SK1792000A3 - 1,3-DIOXOLO(4,5-H)(2,3)BENZODIAZEPINE DERIVATIVES, PROCESS FORì (54) THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION CO - Google Patents
1,3-DIOXOLO(4,5-H)(2,3)BENZODIAZEPINE DERIVATIVES, PROCESS FORì (54) THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION CO Download PDFInfo
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- SK1792000A3 SK1792000A3 SK179-2000A SK1792000A SK1792000A3 SK 1792000 A3 SK1792000 A3 SK 1792000A3 SK 1792000 A SK1792000 A SK 1792000A SK 1792000 A3 SK1792000 A3 SK 1792000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- optionally substituted
- formula
- phenyl
- alkyl
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 23
- CXJGWOVUBVPLNO-UHFFFAOYSA-N 4h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical class C1=C2C=CN=NC=C2CC2=C1OCO2 CXJGWOVUBVPLNO-UHFFFAOYSA-N 0.000 title claims description 22
- 238000002360 preparation method Methods 0.000 title claims description 17
- 230000008569 process Effects 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 160
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims abstract description 4
- -1 amino, phenyl Chemical group 0.000 claims description 111
- 125000001424 substituent group Chemical group 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 82
- 229910052757 nitrogen Inorganic materials 0.000 claims description 80
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 76
- RPBDCDQMCRHNLM-UHFFFAOYSA-N C1=NNC=C2C=CC=CC2=C1 Chemical compound C1=NNC=C2C=CC=CC2=C1 RPBDCDQMCRHNLM-UHFFFAOYSA-N 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 35
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 26
- 125000004193 piperazinyl group Chemical group 0.000 claims description 22
- 125000003277 amino group Chemical group 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- NANRRGDSMNUTLY-UHFFFAOYSA-N 8-methyl-7H-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical class CC1=Cc2cc3OCOc3cc2C=NN1 NANRRGDSMNUTLY-UHFFFAOYSA-N 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000005544 phthalimido group Chemical group 0.000 claims description 7
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 229940049706 benzodiazepine Drugs 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000005543 phthalimide group Chemical group 0.000 claims description 5
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 4
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 239000012050 conventional carrier Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 abstract description 12
- 102000003678 AMPA Receptors Human genes 0.000 abstract description 6
- 108090000078 AMPA Receptors Proteins 0.000 abstract description 6
- 102000000079 Kainic Acid Receptors Human genes 0.000 abstract description 6
- 108010069902 Kainic Acid Receptors Proteins 0.000 abstract description 6
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 137
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 93
- 239000013078 crystal Substances 0.000 description 67
- 230000002829 reductive effect Effects 0.000 description 64
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 59
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- 239000011541 reaction mixture Substances 0.000 description 37
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- 239000012043 crude product Substances 0.000 description 34
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- 238000001704 evaporation Methods 0.000 description 32
- 230000008020 evaporation Effects 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 30
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 29
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000012071 phase Substances 0.000 description 25
- 238000001816 cooling Methods 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- 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 17
- 239000000706 filtrate Substances 0.000 description 17
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 17
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 16
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- 239000008346 aqueous phase Substances 0.000 description 8
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 7
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- 235000011150 stannous chloride Nutrition 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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- 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
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
- 230000007480 spreading Effects 0.000 description 5
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 5
- DJXIVFHYOLZSBW-UHFFFAOYSA-N 8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical compound N=1NC(C)CC2=CC=3OCOC=3C=C2C=1C1=CC=C([N+]([O-])=O)C=C1 DJXIVFHYOLZSBW-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- 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
-
- 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
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9701383A HUP9701383A3 (en) | 1997-08-12 | 1997-08-12 | New 8-methyl-7h-1,3-dioxolo[4,5-h][2,3]-benzodiazepine derivatives, pharmaceutical compositions containing them as active component, and process for producing them |
| HU9701382A HUP9701382A3 (en) | 1997-08-12 | 1997-08-12 | New 7,8-dihydro-8-methyl-9h-1,3-dioxolo-[4,5-h][2,3]-benzodiazepine derivatives, pharmaceutical compositions containing them as active component and process for producing them |
| PCT/HU1998/000076 WO1999007708A1 (fr) | 1997-08-12 | 1998-08-07 | Derives de 1,3-dioxolo/4,5-h//2,3/benzodiazepine utilises comme inhibiteurs des recepteurs ampa/kainate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK1792000A3 true SK1792000A3 (en) | 2000-09-12 |
Family
ID=89995503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK179-2000A SK1792000A3 (en) | 1997-08-12 | 1998-08-07 | 1,3-DIOXOLO(4,5-H)(2,3)BENZODIAZEPINE DERIVATIVES, PROCESS FORì (54) THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION CO |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1015457B1 (fr) |
| JP (1) | JP2001512731A (fr) |
| KR (1) | KR20010022856A (fr) |
| CN (1) | CN1271360A (fr) |
| AT (1) | ATE255112T1 (fr) |
| AU (1) | AU748801B2 (fr) |
| BR (1) | BR9812119A (fr) |
| CA (1) | CA2300142A1 (fr) |
| DE (1) | DE69820081D1 (fr) |
| NO (1) | NO20000654L (fr) |
| NZ (1) | NZ503301A (fr) |
| PL (1) | PL338681A1 (fr) |
| RU (1) | RU2208014C2 (fr) |
| SK (1) | SK1792000A3 (fr) |
| WO (1) | WO1999007708A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP9900354A3 (en) * | 1999-02-15 | 2001-02-28 | Egyt Gyogyszervegyeszeti Gyar | Use of condensed 2,3-benzodiazepine derivatives for the preparation of pharmaceutical compositions treating and preventing diseases related with the inhibition of lipide peroxidation |
| HU227128B1 (en) * | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
| US6858605B2 (en) | 2003-02-04 | 2005-02-22 | Ivax Drug Research Institute, Ltd. | Substituted 2,3-benzodiazepine derivatives |
| EP2338492A1 (fr) | 2009-12-24 | 2011-06-29 | Universidad del Pais Vasco | Procédés et compositions pour le traitement de la maladie d'Alzheimer |
| FR2972454B1 (fr) * | 2011-03-08 | 2013-03-01 | Servier Lab | Nouveaux derives dihydro-oxazolobenzodiazepinones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| HU230684B1 (hu) * | 2014-01-21 | 2017-08-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Új dihidro-oxazino-benzodiazepin vegyületek és eljárás ezek elõállítására, illetve az ezeket tartalmazó gyógyászati készítmények |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU206719B (en) * | 1990-12-21 | 1992-12-28 | Gyogyszerkutato Intezet | Process for producing 1-/4-acylamino-phenyl/-7,8-methylenedioxy-5h-2,3-benzodiazepine derivatives, acid addicional salts and pharmaceutical compositions containing them |
| 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 |
| 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 |
| TR199501071A2 (tr) * | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevlerinin üretilmesi icin stereoselektif islem. |
| TR199501070A2 (tr) * | 1994-08-31 | 1996-06-21 | Lilly Co Eli | Dihidro-2,3-benzodiazepin türevinin kristalli bicimi. |
-
1998
- 1998-08-07 SK SK179-2000A patent/SK1792000A3/sk unknown
- 1998-08-07 BR BR9812119-7A patent/BR9812119A/pt not_active IP Right Cessation
- 1998-08-07 EP EP98939782A patent/EP1015457B1/fr not_active Expired - Lifetime
- 1998-08-07 DE DE69820081T patent/DE69820081D1/de not_active Expired - Lifetime
- 1998-08-07 CN CN98809317A patent/CN1271360A/zh active Pending
- 1998-08-07 KR KR1020007001458A patent/KR20010022856A/ko not_active Ceased
- 1998-08-07 NZ NZ503301A patent/NZ503301A/xx unknown
- 1998-08-07 JP JP2000506211A patent/JP2001512731A/ja active Pending
- 1998-08-07 RU RU2000106061/04A patent/RU2208014C2/ru not_active IP Right Cessation
- 1998-08-07 WO PCT/HU1998/000076 patent/WO1999007708A1/fr not_active Application Discontinuation
- 1998-08-07 CA CA002300142A patent/CA2300142A1/fr not_active Abandoned
- 1998-08-07 AT AT98939782T patent/ATE255112T1/de not_active IP Right Cessation
- 1998-08-07 AU AU88182/98A patent/AU748801B2/en not_active Ceased
- 1998-08-07 PL PL98338681A patent/PL338681A1/xx unknown
-
2000
- 2000-02-09 NO NO20000654A patent/NO20000654L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1271360A (zh) | 2000-10-25 |
| NO20000654L (no) | 2000-04-10 |
| EP1015457A1 (fr) | 2000-07-05 |
| DE69820081D1 (de) | 2004-01-08 |
| PL338681A1 (en) | 2000-11-20 |
| WO1999007708A1 (fr) | 1999-02-18 |
| AU8818298A (en) | 1999-03-01 |
| BR9812119A (pt) | 2004-06-22 |
| KR20010022856A (ko) | 2001-03-26 |
| NZ503301A (en) | 2002-09-27 |
| ATE255112T1 (de) | 2003-12-15 |
| CA2300142A1 (fr) | 1999-02-18 |
| NO20000654D0 (no) | 2000-02-09 |
| JP2001512731A (ja) | 2001-08-28 |
| AU748801B2 (en) | 2002-06-13 |
| RU2208014C2 (ru) | 2003-07-10 |
| EP1015457B1 (fr) | 2003-11-26 |
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