CH501664A - Verfahren zur Herstellung von neuen Thiepinderivaten - Google Patents

Verfahren zur Herstellung von neuen Thiepinderivaten

Info

Publication number: CH501664A
Authority: CH; Switzerland
Prior art keywords: acid; thiepin; methoxy; dibenzo; dihydro
Prior art date: 1968-12-04

Application number

CH1599070A

Other languages

German (de)

English (en)

Inventor

Walter Dr Schindler

Erich Dr Schmid

Armin Dr Zuest

Original Assignee

Ciba Geigy Ag

Priority date (The priority date 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 date listed.)

1968-12-04

Filing date

1968-12-04

Publication date

1971-01-15

1968-12-04 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1968-12-04 Priority to CH1599070A priority Critical patent/CH501664A/de

1968-12-04 Priority claimed from CH1808568A external-priority patent/CH501662A/de

1971-01-15 Publication of CH501664A publication Critical patent/CH501664A/de

Links

DMMJPKKGOIYKPV-UHFFFAOYSA-N 1-(thiepin-2-yl)piperazine Chemical compound N1(CCNCC1)C=1SC=CC=CC1 DMMJPKKGOIYKPV-UHFFFAOYSA-N 0.000 title abstract 2
239000003874 central nervous system depressant Substances 0.000 title abstract 2
150000003839 salts Chemical class 0.000 claims abstract description 14
150000003551 thiepines Chemical class 0.000 claims abstract description 5
150000001875 compounds Chemical class 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
150000007522 mineralic acids Chemical class 0.000 claims description 5
150000007524 organic acids Chemical class 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
238000006894 reductive elimination reaction Methods 0.000 claims description 4
235000005985 organic acids Nutrition 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
239000002253 acid Substances 0.000 abstract description 4
125000005002 aryl methyl group Chemical group 0.000 abstract description 4
125000005101 aryl methoxy carbonyl group Chemical group 0.000 abstract description 3
230000003474 anti-emetic effect Effects 0.000 abstract description 2
230000004899 motility Effects 0.000 abstract description 2
230000008092 positive effect Effects 0.000 abstract description 2
208000019901 Anxiety disease Diseases 0.000 abstract 1
238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
238000012345 traction test Methods 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 8
-1 benzyl ester Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical group C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 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
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-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
DBQYUWWOBWTUPV-UHFFFAOYSA-N 5,6-dihydrobenzo[b][1]benzothiepine Chemical compound C1CC2=CC=CC=C2SC2=CC=CC=C12 DBQYUWWOBWTUPV-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
235000011054 acetic acid Nutrition 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 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
238000006243 chemical reaction Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000013016 damping Methods 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
NWVNXDKZIQLBNM-UHFFFAOYSA-N diphenylmethylpiperazine Chemical compound C1CNCCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 NWVNXDKZIQLBNM-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/14—[b,f]-condensed

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1599070A 1968-12-04 1968-12-04 Verfahren zur Herstellung von neuen Thiepinderivaten CH501664A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1599070A CH501664A (de)	1968-12-04	1968-12-04	Verfahren zur Herstellung von neuen Thiepinderivaten

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH1599070A CH501664A (de)	1968-12-04	1968-12-04	Verfahren zur Herstellung von neuen Thiepinderivaten
CH1808568A CH501662A (de)	1968-02-21	1968-12-04	Verfahren zur Herstellung von neuen Thiepinderivaten

Publications (1)

Publication Number	Publication Date
CH501664A true CH501664A (de)	1971-01-15

Family

ID=4430328

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1599070A CH501664A (de)	1968-12-04	1968-12-04	Verfahren zur Herstellung von neuen Thiepinderivaten

Country Status (2)

Country	Link
CH (1)	CH501664A (es)
ES (1)	ES363848A1 (es)

1968
- 1968-12-04 CH CH1599070A patent/CH501664A/de not_active IP Right Cessation
1969
- 1969-02-20 ES ES363848A patent/ES363848A1/es not_active Expired

Also Published As

Publication number	Publication date
ES363848A1 (es)	1971-01-01

Legal Events

Date	Code	Title	Description
1975-07-15	PL	Patent ceased

Publication	Publication Date	Title
DE2540633C2 (es)	1989-01-19
DE1964761C3 (de)	1981-04-16	Fluorenon- und Fluorenverbindungen und Arzneimittel,welche diese enthalten
CH637956A5 (de)	1983-08-31	In 11-stellung substituierte 5,11-dihydro-6h-pyrido-(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel.
DE1908543A1 (de)	1971-06-24	Verfahren zur Herstellung von neuen Thiepinderivaten
DE2351281C3 (de)	1981-07-30	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung
DE1795176C3 (de)	1974-10-24	hT-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung
DE2707270A1 (de)	1978-08-24	Pyrazolo-diazepine und verfahren zu ihrer herstellung
CH501664A (de)	1971-01-15	Verfahren zur Herstellung von neuen Thiepinderivaten
AT284132B (de)	1970-09-10	Verfahren zur Herstellung von neuen Thiepinderivaten sowie ihrer Säureadditionssalze
DE1695070C3 (de)	1975-10-23	11.02.66 Schweiz 1973-66 Thiepinderivate, Verfahren zu ihrer Herstellung und pharmazeutische Präparate
DE2039722C3 (de)	1974-03-07	Neue Imidazolidinonderivate
DE1908543C (de)	1972-05-04	8-Substituierte lO-Piperazino-10,11dihydro-dibenzo eckige Klammer auf b,f eckige Klammer zu -thiepine
EP0152556A1 (de)	1985-08-28	Aminopropanolderivate von substituierten 2-Hydroxy-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel
AT284133B (de)	1970-09-10	Verfahren zur Herstellung eines neuen Thiepinderivates sowie seiner Säureadditionssalze
AT222120B (de)	1962-07-10	Verfahren zur Herstellung von neuen Tetrahydroisochinolin-Derivaten
DE1908543B (de)		8 Substituierte 10 Piperazmo 10,11 dihydro-dibenzo eckige Klammer auf b,f eckige Klammer zu thiepine
DE2022790C3 (de)	1977-07-07	10-Methyl-5-[ (4-Methylpiperazino)-acetyl J-5,10dihydro-llH-dibenzo [b,e ] [1,4 ] diazepin-11-on, ein Verfahren zu dessen Herstellung sowie dieses enthaltende Arzneimittel
AT217045B (de)	1961-09-11	Verfahren zur Herstellung von neuen monoalkylierten bzw. monohalogenierten N-Derivaten von 10,11-Dihydro-5H-dibenzo[b,f]azepinen und 5H-Dibenzo[b,f]azepinen
AT276381B (de)	1969-11-25	Verfahren zur Herstellung von neuen Phenylisoindolderivaten und deren Salzen
CH473146A (de)	1969-05-31	Verfahren zur Herstellung von neuen 4H-Benzo(4,5)cyclohepta(1,2-b)thiophen-Derivaten
DE1250449B (de)	1967-09-21	Verfahren zur Herstellung von 9, 10-Dihydro-4H-benzo[4, 5]cyclohepta-[1, 2-b]thiophenen
CH542863A (de)	1973-10-15	Verfahren zur Herstellung von neuen Imidazolidinonderivaten
DE1214244B (de)	1966-04-14	Verfahren zur Herstellung von gegebenenfalls in 2- und/oder 9-Stellung substituierten 11-(3-Di-methylaminopropyl)-6, 11-dihydrodibenz(b, e) thiepinen
DE2521497A1 (de)	1975-11-27	Aldehydaddukte von 1,4-benzodiazepin-4-oxiden, azeto- eckige klammer auf 1,4 eckige klammer zu -benzodiazepine, verfahren zur herstellung dieser verbindungen sowie diese verbindungen als wirkstoffe enthaltende arzneimittel
CH611617A5 (en)	1979-06-15	Process for the preparation of a novel piperidine derivative