ES2172461B1 - NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES. - Google Patents

NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES.

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Publication number
ES2172461B1
ES2172461B1 ES200100167A ES200100167A ES2172461B1 ES 2172461 B1 ES2172461 B1 ES 2172461B1 ES 200100167 A ES200100167 A ES 200100167A ES 200100167 A ES200100167 A ES 200100167A ES 2172461 B1 ES2172461 B1 ES 2172461B1
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Spain
Prior art keywords
sub
compound
complexes
reacted
formula
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.)
Expired - Fee Related
Application number
ES200100167A
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Spanish (es)
Other versions
ES2172461A1 (en
Inventor
Garcia Paloma Ballesteros
Garcia-Esteller Sebasti Cerdan
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.)
Laboratorios Farmaceuticos Rovi SA
Original Assignee
Laboratorios Farmaceuticos Rovi SA
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Publication date
Application filed by Laboratorios Farmaceuticos Rovi SA filed Critical Laboratorios Farmaceuticos Rovi SA
Priority to ES200100167A priority Critical patent/ES2172461B1/en
Priority to PCT/ES2002/000031 priority patent/WO2002059097A1/en
Publication of ES2172461A1 publication Critical patent/ES2172461A1/en
Application granted granted Critical
Publication of ES2172461B1 publication Critical patent/ES2172461B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Radiology & Medical Imaging (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1. Un compuesto de Fórmula General A **Figura01** donde los radicales R{sub,1}, R{sub,2}, R{sub,3} y R{sub,4}, tienen los valores conocidos universalmente en la formulación de la química orgánica; que se puede emplear para la preparación de quelatos útiles como agentes de contraste en el diagnóstico por imagen. 2. El compuesto de la Reivindicación 1, en donde X en la Fórmula A es (CH{sub,2}){sub,n}. 3. El compuesto de la Reivindicación 2, en donde n es 0. 4. El compuesto de la Reivindicación 2, en donde n es 1. 5. El compuesto de la Reivindicación 1, en donde X en la Fórmula A es CH{sub,2}OCH{sub,2}. 6. El compuesto de la Reivindicación 1, en donde X en la Fórmula A es CH{sub,2}NHCH{sub,2}. 7. Un procedimiento para la obtención del compuesto de Fórmula general A, de la Reivindicación 1, que se caracteriza porque se hace reaccionar un biazol con 1,2- dibromoetano en presencia de BTBA e hidróxido de sodio, para obtener su correspondiente derivado alquilado, que posteriormente se hace reaccionar con iminodiacetato de metilo, sintetizando el correspondiente derivado metilado que a su vez reacciona con hidróxido sódico en presencia de agua, para conseguir la sal sódica deseada. 8. Un procedimiento para la obtención del compuesto de Fórmula general A, de la Reivindicación 1, que se caracteriza porque se hace reaccionar dos moléculas de 1- cloroetil-3,5-dimetilprazol con paraformaldehido en medio ácido calentándose a continuación la mezcla de reacción, en presencia de ácido clorhídrico, para obtener el correspondiente bispirazol, el cual, a su vez, se hace reaccionar con iminodiacetato de metilo para obtener el correspondiente compuesto intermediario metilado, cuya hidrólisis en medio básico da la sal sódica deseada. 9. Los complejos de los compuestos de la Reivindicación 1 con metales de transición y lantánidos. 10. Los complejos de la Reivindicación 9, en donde el metal a complejar es el Gadolinio. 11. Los complejos de la Reivindicación 9, en donde el metal a complejar es el Disprosio. 12. La utilización clínica, de los compuestos de la Reivindicación 1 y sus correspondientes complejos, en el diagnóstico por imagen.1. A compound of General Formula A ** Figure01 ** where the radicals R {sub, 1}, R {sub, 2}, R {sub, 3} and R {sub, 4}, have universally known values in the formulation of organic chemistry; which can be used for the preparation of chelates useful as contrast agents in diagnostic imaging. 2. The compound of Claim 1, wherein X in Formula A is (CH {sub, 2}) {sub, n}. 3. The compound of Claim 2, wherein n is 0. 4. The compound of Claim 2, wherein n is 1. 5. The compound of Claim 1, wherein X in Formula A is CH {sub , 2} OCH {sub, 2}. 6. The compound of Claim 1, wherein X in Formula A is CH {sub, 2} NHCH {sub, 2}. 7. A process for obtaining the compound of General Formula A, of Claim 1, characterized in that a biazole is reacted with 1,2-dibromoethane in the presence of BTBA and sodium hydroxide, to obtain its corresponding alkylated derivative, which is subsequently reacted with methyl iminodiacetate, synthesizing the corresponding methylated derivative which in turn reacts with sodium hydroxide in the presence of water, to achieve the desired sodium salt. 8. A process for obtaining the compound of General Formula A, of Claim 1, characterized in that two 1- chloroethyl-3,5-dimethylprazole molecules are reacted with paraformaldehyde in acidic medium, the reaction mixture is then heated , in the presence of hydrochloric acid, to obtain the corresponding bispyrazole, which, in turn, is reacted with methyl iminodiacetate to obtain the corresponding methylated intermediate compound, whose hydrolysis in basic medium gives the desired sodium salt. 9. The complexes of the compounds of Claim 1 with transition metals and lanthanides. 10. The complexes of Claim 9, wherein the metal to be complexed is Gadolinium. 11. The complexes of Claim 9, wherein the metal to be complexed is Dysprosium. 12. The clinical use of the compounds of Claim 1 and their corresponding complexes, in diagnostic imaging.

ES200100167A 2001-01-25 2001-01-25 NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES. Expired - Fee Related ES2172461B1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
ES200100167A ES2172461B1 (en) 2001-01-25 2001-01-25 NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES.
PCT/ES2002/000031 WO2002059097A1 (en) 2001-01-25 2002-01-24 Novel gd(iii) ligands with bi- and bis-azolic structures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
ES200100167A ES2172461B1 (en) 2001-01-25 2001-01-25 NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES.

Publications (2)

Publication Number Publication Date
ES2172461A1 ES2172461A1 (en) 2002-09-16
ES2172461B1 true ES2172461B1 (en) 2003-09-16

Family

ID=8496500

Family Applications (1)

Application Number Title Priority Date Filing Date
ES200100167A Expired - Fee Related ES2172461B1 (en) 2001-01-25 2001-01-25 NEW LIGHTS OF GD (III) WITH BI-Y BIS-AZOLICA STRUCTURES.

Country Status (2)

Country Link
ES (1) ES2172461B1 (en)
WO (1) WO2002059097A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2253018B1 (en) * 2003-04-23 2007-11-01 Universidad Nacional De Educacion A Distancia (U.N.E.D.) "1, OMEGA-DI-IMIDAZOL-1-ILPOLIOLES AS EXTRINSECTIVE PH INDICATORS FOR SPECTROSCOPY AND IMAGE BY MAGNETIC RESONANCE".
FR2857967B1 (en) * 2003-07-25 2015-04-24 Centre Nat Rech Scient LANTHANIDE COMPLEXES, THEIR PREPARATION AND USES THEREOF
WO2013018695A1 (en) 2011-07-29 2013-02-07 武田薬品工業株式会社 Heterocyclic compound
CN108164715B (en) * 2018-02-08 2020-06-09 中国科学院福建物质结构研究所 Rare earth organic framework crystal material, preparation method and application thereof
CN111206263B (en) * 2020-01-07 2021-03-12 中国科学院化学研究所 Preparation method of metal boric acid organic film

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2094101B1 (en) * 1995-06-13 1997-08-01 Univ Madrid Nac Educacion COMPLEXONAS OF NATURE OF ACIDS N-2- (AZOL-1 (2) -IL) ETILIMINODIACETICOS, SYNTHESIS, ANALYTICAL STUDY AND BIOLOGICAL APPLICATIONS.

Also Published As

Publication number Publication date
WO2002059097A1 (en) 2002-08-01
ES2172461A1 (en) 2002-09-16

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