AU2003226757A1 - Morpholinyl-urea derivatives for use of the treatment of inflammatory diseases - Google Patents
Morpholinyl-urea derivatives for use of the treatment of inflammatory diseases Download PDFInfo
- Publication number
- AU2003226757A1 AU2003226757A1 AU2003226757A AU2003226757A AU2003226757A1 AU 2003226757 A1 AU2003226757 A1 AU 2003226757A1 AU 2003226757 A AU2003226757 A AU 2003226757A AU 2003226757 A AU2003226757 A AU 2003226757A AU 2003226757 A1 AU2003226757 A1 AU 2003226757A1
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- compound
- formula
- morpholin
- oxadiazol
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims description 15
- 208000027866 inflammatory disease Diseases 0.000 title description 6
- XMVNCHHPCRFUFT-UHFFFAOYSA-N morpholin-4-ylurea Chemical class NC(=O)NN1CCOCC1 XMVNCHHPCRFUFT-UHFFFAOYSA-N 0.000 title 1
- -1 2-methyl-1 ,3-thiazol-4 -yl Chemical group 0.000 claims description 330
- 150000001875 compounds Chemical class 0.000 claims description 307
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 238000006243 chemical reaction Methods 0.000 claims description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 49
- 239000001257 hydrogen Substances 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000001072 heteroaryl group Chemical group 0.000 claims description 39
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
- 239000004202 carbamide Substances 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 24
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 18
- 208000006673 asthma Diseases 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 15
- 125000001544 thienyl group Chemical group 0.000 claims description 15
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- 206010039083 rhinitis Diseases 0.000 claims description 8
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims description 7
- GPCOIPMNDAJLEW-UMJHXOGRSA-N [(2s)-4-[1-(3,4-difluorophenyl)ethyl]morpholin-2-yl]methylcarbamic acid Chemical compound C=1C=C(F)C(F)=CC=1C(C)N1CCO[C@@H](CNC(O)=O)C1 GPCOIPMNDAJLEW-UMJHXOGRSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000004968 inflammatory condition Effects 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 229920005990 polystyrene resin Polymers 0.000 claims description 6
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- VRESBNUEIKZECD-UHFFFAOYSA-N 2-methyltetrazole Chemical compound CN1N=CN=N1 VRESBNUEIKZECD-UHFFFAOYSA-N 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 4
- 125000001359 1,2,3-triazol-4-yl group Chemical group [H]N1N=NC([*])=C1[H] 0.000 claims description 3
- UBRNPKULFLNKTN-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(furan-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2OC=CC=2)OCC1 UBRNPKULFLNKTN-UHFFFAOYSA-N 0.000 claims description 3
- JOAMKEZJIZMCCP-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(pyridin-3-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=NC=CC=2)OCC1 JOAMKEZJIZMCCP-UHFFFAOYSA-N 0.000 claims description 3
- PMMVLXWWCMYNLR-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(thiophen-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2SC=CC=2)OCC1 PMMVLXWWCMYNLR-UHFFFAOYSA-N 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- FWJJBJSRDWAPHW-UHFFFAOYSA-N 5-(aminomethyl)-n-methylfuran-3-carboxamide Chemical compound CNC(=O)C1=COC(CN)=C1 FWJJBJSRDWAPHW-UHFFFAOYSA-N 0.000 claims description 3
- FLDBJBTUVYXSJV-UHFFFAOYSA-N 5-(aminomethyl)-n-methylthiophene-3-carboxamide Chemical compound CNC(=O)C1=CSC(CN)=C1 FLDBJBTUVYXSJV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- FSKWRNINWRUSHD-UHFFFAOYSA-N methyl 2-(aminomethyl)-1,3-oxazole-4-carboxylate Chemical compound COC(=O)C1=COC(CN)=N1 FSKWRNINWRUSHD-UHFFFAOYSA-N 0.000 claims description 3
