NL8302287A - Eburnaanderivaten, werkwijze ter bereiding daarvan en farmaceutische samenstellingen, die deze derivaten bevatten. - Google Patents
Eburnaanderivaten, werkwijze ter bereiding daarvan en farmaceutische samenstellingen, die deze derivaten bevatten. Download PDFInfo
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- NL8302287A NL8302287A NL8302287A NL8302287A NL8302287A NL 8302287 A NL8302287 A NL 8302287A NL 8302287 A NL8302287 A NL 8302287A NL 8302287 A NL8302287 A NL 8302287A NL 8302287 A NL8302287 A NL 8302287A
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- Prior art keywords
- formula
- acid
- racemic
- optically active
- hydrogen
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- 238000000034 method Methods 0.000 title claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
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- 239000007788 liquid Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000006146 oximation reaction Methods 0.000 claims description 2
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- 239000007858 starting material Substances 0.000 description 7
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- 125000003118 aryl group Chemical group 0.000 description 2
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- 238000002329 infrared spectrum Methods 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
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- 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
- 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000003381 stabilizer 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
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension 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
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- 229910052716 thallium Inorganic materials 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU822132A HU187139B (en) | 1982-06-30 | 1982-06-30 | Process for preparing new eburnan derivatives |
| HU213282 | 1982-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8302287A true NL8302287A (nl) | 1984-01-16 |
Family
ID=10957927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8302287A NL8302287A (nl) | 1982-06-30 | 1983-06-28 | Eburnaanderivaten, werkwijze ter bereiding daarvan en farmaceutische samenstellingen, die deze derivaten bevatten. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4551462A (sv) |
| JP (1) | JPS5913781A (sv) |
| AT (1) | ATA238583A (sv) |
| AU (1) | AU554197B2 (sv) |
| BE (1) | BE897152A (sv) |
| DE (1) | DE3322686A1 (sv) |
| DK (1) | DK296783A (sv) |
| ES (1) | ES8600286A1 (sv) |
| FR (1) | FR2529553B1 (sv) |
| GB (1) | GB2124216B (sv) |
| GR (1) | GR77527B (sv) |
| HU (1) | HU187139B (sv) |
| IL (1) | IL68985A0 (sv) |
| NL (1) | NL8302287A (sv) |
| NZ (1) | NZ204757A (sv) |
| PT (1) | PT76952B (sv) |
| SE (1) | SE8303720L (sv) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191403B (en) * | 1984-04-02 | 1987-02-27 | Richter Gedeon Vegyeszeti Gyar Rt,Hu | Process for preparing new, raceme and optically active 14-hydroxyimino-eburnane |
| US4735943A (en) * | 1984-06-29 | 1988-04-05 | Sanwa Kagaku Kenkyusho Co., Ltd. | Eburnamonine oxime derivatives, salts thereof, and pharmaceutical agents containing the same |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1590633A (sv) * | 1968-06-25 | 1970-04-20 | ||
| FR2081587B1 (sv) * | 1970-03-26 | 1973-04-06 | Anvar | |
| US3770724A (en) * | 1970-03-31 | 1973-11-06 | Roussel Uclaf | Process for preparing pentacyclic alkaloids |
| FR2085630A1 (en) * | 1970-04-07 | 1971-12-31 | Le Men Georges | Vincamone compsn - having vasodilator ganglioplegic and antihistamine activity |
| BE797328R (en) * | 1971-08-31 | 1973-07-16 | Omnium Chimique Sa | Aminopropyl vincanols and eburnamines prepn - - by reaction of organo magnesium cpd with a vincanone or substd ebur |
| HU166474B (sv) * | 1971-11-03 | 1975-03-28 | ||
| FR2168853B1 (sv) * | 1972-01-24 | 1975-04-25 | Centre Etd Ind Pharma | |
| FR2175317A5 (en) * | 1972-03-09 | 1973-10-19 | Anvar | Naphthiridine derivs - from dihydro-3,4-beta carboline and chloro-1-ketone-3-carbomethoxy-5-pentane |
| FR2179620B1 (sv) * | 1972-04-14 | 1975-12-26 | Roussel Uclaf | |
| FR2179619A1 (en) * | 1972-04-14 | 1973-11-23 | Roussel Uclaf | Eburnane-16-beta-ols - with hypotensive and cerebral vasodilator activity |
| AT325786B (de) * | 1972-05-17 | 1975-11-10 | Richter Gedeon Vegyeszet | Verfahren zur herstellung von eburnamoninen |
| US3852453A (en) * | 1972-05-26 | 1974-12-03 | Synthelabo | Method of enhancing vincamine compositions |
| US4033969A (en) * | 1972-06-19 | 1977-07-05 | Agence Nationale De Valorisation De La Recherche (Anvar) | Vincamine derivatives |
| FR2190113A5 (sv) * | 1972-06-19 | 1974-01-25 | Anvar | |
| FR2194193A5 (sv) * | 1972-07-31 | 1974-02-22 | Roussel Uclaf | |
| FR2206090A1 (en) * | 1972-11-16 | 1974-06-07 | Omnium Chimique Sa | Homovincamone-contg. medicaments - with vasodilating, spasmolytic anti-arrhythmic and anti-ischaemic properties |
| HU166766B (sv) * | 1972-12-08 | 1975-05-28 | ||
| FR2213276A1 (en) * | 1973-01-09 | 1974-08-02 | Roussel Uclaf | 9H-Pyrido(3,4-B)indole derivs - inters for eburnamonine alkaloids |
| BE802387A (fr) * | 1973-07-16 | 1973-11-16 | Omnium Chimique Sa | Procede de preparation de la vincamone et de l'epi-21 vincamone a partir de la tabersonine et derives indoliques nouveaux. |
| FR2253502A1 (en) * | 1973-12-07 | 1975-07-04 | Synthelabo | 14,15-Dihydro eburnamenine-14-thione - by treatment of 14,15-dihydro eburnamenine-14-one with a phosphorus sulphide |
| FR2268016A1 (en) * | 1974-04-17 | 1975-11-14 | Omnium Chimique Sa | Racemic or opt. active eburnamonines - by reaction of racemic or opt. active vincamines, in an organic solven, with a base |
| 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 |
| 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 |
| FR2414507A1 (fr) * | 1978-01-13 | 1979-08-10 | Omnium Chimique Sa | Trans-eburnamonine et son utilisation pour traiter les insuffisances d'oxygenation tissulaire |
| CA1117939A (en) * | 1978-02-15 | 1982-02-09 | Enrico C. Mora | Derivatives of eburnamomine and related method of manufacturing |
| 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 |
| DE2922316A1 (de) * | 1978-06-12 | 1979-12-20 | Omnium Chimique Sa | Neue halogenderivate des vincamins, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| FR2433528A2 (fr) * | 1978-08-16 | 1980-03-14 | Roussel Uclaf | Nouveaux derives de 20,21-dinoreburnamenine, un procede pour leur preparation et leur application comme medicaments |
| US4316028A (en) * | 1978-11-20 | 1982-02-16 | Sumitomo Chemical Company, Limited | Process for producing eburnane derivatives |
| HU179292B (en) * | 1978-12-01 | 1982-09-28 | Richter Gedeon Vegyeszet | Process for preparing ester derivatives of apovincaminic acid |
| FR2454808A1 (fr) * | 1979-04-26 | 1980-11-21 | Roussel Uclaf | Application a titre de medicaments d'oximes derivees du e-homo eburnane, oximes derivees du e-homo eburnane et preparation |
| HU180928B (en) * | 1979-08-06 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for preparing new brominated 15-hydroxy-e-homo-eburane derivatives |
| HU180929B (en) * | 1979-08-13 | 1983-05-30 | Richter Gedeon Vegyeszet | Process for producing new bromo-vincamone derivatives |
| HU182411B (en) * | 1981-11-03 | 1984-01-30 | Richter Gedeon Vegyeszet | Process for preparing eburnamonine derivatives |
-
1982
- 1982-06-30 HU HU822132A patent/HU187139B/hu not_active IP Right Cessation
-
1983
- 1983-06-14 IL IL68985A patent/IL68985A0/xx unknown
- 1983-06-23 DE DE19833322686 patent/DE3322686A1/de not_active Withdrawn
- 1983-06-27 FR FR8310576A patent/FR2529553B1/fr not_active Expired
- 1983-06-27 JP JP58114432A patent/JPS5913781A/ja active Pending
- 1983-06-27 US US06/508,438 patent/US4551462A/en not_active Expired - Fee Related
- 1983-06-28 DK DK296783A patent/DK296783A/da not_active Application Discontinuation
- 1983-06-28 BE BE0/211072A patent/BE897152A/fr not_active IP Right Cessation
- 1983-06-28 NL NL8302287A patent/NL8302287A/nl not_active Application Discontinuation
- 1983-06-29 GB GB08317613A patent/GB2124216B/en not_active Expired
- 1983-06-29 AT AT0238583A patent/ATA238583A/de not_active Application Discontinuation
- 1983-06-29 ES ES523684A patent/ES8600286A1/es not_active Expired
- 1983-06-29 PT PT76952A patent/PT76952B/pt unknown
- 1983-06-29 AU AU16397/83A patent/AU554197B2/en not_active Ceased
- 1983-06-29 NZ NZ204757A patent/NZ204757A/en unknown
- 1983-06-29 GR GR71807A patent/GR77527B/el unknown
- 1983-06-29 SE SE8303720A patent/SE8303720L/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5913781A (ja) | 1984-01-24 |
| GB8317613D0 (en) | 1983-08-03 |
| DE3322686A1 (de) | 1984-02-16 |
| AU554197B2 (en) | 1986-08-14 |
| PT76952A (en) | 1983-07-01 |
| PT76952B (en) | 1986-01-24 |
| GR77527B (sv) | 1984-09-24 |
| SE8303720L (sv) | 1983-12-31 |
| DK296783D0 (da) | 1983-06-28 |
| ES523684A0 (es) | 1985-10-01 |
| AU1639783A (en) | 1984-01-05 |
| US4551462A (en) | 1985-11-05 |
| FR2529553B1 (fr) | 1986-09-26 |
| HU187139B (en) | 1985-11-28 |
| ATA238583A (de) | 1986-11-15 |
| BE897152A (fr) | 1983-12-28 |
| IL68985A0 (en) | 1983-10-31 |
| FR2529553A1 (fr) | 1984-01-06 |
| GB2124216A (en) | 1984-02-15 |
| DK296783A (da) | 1983-12-31 |
| ES8600286A1 (es) | 1985-10-01 |
| GB2124216B (en) | 1985-09-11 |
| SE8303720D0 (sv) | 1983-06-29 |
| NZ204757A (en) | 1985-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |