SI9111966B - N-acyl-2,3-benzodiazepine derivatives and process for their preparation - Google Patents
N-acyl-2,3-benzodiazepine derivatives and process for their preparation Download PDFInfo
- Publication number
- SI9111966B SI9111966B SI9111966A SI9111966A SI9111966B SI 9111966 B SI9111966 B SI 9111966B SI 9111966 A SI9111966 A SI 9111966A SI 9111966 A SI9111966 A SI 9111966A SI 9111966 B SI9111966 B SI 9111966B
- Authority
- SI
- Slovenia
- Prior art keywords
- group
- general formula
- hydrogen
- atoms
- double bond
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 19
- -1 cyano, carboxyl Chemical group 0.000 claims abstract 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 32
- 239000001257 hydrogen Substances 0.000 claims abstract 32
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 125000002252 acyl group Chemical group 0.000 claims abstract 18
- 229910052736 halogen Inorganic materials 0.000 claims abstract 16
- 150000002367 halogens Chemical class 0.000 claims abstract 16
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 9
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 7
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 230000010933 acylation Effects 0.000 claims 6
- 238000005917 acylation reaction Methods 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 239000000654 additive Substances 0.000 claims 3
- 150000001371 alpha-amino acids Chemical class 0.000 claims 3
- 235000008206 alpha-amino acids Nutrition 0.000 claims 3
- 235000001014 amino acid Nutrition 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000005544 phthalimido group Chemical group 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002828 nitro derivatives Chemical class 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 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 claims 1
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RJOTWZQVHIRPMM-UHFFFAOYSA-N 1-[5-(4-aminophenyl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-7-yl]propan-1-one Chemical compound C12=CC=3OCOC=3C=C2CC(C)N(C(=O)CC)N=C1C1=CC=C(N)C=C1 RJOTWZQVHIRPMM-UHFFFAOYSA-N 0.000 claims 1
- RQKDTQACQPHOQL-UHFFFAOYSA-N 3h-2,3-benzodiazepine Chemical compound C1=NNC=CC2=CC=CC=C21 RQKDTQACQPHOQL-UHFFFAOYSA-N 0.000 claims 1
- KXYYPZFSVRXWHU-UHFFFAOYSA-N 5-[4-[(2-aminoacetyl)amino]phenyl]-n,8-dimethyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-7-carboxamide Chemical compound C12=CC=3OCOC=3C=C2CC(C)N(C(=O)NC)N=C1C1=CC=C(NC(=O)CN)C=C1 KXYYPZFSVRXWHU-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 201000006474 Brain Ischemia Diseases 0.000 claims 1
- IPYGRHRDGNSGLR-UHFFFAOYSA-N C1=C2C=NN(C(C)=O)C(C)CC2=CC2=C1OCO2 Chemical compound C1=C2C=NN(C(C)=O)C(C)CC2=CC2=C1OCO2 IPYGRHRDGNSGLR-UHFFFAOYSA-N 0.000 claims 1
- HHLIBYANEXQAGX-UHFFFAOYSA-N CC1CC2=CC3=C(C=C2C(=NN1C(=O)C)C4=CC=C(C=C4)NC(=O)CN5CCCC5)OCO3 Chemical compound CC1CC2=CC3=C(C=C2C(=NN1C(=O)C)C4=CC=C(C=C4)NC(=O)CN5CCCC5)OCO3 HHLIBYANEXQAGX-UHFFFAOYSA-N 0.000 claims 1
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 102000018899 Glutamate Receptors Human genes 0.000 claims 1
- 108010027915 Glutamate Receptors Proteins 0.000 claims 1
- 206010021118 Hypotonia Diseases 0.000 claims 1
- 208000007101 Muscle Cramp Diseases 0.000 claims 1
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- 239000007868 Raney catalyst Substances 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 claims 1
