CA2241531A1 - Use of inhibitors of the cellular na+/h+ exchanger (nhe) for the preparation of a drug for respiratory stimulation - Google Patents
Use of inhibitors of the cellular na+/h+ exchanger (nhe) for the preparation of a drug for respiratory stimulation Download PDFInfo
- Publication number
- CA2241531A1 CA2241531A1 CA002241531A CA2241531A CA2241531A1 CA 2241531 A1 CA2241531 A1 CA 2241531A1 CA 002241531 A CA002241531 A CA 002241531A CA 2241531 A CA2241531 A CA 2241531A CA 2241531 A1 CA2241531 A1 CA 2241531A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- substituted
- hydrogen
- group
- independently
- 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
- 239000003112 inhibitor Substances 0.000 title claims abstract description 17
- 239000003814 drug Substances 0.000 title claims abstract description 15
- 239000003169 respiratory stimulant agent Substances 0.000 title claims abstract description 6
- 230000001413 cellular effect Effects 0.000 title claims description 3
- 229940079593 drug Drugs 0.000 title abstract description 3
- 208000023504 respiratory system disease Diseases 0.000 claims abstract 5
- 201000002859 sleep apnea Diseases 0.000 claims abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 583
- 239000001257 hydrogen Substances 0.000 claims description 561
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 548
- 229910052731 fluorine Inorganic materials 0.000 claims description 466
- 239000000460 chlorine Substances 0.000 claims description 465
- 229910052801 chlorine Inorganic materials 0.000 claims description 451
- 125000001424 substituent group Chemical group 0.000 claims description 422
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 413
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 403
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 319
- 125000004432 carbon atom Chemical group C* 0.000 claims description 313
- -1 chorine Chemical group 0.000 claims description 307
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 293
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 284
- 229910052760 oxygen Inorganic materials 0.000 claims description 275
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 242
- 239000001301 oxygen Substances 0.000 claims description 241
- 125000000217 alkyl group Chemical group 0.000 claims description 238
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 235
- 150000002431 hydrogen Chemical class 0.000 claims description 154
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 151
- 229910052717 sulfur Inorganic materials 0.000 claims description 151
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 136
- 229910052794 bromium Inorganic materials 0.000 claims description 133
- 229910052740 iodine Inorganic materials 0.000 claims description 102
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 83
- 150000003839 salts Chemical class 0.000 claims description 83
- 229910052799 carbon Inorganic materials 0.000 claims description 77
- 229910052757 nitrogen Inorganic materials 0.000 claims description 77
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 73
- 125000001624 naphthyl group Chemical group 0.000 claims description 68
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 50
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 50
- 150000003254 radicals Chemical class 0.000 claims description 50
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 44
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 235000001508 sulfur Nutrition 0.000 claims description 34
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 33
- 239000011593 sulfur Substances 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 150000001721 carbon Chemical group 0.000 claims description 30
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
- 241001484259 Lacuna Species 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 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 14
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 150000001409 amidines Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000002883 imidazolyl group Chemical group 0.000 claims description 13
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 11
- 125000005493 quinolyl group Chemical group 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005956 isoquinolyl 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
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910020587 CmF2m+1 Inorganic materials 0.000 claims description 5
