CH646696A5 - Dibenzazepine, ihre herstellung und verwendung. - Google Patents
Dibenzazepine, ihre herstellung und verwendung. Download PDFInfo
- Publication number
- CH646696A5 CH646696A5 CH882980A CH882980A CH646696A5 CH 646696 A5 CH646696 A5 CH 646696A5 CH 882980 A CH882980 A CH 882980A CH 882980 A CH882980 A CH 882980A CH 646696 A5 CH646696 A5 CH 646696A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- alkyl
- above meaning
- administered
- Prior art date
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- LCGTWRLJTMHIQZ-UHFFFAOYSA-N 5H-dibenzo[b,f]azepine Chemical compound C1=CC2=CC=CC=C2NC2=CC=CC=C21 LCGTWRLJTMHIQZ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- -1 halogen formates Chemical class 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-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
- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MPZMVUQGXAOJIK-UHFFFAOYSA-N 4-bromopyridine;hydron;chloride Chemical compound Cl.BrC1=CC=NC=C1 MPZMVUQGXAOJIK-UHFFFAOYSA-N 0.000 description 1
- VSNARHBMLUEIRA-UHFFFAOYSA-N 8-chloro-6,11-dihydro-5h-benzo[c][1]benzazepine Chemical compound N1CC2=CC(Cl)=CC=C2CC2=CC=CC=C21 VSNARHBMLUEIRA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000009132 Catalepsy Diseases 0.000 description 1
- 206010015995 Eyelid ptosis Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010047853 Waxy flexibility Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 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
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- QAYPFHIZJSDUSF-UHFFFAOYSA-N azepin-3-one Chemical compound O=C1C=CC=CN=C1 QAYPFHIZJSDUSF-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 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
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013265 extended release Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000035873 hypermotility Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 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
- 239000011976 maleic acid Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000002618 waking effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/20—Dibenz [b, e] azepines; Hydrogenated dibenz [b, e] azepines
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH882980A CH646696A5 (de) | 1980-11-28 | 1980-11-28 | Dibenzazepine, ihre herstellung und verwendung. |
| DE19813145678 DE3145678A1 (de) | 1980-11-28 | 1981-11-19 | Dibenzazepine, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| US06/323,759 US4434171A (en) | 1980-11-28 | 1981-11-23 | Dibenzazepine derivatives, pharmaceutical compositions containing them, and pharmaceutical methods using them |
| GB8135381A GB2088373B (en) | 1980-11-28 | 1981-11-24 | Dibenzazepine derivatives and pharmaceutical compositions containing them |
| IT49760/81A IT1172093B (it) | 1980-11-28 | 1981-11-24 | Dibenzazepine loro preparazione e loro impiego come medicamenti |
| FR8122124A FR2495153A1 (fr) | 1980-11-28 | 1981-11-24 | Nouvelles dibenzazepines, leur preparation et leur application comme medicaments |
| JP56189374A JPS57120586A (en) | 1980-11-28 | 1981-11-27 | Dibenzazepine derivative, manufacture and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH882980A CH646696A5 (de) | 1980-11-28 | 1980-11-28 | Dibenzazepine, ihre herstellung und verwendung. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH646696A5 true CH646696A5 (de) | 1984-12-14 |
Family
ID=4345211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH882980A CH646696A5 (de) | 1980-11-28 | 1980-11-28 | Dibenzazepine, ihre herstellung und verwendung. |
Country Status (7)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5502047A (en) * | 1993-03-22 | 1996-03-26 | Kavey; Neil B. | Treatment for insomnia |
| US5354747A (en) * | 1993-06-16 | 1994-10-11 | G. D. Searle & Co. | 2-, 3-, 4-, 5-, 6-, 7-, 8-, 9- and/or 10-substituted dibenzoxazepine and dibenzthiazepine compounds, pharmaceutical compositions and methods of use |
| US5461047A (en) * | 1993-06-16 | 1995-10-24 | G. D. Searle & Co. | 2-,3-,4-,5-,6-,7-,8-,9- and/or 10-substituted dibenzoxazepine and dibenzthiazepine compounds, pharmaceutical compositions and methods of use |
| US20100179215A1 (en) | 2006-05-19 | 2010-07-15 | Somaxon Pharmaceuticals, Inc. | Doxepin isomers and isomeric mixtures and methods of using the same to treat sleep disorders |
| US20100227916A1 (en) * | 2006-05-19 | 2010-09-09 | Somaxon Pharmaceuticals, Inc | N-desmethyl-doxepin and methods of using the same to treat sleep disorders |
| JP2009537553A (ja) | 2006-05-19 | 2009-10-29 | ソマクソン ファーマシューティカルズ インコーポレイテッド | 睡眠改善のための低用量ドキセピンの使用法 |
| US20090042972A1 (en) * | 2006-05-19 | 2009-02-12 | Somaxon Pharmaceuticals, Inc. | Methods of using low-dose doxepin for the improvement of sleep |
| US20090042971A1 (en) * | 2006-05-19 | 2009-02-12 | Somaxon Pharmaceuticals, Inc. | Method of using low-dose doxepin for the improvement of sleep |
| US20100179214A1 (en) * | 2006-05-19 | 2010-07-15 | Somaxon Pharmaceuticals, Inc. | Doxepin trans isomers and isomeric mixtures and methods of using the same to treat sleep disorders |
| US20080058408A1 (en) * | 2006-05-19 | 2008-03-06 | Rogowski Roberta L | Low-dose doxepin for treatment of sleep disorders in elderly patients |
| US7915307B2 (en) * | 2006-07-20 | 2011-03-29 | Somaxon Pharmaceuticals, Inc. | Methods of improving the pharmacokinetics of doxepin |
| US20080182890A1 (en) * | 2006-10-04 | 2008-07-31 | Somaxon Pharmaceuticals, Inc. | Methods of using low-dose doxepin for the improvement of sleep |
| US20100105614A1 (en) | 2006-10-25 | 2010-04-29 | Somaxon Pharmaceuticals, Inc. | Ultra low dose doxepin and methods of using the same to treat sleep disorders |
| WO2008070795A2 (en) | 2006-12-06 | 2008-06-12 | Somaxon Pharmaceuticals, Inc. | Combination therapy using low-dose doxepin for the improvement of sleep |
| EP2148659A2 (en) | 2007-04-13 | 2010-02-03 | Somaxon Pharmaceuticals, Inc. | Low-dose doxepin formulations |
| WO2021195362A1 (en) | 2020-03-26 | 2021-09-30 | Seagen Inc. | Methods of treating multiple myeloma |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3153652A (en) | 1964-10-20 | Certificate of correction | ||
| US2802007A (en) | 1954-05-24 | 1957-08-06 | Lakeside Lab Inc | Method of reducing 3-hydroxypyridine and its derivatives |
| DE1136706B (de) | 1958-05-30 | 1962-09-20 | Cilag Chemie | Verfahren zur Herstellung von basisch substituierten, schwefelhaltigen 1-Aza-[2, 3:5, 6]-dibenzocycloheptadien-derivaten und deren Salzen |
| US3038896A (en) | 1958-05-30 | 1962-06-12 | Cilag Chemie | 1-(di-lower alkyl amino lower alkyl thio lower alkyl)-aza-[2, 3:5, 6]-dibenzocycloheptadiene compounds |
| US3079394A (en) | 1960-02-10 | 1963-02-26 | Pittsburgh Plate Glass Co | Novel chemical compound |
| GB1057145A (en) | 1963-08-16 | 1967-02-01 | Bellon Labor Sa Roger | Phenylcyclohexylacetonitrile derivatives |
| US3928356A (en) | 1967-10-06 | 1975-12-23 | Fujisawa Pharmaceutical Co | 10-{8 4-({107 -Hydroxy alkyl)-1-piperazimyl{9 -dibenzo (h,f) oxofins and thiepins and acetyl esters thereof |
| SE342045B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1967-12-27 | 1972-01-24 | Yoshitomi Pharmaceutical | |
| FR96408E (fr) | 1968-10-08 | 1972-06-30 | Saint Marcel Mfg | Procédé de fabrication de chaussures ou éléments de chaussures constitués en tout ou partie par une matiere synthétique. |
| US3894001A (en) | 1969-08-07 | 1975-07-08 | Colgate Palmolive Co | 11-Aminoalkyl- and 11-cyclicaminomorphanthridines |
| AR206937A1 (es) | 1974-09-06 | 1976-08-31 | Lilly Co Eli | Procedimiento para preparar compuestos de 1-sustituido-4-alquil-4-fenil-piperidina |
| US4045445A (en) | 1975-12-14 | 1977-08-30 | American Cyanamid Company | 11-(4-Piperidyl)dibenzo-diazepines |
| US4221715A (en) | 1979-08-03 | 1980-09-09 | American Cyanamid Company | Substituted dibenz[b,f][1,4]oxazepin-11-yl pyridinium salts and derivatives thereof |
| EP0026469B1 (en) | 1979-10-01 | 1984-11-28 | Sandoz Ag | Dibenzazepine derivatives, their production and pharmaceutical compositions containing them |
-
1980
- 1980-11-28 CH CH882980A patent/CH646696A5/de not_active IP Right Cessation
-
1981
- 1981-11-19 DE DE19813145678 patent/DE3145678A1/de not_active Withdrawn
- 1981-11-23 US US06/323,759 patent/US4434171A/en not_active Expired - Fee Related
- 1981-11-24 IT IT49760/81A patent/IT1172093B/it active
- 1981-11-24 FR FR8122124A patent/FR2495153A1/fr active Granted
- 1981-11-24 GB GB8135381A patent/GB2088373B/en not_active Expired
- 1981-11-27 JP JP56189374A patent/JPS57120586A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2495153A1 (fr) | 1982-06-04 |
| DE3145678A1 (de) | 1982-07-08 |
| JPS57120586A (en) | 1982-07-27 |
| GB2088373B (en) | 1984-09-19 |
| IT1172093B (it) | 1987-06-18 |
| GB2088373A (en) | 1982-06-09 |
| US4434171A (en) | 1984-02-28 |
| FR2495153B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-01-11 |
| IT8149760A0 (it) | 1981-11-24 |
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