UA80718C2 - 2-thio-substituted imidazole derivatives and their use in pharmaceutics - Google Patents
2-thio-substituted imidazole derivatives and their use in pharmaceutics Download PDFInfo
- Publication number
- UA80718C2 UA80718C2 UAA200502484A UA2005002484A UA80718C2 UA 80718 C2 UA80718 C2 UA 80718C2 UA A200502484 A UAA200502484 A UA A200502484A UA 2005002484 A UA2005002484 A UA 2005002484A UA 80718 C2 UA80718 C2 UA 80718C2
- Authority
- UA
- Ukraine
- Prior art keywords
- alkyl
- halogen
- rug
- phenyl
- substituted
- Prior art date
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- 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
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- 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
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
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- 125000003277 amino group Chemical group 0.000 description 3
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- 238000004821 distillation Methods 0.000 description 3
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- 125000000623 heterocyclic group Chemical group 0.000 description 3
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- 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
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- 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
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- 229910001845 yogo sapphire Inorganic materials 0.000 description 3
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- 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
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- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
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- 239000000375 suspending agent Substances 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 206010047470 viral myocarditis Diseases 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hospice & Palliative Care (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Virology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Communicable Diseases (AREA)
- Endocrinology (AREA)
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 |
Family
ID=31197117
Family Applications (1)
| 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 (ru) |
| EP (1) | EP1539741A1 (ru) |
| JP (1) | JP2005539035A (ru) |
| KR (1) | KR20050058419A (ru) |
| CN (1) | CN100396677C (ru) |
| AU (1) | AU2003267000B2 (ru) |
| BR (1) | BR0313277A (ru) |
| CA (1) | CA2501849A1 (ru) |
| DE (1) | DE10238045A1 (ru) |
| HR (1) | HRP20050239A2 (ru) |
| IS (1) | IS7740A (ru) |
| MX (1) | MXPA05001985A (ru) |
| NO (1) | NO20051477L (ru) |
| PL (1) | PL375793A1 (ru) |
| RS (1) | RS20050131A (ru) |
| RU (1) | RU2331638C2 (ru) |
| UA (1) | UA80718C2 (ru) |
| WO (1) | WO2004018458A1 (ru) |
| ZA (1) | ZA200501455B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE469893T1 (de) * | 2005-02-28 | 2010-06-15 | Merckle Gmbh | 2-sulfinyl- und 2-sulfonyl-substituierte imidazolderivate und deren verwendung als cytokininhibitoren |
| 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 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190666A (en) * | 1975-08-11 | 1980-02-26 | E. I. Du Pont De Nemours And Company | Anti-inflammatory 4,5-diarly-2-(substituted-thio)imidazoles and their corresponding sulfoxides and sulfones |
| CY1302A (en) * | 1978-04-11 | 1985-12-06 | Ciba Geigy Ag | Mercapto-imidazole derivatives,their preparation,their pharmaceutical compositions and applications |
| DE2823197A1 (de) | 1978-05-24 | 1979-11-29 | Schering Ag | Neue imidazolderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3025484A1 (de) * | 1980-07-03 | 1982-02-04 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3141063A1 (de) * | 1981-10-13 | 1983-04-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Neue imidazol-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3504678A1 (de) | 1985-02-12 | 1986-08-14 | A. Nattermann & Cie GmbH, 5000 Köln | Neue imidazolyl-oxyalkansaeuren und -thioalkansaeuren, ihre derivate und verfahren zu ihrer herstellung |
| US4686231A (en) | 1985-12-12 | 1987-08-11 | Smithkline Beckman Corporation | Inhibition of 5-lipoxygenase products |
| SU1415725A1 (ru) | 1986-11-17 | 1996-10-10 | В.М. Виноградов | Дигидрохлорид 4-(4'-метоксифенил)-2-морфолиноэтилтио-5-фенилимидазола, повышающий физическую выносливость |
| JPS6440467A (en) | 1987-08-04 | 1989-02-10 | Hisamitsu Pharmaceutical Co | Novel substituted diphenylimidazole derivative |
| CA2003283A1 (en) | 1988-12-05 | 1990-06-05 | C. Anne Higley | Imidazoles for the treatment of atherosclerosis |
| JPH05503095A (ja) | 1990-01-12 | 1993-05-27 | ローン―プーラン・ロレ・ソシエテ・アノニム | イミダゾール類 |
| GB9005966D0 (en) | 1990-03-16 | 1990-05-09 | May & Baker Ltd | New compositions of matter |
| IL104369A0 (en) * | 1992-01-13 | 1993-05-13 | Smithkline Beecham Corp | Novel compounds and compositions |
| 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 |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5620999A (en) | 1994-07-28 | 1997-04-15 | Weier; Richard M. | Benzenesulfonamide subtituted imidazolyl compounds for the treatment of inflammation |
| US6040320A (en) * | 1997-06-30 | 2000-03-21 | Ortho-Mcneil Pharmaceutical, Inc. | 2-substituted imidazoles useful in the treatment of inflammatory diseases |
| DE19842833B4 (de) * | 1998-09-18 | 2005-04-14 | Merckle Gmbh | 2-Arylalkylthio-imidazole, 2-Arylalkenylthio-imidazole und 2-Arylalkinylthio-imidazole als Entzündungs-Hemmstoffe und Hemmstoffe der Cytokin-Freisetzung |
| 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 CN CNB038197502A patent/CN100396677C/zh not_active Expired - Fee Related
- 2003-08-20 CA CA002501849A patent/CA2501849A1/en not_active Abandoned
- 2003-08-20 KR KR1020057002947A patent/KR20050058419A/ko not_active Application Discontinuation
- 2003-08-20 US US10/524,486 patent/US7582660B2/en not_active Expired - Fee Related
- 2003-08-20 RU RU2005107726/04A patent/RU2331638C2/ru not_active IP Right Cessation
- 2003-08-20 MX MXPA05001985A patent/MXPA05001985A/es active IP Right Grant
- 2003-08-20 BR BR0313277-3A patent/BR0313277A/pt not_active IP Right Cessation
- 2003-08-20 PL PL03375793A patent/PL375793A1/xx not_active Application Discontinuation
- 2003-08-20 EP EP03747916A patent/EP1539741A1/de not_active Withdrawn
- 2003-08-20 RS YUP-2005/0131A patent/RS20050131A/sr unknown
- 2003-08-20 AU AU2003267000A patent/AU2003267000B2/en 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 WO PCT/EP2003/009219 patent/WO2004018458A1/de active Application Filing
-
2005
- 2005-02-18 ZA ZA200501455A patent/ZA200501455B/en unknown
- 2005-03-14 IS IS7740A patent/IS7740A/is unknown
- 2005-03-14 HR HR20050239A patent/HRP20050239A2/hr not_active Application Discontinuation
- 2005-03-18 NO NO20051477A patent/NO20051477L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| RU2331638C2 (ru) | 2008-08-20 |
| US20060235054A1 (en) | 2006-10-19 |
| IS7740A (is) | 2005-03-14 |
| RS20050131A (en) | 2007-06-04 |
| JP2005539035A (ja) | 2005-12-22 |
| AU2003267000B2 (en) | 2009-05-28 |
| HRP20050239A2 (en) | 2005-10-31 |
| ZA200501455B (en) | 2006-10-25 |
| EP1539741A1 (de) | 2005-06-15 |
| US7582660B2 (en) | 2009-09-01 |
| CA2501849A1 (en) | 2004-03-04 |
| WO2004018458A1 (de) | 2004-03-04 |
| BR0313277A (pt) | 2005-06-21 |
| DE10238045A1 (de) | 2004-03-04 |
| KR20050058419A (ko) | 2005-06-16 |
| CN100396677C (zh) | 2008-06-25 |
| AU2003267000A1 (en) | 2004-03-11 |
| CN1675197A (zh) | 2005-09-28 |
| PL375793A1 (en) | 2005-12-12 |
| RU2005107726A (ru) | 2006-01-20 |
| NO20051477L (no) | 2005-05-19 |
| MXPA05001985A (es) | 2005-05-27 |
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