CH647507A5 - Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. - Google Patents
Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. Download PDFInfo
- Publication number
- CH647507A5 CH647507A5 CH2231/82A CH223182A CH647507A5 CH 647507 A5 CH647507 A5 CH 647507A5 CH 2231/82 A CH2231/82 A CH 2231/82A CH 223182 A CH223182 A CH 223182A CH 647507 A5 CH647507 A5 CH 647507A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compounds
- formula
- methyl
- ethyl
- indole
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000001033 ether group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- VSBNMIPKPNHSHQ-DLBZAZTESA-N sdz-205-152 Chemical compound C1C2=CC=C(O)C(O)=C2C2=CC(C)=CC3=C2[C@@H]1N(CC)[C@H]3CCC VSBNMIPKPNHSHQ-DLBZAZTESA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000003291 dopaminomimetic effect Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ARZYRECNZACJLE-UHFFFAOYSA-N 3,4-dimethoxy-6-methylphenanthren-9-amine Chemical compound C1=C(C)C=C2C3=C(OC)C(OC)=CC=C3C=C(N)C2=C1 ARZYRECNZACJLE-UHFFFAOYSA-N 0.000 description 3
- VFVLYVFYBCINCZ-UHFFFAOYSA-N 5-ethyl-4,5-dihydro-4-hydroxy-9,10-dimethoxy-2-methyl-4-n-propyl-dibenz[cd,f]indole Chemical compound CC1=CC(C(CCC)(O)N2CC)=C3C2=CC2=CC=C(OC)C(OC)=C2C3=C1 VFVLYVFYBCINCZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- KOPCDCLRCOJWRT-UHFFFAOYSA-N n-(3,4-dimethoxy-6-methylphenanthren-9-yl)acetamide Chemical compound C1=C(C)C=C2C3=C(OC)C(OC)=CC=C3C=C(NC(C)=O)C2=C1 KOPCDCLRCOJWRT-UHFFFAOYSA-N 0.000 description 2
- PVTGGYFBGTYCRU-UHFFFAOYSA-N n-ethyl-3,4-dimethoxy-6-methylphenanthren-9-amine Chemical compound CC1=CC=C2C(NCC)=CC3=CC=C(OC)C(OC)=C3C2=C1 PVTGGYFBGTYCRU-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- ONGZHQMKACCISB-RBUKOAKNSA-N (-)-(4s,5ar)-5-ethyl-4,5,5a,6-tetrahydro-9,10-dimethoxy-2-methyl-4-n-propyl-dibenz[cd,f]indole Chemical compound C1C2=CC=C(OC)C(OC)=C2C2=CC(C)=CC3=C2[C@@H]1N(CC)[C@H]3CCC ONGZHQMKACCISB-RBUKOAKNSA-N 0.000 description 1
- GVSXSFHRTIJTKP-MCJVGQIASA-N (9R,11S)-10-ethyl-14-methyl-11-propyl-10-azatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2(7),3,5,12,14-hexaene-3,4-diol hydrobromide Chemical compound Br.C1C2=CC=C(O)C(O)=C2C2=CC(C)=CC3=C2[C@@H]1N(CC)[C@H]3CCC GVSXSFHRTIJTKP-MCJVGQIASA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- ILWGYWSBUWKROZ-UHFFFAOYSA-N 1h-indole;hydrobromide Chemical compound Br.C1=CC=C2NC=CC2=C1 ILWGYWSBUWKROZ-UHFFFAOYSA-N 0.000 description 1
- CPITUEMGZMFGTE-UHFFFAOYSA-N 3,4-dimethoxy-6-methylphenanthrene-9-carboxylic acid Chemical compound C1=C(C)C=C2C3=C(OC)C(OC)=CC=C3C=C(C(O)=O)C2=C1 CPITUEMGZMFGTE-UHFFFAOYSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 229920005439 Perspex® Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- ZOMNIUBKTOKEHS-UHFFFAOYSA-L dimercury dichloride Chemical compound Cl[Hg][Hg]Cl ZOMNIUBKTOKEHS-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- BQPIGGFYSBELGY-UHFFFAOYSA-N mercury(2+) Chemical class [Hg+2] BQPIGGFYSBELGY-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- -1 oxo- Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002987 phenanthrenes Chemical class 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 210000003523 substantia nigra Anatomy 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2231/82A CH647507A5 (de) | 1982-04-13 | 1982-04-13 | Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. |
| FI831166A FI78072C (fi) | 1982-04-13 | 1983-04-06 | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara (4r*,5as*)-2-alkyl-9,10-dihydro-4,5,5a,6- tetrahydro-dibens/cd,f/indoler. |
| BE1/10753A BE896389A (fr) | 1982-04-13 | 1983-04-07 | Nouveaux derives du dibenz (cd,f) indole,leur preparation et leur utilisation en therapeutique a titre de principes actifs de medicaments, |
| FR8305824A FR2524882B1 (fr) | 1982-04-13 | 1983-04-07 | Nouveaux derives du dibenz(cd,f)indole, leur preparation et leur utilisation en therapeutique a titre de principes actifs de medicaments |
| DE19833312420 DE3312420A1 (de) | 1982-04-13 | 1983-04-07 | Dibenz(cd,f)indolderivate, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten |
| NL8301238A NL8301238A (nl) | 1982-04-13 | 1983-04-08 | Dibenzcd,findoolderivaten, werkwijzen voor het bereiden van deze derivaten en farmaceutische preparaten die ze bevatten. |
| PT76529A PT76529B (en) | 1982-04-13 | 1983-04-11 | Process for the preparation of dibenzo<cd,f>indole derivatives |
| NZ203842A NZ203842A (en) | 1982-04-13 | 1983-04-11 | (4r*,5as*)-2-alkyl-9,10-dioxy-4,5,5a,6-tetrahydrodibenz(cd,f)-indoles |
| IL68354A IL68354A0 (en) | 1982-04-13 | 1983-04-11 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| CA000425608A CA1194028A (en) | 1982-04-13 | 1983-04-11 | Dibenz¬cd,f|indole derivatives, their preparation and pharmaceutical compositions containing them |
| GB08309728A GB2118185B (en) | 1982-04-13 | 1983-04-11 | Dibenz (cd f) indole derivatives their preparation and pharmaceutical compositions containing them |
| JP58064413A JPS58189147A (ja) | 1982-04-13 | 1983-04-12 | ジベンズ〔ｃｄ，ｆ〕インド−ル誘導体、その製造法およびそれからなる医薬 |
| HU831272A HU191519B (en) | 1982-04-13 | 1983-04-12 | Process for producing dibenzo-/c,d,f/-indol derivatives and pharmaceutical compositions containing them |
| IE829/83A IE55262B1 (en) | 1982-04-13 | 1983-04-12 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| ES521397A ES8505343A1 (es) | 1982-04-13 | 1983-04-12 | Procedimiento para preparar derivados de dibenzo |
| AU13439/83A AU574325B2 (en) | 1982-04-13 | 1983-04-12 | Dibenz(cd,f)-indole derivatives, their preparation and pharmaceutical compositions containing them |
| DK160583A DK155004C (da) | 1982-04-13 | 1983-04-12 | Analogifremgangsmaade til fremstilling af 4,5,5a,6-tetrahydro-dibenz-(cd,f)indolderivater |
| SE8302034A SE453664B (sv) | 1982-04-13 | 1983-04-12 | Dibens (cd,f) indolderivat och en farmaceutisk komposition for anvendning som antiparkinson eller antidepressivt medel |
| PH28764A PH23515A (en) | 1982-04-13 | 1983-04-12 | 9'10-dioxy-4,5,5a,6-tetrahydro-dibenz (c,d,f,) indoles derivatives and pharmaceutical compositions containing them |
| IT48098/83A IT1197627B (it) | 1982-04-13 | 1983-04-13 | Derivati del diben (cd,f) indolo,loro preparazione e loro impiego come medicamenti |
| ZA832599A ZA832599B (en) | 1982-04-13 | 1983-04-13 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| US06/683,378 US4602032A (en) | 1982-04-13 | 1984-12-19 | Dibenz[cd,f]indole derivatives, their preparation and pharmaceutical compositions containing them |
| MY794/87A MY8700794A (en) | 1982-04-13 | 1987-12-30 | Dibenz (cd,f) indole derivatives their preparation and pharmaceutical composition containing them |
| SG569/88A SG56988G (en) | 1982-04-13 | 1988-08-29 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| KE3825A KE3825A (en) | 1982-04-13 | 1988-09-08 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| HK1054/88A HK105488A (en) | 1982-04-13 | 1988-12-29 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
| CY1454A CY1454A (en) | 1982-04-13 | 1989-07-21 | Dibenz(cd,f)indole derivatives,their preparation and pharmaceutical compositions containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2231/82A CH647507A5 (de) | 1982-04-13 | 1982-04-13 | Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH647507A5 true CH647507A5 (de) | 1985-01-31 |
Family
ID=4228931
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2231/82A CH647507A5 (de) | 1982-04-13 | 1982-04-13 | Heterozyklische verbindungen, verfahren zu deren herstellung und pharmazeutische zusammensetzungen, welche diese verbindungen enthalten. |
Country Status (27)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4795759A (en) * | 1985-07-27 | 1989-01-03 | Sandoz Ltd. | Use of dibenz(CD,F)indoles |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE877169C (de) * | 1942-02-10 | 1953-05-21 | Siemens Ag | Amplitudenabhaengiges Netzwerk in Form einer Brueckenschaltung, insbesondere zum Schutz von Messinstrumenten gegen UEberstroeme |
| DK249379A (da) * | 1978-06-23 | 1980-01-22 | Sandoz Ag | Fremgangsmaade til fremstilling af phenanthrenderivater |
| FI75153C (fi) * | 1980-06-27 | 1988-05-09 | Sandoz Ag | Foerfarande foer framstaellning av nya farmakologiskt aktiva (4r*,5as*)-4,5,5a,6-tetrahydro-dibens/cd,f/indolderivat. |
| BE889324A (fr) * | 1980-06-27 | 1981-12-22 | Sandoz Sa | Nouveaux derives du dibenz(cd,f)indole, leur preparation et leur application comme medicaments |
-
1982
- 1982-04-13 CH CH2231/82A patent/CH647507A5/de not_active IP Right Cessation
-
1983
- 1983-04-06 FI FI831166A patent/FI78072C/fi not_active IP Right Cessation
- 1983-04-07 FR FR8305824A patent/FR2524882B1/fr not_active Expired
- 1983-04-07 BE BE1/10753A patent/BE896389A/fr not_active IP Right Cessation
- 1983-04-07 DE DE19833312420 patent/DE3312420A1/de not_active Ceased
- 1983-04-08 NL NL8301238A patent/NL8301238A/xx not_active Application Discontinuation
- 1983-04-11 PT PT76529A patent/PT76529B/pt unknown
- 1983-04-11 GB GB08309728A patent/GB2118185B/en not_active Expired
- 1983-04-11 CA CA000425608A patent/CA1194028A/en not_active Expired
- 1983-04-11 NZ NZ203842A patent/NZ203842A/en unknown
- 1983-04-11 IL IL68354A patent/IL68354A0/xx not_active IP Right Cessation
- 1983-04-12 ES ES521397A patent/ES8505343A1/es not_active Expired
- 1983-04-12 IE IE829/83A patent/IE55262B1/en not_active IP Right Cessation
- 1983-04-12 PH PH28764A patent/PH23515A/en unknown
- 1983-04-12 SE SE8302034A patent/SE453664B/sv not_active IP Right Cessation
- 1983-04-12 JP JP58064413A patent/JPS58189147A/ja active Granted
- 1983-04-12 AU AU13439/83A patent/AU574325B2/en not_active Ceased
- 1983-04-12 HU HU831272A patent/HU191519B/hu not_active IP Right Cessation
- 1983-04-12 DK DK160583A patent/DK155004C/da not_active IP Right Cessation
- 1983-04-13 IT IT48098/83A patent/IT1197627B/it active
- 1983-04-13 ZA ZA832599A patent/ZA832599B/xx unknown
-
1984
- 1984-12-19 US US06/683,378 patent/US4602032A/en not_active Expired - Fee Related
-
1987
- 1987-12-30 MY MY794/87A patent/MY8700794A/xx unknown
-
1988
- 1988-08-29 SG SG569/88A patent/SG56988G/en unknown
- 1988-09-08 KE KE3825A patent/KE3825A/xx unknown
- 1988-12-29 HK HK1054/88A patent/HK105488A/xx unknown
-
1989
- 1989-07-21 CY CY1454A patent/CY1454A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69220258T2 (de) | Azabicyclische Verbindungen, diese enthaltende pharmazeutische Zubereitungen und ihre therapeutische Verwendung | |
| EP0546388B1 (de) | Azaheterocyclylmethyl-chromane als Wirkstoffe zur Behandlung von Erkrankungen des Zentralnervensystems | |
| WO1980000152A1 (fr) | Derives d'un 3-aminopropoxy-aryle, leur preparation et utilisation | |
| DD149071A5 (de) | Herstellung 2-substituierter trans-5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido eckige klammer auf 4,3-b eckige klammer zu indole | |
| DE3510858A1 (de) | Substituierte (alpha)-aminosaeuren, verfahren zu deren herstellung und diese enthaltende arzneimittel | |
| CH625790A5 (cg-RX-API-DMAC10.html) | ||
| DE69517433T2 (de) | Benzozykloalkenverbindungen, deren herstellung und verwendung | |
| EP0413667B1 (de) | Halogenalkylphenyl-Alkohole, -Ketone und deren Hydrate | |
| EP0473550A1 (de) | Indolonaphthyridine | |
| DE68925173T2 (de) | 4-Methyl und 4-Ethyl substituierte Pyrrolidin-2-one | |
| EP0389425B1 (de) | Neue Benzothiopyranylamine | |
| EP0266308B1 (de) | Indolo-pyrazino-benzodiazepin-Derivate | |
| DE3300522C2 (cg-RX-API-DMAC10.html) | ||
| CH641162A5 (de) | Verfahren zur herstellung neuer phenylazacycloalkane. | |
| WO1982000143A1 (en) | Heterocyclic compounds,method for preparing such compounds and pharmaceutical compositions containing them | |
| DE69615845T2 (de) | Polycyclische alkaloid-derivate als nmda-rezeptor-antagonisten | |
| DE3854343T2 (de) | Neuroschützende Cyclooctanmittel. | |
| EP0322361A2 (de) | Weitere hydrierte 1-Benzooxacycloalkylpyridincarbonsäureverbindungen | |
| EP0001585B1 (de) | Piperazino-pyrrolobenzodiazepine, Verfahren zu ihrer Herstellung sowie pharmazeutische Präparate enthaltend diese Verbindungen | |
| EP0056616B1 (de) | Cycloheptenderivate, Verfahren zu ihrer Herstellung, sowie diese enthaltende Arzneimittel | |
| AT375079B (de) | Verfahren zur herstellung von neuen trans-2,3,4,4a ,5,9b-hexahydro-1h-pyrido(4,3-b)indolen und ihren pharmazeutisch annehmbaren salzen | |
| EP0350445A1 (de) | Substituierte Azacyclohexyl-Derivate | |
| EP0483063B1 (de) | Ergolinderivate | |
| CH649288A5 (en) | Tetrahydrobenzindoles, process for their preparation and pharmaceutical compositions which contain these compounds | |
| WO1980000561A1 (fr) | Derives de l'(alpha)-alcoyle-o-oxy-benzylamine, leur preparation et remedes les contenant |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |