FR2463139A1 - Nouveaux derives d'halovincamone, leur procede de preparation et medicaments les contenant - Google Patents
Nouveaux derives d'halovincamone, leur procede de preparation et medicaments les contenant Download PDFInfo
- Publication number
- FR2463139A1 FR2463139A1 FR8017734A FR8017734A FR2463139A1 FR 2463139 A1 FR2463139 A1 FR 2463139A1 FR 8017734 A FR8017734 A FR 8017734A FR 8017734 A FR8017734 A FR 8017734A FR 2463139 A1 FR2463139 A1 FR 2463139A1
- Authority
- FR
- France
- Prior art keywords
- general formula
- derivative
- bromovincamone
- acid
- pharmaceutical
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 239000003814 drug Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 230000000694 effects Effects 0.000 claims abstract description 8
- 239000007800 oxidant agent Substances 0.000 claims abstract description 5
- 229940124549 vasodilator Drugs 0.000 claims abstract description 3
- 239000003071 vasodilator agent Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 239000001273 butane Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 230000001747 exhibiting effect Effects 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 239000011572 manganese Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 15
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 230000017531 blood circulation Effects 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000002792 vascular Effects 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- -1 p-aminobenzoic Chemical compound 0.000 description 4
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- DDPMGIMJSRUULN-UHFFFAOYSA-N buphedrone Chemical compound CCC(NC)C(=O)C1=CC=CC=C1 DDPMGIMJSRUULN-UHFFFAOYSA-N 0.000 description 3
- 210000001105 femoral artery Anatomy 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- RAHBQBFGEFXJNL-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-1-(4-bromophenyl)ethanone Chemical group C1=CC(Br)=CC=C1C(=O)CN1CCN(CC=2C=CC=CC=2)CC1 RAHBQBFGEFXJNL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229960002726 vincamine Drugs 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- OTCCIMWXFLJLIA-UHFFFAOYSA-N N-acetyl-DL-aspartic acid Natural products CC(=O)NC(C(O)=O)CC(O)=O OTCCIMWXFLJLIA-UHFFFAOYSA-N 0.000 description 1
- OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 210000004004 carotid artery internal Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- ZHGASCUQXLPSDT-UHFFFAOYSA-N cyclohexanesulfonic acid Chemical compound OS(=O)(=O)C1CCCCC1 ZHGASCUQXLPSDT-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 230000000916 dilatatory effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 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
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D461/00—Heterocyclic compounds containing indolo [3,2,1-d,e] pyrido [3,2,1,j] [1,5]-naphthyridine ring systems, e.g. vincamine
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79RI722A HU180929B (en) | 1979-08-13 | 1979-08-13 | Process for producing new bromo-vincamone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2463139A1 true FR2463139A1 (fr) | 1981-02-20 |
| FR2463139B1 FR2463139B1 (cg-RX-API-DMAC10.html) | 1983-08-26 |
Family
ID=11001105
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8017734A Granted FR2463139A1 (fr) | 1979-08-13 | 1980-08-12 | Nouveaux derives d'halovincamone, leur procede de preparation et medicaments les contenant |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4356305A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5822154B2 (cg-RX-API-DMAC10.html) |
| AT (1) | AT374200B (cg-RX-API-DMAC10.html) |
| AU (1) | AU530761B2 (cg-RX-API-DMAC10.html) |
| BE (1) | BE884620A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1152076A (cg-RX-API-DMAC10.html) |
| CH (1) | CH645643A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE3026654A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK154083C (cg-RX-API-DMAC10.html) |
| ES (1) | ES8106516A1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI68623C (cg-RX-API-DMAC10.html) |
| FR (1) | FR2463139A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB2056452B (cg-RX-API-DMAC10.html) |
| HU (1) | HU180929B (cg-RX-API-DMAC10.html) |
| IL (1) | IL60588A (cg-RX-API-DMAC10.html) |
| IT (1) | IT1132403B (cg-RX-API-DMAC10.html) |
| NL (1) | NL8004348A (cg-RX-API-DMAC10.html) |
| NO (1) | NO154396C (cg-RX-API-DMAC10.html) |
| NZ (1) | NZ194653A (cg-RX-API-DMAC10.html) |
| PH (1) | PH16002A (cg-RX-API-DMAC10.html) |
| SE (1) | SE441925B (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA804341B (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3322686A1 (de) * | 1982-06-30 | 1984-02-16 | Richter Gedeon Vegyészeti Gyár R.T., 1475 Budapest | Neue eburnanderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische praeparate |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU84664A1 (fr) * | 1983-02-25 | 1984-11-08 | Onmichem S A | Alkyl-4-indolonaphtyridines et leur application therapeutique |
| DE3340025C2 (de) * | 1983-11-03 | 1986-01-09 | Schering AG, 1000 Berlin und 4709 Bergkamen | Verfahren zur Herstellung von 2-Brom-8-ergolinyl-Verbindungen |
| JP2581570B2 (ja) * | 1987-10-19 | 1997-02-12 | 富士写真フイルム株式会社 | ビデオ用磁気記録媒体 |
| FR2623501B1 (fr) * | 1987-11-19 | 1990-03-16 | Roussel Uclaf | Nouveaux derives substitues de 20,21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions pharmaceutiques les renfermant |
| US5202338A (en) * | 1990-10-31 | 1993-04-13 | Vilmos Bar | Dihydroquinoline derivatives, pharmaceutical compositions and methods of use of dihydroquinoline derivatives as modulators of the arachidonic acid cascade |
| JP3135741B2 (ja) * | 1993-05-07 | 2001-02-19 | 富士写真フイルム株式会社 | 研磨体 |
| US5573444A (en) * | 1993-06-22 | 1996-11-12 | Fuji Photo Film Co., Ltd. | Polishing method |
| US5611826A (en) * | 1994-03-01 | 1997-03-18 | Fuji Photo Film Co., Ltd. | Abrasive tape |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2428646A1 (fr) * | 1978-06-12 | 1980-01-11 | Omnium Chimique Sa | Bromo-10-oxo-16-eburnane et bromo-16-14,15-eburnane, procede pour leur preparation et leur application comme medicaments |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2085630A1 (en) * | 1970-04-07 | 1971-12-31 | Le Men Georges | Vincamone compsn - having vasodilator ganglioplegic and antihistamine activity |
| FR2168853B1 (cg-RX-API-DMAC10.html) * | 1972-01-24 | 1975-04-25 | Centre Etd Ind Pharma | |
| US3852453A (en) * | 1972-05-26 | 1974-12-03 | Synthelabo | Method of enhancing vincamine compositions |
| FR2206090A1 (en) * | 1972-11-16 | 1974-06-07 | Omnium Chimique Sa | Homovincamone-contg. medicaments - with vasodilating, spasmolytic anti-arrhythmic and anti-ischaemic properties |
| DE2458164A1 (de) * | 1973-12-18 | 1975-06-26 | Sandoz Ag | Verfahren zur herstellung von neuen heterocyclischen verbindungen |
| US4146643A (en) * | 1973-12-18 | 1979-03-27 | Sandoz Ltd. | Increasing vigilance or treating cerebral insufficiency with substituted vincamines |
| DE2538095A1 (de) * | 1974-09-06 | 1976-03-25 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und verwendung |
| FR2339618A1 (fr) * | 1976-01-30 | 1977-08-26 | Omnium Chimique Sa | Procede de preparation de (-)11-aminovincamone, de 11-aminoeburamonine, de 11-aminovincamone racemique et derives indoliques nouveaux |
| DE2703920A1 (de) * | 1976-02-05 | 1977-08-11 | Sandoz Ag | Neue organische verbindungen, ihre herstellung und verwendung |
| FR2398746A1 (fr) * | 1977-07-25 | 1979-02-23 | Roussel Uclaf | Nouveaux derives d'alcaloides pentacycliques, leur procede de preparation, leur application comme medicaments, et leur application a la synthese de produits du groupe de l'eburnamonine |
| FR2407931A1 (fr) * | 1977-11-02 | 1979-06-01 | Synthelabo | Derives de l'eburnamenine et leur application en therapeutique |
| FR2428644A2 (fr) * | 1978-06-12 | 1980-01-11 | Omnium Chimique Sa | Bromo-10-vincamine et bromo-10-14, 15-vincamine, procede pour leur preparation et leur application comme medicaments |
| DE2922316A1 (de) * | 1978-06-12 | 1979-12-20 | Omnium Chimique Sa | Neue halogenderivate des vincamins, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| CH649295A5 (de) * | 1978-07-12 | 1985-05-15 | Richter Gedeon Vegyeszet | Optisch aktive oder razemische brom-e-homo-eburanderivate. |
| US4285949A (en) * | 1978-12-11 | 1981-08-25 | Omnichem Societe Anonyme | Vincamine derivatives, their preparation and therapeutical use |
| HU180928B (en) * | 1979-08-06 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for preparing new brominated 15-hydroxy-e-homo-eburane derivatives |
| HU181496B (en) * | 1979-08-13 | 1983-07-28 | Richter Gedeon Vegyeszet | Process for preparing 10-bromo-15-hydroxy-e-homo-eburnanes |
-
1979
- 1979-08-13 HU HU79RI722A patent/HU180929B/hu not_active IP Right Cessation
-
1980
- 1980-07-14 DE DE19803026654 patent/DE3026654A1/de not_active Withdrawn
- 1980-07-15 IL IL60588A patent/IL60588A/xx unknown
- 1980-07-17 ZA ZA00804341A patent/ZA804341B/xx unknown
- 1980-07-24 PH PH24346A patent/PH16002A/en unknown
- 1980-07-30 NL NL8004348A patent/NL8004348A/nl not_active Application Discontinuation
- 1980-07-31 AT AT0396380A patent/AT374200B/de not_active IP Right Cessation
- 1980-08-04 BE BE1/9916A patent/BE884620A/fr not_active IP Right Cessation
- 1980-08-05 US US06/175,384 patent/US4356305A/en not_active Expired - Lifetime
- 1980-08-06 JP JP55107242A patent/JPS5822154B2/ja not_active Expired
- 1980-08-07 FI FI802483A patent/FI68623C/fi not_active IP Right Cessation
- 1980-08-08 ES ES494086A patent/ES8106516A1/es not_active Expired
- 1980-08-11 CH CH605180A patent/CH645643A5/de not_active IP Right Cessation
- 1980-08-11 GB GB8026067A patent/GB2056452B/en not_active Expired
- 1980-08-12 FR FR8017734A patent/FR2463139A1/fr active Granted
- 1980-08-12 NO NO802402A patent/NO154396C/no unknown
- 1980-08-12 AU AU61369/80A patent/AU530761B2/en not_active Ceased
- 1980-08-12 SE SE8005686A patent/SE441925B/sv not_active IP Right Cessation
- 1980-08-12 DK DK347980A patent/DK154083C/da active
- 1980-08-12 NZ NZ194653A patent/NZ194653A/xx unknown
- 1980-08-13 IT IT24150/80A patent/IT1132403B/it active
- 1980-08-13 CA CA000358151A patent/CA1152076A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2428646A1 (fr) * | 1978-06-12 | 1980-01-11 | Omnium Chimique Sa | Bromo-10-oxo-16-eburnane et bromo-16-14,15-eburnane, procede pour leur preparation et leur application comme medicaments |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3322686A1 (de) * | 1982-06-30 | 1984-02-16 | Richter Gedeon Vegyészeti Gyár R.T., 1475 Budapest | Neue eburnanderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische praeparate |
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