DD139851A5 - Verfahren zur herstellung von 3-di-n-propyl-acetoxy-benzodiazepin-2-onen - Google Patents

Verfahren zur herstellung von 3-di-n-propyl-acetoxy-benzodiazepin-2-onen Download PDF

Info

Publication number: DD139851A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; propyl; solvent; acetoxy; radical
Prior art date: 1977-12-14

Application number

DD78209726A

Other languages

German (de)

English (en)

Inventor

Ludwig Schlager

Original Assignee

Gerot Pharmazeutika

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.)

1977-12-14

Filing date

1978-12-13

Publication date

1980-01-23

1977-12-14 Priority claimed from AT893877A external-priority patent/AT359509B/de

1978-11-21 Priority claimed from AT831278A external-priority patent/AT358051B/de

1978-12-13 Application filed by Gerot Pharmazeutika filed Critical Gerot Pharmazeutika

1980-01-23 Publication of DD139851A5 publication Critical patent/DD139851A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
238000000034 method Methods 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 14
125000001309 chloro group Chemical group Cl* 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
239000000203 mixture Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
150000003512 tertiary amines Chemical class 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
229940049706 benzodiazepine Drugs 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
150000008064 anhydrides Chemical class 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
MGYAGUUKOYNYAT-UHFFFAOYSA-N 2-(oxan-2-yl)oxane Chemical compound O1CCCCC1C1OCCCC1 MGYAGUUKOYNYAT-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
150000002500 ions Chemical class 0.000 claims 1
239000000463 material Substances 0.000 claims 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
NIJJYAXOARWZEE-UHFFFAOYSA-N Valproic acid Chemical compound CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
150000002148 esters Chemical class 0.000 description 6
229960000604 valproic acid Drugs 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
239000000155 melt Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
-1 Chloro-O-dipropylacetoxyfluor Chemical compound 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000001773 anti-convulsant effect Effects 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
VPVLRXXFPPNURM-UHFFFAOYSA-N 2-propylpentanoic acid;hydrochloride Chemical compound Cl.CCCC(C(O)=O)CCC VPVLRXXFPPNURM-UHFFFAOYSA-N 0.000 description 2
GYIUDLLQLVWKPP-UHFFFAOYSA-N 2-propylpentanoyl 2-propylpentanoate Chemical compound CCCC(CCC)C(=O)OC(=O)C(CCC)CCC GYIUDLLQLVWKPP-UHFFFAOYSA-N 0.000 description 2
PITHYUDHKJKJNQ-UHFFFAOYSA-N 2-propylpentanoyl chloride Chemical compound CCCC(C(Cl)=O)CCC PITHYUDHKJKJNQ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
206010022998 Irritability Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
238000006972 Polonovski rearrangement reaction Methods 0.000 description 2
SEQDDYPDSLOBDC-UHFFFAOYSA-N Temazepam Chemical compound N=1C(O)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 SEQDDYPDSLOBDC-UHFFFAOYSA-N 0.000 description 2
229960003965 antiepileptics Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000013078 crystal Substances 0.000 description 2
ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
229960004535 oxazepam Drugs 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
DIWRORZWFLOCLC-HNNXBMFYSA-N (3s)-7-chloro-5-(2-chlorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N([C@H](C(NC1=CC=C(Cl)C=C11)=O)O)=C1C1=CC=CC=C1Cl DIWRORZWFLOCLC-HNNXBMFYSA-N 0.000 description 1
RXLOMIUDGQAGNA-UHFFFAOYSA-N 1-(2-fluorophenyl)-3h-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1N1C(=O)CN=CC2=CC=CC=C21 RXLOMIUDGQAGNA-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
ZGTHEZQZYSLZDD-UHFFFAOYSA-N ClC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=C(C=CC=C2)F)C1 Chemical compound ClC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=C(C=CC=C2)F)C1 ZGTHEZQZYSLZDD-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
WTZPDTDVHCVLMK-UHFFFAOYSA-N [7-chloro-5-(2-chlorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] 2-propylpentanoate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C(CCC)CCC)N=C1C1=CC=CC=C1Cl WTZPDTDVHCVLMK-UHFFFAOYSA-N 0.000 description 1
QRUFWTOCUCFKLZ-UHFFFAOYSA-N [7-chloro-5-(2-fluorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] 2-propylpentanoate Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(OC(=O)C(CCC)CCC)N=C1C1=CC=CC=C1F QRUFWTOCUCFKLZ-UHFFFAOYSA-N 0.000 description 1
OJDGPERBKOETAX-UHFFFAOYSA-N [O-][N+]1=C(c2ccccc2Cl)c2cc(Cl)ccc2NC(=O)C1 Chemical compound [O-][N+]1=C(c2ccccc2Cl)c2cc(Cl)ccc2NC(=O)C1 OJDGPERBKOETAX-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
238000010908 decantation Methods 0.000 description 1
125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
229960004391 lorazepam Drugs 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000005547 pivalate group Chemical group 0.000 description 1
239000000047 product Substances 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
229960003188 temazepam Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD78209726A 1977-12-14 1978-12-13 Verfahren zur herstellung von 3-di-n-propyl-acetoxy-benzodiazepin-2-onen DD139851A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT893877A AT359509B (de)	1977-12-14	1977-12-14	Verfahren zur herstellung von neuen 3-di-n- -propylacetoxybenzodiazepin-2-onen
AT831278A AT358051B (de)	1978-11-21	1978-11-21	Verfahren zur herstellung von neuen 3-di-n- -propyl-acetoxy-benzodiazepin-2-onen

