HRP20000377A2 - Novel urethanes derived from azacycloalkanes,their thio and dithio analogues, their salts, pharmaceutical preparations containing the indicated compounds and their use and preparation processes - Google Patents
Novel urethanes derived from azacycloalkanes,their thio and dithio analogues, their salts, pharmaceutical preparations containing the indicated compounds and their use and preparation processes Download PDFInfo
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- HRP20000377A2 HRP20000377A2 HR20000377A HRP20000377A HRP20000377A2 HR P20000377 A2 HRP20000377 A2 HR P20000377A2 HR 20000377 A HR20000377 A HR 20000377A HR P20000377 A HRP20000377 A HR P20000377A HR P20000377 A2 HRP20000377 A2 HR P20000377A2
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- 150000001875 compounds Chemical class 0.000 title claims description 112
- 150000003839 salts Chemical class 0.000 title claims description 30
- 238000002360 preparation method Methods 0.000 title claims description 16
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 title claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title claims description 5
- 150000003673 urethanes Chemical class 0.000 title claims description 5
- 150000003976 azacycloalkanes Chemical class 0.000 title claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 69
- 239000000203 mixture Substances 0.000 claims description 43
- 229910052717 sulfur Inorganic materials 0.000 claims description 35
- 125000004434 sulfur atom Chemical group 0.000 claims description 35
- 235000012000 cholesterol Nutrition 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 27
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 20
- -1 methylene, carbonyl Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 14
- 208000001130 gallstones Diseases 0.000 claims description 13
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 12
- 102100032011 Lanosterol synthase Human genes 0.000 claims description 12
- 108010059597 Lanosterol synthase Proteins 0.000 claims description 12
- 239000013543 active substance Substances 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 150000002632 lipids Chemical class 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 7
- 201000001883 cholelithiasis Diseases 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 206010017533 Fungal infection Diseases 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 5
- 235000013601 eggs Nutrition 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- 230000003143 atherosclerotic effect Effects 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000024386 fungal infectious disease Diseases 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 206010017711 Gangrene Diseases 0.000 claims description 3
- 206010022562 Intermittent claudication Diseases 0.000 claims description 3
- 206010008118 cerebral infarction Diseases 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229940125753 fibrate Drugs 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- JSGOXALVDQIOEM-UHFFFAOYSA-N benzyl 4-[4-[(dimethylamino)methyl]phenyl]sulfanylpiperidine-1-carbodithioate Chemical compound C1=CC(CN(C)C)=CC=C1SC1CCN(C(=S)SCC=2C=CC=CC=2)CC1 JSGOXALVDQIOEM-UHFFFAOYSA-N 0.000 claims description 2
- DHDKCCJMEOVNAI-UHFFFAOYSA-N benzyl 4-[[4-[(dimethylamino)methyl]phenyl]methyl]piperidine-1-carbodithioate Chemical compound C1=CC(CN(C)C)=CC=C1CC1CCN(C(=S)SCC=2C=CC=CC=2)CC1 DHDKCCJMEOVNAI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003613 bile acid Substances 0.000 claims description 2
- 230000001906 cholesterol absorption Effects 0.000 claims description 2
- 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 2
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 230000007246 mechanism Effects 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- MZEADIIVVFWIAZ-UHFFFAOYSA-N o-(4-methylphenyl) 4-[[4-[(dimethylamino)methyl]phenyl]methyl]piperidine-1-carbothioate Chemical compound C1=CC(CN(C)C)=CC=C1CC1CCN(C(=S)OC=2C=CC(C)=CC=2)CC1 MZEADIIVVFWIAZ-UHFFFAOYSA-N 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims description 2
- 229960003912 probucol Drugs 0.000 claims description 2
