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GB829763A - Derivatives of thiaxanthene - Google Patents

Derivatives of thiaxanthene

Info

Publication number
GB829763A
GB829763A GB27348/56A GB2734856A GB829763A GB 829763 A GB829763 A GB 829763A GB 27348/56 A GB27348/56 A GB 27348/56A GB 2734856 A GB2734856 A GB 2734856A GB 829763 A GB829763 A GB 829763A
Authority
GB
United Kingdom
Prior art keywords
general formula
hydrogen
prepared
thiaxanthone
ether
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
GB27348/56A
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.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB829763A publication Critical patent/GB829763A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • C07D335/12—Thioxanthenes
    • C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0829763/IV (b)/1> (wherein X and X1 each represent a hydrogen or halogen atom or a C1-5 alkyl or alkoxy radical, each R DEG represents a hydrogen atom or an alkyl radical, the R DEG groups together containing 0-4 carbon atoms, and <FORM:0829763/IV (b)/2> represents a tertiary amino group in which R and R1 are separate or are joined to form a heterocyclic ring with the nitrogen atom, or R1 is joined to any R DEG group that is not hydrogen to form a heterocyclic ring with the nitrogen atom), and their acid addition salts, and the preparation thereof by reacting a Grignard reagent, prepared from magnesium and a 3-aminopropyl halide of the general formula <FORM:0829763/IV (b)/3> with a thiaxanthone derivative of the general formula <FORM:0829763/IV (b)/4> to form a Grignard adduct, hydrolysing this to a compound of the general formula <FORM:0829763/IV (b)/5> which is then dehydrated, and, if desired, treating the product with an acid to form a salt. The Grignard reagent, e.g. 3-dimethylaminopropyl magnesium chloride, is preferably prepared in the presence of tetrahydrofuran, but it can also be prepared in the presence of ether or a mixture of ether and benzene provided the aminopropyl halide is added portionwise, the thiaxanthone derivative thereafter also being added portionwise. The products are useful as therapeutic agents on account of their antiemetic properties. Specification 829,764 is referred to.
GB27348/56A 1955-09-23 1956-09-06 Derivatives of thiaxanthene Expired GB829763A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US829763XA 1955-09-23 1955-09-23

Publications (1)

Publication Number Publication Date
GB829763A true GB829763A (en) 1960-03-09

Family

ID=22174633

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27348/56A Expired GB829763A (en) 1955-09-23 1956-09-06 Derivatives of thiaxanthene

Country Status (1)

Country Link
GB (1) GB829763A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1212101B (en) * 1960-09-13 1966-03-10 Sandoz Ag Process for the preparation of substituted thioxanthylidenes
US3275640A (en) * 1961-09-29 1966-09-27 Merck & Co Inc Substituted 1-hydrocarbyl-4-(10-thiaxanthylidene) piperidines
US3299050A (en) * 1960-09-13 1967-01-17 Sandoz Ltd Thiaxanthene derivatives

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1212101B (en) * 1960-09-13 1966-03-10 Sandoz Ag Process for the preparation of substituted thioxanthylidenes
US3299050A (en) * 1960-09-13 1967-01-17 Sandoz Ltd Thiaxanthene derivatives
US3275640A (en) * 1961-09-29 1966-09-27 Merck & Co Inc Substituted 1-hydrocarbyl-4-(10-thiaxanthylidene) piperidines

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