SK282356B6 - Substituované 1-naftoylguanidíny, spôsob ich výroby, ich použitie ako liečiva alebo diagnostického prostriedku a liečivo, ktoré ich obsahuje - Google Patents
Substituované 1-naftoylguanidíny, spôsob ich výroby, ich použitie ako liečiva alebo diagnostického prostriedku a liečivo, ktoré ich obsahuje Download PDFInfo
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- SK282356B6 SK282356B6 SK669-97A SK66997A SK282356B6 SK 282356 B6 SK282356 B6 SK 282356B6 SK 66997 A SK66997 A SK 66997A SK 282356 B6 SK282356 B6 SK 282356B6
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- 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 title claims abstract description 7
- 239000003814 drug Substances 0.000 title claims description 36
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000011282 treatment Methods 0.000 claims abstract description 36
- 238000011321 prophylaxis Methods 0.000 claims abstract description 11
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 7
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 4
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 150000001875 compounds Chemical class 0.000 claims description 65
- 239000001257 hydrogen Substances 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 30
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 23
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 21
- 229910052717 sulfur Inorganic materials 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 13
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000000302 ischemic effect Effects 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 230000004663 cell proliferation Effects 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 4
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 206010020718 hyperplasia Diseases 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 2
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- 230000000879 anti-atherosclerotic effect Effects 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 230000003176 fibrotic effect Effects 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
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- 230000006793 arrhythmia Effects 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 230000006378 damage Effects 0.000 abstract description 5
- 208000028867 ischemia Diseases 0.000 abstract description 4
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 3
- 230000003293 cardioprotective effect Effects 0.000 abstract description 2
- 230000035778 pathophysiological process Effects 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000011734 sodium Substances 0.000 description 16
- -1 1-imidazolyl Chemical group 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 229960002576 amiloride Drugs 0.000 description 9
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000002265 prevention Effects 0.000 description 9
- 201000001320 Atherosclerosis Diseases 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
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- 229910052708 sodium Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 210000003743 erythrocyte Anatomy 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- 208000035150 Hypercholesterolemia Diseases 0.000 description 4
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
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- 206010012601 diabetes mellitus Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000004941 influx Effects 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 150000005209 naphthoic acids Chemical class 0.000 description 4
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- 210000002966 serum Anatomy 0.000 description 4
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 108010007622 LDL Lipoproteins Proteins 0.000 description 3
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
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- QDERNBXNXJCIQK-UHFFFAOYSA-N ethylisopropylamiloride Chemical compound CCN(C(C)C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl QDERNBXNXJCIQK-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
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- QBWXQZHHVDIJSF-UHFFFAOYSA-N methyl 6-hydroxynaphthalene-1-carboxylate Chemical compound OC1=CC=C2C(C(=O)OC)=CC=CC2=C1 QBWXQZHHVDIJSF-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 2
- RXMUPNVSYKGKMY-UHFFFAOYSA-N 3-amino-6-chloro-n-(diaminomethylidene)-5-(dimethylamino)pyrazine-2-carboxamide Chemical compound CN(C)C1=NC(N)=C(C(=O)N=C(N)N)N=C1Cl RXMUPNVSYKGKMY-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
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- AYJVQAUCUPQCCI-UHFFFAOYSA-N 6-[2-(diethylamino)ethoxy]naphthalene-1-carboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(OCCN(CC)CC)=CC=C21 AYJVQAUCUPQCCI-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
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- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 230000000054 salidiuretic effect Effects 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- TXXHDPDFNKHHGW-ZPUQHVIOSA-N trans,trans-muconic acid Chemical compound OC(=O)\C=C\C=C\C(O)=O TXXHDPDFNKHHGW-ZPUQHVIOSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000009441 vascular protection Effects 0.000 description 1
- 210000004509 vascular smooth muscle cell Anatomy 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19621482A DE19621482A1 (de) | 1996-05-29 | 1996-05-29 | Substituierte 1-Naphthoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK66997A3 SK66997A3 (en) | 1997-12-10 |
| SK282356B6 true SK282356B6 (sk) | 2002-01-07 |
Family
ID=7795548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK669-97A SK282356B6 (sk) | 1996-05-29 | 1997-05-27 | Substituované 1-naftoylguanidíny, spôsob ich výroby, ich použitie ako liečiva alebo diagnostického prostriedku a liečivo, ktoré ich obsahuje |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6600072B2 (cs) |
| EP (1) | EP0810205B1 (cs) |
| JP (1) | JP4039587B2 (cs) |
| KR (1) | KR970074753A (cs) |
| CN (1) | CN1062859C (cs) |
| AR (1) | AR007299A1 (cs) |
| AT (1) | ATE200076T1 (cs) |
| AU (1) | AU710258B2 (cs) |
| BR (1) | BR9703342A (cs) |
| CA (1) | CA2206362C (cs) |
| CZ (1) | CZ292441B6 (cs) |
| DE (2) | DE19621482A1 (cs) |
| DK (1) | DK0810205T3 (cs) |
| ES (1) | ES2155223T3 (cs) |
| GR (1) | GR3035811T3 (cs) |
| HR (1) | HRP970294B1 (cs) |
| HU (1) | HUP9700954A3 (cs) |
| ID (1) | ID17348A (cs) |
| IL (1) | IL120925A0 (cs) |
| NO (1) | NO308528B1 (cs) |
| NZ (1) | NZ314914A (cs) |
| PL (1) | PL185755B1 (cs) |
| PT (1) | PT810205E (cs) |
| RU (1) | RU2182901C2 (cs) |
| SI (1) | SI0810205T1 (cs) |
| SK (1) | SK282356B6 (cs) |
| TR (1) | TR199700427A2 (cs) |
| TW (1) | TW372955B (cs) |
| ZA (1) | ZA974664B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19621483A1 (de) * | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE10023405A1 (de) * | 2000-05-12 | 2001-11-15 | Merck Patent Gmbh | Verfahren zur Herstellung von Sulfonyl-benzoylguanidinum-Salzen |
| AR039156A1 (es) * | 2002-03-28 | 2005-02-09 | Novartis Ag | Amidas del acido piperidinilamino sulfamico o piperazinil sulfamico y su uso para la manufactura de un medicamento en enfermedades mediadas por la accion de la sulfatasa esteroide |
| EP1590338B1 (en) * | 2002-12-04 | 2009-08-26 | Ore Pharmaceuticals Inc. | Modulators of melanocortin receptor |
| KR101153254B1 (ko) * | 2003-06-26 | 2012-07-02 | 바이오트론 리미티드 | 항바이러스 화합물 및 방법 |
| US20110118262A1 (en) * | 2008-07-08 | 2011-05-19 | Boehringer Ingelheim International Gmbh | Pyrrolidinyl and Piperidinyl Compounds Useful as NHE-1 Inhibitiors |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251545A (en) * | 1979-09-19 | 1981-02-17 | Gaf Corporation | Fungicidal process using 1-(alkoxyaroyl)guanidines |
| DE4035961A1 (de) * | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| IL109570A0 (en) * | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| 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 |
| 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 |
| JPH08225513A (ja) * | 1994-12-21 | 1996-09-03 | Kanebo Ltd | ナフトイルグアニジン誘導体 |
| JPH08225135A (ja) | 1995-02-21 | 1996-09-03 | Mitsubishi Heavy Ind Ltd | スクリユ−式土砂搬送機 |
| DE19621483A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1996
- 1996-05-29 DE DE19621482A patent/DE19621482A1/de not_active Withdrawn
-
1997
- 1997-02-28 PL PL97318724A patent/PL185755B1/pl not_active IP Right Cessation
- 1997-05-16 EP EP97108012A patent/EP0810205B1/de not_active Expired - Lifetime
- 1997-05-16 SI SI9730125T patent/SI0810205T1/xx unknown
- 1997-05-16 DE DE59703220T patent/DE59703220D1/de not_active Expired - Lifetime
- 1997-05-16 DK DK97108012T patent/DK0810205T3/da active
- 1997-05-16 ES ES97108012T patent/ES2155223T3/es not_active Expired - Lifetime
- 1997-05-16 AT AT97108012T patent/ATE200076T1/de not_active IP Right Cessation
- 1997-05-16 PT PT97108012T patent/PT810205E/pt unknown
- 1997-05-27 TR TR97/00427A patent/TR199700427A2/xx unknown
- 1997-05-27 CN CN97113186A patent/CN1062859C/zh not_active Expired - Fee Related
- 1997-05-27 CZ CZ19971631A patent/CZ292441B6/cs not_active IP Right Cessation
- 1997-05-27 IL IL12092597A patent/IL120925A0/xx not_active IP Right Cessation
- 1997-05-27 HR HR970294A patent/HRP970294B1/xx not_active IP Right Cessation
- 1997-05-27 SK SK669-97A patent/SK282356B6/sk unknown
- 1997-05-27 AU AU23713/97A patent/AU710258B2/en not_active Ceased
- 1997-05-27 TW TW086107121A patent/TW372955B/zh active
- 1997-05-27 AR ARP970102252A patent/AR007299A1/es unknown
- 1997-05-27 HU HU9700954A patent/HUP9700954A3/hu unknown
- 1997-05-27 NZ NZ314914A patent/NZ314914A/en unknown
- 1997-05-28 RU RU97109002/04A patent/RU2182901C2/ru not_active IP Right Cessation
- 1997-05-28 KR KR1019970021106A patent/KR970074753A/ko not_active Ceased
- 1997-05-28 ID IDP971813A patent/ID17348A/id unknown
- 1997-05-28 NO NO972434A patent/NO308528B1/no not_active IP Right Cessation
- 1997-05-28 CA CA002206362A patent/CA2206362C/en not_active Expired - Fee Related
- 1997-05-28 JP JP13822697A patent/JP4039587B2/ja not_active Expired - Fee Related
- 1997-05-28 ZA ZA9704664A patent/ZA974664B/xx unknown
- 1997-05-30 BR BR9703342A patent/BR9703342A/pt not_active IP Right Cessation
-
2001
- 2001-04-30 GR GR20010400659T patent/GR3035811T3/el not_active IP Right Cessation
-
2002
- 2002-08-14 US US10/217,457 patent/US6600072B2/en not_active Expired - Fee Related
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