GB983848A - Improvements in or relating to indoloquinolizine compounds - Google Patents
Improvements in or relating to indoloquinolizine compoundsInfo
- 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
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
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: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.
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)
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 |
-
1961
- 1961-03-09 GB GB866761A patent/GB983848A/en not_active Expired
Cited By (3)
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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