FR2385718A1 - Cerebral vasodilatory apovincaminic acid ester prepn. - by synthesis from tryptamine derivs. via novel intermediates and novel 16-alkyl derivs. - Google Patents

Cerebral vasodilatory apovincaminic acid ester prepn. - by synthesis from tryptamine derivs. via novel intermediates and novel 16-alkyl derivs.

Info

Publication number
FR2385718A1
FR2385718A1 FR7808739A FR7808739A FR2385718A1 FR 2385718 A1 FR2385718 A1 FR 2385718A1 FR 7808739 A FR7808739 A FR 7808739A FR 7808739 A FR7808739 A FR 7808739A FR 2385718 A1 FR2385718 A1 FR 2385718A1
Authority
FR
France
Prior art keywords
alkyl
derivs
acid ester
novel
tryptamine
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.)
Granted
Application number
FR7808739A
Other languages
French (fr)
Other versions
FR2385718B1 (en
Inventor
Csaba Szantay
Lajos Szabo
Gyorgy Kalaus
Vilmos Simonidesz
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.)
Richter Gedeon Vegyeszeti Gyar Nyrt
Original Assignee
Richter Gedeon Vegyeszeti Gyar RT
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 Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT
Publication of FR2385718A1 publication Critical patent/FR2385718A1/en
Application granted granted Critical
Publication of FR2385718B1 publication Critical patent/FR2385718B1/fr
Granted 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
    • C07D471/02—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 two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
    • 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)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Prepn. of apovincaminic acid esters of formula (I) comprises (a) intramolecular condensation of the tryptamine salt (II); (b) reaction of the obtd. 1-alkyl-3,4-dihydro-beta-carboline (III) with an acrylic acid ester (IV) opt. in the presence of potassium tert-butoxide (c) reaction of the obtd. 1-alkyl-2,3,4,5,6,7-hexahydroindolo (2,3-a)quinolizin-2-one (V) with hydrazine hydrate (d) reaction of the obtd. 1-alkyl-2,3,4,5,6,7-hexahydroindolo (2,3-a)quinolizine (VIa) or its salt (VIb) with a 2-acetoxy-acrylic acid ester (VII) (e) redn. and deacetylation of the hexahydroindolo, (2,3-a) quinolizinium salt (VII) (f) oxidation of the obtained octahydroindolo (2,3-a)-quinolizine (X1) (g) dehydration of the obtained vincaminic and epivincaminic acid esters (X11a and X11b) to yield (I). The racemic prods. may be resolved to give the optical isomers and/or the product may be conberted to its acid addn. or quat. salts. In (I) R1 is 1-5C alkyl and 33 is 1-4C alkyl. Intermediates (VIII), (IX), (X), (XI), (XIIa) and (XIIb) are new and (I) (R3 is not = ethyl) are new. (I) are cerebral vasodilators.
FR7808739A 1977-03-28 1978-03-24 Cerebral vasodilatory apovincaminic acid ester prepn. - by synthesis from tryptamine derivs. via novel intermediates and novel 16-alkyl derivs. Granted FR2385718A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
HU77RI622A HU175527B (en) 1977-03-28 1977-03-28 Totalsynthesis of esters of apovincaminic acid and homologues

Publications (2)

Publication Number Publication Date
FR2385718A1 true FR2385718A1 (en) 1978-10-27
FR2385718B1 FR2385718B1 (en) 1980-04-04

Family

ID=11001023

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7808739A Granted FR2385718A1 (en) 1977-03-28 1978-03-24 Cerebral vasodilatory apovincaminic acid ester prepn. - by synthesis from tryptamine derivs. via novel intermediates and novel 16-alkyl derivs.

Country Status (6)

Country Link
JP (1) JPS53138000A (en)
BE (1) BE865360A (en)
DE (1) DE2813015C2 (en)
ES (1) ES468248A1 (en)
FR (1) FR2385718A1 (en)
HU (1) HU175527B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2444037A1 (en) * 1978-12-15 1980-07-11 Richter Gedeon Vegyeszet PROCESS FOR THE PREPARATION OF 10-BROMOVINCAMINES AND COMPOUNDS OBTAINED
EP0013315A2 (en) * 1978-11-20 1980-07-23 Sumitomo Chemical Company, Limited Eburnane derivatives, their synthesis and pharmaceutical compositions containing them
FR2455037A1 (en) * 1979-04-27 1980-11-21 Carraz Gilbert Methoxy tryptamine succinic amide - having melatonin activity, but administrable parenterally

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU181495B (en) * 1979-05-31 1983-07-28 Richter Gedeon Vegyeszet Process for producing hydroxy-imino-eburnane derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2143657A1 (en) * 1971-05-07 1973-02-09 Richter Gedeon Vegyeszet
FR2314190A1 (en) * 1975-06-13 1977-01-07 Richter Gedeon Vegyeszet Optically active 1-ethyl-octahydroindolo-quinazolidine derivs prepn - via optically active esters

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH567507A5 (en) * 1972-03-29 1975-10-15 Sandoz Ag

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2143657A1 (en) * 1971-05-07 1973-02-09 Richter Gedeon Vegyeszet
FR2314190A1 (en) * 1975-06-13 1977-01-07 Richter Gedeon Vegyeszet Optically active 1-ethyl-octahydroindolo-quinazolidine derivs prepn - via optically active esters

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0013315A2 (en) * 1978-11-20 1980-07-23 Sumitomo Chemical Company, Limited Eburnane derivatives, their synthesis and pharmaceutical compositions containing them
EP0013315A3 (en) * 1978-11-20 1980-10-15 Sumitomo Chemical Company Limited Eburnane derivatives, including intermediates, their synthesis and pharmaceutical compositions containing them
EP0042526A1 (en) * 1978-11-20 1981-12-30 Sumitomo Chemical Company, Limited Process for producing apovincaminic acid esters and their salts
FR2444037A1 (en) * 1978-12-15 1980-07-11 Richter Gedeon Vegyeszet PROCESS FOR THE PREPARATION OF 10-BROMOVINCAMINES AND COMPOUNDS OBTAINED
FR2455037A1 (en) * 1979-04-27 1980-11-21 Carraz Gilbert Methoxy tryptamine succinic amide - having melatonin activity, but administrable parenterally

Also Published As

Publication number Publication date
JPS562072B2 (en) 1981-01-17
HU175527B (en) 1980-08-28
FR2385718B1 (en) 1980-04-04
DE2813015A1 (en) 1978-10-05
BE865360A (en) 1978-07-17
JPS53138000A (en) 1978-12-01
ES468248A1 (en) 1979-09-16
DE2813015C2 (en) 1983-10-20

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