NO326426B1 - Sykloalkenderivater, deres fremstilling og anvendelse - Google Patents

Info

Publication number

NO326426B1

NO326426B1 NO20004485A NO20004485A NO326426B1 NO 326426 B1 NO326426 B1 NO 326426B1 NO 20004485 A NO20004485 A NO 20004485A NO 20004485 A NO20004485 A NO 20004485A NO 326426 B1 NO326426 B1 NO 326426B1

Authority

NO

Norway

Prior art keywords

group

formula

represented

alkyl

compound

Prior art date

1998-03-09

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• 238000002360 preparation method Methods 0.000 title claims description 7
• 150000001875 compounds Chemical class 0.000 claims abstract description 317
• 125000001424 substituent group Chemical group 0.000 claims abstract description 175
• 150000003839 salts Chemical class 0.000 claims abstract description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 66
• 125000001931 aliphatic group Chemical group 0.000 claims abstract description 62
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 55
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 27
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 15
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
• 208000019622 heart disease Diseases 0.000 claims abstract description 8
• -1 carbamoyloxy group Chemical group 0.000 claims description 183
• 239000000203 mixture Substances 0.000 claims description 121
• 125000000217 alkyl group Chemical group 0.000 claims description 100
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 97
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 82
• 238000000034 method Methods 0.000 claims description 81
• 229910052717 sulfur Inorganic materials 0.000 claims description 49
• 125000004434 sulfur atom Chemical group 0.000 claims description 49
• 125000004432 carbon atom Chemical group C* 0.000 claims description 45
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
• 125000005843 halogen group Chemical group 0.000 claims description 42
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000002252 acyl group Chemical group 0.000 claims description 25
• 238000004519 manufacturing process Methods 0.000 claims description 24
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 230000002401 inhibitory effect Effects 0.000 claims description 22
• 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 21
• 125000004122 cyclic group Chemical group 0.000 claims description 20
• 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 19
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 18
• 125000003342 alkenyl group Chemical group 0.000 claims description 17
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 125000003118 aryl group Chemical group 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 206010040070 Septic Shock Diseases 0.000 claims description 12
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 12
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 230000036303 septic shock Effects 0.000 claims description 11
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 10
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 10
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 10
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 10
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 10
• 125000005110 aryl thio group Chemical group 0.000 claims description 10
• 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 10
• 125000005366 cycloalkylthio group Chemical group 0.000 claims description 10
• 230000016396 cytokine production Effects 0.000 claims description 10
• 150000002367 halogens Chemical class 0.000 claims description 10
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 10
• 125000004149 thio group Chemical group *S* 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000004442 acylamino group Chemical group 0.000 claims description 9
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 9
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 9
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
• 125000005842 heteroatom Chemical group 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 9
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 206010040047 Sepsis Diseases 0.000 claims description 7
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 230000008569 process Effects 0.000 claims description 6
• 238000007363 ring formation reaction Methods 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 claims description 4
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• BANYPWGZBGTWFD-UHFFFAOYSA-N ethyl 6-[(2-chloro-4-methylphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical group CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(C)C=C1Cl BANYPWGZBGTWFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 4
• 230000002265 prevention Effects 0.000 claims description 4
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical group COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 3
• FLSDSYNBODHRCV-UHFFFAOYSA-N ethyl 6-[(2,4-dichlorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical group CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(Cl)C=C1Cl FLSDSYNBODHRCV-UHFFFAOYSA-N 0.000 claims description 2
• 201000010099 disease Diseases 0.000 abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
• 230000035939 shock Effects 0.000 abstract description 4
• 208000020446 Cardiac disease Diseases 0.000 abstract 1
• 229940002612 prodrug Drugs 0.000 abstract 1
• 239000000651 prodrug Substances 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 615
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 231
• 230000002829 reductive effect Effects 0.000 description 119
• 238000005160 1H NMR spectroscopy Methods 0.000 description 103
• 239000013078 crystal Substances 0.000 description 94
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 90
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 90
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 72
• 239000002904 solvent Substances 0.000 description 71
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 239000003480 eluent Substances 0.000 description 62
• 239000011541 reaction mixture Substances 0.000 description 62
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
