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WO1992012969A1 - Sels d'un derive de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de la secretion de l'acide gastrique - Google Patents

Sels d'un derive de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de la secretion de l'acide gastrique Download PDF

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Publication number
WO1992012969A1
WO1992012969A1 PCT/EP1992/000200 EP9200200W WO9212969A1 WO 1992012969 A1 WO1992012969 A1 WO 1992012969A1 EP 9200200 W EP9200200 W EP 9200200W WO 9212969 A1 WO9212969 A1 WO 9212969A1
Authority
WO
WIPO (PCT)
Prior art keywords
salts
inhibitors
amino
salt
methylphenylamino
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/EP1992/000200
Other languages
English (en)
Inventor
Robert John Ife
Colin Andrew Leach
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.)
SmithKline Beecham Intercredit BV
Original Assignee
SmithKline Beecham Intercredit BV
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 claimed from GB919101919A external-priority patent/GB9101919D0/en
Priority claimed from GB919101918A external-priority patent/GB9101918D0/en
Application filed by SmithKline Beecham Intercredit BV filed Critical SmithKline Beecham Intercredit BV
Priority to AU11799/92A priority Critical patent/AU652028B2/en
Priority to JP4503051A priority patent/JPH06504541A/ja
Priority to FI933376A priority patent/FI933376A7/fi
Priority to CZ931532A priority patent/CZ153293A3/cs
Priority to SK709-93A priority patent/SK70993A3/sk
Publication of WO1992012969A1 publication Critical patent/WO1992012969A1/fr
Priority to NO93932722A priority patent/NO932722L/no
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
    • 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

Definitions

  • the present invention relates to certain salts of a quinoline compound, pharmaceutical compositions containing them and their use in therapy as inhibitors of gastric acid secretion.
  • EP-330485-A discloses a series of 4-amino-3- acylquinoline derivatives in which the quinoline is substituted in the 8-position by, for example, hydroxyalkyl and hydroxyalkoxy groups.
  • the compounds of EP 330485-A have been found to have poor dissolution rates in water and, as a consequence, could potentially exhibit poor bioavailability in vivo and hence low and poorly reproducible levels of therapeutic activity. It has now been found that the problem of poor dissolution can be overcome by producing the compounds in the form of a particular class of salts. Furthermore, in selecting compounds for use in therapy it is important to take a number or criteria into account, for example, in addition to physical qualities such as good dissolution (and hence good bioavailability) , the desired level of intrinsic potency and duration of action of the chosen compounds has to be at the desired level.
  • strong acid shall be taken to mean an acid with a pka of less than about 4.0.
  • the nature of such acids will be apparent to those skilled in the art and include, for example, mineral acids such as hydrochloric acid, and sulphonic acids such as alkyl sulphonic acids, in particular methane sulphonic acid.
  • Particularly preferred salts of the present invention are those formed by reaction with hydrochloric acid or methane sulphonic acid, that is to say,
  • the salts of the present invention have been found to exhibit exceptionally fast intrinsic dissolution rates when compared to the free base compound of structure (I) disclosed in EP-330485-A.
  • the free base has a poor dissolution rate and, as such, may be expected in vivo to exhibit poorly reproducible bioavailability (and so be less effective therapeutically)
  • the salts of the present invention are expected to exhibit a much more consistent bioavailability (since their dissolution rates are far more favourable) and to prove more effective per given dose and more reliably effective per given dose on administration to patients.
  • the salts described herein can be used in therapy in the treatment of gastrointestinal diseases in mammals, in particular humans. Such diseases include, for example, gastric and duodenal ulcers, aspiration pneumonitis and Zollinger-Ellison syndrome. Further, the salts can be used in the treatment of other disorders where an anti-secretory effect is desirable, for example in patients with a history of chronic and excessive alcohol consumption, and in patients with gastrooesophageal reflux disease (GERD) .
  • GSD gastrooesophageal reflux disease
  • the salts can be administered in a standard pharmaceutical composition comprising the salt and a pharmaceutically acceptable carrier.
  • the present invention provides in a further aspect therefore a pharmaceutical composition comprising a salt as described herein in association with a pharmaceutically acceptable carrier.
  • Suitable pharmaceutical compositions are as described in EP-330485-A.
  • Suitable daily dosage regimens for an adult patient may be, for example, an oral dose of between 1 and 1000 mg, preferably between 1 and 500 mg, or an intravenous, subcutaneous or intramuscular dose of between 0.1 and 100 mg, preferably between 0.1 and 25 mg of the salts described herein, the salt being administered in a unit dosage 1 to 4 times a day.
  • the salts can be co-administered with further active ingredients such as antacids (for example, magnesium carbonate or hydroxide and aluminium hydroxide) , non-steroidal anti-inflammatory drugs, steroids or nitrite scavengers or other drugs used for treating gastric ulcers (for example, prostanoids or H 2 -antagonists such as cimetidine) .
  • antacids for example, magnesium carbonate or hydroxide and aluminium hydroxide
  • non-steroidal anti-inflammatory drugs for example, steroids or nitrite scavengers or other drugs used for treating gastric ulcers (for example, prostanoids or H 2 -antagonists such as cimetidine) .
  • active ingredients such as antacids (for example, magnesium carbonate or hydroxide and aluminium hydroxide) , non-steroidal anti-inflammatory drugs, steroids or nitrite scavengers or other drugs used for treating gastric ulcers (for example, prostanoids or H 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth 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)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

Composé de structure (I) sous la forme d'un sel, procédé de préparation de ce composé et compositions pharmaceutiques comprenant ce sel et son utilisation en thérapie.
PCT/EP1992/000200 1991-01-29 1992-01-27 Sels d'un derive de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de la secretion de l'acide gastrique Ceased WO1992012969A1 (fr)

Priority Applications (6)

Application Number Priority Date Filing Date Title
AU11799/92A AU652028B2 (en) 1991-01-29 1992-01-27 Salts of a 4-amino-3-acyl quinoline derivatives
JP4503051A JPH06504541A (ja) 1991-01-29 1992-01-27 ４−アミノ−３−アシルキノリン誘導体の塩およびその胃酸分泌抑制剤としての使用
FI933376A FI933376A7 (fi) 1991-01-29 1992-01-27 4-amino-3-asyylikinoliinijohdannaisten suolat ja niiden käyttö vatsaha ppoerityksen inhibiittoreina
CZ931532A CZ153293A3 (en) 1991-01-29 1992-01-27 Salts of 4-amino-acylquinoline derivative
SK709-93A SK70993A3 (en) 1991-01-29 1992-01-27 Salts of 4-amino-3-acylquionoline derivative and their use as inhibitors of gastric acid secretion
NO93932722A NO932722L (no) 1991-01-29 1993-07-28 Salter av et 4-amino-3acyl-kinolinderivat og deres anvendelse som inhibatorer for gastrisk syresekresjon

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9101918.2 1991-01-29
GB919101919A GB9101919D0 (en) 1991-01-29 1991-01-29 Compound
GB9101919.0 1991-01-29
GB919101918A GB9101918D0 (en) 1991-01-29 1991-01-29 Compound

Publications (1)

Publication Number Publication Date
WO1992012969A1 true WO1992012969A1 (fr) 1992-08-06

Family

ID=26298350

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/000200 Ceased WO1992012969A1 (fr) 1991-01-29 1992-01-27 Sels d'un derive de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de la secretion de l'acide gastrique

Country Status (18)

Country Link
EP (1) EP0569396A1 (fr)
JP (1) JPH06504541A (fr)
CN (1) CN1064268A (fr)
AP (1) AP337A (fr)
AU (1) AU652028B2 (fr)
CA (1) CA2099117A1 (fr)
CZ (1) CZ153293A3 (fr)
FI (1) FI933376A7 (fr)
HU (1) HUT67609A (fr)
IE (1) IE920267A1 (fr)
IL (1) IL100791A0 (fr)
MA (1) MA22401A1 (fr)
MX (1) MX9200338A (fr)
NO (1) NO932722L (fr)
NZ (1) NZ241408A (fr)
PT (1) PT100056A (fr)
SK (1) SK70993A3 (fr)
WO (1) WO1992012969A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993012090A1 (fr) * 1991-12-12 1993-06-24 Smithkline Beecham Intercredit B.V. Derives de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de secretion d'acide gastrique
WO1994029274A1 (fr) * 1993-06-11 1994-12-22 Astra Aktiebolag Nouveaux composes actifs
WO1996017830A1 (fr) * 1994-12-08 1996-06-13 Astra Aktiebolag Composes destines a inhiber la secretion d'acide gastrique
WO2003043614A3 (fr) * 2001-11-19 2004-03-11 Altana Pharma Ag Agents utiles pour le traitement des troubles des voies aeriennes
US6852739B1 (en) 1999-02-26 2005-02-08 Nitromed Inc. Methods using proton pump inhibitors and nitric oxide donors
US7175854B2 (en) 2000-12-07 2007-02-13 Altana Pharma Ag Pharmaceutical preparation comprising an active dispersed on a matrix
US7211590B2 (en) 2002-08-01 2007-05-01 Nitromed, Inc. Nitrosated proton pump inhibitors, compositions and methods of use
EP1974730A1 (fr) 2003-11-03 2008-10-01 AstraZeneca AB Dérivés d'imidazo[1,2-a]pyridine pour l'utilisation dans le traitement des troubles du sommeil provoqués par un reflux gastro-oesophagien silencieux
US7951397B2 (en) 2002-02-20 2011-05-31 Nycomed Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
USRE43932E1 (en) 1997-07-18 2013-01-15 Novartis Ag Crystal modification of a N-phenyl-2-pyrimidineamine derivative, processes for its manufacture and its use

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0330485A1 (fr) * 1988-02-25 1989-08-30 SmithKline Beecham Intercredit B.V. Dérivés des 4-amino-3-acylquinoléines, et leur utilisation pour l'inhibition de la sécrétion gastrique

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0330485A1 (fr) * 1988-02-25 1989-08-30 SmithKline Beecham Intercredit B.V. Dérivés des 4-amino-3-acylquinoléines, et leur utilisation pour l'inhibition de la sécrétion gastrique

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993012090A1 (fr) * 1991-12-12 1993-06-24 Smithkline Beecham Intercredit B.V. Derives de 4-amino-3-acyle quinoline et leur utilisation comme inhibiteurs de secretion d'acide gastrique
WO1994029274A1 (fr) * 1993-06-11 1994-12-22 Astra Aktiebolag Nouveaux composes actifs
US5556863A (en) * 1993-06-11 1996-09-17 Astra Aktiebolag Compound for gastric acid secretion inhibition
AU680516B2 (en) * 1993-06-11 1997-07-31 Astra Aktiebolag New active compounds
US5889021A (en) * 1993-06-11 1999-03-30 Astra Aktiebolag Active Compounds
CN1045955C (zh) * 1993-06-11 1999-10-27 阿斯特拉公司 喹啉衍生物及其制法和用途以及含该衍生物的药物组合物
WO1996017830A1 (fr) * 1994-12-08 1996-06-13 Astra Aktiebolag Composes destines a inhiber la secretion d'acide gastrique
AU697006B2 (en) * 1994-12-08 1998-09-24 Astra Aktiebolag Compounds for inhibition of gastric acid secretion
USRE43932E1 (en) 1997-07-18 2013-01-15 Novartis Ag Crystal modification of a N-phenyl-2-pyrimidineamine derivative, processes for its manufacture and its use
US7332505B2 (en) 1999-02-26 2008-02-19 Nitromed, Inc. Nitrosated and nitrosylated proton pump inhibitors, compositions and methods of use
US6852739B1 (en) 1999-02-26 2005-02-08 Nitromed Inc. Methods using proton pump inhibitors and nitric oxide donors
US7175854B2 (en) 2000-12-07 2007-02-13 Altana Pharma Ag Pharmaceutical preparation comprising an active dispersed on a matrix
US7951398B2 (en) 2000-12-07 2011-05-31 Nycomed Gmbh Pharmaceutical preparation comprising an active dispersed on a matrix
WO2003043614A3 (fr) * 2001-11-19 2004-03-11 Altana Pharma Ag Agents utiles pour le traitement des troubles des voies aeriennes
US7951397B2 (en) 2002-02-20 2011-05-31 Nycomed Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
US8431154B2 (en) 2002-02-20 2013-04-30 Takeda Gmbh Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidone as excipient
US9468598B2 (en) 2002-02-20 2016-10-18 Astrazeneca Ab Oral dosage form containing a PDE 4 inhibitor as an active ingredient and polyvinylpyrrolidon as excipient
US7211590B2 (en) 2002-08-01 2007-05-01 Nitromed, Inc. Nitrosated proton pump inhibitors, compositions and methods of use
EP1974730A1 (fr) 2003-11-03 2008-10-01 AstraZeneca AB Dérivés d'imidazo[1,2-a]pyridine pour l'utilisation dans le traitement des troubles du sommeil provoqués par un reflux gastro-oesophagien silencieux

Also Published As

Publication number Publication date
EP0569396A1 (fr) 1993-11-18
IE920267A1 (en) 1992-07-29
PT100056A (pt) 1993-03-31
CN1064268A (zh) 1992-09-09
AP9200352A0 (en) 1992-01-31
NO932722D0 (no) 1993-07-28
CZ153293A3 (en) 1993-12-15
JPH06504541A (ja) 1994-05-26
FI933376L (fi) 1993-07-28
AP337A (en) 1994-04-08
CA2099117A1 (fr) 1992-07-30
IL100791A0 (en) 1992-09-06
HU9302201D0 (en) 1993-10-28
NO932722L (no) 1993-07-28
NZ241408A (en) 1994-05-26
FI933376A0 (fi) 1993-07-28
AU1179992A (en) 1992-08-27
HUT67609A (en) 1995-04-28
FI933376A7 (fi) 1993-07-28
AU652028B2 (en) 1994-08-11
SK70993A3 (en) 1994-01-12
MX9200338A (es) 1992-12-01
MA22401A1 (fr) 1992-10-01

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