CZ227397A3 - Použití derivátu N-(4-arythiazol-2-yl)sulfonamidu jako kynurenin-3-hydroxylázových inhibitorů, derivát sulfonamidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje - Google Patents
Použití derivátu N-(4-arythiazol-2-yl)sulfonamidu jako kynurenin-3-hydroxylázových inhibitorů, derivát sulfonamidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje Download PDFInfo
- Publication number
- CZ227397A3 CZ227397A3 CZ972273A CZ227397A CZ227397A3 CZ 227397 A3 CZ227397 A3 CZ 227397A3 CZ 972273 A CZ972273 A CZ 972273A CZ 227397 A CZ227397 A CZ 227397A CZ 227397 A3 CZ227397 A3 CZ 227397A3
- Authority
- CZ
- Czechia
- Prior art keywords
- thiazol
- formula
- mixture
- nitrophenyl
- benzenesulfonamide
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 title claims description 18
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 15
- 108010033242 Kynurenine 3-monooxygenase Proteins 0.000 title abstract description 10
- 102100037652 Kynurenine 3-monooxygenase Human genes 0.000 title abstract description 10
- -1 methylenedioxy, phenoxy Chemical group 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 10
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 10
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 10
- 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 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 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 230000004913 activation Effects 0.000 claims abstract description 5
- 210000000987 immune system Anatomy 0.000 claims abstract description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 4
- 208000026278 immune system disease Diseases 0.000 claims abstract description 4
- 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
- 125000003118 aryl group Chemical group 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 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 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 206010012289 Dementia Diseases 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 208000014674 injury Diseases 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 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 230000008733 trauma Effects 0.000 claims description 6
- 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
- 208000035475 disorder Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 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 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 230000003612 virological effect Effects 0.000 claims description 5
- 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 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 4
- 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 4
- 208000030507 AIDS 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
- 201000006474 Brain Ischemia Diseases 0.000 claims description 4
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
- 208000023105 Huntington disease Diseases 0.000 claims description 4
- 206010021143 Hypoxia Diseases 0.000 claims description 4
- 206010027260 Meningitis viral 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
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 206010008118 cerebral infarction Diseases 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 230000007954 hypoxia Effects 0.000 claims description 4
- 230000005934 immune activation Effects 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- LBUHLNXAGRCQEG-UHFFFAOYSA-N n-[4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=CS1 LBUHLNXAGRCQEG-UHFFFAOYSA-N 0.000 claims description 4
- 238000012261 overproduction Methods 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 208000020431 spinal cord injury Diseases 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 4
- 201000010044 viral meningitis Diseases 0.000 claims description 4
- 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 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 239000013543 active substance Substances 0.000 claims description 3
