FR2518992A1 - Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique - Google Patents
Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2518992A1 FR2518992A1 FR8124244A FR8124244A FR2518992A1 FR 2518992 A1 FR2518992 A1 FR 2518992A1 FR 8124244 A FR8124244 A FR 8124244A FR 8124244 A FR8124244 A FR 8124244A FR 2518992 A1 FR2518992 A1 FR 2518992A1
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- derivatives
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- Prior art date
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- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 239000011575 calcium Substances 0.000 title claims abstract description 5
- 229910052791 calcium Inorganic materials 0.000 title claims abstract description 5
- 230000000694 effects Effects 0.000 title abstract description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 title description 4
- 239000001294 propane Substances 0.000 title description 2
- 206010002383 Angina Pectoris Diseases 0.000 title 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- -1 pyrrolidino, piperidino, hexamethyleneimino Chemical group 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 239000000543 intermediate Substances 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 239000012279 sodium borohydride Substances 0.000 claims description 7
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 6
- 239000011707 mineral Substances 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 3
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 3
- 241000699670 Mus sp. Species 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 abstract description 2
- 239000003071 vasodilator agent Substances 0.000 abstract description 2
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 238000001990 intravenous administration Methods 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000012634 fragment Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- 0 CC(CC1)C(*C2CC(*)CCCC2)CCC1(*)C1(C)CCCC1 Chemical compound CC(CC1)C(*C2CC(*)CCCC2)CCC1(*)C1(C)CCCC1 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- VUBARAGILBSAKW-UHFFFAOYSA-N 1-(2-hydroxy-3,6-dimethoxyphenyl)ethanone Chemical compound COC1=CC=C(OC)C(C(C)=O)=C1O VUBARAGILBSAKW-UHFFFAOYSA-N 0.000 description 1
- SGRGGZWBZAQRQD-UHFFFAOYSA-N 3,7,8-trimethoxy-2-methyl-5-(5-phenylpentyl)-1h-quinolin-4-one Chemical compound N1C(C)=C(OC)C(=O)C=2C1=C(OC)C(OC)=CC=2CCCCCC1=CC=CC=C1 SGRGGZWBZAQRQD-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QJVYIFLZCNCOKC-UHFFFAOYSA-N C(C(=O)O)(=O)O.C(C)(=O)C1=CC=CC=C1 Chemical compound C(C(=O)O)(=O)O.C(C)(=O)C1=CC=CC=C1 QJVYIFLZCNCOKC-UHFFFAOYSA-N 0.000 description 1
- GDOPTJXRTPNYNR-UHFFFAOYSA-N CC1CCCC1 Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000009087 cell motility Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 210000002460 smooth muscle Anatomy 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8124244A FR2518992A1 (fr) | 1981-12-24 | 1981-12-24 | Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique |
| GR70145A GR78370B (enrdf_load_stackoverflow) | 1981-12-24 | 1982-04-13 | |
| SE8207224A SE453916B (sv) | 1981-12-24 | 1982-12-17 | Nya aromatiska aminoalkoxiderivat, deras framstellningssett och lekemedel anvendbart som kalciumantagonist |
| CA000418154A CA1197243A (en) | 1981-12-24 | 1982-12-20 | Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics |
| CH7473/82A CH655313A5 (fr) | 1981-12-24 | 1982-12-21 | Derives aminoalkoxy aromatiques, leur procede de preparation et medicaments les renfermant. |
| US06/451,537 US4536500A (en) | 1981-12-24 | 1982-12-21 | Aromatic derivatives comprising an aminoalkoxy chain and pharmaceutical compositions thereof |
| CH3696/85A CH661509A5 (fr) | 1981-12-24 | 1982-12-21 | Cetones aromatiques. |
| GB08236432A GB2113680B (en) | 1981-12-24 | 1982-12-22 | New aromatic derivatives comprising an aminoalkoxy chain having an activity antagomistic to calcium |
| LU84548A LU84548A1 (fr) | 1981-12-24 | 1982-12-22 | Nouveaux derives aminoalkoxy aromatiques,leur procede de preparation et leur application en therapeutique |
| ES518518A ES8308864A1 (es) | 1981-12-24 | 1982-12-23 | Procedimiento para la fabricacion de nuevos derivados aminoalcoxi aromaticos. |
| DE3250049A DE3250049C2 (de) | 1981-12-24 | 1982-12-23 | Aminoalkoxyaromatische Derivate |
| DE19823247860 DE3247860A1 (de) | 1981-12-24 | 1982-12-23 | Aromatische aminoalkoxyderivate, verfahren zu ihrer herstellung und deren therapeutische verwendung |
| ZA829452A ZA829452B (en) | 1981-12-24 | 1982-12-23 | Aromatic derivatives, process for preparing these derivatives and pharmaceutical compositions thereof |
| BE0/209800A BE895464A (fr) | 1981-12-24 | 1982-12-23 | Nouveaux derives aminoalkoxy aromatiques leur procede de preparation et leur application en therapeutique |
| NL8204978A NL8204978A (nl) | 1981-12-24 | 1982-12-23 | Nieuwe aromatische aminoalkoxyverbindingen, werkwijze voor hun bereiding en hun toepassing in de geneeskunde. |
| IT24964/82A IT1191152B (it) | 1981-12-24 | 1982-12-23 | Derivati aminoalcossi aromatici,loro procedimento di preparazione e loro applicazione in terapia |
| JP57235004A JPS58146536A (ja) | 1981-12-24 | 1982-12-24 | アミノアルコキシ芳香族化合物及び該化合物を有効成分とする薬剤 |
| AU91934/82A AU9193482A (en) | 1981-12-24 | 1982-12-24 | Amino alkoxy aromatics |
| GB08506732A GB2154587B (en) | 1981-12-24 | 1985-03-15 | Aminoalkoxy-substituted aromatic ketones |
| US06/748,862 US4732896A (en) | 1981-12-24 | 1985-06-26 | Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics |
| SE8505219A SE8505219D0 (sv) | 1981-12-24 | 1985-11-06 | Derives aminoalkoxy aromatiques et leur procede de preparation |
| US07/147,268 US4831051A (en) | 1981-12-24 | 1988-01-22 | Aromatic derivatives comprising an aminoalkoxy chain, the salts thereof, the process for preparing these derivatives and salts and the application thereof in therapeutics |
| JP3033043A JPH04210944A (ja) | 1981-12-24 | 1991-02-27 | アミノアルコキシ芳香族化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8124244A FR2518992A1 (fr) | 1981-12-24 | 1981-12-24 | Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2518992A1 true FR2518992A1 (fr) | 1983-07-01 |
| FR2518992B1 FR2518992B1 (enrdf_load_stackoverflow) | 1984-05-18 |
Family
ID=9265407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8124244A Granted FR2518992A1 (fr) | 1981-12-24 | 1981-12-24 | Nouveaux derives aminoalcoxy aromatiques, leur procede de preparation et leur application en therapeutique |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS58146536A (enrdf_load_stackoverflow) |
| BE (1) | BE895464A (enrdf_load_stackoverflow) |
| FR (1) | FR2518992A1 (enrdf_load_stackoverflow) |
| ZA (1) | ZA829452B (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0338937A3 (en) * | 1988-04-22 | 1990-06-27 | Delalande S.A. | 1-û3-(4-hydroxy-phenyl)-1-hydoxy-1-propyl¨-2-(amino-alkyleneoxy)-benzene derivatives, process for their preparation and their therapeutical use |
| EP0600717A1 (en) * | 1992-11-30 | 1994-06-08 | Sankyo Company Limited | Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis |
| EP0535250A4 (en) * | 1991-04-10 | 1994-09-28 | Tsumura & Co | Novel compounds and use thereof as medicine |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2646670A1 (fr) * | 1989-05-05 | 1990-11-09 | Delalande Sa | Utilisation de derives aminoalkoxy aromatiques pour le traitement des troubles du systeme cerebrovasculaire |
| AUPS110302A0 (en) * | 2002-03-14 | 2002-04-18 | Biomolecular Research Institute Limited | Novel chalcone derivatives and uses thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1077722A (fr) * | 1952-04-24 | 1954-11-10 | Hoffmann La Roche | Procédé pour la préparation d'amino-cétones aromatiques |
| FR437M (enrdf_load_stackoverflow) * | 1960-05-25 | 1961-04-24 | ||
| GB1022648A (en) * | 1961-11-08 | 1966-03-16 | Guidotti & C Spa Labor | A process for making a series of ª‰-phenyl-propiophenone derivatives, substituted in the 2- and 4-positions and derivatives thereby obtained |
| FR1499864A (fr) * | 1964-07-24 | 1967-11-03 | Fisons Pharmaceuticals Ltd | Procédé de préparation d'arylcétones |
-
1981
- 1981-12-24 FR FR8124244A patent/FR2518992A1/fr active Granted
-
1982
- 1982-12-23 BE BE0/209800A patent/BE895464A/fr not_active IP Right Cessation
- 1982-12-23 ZA ZA829452A patent/ZA829452B/xx unknown
- 1982-12-24 JP JP57235004A patent/JPS58146536A/ja active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1077722A (fr) * | 1952-04-24 | 1954-11-10 | Hoffmann La Roche | Procédé pour la préparation d'amino-cétones aromatiques |
| FR437M (enrdf_load_stackoverflow) * | 1960-05-25 | 1961-04-24 | ||
| GB1022648A (en) * | 1961-11-08 | 1966-03-16 | Guidotti & C Spa Labor | A process for making a series of ª‰-phenyl-propiophenone derivatives, substituted in the 2- and 4-positions and derivatives thereby obtained |
| FR1499864A (fr) * | 1964-07-24 | 1967-11-03 | Fisons Pharmaceuticals Ltd | Procédé de préparation d'arylcétones |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/74 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0338937A3 (en) * | 1988-04-22 | 1990-06-27 | Delalande S.A. | 1-û3-(4-hydroxy-phenyl)-1-hydoxy-1-propyl¨-2-(amino-alkyleneoxy)-benzene derivatives, process for their preparation and their therapeutical use |
| EP0535250A4 (en) * | 1991-04-10 | 1994-09-28 | Tsumura & Co | Novel compounds and use thereof as medicine |
| EP0600717A1 (en) * | 1992-11-30 | 1994-06-08 | Sankyo Company Limited | Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis |
| US5556864A (en) * | 1992-11-30 | 1996-09-17 | Sankyo Company, Limited | α-ω-diarylalkane compounds serotonin-2 receptor agonists |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA829452B (en) | 1983-10-26 |
| BE895464A (fr) | 1983-06-23 |
| FR2518992B1 (enrdf_load_stackoverflow) | 1984-05-18 |
| JPH0438743B2 (enrdf_load_stackoverflow) | 1992-06-25 |
| JPS58146536A (ja) | 1983-09-01 |
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| TP | Transmission of property | ||
| ST | Notification of lapse |