SK13812000A3 - Benzénsulfónamidové deriváty, spôsob ich prípravy, ich použitie a farmaceutická kompozícia, ktorá ich obsahuje - Google Patents
Benzénsulfónamidové deriváty, spôsob ich prípravy, ich použitie a farmaceutická kompozícia, ktorá ich obsahuje Download PDFInfo
- Publication number
- SK13812000A3 SK13812000A3 SK1381-2000A SK13812000A SK13812000A3 SK 13812000 A3 SK13812000 A3 SK 13812000A3 SK 13812000 A SK13812000 A SK 13812000A SK 13812000 A3 SK13812000 A3 SK 13812000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- group
- carbon atoms
- groups
- optionally substituted
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 321
- 150000001875 compounds Chemical class 0.000 claims abstract description 319
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 183
- 238000000034 method Methods 0.000 claims abstract description 137
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 150000002148 esters Chemical class 0.000 claims abstract description 39
- 238000001727 in vivo Methods 0.000 claims abstract description 38
- 238000002360 preparation method Methods 0.000 claims abstract description 37
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000001424 substituent group Chemical group 0.000 claims abstract description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 20
- 230000000694 effects Effects 0.000 claims abstract description 19
- 241001465754 Metazoa Species 0.000 claims abstract description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 375
- -1 morpholino, thiomorpholino, piperidyl Chemical group 0.000 claims description 242
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 114
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 112
- 229910052757 nitrogen Inorganic materials 0.000 claims description 108
- 125000000623 heterocyclic group Chemical group 0.000 claims description 93
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 80
- 125000003545 alkoxy group Chemical group 0.000 claims description 56
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 49
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 150000001721 carbon Chemical group 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 39
- 125000001589 carboacyl group Chemical group 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000001624 naphthyl group Chemical group 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 30
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000004429 atom Chemical group 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 14
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 14
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 13
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 claims description 13
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 230000001965 increasing effect Effects 0.000 claims description 12
- 125000005936 piperidyl group Chemical group 0.000 claims description 12
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 125000000815 N-oxide group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 6
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 5
- UTKVKYWAOULRJL-UHFFFAOYSA-N n-[4-[di(butan-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCC(C)N(C(C)CC)S(=O)(=O)C1=CC=C(NC(=O)C(C)(O)C(F)(F)F)C=C1 UTKVKYWAOULRJL-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 4
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 150000002009 diols Chemical class 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 150000002924 oxiranes Chemical class 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006241 alcohol protecting group Chemical group 0.000 claims description 3
- 150000001345 alkine derivatives Chemical class 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 150000002829 nitrogen Chemical class 0.000 claims description 3
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 287
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 261
- 239000000243 solution Substances 0.000 description 185
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 104
- 239000000203 mixture Substances 0.000 description 104
- 235000019439 ethyl acetate Nutrition 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 83
- 238000001819 mass spectrum Methods 0.000 description 65
- 239000012267 brine Substances 0.000 description 59
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 59
- 238000005481 NMR spectroscopy Methods 0.000 description 58
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 48
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 37
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 30
- 238000004440 column chromatography Methods 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- 239000007864 aqueous solution Substances 0.000 description 28
- 239000002585 base Substances 0.000 description 27
- 239000002024 ethyl acetate extract Substances 0.000 description 26
- 239000006260 foam Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 23
- 239000003054 catalyst Substances 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 20
- 238000010992 reflux Methods 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 18
- 239000003480 eluent Substances 0.000 description 17
- 239000000284 extract Substances 0.000 description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 13
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- UWKQJZCTQGMHKD-UHFFFAOYSA-N 2,6-di-tert-butylpyridine Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=N1 UWKQJZCTQGMHKD-UHFFFAOYSA-N 0.000 description 11
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 11
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 238000003776 cleavage reaction Methods 0.000 description 10
- 239000008103 glucose Substances 0.000 description 10
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 9
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 239000012258 stirred mixture Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 8
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 8
- 102000053067 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Human genes 0.000 description 8
- 108700009582 Pyruvate Dehydrogenase Acetyl-Transferring Kinase Proteins 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 8
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
- 238000003556 assay Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 206010012601 diabetes mellitus Diseases 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 229940076788 pyruvate Drugs 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- DRYMMXUBDRJPDS-UHFFFAOYSA-N 2-hydroxy-2-methylpropanamide Chemical compound CC(C)(O)C(N)=O DRYMMXUBDRJPDS-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 6
- YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 102000004169 proteins and genes Human genes 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229940054269 sodium pyruvate Drugs 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 241000588724 Escherichia coli Species 0.000 description 5
- 241000282412 Homo Species 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 5
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 5
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 5
- 229950006238 nadide Drugs 0.000 description 5
- 229940124530 sulfonamide Drugs 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 125000001984 thiazolidinyl group Chemical group 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- CTGJACFEVDCYMC-GSVOUGTGSA-N (2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid Chemical compound OC(=O)[C@](O)(C)C(F)(F)F CTGJACFEVDCYMC-GSVOUGTGSA-N 0.000 description 4
- 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 4
- 102000004877 Insulin Human genes 0.000 description 4
- 108090001061 Insulin Proteins 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 125000003435 aroyl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 4
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229940125396 insulin Drugs 0.000 description 4
- 125000000842 isoxazolyl group Chemical group 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 125000003226 pyrazolyl group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YXVCLPJQTZXJLH-UHFFFAOYSA-N thiamine(1+) diphosphate chloride Chemical compound [Cl-].CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N YXVCLPJQTZXJLH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 3
- ALOQYFFSHSEVJH-UHFFFAOYSA-N 4-acetamido-3-chlorobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1Cl ALOQYFFSHSEVJH-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 208000013824 Acidemia Diseases 0.000 description 3
- 208000010444 Acidosis Diseases 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 229920002785 Croscarmellose sodium Polymers 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 description 3
- 108091000080 Phosphotransferase Proteins 0.000 description 3
- 239000002250 absorbent Substances 0.000 description 3
- 230000002745 absorbent Effects 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000007080 aromatic substitution reaction Methods 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000002299 complementary DNA Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229960001681 croscarmellose sodium Drugs 0.000 description 3
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 3
- 229960005215 dichloroacetic acid Drugs 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 3
- 102000020233 phosphotransferase Human genes 0.000 description 3
- 238000003752 polymerase chain reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001422 pyrrolinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 3
- 229960002363 thiamine pyrophosphate Drugs 0.000 description 3
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 3
- 239000011678 thiamine pyrophosphate Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
- RBTCRFLJLUNCLL-UHFFFAOYSA-N (1-chloro-2-methyl-1-oxopropan-2-yl) acetate Chemical compound CC(=O)OC(C)(C)C(Cl)=O RBTCRFLJLUNCLL-UHFFFAOYSA-N 0.000 description 2
- PUAZOPQAOZTOTP-SECBINFHSA-N (2r)-n-(2-chloro-4-sulfamoylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(N)(=O)=O)C=C1Cl PUAZOPQAOZTOTP-SECBINFHSA-N 0.000 description 2
- XJVOPOWBIDUKFI-SECBINFHSA-N (2r)-n-(2-chlorophenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=CC=C1Cl XJVOPOWBIDUKFI-SECBINFHSA-N 0.000 description 2
- XGTKRRGGXYUURY-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[[4-(2-hydroxyethylamino)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(NCCO)C=C1 XGTKRRGGXYUURY-QGZVFWFLSA-N 0.000 description 2
- CTGJACFEVDCYMC-VKHMYHEASA-N (2s)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid Chemical compound OC(=O)[C@@](O)(C)C(F)(F)F CTGJACFEVDCYMC-VKHMYHEASA-N 0.000 description 2
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 2
- RBUQOUQQUQCSAU-UHFFFAOYSA-N 2-(4-aminoanilino)ethanol Chemical compound NC1=CC=C(NCCO)C=C1 RBUQOUQQUQCSAU-UHFFFAOYSA-N 0.000 description 2
- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- YRSMOVHHQNFATG-UHFFFAOYSA-N 2-chloro-4-morpholin-4-ylsulfonylaniline Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)N1CCOCC1 YRSMOVHHQNFATG-UHFFFAOYSA-N 0.000 description 2
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- IVCQKNKGXMVJOZ-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound NC(=O)C(O)(C)C(F)(F)F IVCQKNKGXMVJOZ-UHFFFAOYSA-N 0.000 description 2
- YYVAMBNPSIGVGI-SECBINFHSA-N 3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]benzenesulfonyl chloride Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1Cl YYVAMBNPSIGVGI-SECBINFHSA-N 0.000 description 2
- AGTSXXZWXWHAKH-UHFFFAOYSA-N 4-(1,3-dioxolan-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1OCCO1 AGTSXXZWXWHAKH-UHFFFAOYSA-N 0.000 description 2
- BJHZVGOUZORXET-UHFFFAOYSA-N 4-amino-3-chloro-n-(4-methoxyphenyl)benzenesulfonamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C(Cl)=C1 BJHZVGOUZORXET-UHFFFAOYSA-N 0.000 description 2
- RIBJIKMOCULTTG-UHFFFAOYSA-N 4-amino-3-fluorobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1F RIBJIKMOCULTTG-UHFFFAOYSA-N 0.000 description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 2
- FLDSMVTWEZKONL-AWEZNQCLSA-N 5,5-dimethyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound CC1(CC2=C(NN=C2C(=O)N[C@@H]2C(N(C3=C(OC2)C=CC=C3)C)=O)CCO1)C FLDSMVTWEZKONL-AWEZNQCLSA-N 0.000 description 2
- RSGVKIIEIXOMPY-UHFFFAOYSA-N 5-(trifluoromethyl)pyridin-2-amine Chemical compound NC1=CC=C(C(F)(F)F)C=N1 RSGVKIIEIXOMPY-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- 201000006474 Brain Ischemia Diseases 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- 208000010428 Muscle Weakness Diseases 0.000 description 2
- 208000021642 Muscular disease Diseases 0.000 description 2
- 206010028372 Muscular weakness Diseases 0.000 description 2
- 201000009623 Myopathy Diseases 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- 102000007056 Recombinant Fusion Proteins Human genes 0.000 description 2
- 108010008281 Recombinant Fusion Proteins Proteins 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 125000005101 aryl methoxy carbonyl group Chemical group 0.000 description 2
- 125000005002 aryl methyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
- 230000036983 biotransformation Effects 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- ZDQWVKDDJDIVAL-UHFFFAOYSA-N catecholborane Chemical compound C1=CC=C2O[B]OC2=C1 ZDQWVKDDJDIVAL-UHFFFAOYSA-N 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 206010008118 cerebral infarction Diseases 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 238000013375 chromatographic separation Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 2
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000012894 fetal calf serum Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- 230000004153 glucose metabolism Effects 0.000 description 2
- 210000003494 hepatocyte Anatomy 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- RZXGITJRZKXJCN-UHFFFAOYSA-N methyl 4-[(4-amino-3-chlorophenyl)sulfonylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=C(N)C(Cl)=C1 RZXGITJRZKXJCN-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- LICFRZDRPNUZFK-UHFFFAOYSA-N morpholin-4-ylmethanamine Chemical compound NCN1CCOCC1 LICFRZDRPNUZFK-UHFFFAOYSA-N 0.000 description 2
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 2
- MFYRWKNKSNQQFA-UHFFFAOYSA-N n-[2-chloro-4-[[5-(trifluoromethyl)pyridin-2-yl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(F)(F)F)C=N1 MFYRWKNKSNQQFA-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229940049954 penicillin Drugs 0.000 description 2
- 238000005897 peptide coupling reaction Methods 0.000 description 2
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
- 230000026731 phosphorylation Effects 0.000 description 2
- 238000006366 phosphorylation reaction Methods 0.000 description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000010410 reperfusion Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000001488 sodium phosphate Substances 0.000 description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229960005322 streptomycin Drugs 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- DLNKOYKMWOXYQA-VXNVDRBHSA-N (+)-norephedrine Chemical compound C[C@@H](N)[C@@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-VXNVDRBHSA-N 0.000 description 1
- DLNKOYKMWOXYQA-CBAPKCEASA-N (-)-norephedrine Chemical compound C[C@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-CBAPKCEASA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 description 1
