HRP980488A2 - The use of a sodium-hydrogen exchanger inhibitor in the production of a medicine for the prevention of undesirable effects of substances to a heart - Google Patents
The use of a sodium-hydrogen exchanger inhibitor in the production of a medicine for the prevention of undesirable effects of substances to a heartInfo
- Publication number
- HRP980488A2 HRP980488A2 HR19738604.0A HRP980488A HRP980488A2 HR P980488 A2 HRP980488 A2 HR P980488A2 HR P980488 A HRP980488 A HR P980488A HR P980488 A2 HRP980488 A2 HR P980488A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- substituted
- group
- zero
- atoms
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title claims description 26
- 239000003814 drug Substances 0.000 title claims description 24
- 210000002216 heart Anatomy 0.000 title claims description 16
- 230000000694 effects Effects 0.000 title claims description 14
- 108091006672 Sodium–hydrogen antiporter Proteins 0.000 title claims description 10
- 239000000126 substance Substances 0.000 title claims description 6
- 102000052126 Sodium-Hydrogen Exchangers Human genes 0.000 title description 2
- 230000002265 prevention Effects 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims description 542
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 533
- 239000001257 hydrogen Substances 0.000 claims description 513
- 239000000460 chlorine Substances 0.000 claims description 459
- 229910052731 fluorine Inorganic materials 0.000 claims description 455
- 229910052801 chlorine Inorganic materials 0.000 claims description 451
- 125000001424 substituent group Chemical group 0.000 claims description 437
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 389
- 125000004432 carbon atom Chemical group C* 0.000 claims description 367
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 366
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 331
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 294
- 229910052760 oxygen Inorganic materials 0.000 claims description 285
- -1 C5-C7-cycloalkyl Chemical group 0.000 claims description 254
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 238
- 125000000217 alkyl group Chemical group 0.000 claims description 232
- 239000001301 oxygen Substances 0.000 claims description 229
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 226
- 229910052717 sulfur Inorganic materials 0.000 claims description 178
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 166
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 166
- 150000002431 hydrogen Chemical class 0.000 claims description 146
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 140
- 229910052794 bromium Inorganic materials 0.000 claims description 129
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 97
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000001624 naphthyl group Chemical group 0.000 claims description 81
- 229910052799 carbon Inorganic materials 0.000 claims description 67
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 67
- 229910052757 nitrogen Inorganic materials 0.000 claims description 63
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 62
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 61
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 59
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#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 39
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 35
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 35
- 239000011593 sulfur Substances 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 26
- 150000002367 halogens Chemical group 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 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 21
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 21
- 239000011737 fluorine Substances 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 12
- 150000001409 amidines Chemical group 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 230000001451 cardiotoxic effect Effects 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
- 231100000457 cardiotoxic Toxicity 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl 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 6
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 6
- 150000007513 acids Chemical group 0.000 claims description 6
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 230000001085 cytostatic effect Effects 0.000 claims description 6
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 6
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 5
- 239000000824 cytostatic agent Substances 0.000 claims description 5
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 206010048610 Cardiotoxicity Diseases 0.000 claims description 4
- 229910020587 CmF2m+1 Inorganic materials 0.000 claims description 4
- 231100000259 cardiotoxicity Toxicity 0.000 claims description 4
- 150000002357 guanidines Chemical class 0.000 claims description 4
- 238000011275 oncology therapy Methods 0.000 claims description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 229940088710 antibiotic agent Drugs 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 125000005413 thiopyridyl group Chemical group 0.000 claims description 3
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006313 (C5-C8) alkyl group Chemical group 0.000 claims description 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 description 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 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 229940009456 adriamycin Drugs 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- IWXNYAIICFKCTM-UHFFFAOYSA-N cariporide Chemical compound CC(C)C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O IWXNYAIICFKCTM-UHFFFAOYSA-N 0.000 claims description 2
- 229950008393 cariporide Drugs 0.000 claims description 2
- 239000002934 diuretic Substances 0.000 claims description 2
- 229940030606 diuretics Drugs 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
- 239000003835 ketolide antibiotic agent Substances 0.000 claims description 2
- 239000003120 macrolide antibiotic agent Substances 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
- 125000003831 tetrazolyl 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
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 102000050381 Na+/H+ exchanger Human genes 0.000 claims 8
- 125000003435 aroyl group Chemical group 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 8
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 8
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 125000003107 substituted aryl group Chemical group 0.000 claims 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 229910006069 SO3H Inorganic materials 0.000 claims 4
- 125000001931 aliphatic group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- QZWBOYMQPQVGPM-UHFFFAOYSA-N 2-(1h-indol-2-yl)guanidine Chemical class C1=CC=C2NC(NC(=N)N)=CC2=C1 QZWBOYMQPQVGPM-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000004648 C2-C8 alkenyl 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
- 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
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000002723 alicyclic group Chemical group 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 125000004957 naphthylene group Chemical group 0.000 claims 2
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 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 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000005024 alkenyl aryl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000005025 alkynylaryl group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- FZOCFRPFPKJHHP-UHFFFAOYSA-N benzyl n-(diaminomethylidene)carbamate Chemical class NC(N)=NC(=O)OCC1=CC=CC=C1 FZOCFRPFPKJHHP-UHFFFAOYSA-N 0.000 claims 1
- 244000309464 bull Species 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 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
- 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 group C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005059 halophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 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
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 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
- FNDLQABGYJQJPH-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-propan-2-ylbenzamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O FNDLQABGYJQJPH-UHFFFAOYSA-N 0.000 claims 1
- APOPAXUENTVHHC-UHFFFAOYSA-N n-(diaminomethylidene)naphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=O)NC(=N)N)=CC=CC2=C1 APOPAXUENTVHHC-UHFFFAOYSA-N 0.000 claims 1
- OECMIBNCPUMKFU-UHFFFAOYSA-N n-(diaminomethylidene)naphthalene-2-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C21 OECMIBNCPUMKFU-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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)
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- 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
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- 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
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
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- 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)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Toxicology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19738604A DE19738604A1 (de) | 1997-09-04 | 1997-09-04 | Die Verwendung von Hemmern des Natrium-Wasserstoff-Austauschers zur Herstellung eines Medikaments zur Verminderung der Giftigkeit cardiotoxischer Stoffe |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP980488A2 true HRP980488A2 (en) | 1999-06-30 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| HR19738604.0A HRP980488A2 (en) | 1997-09-04 | 1998-09-03 | The use of a sodium-hydrogen exchanger inhibitor in the production of a medicine for the prevention of undesirable effects of substances to a heart |
Country Status (22)
| Country | Link |
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| US (1) | US6462024B1 (cs) |
| EP (1) | EP0916337A3 (cs) |
| JP (1) | JP4555409B2 (cs) |
| KR (1) | KR19990029520A (cs) |
| CN (1) | CN1195508C (cs) |
| AR (1) | AR015718A1 (cs) |
| AU (1) | AU753899B2 (cs) |
| BR (1) | BR9803319A (cs) |
| CA (1) | CA2246633A1 (cs) |
| CZ (1) | CZ280898A3 (cs) |
| DE (1) | DE19738604A1 (cs) |
| HR (1) | HRP980488A2 (cs) |
| HU (1) | HUP9802005A3 (cs) |
| IL (1) | IL126068A0 (cs) |
| NO (1) | NO984071L (cs) |
| NZ (1) | NZ331682A (cs) |
| PL (1) | PL328366A1 (cs) |
| RU (1) | RU2252754C2 (cs) |
| SK (1) | SK121198A3 (cs) |
| TR (1) | TR199801728A2 (cs) |
| TW (1) | TW592693B (cs) |
| ZA (1) | ZA988066B (cs) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7375138B2 (en) * | 2002-05-18 | 2008-05-20 | Sanofi-Aventis Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, processes for their preparation, their use as medicaments or diagnostic aids, and medicaments comprising them |
| FR2840302B1 (fr) * | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | Derives d'isoindolones, procede de preparation et intermediaire de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| US6878748B2 (en) | 2002-06-13 | 2005-04-12 | Aventis Pharma Deutschland Gmbh | Fluorinated cycloalkyl-derivatized benzoylguanidines, process for their preparation, their uses as medicament, and medicament containing them |
| BRPI0410022A (pt) * | 2003-05-06 | 2006-04-25 | Merck Patent Gmbh | processo para a cristalização de sais de guanidìnio |
| CN112107568B (zh) * | 2019-06-19 | 2022-03-25 | 北京龙嘉博创医药科技有限公司 | 二芳基酰胺类化合物及其应用 |
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| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| DE4127026A1 (de) * | 1991-08-16 | 1993-02-18 | Boehringer Ingelheim Kg | Neue pyrazinderivate, ihre herstellung und verwendung |
| CZ284456B6 (cs) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje |
| EP0589336B1 (de) * | 1992-09-22 | 1997-01-08 | Hoechst Aktiengesellschaft | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
| TW250479B (cs) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| DE4337609A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| DE4422685A1 (de) * | 1994-06-29 | 1996-01-04 | Hoechst Ag | Ortho-amino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4428480A1 (de) * | 1994-08-11 | 1996-03-07 | Hoechst Ag | Substituierte Benzoesäureester, Verfahren zu ihrer Herstellung und ihre Verwendung zur Synthese von Inhibitoren des zellulären Na·+·/H·+·-Austauschs |
| DE4430861A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Heterocyclyl-benzoylguanidine |
| DE4441880A1 (de) * | 1994-11-24 | 1996-05-30 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19734693A1 (de) * | 1997-08-11 | 1998-01-22 | Hoechst Marion Roussel De Gmbh | Verwendung von Cariporide als Inhibitor des zellulären NA+/H+-Exchangers (NHE) zur Herstellung eines Medikaments zur Behandlung von cardialen und nichtcardialen Krankheiten |
-
1997
- 1997-09-04 DE DE19738604A patent/DE19738604A1/de not_active Withdrawn
-
1998
- 1998-08-29 EP EP98116434A patent/EP0916337A3/de not_active Withdrawn
- 1998-09-01 BR BR9803319A patent/BR9803319A/pt not_active Application Discontinuation
- 1998-09-02 SK SK1211-98A patent/SK121198A3/sk unknown
- 1998-09-02 NZ NZ331682A patent/NZ331682A/en unknown
- 1998-09-02 AR ARP980104391A patent/AR015718A1/es unknown
- 1998-09-02 TR TR1998/01728A patent/TR199801728A2/xx unknown
- 1998-09-03 CZ CZ982808A patent/CZ280898A3/cs unknown
- 1998-09-03 AU AU83073/98A patent/AU753899B2/en not_active Ceased
- 1998-09-03 JP JP25017198A patent/JP4555409B2/ja not_active Expired - Fee Related
- 1998-09-03 HR HR19738604.0A patent/HRP980488A2/hr not_active Application Discontinuation
- 1998-09-03 CN CNB981188400A patent/CN1195508C/zh not_active Expired - Fee Related
- 1998-09-03 IL IL12606898A patent/IL126068A0/xx unknown
- 1998-09-03 ZA ZA988066A patent/ZA988066B/xx unknown
- 1998-09-03 HU HU9802005A patent/HUP9802005A3/hu unknown
- 1998-09-03 RU RU98116473/14A patent/RU2252754C2/ru not_active IP Right Cessation
- 1998-09-04 NO NO984071A patent/NO984071L/no not_active Application Discontinuation
- 1998-09-04 CA CA002246633A patent/CA2246633A1/en not_active Abandoned
- 1998-09-04 KR KR1019980036405A patent/KR19990029520A/ko not_active Ceased
- 1998-09-04 PL PL98328366A patent/PL328366A1/xx unknown
- 1998-09-23 TW TW087114509A patent/TW592693B/zh not_active IP Right Cessation
-
2000
- 2000-07-11 US US09/614,122 patent/US6462024B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HU9802005D0 (en) | 1998-11-30 |
| EP0916337A2 (de) | 1999-05-19 |
| NO984071D0 (no) | 1998-09-04 |
| NZ331682A (en) | 2001-08-31 |
| SK121198A3 (en) | 1999-03-12 |
| HUP9802005A3 (en) | 2005-06-28 |
| JP4555409B2 (ja) | 2010-09-29 |
| AU753899B2 (en) | 2002-10-31 |
| BR9803319A (pt) | 2000-03-21 |
| CN1195508C (zh) | 2005-04-06 |
| NO984071L (no) | 1999-03-05 |
| AR015718A1 (es) | 2001-05-16 |
| HUP9802005A2 (hu) | 1999-04-28 |
| HK1018212A1 (en) | 1999-12-17 |
| TW592693B (en) | 2004-06-21 |
| CZ280898A3 (cs) | 1999-03-17 |
| US6462024B1 (en) | 2002-10-08 |
| ZA988066B (en) | 1999-03-11 |
| RU2252754C2 (ru) | 2005-05-27 |
| CA2246633A1 (en) | 1999-03-04 |
| DE19738604A1 (de) | 1999-03-11 |
| EP0916337A3 (de) | 2004-03-17 |
| CN1209995A (zh) | 1999-03-10 |
| TR199801728A2 (xx) | 1999-04-21 |
| PL328366A1 (en) | 1999-03-15 |
| JPH11180896A (ja) | 1999-07-06 |
| KR19990029520A (ko) | 1999-04-26 |
| AU8307398A (en) | 1999-03-18 |
| IL126068A0 (en) | 1999-05-09 |
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