GB893920A - Polycyclic amino compounds and methods for their production - Google Patents

Polycyclic amino compounds and methods for their production

Info

Publication number
GB893920A
GB893920A GB15813/60A GB1581360A GB893920A GB 893920 A GB893920 A GB 893920A GB 15813/60 A GB15813/60 A GB 15813/60A GB 1581360 A GB1581360 A GB 1581360A GB 893920 A GB893920 A GB 893920A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
alkyl
radical
general formula
ch2ch2
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
GB15813/60A
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.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co 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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Publication of GB893920A publication Critical patent/GB893920A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C61/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C61/16—Unsaturated compounds
    • C07C61/39—Unsaturated compounds containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
    • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0893920/IV (b)/1> (wherein R1 represents hydrogen, an alkyl or alkoxyalkyl radical of not more than 6 carbon atoms, or a benzyl radical, R2 represents hydrogen or a C1-6 alkyl radical, R3 and R4 represent hydrogen atoms or jointly a methylenedioxy radical, A represents -CH2CH2- or -CH=CH-, and Z represents oxygen or CH2) and their acid addition salts, and the preparation thereof by the following processes: (a) (where R1 is other than hydrogen, R2 is hydrogen and A is -CH2CH2-) reacting an imine of the general formula <FORM:0893920/IV (b)/2> (wherein X represents a halogen atom and R5 represents an alkyl or alkoxyalkyl radical of not more than 6 carbon atoms or a benzyl radical) with a reactive organometallic compound under anhydrous conditions and decomposing the product with an aqueous medium; (b) (when R1 is hydrogen and R2 is CH3) reducing a carbamate of the general formula <FORM:0893920/IV (b)/3> (c) (when R1=R2=H) hydrolysing a carbamate of the general formula given in (b); (d) (when R1=R2=H and A is -CH2CH2) catalytically hydrogenating the N-monobenzyl derivatives of the desired products; (e) (when R2 is C1-6 alkyl) alkylating the compounds in which R2 is hydrogen (e.g. by acylation followed by reduction); (f) (when R1 is hydrogen or C1-6 alkyl and A is -CH2CH2-) catalytically hydrogenating the corresponding compounds in which A is -CH=CH-. The products are p useful as central nervous system depressants (see Group VI). Imines of the second general formula above are prepared by condensing a primary amine with the corresponding ketones, obtainable, when Z is oxygen, from a sodium o-halophenate and a 2-halocylohexanone, or, when Z is CH2 from an o-halobenzyl halide and cyclohexanone in the presence of sodamide. Carbamates of the third general formula above (R3=R4=H) are prepared by esterifying indene- or benzofuran-3-carboxylic acid to an alkyl ester, reacting this with butadiene to form an alkyl ester of 1,4,4a,9a-tetrahydrofluorene-4a-carboxylic acid or 5a,6,9,9a-tetrahydrodibenzofuran-9a-carboxylic acid and then performing the transformations <FORM:0893920/IV (b)/4> preceded, if desired, by <FORM:0893920/IV (b)/5>ALSO:Compounds of the general formula <FORM:0893920/VI/1> (wherein R1 represents hydrogen, an alkyl or alkoxyalkyl radical of not more than 6 carbon atoms, or a benzyl radical, R2 represents hydrogen or a C1-6 alkyl radical, R3 and R4 represent hydrogen atoms or jointly a methylenedioxy radical, A represents -CH2CH2- or -CH = CH-, and Z represents oxygen or CH2) and their addition salts with inorganic or organic acids (including ascorbic acid) may be administered orally or parenterally as central nervous system depressants. For anaesthetic purposes they may be used in combination into barbiturates.
GB15813/60A 1959-05-05 1960-05-04 Polycyclic amino compounds and methods for their production Expired GB893920A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US893920XA 1959-05-05 1959-05-05

Publications (1)

Publication Number Publication Date
GB893920A true GB893920A (en) 1962-04-18

Family

ID=22217397

Family Applications (1)

Application Number Title Priority Date Filing Date
GB15813/60A Expired GB893920A (en) 1959-05-05 1960-05-04 Polycyclic amino compounds and methods for their production

Country Status (1)

Country Link
GB (1) GB893920A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4837226A (en) * 1988-04-27 1989-06-06 Warner-Lambert Company Polycyclic amine derivatives useful as cerebrovascular agents
US5071853A (en) * 1989-03-23 1991-12-10 Bigge Christopher F Polycyclic amines useful as cerebrovascular agents
US5180736A (en) * 1989-03-23 1993-01-19 Warner-Lambert Company Polycyclic amines useful as cerebrovascular agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4837226A (en) * 1988-04-27 1989-06-06 Warner-Lambert Company Polycyclic amine derivatives useful as cerebrovascular agents
US5071853A (en) * 1989-03-23 1991-12-10 Bigge Christopher F Polycyclic amines useful as cerebrovascular agents
US5180736A (en) * 1989-03-23 1993-01-19 Warner-Lambert Company Polycyclic amines useful as cerebrovascular agents
US5276053A (en) * 1989-03-23 1994-01-04 Warner-Lambert Company Polycyclic amines useful as cerebrovascular agents

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