NZ549330A - 2H or 3H-benzo[e]indazol-1-yl carbamate derivatives, the preparation and therapeutic use thereof - Google Patents
2H or 3H-benzo[e]indazol-1-yl carbamate derivatives, the preparation and therapeutic use thereofInfo
- Publication number
- NZ549330A NZ549330A NZ549330A NZ54933005A NZ549330A NZ 549330 A NZ549330 A NZ 549330A NZ 549330 A NZ549330 A NZ 549330A NZ 54933005 A NZ54933005 A NZ 54933005A NZ 549330 A NZ549330 A NZ 549330A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- group
- compound
- groups
- aryl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- UIGCZRSWLFFOGB-UHFFFAOYSA-N 3h-benzo[e]indazol-1-yl carbamate Chemical class C1=CC=CC2=C3C(OC(=O)N)=NNC3=CC=C21 UIGCZRSWLFFOGB-UHFFFAOYSA-N 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 125000003118 aryl group Chemical group 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 102100031274 Translocator protein Human genes 0.000 claims abstract description 20
- 101710166801 Translocator protein Proteins 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 19
- 239000012453 solvate Substances 0.000 claims abstract description 15
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 230000000694 effects Effects 0.000 claims abstract description 9
- 230000007170 pathology Effects 0.000 claims abstract description 9
- 210000002161 motor neuron Anatomy 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 230000001154 acute effect Effects 0.000 claims abstract description 5
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 5
- 230000035755 proliferation Effects 0.000 claims abstract description 5
- 208000009304 Acute Kidney Injury Diseases 0.000 claims abstract description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 4
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 4
- 206010003225 Arteriospasm coronary Diseases 0.000 claims abstract description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
- 208000003890 Coronary Vasospasm Diseases 0.000 claims abstract description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims abstract description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims abstract description 4
- 208000033626 Renal failure acute Diseases 0.000 claims abstract description 4
- 206010052779 Transplant rejections Diseases 0.000 claims abstract description 4
- 230000036506 anxiety Effects 0.000 claims abstract description 4
- 208000020832 chronic kidney disease Diseases 0.000 claims abstract description 4
- 201000011634 coronary artery vasospasm Diseases 0.000 claims abstract description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims abstract description 4
- 206010015037 epilepsy Diseases 0.000 claims abstract description 4
- 208000019622 heart disease Diseases 0.000 claims abstract description 4
- 210000003709 heart valve Anatomy 0.000 claims abstract description 4
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 4
- 208000028867 ischemia Diseases 0.000 claims abstract description 4
- 210000003141 lower extremity Anatomy 0.000 claims abstract description 4
- 230000005012 migration Effects 0.000 claims abstract description 4
- 238000013508 migration Methods 0.000 claims abstract description 4
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 4
- 208000031225 myocardial ischemia Diseases 0.000 claims abstract description 4
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 4
- 208000027232 peripheral nervous system disease Diseases 0.000 claims abstract description 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims abstract description 4
- 230000002685 pulmonary effect Effects 0.000 claims abstract description 4
- 208000037803 restenosis Diseases 0.000 claims abstract description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 4
- 208000019116 sleep disease Diseases 0.000 claims abstract description 4
- 210000000329 smooth muscle myocyte Anatomy 0.000 claims abstract description 4
- 238000001356 surgical procedure Methods 0.000 claims abstract description 4
- 230000009424 thromboembolic effect Effects 0.000 claims abstract description 4
- 206010019280 Heart failures Diseases 0.000 claims abstract description 3
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 21
- 125000004429 atom Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 claims 1
- 230000003177 cardiotonic effect Effects 0.000 claims 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 abstract description 3
- 231100000457 cardiotoxic Toxicity 0.000 abstract description 2
- 230000001451 cardiotoxic effect Effects 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000047 product Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 239000012074 organic phase Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 238000007792 addition Methods 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- -1 indazol-l-yl carbamate derivatives Chemical class 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 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
- 241000700159 Rattus Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004076 pyridyl group Chemical group 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NSWPIPPPJGLXNI-UHFFFAOYSA-N Cl.C(C)N(C(OC1=NNC=2C=CC3=C(C12)C=CC=C3)=O)CC Chemical compound Cl.C(C)N(C(OC1=NNC=2C=CC3=C(C12)C=CC=C3)=O)CC NSWPIPPPJGLXNI-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 210000000256 facial nerve Anatomy 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- 210000004379 membrane Anatomy 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 230000035882 stress Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 150000004677 hydrates Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 125000002757 morpholinyl group Chemical group 0.000 description 3
- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000004193 piperazinyl group Chemical group 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
- RTLUPHDWSUGAOS-UHFFFAOYSA-N 4-iodopyridine Chemical compound IC1=CC=NC=C1 RTLUPHDWSUGAOS-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 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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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 102000004300 GABA-A Receptors Human genes 0.000 description 2
- 108090000839 GABA-A Receptors Proteins 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- 208000003251 Pruritus Diseases 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000005864 Sulphur Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 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
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- MOTPVGIVYNFZCR-UHFFFAOYSA-N (7-chloro-2-pyridin-4-yl-4,5-dihydrobenzo[e]indazol-1-yl) n,n-diethylcarbamate;hydrochloride Chemical compound Cl.CCN(CC)C(=O)OC1=C(C2=CC=C(Cl)C=C2CC2)C2=NN1C1=CC=NC=C1 MOTPVGIVYNFZCR-UHFFFAOYSA-N 0.000 description 1
- MVLRWUSFABMCCS-UHFFFAOYSA-N (7-chloro-3-pyridin-4-yl-4,5-dihydrobenzo[e]indazol-1-yl) n,n-di(propan-2-yl)carbamate Chemical compound C1=2CCC3=CC(Cl)=CC=C3C=2C(OC(=O)N(C(C)C)C(C)C)=NN1C1=CC=NC=C1 MVLRWUSFABMCCS-UHFFFAOYSA-N 0.000 description 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
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| Publication Number | Publication Date |
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| NZ549330A true NZ549330A (en) | 2010-08-27 |
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| NZ549330A NZ549330A (en) | 2004-05-11 | 2005-05-10 | 2H or 3H-benzo[e]indazol-1-yl carbamate derivatives, the preparation and therapeutic use thereof |
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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. |
Family Cites Families (9)
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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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