Publications (1)

Publication Number	Publication Date
DD139851A5 true DD139851A5 (de)	1980-01-23

Family

ID=25604664

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78209726A DD139851A5 (de)	1977-12-14	1978-12-13	Verfahren zur herstellung von 3-di-n-propyl-acetoxy-benzodiazepin-2-onen

Country Status (20)

Country	Link
US (1)	US4261987A (fr)
JP (1)	JPS54138589A (fr)
AU (1)	AU4255778A (fr)
BG (2)	BG29285A3 (fr)
DD (1)	DD139851A5 (fr)
DE (1)	DE2852606A1 (fr)
DK (1)	DK562478A (fr)
ES (1)	ES475960A1 (fr)
FI (1)	FI783743A7 (fr)
FR (1)	FR2411836A1 (fr)
GB (1)	GB2010267A (fr)
GR (1)	GR65190B (fr)
IT (1)	IT1104583B (fr)
LU (1)	LU80632A1 (fr)
NL (1)	NL7812144A (fr)
NO (1)	NO784094L (fr)
PL (1)	PL114759B1 (fr)
RO (1)	RO79702A (fr)
SE (1)	SE7812649L (fr)
YU (1)	YU294378A (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1190133B (it) *	1986-06-19	1988-02-10	Chiesi Farma Spa	Derivati di acido valproico e di acido (e)-2-valproenoico,procedimento per la loro preparazione e relative composizioni farmaceutiche
US5030632A (en) *	1986-09-23	1991-07-09	Sandoz Pharm. Corp.	Low dose temazepam
US5629310A (en) *	1986-09-23	1997-05-13	Sterling; William R.	Low dose temazepam
US5211954A (en) *	1986-09-23	1993-05-18	Sandoz Ltd.	Low dose temazepam

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3176009A (en) *		1965-03-30		Hydrolysis of l-acylated-j-acyloxy benzodiazepines
BE621819A (fr) *	1961-08-29
AT242706B (de) *	1962-11-28	1965-10-11	Hoffmann La Roche	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten
GB1051795A (fr) *	1964-02-11
US3236838A (en) *	1964-06-09	1966-02-22	Hoffmann La Roche	Certain 1-substituted-benzodiazepin-2-one compounds
FR135F (fr) *	1964-08-13
US3801568A (en) *	1972-02-07	1974-04-02	American Home Prod	Optically active 1,3-dihydro-3-substituted 5-phenyl-2h-1,4-benzodiazepin-2-ones and process for their separation
NL173269C (nl) *	1974-04-30	1984-01-02	Ferrer Int	Werkwijze voor de bereiding van een geneesmiddel met als werkzaam bestanddeel een 1,4-benzodiazepinederivaat, alsmede werkwijze voor de bereiding van het 1,4-benzodiazepinederivaat.