- 230000007257 malfunction Effects 0.000 claims description 3
- 230000024587 synaptic transmission, glutamatergic Effects 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- 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
- 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 2
- 208000029028 brain injury Diseases 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
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 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
- 150000007979 thiazole derivatives Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 206010061216 Infarction Diseases 0.000 claims 3
- 208000006011 Stroke Diseases 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- 230000007574 infarction Effects 0.000 claims 2
- 230000005062 synaptic transmission Effects 0.000 claims 2
- ODVLMCWNGKLROU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)acetic acid Chemical class OC(=O)CC1=CC=C2OCOC2=C1 ODVLMCWNGKLROU-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 208000013557 cerebral hemisphere cancer Diseases 0.000 claims 1
- 201000008860 cerebrum cancer Diseases 0.000 claims 1
- 230000000848 glutamatergic effect Effects 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 claims 1
- 230000000926 neurological effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 6
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 220
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 180
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 158
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 156
- 239000000203 mixture Substances 0.000 description 148
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 70
- 239000000243 solution Substances 0.000 description 66
- 239000013078 crystal Substances 0.000 description 53
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 46
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 46
- 239000000725 suspension Substances 0.000 description 42
- 238000006386 neutralization reaction Methods 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 35
- 235000019341 magnesium sulphate Nutrition 0.000 description 35
- 239000012074 organic phase Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 238000001953 recrystallisation Methods 0.000 description 23
- 239000007787 solid Substances 0.000 description 23
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 238000001816 cooling Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 11
- 102000004190 Enzymes Human genes 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000000338 in vitro Methods 0.000 description 9
- YGPSJZOEDVAXAB-UHFFFAOYSA-N kynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- 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
- 150000003456 sulfonamides Chemical class 0.000 description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 230000005764 inhibitory process Effects 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
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 5
- 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 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RISZJRXLNZJZIF-UHFFFAOYSA-N 4-(3-phenylmethoxyphenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C1 RISZJRXLNZJZIF-UHFFFAOYSA-N 0.000 description 4
- CREMYEDHKUWVTB-UHFFFAOYSA-N 4-cyclohexylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1CCCCC1 CREMYEDHKUWVTB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- HCZHHEIFKROPDY-UHFFFAOYSA-N kynurenic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC(=O)C2=C1 HCZHHEIFKROPDY-UHFFFAOYSA-N 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 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
- 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 3
- NXEJAPAAZPULON-UHFFFAOYSA-N 4-[3-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(C=C(F)C=2)C(F)(F)F)=C1 NXEJAPAAZPULON-UHFFFAOYSA-N 0.000 description 3
