SK282052B6 - Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDF

Info

Publication number: SK282052B6
Authority: SK; Slovakia
Prior art keywords: formula; benzoylguanidine; general formula; compounds; methyl
Prior art date: 1995-05-16

Application number

SK590-96A

Other languages

English (en)

Slovak (sk)

Other versions

SK59096A3 (en

Inventor

Dieter Dorsch

Manfred Baumgarth

Rolf Gericke

Klaus-Otto Minck

Norbert Beier

Original Assignee

Merck Patent Gmbh

Priority date (The priority date 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 date listed.)

1995-05-16

Filing date

1996-05-09

Publication date

2001-10-08

1996-05-09 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1996-12-04 Publication of SK59096A3 publication Critical patent/SK59096A3/sk

2001-10-08 Publication of SK282052B6 publication Critical patent/SK282052B6/sk

Links

238000002360 preparation method Methods 0.000 title claims description 9
AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 title claims description 7
229910052731 fluorine Inorganic materials 0.000 title description 4
239000011737 fluorine Substances 0.000 title description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 title 1
239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 48
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 19
238000011282 treatment Methods 0.000 claims abstract description 14
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 12
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 12
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 9
206010002383 Angina Pectoris Diseases 0.000 claims abstract description 4
206010003119 arrhythmia Diseases 0.000 claims abstract description 4
230000006793 arrhythmia Effects 0.000 claims abstract description 4
-1 sulfonylmethyl Chemical group 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
206010061216 Infarction Diseases 0.000 claims description 4
230000007574 infarction Effects 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
230000008569 process Effects 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
238000010306 acid treatment Methods 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
XYEIQWWYUKARGX-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(C(F)(F)F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N XYEIQWWYUKARGX-UHFFFAOYSA-N 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000001153 fluoro group Chemical class F* 0.000 claims 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
FDSCJJYUFRNFSU-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-(trifluoromethoxy)benzamide Chemical compound CC1=CC(OC(F)(F)F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N FDSCJJYUFRNFSU-UHFFFAOYSA-N 0.000 claims 1
102000003669 Antiporters Human genes 0.000 abstract description 5
108090000084 Antiporters Proteins 0.000 abstract description 5
230000003288 anthiarrhythmic effect Effects 0.000 abstract description 4
230000001413 cellular effect Effects 0.000 abstract description 4
239000003112 inhibitor Substances 0.000 abstract description 3
208000010125 myocardial infarction Diseases 0.000 abstract 1
238000006243 chemical reaction Methods 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
206010021143 Hypoxia Diseases 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000003708 ampul Substances 0.000 description 3
239000003416 antiarrhythmic agent Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000003449 preventive effect Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229940033134 talc Drugs 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000282693 Cercopithecidae Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
206010020880 Hypertrophy Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000004913 activation Effects 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
150000001558 benzoic acid derivatives Chemical class 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
239000003086 colorant Substances 0.000 description 2
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
239000008298 dragée Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
206010020718 hyperplasia Diseases 0.000 description 2
230000001146 hypoxic effect Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
208000028867 ischemia Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
210000000653 nervous system Anatomy 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 2
229920001592 potato starch Polymers 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
LVQJKHIGKSZQFN-UHFFFAOYSA-N 2-methyl-4-phenoxy-5-(trifluoromethyl)benzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC(OC=2C=CC=CC=2)=C1C(F)(F)F LVQJKHIGKSZQFN-UHFFFAOYSA-N 0.000 description 1
CNRCFIFMZGXXRA-UHFFFAOYSA-N 4-amino-n-(diaminomethylidene)benzamide Chemical class NC(=N)NC(=O)C1=CC=C(N)C=C1 CNRCFIFMZGXXRA-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
206010048962 Brain oedema Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
206010016654 Fibrosis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020852 Hypertonia Diseases 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
229960002576 amiloride Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
NZLBHDRPUJLHCE-UHFFFAOYSA-N aprindine Chemical compound C1C2=CC=CC=C2CC1N(CCCN(CC)CC)C1=CC=CC=C1 NZLBHDRPUJLHCE-UHFFFAOYSA-N 0.000 description 1
229960004957 aprindine Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
208000006752 brain edema Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
KDQPSPMLNJTZAL-UHFFFAOYSA-L disodium hydrogenphosphate dihydrate Chemical compound O.O.[Na+].[Na+].OP([O-])([O-])=O KDQPSPMLNJTZAL-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000006196 drop Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
210000003743 erythrocyte Anatomy 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
230000004761 fibrosis Effects 0.000 description 1
230000003176 fibrotic effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000013773 glyceryl triacetate Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
230000007654 ischemic lesion Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
229940057948 magnesium stearate Drugs 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
UKIMWXUUSVBJJS-UHFFFAOYSA-N methyl 2-methyl-5-methylsulfonyl-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC(S(C)(=O)=O)=C(C(F)(F)F)C=C1C UKIMWXUUSVBJJS-UHFFFAOYSA-N 0.000 description 1
LQODVVRNKLSHHZ-UHFFFAOYSA-N methyl 3-methylsulfonyl-4-(trifluoromethyl)benzoate Chemical compound COC(=O)C1=CC=C(C(F)(F)F)C(S(C)(=O)=O)=C1 LQODVVRNKLSHHZ-UHFFFAOYSA-N 0.000 description 1
QGAGCQPVCPGBJM-UHFFFAOYSA-N methyl 4-bromo-3-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C(S(C)(=O)=O)=C1 QGAGCQPVCPGBJM-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
PJNVHCLQAAYUSK-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-phenoxy-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(OC=2C=CC=CC=2)=C1C(F)(F)F PJNVHCLQAAYUSK-UHFFFAOYSA-N 0.000 description 1
TWANYRKMWKQXDZ-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-(trifluoromethoxy)benzamide;2-methyl-5-methylsulfonyl-4-(trifluoromethoxy)benzoic acid Chemical compound CC1=CC(OC(F)(F)F)=C(S(C)(=O)=O)C=C1C(O)=O.CC1=CC(OC(F)(F)F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N TWANYRKMWKQXDZ-UHFFFAOYSA-N 0.000 description 1
URBDIHSNGQFELA-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C1=CC(C(=O)N=C(N)N)=CC=C1C(F)(F)F URBDIHSNGQFELA-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
238000007339 nucleophilic aromatic substitution reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
208000037920 primary disease Diseases 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
230000000894 saliuretic effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
208000037921 secondary disease Diseases 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
230000002792 vascular Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Vascular Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Phenolic Resins Or Amino Resins (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

SK590-96A 1995-05-16 1996-05-09 Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje SK282052B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19517848A DE19517848A1 (de)	1995-05-16	1995-05-16	Fluorhaltige Benzoylguanidine

Publications (2)

Publication Number	Publication Date
SK59096A3 SK59096A3 (en)	1996-12-04
SK282052B6 true SK282052B6 (sk)	2001-10-08

Family

ID=7761987

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK590-96A SK282052B6 (sk)	1995-05-16	1996-05-09	Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje

Country Status (23)

Country	Link
US (1)	US5747539A (ru)
EP (1)	EP0743301B1 (ru)
JP (1)	JPH08311011A (ru)
KR (1)	KR960041154A (ru)
CN (1)	CN1064955C (ru)
AT (1)	ATE204856T1 (ru)
AU (1)	AU713743B2 (ru)
CA (1)	CA2176553A1 (ru)
CZ (1)	CZ287750B6 (ru)
DE (2)	DE19517848A1 (ru)
DK (1)	DK0743301T3 (ru)
ES (1)	ES2161936T3 (ru)
GR (1)	GR3037033T3 (ru)
HU (1)	HU223046B1 (ru)
NO (1)	NO306157B1 (ru)
PL (1)	PL184192B1 (ru)
PT (1)	PT743301E (ru)
RU (1)	RU2159230C2 (ru)
SI (1)	SI0743301T1 (ru)
SK (1)	SK282052B6 (ru)
TW (1)	TW363052B (ru)
UA (1)	UA44260C2 (ru)
ZA (1)	ZA963870B (ru)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4328352A1 (de)	1993-08-24	1995-03-02	Hoechst Ag	Substituierte N,N'-Di-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19606509A1 (de) *	1996-02-22	1997-08-28	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE19608161A1 (de) *	1996-03-04	1997-09-11	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
US5747639A (en) *	1996-03-06	1998-05-05	Amgen Boulder Inc.	Use of hydrophobic interaction chromatography to purify polyethylene glycols
DE19713427A1 (de) *	1997-04-01	1998-10-08	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
JP2002530325A (ja) *	1998-11-26	2002-09-17	メルクパテントゲゼルシャフトミットベシュレンクテルハフトング	非インスリン依存型真性糖尿病の治療へのベンゾイルグアニジンの使用
DE10222192A1 (de) *	2002-05-18	2003-11-27	Aventis Pharma Gmbh	Pentafluorsulfuranyl-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
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
DE10353204A1 (de) *	2003-11-13	2005-06-16	Aventis Pharma Deutschland Gmbh	Verfahren zur Herstellung von 4-Pentafluorsulfanyl-benzoylguanidinen
US20050124666A1 (en) *	2003-11-13	2005-06-09	Aventis Pharma Deutschland Gmbh	Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same
OA13285A (en) *	2003-11-13	2007-01-31	Sanofi Aventis Deutschland	Pentafluorosulfanyl benzoylguanidines, method for their production, their use as medicaments or diagnostic agents and medicament containing the same.

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3929582A1 (de) *	1989-09-06	1991-03-07	Hoechst Ag	Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament
DE59302959D1 (de) *	1992-02-15	1996-07-25	Hoechst Ag	3,5-Substituierte Benzoylguanidine, mit antiarrythmischer Wirkung und inhibierender Wirkung auf die Proliferationen von Zellen
ATE158278T1 (de) *	1992-02-15	1997-10-15	Hoechst Ag	Ortho-substituierte benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltendes medikament
ATE147375T1 (de) *	1992-09-22	1997-01-15	Hoechst Ag	Benzoylguanidine, verfahren zu ihrer herstellung, sowie ihre verwendung als antiarrhythmika
TW250477B (ru) *	1992-12-15	1995-07-01	Hoechst Ag
TW250479B (ru) *	1992-12-15	1995-07-01	Hoechst Ag
DE4318756A1 (de) *	1993-06-05	1994-12-08	Hoechst Ag	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4328869A1 (de) *	1993-08-27	1995-03-02	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4417004A1 (de) *	1994-05-13	1995-11-16	Hoechst Ag	Perfluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DE4430916A1 (de) *	1994-08-31	1996-03-07	Merck Patent Gmbh	Alkyl-benzoylguanidin-Derivate

1995
- 1995-05-16 DE DE19517848A patent/DE19517848A1/de not_active Withdrawn
1996
- 1996-03-25 TW TW085103561A patent/TW363052B/zh active
- 1996-05-02 DK DK96106881T patent/DK0743301T3/da active
- 1996-05-02 AT AT96106881T patent/ATE204856T1/de not_active IP Right Cessation
- 1996-05-02 EP EP96106881A patent/EP0743301B1/de not_active Expired - Lifetime
- 1996-05-02 ES ES96106881T patent/ES2161936T3/es not_active Expired - Lifetime
- 1996-05-02 DE DE59607559T patent/DE59607559D1/de not_active Expired - Fee Related
- 1996-05-02 SI SI9630361T patent/SI0743301T1/xx unknown
- 1996-05-02 PT PT96106881T patent/PT743301E/pt unknown
- 1996-05-09 SK SK590-96A patent/SK282052B6/sk unknown
- 1996-05-13 CN CN961058854A patent/CN1064955C/zh not_active Expired - Fee Related
- 1996-05-13 UA UA96051860A patent/UA44260C2/uk unknown
- 1996-05-13 AU AU52252/96A patent/AU713743B2/en not_active Ceased
- 1996-05-14 CA CA002176553A patent/CA2176553A1/en not_active Abandoned
- 1996-05-15 CZ CZ19961408A patent/CZ287750B6/cs not_active IP Right Cessation
- 1996-05-15 HU HU9601305A patent/HU223046B1/hu not_active IP Right Cessation
- 1996-05-15 PL PL96314259A patent/PL184192B1/pl unknown
- 1996-05-15 US US08/647,789 patent/US5747539A/en not_active Expired - Fee Related
- 1996-05-15 ZA ZA963870A patent/ZA963870B/xx unknown
- 1996-05-15 NO NO961997A patent/NO306157B1/no not_active IP Right Cessation
- 1996-05-15 KR KR1019960016096A patent/KR960041154A/ko active IP Right Grant
- 1996-05-15 RU RU96109204/04A patent/RU2159230C2/ru not_active IP Right Cessation
- 1996-05-16 JP JP8144881A patent/JPH08311011A/ja active Pending
2001
- 2001-10-30 GR GR20010401903T patent/GR3037033T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE204856T1 (de)	2001-09-15
DE19517848A1 (de)	1996-11-21
NO961997L (no)	1996-11-18
AU5225296A (en)	1996-11-28
DK0743301T3 (da)	2001-11-26
HU9601305D0 (en)	1996-07-29
TW363052B (en)	1999-07-01
ES2161936T3 (es)	2001-12-16
HUP9601305A3 (en)	1997-11-28
NO306157B1 (no)	1999-09-27
PL184192B1 (pl)	2002-09-30
DE59607559D1 (de)	2001-10-04
SK59096A3 (en)	1996-12-04
CZ287750B6 (en)	2001-01-17
NO961997D0 (no)	1996-05-15
CN1064955C (zh)	2001-04-25
GR3037033T3 (en)	2002-01-31
ZA963870B (en)	1996-11-21
HUP9601305A2 (en)	1997-05-28
EP0743301A2 (de)	1996-11-20
CN1143632A (zh)	1997-02-26
RU2159230C2 (ru)	2000-11-20
UA44260C2 (uk)	2002-02-15
CA2176553A1 (en)	1996-11-17
AU713743B2 (en)	1999-12-09
EP0743301B1 (de)	2001-08-29
JPH08311011A (ja)	1996-11-26
PT743301E (pt)	2002-01-30
PL314259A1 (en)	1996-11-25
EP0743301A3 (de)	1997-06-11
CZ140896A3 (en)	1997-02-12
HU223046B1 (hu)	2004-03-01
SI0743301T1 (en)	2002-02-28
KR960041154A (ko)	1996-12-19
US5747539A (en)	1998-05-05

