CA2364906A1 - 4-heterocyclysulfonamidyl-6-methoxy-5-(2-methoxy-phenoxy)-2-pyridyl-pyrimidine derivatives, their preparation and use as endothelin receptor antagonists - Google Patents

4-heterocyclysulfonamidyl-6-methoxy-5-(2-methoxy-phenoxy)-2-pyridyl-pyrimidine derivatives, their preparation and use as endothelin receptor antagonists Download PDF

Info

Publication number
CA2364906A1
CA2364906A1 CA002364906A CA2364906A CA2364906A1 CA 2364906 A1 CA2364906 A1 CA 2364906A1 CA 002364906 A CA002364906 A CA 002364906A CA 2364906 A CA2364906 A CA 2364906A CA 2364906 A1 CA2364906 A1 CA 2364906A1
Authority
CA
Canada
Prior art keywords
methoxy
heterocyclysulfonamidyl
phenoxy
pyridyl
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.)
Granted
Application number
CA002364906A
Other languages
French (fr)
Other versions
CA2364906C (en
Inventor
Volker Breu
Philippe Coassolo
Werner Neidhart
Sebastien Roux
Peter Weiss
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.)
F Hoffmann La Roche AG
Original Assignee
F. Hoffmann-La Roche Ag
Volker Breu
Philippe Coassolo
Werner Neidhart
Sebastien Roux
Peter Weiss
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 F. Hoffmann-La Roche Ag, Volker Breu, Philippe Coassolo, Werner Neidhart, Sebastien Roux, Peter Weiss filed Critical F. Hoffmann-La Roche Ag
Publication of CA2364906A1 publication Critical patent/CA2364906A1/en
Application granted granted Critical
Publication of CA2364906C publication Critical patent/CA2364906C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/06—Antimigraine agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Abstract

The compounds of formula (I) wherein R1 is a heterocyclic residue selected form pyridil and thiazolyl, where said heterocyclic residue may optionally be substituted with lower alkyl or lower alkenyl; and pharmaceutically acceptable salts thereof, are inhibitors of endothelin receptors and can therefore be used for the treatment of disorders which are associated with abnormal vascular tone and endothelial dysfunction; and the corresponding intermediates of formulae (III) and (V).
CA002364906A 1999-03-03 2000-02-28 4-heterocyclysulfonamidyl-6-methoxy-5-(2-methoxy-phenoxy)-2-pyridyl-pyrimidine derivatives, their preparation and use as endothelin receptor antagonists Expired - Lifetime CA2364906C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP99104306 1999-03-03
EP99104306.8 1999-03-03
PCT/EP2000/001660 WO2000052007A1 (en) 1999-03-03 2000-02-28 4-heterocyclysulfonamidyl-6-methoxy-5-(2-methoxy-phenoxy)-2-pyridyl-pyrimidine derivatives, their preparation and use as endothelin receptor antagonists

Publications (2)

Publication Number Publication Date
CA2364906A1 true CA2364906A1 (en) 2000-09-08
CA2364906C CA2364906C (en) 2006-01-10

Family

ID=8237697

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002364906A Expired - Lifetime CA2364906C (en) 1999-03-03 2000-02-28 4-heterocyclysulfonamidyl-6-methoxy-5-(2-methoxy-phenoxy)-2-pyridyl-pyrimidine derivatives, their preparation and use as endothelin receptor antagonists

Country Status (30)

Country Link
US (2) US6417360B1 (en)
EP (1) EP1185525B1 (en)
JP (1) JP3488203B2 (en)
KR (1) KR100478798B1 (en)
CN (1) CN1342158B (en)
AR (1) AR044720A1 (en)
AT (1) ATE353325T1 (en)
AU (1) AU756738B2 (en)
BR (1) BR0008717A (en)
CA (1) CA2364906C (en)
CY (1) CY1108002T1 (en)
CZ (1) CZ300324B6 (en)
DE (1) DE60033280T2 (en)
DK (1) DK1185525T3 (en)
ES (1) ES2280198T3 (en)
HK (1) HK1044943B (en)
HR (1) HRP20010630B1 (en)
HU (1) HUP0200080A3 (en)
ID (1) ID30484A (en)
IL (1) IL145051A0 (en)
MA (1) MA26776A1 (en)
NO (1) NO320809B1 (en)
NZ (1) NZ513671A (en)
PL (1) PL198815B1 (en)
PT (1) PT1185525E (en)
RS (1) RS50109B (en)
RU (1) RU2201928C1 (en)
TR (1) TR200102562T2 (en)
WO (1) WO2000052007A1 (en)
ZA (1) ZA200107157B (en)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
MY140724A (en) 2000-07-21 2010-01-15 Actelion Pharmaceuticals Ltd Novel arylethene-sulfonamides
US20020184047A1 (en) * 2001-04-03 2002-12-05 Plotnick Michael A. Universal ad queue
EP1454625A1 (en) * 2003-03-06 2004-09-08 Speedel Development AG Pyridylsulfonamidyl-pyrimidines for the treatment of diabetic nephropathies
EP1595880A1 (en) * 2004-05-13 2005-11-16 Speedel Pharma AG Crystalline forms of a pyridinyl-sulfonamide and their use as endothelin receptor antagonists
JP2009507890A (en) * 2005-09-12 2009-02-26 シュペーデル・ファルマ・アーゲー Pyridylsulfonamidyl-pyrimidines for the prevention of vascular graft dysfunction
MX2008013034A (en) * 2006-04-13 2008-10-17 Actelion Pharmaceuticals Ltd Endothelin receptor antagonists for early stage idiopathic pulmonary fibrosis.
EP1938812A1 (en) * 2006-12-22 2008-07-02 Speedel Pharma AG Pharmaceutical composition using aliskiren and avosentan
WO2010011868A2 (en) * 2008-07-23 2010-01-28 Auspex Pharmaceuticals Pyridine sulfonamide modulators of endothelin-a-receptor
CA2975260A1 (en) 2015-01-29 2016-08-04 Signal Pharmaceuticals Llc Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide
KR101936054B1 (en) 2017-06-23 2019-01-11 한국과학기술연구원 Anti-inflammatory 6-phenoxypyrimidine derivatives, process for their preparation and pharmaceutical composition containing them
WO2023111299A1 (en) 2021-12-17 2023-06-22 Idorsia Pharmaceuticals Ltd Clazosentan disodium salt, its preparation and pharmaceutical compositions comprising the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5837708A (en) 1994-11-25 1998-11-17 Hoffmann-La Roche Inc. Sulphonamides
CN1064965C (en) * 1994-11-25 2001-04-25 弗·哈夫曼-拉罗切有限公司 Novel sulfonamides compound and its use as medicine
CA2162630C (en) 1994-11-25 2007-05-01 Volker Breu Sulfonamides
TW313568B (en) * 1994-12-20 1997-08-21 Hoffmann La Roche
DK0897914T3 (en) 1997-08-19 2004-09-27 Hoffmann La Roche Process for Preparation of 2,5-Disubstituted Pyridines
TWI284642B (en) * 1999-01-18 2007-08-01 Hoffmann La Roche Novel heterocyclic sulfonamides

Also Published As

Publication number Publication date
HRP20010630B1 (en) 2010-08-31
HUP0200080A3 (en) 2003-01-28
NO20014224D0 (en) 2001-08-31
BR0008717A (en) 2001-12-26
AR044720A1 (en) 2005-10-05
HK1044943A1 (en) 2002-11-08
PL351794A1 (en) 2003-06-16
IL145051A0 (en) 2002-06-30
CZ20013108A3 (en) 2002-02-13
RU2201928C1 (en) 2003-04-10
MA26776A1 (en) 2004-12-20
EP1185525B1 (en) 2007-02-07
KR100478798B1 (en) 2005-03-24
CN1342158A (en) 2002-03-27
RU2001126348A (en) 2004-03-20
HK1044943B (en) 2013-03-22
YU62801A (en) 2004-07-15
JP2002538156A (en) 2002-11-12
EP1185525A1 (en) 2002-03-13
NO320809B1 (en) 2006-01-30
WO2000052007A1 (en) 2000-09-08
US6521631B2 (en) 2003-02-18
NO20014224L (en) 2001-08-31
PT1185525E (en) 2007-05-31
JP3488203B2 (en) 2004-01-19
ATE353325T1 (en) 2007-02-15
US6417360B1 (en) 2002-07-09
HRP20010630A2 (en) 2002-08-31
AU756738B2 (en) 2003-01-23
PL198815B1 (en) 2008-07-31
RS50109B (en) 2009-03-25
AU3161100A (en) 2000-09-21
ID30484A (en) 2001-12-13
DK1185525T3 (en) 2007-06-04
ES2280198T3 (en) 2007-09-16
CA2364906C (en) 2006-01-10
CY1108002T1 (en) 2013-09-04
ZA200107157B (en) 2002-11-29
KR20010102480A (en) 2001-11-15
DE60033280D1 (en) 2007-03-22
CZ300324B6 (en) 2009-04-22
CN1342158B (en) 2012-06-06
HUP0200080A2 (en) 2002-06-29
DE60033280T2 (en) 2007-11-22
US20020137933A1 (en) 2002-09-26
TR200102562T2 (en) 2002-02-21
NZ513671A (en) 2003-04-29

Similar Documents

Publication Publication Date Title
CA2359363A1 (en) 4-(heterocyclylsulfonamido)-5-methoxy-6-(2-methoxyphenoxy)-2-phenyl- or pyridylpyrimidines as endothelin receptor antagonists
NO20020823D0 (en) Heterocyclic compounds and their use as metabotrophic glutamate receptor antagonists
DK0889877T3 (en) Meta-substituted phenylene derivatives and their use as alpha-beta3 integrin antagonists or inhibitors
NO986055D0 (en) New heterocyclic compounds, their preparation, pharmaceutical preparations
CY1108002T1 (en) 4-HETEROCYLICULYSULPHONAMYLYL-6-Methoxy-5- (2-Methoxy-phenoxy) -2-Pyridyl-Pyrimidine Derivative, Producing
DE69705829D1 (en) META-SUBSTITUTED PHENYLSULPHONAMIDE DERIVATIVES
AR039329A1 (en) TRIAZOL DERIVATIVES, TAQUYCININE RECEIVER ANTAGONISTS
ATE219077T1 (en) ENDOTHELIN ANTAGONIST
HK1019334A1 (en) 2-(arylphenyl) amino-imidazoline derivatives
CA2388470A1 (en) Use of carbonylamino derivatives against cns disorders
DE60016786D1 (en) BICYCLIC VASOPRESSINE AGONIST
IL150276A0 (en) Indole derivatives as mcp-1 receptor antagonists
YU38498A (en) 2-(arylphenyl)amino-imidazoline derivatives
EP1582519A3 (en) Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20200228