NZ506251A - Benzothiadiazine and benzothiadiazepine derivatives and their use as positive AMPA receptor modulators - Google Patents

Benzothiadiazine and benzothiadiazepine derivatives and their use as positive AMPA receptor modulators

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Publication number
NZ506251A
NZ506251A NZ506251A NZ50625199A NZ506251A NZ 506251 A NZ506251 A NZ 506251A NZ 506251 A NZ506251 A NZ 506251A NZ 50625199 A NZ50625199 A NZ 50625199A NZ 506251 A NZ506251 A NZ 506251A
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NZ
New Zealand
Prior art keywords
alkyl
optionally substituted
aryl
halogen
alkoxy
Prior art date
Application number
NZ506251A
Inventor
Gunnar M Olsen
Elsebet Ostergaard Nielsen
Alex Haahr Gouliaev
Mogens Larsen
Thomas Varming
Claus Mathiesen
Tina Holm Johansen
Jorgen Scheel-Kruger
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Neurosearch As
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Publication of NZ506251A publication Critical patent/NZ506251A/en

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    • 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
    • C07D417/02—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 two hetero rings
    • C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88—Oxygen atoms
    • C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
    • C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
    • C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/15—Six-membered rings
    • C07D285/16—Thiadiazines; Hydrogenated thiadiazines
    • C07D285/18—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines
    • C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
    • C07D285/22—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D285/24—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom
    • C07D285/26—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals
    • C07D285/28—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with oxygen atoms directly attached to the ring sulfur atom substituted in position 6 or 7 by sulfamoyl or substituted sulfamoyl radicals with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Abstract

The compound of the formula shown, where: X is SO2; Y is CH(R4), N(R4), N(R4)-CH2 or O; R2 is H R3 is H, cycloalkyl, alkyl, cycloalkylalkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, alkoxyalkyl, alkoxy, haloalkoxy, -alkyl-NR13R14, -alkyl-S-R13, an optionally substituted carbocyclic 7- to 12- membered ring, an optionally substituted heterocyclic 3- to 8- membered ring (optionally fused to an aryl), optionally substituted benzyl; or R3 and R4 together with the atoms to which they are attached form an optionally substituted 4- to 7- membered ring that optionally contains heteroatoms and carbonyl groups. R4 is H, alkyl, cycloalkyl, cycloalkylalkyl, aryl, -CO-R10, or CO2R10; R5 is H, halogen, alkyl, alkenyl, alkynyl, aryl, or -SO2-NR11R12; R6 is H, halogen, alkyl, cyano, cyanoalkyl, nitro, alkoxy, haloalkoxy, hydroxyalkyl, cycloalkyl, cyclohaloalkyl, -NR15R16, -NHSO2-R15, -NHSO2-aryl, optionally substituted aryl, optionally substituted heterocyclic, -(alkyl)m-S-R15, -(alkyl)m-SO-R15, -(alkyl)m-SO2-R15, -(alkyl)m-SO2OR15, -(alkyl)m-SO2-NR15R16, -(alkyl)m-NHCOR15, -(alkyl)m-CONR15R16, -(alkyl)m-CR'=NOR", -(alkyl)m-CO-R15, or -(alkyl)m-CO2-R15; R7 is halogen, alkyl, cyano, cyanoalkyl, nitroalkyl, alkoxy, haloalkoxy, haloalkyl, hydroalkyl, cycloalkyl, cyclohaloalkyl, -NR17R18, -NHSO2-R17, -NHSO2-aryl, (alkyl)m-S-R17, -(alkyl)m-SO-R17, -(alkyl)m-SO2-R17, -(alkyl)m-SO2OR17, -(alkyl)mNHCOR17, -(alkyl)mCONR17R18, -(alkyl)m-CR'=NOR", -(alkyl)m-CO-R17, -(alkyl)mCO2-R17, -(alkyl)m-SO2-NR17R18, optionally substituted aryl, or optionally substituted heterocyclic; or R7 together with R6, or together with R8, forms a 5- to 7- membered ring; R8 is H, alkyl, alkoxy, hydroxyalkyl, halogen, haloalkyl, cyano, cyanoalkyl, nitro, nitroalkyl, optionally substituted aryl, optionally substituted heterocyclic, -(alkyl)m-S-R19, -(alkyl)m-SO-R19, -(alkyl)m-SO2-R19, -(alkyl)m-SO2OR19, -(alkyl)m-SO2-NR19R20, -(alkyl)mNHCOR19, -(alkyl)mCONR19R20, (alkyl)m-CR'=NOR", -(alkyl)m-CO-R19, or (alkyl)m-CO2-R19; The following proviso applies to the compounds described above: If one of R5, R6, R7, and R8 is halogen or alkyl or alkoxy, then one or more of the remainder of R5, R6, R7, and R8 is/are not halogen or alkyl, and then one or more of the remainder of R5, R6, R7, and R8 is/are not hydrogen. Also described are pharmaceutical compositions comprising the compound described above. The compounds described above are useful for the treatment of diseases and disorders that are responsive to the modulation of the AMPA receptor complex of the central nervous system.
NZ506251A 1998-02-18 1999-02-18 Benzothiadiazine and benzothiadiazepine derivatives and their use as positive AMPA receptor modulators NZ506251A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DK22698 1998-02-18
PCT/DK1999/000070 WO1999042456A2 (en) 1998-02-18 1999-02-18 Novel compounds and their use as positive ampa receptor modulators

Publications (1)

Publication Number Publication Date
NZ506251A true NZ506251A (en) 2003-01-31

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EP (1) EP1071426A2 (en)
JP (1) JP2002504481A (en)
CN (1) CN1293665A (en)
AU (1) AU751384B2 (en)
CA (1) CA2320354A1 (en)
EE (1) EE200000468A (en)
HU (1) HUP0101280A3 (en)
IL (1) IL137720A0 (en)
IS (1) IS5581A (en)
NO (1) NO20004121L (en)
NZ (1) NZ506251A (en)
PL (1) PL342843A1 (en)
RU (1) RU2214405C2 (en)
SK (1) SK11892000A3 (en)
TR (1) TR200002427T2 (en)
WO (1) WO1999042456A2 (en)
ZA (1) ZA991301B (en)

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CA2320354A1 (en) 1999-08-26
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PL342843A1 (en) 2001-07-16
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HUP0101280A3 (en) 2003-02-28
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