WO1979000319A1 - Nouvelles indolo (2, 3-a) quinolizidines, leur preparation et leur utilisation therapeutique - Google Patents
Nouvelles indolo (2, 3-a) quinolizidines, leur preparation et leur utilisation therapeutique Download PDFInfo
- Publication number
- WO1979000319A1 WO1979000319A1 PCT/FR1978/000043 FR7800043W WO7900319A1 WO 1979000319 A1 WO1979000319 A1 WO 1979000319A1 FR 7800043 W FR7800043 W FR 7800043W WO 7900319 A1 WO7900319 A1 WO 7900319A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- indolo
- ethyl
- product
- preparation
- quinolizidine
- Prior art date
Links
- CDNDCHPZSHJMJN-PPUHSXQSSA-N CCCCC(CC)(CC(O)=O)[C@H](CCCC1)C(C)=C1c(cccc1)c1N Chemical compound CCCCC(CC)(CC(O)=O)[C@H](CCCC1)C(C)=C1c(cccc1)c1N CDNDCHPZSHJMJN-PPUHSXQSSA-N 0.000 description 1
- 0 CC[C@](C*)(CCC1)[C@@]2N1CCc1c2[n]c2ccccc12 Chemical compound CC[C@](C*)(CCC1)[C@@]2N1CCc1c2[n]c2ccccc12 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
Definitions
- the present invention relates to indolo (2, 3-a) quinolizidines, their methods of preparation and the therapeutic compositions containing them.
- R represents -COOC 2 H 5 ; COOH; CN, a primary or secondary amino methylene group, a methylenido group, or in which R, with the indolo ring nitrogen, represents one of the groups N-CO-NH-CH 2 or N-CO; the latter derivatives are D homo azaeburnamonines or D eburnamonines.
- the present invention also relates, where appropriate, to the acid addition salts of the above compounds.
- R can be, for example, a methylenaminocarbalcoxy, a methylaminoaryloxycarbonyl, a methyleaminoalkanoyl, a methyleaminoalkyl or a substituted methylenideido group.
- R can represent COOH, NH 2 , methylenaminocarbethoxy, methylenamino- (trimethoxy-3,4,5) -benzoyl, methylenaminophenoxycarbonyl, methylenideidodiethylaminoethyl, methylenaminopentanoyl, methylenaminopentyl and amidopiperyl.
- compositions therapeutic comprising one or more of these compounds mixed with a diluent or support for therapeutically acceptable reactions.
- the above compounds can be prepared according to the present invention, by condensing together aminoethyl-2-indole-3 and chloro-1-chlorocarbonyl-4- (A) -4-hexane, where A represents -COOC 2 H 5 or -CN, to form the corresponding amide; by subjecting the amide to a strongly basic agent to eliminate HCl and carry out the formation of a cycle with the nitrogen atom on the substituent indole3; by carrying out the formation of a quinolizidine cycle of the product by the action of a dehydrating agent then of a perchlorate; hydrogenating the quinolizidinium perchlorate obtained to produce the isomeric mixture of indolo (2,3-a.) quinolizidine and separating the isomers; the corresponding reaction schemes are represented below under the title "Common initial sequence" and lead only to the compounds where R is -COOC 2 H 5 or -CN (2 isomeric forms in each case, that is to say 4 compounds) .
- - 1 (a) to 1 (i) are references to the different steps of Example 1 where the starting material is the derivative of ethoxycarbonyl-4 and the final products, acids or derivatives thereof, and - 2 (a) to 2 (g) are references to the different steps of Example 2, where the starting product is the cyano-4 derivative and the final products, methylamino derivatives.
- Example 1 The present invention is illustrated by the following examples: Example 1
- a solution of 6.25 g (0.0147 mole) of the perchlorate salt of the previous step in 80 ml of ethanol is hydrogenated for 12 hours in the presence of 0.3 g of platinum oxide. After filtration, the ethanol is evaporated under reduced pressure and the residue taken up with methylene dichloride and stirred with 5% sodium hydroxide. The organic phase is decanted and washed with distilled water.
