CA2210613A1 - N-(4-aryl-thiazol-2-yl)-sulphonamide derivatives and their use - Google Patents
N-(4-aryl-thiazol-2-yl)-sulphonamide derivatives and their useInfo
- Publication number
- CA2210613A1 CA2210613A1 CA002210613A CA2210613A CA2210613A1 CA 2210613 A1 CA2210613 A1 CA 2210613A1 CA 002210613 A CA002210613 A CA 002210613A CA 2210613 A CA2210613 A CA 2210613A CA 2210613 A1 CA2210613 A1 CA 2210613A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- thiazol
- nitro
- mixture
- amino
- 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.)
- Abandoned
Links
- -1 nitro, amino, methylenedioxy, phenoxy Chemical group 0.000 claims abstract description 41
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
- 150000002367 halogens Chemical class 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 13
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 9
- 230000002265 prevention Effects 0.000 claims abstract description 9
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 9
- 230000004913 activation Effects 0.000 claims abstract description 8
- 210000000987 immune system Anatomy 0.000 claims abstract description 8
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 73
- 238000000034 method Methods 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 230000002490 cerebral effect Effects 0.000 claims description 8
- 230000006378 damage Effects 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- 230000008733 trauma Effects 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 claims description 7
- CQTUVGBSDYRJEU-UHFFFAOYSA-N 4-methyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 CQTUVGBSDYRJEU-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 206010027202 Meningitis bacterial Diseases 0.000 claims description 5
- 201000009904 bacterial meningitis Diseases 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000003612 virological effect Effects 0.000 claims description 5
- FKPKAHJGASPYDU-UHFFFAOYSA-N 4-amino-n-[4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=CS1 FKPKAHJGASPYDU-UHFFFAOYSA-N 0.000 claims description 4
- PQIXZNOJCVFICV-UHFFFAOYSA-N 4-methoxy-n-(4-naphthalen-2-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C3C=CC=CC3=CC=2)=CS1 PQIXZNOJCVFICV-UHFFFAOYSA-N 0.000 claims description 4
- 206010065040 AIDS dementia complex Diseases 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 4
- 206010027260 Meningitis viral Diseases 0.000 claims description 4
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- NDPBMCKQJOZAQX-UHFFFAOYSA-N Ro 61-8048 Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 NDPBMCKQJOZAQX-UHFFFAOYSA-N 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 201000004810 Vascular dementia Diseases 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 230000007954 hypoxia Effects 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 230000004807 localization Effects 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- NJXAUNJKBBCJKI-UHFFFAOYSA-N n-[4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=C(F)C=2)C(F)(F)F)=CS1 NJXAUNJKBBCJKI-UHFFFAOYSA-N 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 210000000278 spinal cord Anatomy 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- 201000010044 viral meningitis Diseases 0.000 claims description 4
- IRCPPACQBUIBNT-UHFFFAOYSA-N 4-methoxy-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 IRCPPACQBUIBNT-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 230000007257 malfunction Effects 0.000 claims description 3
- HEONEOMFRWFNEL-UHFFFAOYSA-N n-[4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-3,4-dimethoxybenzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=CS1 HEONEOMFRWFNEL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- JCRDSLRMAQGMHH-UHFFFAOYSA-N 4-methyl-n-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(=CC=2)[N+]([O-])=O)=CS1 JCRDSLRMAQGMHH-UHFFFAOYSA-N 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- QEVQBRTZBNHUIG-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]naphthalene-2-sulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=C4C=CC=CC4=CC=3)SC=2)=C1 QEVQBRTZBNHUIG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 claims description 2
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 2
- 201000010901 lateral sclerosis Diseases 0.000 claims 1
- 208000005264 motor neuron disease Diseases 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 abstract description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 217
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 165
- 239000000203 mixture Substances 0.000 description 162
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 150
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 126
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 92
- 239000003610 charcoal Substances 0.000 description 84
- 235000011167 hydrochloric acid Nutrition 0.000 description 82
- 229960000443 hydrochloric acid Drugs 0.000 description 82
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- 239000000243 solution Substances 0.000 description 70
- 239000013078 crystal Substances 0.000 description 55
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 46
- 239000000725 suspension Substances 0.000 description 43
- 238000006386 neutralization reaction Methods 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 39
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 32
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 24
- 238000001953 recrystallisation Methods 0.000 description 24
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000003480 eluent Substances 0.000 description 14
- 102000004190 Enzymes Human genes 0.000 description 13
- 108090000790 Enzymes Proteins 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- MSUUWZQPNLHQQH-UHFFFAOYSA-N 4-(3-nitrophenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 MSUUWZQPNLHQQH-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- RSJSYCZYQNJQPY-UHFFFAOYSA-N 3,4-dimethoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1OC RSJSYCZYQNJQPY-UHFFFAOYSA-N 0.000 description 5
- SSPZQMFKVVFCAS-UHFFFAOYSA-N 4-(3-nitrophenyl)-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.S1C(N)=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 SSPZQMFKVVFCAS-UHFFFAOYSA-N 0.000 description 5
- HBNCZXYGAZZYRJ-UHFFFAOYSA-N 4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=C1 HBNCZXYGAZZYRJ-UHFFFAOYSA-N 0.000 description 5
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 5
- 239000001828 Gelatine Substances 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- CHBDOPARQRNCDM-UHFFFAOYSA-N 4-(3-nitrophenyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=C1 CHBDOPARQRNCDM-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- YGPSJZOEDVAXAB-QMMMGPOBSA-N L-kynurenine Chemical compound OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-QMMMGPOBSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LQPAQYQHUGXFED-UHFFFAOYSA-N 2-bromo-1-[2-fluoro-5-(trifluoromethyl)phenyl]ethanone Chemical compound FC1=CC=C(C(F)(F)F)C=C1C(=O)CBr LQPAQYQHUGXFED-UHFFFAOYSA-N 0.000 description 3
- SQVOBBIFCRMZOB-UHFFFAOYSA-N 2-bromo-1-[3-fluoro-5-(trifluoromethyl)phenyl]ethanone Chemical compound FC1=CC(C(=O)CBr)=CC(C(F)(F)F)=C1 SQVOBBIFCRMZOB-UHFFFAOYSA-N 0.000 description 3
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 description 3
- CREMYEDHKUWVTB-UHFFFAOYSA-N 4-cyclohexylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1CCCCC1 CREMYEDHKUWVTB-UHFFFAOYSA-N 0.000 description 3
- CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 210000003734 kidney Anatomy 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NHWPCLBEANNEBP-UHFFFAOYSA-N n-(methoxymethyl)-4-methyl-n-[4-(3-phenylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C=1C=C(C)C=CC=1S(=O)(=O)N(COC)C(SC=1)=NC=1C(C=1)=CC=CC=1C1=CC=CC=C1 NHWPCLBEANNEBP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 229960005404 sulfamethoxazole Drugs 0.000 description 3
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96111661.3 | 1996-07-19 | ||
| EP96111661 | 1996-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2210613A1 true CA2210613A1 (en) | 1998-01-19 |
Family
ID=8223010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002210613A Abandoned CA2210613A1 (en) | 1996-07-19 | 1997-07-16 | N-(4-aryl-thiazol-2-yl)-sulphonamide derivatives and their use |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US5877193A (en:Method) |
| EP (1) | EP0819681A3 (en:Method) |
| JP (1) | JP2991679B2 (en:Method) |
| KR (1) | KR100247672B1 (en:Method) |
| CN (1) | CN1176101A (en:Method) |
| AU (1) | AU725496B2 (en:Method) |
| BR (1) | BR9704023A (en:Method) |
| CA (1) | CA2210613A1 (en:Method) |
| CO (1) | CO4900053A1 (en:Method) |
| CZ (1) | CZ227397A3 (en:Method) |
| HR (1) | HRP970393A2 (en:Method) |
| HU (1) | HUP9701193A3 (en:Method) |
| IL (1) | IL121298A (en:Method) |
| MA (1) | MA24273A1 (en:Method) |
| MX (1) | MX9705385A (en:Method) |
| NO (1) | NO973338L (en:Method) |
| NZ (1) | NZ328331A (en:Method) |
| PE (1) | PE91298A1 (en:Method) |
| PL (1) | PL321203A1 (en:Method) |
| SG (1) | SG91796A1 (en:Method) |
| TR (1) | TR199700653A2 (en:Method) |
| YU (1) | YU30297A (en:Method) |
| ZA (1) | ZA976222B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618961B2 (en) | 2000-05-22 | 2009-11-17 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9725138D0 (en) * | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Thiophenesulfonamide compounds |
| GB9725141D0 (en) * | 1997-11-27 | 1998-01-28 | Pharmacia & Upjohn Spa | Benzenesulfonamide compounds |
| US6211185B1 (en) | 1999-05-05 | 2001-04-03 | Veterinary Pharmacy Corporation | Concentrate comprising a sulfonamide in solution, a 2,4-diaminopyrimidine in stable suspension within said solution, and a suspending agent |
| NZ538100A (en) * | 2000-12-13 | 2006-07-28 | Arqule Inc | Heterocyclic sulfonamide inhibitors of beta amyloid production |
| RS44304A (sr) | 2001-11-22 | 2007-06-04 | Biovitrum Ab., | Inhibitori 11-beta- hidroksistereoidne dehidrogenaze tipa 1 |
| US6869970B2 (en) * | 2002-02-04 | 2005-03-22 | Novartis Ag | Crystalline salt forms of valsartan |
| FR2849599B1 (fr) * | 2003-01-07 | 2006-12-29 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete |
| FR2849598B1 (fr) * | 2003-01-07 | 2006-09-22 | Merck Sante Sas | Utilisation d'inhibiteurs de la kynurenine-3-hydroxylase pour le traitement du diabete, par augmentation du nombre de cellules des ilots de langerhans |
| WO2005054216A1 (ja) * | 2003-12-01 | 2005-06-16 | Reverse Proteomics Research Institute Co., Ltd. | 新規抗癌剤「スルコキシン」 |
| DK2054397T3 (en) * | 2006-08-16 | 2016-01-18 | J David Gladstone Inst A Testamentary Trust Established Under The Will Of J David Gladstone | SMALL MOLECULAR INHIBITORS OF KYNURENIN-3-MONOOXYGENASE |
| EP2420494B1 (en) | 2006-08-16 | 2014-10-08 | The J. David Gladstone Institutes, A Testamentary Trust Established under The Will of J. David Gladstone | Use of thiadiazole compounds as inhibitors of kynurenine-3-monooxygenase |
| US8623347B2 (en) * | 2008-01-15 | 2014-01-07 | Siga Technologies, Inc. | Antiviral drugs for treatment of arenavirus infection |
| WO2009124086A2 (en) * | 2008-04-04 | 2009-10-08 | Siga Technologies, Inc. | Antibacterial drug for treatment of staphylococcus aureus and other gram-positive bacterial infections |
| UA103319C2 (en) * | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Thiazole- and oxazole-benzene sulfonamide compounds |
| CN101602687A (zh) * | 2008-06-13 | 2009-12-16 | 上海特化医药科技有限公司 | 6-硝基苯乙酮类化合物、其制备方法及用途 |
| CN106518845B (zh) * | 2011-08-30 | 2019-09-13 | Chdi基金会股份有限公司 | 犬尿氨酸-3-单加氧酶抑制剂、药物组合物及其使用方法 |
| CN102627589A (zh) * | 2012-04-05 | 2012-08-08 | 天津理工大学 | 一种两步合成制备4-异丙基苯磺酰氯的方法和工艺 |
| CN102633696A (zh) * | 2012-04-05 | 2012-08-15 | 天津理工大学 | 一种两步合成制备对位取代烷基苯磺酰氯的方法和工艺 |
| CN102633695A (zh) * | 2012-04-05 | 2012-08-15 | 天津理工大学 | 一种4-异丙基苯磺酰氯的制备方法和工艺 |
| CN102633687B (zh) * | 2012-04-05 | 2016-06-08 | 天津瑞岭化工有限公司 | 一种对位取代烷基苯磺酰氯的制备方法和工艺 |
| JP6469009B2 (ja) * | 2012-09-21 | 2019-02-13 | ロード アイランド ホスピタル | がん処置用β−ヒドロキシラーゼ阻害剤 |
| ES3022639T3 (en) | 2016-05-20 | 2025-05-28 | Xenon Pharmaceuticals Inc | Benzenesulfonamide compounds and their use as therapeutic agents |
| MX2019006697A (es) | 2016-12-09 | 2019-08-16 | Xenon Pharmaceuticals Inc | Compuestos de bencenosulfonamida y su uso como agentes terapeuticos. |
| WO2019241533A1 (en) | 2018-06-13 | 2019-12-19 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| WO2020047312A1 (en) | 2018-08-31 | 2020-03-05 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
| BR112021000209A2 (pt) | 2018-08-31 | 2021-08-24 | Xenon Pharmaceuticals Inc. | Compostos de sulfonamida substituída por heteroarila e seu uso como agentes terapêuticos |
| CN113164419A (zh) * | 2018-09-07 | 2021-07-23 | 皮克医疗公司 | Eif4e抑制剂和其用途 |
| CN114516807B (zh) * | 2022-02-24 | 2023-11-17 | 南京大学 | 一种含硝基多取代芳香二胺单体及其制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5591761A (en) * | 1993-05-20 | 1997-01-07 | Texas Biotechnology Corporation | Thiophenyl-, furyl-and pyrrolyl-sulfonamides and derivatives thereof that modulate the activity of endothelin |
| NZ247440A (en) * | 1992-05-06 | 1995-04-27 | Squibb & Sons Inc | Phenyl sulphonamide derivatives, preparation and pharmaceutical compositions thereof |
| WO1996016650A1 (en) * | 1994-11-29 | 1996-06-06 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial or bactericide comprising 2-aminothiazole derivative and salts thereof |
| GB9702194D0 (en) * | 1997-02-04 | 1997-03-26 | Lilly Co Eli | Sulphonide derivatives |
-
1997
- 1997-06-12 US US08/874,050 patent/US5877193A/en not_active Expired - Fee Related
- 1997-07-09 SG SG9702412A patent/SG91796A1/en unknown
- 1997-07-10 EP EP97111745A patent/EP0819681A3/de not_active Ceased
- 1997-07-11 YU YU30297A patent/YU30297A/sh unknown
- 1997-07-11 PE PE1997000613A patent/PE91298A1/es not_active Application Discontinuation
- 1997-07-14 HU HU9701193A patent/HUP9701193A3/hu unknown
- 1997-07-14 IL IL12129897A patent/IL121298A/xx not_active IP Right Cessation
- 1997-07-14 ZA ZA9706222A patent/ZA976222B/xx unknown
- 1997-07-14 NZ NZ328331A patent/NZ328331A/xx unknown
- 1997-07-16 JP JP9190990A patent/JP2991679B2/ja not_active Expired - Fee Related
- 1997-07-16 CA CA002210613A patent/CA2210613A1/en not_active Abandoned
- 1997-07-16 MX MX9705385A patent/MX9705385A/es not_active Application Discontinuation
- 1997-07-17 CO CO97040540A patent/CO4900053A1/es unknown
- 1997-07-17 CZ CZ972273A patent/CZ227397A3/cs unknown
- 1997-07-17 TR TR97/00653A patent/TR199700653A2/xx unknown
- 1997-07-17 MA MA24722A patent/MA24273A1/fr unknown
- 1997-07-18 BR BR9704023A patent/BR9704023A/pt active Search and Examination
- 1997-07-18 NO NO973338A patent/NO973338L/no not_active Application Discontinuation
- 1997-07-18 AU AU28752/97A patent/AU725496B2/en not_active Ceased
- 1997-07-18 PL PL97321203A patent/PL321203A1/xx unknown
- 1997-07-18 CN CN97114715A patent/CN1176101A/zh active Pending
- 1997-07-18 HR HR96111661.3A patent/HRP970393A2/xx not_active Application Discontinuation
- 1997-07-19 KR KR1019970033826A patent/KR100247672B1/ko not_active Expired - Fee Related
-
1998
- 1998-11-20 US US09/197,070 patent/US5958910A/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7618961B2 (en) | 2000-05-22 | 2009-11-17 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 1 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR980008228A (ko) | 1998-04-30 |
| US5877193A (en) | 1999-03-02 |
| YU30297A (sh) | 2000-10-30 |
| HUP9701193A3 (en) | 2000-08-28 |
| AU2875297A (en) | 1998-01-29 |
| EP0819681A2 (de) | 1998-01-21 |
| KR100247672B1 (ko) | 2000-04-01 |
| HUP9701193A2 (hu) | 1999-02-01 |
| CN1176101A (zh) | 1998-03-18 |
| JP2991679B2 (ja) | 1999-12-20 |
| NZ328331A (en) | 1999-05-28 |
| PL321203A1 (en) | 1998-02-02 |
| NO973338D0 (no) | 1997-07-18 |
| HU9701193D0 (en) | 1997-09-29 |
| NO973338L (no) | 1998-01-20 |
| TR199700653A2 (xx) | 1998-02-21 |
| IL121298A (en) | 2001-03-19 |
| PE91298A1 (es) | 1998-12-31 |
| AU725496B2 (en) | 2000-10-12 |
| MA24273A1 (fr) | 1998-04-01 |
| BR9704023A (pt) | 1998-11-17 |
| EP0819681A3 (de) | 1998-02-04 |
| CO4900053A1 (es) | 2000-03-27 |
| HRP970393A2 (en) | 1998-04-30 |
| JPH1067761A (ja) | 1998-03-10 |
| ZA976222B (en) | 1998-01-19 |
| IL121298A0 (en) | 1998-01-04 |
| SG91796A1 (en) | 2002-10-15 |
| US5958910A (en) | 1999-09-28 |
| MX9705385A (es) | 1998-04-30 |
| CZ227397A3 (cs) | 1998-02-18 |
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