UA76168C2 - COMPOUNDS BEING DRASTIC INHIBITORS OF Na+/Ca+2 EXCHANGE MECHANISM IN TREATMENT OF ARRHYTHMIA - Google Patents
COMPOUNDS BEING DRASTIC INHIBITORS OF Na+/Ca+2 EXCHANGE MECHANISM IN TREATMENT OF ARRHYTHMIA Download PDFInfo
- Publication number
- UA76168C2 UA76168C2 UA2004020928A UA2004020928A UA76168C2 UA 76168 C2 UA76168 C2 UA 76168C2 UA 2004020928 A UA2004020928 A UA 2004020928A UA 2004020928 A UA2004020928 A UA 2004020928A UA 76168 C2 UA76168 C2 UA 76168C2
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- UA
- Ukraine
- Prior art keywords
- yloxy
- chroman
- phenylchroman
- nmr
- dmso
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 60
- 230000007246 mechanism Effects 0.000 title claims abstract description 10
- 206010003119 arrhythmia Diseases 0.000 title claims description 7
- 230000006793 arrhythmia Effects 0.000 title claims description 7
- 239000003112 inhibitor Substances 0.000 title abstract description 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical group [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 title abstract description 3
- -1 -NR14R19 Chemical group 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 125000002252 acyl group Chemical group 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 171
- 238000005342 ion exchange Methods 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000003389 potentiating effect Effects 0.000 abstract description 3
- 229910001424 calcium ion Inorganic materials 0.000 abstract description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 216
- 238000005160 1H NMR spectroscopy Methods 0.000 description 180
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 169
- 238000002360 preparation method Methods 0.000 description 144
- 239000000203 mixture Substances 0.000 description 116
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 108
- 239000000047 product Substances 0.000 description 82
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 69
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- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 48
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 43
- 239000003480 eluent Substances 0.000 description 40
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 38
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 238000004440 column chromatography Methods 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000005481 NMR spectroscopy Methods 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 19
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- SWAJPHCXKPCPQZ-UHFFFAOYSA-N 7-hydroxyflavanone Chemical class O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=CC=C1 SWAJPHCXKPCPQZ-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000012299 nitrogen atmosphere Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- LDZUBFDZRMMINH-UHFFFAOYSA-N 2-(3-fluorophenyl)-6-hydroxy-2,3-dihydrochromen-4-one Chemical compound C1C(=O)C2=CC(O)=CC=C2OC1C1=CC=CC(F)=C1 LDZUBFDZRMMINH-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 8
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- BHJGJIOVSSSXDF-UHFFFAOYSA-N 2-phenyl-2,3-dihydro-1h-inden-5-ol Chemical class C1C2=CC(O)=CC=C2CC1C1=CC=CC=C1 BHJGJIOVSSSXDF-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- TYFYMEPJWNTIHE-UHFFFAOYSA-N 6-(4-methoxy-2-nitrophenoxy)-2-phenyl-3,4-dihydro-2h-chromene Chemical compound [O-][N+](=O)C1=CC(OC)=CC=C1OC1=CC=C(OC(CC2)C=3C=CC=CC=3)C2=C1 TYFYMEPJWNTIHE-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 6
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 6
- 239000012266 salt solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 5
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 5
- 244000166550 Strophanthus gratus Species 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 5
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- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 5
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 5
- 238000012746 preparative thin layer chromatography Methods 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 229910052725 zinc Inorganic materials 0.000 description 5
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- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 4
- LKMWTIGVJAWQHQ-UHFFFAOYSA-N 3-phenyl-3,4-dihydro-2h-chromen-7-ol Chemical class C1OC2=CC(O)=CC=C2CC1C1=CC=CC=C1 LKMWTIGVJAWQHQ-UHFFFAOYSA-N 0.000 description 4
- FAPPSXLVAAMKLI-UHFFFAOYSA-N 6-(2-azidoethoxy)-2-phenyl-3,4-dihydro-2h-chromene Chemical compound C1CC2=CC(OCCN=[N+]=[N-])=CC=C2OC1C1=CC=CC=C1 FAPPSXLVAAMKLI-UHFFFAOYSA-N 0.000 description 4
- TVXUDQOJNBCQSC-UHFFFAOYSA-N 6-(5-nitropyridin-2-yl)oxy-2-phenyl-3,4-dihydro-2h-chromen-4-amine Chemical compound C1=C2C(N)CC(C=3C=CC=CC=3)OC2=CC=C1OC1=CC=C([N+]([O-])=O)C=N1 TVXUDQOJNBCQSC-UHFFFAOYSA-N 0.000 description 4
- WMKOZARWBMFKAS-UHFFFAOYSA-N 7-hydroxyisoflavone Chemical class C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 WMKOZARWBMFKAS-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
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- 150000001540 azides Chemical class 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 3
- OOXOWBLOFXAPBK-UHFFFAOYSA-N 1-methoxy-2,3-dihydro-1h-indene Chemical compound C1=CC=C2C(OC)CCC2=C1 OOXOWBLOFXAPBK-UHFFFAOYSA-N 0.000 description 3
- JERAORCDTYWXHM-UHFFFAOYSA-N 2-(2-hydroxy-2-phenylethoxy)benzene-1,4-diol Chemical compound C=1C=CC=CC=1C(O)COC1=CC(O)=CC=C1O JERAORCDTYWXHM-UHFFFAOYSA-N 0.000 description 3
- BUWLEOGMFBKKRL-UHFFFAOYSA-N 2-(2-methoxyphenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound COC1=CC=CC=C1C1OC2=CC=C(O)C=C2C(O)C1 BUWLEOGMFBKKRL-UHFFFAOYSA-N 0.000 description 3
- IHXQLBMVFWEJCT-UHFFFAOYSA-N 2-(3-bromophenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=CC(Br)=C1 IHXQLBMVFWEJCT-UHFFFAOYSA-N 0.000 description 3
- HSZPPVWRPVXNRL-UHFFFAOYSA-N 2-(3-fluorophenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=CC(F)=C1 HSZPPVWRPVXNRL-UHFFFAOYSA-N 0.000 description 3
- AXPMHEYKFSFCHG-UHFFFAOYSA-N 2-(4-chlorophenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=C(Cl)C=C1 AXPMHEYKFSFCHG-UHFFFAOYSA-N 0.000 description 3
- CXFCPHACGDFVOB-UHFFFAOYSA-N 2-(4-fluorophenyl)-3,4-dihydro-2h-chromene-4,6-diol Chemical compound O1C2=CC=C(O)C=C2C(O)CC1C1=CC=C(F)C=C1 CXFCPHACGDFVOB-UHFFFAOYSA-N 0.000 description 3
- PVUIZYXXGZBWPJ-UHFFFAOYSA-N 2-[(2-phenyl-2,3-dihydro-1h-inden-5-yl)oxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 PVUIZYXXGZBWPJ-UHFFFAOYSA-N 0.000 description 3
- KFUMHIDDQQILEL-UHFFFAOYSA-N 2-phenyl-3,4-dihydro-2h-chromen-7-ol Chemical class O1C2=CC(O)=CC=C2CCC1C1=CC=CC=C1 KFUMHIDDQQILEL-UHFFFAOYSA-N 0.000 description 3
- FJUORDALKHVXDF-UHFFFAOYSA-N 3-(3-fluorophenyl)-7-hydroxychromen-4-one Chemical compound C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC=CC(F)=C1 FJUORDALKHVXDF-UHFFFAOYSA-N 0.000 description 3
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- QNGNSVIICDLXHT-UHFFFAOYSA-N 4-Ethylbenzaldehyde Chemical compound CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- PNMCKVAPCWRGFZ-UHFFFAOYSA-N 5-(2-nitrophenoxy)-2-phenyl-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 PNMCKVAPCWRGFZ-UHFFFAOYSA-N 0.000 description 3
- AKUGDKNHJWEWDZ-UHFFFAOYSA-N 5-[2,6-dinitro-4-(trifluoromethyl)phenoxy]-2-phenyl-2,3-dihydro-1h-indene Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC([N+]([O-])=O)=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 AKUGDKNHJWEWDZ-UHFFFAOYSA-N 0.000 description 3
- NRAREULSAFAWRH-UHFFFAOYSA-N 5-methoxy-2-[(2-phenyl-2,3-dihydro-1h-inden-5-yl)oxy]aniline Chemical compound NC1=CC(OC)=CC=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 NRAREULSAFAWRH-UHFFFAOYSA-N 0.000 description 3
- OUYPJKIKPBDKMY-UHFFFAOYSA-N 5-nitro-2-[(2-phenyl-2,3-dihydro-1h-inden-5-yl)oxy]pyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1=CC=C(CC(C2)C=3C=CC=CC=3)C2=C1 OUYPJKIKPBDKMY-UHFFFAOYSA-N 0.000 description 3
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 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
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/90—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. amino-diphenylethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FI20011507A FI20011507A0 (fi) | 2001-07-10 | 2001-07-10 | Uusia yhdisteitä |
PCT/FI2002/000621 WO2003006452A1 (en) | 2001-07-10 | 2002-07-10 | New compounds, which are potent inhibitors of na+/ca2+ exchange mechanism and are useful in the treatment of arrhythmias |
Publications (1)
Publication Number | Publication Date |
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UA76168C2 true UA76168C2 (en) | 2006-07-17 |
Family
ID=8561628
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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UA2004020928A UA76168C2 (en) | 2001-07-10 | 2002-10-07 | COMPOUNDS BEING DRASTIC INHIBITORS OF Na+/Ca+2 EXCHANGE MECHANISM IN TREATMENT OF ARRHYTHMIA |
Country Status (28)
Country | Link |
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US (1) | US7425568B2 (sr) |
EP (1) | EP1412343B1 (sr) |
JP (1) | JP4113839B2 (sr) |
KR (1) | KR20040025697A (sr) |
CN (1) | CN1281597C (sr) |
AR (1) | AR036236A1 (sr) |
AT (1) | ATE338038T1 (sr) |
AU (1) | AU2002321339B2 (sr) |
BR (1) | BR0211070A (sr) |
CA (1) | CA2452918C (sr) |
DE (1) | DE60214388T2 (sr) |
DK (1) | DK1412343T3 (sr) |
EA (1) | EA006580B1 (sr) |
ES (1) | ES2269746T3 (sr) |
FI (1) | FI20011507A0 (sr) |
HK (1) | HK1068611A1 (sr) |
HR (1) | HRP20040133A2 (sr) |
HU (1) | HUP0400391A3 (sr) |
IL (2) | IL159647A0 (sr) |
MX (1) | MXPA04000267A (sr) |
NO (1) | NO20035821L (sr) |
NZ (1) | NZ530490A (sr) |
PL (1) | PL367958A1 (sr) |
PT (1) | PT1412343E (sr) |
RS (1) | RS50886B (sr) |
UA (1) | UA76168C2 (sr) |
WO (1) | WO2003006452A1 (sr) |
ZA (1) | ZA200400145B (sr) |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FI20030030A0 (fi) * | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
ZA200707427B (en) | 2005-03-11 | 2008-11-26 | Florey Howard Inst | Flavonoid compounds and uses thereof |
US8912224B2 (en) | 2011-09-12 | 2014-12-16 | Sanofi | Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals |
JP5941637B2 (ja) * | 2011-09-12 | 2016-06-29 | サノフイ | 置換2−(クロマン−6−イルオキシ)−チアゾール及び医薬としてのその使用 |
SG11201400518RA (en) * | 2011-09-12 | 2014-04-28 | Sanofi Sa | Substituted 2-(chroman-6-yloxy)-thiazoles and their use as pharmaceuticals |
PT2567958E (pt) | 2011-09-12 | 2015-01-14 | Sanofi Sa | 2-(croman-6-iloxi)-tiazoles substituídos e sua utilização como produtos farmacêuticos |
CN102993195B (zh) * | 2011-09-14 | 2017-05-17 | 赛诺菲 | 取代的2‑(色满‑6‑基氧基)噻唑及其作为药物的用途 |
CN103030646B (zh) * | 2011-09-29 | 2016-08-24 | 上海恒瑞医药有限公司 | 苯并二氧六环类衍生物、其制备方法及其在医药上的应用 |
TWI633095B (zh) * | 2013-03-08 | 2018-08-21 | 賽諾菲公司 | 經取代-6-基氧基-環烷類及其作為醫藥品之用途 |
GB201416186D0 (en) | 2014-09-12 | 2014-10-29 | Redx Pharma Ltd | Compounds |
WO2019175464A1 (en) | 2018-03-14 | 2019-09-19 | Orion Corporation | Compounds useful as inhibitors of sodium-calcium exchanger (ncx) |
