WO2014052091A1 - Preparation of an intermediate compound of ioforminol - Google Patents

Preparation of an intermediate compound of ioforminol Download PDF

Info

Publication number
WO2014052091A1
WO2014052091A1 PCT/US2013/060081 US2013060081W WO2014052091A1 WO 2014052091 A1 WO2014052091 A1 WO 2014052091A1 US 2013060081 W US2013060081 W US 2013060081W WO 2014052091 A1 WO2014052091 A1 WO 2014052091A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
compound mixture
mixture
preparation
bis
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.)
Ceased
Application number
PCT/US2013/060081
Other languages
English (en)
French (fr)
Inventor
Mikkel Thaning
Andreas Olsson
Christian Glogard
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.)
GE Healthcare AS
Medi Physics Inc
Original Assignee
GE Healthcare AS
Medi Physics 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.)
Filing date
Publication date
Priority to CN201380050455.8A priority Critical patent/CN104661996A/zh
Priority to RU2015107016A priority patent/RU2654461C2/ru
Priority to KR1020157007427A priority patent/KR20150061635A/ko
Priority to US14/430,155 priority patent/US9884808B2/en
Priority to MX2015003912A priority patent/MX354604B/es
Priority to CA2881852A priority patent/CA2881852A1/en
Priority to BR112015004591A priority patent/BR112015004591A2/pt
Priority to EP13771008.3A priority patent/EP2900632B1/en
Application filed by GE Healthcare AS, Medi Physics Inc filed Critical GE Healthcare AS
Priority to JP2015534549A priority patent/JP6431842B2/ja
Priority to AU2013323981A priority patent/AU2013323981B2/en
Publication of WO2014052091A1 publication Critical patent/WO2014052091A1/en
Priority to IN1185DEN2015 priority patent/IN2015DN01185A/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • C07C231/24—Separation; Purification
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and at least three atoms of bromine or iodine, bound to carbon atoms of the same non-condensed six-membered aromatic ring

Definitions

  • the process comprises the steps of:
  • the amount of alcohol used in the washing may be about the same amount as used in the precipitation, divided on the number of portions. It has been found that it is beneficially for the further synthesis that some alcohol is left in the compound mixture (3) after the work-up procedure has finished, hence the drying should be adjusted accordingly. Preparation of compound mixture (3) with a rest alcohol content of 0-7 % has been found appropriate.
  • the compounds prepared according to the invention may be used as contrast agents and may be formulated with conventional carriers and excipients to produce diagnostic contrast media.
  • the invention provides a diagnostic composition comprising loforminol prepared according to the process of the invention, together with at least one physiologically tolerable carrier or excipient, e.g. in aqueous solution for injection optionally together with added plasma ions or dissolved oxygen.
  • the contrast agent composition of the invention may be in a ready to use concentration or may be a concentrate form for dilution prior to administration.
  • the invention further embraces use of loforminol prepared according to the process of preparation, and a diagnostic composition containing such, in X-ray contrast examinations.
  • the invention is illustrated with reference to the following non-limiting examples.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
PCT/US2013/060081 2012-09-27 2013-09-17 Preparation of an intermediate compound of ioforminol Ceased WO2014052091A1 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
BR112015004591A BR112015004591A2 (pt) 2012-09-27 2013-09-17 processos para a preparação de uma mistura de um composto e para preparar ioforminol, e, mistura de um composto na forma de pó
KR1020157007427A KR20150061635A (ko) 2012-09-27 2013-09-17 아이오포르미놀의 중간체 화합물의 제조법
US14/430,155 US9884808B2 (en) 2012-09-27 2013-09-17 Preparation of an intermediate compound of ioforminol
MX2015003912A MX354604B (es) 2012-09-27 2013-09-17 Preparacion de un compuesto intermediario de ioforminol.
CA2881852A CA2881852A1 (en) 2012-09-27 2013-09-17 Preparation of an intermediate compound of ioforminol
CN201380050455.8A CN104661996A (zh) 2012-09-27 2013-09-17 Ioforminol的中间体化合物的制备
AU2013323981A AU2013323981B2 (en) 2012-09-27 2013-09-17 Preparation of an intermediate compound of Ioforminol
EP13771008.3A EP2900632B1 (en) 2012-09-27 2013-09-17 Preparation of an intermediate compound of ioforminol
JP2015534549A JP6431842B2 (ja) 2012-09-27 2013-09-17 イオホルミノールの中間体化合物の調製
RU2015107016A RU2654461C2 (ru) 2012-09-27 2013-09-17 Получение промежуточного соединения синтеза иоформинола
IN1185DEN2015 IN2015DN01185A (enExample) 2012-09-27 2015-02-13

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
NO20121102 2012-09-27
NO20121102 2012-09-27

Publications (1)

Publication Number Publication Date
WO2014052091A1 true WO2014052091A1 (en) 2014-04-03

Family

ID=49274871

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2013/060081 Ceased WO2014052091A1 (en) 2012-09-27 2013-09-17 Preparation of an intermediate compound of ioforminol

Country Status (12)

Country Link
US (1) US9884808B2 (enExample)
EP (1) EP2900632B1 (enExample)
JP (1) JP6431842B2 (enExample)
KR (1) KR20150061635A (enExample)
CN (2) CN110003038A (enExample)
AU (1) AU2013323981B2 (enExample)
BR (1) BR112015004591A2 (enExample)
CA (1) CA2881852A1 (enExample)
IN (1) IN2015DN01185A (enExample)
MX (1) MX354604B (enExample)
RU (1) RU2654461C2 (enExample)
WO (1) WO2014052091A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9884808B2 (en) 2012-09-27 2018-02-06 Ge Healthcare As Preparation of an intermediate compound of ioforminol

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0108638A1 (en) 1982-11-08 1984-05-16 NYEGAARD & CO. A/S X-ray contrast agents
WO1998023296A1 (en) 1996-11-26 1998-06-04 Nycomed Imaging As Process for the production of iodinated organic x-ray contrast agents
WO2000047549A1 (en) * 1999-02-11 2000-08-17 Nycomed Imaging As Preparation of iodixanol
WO2006016815A1 (en) 2004-08-09 2006-02-16 Ge Healthcare As Preparation of iodixanol
WO2009008734A2 (en) 2007-07-12 2009-01-15 Ge Healthcare As Contrast agents

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997000240A1 (en) 1995-06-16 1997-01-03 Biophysica Foundation Formyl derivatives as nonionic contrast media
NO20053687D0 (no) * 2005-07-29 2005-07-29 Amersham Health As Crystallisation Process.
US20110021822A1 (en) * 2009-07-21 2011-01-27 Ge Healthcare As continuous deacetylation and purification process in synthesis of non-ionic x-ray contrast agents
JP6325547B2 (ja) * 2012-09-27 2018-05-16 ジーイー・ヘルスケア・アクスイェ・セルスカプ Ｘ線造影剤イオホルミノールの調製
EP2900632B1 (en) 2012-09-27 2019-10-30 Ge Healthcare As Preparation of an intermediate compound of ioforminol

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0108638A1 (en) 1982-11-08 1984-05-16 NYEGAARD & CO. A/S X-ray contrast agents
WO1998023296A1 (en) 1996-11-26 1998-06-04 Nycomed Imaging As Process for the production of iodinated organic x-ray contrast agents
WO2000047549A1 (en) * 1999-02-11 2000-08-17 Nycomed Imaging As Preparation of iodixanol
WO2006016815A1 (en) 2004-08-09 2006-02-16 Ge Healthcare As Preparation of iodixanol
WO2009008734A2 (en) 2007-07-12 2009-01-15 Ge Healthcare As Contrast agents

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
BANDGAR, B.P. ET AL: "Clean and Green Approach for N-formylation of Amines using Formic acid under neat reaction condition", ARCHIVES OF APPLIED SCIENE RESEARCH, vol. 3, no. 3, 2011, pages 246 - 251, XP002716852, ISSN: 0975-508X *
CHAI ET AL.: "Predicting cardiotoxicity propensity of the novel iodinated contrast medium GE-145: ventricular fibrillation during left coronary arteriography in pigs", ACTA RADIOL, 2010
WISTRAND, L.G. ET AL.: "GE-145, a new low-osmolar dimeric radiographic contrast medium", ACTA RADIOL, 2010

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9884808B2 (en) 2012-09-27 2018-02-06 Ge Healthcare As Preparation of an intermediate compound of ioforminol

Also Published As

Publication number Publication date
CA2881852A1 (en) 2014-04-03
US20150246871A1 (en) 2015-09-03
MX2015003912A (es) 2015-08-05
IN2015DN01185A (enExample) 2015-06-26
JP6431842B2 (ja) 2018-11-28
BR112015004591A2 (pt) 2017-07-04
AU2013323981B2 (en) 2017-09-14
AU2013323981A1 (en) 2015-03-05
US9884808B2 (en) 2018-02-06
CN104661996A (zh) 2015-05-27
JP2015532280A (ja) 2015-11-09
KR20150061635A (ko) 2015-06-04
RU2015107016A (ru) 2016-11-20
CN110003038A (zh) 2019-07-12
RU2654461C2 (ru) 2018-05-18
MX354604B (es) 2018-03-07
EP2900632A1 (en) 2015-08-05
EP2900632B1 (en) 2019-10-30

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