CA1249269A - Benzodiazepines, processes for their preparation and their use - Google Patents

Benzodiazepines, processes for their preparation and their use

Info

Publication number: CA1249269A
Authority: CA; Canada
Prior art keywords: phenyl; chloro; spiro; piperidin; acceptable salt
Prior art date: 1984-08-24
Legal status (The legal status 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 status listed.): Expired

Application number

CA000489254A

Other languages

English (en)

French (fr)

Inventor

Karl-Heinz Boltze

Eugen Etschenberg

Jorg Traber

Herbert Busgen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Troponwerke GmbH

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.)

1984-08-24

Filing date

1985-08-22

Publication date

1989-01-24

1985-08-22 Application filed by Troponwerke GmbH filed Critical Troponwerke GmbH

1989-01-24 Application granted granted Critical

1989-01-24 Publication of CA1249269A publication Critical patent/CA1249269A/en

Status Expired legal-status Critical Current

Links

229940049706 benzodiazepine Drugs 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims abstract description 14
230000008569 process Effects 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title abstract description 12
150000001557 benzodiazepines Chemical class 0.000 title abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 47
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims description 96
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 67
239000000203 mixture Substances 0.000 claims description 46
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 37
229910052731 fluorine Inorganic materials 0.000 claims description 28
-1 6-membered hetero-cyclic radical Chemical class 0.000 claims description 27
229910052794 bromium Inorganic materials 0.000 claims description 27
125000004432 carbon atom Chemical group C* 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
229910052801 chlorine Inorganic materials 0.000 claims description 26
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 26
125000001424 substituent group Chemical group 0.000 claims description 25
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 23
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 14
125000002947 alkylene group Chemical group 0.000 claims description 11
238000005804 alkylation reaction Methods 0.000 claims description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003884 phenylalkyl group Chemical group 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
229910052740 iodine Inorganic materials 0.000 claims description 8
230000029936 alkylation Effects 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000000335 thiazolyl group Chemical group 0.000 claims description 6
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238000009835 boiling Methods 0.000 claims description 5
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229910052760 oxygen Inorganic materials 0.000 claims description 5
150000003254 radicals Chemical class 0.000 claims description 5
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125000004429 atom Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
PLPMGHXRBOJVHR-UHFFFAOYSA-N 4-amino-1-benzylpiperidine-4-carbonyl chloride;dihydrochloride Chemical compound Cl.Cl.C1CC(N)(C(Cl)=O)CCN1CC1=CC=CC=C1 PLPMGHXRBOJVHR-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
108090000765 processed proteins & peptides Proteins 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
