DE3016647A1 - Pyrazinobenzodiazepine, ihre herstellung und verwendung - Google Patents
Pyrazinobenzodiazepine, ihre herstellung und verwendungInfo
- Publication number
- DE3016647A1 DE3016647A1 DE19803016647 DE3016647A DE3016647A1 DE 3016647 A1 DE3016647 A1 DE 3016647A1 DE 19803016647 DE19803016647 DE 19803016647 DE 3016647 A DE3016647 A DE 3016647A DE 3016647 A1 DE3016647 A1 DE 3016647A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- hydrogen
- formula
- alkyl
- compounds
- 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.)
- Withdrawn
Links
- VKOLNWDZIIKVOE-UHFFFAOYSA-N 1h-pyrazino[2,3-i][1,2]benzodiazepine Chemical compound N1N=CC=CC2=CC=C(N=CC=N3)C3=C12 VKOLNWDZIIKVOE-UHFFFAOYSA-N 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 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
- 229940126601 medicinal product Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-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
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
- WNQYIRLZXQESIK-UHFFFAOYSA-N 8-chloro-11-methyl-6h-pyrazino[2,3-b][1,5]benzodiazepin-5-one Chemical compound N1C(=O)C2=NC=CN=C2N(C)C2=CC=C(Cl)C=C21 WNQYIRLZXQESIK-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- -1 hydroxy - Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 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
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 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
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 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
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012458 free base Substances 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
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- CMITUAXQMWSHLL-UHFFFAOYSA-N methyl 3-bromopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=CN=C1Br CMITUAXQMWSHLL-UHFFFAOYSA-N 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 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
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000007958 sleep Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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)
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 |
|---|---|
| DE3016647A1 true DE3016647A1 (de) | 1980-11-20 |
Family
ID=4275759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803016647 Withdrawn DE3016647A1 (de) | 1979-05-11 | 1980-04-30 | Pyrazinobenzodiazepine, 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273239A1 (de) * | 1986-12-20 | 1988-07-06 | Dr. Karl Thomae GmbH | Neue kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Families Citing this family (11)
| 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 |
| 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
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0273239A1 (de) * | 1986-12-20 | 1988-07-06 | Dr. Karl Thomae GmbH | Neue kondensierte Diazepinone, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Also Published As
| Publication number | Publication date |
|---|---|
| CH643263A5 (de) | 1984-05-30 |
| DK205580A (da) | 1980-11-12 |
| AU539187B2 (en) | 1984-09-13 |
| PT71209B (fr) | 1981-08-04 |
| 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 |
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