BE898233A - Dérivés benzylidéniques hydroxylés, leur préparation et leur application en thérapeutique. - Google Patents

Dérivés benzylidéniques hydroxylés, leur préparation et leur application en thérapeutique. Download PDF

Info

Publication number: BE898233A
Authority: BE; Belgium
Prior art keywords: phenyl; formula; chloro; sep; compound
Prior art date: 1982-11-15

Application number

BE0/211882A

Other languages

English (en)

French (fr)

Inventor

J P Kaplan

B Raizon

Original Assignee

Synthelabo

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.)

1982-11-15

Filing date

1983-11-16

Publication date

1984-05-16

1983-11-16 Application filed by Synthelabo filed Critical Synthelabo

1984-05-16 Publication of BE898233A publication Critical patent/BE898233A/fr

Links

238000002360 preparation method Methods 0.000 title claims description 6
230000001225 therapeutic effect Effects 0.000 title description 3
-1 atom halogen Chemical class 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract 4
239000003513 alkali Substances 0.000 claims abstract 2
150000001342 alkaline earth metals Chemical class 0.000 claims abstract 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 25
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 9
239000012965 benzophenone Substances 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 5
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
150000008366 benzophenones Chemical class 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
150000003254 radicals Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
238000000605 extraction Methods 0.000 claims description 2
238000000338 in vitro Methods 0.000 claims description 2
238000001727 in vivo Methods 0.000 claims description 2
210000004185 liver Anatomy 0.000 claims description 2
230000004060 metabolic process Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
238000000034 method Methods 0.000 claims 2
239000002585 base Substances 0.000 claims 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 abstract 1
238000010992 reflux Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
IYGYMKDQCDOMRE-QRWMCTBCSA-N Bicculine Chemical compound O([C@H]1C2C3=CC=4OCOC=4C=C3CCN2C)C(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-QRWMCTBCSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
210000000941 bile Anatomy 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
IYGYMKDQCDOMRE-UHFFFAOYSA-N d-Bicucullin Natural products CN1CCC2=CC=3OCOC=3C=C2C1C1OC(=O)C2=C1C=CC1=C2OCO1 IYGYMKDQCDOMRE-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
CQNMGUMYWZFMRJ-UHFFFAOYSA-N (5-chloro-2,3-dihydroxyphenyl)-(4-chlorophenyl)methanone Chemical compound OC1=CC(Cl)=CC(C(=O)C=2C=CC(Cl)=CC=2)=C1O CQNMGUMYWZFMRJ-UHFFFAOYSA-N 0.000 description 2
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
AACMFFIUYXGCOC-UHFFFAOYSA-N bicuculline Natural products CN1CCc2cc3OCOc3cc2C1C4OCc5c6OCOc6ccc45 AACMFFIUYXGCOC-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012065 filter cake Substances 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical group COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WCVPFJVXEXJFLB-UHFFFAOYSA-N 4-aminobutanamide Chemical compound NCCCC(N)=O WCVPFJVXEXJFLB-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
241001274216 Naso Species 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
PBBVMOBELJQARG-UHFFFAOYSA-N bicucullinine Natural products CN(C)CCc1cc2OCOc2cc1C(=O)C(=O)c1ccc2OCOc2c1C(O)=O PBBVMOBELJQARG-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000001953 common bile duct Anatomy 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000003371 gabaergic effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
150000002634 lipophilic molecules Chemical class 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/86—Ketones containing a keto group bound to a six-membered aromatic ring containing —CHO groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/515—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an acetalised, ketalised hemi-acetalised, or hemi-ketalised hydroxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE0/211882A 1982-11-15 1983-11-16 Dérivés benzylidéniques hydroxylés, leur préparation et leur application en thérapeutique. BE898233A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8219078A FR2536070A1 (fr)	1982-11-15	1982-11-15	Diphenyl-azomethines hydroxylees, leur preparation et leur application en therapeutique

Publications (1)

Publication Number	Publication Date
BE898233A true BE898233A (fr)	1984-05-16

Family

ID=9279176

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/211882A BE898233A (fr)	1982-11-15	1983-11-16	Dérivés benzylidéniques hydroxylés, leur préparation et leur application en thérapeutique.

Country Status (9)

Country	Link
JP (1)	JPS59108755A (it)
BE (1)	BE898233A (it)
DE (1)	DE3341198A1 (it)
FR (1)	FR2536070A1 (it)
GB (1)	GB2129804A (it)
IL (1)	IL70227A0 (it)
IT (1)	IT1170245B (it)
LU (1)	LU85090A1 (it)
NL (1)	NL8303903A (it)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2319338A1 (fr) *	1975-08-01	1977-02-25	Synthelabo	Nouveaux derives de a- phenyl benzylideniques des acides amines, leur preparation et les medicaments qui en contiennent

