CA2274132A1 - Macrocyclic metal complex carboxylic acids, use and method for the production thereof - Google Patents

Macrocyclic metal complex carboxylic acids, use and method for the production thereof Download PDF

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Publication number
CA2274132A1
CA2274132A1 CA002274132A CA2274132A CA2274132A1 CA 2274132 A1 CA2274132 A1 CA 2274132A1 CA 002274132 A CA002274132 A CA 002274132A CA 2274132 A CA2274132 A CA 2274132A CA 2274132 A1 CA2274132 A1 CA 2274132A1
Authority
CA
Canada
Prior art keywords
carboxylic acids
metal complex
production
complex carboxylic
macrocyclic metal
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002274132A
Other languages
French (fr)
Other versions
CA2274132C (en
Inventor
Johannes Platzek
Heribert Schmitt-Willich
Bernd Raduchel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering Aktiengesellschaft
Johannes Platzek
Heribert Schmitt-Willich
Bernd Raduchel
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 Schering Aktiengesellschaft, Johannes Platzek, Heribert Schmitt-Willich, Bernd Raduchel filed Critical Schering Aktiengesellschaft
Publication of CA2274132A1 publication Critical patent/CA2274132A1/en
Application granted granted Critical
Publication of CA2274132C publication Critical patent/CA2274132C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • A61K49/085—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by the carrier conjugated systems
    • 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
    • A61K49/12—Macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Radiology & Medical Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

The invention relates to novel macrocyclic metal complex carboxylic acids of formula (II), (see formula I) wherein Z means a metal iron equivalent of atomic numbers 58-71 and R is a CHX1-CO-NH-CHY1-(CH2)f-COOH group, wherein X1 and Y1 mean individually a hydrogen atom, a straight--chained or branched C1-C7-alkyl radical, a phenyl or benzyl group and f means the figures 0-9. Said acids can be used as intermediate preparations for synthesis of cascade polymer complexes suitable as diagnostic agents.
CA002274132A 1996-12-04 1997-11-26 Macrocyclic metal complex carboxylic acids, use and method for the production thereof Expired - Fee Related CA2274132C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19652387A DE19652387A1 (en) 1996-12-04 1996-12-04 Macrocyclic metal complex carboxylic acids, their use and processes for their preparation
DE19652387.7 1996-12-04
PCT/EP1997/006593 WO1998024774A1 (en) 1996-12-04 1997-11-26 Macrocyclic metal complex carboxylic acids, use and method for the production thereof

Publications (2)

Publication Number Publication Date
CA2274132A1 true CA2274132A1 (en) 1998-06-11
CA2274132C CA2274132C (en) 2008-02-12

Family

ID=7814929

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002274132A Expired - Fee Related CA2274132C (en) 1996-12-04 1997-11-26 Macrocyclic metal complex carboxylic acids, use and method for the production thereof

Country Status (16)

Country Link
EP (1) EP0946526B1 (en)
JP (1) JP4252112B2 (en)
KR (1) KR100495846B1 (en)
CN (1) CN1100767C (en)
AT (1) ATE253056T1 (en)
AU (1) AU734983B2 (en)
CA (1) CA2274132C (en)
DE (2) DE19652387A1 (en)
DK (1) DK0946526T3 (en)
ES (1) ES2208968T3 (en)
HK (1) HK1022153A1 (en)
IL (1) IL130271A (en)
PT (1) PT946526E (en)
TW (1) TW434232B (en)
WO (1) WO1998024774A1 (en)
ZA (1) ZA9710931B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3303307B1 (en) 2015-06-04 2019-09-04 Bayer Pharma Aktiengesellschaft New gadolinium chelate compounds for use in magnetic resonance imaging
US11814369B2 (en) 2016-11-28 2023-11-14 Bayer Pharma Aktiengesellschaft High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging
US11944690B2 (en) 2018-11-23 2024-04-02 Bayer Aktiengesellschaft Formulation of contrast media and process of preparation thereof

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1369134A1 (en) 2002-06-05 2003-12-10 Bracco Imaging S.p.A. New agents for magnetic imaging method
DE102007058220A1 (en) 2007-12-03 2009-06-04 Bayer Schering Pharma Aktiengesellschaft New metal complexes useful e.g. for manufacturing agent for X-ray diagnostics and magnetic resonance tomography-diagnostics of brain infarcts and liver tumor, and/or space-process in liver and abdomen tumors and musculoskeletal tumors
KR101334780B1 (en) 2010-08-13 2013-12-02 한국생명공학연구원 Iodine-containing radial-shape macromolecular compounds, preparation method thereof and contrast medium compositions for CT comprising the same
JP2020517584A (en) * 2017-04-27 2020-06-18 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア Modified MRI contrast agents and uses thereof
CN114573521B (en) * 2020-12-01 2023-10-27 威智医药股份有限公司 Preparation method of gadobutrol and intermediate thereof

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA894792B (en) * 1988-06-24 1991-04-24 Dow Chemical Co Macrocyclic bifunctional chelants,complexes thereof and their antibody conjugates
DE3938992A1 (en) * 1989-11-21 1991-05-23 Schering Ag Cascade polymer-bound complex formers, their complexes and conjugates, process for their preparation and pharmaceutical compositions containing them
DE4009119A1 (en) * 1990-03-19 1991-09-26 Schering Ag 1,4,7,10-TETRAAZACYCLODODECANE-BUTYLTRIOLS, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL AGENTS CONTAINING THEM
DE4344460A1 (en) * 1993-12-22 1995-06-29 Schering Ag Metal complexes of dendrimeric macromolecules, diagnostic agents containing them and methods for producing the complexes and agents
DE4425857A1 (en) * 1994-07-07 1996-01-11 Schering Ag Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them
DE19525924A1 (en) * 1995-07-04 1997-01-09 Schering Ag Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them
DE19549286A1 (en) * 1995-12-22 1997-06-26 Schering Ag Cascade polymer complexes, processes for their preparation and pharmaceutical compositions containing them

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3303307B1 (en) 2015-06-04 2019-09-04 Bayer Pharma Aktiengesellschaft New gadolinium chelate compounds for use in magnetic resonance imaging
EP3611169B1 (en) 2015-06-04 2021-07-21 Bayer Pharma Aktiengesellschaft New gadolinium chelate compounds for use in magnetic resonance imaging
US11814369B2 (en) 2016-11-28 2023-11-14 Bayer Pharma Aktiengesellschaft High relaxivity gadolinium chelate compounds for use in magnetic resonance imaging
US11944690B2 (en) 2018-11-23 2024-04-02 Bayer Aktiengesellschaft Formulation of contrast media and process of preparation thereof

Also Published As

Publication number Publication date
DE59710931D1 (en) 2003-12-04
AU5655498A (en) 1998-06-29
EP0946526A1 (en) 1999-10-06
AU734983B2 (en) 2001-06-28
CN1239958A (en) 1999-12-29
IL130271A0 (en) 2000-06-01
KR100495846B1 (en) 2005-06-17
JP4252112B2 (en) 2009-04-08
WO1998024774A1 (en) 1998-06-11
JP2001504843A (en) 2001-04-10
EP0946526B1 (en) 2003-10-29
PT946526E (en) 2004-02-27
ES2208968T3 (en) 2004-06-16
ATE253056T1 (en) 2003-11-15
IL130271A (en) 2005-05-17
ZA9710931B (en) 1998-06-15
DE19652387A1 (en) 1998-06-10
CN1100767C (en) 2003-02-05
DK0946526T3 (en) 2004-01-12
KR20000057402A (en) 2000-09-15
CA2274132C (en) 2008-02-12
HK1022153A1 (en) 2000-07-28
TW434232B (en) 2001-05-16

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