• HNDUKOBQKAFGCT-UHFFFAOYSA-N ethyl 2-chlorosulfonylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C(S(Cl)(=O)=O)CCCC1 HNDUKOBQKAFGCT-UHFFFAOYSA-N 0.000 description 51
• 239000000243 solution Substances 0.000 description 46
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 46
• 238000001816 cooling Methods 0.000 description 45
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 43
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
• 238000006243 chemical reaction Methods 0.000 description 34
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
• SIIGGFCBVDNNNU-UHFFFAOYSA-N 2-ethoxycarbonylcyclohexene-1-sulfonic acid Chemical compound CCOC(=O)C1=C(S(O)(=O)=O)CCCC1 SIIGGFCBVDNNNU-UHFFFAOYSA-N 0.000 description 28
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
• 238000010898 silica gel chromatography Methods 0.000 description 25
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
• 238000004440 column chromatography Methods 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 23
• 229910002027 silica gel Inorganic materials 0.000 description 23
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 238000009472 formulation Methods 0.000 description 21
• 238000010992 reflux Methods 0.000 description 20
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 19
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 19
• 239000000706 filtrate Substances 0.000 description 18
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 17
• 239000012267 brine Substances 0.000 description 17
• 238000001704 evaporation Methods 0.000 description 17
• 230000008020 evaporation Effects 0.000 description 17
• 239000000126 substance Substances 0.000 description 17
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
• 239000002585 base Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• 102000004127 Cytokines Human genes 0.000 description 15
• 108090000695 Cytokines Proteins 0.000 description 15
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• 239000000843 powder Substances 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 239000002158 endotoxin Substances 0.000 description 11
• 229920006008 lipopolysaccharide Polymers 0.000 description 11
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
• 235000019341 magnesium sulphate Nutrition 0.000 description 11
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
• 108090001005 Interleukin-6 Proteins 0.000 description 10
• 230000002411 adverse Effects 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• VSOMGDDXCKLSIG-UHFFFAOYSA-N ethyl 6-[(2,4-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1F VSOMGDDXCKLSIG-UHFFFAOYSA-N 0.000 description 10
• 238000003818 flash chromatography Methods 0.000 description 10
• 150000007530 organic bases Chemical class 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• 239000007864 aqueous solution Substances 0.000 description 9
• 210000004369 blood Anatomy 0.000 description 9
• 239000008280 blood Substances 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
• 102100040247 Tumor necrosis factor Human genes 0.000 description 8
• 238000002474 experimental method Methods 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 238000005406 washing Methods 0.000 description 8
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 7
• XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 7
• 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 7
• 102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 7
• 125000005037 alkyl phenyl group Chemical group 0.000 description 7
• 238000004587 chromatography analysis Methods 0.000 description 7
• 239000003814 drug Substances 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
• 238000000926 separation method Methods 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• 229940124597 therapeutic agent Drugs 0.000 description 7
• HOOCZFRHVPMDTH-UHFFFAOYSA-M trisodium;dioxido(oxidooxy)borane;tetrahydrate Chemical compound O.O.O.O.[Na+].[Na+].[Na+].[O-]OB([O-])[O-] HOOCZFRHVPMDTH-UHFFFAOYSA-M 0.000 description 7
• CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
• 235000001014 amino acid Nutrition 0.000 description 6
• 150000001413 amino acids Chemical class 0.000 description 6
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
• 230000002500 effect on skin Effects 0.000 description 6
• 230000002757 inflammatory effect Effects 0.000 description 6
• 150000007529 inorganic bases Chemical class 0.000 description 6
• 229910052740 iodine Inorganic materials 0.000 description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 230000003287 optical effect Effects 0.000 description 6
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
• 230000000069 prophylactic effect Effects 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
• 108010002352 Interleukin-1 Proteins 0.000 description 5
• 102000000589 Interleukin-1 Human genes 0.000 description 5
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
• 102100022397 Nitric oxide synthase, brain Human genes 0.000 description 5
• 101710111444 Nitric oxide synthase, brain Proteins 0.000 description 5
• 101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 5
• IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 5
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
• 239000002253 acid Substances 0.000 description 5
• 230000001154 acute effect Effects 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 239000000460 chlorine Substances 0.000 description 5
• 150000008282 halocarbons Chemical class 0.000 description 5
• 238000011534 incubation Methods 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 239000011630 iodine Substances 0.000 description 5
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 210000002540 macrophage Anatomy 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 150000007522 mineralic acids Chemical class 0.000 description 5
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 150000002825 nitriles Chemical class 0.000 description 5
• 229940005654 nitrite ion Drugs 0.000 description 5
• 239000000047 product Substances 0.000 description 5
• 230000035484 reaction time Effects 0.000 description 5
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
• CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
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