- SAJMJWKYJRZVSC-UHFFFAOYSA-N 4-amino-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 SAJMJWKYJRZVSC-UHFFFAOYSA-N 0.000 description 3
- MLVVXRJBNCWRRD-UHFFFAOYSA-N 4-naphthalen-1-yl-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 MLVVXRJBNCWRRD-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
- 229920002261 Corn starch Polymers 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000002438 mitochondrial effect Effects 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
- VYYXLOSXJVFTSJ-UHFFFAOYSA-N n-[4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=CS1 VYYXLOSXJVFTSJ-UHFFFAOYSA-N 0.000 description 3
- MLBUADLFSPTJJO-UHFFFAOYSA-N n-[4-[[4-(3-nitrophenyl)-1,3-thiazol-2-yl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 MLBUADLFSPTJJO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 229960005404 sulfamethoxazole Drugs 0.000 description 3
- 150000003461 sulfonyl halides Chemical class 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
- NQKRXWYQYPNMCO-UHFFFAOYSA-N (4-methylphenyl)sulfonylthiourea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=S)C=C1 NQKRXWYQYPNMCO-UHFFFAOYSA-N 0.000 description 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
- ZXRFOUZBIPGLLS-UHFFFAOYSA-N 1,3-thiazol-2-ylazanium;bromide Chemical compound Br.NC1=NC=CS1 ZXRFOUZBIPGLLS-UHFFFAOYSA-N 0.000 description 2
- WKXVETMYCFRGET-UHFFFAOYSA-N 1,3-thiazole-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CS1 WKXVETMYCFRGET-UHFFFAOYSA-N 0.000 description 2
- TZIYNLSEBAYCBZ-UHFFFAOYSA-N 2-bromo-1-[3-(trifluoromethyl)phenyl]ethanone Chemical compound FC(F)(F)C1=CC=CC(C(=O)CBr)=C1 TZIYNLSEBAYCBZ-UHFFFAOYSA-N 0.000 description 2
- SIXKRNBZGWCFKP-UHFFFAOYSA-N 3,4-dichloro-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=C(Cl)C(Cl)=CC=3)SC=2)=C1 SIXKRNBZGWCFKP-UHFFFAOYSA-N 0.000 description 2
- NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 2
- VCKPUUFAIGNJHC-UHFFFAOYSA-N 3-hydroxykynurenine Chemical compound OC(=O)C(N)CC(=O)C1=CC=CC(O)=C1N VCKPUUFAIGNJHC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BACIUSFCOJKQHD-UHFFFAOYSA-N 4-[3,4-bis(phenylmethoxy)phenyl]-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(OCC=3C=CC=CC=3)C(OCC=3C=CC=CC=3)=CC=2)=C1 BACIUSFCOJKQHD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QMTUGYVKSXGQAX-UHFFFAOYSA-N 4-chloro-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=CC(Cl)=CC=3)SC=2)=C1 QMTUGYVKSXGQAX-UHFFFAOYSA-N 0.000 description 2
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 2
- QWVKRQQPNGVENK-UHFFFAOYSA-N 4-cyclohexyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=CC(=CC=3)C3CCCCC3)SC=2)=C1 QWVKRQQPNGVENK-UHFFFAOYSA-N 0.000 description 2
- MEHNQRWDJIFGRO-UHFFFAOYSA-N 4-methyl-n-(4-naphthalen-1-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C3=CC=CC=C3C=CC=2)=CS1 MEHNQRWDJIFGRO-UHFFFAOYSA-N 0.000 description 2
- WGYFCNUJZHAUII-UHFFFAOYSA-N 4-methyl-n-[4-(2-phenylmethoxyphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC=CC=2)OCC=2C=CC=CC=2)=CS1 WGYFCNUJZHAUII-UHFFFAOYSA-N 0.000 description 2
- YYQNPYJOQPOBJK-UHFFFAOYSA-N 4-methyl-n-[4-(3-phenylmethoxyphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=CS1 YYQNPYJOQPOBJK-UHFFFAOYSA-N 0.000 description 2
- RWNIDXQAHBPABU-UHFFFAOYSA-N 4-methyl-n-[4-(3-phenylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=CS1 RWNIDXQAHBPABU-UHFFFAOYSA-N 0.000 description 2
- HCFSSMPIXTYGLE-UHFFFAOYSA-N 4-methyl-n-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 HCFSSMPIXTYGLE-UHFFFAOYSA-N 0.000 description 2
- BKMMHCVPKNADSR-UHFFFAOYSA-N 4-methyl-n-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)C(F)(F)F)=CS1 BKMMHCVPKNADSR-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000186781 Listeria Species 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000194017 Streptococcus Species 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000006806 disease prevention Effects 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- BIFVAKUCWOQMRB-UHFFFAOYSA-N n-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(Cl)C(Cl)=CC=2)=CS1 BIFVAKUCWOQMRB-UHFFFAOYSA-N 0.000 description 2
- PUYGUIOZMGDJNE-UHFFFAOYSA-N n-[4-(3-aminophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(N)C=CC=2)=CS1 PUYGUIOZMGDJNE-UHFFFAOYSA-N 0.000 description 2
- GTDOXIHKRGCHGU-UHFFFAOYSA-N n-[4-(3-bromophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(Br)C=CC=2)=CS1 GTDOXIHKRGCHGU-UHFFFAOYSA-N 0.000 description 2
- NJVLSSHEOPSCEA-UHFFFAOYSA-N n-[4-(3-cyanophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)C#N)=CS1 NJVLSSHEOPSCEA-UHFFFAOYSA-N 0.000 description 2
- FOYYSRGAKDMMHI-UHFFFAOYSA-N n-[4-(3-hydroxy-4-methoxy-5-nitrophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=C([N+]([O-])=O)C(OC)=C(O)C=C1C1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 FOYYSRGAKDMMHI-UHFFFAOYSA-N 0.000 description 2
- QTTAYGLMSQIWFL-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-1-phenylmethanesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)CC=3C=CC=CC=3)SC=2)=C1 QTTAYGLMSQIWFL-UHFFFAOYSA-N 0.000 description 2
- DEFQWBMGFWZHNA-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 DEFQWBMGFWZHNA-UHFFFAOYSA-N 0.000 description 2
- BCSTXMINPUJFLR-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=CC=CC=3)SC=2)=C1 BCSTXMINPUJFLR-UHFFFAOYSA-N 0.000 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 description 2
- JMUKNDGBHXBZCS-UHFFFAOYSA-N n-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(Br)=CC=2)=CS1 JMUKNDGBHXBZCS-UHFFFAOYSA-N 0.000 description 2
- NHZJRACGGVBOLR-UHFFFAOYSA-N n-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(Cl)=CC=2)=CS1 NHZJRACGGVBOLR-UHFFFAOYSA-N 0.000 description 2
- WDKSPOUHIKJSCI-UHFFFAOYSA-N n-[4-(4-cyclohexylphenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(=CC=2)C2CCCCC2)=CS1 WDKSPOUHIKJSCI-UHFFFAOYSA-N 0.000 description 2
- JNLUXBUTTJOENI-UHFFFAOYSA-N n-[4-(4-hydroxy-3-methylphenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C)C(O)=CC=2)=CS1 JNLUXBUTTJOENI-UHFFFAOYSA-N 0.000 description 2
- HOSHSOKROXGRMT-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NS(=O)(=O)C=2C=CC(C)=CC=2)=N1 HOSHSOKROXGRMT-UHFFFAOYSA-N 0.000 description 2
- 230000000324 neuroprotective effect Effects 0.000 description 2
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000008057 potassium phosphate buffer Substances 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- JPBSJQZUINELEA-UHFFFAOYSA-N 1,2-oxazole-3-sulfonamide Chemical class NS(=O)(=O)C=1C=CON=1 JPBSJQZUINELEA-UHFFFAOYSA-N 0.000 description 1
- WOZCSRYOBKSMBL-UHFFFAOYSA-N 1,3-benzodioxole-5-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2OCOC2=C1 WOZCSRYOBKSMBL-UHFFFAOYSA-N 0.000 description 1
- ICUBASIDCXDQAW-UHFFFAOYSA-N 1,3-benzodioxole-5-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C2OCOC2=C1 ICUBASIDCXDQAW-UHFFFAOYSA-N 0.000 description 1
- JJDKSBUYHPCWPS-UHFFFAOYSA-N 1,3-dioxole-4-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=COCO1 JJDKSBUYHPCWPS-UHFFFAOYSA-N 0.000 description 1
- MHSHMGJHXSPXDH-UHFFFAOYSA-N 2-bromo-1-(2-phenylmethoxyphenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 MHSHMGJHXSPXDH-UHFFFAOYSA-N 0.000 description 1
- GANOKOPJCWEJLV-UHFFFAOYSA-N 2-bromo-1-(3,4-dihydroxy-5-nitrophenyl)ethanone Chemical compound OC1=CC(C(=O)CBr)=CC([N+]([O-])=O)=C1O GANOKOPJCWEJLV-UHFFFAOYSA-N 0.000 description 1
- RNOVVVKWCOIIEH-UHFFFAOYSA-N 2-bromo-1-(3-methoxy-4-phenylmethoxyphenyl)ethanone Chemical compound COC1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 RNOVVVKWCOIIEH-UHFFFAOYSA-N 0.000 description 1
- GFZOJLIHCWKKPR-UHFFFAOYSA-N 2-bromo-1-(3-phenylmethoxyphenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 GFZOJLIHCWKKPR-UHFFFAOYSA-N 0.000 description 1
- UDORKTOXFJWYDF-UHFFFAOYSA-N 2-bromo-1-(4-hydroxy-3-methylphenyl)ethanone Chemical compound CC1=CC(C(=O)CBr)=CC=C1O UDORKTOXFJWYDF-UHFFFAOYSA-N 0.000 description 1
- NHRZODGWBCYVRZ-UHFFFAOYSA-N 2-oxo-n-(1,3-thiazol-2-yl)-1h-pyrimidine-5-sulfonamide Chemical class C1=NC(O)=NC=C1S(=O)(=O)NC1=NC=CS1 NHRZODGWBCYVRZ-UHFFFAOYSA-N 0.000 description 1
- CUVRMFPIOIUHSV-UHFFFAOYSA-N 3,4-dimethoxy-n-(4-naphthalen-1-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C3=CC=CC=C3C=CC=2)=CS1 CUVRMFPIOIUHSV-UHFFFAOYSA-N 0.000 description 1
- YRRQAALAOMOXJW-UHFFFAOYSA-N 3-(2-amino-1,3-thiazol-4-yl)benzonitrile Chemical compound S1C(N)=NC(C=2C=C(C=CC=2)C#N)=C1 YRRQAALAOMOXJW-UHFFFAOYSA-N 0.000 description 1
- XWCGNFLHRINYCE-UHFFFAOYSA-N 3-(2-bromoacetyl)benzonitrile Chemical compound BrCC(=O)C1=CC=CC(C#N)=C1 XWCGNFLHRINYCE-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VYYLGKOLRSZXDQ-UHFFFAOYSA-N 3-bromo-4-methoxy-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=C(Br)C(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 VYYLGKOLRSZXDQ-UHFFFAOYSA-N 0.000 description 1
- LTVLATJRJIBHDR-UHFFFAOYSA-N 3-bromo-4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1Br LTVLATJRJIBHDR-UHFFFAOYSA-N 0.000 description 1
- UHXPUJVICKIDPM-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C(=CC(Cl)=CC=2)Cl)=C1 UHXPUJVICKIDPM-UHFFFAOYSA-N 0.000 description 1
- GIOVLGFPWZJIHQ-UHFFFAOYSA-N 4-(2-nitrophenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C(=CC=CC=2)[N+]([O-])=O)=C1 GIOVLGFPWZJIHQ-UHFFFAOYSA-N 0.000 description 1
- QNLNRENPKAQTMJ-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-1,3-thiazol-2-amine Chemical compound C1=C(OC)C(OC)=CC=C1C1=CSC(N)=N1 QNLNRENPKAQTMJ-UHFFFAOYSA-N 0.000 description 1
- LVBCVXLRBZQTDY-UHFFFAOYSA-N 4-(3-bromophenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(Br)C=CC=2)=C1 LVBCVXLRBZQTDY-UHFFFAOYSA-N 0.000 description 1
- IYWRIJUSOJGISM-UHFFFAOYSA-N 4-(3-methoxy-4-phenylmethoxyphenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.COC1=CC(C=2N=C(N)SC=2)=CC=C1OCC1=CC=CC=C1 IYWRIJUSOJGISM-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- DWGWNNCHJPKZNC-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC(Cl)=CC=2)=C1 DWGWNNCHJPKZNC-UHFFFAOYSA-N 0.000 description 1
- HXTRTCLUZHCDQS-UHFFFAOYSA-N 4-(4-cyclohexylphenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=CC(=CC=2)C2CCCCC2)=C1 HXTRTCLUZHCDQS-UHFFFAOYSA-N 0.000 description 1
- LSSLSLIGEXNGHL-UHFFFAOYSA-N 4-(4-methoxy-3-methylphenyl)-1,3-thiazol-2-amine Chemical compound C1=C(C)C(OC)=CC=C1C1=CSC(N)=N1 LSSLSLIGEXNGHL-UHFFFAOYSA-N 0.000 description 1
- YPVVEXKDPBRGIK-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1C1=CSC(N)=N1 YPVVEXKDPBRGIK-UHFFFAOYSA-N 0.000 description 1
- RYGLGFKXSWZERM-UHFFFAOYSA-N 4-(4-methylphenyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound [Br-].C1=CC(C)=CC=C1C1=CSC(N)=[NH+]1 RYGLGFKXSWZERM-UHFFFAOYSA-N 0.000 description 1
- FPIUGVQEXYOXEA-UHFFFAOYSA-N 4-[2-fluoro-5-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C(=CC=C(C=2)C(F)(F)F)F)=C1 FPIUGVQEXYOXEA-UHFFFAOYSA-N 0.000 description 1
- DBMHEYIHKLKSEW-UHFFFAOYSA-N 4-[3,4-bis(phenylmethoxy)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=C(OCC=3C=CC=CC=3)C(OCC=3C=CC=CC=3)=CC=2)=C1 DBMHEYIHKLKSEW-UHFFFAOYSA-N 0.000 description 1
- ZZDBATBJNFVJCB-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=C(C=CC=2)C(F)(F)F)=C1 ZZDBATBJNFVJCB-UHFFFAOYSA-N 0.000 description 1
- KTJWBJJBLRVZRM-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C(C=CC=2)C(F)(F)F)=C1 KTJWBJJBLRVZRM-UHFFFAOYSA-N 0.000 description 1
- PLOCBPFPBPRDRX-UHFFFAOYSA-N 4-methoxy-n-(4-naphthalen-1-yl-1,3-thiazol-2-yl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NC1=NC(C=2C3=CC=CC=C3C=CC=2)=CS1 PLOCBPFPBPRDRX-UHFFFAOYSA-N 0.000 description 1
- QPUUXPSDANGLOK-UHFFFAOYSA-N 4-methyl-n-[4-(4-phenylmethoxyphenyl)-1,3-thiazol-2-yl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=CS1 QPUUXPSDANGLOK-UHFFFAOYSA-N 0.000 description 1
