GB946864A - Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides - Google Patents

Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides

Info

Publication number
GB946864A
GB946864A GB1616960A GB1616960A GB946864A GB 946864 A GB946864 A GB 946864A GB 1616960 A GB1616960 A GB 1616960A GB 1616960 A GB1616960 A GB 1616960A GB 946864 A GB946864 A GB 946864A
Authority
GB
United Kingdom
Prior art keywords
treating
aliphatic hydrocarbon
group
formula
alkyl
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.)
Expired
Application number
GB1616960A
Inventor
Peter Werner Feit
Erling Juhl Nielsen
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.)
KNUD ABILDGAARD
Original Assignee
KNUD ABILDGAARD
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 KNUD ABILDGAARD filed Critical KNUD ABILDGAARD
Priority to GB1616960A priority Critical patent/GB946864A/en
Priority to CH506161A priority patent/CH393341A/en
Priority to DK184864A priority patent/DK104349C/en
Priority to DK185961A priority patent/DK105274C/en
Publication of GB946864A publication Critical patent/GB946864A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • 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
    • C07D285/30—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 hydrocarbon radicals, substituted by hetero atoms, attached in position 3

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

3:4 - Dihydro - 1:2:4 - benzothiadiazine - 1:1 - dioxides of the formula: <FORM:0946864/C2/1> in which R1 is halogen, e.g. Cl or Br, or CF3, R2 is hydrogen or a C1-6 aliphatic hydrocarbon radical, a C3-6 monocyclic aliphatic hydrocarbon, e.g. cycloalkyl or cycloalkenyl, radical, an alkyl group substituted by a C3-6 monocyclic aliphatic hydrocarbon radical or a phenyl, phenylalkyl or phenylalkyl radical, all of which radicals may optionally bear halogen, nitro or esterified or etherified hydroxy or mercapto substituents, R3 and R4 are hydrogen or alkyl, phenyl, phenylalkyl or C3-6 monocyclic aliphatic hydrocarbon groups or alkyl groups substituted by a C3-6 monocyclic aliphatic hydrocarbon group, or R3 and R4 form with the N-atom of the sulphamoyl group a heterocyclic ring such as piperidine, pyrrolidine or morpholine and R5 is a hydrogen atom or a C1-6 alkyl or alkenyl group, are prepared by treating a disulphide of the formula: <FORM:0946864/C2/2> wherein X is an amino group and Y is a substituted or unsubstituted sulphamyl group or X and Y together with the two carbon atoms of the benzene ring form a dihydrothiadiazine ring (optionally bearing substituents R2 and R5), with oxidising and sulphonyl halide forming agents, e.g. (a) with hydrogen peroxide to give a sulphinic acid which is then treated with an aqueous solution of a halogen, (b) with an excess of hydrogen peroxide to give a suplhonic acid which is halogenated with an inorganic acid halide, or (c) in one step by treating the compound of formula II with chlorine; treating the 2 - sulphamoyl-aniline - 4 - sulphonyl halide if formed i.e. in the case where X is amino and Y is sulphamoyl with an aldehyde R2CHO to effect cyclization and condensing the resulting 3,4 - dihydrobenzo -thiadiazine - 7 - sulphonyl halide with ammonia or an amine R3-NH-R4. Bis - (6 - R1 - 3,4 - dihydro - 1,2,4 - benzothiadiazine - 1,1 - dioxide-7) - disulphides corresponding to the formula II wherein X and Y form a dihydrothiadiazine ring, are prepared by treating a 5 - R1 - 2 - sulphamyl - aniline with thiocyanogen in acetic acid, treating the resulting 4-thiocyanate with ammonia to give a bis-(2-R1-4-amino-5-sulphamyl - phenyl) - disulphide and condensing with an aldehyde R2CHO. Cyclopentyl - acetaldehyde - dimethylacetal is made by reaction of methylorthoformate with cyclopentylmethyl magnesium bromide. Specifications 847,064, 861,367 and 863,474 are referred to.
GB1616960A 1960-05-06 1960-05-06 Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides Expired GB946864A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
GB1616960A GB946864A (en) 1960-05-06 1960-05-06 Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides
CH506161A CH393341A (en) 1960-05-06 1961-05-01 Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxydes
DK184864A DK104349C (en) 1960-05-06 1961-05-05 Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide derivatives.
DK185961A DK105274C (en) 1960-05-06 1961-05-05 Process for the preparation of substituted 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxide derivatives.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1616960A GB946864A (en) 1960-05-06 1960-05-06 Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides
DEL0038926 1961-05-05

Publications (1)

Publication Number Publication Date
GB946864A true GB946864A (en) 1964-01-15

Family

ID=25985420

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1616960A Expired GB946864A (en) 1960-05-06 1960-05-06 Method for the production of 3,4-dihydro-1,2,4-benzothiadiazine-1,1-dioxides

Country Status (1)

Country Link
GB (1) GB946864A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999042456A2 (en) * 1998-02-18 1999-08-26 Neurosearch A/S Novel compounds and their use as positive ampa receptor modulators
US6943159B1 (en) 1998-02-18 2005-09-13 Neurosearch A/S Compounds and their use as positive AMPA receptor modulators

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999042456A2 (en) * 1998-02-18 1999-08-26 Neurosearch A/S Novel compounds and their use as positive ampa receptor modulators
WO1999042456A3 (en) * 1998-02-18 1999-10-07 Neurosearch As Novel compounds and their use as positive ampa receptor modulators
US6943159B1 (en) 1998-02-18 2005-09-13 Neurosearch A/S Compounds and their use as positive AMPA receptor modulators
US7235548B2 (en) 1998-02-18 2007-06-26 Neurosearch A/S Compounds and their use as positive AMPA receptor modulators

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