- 229920005989 resin Polymers 0.000 claims description 2
- 239000011347 resin Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- MMRZFYXYJJVVQD-UHFFFAOYSA-N benzyl 4-[[4-[(dimethylamino)methyl]phenyl]methylidene]piperidine-1-carbodithioate Chemical compound C1=CC(CN(C)C)=CC=C1C=C1CCN(C(=S)SCC=2C=CC=CC=2)CC1 MMRZFYXYJJVVQD-UHFFFAOYSA-N 0.000 claims 1
- 238000001311 chemical methods and process Methods 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 238000002844 melting Methods 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000003112 inhibitor Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 18
- 239000012458 free base Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000003208 petroleum Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 10
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 9
- PTNVBAZHLFJXIY-UHFFFAOYSA-N n,n-dimethyl-1-[4-(piperidin-4-ylmethyl)phenyl]methanamine Chemical compound C1=CC(CN(C)C)=CC=C1CC1CCNCC1 PTNVBAZHLFJXIY-UHFFFAOYSA-N 0.000 description 9
- 210000003491 skin Anatomy 0.000 description 9
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 8
- 229960004844 lovastatin Drugs 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 230000002349 favourable effect Effects 0.000 description 7
- 230000003463 hyperproliferative effect Effects 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000000699 topical effect Effects 0.000 description 7
- QYIMSPSDBYKPPY-BANQPHDMSA-N 2,3-epoxysqualene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC1OC1(C)C QYIMSPSDBYKPPY-BANQPHDMSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- QCFFKKDOYQCKLR-UHFFFAOYSA-N n,n-dimethyl-1-(4-piperidin-4-ylsulfanylphenyl)methanamine Chemical compound C1=CC(CN(C)C)=CC=C1SC1CCNCC1 QCFFKKDOYQCKLR-UHFFFAOYSA-N 0.000 description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 150000003431 steroids Chemical class 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 102000005782 Squalene Monooxygenase Human genes 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 230000000326 anti-hypercholesterolaemic effect Effects 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
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- 230000003780 keratinization Effects 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
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- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 3
- RYWGPCLTVXMMHO-UHFFFAOYSA-N (4-chlorophenyl) carbonochloridate Chemical compound ClC(=O)OC1=CC=C(Cl)C=C1 RYWGPCLTVXMMHO-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
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- 206010004146 Basal cell carcinoma Diseases 0.000 description 3
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- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 3
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- 241001465754 Metazoa Species 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 3
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- 150000001408 amides Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 229910052794 bromium 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
- 238000003776 cleavage reaction Methods 0.000 description 3
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- 208000035475 disorder Diseases 0.000 description 3
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- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 3
- 230000008686 ergosterol biosynthesis Effects 0.000 description 3
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 230000002538 fungal effect Effects 0.000 description 3
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- OZGNYLLQHRPOBR-DHZHZOJOSA-N naftifine Chemical compound C=1C=CC2=CC=CC=C2C=1CN(C)C\C=C\C1=CC=CC=C1 OZGNYLLQHRPOBR-DHZHZOJOSA-N 0.000 description 1
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- 150000002923 oximes Chemical class 0.000 description 1
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- JSLPLJJRYKMRAA-UHFFFAOYSA-N phenyl 4-[4-(piperidin-1-ylmethyl)phenyl]sulfanylpiperidine-1-carboxylate;hydrochloride Chemical compound Cl.C1CC(SC=2C=CC(CN3CCCCC3)=CC=2)CCN1C(=O)OC1=CC=CC=C1 JSLPLJJRYKMRAA-UHFFFAOYSA-N 0.000 description 1
- WMASOBIUXARKQP-UHFFFAOYSA-N phenyl 4-[4-[(dimethylamino)methyl]phenyl]sulfanylpiperidine-1-carbodithioate;hydrochloride Chemical compound Cl.C1=CC(CN(C)C)=CC=C1SC1CCN(C(=S)SC=2C=CC=CC=2)CC1 WMASOBIUXARKQP-UHFFFAOYSA-N 0.000 description 1
- IHCZWWKERARLHF-UHFFFAOYSA-N phenyl 4-[4-[(dimethylamino)methyl]phenyl]sulfanylpiperidine-1-carboxylate;hydrochloride Chemical compound Cl.C1=CC(CN(C)C)=CC=C1SC1CCN(C(=O)OC=2C=CC=CC=2)CC1 IHCZWWKERARLHF-UHFFFAOYSA-N 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
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- 235000019148 tocotrienols Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- SYHDSBBKRLVLFF-UHFFFAOYSA-N triparanol Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(O)(C=1C=CC(C)=CC=1)CC1=CC=C(Cl)C=C1 SYHDSBBKRLVLFF-UHFFFAOYSA-N 0.000 description 1
- 229950005498 triparanol Drugs 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- 229940035936 ubiquinone Drugs 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
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- 208000021331 vascular occlusion disease Diseases 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- DFKDOZMCHOGOBR-NCSQYGPNSA-N zaragozic acid A Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CC[C@]12[C@H](O)[C@H]([C@](O2)(C(O)=O)[C@@](O)([C@H](O1)C(O)=O)C(O)=O)OC(=O)/C=C/[C@@H](C)C[C@@H](C)CC)C1=CC=CC=C1 DFKDOZMCHOGOBR-NCSQYGPNSA-N 0.000 description 1
- DFKDOZMCHOGOBR-UHFFFAOYSA-N zaragozic acid A Natural products O1C(C(O)(C(O2)C(O)=O)C(O)=O)(C(O)=O)C(OC(=O)C=CC(C)CC(C)CC)C(O)C21CCC(=C)C(OC(C)=O)C(C)CC1=CC=CC=C1 DFKDOZMCHOGOBR-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/132—Heterocyclic compounds containing only one nitrogen as hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/70—Feeding-stuffs specially adapted for particular animals for birds
- A23K50/75—Feeding-stuffs specially adapted for particular animals for birds for poultry
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Polymers & Plastics (AREA)
- Heart & Thoracic Surgery (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Birds (AREA)
- Food Science & Technology (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Oncology (AREA)
- Obesity (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19754796A DE19754796A1 (de) | 1997-12-10 | 1997-12-10 | Neue, von Azacycloalkanen abgeleitete Urethane, ihre Thio- und Dithioanaloga, deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
PCT/EP1998/007965 WO1999029669A1 (de) | 1997-12-10 | 1998-12-08 | Von azacycloalkanen abgeleitete urethane, ihre thio- und dithioanaloga, deren herstellung und deren verwendung als 2,3-epoxisqualen-lanosterol-cyclase inhibitoren |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000377A2 true HRP20000377A2 (en) | 2000-12-31 |
Family
ID=7851381
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000377A HRP20000377A2 (en) | 1997-12-10 | 2000-06-07 | Novel urethanes derived from azacycloalkanes,their thio and dithio analogues, their salts, pharmaceutical preparations containing the indicated compounds and their use and preparation processes |
Country Status (27)
Country | Link |
---|---|
EP (1) | EP1060162B1 (ko) |
JP (1) | JP3418688B2 (ko) |
KR (1) | KR20010032977A (ko) |
CN (1) | CN1281434A (ko) |
AR (1) | AR017827A1 (ko) |
AT (1) | ATE234816T1 (ko) |
AU (1) | AU1759499A (ko) |
BG (1) | BG104500A (ko) |
BR (1) | BR9813495A (ko) |
CA (1) | CA2309388A1 (ko) |
CO (1) | CO5370694A1 (ko) |
DE (2) | DE19754796A1 (ko) |
DK (1) | DK1060162T3 (ko) |
EA (1) | EA200000631A1 (ko) |
EE (1) | EE200000342A (ko) |
ES (1) | ES2190130T3 (ko) |
HR (1) | HRP20000377A2 (ko) |
HU (1) | HUP0100335A3 (ko) |
IL (1) | IL135738A0 (ko) |
NO (1) | NO20002967L (ko) |
PL (1) | PL341060A1 (ko) |
PT (1) | PT1060162E (ko) |
SK (1) | SK8612000A3 (ko) |
TR (1) | TR200001635T2 (ko) |
WO (1) | WO1999029669A1 (ko) |
YU (1) | YU35600A (ko) |
ZA (1) | ZA9811262B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1351935A1 (en) * | 2001-01-15 | 2003-10-15 | Glaxo Group Limited | Aryl piperidine derivatives as inducers of ldl-receptor expression |
US20040147557A1 (en) * | 2001-01-15 | 2004-07-29 | Anne Bouillot | Aryl piperidine derivatives as inducers of ldl-receptor expression |
WO2002055496A1 (en) * | 2001-01-15 | 2002-07-18 | Glaxo Group Limited | Aryl piperidine and piperazine derivatives as inducers of ldl-receptor expression |
DE10132686A1 (de) * | 2001-07-05 | 2003-01-16 | Boehringer Ingelheim Pharma | Heteroarylcarbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
JP4664634B2 (ja) * | 2003-09-05 | 2011-04-06 | 富山化学工業株式会社 | 新規なベンズアミジン誘導体またはその塩 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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JPH04312572A (ja) * | 1991-04-12 | 1992-11-04 | Takeda Chem Ind Ltd | 環状アミン化合物 |
DE4407136A1 (de) * | 1994-03-04 | 1995-09-07 | Thomae Gmbh Dr K | Aroyl-1-azacycloalkane, deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
DE4407138A1 (de) * | 1994-03-04 | 1995-09-07 | Thomae Gmbh Dr K | Aryliden-1-azacycloalkane und Arylalkyl-1-azacycloalkane, deren Salze, diese Verbindungen enthaltende Arzneimittel und deren Verwendung sowie Verfahren zu ihrer Herstellung |
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1997
- 1997-12-10 DE DE19754796A patent/DE19754796A1/de not_active Withdrawn
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1998
- 1998-12-08 JP JP2000524266A patent/JP3418688B2/ja not_active Expired - Fee Related
- 1998-12-08 AT AT98962423T patent/ATE234816T1/de not_active IP Right Cessation
- 1998-12-08 ES ES98962423T patent/ES2190130T3/es not_active Expired - Lifetime
- 1998-12-08 PL PL98341060A patent/PL341060A1/xx unknown
- 1998-12-08 EE EEP200000342A patent/EE200000342A/xx unknown
- 1998-12-08 YU YU35600A patent/YU35600A/sh unknown
- 1998-12-08 BR BR9813495-7A patent/BR9813495A/pt not_active IP Right Cessation
- 1998-12-08 CA CA002309388A patent/CA2309388A1/en not_active Abandoned
- 1998-12-08 TR TR2000/01635T patent/TR200001635T2/xx unknown
- 1998-12-08 KR KR1020007006326A patent/KR20010032977A/ko not_active Application Discontinuation
- 1998-12-08 AU AU17594/99A patent/AU1759499A/en not_active Abandoned
- 1998-12-08 SK SK861-2000A patent/SK8612000A3/sk unknown
- 1998-12-08 DE DE59807591T patent/DE59807591D1/de not_active Expired - Fee Related
- 1998-12-08 EA EA200000631A patent/EA200000631A1/ru unknown
- 1998-12-08 HU HU0100335A patent/HUP0100335A3/hu unknown
- 1998-12-08 DK DK98962423T patent/DK1060162T3/da active
- 1998-12-08 EP EP98962423A patent/EP1060162B1/de not_active Expired - Lifetime
- 1998-12-08 CN CN98811959A patent/CN1281434A/zh active Pending
- 1998-12-08 WO PCT/EP1998/007965 patent/WO1999029669A1/de not_active Application Discontinuation
- 1998-12-08 IL IL13573898A patent/IL135738A0/xx unknown
- 1998-12-08 PT PT98962423T patent/PT1060162E/pt unknown
- 1998-12-09 ZA ZA9811262A patent/ZA9811262B/xx unknown
- 1998-12-09 AR ARP980106228A patent/AR017827A1/es not_active Withdrawn
- 1998-12-09 CO CO98073126A patent/CO5370694A1/es not_active Application Discontinuation
-
2000
- 2000-06-02 BG BG104500A patent/BG104500A/bg active Pending
- 2000-06-07 HR HR20000377A patent/HRP20000377A2/hr not_active Application Discontinuation
- 2000-06-09 NO NO20002967A patent/NO20002967L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
SK8612000A3 (en) | 2000-11-07 |
WO1999029669A1 (de) | 1999-06-17 |
DE19754796A1 (de) | 1999-06-17 |
EA200000631A1 (ru) | 2000-12-25 |
CO5370694A1 (es) | 2004-02-27 |
EE200000342A (et) | 2001-08-15 |
ZA9811262B (en) | 2000-06-09 |
KR20010032977A (ko) | 2001-04-25 |
AR017827A1 (es) | 2001-10-24 |
EP1060162A1 (de) | 2000-12-20 |
PL341060A1 (en) | 2001-03-26 |
TR200001635T2 (tr) | 2000-11-21 |
NO20002967L (no) | 2000-08-09 |
PT1060162E (pt) | 2003-08-29 |
ES2190130T3 (es) | 2003-07-16 |
DK1060162T3 (da) | 2003-07-14 |
HUP0100335A2 (hu) | 2001-07-30 |
BG104500A (bg) | 2001-03-30 |
JP2001525397A (ja) | 2001-12-11 |
BR9813495A (pt) | 2000-10-10 |
DE59807591D1 (de) | 2003-04-24 |
CN1281434A (zh) | 2001-01-24 |
YU35600A (sh) | 2002-09-19 |
CA2309388A1 (en) | 1999-06-17 |
JP3418688B2 (ja) | 2003-06-23 |
ATE234816T1 (de) | 2003-04-15 |
EP1060162B1 (de) | 2003-03-19 |
HUP0100335A3 (en) | 2001-11-28 |
NO20002967D0 (no) | 2000-06-09 |
IL135738A0 (en) | 2001-05-20 |
AU1759499A (en) | 1999-06-28 |
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