CA2162630A1 - Sulfonamides - Google Patents

Sulfonamides

Info

Publication number
CA2162630A1
CA2162630A1 CA002162630A CA2162630A CA2162630A1 CA 2162630 A1 CA2162630 A1 CA 2162630A1 CA 002162630 A CA002162630 A CA 002162630A CA 2162630 A CA2162630 A CA 2162630A CA 2162630 A1 CA2162630 A1 CA 2162630A1
Authority
CA
Canada
Prior art keywords
alkyl
alkoxy
signifies
phenyl
heterocyclyl
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
CA002162630A
Other languages
French (fr)
Other versions
CA2162630C (en
Inventor
Volker Breu
Kaspar Burri
Jean-Marie Cassal
Martine Clozel
Georges Hirth
Bernd-Michael Loffler
Marcel Muller
Werner Neidhart
Henri Ramuz
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
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 filed Critical F Hoffmann La Roche AG
Publication of CA2162630A1 publication Critical patent/CA2162630A1/en
Application granted granted Critical
Publication of CA2162630C publication Critical patent/CA2162630C/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
    • C07D401/02—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 two hetero rings
    • C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • 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
    • 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
    • A61P9/10—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Bipolar Transistors (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Steroid Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Lubricants (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Compounds of the formula, (see formula I) wherein R1 signifies heterocyclyl; R2 signifies hydrogen, lower-alkyl, lower-alkoxy, lower-alkylthio, lower-alkoxy-lower-alkyl, lower-alkylsulphonyl-lower-alkoxy, phenyl, lower alkylphenyl, lower-alkoxy-phenyl, lower-alkylene-dioxyphenyl, phenyl-lower alkyl, lower alkyl-phenyl-lower alkyl, lower alkoxy-phenyl-lower alkyl, lower alkylenedioxyphenyl-lower alkyl, heterocyclyl or heterocyclyl-lower alkyl; R3 signifies lower-alkyl, lower-alkoxy, formyl, halo-lower-alkyl, hydroxy-lower-alkyl, amino-lower-alkyl or a residue -CH2O-A-lower-alkyl, -(CH2)m-O-(CR a R b)n OH, -(CH2)m-O-(CR a R b)n OR9, -(CH2)m-O-(CR a R b)n NH2 or -(CH2)m-O-(CR a R b)n-B-R9; R4-R8 signify hydrogen, lower-alkoxy or halogen; R9 signifies heterocyclyl; phenyl or phenyl substituted by lower-alkyl, lower-alkoxy and/or halogen, or lower-alkyl; R a and R b signify hydrogen or lower-alkyl; A signifies a ketalized 1,2-dihydroxy-ethylene group; B signifies -OC(O)O-, -O(C(O)NH-, -NH(C(O)NH- or -NHC(O)O-: n signifies 2, 3 or 4; and m signifies 0 or 1 are inhibitors for endothelin receptors. They can be used for the treatment of disorders which are associated with endothelin activities, especially circulatory disorders such as hypertension, ischaemia, vasospasms and angina pectoris.
CA002162630A 1994-11-25 1995-11-10 Sulfonamides Expired - Lifetime CA2162630C (en)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
CH355994 1994-11-25
CH3559/94 1994-11-25
CH284295 1995-10-09
CH2842/95 1995-10-09

Publications (2)

Publication Number Publication Date
CA2162630A1 true CA2162630A1 (en) 1996-05-26
CA2162630C CA2162630C (en) 2007-05-01

Family

ID=25691537

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002162630A Expired - Lifetime CA2162630C (en) 1994-11-25 1995-11-10 Sulfonamides

Country Status (22)

Country Link
EP (1) EP0713875B1 (en)
JP (1) JP2755565B2 (en)
KR (1) KR100415030B1 (en)
AT (1) ATE199905T1 (en)
AU (1) AU691353B2 (en)
CA (1) CA2162630C (en)
CZ (1) CZ289920B6 (en)
DE (1) DE59509107D1 (en)
DK (1) DK0713875T3 (en)
ES (1) ES2156179T3 (en)
FI (1) FI117896B (en)
GR (1) GR3036065T3 (en)
HK (1) HK1012345A1 (en)
HU (1) HU225112B1 (en)
IL (1) IL116064A (en)
MA (1) MA23725A1 (en)
MY (1) MY119409A (en)
NO (1) NO307606B1 (en)
NZ (1) NZ280495A (en)
PT (1) PT713875E (en)
RU (1) RU2162084C2 (en)
TW (1) TW394763B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2217034A1 (en) * 1995-04-03 1996-10-10 Sumitomo Pharmaceuticals Company, Limited Novel pyrimidine derivatives effective as psychotropic drug and process for the production thereof
DE69824090T2 (en) * 1997-08-19 2005-07-07 F. Hoffmann-La Roche Ag Process for the preparation of 2,5-disubstituted pyridines
TWI284642B (en) * 1999-01-18 2007-08-01 Hoffmann La Roche Novel heterocyclic sulfonamides
US6417360B1 (en) * 1999-03-03 2002-07-09 Hoffmann-La Roche Inc. Heterocyclic sulfonamides
CA2361402C (en) * 1999-09-03 2009-05-12 Actelion Pharmaceuticals Ltd Bis-sulfonamides
CN1407973A (en) * 1999-12-22 2003-04-02 埃科特莱茵药品有限公司 Butyne diol derivatives
AU2001265871A1 (en) * 2000-04-25 2001-11-07 Actelion Pharmaceuticals Ltd Substituted sulfonylaminopyrimidines
US6387915B2 (en) 2000-05-31 2002-05-14 Pfizer Inc. Isoxazole-sulfonamide endothelin antagonists
US6670362B2 (en) 2000-09-20 2003-12-30 Pfizer Inc. Pyridazine endothelin antagonists
DE60207890T2 (en) * 2001-12-18 2006-08-10 Astrazeneca Ab NEW CONNECTIONS
TWI328007B (en) 2002-01-16 2010-08-01 Astrazeneca Ab Novel compounds
EP1454625A1 (en) * 2003-03-06 2004-09-08 Speedel Development AG Pyridylsulfonamidyl-pyrimidines for the treatment of diabetic nephropathies
DK1725540T5 (en) * 2004-03-05 2012-10-22 Hoffmann La Roche DIAMINOPYRIMIDINES AS P2X3 AND P2X2 / 3 ANTAGONISTS

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2086544C1 (en) * 1991-06-13 1997-08-10 Хоффманн-Ля Рош АГ Benzenesulfonamide derivatives of pyrimidine or their salts, pharmaceutical composition for treatment of diseases associated with endothelin activity
TW287160B (en) * 1992-12-10 1996-10-01 Hoffmann La Roche
TW394761B (en) * 1993-06-28 2000-06-21 Hoffmann La Roche Novel Sulfonylamino Pyrimidines

Also Published As

Publication number Publication date
CZ289920B6 (en) 2002-04-17
EP0713875A1 (en) 1996-05-29
NO307606B1 (en) 2000-05-02
DK0713875T3 (en) 2001-06-11
EP0713875B1 (en) 2001-03-21
JP2755565B2 (en) 1998-05-20
CA2162630C (en) 2007-05-01
NO954718D0 (en) 1995-11-22
NZ280495A (en) 1996-12-20
PT713875E (en) 2001-09-28
AU691353B2 (en) 1998-05-14
MA23725A1 (en) 1996-07-01
ATE199905T1 (en) 2001-04-15
FI955669A (en) 1996-05-26
JPH08208625A (en) 1996-08-13
KR960017644A (en) 1996-06-17
CZ308895A3 (en) 1997-07-16
MY119409A (en) 2005-05-31
NO954718L (en) 1996-05-28
AU3789595A (en) 1996-05-30
KR100415030B1 (en) 2004-05-17
HK1012345A1 (en) 1999-07-30
IL116064A (en) 2000-06-29
GR3036065T3 (en) 2001-09-28
TW394763B (en) 2000-06-21
ES2156179T3 (en) 2001-06-16
FI117896B (en) 2007-04-13
HUT75030A (en) 1997-03-28
IL116064A0 (en) 1996-01-31
HU9503311D0 (en) 1996-01-29
DE59509107D1 (en) 2001-04-26
HU225112B1 (en) 2006-06-28
FI955669A0 (en) 1995-11-24
RU2162084C2 (en) 2001-01-20

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Effective date: 20151110