1982
- 1982-11-15 FR FR8219078A patent/FR2536070A1/fr active Granted
1983
- 1983-11-14 IT IT23700/83A patent/IT1170245B/it active
- 1983-11-14 LU LU85090A patent/LU85090A1/fr unknown
- 1983-11-14 JP JP58214916A patent/JPS59108755A/ja active Pending
- 1983-11-14 NL NL8303903A patent/NL8303903A/nl not_active Application Discontinuation
- 1983-11-14 DE DE19833341198 patent/DE3341198A1/de not_active Withdrawn
- 1983-11-14 GB GB08330288A patent/GB2129804A/en not_active Withdrawn
- 1983-11-14 IL IL70227A patent/IL70227A0/xx unknown
- 1983-11-16 BE BE0/211882A patent/BE898233A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB8330288D0 (en)	1983-12-21
IT8323700A0 (it)	1983-11-14
FR2536070A1 (fr)	1984-05-18
IT1170245B (it)	1987-06-03
DE3341198A1 (de)	1984-05-17
JPS59108755A (ja)	1984-06-23
LU85090A1 (fr)	1985-07-17
IL70227A0 (en)	1984-02-29
FR2536070B1 (it)	1985-03-08
GB2129804A (en)	1984-05-23
NL8303903A (nl)	1984-06-01

Legal Events

Date

Code

Title

Description

1986-05-31

RE

Patent lapsed

Owner name: SYNTHELABO

Effective date: 19851130

Publication	Publication Date	Title
EP0107569B1 (fr)	1987-03-18	Nouveaux dérivés de la 6-amino 7-hydroxy 4,5,6,7-tétrahydroimidazo/4,5,1-j-k/ /1/ benzazépin-2(1H)-one, leurs sels, leur préparation, leur application à titre de médicaments, les compositions les renfermant
EP0399856B1 (fr)	1995-08-09	Pteridin-4 (3H)-ones, procédés de préparation et médicaments les contenant
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EP0307303B1 (fr)	1991-12-04	[(Pyrimidinyl-2)-aminoalkyl]-1 pipéridines, leur préparation et leur application en thérapeutique
FR2511366A1 (fr)	1983-02-18	Nouveaux derives de la pyridazine, leur procede de preparation et les medicaments, actifs sur le systeme nerveux central, qui en contiennent
EP0239461A1 (fr)	1987-09-30	Dérivés de N-¬¬(hydroxy-2 phényl) (phényl) méthylène amino-2 éthyl acétamide, leur préparation et leur application en thérapeutique
EP0418933A1 (fr)	1991-03-27	Dérivés d'alcadiènes, leurs préparations, les médicaments les contenant et produits intermédiaires
FR2601011A1 (fr)	1988-01-08	Nouveaux derives tricycliques agonistes des recepteurs cholinergiques et medicaments en contenant
EP0006789A1 (fr)	1980-01-09	Composés bis (aryloxyalcanecarboxyliques), leur préparation et leur utilisation en thérapeutique
FR2737494A1 (fr)	1997-02-07	Derives de benzenesulfonamide, leur preparation et leur application en therapeutique
EP0301936A1 (fr)	1989-02-01	Dérivés de pipéridine, leur préparation et leur application en thérapeutique
EP0233105B1 (fr)	1991-01-09	Compositions thérapeutiques à base de dérivés de 3-alkoxyflavones et nouveaux dérivés de 3-alkoxyflavones
BE898233A (fr)	1984-05-16	Dérivés benzylidéniques hydroxylés, leur préparation et leur application en thérapeutique.
CA1115294A (fr)	1981-12-29	Procede de preparation de nouveaux derives de la 5h-benzocyclohepten-7-amine et leurs sels
FR2600647A1 (fr)	1987-12-31	Derives de la glycine
BE898324A (fr)	1984-05-28	Derives benzylideniques soufres, leur preparation et leur application en therapeutique.
FR2581646A1 (fr)	1986-11-14	Derives d'imidazopyridine, leur preparation et leur application en therapeutique
EP0125975B1 (fr)	1986-03-26	Diphénylazométhines portant une chaîne esterifiée, leur préparation et leur application en thérapeutique
EP0347305B1 (fr)	1993-05-12	[(Aryl-4-pipérazinyl-1)-2 éthoxy]-3 p-cymène, les dérivés ortho, méta, para monosubstitués ou disubstitués sur le noyau phényle dudit produit, le procédé de préparation desdits dérivés, et les médicaments contenant lesdits composés comme principe actif
FR2475543A1 (fr)	1981-08-14	Derives benzylideniques, leur preparation et leur application en therapeutique
BE884977A (fr)	1981-03-02	Nouveau n-phenyl-benzamides utiles dans le traitement de l'inflammation et de la douleur des mammiferes
FR2544309A1 (fr)	1984-10-19	Diphenylazomethines hydroxylees, leur preparation et leur application en therapeutique
MC1054A1 (fr)	1976-02-20	Nouveaux ethers d'enol basiques,leurs sels et procedes pour leur preparation
FR2511364A1 (fr)	1983-02-18	Derives d'acides (4-cycloalkyl-naphtyl) methylene aminooxy alcanoiques, procede d'obtention et application en therapeutique
BE898323A (fr)	1984-05-28	Derives benzylideniques alkyles, leur preparation et leur application en therapeutique.