FR2536749A1 - (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique - Google Patents
(amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique Download PDFInfo
- Publication number
- FR2536749A1 FR2536749A1 FR8219812A FR8219812A FR2536749A1 FR 2536749 A1 FR2536749 A1 FR 2536749A1 FR 8219812 A FR8219812 A FR 8219812A FR 8219812 A FR8219812 A FR 8219812A FR 2536749 A1 FR2536749 A1 FR 2536749A1
- Authority
- FR
- France
- Prior art keywords
- radical
- ethyl
- methyl
- compounds
- benzoxazolinone
- 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
- -1 AMINO-2 ETHYL Chemical class 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 230000000147 hypnotic effect Effects 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003254 radicals Chemical class 0.000 claims abstract description 7
- 238000010992 reflux Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003326 hypnotic agent Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- WXPOMCTYFGXESK-UHFFFAOYSA-N 2-(2-bromoethyl)-2H-1,3-benzoxazol-6-one Chemical compound BrCCC1OC=2C(=N1)C=CC(C=2)=O WXPOMCTYFGXESK-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical group C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 abstract description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical class C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 230000004899 motility Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000000506 psychotropic effect Effects 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UEPQARRQRBFTHK-UHFFFAOYSA-N 3-(1-bromoethyl)-2-methyl-2,5-dihydro-1,3-benzoxazol-6-one Chemical compound CC1OC=2C(N1C(C)Br)=CCC(C=2)=O UEPQARRQRBFTHK-UHFFFAOYSA-N 0.000 description 2
- IGKPISCESKQDFH-UHFFFAOYSA-N 4-(2-bromoethyl)-3H-1,3-benzoxazol-2-one Chemical compound BrCCC1=CC=CC2=C1NC(O2)=O IGKPISCESKQDFH-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 239000004312 hexamethylene tetramine Substances 0.000 description 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- YAONEUNUMVOKNQ-UHFFFAOYSA-N 15-(4-iodophenyl)pentadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCC1=CC=C(I)C=C1 YAONEUNUMVOKNQ-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- BQIHAYHNMVVRAN-UHFFFAOYSA-N 6-ethyl-3h-1,3-benzoxazol-2-one Chemical compound CCC1=CC=C2NC(=O)OC2=C1 BQIHAYHNMVVRAN-UHFFFAOYSA-N 0.000 description 1
- 206010001541 Akinesia Diseases 0.000 description 1
- PTOCQTDPMAGHOC-UHFFFAOYSA-N CC1OC=2C(N1CCBr)=CCC(C=2)=O Chemical compound CC1OC=2C(N1CCBr)=CCC(C=2)=O PTOCQTDPMAGHOC-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 241000030781 Ippa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000001670 myorelaxant effect Effects 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 101150009274 nhr-1 gene Proteins 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
-
- 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
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219812A FR2536749A1 (fr) | 1982-11-25 | 1982-11-25 | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
| ZA838684A ZA838684B (en) | 1982-11-25 | 1983-11-21 | Benzoxazolinones |
| US06/554,194 US4558060A (en) | 1982-11-25 | 1983-11-22 | Benzoxazolinones |
| AU21612/83A AU562113B2 (en) | 1982-11-25 | 1983-11-23 | Benzoxazolinones |
| CA000441918A CA1208220A (en) | 1982-11-25 | 1983-11-24 | Benzoxazolinones |
| AT83402267T ATE26270T1 (de) | 1982-11-25 | 1983-11-24 | Substituierte (amino-2-ethyl)-6-benzoxazolinone, ihre herstellung und pharmazeutische zusammenstellung die sie enthaelt. |
| DE8383402267T DE3370624D1 (en) | 1982-11-25 | 1983-11-24 | Substituted (amino-2-ethyl)-6-benzoxazolinones, their preparation and a pharmaceutical composition containing them |
| EP83402267A EP0110781B1 (fr) | 1982-11-25 | 1983-11-24 | (Amino-2 éthyl)-6 benzoxazolinones substituées, leur préparation et une composition pharmaceutique les contenant |
| ES527521A ES8501233A1 (es) | 1982-11-25 | 1983-11-24 | Un procedimiento para la preparacion de nuevos derivados de benzoxazolinona sustituidos |
| GR73064A GR81294B (enExample) | 1982-11-25 | 1983-11-24 | |
| FI834315A FI78079C (fi) | 1982-11-25 | 1983-11-24 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara substituerade 6-(2-aminoetyl)-bensoxazolinoner. |
| JP58221350A JPS59112976A (ja) | 1982-11-25 | 1983-11-24 | 置換された６−（２−アミノエチル）−ベンゾオキサゾリノン、その製法及び使用 |
| HU834038A HU190635B (en) | 1982-11-25 | 1983-11-24 | Process for preparing benzoxazoline-derivatives and the pharmaceutically acceptable salts of these compounds as well as pharmaceutical compositions comprising the same as active substance |
| IE2756/83A IE56285B1 (en) | 1982-11-25 | 1983-11-24 | Substituted 6-(2-aminoethyl)-benzoxazolinones,their preparation and a composition containing them |
| DK539983A DK539983A (da) | 1982-11-25 | 1983-11-25 | Benzoxazolinoner og fremgangsmaade til fremstilling deraf |
| PT77735A PT77735B (fr) | 1982-11-25 | 1983-11-25 | Procede de preparation de derives de benzoxazolinone |
| KR1019830005578A KR910000416B1 (ko) | 1982-11-25 | 1983-11-25 | 벤족사졸리논 유도체의 제조방법 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8219812A FR2536749A1 (fr) | 1982-11-25 | 1982-11-25 | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2536749A1 true FR2536749A1 (fr) | 1984-06-01 |
| FR2536749B1 FR2536749B1 (enExample) | 1985-04-26 |
Family
ID=9279533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8219812A Granted FR2536749A1 (fr) | 1982-11-25 | 1982-11-25 | (amino-2 ethyl)-6 benzoxazolinones substituees, leur preparation et leurs applications en therapeutique |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4558060A (enExample) |
| EP (1) | EP0110781B1 (enExample) |
| JP (1) | JPS59112976A (enExample) |
| KR (1) | KR910000416B1 (enExample) |
| AT (1) | ATE26270T1 (enExample) |
| AU (1) | AU562113B2 (enExample) |
| CA (1) | CA1208220A (enExample) |
| DE (1) | DE3370624D1 (enExample) |
| DK (1) | DK539983A (enExample) |
| ES (1) | ES8501233A1 (enExample) |
| FI (1) | FI78079C (enExample) |
| FR (1) | FR2536749A1 (enExample) |
| GR (1) | GR81294B (enExample) |
| HU (1) | HU190635B (enExample) |
| IE (1) | IE56285B1 (enExample) |
| PT (1) | PT77735B (enExample) |
| ZA (1) | ZA838684B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960778A (en) * | 1988-10-04 | 1990-10-02 | Adir Et Cie | Benzoxazolinone compounds |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4554284A (en) * | 1984-09-12 | 1985-11-19 | Smithkline Beckman Corporation | 7-(2-Aminoethyl)-1,3-benzthia- or oxa-zol-2(3H)-ones |
| MX173362B (es) * | 1987-03-02 | 1994-02-23 | Pfizer | Compuestos de piperazinil heterociclicos y procedimiento para su preparacion |
| US4883795A (en) * | 1988-01-22 | 1989-11-28 | Pfizer Inc. | Piperazinyl-heterocyclic compounds |
| FR2643634A1 (fr) * | 1989-02-28 | 1990-08-31 | Adir | Nouveaux derives benzoxazolinoniques, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| US5182278A (en) * | 1989-02-28 | 1993-01-26 | Adir Et Compagnie | Analgesic benzoxazolinones having at the 6-position a 1-hydroxy-3-morpholinopropyl side chain |
| US5268381A (en) * | 1990-09-26 | 1993-12-07 | Adir Et Compagnie | Aminoalkyl-benzothiazolinone and -benzoxazolinone compounds having a high 5-HT1A affinity |
| FR2667068B1 (fr) * | 1990-09-26 | 1994-09-09 | Adir | Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5147881A (en) * | 1990-11-14 | 1992-09-15 | Pfizer Inc | 4-(1,2-benzisoxazolyl)piperidine antipsychotic agents |
| FR2674524B1 (fr) * | 1991-03-25 | 1993-05-21 | Adir | Nouveaux amides alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| US5338846A (en) * | 1992-08-26 | 1994-08-16 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds with a piperazine salt |
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| FR2717810B1 (fr) * | 1994-03-22 | 1996-04-26 | Adir | Nouvelles aminoalkyl benzoxazolinones et benzothiazolinones, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| CN1182103C (zh) * | 1997-08-07 | 2004-12-29 | 株式会社富吉摩托普拉泽兹 | 乙胺衍生物 |
| US7213005B2 (en) * | 1999-12-09 | 2007-05-01 | International Business Machines Corporation | Digital content distribution using web broadcasting services |
| US20040192669A1 (en) * | 2000-04-13 | 2004-09-30 | Rosenfeld Mark J. | Novel compounds for use in weight loss and appetite suppression in humans |
| US7794761B2 (en) * | 2000-04-13 | 2010-09-14 | Seroctin Research & Technology, Inc. | Methods for inducing anti-anxiety and calming effects in animals and humans |
| US7524877B2 (en) | 2003-11-20 | 2009-04-28 | Seroctin Research & Technology, Inc. | Compounds for use in weight loss and appetite suppression in humans |
| EP1687300A4 (en) * | 2003-11-28 | 2007-08-01 | Wockhardt Ltd | PROCESS FOR THE PREPARATION OF ZIPRASIDONE MONOHYDROCHLORIDE HYDRATE |
| KR100812310B1 (ko) * | 2005-12-27 | 2008-03-10 | 주식회사이에스이 | 위치제어용 얼라인 장치 |
| CA2968806A1 (en) | 2014-12-05 | 2016-06-09 | Semmelweis University | Use of arylalkylamine monoamine oxidase inhibitors in the treatment or prevention of cancer |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4034100A (en) * | 1976-02-13 | 1977-07-05 | Merck & Co., Inc. | Antihypertensive agents |
| EP0049203A1 (fr) * | 1980-09-29 | 1982-04-07 | RIOM LABORATOIRES- C.E.R.M. (Société Anonyme) | Nouvelles benzoxazolinones substituées en 6 par une chaîne aminoalcool ou aminocétone, leur préparation et leur application en thérapeutique |
| FR2491471A1 (fr) * | 1980-10-03 | 1982-04-09 | Cerm Cent Europ Rech Mauvernay | Benzoxazolinones substituees, leur preparation et leur application en therapeutique |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57123103A (en) * | 1981-01-26 | 1982-07-31 | Hokko Chem Ind Co Ltd | Agricultural and horticultural fungicide |
| JPS61231548A (ja) * | 1985-04-05 | 1986-10-15 | Konishiroku Photo Ind Co Ltd | 写真廃液の処理方法及び写真自動現像機 |
-
1982
- 1982-11-25 FR FR8219812A patent/FR2536749A1/fr active Granted
-
1983
- 1983-11-21 ZA ZA838684A patent/ZA838684B/xx unknown
- 1983-11-22 US US06/554,194 patent/US4558060A/en not_active Expired - Fee Related
- 1983-11-23 AU AU21612/83A patent/AU562113B2/en not_active Ceased
- 1983-11-24 JP JP58221350A patent/JPS59112976A/ja active Pending
- 1983-11-24 AT AT83402267T patent/ATE26270T1/de not_active IP Right Cessation
- 1983-11-24 EP EP83402267A patent/EP0110781B1/fr not_active Expired
- 1983-11-24 ES ES527521A patent/ES8501233A1/es not_active Expired
- 1983-11-24 FI FI834315A patent/FI78079C/fi not_active IP Right Cessation
- 1983-11-24 GR GR73064A patent/GR81294B/el unknown
- 1983-11-24 IE IE2756/83A patent/IE56285B1/en not_active IP Right Cessation
- 1983-11-24 DE DE8383402267T patent/DE3370624D1/de not_active Expired
- 1983-11-24 HU HU834038A patent/HU190635B/hu not_active IP Right Cessation
- 1983-11-24 CA CA000441918A patent/CA1208220A/en not_active Expired
- 1983-11-25 PT PT77735A patent/PT77735B/pt not_active IP Right Cessation
- 1983-11-25 KR KR1019830005578A patent/KR910000416B1/ko not_active Expired
- 1983-11-25 DK DK539983A patent/DK539983A/da not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4034100A (en) * | 1976-02-13 | 1977-07-05 | Merck & Co., Inc. | Antihypertensive agents |
| EP0049203A1 (fr) * | 1980-09-29 | 1982-04-07 | RIOM LABORATOIRES- C.E.R.M. (Société Anonyme) | Nouvelles benzoxazolinones substituées en 6 par une chaîne aminoalcool ou aminocétone, leur préparation et leur application en thérapeutique |
| FR2491471A1 (fr) * | 1980-10-03 | 1982-04-09 | Cerm Cent Europ Rech Mauvernay | Benzoxazolinones substituees, leur preparation et leur application en therapeutique |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4960778A (en) * | 1988-10-04 | 1990-10-02 | Adir Et Cie | Benzoxazolinone compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| DK539983A (da) | 1984-05-26 |
| EP0110781B1 (fr) | 1987-04-01 |
| FI78079C (fi) | 1989-06-12 |
| US4558060A (en) | 1985-12-10 |
| EP0110781A1 (fr) | 1984-06-13 |
| FI834315L (fi) | 1984-05-26 |
| HU190635B (en) | 1986-09-29 |
| CA1208220A (en) | 1986-07-22 |
| IE832756L (en) | 1984-05-25 |
| ZA838684B (en) | 1984-07-25 |
| AU2161283A (en) | 1984-05-31 |
| KR840006633A (ko) | 1984-12-01 |
| AU562113B2 (en) | 1987-05-28 |
| FI834315A0 (fi) | 1983-11-24 |
| DE3370624D1 (en) | 1987-05-07 |
| FI78079B (fi) | 1989-02-28 |
| ES527521A0 (es) | 1984-12-01 |
| DK539983D0 (da) | 1983-11-25 |
| ES8501233A1 (es) | 1984-12-01 |
| PT77735A (fr) | 1983-12-01 |
| ATE26270T1 (de) | 1987-04-15 |
| IE56285B1 (en) | 1991-06-05 |
| KR910000416B1 (ko) | 1991-01-25 |
| PT77735B (fr) | 1986-03-27 |
| FR2536749B1 (enExample) | 1985-04-26 |
| JPS59112976A (ja) | 1984-06-29 |
| GR81294B (enExample) | 1984-12-11 |
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