- 125000002541 furyl 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
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 4
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 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 description 3
- 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 description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- 150000002357 guanidines Chemical class 0.000 claims description 3
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 2
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006313 (C5-C8) alkyl group Chemical group 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- XMSZANIMCDLNKA-UHFFFAOYSA-N methyl hypofluorite Chemical group COF XMSZANIMCDLNKA-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
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- 150000003456 sulfonamides Chemical class 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 22
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 6
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 241000687983 Cerobasis alpha Species 0.000 claims 4
- 229910006069 SO3H Inorganic materials 0.000 claims 4
- 125000003435 aroyl group Chemical group 0.000 claims 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims 4
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 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
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 3
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 2
- 125000005025 alkynylaryl group Chemical group 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 150000005840 aryl radicals Chemical class 0.000 claims 2
- FZOCFRPFPKJHHP-UHFFFAOYSA-N benzyl n-(diaminomethylidene)carbamate Chemical class NC(N)=NC(=O)OCC1=CC=CC=C1 FZOCFRPFPKJHHP-UHFFFAOYSA-N 0.000 claims 2
- 229930016911 cinnamic acid Natural products 0.000 claims 2
- 235000013985 cinnamic acid Nutrition 0.000 claims 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims 2
- 125000004122 cyclic group Chemical group 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- 206010020591 Hypercapnia Diseases 0.000 claims 1
- 206010021143 Hypoxia Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 claims 1
- 229960000571 acetazolamide Drugs 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 230000006978 adaptation Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 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
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 claims 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 1
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical compound C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 230000007954 hypoxia Effects 0.000 claims 1
- 230000001771 impaired effect Effects 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
- 230000007774 longterm Effects 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- WBCXYMNAMCHKSU-UHFFFAOYSA-N n-(diaminomethylidene)-1h-indene-1-carboxamide Chemical class C1=CC=C2C(C(=O)NC(=N)N)C=CC2=C1 WBCXYMNAMCHKSU-UHFFFAOYSA-N 0.000 claims 1
- QAKJXJZBXCVFLX-UHFFFAOYSA-N n-(diaminomethylidene)-1h-indole-2-carboxamide Chemical class C1=CC=C2NC(C(=O)N=C(N)N)=CC2=C1 QAKJXJZBXCVFLX-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
- 230000000414 obstructive effect Effects 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 238000009423 ventilation Methods 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
-
- 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
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L50/00—Electric propulsion with power supplied within the vehicle
- B60L50/50—Electric propulsion with power supplied within the vehicle using propulsion power supplied by batteries or fuel cells
- B60L50/60—Electric propulsion with power supplied within the vehicle using propulsion power supplied by batteries or fuel cells using power supplied by batteries
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L7/00—Electrodynamic brake systems for vehicles in general
- B60L7/10—Dynamic electric regenerative braking
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60L—PROPULSION OF ELECTRICALLY-PROPELLED VEHICLES; SUPPLYING ELECTRIC POWER FOR AUXILIARY EQUIPMENT OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRODYNAMIC BRAKE SYSTEMS FOR VEHICLES IN GENERAL; MAGNETIC SUSPENSION OR LEVITATION FOR VEHICLES; MONITORING OPERATING VARIABLES OF ELECTRICALLY-PROPELLED VEHICLES; ELECTRIC SAFETY DEVICES FOR ELECTRICALLY-PROPELLED VEHICLES
- B60L7/00—Electrodynamic brake systems for vehicles in general
- B60L7/10—Dynamic electric regenerative braking
- B60L7/16—Dynamic electric regenerative braking for vehicles comprising converters between the power source and the motor
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
- E01C19/22—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for consolidating or finishing laid-down unset materials
- E01C19/23—Rollers therefor; Such rollers usable also for compacting soil
- E01C19/26—Rollers therefor; Such rollers usable also for compacting soil self-propelled or fitted to road vehicles
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
- E01C19/22—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for consolidating or finishing laid-down unset materials
- E01C19/23—Rollers therefor; Such rollers usable also for compacting soil
- E01C19/28—Vibrated rollers or rollers subjected to impacts, e.g. hammering blows
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Mechanical Engineering (AREA)
- Transportation (AREA)
- Power Engineering (AREA)
- Civil Engineering (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Sustainable Energy (AREA)
- Sustainable Development (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19548812A DE19548812A1 (de) | 1995-12-27 | 1995-12-27 | Verwendung von Inhibitoren des zellulären Na·+·/H·+·-Exchangers (NHE) zur Herstellung eines Medikaments zur Atemstimulation |
| DE19548812.1 | 1995-12-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2241531A1 true CA2241531A1 (en) | 1997-07-10 |
Family
ID=7781474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002241531A Abandoned CA2241531A1 (en) | 1995-12-27 | 1996-12-13 | Use of inhibitors of the cellular na+/h+ exchanger (nhe) for the preparation of a drug for respiratory stimulation |
Country Status (16)
| Country | Link |
|---|---|
| EP (1) | EP0869779A1 (cs) |
| KR (1) | KR19990076802A (cs) |
| CN (1) | CN1207676A (cs) |
| AU (1) | AU717247B2 (cs) |
| BR (1) | BR9612287A (cs) |
| CA (1) | CA2241531A1 (cs) |
| CZ (1) | CZ202198DA3 (cs) |
| DE (1) | DE19548812A1 (cs) |
| HU (1) | HUP9900807A3 (cs) |
| IL (1) | IL125114A0 (cs) |
| MX (1) | MX9805141A (cs) |
| NO (1) | NO982989L (cs) |
| PL (1) | PL327693A1 (cs) |
| SK (1) | SK88398A3 (cs) |
| TR (1) | TR199801235T2 (cs) |
| WO (1) | WO1997024113A1 (cs) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6686384B2 (en) | 2000-12-05 | 2004-02-03 | Aventis Pharma Deutschland Gmbh | Substituted benzimidazoles, processes for their preparation, their use as medicaments, and medicaments comprising them |
| WO2014029983A1 (en) | 2012-08-21 | 2014-02-27 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US9932331B2 (en) | 2014-07-25 | 2018-04-03 | Taisho Pharmaceutical Co., Ltd. | Phenyl tetrahydroisoquinoline compound substituted with heteroaryl |
| WO2018129552A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| WO2018129557A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| EP3351248A1 (en) | 2008-12-31 | 2018-07-25 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2019060051A1 (en) | 2017-08-04 | 2019-03-28 | Ardelyx, Inc. | GLYCYRRHETINIC ACID DERIVATIVES FOR THE TREATMENT OF HYPERKALIEMIA |
| US10272079B2 (en) | 2013-04-12 | 2019-04-30 | Ardelyx, Inc. | NHE3-binding compounds and methods for inhibiting phosphate transport |
| WO2020163642A1 (en) | 2019-02-07 | 2020-08-13 | Ardelyx, Inc. | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE9504537D0 (sv) * | 1995-12-19 | 1995-12-19 | Jan Hedner | Sätt att behandla och diagnosticera andningsstörningar under sömn och medel för utförande av sättet |
| DE19945302A1 (de) * | 1999-09-22 | 2001-03-29 | Merck Patent Gmbh | Biphenylderivate als NHE-3-Inhibitoren |
| DE10163239A1 (de) * | 2001-12-21 | 2003-07-10 | Aventis Pharma Gmbh | Substituierte Imidazolidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie enthaltendes Medikament |
| US10376481B2 (en) | 2012-08-21 | 2019-08-13 | Ardelyx, Inc. | Compounds and methods for inhibiting NHE-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| EP0639573A1 (de) * | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| DE4337609A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4415873A1 (de) * | 1994-05-05 | 1995-11-09 | Hoechst Ag | Substituierte bizyklische Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1995
- 1995-12-27 DE DE19548812A patent/DE19548812A1/de not_active Withdrawn
-
1996
- 1996-12-13 BR BR9612287-0A patent/BR9612287A/pt unknown
- 1996-12-13 SK SK883-98A patent/SK88398A3/sk unknown
- 1996-12-13 PL PL96327693A patent/PL327693A1/xx unknown
- 1996-12-13 IL IL12511496A patent/IL125114A0/xx unknown
- 1996-12-13 CA CA002241531A patent/CA2241531A1/en not_active Abandoned
- 1996-12-13 KR KR1019980704927A patent/KR19990076802A/ko not_active Withdrawn
- 1996-12-13 EP EP96943956A patent/EP0869779A1/de not_active Withdrawn
- 1996-12-13 AU AU13720/97A patent/AU717247B2/en not_active Ceased
- 1996-12-13 WO PCT/EP1996/005614 patent/WO1997024113A1/de not_active Application Discontinuation
- 1996-12-13 TR TR1998/01235T patent/TR199801235T2/xx unknown
- 1996-12-13 CN CN96199403A patent/CN1207676A/zh active Pending
- 1996-12-13 HU HU9900807A patent/HUP9900807A3/hu unknown
-
1998
- 1998-06-24 MX MX9805141A patent/MX9805141A/es unknown
- 1998-06-26 NO NO982989A patent/NO982989L/no not_active Application Discontinuation
-
2021
- 2021-03-03 CZ CZ982021A patent/CZ202198DA3/cs unknown
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6958357B2 (en) | 2000-12-05 | 2005-10-25 | Aventis Pharma Deutschland Gmbh | Substituted benzimidazoles, processes for their preparation, their use as medicaments, and medicaments comprising them |
| US6686384B2 (en) | 2000-12-05 | 2004-02-03 | Aventis Pharma Deutschland Gmbh | Substituted benzimidazoles, processes for their preparation, their use as medicaments, and medicaments comprising them |
| EP3939964A1 (en) | 2008-12-31 | 2022-01-19 | Ardelyx, Inc. | Combinations for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| EP3351248A1 (en) | 2008-12-31 | 2018-07-25 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2014029983A1 (en) | 2012-08-21 | 2014-02-27 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| US10272079B2 (en) | 2013-04-12 | 2019-04-30 | Ardelyx, Inc. | NHE3-binding compounds and methods for inhibiting phosphate transport |
| US10940146B2 (en) | 2013-04-12 | 2021-03-09 | Ardelyx, Inc. | NHE3-binding compounds and methods for inhibiting phosphate transport |
| EP3988120A1 (en) | 2013-04-12 | 2022-04-27 | Ardelyx, Inc. | Nhe3-binding compounds and methods for inhibiting phosphate transport |
| EP3552630A1 (en) | 2013-04-12 | 2019-10-16 | Ardelyx, Inc. | Nhe3-binding compounds for inhibiting phosphate transport |
| US9932331B2 (en) | 2014-07-25 | 2018-04-03 | Taisho Pharmaceutical Co., Ltd. | Phenyl tetrahydroisoquinoline compound substituted with heteroaryl |
| WO2018129556A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds and methods for inhibiting nhe-mediated antiport in the treatment of disorders associated with fluid retention or salt overload and gastrointestinal tract disorders |
| WO2018129557A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Inhibitors of nhe-mediated antiport |
| WO2018129552A1 (en) | 2017-01-09 | 2018-07-12 | Ardelyx, Inc. | Compounds useful for treating gastrointestinal tract disorders |
| WO2019060051A1 (en) | 2017-08-04 | 2019-03-28 | Ardelyx, Inc. | GLYCYRRHETINIC ACID DERIVATIVES FOR THE TREATMENT OF HYPERKALIEMIA |
| EP4397366A2 (en) | 2017-08-04 | 2024-07-10 | Ardelyx, Inc. | Glycyrrhetinic acid derivatives for treating hyperkalemia |
| WO2020163642A1 (en) | 2019-02-07 | 2020-08-13 | Ardelyx, Inc. | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| EP4234016A2 (en) | 2019-02-07 | 2023-08-30 | Ardelyx, Inc. | Glycyrrhetinic acid derivatives for use in treating hyperkalemia |
| WO2020237096A1 (en) | 2019-05-21 | 2020-11-26 | Ardelyx, Inc. | Combination for lowering serum phosphate in a patient |
Also Published As
| Publication number | Publication date |
|---|---|
| SK88398A3 (en) | 1999-03-12 |
| IL125114A0 (en) | 1999-01-26 |
| TR199801235T2 (xx) | 1998-10-21 |
| MX9805141A (es) | 1998-10-31 |
| CZ202198DA3 (cs) | 1998-11-11 |
| NO982989L (no) | 1998-08-06 |
| BR9612287A (pt) | 2005-05-24 |
| WO1997024113A1 (de) | 1997-07-10 |
| DE19548812A1 (de) | 1997-07-03 |
| AU1372097A (en) | 1997-07-28 |
| CN1207676A (zh) | 1999-02-10 |
| EP0869779A1 (de) | 1998-10-14 |
| HUP9900807A2 (hu) | 1999-07-28 |
| AU717247B2 (en) | 2000-03-23 |
| NO982989D0 (no) | 1998-06-26 |
| KR19990076802A (ko) | 1999-10-15 |
| HUP9900807A3 (en) | 2000-11-28 |
| PL327693A1 (en) | 1998-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |