CA2557942C - Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique - Google Patents
Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique Download PDFInfo
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- CA2557942C CA2557942C CA2557942A CA2557942A CA2557942C CA 2557942 C CA2557942 C CA 2557942C CA 2557942 A CA2557942 A CA 2557942A CA 2557942 A CA2557942 A CA 2557942A CA 2557942 C CA2557942 C CA 2557942C
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- Prior art keywords
- alkyl
- groups
- aryl
- heteroaryl
- atom
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- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 230000001225 therapeutic effect Effects 0.000 title abstract description 7
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 31
- 125000004429 atom Chemical group 0.000 claims abstract description 28
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims abstract description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 206010028980 Neoplasm Diseases 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 9
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
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- 230000007170 pathology Effects 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- 206010002383 Angina Pectoris Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010003225 Arteriospasm coronary Diseases 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 3
- 208000003890 Coronary Vasospasm Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
- 208000033626 Renal failure acute Diseases 0.000 claims description 3
- 201000011040 acute kidney failure Diseases 0.000 claims description 3
- 208000012998 acute renal failure Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 231100000457 cardiotoxic Toxicity 0.000 claims description 3
- 230000001451 cardiotoxic effect Effects 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 208000037976 chronic inflammation Diseases 0.000 claims description 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 3
- 208000020832 chronic kidney disease Diseases 0.000 claims description 3
- 208000022831 chronic renal failure syndrome Diseases 0.000 claims description 3
- 201000011634 coronary artery vasospasm Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
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- 210000003141 lower extremity Anatomy 0.000 claims description 3
- 230000005012 migration Effects 0.000 claims description 3
- 238000013508 migration Methods 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 208000027232 peripheral nervous system disease Diseases 0.000 claims description 3
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- 230000002685 pulmonary effect Effects 0.000 claims description 3
- 208000037803 restenosis Diseases 0.000 claims description 3
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- 210000000329 smooth muscle myocyte Anatomy 0.000 claims description 3
- 230000009424 thromboembolic effect Effects 0.000 claims description 3
- 238000007675 cardiac surgery Methods 0.000 claims description 2
- 210000003709 heart valve Anatomy 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 208000005264 motor neuron disease Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 abstract description 9
- 239000012453 solvate Substances 0.000 abstract description 7
- 239000003446 ligand Substances 0.000 abstract description 5
- 102000004300 GABA-A Receptors Human genes 0.000 abstract 1
- 108090000839 GABA-A Receptors Proteins 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- 239000000047 product Substances 0.000 description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- -1 3H-benzo [e] indazol-1-yl Chemical group 0.000 description 21
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 18
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 229940049706 benzodiazepine Drugs 0.000 description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
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- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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- 239000011734 sodium Substances 0.000 description 4
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- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
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- 241000282414 Homo sapiens Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
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- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 210000000256 facial nerve Anatomy 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- RDPLOLUNEKBWBR-UHFFFAOYSA-L magnesium;sodium;sulfate Chemical compound [Na+].[Mg+2].[O-]S([O-])(=O)=O RDPLOLUNEKBWBR-UHFFFAOYSA-L 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
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- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- BGPWZVVCRUNVNB-UHFFFAOYSA-N di(propan-2-yl)carbamic acid;hydrochloride Chemical compound Cl.CC(C)N(C(C)C)C(O)=O BGPWZVVCRUNVNB-UHFFFAOYSA-N 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
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- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0405055 | 2004-05-11 | ||
| FR0405055A FR2870239B1 (fr) | 2004-05-11 | 2004-05-11 | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique. |
| PCT/FR2005/001154 WO2005121099A1 (fr) | 2004-05-11 | 2005-05-10 | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2557942A1 CA2557942A1 (fr) | 2005-12-22 |
| CA2557942C true CA2557942C (fr) | 2013-08-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2557942A Expired - Fee Related CA2557942C (fr) | 2004-05-11 | 2005-05-10 | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2870239B1 (fr) * | 2004-05-11 | 2006-06-16 | Sanofi Synthelabo | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique. |
| WO2007088528A1 (en) * | 2006-02-03 | 2007-08-09 | The Provost, Fellows And Scholars Of The College Of The Holy And Undivided Trinity Of Queen Elizabeth, Near Dublin | Microtubule targeting agents |
| CL2008000793A1 (es) * | 2007-03-23 | 2008-05-30 | Xenon Pharmaceuticals Inc | Compuestos derivados de dihidroindazol; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar un trastorno del hierro. |
| MX2016000669A (es) * | 2013-07-15 | 2016-11-11 | Basf Se | Compuestos plaguicidas. |
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| EP0607076A1 (fr) * | 1993-01-15 | 1994-07-20 | Synthelabo | Dérivés de 9h-imidazo 1,2-a benzimidazole-3-acétamide à activité GABA |
| TW403738B (en) * | 1994-08-12 | 2000-09-01 | Hoffmann La Roche | Tricyclic pyrazole derivatives |
| FR2741073B1 (fr) * | 1995-11-09 | 1997-12-12 | Synthelabo | Derives de 4,5-dihydroimidazo(1,2-a)pyrrolo(1,2,3-cd) benzimidazole, leur preparation et leur application en therapeutique |
| ID16283A (id) * | 1996-03-20 | 1997-09-18 | Astra Pharma Prod | Senyawa yang berguna dibidang farmasi |
| ZA9810490B (en) * | 1997-12-03 | 1999-05-20 | Dainippon Pharmaceutical Co | 2-Aryl-8-oxodihydropurine derivative process for the preparation thereof pharmaceutical composition containing the same and intermediate therefor |
| WO1999058117A1 (fr) * | 1998-05-13 | 1999-11-18 | Sanofi-Synthelabo | Utilisation de composes reduisant l'apoptose |
| MXPA03001945A (es) * | 2000-09-06 | 2003-09-10 | Neurogen Corp | Tetrahidroindazoles sustituidos con arilo y su uso como ligandos para el receptor gaba-a. |
| ATE425148T1 (de) * | 2000-09-18 | 2009-03-15 | Eisai R&D Man Co Ltd | Triazinone sowie deren medizinale anwendung |
| FR2870239B1 (fr) * | 2004-05-11 | 2006-06-16 | Sanofi Synthelabo | Derives de carbamate de 2h- ou 3h-benzo[e]indazol-1-yle, leur preparation et leur application en therapeutique. |
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2004
- 2004-05-11 FR FR0405055A patent/FR2870239B1/fr not_active Expired - Fee Related
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- 2005-05-09 AR ARP050101865A patent/AR049090A1/es unknown
- 2005-05-10 BR BRPI0508563-2A patent/BRPI0508563A/pt not_active IP Right Cessation
- 2005-05-10 NZ NZ549330A patent/NZ549330A/en not_active IP Right Cessation
- 2005-05-10 ES ES05770962T patent/ES2315898T3/es not_active Expired - Lifetime
- 2005-05-10 KR KR1020067018339A patent/KR101165483B1/ko not_active Expired - Fee Related
- 2005-05-10 DE DE602005010418T patent/DE602005010418D1/de not_active Expired - Lifetime
- 2005-05-10 WO PCT/FR2005/001154 patent/WO2005121099A1/fr not_active Ceased
- 2005-05-10 AT AT05770962T patent/ATE411295T1/de active
- 2005-05-10 SI SI200530546T patent/SI1747201T1/sl unknown
- 2005-05-10 PT PT05770962T patent/PT1747201E/pt unknown
- 2005-05-10 JP JP2007512277A patent/JP4909889B2/ja not_active Expired - Fee Related
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- 2005-05-10 RU RU2006132325/04A patent/RU2379293C2/ru not_active IP Right Cessation
- 2005-05-10 DK DK05770962T patent/DK1747201T3/da active
- 2005-05-10 CN CN200580007686A patent/CN100577648C/zh not_active Expired - Fee Related
- 2005-05-10 EP EP05770962A patent/EP1747201B8/fr not_active Expired - Lifetime
- 2005-05-10 RS RSP-2009/0012A patent/RS50724B/sr unknown
- 2005-05-10 TW TW094114981A patent/TWI349004B/zh not_active IP Right Cessation
- 2005-05-10 AU AU2005251982A patent/AU2005251982B2/en not_active Ceased
- 2005-05-10 HR HR20090012T patent/HRP20090012T3/xx unknown
- 2005-10-05 UA UAA200609699A patent/UA85866C2/uk unknown
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2006
- 2006-08-15 TN TNP2006000258A patent/TNSN06258A1/fr unknown
- 2006-08-22 IL IL177632A patent/IL177632A/en not_active IP Right Cessation
- 2006-08-24 CR CR8570A patent/CR8570A/es unknown
- 2006-08-29 MA MA29294A patent/MA28372A1/fr unknown
- 2006-08-29 EC EC2006006810A patent/ECSP066810A/es unknown
- 2006-08-30 ZA ZA2006/07244A patent/ZA200607244B/en unknown
- 2006-09-11 NO NO20064073A patent/NO20064073L/no not_active Application Discontinuation
- 2006-10-13 US US11/549,293 patent/US7501449B2/en not_active Expired - Fee Related
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2009
- 2009-01-14 CY CY20091100042T patent/CY1108710T1/el unknown
- 2009-01-27 US US12/360,535 patent/US8114899B2/en not_active Expired - Fee Related
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2012
- 2012-01-11 US US13/348,241 patent/US8258168B2/en not_active Expired - Fee Related
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