CA1186311A - Procede de preparation de nouveaux derives de 20,21- d'inoreburnamenine eventuellement substitues sur le cycle e - Google Patents
Procede de preparation de nouveaux derives de 20,21- d'inoreburnamenine eventuellement substitues sur le cycle eInfo
- Publication number
- CA1186311A CA1186311A CA000413069A CA413069A CA1186311A CA 1186311 A CA1186311 A CA 1186311A CA 000413069 A CA000413069 A CA 000413069A CA 413069 A CA413069 A CA 413069A CA 1186311 A CA1186311 A CA 1186311A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- product
- hydrogen atom
- organic
- addition salts
- 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.)
- Expired
Links
- 238000002360 preparation method Methods 0.000 title claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 42
- 239000002253 acid Substances 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 32
- 150000007513 acids Chemical class 0.000 claims abstract description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000005304 joining Methods 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 29
- 239000011707 mineral Substances 0.000 claims description 29
- -1 alkyl radical Chemical group 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 150000007522 mineralic acids Chemical class 0.000 claims description 13
- 150000007524 organic acids Chemical class 0.000 claims description 13
- 235000005985 organic acids Nutrition 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 238000006297 dehydration reaction Methods 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 230000018044 dehydration Effects 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 241001331845 Equus asinus x caballus Species 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 230000035943 smell Effects 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 16
- 239000001257 hydrogen Substances 0.000 abstract description 16
- 230000002490 cerebral effect Effects 0.000 abstract description 8
- 239000003814 drug Substances 0.000 abstract description 6
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 229940079593 drug Drugs 0.000 abstract description 5
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 125000003118 aryl group Chemical group 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
- 239000002904 solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-QYKNYGDISA-N 2-deuteriopyridine Chemical compound [2H]C1=CC=CC=N1 JUJWROOIHBZHMG-QYKNYGDISA-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
- 244000215068 Acacia senegal Species 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 241000272814 Anser sp. Species 0.000 description 1
- 206010065559 Cerebral arteriosclerosis Diseases 0.000 description 1
- 208000010248 Cerebrovascular Trauma Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 208000032843 Hemorrhage Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- RQIFXTOWUNAUJC-UHFFFAOYSA-N ethanesulfinic acid Chemical compound CCS(O)=O RQIFXTOWUNAUJC-UHFFFAOYSA-N 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 201000005851 intracranial arteriosclerosis Diseases 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 210000002418 meninge Anatomy 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 230000004089 microcirculation Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [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
- 238000011017 operating method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021178 picnic Nutrition 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940116269 uric acid Drugs 0.000 description 1
- 208000010926 vascular brain injury Diseases 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR81-18935 | 1981-10-08 | ||
| FR8118935A FR2514357A1 (fr) | 1981-10-08 | 1981-10-08 | Nouveaux derives de 20,21-dinoreburnamenine eventuellement substitues sur le cycle e, procede de preparation et application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1186311A true CA1186311A (fr) | 1985-04-30 |
Family
ID=9262847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000413069A Expired CA1186311A (fr) | 1981-10-08 | 1982-10-07 | Procede de preparation de nouveaux derives de 20,21- d'inoreburnamenine eventuellement substitues sur le cycle e |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4501740A (oth) |
| JP (1) | JPH0651700B2 (oth) |
| AT (1) | AT385989B (oth) |
| BE (1) | BE894630A (oth) |
| CA (1) | CA1186311A (oth) |
| CH (1) | CH655319A5 (oth) |
| DE (1) | DE3237429A1 (oth) |
| ES (1) | ES516299A0 (oth) |
| FR (1) | FR2514357A1 (oth) |
| GB (1) | GB2107317B (oth) |
| GR (1) | GR77710B (oth) |
| HU (1) | HU188330B (oth) |
| IT (1) | IT1149103B (oth) |
| LU (1) | LU84412A1 (oth) |
| MX (1) | MX159206A (oth) |
| NL (1) | NL8203859A (oth) |
| PT (1) | PT75656B (oth) |
| SE (1) | SE452885B (oth) |
| ZA (1) | ZA827058B (oth) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2623503B1 (oth) * | 1987-11-19 | 1991-04-05 | Roussel Uclaf | |
| DE3916143C5 (de) * | 1988-05-20 | 2008-09-18 | Amada Co., Ltd., Isehara | Schneidmaschine und Verfahren zum Anordnen eines Werkstückes in dieser |
| FR2653124B1 (fr) * | 1989-10-17 | 1992-01-17 | Roussel Uclaf | Nouveaux derives substitues en 15 de la 20, 21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions les renfermant. |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2168853B1 (oth) * | 1972-01-24 | 1975-04-25 | Centre Etd Ind Pharma | |
| US4033969A (en) * | 1972-06-19 | 1977-07-05 | Agence Nationale De Valorisation De La Recherche (Anvar) | Vincamine derivatives |
| FR2190113A5 (oth) * | 1972-06-19 | 1974-01-25 | Anvar | |
| HU171663B (hu) * | 1975-09-01 | 1978-02-28 | Richter Gedeon Vegyeszet | Sposob poluchenija novykh proizvodnykh 14-skobka-zamehhennogo metil-skobka zakryta-vinkana |
| HU173511B (hu) * | 1976-07-21 | 1979-05-28 | Richter Gedeon Vegyeszet | Sposob poluchenija vinkamenina, ego solejj i molekuljarnykh soedinenijj |
| HU174214B (hu) * | 1976-07-21 | 1979-11-28 | Richter Gedeon Vegyeszet | Sposob poluchenija vinkana i solejj |
| GB1568417A (en) * | 1976-07-21 | 1980-05-29 | Richter Gedeon Vegyeszet | Vincamine derivatives |
| FR2381048A1 (fr) * | 1977-02-22 | 1978-09-15 | Roussel Uclaf | Nouveaux derives de 20,21-dinoreburnamenine, un procede pour leur preparation et leur application comme medicaments |
| FR2475549A1 (fr) * | 1980-02-12 | 1981-08-14 | Synthelabo | Derives vincaminiques desethyles, leur synthese et leur application en therapeutique |
-
1981
- 1981-10-08 FR FR8118935A patent/FR2514357A1/fr active Granted
-
1982
- 1982-09-17 SE SE8205335A patent/SE452885B/sv not_active IP Right Cessation
- 1982-09-21 US US06/420,791 patent/US4501740A/en not_active Expired - Fee Related
- 1982-09-27 ZA ZA827058A patent/ZA827058B/xx unknown
- 1982-10-05 NL NL8203859A patent/NL8203859A/nl not_active Application Discontinuation
- 1982-10-06 GR GR69457A patent/GR77710B/el unknown
- 1982-10-07 HU HU823219A patent/HU188330B/hu not_active IP Right Cessation
- 1982-10-07 ES ES516299A patent/ES516299A0/es active Granted
- 1982-10-07 GB GB08228739A patent/GB2107317B/en not_active Expired
- 1982-10-07 BE BE0/209193A patent/BE894630A/fr not_active IP Right Cessation
- 1982-10-07 PT PT75656A patent/PT75656B/pt not_active IP Right Cessation
- 1982-10-07 MX MX194700A patent/MX159206A/es unknown
- 1982-10-07 IT IT49226/82A patent/IT1149103B/it active
- 1982-10-07 CA CA000413069A patent/CA1186311A/fr not_active Expired
- 1982-10-07 JP JP57175447A patent/JPH0651700B2/ja not_active Expired - Lifetime
- 1982-10-07 LU LU84412A patent/LU84412A1/fr unknown
- 1982-10-07 CH CH5905/82A patent/CH655319A5/fr not_active IP Right Cessation
- 1982-10-08 DE DE19823237429 patent/DE3237429A1/de not_active Withdrawn
- 1982-10-08 AT AT0373182A patent/AT385989B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT75656B (fr) | 1986-04-09 |
| DE3237429A1 (de) | 1983-04-21 |
| CH655319A5 (fr) | 1986-04-15 |
| BE894630A (fr) | 1983-04-07 |
| PT75656A (fr) | 1982-11-01 |
| ZA827058B (en) | 1983-07-27 |
| GB2107317A (en) | 1983-04-27 |
| SE8205335D0 (sv) | 1982-09-17 |
| JPH0651700B2 (ja) | 1994-07-06 |
| SE8205335L (sv) | 1983-04-09 |
| FR2514357A1 (fr) | 1983-04-15 |
| JPS5872582A (ja) | 1983-04-30 |
| MX159206A (es) | 1989-05-02 |
| AT385989B (de) | 1988-06-10 |
| HU188330B (en) | 1986-04-28 |
| ES8307247A1 (es) | 1983-06-16 |
| GR77710B (oth) | 1984-09-25 |
| GB2107317B (en) | 1985-07-03 |
| LU84412A1 (fr) | 1983-06-13 |
| ATA373182A (de) | 1987-11-15 |
| FR2514357B1 (oth) | 1984-12-28 |
| ES516299A0 (es) | 1983-06-16 |
| IT1149103B (it) | 1986-12-03 |
| IT8249226A0 (it) | 1982-10-07 |
| NL8203859A (nl) | 1983-05-02 |
| SE452885B (sv) | 1987-12-21 |
| US4501740A (en) | 1985-02-26 |
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| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |