UA80718C2 - 2-thio-substituted imidazole derivatives and their use in pharmaceutics - Google Patents

2-thio-substituted imidazole derivatives and their use in pharmaceutics Download PDF

Info

Publication number: UA80718C2
Authority: UA; Ukraine
Prior art keywords: alkyl; halogen; rug; phenyl; substituted
Prior art date: 2002-08-20

Application number

UAA200502484A

Other languages

English (en)

Ukrainian (uk)

Inventor

Hans-Gunter Striegel

Volfgang Albrecht

Original Assignee

Merckle Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-20

Filing date

2003-08-20

Publication date

2007-10-25

2003-08-20 Application filed by Merckle Gmbh filed Critical Merckle Gmbh

2007-10-25 Publication of UA80718C2 publication Critical patent/UA80718C2/uk

Links

150000002460 imidazoles Chemical class 0.000 title claims abstract description 17
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 12
150000001875 compounds Chemical class 0.000 claims abstract description 125
102000004127 Cytokines Human genes 0.000 claims abstract description 12
108090000695 Cytokines Proteins 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
230000002519 immonomodulatory effect Effects 0.000 claims abstract description 6
210000000987 immune system Anatomy 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 30
150000003254 radicals Chemical class 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
208000035475 disorder Diseases 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
150000005840 aryl radicals Chemical class 0.000 claims description 3
125000002619 bicyclic group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 2
210000005056 cell body Anatomy 0.000 claims description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000000165 tricyclic carbocycle group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 1
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
230000009471 action Effects 0.000 abstract description 3
201000010099 disease Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 70
238000006243 chemical reaction Methods 0.000 description 66
238000005160 1H NMR spectroscopy Methods 0.000 description 59
238000007429 general method Methods 0.000 description 57
-1 thiazolyl radical Chemical class 0.000 description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
238000004440 column chromatography Methods 0.000 description 45
239000011541 reaction mixture Substances 0.000 description 38
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 37
239000000203 mixture Substances 0.000 description 37
238000005481 NMR spectroscopy Methods 0.000 description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
230000015572 biosynthetic process Effects 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
238000000926 separation method Methods 0.000 description 26
238000003786 synthesis reaction Methods 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
238000010992 reflux Methods 0.000 description 21
239000000725 suspension Substances 0.000 description 21
150000001412 amines Chemical class 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
239000002244 precipitate Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
238000001816 cooling Methods 0.000 description 15
239000000284 extract Substances 0.000 description 15
NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical class S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 description 15
239000000706 filtrate Substances 0.000 description 13
239000000126 substance Substances 0.000 description 12
238000001665 trituration Methods 0.000 description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 11
238000000746 purification Methods 0.000 description 11
239000012047 saturated solution Substances 0.000 description 11
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000012043 crude product Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 8
238000000354 decomposition reaction Methods 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
150000001408 amides Chemical class 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000003921 oil Substances 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 6
229940116357 potassium thiocyanate Drugs 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
SWLMSOXBPVFLNF-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-pyridin-4-ylethanone Chemical compound C1=CC(F)=CC=C1CC(=O)C1=CC=NC=C1 SWLMSOXBPVFLNF-UHFFFAOYSA-N 0.000 description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
241000282414 Homo sapiens Species 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
235000011114 ammonium hydroxide Nutrition 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
230000003197 catalytic effect Effects 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 5
230000003993 interaction Effects 0.000 description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
