GB983848A - Improvements in or relating to indoloquinolizine compounds - Google Patents

Improvements in or relating to indoloquinolizine compounds

Info

Publication number
GB983848A
GB983848A GB866761A GB866761A GB983848A GB 983848 A GB983848 A GB 983848A GB 866761 A GB866761 A GB 866761A GB 866761 A GB866761 A GB 866761A GB 983848 A GB983848 A GB 983848A
Authority
GB
United Kingdom
Prior art keywords
group
general formula
reaction
cyclizing
converting
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
GB866761A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB983848A publication Critical patent/GB983848A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems

Abstract

The invention comprises compounds of the general formula <FORM:0983848/C2/1> (wherein Y is a free, etherified or esterified hydroxyl group, n1 is 0, 1 or 2, X is a free or esterified hydroxyl group, a -C­N group or carboxyl group esterified by a C1- 4 aliphatic alcohol, and n is 0-4) and acid addition salts thereof, pharmaceutical preparations containing them, and their preparation by (a), cyclizing a compound of the general formula <FORM:0983848/C2/2> (wherein X1 represents X or a group convertible thereto, and R1 represents a C1- 4 alkyl group) by a Dieckmann reaction, isolating the reaction product which has a keto group at the 2-position and a -CO(CH2)n- 1X1 group at the 3-position, reducing the 2-keto group to a methylene group and, if necessary, converting X1 to X, (b) cyclizing a compound of the general formula <FORM:0983848/C2/3> (wherein R2 represents -(CH2)nX or a group convertible thereto) by a Bischler-Napieralsky reaction, reducing the product of the general formula <FORM:0983848/C2/4> (wherein Z- represents an anion) and, if necessary, converting R2 to -(CH2)nX, or (c) reacting a compound of the general formula <FORM:0983848/C2/5> with phenylhydrazine or an appropriately substituted phenylhydrazine, and cyclizing the product of the general formula <FORM:0983848/C2/6> by the Fischer indole synthesis reaction and, if necessary, converting R2 to -(CH2)nX, optionally followed in each case by acid addition salt formation. The following intermediates are prepared from the starting materials indicated in parentheses: 1 - [21 - (311 - indolyl)ethyl] - 5 - carbethoxy - a - piperidone - 2 (diethyl glutarate and ethyl formate, via diethyl a -oxymethylene-glutarate and diethyl a - [2 - (3 - indolyl) - ethylaminomethylene] - glutarate); 7 - carbethoxy - 1 - oxo - octahydroquinolizine (dimethyl pyridine - 2,5 - dicarboxylate, via 2,5 - bis - carbomethoxypiperidine and ethyl g - (2,5 - bis - carbomethoxypiperidino)-butyrate). The compounds of the invention are sedatives, and may be administered orally or parenterally in the form of pharmaceutical preparations (e.g. tablets and injectable solutions) containing them together with a carrier. Specification 841,225 is referred to.
GB866761A 1960-03-12 1961-03-09 Improvements in or relating to indoloquinolizine compounds Expired GB983848A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL249361 1960-03-12

Publications (1)

Publication Number Publication Date
GB983848A true GB983848A (en) 1965-02-17

Family

ID=19752218

Family Applications (1)

Application Number Title Priority Date Filing Date
GB866761A Expired GB983848A (en) 1960-03-12 1961-03-09 Improvements in or relating to indoloquinolizine compounds

Country Status (1)

Country Link
GB (1) GB983848A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173642A (en) * 1976-12-30 1979-11-06 Richter Gedeon Vegyeszeti Gyar Rt Vasodilating 1,1-di-(2-methoxycarbonyl-ethyl)-1,2,3,4,5,6,12,12b-octahydro-indolo[2,3-a]quinolizine
US7592350B2 (en) 2002-04-03 2009-09-22 Orion Corporation Polycyclic compounds as potent alpha2-adrenoceptor antagonists

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4173642A (en) * 1976-12-30 1979-11-06 Richter Gedeon Vegyeszeti Gyar Rt Vasodilating 1,1-di-(2-methoxycarbonyl-ethyl)-1,2,3,4,5,6,12,12b-octahydro-indolo[2,3-a]quinolizine
US4278682A (en) * 1976-12-30 1981-07-14 Richter Gedeon Vegyeszeti Gyar Rt. Vasodilating method of treatment using a indolo-quinolizine-monoester, diester or nitrile
US7592350B2 (en) 2002-04-03 2009-09-22 Orion Corporation Polycyclic compounds as potent alpha2-adrenoceptor antagonists

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