CS235173B1 - Ester of aminoalcohol of dibenzo-(b,e)-thiepin series - Google Patents
Ester of aminoalcohol of dibenzo-(b,e)-thiepin series Download PDFInfo
- Publication number
- CS235173B1 CS235173B1 CS781483A CS781483A CS235173B1 CS 235173 B1 CS235173 B1 CS 235173B1 CS 781483 A CS781483 A CS 781483A CS 781483 A CS781483 A CS 781483A CS 235173 B1 CS235173 B1 CS 235173B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- mixture
- chloro
- thiepine
- ether
- piperidylidene
- Prior art date
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- 150000002148 esters Chemical class 0.000 title claims description 3
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 title claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- -1 1-methyl-4-piperidylidene Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 8
- BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 claims 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 3
- 235000019341 magnesium sulphate Nutrition 0.000 claims 3
- 239000003208 petroleum Substances 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- 238000010828 elution Methods 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 150000001414 amino alcohols Chemical class 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002903 catalepsic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- VIQCGTZFEYDQMR-UHFFFAOYSA-N fluphenazine decanoate Chemical compound C1CN(CCOC(=O)CCCCCCCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 VIQCGTZFEYDQMR-UHFFFAOYSA-N 0.000 description 2
- 229960001374 fluphenazine decanoate Drugs 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
- 229960004046 apomorphine Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960000762 perphenazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003551 thiepines Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
233173 3 4233173 3 4
Vynález se týká esteru aminoalkoholu di-benzo(b,e)thiepinové řady vzorce I,BACKGROUND OF THE INVENTION The present invention relates to an aminoalcohol of the di-benzo (b, e) thiepine series of formula I,
CH^CH^OCO (CH^CH^ (I) t j. 2-chlor-ll- [ 1- (2-dekanoyloxyethyl] -4-pi-perldyliden] -6,11-dihydrodibenzo (b,e ] -thiepinu. Látka podle vynálezu vzorce I připomínásivou strukturou depotní neuroleptika (na-příklad flufenazindekanoát). Překvapivěvšak vůbec nevykazuje vlastnosti depotníhoneuroleptika, ale spíše vlastnosti mírně aprotrahovaně působícího dopamlnomimetika.Jako taková přichází v úvahu k praktickémupoužití například v terapii parkinsonismu.Vlastnosti látky byly ověřeny v testech nazvířatech a v bioehemicko-farmakologickýchtestech; látka vzorce I byla aplikována in-tramuskulárně ve formě 5% roztoku v Mig-lyolu (rafinovaná směs triglyceridů rostlin-ných mastných kyselin Cs až C12). V dávce25 mg/kg nevykazuje antiapomorfinové pů-sobení u krys (vůči stereotypům ani agita-ci], zatímco flufenazindekanoát v téže jed-norázové dávce významně tlumí oba para-metry po dobu 2 týdnů. V dávce 5 mg/kglátka vzorce I u psů neflumí apomorfinemindukovanou emesi; naopak v době 1 až 2týdnů po podání signifikantně potencujeemetický účinek apomorfinu (maximum vprvním týdnu po podání, kdy byl počet eme-tických záchvatů zvýšen 2,7krát). V dávce25 mg/kg nevykazuje kataleptické působeníu krys; naopak v interakci s perfenazinem(4,5 mg/kg i. p.) oslabuje jeho kataleptickouaktivitu o 20 %. V dávce 50 mg/kg snižujehladinu kyseliny homovanilové (HVA) vestriatu krysího: mozku; účinek je protraho-vaný, protože za 2 dny po podání je pokleshladiny HVA maximální (o 69 %), avšakještě za 5 dní činí 58 °/o. Látka vzorce I se připravuje esterifikacíamlnoalkoholu vzorce II,CH 2 CH 2 OCO (CH 2 CH 2 (I) t) 2-chloro-11- [1- (2-decanoyloxyethyl) -4-piperidylidene] -6,11-dihydrodibenzo (b, e] thiepine) The substance of the invention of formula (I) is reminiscent of the depot neuroleptic structure (for example, flufenazinedecanoate), but surprisingly, it does not exhibit the properties of depothonuroleptics, but rather the properties of a moderately protracted dopamnomimetic.As such as practical use in parkinsonism for example. and in bio-chemical-pharmacological tests, the compound of formula I was administered intramuscularly in the form of a 5% solution in Mig-lyol (refined mixture of triglycerides of vegetable fatty acids C5 to C12), and did not exhibit antiapomorphic activity in rats at 25 mg / kg ( against stereotypes or agitation, while flufenazinedecanoate significantly attenuates both parameters for 2 weeks in the same single dose, at 5 mg / kg of Formula I in dogs on the contrary, in the period of 1-2 weeks after administration, the potentemic effect of apomorphine (maximum in the first week after administration, when the number of emetic seizures was increased by 2.7-fold) was significantly potentiated. It does not show cataleptic action at 25 mg / kg; conversely, its interaction with perphenazine (4.5 mg / kg i.p.) weakens its cataleptic activity by 20%. At a dose of 50 mg / kg, the homovanilic acid (HVA) level of the rat vestibrium decreases; the effect is ruptured because, at 2 days after administration, the decrease in HVA level is maximal (by 69%), but still at 58% in 5 days. The compound of formula I is prepared by esterification of an amino alcohol of formula II,
(II) přičemž lze použít všech obvyklých metod,tj. zejména reakce aminoalkoholu II s ky-selinou děkanovou ve vroucím toluenu ne-bo xylenu za kontinuálního oddestilováváníazeotropické směsi vody s příslušným roz-pouštědlem (za katalýzy malým množstvímkyseliny sírové nebo- bez této katalýzy], re-akce aminoalkoholu II s dekanoylchloridemnebo- reesterifikace nižších alkylesterů ky-seliny děkanové pomocí aminoalkoholu II.V dále uvedených příkladech je popsánapříprava esteru vzorce I reakcí aminoalko-holu II s dekanoylchloridem (Η. E. Fierz--David a W. Kuster, Helv. Chim. Acta 22, 821939] ve směsi chloroformu a benzenu přiteplotě místnosti. Získaná surová báze vzor-ce I se přečistí chrom,atografií na oxidu hli-nitém. Jiný způsob rafinace spočívá v pře-vedení surové báze vzorce i na hydrochlo-rid, který se vyčistí krystalizací a zředěnýmvodným amoniakem nebo alkalickým hydro-xidem se uvolní čistá báze. Výchozí amino-alkohol vzorce II je látkou novou a jeho pří-prava je popsána v příkladu. Identita koneč-ného produktu vzorce I, jakož i nových me-ziproduktů, byla zajištěna pomocí analýz aspekter. Dále uvedené příklady představujíilustraci možností vynálezu, avšak není je-jich účelem všechny tyto- možnosti vyčerpá-vajícím způsobem popisovat. Příklad 1 K suspenzi 11,8 g hydrochlorídu 2-chlor--11-(1- (2-hydroxyethyl ] -4-piperidyliden ] --6,11-dihydrodibenzo (b,e]thiepinu ve 100 mlvody se přidá slabý přebytek vodného amo-niaku a uvolněná báze se izoluje extrakcíbenzenem, extrakt se vysuší a, odpaří. Zby-tek se rozpustí ve směsi 20 ml chloroformu(II) wherein all conventional methods can be used, ie. in particular the reaction of amino alcohol II with decanoic acid in boiling toluene or xylene under continuous distillation of the azeotropic water mixture with the appropriate solvent (catalysed by a small amount of sulfuric acid or without such catalysis), re-action of amino alcohol II with decanoyl chloride or esterification of lower alkyl esters The following examples describe the preparation of an ester of formula I by reacting aminoalcohol II with decanoyl chloride (E. Fierz - David and W. Kuster, Helv. Chim. Acta 22, 821939) in a chloroform mixture. The crude base of formula I obtained is purified by chromium, by chromatography on aluminum oxide, and another method of refining consists in transferring the crude base of formula I to hydrochloride, which is purified by crystallization and dilute aqueous ammonia or alkali hydrocarbon. The starting amino alcohol of formula (II) is new and its additive The identity of the final product of formula (I) as well as of the new intermediates was ensured by means of aspect analyzes. The following examples illustrate the possibilities of the invention, but are not intended to describe all these possibilities exhaustively. Example 1 A slight excess of aqueous is added to a suspension of 11.8 g of 2-chloro-11- (1- (2-hydroxyethyl) -4-piperidylidene) - 6,11-dihydrodibenzo (b, e] thiepine) hydrochloride in 100 ml of water. the ammonium nitrate and the liberated base is isolated by extraction with benzene, the extract is dried and evaporated, the residue is dissolved in a mixture of 20 ml of chloroform.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CS781483A CS235173B1 (en) | 1983-10-24 | 1983-10-24 | Ester of aminoalcohol of dibenzo-(b,e)-thiepin series |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS781483A CS235173B1 (en) | 1983-10-24 | 1983-10-24 | Ester of aminoalcohol of dibenzo-(b,e)-thiepin series |
Publications (1)
Publication Number | Publication Date |
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CS235173B1 true CS235173B1 (en) | 1985-05-15 |
Family
ID=5427964
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CS781483A CS235173B1 (en) | 1983-10-24 | 1983-10-24 | Ester of aminoalcohol of dibenzo-(b,e)-thiepin series |
Country Status (1)
Country | Link |
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CS (1) | CS235173B1 (en) |
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1983
- 1983-10-24 CS CS781483A patent/CS235173B1/en unknown
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