1978
- 1978-12-05 FI FI783743A patent/FI783743A7/fi unknown
- 1978-12-05 DE DE19782852606 patent/DE2852606A1/de not_active Withdrawn
- 1978-12-06 GR GR57804A patent/GR65190B/el unknown
- 1978-12-06 NO NO784094A patent/NO784094L/no unknown
- 1978-12-08 LU LU80632A patent/LU80632A1/de unknown
- 1978-12-08 SE SE7812649A patent/SE7812649L/xx unknown
- 1978-12-12 BG BG044352A patent/BG29285A3/xx unknown
- 1978-12-12 PL PL1978211668A patent/PL114759B1/pl unknown
- 1978-12-12 FR FR7834868A patent/FR2411836A1/fr not_active Withdrawn
- 1978-12-12 BG BG041705A patent/BG29284A3/xx unknown
- 1978-12-12 GB GB7848060A patent/GB2010267A/en not_active Withdrawn
- 1978-12-13 ES ES475960A patent/ES475960A1/es not_active Expired
- 1978-12-13 DD DD78209726A patent/DD139851A5/de unknown
- 1978-12-13 IT IT7830778A patent/IT1104583B/it active
- 1978-12-13 NL NL7812144A patent/NL7812144A/xx not_active Application Discontinuation
- 1978-12-14 DK DK562478A patent/DK562478A/da unknown
- 1978-12-14 JP JP15565978A patent/JPS54138589A/ja active Pending
- 1978-12-14 RO RO78101144A patent/RO79702A/fr unknown
- 1978-12-14 YU YU02943/78A patent/YU294378A/xx unknown
- 1978-12-14 AU AU42557/78A patent/AU4255778A/en active Pending
- 1978-12-14 US US05/970,057 patent/US4261987A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
IT1104583B (it)	1985-10-21
JPS54138589A (en)	1979-10-27
GB2010267A (en)	1979-06-27
GR65190B (en)	1980-07-29
GB2010267B (fr)
FR2411836A1 (fr)	1979-07-13
AU4255778A (en)	1979-06-21
ES475960A1 (es)	1979-05-01
NO784094L (no)	1979-06-15
US4261987A (en)	1981-04-14
PL114759B1 (en)	1981-02-28
FI783743A7 (fi)	1979-06-15
BG29285A3 (bg)	1980-10-15
YU294378A (en)	1983-06-30
RO79702A (fr)	1982-08-17
PL211668A1 (pl)	1979-07-30
LU80632A1 (de)	1979-04-09
IT7830778A0 (it)	1978-12-13
SE7812649L (sv)	1979-06-15
NL7812144A (nl)	1979-06-18
BG29284A3 (bg)	1980-10-15
DK562478A (da)	1979-06-15
DE2852606A1 (de)	1979-06-21

Publication	Publication Date	Title
DE2940483A1 (de)	1980-04-30	5h-2,3-benzodiazepinderivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel
DD143906A5 (de)	1980-09-17	Trianzin-derivate
DE1236510B (de)	1967-03-16	Verfahren zur Herstellung von Acylaminotetramsaeuren
DD139851A5 (de)	1980-01-23	Verfahren zur herstellung von 3-di-n-propyl-acetoxy-benzodiazepin-2-onen
DE2223681A1 (de)	1972-11-30	Neue heterocyclische Verbindungen und Verfahren zu ihrer Herstellung
DE2523250A1 (de)	1975-12-18	Benzodiazepinderivate und verfahren zu deren herstellung
DE2225149A1 (de)	1972-12-14	Neue Oxofurylesterdenvate von Penicillin und Cephalosporin
AT359509B (de)	1980-11-10	Verfahren zur herstellung von neuen 3-di-n- -propylacetoxybenzodiazepin-2-onen
DE2314993A1 (de)	1974-10-03	Neue benzodiazepinderivate und verfahren zu deren herstellung
DE2511802A1 (de)	1975-09-25	Alkoxyanilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
AT358051B (de)	1980-08-25	Verfahren zur herstellung von neuen 3-di-n- -propyl-acetoxy-benzodiazepin-2-onen
DE2035797A1 (de)	1972-01-27	Neue Nitrofurandenvate , ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Arzneimittel
DE2265139C3 (de)	1978-07-13	Substituierte l-Methyl-5-phenyl-13-Dihydro-2H-1,4-benzodiazepin-2-on-derivate
AT325627B (de)	1975-10-27	Verfahren zur herstellung von neuen 1-substituierten 1,4-benzodiazepinen sowie deren säureadditionssalzen
DE2360852A1 (de)	1974-06-12	Neue azabenzo-1,5-diazepine
DE1445858C3 (de)	1976-02-26	7-Cyan-5-phenyl-1,2-dihydro-3H-l,4benzodiazepin-2-on-Derivate
AT346346B (de)	1978-11-10	Verfahren zur herstellung von neuen derivaten des 5h-dibenz(b,f)azepins
AT235272B (de)	1964-08-25	Verfahren zur Herstellung von neuen 2-Glycylamidobenzophenonen
AT308115B (de)	1973-06-25	Verfahren zur Herstellung von Benzodiazepinderivaten sowie von Säureadditionssalzen dieser Verbindungen
DE3204074A1 (de)	1982-10-28	Neue 1-benzyl-4-(4-(2-pyrimidinylamino)-benzyl)-2,3-dioxopiperazin-derivate, salze derselben, verfahren zur herstellung derselben und carcinostatische mittel mit einem gehalt derselben
CH634835A5 (de)	1983-02-28	Verfahren zur herstellung von neuen benzodiazepinderivaten.
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