JP2006516647A5 - - Google Patents
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- Publication number
- JP2006516647A5 JP2006516647A5 JP2006503283A JP2006503283A JP2006516647A5 JP 2006516647 A5 JP2006516647 A5 JP 2006516647A5 JP 2006503283 A JP2006503283 A JP 2006503283A JP 2006503283 A JP2006503283 A JP 2006503283A JP 2006516647 A5 JP2006516647 A5 JP 2006516647A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- dihydro
- dioxolo
- benzodiazepine
- thiadiazol
- Prior art date
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229940049706 benzodiazepine Drugs 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 43
- -1 cyanomethyl group Chemical group 0.000 claims 22
- 239000003814 drug Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- RPBDCDQMCRHNLM-UHFFFAOYSA-N C1=NNC=C2C=CC=CC2=C1 Chemical compound C1=NNC=C2C=CC=CC2=C1 RPBDCDQMCRHNLM-UHFFFAOYSA-N 0.000 claims 6
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 6
- 230000001154 acute effect Effects 0.000 claims 6
- 229930195712 glutamate Natural products 0.000 claims 6
- 208000027866 inflammatory disease Diseases 0.000 claims 6
- DBDUGNPURSLMPS-GFCCVEGCSA-N 2-methyl-4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(C)C(N)=CC=2)=NN1C1=NN=C(C)S1 DBDUGNPURSLMPS-GFCCVEGCSA-N 0.000 claims 5
- ZMKBCJHGTFWHJI-GFCCVEGCSA-N 4-[(8r)-7-(4,5-dihydro-1,3-thiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NCCS1 ZMKBCJHGTFWHJI-GFCCVEGCSA-N 0.000 claims 5
- JRXDNQCAOCOIGM-GFCCVEGCSA-N 4-[(8r)-7-(5-ethyl-1,3,4-thiadiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound S1C(CC)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=CC(N)=CC=2)=N1 JRXDNQCAOCOIGM-GFCCVEGCSA-N 0.000 claims 5
- AQVHOPUVJNUMRK-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=CS1 AQVHOPUVJNUMRK-LLVKDONJSA-N 0.000 claims 5
- CUFZAXVDJYYCST-GFCCVEGCSA-N 4-[(8r)-8-methyl-7-(1,3-thiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NC=CS1 CUFZAXVDJYYCST-GFCCVEGCSA-N 0.000 claims 5
- CNJBMCKQTBPYCD-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(5-methyl-1,3,4-oxadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=C(C)O1 CNJBMCKQTBPYCD-LLVKDONJSA-N 0.000 claims 5
- SGQFSRKCDSMQQY-LLVKDONJSA-N 4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=CC(N)=CC=2)=NN1C1=NN=C(C)S1 SGQFSRKCDSMQQY-LLVKDONJSA-N 0.000 claims 5
- 230000004064 dysfunction Effects 0.000 claims 5
- 208000030090 Acute Disease Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 230000000172 allergic effect Effects 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 208000010668 atopic eczema Diseases 0.000 claims 4
- 208000029028 brain injury Diseases 0.000 claims 4
- 206010006451 bronchitis Diseases 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 201000006517 essential tremor Diseases 0.000 claims 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 4
- 201000006417 multiple sclerosis Diseases 0.000 claims 4
- 230000004770 neurodegeneration Effects 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 210000002345 respiratory system Anatomy 0.000 claims 4
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 208000017667 Chronic Disease Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 208000010412 Glaucoma Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 206010046543 Urinary incontinence Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 208000007451 chronic bronchitis Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 208000037976 chronic inflammation Diseases 0.000 claims 2
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000020431 spinal cord injury Diseases 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 claims 1
- OGVWWGVZVJUPHF-UHFFFAOYSA-N 1,2,4-thiadiazol-3-one Chemical compound O=C1N=CSN1 OGVWWGVZVJUPHF-UHFFFAOYSA-N 0.000 claims 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- FNMGRVLXWOVONV-UHFFFAOYSA-N 1,3-thiazin-4-one Chemical compound O=C1C=CSC=N1 FNMGRVLXWOVONV-UHFFFAOYSA-N 0.000 claims 1
- CEBAFUFWRQAHJL-UHFFFAOYSA-N 1,4,2-oxathiazole Chemical compound C1ON=CS1 CEBAFUFWRQAHJL-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims 1
- CPDCZSIMXFZSGX-SNVBAGLBSA-N 2-chloro-4-[(8r)-8-methyl-7-(5-methyl-1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(Cl)C(N)=CC=2)=NN1C1=NN=C(C)S1 CPDCZSIMXFZSGX-SNVBAGLBSA-N 0.000 claims 1
- HCOJNYUPUOBYDH-GFCCVEGCSA-N 2-methyl-4-[(8r)-8-methyl-7-(1,3,4-thiadiazol-2-yl)-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound C([C@H]1C)C2=CC=3OCOC=3C=C2C(C=2C=C(C)C(N)=CC=2)=NN1C1=NN=CS1 HCOJNYUPUOBYDH-GFCCVEGCSA-N 0.000 claims 1
- DZISRJWEOMPAIL-ISZGNANSSA-N 2-methyl-4-[(8r)-8-methyl-7-[5-[(e)-prop-1-enyl]-1,3,4-thiadiazol-2-yl]-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]aniline Chemical compound S1C(/C=C/C)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=C(C)C(N)=CC=2)=N1 DZISRJWEOMPAIL-ISZGNANSSA-N 0.000 claims 1
- OBQQXJNPNJYUKU-UHFFFAOYSA-N 2h-1,3,4-thiadiazol-5-one Chemical compound O=C1SCN=N1 OBQQXJNPNJYUKU-UHFFFAOYSA-N 0.000 claims 1
- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical compound OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 claims 1
- OTLOBZLSZJVQQA-CYBMUJFWSA-N 4-[(8r)-7-(5-ethyl-1,3,4-thiadiazol-2-yl)-8-methyl-8,9-dihydro-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-5-yl]-2-methylaniline Chemical compound S1C(CC)=NN=C1N1[C@H](C)CC2=CC(OCO3)=C3C=C2C(C=2C=C(C)C(N)=CC=2)=N1 OTLOBZLSZJVQQA-CYBMUJFWSA-N 0.000 claims 1
- CXJGWOVUBVPLNO-UHFFFAOYSA-N 4h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical compound C1=C2C=CN=NC=C2CC2=C1OCO2 CXJGWOVUBVPLNO-UHFFFAOYSA-N 0.000 claims 1
- ATDLUVGEFJWWGK-UHFFFAOYSA-N 7h-[1,3]dioxolo[4,5-h][2,3]benzodiazepine Chemical compound C1=CNN=CC2=C1C=C1OCOC1=C2 ATDLUVGEFJWWGK-UHFFFAOYSA-N 0.000 claims 1
- QBZMIFMKDXUHIR-NFKWMPFVSA-N C[C@H](C1)N(C2=NN=C(OC)[S+]2C)N=C(C(C=C2)=CC(Cl)=C2N)C2=C1C=C1OCOC1=C2 Chemical compound C[C@H](C1)N(C2=NN=C(OC)[S+]2C)N=C(C(C=C2)=CC(Cl)=C2N)C2=C1C=C1OCOC1=C2 QBZMIFMKDXUHIR-NFKWMPFVSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 208000013403 hyperactivity Diseases 0.000 claims 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 1
- 150000002545 isoxazoles Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 150000003536 tetrazoles Chemical class 0.000 claims 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 claims 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/358,053 US6858605B2 (en) | 2003-02-04 | 2003-02-04 | Substituted 2,3-benzodiazepine derivatives |
| PCT/US2004/003041 WO2004069197A2 (en) | 2003-02-04 | 2004-02-03 | Novel substituted 2,3-benzodiazepine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006516647A JP2006516647A (ja) | 2006-07-06 |
| JP2006516647A5 true JP2006516647A5 (enExample) | 2007-03-22 |
Family
ID=32771128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006503283A Withdrawn JP2006516647A (ja) | 2003-02-04 | 2004-02-03 | 新規置換２，３−ベンゾジアゼピン誘導体 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6858605B2 (enExample) |
| EP (1) | EP1592673A4 (enExample) |
| JP (1) | JP2006516647A (enExample) |
| KR (1) | KR20050105443A (enExample) |
| CN (1) | CN1747938A (enExample) |
| AR (1) | AR043023A1 (enExample) |
| AU (1) | AU2004208825A1 (enExample) |
| BR (1) | BRPI0407247A (enExample) |
| CA (1) | CA2512616A1 (enExample) |
| HR (1) | HRP20050765A2 (enExample) |
| MX (1) | MXPA05008236A (enExample) |
| NO (1) | NO20054067L (enExample) |
| RU (1) | RU2005127584A (enExample) |
| TW (1) | TW200500347A (enExample) |
| WO (1) | WO2004069197A2 (enExample) |
| ZA (1) | ZA200505352B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004030663D1 (de) | 2003-03-05 | 2011-02-03 | Toray Industries | Aromatisches polymer, folie, elektrolytmembran und separator |
| WO2005037805A2 (en) * | 2003-10-15 | 2005-04-28 | Sumitomo Chemical Company, Limited | 1,2,4-thiadiazole compounds and pests controlling composition containing the same |
| AU2006334172A1 (en) * | 2005-12-30 | 2007-07-12 | Egis Gyogyszergyar Nyilvanosan Mukodo Reszvenytarsasag | Optical isomers of dihydro-2,3-benzodiazepines and their stereoselective synthesis |
| RU2314829C1 (ru) * | 2006-03-21 | 2008-01-20 | Войсковая Часть 41598 | Композиция для терапии судорожного синдрома |
| TW200902024A (en) * | 2007-04-02 | 2009-01-16 | Teva Pharma | Novel 2,3-benzodiazepine derivatives and their use as antipsychotic agents |
| PE20150729A1 (es) * | 2012-08-16 | 2015-06-14 | Bayer Pharma AG | 2,3-benzodiazepines |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU191698B (en) | 1984-07-27 | 1987-03-30 | Gyogyszerkutato Intezet | Process for producing new 1-aryl-5h-2beta-benzodiazepines |
| 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 |
| 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 |
| 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. |
| DE69525342T2 (de) | 1994-08-31 | 2002-11-07 | Eli Lilly And Co., Indianapolis | Dihydro-2,3-benzodiazepinderivate |
| DE19604920A1 (de) | 1996-02-01 | 1997-08-07 | Schering Ag | Neue 2,3-Benzodiazepinderivate, deren Herstellung und Verwendung als Arzneimittel |
| HU9600871D0 (en) | 1996-04-04 | 1996-05-28 | Gyogyszerkutato Intezet | New 2,3-benzodiazepine derivatives |
| 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 |
| SK1792000A3 (en) | 1997-08-12 | 2000-09-12 | Egyt Gyogyszervegyeszeti Gyar | 1,3-DIOXOLO(4,5-H)(2,3)BENZODIAZEPINE DERIVATIVES, PROCESS FORì (54) THE PREPARATION THEREOF, PHARMACEUTICAL COMPOSITION CO |
| HU227128B1 (en) | 1999-07-07 | 2010-07-28 | Egyt Gyogyszervegyeszeti Gyar | New 2,3-benzodiazepine derivatives |
-
2003
- 2003-02-04 US US10/358,053 patent/US6858605B2/en not_active Expired - Fee Related
-
2004
- 2004-02-03 BR BR0407247-2A patent/BRPI0407247A/pt not_active IP Right Cessation
- 2004-02-03 CN CNA200480003526XA patent/CN1747938A/zh active Pending
- 2004-02-03 WO PCT/US2004/003041 patent/WO2004069197A2/en not_active Ceased
- 2004-02-03 AU AU2004208825A patent/AU2004208825A1/en not_active Abandoned
- 2004-02-03 HR HR20050765A patent/HRP20050765A2/xx not_active Application Discontinuation
- 2004-02-03 US US10/771,847 patent/US20070027143A1/en not_active Abandoned
- 2004-02-03 ZA ZA200505352A patent/ZA200505352B/xx unknown
- 2004-02-03 MX MXPA05008236A patent/MXPA05008236A/es not_active Application Discontinuation
- 2004-02-03 KR KR1020057013696A patent/KR20050105443A/ko not_active Withdrawn
- 2004-02-03 CA CA002512616A patent/CA2512616A1/en not_active Abandoned
- 2004-02-03 EP EP04707792A patent/EP1592673A4/en not_active Withdrawn
- 2004-02-03 RU RU2005127584/04A patent/RU2005127584A/ru not_active Application Discontinuation
- 2004-02-03 JP JP2006503283A patent/JP2006516647A/ja not_active Withdrawn
- 2004-02-04 AR ARP040100342A patent/AR043023A1/es not_active Application Discontinuation
- 2004-02-04 TW TW093102551A patent/TW200500347A/zh unknown
-
2005
- 2005-09-01 NO NO20054067A patent/NO20054067L/no not_active Application Discontinuation
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