR055200A1 ARP060103021A ARP060103021A AR055200A1 AR 055200 A1 AR055200 A1 AR 055200A1 AR P060103021 A ARP060103021 A AR P060103021A AR P060103021 A ARP060103021 A AR P060103021A AR 055200 A1 AR055200 A1 AR 055200A1
Authority
AR
Argentina
Prior art keywords
groups
general formula
site
optionally
omega
Prior art date
Application number
ARP060103021A
Other languages
Spanish (es)
Inventor
Heiko Schirmer
Hanns-Joachim Weinmann
Johannes Platzek
Ludwig Zorn
Bernd Misselwitz
Joerg Meding
Heribert Schmitt-Willich
Thomas Brumby
Original Assignee
Epix Delaware Inc
Schering Ag
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Epix Delaware Inc, Schering Ag filed Critical Epix Delaware Inc
Publication of AR055200A1 publication Critical patent/AR055200A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
    • 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
    • A61K49/103—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
    • 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
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
    • A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
    • A61K51/02—Preparations 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
    • A61K51/04—Organic compounds
    • A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Organic Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Radiology & Medical Imaging (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Procedimientos para su preparacion y a su uso en el diagnostico por RMN y rayos X, en el radiodiagnostico y la radioterapia, así como en la linfografía MRT. Reivindicacion 1: .Complejos con contenido de perfluoroalquilo con grupo N-alquilo de la formula general 1 en donde R representa un radical mono- u oligosacárido unido a través de 1-OH, que está opcionalmente peralquilado, en este caso Q tiene el significado de un grupo seleccionado de delta-CO-(CH2)nö-e, delta-NH-(CH2)nö-e,delta-(CH2)m- e en donde n'' es un numero entero de 1 y 5, y m es un numero entero de 1 y 6, y en donde delta indica el sitio de union con el ligador L y e indica el sitio de union con el radical R; o R tiene uno de los siguientes significados, entonces Q tiene el significado de un enlace directo: R significa un radical polar seleccionado de los complejos K de las formulas generales (2) a (7'), en donde R1 significa aquí un átomo de hidrogeno o un equivalente de ion metálico de los numeros atomicos 20-29, 31-33, 37-39, 42-44, 49 o 57-83, y los radicales R2, R3, R4, U, U2 y U1 presentan el significado indicado más abajo, o una cadena de carbonos unida a través de -CO-, -NR6- o un enlace directo con el ligador L con 1-30 átomos de C, que puede ser lineal o ramificada, saturada o insaturada, y está eventualmente interrumpida por 1-10 átomos de oxígeno, 1-5 grupos -NHCO, 1-5 grupos -CONH, 1-2 átomos de azufre, 1-5 grupos -NH o 1-2 grupos fenileno, que opcionalmente pueden estar sustituidos con 1-2 grupos OH, 1-2 grupos NH2, 1-2 grupos -COOH, o 1-2 grupos -SO3H, - y que está opcionalmente sustituida con 1-10 grupos -OH, 1-5 grupos -COOH, 1-2 grupos -SO3H, 1-5 grupos NH2, 1-5 grupos alcoxi C1-4, en donde R6 es H o alquilo C1-4, Rf es una cadena de carbonos perfluorada, lineal a ramificada, con la formula -CnF2nE, en la que E representa un átomode F, Cl, Br, I o H terminal y n son los numeros 4-30, X es un grupo de la formula (11) y G es -O- o -SO2-, s y s' son, de modo independientemente entre sí 1 o 2, t es 0 o 1 y p representa el sitio de union de X con L y x representa el sitio de union de X con Rf, K es un complejo metálico de la formula general (2), en donde R1 es un átomo de H o un equivalente de iones metálicos de los numeros atomicos 21-29, 31-33, 37-39, 42-44, 49 o 57-83, con la condicion de que al menos dos R1 sean equivalentes de iones metálicos R2 y R3 presentan, de modo independiente entre sí, hidrogeno, alquilo C1-7, bencilo, fenilo, - CH2OH o -CH2OCH3 y U representa -C6H4-O-CH2-omega-, -(CH2)1-5-omega, un grupo fenileno, -CH2-NHCO- CH2-CH (CH2COOH)-C6H4-omega, -C6H4-(OCH2CH2)0-1-N(CH2COOH)-CH2-omega o un grupo alquileno C1-12 o -(CH2)7-12-C6H4-O- opcionalmente interrumpido con uno o varios átomos de oxígeno, 1 a 3 grupos -NHCO-, 1 a 3 grupos -CONH y/o sustituido con 1 a 3 grupos -(CH2)0-5COOH, en donde omega es el sitio de union con -CO-, o de la formula general (3) en donde R1 tiene el significado indicado con anterioridad, R4 representa hidrogeno o un equivalente de iones metálicos mencionado en R1 y U1 representa -C6H4-O-CH2-omega- o un grupo -(CH2)p'-, en donde omega es el sitio de union con -CO- y p' es un numero entero entre 1 y 4, o de la formula general (4) en donde R1 y R2 tienen el significado mencionado con anterioridad o de la formula general (5a) o (5b) en donde R1 tiene el significado indicado con anterioridad, o de la formula general (6) en donde R1 tiene el significado indicado con anterioridad, o de la formula general (7) en donde R1 y U1 tienen el significado mencionado con anterioridad, o de la formula general (8) en donde R1 tiene el significado indicado con anterioridad, y U2 representa un grupo alquileno C1-20 saturado o insaturado, de cadena lineal o ramificada, que opcionalmente contiene grupos imino, fenileno, fenilenoxi, fenilenimino, amida, hidrazida, carbonilo, éster, átomos de oxígeno, azufre y/u oxígeno, opcionalmente sustituido con grupos hidroxi, mercapto, oxo, tioxo, carboxi, carboxialquilo, éster y/o amino, o de la formula general (8') en donde R1 tiene el significado indicado con anterioridad, y en el radical K puede haber grupos ácidos eventualmente existentes, opcionalmente como sales de bases o aminoácidos o amidas de aminoácidos orgánicos y/o inorgánicos y L representa un radical seleccionado de los siguientes radicales (9a) a (9g): en donde q' es 1, 2, 3 o 4, y en donde alfa es el sitio de union de L con el complejo K, beta es el sitio de union de L con el radical Q y gamma presenta el sitio de union de L con N de la formula (1), y A representa una cadena de carbonos C1-15 lineal o ramificada, saturada o insaturada que puede estar interrumpida por 1-4 átomos de O, 1-3 grupos - NHCO, 1-3 grupos -CONH, 1-2 grupos -SO2-, 1-2 átomos de azufre, 1-3 grupos -NH o 1-2 grupos fenileno, que opcionalmente pueden estar sustituidos con 1-2 grupos -OH, 1-2 grupos -NH2, 1-2 grupos -COOH, o 1-2 grupos -SO3H, y que está opcionalmente sustituida con 1-10 grupos -OH, 1-5 grupos -COOH, 1-2 grupos -SO3H, 1-5 grupos -NH2, 1-5 grupos alcoxi C1-4.Procedures for its preparation and its use in the diagnosis of MRI and X-rays, in radiodiagnosis and radiotherapy, as well as in MRT lymphography. Claim 1: Perfluoroalkyl-containing complexes with an N-alkyl group of the general formula 1 wherein R represents a mono- or oligosaccharide radical linked through 1-OH, which is optionally peralkylated, in this case Q has the meaning of a selected group of delta-CO- (CH2) nö-e, delta-NH- (CH2) nö-e, delta- (CH2) m- e where n '' is an integer of 1 and 5, and m is an integer of 1 and 6, and where delta indicates the site of union with the linker L and indicates the site of union with the radical R; or R has one of the following meanings, then Q has the meaning of a direct bond: R means a polar radical selected from the complexes K of the general formulas (2) to (7 '), where R1 here means an atom of hydrogen or a metal ion equivalent of the atomic numbers 20-29, 31-33, 37-39, 42-44, 49 or 57-83, and the radicals R2, R3, R4, U, U2 and U1 have the meaning indicated below, or a carbon chain linked through -CO-, -NR6- or a direct link with linker L with 1-30 C atoms, which can be linear or branched, saturated or unsaturated, and is eventually interrupted by 1-10 oxygen atoms, 1-5 -NHCO groups, 1-5 -CONH groups, 1-2 sulfur atoms, 1-5 -NH groups or 1-2 phenylene groups, which may optionally be substituted with 1 -2 OH groups, 1-2 NH2 groups, 1-2 -COOH groups, or 1-2 -SO3H groups, - and which is optionally substituted with 1-10 -OH groups, 1-5 -COOH groups, 1-2 -SO3H groups, 1-5 NH2 groups, 1-5 C1-4 alkoxy groups, wherein R6 is H or C1-4 alkyl, Rf is a perfluorinated carbon chain, linear to branched, with the formula -CnF2nE, in which E represents an atom F, Cl, Br, I or H terminal and n are numbers 4-30, X is a group of the formula (11) and G is -O- or -SO2-, sys' are, independently of each other 1 or 2, t is 0 or 1 and p represents the site of union of X with L and x represents the site of union of X with Rf, K is a metal complex of the general formula (2), where R1 is an atom of H or an equivalent of metal ions of the numbers Atomic 21-29, 31-33, 37-39, 42-44, 49 or 57-83, with the proviso that at least two R1 are equivalent of metal ions R2 and R3, independently of each other, hydrogen, C1-7 alkyl, benzyl, phenyl, - CH2OH or -CH2OCH3 and U represents -C6H4-O-CH2-omega-, - (CH2) 1-5-omega, a phenylene group, -CH2-NHCO- CH2-CH ( CH2COOH) -C6H4-omega, -C6H4- (OCH2CH2) 0-1-N (CH2COOH) -CH2-omega or a C1-12 alkylene group or - (CH2) 7-12-C6H4-O- optionally interrupted with one or several oxygen atoms, 1 to 3 groups -NHCO-, 1 to 3 groups -CONH and / or substituted with 1 to 3 groups - (CH2) 0-5COOH, in where omega is the binding site with -CO-, or of the general formula (3) where R1 has the meaning indicated above, R4 represents hydrogen or a metal ion equivalent mentioned in R1 and U1 represents -C6H4-O- CH2-omega- or a group - (CH2) p'-, where omega is the binding site with -CO- and p 'is an integer between 1 and 4, or of the general formula (4) where R1 and R2 have the meaning mentioned above or of the general formula (5a) or (5b) where R1 has the meaning indicated above, or of the general formula (6) where R1 has the meaning indicated above, or of the general formula (7) where R1 and U1 have the meaning mentioned above, or of the general formula (8) where R1 has the meaning indicated above, and U2 represents a g saturated or unsaturated C1-20 alkylene rupo, straight or branched chain, which optionally contains imino, phenylene, phenyloxy, phenyleneimino, amide, hydrazide, carbonyl, ester, oxygen atoms, sulfur and / or oxygen groups, optionally substituted with hydroxy groups , mercapto, oxo, thioxo, carboxy, carboxyalkyl, ester and / or amino, or of the general formula (8 ') wherein R1 has the meaning indicated above, and in the radical K there may be optionally existing acid groups, optionally as salts of bases or amino acids or amides of organic and / or inorganic amino acids and L represents a radical selected from the following radicals (9a) to (9g): where q 'is 1, 2, 3 or 4, and where alpha is the site of union of L with the complex K, beta is the site of union of L with the radical Q and gamma has the site of union of L with N of the formula (1), and A represents a carbon chain C1- 15 linear or branched, saturated or unsaturated that may be interrupted by 1-4 O atoms, 1-3 groups - NHCO, 1-3 groups -CONH, 1-2 groups -SO2-, 1-2 sulfur atoms, 1-3 -NH groups or 1-2 phenylene groups, which may optionally be substituted with 1-2 -OH groups, 1-2 -NH2 groups, 1-2 -COOH groups, or 1-2 -SO3H groups, and which is optionally substituted with 1-10 -OH groups, 1- 5 -COOH groups, 1-2 -SO3H groups, 1-5 -NH2 groups, 1-5 C1-4 alkoxy groups.

