GB1147832A - Fluorene xanthene and thioxanthene derivatives - Google Patents

Fluorene xanthene and thioxanthene derivatives

Info

Publication number
GB1147832A
GB1147832A GB6777/67A GB677767A GB1147832A GB 1147832 A GB1147832 A GB 1147832A GB 6777/67 A GB6777/67 A GB 6777/67A GB 677767 A GB677767 A GB 677767A GB 1147832 A GB1147832 A GB 1147832A
Authority
GB
United Kingdom
Prior art keywords
radical
general formula
amide
formula
compound
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
GB6777/67A
Inventor
John Frederick Cavalla
Roy Simpson
Alan Chapman White
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.)
John Wyeth and Brother Ltd
Original Assignee
John Wyeth and Brother Ltd
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 John Wyeth and Brother Ltd filed Critical John Wyeth and Brother Ltd
Priority to GB6777/67A priority Critical patent/GB1147832A/en
Publication of GB1147832A publication Critical patent/GB1147832A/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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,147,832. Derivatives of fluorene, xanthene and thioxanthene. JOHN WYETH & BROTHER Ltd. 30 Jan., 1968 [13 Feb., 1967], No. 6777/67. Heading C2C. Novel compounds of the general formula and acid addition and quaternary ammonium salts thereof, wherein R<SP>1</SP> and R<SP>2</SP> are bonds joined directly together to complete a 5- membered ring or linked through an oxygen or sulphur atom to complete a 6-membered ring, R<SP>3</SP> is a hydrogen atom or a lower-alkyl, e.g. methyl radical, R<SP>4</SP> and R<SP>5</SP> are the same or different and each is a lower alkyl radical, hydroxy lower alkyl radical or a benzyl radical or R<SP>4</SP> and R<SP>5</SP> together complete a ring which may contain a further hetero atom, X is a cyano, esterified carboxyl or N,N-disubstituted carbamoyl radical and rings A and B are unsubstituted or substituted by halogen, lower alkyl, lower alkoxy, trihalomethyl or nitro (the term "lower" as used herein means that the radical contains 1 to 6, preferably 1 to 4, carbon atoms) are prepared by carrying out a Mannich reaction on the corresponding starting material of general formula and a secondary amine of formula HNR<SP>4</SP>R<SP>5</SP> in the presence of formaldehyde or paraformaldehyde optionally followed by conversion of one X group into another, e.g. hydrolysis to give carboxy group which may then be reacted with ammonia or an alkylamine or benzylamine to give an amide and in all cases optionally followed by salt formation or quaternization. Alcohols and their esters of the first general formula above wherein X is a hydroxy methyl radical or an ester thereof are prepared by reduction of a compound of the first formula above wherein X is an alkoxy carbonyl radical optionally followed by esterification. Acids and amides of the second general formula above, i.e. wherein X is a carboxylic or carboxylic amide radical, are prepared by reaction of an alkali metal salt of a compound of the formula with an unsaturated compound of the formula Y-CH.(R<SP>3</SP>)-C#CH, in which Y is halogen, and, in the case of the carboxylic amide, the resulting carboxylic acid is reacted with thionyl chloride and then an alkylamine to give the amide. Pharmaceutical compositions having central nervous system, anti-ulcer or anti-inflammatory activities and being in conventional forms for oral or parenteral administration comprise an above novel compound and a pharmaceutical carrier therefor.
GB6777/67A 1967-02-13 1967-02-13 Fluorene xanthene and thioxanthene derivatives Expired GB1147832A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB6777/67A GB1147832A (en) 1967-02-13 1967-02-13 Fluorene xanthene and thioxanthene derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB6777/67A GB1147832A (en) 1967-02-13 1967-02-13 Fluorene xanthene and thioxanthene derivatives

Publications (1)

Publication Number Publication Date
GB1147832A true GB1147832A (en) 1969-04-10

Family

ID=9820557

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6777/67A Expired GB1147832A (en) 1967-02-13 1967-02-13 Fluorene xanthene and thioxanthene derivatives

Country Status (1)

Country Link
GB (1) GB1147832A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2081488A1 (en) * 1970-02-03 1971-12-03 Bayer Ag
EP0095880A1 (en) * 1982-05-24 1983-12-07 Sds Biotech Corporation Fluorenecarboxylic acid derivatives, their preparation and use as plant growth regulators
EP0904262A1 (en) * 1996-01-16 1999-03-31 Bristol-Myers Squibb Company 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

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2081488A1 (en) * 1970-02-03 1971-12-03 Bayer Ag
EP0095880A1 (en) * 1982-05-24 1983-12-07 Sds Biotech Corporation Fluorenecarboxylic acid derivatives, their preparation and use as plant growth regulators
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
US6472414B1 (en) 1996-12-17 2002-10-29 Bristol-Myers Squibb Company Conformationally restricted aromatic inhibitors of microsomal triglyceride transfer protein and method

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