- KHFRBUAUDKIMKB-MRXNPFEDSA-N (2R)-N-[2-chloro-4-[(2,4-difluorophenyl)methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound ClC1=C(C=CC(=C1)S(=O)(=O)NCC1=C(C=C(C=C1)F)F)NC([C@@](C(F)(F)F)(C)O)=O KHFRBUAUDKIMKB-MRXNPFEDSA-N 0.000 description 1
- SKGWNVUOJSEKCI-OAHLLOKOSA-N (2R)-N-[2-chloro-4-[3-(dimethylamino)propyl-methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CN(C)CCCN(C)S(=O)(=O)C1=CC(Cl)=C(NC(=O)[C@@](C)(O)C(F)(F)F)C=C1 SKGWNVUOJSEKCI-OAHLLOKOSA-N 0.000 description 1
- PKVHTUMFSHORCQ-OAHLLOKOSA-N (2R)-N-[2-chloro-4-[4-(hydroxymethyl)piperidin-1-yl]sulfonylphenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound ClC1=C(C=CC(=C1)S(=O)(=O)N1CCC(CC1)CO)NC([C@@](C(F)(F)F)(C)O)=O PKVHTUMFSHORCQ-OAHLLOKOSA-N 0.000 description 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- DIHXWDZLQAERDA-VKHMYHEASA-N (2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl chloride Chemical compound ClC(=O)[C@@](O)(C)C(F)(F)F DIHXWDZLQAERDA-VKHMYHEASA-N 0.000 description 1
- OXWVRUALJKVSFN-MRXNPFEDSA-N (2r)-3,3,3-trifluoro-n-[2-fluoro-4-[(2-methylsulfonylphenyl)sulfamoyl]phenyl]-2-hydroxy-2-methylpropanamide Chemical compound C1=C(F)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC=C1S(C)(=O)=O OXWVRUALJKVSFN-MRXNPFEDSA-N 0.000 description 1
- MXXIRUANQAJXBK-MRXNPFEDSA-N (2r)-3,3,3-trifluoro-n-[2-fluoro-4-[(3-methylsulfonylphenyl)sulfamoyl]phenyl]-2-hydroxy-2-methylpropanamide Chemical compound C1=C(F)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC(S(C)(=O)=O)=C1 MXXIRUANQAJXBK-MRXNPFEDSA-N 0.000 description 1
- YHMOOWZTQUUEQM-CYBMUJFWSA-N (2r)-n-(2-chloro-4-morpholin-4-ylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCOCC1 YHMOOWZTQUUEQM-CYBMUJFWSA-N 0.000 description 1
- WTNCKLVOKCXDAU-CYBMUJFWSA-N (2r)-n-(2-chloro-4-piperazin-1-ylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCNCC1 WTNCKLVOKCXDAU-CYBMUJFWSA-N 0.000 description 1
- UBBYHHILHAORHT-CYBMUJFWSA-N (2r)-n-(2-chloro-4-pyrrolidin-1-ylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCCC1 UBBYHHILHAORHT-CYBMUJFWSA-N 0.000 description 1
- KDRDLRPNYQHNHI-CYBMUJFWSA-N (2r)-n-[2-chloro-4-(2,5-dihydropyrrol-1-ylsulfonyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CC=CC1 KDRDLRPNYQHNHI-CYBMUJFWSA-N 0.000 description 1
- HSYSJPPEPJWUCH-LLVKDONJSA-N (2r)-n-[2-chloro-4-(2-hydroxyethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)NCCO)C=C1Cl HSYSJPPEPJWUCH-LLVKDONJSA-N 0.000 description 1
- PCEQDXNYTUNMSF-MRXNPFEDSA-N (2r)-n-[2-chloro-4-(2-piperidin-1-ylethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCCN1CCCCC1 PCEQDXNYTUNMSF-MRXNPFEDSA-N 0.000 description 1
- ZSRDAOYQIHISJX-GFCCVEGCSA-N (2r)-n-[2-chloro-4-(3-hydroxypropylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)NCCCO)C=C1Cl ZSRDAOYQIHISJX-GFCCVEGCSA-N 0.000 description 1
- MVZAQJWVSGPVAT-CYBMUJFWSA-N (2r)-n-[2-chloro-4-(4-hydroxybutylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)NCCCCO)C=C1Cl MVZAQJWVSGPVAT-CYBMUJFWSA-N 0.000 description 1
- YBHHDKXWEIEIQJ-CQSZACIVSA-N (2r)-n-[2-chloro-4-(4-hydroxypiperidin-1-yl)sulfonylphenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCC(O)CC1 YBHHDKXWEIEIQJ-CQSZACIVSA-N 0.000 description 1
- GWSWOKZGTIKBDL-GOSISDBHSA-N (2r)-n-[2-chloro-4-(4-pyrrolidin-1-ylpiperidin-1-yl)sulfonylphenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCC(N2CCCC2)CC1 GWSWOKZGTIKBDL-GOSISDBHSA-N 0.000 description 1
- DEEWWEKZQZLEAH-GFCCVEGCSA-N (2r)-n-[2-chloro-4-(cyclopropylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1CC1 DEEWWEKZQZLEAH-GFCCVEGCSA-N 0.000 description 1
- SRAUODURYYKAAX-CYBMUJFWSA-N (2r)-n-[2-chloro-4-(diethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 SRAUODURYYKAAX-CYBMUJFWSA-N 0.000 description 1
- FIFGJPMAGITGFC-LLVKDONJSA-N (2r)-n-[2-chloro-4-(dimethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 FIFGJPMAGITGFC-LLVKDONJSA-N 0.000 description 1
- MQXWKDYMNRRCJG-LLVKDONJSA-N (2r)-n-[2-chloro-4-(ethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCNS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 MQXWKDYMNRRCJG-LLVKDONJSA-N 0.000 description 1
- RPMXSKCXTLFSCU-GFCCVEGCSA-N (2r)-n-[2-chloro-4-(propylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCCNS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 RPMXSKCXTLFSCU-GFCCVEGCSA-N 0.000 description 1
- UTZSWEGCKNIASP-OAHLLOKOSA-N (2r)-n-[2-chloro-4-(pyridin-2-ylmethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=CC=N1 UTZSWEGCKNIASP-OAHLLOKOSA-N 0.000 description 1
- OBEAYRCLKKAQKP-CQSZACIVSA-N (2r)-n-[2-chloro-4-(pyridin-2-ylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC=N1 OBEAYRCLKKAQKP-CQSZACIVSA-N 0.000 description 1
- VPETUWRKODTKNY-OAHLLOKOSA-N (2r)-n-[2-chloro-4-(pyridin-3-ylmethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=CN=C1 VPETUWRKODTKNY-OAHLLOKOSA-N 0.000 description 1
- AQUNRYUSXGMBKR-OAHLLOKOSA-N (2r)-n-[2-chloro-4-(pyridin-4-ylmethylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=NC=C1 AQUNRYUSXGMBKR-OAHLLOKOSA-N 0.000 description 1
- HPOCAYUNDOVFIU-CYBMUJFWSA-N (2r)-n-[2-chloro-4-(pyrimidin-2-ylsulfamoyl)phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=NC=CC=N1 HPOCAYUNDOVFIU-CYBMUJFWSA-N 0.000 description 1
- VZFNQGRXOOTBOX-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(2,4-dichlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1Cl VZFNQGRXOOTBOX-OAHLLOKOSA-N 0.000 description 1
- PWCAEXPVNCMHRC-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(2-chloro-4-iodophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(I)C=C1Cl PWCAEXPVNCMHRC-OAHLLOKOSA-N 0.000 description 1
- UIGRNALSDWNTGX-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(2-chlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC=C1Cl UIGRNALSDWNTGX-OAHLLOKOSA-N 0.000 description 1
- AGFAGQYHGGVOEO-CQSZACIVSA-N (2r)-n-[2-chloro-4-[(2-chloropyridin-3-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CN=C1Cl AGFAGQYHGGVOEO-CQSZACIVSA-N 0.000 description 1
- ICPNPKWEJBSXKL-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(2-fluoro-4-iodophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(I)C=C1F ICPNPKWEJBSXKL-OAHLLOKOSA-N 0.000 description 1
- YGCBZOYPILMKCP-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(2-nitrophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC=C1[N+]([O-])=O YGCBZOYPILMKCP-OAHLLOKOSA-N 0.000 description 1
- BGRPORXONCPXEA-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(3,4-dichlorophenyl)methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=C(Cl)C(Cl)=C1 BGRPORXONCPXEA-MRXNPFEDSA-N 0.000 description 1
- KIBYYXOWNUNOQT-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(3,4-dichlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Cl)=C1 KIBYYXOWNUNOQT-OAHLLOKOSA-N 0.000 description 1
- NTVXHRJMAUFHPI-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[(3,4-dimethylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(C)C(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 NTVXHRJMAUFHPI-QGZVFWFLSA-N 0.000 description 1
- SEXZRERAGITJIO-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(3,5-dichlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC(Cl)=CC(Cl)=C1 SEXZRERAGITJIO-OAHLLOKOSA-N 0.000 description 1
- BWKDQNVJWOZLDB-CQSZACIVSA-N (2r)-n-[2-chloro-4-[(3,5-dichloropyridin-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=NC=C(Cl)C=C1Cl BWKDQNVJWOZLDB-CQSZACIVSA-N 0.000 description 1
- AJQIFUQRTWYDJH-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(3-chlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC(Cl)=C1 AJQIFUQRTWYDJH-OAHLLOKOSA-N 0.000 description 1
- IEFSCIPAWRXTAP-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(3-iodophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC(I)=C1 IEFSCIPAWRXTAP-OAHLLOKOSA-N 0.000 description 1
- BEKBXNJXKGLLLS-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(3-methylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC1=CC=CC(NS(=O)(=O)C=2C=C(Cl)C(NC(=O)[C@@](C)(O)C(F)(F)F)=CC=2)=C1 BEKBXNJXKGLLLS-MRXNPFEDSA-N 0.000 description 1
- NMWMAKLHXQUTSR-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(4,6-dimethylpyridin-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC1=CC(C)=NC(NS(=O)(=O)C=2C=C(Cl)C(NC(=O)[C@@](C)(O)C(F)(F)F)=CC=2)=C1 NMWMAKLHXQUTSR-MRXNPFEDSA-N 0.000 description 1
- WNDSPJROXGTFOX-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(4-chlorophenyl)methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=C(Cl)C=C1 WNDSPJROXGTFOX-MRXNPFEDSA-N 0.000 description 1
- AFTODSJCGHAVQL-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(4-chlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1 AFTODSJCGHAVQL-OAHLLOKOSA-N 0.000 description 1
- XLOOVLJTKWOHJE-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(4-fluorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(F)C=C1 XLOOVLJTKWOHJE-OAHLLOKOSA-N 0.000 description 1
- BCVJTYZEHLDSOV-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(4-formylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C=O)C=C1 BCVJTYZEHLDSOV-MRXNPFEDSA-N 0.000 description 1
- QDBICXBZNPPQDD-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(4-hydroxyphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(O)C=C1 QDBICXBZNPPQDD-OAHLLOKOSA-N 0.000 description 1
- OXMFFAWDRBFZMI-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(4-methoxyphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(OC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 OXMFFAWDRBFZMI-MRXNPFEDSA-N 0.000 description 1
- ZUMDWRIKNLNJFV-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(4-methyl-1,4-diazepan-1-yl)sulfonyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1CN(C)CCCN1S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 ZUMDWRIKNLNJFV-OAHLLOKOSA-N 0.000 description 1
- NCFACCWJKRDCBY-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[(4-methylbenzenecarbothioyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(C)=CC=C1C(=S)NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 NCFACCWJKRDCBY-QGZVFWFLSA-N 0.000 description 1
- NVRHCAVGTUXKCB-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[(4-methylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 NVRHCAVGTUXKCB-MRXNPFEDSA-N 0.000 description 1
- RXJYDTZNABLFPL-CQSZACIVSA-N (2r)-n-[2-chloro-4-[(5-chloropyridin-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=N1 RXJYDTZNABLFPL-CQSZACIVSA-N 0.000 description 1
- RTUZURVNCFFTSC-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[(5-methylpyridin-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound N1=CC(C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 RTUZURVNCFFTSC-OAHLLOKOSA-N 0.000 description 1
- PKZHCTMVDQOSFQ-CQSZACIVSA-N (2r)-n-[2-chloro-4-[2-(dimethylamino)ethyl-methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CN(C)CCN(C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 PKZHCTMVDQOSFQ-CQSZACIVSA-N 0.000 description 1
- SQTQHESHCFUIPR-BTQNPOSSSA-N (2r)-n-[2-chloro-4-[2-(dimethylamino)ethylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide;hydrochloride Chemical compound Cl.CN(C)CCNS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 SQTQHESHCFUIPR-BTQNPOSSSA-N 0.000 description 1
- SFLNRTRYUWNXTH-CQSZACIVSA-N (2r)-n-[2-chloro-4-[2-hydroxyethyl(3-hydroxypropyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)N(CCO)CCCO)C=C1Cl SFLNRTRYUWNXTH-CQSZACIVSA-N 0.000 description 1
- SBXHSBCIMWARFB-CQSZACIVSA-N (2r)-n-[2-chloro-4-[2-hydroxyethyl(propan-2-yl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound OCCN(C(C)C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 SBXHSBCIMWARFB-CQSZACIVSA-N 0.000 description 1
- ZYGVHJBFXFASPX-CQSZACIVSA-N (2r)-n-[2-chloro-4-[3-(dimethylamino)propylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CN(C)CCCNS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 ZYGVHJBFXFASPX-CQSZACIVSA-N 0.000 description 1
- NFOGGRDZEXYUMW-GENIYJEYSA-N (2r)-n-[2-chloro-4-[4-(1-hydroxyethyl)piperazin-1-yl]sulfonylphenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1CN(C(O)C)CCN1S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 NFOGGRDZEXYUMW-GENIYJEYSA-N 0.000 description 1
- DCSWZNKKJQRBLA-OAHLLOKOSA-N (2r)-n-[2-chloro-4-[4-(dimethylamino)butylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CN(C)CCCCNS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 DCSWZNKKJQRBLA-OAHLLOKOSA-N 0.000 description 1
- MLGBGQTYQYTKKA-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[[2-fluoro-4-(trifluoromethyl)phenyl]methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=C(C(F)(F)F)C=C1F MLGBGQTYQYTKKA-MRXNPFEDSA-N 0.000 description 1
- HOMAJARSKKGDCW-LJQANCHMSA-N (2r)-n-[2-chloro-4-[[4-(2-ethoxyethylsulfanyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(SCCOCC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 HOMAJARSKKGDCW-LJQANCHMSA-N 0.000 description 1
- YUXDXBAZXUCIFR-LJQANCHMSA-N (2r)-n-[2-chloro-4-[[4-(2-ethoxyethylsulfonyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(S(=O)(=O)CCOCC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 YUXDXBAZXUCIFR-LJQANCHMSA-N 0.000 description 1
- BIAUWKUHBZPLIY-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[[4-(2-hydroxyethylsulfanyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(SCCO)C=C1 BIAUWKUHBZPLIY-QGZVFWFLSA-N 0.000 description 1
- HJOMCKKSPIVJKG-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[[4-(2-hydroxyethylsulfonyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(S(=O)(=O)CCO)C=C1 HJOMCKKSPIVJKG-QGZVFWFLSA-N 0.000 description 1
- YEKPMRAGWNVMEN-OAQYLSRUSA-N (2r)-n-[2-chloro-4-[[4-(4-methylpiperazine-1-carbonyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 YEKPMRAGWNVMEN-OAQYLSRUSA-N 0.000 description 1
- UHWLMNZMLYFGSN-QGZVFWFLSA-N (2r)-n-[2-chloro-4-[[4-(ethylsulfamoyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 UHWLMNZMLYFGSN-QGZVFWFLSA-N 0.000 description 1
- DADIJLGRUUKIAO-MRXNPFEDSA-N (2r)-n-[2-chloro-4-[[4-(methylsulfamoyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 DADIJLGRUUKIAO-MRXNPFEDSA-N 0.000 description 1
- KXWCGUYUHZEYNT-HXUWFJFHSA-N (2r)-n-[2-chloro-4-[[4-(morpholine-4-carbonyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(=O)N2CCOCC2)C=C1 KXWCGUYUHZEYNT-HXUWFJFHSA-N 0.000 description 1
- YFRPPZMAKZNDIS-GOSISDBHSA-N (2r)-n-[2-chloro-4-[[4-(thiadiazol-4-yl)phenyl]methylsulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NCC1=CC=C(C=2N=NSC=2)C=C1 YFRPPZMAKZNDIS-GOSISDBHSA-N 0.000 description 1
- MFYRWKNKSNQQFA-CQSZACIVSA-N (2r)-n-[2-chloro-4-[[5-(trifluoromethyl)pyridin-2-yl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(F)(F)F)C=N1 MFYRWKNKSNQQFA-CQSZACIVSA-N 0.000 description 1
- XUIYVCZIMJIZSW-CYBMUJFWSA-N (2r)-n-[2-chloro-4-[methyl(propyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CCCN(C)S(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 XUIYVCZIMJIZSW-CYBMUJFWSA-N 0.000 description 1
- UUZHXPBYBOMHBX-OAHLLOKOSA-N (2r)-n-[2-chloro-5-[(2-chlorophenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC(S(=O)(=O)NC=2C(=CC=CC=2)Cl)=C1 UUZHXPBYBOMHBX-OAHLLOKOSA-N 0.000 description 1
- ITGPOSJNHCTDAY-RFVHGSKJSA-N (2r)-n-[4-(2-aminoethylsulfamoyl)-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide;hydrochloride Chemical compound Cl.FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)NCCN)C=C1Cl ITGPOSJNHCTDAY-RFVHGSKJSA-N 0.000 description 1
- LOTVMZZCGNZRCK-LLVKDONJSA-N (2r)-n-[4-(acetylsulfamoyl)-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC(=O)NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 LOTVMZZCGNZRCK-LLVKDONJSA-N 0.000 description 1
- MBANDMVPSQCBSC-RFVHGSKJSA-N (2r)-n-[4-[(2-aminoacetyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide;hydrochloride Chemical compound Cl.FC(F)(F)[C@@](O)(C)C(=O)NC1=CC=C(S(=O)(=O)NC(=O)CN)C=C1Cl MBANDMVPSQCBSC-RFVHGSKJSA-N 0.000 description 1
- UOFXJKQYRZWEDR-OAHLLOKOSA-N (2r)-n-[4-[(3-bromophenyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=CC(Br)=C1 UOFXJKQYRZWEDR-OAHLLOKOSA-N 0.000 description 1
- VFBFTDSEBQIGDB-QGZVFWFLSA-N (2r)-n-[4-[(4-acetylphenyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(C(=O)C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 VFBFTDSEBQIGDB-QGZVFWFLSA-N 0.000 description 1
- DYDLVKHJGMHAEW-QGZVFWFLSA-N (2r)-n-[4-[(4-aminophenyl)-(2-hydroxyethyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N(CCO)C1=CC=C(N)C=C1 DYDLVKHJGMHAEW-QGZVFWFLSA-N 0.000 description 1
- TZJQLAQXGGVULP-OAHLLOKOSA-N (2r)-n-[4-[(4-aminophenyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(N)C=C1 TZJQLAQXGGVULP-OAHLLOKOSA-N 0.000 description 1
- CPDYFQIPTGIMIB-LJQANCHMSA-N (2r)-n-[4-[(4-tert-butylphenyl)sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(C(C)(C)C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 CPDYFQIPTGIMIB-LJQANCHMSA-N 0.000 description 1
- NZKPRXGLIFQGCF-QGZVFWFLSA-N (2r)-n-[4-[[4-(acetylsulfamoyl)phenyl]sulfamoyl]-2-chlorophenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=CC(S(=O)(=O)NC(=O)C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 NZKPRXGLIFQGCF-QGZVFWFLSA-N 0.000 description 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 description 1
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical compound O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- WHZIZZOTISTHCT-UHFFFAOYSA-N 2-aminothiophene-3-carboxamide Chemical compound NC(=O)C=1C=CSC=1N WHZIZZOTISTHCT-UHFFFAOYSA-N 0.000 description 1
- WTBLIFRXXFPOID-MRXNPFEDSA-N 2-chloro-n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylbenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1Cl WTBLIFRXXFPOID-MRXNPFEDSA-N 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- INSUSOZBMWJGDG-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazol-4-amine Chemical compound CC1=NOC(C)=C1N INSUSOZBMWJGDG-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- FVZODFVCIDBDGS-UHFFFAOYSA-N 3-bromo-4-chloroaniline Chemical compound NC1=CC=C(Cl)C(Br)=C1 FVZODFVCIDBDGS-UHFFFAOYSA-N 0.000 description 1
- JUVRXJXSPNIFBZ-UHFFFAOYSA-N 4-(trifluoromethoxy)thiadiazole Chemical group FC(OC=1N=NSC1)(F)F JUVRXJXSPNIFBZ-UHFFFAOYSA-N 0.000 description 1
- PPVRMPPLECDING-UHFFFAOYSA-N 4-[(4-aminophenyl)diazenyl]benzenesulfonic acid Chemical compound C1=CC(N)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 PPVRMPPLECDING-UHFFFAOYSA-N 0.000 description 1
- PMCJNKSHDBZAMD-HXUWFJFHSA-N 4-[[3-chloro-4-[[(2R)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]-N-(2-methylpropyl)benzamide Chemical compound ClC1=C(C=CC(=C1)S(=O)(=O)NC1=CC=C(C=C1)C(=O)NCC(C)C)NC([C@@](C(F)(F)F)(C)O)=O PMCJNKSHDBZAMD-HXUWFJFHSA-N 0.000 description 1
- KXTAZWRSDHXQAR-GOSISDBHSA-N 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]-n,n-dimethylbenzamide Chemical compound C1=CC(C(=O)N(C)C)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 KXTAZWRSDHXQAR-GOSISDBHSA-N 0.000 description 1
- DBVDPVBXYHVAIJ-GOSISDBHSA-N 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]-n-ethylbenzamide Chemical compound C1=CC(C(=O)NCC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 DBVDPVBXYHVAIJ-GOSISDBHSA-N 0.000 description 1
- YWMNXVFXAQNUMG-QGZVFWFLSA-N 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]-n-methylsulfonylbenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(=O)NS(C)(=O)=O)C=C1 YWMNXVFXAQNUMG-QGZVFWFLSA-N 0.000 description 1
- DXOIFELAAPYDRO-OAHLLOKOSA-N 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]benzenesulfonyl fluoride Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(S(F)(=O)=O)C=C1 DXOIFELAAPYDRO-OAHLLOKOSA-N 0.000 description 1
- SUKNIPCMSFNQQV-MRXNPFEDSA-N 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]benzoic acid Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C(O)=O)C=C1 SUKNIPCMSFNQQV-MRXNPFEDSA-N 0.000 description 1
- RBUAGOAZCLYMDO-UHFFFAOYSA-N 4-amino-3-chloro-n-(4-sulfamoylphenyl)benzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)NC1=CC=C(S(N)(=O)=O)C=C1 RBUAGOAZCLYMDO-UHFFFAOYSA-N 0.000 description 1
- INCQBYVCFYAOQQ-UHFFFAOYSA-N 4-amino-3-chloro-n-(thiophen-2-ylmethyl)benzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)NCC1=CC=CS1 INCQBYVCFYAOQQ-UHFFFAOYSA-N 0.000 description 1
- YAGPSYLKPLEGEE-UHFFFAOYSA-N 4-amino-3-chloro-n-[4-(2-ethoxyethylsulfanyl)phenyl]benzenesulfonamide Chemical compound C1=CC(SCCOCC)=CC=C1NS(=O)(=O)C1=CC=C(N)C(Cl)=C1 YAGPSYLKPLEGEE-UHFFFAOYSA-N 0.000 description 1
- BJMIFIOWLMZTOA-UHFFFAOYSA-N 4-amino-3-chloro-n-[4-(2-hydroxyethylsulfanyl)phenyl]benzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)NC1=CC=C(SCCO)C=C1 BJMIFIOWLMZTOA-UHFFFAOYSA-N 0.000 description 1
- PYRUUCYNAXPEBA-UHFFFAOYSA-N 4-amino-3-chlorobenzenesulfonyl fluoride Chemical compound NC1=CC=C(S(F)(=O)=O)C=C1Cl PYRUUCYNAXPEBA-UHFFFAOYSA-N 0.000 description 1
- JPOMPDKGTPZRAJ-UHFFFAOYSA-N 4-amino-3-fluoro-n-(2-fluorophenyl)benzenesulfonamide Chemical compound C1=C(F)C(N)=CC=C1S(=O)(=O)NC1=CC=CC=C1F JPOMPDKGTPZRAJ-UHFFFAOYSA-N 0.000 description 1
- WQTCZINVPXJNEL-UHFFFAOYSA-N 4-amino-3-methylbenzenesulfonic acid Chemical compound CC1=CC(S(O)(=O)=O)=CC=C1N WQTCZINVPXJNEL-UHFFFAOYSA-N 0.000 description 1
- DEKVFRVOUAQXLA-UHFFFAOYSA-N 4-amino-n-(3-bromo-4-chlorophenyl)-3-chlorobenzenesulfonamide Chemical compound C1=C(Cl)C(N)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C(Br)=C1 DEKVFRVOUAQXLA-UHFFFAOYSA-N 0.000 description 1
- BPUKPIBWYZWYQV-UHFFFAOYSA-N 4-aminobenzenesulfonyl fluoride Chemical compound NC1=CC=C(S(F)(=O)=O)C=C1 BPUKPIBWYZWYQV-UHFFFAOYSA-N 0.000 description 1
- SEWNAJIUKSTYOP-UHFFFAOYSA-N 4-chloro-3-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC(S(Cl)(=O)=O)=CC=C1Cl SEWNAJIUKSTYOP-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- RMTCWOLYVMOKBR-UHFFFAOYSA-N 4-n,4-n,6-trimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC(C)=NC(N)=N1 RMTCWOLYVMOKBR-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- JTPCVJQUFYRJES-UHFFFAOYSA-N 5,6-dimethylpyrazin-2-amine Chemical compound CC1=NC=C(N)N=C1C JTPCVJQUFYRJES-UHFFFAOYSA-N 0.000 description 1
- FFUWOTHSVPGSAL-UHFFFAOYSA-N 5-(6-amino-1-chlorocyclohexa-2,4-dien-1-yl)sulfonyl-2-chloroaniline Chemical compound NC1C=CC=CC1(Cl)S(=O)(=O)C1=CC=C(Cl)C(N)=C1 FFUWOTHSVPGSAL-UHFFFAOYSA-N 0.000 description 1
- 230000002407 ATP formation Effects 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229930024421 Adenine Natural products 0.000 description 1
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 108010039627 Aprotinin Proteins 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YPLZARFSMFAACF-UHFFFAOYSA-N CC(C(=O)NC1=C(C=C(C=C1)S(=O)(=O)N(C)C2=NC=C(C=C2)C(F)(F)F)Cl)(C(F)(F)F)O Chemical compound CC(C(=O)NC1=C(C=C(C=C1)S(=O)(=O)N(C)C2=NC=C(C=C2)C(F)(F)F)Cl)(C(F)(F)F)O YPLZARFSMFAACF-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 208000020446 Cardiac disease Diseases 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- DIHXWDZLQAERDA-GSVOUGTGSA-N ClC(=O)[C@](O)(C)C(F)(F)F Chemical compound ClC(=O)[C@](O)(C)C(F)(F)F DIHXWDZLQAERDA-GSVOUGTGSA-N 0.000 description 1
- 102000029816 Collagenase Human genes 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 206010019280 Heart failures Diseases 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
- 206010052341 Impaired insulin secretion Diseases 0.000 description 1
- 229940122199 Insulin secretagogue Drugs 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 102000002568 Multienzyme Complexes Human genes 0.000 description 1
- 108010093369 Multienzyme Complexes Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FEYNFHSRETUBEM-UHFFFAOYSA-N N-[3-(1,1-difluoroethyl)phenyl]-1-(4-methoxyphenyl)-3-methyl-5-oxo-4H-pyrazole-4-carboxamide Chemical compound COc1ccc(cc1)N1N=C(C)C(C(=O)Nc2cccc(c2)C(C)(F)F)C1=O FEYNFHSRETUBEM-UHFFFAOYSA-N 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion 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](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- SJQUMIONUUOXIP-UHFFFAOYSA-N OCS(=O)(=O)NCC(C)C Chemical group OCS(=O)(=O)NCC(C)C SJQUMIONUUOXIP-UHFFFAOYSA-N 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 102000020286 Pyruvate Dehydrogenase (Lipoamide)-Phosphatase Human genes 0.000 description 1
- 108010040259 Pyruvate Dehydrogenase (Lipoamide)-Phosphatase Proteins 0.000 description 1
- GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 description 1
- 108020004511 Recombinant DNA Proteins 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 238000012300 Sequence Analysis Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 description 1
- 229940123464 Thiazolidinedione Drugs 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 102000004357 Transferases Human genes 0.000 description 1
- 108090000992 Transferases Proteins 0.000 description 1
- 229920004890 Triton X-100 Polymers 0.000 description 1
- 239000013504 Triton X-100 Substances 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- AAUIINNRORIKRW-UHFFFAOYSA-N [1-(2-chloro-4-fluorosulfonylanilino)-2-methyl-1-oxopropan-2-yl] acetate Chemical compound CC(=O)OC(C)(C)C(=O)NC1=CC=C(S(F)(=O)=O)C=C1Cl AAUIINNRORIKRW-UHFFFAOYSA-N 0.000 description 1
- YKGFHQXVLAEVEC-UHFFFAOYSA-N [Mg+2].[C-]#[C-] Chemical compound [Mg+2].[C-]#[C-] YKGFHQXVLAEVEC-UHFFFAOYSA-N 0.000 description 1
- JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229960000643 adenine Drugs 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 229960004405 aprotinin Drugs 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- 150000008331 benzenesulfonamides Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- CWBHKBKGKCDGDM-UHFFFAOYSA-N bis[(2,2,2-trifluoroacetyl)oxy]boranyl 2,2,2-trifluoroacetate Chemical compound FC(F)(F)C(=O)OB(OC(=O)C(F)(F)F)OC(=O)C(F)(F)F CWBHKBKGKCDGDM-UHFFFAOYSA-N 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001669 calcium Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 description 1
- 229960004588 cilostazol Drugs 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229950001485 cocarboxylase Drugs 0.000 description 1
- 229960002424 collagenase Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 235000020776 essential amino acid Nutrition 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([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
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 239000011536 extraction buffer Substances 0.000 description 1
- 238000010265 fast atom bombardment Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229960004580 glibenclamide Drugs 0.000 description 1
- 230000004110 gluconeogenesis Effects 0.000 description 1
- 230000010030 glucose lowering effect Effects 0.000 description 1
- ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
- 230000002641 glycemic effect Effects 0.000 description 1
- 230000002414 glycolytic effect Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003914 insulin secretion Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000002427 irreversible effect Effects 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000006262 isopropyl amino sulfonyl group Chemical group 0.000 description 1
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
- 108010052968 leupeptin Proteins 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 1
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 210000005228 liver tissue Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- MYTLOWRQCZQAME-QGZVFWFLSA-N methyl 4-[[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 MYTLOWRQCZQAME-QGZVFWFLSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 description 1
- DJIYVRKXDRXMIZ-UHFFFAOYSA-N n-(2-chloro-4-morpholin-4-ylsulfonylphenyl)-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(C)(O)C)=CC=C1S(=O)(=O)N1CCOCC1 DJIYVRKXDRXMIZ-UHFFFAOYSA-N 0.000 description 1
- WTNCKLVOKCXDAU-UHFFFAOYSA-N n-(2-chloro-4-piperazin-1-ylsulfonylphenyl)-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(O)(C)C(F)(F)F)=CC=C1S(=O)(=O)N1CCNCC1 WTNCKLVOKCXDAU-UHFFFAOYSA-N 0.000 description 1
- HSQAFALWFIZAPS-UHFFFAOYSA-N n-(2-chloro-4-piperidin-1-ylsulfonylphenyl)-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(C)(O)C)=CC=C1S(=O)(=O)N1CCCCC1 HSQAFALWFIZAPS-UHFFFAOYSA-N 0.000 description 1
- FZAWEXLBDFYNIP-UHFFFAOYSA-N n-[2-chloro-4-(methylsulfamoyl)phenyl]-2-hydroxy-2-methylpropanamide Chemical compound CNS(=O)(=O)C1=CC=C(NC(=O)C(C)(C)O)C(Cl)=C1 FZAWEXLBDFYNIP-UHFFFAOYSA-N 0.000 description 1
- HCVIHPAIVPEHPN-UHFFFAOYSA-N n-[2-chloro-4-[(2,4-dibromophenyl)sulfamoyl]phenyl]-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(C)(O)C)=CC=C1S(=O)(=O)NC1=CC=C(Br)C=C1Br HCVIHPAIVPEHPN-UHFFFAOYSA-N 0.000 description 1
- BCVJTYZEHLDSOV-UHFFFAOYSA-N n-[2-chloro-4-[(4-formylphenyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(C=O)C=C1 BCVJTYZEHLDSOV-UHFFFAOYSA-N 0.000 description 1
- BIAUWKUHBZPLIY-UHFFFAOYSA-N n-[2-chloro-4-[[4-(2-hydroxyethylsulfanyl)phenyl]sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC1=CC=C(SCCO)C=C1 BIAUWKUHBZPLIY-UHFFFAOYSA-N 0.000 description 1
- PFZDKZNIAKIPLV-MRXNPFEDSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-3-iodobenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC(I)=C1 PFZDKZNIAKIPLV-MRXNPFEDSA-N 0.000 description 1
- QNYNYQHTVVRXAY-QGZVFWFLSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-4-cyanobenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(C#N)C=C1 QNYNYQHTVVRXAY-QGZVFWFLSA-N 0.000 description 1
- GEGGTXKYOMGVHL-MRXNPFEDSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-4-hydroxybenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(O)C=C1 GEGGTXKYOMGVHL-MRXNPFEDSA-N 0.000 description 1
- UHKMVLRVYGOCIP-QGZVFWFLSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NS(=O)(=O)C1=CC=C(NC(=O)[C@@](C)(O)C(F)(F)F)C(Cl)=C1 UHKMVLRVYGOCIP-QGZVFWFLSA-N 0.000 description 1
- JNTBVKHQOMSHEZ-QGZVFWFLSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonyl-4-methylsulfonylbenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=C(S(C)(=O)=O)C=C1 JNTBVKHQOMSHEZ-QGZVFWFLSA-N 0.000 description 1
- HGYGLKDBTHNZNC-MRXNPFEDSA-N n-[3-chloro-4-[[(2r)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoyl]amino]phenyl]sulfonylbenzamide Chemical compound C1=C(Cl)C(NC(=O)[C@](O)(C)C(F)(F)F)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1 HGYGLKDBTHNZNC-MRXNPFEDSA-N 0.000 description 1
- FYWZEJLRPPEHSJ-UHFFFAOYSA-N n-[4-(benzylsulfamoyl)-2-chlorophenyl]-2-hydroxy-2-methylpropanamide Chemical compound C1=C(Cl)C(NC(=O)C(C)(O)C)=CC=C1S(=O)(=O)NCC1=CC=CC=C1 FYWZEJLRPPEHSJ-UHFFFAOYSA-N 0.000 description 1
- LBPGWELZWXAITN-UHFFFAOYSA-N n-[4-[bis(2-methylpropyl)sulfamoyl]phenyl]-3,3,3-trifluoro-2-hydroxy-2-methylpropanamide Chemical compound CC(C)CN(CC(C)C)S(=O)(=O)C1=CC=C(NC(=O)C(C)(O)C(F)(F)F)C=C1 LBPGWELZWXAITN-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 229940101270 nicotinamide adenine dinucleotide (nad) Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007523 nucleic acids Chemical group 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 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
- 239000008363 phosphate buffer Substances 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 230000000865 phosphorylative effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000013612 plasmid Substances 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 108091006091 regulatory enzymes Proteins 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000011125 single therapy Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000000565 sulfonamide group Chemical group 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
- 239000000829 suppository Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- YWKQAWIOKSTNDF-UHFFFAOYSA-N tert-butyl 4-(4-amino-3-chlorophenyl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=CC=C(N)C(Cl)=C1 YWKQAWIOKSTNDF-UHFFFAOYSA-N 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- GPTXCAZYUMDUMN-UHFFFAOYSA-N tert-butyl n-(2-hydroxyethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCO GPTXCAZYUMDUMN-UHFFFAOYSA-N 0.000 description 1
- HRFQCZCIZZAJBB-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)-n-[2-(oxan-2-yloxy)ethyl]carbamate Chemical compound C=1C=C(N)C=CC=1N(C(=O)OC(C)(C)C)CCOC1CCCCO1 HRFQCZCIZZAJBB-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
- VFJYIHQDILEQNR-UHFFFAOYSA-M trimethylsulfanium;iodide Chemical compound [I-].C[S+](C)C VFJYIHQDILEQNR-UHFFFAOYSA-M 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical class C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- LYRCQNDYYRPFMF-UHFFFAOYSA-N trimethyltin Chemical compound C[Sn](C)C LYRCQNDYYRPFMF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
- C07C311/46—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/51—Y being a hydrogen or a carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/49—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/62—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/96—Sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
- C07D241/20—Nitrogen atoms
- C07D241/22—Benzenesulfonamido pyrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/14—Nitrogen atoms
- C07D261/16—Benzene-sulfonamido isoxazoles
-
- 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
- C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/22—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
- C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9805520.5A GB9805520D0 (en) | 1998-03-17 | 1998-03-17 | Chemical compounds |
PCT/GB1999/000739 WO1999047508A1 (fr) | 1998-03-17 | 1999-03-11 | Derives de benzenesulfamide et leur utilisation comme medicaments |
Publications (1)
Publication Number | Publication Date |
---|---|
SK13812000A3 true SK13812000A3 (sk) | 2001-04-09 |
Family
ID=10828601
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1381-2000A SK13812000A3 (sk) | 1998-03-17 | 1999-03-11 | Benzénsulfónamidové deriváty, spôsob ich prípravy, ich použitie a farmaceutická kompozícia, ktorá ich obsahuje |
Country Status (23)
Country | Link |
---|---|
US (1) | US6667342B1 (fr) |
EP (1) | EP1064274B1 (fr) |
JP (1) | JP2002506859A (fr) |
KR (1) | KR20010041837A (fr) |
CN (1) | CN1293666A (fr) |
AT (1) | ATE323687T1 (fr) |
AU (1) | AU744579B2 (fr) |
BR (1) | BR9908764A (fr) |
CA (1) | CA2323783A1 (fr) |
DE (1) | DE69930926T2 (fr) |
EE (1) | EE200000545A (fr) |
ES (1) | ES2262313T3 (fr) |
GB (2) | GB9805520D0 (fr) |
HU (1) | HUP0102556A3 (fr) |
ID (1) | ID26179A (fr) |
IL (1) | IL138516A0 (fr) |
IS (1) | IS5578A (fr) |
NO (1) | NO20004624L (fr) |
PL (1) | PL342937A1 (fr) |
SK (1) | SK13812000A3 (fr) |
TR (1) | TR200002606T2 (fr) |
WO (1) | WO1999047508A1 (fr) |
ZA (1) | ZA992017B (fr) |
Families Citing this family (57)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
JP2003508509A (ja) | 1999-09-04 | 2003-03-04 | アストラゼネカ アクチボラグ | ピルビン酸デヒドロゲナーゼの阻害剤としてのアミド |
MY127036A (en) * | 1999-09-04 | 2006-11-30 | Astrazeneca Ab | Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3- trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity |
US6552225B1 (en) | 1999-09-04 | 2003-04-22 | Astrazeneca Ab | Chemical compounds |
GB0012012D0 (en) * | 2000-05-19 | 2000-07-05 | Astrazeneca Ab | Chemical compound |
GB0120471D0 (en) * | 2001-08-23 | 2001-10-17 | Astrazeneca Ab | Chemical compounds |
AR037097A1 (es) | 2001-10-05 | 2004-10-20 | Novartis Ag | Compuestos acilsulfonamidas, composiciones farmaceuticas y el uso de dichos compuestos para la preparacion de un medicamento |
BR0311767A (pt) | 2002-06-11 | 2005-03-08 | Wyeth Corp | Compostos inibidores de sulfonamida substituìda da produção de beta amilóide, suas composições e usos |
AU2004305321A1 (en) * | 2003-12-19 | 2005-07-07 | Pfizer Inc. | Benzenesulfonylamino-pyridin-2-yl derivatives and related compounds as inhibitors of 11-beta-hydroxysteroid dehydrogenase type 1 (11-beta-hsd-1) for the treatment of diabetes and obesity |
DE102004021779A1 (de) * | 2004-04-30 | 2005-11-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
CA2581865C (fr) | 2004-09-29 | 2010-04-20 | F. Hoffmann-La Roche Ag | Derives d'indozolone utilises en tant qu'inhibiteurs de la 11b-hsd1 |
TW200630337A (en) | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
WO2006105127A2 (fr) * | 2005-03-31 | 2006-10-05 | Takeda San Diego, Inc. | Inhibiteurs de l'hydroxysteroide deshydrogenase |
CA2621310C (fr) | 2005-09-27 | 2014-08-12 | Shionogi & Co., Ltd. | Derive sulfonamide ayant une activite antagoniste de recepteur pgd2 |
DE102005052102A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
DE102005052127A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue indol-haltige Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
DE102005052101A1 (de) * | 2005-10-28 | 2007-05-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
RU2008129797A (ru) * | 2006-02-17 | 2010-03-27 | Вайет (Us) | Способы получения сульфонамид-замещенных спиртов и их промежуточных соединений |
CA2637615A1 (fr) * | 2006-02-17 | 2007-08-30 | Wyeth | N-sulfonylation selective d'alcools porteurs d'une substitution par un 2-amino trifluoroalkyle |
WO2007110449A1 (fr) | 2006-03-29 | 2007-10-04 | Euro-Celtique S.A. | Composés de benzènesulfonamide et utilisation de ceux-ci |
US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
WO2007118854A1 (fr) | 2006-04-13 | 2007-10-25 | Euro-Celtique S.A. | Composés à base de benzènesulfonamide et leur utilisation |
JP4891111B2 (ja) * | 2007-02-16 | 2012-03-07 | 富士フイルム株式会社 | ズームレンズ |
JP5361857B2 (ja) | 2007-03-23 | 2013-12-04 | ファイザー・リミテッド | イオンチャネルの阻害剤 |
WO2008124118A1 (fr) * | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Composés benzènesulfonylés et leur utilisation |
US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
US8785450B2 (en) * | 2009-06-29 | 2014-07-22 | Agios Pharmaceuticals, Inc. | Therapeutic compounds and compositions |
EP2590951B1 (fr) | 2010-07-09 | 2015-01-07 | Pfizer Limited | Benzènesulfonamides utiles en tant qu'inhibiteurs des canaux sodiques |
CA2804351A1 (fr) | 2010-07-12 | 2012-01-19 | Pfizer Limited | Composes chimiques |
JP2013532185A (ja) | 2010-07-12 | 2013-08-15 | ファイザー・リミテッド | 化合物 |
JP2013536165A (ja) | 2010-07-12 | 2013-09-19 | ファイザー・リミテッド | 痛みの処置のためのnav1.7阻害薬としてのスルホンアミド誘導体 |
US9102621B2 (en) | 2010-07-12 | 2015-08-11 | Pfizer Limited | Acyl sulfonamide compounds |
JP2013532184A (ja) | 2010-07-12 | 2013-08-15 | ファイザー・リミテッド | 電位開口型ナトリウムチャネル阻害剤として有用なn−スルホニルベンズアミド誘導体 |
EP2763673B1 (fr) * | 2011-09-15 | 2018-08-01 | Taipei Medical University | Utilisation d'hydroxamates d'indolyle dans le traitement de l'insuffisance cardiaque ou de lésion neuronale |
GB201218084D0 (en) | 2012-10-09 | 2012-11-21 | Univ Aston | Novel compounds and methods for use in medicine |
WO2016161268A1 (fr) | 2015-04-01 | 2016-10-06 | Enanta Pharmaceuticals, Inc. | Agents antiviraux contre l'hépatite b |
WO2016183266A1 (fr) * | 2015-05-13 | 2016-11-17 | Enanta Pharmaceuticals, Inc. | Agents antiviraux de l'hépatite b |
US10179131B2 (en) | 2015-07-13 | 2019-01-15 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
US10301255B2 (en) | 2015-07-22 | 2019-05-28 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
WO2017136403A1 (fr) | 2016-02-02 | 2017-08-10 | Enanta Pharmaceuticals, Inc. | Agents antiviraux contre l'hépatite b |
ES2938341T3 (es) | 2016-03-07 | 2023-04-10 | Enanta Pharm Inc | Agentes antivirales contra la hepatitis B |
JP2019521972A (ja) | 2016-06-10 | 2019-08-08 | エナンタ ファーマシューティカルズ インコーポレイテッド | B型肝炎抗ウイルス剤 |
CA3073986A1 (fr) | 2017-08-28 | 2019-03-07 | Enanta Pharmaceuticals, Inc. | Agents antiviraux contre l'hepatite b |
TW201936192A (zh) | 2017-12-06 | 2019-09-16 | 美商因那塔製藥公司 | B 型肝炎抗病毒試劑 |
WO2019113173A1 (fr) | 2017-12-06 | 2019-06-13 | Enanta Pharmaceuticals, Inc. | Agents antiviraux contre l'hépatite b |
US11058678B2 (en) | 2018-01-22 | 2021-07-13 | Enanta Pharmaceuticals, Inc. | Substituted heterocycles as antiviral agents |
WO2019191166A1 (fr) | 2018-03-29 | 2019-10-03 | Enanta Pharmaceuticals, Inc. | Agents antiviraux de l'hépatite b |
CN112955142A (zh) | 2018-09-21 | 2021-06-11 | 英安塔制药有限公司 | 官能化杂环化合物作为抗病毒剂 |
UY38483A (es) | 2018-11-21 | 2020-06-30 | Enanta Pharm Inc | Heterociclos funcionalizados como agentes antivirales |
US11236111B2 (en) | 2019-06-03 | 2022-02-01 | Enanta Pharmaceuticals, Inc. | Hepatitis B antiviral agents |
WO2020247575A1 (fr) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc. | Agents antiviraux de l'hépatite b |
WO2020247561A1 (fr) | 2019-06-04 | 2020-12-10 | Enanta Pharmaceuticals, Inc, | Agents antiviraux de l'hépatite b |
WO2021007488A1 (fr) | 2019-07-11 | 2021-01-14 | Enanta Pharmaceuticals, Inc. | Hétérocycles substitués utilisés en tant qu'agents antiviraux |
WO2021055425A2 (fr) | 2019-09-17 | 2021-03-25 | Enanta Pharmaceuticals, Inc. | Hétérocycles fonctionnalisés utiles en tant qu'agents antiviraux |
US11802125B2 (en) | 2020-03-16 | 2023-10-31 | Enanta Pharmaceuticals, Inc. | Functionalized heterocyclic compounds as antiviral agents |
CN114716388B (zh) * | 2021-11-04 | 2024-02-13 | 江苏冠军科技集团股份有限公司 | 一种磺胺-银化合物及其制备方法 |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2862100D1 (en) | 1977-10-12 | 1983-01-05 | Ici Plc | Acylanilides, process for their manufacture and pharmaceutical and veterinary compositions containing them |
US4191775A (en) | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
NZ197008A (en) | 1980-05-22 | 1984-10-19 | Ici Ltd | Acylanilide derivatives and pharmaceutical compositions |
AU8961382A (en) | 1981-11-06 | 1983-05-12 | Imperial Chemical Industries Plc | Amide derivatives |
US4537618A (en) | 1982-05-26 | 1985-08-27 | Ciba Geigy Corporation | N-phenylsulfonyl-N'-pyrimidinylureas |
ATE28864T1 (de) | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
GB8617653D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
GB8617652D0 (en) | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
GB9214120D0 (en) | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
EP0539329A1 (fr) * | 1991-10-25 | 1993-04-28 | Ciba-Geigy Ag | Acétylène composés, utiles comme antagonistes de leukotriènes |
SE9103397D0 (sv) * | 1991-11-18 | 1991-11-18 | Kabi Pharmacia Ab | Nya substituerade salicylsyror |
IL105558A (en) | 1992-05-18 | 1998-04-05 | Zeneca Ltd | Tertiary carbinols with channel activity potassium process for their preparation and pharmaceutical preparations containing them |
GB9305295D0 (en) | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
GB9309716D0 (en) | 1993-05-12 | 1993-06-23 | Zeneca Ltd | Heterocyclic derivatives |
GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
GB9310069D0 (en) | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Heterocyclic compounds |
GB2278054A (en) | 1993-05-18 | 1994-11-23 | Zeneca Ltd | Compounds for the treatment of urinary incontinence |
GB9505082D0 (en) | 1995-03-14 | 1995-05-03 | Zeneca Ltd | Medicament |
US5806636A (en) | 1995-08-16 | 1998-09-15 | Northrop Grumman Corporation | Brake rotors/drums and brake pads particulary adapted for motorized vehicles |
GB9607458D0 (en) | 1996-04-10 | 1996-06-12 | Zeneca Ltd | Enzymatic process for stereoselective preparation of therapeutic amides |
GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
GB9811932D0 (en) | 1998-06-04 | 1998-07-29 | Zeneca Ltd | Chemical compunds |
-
1998
- 1998-03-17 GB GBGB9805520.5A patent/GB9805520D0/en not_active Ceased
-
1999
- 1999-03-03 GB GBGB9904716.9A patent/GB9904716D0/en not_active Ceased
- 1999-03-11 BR BR9908764-2A patent/BR9908764A/pt not_active IP Right Cessation
- 1999-03-11 DE DE69930926T patent/DE69930926T2/de not_active Expired - Fee Related
- 1999-03-11 AT AT99907772T patent/ATE323687T1/de not_active IP Right Cessation
- 1999-03-11 WO PCT/GB1999/000739 patent/WO1999047508A1/fr active IP Right Grant
- 1999-03-11 ID IDW20001798A patent/ID26179A/id unknown
- 1999-03-11 SK SK1381-2000A patent/SK13812000A3/sk unknown
- 1999-03-11 IL IL13851699A patent/IL138516A0/xx unknown
- 1999-03-11 ES ES99907772T patent/ES2262313T3/es not_active Expired - Lifetime
- 1999-03-11 EP EP99907772A patent/EP1064274B1/fr not_active Expired - Lifetime
- 1999-03-11 PL PL99342937A patent/PL342937A1/xx unknown
- 1999-03-11 CN CN99803991A patent/CN1293666A/zh active Pending
- 1999-03-11 KR KR1020007010127A patent/KR20010041837A/ko not_active Application Discontinuation
- 1999-03-11 CA CA002323783A patent/CA2323783A1/fr not_active Abandoned
- 1999-03-11 EE EEP200000545A patent/EE200000545A/xx unknown
- 1999-03-11 HU HU0102556A patent/HUP0102556A3/hu unknown
- 1999-03-11 JP JP2000536705A patent/JP2002506859A/ja active Pending
- 1999-03-11 US US09/622,678 patent/US6667342B1/en not_active Expired - Fee Related
- 1999-03-11 AU AU27401/99A patent/AU744579B2/en not_active Ceased
- 1999-03-11 TR TR2000/02606T patent/TR200002606T2/xx unknown
- 1999-03-16 ZA ZA9902017A patent/ZA992017B/xx unknown
-
2000
- 2000-07-28 IS IS5578A patent/IS5578A/is unknown
- 2000-09-15 NO NO20004624A patent/NO20004624L/no unknown
Also Published As
Publication number | Publication date |
---|---|
KR20010041837A (ko) | 2001-05-25 |
GB9805520D0 (en) | 1998-05-13 |
DE69930926T2 (de) | 2007-01-25 |
JP2002506859A (ja) | 2002-03-05 |
NO20004624L (no) | 2000-10-30 |
GB9904716D0 (en) | 1999-04-21 |
AU744579B2 (en) | 2002-02-28 |
ZA992017B (en) | 1999-09-17 |
CA2323783A1 (fr) | 1999-09-23 |
DE69930926D1 (de) | 2006-05-24 |
EP1064274B1 (fr) | 2006-04-19 |
US6667342B1 (en) | 2003-12-23 |
HUP0102556A3 (en) | 2002-12-28 |
EE200000545A (et) | 2002-02-15 |
CN1293666A (zh) | 2001-05-02 |
ID26179A (id) | 2000-12-07 |
TR200002606T2 (tr) | 2001-01-22 |
WO1999047508A1 (fr) | 1999-09-23 |
HUP0102556A2 (hu) | 2002-05-29 |
ES2262313T3 (es) | 2006-11-16 |
IS5578A (is) | 2000-07-28 |
PL342937A1 (en) | 2001-07-16 |
IL138516A0 (en) | 2001-10-31 |
NO20004624D0 (no) | 2000-09-15 |
EP1064274A1 (fr) | 2001-01-03 |
AU2740199A (en) | 1999-10-11 |
BR9908764A (pt) | 2000-11-14 |
ATE323687T1 (de) | 2006-05-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
SK13812000A3 (sk) | Benzénsulfónamidové deriváty, spôsob ich prípravy, ich použitie a farmaceutická kompozícia, ktorá ich obsahuje | |
RU2242224C2 (ru) | Применение соединений для повышения активности пируватдегидрогеназы | |
US6878712B1 (en) | Amides as inhibitors for pyruvate dehydrogenase | |
US7253189B2 (en) | Cannabinoid receptor ligands | |
KR100692232B1 (ko) | 피루베이트 탈수소효소 활성을 증가시키는 치환된 n-페닐2-히드록시-2-메틸-3,3,3-트리플루오로프로판아미드 유도체 | |
ES2273725T3 (es) | Derivados de hidroxiacetamidobencenosulfonamida. | |
WO1999062873A1 (fr) | Derives de benzenesulphonamide comme activateurs des deshydrogenases de pyruvate | |
CZ20003370A3 (cs) | Benzensulfonamidové deriváty a jejich použití jako léčiv | |
MXPA00008710A (en) | Benzenesulfonamide-derivatives and their use as medicaments |