AR054865A1 - METAL COMPLEXES WITH CONTENT OF PERFLUOROALQUILO, PROCEDURES FOR THEIR PREPARATION, AS WELL AS ITS USE - Google Patents

METAL COMPLEXES WITH CONTENT OF PERFLUOROALQUILO, PROCEDURES FOR THEIR PREPARATION, AS WELL AS ITS USE

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Publication number
AR054865A1
AR054865A1 ARP060103020A ARP060103020A AR054865A1 AR 054865 A1 AR054865 A1 AR 054865A1 AR P060103020 A ARP060103020 A AR P060103020A AR P060103020 A ARP060103020 A AR P060103020A AR 054865 A1 AR054865 A1 AR 054865A1
Authority
AR
Argentina
Prior art keywords
groups
site
omega
union
group
Prior art date
Application number
ARP060103020A
Other languages
Spanish (es)
Inventor
Heiko Schirmer
Hanns-Joachim Weinmann
Johannes Platzek
Bernd Misselwitz
Heribert Schmitt-Willich
Thomas Brumby
Ludwig Zorn
Joerg Meding
Original Assignee
Schering Ag
Epix Pharm Inc
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.)
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Publication date
Application filed by Schering Ag, Epix Pharm Inc filed Critical Schering Ag
Publication of AR054865A1 publication Critical patent/AR054865A1/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D257/00Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00Preparations for testing in vivo
    • A61K49/06Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Radiology & Medical Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Reivindicacion 1: Complejos con contenido de perfluoroalquilo con estructura de ligador con nitrogeno de la formula general (1), en donde: R representa un radical mono- u oligosacárido unido a través de 1-OH, en este caso Q tiene el significado de un grupo seleccionado de. delta-CO-(CH2)n''-épsilon; delta-NH-(CH2)n''-épsilon; delta-(CH2)m-épsilon; 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 épsilon 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 V, 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 y U1 representan el significado indicado más abajo; o una cadena de carbonos con C1-30 unida con el ligador L a través de -CO-, -NR7- o un enlace directo; que puede ser lineal o ramificada, saturada o insaturada, y que está opcionalmente interrumpida por 1-10 átomos de oxígeno, 1-5 grupos -NHCO, 1-5 -CONH, 1-2 átomos de azufre, 1-5 grupos -NH o 1-2 grupos fenileno, que pueden estar opcionalmente 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, grupos alcoxi C1-4; en donde R7 es H o alquilo C1-4; Rf es una cadena de carbonos perfluorada, lineal o ramificada, con la formula -CnF2nE, en la que E representa un átomo de fluor, cloro, bromo, yodo o hidrogeno terminal y n son los numeros 4-30; K es un complejo metálico de la formula general (2), en donde R1 es un átomo de hidrogeno 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 representan, 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 por 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 ion metálico 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 (5) o (6), en donde R1 tiene el significado indicado con anterioridad, o de la formula general (7), en donde R1 tiene el significado indicado con anterioridad, o de la formula general (8), en donde R1 y U1 tienen el significado mencionado con anterioridad en donde omega es el sitio de union con -CO- o de la formula general (9), en donde R1 tiene el significado indicado con anterioridad, y U2 representa un grupo alquileno C1-20 de cadena lineal o ramificada, saturado o insaturado, que opcionalmente contiene grupo imino, fenileno, fenilenoxi, fenilenimino, amida, hidrazida, carbonilo, éster, átomos de oxígeno, azufre y/u oxígeno, opcionalmente sustituido por grupos hidroxi, mercapto, oxo, tioxo, carboxi, carboxialquilo, éster y/o amino, 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 de formulas (10) a (12), en donde n' y m' representan, de modo independientes entre sí, un numero entero entre 0 y 4, y m' + n' mayor o igual 1, y R8 y R8' son, de modo independiente entre sí, ya sea -H u -OH, en donde en el caso de m' + n' > 1, cada grupo -(CR8R8')- puede ser igual o diferente; y W es un enlace directo, -O- o un grupo fenileno, que puede estar opcionalmente sustituido con 1 a 4 grupos hidroxi, y q' es 1, 2, 3 o 4; 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 representa el sitio de union del L con el radical X; y X es un grupo de la formula (13), en donde Y es un enlace directo, un grupo -CO- o un grupo NR6; en donde R6 es -H o 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, 1-3grupos -CONH,, 1-2 grupos -SO2, 1,2 átomos de azufre, 1-3 grupos -NH o 1-2 grupos fenileno, que pueden estar opcionalmente 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; y G es -O- o -SO2-; s y s' son, de modo independiente entre sí, 1 o 2, t es 0 o 1; y (rho) representa el sitio de union de X con L y (xi) representa el sitio de union de X con Rf.Claim 1: Complexes with perfluoroalkyl content with a linker structure with nitrogen of the general formula (1), wherein: R represents a mono- or oligosaccharide radical linked through 1-OH, in this case Q has the meaning of a selected group of. delta-CO- (CH2) n '' - epsilon; delta-NH- (CH2) n '' - epsilon; delta- (CH2) m-epsilon; where n '' is an integer of 1 and 5, and m is an integer of 1 and 6; and where delta indicates the binding site with the linker L and epsilon indicates the binding site 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 V, where R1 here means a hydrogen atom 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 and U1 represent the meaning indicated below; or a carbon chain with C1-30 attached to linker L through -CO-, -NR7- or a direct link; which can be linear or branched, saturated or unsaturated, and which is optionally interrupted by 1-10 oxygen atoms, 1-5 -NHCO groups, 1-5 -CONH, 1-2 sulfur atoms, 1-5 -NH groups or 1-2 phenylene groups, which may be optionally 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, C1-4 alkoxy groups; wherein R7 is H or C1-4 alkyl; Rf is a perfluorinated, linear or branched carbon chain, with the formula -CnF2nE, in which E represents a fluorine, chlorine, bromine, iodine or terminal hydrogen atom and n are numbers 4-30; K is a metal complex of the general formula (2), wherein R1 is a hydrogen atom or a metal ion equivalent of the atomic numbers 21-29, 31-33, 37-39, 42-44, 49 or 57 -83, with the proviso that at least two R1s are equivalent to metal ions; R2 and R3 independently represent 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 by one or more oxygen atoms, 1 to 3 -NHCO- groups, 1 to 3 groups -CONH and / or substituted with 1 to 3 groups - (CH2) 0-5COOH, where omega is the site of union with -CO-; or of the general formula (3), wherein 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 site of union with -CO- and p 'is an integer between 1 and 4; or of the general formula (4), wherein R1 and R2 have the meaning mentioned above; or of the general formula (5) or (6), where R1 has the meaning indicated above, or of the general formula (7), where R1 has the meaning indicated above, or of the general formula (8) , where R1 and U1 have the aforementioned meaning where omega is the site of union with -CO- or of the general formula (9), where R1 has the meaning indicated above, and U2 represents a C1 alkylene group -20 straight or branched chain, saturated or unsaturated, which optionally contains imino, phenylene, phenyloxy, phenyleneimino, amide, hydrazide, carbonyl, ester, oxygen atoms, sulfur and / or oxygen groups, optionally substituted by hydroxy, mercapto groups, oxo, thioxo, carboxy, carboxy alkyl, ester and / or amino, 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 of formulas (10) to (12), where n 'and m' represent, independently of each other, an integer between 0 and 4, and m '+ n' greater than or equal to 1, and R8 and R8 'are, independently of each other, either -H or -OH, where in the case of m' + n '> 1, each group - (CR8R8') - can be the same or different ; and W is a direct bond, -O- or a phenylene group, which may be optionally substituted with 1 to 4 hydroxy groups, and q 'is 1, 2, 3 or 4; 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 represents the site of union of L with the radical X; and X is a group of the formula (13), wherein Y is a direct link, a group -CO- or an NR6 group; wherein R6 is -H or a linear or branched, saturated or unsaturated C1-15 carbon chain that may be interrupted by 1-4 O atoms, 1-3 -NHCO groups, 1-3 -CONH groups, 1-2 -SO2 groups, 1.2 sulfur atoms, 1-3 -NH groups or 1-2 phenylene groups, which may be optionally substituted with 1-2 OH groups, 1.2 NH2 groups, 1-2 -COOH groups or 1 -2 groups -SO3H; 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; and G is -O- or -SO2-; s and s' are, independently of each other, 1 or 2, t is 0 or 1; and (rho) represents the site of union of X with L and (xi) represents the site of union of X with Rf.

