SK165898A3 - Use of inhibitors of the cellular na+/h+ exchanger (nhe) for preparing a medicament for normalizing serum lipids - Google Patents
Use of inhibitors of the cellular na+/h+ exchanger (nhe) for preparing a medicament for normalizing serum lipids Download PDFInfo
- Publication number
- SK165898A3 SK165898A3 SK1658-98A SK165898A SK165898A3 SK 165898 A3 SK165898 A3 SK 165898A3 SK 165898 A SK165898 A SK 165898A SK 165898 A3 SK165898 A3 SK 165898A3
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- SK
- Slovakia
- Prior art keywords
- group
- carbon atoms
- alkyl
- atom
- hydrogen
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- 239000003814 drug Substances 0.000 title claims abstract description 21
- 239000003112 inhibitor Substances 0.000 title claims abstract description 21
- 150000002632 lipids Chemical class 0.000 title claims abstract description 9
- 210000002966 serum Anatomy 0.000 title abstract description 3
- 230000001413 cellular effect Effects 0.000 title abstract 2
- 208000011580 syndromic disease Diseases 0.000 claims abstract 6
- 239000008280 blood Substances 0.000 claims abstract 3
- 210000004369 blood Anatomy 0.000 claims abstract 3
- 201000010099 disease Diseases 0.000 claims abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 903
- 125000000217 alkyl group Chemical group 0.000 claims description 573
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 380
- 229910052731 fluorine Inorganic materials 0.000 claims description 348
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 344
- 125000001424 substituent group Chemical group 0.000 claims description 343
- 229910052801 chlorine Inorganic materials 0.000 claims description 339
- 229910052739 hydrogen Inorganic materials 0.000 claims description 312
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 289
- 125000001153 fluoro group Chemical group F* 0.000 claims description 283
- 239000001257 hydrogen Substances 0.000 claims description 277
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 252
- -1 CF 3 group Chemical group 0.000 claims description 233
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 230
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 225
- 229910052717 sulfur Inorganic materials 0.000 claims description 193
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 173
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 156
- 239000000460 chlorine Substances 0.000 claims description 122
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 118
- 150000002431 hydrogen Chemical class 0.000 claims description 116
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 105
- 125000004434 sulfur atom Chemical group 0.000 claims description 103
- 229910052760 oxygen Inorganic materials 0.000 claims description 99
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 93
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 91
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 84
- 239000011737 fluorine Substances 0.000 claims description 81
- 229910052799 carbon Inorganic materials 0.000 claims description 79
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 78
- 125000003118 aryl group Chemical group 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 70
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 69
- 125000003342 alkenyl group Chemical group 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000003277 amino group Chemical group 0.000 claims description 63
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 61
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 229910052740 iodine Inorganic materials 0.000 claims description 61
- 239000001301 oxygen Substances 0.000 claims description 61
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 59
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 58
- 125000001624 naphthyl group Chemical group 0.000 claims description 47
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 45
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 43
- 229910052794 bromium Inorganic materials 0.000 claims description 43
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 42
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 39
- 150000001721 carbon Chemical group 0.000 claims description 34
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 239000011593 sulfur Substances 0.000 claims description 19
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000005493 quinolyl group Chemical group 0.000 claims description 9
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000000320 amidine group Chemical group 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 150000002357 guanidines Chemical class 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- XSDLDLIXLLMXDY-UHFFFAOYSA-N n-methoxyhydroxylamine Chemical group CONO XSDLDLIXLLMXDY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000005413 thiopyridyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 110
- SVSARCCKBMZNMR-UHFFFAOYSA-N [1-[2-[methyl-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethyl]amino]ethyl]pyridin-4-ylidene]methyl-oxoazanium;dichloride Chemical compound [Cl-].[Cl-].C1=CC(=C[NH+]=O)C=CN1CCN(C)CCN1C=CC(=C[NH+]=O)C=C1 SVSARCCKBMZNMR-UHFFFAOYSA-N 0.000 claims 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 27
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 19
- MNLAVFKVRUQAKW-UHFFFAOYSA-N VR nerve agent Chemical compound CCN(CC)CCSP(C)(=O)OCC(C)C MNLAVFKVRUQAKW-UHFFFAOYSA-N 0.000 claims 18
- 150000003254 radicals Chemical class 0.000 claims 18
- 125000004429 atom Chemical group 0.000 claims 16
- 125000001589 carboacyl group Chemical group 0.000 claims 13
- PCPQWYHRMVULIX-UHFFFAOYSA-P [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;dinitrate Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 PCPQWYHRMVULIX-UHFFFAOYSA-P 0.000 claims 12
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims 12
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 11
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 11
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 10
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 9
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims 8
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 claims 6
- 230000002265 prevention Effects 0.000 claims 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 5
- 206010048554 Endothelial dysfunction Diseases 0.000 claims 5
- 230000008694 endothelial dysfunction Effects 0.000 claims 5
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 claims 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 5
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- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 claims 4
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 claims 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
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- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000011630 iodine Substances 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000003435 aroyl group Chemical group 0.000 claims 3
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- 125000004122 cyclic group Chemical group 0.000 claims 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
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- FZOCFRPFPKJHHP-UHFFFAOYSA-N benzyl n-(diaminomethylidene)carbamate Chemical compound NC(N)=NC(=O)OCC1=CC=CC=C1 FZOCFRPFPKJHHP-UHFFFAOYSA-N 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
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- 231100000252 nontoxic Toxicity 0.000 claims 2
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- 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 claims 1
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- 102000029797 Prion Human genes 0.000 claims 1
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- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 230000036772 blood pressure Effects 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims 1
- 201000011634 coronary artery vasospasm Diseases 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims 1
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 229960004844 lovastatin Drugs 0.000 claims 1
- 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 claims 1
- 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 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 claims 1
- 229960002965 pravastatin Drugs 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000013543 active substance Substances 0.000 abstract description 2
- 230000003511 endothelial effect Effects 0.000 abstract 1
- BWBONKHPVHMQHE-UHFFFAOYSA-N tiocarlide Chemical group C1=CC(OCCC(C)C)=CC=C1NC(=S)NC1=CC=C(OCCC(C)C)C=C1 BWBONKHPVHMQHE-UHFFFAOYSA-N 0.000 description 7
- 229960002171 tiocarlide Drugs 0.000 description 7
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
-
- 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
-
- 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- 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
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19622222A DE19622222A1 (de) | 1996-06-03 | 1996-06-03 | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikament zur Normalisierung der Serumlipide |
| DE19712636A DE19712636A1 (de) | 1997-03-26 | 1997-03-26 | Verwendung von Inhibitoren des zellulären Na+/H+Exchangers (NHE) zur Herstellung eines Medikament zur Normalisierung der Serumlipide |
| PCT/EP1997/002548 WO1997046226A2 (fr) | 1996-06-03 | 1997-05-20 | UTILISATION D'INHIBITEURS DE L'ECHANGEUR CELLULAIRE Na+/H+ (NHE) POUR PREPARER UN MEDICAMENT PERMETTANT DE NORMALISER LES LIPIDES SERIQUES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK165898A3 true SK165898A3 (en) | 1999-05-07 |
Family
ID=26026256
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1658-98A SK165898A3 (en) | 1996-06-03 | 1997-05-20 | Use of inhibitors of the cellular na+/h+ exchanger (nhe) for preparing a medicament for normalizing serum lipids |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0918515B1 (fr) |
| JP (1) | JP4527811B2 (fr) |
| KR (1) | KR100511711B1 (fr) |
| CN (1) | CN1221339A (fr) |
| AR (1) | AR007353A1 (fr) |
| AT (1) | ATE293965T1 (fr) |
| AU (1) | AU722166B2 (fr) |
| BR (1) | BR9709516A (fr) |
| CA (1) | CA2257299A1 (fr) |
| DE (2) | DE19622222A1 (fr) |
| DK (1) | DK0918515T3 (fr) |
| ES (1) | ES2241049T3 (fr) |
| IL (1) | IL126935A0 (fr) |
| NO (1) | NO985480L (fr) |
| NZ (1) | NZ333095A (fr) |
| PL (1) | PL189950B1 (fr) |
| PT (1) | PT918515E (fr) |
| RU (1) | RU2211032C2 (fr) |
| SI (1) | SI0918515T1 (fr) |
| SK (1) | SK165898A3 (fr) |
| TR (1) | TR199802505T2 (fr) |
| WO (1) | WO1997046226A2 (fr) |
| ZA (1) | ZA974828B (fr) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6160134A (en) * | 1997-12-24 | 2000-12-12 | Bristol-Myers Squibb Co. | Process for preparing chiral cyclopropane carboxylic acids and acyl guanidines |
| US6011059A (en) * | 1997-12-24 | 2000-01-04 | Bristol-Myers Squibb Company | Acyl guanidine sodium/proton exchange inhibitors and method |
| DE19859727A1 (de) | 1998-12-23 | 2000-06-29 | Aventis Pharma Gmbh | Die Verwendung von Hemmern des Natrium-Wasserstoff-Austauschers zur Herstellung eines Medikaments zur Verhinderung von altersbedingten Organ-Dysfunktionen, altersbedingten Erkrankungen zur Lebensverlängerung |
| EP1180029A4 (fr) | 1999-04-23 | 2002-10-02 | Bristol Myers Squibb Co | Inhibiteurs d'echange sodium-protons a base de guandines d'acyle bicyclique et procede correspondant |
| DE19945302A1 (de) * | 1999-09-22 | 2001-03-29 | Merck Patent Gmbh | Biphenylderivate als NHE-3-Inhibitoren |
| US6423705B1 (en) | 2001-01-25 | 2002-07-23 | Pfizer Inc. | Combination therapy |
| US6984645B2 (en) | 2001-11-16 | 2006-01-10 | Bristol-Myers Squibb Company | Dual inhibitors of adipocyte fatty acid binding protein and keratinocyte fatty acid binding protein |
| FR2856062B1 (fr) * | 2003-06-12 | 2005-11-11 | Aventis Pharma Sa | Derives 3-guanidinocarbonyl-heterocycle, procede de preparation et intermediaires de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| US7230007B2 (en) | 2003-06-12 | 2007-06-12 | Sanofi-Aventis Deutschland Gmbh | Derivatives of 3-(Guanidinocarbonyl) heterocycle, methods of preparation and intermediates thereof, their use as medicaments, and pharmaceutical compositions therefrom |
| EP2617709B8 (fr) * | 2003-06-26 | 2022-12-21 | Biotron Limited | Dérivés de guanidine comme agents antiviraux |
| US7371759B2 (en) | 2003-09-25 | 2008-05-13 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
| US7420059B2 (en) | 2003-11-20 | 2008-09-02 | Bristol-Myers Squibb Company | HMG-CoA reductase inhibitors and method |
| US7572805B2 (en) | 2004-07-14 | 2009-08-11 | Bristol-Myers Squibb Company | Pyrrolo(oxo)isoquinolines as 5HT ligands |
| US7517991B2 (en) | 2004-10-12 | 2009-04-14 | Bristol-Myers Squibb Company | N-sulfonylpiperidine cannabinoid receptor 1 antagonists |
| WO2006076569A2 (fr) | 2005-01-12 | 2006-07-20 | Bristol-Myers Squibb Company | Heterocycles bicycliques servant de modulateurs aux recepteurs cannabinoides |
| US7314882B2 (en) | 2005-01-12 | 2008-01-01 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid receptor modulators |
| WO2006078697A1 (fr) | 2005-01-18 | 2006-07-27 | Bristol-Myers Squibb Company | Heterocycles bicycliques utilises comme modulateurs des recepteurs de cannabinoide |
| EP1846410B1 (fr) | 2005-02-10 | 2009-01-21 | Bristol-Myers Squibb Company | Dihydroquinazolinones utilisees comme modulateurs de la 5ht |
| US7572808B2 (en) | 2005-06-17 | 2009-08-11 | Bristol-Myers Squibb Company | Triazolopyridine cannabinoid receptor 1 antagonists |
| US7317012B2 (en) | 2005-06-17 | 2008-01-08 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoind-1 receptor modulators |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| US7629342B2 (en) | 2005-06-17 | 2009-12-08 | Bristol-Myers Squibb Company | Azabicyclic heterocycles as cannabinoid receptor modulators |
| US7452892B2 (en) | 2005-06-17 | 2008-11-18 | Bristol-Myers Squibb Company | Triazolopyrimidine cannabinoid receptor 1 antagonists |
| US7795436B2 (en) | 2005-08-24 | 2010-09-14 | Bristol-Myers Squibb Company | Substituted tricyclic heterocycles as serotonin receptor agonists and antagonists |
| AR056155A1 (es) | 2005-10-26 | 2007-09-19 | Bristol Myers Squibb Co | Antagonistas del receptor 1 de la hormona de concentracion de melanina no basica |
| US7553836B2 (en) | 2006-02-06 | 2009-06-30 | Bristol-Myers Squibb Company | Melanin concentrating hormone receptor-1 antagonists |
| US20090011994A1 (en) | 2007-07-06 | 2009-01-08 | Bristol-Myers Squibb Company | Non-basic melanin concentrating hormone receptor-1 antagonists and methods |
| PE20091928A1 (es) | 2008-05-29 | 2009-12-31 | Bristol Myers Squibb Co | Tienopirimidinas hidroxisustituidas como antagonistas de receptor-1 de hormona concentradora de melanina no basicos |
| US10517839B2 (en) | 2008-06-09 | 2019-12-31 | Cornell University | Mast cell inhibition in diseases of the retina and vitreous |
| KR20110135411A (ko) | 2009-03-27 | 2011-12-16 | 브리스톨-마이어스 스큅 컴퍼니 | Ｄｐｐ-ｉｖ 억제제로 주요 유해 심장혈관 이벤트를 예방하는 방법 |
| CN102844313B (zh) | 2010-01-28 | 2016-10-05 | 哈佛大学校长及研究员协会 | 提高蛋白酶体活性的组合物和方法 |
| US9556166B2 (en) | 2011-05-12 | 2017-01-31 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| WO2014039411A1 (fr) | 2012-09-05 | 2014-03-13 | Bristol-Myers Squibb Company | Antagonistes du récepteur 1 de l'hormone de concentration de pyrrolone ou pyrrolidinone mélanine |
| WO2014039412A1 (fr) | 2012-09-05 | 2014-03-13 | Bristol-Myers Squibb Company | Antagonistes du récepteur 1 d'hormone concentrant la mélanine de type pyrrolone ou pyrrolidinone |
| WO2014116228A1 (fr) | 2013-01-25 | 2014-07-31 | President And Fellows Of Harvard College | Inhibiteurs de l'usp14 utilisables en vue du traitement ou de la prévention d'infections virales |
| WO2015073528A1 (fr) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Composés renforçant l'activité des protéasomes |
| BR112021000139A2 (pt) | 2018-07-19 | 2021-04-06 | Astrazeneca Ab | Métodos de tratamento da hfpef empregando dapagliflozina e composições compreendendo a mesma |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5110817A (en) * | 1988-10-21 | 1992-05-05 | Beyer Jr Karl H | Method for controlling and/or lowering serum triglyceride and/or cholesterol levels in mammals |
| US4920123A (en) * | 1988-10-21 | 1990-04-24 | Beyer Jr Karl H | Method for controlling and/or lowering serum triglyceride and/or cholesterol levels in mammals |
| AU7316591A (en) * | 1990-02-28 | 1991-09-18 | Upjohn Company, The | Use of 3-guanidinopropionic acid in the treatment and prevention of metabolic disorders |
| EP0600973A1 (fr) * | 1991-08-27 | 1994-06-15 | The Upjohn Company | Procede de traitement de troubles metaboliques et du metabolisme |
| ES2092729T3 (es) * | 1992-07-01 | 1996-12-01 | Hoechst Ag | Benzoilguanidinas 3,4,5-sustituidas, procedimiento para su preparacion, su empleo como medicamento o agente de diagnostico, asi como medicamento que las contiene. |
| EP0612723B1 (fr) * | 1993-02-20 | 1997-08-27 | Hoechst Aktiengesellschaft | Benzoylguanidines substituées, procédé de leur préparation, leur utilisation comme médicament, comme inhibiteurs de l'échange cellulaire de Na+/H+ ou comme agent diagnostique et médicament les contenant |
| DE4318658A1 (de) * | 1993-06-04 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4325822A1 (de) * | 1993-07-31 | 1995-02-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| AU1882395A (en) * | 1994-02-23 | 1995-09-11 | Cambridge Neuroscience, Inc. | Blockers of ion channels and methods of use thereof |
| IL114670A0 (en) * | 1994-08-05 | 1995-11-27 | Fujisawa Pharmaceutical Co | Guanidine derivatives pharmaceutical compositions containing the same and processes for the preparation thereof |
-
1996
- 1996-06-03 DE DE19622222A patent/DE19622222A1/de not_active Withdrawn
-
1997
- 1997-05-20 DE DE59712287T patent/DE59712287D1/de not_active Expired - Lifetime
- 1997-05-20 EP EP97923937A patent/EP0918515B1/fr not_active Expired - Lifetime
- 1997-05-20 TR TR1998/02505T patent/TR199802505T2/xx unknown
- 1997-05-20 PL PL97330412A patent/PL189950B1/pl not_active IP Right Cessation
- 1997-05-20 AT AT97923937T patent/ATE293965T1/de not_active IP Right Cessation
- 1997-05-20 NZ NZ333095A patent/NZ333095A/xx unknown
- 1997-05-20 JP JP50014498A patent/JP4527811B2/ja not_active Expired - Fee Related
- 1997-05-20 CA CA002257299A patent/CA2257299A1/fr not_active Abandoned
- 1997-05-20 AU AU29576/97A patent/AU722166B2/en not_active Ceased
- 1997-05-20 RU RU99100084/14A patent/RU2211032C2/ru not_active IP Right Cessation
- 1997-05-20 ES ES97923937T patent/ES2241049T3/es not_active Expired - Lifetime
- 1997-05-20 PT PT97923937T patent/PT918515E/pt unknown
- 1997-05-20 CN CN97195194A patent/CN1221339A/zh active Pending
- 1997-05-20 DK DK97923937T patent/DK0918515T3/da active
- 1997-05-20 WO PCT/EP1997/002548 patent/WO1997046226A2/fr not_active Ceased
- 1997-05-20 IL IL12693597A patent/IL126935A0/xx not_active IP Right Cessation
- 1997-05-20 SI SI9730705T patent/SI0918515T1/sl unknown
- 1997-05-20 BR BR9709516A patent/BR9709516A/pt not_active Application Discontinuation
- 1997-05-20 KR KR10-1998-0709811A patent/KR100511711B1/ko not_active Expired - Fee Related
- 1997-05-20 SK SK1658-98A patent/SK165898A3/sk unknown
- 1997-05-30 AR ARP970102344A patent/AR007353A1/es unknown
- 1997-06-02 ZA ZA9704828A patent/ZA974828B/xx unknown
-
1998
- 1998-11-24 NO NO985480A patent/NO985480L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL126935A0 (en) | 1999-09-22 |
| TR199802505T2 (xx) | 1999-04-21 |
| KR100511711B1 (ko) | 2005-12-26 |
| WO1997046226A3 (fr) | 1998-03-05 |
| SI0918515T1 (sl) | 2005-12-31 |
| DE19622222A1 (de) | 1997-12-04 |
| AU2957697A (en) | 1998-01-05 |
| KR20000016240A (ko) | 2000-03-25 |
| PL330412A1 (en) | 1999-05-10 |
| CN1221339A (zh) | 1999-06-30 |
| AU722166B2 (en) | 2000-07-20 |
| NO985480L (no) | 1999-01-28 |
| NZ333095A (en) | 2000-08-25 |
| BR9709516A (pt) | 1999-08-10 |
| WO1997046226A2 (fr) | 1997-12-11 |
| DK0918515T3 (da) | 2005-08-15 |
| EP0918515B1 (fr) | 2005-04-27 |
| AR007353A1 (es) | 1999-10-27 |
| DE59712287D1 (de) | 2005-06-02 |
| RU2211032C2 (ru) | 2003-08-27 |
| EP0918515A2 (fr) | 1999-06-02 |
| JP2000506906A (ja) | 2000-06-06 |
| CA2257299A1 (fr) | 1997-12-11 |
| JP4527811B2 (ja) | 2010-08-18 |
| ES2241049T3 (es) | 2005-10-16 |
| PL189950B1 (pl) | 2005-10-31 |
| ZA974828B (en) | 1997-12-03 |
| PT918515E (pt) | 2005-06-30 |
| NO985480D0 (no) | 1998-11-24 |
| ATE293965T1 (de) | 2005-05-15 |
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