WO2004113271A2 - A method for the preparation of crystalline dexloxiglumide - Google Patents

A method for the preparation of crystalline dexloxiglumide Download PDF

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Publication number
WO2004113271A2
WO2004113271A2 PCT/IB2004/002208 IB2004002208W WO2004113271A2 WO 2004113271 A2 WO2004113271 A2 WO 2004113271A2 IB 2004002208 W IB2004002208 W IB 2004002208W WO 2004113271 A2 WO2004113271 A2 WO 2004113271A2
Authority
WO
WIPO (PCT)
Prior art keywords
dexloxiglumide
pharmaceutical composition
crystallization
crystalline
preparation
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/IB2004/002208
Other languages
English (en)
French (fr)
Other versions
WO2004113271A3 (en
WO2004113271A8 (en
Inventor
Francesco Makovec
Lucio Claudio Rovati
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.)
Rottapharm SpA
Original Assignee
Rottapharm SpA
Rotta Research Laboratorium SpA
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 Rottapharm SpA, Rotta Research Laboratorium SpA filed Critical Rottapharm SpA
Priority to CA2529018A priority Critical patent/CA2529018C/en
Priority to US10/562,013 priority patent/US7662994B2/en
Priority to DE602004028830T priority patent/DE602004028830D1/de
Priority to DK04743871.8T priority patent/DK1646607T3/da
Priority to AT04743871T priority patent/ATE478839T1/de
Priority to EP04743871A priority patent/EP1646607B1/en
Priority to AU2004249526A priority patent/AU2004249526B2/en
Priority to HK06111355.0A priority patent/HK1089750B/en
Priority to JP2006516595A priority patent/JP5197955B2/ja
Publication of WO2004113271A2 publication Critical patent/WO2004113271A2/en
Publication of WO2004113271A3 publication Critical patent/WO2004113271A3/en
Publication of WO2004113271A8 publication Critical patent/WO2004113271A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • 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

Definitions

  • the subject of the present invention is a novel method for the preparation, by crystallization from isopropyl ether, of (R) -4- [ (3 , 4-dichlorobenzoyl) amino] -5- [ (3-methoxypropyl) - pentylamino] -5-oxo-pentanoic acid (dexloxiglumide, CR 2017) ; molecular formula: C 2 ⁇ H 30 Cl 2 N 2 O 5 ; CAS Registry Number: 119818- 90-2.
  • the PSD is determined by the "laser light scattering” technique, that is, the scattering (diffraction) which a high-energy, monochromatic light beam (a laser beam) undergoes when it encounters a particle of a particular size on its optical path.
  • the principal statistical distribution values calculated by the software of this apparatus are, amongst other things, the D 50 , that is, the size in microns for which 50% of the sample is smaller and 50% is larger. Another important measurement is the “span”, which is the measurement of the width of the distribution.
  • Figures 2A and 2B are photographs taken with 300x magnification of a dexloxiglumide sample prepared in accordance with the method of the invention ( Figure 2A) and of a sample crystallized from aqueous/alcoholic solvent in accordance with the prior art ( Figure 2B) , respectively.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicinal Preparation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
PCT/IB2004/002208 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide Ceased WO2004113271A2 (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
CA2529018A CA2529018C (en) 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide and products obtained thereby
US10/562,013 US7662994B2 (en) 2003-06-23 2004-06-21 Method for the preparation of crystalline dexloxiglumide and products obtained
DE602004028830T DE602004028830D1 (de) 2003-06-23 2004-06-21 Verfahren zur herstellung von kristallinem dexloxiglumid
DK04743871.8T DK1646607T3 (da) 2003-06-23 2004-06-21 Fremgangsmåde til fremstilling af krystallinsk dexloxiglumid
AT04743871T ATE478839T1 (de) 2003-06-23 2004-06-21 Verfahren zur herstellung von kristallinem dexloxiglumid
EP04743871A EP1646607B1 (en) 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide
AU2004249526A AU2004249526B2 (en) 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide
HK06111355.0A HK1089750B (en) 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide
JP2006516595A JP5197955B2 (ja) 2003-06-23 2004-06-21 結晶性デキスロキシグルミドの製造法

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IT000474A ITTO20030474A1 (it) 2003-06-23 2003-06-23 Procedimento per la preparazione di dexloxiglumide
ITTO2003A000474 2003-06-23

Publications (3)

Publication Number Publication Date
WO2004113271A2 true WO2004113271A2 (en) 2004-12-29
WO2004113271A3 WO2004113271A3 (en) 2005-01-27
WO2004113271A8 WO2004113271A8 (en) 2005-05-06

Family

ID=33524063

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2004/002208 Ceased WO2004113271A2 (en) 2003-06-23 2004-06-21 A method for the preparation of crystalline dexloxiglumide

Country Status (12)

Country Link
US (1) US7662994B2 (https=)
EP (1) EP1646607B1 (https=)
JP (1) JP5197955B2 (https=)
AT (1) ATE478839T1 (https=)
AU (1) AU2004249526B2 (https=)
CA (1) CA2529018C (https=)
DE (1) DE602004028830D1 (https=)
DK (1) DK1646607T3 (https=)
ES (1) ES2351662T3 (https=)
IT (1) ITTO20030474A1 (https=)
PT (1) PT1646607E (https=)
WO (1) WO2004113271A2 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007144345A3 (en) * 2006-06-14 2008-09-12 Rottapharm Spa Cholecystokinin-1 (cck1) receptor antagonists in the treatment of gastrointestinal and related disorders

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5602179A (en) 1987-02-05 1997-02-11 Rotta Research Laboratorium S.P.A. Optically-active derivatives of (R) 5-pentylamino-5-oxopentanoic acid with antagonistic activity towards cholecystokinin and a method for their preparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69112917T2 (de) * 1990-06-15 1996-05-15 Merck & Co Inc Kristallisationsverfahren zur Verbesserung der Kristallstruktur und -grösse.
US7122083B2 (en) * 2002-04-02 2006-10-17 E. I. Du Pont De Nemours And Company Apparatus and process used in growing crystals

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5602179A (en) 1987-02-05 1997-02-11 Rotta Research Laboratorium S.P.A. Optically-active derivatives of (R) 5-pentylamino-5-oxopentanoic acid with antagonistic activity towards cholecystokinin and a method for their preparation

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
"STN Database", Database accession no. 1196:398396
"STN Database", Database accession no. 1998:370098
"STN Database", Database accession no. 1999:656782
"STN Database", Database accession no. 2002:485631
"STN Database", Database accession no. 2002:50662
"STN Database", Database accession no. 2002:577063
"STN Database", Database accession no. 2002:580010
"STN Database", Database accession no. 2002:580170

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007144345A3 (en) * 2006-06-14 2008-09-12 Rottapharm Spa Cholecystokinin-1 (cck1) receptor antagonists in the treatment of gastrointestinal and related disorders
JP2009539929A (ja) * 2006-06-14 2009-11-19 ロッタファルム・ソシエタ・ペル・アチオニ 胃腸障害および関連障害の治療におけるコレシストキニン−１（ｃｃｋ１）受容体アンタゴニスト
JP2013006858A (ja) * 2006-06-14 2013-01-10 Rottapharm Spa 胃腸障害および関連障害の治療におけるコレシストキニン−１（ｃｃｋ１）受容体アンタゴニスト

Also Published As

Publication number Publication date
HK1089750A1 (en) 2006-12-08
EP1646607A2 (en) 2006-04-19
EP1646607B1 (en) 2010-08-25
ES2351662T3 (es) 2011-02-09
AU2004249526A1 (en) 2004-12-29
CA2529018A1 (en) 2004-12-29
AU2004249526B2 (en) 2011-02-24
PT1646607E (pt) 2010-10-12
DE602004028830D1 (de) 2010-10-07
WO2004113271A3 (en) 2005-01-27
CA2529018C (en) 2013-05-28
US7662994B2 (en) 2010-02-16
WO2004113271A8 (en) 2005-05-06
US20060154987A1 (en) 2006-07-13
ITTO20030474A1 (it) 2004-12-24
JP2007521253A (ja) 2007-08-02
DK1646607T3 (da) 2010-11-22
JP5197955B2 (ja) 2013-05-15
ATE478839T1 (de) 2010-09-15

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