238000006467 substitution reaction Methods 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
238000012360 testing method Methods 0.000 description 5
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000007789 gas Substances 0.000 description 4
150000002430 hydrocarbons Chemical class 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
150000002923 oximes Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 3
IRJGKBJLGZJJEL-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfinylbenzene Chemical compound CS(=O)C1=CC=C(CCl)C=C1 IRJGKBJLGZJJEL-UHFFFAOYSA-N 0.000 description 3
DATDARDTUZHWMK-UHFFFAOYSA-N 2-hydroxy-5-methylsulfanylbenzoic acid Chemical compound CSC1=CC=C(O)C(C(O)=O)=C1 DATDARDTUZHWMK-UHFFFAOYSA-N 0.000 description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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208000013616 Respiratory Distress Syndrome Diseases 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
241001061127 Thione Species 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
239000000872 buffer Substances 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
229910052593 corundum Inorganic materials 0.000 description 3
239000013078 crystal Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
238000004821 distillation Methods 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003860 storage Methods 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
150000003672 ureas Chemical class 0.000 description 3
150000003673 urethanes Chemical class 0.000 description 3
229910001845 yogo sapphire Inorganic materials 0.000 description 3
UWHSPZZUAYSGTB-UHFFFAOYSA-N 1,1,3,3-tetraethylurea Chemical compound CCN(CC)C(=O)N(CC)CC UWHSPZZUAYSGTB-UHFFFAOYSA-N 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
LXPRVXKHIXWBJZ-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CCl)C=C1 LXPRVXKHIXWBJZ-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
YELDSRZWSMAJAM-UHFFFAOYSA-N 2-(2-chloropyridin-4-yl)-1-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1C(=O)CC1=CC=NC(Cl)=C1 YELDSRZWSMAJAM-UHFFFAOYSA-N 0.000 description 2
FFZMECXFDGAEHI-UHFFFAOYSA-N 2-(hydroxymethyl)-4-methylsulfanylphenol Chemical compound CSC1=CC=C(O)C(CO)=C1 FFZMECXFDGAEHI-UHFFFAOYSA-N 0.000 description 2
VRSJMAPIRMHLTI-UHFFFAOYSA-N 2-amino-1-(4-fluorophenyl)-2-(2-methoxypyridin-4-yl)ethanone;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(C(N)C(=O)C=2C=CC(F)=CC=2)=C1 VRSJMAPIRMHLTI-UHFFFAOYSA-N 0.000 description 2
PEAJNZNKOKIMPP-UHFFFAOYSA-N 2-amino-1-(4-fluorophenyl)-2-(2-propan-2-yloxypyridin-4-yl)ethanone;hydrochloride Chemical compound Cl.C1=NC(OC(C)C)=CC(C(N)C(=O)C=2C=CC(F)=CC=2)=C1 PEAJNZNKOKIMPP-UHFFFAOYSA-N 0.000 description 2
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MZVSTDHRRYQFGI-UHFFFAOYSA-N 2-chloro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1 MZVSTDHRRYQFGI-UHFFFAOYSA-N 0.000 description 2
MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 2
UEFUHPOUXWUJPA-UHFFFAOYSA-N 2-hydroxy-5-methylsulfanylbenzaldehyde Chemical compound CSC1=CC=C(O)C(C=O)=C1 UEFUHPOUXWUJPA-UHFFFAOYSA-N 0.000 description 2
QTCQXOXUIPNFNH-UHFFFAOYSA-N 2-hydroxy-5-sulfanylbenzoic acid Chemical compound OC(=O)C1=CC(S)=CC=C1O QTCQXOXUIPNFNH-UHFFFAOYSA-N 0.000 description 2
OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
OUGKBBLPRJESSG-UHFFFAOYSA-N 4-(2-chloropyridin-4-yl)-5-(4-fluorophenyl)-1,3-dihydroimidazole-2-thione Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(Cl)N=CC=2)NC(=S)N1 OUGKBBLPRJESSG-UHFFFAOYSA-N 0.000 description 2
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JCJRWCIKESVJNQ-UHFFFAOYSA-N 4-(hydroxymethyl)-2-methylsulfanylphenol Chemical compound CSC1=CC(CO)=CC=C1O JCJRWCIKESVJNQ-UHFFFAOYSA-N 0.000 description 2
CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
IKLIRIKNLSNYOF-UHFFFAOYSA-N 4-methoxy-3-methylsulfanylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1SC IKLIRIKNLSNYOF-UHFFFAOYSA-N 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
MUXAWPOBIFIKIA-UHFFFAOYSA-N 5-chloro-2-hydroxy-3-methylsulfanylbenzoic acid Chemical compound CSC1=CC(Cl)=CC(C(O)=O)=C1O MUXAWPOBIFIKIA-UHFFFAOYSA-N 0.000 description 2
102000002260 Alkaline Phosphatase Human genes 0.000 description 2
108020004774 Alkaline Phosphatase Proteins 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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UAA200502484A 2002-08-20 2003-08-20 2-thio-substituted imidazole derivatives and their use in pharmaceutics UA80718C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10238045A DE10238045A1 (de)	2002-08-20	2002-08-20	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
PCT/EP2003/009219 WO2004018458A1 (de)	2002-08-20	2003-08-20	2-thio-substituierte imidazolderivate und ihre verwendung in der pharmazie

Publications (1)

Publication Number	Publication Date
UA80718C2 true UA80718C2 (en)	2007-10-25

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ID=31197117

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Application Number	Title	Priority Date	Filing Date
UAA200502484A UA80718C2 (en)	2002-08-20	2003-08-20	2-thio-substituted imidazole derivatives and their use in pharmaceutics

Country Status (19)

Country	Link
US (1)	US7582660B2 (sr)
EP (1)	EP1539741A1 (sr)
JP (1)	JP2005539035A (sr)
KR (1)	KR20050058419A (sr)
CN (1)	CN100396677C (sr)
AU (1)	AU2003267000B2 (sr)
BR (1)	BR0313277A (sr)
CA (1)	CA2501849A1 (sr)
DE (1)	DE10238045A1 (sr)
HR (1)	HRP20050239A2 (sr)
IS (1)	IS7740A (sr)
MX (1)	MXPA05001985A (sr)
NO (1)	NO20051477L (sr)
PL (1)	PL375793A1 (sr)
RS (1)	RS20050131A (sr)
RU (1)	RU2331638C2 (sr)
UA (1)	UA80718C2 (sr)
WO (1)	WO2004018458A1 (sr)
ZA (1)	ZA200501455B (sr)

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CN101128453A (zh) *	2005-02-28	2008-02-20	默克勒有限公司	2-亚磺酰基-和2-磺酰基-取代的咪唑衍生物和它们作为细胞因子抑制剂的用途
EP1894925A1 (en) *	2006-08-24	2008-03-05	Merckle Gmbh	Imidazole compounds having an antiinflammatory effect
US8143294B2 (en) *	2007-12-31	2012-03-27	Michael Burnet	2-sulfanyl-substituted imidazole derivatives and their use as cytokine inhibitors
JP5912946B2 (ja) *	2012-01-11	2016-04-27	株式会社Adeka	感光性樹脂組成物
WO2022067063A1 (en) *	2020-09-25	2022-03-31	Dana-Farber Cancer Institute, Inc.	Mutant selective egfr inhibitors and methods of use thereof

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GB9005966D0 (en)	1990-03-16	1990-05-09	May & Baker Ltd	New compositions of matter
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US5364875A (en) *	1992-05-11	1994-11-15	The Du Pont Merck Pharmaceutical Company	Imidazoles linked to bicyclic heterocyclic groups for the treatment of atherosclerosis
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DE10107683A1 (de)	2001-02-19	2002-08-29	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
DE10114775A1 (de)	2001-03-26	2002-10-10	Gerhard Dannhardt	2-Mercapto-4,5-diarylimidazolderivate und ihre Verwendung in der Pharmazie
DE10222103A1 (de)	2002-05-17	2003-11-27	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie

2002
- 2002-08-20 DE DE10238045A patent/DE10238045A1/de not_active Withdrawn
2003
- 2003-08-20 US US10/524,486 patent/US7582660B2/en not_active Expired - Fee Related
- 2003-08-20 HR HR20050239A patent/HRP20050239A2/hr not_active Application Discontinuation
- 2003-08-20 CA CA002501849A patent/CA2501849A1/en not_active Abandoned
- 2003-08-20 AU AU2003267000A patent/AU2003267000B2/en not_active Ceased
- 2003-08-20 WO PCT/EP2003/009219 patent/WO2004018458A1/de not_active Ceased
- 2003-08-20 JP JP2004530221A patent/JP2005539035A/ja active Pending
- 2003-08-20 UA UAA200502484A patent/UA80718C2/uk unknown
- 2003-08-20 CN CNB038197502A patent/CN100396677C/zh not_active Expired - Fee Related
- 2003-08-20 PL PL03375793A patent/PL375793A1/xx not_active Application Discontinuation
- 2003-08-20 KR KR1020057002947A patent/KR20050058419A/ko not_active Ceased
- 2003-08-20 EP EP03747916A patent/EP1539741A1/de not_active Withdrawn
- 2003-08-20 MX MXPA05001985A patent/MXPA05001985A/es active IP Right Grant
- 2003-08-20 RS YUP-2005/0131A patent/RS20050131A/sr unknown
- 2003-08-20 BR BR0313277-3A patent/BR0313277A/pt not_active IP Right Cessation
- 2003-08-20 RU RU2005107726/04A patent/RU2331638C2/ru not_active IP Right Cessation
2005
- 2005-02-18 ZA ZA200501455A patent/ZA200501455B/en unknown
- 2005-03-14 IS IS7740A patent/IS7740A/is unknown
- 2005-03-18 NO NO20051477A patent/NO20051477L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
US7582660B2 (en)	2009-09-01
BR0313277A (pt)	2005-06-21
PL375793A1 (en)	2005-12-12
CN1675197A (zh)	2005-09-28
KR20050058419A (ko)	2005-06-16
IS7740A (is)	2005-03-14
HRP20050239A2 (en)	2005-10-31
WO2004018458A1 (de)	2004-03-04
CN100396677C (zh)	2008-06-25
US20060235054A1 (en)	2006-10-19
CA2501849A1 (en)	2004-03-04
ZA200501455B (en)	2006-10-25
EP1539741A1 (de)	2005-06-15
AU2003267000A1 (en)	2004-03-11
RU2005107726A (ru)	2006-01-20
JP2005539035A (ja)	2005-12-22
AU2003267000B2 (en)	2009-05-28
MXPA05001985A (es)	2005-05-27
NO20051477L (no)	2005-05-19
DE10238045A1 (de)	2004-03-04
RU2331638C2 (ru)	2008-08-20
RS20050131A (sr)	2007-06-04

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KR19990022574A (ko)	1999-03-25	이미다졸 화합물
JPH10512264A (ja)	1998-11-24	新規化合物
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SE466309B (sv)	1992-01-27	1-pyrimidinyloxi-3-hetarylalkylamino-2-propanoler, farmaceutisk komposition och framstaellning daerav
JP2000505428A (ja)	2000-05-09	ヒスタミンｈ▲下３▼レセプターリガンド
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UA80718C2 (en)	2007-10-25	2-thio-substituted imidazole derivatives and their use in pharmaceutics
CA1257274A (en)	1989-07-11	Amidine derivatives of 2-substituted 4- phenylimidazole
NZ538222A (en)	2006-11-30	2-Thio-substituted imidazole derivatives and their use in pharmaceuticals
KR19990077166A (ko)	1999-10-25	신규한 시클로알킬 치환 이미다졸