ARP060103020A 2005-07-15 2006-07-14 METAL COMPLEXES WITH CONTENT OF PERFLUOROALQUILO, PROCEDURES FOR THEIR PREPARATION, AS WELL AS ITS USE AR054865A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102005033902A DE102005033902B3 (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
AR054865A1 true AR054865A1 (en) 2007-07-25

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ID=37057146

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP060103020A AR054865A1 (en) 2005-07-15 2006-07-14 METAL COMPLEXES WITH CONTENT OF PERFLUOROALQUILO, PROCEDURES FOR THEIR PREPARATION, AS WELL AS ITS USE

Country Status (22)

Country Link
EP (1) EP1904463A2 (en)
JP (1) JP2009501174A (en)
KR (1) KR20080043762A (en)
CN (1) CN101223148A (en)
AR (1) AR054865A1 (en)
AU (1) AU2006272025A1 (en)
BR (1) BRPI0613407A2 (en)
CA (1) CA2615443A1 (en)
CR (1) CR9645A (en)
DE (1) DE102005033902B3 (en)
DO (1) DOP2006000167A (en)
EC (1) ECSP088100A (en)
GT (1) GT200600313A (en)
IL (1) IL187926A0 (en)
NO (1) NO20080813L (en)
PE (1) PE20070376A1 (en)
RU (1) RU2008105356A (en)
TN (1) TNSN08016A1 (en)
TW (1) TW200706538A (en)
UY (1) UY29664A1 (en)
WO (1) WO2007009638A2 (en)
ZA (1) ZA200801523B (en)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007015598A1 (en) * 2007-03-29 2008-10-02 Heinrich-Heine-Universität Düsseldorf Use of fluorochemical compounds for diagnostic purposes using imaging techniques
MX2010007501A (en) 2008-01-08 2010-08-16 Lantheus Medical Imaging Inc N-alkoxyamide conjugates as imaging agents.
US20210101905A1 (en) * 2019-10-04 2021-04-08 Llnited States Government as represented by the Department of Veterans Affairs Development of Imaging and Therapeutic Glucose Analogues for Sodium Dependent Glucose Transporters
EP4059925A1 (en) 2021-03-15 2022-09-21 Bayer Aktiengesellschaft New contrast agent for use in magnetic resonance imaging
CN114181164A (en) * 2021-12-13 2022-03-15 武汉大学中南医院 Synthesis method and application of MRI contrast agent based on Fe (II) specificity
EP4335840A1 (en) 2022-09-09 2024-03-13 Bayer Aktiengesellschaft New contrast agents for use in diagnostic imaging
EP4335462A1 (en) 2022-09-09 2024-03-13 Bayer AG Contrast agents for use in diagnostic computed tomography imaging

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

Also Published As

Publication number Publication date
WO2007009638A2 (en) 2007-01-25
WO2007009638A3 (en) 2007-04-26
AU2006272025A1 (en) 2007-01-25
RU2008105356A (en) 2009-08-20
ZA200801523B (en) 2008-11-26
CA2615443A1 (en) 2007-01-25
JP2009501174A (en) 2009-01-15
NO20080813L (en) 2008-04-09
DOP2006000167A (en) 2007-02-28
CN101223148A (en) 2008-07-16
IL187926A0 (en) 2008-03-20
BRPI0613407A2 (en) 2011-01-11
DE102005033902B3 (en) 2007-04-05
CR9645A (en) 2008-05-21
TW200706538A (en) 2007-02-16
GT200600313A (en) 2007-04-23
TNSN08016A1 (en) 2009-07-14
ECSP088100A (en) 2008-05-30
KR20080043762A (en) 2008-05-19
EP1904463A2 (en) 2008-04-02
PE20070376A1 (en) 2007-04-20
UY29664A1 (en) 2007-02-28

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