CH643263A5 - Benzodiazepine, ihre herstellung und verwendung. - Google Patents
Benzodiazepine, ihre herstellung und verwendung. Download PDFInfo
- Publication number
- CH643263A5 CH643263A5 CH441879A CH441879A CH643263A5 CH 643263 A5 CH643263 A5 CH 643263A5 CH 441879 A CH441879 A CH 441879A CH 441879 A CH441879 A CH 441879A CH 643263 A5 CH643263 A5 CH 643263A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- carbon atoms
- alkyl
- hydrogen
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title 1
- 229940049706 benzodiazepine Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 8
- 150000002367 halogens Chemical class 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- -1 4-methylpiperazinyl Chemical group 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- WSNPRYLYXKGBEF-UHFFFAOYSA-N 6,11-dihydropyrazino[2,3-b][1,5]benzodiazepin-5-one Chemical compound O=C1NC2=CC=CC=C2NC2=NC=CN=C12 WSNPRYLYXKGBEF-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- CMITUAXQMWSHLL-UHFFFAOYSA-N methyl 3-bromopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1Br CMITUAXQMWSHLL-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 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
- 239000008298 dragée Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- JOSFXAFPJCYBAL-UHFFFAOYSA-N methyl 3-(4-chloro-2-nitroanilino)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1NC1=CC=C(Cl)C=C1[N+]([O-])=O JOSFXAFPJCYBAL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 230000002618 waking effect Effects 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH441879A CH643263A5 (de) | 1979-05-11 | 1979-05-11 | Benzodiazepine, ihre herstellung und verwendung. |
| US06/143,263 US4337198A (en) | 1979-05-11 | 1980-04-24 | Pyrazinobenzodiazepines |
| PH23968A PH15678A (en) | 1979-05-11 | 1980-04-29 | Improvements in or relating to pyrazinobenzodiazepines |
| DE19803016647 DE3016647A1 (de) | 1979-05-11 | 1980-04-30 | Pyrazinobenzodiazepine, ihre herstellung und verwendung |
| BE1/9805A BE883080A (fr) | 1979-05-11 | 1980-05-02 | Nouvelles pyrazinobenzodiazepines, leur preparation et leur application comme medicaments |
| GB8014843A GB2053197B (en) | 1979-05-11 | 1980-05-02 | Pyrazinobenzodiazepines |
| FI801444A FI66869C (fi) | 1979-05-11 | 1980-05-05 | Foerfarande foer framstaellning av terapeutiskt verksamma 11-(1-piperazinyl-pyrazino(2,3-b)(1,5)bensodiazepiner |
| NL8002610A NL8002610A (nl) | 1979-05-11 | 1980-05-07 | Heterocyclische verbindingen en werkwijzen voor het bereiden en toepassen van deze verbindingen. |
| IT8048615A IT8048615A0 (it) | 1979-05-11 | 1980-05-07 | Pirazinobenzodiazepine loro preparazione e loro impiego come medicamenti |
| SE8003485A SE433746B (sv) | 1979-05-11 | 1980-05-08 | Pyrazino(2,3-b)(1,5)bensodiazepiner, deras framstellning och anvendning |
| YU01238/80A YU123880A (en) | 1979-05-11 | 1980-05-09 | Process for preparing pyrazinobenzoidiazepines |
| AT0246780A ATA246780A (de) | 1979-05-11 | 1980-05-09 | Verfahren zur herstellung neuer pyrazinobenzodiazepine |
| JP6079680A JPS55151585A (en) | 1979-05-11 | 1980-05-09 | Pyradinobenzodiazepines |
| ZA00802800A ZA802800B (en) | 1979-05-11 | 1980-05-09 | Pyrazinobenzodiazepines |
| NZ193675A NZ193675A (en) | 1979-05-11 | 1980-05-09 | 11-(piperazin-1-yl)pyrazino(2,3-6)benzo(1,5)diazepines |
| PT71209A PT71209B (fr) | 1979-05-11 | 1980-05-09 | Procede pour la preparation de nouveaux composes organiques |
| IE968/80A IE49795B1 (en) | 1979-05-11 | 1980-05-09 | Improvements in or relating to pyrazinobenzodiazepines |
| IL60037A IL60037A (en) | 1979-05-11 | 1980-05-09 | Pyrazinobenzodiazepines,their production and pharmaceutical compositions containing them |
| CA000351559A CA1140546A (en) | 1979-05-11 | 1980-05-09 | Pyrazinobenzodiazepines |
| ES491370A ES491370A0 (es) | 1979-05-11 | 1980-05-09 | Un procedimiento para la preparacion de piridizinobenzodiazepinas |
| DK205580A DK205580A (da) | 1979-05-11 | 1980-05-09 | Fremgangsmaade til fremstilling af benzodiazepinderivater |
| FR8010402A FR2456104A1 (fr) | 1979-05-11 | 1980-05-09 | Nouvelles pyrazinobenzodiazepines, leur preparation et leur application comme medicaments |
| AU58288/80A AU539187B2 (en) | 1979-05-11 | 1980-05-09 | Pyrazinobenzodiazepines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH441879A CH643263A5 (de) | 1979-05-11 | 1979-05-11 | Benzodiazepine, ihre herstellung und verwendung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643263A5 true CH643263A5 (de) | 1984-05-30 |
Family
ID=4275759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH441879A CH643263A5 (de) | 1979-05-11 | 1979-05-11 | Benzodiazepine, ihre herstellung und verwendung. |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4337198A (enExample) |
| JP (1) | JPS55151585A (enExample) |
| AT (1) | ATA246780A (enExample) |
| AU (1) | AU539187B2 (enExample) |
| BE (1) | BE883080A (enExample) |
| CA (1) | CA1140546A (enExample) |
| CH (1) | CH643263A5 (enExample) |
| DE (1) | DE3016647A1 (enExample) |
| DK (1) | DK205580A (enExample) |
| ES (1) | ES491370A0 (enExample) |
| FI (1) | FI66869C (enExample) |
| FR (1) | FR2456104A1 (enExample) |
| GB (1) | GB2053197B (enExample) |
| IE (1) | IE49795B1 (enExample) |
| IL (1) | IL60037A (enExample) |
| IT (1) | IT8048615A0 (enExample) |
| NL (1) | NL8002610A (enExample) |
| NZ (1) | NZ193675A (enExample) |
| PH (1) | PH15678A (enExample) |
| PT (1) | PT71209B (enExample) |
| SE (1) | SE433746B (enExample) |
| YU (1) | YU123880A (enExample) |
| ZA (1) | ZA802800B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4404137A (en) * | 1979-10-16 | 1983-09-13 | Lilly Industries Limited | Pyrazolo [3,4-b][1,5]benzodiazepine compounds |
| US4431589A (en) * | 1980-12-11 | 1984-02-14 | Lilly House | Benzodiazepine compounds and their use as pharmaceuticals |
| US4460508A (en) * | 1981-12-07 | 1984-07-17 | Ciba-Geigy Corporation | 5-Diazacycloalkylimidazo[1,2-c][1,3]benzodiazepines |
| US4507311A (en) * | 1981-12-07 | 1985-03-26 | Ciba-Geigy Corporation | Imidazo[1,2-c][1,3]benzodiazepines |
| US4460587A (en) * | 1981-12-07 | 1984-07-17 | Ciba-Geigy Corporation | 5-Diazacycloalkyl imidazo[1,2-c][1,3]benzodiazepines |
| US4459232A (en) * | 1981-12-07 | 1984-07-10 | Ciba-Geigy Corporation | Imidazo[1,2-c][1,3]benzodiazepines |
| US4469868A (en) * | 1982-05-24 | 1984-09-04 | Warner-Lambert Company | Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines |
| DE3643666A1 (de) * | 1986-12-20 | 1988-06-30 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| BE1004596A4 (fr) * | 1990-09-26 | 1992-12-22 | Therabel Res S A N V | Derives de methylpiperazinoazepine, leur preparation et leur utilisation. |
| US5393752A (en) * | 1992-05-26 | 1995-02-28 | Therabel Research S.A./N.V. | Methylpiperazinoazepine compounds, preparation and use thereof |
| US5637584A (en) * | 1995-03-24 | 1997-06-10 | Eli Lilly And Company | Solvate of olanzapine |
| US5631250A (en) * | 1995-03-24 | 1997-05-20 | Eli Lilly And Company | Process and solvate of 2-methyl-thieno-benzodiazepine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458516A (en) * | 1968-02-16 | 1969-07-29 | American Cyanamid Co | 11-(piperazinyl)dibenz(b,f)(1,4)oxazepines and analogous thiazepines |
| AT327200B (de) * | 1972-09-06 | 1976-01-26 | Degussa | Verfahren zur herstellung von neuen aza-10,11-dihydro-5h-dibenzo (b,e)-(1,4) diazepinen sowie deren salzen |
-
1979
- 1979-05-11 CH CH441879A patent/CH643263A5/de not_active IP Right Cessation
-
1980
- 1980-04-24 US US06/143,263 patent/US4337198A/en not_active Expired - Lifetime
- 1980-04-29 PH PH23968A patent/PH15678A/en unknown
- 1980-04-30 DE DE19803016647 patent/DE3016647A1/de not_active Withdrawn
- 1980-05-02 BE BE1/9805A patent/BE883080A/fr not_active IP Right Cessation
- 1980-05-02 GB GB8014843A patent/GB2053197B/en not_active Expired
- 1980-05-05 FI FI801444A patent/FI66869C/fi not_active IP Right Cessation
- 1980-05-07 IT IT8048615A patent/IT8048615A0/it unknown
- 1980-05-07 NL NL8002610A patent/NL8002610A/nl not_active Application Discontinuation
- 1980-05-08 SE SE8003485A patent/SE433746B/sv unknown
- 1980-05-09 NZ NZ193675A patent/NZ193675A/en unknown
- 1980-05-09 JP JP6079680A patent/JPS55151585A/ja active Pending
- 1980-05-09 CA CA000351559A patent/CA1140546A/en not_active Expired
- 1980-05-09 DK DK205580A patent/DK205580A/da not_active Application Discontinuation
- 1980-05-09 IL IL60037A patent/IL60037A/xx unknown
- 1980-05-09 IE IE968/80A patent/IE49795B1/en unknown
- 1980-05-09 FR FR8010402A patent/FR2456104A1/fr active Granted
- 1980-05-09 ES ES491370A patent/ES491370A0/es active Granted
- 1980-05-09 ZA ZA00802800A patent/ZA802800B/xx unknown
- 1980-05-09 YU YU01238/80A patent/YU123880A/xx unknown
- 1980-05-09 PT PT71209A patent/PT71209B/pt unknown
- 1980-05-09 AT AT0246780A patent/ATA246780A/de not_active Application Discontinuation
- 1980-05-09 AU AU58288/80A patent/AU539187B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| DK205580A (da) | 1980-11-12 |
| AU539187B2 (en) | 1984-09-13 |
| PT71209B (fr) | 1981-08-04 |
| DE3016647A1 (de) | 1980-11-20 |
| US4337198A (en) | 1982-06-29 |
| PH15678A (en) | 1983-03-11 |
| NZ193675A (en) | 1984-05-31 |
| IE800968L (en) | 1980-11-11 |
| IE49795B1 (en) | 1985-12-11 |
| AU5828880A (en) | 1980-11-13 |
| YU123880A (en) | 1983-02-28 |
| PT71209A (fr) | 1980-06-01 |
| GB2053197B (en) | 1983-02-23 |
| IL60037A0 (en) | 1980-07-31 |
| IT8048615A0 (it) | 1980-05-07 |
| IL60037A (en) | 1983-05-15 |
| BE883080A (fr) | 1980-11-03 |
| SE8003485L (sv) | 1980-11-12 |
| ATA246780A (de) | 1987-05-15 |
| FR2456104A1 (fr) | 1980-12-05 |
| FI801444A7 (fi) | 1980-11-12 |
| FI66869C (fi) | 1984-12-10 |
| ZA802800B (en) | 1981-12-30 |
| ES8105730A1 (es) | 1981-05-16 |
| ES491370A0 (es) | 1981-05-16 |
| GB2053197A (en) | 1981-02-04 |
| JPS55151585A (en) | 1980-11-26 |
| FI66869B (fi) | 1984-08-31 |
| SE433746B (sv) | 1984-06-12 |
| NL8002610A (nl) | 1980-11-13 |
| CA1140546A (en) | 1983-02-01 |
| FR2456104B1 (enExample) | 1983-06-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69518373T2 (de) | Neue Zusammensetzungen, die Sertralin und einem 5-HT1D-Rezeptoragonisten oder Antagonisten enthalten | |
| DE3527117C2 (de) | 1-(Aminophenyl)-4-(methyl)-5H-2,3-benzodiazepinderivate, Verfahren zur Herstellung derselben und diese enthaltende Arzneimittel | |
| DE2915318A1 (de) | Cycloalkyltriazole, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| EP0148440B1 (de) | 1,3,4,5-Tetrahydrobenz[c,d]indole, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2756113A1 (de) | Neue 4-hydroxy-2h-1,2-benzothiazin- 3-carboxamid-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE3342164A1 (de) | Antipsychotisch wirkende benzoxazine, verfahren zu deren herstellung sowie pharmazeutische zubereitungen, die diese enthalten | |
| CH643263A5 (de) | Benzodiazepine, ihre herstellung und verwendung. | |
| EP0163260A1 (de) | Neue substituierte Pyrrolidinone, Verfahren zu ihrer Herstellung und Arzneimittel | |
| CH646696A5 (de) | Dibenzazepine, ihre herstellung und verwendung. | |
| DE3309596A1 (de) | 2-substituierte 1-(3'-aminoalkyl)-1,2,3,4-tetrahydro-ss-carboline, ihre herstellung und verwendung als arzneimittel | |
| DE3500251C2 (de) | Neue 8alpha-Acylaminoergoline | |
| DE3439450A1 (de) | 1,2,4-triazolo-carbamate und ihre saeureadditionssalze, verfahren zu ihrer herstellung und arzneimittel | |
| CH649553A5 (de) | Azepinoindole und verfahren zu deren herstellung. | |
| WO1983004254A1 (fr) | Composes derives de la piperazine, procede de leur fabrication et medicaments les contenant | |
| DE68902490T2 (de) | Pharmazeutische zusammensetzung. | |
| DE2051962A1 (de) | Benzimidazo eckige Klammer auf l,2d eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin 6 (5H) one und Verfahren zu deren Her stellung | |
| DE2258318A1 (de) | Neue organische verbindungen und verfahren zu deren herstellung | |
| DE2229845B2 (de) | 6-o-Halogenphenyl-4H-s-triazolo [3,4-c] thieno [2,3e] [1,4] diazepine, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Massen | |
| DE3503074A1 (de) | Hydantoinderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten | |
| DE2854727A1 (de) | Polyfluorhydroxyisopropyl-substituierte bicyclische und tricyclische carbostyrile, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| EP0273239A1 (de) | Neue kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0138034B1 (de) | Substituierte Pyrido(1,2-c)imidazo((1,2-a)benzimidazole, Verfahren zu ihrer Herstellung, ihre Verwendung sowie pharmazeutische Präparate auf Basis dieser Verbindungen | |
| DE2519077C3 (de) | 3-Amino-4,5,6,7-tetrahydroindazole, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen | |
| DE2820718A1 (de) | Neue 5-phenyl-1h-3-benzazepine, ihre herstellung und verwendung | |
| CH579565A5 (en) | Imidazolin-2-ylamino-2,1,3-benzothiadiazoles prodn. - by cyclising corresp. beta aminoethyl (thio) ureas, active against muscle tremors and rigor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |