GB773756A - 9-aminoalkyl-9-xanthenecarboxamides and derivatives thereof - Google Patents

9-aminoalkyl-9-xanthenecarboxamides and derivatives thereof

Info

Publication number
GB773756A
GB773756A GB23042/55A GB2304255A GB773756A GB 773756 A GB773756 A GB 773756A GB 23042/55 A GB23042/55 A GB 23042/55A GB 2304255 A GB2304255 A GB 2304255A GB 773756 A GB773756 A GB 773756A
Authority
GB
United Kingdom
Prior art keywords
xanthene
xanthenecarbonylpyrrolidine
carboxamide
carboxylic acid
xanthenecarboxamide
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
GB23042/55A
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.)
GD Searle LLC
Original Assignee
GD Searle LLC
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 GD Searle LLC filed Critical GD Searle LLC
Publication of GB773756A publication Critical patent/GB773756A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9

Landscapes

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

Abstract

The invention comprises xanthene carboxamides of the general formula <FORM:0773756/IV(b)/1> and acid addition salts thereof, wherein Alk is a lower alkylene group and NRR1 and NXX1 are amino groups or lower alkyl, alkenyl or hydroxyalkyl substituted amino groups or are nitrogen-containing heteromonocyclic radicals attached to the radical Alk through the ring nitrogen atom, the lower alkyl, alkenyl, hydroxyalkyl and alkylene radicals being radicals containing less than 7 carbon atoms. The compounds may be prepared by the following methods: (a) reaction of the 9-alkali metal derivative of a 9-xanthene carboxamide with a haloalkylamine of the formula Halogen-Alk-NXX1; (b) ammonolysis of a compound of the structure <FORM:0773756/IV(b)/2> wherein Y is a halogen atom, a hydroxy radical or a hydrocarbon-oxy radical such as CH3O-, C2H5O-, C6H5O-, with ammonia or an amine of the type HNRR1; (c) ammonolysis of a 9-haloalkyl - 9 - xanthenecarboxamide with an amine of the type HNXX1 and (d) reaction of a 9-haloalkyl-9-xanthene carboxylic halide with ammonia or a primary or secondary amine. The products may be converted into acid addition and quaternary salts and are used as therapeutic agents. Examples describe the preparation of compounds of the general formula I comprising xanthene - 9 - carboxylic acid - 9 - diethylaminoethyl, amide, dimethylamide, pyrrolidide, diethylamide, piperidide, morpholide and hydroxyethylamide; xanthene-9-pyrrolidinoethyl - 9 - carboxamide, 9 - (d - piperidinobutyl) - 9 - carboxamide, 9 - (b - diisopropylaminoethyl) - 9 - N - methyl carboxamide, the 9 - (g - butylaminopropyl), 9 - (g - aminopropyl) and 9 - (b - diisopropylaminoethyl), 9 - xanthenecarbonylpiperidines; the 9-(b -dimethylaminoethyl), 9 - (g - dimethylaminopropyl), 9 - (b - dimethylamino - a - methylethyl), 9 - (b - dimethylaminopropyl), 9 - (b - diallylaminoethyl), 9 - (b - di - n - propylaminoethyl), 9 - (b - di - isopropylaminoethyl), 9 - (b - pyrrolidinoethyl), 9 - (g - pyrrolidinopropyl), 9 - (2 : 5 - dimethylpyrrolidinoethyl), 9 - (b - piperidinoethyl) 9 - [b - (2 : 6 - lupetidino) - ethyl], 9 - (b - morpholinoethyl), 9 - [b - (N - hydroxyethyl - N - methylamino) ethyl] and 9-(b -dimethylaminoethyl) 9-xanthene-carbonyl-pyrrolidines. Starting materials. The preparation of 9-(b -diethylaminoethyl) - 9 - xanthene carboxylic acid methyl ester, the corresponding free acid and the methiodide, 9 - (b - pyrrolidinoethyl) - 9 - xanthene carboxylic acid methyl ester, 9-(b -diisopropylaminoethyl) - 9 - xanthene carboxylic acid methyl ester, N : N-dimethyl-9-xanthenecarboxamide, 9 - xanthenecarbonylpiperidine, 9 - xanthenecarbonylpyrrolidine, N : N - diethyl - 9 - xanthenecarboxamide, 9 - xanthenecarbonylmorpholine, 9 - (b - vinyloxyethyl) - 9 - xanthenecarbonylpyrrolidine, 9 - (b - hydroxyethyl) - 9 - xanthenecarbonylpyrrolidine and 9 - (b - chloroethyl) - 9 - xanthenecarbonylpyrrolidine is described in detail.
GB23042/55A 1954-08-18 1955-08-10 9-aminoalkyl-9-xanthenecarboxamides and derivatives thereof Expired GB773756A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US773756XA 1954-08-18 1954-08-18

Publications (1)

Publication Number Publication Date
GB773756A true GB773756A (en) 1957-05-01

Family

ID=22137691

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23042/55A Expired GB773756A (en) 1954-08-18 1955-08-10 9-aminoalkyl-9-xanthenecarboxamides and derivatives thereof

Country Status (1)

Country Link
GB (1) GB773756A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5760246A (en) * 1996-12-17 1998-06-02 Biller; Scott A. Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
EP0904262A1 (en) * 1996-01-16 1999-03-31 Bristol-Myers Squibb Company Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
US11084807B2 (en) 2016-08-18 2021-08-10 Vidac Pharama Ltd. Piperazine derivatives, pharmaceutical compositions and methods of use thereof

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0904262A1 (en) * 1996-01-16 1999-03-31 Bristol-Myers Squibb Company Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
EP0904262A4 (en) * 1996-01-16 2000-10-04 Bristol Myers Squibb Co Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
US5760246A (en) * 1996-12-17 1998-06-02 Biller; Scott A. Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
US6472414B1 (en) 1996-12-17 2002-10-29 Bristol-Myers Squibb Company Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method
US11084807B2 (en) 2016-08-18 2021-08-10 Vidac Pharama Ltd. Piperazine derivatives, pharmaceutical compositions and methods of use thereof

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