ARP060103021A 2005-07-15 2006-07-14 METALLIC COMPLEXES WITH CONTENT OF PERFLUOR OR RENT PROCEDURES FOR THEIR PREPARATION, AS WELL AS THEIR USE AR055200A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005033903A DE102005033903B4 (en) 2005-07-15 2005-07-15 Perfluoroalkyl-containing complexes, processes for their preparation, and their use and pharmaceutical compositions containing them

Publications (1)

Publication Number Publication Date
AR055200A1 true AR055200A1 (en) 2007-08-08

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AR (1) AR055200A1 (en)
DE (1) DE102005033903B4 (en)

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4317588C2 (en) * 1993-05-24 1998-04-16 Schering Ag Macrocyclic metal complexes containing fluorine, process for their preparation and their use
DE19603033A1 (en) * 1996-01-19 1997-07-24 Schering Ag Perfluoroalkyl-containing metal complexes, processes for their preparation and their use in NMR diagnostics
DE19744003B4 (en) * 1997-09-26 2004-07-08 Schering Ag Contrast agent for infarct and necrosis imaging
DE19744004C1 (en) * 1997-09-26 1999-07-22 Schering Ag Lipophilic metal complexes for necrosis and infarct imaging
DE19914101C1 (en) * 1999-03-22 2000-10-12 Schering Ag Perfluoroalkylamides, their preparation and their use in diagnostics
DE10040858C2 (en) * 2000-08-11 2003-12-18 Schering Ag Perfluoroalkyl-containing complexes with polar residues, process for their preparation and their use

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DE102005033903A1 (en) 2007-01-18
DE102005033903B4 (en) 2007-08-09

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