- UNHWIEGKCBNIBF-UHFFFAOYSA-N tert-butyl n-[2-(5-methyl-1,3,4-oxadiazol-2-yl)ethyl]carbamate Chemical compound CC1=NN=C(CCNC(=O)OC(C)(C)C)O1 UNHWIEGKCBNIBF-UHFFFAOYSA-N 0.000 claims description 3
- CBYLTQKFXCIQCV-HNNXBMFYSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[4-(hydrazinecarbonyl)furan-2-yl]methyl]urea Chemical compound NNC(=O)C1=COC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 CBYLTQKFXCIQCV-HNNXBMFYSA-N 0.000 claims description 2
- LJQCWQGMVJGSKQ-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1h-indol-4-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=3C=CNC=3C=CC=2)OCC1 LJQCWQGMVJGSKQ-UHFFFAOYSA-N 0.000 claims description 2
- YSSDLSCDXACWQT-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1h-indol-5-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=C3C=CNC3=CC=2)OCC1 YSSDLSCDXACWQT-UHFFFAOYSA-N 0.000 claims description 2
- YESMWHHSKLCUDO-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(2-thiophen-2-ylethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCCC=2SC=CC=2)OCC1 YESMWHHSKLCUDO-UHFFFAOYSA-N 0.000 claims description 2
- KKDYVYFNQWWRRG-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(5-methyl-1,2-oxazol-3-yl)methyl]urea Chemical compound O1C(C)=CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 KKDYVYFNQWWRRG-UHFFFAOYSA-N 0.000 claims description 2
- PONVDQFSFUCTIN-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(6-methoxypyridin-3-yl)methyl]urea Chemical compound C1=NC(OC)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 PONVDQFSFUCTIN-UHFFFAOYSA-N 0.000 claims description 2
- WQNPBIUZGHSLPX-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[5-[(dimethylamino)methyl]furan-2-yl]methyl]urea Chemical compound O1C(CN(C)C)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 WQNPBIUZGHSLPX-UHFFFAOYSA-N 0.000 claims description 2
- NYLJYXFMJQIKII-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[[5-[(dimethylamino)methyl]thiophen-2-yl]methyl]urea Chemical compound S1C(CN(C)C)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 NYLJYXFMJQIKII-UHFFFAOYSA-N 0.000 claims description 2
- GUQLIIDOUGKDRN-UHFFFAOYSA-N 2-(5-methyl-1,3,4-oxadiazol-2-yl)ethanamine;hydrochloride Chemical compound Cl.CC1=NN=C(CCN)O1 GUQLIIDOUGKDRN-UHFFFAOYSA-N 0.000 claims description 2
- HBAHZZVIEFRTEY-UHFFFAOYSA-N 2-heptylcyclohex-2-en-1-one Chemical compound CCCCCCCC1=CCCCC1=O HBAHZZVIEFRTEY-UHFFFAOYSA-N 0.000 claims description 2
- SHWHZSUZZGMZID-UHFFFAOYSA-N 5-(aminomethyl)-n-methyl-1,3,4-oxadiazole-2-carboxamide;hydrochloride Chemical compound Cl.CNC(=O)C1=NN=C(CN)O1 SHWHZSUZZGMZID-UHFFFAOYSA-N 0.000 claims description 2
- 229920001367 Merrifield resin Polymers 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- ISFLPHCDIDWDHE-JTQLQIEISA-N [(2s)-4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methylcarbamic acid Chemical compound C1CO[C@@H](CNC(=O)O)CN1CC1=CC=C(F)C(Cl)=C1 ISFLPHCDIDWDHE-JTQLQIEISA-N 0.000 claims description 2
- 125000004532 benzofuran-3-yl group Chemical group O1C=C(C2=C1C=CC=C2)* 0.000 claims description 2
- GACCYZRDGNSLGQ-INIZCTEOSA-N n-[[5-[[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]furan-3-carbonyl]amino]formamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@H](CNC(=O)NCC=2OC=C(C=2)C(=O)NNC=O)OCC1 GACCYZRDGNSLGQ-INIZCTEOSA-N 0.000 claims description 2
- BNCNNWWRGRSEDP-UHFFFAOYSA-N n-methyl-5-[[(2,2,2-trifluoroacetyl)amino]methyl]furan-3-carboxamide Chemical compound CNC(=O)C1=COC(CNC(=O)C(F)(F)F)=C1 BNCNNWWRGRSEDP-UHFFFAOYSA-N 0.000 claims description 2
- RSHUXWPDNREGKV-UHFFFAOYSA-N n-methyl-5-[[(2,2,2-trifluoroacetyl)amino]methyl]thiophene-3-carboxamide Chemical compound CNC(=O)C1=CSC(CNC(=O)C(F)(F)F)=C1 RSHUXWPDNREGKV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 2
- CUTTVDFLPQWLBT-UHFFFAOYSA-N tert-butyl n-[3-(2-acetylhydrazinyl)-3-oxopropyl]carbamate Chemical compound CC(=O)NNC(=O)CCNC(=O)OC(C)(C)C CUTTVDFLPQWLBT-UHFFFAOYSA-N 0.000 claims description 2
- PMWQINVTMXVGNI-UHFFFAOYSA-N tert-butyl n-[[5-(methylcarbamoyl)-1,3,4-oxadiazol-2-yl]methyl]carbamate Chemical compound CNC(=O)C1=NN=C(CNC(=O)OC(C)(C)C)O1 PMWQINVTMXVGNI-UHFFFAOYSA-N 0.000 claims description 2
- VIYRXFZMEZXIIV-SFHVURJKSA-N tert-butyl n-[[5-[[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]furan-3-carbonyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=COC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 VIYRXFZMEZXIIV-SFHVURJKSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZALONBKTWCFUDD-UHFFFAOYSA-N 1-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(3-methoxy-1,2-thiazol-5-yl)methyl]urea Chemical compound S1N=C(OC)C=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 ZALONBKTWCFUDD-UHFFFAOYSA-N 0.000 claims 1
- JFLBVUOVXQIGRP-LBPRGKRZSA-N 1-[[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]methyl]-3-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound O1C(CCl)=NN=C1CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 JFLBVUOVXQIGRP-LBPRGKRZSA-N 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- QOYKPLLIAVKPQG-UHFFFAOYSA-N 5-[[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 QOYKPLLIAVKPQG-UHFFFAOYSA-N 0.000 claims 1
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical compound NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims 1
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- XYHFNWLMOULUAT-ZDUSSCGKSA-N tert-butyl n-[[(2s)-4-[(3-chloro-4-fluorophenyl)methyl]morpholin-2-yl]methyl]carbamate Chemical compound C1CO[C@@H](CNC(=O)OC(C)(C)C)CN1CC1=CC=C(F)C(Cl)=C1 XYHFNWLMOULUAT-ZDUSSCGKSA-N 0.000 claims 1
- HWTMFHDEXRMMSD-PYMCNQPYSA-N tert-butyl n-[[(2s)-4-[1-(3,4-difluorophenyl)ethyl]morpholin-2-yl]methyl]carbamate Chemical compound C=1C=C(F)C(F)=CC=1C(C)N1CCO[C@@H](CNC(=O)OC(C)(C)C)C1 HWTMFHDEXRMMSD-PYMCNQPYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 329
- 239000000243 solution Substances 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 239000000203 mixture Substances 0.000 description 93
- 239000002904 solvent Substances 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 62
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 59
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 50
- 125000001424 substituent group Chemical group 0.000 description 46
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- 229910052757 nitrogen Inorganic materials 0.000 description 35
- 239000007787 solid Substances 0.000 description 35
- 239000000725 suspension Substances 0.000 description 34
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- 239000002585 base Substances 0.000 description 26
- 229910021529 ammonia Inorganic materials 0.000 description 25
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 23
- 238000005342 ion exchange Methods 0.000 description 21
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- 125000005843 halogen group Chemical group 0.000 description 20
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 210000003979 eosinophil Anatomy 0.000 description 15
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- 238000001819 mass spectrum Methods 0.000 description 14
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000010189 synthetic method Methods 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000012298 atmosphere Substances 0.000 description 13
