SK10242003A3 - 2-Tiosubstituované imidazolové deriváty a ich použitie vo farmácii - Google Patents

2-Tiosubstituované imidazolové deriváty a ich použitie vo farmácii Download PDF

Info

Publication number: SK10242003A3
Authority: SK; Slovakia
Prior art keywords: alkyl; substituted; phenyl; group; pyridyl
Prior art date: 2001-02-19

Application number

SK1024-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Stefan Laufer

Dunja Kotschenreuther

Philipp Merckle

Karola Tollmann

Hans-G�Nter Striegel

Original Assignee

Merckle Gmbh, Chem.-Pharm. Fabrik

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.)

2001-02-19

Filing date

2002-02-19

Publication date

2004-03-02

2002-02-19 Application filed by Merckle Gmbh, Chem.-Pharm. Fabrik filed Critical Merckle Gmbh, Chem.-Pharm. Fabrik

2004-03-02 Publication of SK10242003A3 publication Critical patent/SK10242003A3/sk

Links

150000002460 imidazoles Chemical class 0.000 title claims abstract description 12
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 118
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 4
210000000987 immune system Anatomy 0.000 claims abstract description 4
-1 aromatic heterocyclic radical Chemical class 0.000 claims description 96
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 72
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 46
238000000034 method Methods 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 24
125000003118 aryl group Chemical group 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 22
229910052717 sulfur Inorganic materials 0.000 claims description 22
125000005842 heteroatom Chemical group 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 17
125000006413 ring segment Chemical group 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 16
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 14
125000000217 alkyl group Chemical group 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
NBGMRMDAEWWFIR-UHFFFAOYSA-N imidazole-2-thione Chemical compound S=C1N=CC=N1 NBGMRMDAEWWFIR-UHFFFAOYSA-N 0.000 claims description 6
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
125000005001 aminoaryl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
230000001010 compromised effect Effects 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
230000001771 impaired effect Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 6
230000002519 immonomodulatory effect Effects 0.000 abstract description 4
201000010099 disease Diseases 0.000 abstract 1
230000004064 dysfunction Effects 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 72
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
239000000203 mixture Substances 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
239000011541 reaction mixture Substances 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000002244 precipitate Substances 0.000 description 21
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
238000001816 cooling Methods 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
238000005574 benzylation reaction Methods 0.000 description 15
239000000460 chlorine Substances 0.000 description 15
238000010992 reflux Methods 0.000 description 15
239000002904 solvent Substances 0.000 description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 14
150000003254 radicals Chemical class 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000002390 rotary evaporation Methods 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
229940125898 compound 5 Drugs 0.000 description 11
150000002466 imines Chemical class 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-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
238000004440 column chromatography Methods 0.000 description 10
239000012153 distilled water Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
239000012043 crude product Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
DRVNNGHVOPNCGY-UHFFFAOYSA-N 1,3,5-tricyclopropyl-1,3,5-triazinane Chemical compound C1CC1N1CN(C2CC2)CN(C2CC2)C1 DRVNNGHVOPNCGY-UHFFFAOYSA-N 0.000 description 4
IOXAEZSQRZMYNX-UHFFFAOYSA-N 1-(2-aminopyridin-4-yl)-2-(4-fluorophenyl)ethanone Chemical compound C1=NC(N)=CC(C(=O)CC=2C=CC(F)=CC=2)=C1 IOXAEZSQRZMYNX-UHFFFAOYSA-N 0.000 description 4
LXPRVXKHIXWBJZ-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CCl)C=C1 LXPRVXKHIXWBJZ-UHFFFAOYSA-N 0.000 description 4
VNQIEKXUBYBTPS-UHFFFAOYSA-N 2-acetamidopyridine-4-carboxylic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC=N1 VNQIEKXUBYBTPS-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
CJSAWDBVCZUIGO-UHFFFAOYSA-N 4-[3-(1,3,5-triazinan-1-yl)propyl]morpholine Chemical compound O1CCN(CC1)CCCN1CNCNC1 CJSAWDBVCZUIGO-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000002585 base Substances 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
WRAMFBNOYKKPPJ-UHFFFAOYSA-N n-[4-[2-cyano-2-(4-fluorophenyl)acetyl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C(=O)C(C#N)C=2C=CC(F)=CC=2)=C1 WRAMFBNOYKKPPJ-UHFFFAOYSA-N 0.000 description 4
125000003386 piperidinyl group Chemical group 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
OZFAFGSSMRRTDW-UHFFFAOYSA-N (2,4-dichlorophenyl) benzenesulfonate Chemical compound ClC1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=CC=C1 OZFAFGSSMRRTDW-UHFFFAOYSA-N 0.000 description 3
LKLLNYWECKEQIB-UHFFFAOYSA-N 1,3,5-triazinane Chemical compound C1NCNCN1 LKLLNYWECKEQIB-UHFFFAOYSA-N 0.000 description 3
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 3
DPHBVWJGMBYPMK-UHFFFAOYSA-N 1,3,5-tripropyl-1,3,5-triazinane Chemical compound CCCN1CN(CCC)CN(CCC)C1 DPHBVWJGMBYPMK-UHFFFAOYSA-N 0.000 description 3
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 3
YZAOXPVBHKVFBR-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-pyridin-4-ylpropanenitrile Chemical compound C1=CC(F)=CC=C1C(C#N)CC1=CC=NC=C1 YZAOXPVBHKVFBR-UHFFFAOYSA-N 0.000 description 3
JHQBLYITVCBGTO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetonitrile Chemical compound FC1=CC=C(CC#N)C=C1 JHQBLYITVCBGTO-UHFFFAOYSA-N 0.000 description 3
IBKMZYWDWWIWEL-UHFFFAOYSA-N 4-methylpyridin-3-amine Chemical compound CC1=CC=NC=C1N IBKMZYWDWWIWEL-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 3
206010007559 Cardiac failure congestive Diseases 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
239000012591 Dulbecco’s Phosphate Buffered Saline Substances 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241001484259 Lacuna Species 0.000 description 3
108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
QGZHGSGLCZEGHA-UHFFFAOYSA-N n-(4-methylpyridin-2-yl)acetamide Chemical compound CC(=O)NC1=CC(C)=CC=N1 QGZHGSGLCZEGHA-UHFFFAOYSA-N 0.000 description 3
IBIRZTPHSLNZFC-UHFFFAOYSA-N n-[4-[2-(4-fluorophenyl)acetyl]pyridin-2-yl]acetamide Chemical compound C1=NC(NC(=O)C)=CC(C(=O)CC=2C=CC(F)=CC=2)=C1 IBIRZTPHSLNZFC-UHFFFAOYSA-N 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
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UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
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238000005935 nucleophilic addition reaction Methods 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
208000028169 periodontal disease Diseases 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000006187 phenyl benzyl group Chemical group 0.000 description 1
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125000004660 phenylalkylthio group Chemical group 0.000 description 1
125000000286 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
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 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
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
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
206010047470 viral myocarditis Diseases 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

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- 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
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- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
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Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Immunology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Physical Education & Sports Medicine (AREA)
Rheumatology (AREA)
Communicable Diseases (AREA)
Diabetes (AREA)
Virology (AREA)
Oncology (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Pulmonology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Dermatology (AREA)
Hospice & Palliative Care (AREA)
Hematology (AREA)
Molecular Biology (AREA)
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Tropical Medicine & Parasitology (AREA)
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SK1024-2003A 2001-02-19 2002-02-19 2-Tiosubstituované imidazolové deriváty a ich použitie vo farmácii SK10242003A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10107683A DE10107683A1 (de)	2001-02-19	2001-02-19	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
PCT/EP2002/001746 WO2002066458A2 (de)	2001-02-19	2002-02-19	2-thio-substituierte imidazolderivate und ihre verwendung in der pharmazie

Publications (1)

Publication Number	Publication Date
SK10242003A3 true SK10242003A3 (sk)	2004-03-02

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SK1024-2003A SK10242003A3 (sk)	2001-02-19	2002-02-19	2-Tiosubstituované imidazolové deriváty a ich použitie vo farmácii

Country Status (22)

Country	Link
US (1)	US7253191B2 (cs)
EP (1)	EP1362045B1 (cs)
JP (1)	JP2004521913A (cs)
KR (1)	KR100642231B1 (cs)
CN (1)	CN1291984C (cs)
AT (1)	ATE282605T1 (cs)
AU (1)	AU2002247726C1 (cs)
BR (1)	BR0207254A (cs)
CA (1)	CA2453078A1 (cs)
CZ (1)	CZ20032224A3 (cs)
DE (2)	DE10107683A1 (cs)
DK (1)	DK1362045T3 (cs)
ES (1)	ES2233808T3 (cs)
HU (1)	HUP0303155A3 (cs)
IL (1)	IL157050A0 (cs)
IS (1)	IS6914A (cs)
MX (1)	MXPA03007380A (cs)
PL (1)	PL367397A1 (cs)
PT (1)	PT1362045E (cs)
RU (1)	RU2284326C2 (cs)
SK (1)	SK10242003A3 (cs)
WO (1)	WO2002066458A2 (cs)

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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
DE10222103A1 (de)	2002-05-17	2003-11-27	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
DE10238045A1 (de) *	2002-08-20	2004-03-04	Merckle Gmbh Chem.-Pharm. Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie
DE10256881A1 (de) *	2002-12-05	2004-06-24	Beiersdorf Ag	Neue topische Verwendung von Bis-Arylimidazo[1,2-a]thiolanderivaten
AR049386A1 (es)	2004-05-26	2006-07-26	Janssen Pharmaceutica Nv	Mercaptoimidazoles como antagonistas del receptor ccr2
CN1956976A (zh) *	2004-05-26	2007-05-02	詹森药业有限公司	作为ccr2受体拮抗剂的巯基咪唑化合物
EP1778646A1 (en) *	2004-08-11	2007-05-02	Janssen Pharmaceutica N.V.	Mercaptoimidazoles as ccr2 receptor antagonists
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
WO2008085008A1 (en) *	2007-01-11	2008-07-17	Mogam Biotechnology Research Institute	T-cell inhibiting compounds and their use for the treatment of t-cell-mediated diseases
US8143294B2 (en)	2007-12-31	2012-03-27	Michael Burnet	2-sulfanyl-substituted imidazole derivatives and their use as cytokine inhibitors
CN102249992A (zh) *	2011-07-05	2011-11-23	广东工业大学	一种制备2-氨基异烟酸的方法
DE102013102069A1 (de)	2013-03-01	2014-09-04	Fsp Fluid Systems Partners Holding Ag	Proportional-Wegeventil sowie hydraulische Schaltung und hydropneumatisches Federungssystem mit einem derartigen Ventil
US20190060286A1 (en)	2016-02-29	2019-02-28	University Of Florida Research Foundation, Incorpo	Chemotherapeutic Methods
US11795160B2 (en) *	2019-02-22	2023-10-24	Insilico Medicine Ip Limited	Kinase inhibitors
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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

2001
- 2001-02-19 DE DE10107683A patent/DE10107683A1/de not_active Withdrawn
2002
- 2002-02-19 EP EP02716791A patent/EP1362045B1/de not_active Expired - Lifetime
- 2002-02-19 CZ CZ20032224A patent/CZ20032224A3/cs unknown
- 2002-02-19 PL PL02367397A patent/PL367397A1/xx not_active Application Discontinuation
- 2002-02-19 MX MXPA03007380A patent/MXPA03007380A/es active IP Right Grant
- 2002-02-19 US US10/467,064 patent/US7253191B2/en not_active Expired - Fee Related
- 2002-02-19 SK SK1024-2003A patent/SK10242003A3/sk not_active Application Discontinuation
- 2002-02-19 WO PCT/EP2002/001746 patent/WO2002066458A2/de not_active Ceased
- 2002-02-19 CN CNB028051548A patent/CN1291984C/zh not_active Expired - Fee Related
- 2002-02-19 HU HU0303155A patent/HUP0303155A3/hu unknown
- 2002-02-19 KR KR1020037010839A patent/KR100642231B1/ko not_active Expired - Fee Related
- 2002-02-19 DK DK02716791T patent/DK1362045T3/da active
- 2002-02-19 DE DE50201565T patent/DE50201565D1/de not_active Expired - Lifetime
- 2002-02-19 CA CA002453078A patent/CA2453078A1/en not_active Abandoned
- 2002-02-19 AT AT02716791T patent/ATE282605T1/de not_active IP Right Cessation
- 2002-02-19 PT PT02716791T patent/PT1362045E/pt unknown
- 2002-02-19 RU RU2003128068/04A patent/RU2284326C2/ru not_active IP Right Cessation
- 2002-02-19 JP JP2002565973A patent/JP2004521913A/ja active Pending
- 2002-02-19 BR BR0207254-8A patent/BR0207254A/pt not_active IP Right Cessation
- 2002-02-19 AU AU2002247726A patent/AU2002247726C1/en not_active Ceased
- 2002-02-19 ES ES02716791T patent/ES2233808T3/es not_active Expired - Lifetime
- 2002-02-19 IL IL15705002A patent/IL157050A0/xx unknown
2003
- 2003-08-15 IS IS6914A patent/IS6914A/is unknown

Also Published As

Publication number	Publication date
KR100642231B1 (ko)	2006-11-02
RU2284326C2 (ru)	2006-09-27
US20040116416A1 (en)	2004-06-17
WO2002066458A3 (de)	2002-12-12
KR20030082940A (ko)	2003-10-23
CZ20032224A3 (en)	2004-06-16
HUP0303155A3 (en)	2007-08-28
JP2004521913A (ja)	2004-07-22
ES2233808T3 (es)	2005-06-16
CN1511149A (zh)	2004-07-07
BR0207254A (pt)	2004-02-10
IS6914A (is)	2003-08-15
EP1362045A2 (de)	2003-11-19
DE10107683A1 (de)	2002-08-29
CN1291984C (zh)	2006-12-27
RU2003128068A (ru)	2005-01-27
WO2002066458A2 (de)	2002-08-29
IL157050A0 (en)	2004-02-08
AU2002247726B2 (en)	2006-01-19
PT1362045E (pt)	2005-04-29
DE50201565D1 (de)	2004-12-23
US7253191B2 (en)	2007-08-07
MXPA03007380A (es)	2004-03-16
PL367397A1 (en)	2005-02-21
AU2002247726C1 (en)	2006-08-17
HK1056725A1 (en)	2004-02-27
CA2453078A1 (en)	2002-08-29
DK1362045T3 (da)	2005-03-29
ATE282605T1 (de)	2004-12-15
EP1362045B1 (de)	2004-11-17
HUP0303155A2 (hu)	2003-12-29

Legal Events

Date	Code	Title	Description
2011-04-05	FC9A	Refused patent application

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