GB975921A - Improvements in or relating to 9-substituted-1-azathiaxanthenes - Google Patents

Improvements in or relating to 9-substituted-1-azathiaxanthenes

Info

Publication number
GB975921A
GB975921A GB597461A GB597461A GB975921A GB 975921 A GB975921 A GB 975921A GB 597461 A GB597461 A GB 597461A GB 597461 A GB597461 A GB 597461A GB 975921 A GB975921 A GB 975921A
Authority
GB
United Kingdom
Prior art keywords
compounds
formula
acid
atom
salt
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
GB597461A
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.)
Sandoz AG
Original Assignee
Sandoz 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
Priority claimed from CH328060A external-priority patent/CH383382A/en
Application filed by Sandoz AG filed Critical Sandoz AG
Publication of GB975921A publication Critical patent/GB975921A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Abstract

The invention comprises compounds of the general formula <FORM:0975921/C1/1> and their acid addition salts, wherein R1 represents a hydrogen or halogen atom, each of R2 and R3 represent a hydrogen atom and each of R4 and R5 represents an alkyl group containing 4 or less carbon atoms or R5 together with R2 or R3 or R4 represents an alkylene group containing at most 4 carbon atoms in a straight chain with the proviso that when a heterocyclic radical is attached to carbon atom 9 of the azathiaxanthene nucleus, it must contain 5 or 6-members, and the preparation thereof by reacting an organic metal compound of the formula <FORM:0975921/C1/2> wherein Hal represents a chlorine, bromine or iodine atom, with a 1-azathiaxanthone of the formula <FORM:0975921/C1/3> hydrolyzing the reaction product to form a 1-azathiaxanthydiol of the formula <FORM:0975921/C1/4> and treating this with a dehydrating agent, and, if desired, reacting the base with an organic or inorganic acid to produce the acid addition salt. The process of the invention may be combined with one for the preparation of the halo-1-azathiaxanthones by heating a halogenothiophenol with a solution of a diazonium salt of 3-aminopyridine-2-carboxylic acid in the presence of an alkali metal hydroxide, converting the alkali-metal salt of 2-carboxypyridyl-3-halogenophenyl sulphide resulting thereby to the free acid and then cyclising the corresponding acid halide in the presence of a cyclization agent. Separation of the compounds of the invention into the individual stereoisomers and separation of the halo-1-azathiaxanthones into the individual positional isomers are carried out by fractional crystallization. m-Dichlorodiphenyldisulphide is formed as a byproduct in the reaction between the diazonium salt and m-chlorothiophenol above. Pharmaceutical compositions comprise the compounds of the invention and an inert carrier. The compounds show marked histamine inhibition, seratonin inhibition, narcosis potentiation, adrenolytic, sedative, antipyretic or hypothermal effects according to the nature of the substituent groups therein.
GB597461A 1960-03-24 1961-02-17 Improvements in or relating to 9-substituted-1-azathiaxanthenes Expired GB975921A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH328060A CH383382A (en) 1960-03-24 1960-03-24 Process for the preparation of new heterocyclic compounds
CH1182060 1960-10-21

Publications (1)

Publication Number Publication Date
GB975921A true GB975921A (en) 1964-11-25

Family

ID=25692645

Family Applications (1)

Application Number Title Priority Date Filing Date
GB597461A Expired GB975921A (en) 1960-03-24 1961-02-17 Improvements in or relating to 9-substituted-1-azathiaxanthenes

Country Status (5)

Country Link
BE (1) BE601668A (en)
DE (1) DE1445132A1 (en)
DK (1) DK105763C (en)
ES (1) ES265955A1 (en)
GB (1) GB975921A (en)

Also Published As

Publication number Publication date
ES265955A1 (en) 1961-10-16
BE601668A (en) 1961-09-22
DE1445132A1 (en) 1968-12-19
DK105763C (en) 1966-11-07

Similar Documents

Publication Publication Date Title
ES445928A1 (en) Quaternary imidazole compounds as microbicides
GB1120463A (en) Derivatives of 1,3-diazafluoranthene-1-oxide
GB1364403A (en) 1 - aminosulphonyl - 2 - aminobenzimidazoles process for their preparation and their fungicidal use
GB842804A (en) Preparation of substituted piperazines
IN167606B (en)
US3714231A (en) Production of 2-acyloxy-thionobenzamides
GB975921A (en) Improvements in or relating to 9-substituted-1-azathiaxanthenes
US2974085A (en) 3-trichloromethyl-thio benzoxazolones
US3084171A (en) 5-nitro-2-furylamidine and alkyl 5-nitro-2-furylimidate
ES448629A1 (en) Benzoxazole derivatives, process for their preparation and their use as optical brighteners
GB1124246A (en) Novel quinazoline derivatives and a process for the preparation thereof
US2697101A (en) N-(heterocyclic mercuri) derivatives of hexachloro endophthalimide
GB1070139A (en) Novel imidazothiazole derivatives and a process for preparation thereof
IL56507A (en) (trihalomethyl)dimethyloxabicyclohexanone derivatives for the preparation of cis dihalovinyldimethylcyclopropanecarboxylic acids
US2777847A (en) Products
US3696114A (en) Antifungal thiocyanatobenzothiazoles
GB1010231A (en) Substituted 3-phenyl-5-imino-4,5 dihydro-1,2,4-oxadiazoles, process for their manufacture and therapeutic compositions containing same
GB1456946A (en) 6-phenyl-4h-imidazo-1,2-a-1,4-benzodiazepines
GB902058A (en) Process for the preparation of di-benzoxazolyl-ethylene compounds
ES393554A1 (en) Thiazole derivatives and a process for the manufacture thereof
GB920019A (en) 2-substituted sulphanilamidoquinazolines and process
GB951654A (en) Improvements in or relating to 6-pteridine carboxamidine and amidoxime derivatives
US2819287A (en) 3-thioureaphthalides
GB2119788A (en) Process for removing 1-sulfonyl groups from benzimidazoles
GB951653A (en) Improvements in or relating to 6-pteridinehydrazide and amidrazone derivatives