SK1772000A3 - 8-substituted-9h-1,3-dioxolo(4,5-h)(2,3)benzodiazepine derivatives, as ampa/kainate receptor inhibitors - Google Patents
8-substituted-9h-1,3-dioxolo(4,5-h)(2,3)benzodiazepine derivatives, as ampa/kainate receptor inhibitors Download PDFInfo
- Publication number
- SK1772000A3 SK1772000A3 SK177-2000A SK1772000A SK1772000A3 SK 1772000 A3 SK1772000 A3 SK 1772000A3 SK 1772000 A SK1772000 A SK 1772000A SK 1772000 A3 SK1772000 A3 SK 1772000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- group
- benzodiazepine
- dioxolo
- hydrogen
- Prior art date
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- -1 8-substituted-9h-1,3-dioxolo(4,5-h)(2,3)benzodiazepine Chemical class 0.000 title claims description 88
- UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 title abstract description 15
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title abstract description 11
- 102000003678 AMPA Receptors Human genes 0.000 title abstract description 7
- 108090000078 AMPA Receptors Proteins 0.000 title abstract description 7
- 102000000079 Kainic Acid Receptors Human genes 0.000 title abstract description 6
- 108010069902 Kainic Acid Receptors Proteins 0.000 title abstract description 6
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 239
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 158
- 229910052757 nitrogen Inorganic materials 0.000 claims description 139
- 239000002253 acid Substances 0.000 claims description 58
- RPBDCDQMCRHNLM-UHFFFAOYSA-N C1=NNC=C2C=CC=CC2=C1 Chemical compound C1=NNC=C2C=CC=CC2=C1 RPBDCDQMCRHNLM-UHFFFAOYSA-N 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 48
- 125000001424 substituent group Chemical group 0.000 claims description 45
- 238000002360 preparation method Methods 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 35
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 34
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 230000008569 process Effects 0.000 claims description 22
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 239000004480 active ingredient Substances 0.000 claims description 11
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- 125000005843 halogen group Chemical group 0.000 claims description 9
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- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- DJUXLOLHUAHBTN-UHFFFAOYSA-N 5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carboxylic acid Chemical compound C12=CC=3OCOC=3C=C2CC(C(=O)O)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 DJUXLOLHUAHBTN-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
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- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- GEEMYQISCQSQQT-UHFFFAOYSA-N 5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carbaldehyde Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C1=C2)=NN=C(C=O)CC1=CC1=C2OCO1 GEEMYQISCQSQQT-UHFFFAOYSA-N 0.000 claims description 6
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 6
- QTEAWONONNTDLO-UHFFFAOYSA-N 4-[8-(2h-tetrazol-5-yl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C1=CC(N)=CC=C1C(C1=C2)=NN=C(C=3NN=NN=3)CC1=CC1=C2OCO1 QTEAWONONNTDLO-UHFFFAOYSA-N 0.000 claims description 5
- QAQUKRNWQJKIOZ-UHFFFAOYSA-N 5-(4-aminophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carboxamide Chemical compound C12=CC=3OCOC=3C=C2CC(C(=O)N)=NN=C1C1=CC=C(N)C=C1 QAQUKRNWQJKIOZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
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- 239000007800 oxidant agent Substances 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- RNQRLYWVOJJHKD-UHFFFAOYSA-N 8-methyl-5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical compound C12=CC=3OCOC=3C=C2CC(C)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 RNQRLYWVOJJHKD-UHFFFAOYSA-N 0.000 claims description 3
- JOZNXHMSEPHUCI-UHFFFAOYSA-N 9h-1,2-benzodiazepine-8-carboxylic acid Chemical compound C1=CC=NN=C2CC(C(=O)O)=CC=C21 JOZNXHMSEPHUCI-UHFFFAOYSA-N 0.000 claims description 3
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- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000035939 shock Effects 0.000 claims description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000012050 conventional carrier Substances 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 10
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- NJBBOOFPBBAQMM-UHFFFAOYSA-N 5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine-8-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(C1=C2)=NN=C(C#N)CC1=CC1=C2OCO1 NJBBOOFPBBAQMM-UHFFFAOYSA-N 0.000 claims 1
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- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- ZJEHXSSAXVIPJF-UHFFFAOYSA-N [5-(4-nitrophenyl)-9h-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-8-yl]methanol Chemical compound C12=CC=3OCOC=3C=C2CC(CO)=NN=C1C1=CC=C([N+]([O-])=O)C=C1 ZJEHXSSAXVIPJF-UHFFFAOYSA-N 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 3
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- 239000013543 active substance Substances 0.000 abstract 1
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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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU9701381A HUP9701381A3 (en) | 1997-08-12 | 1997-08-12 | New 7,8-dihydro-8,8-disubstituted-9h-1,3-dioxolo-[4,5-h][2,3]-benzodiazepine derivatives, pharmaceutical compositions containing them as active component, and process for producing them |
| HU9701380A HUP9701380A3 (en) | 1997-08-12 | 1997-08-12 | New 8-substituted-9h-1,3-dioxolo-[4,5-h][2,3]-benzodiazepine derivatives, pharmaceutical compositions containing them as active component, and process for producing them |
| PCT/HU1998/000075 WO1999007707A1 (en) | 1997-08-12 | 1998-08-07 | 8-SUBSTITUTED-9H-1,3-DIOXOLO/4,5-h//2,3/BENZODIAZEPINE DERIVATIVES, AS AMPA/KAINATE RECEPTOR INHIBITORS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK1772000A3 true SK1772000A3 (en) | 2000-10-09 |
Family
ID=89995497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK177-2000A SK1772000A3 (en) | 1997-08-12 | 1998-08-07 | 8-substituted-9h-1,3-dioxolo(4,5-h)(2,3)benzodiazepine derivatives, as ampa/kainate receptor inhibitors |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6562810B1 (pt) |
| EP (1) | EP1003749B1 (pt) |
| JP (1) | JP2001512730A (pt) |
| KR (1) | KR20010022862A (pt) |
| CN (1) | CN1109033C (pt) |
| AT (1) | ATE252586T1 (pt) |
| AU (1) | AU735490B2 (pt) |
| BR (1) | BR9812120A (pt) |
| CA (1) | CA2300302A1 (pt) |
| DE (1) | DE69819166T2 (pt) |
| DK (1) | DK1003749T3 (pt) |
| NO (1) | NO20000655L (pt) |
| NZ (1) | NZ503300A (pt) |
| PL (1) | PL338680A1 (pt) |
| RU (1) | RU2208013C2 (pt) |
| SK (1) | SK1772000A3 (pt) |
| UA (1) | UA67749C2 (pt) |
| WO (1) | WO1999007707A1 (pt) |
Families Citing this family (11)
| 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 |
| CN100558834C (zh) * | 2006-07-21 | 2009-11-11 | 华南理工大学 | 一种环保型干粉涂料及其制备方法 |
| 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 (en) * | 2014-01-21 | 2017-08-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | New dihydro-oxazinobenzodiazepine compounds, a process for their preparation and pharmaceutical compositions containing them |
| CN104391999B (zh) * | 2014-12-15 | 2018-02-02 | 北京国双科技有限公司 | 信息推荐方法和装置 |
| PL3321252T3 (pl) * | 2015-07-06 | 2021-04-06 | Public University Corporation Yokohama City University | Nowy związek, który specyficznie wiąże się z receptorem AMPA |
| RU2634594C1 (ru) * | 2016-11-30 | 2017-11-01 | федеральное государственное автономное образовательное учреждение высшего образования "Казанский (Приволжский) федеральный университет" (ФГАОУ ВО КФУ) | Ингибиторы образования конечных продуктов гликирования на основе азопроизводных фенилсульфокислот |
| WO2023042887A1 (ja) | 2021-09-15 | 2023-03-23 | 国立大学法人 琉球大学 | 認知機能低下、または過体重もしくは肥満症を処置することに用いるための医薬組成物 |
| WO2023042888A1 (ja) | 2021-09-15 | 2023-03-23 | 国立大学法人 琉球大学 | 認知機能低下、または過体重もしくは肥満症を処置することに用いるための医薬組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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. |
| DE19604919A1 (de) * | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
-
1998
- 1998-07-08 UA UA2000031380A patent/UA67749C2/uk unknown
- 1998-08-07 PL PL98338680A patent/PL338680A1/xx unknown
- 1998-08-07 RU RU2000106060/04A patent/RU2208013C2/ru not_active IP Right Cessation
- 1998-08-07 DK DK98939781T patent/DK1003749T3/da active
- 1998-08-07 BR BR9812120-0A patent/BR9812120A/pt not_active IP Right Cessation
- 1998-08-07 JP JP2000506210A patent/JP2001512730A/ja active Pending
- 1998-08-07 EP EP98939781A patent/EP1003749B1/en not_active Expired - Lifetime
- 1998-08-07 AT AT98939781T patent/ATE252586T1/de not_active IP Right Cessation
- 1998-08-07 US US09/485,391 patent/US6562810B1/en not_active Expired - Fee Related
- 1998-08-07 CN CN98809765A patent/CN1109033C/zh not_active Expired - Fee Related
- 1998-08-07 DE DE69819166T patent/DE69819166T2/de not_active Expired - Fee Related
- 1998-08-07 NZ NZ503300A patent/NZ503300A/en unknown
- 1998-08-07 WO PCT/HU1998/000075 patent/WO1999007707A1/en not_active Application Discontinuation
- 1998-08-07 CA CA002300302A patent/CA2300302A1/en not_active Abandoned
- 1998-08-07 KR KR1020007001464A patent/KR20010022862A/ko not_active Application Discontinuation
- 1998-08-07 AU AU88181/98A patent/AU735490B2/en not_active Ceased
- 1998-08-07 SK SK177-2000A patent/SK1772000A3/sk unknown
-
2000
- 2000-02-09 NO NO20000655A patent/NO20000655L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20000655L (no) | 2000-04-10 |
| NZ503300A (en) | 2001-06-29 |
| DK1003749T3 (da) | 2004-03-08 |
| UA67749C2 (uk) | 2004-07-15 |
| WO1999007707A1 (en) | 1999-02-18 |
| JP2001512730A (ja) | 2001-08-28 |
| DE69819166T2 (de) | 2004-07-22 |
| PL338680A1 (en) | 2000-11-20 |
| KR20010022862A (ko) | 2001-03-26 |
| AU8818198A (en) | 1999-03-01 |
| EP1003749A1 (en) | 2000-05-31 |
| CN1272846A (zh) | 2000-11-08 |
| RU2208013C2 (ru) | 2003-07-10 |
| CA2300302A1 (en) | 1999-02-18 |
| EP1003749B1 (en) | 2003-10-22 |
| DE69819166D1 (de) | 2003-11-27 |
| ATE252586T1 (de) | 2003-11-15 |
| NO20000655D0 (no) | 2000-02-09 |
| US6562810B1 (en) | 2003-05-13 |
| CN1109033C (zh) | 2003-05-21 |
| AU735490B2 (en) | 2001-07-12 |
| BR9812120A (pt) | 2001-11-20 |
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