- 201000010099 disease Diseases 0.000 description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 235000011114 ammonium hydroxide Nutrition 0.000 description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 125000003831 tetrazolyl group Chemical group 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical group ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 125000000842 isoxazolyl group Chemical group 0.000 description 11
- 125000001715 oxadiazolyl group Chemical group 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 102000019034 Chemokines Human genes 0.000 description 10
- 108010012236 Chemokines Proteins 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000002808 molecular sieve Substances 0.000 description 10
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- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000011886 peripheral blood Substances 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
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- 125000005544 phthalimido group Chemical group 0.000 description 1
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- 208000015768 polyposis Diseases 0.000 description 1
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- 229920001592 potato starch Polymers 0.000 description 1
- 229940116317 potato starch Drugs 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 230000000770 proinflammatory effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
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- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
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- 229940080313 sodium starch Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- ZAZZTLVROMYWLQ-UHFFFAOYSA-N sodium;5-(trifluoromethyl)-2h-tetrazole Chemical compound [Na].FC(F)(F)C=1N=NNN=1 ZAZZTLVROMYWLQ-UHFFFAOYSA-N 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000195 terbutaline Drugs 0.000 description 1
- IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 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
- SMZKPZXYDDZDJG-UHFFFAOYSA-N tert-butyl n-(cyanomethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC#N SMZKPZXYDDZDJG-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- IYHJNCQAADULQE-MRVPVSSYSA-N tert-butyl n-[[(2r)-morpholin-2-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@H]1CNCCO1 IYHJNCQAADULQE-MRVPVSSYSA-N 0.000 description 1
- DQGJTJIAHLAYRH-PYMCNQPYSA-N tert-butyl n-[[(2s)-4-[1-(3,4-dichlorophenyl)ethyl]morpholin-2-yl]methyl]carbamate Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)N1CCO[C@@H](CNC(=O)OC(C)(C)C)C1 DQGJTJIAHLAYRH-PYMCNQPYSA-N 0.000 description 1
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- 238000002054 transplantation Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 239000002750 tryptase inhibitor Substances 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0207434A GB0207434D0 (en) | 2002-03-28 | 2002-03-28 | Novel compounds |
| GB0207434.2 | 2002-03-28 | ||
| GB0301608.6 | 2003-01-24 | ||
| GB0301608A GB0301608D0 (en) | 2003-01-24 | 2003-01-24 | Novel compounds |
| PCT/EP2003/003335 WO2003082861A2 (en) | 2002-03-28 | 2003-03-27 | Morpholinyl-urea derivatives for use of the treatment of inflammatory diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2003226757A1 true AU2003226757A1 (en) | 2003-10-13 |
Family
ID=28676494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003226757A Abandoned AU2003226757A1 (en) | 2002-03-28 | 2003-03-27 | Morpholinyl-urea derivatives for use of the treatment of inflammatory diseases |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7622464B2 (enExample) |
| EP (1) | EP1487828B1 (enExample) |
| JP (1) | JP4465195B2 (enExample) |
| KR (1) | KR20040093488A (enExample) |
| CN (1) | CN1656092A (enExample) |
| AR (1) | AR040403A1 (enExample) |
| AT (1) | ATE413399T1 (enExample) |
| AU (1) | AU2003226757A1 (enExample) |
| BR (1) | BR0308780A (enExample) |
| CA (1) | CA2480106A1 (enExample) |
| CY (1) | CY1108652T1 (enExample) |
| DE (1) | DE60324535D1 (enExample) |
| DK (1) | DK1487828T3 (enExample) |
| ES (1) | ES2315519T3 (enExample) |
| IL (1) | IL164047A0 (enExample) |
| IS (1) | IS7444A (enExample) |
| MX (1) | MXPA04009459A (enExample) |
| NO (1) | NO20044448L (enExample) |
| PT (1) | PT1487828E (enExample) |
| RU (1) | RU2004127928A (enExample) |
| SI (1) | SI1487828T1 (enExample) |
| TW (1) | TW200400035A (enExample) |
| WO (1) | WO2003082861A2 (enExample) |
Families Citing this family (21)
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| KR20050100615A (ko) | 2003-01-14 | 2005-10-19 | 싸이토키네틱스, 인코포레이티드 | 화합물, 조성물 및 방법 |
| WO2004089296A2 (en) | 2003-04-03 | 2004-10-21 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| NZ552404A (en) | 2004-06-17 | 2010-04-30 | Cytokinetics Inc | Compounds, compositions and methods |
| EP2289560B1 (en) * | 2004-07-08 | 2015-04-22 | Novo Nordisk A/S | Polypeptide protracting tags comprising a tetrazole moiety |
| US7176222B2 (en) | 2004-07-27 | 2007-02-13 | Cytokinetics, Inc. | Syntheses of ureas |
| JP4970946B2 (ja) | 2004-09-08 | 2012-07-11 | 田辺三菱製薬株式会社 | モルホリン化合物 |
| NZ554555A (en) | 2004-10-20 | 2011-09-30 | Univ California | Cyclohexyl-urea derivatives as improved inhibitors for the soluble epoxide hydrolase |
| US7538223B2 (en) | 2005-08-04 | 2009-05-26 | Cytokinetics, Inc. | Compounds, compositions and methods |
| EP1959960B1 (en) | 2005-12-15 | 2013-04-10 | Cytokinetics, Inc. | Certain chemical entities, compositions and methods |
| US7825120B2 (en) | 2005-12-15 | 2010-11-02 | Cytokinetics, Inc. | Certain substituted ((piperazin-1-ylmethyl)benzyl)ureas |
| WO2007078815A2 (en) | 2005-12-16 | 2007-07-12 | Cytokinetics, Inc. | Certain chemical entities, compositions, and methods |
| WO2007078839A2 (en) | 2005-12-19 | 2007-07-12 | Cytokinetics, Inc. | Compounds, compositions and methods |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| WO2009029632A1 (en) | 2007-08-27 | 2009-03-05 | Helicon Therapeutics, Inc. | Therapeutic isoxazole compounds |
| WO2012054093A2 (en) | 2010-01-29 | 2012-04-26 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
| RU2512293C1 (ru) * | 2012-12-13 | 2014-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" | Способ получения этил 1,2,4-оксадиазол-5-карбоксилатов |
| CN107362362B (zh) * | 2017-07-20 | 2019-01-01 | 复旦大学 | Sirt1抑制剂在预防和治疗放射引起的肠道疾病中的应用 |
| EP4178948A2 (en) * | 2020-07-29 | 2023-05-17 | Universidade de Santiago de Compostela | Functionalized isonitriles and products, preparation and uses thereof |
| WO2022031735A1 (en) * | 2020-08-03 | 2022-02-10 | Global Blood Therapeutics, Inc. | Urea derivatives as pyruvate kinase activators |
| CN119330881A (zh) * | 2024-09-06 | 2025-01-21 | 苏州汉德创宏生化科技有限公司 | 一种3-氨甲基-1-h吡唑的合成方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4851526A (en) | 1987-09-04 | 1989-07-25 | Schering A.G. | 1-(4-Substituted phenyl)-1H-imidazoles compounds |
| JP3087763B2 (ja) | 1990-11-30 | 2000-09-11 | 三井化学株式会社 | 新規な複素環式化合物およびそれを含有する医薬組成物 |
| US5219856A (en) | 1992-04-06 | 1993-06-15 | E. I. Du Pont De Nemours And Company | Angiotensin-II receptor blocking, heterocycle substituted imidazoles |
| WO1995032196A1 (en) | 1994-05-19 | 1995-11-30 | Merck Sharp & Dohme Limited | Piperazine, piperidine and tetrahydropyridine derivatives of indol-3-ylalkyl as 5-ht1d-alpha agonists |
| EP0772611A1 (de) | 1994-07-20 | 1997-05-14 | Byk Gulden Lomberg Chemische Fabrik GmbH | Piperazinothiopyridine zur bekämpfung von helicobacter-bakterien |
| US5654316A (en) | 1995-06-06 | 1997-08-05 | Schering Corporation | Piperidine derivatives as neurokinin antagonists |
| JP3531169B2 (ja) | 1996-06-11 | 2004-05-24 | 三菱ウェルファーマ株式会社 | 縮合ヘテロ環化合物およびその医薬用途 |
| US5919776A (en) * | 1996-12-20 | 1999-07-06 | Merck & Co., Inc. | Substituted aminoquinolines as modulators of chemokine receptor activity |
| US6207665B1 (en) | 1997-06-12 | 2001-03-27 | Schering Aktiengesellschaft | Piperazine derivatives and their use as anti-inflammatory agents |
| IT1293807B1 (it) | 1997-08-01 | 1999-03-10 | Recordati Chem Pharm | Derivati 1- (n-fenilaminoalchil) piperazinici sostituiti alla posizione 2 dell'anello fenilico |
| US6031097A (en) | 1997-10-27 | 2000-02-29 | Neurogen Corporation | 1-(N-(arylalkylaminoalkyl) aminoisoquinolines; a new class of dopamine receptor subtype specific ligands |
| AU1122399A (en) | 1997-10-27 | 1999-05-17 | Neurogen Corporation | Novel 1-(n'-(arylalkylaminoalkyl))aminoisoindoles; a new class of dopamine receptor subtype specific ligands |
| CN1325397A (zh) | 1998-09-30 | 2001-12-05 | 纽罗根公司 | 2－哌嗪烷基氨基苯并吡咯衍生物∶多巴胺受体亚型特异配体 |
| CZ20031195A3 (cs) | 2000-09-29 | 2003-09-17 | Glaxo Group Limited | Morfolinacetamidové deriváty |
| ES2275729T3 (es) | 2000-09-29 | 2007-06-16 | Glaxo Group Limited | Compuestos utiles en el tratamiento de enfermedades inflamatorias. |
-
2003
- 2003-03-26 TW TW092106766A patent/TW200400035A/zh unknown
- 2003-03-27 DK DK03745294T patent/DK1487828T3/da active
- 2003-03-27 CN CNA038115506A patent/CN1656092A/zh active Pending
- 2003-03-27 KR KR10-2004-7015398A patent/KR20040093488A/ko not_active Withdrawn
- 2003-03-27 SI SI200331471T patent/SI1487828T1/sl unknown
- 2003-03-27 JP JP2003580326A patent/JP4465195B2/ja not_active Expired - Lifetime
- 2003-03-27 DE DE60324535T patent/DE60324535D1/de not_active Expired - Lifetime
- 2003-03-27 WO PCT/EP2003/003335 patent/WO2003082861A2/en not_active Ceased
- 2003-03-27 IL IL16404703A patent/IL164047A0/xx unknown
- 2003-03-27 AR AR20030101081A patent/AR040403A1/es unknown
- 2003-03-27 RU RU2004127928/04A patent/RU2004127928A/ru not_active Application Discontinuation
- 2003-03-27 AT AT03745294T patent/ATE413399T1/de active
- 2003-03-27 US US10/509,162 patent/US7622464B2/en active Active
- 2003-03-27 ES ES03745294T patent/ES2315519T3/es not_active Expired - Lifetime
- 2003-03-27 PT PT03745294T patent/PT1487828E/pt unknown
- 2003-03-27 CA CA002480106A patent/CA2480106A1/en not_active Abandoned
- 2003-03-27 MX MXPA04009459A patent/MXPA04009459A/es unknown
- 2003-03-27 AU AU2003226757A patent/AU2003226757A1/en not_active Abandoned
- 2003-03-27 BR BR0308780-8A patent/BR0308780A/pt not_active Application Discontinuation
- 2003-03-27 EP EP03745294A patent/EP1487828B1/en not_active Expired - Lifetime
-
2004
- 2004-09-13 IS IS7444A patent/IS7444A/is unknown
- 2004-10-19 NO NO20044448A patent/NO20044448L/no not_active Application Discontinuation
-
2008
- 2008-12-19 CY CY20081101474T patent/CY1108652T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003082861A2 (en) | 2003-10-09 |
| CY1108652T1 (el) | 2014-08-13 |
| EP1487828B1 (en) | 2008-11-05 |
| RU2004127928A (ru) | 2005-06-27 |
| CN1656092A (zh) | 2005-08-17 |
| IL164047A0 (en) | 2005-12-18 |
| WO2003082861A3 (en) | 2004-03-11 |
| US20060063765A1 (en) | 2006-03-23 |
| MXPA04009459A (es) | 2005-01-25 |
| ES2315519T3 (es) | 2009-04-01 |
| CA2480106A1 (en) | 2003-10-09 |
| EP1487828A2 (en) | 2004-12-22 |
| DK1487828T3 (da) | 2009-02-02 |
| SI1487828T1 (sl) | 2009-04-30 |
| AR040403A1 (es) | 2005-04-06 |
| IS7444A (is) | 2004-09-13 |
| PT1487828E (pt) | 2009-01-06 |
| TW200400035A (en) | 2004-01-01 |
| BR0308780A (pt) | 2004-12-28 |
| DE60324535D1 (de) | 2008-12-18 |
| JP2005526815A (ja) | 2005-09-08 |
| KR20040093488A (ko) | 2004-11-05 |
| US7622464B2 (en) | 2009-11-24 |
| NO20044448L (no) | 2004-10-26 |
| ATE413399T1 (de) | 2008-11-15 |
| JP4465195B2 (ja) | 2010-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |