AT388379B - Verfahren zur herstellung von neuen diazepinoindolen - Google Patents
Verfahren zur herstellung von neuen diazepinoindolenInfo
- Publication number
- AT388379B AT388379B AT0052285A AT52285A AT388379B AT 388379 B AT388379 B AT 388379B AT 0052285 A AT0052285 A AT 0052285A AT 52285 A AT52285 A AT 52285A AT 388379 B AT388379 B AT 388379B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- compounds
- formula
- alkyl
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 239000002253 acid Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 4
- 239000003814 drug Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000001430 anti-depressive effect Effects 0.000 abstract description 3
- 239000000935 antidepressant agent Substances 0.000 abstract description 3
- 229940005513 antidepressants Drugs 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 230000000701 neuroleptic effect Effects 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 230000001603 reducing effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 206010044565 Tremor Diseases 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- -1 diborane Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 229950001675 spiperone Drugs 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- GNKPIBQHOLYNER-UHFFFAOYSA-N 2-chloro-n-methyl-n-[2-(3-phenyl-1h-indol-2-yl)ethyl]acetamide Chemical compound ClCC(=O)N(C)CCC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 GNKPIBQHOLYNER-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 108091002531 OF-1 protein Proteins 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000027455 binding Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000012417 linear regression Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 230000033001 locomotion Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 230000009871 nonspecific binding Effects 0.000 description 2
- FWFGVMYFCODZRD-UHFFFAOYSA-N oxidanium;hydrogen sulfate Chemical compound O.OS(O)(=O)=O FWFGVMYFCODZRD-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000009870 specific binding Effects 0.000 description 2
- 238000013268 sustained release Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SJJKLOLDEMVAFA-UHFFFAOYSA-N 1,3,4,5-tetrahydro-[1,4]diazepino[1,7-a]indol-2-one Chemical compound C1CNC(=O)CC2=CC3=CC=CC=C3N21 SJJKLOLDEMVAFA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MXNWZMSJUIEZOY-UHFFFAOYSA-N 2-chloro-n-[1-(1h-indol-2-yl)ethyl]acetamide Chemical compound C1=CC=C2NC(C(NC(=O)CCl)C)=CC2=C1 MXNWZMSJUIEZOY-UHFFFAOYSA-N 0.000 description 1
- WNZTZMZSYKQPMJ-UHFFFAOYSA-N 3-methyl-11-phenyl-1,2,4,5-tetrahydro-[1,4]diazepino[1,7-a]indole Chemical compound C12=CC=CC=C2N2CCN(C)CCC2=C1C1=CC=CC=C1 WNZTZMZSYKQPMJ-UHFFFAOYSA-N 0.000 description 1
- 102000056834 5-HT2 Serotonin Receptors Human genes 0.000 description 1
- 108091005479 5-HT2 receptors Proteins 0.000 description 1
- 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 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001071900 Scapanus orarius Species 0.000 description 1
- 206010041243 Social avoidant behaviour Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000001705 anti-serotonergic effect Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 229940005530 anxiolytics Drugs 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 210000005153 frontal cortex Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DDUIBNCWOUBYON-UHFFFAOYSA-N n-methyl-2-(3-phenyl-1h-indol-2-yl)ethanamine Chemical compound CNCCC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 DDUIBNCWOUBYON-UHFFFAOYSA-N 0.000 description 1
- 230000028570 negative regulation of locomotion Effects 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 230000000803 paradoxical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006349 photocyclization reaction Methods 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- BSYFXFLGOGQHFU-UHFFFAOYSA-N pyrrolo[2,3-g][1,2]benzodiazepine Chemical class N1=NC=CC=C2C3=NC=CC3=CC=C21 BSYFXFLGOGQHFU-UHFFFAOYSA-N 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH86384 | 1984-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA52285A ATA52285A (de) | 1988-11-15 |
| AT388379B true AT388379B (de) | 1989-06-12 |
Family
ID=4196936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT0052285A AT388379B (de) | 1984-02-22 | 1985-02-21 | Verfahren zur herstellung von neuen diazepinoindolen |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4673674A (en, 2012) |
| JP (1) | JPS60202887A (en, 2012) |
| AT (1) | AT388379B (en, 2012) |
| BE (1) | BE901725A (en, 2012) |
| CA (1) | CA1271193A (en, 2012) |
| DE (1) | DE3505017A1 (en, 2012) |
| DK (1) | DK78385A (en, 2012) |
| ES (2) | ES8706681A1 (en, 2012) |
| FI (1) | FI79316C (en, 2012) |
| FR (1) | FR2609715B1 (en, 2012) |
| GB (1) | GB2154584B (en, 2012) |
| GR (1) | GR850443B (en, 2012) |
| HU (1) | HU193083B (en, 2012) |
| IL (1) | IL74388A (en, 2012) |
| IT (1) | IT1199949B (en, 2012) |
| LU (1) | LU85778A1 (en, 2012) |
| MY (1) | MY100083A (en, 2012) |
| NL (1) | NL8500370A (en, 2012) |
| PH (1) | PH22247A (en, 2012) |
| PL (2) | PL144329B1 (en, 2012) |
| PT (1) | PT79990B (en, 2012) |
| SE (1) | SE8500822L (en, 2012) |
| ZA (1) | ZA851373B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3635071A1 (de) * | 1986-10-15 | 1988-04-28 | Autoflug Gmbh | Rueckenlehnenverriegelung fuer einen mit sicherheitsgurten ausgeruesteten fahrzeugsitz |
| EP1328525A2 (en) * | 2000-03-14 | 2003-07-23 | PHARMACIA & UPJOHN COMPANY | 2,3,4,5-tetrahydro-1h-[1,4]diazepino[1,7-a]indole compounds |
| EP1896062B1 (en) * | 2005-06-27 | 2010-03-31 | GlaxoSmithKline Biologicals S.A. | Immunogenic composition |
| HU230880B1 (hu) * | 2015-04-15 | 2018-11-29 | Richter Gedeon Nyrt | Indol származékok |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1593146A (en) * | 1976-11-05 | 1981-07-15 | Beecham Group Ltd | Octahydro-quinolizinyl benzamide derivatives |
| US4210590A (en) * | 1978-01-06 | 1980-07-01 | Mcneil Laboratories, Incorporated | Reduction of indole compounds to indoline compounds |
| CH649553A5 (de) * | 1982-05-06 | 1985-05-31 | Sandoz Ag | Azepinoindole und verfahren zu deren herstellung. |
-
1985
- 1985-02-11 NL NL8500370A patent/NL8500370A/nl not_active Application Discontinuation
- 1985-02-11 HU HU85510A patent/HU193083B/hu not_active IP Right Cessation
- 1985-02-13 BE BE1/11188A patent/BE901725A/fr unknown
- 1985-02-14 PH PH31856A patent/PH22247A/en unknown
- 1985-02-14 DE DE19853505017 patent/DE3505017A1/de not_active Withdrawn
- 1985-02-19 GB GB08504179A patent/GB2154584B/en not_active Expired
- 1985-02-20 FI FI850702A patent/FI79316C/fi not_active IP Right Cessation
- 1985-02-20 IL IL74388A patent/IL74388A/xx unknown
- 1985-02-20 SE SE8500822A patent/SE8500822L/xx not_active Application Discontinuation
- 1985-02-20 IT IT47704/85A patent/IT1199949B/it active
- 1985-02-20 LU LU85778A patent/LU85778A1/fr unknown
- 1985-02-20 PT PT79990A patent/PT79990B/pt unknown
- 1985-02-20 DK DK78385A patent/DK78385A/da not_active Application Discontinuation
- 1985-02-20 GR GR850443A patent/GR850443B/el unknown
- 1985-02-20 ES ES540559A patent/ES8706681A1/es not_active Expired
- 1985-02-21 JP JP60034261A patent/JPS60202887A/ja active Pending
- 1985-02-21 CA CA000474852A patent/CA1271193A/en not_active Expired - Lifetime
- 1985-02-21 PL PL1985252065A patent/PL144329B1/pl unknown
- 1985-02-21 PL PL1985268394A patent/PL146274B1/pl unknown
- 1985-02-21 US US06/704,040 patent/US4673674A/en not_active Expired - Fee Related
- 1985-02-21 AT AT0052285A patent/AT388379B/de not_active IP Right Cessation
- 1985-02-22 ZA ZA851373A patent/ZA851373B/xx unknown
-
1986
- 1986-05-16 ES ES555042A patent/ES8707204A1/es not_active Expired
-
1987
- 1987-09-25 MY MYPI87001944A patent/MY100083A/en unknown
- 1987-11-23 FR FR878716324A patent/FR2609715B1/fr not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69020694T2 (de) | Tricyclische Verbindungen. | |
| DE60309057T2 (de) | Azabicycloderivate als antagonisten des muscarinischen rezeptors | |
| DE2614406A1 (de) | Tetracyclische verbindungen, verfahren zu deren herstellung und arzneimittel, enthaltend diese verbindungen | |
| DE2025248A1 (en, 2012) | ||
| EP0022078A1 (de) | Pyrazolochinoline, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate enthaltend diese Verbindungen | |
| DE60204044T2 (de) | Piperazin derivate mit sst1 antagonistischer wirkung | |
| EP0387618B1 (de) | 1,7-anellierte 1H-Indol-2-carbonsäure-N-(1,4-benzodiazepin-3-yl)amide | |
| EP0163260A1 (de) | Neue substituierte Pyrrolidinone, Verfahren zu ihrer Herstellung und Arzneimittel | |
| AT388379B (de) | Verfahren zur herstellung von neuen diazepinoindolen | |
| CH649553A5 (de) | Azepinoindole und verfahren zu deren herstellung. | |
| DE69810560T2 (de) | Indanol-Derivate, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| EP0085899B1 (de) | Neue Pyridobenzodiazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0085892B1 (de) | Substituierte Dibenzodiazepinone, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE2918778A1 (de) | 6-substituierte 11-alkylen-morphantridine | |
| DE69131057T2 (de) | 3-[1,Thiazolidinylbutyl-4-piperazinyl]-1H-Indazole, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikamente | |
| DD219765A5 (de) | Verfahren zur herstellung von substituierten hexahydropyrrolo (-1,2-a)-chinolin-, hexahydro-1h-pyrido (1,2-a)chinolin-, hexahydrobenzo(e)inden- und octahydrophenanthren-zns-mitteln | |
| EP0074929A1 (de) | Neue polycyclische Polyazaheterocyclen, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate | |
| CH630903A5 (en) | Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline. | |
| DE1076691B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| DE19526233B4 (de) | Hydroxylierte Azabicyclooctyl-tetra- und -hexahydrobenz[d,e]isochinolone, deren Herstellung und pharmazeutische Zusammensetzungen, die diese enthalten | |
| EP0086980B1 (de) | Substituierte Dibenzodiazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| CH667270A5 (en) | New diazepino-indole derivs. - useful as antidepressant, anti-aggressive, anxiolytic and neuroleptic agents | |
| EP0014996B1 (de) | Heterocyclische spiroverknüpfte Amidine, ihre Stereoisomeren und optischen Isomeren, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| AT346346B (de) | Verfahren zur herstellung von neuen derivaten des 5h-dibenz(b,f)azepins | |
| 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 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| REN | Ceased due to non-payment of the annual fee |