FR2383181A2 - Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities - Google Patents

Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities

Info

Publication number
FR2383181A2
FR2383181A2 FR7707248A FR7707248A FR2383181A2 FR 2383181 A2 FR2383181 A2 FR 2383181A2 FR 7707248 A FR7707248 A FR 7707248A FR 7707248 A FR7707248 A FR 7707248A FR 2383181 A2 FR2383181 A2 FR 2383181A2
Authority
FR
France
Prior art keywords
naphthyridine
oxo
indolo
methyl
antianoxia
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
FR7707248A
Other languages
French (fr)
Other versions
FR2383181B2 (en
Inventor
Gabor Istvan Koletar
Henry Najer
Regis Dupont
Jean Pierre Gaston Lefevre
Don Pierre Rene Luc Giudicelli
Claude Constant Henri Morel
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.)
Synthelabo SA
Original Assignee
Synthelabo SA
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 Synthelabo SA filed Critical Synthelabo SA
Priority to FR7707248A priority Critical patent/FR2383181A2/en
Priority to DD7700198314A priority patent/DD129791A5/en
Priority to US05/786,557 priority patent/US4190657A/en
Priority to MT811A priority patent/MTP811B/en
Priority to JP52041904A priority patent/JPS5823877B2/en
Priority to IL51853A priority patent/IL51853A/en
Priority to YU00948/77A priority patent/YU94877A/en
Priority to GB15165/77A priority patent/GB1543283A/en
Priority to MX775626U priority patent/MX5340E/en
Priority to CH450777A priority patent/CH622795A5/fr
Priority to AU24189/77A priority patent/AU506031B2/en
Priority to DK161377A priority patent/DK143703C/en
Priority to AT254277A priority patent/AT352741B/en
Priority to LU77100A priority patent/LU77100A1/xx
Priority to SE7704172A priority patent/SE432932B/en
Priority to NO77771263A priority patent/NO146777C/en
Priority to CS239477A priority patent/CS220313B2/en
Priority to DE19772716190 priority patent/DE2716190A1/en
Priority to AR267179A priority patent/AR214519A1/en
Priority to CA275,948A priority patent/CA1072960A/en
Priority to CS578381A priority patent/CS220344B2/en
Priority to HUSI001569 priority patent/HU181958B/en
Priority to PT66428A priority patent/PT66428B/en
Priority to NZ183846A priority patent/NZ183846A/en
Priority to GR53198A priority patent/GR63658B/en
Priority to FI771159A priority patent/FI63404C/en
Priority to SU772470258A priority patent/SU655314A3/en
Priority to PL19737377A priority patent/PL197373A1/en
Priority to IE758/77A priority patent/IE44989B1/en
Priority to AT656178A priority patent/AT355583B/en
Publication of FR2383181A2 publication Critical patent/FR2383181A2/en
Application granted granted Critical
Publication of FR2383181B2 publication Critical patent/FR2383181B2/fr
Priority to FI803790A priority patent/FI803790L/en
Priority to SE8201181A priority patent/SE8201181L/en
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
    • C07D471/12—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
    • C07D471/16—Peri-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Naphthyridine derivs. of formula (I), as racemates or optical isomers, and their suitable salts with acids are new. In (I) R1=H, 1-4C alkyl, 2-oxopropyl, 2-hydroxypropyl, 3-oxobutyl, 3-hydroxybutyl, cyclopropyl methyl, benzyl (opt. halogenated esp. by F or Cl), acetyl, cyclopropylcarbonyl, benzoyl or (CH2)nR1. R2=H, halo, CH3 or CH3O. R6=H or COR7. R3=CH3 or C2H5, and R4=OH or H and R5=H, or R3+R4=oxo and R5=H, or R3=CH3 or C2H5 and R4+R5=an additional C-C bond. n=1 or 2. R1=(m)ethoxycarbonyl or CN. R7=OH, 1-4C alkoxy, NH2(opt. substd. by 1 or 2 CH3 or by one cyclopropyl). The following cpds. are excluded: R3+R4=oxo; (a) R1=H=R6 and R2=10-CH3O and (b) R1=R2=R6=H; but when R6=alkoxycarbonyl stereoisomers are included. Dose is 10-100 mg/day. In an example methyl 1,2,3,3a,4,5,-hexahydro-3-methyl-6-oxo-6H-indolo 3,2,1-de 1,5 naphthyridine-4-carboxylate was prepd. fron Nb-methyltryptamine and diethyl alpha-formyl succinate.
FR7707248A 1976-03-11 1977-03-11 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities Granted FR2383181A2 (en)

Priority Applications (32)

Application Number Priority Date Filing Date Title
FR7707248A FR2383181A2 (en) 1977-03-11 1977-03-11 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities
DD7700198314A DD129791A5 (en) 1976-04-13 1977-04-07 PROCESS FOR THE PREPARATION OF NAPHTYRIDINE DERIVATIVES
MT811A MTP811B (en) 1976-04-13 1977-04-11 Indolo (3,2,1-de)(1.5) naphthyzidine derivatives
JP52041904A JPS5823877B2 (en) 1976-04-13 1977-04-11 Naphthyridine derivatives and their production method
IL51853A IL51853A (en) 1976-04-13 1977-04-11 1,2,3,3a-tetrahydro(or 1,2,3,3a,4,5-hexahydro)indolo(3,2,1-de)naphthyridine derivatives,their preparation and pharmaceutical compositions containing them
YU00948/77A YU94877A (en) 1976-04-13 1977-04-11 Process for obtaining naphthiridine derivatives
US05/786,557 US4190657A (en) 1976-03-11 1977-04-11 Naphthyridine derivatives
PT66428A PT66428B (en) 1976-04-13 1977-04-12 PROCESS FOR THE PREPARATION OF NEW NAPHTHYRIDINE DERIVATIVES
CH450777A CH622795A5 (en) 1976-04-13 1977-04-12
AU24189/77A AU506031B2 (en) 1976-04-13 1977-04-12 Indolo(3, 2, 1-de) (1, 5) naphthyrudune derivatives
DK161377A DK143703C (en) 1976-04-13 1977-04-12 ANALOGY PROCEDURE FOR PREPARING 1,2,3,3A, 4,5-HEXAHYDRO-6-OXO-6H-INDOLO (3,2,1-DE) = (1,5) NAPHTHYRIDINE DERIVATIVES OR ACID ADDITION SALTS THEREOF
AT254277A AT352741B (en) 1976-04-13 1977-04-12 PROCESS FOR THE PREPARATION OF NEW NAPHTYRIDE DERIVATIVES, THEIR SALT AND OPTICAL ISOMERS
LU77100A LU77100A1 (en) 1976-04-13 1977-04-12
SE7704172A SE432932B (en) 1976-04-13 1977-04-12 ANALOGY PROCEDURE FOR PREPARING DERIVATIVES OF 1,2,3,3A-TETRAHYDRO-INDOLO / 3,2,1-DE / / 1,5 / NAFTYRIDINE
NO77771263A NO146777C (en) 1976-04-13 1977-04-12 ANALOGY PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE 6H-INDOLO (3,2,1-DE) - (1,5) -NAPHYRIDINE INGREDIATES
CS239477A CS220313B2 (en) 1976-04-13 1977-04-12 Method of producing new naphtyridine derivatives
GB15165/77A GB1543283A (en) 1976-04-13 1977-04-12 Indolo-(3,2,1-de)(1,5)naphthyridine derivatives
AR267179A AR214519A1 (en) 1976-04-13 1977-04-12 PROCEDURE TO OBTAIN TETRAHYDRO-1,2,3,3A-INDOL- (3,2,1-DE) NAPHTHYRIDINE
CA275,948A CA1072960A (en) 1976-04-13 1977-04-12 Indolo (3,2,1-de) (1,5) naphthyridine derivatives
CS578381A CS220344B2 (en) 1976-04-13 1977-04-12 Method of preparing new naphtyridine derivatives
HUSI001569 HU181958B (en) 1976-04-13 1977-04-12 Process for producing new 1,2,3,3a-tetrahydro-indolo-bracket-3,2,1-d,e-bracket closed-bracket-1,5-bracket closed-naphtridine derivatives
MX775626U MX5340E (en) 1976-04-13 1977-04-12 PROCEDURE FOR PREPARING HEXAHYDRO DERIVATIVES 1,2,3,3A.4,5-OXO-6-6H-INDOLO (3,2,1-DE) NAFTIRIDINE
DE19772716190 DE2716190A1 (en) 1976-04-13 1977-04-12 NAPHTYRIDE DERIVATIVES, A PROCESS FOR THEIR MANUFACTURING, AND THESE COMPOUNDS AS MEDICINAL PRODUCTS CONTAINING ACTIVE SUBSTANCES
GR53198A GR63658B (en) 1976-04-13 1977-04-13 Process for derivatives preparation of naphyridine
FI771159A FI63404C (en) 1976-04-13 1977-04-13 FRONTAL PROTECTION OF ANTANOXIC 1,2,3,3A, 4,5-HEXAHYDRO-6-OXO-6H-INDOLO (3,2,1-DE) (1,5) NAPHTHYRIDINE
SU772470258A SU655314A3 (en) 1976-04-13 1977-04-13 Method of obtaining naphthyridine derivatives or their stereoisomers or their salts
PL19737377A PL197373A1 (en) 1976-04-13 1977-04-13 METHOD OF MAKING NEW DERIVATIVES 1,2,3,3A-TETRAHYDROGENINDOLO / 3,2,1 // 1,5 / NAPHTHRIDINE
IE758/77A IE44989B1 (en) 1976-04-13 1977-04-13 Indolo(3,2,1-d,e)(1,5)naphthyridine derivatives
NZ183846A NZ183846A (en) 1976-04-13 1977-04-13 1,2,3,3a,4,5-hexahydro-6h-indolo(3,2,1-de) (1,5)-naphthyridines
AT656178A AT355583B (en) 1976-04-13 1978-09-11 METHOD FOR PRODUCING NEW NAPHTYRIDINE DERIVATIVES IN THE FORM OF ITS RACEMATE OR ITS OPTICAL ISOMERS AND THEIR SALTS
FI803790A FI803790L (en) 1976-04-13 1980-12-05 FREQUENCY REFRIGERATION OF ANTIANOXIC 1,2,3,3A, 4,5-HEXAHYDRO-6-OXO-6H-INDOLO / 3,2,1-DE / / 1,5 / NAPHTHYRIDINE
SE8201181A SE8201181L (en) 1976-04-13 1982-02-25 PROCEDURE FOR PREPARING NEW DERIVATIVES OF 1,2,3,3A-TETRA-HYDRO-INDOLO- (3,2,1-DE) (1,5) NAFTYRIDINE

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7707248A FR2383181A2 (en) 1977-03-11 1977-03-11 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities

Publications (2)

Publication Number Publication Date
FR2383181A2 true FR2383181A2 (en) 1978-10-06
FR2383181B2 FR2383181B2 (en) 1979-09-07

Family

ID=9187949

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7707248A Granted FR2383181A2 (en) 1976-03-11 1977-03-11 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities

Country Status (1)

Country Link
FR (1) FR2383181A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2548667A1 (en) * 1983-07-05 1985-01-11 Synthelabo Benzindolonaphthyridine derivatives, their preparation and their application in therapeutics

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2548667A1 (en) * 1983-07-05 1985-01-11 Synthelabo Benzindolonaphthyridine derivatives, their preparation and their application in therapeutics

Also Published As

Publication number Publication date
FR2383181B2 (en) 1979-09-07

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