- 208000005392 Spasm Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 125000005257 alkyl acyl group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000002461 excitatory amino acid Effects 0.000 claims 1
- 239000003257 excitatory amino acid Substances 0.000 claims 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 1
- 230000036640 muscle relaxation Effects 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- AKIXUHGYYKCAAZ-UHFFFAOYSA-N n-[4-(7-acetyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]-2,2,2-trifluoroacetamide Chemical compound N=1N(C(C)=O)C(C)CC2=CC=3OCOC=3C=C2C=1C1=CC=C(NC(=O)C(F)(F)F)C=C1 AKIXUHGYYKCAAZ-UHFFFAOYSA-N 0.000 claims 1
- SRWVVWKUQALTDV-UHFFFAOYSA-N n-[4-(7-acetyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]-2-(diethylamino)acetamide Chemical compound C1=CC(NC(=O)CN(CC)CC)=CC=C1C(C1=C2)=NN(C(C)=O)C(C)CC1=CC1=C2OCO1 SRWVVWKUQALTDV-UHFFFAOYSA-N 0.000 claims 1
- JAWNYLRBTBQKBE-UHFFFAOYSA-N n-[4-(7-acetyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]-2-(dimethylamino)acetamide Chemical compound N=1N(C(C)=O)C(C)CC2=CC=3OCOC=3C=C2C=1C1=CC=C(NC(=O)CN(C)C)C=C1 JAWNYLRBTBQKBE-UHFFFAOYSA-N 0.000 claims 1
- RNJAHAXIBIIAHU-UHFFFAOYSA-N n-[4-(7-acetyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]acetamide Chemical compound N=1N(C(C)=O)C(C)CC2=CC=3OCOC=3C=C2C=1C1=CC=C(NC(C)=O)C=C1 RNJAHAXIBIIAHU-UHFFFAOYSA-N 0.000 claims 1
- JLAHAVHKKNXOJO-UHFFFAOYSA-N n-[4-(7-acetyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C(C1=C2)=NN(C(C)=O)C(C)CC1=CC1=C2OCO1 JLAHAVHKKNXOJO-UHFFFAOYSA-N 0.000 claims 1
- WVZGYNZLTJGVPW-UHFFFAOYSA-N n-[4-(7-formyl-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C(C1=C2)=NN(C=O)C(C)CC1=CC1=C2OCO1 WVZGYNZLTJGVPW-UHFFFAOYSA-N 0.000 claims 1
- FEDXABXPSDVMMS-UHFFFAOYSA-N n-[4-(8-methyl-7-propanoyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]acetamide Chemical compound C12=CC=3OCOC=3C=C2CC(C)N(C(=O)CC)N=C1C1=CC=C(NC(C)=O)C=C1 FEDXABXPSDVMMS-UHFFFAOYSA-N 0.000 claims 1
- KXSOVXOKIJTMIP-UHFFFAOYSA-N n-[4-(8-methyl-7-propanoyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl)phenyl]propanamide Chemical compound C1=CC(NC(=O)CC)=CC=C1C(C1=C2)=NN(C(=O)CC)C(C)CC1=CC1=C2OCO1 KXSOVXOKIJTMIP-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 210000002027 skeletal muscle Anatomy 0.000 claims 1
- 230000005062 synaptic transmission Effects 0.000 claims 1
- JACAAXNEHGBPOQ-UHFFFAOYSA-N talampanel Chemical compound N=1N(C(C)=O)C(C)CC2=CC=3OCOC=3C=C2C=1C1=CC=C(N)C=C1 JACAAXNEHGBPOQ-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 2
- 210000003169 central nervous system Anatomy 0.000 abstract 2
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 230000000324 neuroprotective effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU398/90A HU219778B (hu) | 1990-12-21 | 1990-12-21 | 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 |
| YU196691A YU48661B (sh) | 1990-12-21 | 1991-12-20 | N-acil-2,3-benzodiazepin derivati, postupak za njihovo dobijanje i postupak za dobijanje farmaceutskog preparata |
| US08/080,604 US5459137A (en) | 1990-12-21 | 1993-06-21 | N-acyl-2,3-benzodiazepine derivatives, pharmaceutical compositions containing them and process for preparing same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9111966A SI9111966A (sl) | 1998-04-30 |
| SI9111966B true SI9111966B (en) | 2001-04-30 |
Family
ID=26317922
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9111966A SI9111966B (en) | 1990-12-21 | 1991-12-20 | N-acyl-2,3-benzodiazepine derivatives and process for their preparation |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US5459137A (cs) |
| EP (1) | EP0492485B1 (cs) |
| JP (1) | JP2756742B2 (cs) |
| KR (1) | KR0169134B1 (cs) |
| CN (2) | CN1041420C (cs) |
| AT (1) | ATE160350T1 (cs) |
| AU (1) | AU641578B2 (cs) |
| BR (1) | BR9105517A (cs) |
| CA (1) | CA2057504C (cs) |
| CZ (1) | CZ280769B6 (cs) |
| DE (1) | DE69128236T2 (cs) |
| DK (1) | DK0492485T3 (cs) |
| ES (1) | ES2112848T3 (cs) |
| FI (1) | FI102611B (cs) |
| GR (1) | GR3026127T3 (cs) |
| HR (1) | HRP920677B1 (cs) |
| HU (1) | HU219778B (cs) |
| IE (1) | IE914518A1 (cs) |
| IL (1) | IL100449A (cs) |
| MX (1) | MX9102734A (cs) |
| NO (1) | NO300376B1 (cs) |
| NZ (1) | NZ241110A (cs) |
| RU (1) | RU2102387C1 (cs) |
| SI (1) | SI9111966B (cs) |
| ZA (1) | ZA9110064B (cs) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5519019A (en) * | 1990-12-21 | 1996-05-21 | Gyogyszerkutato Intezet | N-acyl-2,3-benzoidazepine derivatives, pharmaceutical compositions containing them and process for preparing same |
| 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 |
| US5521174A (en) * | 1990-12-21 | 1996-05-28 | Gyogyszerkutato Intezet Kv. | N-acyl-2,3-benzodiazepine derivatives and a method of treating spasms of the skeletal musculature therewith |
| US5639751A (en) * | 1990-12-21 | 1997-06-17 | Cyogyszerkutato Intezet Kft | N-acyl-2,3-benzodiazepine derivatives for treating acute and chronic neurodegenerative disorders |
| HU219777B (hu) * | 1993-07-02 | 2001-07-30 | Gyógyszerkutató Intézet Kft. | Optikailag aktív 1-(4-nitro-fenil)-4-metil-7,8-metiléndioxi-3,4-dihidro-5H-2,3-benzodiazepin és eljárás előállítására |
| DE4428835A1 (de) * | 1994-08-01 | 1996-02-08 | Schering Ag | Neue 3-substituierte 3H-2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| TR199501070A2 (tr) * | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevinin kristalli bicimi. |
| PT771198E (pt) * | 1994-08-31 | 2002-06-28 | Lilly Co Eli | Derivados de di-hidro-2,3-benzodiazepina |
| US6288057B1 (en) | 1994-08-31 | 2001-09-11 | Eli Lilly And Company | Physical form of dihydro-2,3-benzodiazepine derivative |
| TR199501071A2 (tr) * | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevlerinin üretilmesi icin stereoselektif islem. |
| TR199501072A2 (tr) * | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevinin fiziksel bicimi. |
| US5670640A (en) * | 1996-02-02 | 1997-09-23 | Hoffmann-La Roche Inc. | Process for the manufacture of imidazodiazepine derivatives |
| US5891871A (en) * | 1996-03-21 | 1999-04-06 | Cocensys, Inc. | Substituted 2,3-benzodiazepin-4-ones and the use thereof |
| HU9600871D0 (en) * | 1996-04-04 | 1996-05-28 | Gyogyszerkutato Intezet | New 2,3-benzodiazepine derivatives |
| ZA972746B (en) * | 1996-04-04 | 1998-10-09 | Egyt Gyogyszervegyeszeti Gyar | Novel 2,3-benzodiazepine derivatives |
| HUP9701325A1 (hu) | 1997-07-31 | 2000-08-28 | Gyógyszerkutató Intézet Kft. | Új 2,3-benzodiazepin-származékok |
| UA67749C2 (uk) | 1997-08-12 | 2004-07-15 | Егіш Дьйодьсердьяр Рт. | Похідна 8-заміщеного-9н-1,3-діоксол/4,5-h//2,3/бензодіазепіну з властивостями амра/каїнатного антагоніста, спосіб одержання похідних, фармацевтична композиція (варіанти), спосіб її одержання та спосіб лікування |
| AU748801B2 (en) * | 1997-08-12 | 2002-06-13 | Egis Gyogyszergyar Rt. | 1,3-dioxolo/4,5-H//2,3/benzodiazepine derivatives as ampa/kainate receptor inhibitors |
| WO2000001376A2 (en) * | 1998-07-02 | 2000-01-13 | Eisai Co., Ltd | Pharmaceutical compositions and their uses for treatment of demyelinating disorders |
| HU227128B1 (en) * | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
| EP1248959B1 (de) | 1999-12-22 | 2006-06-21 | Schott Ag | Uv-reflektierendes interferenzschichtsystem |
| EP1296960A2 (en) * | 2000-06-16 | 2003-04-02 | Annovis, Inc. | 5h-2,3-benzodiazepine antagonists of excitatory amino acid receptors |
| HU225100B1 (hu) * | 2000-12-21 | 2006-06-28 | Egyt Gyogyszervegyeszeti Gyar | 2,3-Benzodiazepinszármazékok, ilyen hatóanyagot tartalmazó gyógyászati készítmények és alkalmazásuk |
| US6649607B2 (en) * | 2001-05-18 | 2003-11-18 | Vela Pharmaceuticals, Inc. | Compositions and methods for treating or preventing convulsions or seizures |
| US7645442B2 (en) | 2001-05-24 | 2010-01-12 | Alexza Pharmaceuticals, Inc. | Rapid-heating drug delivery article and method of use |
| US7090830B2 (en) | 2001-05-24 | 2006-08-15 | Alexza Pharmaceuticals, Inc. | Drug condensation aerosols and kits |
| US20070122353A1 (en) | 2001-05-24 | 2007-05-31 | Hale Ron L | Drug condensation aerosols and kits |
| US7458374B2 (en) | 2002-05-13 | 2008-12-02 | Alexza Pharmaceuticals, Inc. | Method and apparatus for vaporizing a compound |
| US7766013B2 (en) | 2001-06-05 | 2010-08-03 | Alexza Pharmaceuticals, Inc. | Aerosol generating method and device |
| US7585493B2 (en) | 2001-05-24 | 2009-09-08 | Alexza Pharmaceuticals, Inc. | Thin-film drug delivery article and method of use |
| US20040105818A1 (en) | 2002-11-26 | 2004-06-03 | Alexza Molecular Delivery Corporation | Diuretic aerosols and methods of making and using them |
| US7913688B2 (en) | 2002-11-27 | 2011-03-29 | Alexza Pharmaceuticals, Inc. | Inhalation device for producing a drug aerosol |
| WO2004050040A2 (en) | 2002-12-03 | 2004-06-17 | Vela Pharmaceuticals, Inc. | Pharmaceutical composition of 1-(3,4-dimethoxyphenyl)-4-methyl-5-ethyl-7-methoxy-8-hydroxy-5h-2,3-benzodiazepine and uses thereof |
| US6864251B2 (en) * | 2002-12-03 | 2005-03-08 | Vela Pharmaceuticals, Inc. | Treatment of LTB4-mediated inflammatory disorders with optically-pure (R)-2,3-benzodiazepines |
| AU2003303312A1 (en) * | 2002-12-03 | 2004-08-30 | Vela Pharmaceuticals, Inc. | Pharmaceutical composition of 1-(3-hydroxy-4-methoxyphenyl)-4-methyl-5-ethyl-7,8-dimethoxy-5h-2,3-benzodiazepine and uses therof |
| US7022700B2 (en) | 2002-12-03 | 2006-04-04 | Vela Pharmaceuticals, Inc. | Method of increasing neutrophil production using optically-pure (R)-2,3-benzodiazepines |
| US6638928B1 (en) | 2002-12-03 | 2003-10-28 | Vela Pharmaceuticals, Inc. | Treatment of irritable bowel syndrome and nonulcer dyspepsia with substituted 2,3-benzodiazepines |
| US20040152694A1 (en) * | 2003-02-04 | 2004-08-05 | Istvan Kurucz | Methods and compositions for treating inflammatory disorders of the airways |
| US6858605B2 (en) * | 2003-02-04 | 2005-02-22 | Ivax Drug Research Institute, Ltd. | Substituted 2,3-benzodiazepine derivatives |
| US20040224943A1 (en) * | 2003-02-19 | 2004-11-11 | Leventer Steven M. | Method of lowering body temperature with (R) - 2,3-benzodiazepines |
| US20040162284A1 (en) * | 2003-02-19 | 2004-08-19 | Harris Herbert W. | Method of lowering body temperature with (S) tofisopam |
| JP2007516149A (ja) | 2003-05-21 | 2007-06-21 | アレックザ ファーマシューティカルズ， インコーポレイテッド | 基板温度の均一性を制御する方法、および、内蔵式加熱ユニットおよびそれを使用する薬剤供給ユニット |
| WO2005007106A2 (en) * | 2003-07-10 | 2005-01-27 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a non-nmda glutamate modulator for the treatment of central nervous system damage |
| US7540286B2 (en) | 2004-06-03 | 2009-06-02 | Alexza Pharmaceuticals, Inc. | Multiple dose condensation aerosol devices and methods of forming condensation aerosols |
| WO2006022714A1 (en) | 2004-08-12 | 2006-03-02 | Alexza Pharmaceuticals, Inc. | Aerosol drug delivery device incorporating percussively activated heat packages |
| GB0507298D0 (en) | 2005-04-11 | 2005-05-18 | Novartis Ag | Organic compounds |
| WO2007077469A1 (en) * | 2005-12-30 | 2007-07-12 | Egis Gyógyszergyár | Optical isomers of dihydro-2,3-benzodiazepines and their stereoselective synthesis |
| US20080108603A1 (en) * | 2006-10-19 | 2008-05-08 | Eisenach James C | Combination therapy for the treatment of pain |
| US20080108622A1 (en) * | 2006-10-19 | 2008-05-08 | Eisenach James C | Combination therapy for the treatment of pain |
| WO2008112661A2 (en) | 2007-03-09 | 2008-09-18 | Alexza Pharmaceuticals, Inc. | Heating unit for use in a drug delivery device |
| TW200902024A (en) * | 2007-04-02 | 2009-01-16 | Teva Pharma | Novel 2,3-benzodiazepine derivatives and their use as antipsychotic agents |
| EP3746138A4 (en) | 2018-02-02 | 2021-11-03 | Alexza Pharmaceuticals, Inc. | ELECTRIC CONDENSING AEROSOL DEVICE |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2353187A1 (de) * | 1973-05-02 | 1974-11-14 | Kali Chemie Ag | Neue benzodiazepinderivate |
| US4164740A (en) * | 1976-03-04 | 1979-08-14 | Constant James N | Synthetic aperture using image scanner |
| HU186760B (en) * | 1981-03-12 | 1985-09-30 | Gyogyszerkutato Intezet | Process for preparing 3,4-dihydro-5h-2,3-aenzodiazepine derivatives |
| HU191702B (en) * | 1984-06-27 | 1987-03-30 | Gyogyszerkutato Intezet | New process for preparing 1-aryl-5 h-2,3-benzodiazepines |
| HU191698B (en) * | 1984-07-27 | 1987-03-30 | Gyogyszerkutato Intezet | Process for producing new 1-aryl-5h-2beta-benzodiazepines |
| HU195788B (en) * | 1986-05-21 | 1988-07-28 | Gyogyszerkutato Intezet | Process for producing 1-/hydroxy-stiryl/-5h-2,3-benzobiazepines and pharmaceutical compositions containing them |
| HU198494B (en) * | 1986-08-15 | 1989-10-30 | Gyogyszerkutato Intezet | Process for producing new 3,4-dihydro-5h-2,3-benzodiazepine derivative and acid addition salts thereof, as well as pharmaceutical compositions comprising same |
| 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 |
-
1990
- 1990-12-21 HU HU398/90A patent/HU219778B/hu unknown
-
1991
- 1991-12-12 CA CA002057504A patent/CA2057504C/en not_active Expired - Lifetime
- 1991-12-18 KR KR1019910023297A patent/KR0169134B1/ko not_active Expired - Fee Related
- 1991-12-19 RU SU5010635A patent/RU2102387C1/ru active
- 1991-12-19 BR BR919105517A patent/BR9105517A/pt not_active Application Discontinuation
- 1991-12-20 NO NO915060A patent/NO300376B1/no not_active IP Right Cessation
- 1991-12-20 IE IE451891A patent/IE914518A1/en not_active IP Right Cessation
- 1991-12-20 NZ NZ241110A patent/NZ241110A/en not_active IP Right Cessation
- 1991-12-20 CZ CS913985A patent/CZ280769B6/cs not_active IP Right Cessation
- 1991-12-20 CN CN91111088A patent/CN1041420C/zh not_active Expired - Fee Related
- 1991-12-20 MX MX9102734A patent/MX9102734A/es unknown
- 1991-12-20 SI SI9111966A patent/SI9111966B/sl unknown
- 1991-12-20 IL IL10044991A patent/IL100449A/en not_active IP Right Cessation
- 1991-12-20 AU AU89963/91A patent/AU641578B2/en not_active Ceased
- 1991-12-20 FI FI916032A patent/FI102611B/fi not_active IP Right Cessation
- 1991-12-20 ZA ZA9110064A patent/ZA9110064B/xx unknown
- 1991-12-20 JP JP3354972A patent/JP2756742B2/ja not_active Expired - Fee Related
- 1991-12-23 AT AT91121882T patent/ATE160350T1/de not_active IP Right Cessation
- 1991-12-23 DK DK91121882T patent/DK0492485T3/da active
- 1991-12-23 ES ES91121882T patent/ES2112848T3/es not_active Expired - Lifetime
- 1991-12-23 DE DE69128236T patent/DE69128236T2/de not_active Expired - Lifetime
- 1991-12-23 EP EP91121882A patent/EP0492485B1/en not_active Expired - Lifetime
-
1992
- 1992-09-30 HR HRP-1966/91A patent/HRP920677B1/xx not_active IP Right Cessation
-
1993
- 1993-06-21 US US08/080,604 patent/US5459137A/en not_active Expired - Lifetime
-
1995
- 1995-03-21 US US08/423,032 patent/US5604223A/en not_active Expired - Lifetime
- 1995-04-17 US US08/423,153 patent/US5536832A/en not_active Expired - Lifetime
-
1998
- 1998-01-10 CN CNB981039766A patent/CN1135982C/zh not_active Expired - Fee Related
- 1998-02-12 GR GR980400299T patent/GR3026127T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SI9111966B (en) | N-acyl-2,3-benzodiazepine derivatives and process for their preparation | |
| DE69930308T2 (de) | Selektive 5-ht 6-rezeptor-liganden | |
| DE59010017D1 (de) | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung | |
| CH643817A5 (de) | Verfahren zur herstellung von neuen benzamid-derivaten. | |
| ATE151766T1 (de) | Benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung | |
| DE60132637T2 (de) | Verfahren zum herstellen von pyrimidionverbindungen und deren pharmazeutisch unbedenklichen salzen | |
| DE68904102T2 (de) | Antivirale tetrahydroimidazo(1,4)benzodiazepin-2-one. | |
| SK89393A3 (en) | New polyiodated compounds, method of preparation, contrast product containing them | |
| WO2002004403A1 (de) | Biphenylcarbonsäureamide, ihre herstellung und ihre verwendung als arzneimittel | |
| US4873241A (en) | 2-amino-N-(2-phenylindan-2-yl)acetamides useful as anti-epileptics | |
| DE68925933T2 (de) | Arylalkylamine und -amide mit krampflösender und nervenschützender Wirkung | |
| JPS6212788B2 (cs) | ||
| CH441366A (de) | Verfahren zur Herstellung von substituierten Hydrazinverbindungen | |
| CA2380986A1 (en) | Carboxylic acid amides, the preparation thereof and their use as pharmaceutical compositions | |
| DE4232739A1 (de) | Neue asymmetrisch substituierte bis-Naphthalimide | |
| DE2747369C2 (cs) | ||
| DE69600231T2 (de) | N-Arylalkylphenylacetamidderivate | |
| DE3879985T2 (de) | Anticonvulsive agenzien. | |
| FI91853C (fi) | Menetelmä farmakologisesti aktiivisten 2-amino-N-(1,2-difenyylietyyli)asetamidijohdannaisten valmistamiseksi | |
| DE3788955T2 (de) | Pyridinyl-Derivate von 2-Aminoacetamid. | |
| US4146645A (en) | Hypertensive phenylalkylamines and salts thereof | |
| AU689478B2 (en) | Pharmacologically active enantiomers of triazolone compounds | |
| FI66353C (fi) | Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara 1-amino-(laegre-alkyl)-3,4-difenyl-1h-pyrazoler | |
| US3429886A (en) | 1-tertiaryaminoalkyl-3-(4-pyridyl)-indoles | |
| RU98112496A (ru) | Производные 5-нафталин-1-ил-1,3-диоксана, их получение и терапевтическое применение |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF | Valid on the event date |