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239000004480 active ingredient Substances 0.000 claims 17
UMPFWXKTYANUAO-UHFFFAOYSA-N 1'-benzyl-7-chloro-1-methyl-5-phenylspiro[1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC=CC=2)=NC1(CC1)CCN1CC1=CC=CC=C1 UMPFWXKTYANUAO-UHFFFAOYSA-N 0.000 claims 2
HOIDHMTWECEBAF-UHFFFAOYSA-N 1'-benzyl-7-chloro-5-phenylspiro[1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2NC(=O)C1(CC1)CCN1CC1=CC=CC=C1 HOIDHMTWECEBAF-UHFFFAOYSA-N 0.000 claims 2
DULSJKXBUGUHOI-UHFFFAOYSA-N 7-chloro-1',4-dimethyl-5-phenylspiro[1,5-dihydro-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)N2C DULSJKXBUGUHOI-UHFFFAOYSA-N 0.000 claims 2
BBZDURHUDVJOMJ-UHFFFAOYSA-N 7-chloro-1'-methyl-5-phenylspiro[4,5-dihydro-1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)N2 BBZDURHUDVJOMJ-UHFFFAOYSA-N 0.000 claims 2
HUZLOWKVQBKMCB-UHFFFAOYSA-N 7-chloro-1,1',4-trimethyl-5-phenylspiro[5h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)N(C)C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)N2C HUZLOWKVQBKMCB-UHFFFAOYSA-N 0.000 claims 2
DNTOCGRDWRDLQX-UHFFFAOYSA-N 7-chloro-1,1'-dimethyl-5-phenylspiro[4,5-dihydro-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)N(C)C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)N2 DNTOCGRDWRDLQX-UHFFFAOYSA-N 0.000 claims 2
JHLASPMQEQHGJC-UHFFFAOYSA-N 7-chloro-1-ethyl-5-phenylspiro[4,5-dihydro-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound O=C1N(CC)C2=CC=C(Cl)C=C2C(C=2C=CC=CC=2)NC21CCNCC2 JHLASPMQEQHGJC-UHFFFAOYSA-N 0.000 claims 2
ZJIIWKMQNNHOCS-UHFFFAOYSA-N 7-chloro-5-phenylspiro[1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound N1=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2NC(=O)C21CCNCC2 ZJIIWKMQNNHOCS-UHFFFAOYSA-N 0.000 claims 2
VHTGMXAERGPNGV-UHFFFAOYSA-N 7-chloro-5-phenylspiro[4,5-dihydro-1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound N1C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2NC(=O)C21CCNCC2 VHTGMXAERGPNGV-UHFFFAOYSA-N 0.000 claims 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
238000004519 manufacturing process Methods 0.000 claims 2
JBKFVAVNIDDFFD-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(4-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=C(Cl)C=C1 JBKFVAVNIDDFFD-UHFFFAOYSA-N 0.000 claims 1
OIHCPMHJUCEIBG-UHFFFAOYSA-N 1'-benzyl-5-methylspiro[1H-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical group O=C1NC2=CC=CC=C2C(C)=NC1(CC1)CCN1CC1=CC=CC=C1 OIHCPMHJUCEIBG-UHFFFAOYSA-N 0.000 claims 1
AJSZCJYOEGCKQB-UHFFFAOYSA-N 1'-benzyl-7-chloro-5-(4-chlorophenyl)spiro[1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1=CC(Cl)=CC=C1C(C1=CC(Cl)=CC=C1NC1=O)=NC11CCN(CC=2C=CC=CC=2)CC1 AJSZCJYOEGCKQB-UHFFFAOYSA-N 0.000 claims 1
125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
SFGCCFUULMZVND-UHFFFAOYSA-N 7-chloro-1'-methyl-5-phenylspiro[1h-1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)NC1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)=N2 SFGCCFUULMZVND-UHFFFAOYSA-N 0.000 claims 1
PHPKWPGXEDJLKG-UHFFFAOYSA-N 7-chloro-1,1'-dimethyl-5-phenylspiro[1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound C1CN(C)CCC21C(=O)N(C)C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)=N2 PHPKWPGXEDJLKG-UHFFFAOYSA-N 0.000 claims 1
WDLSJVRXVPVVAL-UHFFFAOYSA-N 7-chloro-1-methyl-5-phenylspiro[1,4-benzodiazepine-3,4'-piperidine]-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C=CC=CC=2)=NC21CCNCC2 WDLSJVRXVPVVAL-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

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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)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA000489254A 1984-08-24 1985-08-22 Benzodiazepines, processes for their preparation and their use Expired CA1249269A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP3431195.5		1984-08-24
DE19843431195 DE3431195A1 (de)	1984-08-24	1984-08-24	Neue benzodiazepine, verfahren zu ihrer herstellung sowie ihre verwendung

Publications (1)

Publication Number	Publication Date
CA1249269A true CA1249269A (en)	1989-01-24

Family

ID=6243820

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000489254A Expired CA1249269A (en)	1984-08-24	1985-08-22	Benzodiazepines, processes for their preparation and their use

Country Status (19)

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US (1)	US4647560A (2)
EP (1)	EP0172526B1 (2)
JP (1)	JPS6157582A (2)
KR (1)	KR920000763B1 (2)
AT (1)	ATE46905T1 (2)
AU (1)	AU574216B2 (2)
CA (1)	CA1249269A (2)
DE (2)	DE3431195A1 (2)
DK (1)	DK384585A (2)
ES (1)	ES8702910A1 (2)
FI (1)	FI79315C (2)
GR (1)	GR852035B (2)
HU (1)	HU201933B (2)
IL (1)	IL76153A0 (2)
NO (1)	NO161494C (2)
NZ (1)	NZ213186A (2)
PH (1)	PH23803A (2)
PT (1)	PT81003B (2)
ZA (1)	ZA856409B (2)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4957915A (en) *	1989-02-27	1990-09-18	Biomeasure, Inc.	Benzodiazepine analogs
WO1994026723A2 (en) *	1993-05-14	1994-11-24	Genentech, Inc.	ras FARNESYL TRANSFERASE INHIBITORS
US20040242904A1 (en) *	2001-12-14	2004-12-02	Angelo Basilio	Novel sordarin derivative isolated from culture fermentations and functions as an antifungal agent
US7625887B2 (en) *	2003-01-28	2009-12-01	Takeda Pharmaceutical Company Limited	Receptor agonists

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3998811A (en) *	1971-03-17	1976-12-21	Crc Compagnia Di Recerca Chimica S.A.	Optically active 1,4-benzodiazepines and process for the preparation thereof
HU171033B (hu) *	1974-05-29	1977-10-28	Richter Gedeon Vegyeszet	Sposob poluchenija proizvodnykh benzodiazepina
CA1157855A (en) *	1980-07-31	1983-11-29	Albert E. Fischli	Benzodiazepine derivatives
HUT36793A (en) *	1983-06-27	1985-10-28	Sandoz Ag	Process for producing new spirosuccunimide derivatives and pharmaceutical composition containing them

1984
- 1984-08-24 DE DE19843431195 patent/DE3431195A1/de not_active Withdrawn
1985
- 1985-08-05 NO NO853089A patent/NO161494C/no unknown
- 1985-08-08 US US06/763,746 patent/US4647560A/en not_active Expired - Fee Related
- 1985-08-14 DE DE8585110191T patent/DE3573425D1/de not_active Expired
- 1985-08-14 AT AT85110191T patent/ATE46905T1/de not_active IP Right Cessation
- 1985-08-14 EP EP85110191A patent/EP0172526B1/de not_active Expired
- 1985-08-21 PH PH32676A patent/PH23803A/en unknown
- 1985-08-21 NZ NZ213186A patent/NZ213186A/en unknown
- 1985-08-21 IL IL76153A patent/IL76153A0/xx not_active IP Right Cessation
- 1985-08-22 PT PT81003A patent/PT81003B/pt not_active IP Right Cessation
- 1985-08-22 FI FI853229A patent/FI79315C/fi not_active IP Right Cessation
- 1985-08-22 AU AU46574/85A patent/AU574216B2/en not_active Ceased
- 1985-08-22 GR GR852035A patent/GR852035B/el unknown
- 1985-08-22 CA CA000489254A patent/CA1249269A/en not_active Expired
- 1985-08-23 ES ES546378A patent/ES8702910A1/es not_active Expired
- 1985-08-23 JP JP60184317A patent/JPS6157582A/ja active Granted
- 1985-08-23 HU HU853222A patent/HU201933B/hu not_active IP Right Cessation
- 1985-08-23 KR KR1019850006080A patent/KR920000763B1/ko not_active Expired
- 1985-08-23 ZA ZA856409A patent/ZA856409B/xx unknown
- 1985-08-23 DK DK384585A patent/DK384585A/da not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI79315B (fi)	1989-08-31
EP0172526B1 (de)	1989-10-04
FI853229A0 (fi)	1985-08-22
KR860001812A (ko)	1986-03-22
FI853229L (fi)	1986-02-25
US4647560A (en)	1987-03-03
DK384585D0 (da)	1985-08-23
NZ213186A (en)	1988-04-29
PT81003A (en)	1985-09-01
ES546378A0 (es)	1987-01-16
ZA856409B (en)	1986-04-30
KR920000763B1 (ko)	1992-01-21
ATE46905T1 (de)	1989-10-15
FI79315C (fi)	1989-12-11
NO161494C (no)	1989-08-23
PT81003B (pt)	1987-12-30
NO853089L (no)	1986-02-25
DE3573425D1 (en)	1989-11-09
JPH0378868B2 (2)	1991-12-17
HUT39449A (en)	1986-09-29
AU574216B2 (en)	1988-06-30
EP0172526A1 (de)	1986-02-26
DE3431195A1 (de)	1986-03-06
PH23803A (en)	1989-11-03
DK384585A (da)	1986-02-25
NO161494B (no)	1989-05-16
GR852035B (2)	1985-12-18
IL76153A0 (en)	1985-12-31
JPS6157582A (ja)	1986-03-24
HU201933B (en)	1991-01-28
ES8702910A1 (es)	1987-01-16
AU4657485A (en)	1986-02-27

Legal Events

Date	Code	Title	Description
2006-01-24	MKEX	Expiry

Publication	Publication Date	Title
AU2004212191B2 (en)	2009-12-03	Antiparasitic terpene alkaloids
CA2116068A1 (en)	1994-08-23	Cyclic derivatives, pharmaceutical compositions containing these compounds and processes for preparing them
US4382030A (en)	1983-05-03	2-Acylaminomethyl-1,4-benzodiazepine derivatives and their salts, pharmaceutical compositions thereof and process for their preparation
JP2690282B2 (ja)	1997-12-10	イミダゾジアゼピン
Hester Jr et al.	1980	1-(Aminoalkyl)-6-aryl-4H-s-triazolo [4, 3-a][1, 4] benzodiazepines with antianxiety and antidepressant activity
HUT75875A (en)	1997-05-28	Benzodioxane, chromane and naphtalene derivatives, process for their preparation and pharmaceutical compositions containing the same
MC1999A1 (fr)	1990-01-26	Composes tricycliques
AU649319B2 (en)	1994-05-19	6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles
IE51015B1 (en)	1986-09-03	Heterocyclic compounds,processes for their preparation and pharmaceutical compositions containing them
JP2506263B2 (ja)	1996-06-12	新規ベンズイミダゾ―ル化合物
CA1073904A (en)	1980-03-18	Substituted 6-aryl-4h-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepines and processes for production thereof
ES2241752T3 (es)	2005-11-01	Derivados de azabicicloalcanos para usar como inhibidores de la recaptacion de serotonina y antagonistas de 5ht2a.
AU8548098A (en)	1999-02-22	Therapeutically active 1,2,4-triazolo(4.,3-b) pyridazine derivatives as ligands for gaba receptors
JPH0565288A (ja)	1993-03-19	新規なアシルアミノ置換ヘトラゼピン誘導体、その製法及びそれを含有する医薬組成物
CA1249269A (en)	1989-01-24	Benzodiazepines, processes for their preparation and their use
US3816422A (en)	1974-06-11	2,3-dihydro-oxo-imidazo(1,2-a)pyrimidines and salts thereof
JPH04334367A (ja)	1992-11-20	置換された１，２，３，４−テトラヒドロシクロペント〔ｂ〕インドール、１，２，３，３ａ，４，８ａ−ヘキサヒドロシクロペント〔ｂ〕インドールおよび関連化合物
IE59830B1 (en)	1994-04-20	Heterocyclic compounds and their preparation and use
CS227025B2 (en)	1984-04-16	Method of preparing benzodiazepine
JP2001508419A (ja)	2001-06-26	５−ｈｔ受容体活性を有するスルホンアミド化合物
SK8952002A3 (en)	2002-10-08	Pyrazolo[1,5-d][1,2,4]triazine derivatives, method for their preparation, pharmaceutical composition containing them and use thereof
CA1087182A (en)	1980-10-07	Substituted 1-piperazinyl-triazolo-thieno-1,4- diazepines
US5114944A (en)	1992-05-19	2-phenylpyrazolo[1,5-a]pyrimidine-3-acetic acid derivatives exhibiting therapeutic effects
WO2002016363A1 (en)	2002-02-28	Imidazolophthalazine derivatives as ligands for gabaa receptors
CS209929B2 (en)	1981-12-31	Method of making the new substituted 4h-s-triazolo/3,4c/-thieno/2,3e/-1,4 diazepins