- GWDNDNTTXIIXRS-UHFFFAOYSA-N 4-naphthalen-2-yl-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=C3C=CC=CC3=CC=2)=C1 GWDNDNTTXIIXRS-UHFFFAOYSA-N 0.000 description 1
- CCGAWSBUYAXXNK-UHFFFAOYSA-N 4-naphthalen-2-yl-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.S1C(N)=NC(C=2C=C3C=CC=CC3=CC=2)=C1 CCGAWSBUYAXXNK-UHFFFAOYSA-N 0.000 description 1
- BRTDEKQMIKCPKH-UHFFFAOYSA-N 4-phenylmethoxybenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1OCC1=CC=CC=C1 BRTDEKQMIKCPKH-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- JSBVVLSVARQKMS-UHFFFAOYSA-N 5-propan-2-ylpyridine-2-sulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)N=C1 JSBVVLSVARQKMS-UHFFFAOYSA-N 0.000 description 1
- JNPMWKWGLLFCSP-UHFFFAOYSA-N 5-tert-butyl-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]thiophene-2-sulfonamide Chemical compound S1C(C(C)(C)C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 JNPMWKWGLLFCSP-UHFFFAOYSA-N 0.000 description 1
- VQIKSHUGHZMRPE-UHFFFAOYSA-N 5-tert-butylthiophene-2-sulfonic acid Chemical compound CC(C)(C)C1=CC=C(S(O)(=O)=O)S1 VQIKSHUGHZMRPE-UHFFFAOYSA-N 0.000 description 1
- JWHLHIKHBZVZNS-UHFFFAOYSA-N 5-tert-butylthiophene-2-sulfonyl chloride Chemical compound CC(C)(C)C1=CC=C(S(Cl)(=O)=O)S1 JWHLHIKHBZVZNS-UHFFFAOYSA-N 0.000 description 1
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 1
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- RHSDLMPWPJDALQ-UHFFFAOYSA-N CC1(CC=CC=C1)S(=O)(=O)NC=1SC=C(N1)C1=CC(=CC=C1)[N+](=O)[O-] Chemical compound CC1(CC=CC=C1)S(=O)(=O)NC=1SC=C(N1)C1=CC(=CC=C1)[N+](=O)[O-] RHSDLMPWPJDALQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- 241000194033 Enterococcus Species 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 1
- 102000018899 Glutamate Receptors Human genes 0.000 description 1
- 108010027915 Glutamate Receptors Proteins 0.000 description 1
- 101001027246 Homo sapiens Kynurenine 3-monooxygenase Proteins 0.000 description 1
- 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 1
- YGPSJZOEDVAXAB-QMMMGPOBSA-N L-kynurenine Chemical compound OC(=O)[C@@H](N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-QMMMGPOBSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 101710138657 Neurotoxin Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- KPPOELIZRLLPGI-UHFFFAOYSA-N [4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]azanium;bromide Chemical compound Br.S1C(N)=NC(C=2C=C(Cl)C(Cl)=CC=2)=C1 KPPOELIZRLLPGI-UHFFFAOYSA-N 0.000 description 1
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000005620 boronic acid group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- WEDIIKBPDQQQJU-UHFFFAOYSA-N butane-1-sulfonyl chloride Chemical compound CCCCS(Cl)(=O)=O WEDIIKBPDQQQJU-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000006652 catabolic pathway Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001952 enzyme assay Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
- 238000010228 ex vivo assay Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012628 flowing agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000011539 homogenization buffer Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000005309 metal halides Chemical group 0.000 description 1
- SIXPZCDCMFKMQH-UHFFFAOYSA-N methanol;thiourea Chemical compound OC.NC(N)=S SIXPZCDCMFKMQH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- DNFMWWQJKOARGB-UHFFFAOYSA-N n-[4-(2,4-dichlorophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=CS1 DNFMWWQJKOARGB-UHFFFAOYSA-N 0.000 description 1
- FZEMPNPLMHGRJG-UHFFFAOYSA-N n-[4-(3,4-dihydroxy-5-nitrophenyl)-1,3-thiazol-2-yl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=CS1 FZEMPNPLMHGRJG-UHFFFAOYSA-N 0.000 description 1
- MKOBQAFOMQIZKE-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-1,3-benzodioxole-5-sulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=C4OCOC4=CC=3)SC=2)=C1 MKOBQAFOMQIZKE-UHFFFAOYSA-N 0.000 description 1
- RJHOOXQXHLKHBQ-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-4-phenylmethoxybenzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NS(=O)(=O)C=3C=CC(OCC=4C=CC=CC=4)=CC=3)SC=2)=C1 RJHOOXQXHLKHBQ-UHFFFAOYSA-N 0.000 description 1
- KOZLFFQOEMJNFN-UHFFFAOYSA-N n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]-5-propan-2-ylpyridine-2-sulfonamide Chemical compound N1=CC(C(C)C)=CC=C1S(=O)(=O)NC1=NC(C=2C=C(C=CC=2)[N+]([O-])=O)=CS1 KOZLFFQOEMJNFN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 239000002581 neurotoxin Substances 0.000 description 1
- 231100000618 neurotoxin Toxicity 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- OAHKWDDSKCRNFE-UHFFFAOYSA-N phenylmethanesulfonyl chloride Chemical compound ClS(=O)(=O)CC1=CC=CC=C1 OAHKWDDSKCRNFE-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000003765 sweetening agent Substances 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
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
- 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)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP96111661 | 1996-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ227397A3 true CZ227397A3 (cs) | 1998-02-18 |
Family
ID=8223010
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ972273A CZ227397A3 (cs) | 1996-07-19 | 1997-07-17 | Použití derivátu N-(4-arythiazol-2-yl)sulfonamidu jako kynurenin-3-hydroxylázových inhibitorů, derivát sulfonamidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje |
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) |
Families Citing this family (29)
| 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 |
| SE0001899D0 (sv) | 2000-05-22 | 2000-05-22 | Pharmacia & Upjohn Ab | New compounds |
| BR0116063A (pt) * | 2000-12-13 | 2004-08-03 | Wyeth Corp | Inibidores de sulfonamida heterocìclica da produção de beta amilóide e seus usos |
| US7094792B2 (en) | 2001-11-22 | 2006-08-22 | Biovitrum Ab | Inhibitors of 11-beta-hydroxy steroid dehydrogenase type 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 |
| JPWO2005054216A1 (ja) * | 2003-12-01 | 2007-06-28 | 株式会社リバース・プロテオミクス研究所 | 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 |
| US8071631B2 (en) * | 2006-08-16 | 2011-12-06 | The J. David Gladstone Institutes, A Testamentary Trust Established Under The Will Of J. David Gladstone | Small molecule inhibitors of kynurenine-3-monooxygenase |
| BRPI0905388A2 (pt) * | 2008-01-15 | 2015-10-13 | Siga Technologies Inc | "composição farmacêutica; compostos e métodos de tratamento de infecção por arenavirus" |
| 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 |
| CA2844128C (en) * | 2011-08-30 | 2020-09-01 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| 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 |
| 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 |
| 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 |
| CA2885762C (en) * | 2012-09-21 | 2022-05-03 | Rhode Island Hospital | Inhibitors of beta-hydroxylase for treatment of cancer |
| ES3022639T3 (en) | 2016-05-20 | 2025-05-28 | Xenon Pharmaceuticals Inc | Benzenesulfonamide compounds and their use as therapeutic agents |
| SG10201912372XA (en) | 2016-12-09 | 2020-02-27 | Xenon Pharmaceuticals Inc | Benzenesulfonamide compounds and their use as therapeutic agents |
| EP3807281A1 (en) | 2018-06-13 | 2021-04-21 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| PE20211066A1 (es) | 2018-08-31 | 2021-06-09 | Xenon Pharmaceuticals Inc | Compuestos de sulfonamida sustituidos con heteroarilo y su uso como agentes terapeuticos |
| US10752623B2 (en) | 2018-08-31 | 2020-08-25 | Xenon Pharmaceuticals Inc. | Heteroaryl-substituted sulfonamide compounds and their use as sodium channel inhibitors |
| US12030875B2 (en) * | 2018-09-07 | 2024-07-09 | PIC Therapeutics, Inc. | EIF4E inhibitors and uses thereof |
| 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 |
| AU689972B2 (en) * | 1994-11-29 | 1998-04-09 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/or salt 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 ZA ZA9706222A patent/ZA976222B/xx unknown
- 1997-07-14 IL IL12129897A patent/IL121298A/xx not_active IP Right Cessation
- 1997-07-14 NZ NZ328331A patent/NZ328331A/xx unknown
- 1997-07-14 HU HU9701193A patent/HUP9701193A3/hu 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 TR TR97/00653A patent/TR199700653A2/xx unknown
- 1997-07-17 CO CO97040540A patent/CO4900053A1/es unknown
- 1997-07-17 CZ CZ972273A patent/CZ227397A3/cs unknown
- 1997-07-17 MA MA24722A patent/MA24273A1/fr unknown
- 1997-07-18 AU AU28752/97A patent/AU725496B2/en not_active Ceased
- 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 HR HR96111661.3A patent/HRP970393A2/xx not_active Application Discontinuation
- 1997-07-18 CN CN97114715A patent/CN1176101A/zh active Pending
- 1997-07-18 PL PL97321203A patent/PL321203A1/xx unknown
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| IL121298A0 (en) | 1998-01-04 |
| ZA976222B (en) | 1998-01-19 |
| KR980008228A (ko) | 1998-04-30 |
| US5958910A (en) | 1999-09-28 |
| HUP9701193A2 (hu) | 1999-02-01 |
| AU2875297A (en) | 1998-01-29 |
| NZ328331A (en) | 1999-05-28 |
| JPH1067761A (ja) | 1998-03-10 |
| EP0819681A3 (de) | 1998-02-04 |
| MA24273A1 (fr) | 1998-04-01 |
| CO4900053A1 (es) | 2000-03-27 |
| BR9704023A (pt) | 1998-11-17 |
| CN1176101A (zh) | 1998-03-18 |
| HU9701193D0 (en) | 1997-09-29 |
| EP0819681A2 (de) | 1998-01-21 |
| AU725496B2 (en) | 2000-10-12 |
| IL121298A (en) | 2001-03-19 |
| SG91796A1 (en) | 2002-10-15 |
| NO973338L (no) | 1998-01-20 |
| TR199700653A2 (xx) | 1998-02-21 |
| HRP970393A2 (en) | 1998-04-30 |
| PL321203A1 (en) | 1998-02-02 |
| JP2991679B2 (ja) | 1999-12-20 |
| NO973338D0 (no) | 1997-07-18 |
| MX9705385A (es) | 1998-04-30 |
| US5877193A (en) | 1999-03-02 |
| YU30297A (sh) | 2000-10-30 |
| HUP9701193A3 (en) | 2000-08-28 |
| KR100247672B1 (ko) | 2000-04-01 |
| CA2210613A1 (en) | 1998-01-19 |
| PE91298A1 (es) | 1998-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ227397A3 (cs) | Použití derivátu N-(4-arythiazol-2-yl)sulfonamidu jako kynurenin-3-hydroxylázových inhibitorů, derivát sulfonamidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje | |
| MXPA97005385A (en) | Derivatives of n- (4-aril-tiazol-2-il) -sulfonam | |
| AU2017254523B2 (en) | Compounds and compositions for treating conditions associated with NLRP activity | |
| ES2494918T3 (es) | Compuestos de guanidina y su uso como componentes de unión para receptores 5-HT5 | |
| JP6648137B2 (ja) | ヘテロ環式誘導体およびその使用 | |
| KR101426093B1 (ko) | 뒤시엔느 근이영양증의 치료 | |
| JP5463285B2 (ja) | ナトリウムチャネル阻害物質 | |
| KR19990082622A (ko) | Il-8 수용체 길항제 | |
| JP6539839B2 (ja) | 新規のベンゼンスルホンアミドチアゾール化合物 | |
| BRPI0807626B1 (pt) | Processo para a síntese de compostos de 2-aminotiazol como inibidores de quinase | |
| HUE028656T2 (en) | Biphenyl-4-ylsulfonic acid arylamides and their use as therapeutic agents | |
| JP2003501459A (ja) | Il−8受容体アンタゴニスト | |
| JP2002531500A (ja) | Myt1キナーゼ阻害剤 | |
| AU2013318962A1 (en) | Coumarin derivative | |
| CA2624383C (en) | Salts of modulators of ppar and methods of treating metabolic disorders | |
| US7022702B2 (en) | Antiproliferative 1,2,3-thiadiazole compounds | |
| CA3220896A1 (en) | Inhibitors of .alpha.-hemolysin of staphylococcus aureus | |
| KR20210000564A (ko) | 신규 아만타딘 유도체 화합물 및 이의 용도 | |
| CN104220058A (zh) | 丝氨酸消旋酶抑制剂 | |
| WO2007047432A1 (en) | Sulfonamide derivatives as modulators of ppar | |
| NZ715751A (en) | Sulfonamides as modulators of sodium channels | |
| NZ715751B2 (en) | Sulfonamides as modulators of sodium channels | |
| BR112017011312B1 (pt) | Composto, composição farmacêutica e uso do composto | |
| AU2766100A (en) | Myt1 kinase inhibitors | |
| CZ256998A3 (cs) | Antagonista IL-8 receptoru |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic |