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FR2358146A1 - 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
FR2358146A1
FR2358146A1 FR7610773A FR7610773A FR2358146A1 FR 2358146 A1 FR2358146 A1 FR 2358146A1 FR 7610773 A FR7610773 A FR 7610773A FR 7610773 A FR7610773 A FR 7610773A FR 2358146 A1 FR2358146 A1 FR 2358146A1
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
FR7610773A
Other languages
French (fr)
Other versions
FR2358146B1 (en
Inventor
Gabor Istvan Koletar
Henry Najer
Jean Pierre Gaston Lefevre
Regis Dupont
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 FR7610773A priority Critical patent/FR2358146A1/en
Priority to IN409/CAL/77A priority patent/IN145423B/en
Priority to DD7700198314A priority patent/DD129791A5/en
Priority to BE176581A priority patent/BE853435A/en
Priority to US05/786,557 priority patent/US4190657A/en
Priority to ES457692A priority patent/ES457692A1/en
Priority to IL51853A priority patent/IL51853A/en
Priority to JP52041904A priority patent/JPS5823877B2/en
Priority to YU00948/77A priority patent/YU94877A/en
Priority to MT811A priority patent/MTP811B/en
Priority to PT66428A priority patent/PT66428B/en
Priority to CH450777A priority patent/CH622795A5/fr
Priority to CA275,948A priority patent/CA1072960A/en
Priority to MX775626U priority patent/MX5340E/en
Priority to DK161377A priority patent/DK143703C/en
Priority to HUSI001569 priority patent/HU181958B/en
Priority to CS239477A priority patent/CS220313B2/en
Priority to AT254277A priority patent/AT352741B/en
Priority to AR267179A priority patent/AR214519A1/en
Priority to CS578381A priority patent/CS220344B2/en
Priority to ZA00772209A priority patent/ZA772209B/en
Priority to AU24189/77A priority patent/AU506031B2/en
Priority to DE19772716190 priority patent/DE2716190A1/en
Priority to GB15165/77A priority patent/GB1543283A/en
Priority to NO77771263A priority patent/NO146777C/en
Priority to LU77100A priority patent/LU77100A1/xx
Priority to SE7704172A priority patent/SE432932B/en
Priority to SU772470258A priority patent/SU655314A3/en
Priority to NZ183846A priority patent/NZ183846A/en
Priority to FI771159A priority patent/FI63404C/en
Priority to GR53198A priority patent/GR63658B/en
Priority to NL7704004A priority patent/NL7704004A/en
Priority to PL19737377A priority patent/PL197373A1/en
Priority to FI803790A priority patent/FI803790A7/en
Priority to IE758/77A priority patent/IE44989B1/en
Publication of FR2358146A1 publication Critical patent/FR2358146A1/en
Priority to AT656178A priority patent/AT355583B/en
Publication of FR2358146B1 publication Critical patent/FR2358146B1/fr
Application granted granted Critical
Priority to SE8201181A priority patent/SE8201181L/en
Granted legal-status Critical Current

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  • 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.
FR7610773A 1976-03-11 1976-04-13 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities Granted FR2358146A1 (en)

Priority Applications (37)

Application Number Priority Date Filing Date Title
FR7610773A FR2358146A1 (en) 1976-04-13 1976-04-13 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities
IN409/CAL/77A IN145423B (en) 1976-04-13 1977-03-21
DD7700198314A DD129791A5 (en) 1976-04-13 1977-04-07 PROCESS FOR THE PREPARATION OF NAPHTYRIDINE DERIVATIVES
BE176581A BE853435A (en) 1976-04-13 1977-04-08 NAPHTYRIDINE DERIVATIVES
ES457692A ES457692A1 (en) 1976-04-13 1977-04-11 Procedure for preparing naftiridine derivatives. (Machine-translation by Google Translate, not legally binding)
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
JP52041904A JPS5823877B2 (en) 1976-04-13 1977-04-11 Naphthyridine derivatives and their production method
YU00948/77A YU94877A (en) 1976-04-13 1977-04-11 Process for obtaining naphthiridine derivatives
MT811A MTP811B (en) 1976-04-13 1977-04-11 Indolo (3,2,1-de)(1.5) naphthyzidine derivatives
US05/786,557 US4190657A (en) 1976-03-11 1977-04-11 Naphthyridine derivatives
LU77100A LU77100A1 (en) 1976-04-13 1977-04-12
CA275,948A CA1072960A (en) 1976-04-13 1977-04-12 Indolo (3,2,1-de) (1,5) naphthyridine 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
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
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
CS239477A CS220313B2 (en) 1976-04-13 1977-04-12 Method of producing new naphtyridine derivatives
AT254277A AT352741B (en) 1976-04-13 1977-04-12 PROCESS FOR THE PREPARATION OF NEW NAPHTYRIDE DERIVATIVES, THEIR SALT AND OPTICAL ISOMERS
AR267179A AR214519A1 (en) 1976-04-13 1977-04-12 PROCEDURE TO OBTAIN TETRAHYDRO-1,2,3,3A-INDOL- (3,2,1-DE) NAPHTHYRIDINE
PT66428A PT66428B (en) 1976-04-13 1977-04-12 PROCESS FOR THE PREPARATION OF NEW NAPHTHYRIDINE DERIVATIVES
ZA00772209A ZA772209B (en) 1976-04-13 1977-04-12 Naphtyridine derivatives
AU24189/77A AU506031B2 (en) 1976-04-13 1977-04-12 Indolo(3, 2, 1-de) (1, 5) naphthyrudune derivatives
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
GB15165/77A GB1543283A (en) 1976-04-13 1977-04-12 Indolo-(3,2,1-de)(1,5)naphthyridine derivatives
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
CH450777A CH622795A5 (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
CS578381A CS220344B2 (en) 1976-04-13 1977-04-12 Method of preparing new naphtyridine derivatives
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
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
GR53198A GR63658B (en) 1976-04-13 1977-04-13 Process for derivatives preparation of naphyridine
NL7704004A NL7704004A (en) 1976-04-13 1977-04-13 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities
SU772470258A SU655314A3 (en) 1976-04-13 1977-04-13 Method of obtaining naphthyridine derivatives or their stereoisomers or their salts
FI803790A FI803790A7 (en) 1976-04-13 1977-04-13 Method for the preparation of anoxemic 1,2,3,3a,4,5-hexahydro-6-oxo-6H-indolo[3,2,1-de/ /1,5/naphthyridines.
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
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
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
FR7610773A FR2358146A1 (en) 1976-04-13 1976-04-13 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities

Publications (2)

Publication Number Publication Date
FR2358146A1 true FR2358146A1 (en) 1978-02-10
FR2358146B1 FR2358146B1 (en) 1978-12-08

Family

ID=9171744

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7610773A Granted FR2358146A1 (en) 1976-03-11 1976-04-13 Indolo-(1,5)-naphthyridine derivs. - having antianoxia and psychotropic activities

Country Status (4)

Country Link
BE (1) BE853435A (en)
FR (1) FR2358146A1 (en)
IN (1) IN145423B (en)
ZA (1) ZA772209B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2475394A1 (en) * 1980-02-12 1981-08-14 Synthelabo PHARMACEUTICAL COMPOSITIONS CONTAINING HEXAHYDRO-1, 2, 3, 3A, 4, 5, 6H INDOLO (3, 2, 1 - D. E) (1, 5) NAPHTHYRIDINONE - 6

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5337696A (en) * 1976-08-26 1978-04-06 Omnium Chimique Sa Hexahydrocantinonee6 derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2475394A1 (en) * 1980-02-12 1981-08-14 Synthelabo PHARMACEUTICAL COMPOSITIONS CONTAINING HEXAHYDRO-1, 2, 3, 3A, 4, 5, 6H INDOLO (3, 2, 1 - D. E) (1, 5) NAPHTHYRIDINONE - 6

Also Published As

Publication number Publication date
BE853435A (en) 1977-10-10
FR2358146B1 (en) 1978-12-08
ZA772209B (en) 1978-03-29
IN145423B (en) 1978-10-07

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