LU81990A1 - Derives de 3-hydroxy-1,4-benzodiazepin-2-one,leur procede de preparation et leur application therapeutique - Google Patents

Derives de 3-hydroxy-1,4-benzodiazepin-2-one,leur procede de preparation et leur application therapeutique Download PDF

Info

Publication number: LU81990A1
Authority: LU; Luxembourg
Prior art keywords: hydroxy; benzodiazepin; chloro; phenyl; dihydro
Prior art date: 1978-12-18

Application number

LU81990A

Other languages

English (en)

French (fr)

Inventor

L 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.)

1978-12-18

Filing date

1979-12-13

Publication date

1981-07-23

1979-12-13 Application filed by Gerot Pharmazeutika filed Critical Gerot Pharmazeutika

1981-07-23 Publication of LU81990A1 publication Critical patent/LU81990A1/fr

Links

YSPYFFRTSUIPCB-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2,3-dione Chemical class N1C(=O)C(=O)N=CC2=CC=CC=C21 YSPYFFRTSUIPCB-UHFFFAOYSA-N 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 2
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 20
125000005843 halogen group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 8
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 claims description 2
150000003983 crown ethers Chemical class 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 claims description 2
229960002456 hexobarbital Drugs 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000003444 phase transfer catalyst Substances 0.000 claims description 2
230000003389 potentiating effect Effects 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
239000012429 reaction media Substances 0.000 claims description 2
230000001624 sedative effect Effects 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims 2
GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical compound ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 claims 1
CGUAABBXJZGDPW-UHFFFAOYSA-N 7-chloro-3-hydroxy-1-(2-methoxyethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1C(O)C(=O)N(CCOC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 CGUAABBXJZGDPW-UHFFFAOYSA-N 0.000 claims 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
150000004714 phosphonium salts Chemical class 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000002244 precipitate Substances 0.000 description 7
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000047 product Substances 0.000 description 5
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 4
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 4
229960004535 oxazepam Drugs 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
-1 for example Chemical class 0.000 description 3
229960004391 lorazepam Drugs 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
150000003109 potassium Chemical class 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
RFCIQRONWHKMIR-UHFFFAOYSA-N 1h-1,4-benzodiazepin-3-ol Chemical class C1=NC(O)=CNC2=CC=CC=C21 RFCIQRONWHKMIR-UHFFFAOYSA-N 0.000 description 1
FERBACJQVQVCKH-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-3-hydroxy-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1F FERBACJQVQVCKH-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010022998 Irritability Diseases 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
229960001413 acetanilide Drugs 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000007278 cyanoethylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000002547 new drug Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000000284 resting effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
230000017105 transposition Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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

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)
Plural Heterocyclic Compounds (AREA)

LU81990A 1978-12-18 1979-12-13 Derives de 3-hydroxy-1,4-benzodiazepin-2-one,leur procede de preparation et leur application therapeutique LU81990A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT903178		1978-12-18
AT903178A AT361492B (de)	1978-12-18	1978-12-18	Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen

Publications (1)

Publication Number	Publication Date
LU81990A1 true LU81990A1 (fr)	1981-07-23

Family

ID=3610590

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81990A LU81990A1 (fr)	1978-12-18	1979-12-13	Derives de 3-hydroxy-1,4-benzodiazepin-2-one,leur procede de preparation et leur application therapeutique

Country Status (25)

Country	Link
US (1)	US4388313A (de)
JP (1)	JPS5583764A (de)
AT (1)	AT361492B (de)
AU (1)	AU532331B2 (de)
BE (1)	BE880632A (de)
BG (1)	BG60474B2 (de)
CA (1)	CA1113464A (de)
CH (1)	CH643248A5 (de)
DE (1)	DE2950235A1 (de)
DK (1)	DK154973C (de)
ES (1)	ES486895A0 (de)
FI (1)	FI67375C (de)
FR (1)	FR2444672A1 (de)
GB (1)	GB2043630B (de)
GR (1)	GR73901B (de)
HK (1)	HK33385A (de)
IT (1)	IT1193345B (de)
LU (1)	LU81990A1 (de)
MY (1)	MY8600020A (de)
NL (1)	NL187068C (de)
NO (1)	NO151859C (de)
SE (1)	SE440351B (de)
SG (1)	SG13585G (de)
YU (1)	YU40586B (de)
ZA (1)	ZA796600B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2084577T3 (es) *	1986-10-24	1996-05-16	Abbott Lab	Ensayo, trazadores, inmunogenos y anticuerpos para benzodiazepinas.

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3311612A (en) *		1967-03-28		Process for preparing
US3371085A (en) *	1959-12-10	1968-02-27	Hoffmann La Roche	5-aryl-3h-1,4-benzodiazepin-2(1h)-ones
BE621819A (de) *	1961-08-29
GB1050401A (de) *	1963-02-19	1900-01-01
NL298071A (de) *	1963-06-04
GB1051795A (de) *	1964-02-11
FR135F (de) *	1964-08-13
NO120269B (de) *	1965-11-02	1970-09-28	Hoffmann La Roche
US3464978A (en) *	1967-04-21	1969-09-02	Hoffmann La Roche	1-substituted urea alkyl 1,2-dihydro-1,4-benzodiazepines and benzodiazepin - 2-ones
CH574421A5 (en) *	1969-02-14	1976-04-15	Hoffmann La Roche	Benzodiazepines
AT309436B (de) *	1970-06-23	1973-08-27	Gerot Pharmazeutika	Verfahren zur Herstellung von 3-Hydroxy-1,4-benzodiazepin Derivaten oder deren Salzen
US4065451A (en) *	1971-03-30	1977-12-27	American Home Products	1,3-Dihydro-3-hydroxy-5-phenyl-2H-1,4-benzodiazepin-2-one, substituted diamino acetate esters and their acid salts
CH573416A5 (de) *	1971-07-30	1976-03-15	Sumitomo Chemical Co
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
JPS494226A (de) *	1972-04-27	1974-01-16

1978
- 1978-12-18 AT AT903178A patent/AT361492B/de not_active IP Right Cessation
1979
- 1979-11-26 NO NO793827A patent/NO151859C/no unknown
- 1979-11-30 DK DK510379A patent/DK154973C/da not_active IP Right Cessation
- 1979-12-05 ZA ZA00796600A patent/ZA796600B/xx unknown
- 1979-12-05 FR FR7929879A patent/FR2444672A1/fr active Granted
- 1979-12-11 NL NLAANVRAGE7908919,A patent/NL187068C/xx not_active IP Right Cessation
- 1979-12-11 AU AU53664/79A patent/AU532331B2/en not_active Expired
- 1979-12-13 DE DE19792950235 patent/DE2950235A1/de active Granted
- 1979-12-13 LU LU81990A patent/LU81990A1/fr unknown
- 1979-12-14 BE BE0/198574A patent/BE880632A/fr not_active IP Right Cessation
- 1979-12-14 ES ES486895A patent/ES486895A0/es active Granted
- 1979-12-14 FI FI793924A patent/FI67375C/fi not_active IP Right Cessation
- 1979-12-14 GB GB7943107A patent/GB2043630B/en not_active Expired
- 1979-12-14 SE SE7910333A patent/SE440351B/sv not_active IP Right Cessation
- 1979-12-17 CA CA342,046A patent/CA1113464A/en not_active Expired
- 1979-12-17 GR GR60778A patent/GR73901B/el unknown
- 1979-12-17 YU YU3087/79A patent/YU40586B/xx unknown
- 1979-12-18 JP JP16367879A patent/JPS5583764A/ja active Granted
- 1979-12-18 IT IT28149/79A patent/IT1193345B/it active
- 1979-12-18 CH CH1123179A patent/CH643248A5/de not_active IP Right Cessation
1981
- 1981-05-11 US US06/262,676 patent/US4388313A/en not_active Expired - Lifetime
1985
- 1985-02-19 SG SG135/85A patent/SG13585G/en unknown
- 1985-05-02 HK HK333/85A patent/HK33385A/xx not_active IP Right Cessation
1986
- 1986-12-30 MY MY20/86A patent/MY8600020A/xx unknown
1993
- 1993-07-21 BG BG097977A patent/BG60474B2/bg unknown

Also Published As

Publication number	Publication date
HK33385A (en)	1985-05-10
FI793924A7 (fi)	1980-06-19
US4388313A (en)	1983-06-14
NO793827L (no)	1980-06-19
ES8103738A1 (es)	1980-10-01
YU308779A (en)	1983-02-28
FR2444672A1 (fr)	1980-07-18
ZA796600B (en)	1981-07-29
SE440351B (sv)	1985-07-29
SE7910333L (sv)	1980-06-19
CA1113464A (en)	1981-12-01
MY8600020A (en)	1986-12-31
NO151859C (no)	1985-06-19
GR73901B (de)	1984-05-18
ATA903178A (de)	1980-08-15
NL187068B (nl)	1990-12-17
ES486895A0 (es)	1980-10-01
AU5366479A (en)	1980-06-26
DE2950235A1 (de)	1980-06-26
JPS5583764A (en)	1980-06-24
YU40586B (en)	1986-02-28
AT361492B (de)	1981-03-10
GB2043630B (en)	1983-06-15
NL7908919A (nl)	1980-06-20
AU532331B2 (en)	1983-09-29
BE880632A (fr)	1980-06-16
FI67375B (fi)	1984-11-30
NO151859B (no)	1985-03-11
DK154973B (da)	1989-01-16
NL187068C (nl)	1991-05-16
BG60474B2 (bg)	1995-04-28
SG13585G (en)	1985-08-16
FI67375C (fi)	1985-03-11
IT7928149A0 (it)	1979-12-18
JPS6310699B2 (de)	1988-03-08
DE2950235C2 (de)	1987-08-27
IT1193345B (it)	1988-06-15
DK154973C (da)	1989-06-05
CH643248A5 (de)	1984-05-30
DK510379A (da)	1980-06-19
GB2043630A (en)	1980-10-08
FR2444672B1 (de)	1983-05-13

Publication	Publication Date	Title
JPH0529216B2 (de)	1993-04-28
EP0306408B1 (de)	1992-03-18	Imidazo[1,2-b]pyridazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0114770B1 (de)	1987-07-22	Verbindungen mit diazotiertem heterocyclischem Kern, Verfahren zu deren Herstellung und diese enthaltende, auf das zentrale Nervensystem wirkende Arzneimittel
EP0011059A1 (de)	1980-05-14	Verfahren zur Herstellung von (+,-) Vincadifformin und anderen verwandten pentacyclischen Derivaten
FR2747121A1 (fr)	1997-10-10	Nouveaux derives de 2,3-benzodiazepine
LU81990A1 (fr)	1981-07-23	Derives de 3-hydroxy-1,4-benzodiazepin-2-one,leur procede de preparation et leur application therapeutique
FR2722195A1 (fr)	1996-01-12	Nouveaux derives de 1,3-dihydro-2h-pyrrolo(2,3-b) pyridin-2-ones et oxazolo(4,5-b) pyridin-2(3h)-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
FR2618777A1 (fr)	1989-02-03	Benzazepines a action therapeutique
BE779775A (fr)	1972-08-24	Derives de l'uree, procede pour les preparer et leurs applications
BE839365R (fr)	1976-09-09	Derives de diazepine
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