AU720745B2 - Novel 2,3-benzodiazepine derivatives - Google Patents

Novel 2,3-benzodiazepine derivatives Download PDF

Info

Publication number: AU720745B2
Authority: AU; Australia
Prior art keywords: group; hydrogen; methyl; formula; benzodiazepine
Prior art date: 1996-04-04
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.): Ceased

Application number

AU17734/97A

Other languages

English (en)

Other versions

AU1773497A (en

Inventor

Gizella Abraham

Ferenc Dr. Andrasi

Pal Dr. Berzsenyi

Emese Csuzdi

Melinda Dr. Gal

Tamas Dr. Hamori

Katalin Dr. Horvath

Istvan Dr. Ling

Imre Moravcsik

Sandor Dr. Solyom

Marta Szollosy

Istvan Dr. Tarnawa

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.)

Egis Pharmaceuticals PLC

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

Egis Pharmaceuticals PLC

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.)

1996-04-04

Filing date

1997-04-04

Publication date

2000-06-08

1996-04-04 Priority claimed from HU9600871A external-priority patent/HU9600871D0/hu

1997-04-04 Application filed by Egyt Gyogyszervegyeszeti Gyar, Egis Pharmaceuticals PLC filed Critical Egyt Gyogyszervegyeszeti Gyar

1997-10-09 Publication of AU1773497A publication Critical patent/AU1773497A/en

2000-06-08 Application granted granted Critical

2000-06-08 Publication of AU720745B2 publication Critical patent/AU720745B2/en

2017-04-04 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

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229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 9
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 4
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150000001875 compounds Chemical class 0.000 claims description 124
238000000034 method Methods 0.000 claims description 70
239000001257 hydrogen Substances 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 13
239000008194 pharmaceutical composition Substances 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
125000001246 bromo group Chemical group Br* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
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125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 5
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
BOTFWTSXHPAQNN-UHFFFAOYSA-N 1-[5-(4-aminophenyl)-7-chloro-2-methyl-1,3-dihydro-2,4-benzodiazepin-3-yl]ethanone Chemical compound N=1C(C(C)=O)N(C)CC2=CC=C(Cl)C=C2C=1C1=CC=C(N)C=C1 BOTFWTSXHPAQNN-UHFFFAOYSA-N 0.000 claims 1
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 14
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239000013078 crystal Substances 0.000 description 11
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NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
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238000004587 chromatography analysis Methods 0.000 description 7
239000003480 eluent Substances 0.000 description 7
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230000000694 effects Effects 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
238000001914 filtration Methods 0.000 description 6
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125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 6
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238000000746 purification Methods 0.000 description 6
HRHBVUZLRNLXQM-UHFFFAOYSA-N 8-chloro-4-methyl-1-(4-nitrophenyl)-4,5-dihydro-3h-2,3-benzodiazepine Chemical compound N=1NC(C)CC2=CC=C(Cl)C=C2C=1C1=CC=C([N+]([O-])=O)C=C1 HRHBVUZLRNLXQM-UHFFFAOYSA-N 0.000 description 5
VLSMHEGGTFMBBZ-OOZYFLPDSA-M Kainate Chemical compound CC(=C)[C@H]1C[NH2+][C@H](C([O-])=O)[C@H]1CC([O-])=O VLSMHEGGTFMBBZ-OOZYFLPDSA-M 0.000 description 5
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
229910000564 Raney nickel Inorganic materials 0.000 description 5
125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 5
238000009835 boiling Methods 0.000 description 5
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238000003328 mesylation reaction Methods 0.000 description 5
230000036963 noncompetitive effect Effects 0.000 description 5
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VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 4
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QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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YHFMUIZNYMFKHD-UHFFFAOYSA-N ethyl 8-bromo-4-methyl-1-(4-nitrophenyl)-4,5-dihydro-2,3-benzodiazepine-3-carboxylate Chemical compound C12=CC(Br)=CC=C2CC(C)N(C(=O)OCC)N=C1C1=CC=C([N+]([O-])=O)C=C1 YHFMUIZNYMFKHD-UHFFFAOYSA-N 0.000 description 3
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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
238000004949 mass spectrometry Methods 0.000 description 1
102000006239 metabotropic receptors Human genes 0.000 description 1
108020004083 metabotropic receptors Proteins 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
230000004112 neuroprotection Effects 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
230000006959 non-competitive inhibition Effects 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004224 protection Effects 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
210000001525 retina Anatomy 0.000 description 1
230000002207 retinal effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 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
- C07D243/02—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AU17734/97A 1996-04-04 1997-04-04 Novel 2,3-benzodiazepine derivatives Ceased AU720745B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU9600871A HU9600871D0 (en)	1996-04-04	1996-04-04	New 2,3-benzodiazepine derivatives
HU871/96		1996-04-04

Publications (2)

Publication Number	Publication Date
AU1773497A AU1773497A (en)	1997-10-09
AU720745B2 true AU720745B2 (en)	2000-06-08

Family

ID=89993864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU17734/97A Ceased AU720745B2 (en)	1996-04-04	1997-04-04	Novel 2,3-benzodiazepine derivatives

Country Status (11)

Country	Link
KR (1)	KR970069997A (fr)
AT (1)	ATE254608T1 (fr)
AU (1)	AU720745B2 (fr)
BE (1)	BE1010962A4 (fr)
DE (1)	DE59711013D1 (fr)
ES (1)	ES2127699B1 (fr)
IT (1)	IT1290453B1 (fr)
NZ (1)	NZ314517A (fr)
UA (1)	UA45358C2 (fr)
YU (1)	YU13197A (fr)
ZA (1)	ZA972746B (fr)

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5288863A (en) *	1991-05-03	1994-02-22	Egis Gyogyszergyar Rt.	Process for the preparation of high-purity 1-(3-chloro-phenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU179018B (en) *	1978-10-19	1982-08-28	Gyogyszerkutato Intezet	Process for producing new 5h-2,3-benzodiazepine derivatives
HU186760B (en) *	1981-03-12	1985-09-30	Gyogyszerkutato Intezet	Process for preparing 3,4-dihydro-5h-2,3-aenzodiazepine derivatives
HU219778B (hu) *	1990-12-21	2001-07-30	Gyógyszerkutató Intézet Közös Vállalat	Eljárás N-acil-2,3-benzodiazepin-származékok, savaddíciós sóik és az ezeket tartalmazó gyógyászati készítmények előállítására, valamint a vegyületek egy csoportja, és az ezeket tartalmazó gyógyászati készítmények
PT1157992E (pt) *	1994-08-31	2005-10-31	Lilly Co Eli	Derivados de di-hidro-2,3-benzodiazepina

1997
- 1997-04-01 ZA ZA972746A patent/ZA972746B/xx unknown
- 1997-04-03 YU YU13197A patent/YU13197A/sh unknown
- 1997-04-03 KR KR1019970012301A patent/KR970069997A/ko not_active Ceased
- 1997-04-03 BE BE9700308A patent/BE1010962A4/fr not_active IP Right Cessation
- 1997-04-03 UA UA97041584A patent/UA45358C2/uk unknown
- 1997-04-03 NZ NZ314517A patent/NZ314517A/xx unknown
- 1997-04-04 AT AT97105591T patent/ATE254608T1/de not_active IP Right Cessation
- 1997-04-04 DE DE59711013T patent/DE59711013D1/de not_active Expired - Fee Related
- 1997-04-04 AU AU17734/97A patent/AU720745B2/en not_active Ceased
- 1997-04-04 ES ES009700703A patent/ES2127699B1/es not_active Expired - Fee Related
- 1997-04-04 IT IT000776 patent/IT1290453B1/it active IP Right Grant

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5288863A (en) *	1991-05-03	1994-02-22	Egis Gyogyszergyar Rt.	Process for the preparation of high-purity 1-(3-chloro-phenyl)-4-methyl-7,8-dimethoxy-5H-2,3-benzodiazepine

Also Published As

Publication number	Publication date
DE59711013D1 (de)	2003-12-24
KR970069997A (ko)	1997-11-07
NZ314517A (en)	2000-03-27
ES2127699B1 (es)	2000-01-16
AU1773497A (en)	1997-10-09
UA45358C2 (uk)	2002-04-15
ZA972746B (en)	1998-10-09
BE1010962A4 (fr)	1999-03-02
IT1290453B1 (it)	1998-12-03
YU13197A (sh)	1999-09-27
ES2127699A1 (es)	1999-04-16
ATE254608T1 (de)	2003-12-15
ITMI970776A1 (it)	1998-10-04

Legal Events

Date	Code	Title	Description
2000-10-05	FGA	Letters patent sealed or granted (standard patent)
2004-11-04	MK14	Patent ceased section 143(a) (annual fees not paid) or expired

Publication	Publication Date	Title
US5519019A (en)	1996-05-21	N-acyl-2,3-benzoidazepine derivatives, pharmaceutical compositions containing them and process for preparing same
US5807851A (en)	1998-09-15	2,3-Benzodiazepine Derivatives as non-competitive AMPA
HU219778B (hu)	2001-07-30	Eljárás N-acil-2,3-benzodiazepin-származékok, savaddíciós sóik és az ezeket tartalmazó gyógyászati készítmények előállítására, valamint a vegyületek egy csoportja, és az ezeket tartalmazó gyógyászati készítmények
BG60270B2 (bg)	1994-03-31	Метод за получаване на 5н-2,3-бензодиазепинови производни
PL194118B1 (pl)	2007-04-30	Związki N-arylopiperydyny, sposób wytwarzania związków N-arylopiperydyny, oraz kompozycje farmaceutyczne zawierające te związki
US5639751A (en)	1997-06-17	N-acyl-2,3-benzodiazepine derivatives for treating acute and chronic neurodegenerative disorders
SK130694A3 (en)	1995-07-11	1-£2h-1-benzopyran-2-on-8-yl\| pyperazine derivatives, method of their production, pharmaceutical agents containing these compounds as effective matters and their using
US5521174A (en)	1996-05-28	N-acyl-2,3-benzodiazepine derivatives and a method of treating spasms of the skeletal musculature therewith
EP2861593A1 (fr)	2015-04-22	Composés tricycliques en tant qu'inhibiteurs de kat ii
AU720745B2 (en)	2000-06-08	Novel 2,3-benzodiazepine derivatives
WO1999007707A1 (fr)	1999-02-18	DERIVES DE 9H-1,3-DIOXOLO/4,5-h//2,3/BENZODIAZEPINE SUBSTITUEE EN HUIT UTILISES COMME INHIBITEURS DES RECEPTEURS D'AMPA/KAINATE
HRP960065A2 (en)	1997-12-31	1-/2-(substituted vinyl)/-3, 4-dihydro-5h-2,3-benzodiazepine derivatives
NO319151B1 (no)	2005-06-27	Nye, 3-substituerte 3H-2,3-benzodiazepinderivater, fremstilling av dem og anvendelse av dem for fremstilling av legemidler
FR2760014A1 (fr)	1998-08-28	Nouveaux composes de 2-amino indane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP0511152A2 (fr)	1992-10-28	Quinoxalines, leur préparation et utilisation
US6482819B1 (en)	2002-11-19	2,3-benzodiazepine derivatives
EP0299345A2 (fr)	1989-01-18	Dihydro-1,4-oxazino(2,3-c)quinoléines, procédé et composés intermédiaires pour leur préparation et leur utilisation comme médicaments
NZ210123A (en)	1987-05-29	Thiadiazinone derivatives and pharmaceutical compositions
JP2001512095A (ja)	2001-08-21	プロパルギルアミンｎ−オキシドをエナミノンに変換する方法
BG66199B1 (bg)	2012-01-31	2,3-беhзодиазепинови производни и фармацевтични състави, които ги съдържат като активен компонент
US3968230A (en)	1976-07-06	Compositions containing benzodiazepindiones and method of use
US3931226A (en)	1976-01-06	Process for the preparation of diazepino[1,2-a]indoles
FR2716194A1 (fr)	1995-08-18	Dérivés de 3-acylamino-5-phényl-1,4-benzodiazépin-2-one polysubstitués, leur procédé de préparation et les compositions pharmaceutiques les contenant.
TW200413327A (en)	2004-08-01	Novel process for the preparation of imidazolyl compounds