JP2023535790A (ja) | 2020-07-28 | 2023-08-21 | ジャズ ファーマシューティカルズ アイルランド リミテッド | 縮合二環式raf阻害薬及びその使用方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
US3862232A (en) * | 1963-07-03 | 1975-01-21 | Upjohn Co | 1-(p-hydroxyphenyl)-2-phenyl-6-(2-diethylaminoethoxy)-3,4-dihydronaphthalene and the salts thereof |
BE650081A (sr) * | 1963-07-03 | |||
GB1154119A (en) * | 1968-05-20 | 1969-06-04 | Merck Ag E | 3-Alkyl-Flavanones |
FR2733685B1 (fr) * | 1995-05-05 | 1997-05-30 | Adir | Utilisation des derives du benzopyrane pour l'obtention de compositions pharmaceutiques destinees au traitement des pathologies liees a l'echangeur c1-/hc03-, na+ independant |
JPH0967336A (ja) | 1995-09-04 | 1997-03-11 | Kanebo Ltd | 新規なイソチオウレア誘導体 |
ATE230720T1 (de) | 1997-03-27 | 2003-01-15 | Taisho Pharmaceutical Co Ltd | 2-phenoxyanilinderivate |
JPH1149752A (ja) * | 1997-08-05 | 1999-02-23 | Taisho Pharmaceut Co Ltd | フェノキシピリジン誘導体 |
DE19742508A1 (de) | 1997-09-26 | 1999-04-01 | Hoechst Marion Roussel De Gmbh | Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen |
ATE231487T1 (de) * | 1997-10-20 | 2003-02-15 | Taisho Pharmaceutical Co Ltd | 2-phenoxyanilin-derivate |
JPH11302235A (ja) | 1998-04-15 | 1999-11-02 | Taisho Pharmaceut Co Ltd | フェノキシアルキルアミン誘導体 |
EP1180029A4 (en) * | 1999-04-23 | 2002-10-02 | Bristol Myers Squibb Co | BICYCLIC ACYL IHIBITORING SODIUM / PROTON EXCHANGER AND RELATED PROCEDURE. |
AU766935B2 (en) | 1999-09-17 | 2003-10-23 | Nissan Chemical Industries Ltd. | Benzopyran derivative |
FI20030030A0 (fi) | 2003-01-09 | 2003-01-09 | Orion Corp | Uusia yhdisteitä |
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- 2002-07-10 US US10/482,396 patent/US7425568B2/en not_active Expired - Fee Related
- 2002-07-10 PT PT02755036T patent/PT1412343E/pt unknown
- 2002-07-10 PL PL02367958A patent/PL367958A1/xx unknown
- 2002-07-10 DK DK02755036T patent/DK1412343T3/da active
- 2002-07-10 AR ARP020102586A patent/AR036236A1/es unknown
- 2002-07-10 EP EP02755036A patent/EP1412343B1/en not_active Expired - Lifetime
- 2002-07-10 WO PCT/FI2002/000621 patent/WO2003006452A1/en active IP Right Grant
- 2002-07-10 AT AT02755036T patent/ATE338038T1/de not_active IP Right Cessation
- 2002-07-10 CN CNB028138635A patent/CN1281597C/zh not_active Expired - Fee Related
- 2002-07-10 ES ES02755036T patent/ES2269746T3/es not_active Expired - Lifetime
- 2002-07-10 AU AU2002321339A patent/AU2002321339B2/en not_active Ceased
- 2002-07-10 JP JP2003512224A patent/JP4113839B2/ja not_active Expired - Fee Related
- 2002-07-10 CA CA2452918A patent/CA2452918C/en not_active Expired - Fee Related
- 2002-07-10 IL IL15964702A patent/IL159647A0/xx active IP Right Grant
- 2002-07-10 RS YUP-6/04A patent/RS50886B/sr unknown
- 2002-07-10 KR KR10-2004-7000332A patent/KR20040025697A/ko not_active Application Discontinuation
- 2002-07-10 HU HU0400391A patent/HUP0400391A3/hu unknown
- 2002-07-10 NZ NZ530490A patent/NZ530490A/en not_active IP Right Cessation
- 2002-07-10 BR BR0211070-9A patent/BR0211070A/pt not_active IP Right Cessation
- 2002-07-10 EA EA200400161A patent/EA006580B1/ru not_active IP Right Cessation
- 2002-07-10 DE DE60214388T patent/DE60214388T2/de not_active Expired - Fee Related
- 2002-10-07 UA UA2004020928A patent/UA76168C2/uk unknown
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- 2003-12-30 IL IL159647A patent/IL159647A/en not_active IP Right Cessation
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2004
- 2004-01-08 ZA ZA200400145A patent/ZA200400145B/en unknown
- 2004-02-09 HR HR20040133A patent/HRP20040133A2/hr not_active Application Discontinuation
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