- the hydrochloride is obtained by treatment with HCl in hydroalcoholic solution. Mp 225 ° C.
- 107.426 C O; -13.712 CH; -82.162 CH.
- the CN peak at around 2250 cm is absent.
- phenoxycarbonylaminomethyl-1-ethyl-1-indolo (2, 3-a) quinolizidine (12b-H; 1-C 2 H 5 trans-isomer) is prepared according to the method of Example 3, but in replacing ethyl chloroformate with phenyl chloroformate.
- the hydrochloride is prepared by treating the above oil, with hydrochloric acid in 20 ml of ethanol, then by centrifuging. The yield is 60%, calculated on the starting amine (II) .F ⁇ 260 ° C. The product precipitates with 1/2 mole of water of crystallization.
- the corresponding derivative of phenoxycarbonylamino-methyl-1-ethyl-1 is prepared, 7 g of the trans II derivative of Example 2 (f) and 100 ml of tetrahydrofuran are placed in a 500 ml three-necked flask, provided with 'an agitator and two bromine bulbs. The flask is cooled to 0-5 ° C. and, at this temperature, 4.25 g of phenyl chloroformate in 50 ml of tetrahydrofuran and 2.9 g of sodium bicarbonate in 50 ml are simultaneously added of water (the quantities added were calculated so as to maintain the pH at 6-7). The mixture is then allowed to warm to ambient temperature, and the mixture is stirred for 3 hours. The product is extracted with 100 ml of methylene chloride, and the extract is washed several times with water before being dried with sodium sulfate and concentrated by evaporation. 11 g of the product, which is an oil, are obtained.
- the ureidomethyl-1 product is prepared as follows:
- the first step gave 4.6 g of crystals, melting at 202 ° C, and the second step, 0.8 g of crystals, melting at 198 ° C.
- the combined products are then recrystallized from benzene to give 4.65 g of the final product.
- Example 5 Using conditions and techniques identical to those of Example 5, a solution of 5.7 g of the trans derivative of Example 2 (f) and 2.1 g of triethylamine in 120 ml of chloride is reacted. methylene, and a solution of 2.45 g of pentanoyl chloride in 20 ml of methylene chloride. 7.8 g of an oil which contains one is therefore obtained. little triethylamine residue.
- the acid addition salt is prepared with maleic acid in solution in a mixture of isopropanol and di-isopropyl ether. Initially, the salt appears as an oil, but can be recrystallized from ethyl acetate to give 6.7 g of dimaleate, melting at 105 ° C.
- the hydrochloride is obtained by adding 4N HCl to a solution of the base in a 1: 1 mixture of ethanol and ethyl ether.
- Example 3 The process of Example 3 is repeated, except that the cis derivative (I) of Example 2 (g) is used instead of the trans derivative (II) of Example 2 (f). 2.1 g of free base are obtained (yield 84%). Mp 210 ° C.
- the hydrochloride is obtained by the action of 4N hydrochloric acid in acetone.
- Example 6 The procedure is first carried out as in the first part of Example 6, using the cis derivative I of Example 2 (g) instead of the trans derivative II of Example 2 (f).
- the LD 50 was determined per os on mice.
- the compounds of the invention have a toxicity comparable to that of vincamine or lower.
- the most toxic (LD 50: 400 mg / kg: vincamine 450 mg / kg) are those of Examples 2 (f), 3 and 4; the least toxic are those of Examples 5, 10 and 12 while the remaining compounds exhibit intermediate toxicity.
- the compounds of the present invention can be administered i.v. or per os in doses comparable to those used for vincamine (dosage units containing from 5 to 40 mg).
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP54500118A JPS6147838B2 (zh) | 1977-11-25 | 1978-11-24 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB49201/77 | 1977-11-25 | ||
GB4920177 | 1977-11-25 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1979000319A1 true WO1979000319A1 (fr) | 1979-06-14 |
Family
ID=10451538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1978/000043 WO1979000319A1 (fr) | 1977-11-25 | 1978-11-24 | Nouvelles indolo (2, 3-a) quinolizidines, leur preparation et leur utilisation therapeutique |
Country Status (28)
Country | Link |
---|---|
JP (1) | JPS6147838B2 (zh) |
AR (1) | AR218514A1 (zh) |
AT (1) | AT372384B (zh) |
AU (1) | AU529108B2 (zh) |
BE (1) | BE872134A (zh) |
CA (1) | CA1100959A (zh) |
CH (1) | CH641181A5 (zh) |
DE (1) | DE2851028A1 (zh) |
DK (1) | DK154430C (zh) |
EG (1) | EG13683A (zh) |
ES (1) | ES475328A1 (zh) |
FI (1) | FI64372C (zh) |
FR (2) | FR2409755A1 (zh) |
HK (1) | HK60884A (zh) |
IE (1) | IE47518B1 (zh) |
IN (1) | IN151146B (zh) |
IT (1) | IT1160263B (zh) |
LU (1) | LU80576A1 (zh) |
MX (1) | MX5529E (zh) |
MY (1) | MY8500029A (zh) |
NL (1) | NL7811562A (zh) |
NO (1) | NO151288C (zh) |
NZ (1) | NZ188974A (zh) |
PT (1) | PT68825A (zh) |
SE (2) | SE431650B (zh) |
SG (1) | SG61182G (zh) |
WO (1) | WO1979000319A1 (zh) |
ZA (1) | ZA786426B (zh) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0079411A1 (fr) * | 1981-11-18 | 1983-05-25 | Thal, Claude | Dérivés d'indoloquinolizine, leur procédé de préparation et leur application en thérapeutique |
FR2529552A1 (fr) * | 1982-07-05 | 1984-01-06 | Centre Nat Rech Scient | Nouveau procede de preparation d'intermediaires de synthese de la vindoline et intermediaires de synthese |
EP0177361A2 (en) * | 1984-10-05 | 1986-04-09 | Richter Gedeon Vegyeszeti Gyar R.T. | Octahydroindolo-[2,3-a]quinolizin-l-yl-alkanecarboxylic acid amides and salts thereof |
EP0200436A2 (en) * | 1985-04-19 | 1986-11-05 | Richter Gedeon Vegyeszeti Gyar R.T. | 12b-Substituted 1-hydroxymethyl-octahydroindolo[2,3-a]quinolizine derivatives |
EP0202774A2 (en) * | 1985-04-19 | 1986-11-26 | Richter Gedeon Vegyeszeti Gyar R.T. | 1,12b-Disubstituted octahydroindolo [2,3-a]-Quinolizine derivatives |
FR2713644A1 (fr) * | 1993-12-14 | 1995-06-16 | Adir | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
FR2713643A1 (fr) * | 1993-12-14 | 1995-06-16 | Adir | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
EP0704439A4 (en) * | 1993-06-18 | 1996-02-19 | Fujisawa Pharmaceutical Co | NOVEL INTERMEDIATE FOR USE AND TREATMENT OF SYNTHESIS OF PRODUCTION OF AN AMINOPIPERAZINE DERIVATIVE |
FR2911141A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Nouveaux derives triazabenzo[a]naphtho[2,1,8-cde]azulene, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
FR2911143A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Utilisation de composes neuroprotecteurs pour l'obtention de medicaments destines au traitement de maladies neurodegeneratives. |
FR2911142A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Nouveaux derives aminopyrrolo[1,2-a]indole et aminopyridazino[1,6-a]indole,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI95572C (fi) | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
US7798176B2 (en) † | 2002-06-24 | 2010-09-21 | Saint-Gobain Isover | Insulating panel for supply duct |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7312084A (zh) * | 1972-09-06 | 1974-03-08 | ||
FR2237901A1 (en) * | 1973-07-16 | 1975-02-14 | Omnium Chimique Sa | Vincamone and 21-epi-n-vincamone synthesis - from tabersone |
FR2285877A1 (fr) * | 1974-09-27 | 1976-04-23 | Richter Gedeon Vegyeszet | Composes polycycliques azotes et leur procede de preparation |
FR2315277A1 (fr) * | 1975-06-25 | 1977-01-21 | Anvar | Nouveaux derives pentacycliques, leur preparation et les compositions qui les contiennent |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU171165B (hu) * | 1974-11-26 | 1977-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija proizvodnykh oktagidro-indolo-skobka-2,3-a-skobka zakryta-kinolizina |
-
1978
- 1978-11-15 ZA ZA00786426A patent/ZA786426B/xx unknown
- 1978-11-20 BE BE191824A patent/BE872134A/xx not_active IP Right Cessation
- 1978-11-22 NZ NZ188974A patent/NZ188974A/xx unknown
- 1978-11-23 AU AU41874/78A patent/AU529108B2/en not_active Expired
- 1978-11-23 AR AR274552A patent/AR218514A1/es active
- 1978-11-23 ES ES475328A patent/ES475328A1/es not_active Expired
- 1978-11-23 NO NO783958A patent/NO151288C/no unknown
- 1978-11-23 AT AT0837478A patent/AT372384B/de active
- 1978-11-23 PT PT68825A patent/PT68825A/pt unknown
- 1978-11-23 FI FI783581A patent/FI64372C/fi not_active IP Right Cessation
- 1978-11-24 NL NL7811562A patent/NL7811562A/xx not_active Application Discontinuation
- 1978-11-24 JP JP54500118A patent/JPS6147838B2/ja not_active Expired
- 1978-11-24 MX MX787557U patent/MX5529E/es unknown
- 1978-11-24 FR FR7833176A patent/FR2409755A1/fr active Granted
- 1978-11-24 LU LU80576A patent/LU80576A1/xx unknown
- 1978-11-24 IT IT30171/78A patent/IT1160263B/it active
- 1978-11-24 IN IN851/DEL/78A patent/IN151146B/en unknown
- 1978-11-24 CH CH683579A patent/CH641181A5/fr not_active IP Right Cessation
- 1978-11-24 DK DK524978A patent/DK154430C/da not_active IP Right Cessation
- 1978-11-24 WO PCT/FR1978/000043 patent/WO1979000319A1/fr unknown
- 1978-11-24 FR FR7833175A patent/FR2423492A1/fr active Granted
- 1978-11-24 DE DE19782851028 patent/DE2851028A1/de active Granted
- 1978-11-24 IE IE2328/78A patent/IE47518B1/en unknown
- 1978-11-24 CA CA316,809A patent/CA1100959A/en not_active Expired
- 1978-11-25 EG EG669/78A patent/EG13683A/xx active
-
1979
- 1979-07-23 SE SE7906287A patent/SE431650B/sv not_active IP Right Cessation
-
1980
- 1980-11-07 SE SE8007845A patent/SE435622B/sv not_active IP Right Cessation
-
1982
- 1982-12-03 SG SG611/82A patent/SG61182G/en unknown
-
1984
- 1984-08-02 HK HK608/84A patent/HK60884A/xx unknown
-
1985
- 1985-12-30 MY MY29/85A patent/MY8500029A/xx unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL7312084A (zh) * | 1972-09-06 | 1974-03-08 | ||
FR2237901A1 (en) * | 1973-07-16 | 1975-02-14 | Omnium Chimique Sa | Vincamone and 21-epi-n-vincamone synthesis - from tabersone |
FR2285877A1 (fr) * | 1974-09-27 | 1976-04-23 | Richter Gedeon Vegyeszet | Composes polycycliques azotes et leur procede de preparation |
FR2315277A1 (fr) * | 1975-06-25 | 1977-01-21 | Anvar | Nouveaux derives pentacycliques, leur preparation et les compositions qui les contiennent |
Non-Patent Citations (1)
Title |
---|
Helvetica Chimica Acta, volume 60, (1977), 1801-10, publié le 13 juillet 1977 * |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0079411A1 (fr) * | 1981-11-18 | 1983-05-25 | Thal, Claude | Dérivés d'indoloquinolizine, leur procédé de préparation et leur application en thérapeutique |
FR2529552A1 (fr) * | 1982-07-05 | 1984-01-06 | Centre Nat Rech Scient | Nouveau procede de preparation d'intermediaires de synthese de la vindoline et intermediaires de synthese |
EP0177361A2 (en) * | 1984-10-05 | 1986-04-09 | Richter Gedeon Vegyeszeti Gyar R.T. | Octahydroindolo-[2,3-a]quinolizin-l-yl-alkanecarboxylic acid amides and salts thereof |
EP0177361A3 (en) * | 1984-10-05 | 1987-09-02 | Richter Gedeon Vegyeszeti Gyar R.T. | Octahydroindolo-[2,3-a]quinolizin-l-yl-alkanecarboxylic acid amides and salts thereof |
EP0200436A2 (en) * | 1985-04-19 | 1986-11-05 | Richter Gedeon Vegyeszeti Gyar R.T. | 12b-Substituted 1-hydroxymethyl-octahydroindolo[2,3-a]quinolizine derivatives |
EP0202774A2 (en) * | 1985-04-19 | 1986-11-26 | Richter Gedeon Vegyeszeti Gyar R.T. | 1,12b-Disubstituted octahydroindolo [2,3-a]-Quinolizine derivatives |
EP0200436A3 (en) * | 1985-04-19 | 1989-01-18 | Richter Gedeon Vegyeszeti Gyar R.T. | 12b-Substituted 1-hydroxymethyl-octahydroindolo[2,3-a]quinolizine derivatives |
EP0202774A3 (en) * | 1985-04-19 | 1989-03-15 | Richter Gedeon Vegyeszeti Gyar R.T. | 1,12b-Disubstituted octahydroindolo [2,3-a]-Quinolizine derivatives |
EP0704439A1 (en) * | 1993-06-18 | 1996-04-03 | Fujisawa Pharmaceutical Co., Ltd. | Novel intermediate for synthetic use and process for producing aminopiperazine derivative |
EP0704439A4 (en) * | 1993-06-18 | 1996-02-19 | Fujisawa Pharmaceutical Co | NOVEL INTERMEDIATE FOR USE AND TREATMENT OF SYNTHESIS OF PRODUCTION OF AN AMINOPIPERAZINE DERIVATIVE |
EP0658557A1 (fr) * | 1993-12-14 | 1995-06-21 | Adir Et Compagnie | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
FR2713643A1 (fr) * | 1993-12-14 | 1995-06-16 | Adir | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
FR2713644A1 (fr) * | 1993-12-14 | 1995-06-16 | Adir | Nouveaux analogues de l'éburnane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
FR2911141A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Nouveaux derives triazabenzo[a]naphtho[2,1,8-cde]azulene, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
FR2911143A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Utilisation de composes neuroprotecteurs pour l'obtention de medicaments destines au traitement de maladies neurodegeneratives. |
FR2911142A1 (fr) * | 2007-01-05 | 2008-07-11 | Servier Lab | Nouveaux derives aminopyrrolo[1,2-a]indole et aminopyridazino[1,6-a]indole,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
WO2008099083A2 (fr) * | 2007-01-05 | 2008-08-21 | Les Laboratoires Servier | Utilisation de composes neuroprotecteurs pour l'obtention de médicaments destines au traitement de maladies neurodegeneratives |
WO2008099081A2 (fr) * | 2007-01-05 | 2008-08-21 | Les Laboratoires Servier | NOUVEAUX DÉRIVÉS TRIAZABENZO[α]NAPHTHO[2,L,8-CDE]AZULÈNE, LEUR PROCÉDÉ DE PRÉPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
WO2008099081A3 (fr) * | 2007-01-05 | 2008-10-23 | Servier Lab | NOUVEAUX DÉRIVÉS TRIAZABENZO[α]NAPHTHO[2,L,8-CDE]AZULÈNE, LEUR PROCÉDÉ DE PRÉPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
WO2008099083A3 (fr) * | 2007-01-05 | 2008-12-11 | Servier Lab | Utilisation de composes neuroprotecteurs pour l'obtention de médicaments destines au traitement de maladies neurodegeneratives |
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