FR2669821A1 - Utilisation de phenylethanolaminotetralines pour la preparation de medicaments destines au traitement de la depression. - Google Patents
Utilisation de phenylethanolaminotetralines pour la preparation de medicaments destines au traitement de la depression. Download PDFInfo
- Publication number
- FR2669821A1 FR2669821A1 FR9015171A FR9015171A FR2669821A1 FR 2669821 A1 FR2669821 A1 FR 2669821A1 FR 9015171 A FR9015171 A FR 9015171A FR 9015171 A FR9015171 A FR 9015171A FR 2669821 A1 FR2669821 A1 FR 2669821A1
- Authority
- FR
- France
- Prior art keywords
- formula
- treatment
- compounds
- preparation
- pharmaceutically acceptable
- 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
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000003814 drug Substances 0.000 title claims abstract description 8
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- -1 2-ethoxycarbonylmethoxy Chemical group 0.000 claims description 7
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 abstract description 5
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 208000020401 Depressive disease Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 8
- 230000008485 antagonism Effects 0.000 description 8
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- STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 description 8
- 229960002052 salbutamol Drugs 0.000 description 8
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- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- GQDDNDAYOVNZPG-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C[C]2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3N=C21 GQDDNDAYOVNZPG-SCYLSFHTSA-N 0.000 description 6
- 229960000317 yohimbine Drugs 0.000 description 6
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- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 5
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 5
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 5
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 5
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
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- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
- 239000000935 antidepressant agent Substances 0.000 description 3
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- 239000000470 constituent Substances 0.000 description 3
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- 239000000021 stimulant Substances 0.000 description 3
- NRHVNPYOTNGECT-UHFFFAOYSA-N 2-(3-chlorophenyl)ethanamine Chemical compound NCCC1=CC=CC(Cl)=C1 NRHVNPYOTNGECT-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
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- 230000001430 anti-depressive effect Effects 0.000 description 2
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
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- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 150000001510 aspartic acids Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229940124748 beta 2 agonist Drugs 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
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- 229940110456 cocoa butter Drugs 0.000 description 1
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- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 150000002307 glutamic acids Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 231100000171 higher toxicity Toxicity 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940041476 lactose 100 mg Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
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- 230000002269 spontaneous effect Effects 0.000 description 1
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- 230000000638 stimulation Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
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- 239000007929 subcutaneous injection Substances 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 230000006794 tachycardia Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9015171A FR2669821A1 (fr) | 1990-12-04 | 1990-12-04 | Utilisation de phenylethanolaminotetralines pour la preparation de medicaments destines au traitement de la depression. |
| EP91403263A EP0489640B1 (fr) | 1990-12-04 | 1991-12-03 | Utilisation de phényléthanolaminotétralines pour la préparation de médicaments antidépressifs et anti-stress |
| IE419591A IE76322B1 (en) | 1990-12-04 | 1991-12-03 | Use of phenylethanolaminotetralines for preparing antidepressant and anti-stress medicines |
| DE69122480T DE69122480T2 (de) | 1990-12-04 | 1991-12-03 | Verwendung von Phenyläthanolaminotetralinen zur Herstellung eines antidepressiven und Antistress-Arzneimittels |
| AT91403263T ATE143592T1 (de) | 1990-12-04 | 1991-12-03 | Verwendung von phenyläthanolaminotetralinen zur herstellung eines antidepressiven und antistress- arzneimittels |
| DK91403263.6T DK0489640T3 (da) | 1990-12-04 | 1991-12-03 | Anvendelse af phenylethanolaminotetraliner til fremstilling af antidepressive lægemidler og anti-stress-lægemidler |
| SG1996001786A SG47450A1 (en) | 1990-12-04 | 1991-12-03 | Use of phenylethanolaminotetralins for the preparation of antidepressant and anti-stress medicaments |
| CA002056906A CA2056906C (en) | 1990-12-04 | 1991-12-04 | Use of phenylethanolaminotetralins for the preparation of anti-depressant and anti-stress pharmaceutical compositions |
| AU88395/91A AU653968B2 (en) | 1990-12-04 | 1991-12-04 | Use of phenylethanolaminotetralins for the preparation of anti-depressant and anti-stress pharmaceutical compositions |
| JP3320532A JP2610735B2 (ja) | 1990-12-04 | 1991-12-04 | 抗鬱剤および抗ストレス剤組成物 |
| US07/804,580 US5270341A (en) | 1990-12-04 | 1991-12-04 | Method of treatment or prophylaxis of depression and stress |
| MX9102365A MX9102365A (es) | 1990-12-04 | 1991-12-04 | Composicion farmaceutica que contiene fenil etanolcomposicion farmaceutica que contiene fenil etanol amino tetralinas. amino tetralinas. |
| HU913800A HU207793B (en) | 1990-12-04 | 1991-12-04 | Process for producing antidepressant and antistress active pharmaceutical compositions containingphenyl-ethanol-amino-tetralines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9015171A FR2669821A1 (fr) | 1990-12-04 | 1990-12-04 | Utilisation de phenylethanolaminotetralines pour la preparation de medicaments destines au traitement de la depression. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2669821A1 true FR2669821A1 (fr) | 1992-06-05 |
| FR2669821B1 FR2669821B1 (https=) | 1994-12-09 |
Family
ID=9402882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9015171A Granted FR2669821A1 (fr) | 1990-12-04 | 1990-12-04 | Utilisation de phenylethanolaminotetralines pour la preparation de medicaments destines au traitement de la depression. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5270341A (https=) |
| EP (1) | EP0489640B1 (https=) |
| JP (1) | JP2610735B2 (https=) |
| AT (1) | ATE143592T1 (https=) |
| AU (1) | AU653968B2 (https=) |
| CA (1) | CA2056906C (https=) |
| DE (1) | DE69122480T2 (https=) |
| DK (1) | DK0489640T3 (https=) |
| FR (1) | FR2669821A1 (https=) |
| HU (1) | HU207793B (https=) |
| IE (1) | IE76322B1 (https=) |
| MX (1) | MX9102365A (https=) |
| SG (1) | SG47450A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2826651B1 (fr) * | 2001-06-28 | 2005-09-02 | Sanofi Synthelabo | Forme cristalline d'une phenylethanolamine, sa preparation et compositions pharmaceutiques la contenant |
| EP1623705A1 (en) * | 2004-07-09 | 2006-02-08 | Sanofi-Aventis | Use of phenylethanolaminotetralines for preparing anxiolytic drugs |
| FR2890862B1 (fr) * | 2005-09-19 | 2008-01-25 | Sanofi Aventis Sa | Association d'agoniste aux recepteurs beta 3 et d'inhibiteur de la recapture de monoamnies, compostion pharmaceutique la contenant et son utilisation en therapeutique. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2584712A1 (fr) * | 1985-07-10 | 1987-01-16 | Midy Spa | Phenylethanolamines a activite lipolytique, un procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2643076A1 (fr) * | 1989-02-14 | 1990-08-17 | Midy Spa | Carboxyalkyl-ethers de la 2-amino-7-hydroxytetraline |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH637363A5 (en) * | 1977-11-24 | 1983-07-29 | Sandoz Ag | Process for preparing novel 2-aminotetralins |
| IL79323A (en) * | 1985-07-10 | 1990-03-19 | Sanofi Sa | Phenylethanolaminotetralines,their preparation and pharmaceutical compositions containing them |
| US4927955A (en) * | 1987-08-12 | 1990-05-22 | Sanofi | Process for the O-alkylation of N-(hydroxy)aralkylphenylethanolamines |
| DE3872100T2 (de) * | 1987-08-12 | 1993-01-28 | Sanofi Elf | Verfahren zur herstellung von phenylaethanolaminotetralinen. |
| EP0452390B1 (en) * | 1989-01-09 | 1994-10-26 | The Upjohn Company | Halo substituted aminotetralins |
| DE69028877T2 (de) * | 1989-06-13 | 1997-02-27 | Sanofi Sa | Verwendung von Phenylethanolaminen zur Herstellung von Medikamenten gegen Augenleiden |
-
1990
- 1990-12-04 FR FR9015171A patent/FR2669821A1/fr active Granted
-
1991
- 1991-12-03 SG SG1996001786A patent/SG47450A1/en unknown
- 1991-12-03 DK DK91403263.6T patent/DK0489640T3/da active
- 1991-12-03 AT AT91403263T patent/ATE143592T1/de not_active IP Right Cessation
- 1991-12-03 EP EP91403263A patent/EP0489640B1/fr not_active Expired - Lifetime
- 1991-12-03 IE IE419591A patent/IE76322B1/en not_active IP Right Cessation
- 1991-12-03 DE DE69122480T patent/DE69122480T2/de not_active Expired - Lifetime
- 1991-12-04 MX MX9102365A patent/MX9102365A/es unknown
- 1991-12-04 CA CA002056906A patent/CA2056906C/en not_active Expired - Lifetime
- 1991-12-04 HU HU913800A patent/HU207793B/hu not_active IP Right Cessation
- 1991-12-04 JP JP3320532A patent/JP2610735B2/ja not_active Expired - Lifetime
- 1991-12-04 US US07/804,580 patent/US5270341A/en not_active Expired - Lifetime
- 1991-12-04 AU AU88395/91A patent/AU653968B2/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2584712A1 (fr) * | 1985-07-10 | 1987-01-16 | Midy Spa | Phenylethanolamines a activite lipolytique, un procede pour leur preparation et compositions pharmaceutiques en contenant |
| FR2643076A1 (fr) * | 1989-02-14 | 1990-08-17 | Midy Spa | Carboxyalkyl-ethers de la 2-amino-7-hydroxytetraline |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0489640B1 (fr) | 1996-10-02 |
| DE69122480T2 (de) | 1997-04-24 |
| JPH0525040A (ja) | 1993-02-02 |
| HUT59595A (en) | 1992-06-29 |
| JP2610735B2 (ja) | 1997-05-14 |
| SG47450A1 (en) | 1998-04-17 |
| US5270341A (en) | 1993-12-14 |
| CA2056906A1 (en) | 1992-06-05 |
| DK0489640T3 (da) | 1997-02-17 |
| FR2669821B1 (https=) | 1994-12-09 |
| IE914195A1 (en) | 1992-06-17 |
| AU653968B2 (en) | 1994-10-20 |
| HU207793B (en) | 1993-06-28 |
| IE76322B1 (en) | 1997-10-22 |
| DE69122480D1 (de) | 1996-11-07 |
| EP0489640A1 (fr) | 1992-06-10 |
| AU8839591A (en) | 1992-06-11 |
| CA2056906C (en) | 1998-04-28 |
| HU913800D0 (en) | 1992-02-28 |
| ATE143592T1 (de) | 1996-10-15 |
| MX9102365A (es) | 1992-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |