LU82833A1 - Derives de l'acide oxayohimbane-carboxylique - Google Patents
Derives de l'acide oxayohimbane-carboxylique Download PDFInfo
- Publication number
- LU82833A1 LU82833A1 LU82833A LU82833A LU82833A1 LU 82833 A1 LU82833 A1 LU 82833A1 LU 82833 A LU82833 A LU 82833A LU 82833 A LU82833 A LU 82833A LU 82833 A1 LU82833 A1 LU 82833A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- radical
- compounds
- alkoxycarbonyl
- acid
- raubasine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 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 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 238000007796 conventional method Methods 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 159000000011 group IA salts Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 230000009435 amidation Effects 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- -1 atom halogen Chemical class 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 230000007928 solubilization Effects 0.000 claims 1
- 238000005063 solubilization Methods 0.000 claims 1
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- CZJDUZOWQVAEEV-XIEZEKGWSA-N (+)-19-epi-Ajmalicine Natural products O=C(OC)C=1[C@@H]2[C@@H]([C@@H](C)OC=1)C[N+]1[C@H](c3[nH]c4c(c3CC1)cccc4)C2 CZJDUZOWQVAEEV-XIEZEKGWSA-N 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 229940007897 ajmalicine Drugs 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000007953 anoxia Effects 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000020401 Depressive disease Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 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 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- GRTOGORTSDXSFK-UHFFFAOYSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-UHFFFAOYSA-N 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
- 230000000496 anti-anoxic effect Effects 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VKQFCGNPDRICFG-UHFFFAOYSA-N methyl 2-methylpropyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCC(C)C)C1C1=CC=CC=C1[N+]([O-])=O VKQFCGNPDRICFG-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940035718 sular Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 208000009999 tuberous sclerosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preventing Corrosion Or Incrustation Of Metals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925353 | 1979-10-11 | ||
| FR7925353A FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU82833A1 true LU82833A1 (fr) | 1982-05-10 |
Family
ID=9230588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU82833A LU82833A1 (fr) | 1979-10-11 | 1980-10-10 | Derives de l'acide oxayohimbane-carboxylique |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5661382A (enExample) |
| AU (1) | AU6316580A (enExample) |
| BE (1) | BE885656A (enExample) |
| DE (1) | DE3038401A1 (enExample) |
| DK (1) | DK428780A (enExample) |
| ES (1) | ES8206521A1 (enExample) |
| FR (1) | FR2467206A1 (enExample) |
| GB (1) | GB2060639A (enExample) |
| GR (1) | GR70751B (enExample) |
| IL (1) | IL61246A0 (enExample) |
| IT (1) | IT1195761B (enExample) |
| LU (1) | LU82833A1 (enExample) |
| NL (1) | NL8005609A (enExample) |
| NO (1) | NO803038L (enExample) |
| PT (1) | PT71901B (enExample) |
| SE (1) | SE8007121L (enExample) |
| ZA (1) | ZA806246B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4125137C2 (de) * | 1991-07-30 | 1995-06-14 | Icos Ges Fuer Ind Communicatio | Steuerpult für Bearbeitungs- und Meßmaschinen |
-
1979
- 1979-10-11 FR FR7925353A patent/FR2467206A1/fr active Granted
-
1980
- 1980-10-09 ZA ZA00806246A patent/ZA806246B/xx unknown
- 1980-10-09 IT IT25251/80A patent/IT1195761B/it active
- 1980-10-09 JP JP14184380A patent/JPS5661382A/ja active Pending
- 1980-10-10 NO NO803038A patent/NO803038L/no unknown
- 1980-10-10 GB GB8032835A patent/GB2060639A/en not_active Withdrawn
- 1980-10-10 BE BE0/202429A patent/BE885656A/fr unknown
- 1980-10-10 DK DK428780A patent/DK428780A/da unknown
- 1980-10-10 ES ES495797A patent/ES8206521A1/es not_active Expired
- 1980-10-10 NL NL8005609A patent/NL8005609A/nl not_active Application Discontinuation
- 1980-10-10 AU AU63165/80A patent/AU6316580A/en not_active Abandoned
- 1980-10-10 PT PT71901A patent/PT71901B/pt unknown
- 1980-10-10 IL IL61246A patent/IL61246A0/xx unknown
- 1980-10-10 LU LU82833A patent/LU82833A1/fr unknown
- 1980-10-10 GR GR63108A patent/GR70751B/el unknown
- 1980-10-10 DE DE19803038401 patent/DE3038401A1/de not_active Withdrawn
- 1980-10-10 SE SE8007121A patent/SE8007121L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL61246A0 (en) | 1980-12-31 |
| FR2467206B1 (enExample) | 1983-01-28 |
| SE8007121L (sv) | 1981-04-12 |
| NO803038L (no) | 1981-04-13 |
| IT1195761B (it) | 1988-10-27 |
| ES495797A0 (es) | 1982-01-16 |
| ES8206521A1 (es) | 1982-01-16 |
| GB2060639A (en) | 1981-05-07 |
| JPS5661382A (en) | 1981-05-26 |
| ZA806246B (en) | 1981-10-28 |
| DE3038401A1 (de) | 1981-04-23 |
| IT8025251A0 (it) | 1980-10-09 |
| BE885656A (fr) | 1981-04-10 |
| GR70751B (enExample) | 1983-03-14 |
| PT71901B (fr) | 1981-08-31 |
| NL8005609A (nl) | 1981-04-14 |
| DK428780A (da) | 1981-04-12 |
| PT71901A (fr) | 1980-11-01 |
| AU6316580A (en) | 1981-04-16 |
| FR2467206A1 (fr) | 1981-04-17 |
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