Publication	Publication Date	Title
KR100275603B1 (ko)	2000-12-15	아미노-치환된 벤조일구아니딘, 이의 제조방법 및 이를 함유하는 약제학적 조성물
EP0640593B1 (de)	1997-12-29	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
SK281766B6 (sk)	2001-07-10	Substituované sulfónimidamidy, spôsob ich prípravy, ich použitie ako liečiva alebo diagnostika, ako i liečivo, ktoré ich obsahuje
US5849796A (en)	1998-12-15	Ortho-substituted benzoil acid derivatives
SK282052B6 (sk)	2001-10-08	Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
PL184320B1 (pl)	2002-10-31	Nowe związki, pochodne 4-sulfonylo-lub 4-sulfinylobenzoiloguanidyny, sposób ich wytwarzania oraz preparat farmaceutyczny
SK13196A3 (en)	1996-09-04	Alkalicly substituted benzoylguanidines, manufacturing process thereof, their use as drug or diagnostic agent and drugs containing these compositions
EP0602522B1 (de)	1996-05-29	Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Antiarrhythmika
SK96596A3 (en)	1997-03-05	Substituted guanidines of cinnamic acid, manufacturing process thereof, their use as drug or diagnosticum as a drug containing them
SK62996A3 (en)	1996-12-04	Substituted benzyloxycarbonyl guanidines, method of their producing, their use and drugs containing them
CZ288015B6 (cs)	2001-04-11	Derivát alkylbenzoylguanidinu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
UA44237C2 (uk)	2002-02-15	Арилбензоїлгуанідини, спосіб їх отримання, фармацевтична композиція
SK281198B6 (sk)	2001-01-18	Derivát 4-aminobenzoylguanidínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje
US5756535A (en)	1998-05-26	Substituted thiophenylalkenylcarboxylic acid guanidines, processes for their preparation, their use as a medicament or diagnositc, and a medicament containing them
HU224011B1 (hu)	2005-04-28	Alkil-5-metil-szulfonil-benzoil-guanidin-származékok, eljárás előállításukra az ezeket tartalmazó gyógyászati készítmények és alkalmazásuk
SK281199B6 (sk)	2001-01-18	Derivát 4-merkaptobenzoylguanidínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje
SK283040B6 (sk)	2003-02-04	Heterocyklyloxybenzoylguanidíny, spôsob ich výroby, ich použitie a farmaceutické prostriedky na ich báze
SK146596A3 (en)	1997-11-05	Sulfonylaminosubstituted benzoylguanidines, producing method, their use as a drug or diagnostic agent, as well as a drug containing the same
DE19950898A1 (de)	2001-04-26	Heterocyclisch substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
SK283934B6 (sk)	2004-05-04	Orto-substituované benzoylguanidíny, spôsob ich prípravy, ich použitie ako liečiva a liečivá, ktoré ich obsahujú
SK23797A3 (en)	1997-11-05	Ortho-substituted benzoylguanidines, producing method, their use as a drug or diagnostic agent, as well as a drug containing the same
EP0774457A1 (de)	1997-05-21	Substituierte Benzoldicarbonsäure-diguanidide, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament