FR2467206A1 - Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique - Google Patents
Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique Download PDFInfo
- Publication number
- FR2467206A1 FR2467206A1 FR7925353A FR7925353A FR2467206A1 FR 2467206 A1 FR2467206 A1 FR 2467206A1 FR 7925353 A FR7925353 A FR 7925353A FR 7925353 A FR7925353 A FR 7925353A FR 2467206 A1 FR2467206 A1 FR 2467206A1
- Authority
- FR
- France
- Prior art keywords
- radical
- compounds
- alkyl
- alkoxycarbonyl
- oxayohimbane
- 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
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002252 acyl group Chemical group 0.000 claims abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229930013930 alkaloid Natural products 0.000 claims description 2
- 150000003797 alkaloid derivatives Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 241001122767 Theaceae Species 0.000 claims 1
- -1 atom halogen Chemical class 0.000 abstract description 11
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract description 2
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 abstract 1
- ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 description 6
- 239000002585 base Substances 0.000 description 6
- GRTOGORTSDXSFK-DLLGKBFGSA-N tetrahydroalstonine 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-DLLGKBFGSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- PEYPCTZOXFDFFW-UHFFFAOYSA-N 3-Iso-19-epi-ajnalicin Natural products C1=CC=C2C3CCN4CC5C(C)OC=C(C(=O)OC)C5CC4C3NC2=C1 PEYPCTZOXFDFFW-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KXEMQEGRZWUKJS-UHFFFAOYSA-N Raufloridine Natural products COC1=CC=C2C(CCN3CC4C(C)OC=C(C4CC33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- FVMMOSQBOWPRQW-UHFFFAOYSA-N heterophylline Natural products CC(=O)OC1C2(C)C(OC(=O)C=3C=CC=CC=3)CC(C(O3)(C)C)C(OC(=O)C=4C=NC=CC=4)C32C(C)CC1OC(=O)C1=CC=CN=C1 FVMMOSQBOWPRQW-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000007953 anoxia Effects 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- KXEMQEGRZWUKJS-OVXHWVBHSA-N raunitidine Chemical compound COC1=CC=C2C(CCN3C[C@H]4[C@@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-OVXHWVBHSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 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 1
- SZLZWPPUNLXJEA-UHFFFAOYSA-N 11,17-dimethoxy-18-[3-(3,4,5-trimethoxy-phenyl)-acryloyloxy]-yohimbane-16-carboxylic acid methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(OC)C1OC(=O)C=CC1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-UHFFFAOYSA-N 0.000 description 1
- DTDADHMBRZKXSC-GKASHWOUSA-N Aricine Chemical compound C1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DTDADHMBRZKXSC-GKASHWOUSA-N 0.000 description 1
- DTDADHMBRZKXSC-IEGSVRCHSA-N Cabucine Chemical compound C1=C(OC)C=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 DTDADHMBRZKXSC-IEGSVRCHSA-N 0.000 description 1
- 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
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- VQMBBGRNTJZIFV-UHFFFAOYSA-N Rauvanin Natural products COC(=O)C1=COC(C)C2CN3CCC4C(Nc5cc(OC)c(OC)cc45)C3CC12 VQMBBGRNTJZIFV-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 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
- 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
- 239000004480 active ingredient Substances 0.000 description 1
- 229940007897 ajmalicine Drugs 0.000 description 1
- GRTOGORTSDXSFK-BMYCAMMWSA-N akuammigine 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-BMYCAMMWSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- QVBOOBQEGOUUGN-RCBQFDQVSA-N alstonine Chemical compound C1=C[CH]C2=NC3=C(C[C@@H]4C(C(=O)OC)=CO[C@@H](C)[C@@H]4C4)[N+]4=CC=C3C2=C1 QVBOOBQEGOUUGN-RCBQFDQVSA-N 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
- UHDJCSZGZJGMDR-UHFFFAOYSA-N aricine Natural products COC(=O)C1=COC(C)C2(C)CN3CCc4c([nH]c5ccc(OC)cc45)C3(C)CC12C UHDJCSZGZJGMDR-UHFFFAOYSA-N 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- XXZJUUFVWAGZEG-UHFFFAOYSA-N cabucine Natural products COC(=O)C1=COC(C)C2CN3CCc4c([nH]c5ccc(C)cc45)C3CC12 XXZJUUFVWAGZEG-UHFFFAOYSA-N 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- FGWJRZQNNZVCHR-HAHWVIBASA-N iso-reserpiline Chemical compound COC1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 FGWJRZQNNZVCHR-HAHWVIBASA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- KXEMQEGRZWUKJS-VDESFZGPSA-N methyl (3β,19α)-16,17-didehydro-11-methoxy-19-methyloxayohimban-16-carboxylate Chemical compound COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-VDESFZGPSA-N 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
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- QXSGZNGSUBCBAZ-UHFFFAOYSA-N mitrajavine Natural products COC(=O)C1=COC(C)C2CN3CCc4c([nH]c5cccc(OC)c45)C3CC12 QXSGZNGSUBCBAZ-UHFFFAOYSA-N 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
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- FGWJRZQNNZVCHR-FERZIJSQSA-N rauvanin Chemical compound COC1=C(OC)C=C2C(CCN3C[C@@H]4[C@@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 FGWJRZQNNZVCHR-FERZIJSQSA-N 0.000 description 1
- SZLZWPPUNLXJEA-QEGASFHISA-N rescinnamine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)\C=C\C1=CC(OC)=C(OC)C(OC)=C1 SZLZWPPUNLXJEA-QEGASFHISA-N 0.000 description 1
- 229960001965 rescinnamine Drugs 0.000 description 1
- FGWJRZQNNZVCHR-BCRCDCHUSA-N reserpiline Chemical compound COC1=C(OC)C=C2C(CCN3C[C@H]4[C@H](C)OC=C([C@H]4C[C@@H]33)C(=O)OC)=C3NC2=C1 FGWJRZQNNZVCHR-BCRCDCHUSA-N 0.000 description 1
- 229950010889 reserpiline Drugs 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
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 229940035718 sular Drugs 0.000 description 1
- KXEMQEGRZWUKJS-QIYNHLNTSA-N tetraphylline Chemical compound COC1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 KXEMQEGRZWUKJS-QIYNHLNTSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925353A FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
| JP14184380A JPS5661382A (en) | 1979-10-11 | 1980-10-09 | Oxayohimbine derivative |
| IT25251/80A IT1195761B (it) | 1979-10-11 | 1980-10-09 | Derivati dell'acido ossayohimban-carbossilico |
| ZA00806246A ZA806246B (en) | 1979-10-11 | 1980-10-09 | Oxayohimbane-carboxylic acid derivatives |
| PT71901A PT71901B (fr) | 1979-10-11 | 1980-10-10 | Procede de preparation de derives de l'acide oxayohimbane-carboxylique |
| AU63165/80A AU6316580A (en) | 1979-10-11 | 1980-10-10 | Oxayohimbane derivatives |
| NO803038A NO803038L (no) | 1979-10-11 | 1980-10-10 | Fremgangsmaate for fremstilling av oksayohimbankarboksylsyre-derivater. |
| NL8005609A NL8005609A (nl) | 1979-10-11 | 1980-10-10 | Derivaten van oxayohimbaancarbonzuur, de bereiding hiervan en de toepassing van deze derivaten in genees- middelen. |
| GR63108A GR70751B (enExample) | 1979-10-11 | 1980-10-10 | |
| GB8032835A GB2060639A (en) | 1979-10-11 | 1980-10-10 | Novel oxayohimbane derivatives useful in therapy |
| LU82833A LU82833A1 (fr) | 1979-10-11 | 1980-10-10 | Derives de l'acide oxayohimbane-carboxylique |
| DK428780A DK428780A (da) | 1979-10-11 | 1980-10-10 | Oxayohimbancarboxylsyrederivater samt fremgangsmaade til deresfremstilling |
| DE19803038401 DE3038401A1 (de) | 1979-10-11 | 1980-10-10 | Oxayohimban-carbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| ES495797A ES8206521A1 (es) | 1979-10-11 | 1980-10-10 | Un procedimiento de preparacion de derivados del acido oxa- yohimbano-carboxilico |
| IL61246A IL61246A0 (en) | 1979-10-11 | 1980-10-10 | Oxayohimbane derivatives, their preparation and pharmaceutical compositions containing them |
| SE8007121A SE8007121L (sv) | 1979-10-11 | 1980-10-10 | Oxyohimbankarboxylsyra derivat |
| BE0/202429A BE885656A (fr) | 1979-10-11 | 1980-10-10 | Derives de l'acide oxayohimbane-carboxylique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7925353A FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2467206A1 true FR2467206A1 (fr) | 1981-04-17 |
| FR2467206B1 FR2467206B1 (enExample) | 1983-01-28 |
Family
ID=9230588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7925353A Granted FR2467206A1 (fr) | 1979-10-11 | 1979-10-11 | Derives de l'acide oxayohimbane-carboxylique, leur preparation et leur application en therapeutique |
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 |
| LU82833A1 (fr) | 1982-05-10 |
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |