SK281661B6 - Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDF

Info

Publication number: SK281661B6
Authority: SK; Slovakia
Prior art keywords: diaminomethylene; formula; methyl; ethyl; methylsulfonylbenzamide
Prior art date: 1995-08-11

Application number

SK1033-96A

Other languages

English (en)

Slovak (sk)

Other versions

SK103396A3 (en

Inventor

Rolf Gericke

Manfred Baumgarth

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.)

1995-08-11

Filing date

1996-08-07

Publication date

2001-06-11

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7769293&utm_source=***_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=SK281661(B6) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1996-08-07 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1997-03-05 Publication of SK103396A3 publication Critical patent/SK103396A3/sk

2001-06-11 Publication of SK281661B6 publication Critical patent/SK281661B6/sk

Links

238000000034 method Methods 0.000 title claims abstract description 14
XOFVXSMENNKBRH-UHFFFAOYSA-N n-[amino-(sulfinylamino)methylidene]benzamide Chemical class O=S=NC(N)=NC(=O)C1=CC=CC=C1 XOFVXSMENNKBRH-UHFFFAOYSA-N 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 79
238000011282 treatment Methods 0.000 claims abstract description 15
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
238000004519 manufacturing process Methods 0.000 claims abstract description 11
LAGJGWGBDKKIQX-UHFFFAOYSA-N n-[amino-(sulfonylamino)methylidene]benzamide Chemical compound O=S(=O)=NC(N)=NC(=O)C1=CC=CC=C1 LAGJGWGBDKKIQX-UHFFFAOYSA-N 0.000 claims abstract description 11
201000010099 disease Diseases 0.000 claims abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
102000003669 Antiporters Human genes 0.000 claims abstract description 6
108090000084 Antiporters Proteins 0.000 claims abstract description 6
206010003119 arrhythmia Diseases 0.000 claims abstract description 6
230000008569 process Effects 0.000 claims abstract description 5
230000006793 arrhythmia Effects 0.000 claims abstract description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 32
150000003839 salts Chemical class 0.000 claims description 20
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 16
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
206010061216 Infarction Diseases 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
230000007574 infarction Effects 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
GROMEQPXDKRRIE-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4,5-bis(methylsulfonyl)benzamide Chemical compound CC1=CC(S(C)(=O)=O)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N GROMEQPXDKRRIE-UHFFFAOYSA-N 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
RSKNQTWLPWOKCV-UHFFFAOYSA-N 4-(benzenesulfonyl)-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1S(C)(=O)=O RSKNQTWLPWOKCV-UHFFFAOYSA-N 0.000 claims description 3
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239000003795 chemical substances by application Substances 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
239000011630 iodine Substances 0.000 claims description 3
238000001465 metallisation Methods 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
BJWRCFVWJBOFDD-UHFFFAOYSA-N 4-tert-butylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(S(=O)(=O)C(C)(C)C)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N BJWRCFVWJBOFDD-UHFFFAOYSA-N 0.000 claims description 2
238000010306 acid treatment Methods 0.000 claims description 2
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
238000006478 transmetalation reaction Methods 0.000 claims description 2
UJURHIFLDARYMY-UHFFFAOYSA-N 4-cyclohexylsulfonyl-n-(diaminomethylidene)-2-methyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C2CCCCC2)=C1S(C)(=O)=O UJURHIFLDARYMY-UHFFFAOYSA-N 0.000 claims 1
XNFHCESYDYHGSU-UHFFFAOYSA-N 4-cyclopentylsulfonyl-n-(diaminomethylidene)-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C2CCCC2)=C1S(C)(=O)=O XNFHCESYDYHGSU-UHFFFAOYSA-N 0.000 claims 1
MDDZBMOWENBNCP-UHFFFAOYSA-N 5-(4-chlorophenyl)sulfonyl-n-(diaminomethylidene)-2-methyl-4-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(C)(=O)=O)=C1S(=O)(=O)C1=CC=C(Cl)C=C1 MDDZBMOWENBNCP-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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239000004480 active ingredient Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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 description 9
125000006239 protecting group Chemical group 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
239000011734 sodium Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
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210000004351 coronary vessel Anatomy 0.000 description 5
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125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 4
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
FFGPTBGBLSHEPO-UHFFFAOYSA-N carbamazepine Chemical compound C1=CC2=CC=CC=C2N(C(=O)N)C2=CC=CC=C21 FFGPTBGBLSHEPO-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000007327 hydrogenolysis reaction Methods 0.000 description 4
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239000003112 inhibitor 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
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239000007858 starting material Substances 0.000 description 4
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NFZMWSDZYXFMLH-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=C(C=CC=2)C(F)(F)F)=C1S(C)(=O)=O NFZMWSDZYXFMLH-UHFFFAOYSA-N 0.000 description 1
WVZNBVWOMAPNAW-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[3-(trifluoromethyl)phenyl]sulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(S(=O)(=O)C=2C=C(C=CC=2)C(F)(F)F)=C1S(C)(=O)=O WVZNBVWOMAPNAW-UHFFFAOYSA-N 0.000 description 1
VAHSYQRAUVRLJY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-[4-(trifluoromethyl)phenyl]sulfanylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(SC=2C=CC(=CC=2)C(F)(F)F)=C1S(C)(=O)=O VAHSYQRAUVRLJY-UHFFFAOYSA-N 0.000 description 1
ZFVIMWBMDDQEEY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propan-2-ylsulfinylbenzamide Chemical compound CC(C)S(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O ZFVIMWBMDDQEEY-UHFFFAOYSA-N 0.000 description 1
SPVMMRALAJYBSX-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-propylsulfinylbenzamide Chemical compound CCCS(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O SPVMMRALAJYBSX-UHFFFAOYSA-N 0.000 description 1
GTOYOXDESAEYOG-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-nitro-4-propan-2-ylsulfonylbenzamide Chemical compound CC(C)S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1[N+]([O-])=O GTOYOXDESAEYOG-UHFFFAOYSA-N 0.000 description 1
CFLLWKVNYSULCQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC(C)=CC=2)C)=C1C(F)(F)F CFLLWKVNYSULCQ-UHFFFAOYSA-N 0.000 description 1
XEFOFHWFNFZJGG-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(SC=2C(=CC(C)=CC=2)C)=C1S(C)(=O)=O XEFOFHWFNFZJGG-UHFFFAOYSA-N 0.000 description 1
SYHWZGMHTGKSEP-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfanyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1SC1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F SYHWZGMHTGKSEP-UHFFFAOYSA-N 0.000 description 1
UUBNPEYIPPEJQQ-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-ethyl-5-(trifluoromethyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC(C)=CC=2)C)=C1C(F)(F)F UUBNPEYIPPEJQQ-UHFFFAOYSA-N 0.000 description 1
FAFYOAANLIJPSH-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-ethyl-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(S(=O)(=O)C=2C(=CC(C)=CC=2)C)=C1S(C)(=O)=O FAFYOAANLIJPSH-UHFFFAOYSA-N 0.000 description 1
IJDATBYDQVJVRG-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F IJDATBYDQVJVRG-UHFFFAOYSA-N 0.000 description 1
PTJVDVWCWUYBKI-UHFFFAOYSA-N n-(diaminomethylidene)-4-(2,4-dimethylphenyl)sulfonyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O PTJVDVWCWUYBKI-UHFFFAOYSA-N 0.000 description 1
GELRCTZDSRLROA-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethylsulfinyl-2-methyl-5-methylsulfonylbenzamide Chemical compound CCS(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O GELRCTZDSRLROA-UHFFFAOYSA-N 0.000 description 1
REACOYHFNDUUHP-UHFFFAOYSA-N n-(diaminomethylidene)-4-ethylsulfonyl-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CCS(=O)(=O)C1=CC(C)=C(C(=O)N=C(N)N)C=C1C(F)(F)F REACOYHFNDUUHP-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 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
125000002524 organometallic group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
229960001412 pentobarbital Drugs 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
239000000902 placebo Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000002028 premature Effects 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
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
208000017497 prostate disease Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
230000010410 reperfusion 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
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
208000037921 secondary disease Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 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
125000003107 substituted aryl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
238000012360 testing method Methods 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
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 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
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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 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
238000009423 ventilation Methods 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
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/38—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atom of at least one amino group being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfones
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- 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

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Life Sciences & Earth Sciences (AREA)
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Urology & Nephrology (AREA)
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Reproductive Health (AREA)
Pulmonology (AREA)
Gastroenterology & Hepatology (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Measuring Leads Or Probes (AREA)

SK1033-96A 1995-08-11 1996-08-07 Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje SK281661B6 (sk)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19529612A DE19529612A1 (de)	1995-08-11	1995-08-11	Sulfonyl- oder Sulfinyl-benzoylguanidin-Derivate

Publications (2)

Publication Number	Publication Date
SK103396A3 SK103396A3 (en)	1997-03-05
SK281661B6 true SK281661B6 (sk)	2001-06-11

Family

ID=7769293

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1033-96A SK281661B6 (sk)	1995-08-11	1996-08-07	Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje

Country Status (25)

Country	Link
US (1)	US5744641A (ru)
EP (1)	EP0758644B1 (ru)
JP (1)	JP3901766B2 (ru)
KR (1)	KR100447111B1 (ru)
CN (1)	CN1071743C (ru)
AR (1)	AR004677A1 (ru)
AT (1)	ATE252075T1 (ru)
AU (1)	AU709800B2 (ru)
BR (1)	BR9603377B1 (ru)
CA (1)	CA2183050C (ru)
CZ (1)	CZ292974B6 (ru)
DE (2)	DE19529612A1 (ru)
DK (1)	DK0758644T3 (ru)
ES (1)	ES2206534T3 (ru)
HU (1)	HU226134B1 (ru)
MX (1)	MX9603300A (ru)
NO (1)	NO306858B1 (ru)
PL (1)	PL184320B1 (ru)
PT (1)	PT758644E (ru)
RU (1)	RU2159232C2 (ru)
SI (1)	SI0758644T1 (ru)
SK (1)	SK281661B6 (ru)
TW (1)	TW432039B (ru)
UA (1)	UA45965C2 (ru)
ZA (1)	ZA966773B (ru)

Families Citing this family (15)

* 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
DE19833118C2 (de) *	1998-07-23	2000-07-27	Merck Patent Gmbh	Verfahren zur Herstellung von orthoalkylierten Benzoesäurederivaten
DE19903275A1 (de) *	1999-01-28	2000-08-03	Merck Patent Gmbh	Lyophilisate mit verbesserter Rekonstituierbarkeit
DE19951418A1 (de) *	1999-10-26	2001-05-03	Merck Patent Gmbh	Verfahren zur Herstellung von N-(4,5-Bismethansulfonyl-2-methyl-benzoyl) -guanidin, Hydrochlorid
DE10001879A1 (de) *	2000-01-19	2001-07-19	Aventis Pharma Gmbh	Substituierte Benzoylguanidine, Verfahren zu 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
KR100643561B1 (ko) *	2000-12-08	2006-11-10	엘지.필립스 엘시디 주식회사	액정표시장치용 어레이기판과 어레이기판의 제조방법
DE10305070A1 (de) *	2003-02-07	2004-08-26	Merck Patent Gmbh	Verwendung von N-(4,5-Methansulfonyl-2-methyl-benzoyl)-guanidin
DE502004007841D1 (de) *	2003-05-06	2008-09-25	Merck Patent Gmbh	Verfahren zur kristallisation von guanidinium-salzen
DE102004045825A1 (de) *	2004-09-22	2006-03-23	Merck Patent Gmbh	Lyophilisat enthaltend N-Diaminomethylen-2-methyl-4,5-di-(methylsulfonyl)-benzamid
ES2804574T3 (es) *	2008-05-09	2021-02-08	Merck Patent Gmbh	Composición farmacéutica para tratar enfermedades asociadas con la resistencia a la insulina y la disfunción de células beta
MX2011001821A (es)	2008-09-02	2011-03-25	Sanofi Aventis	Aminoindanos sustituidos y sus analogos, y el uso farmaceutico de los mismos.
FR2948028B1 (fr)	2009-07-17	2011-12-02	Merck Sante Sas	Association d'un inhibiteur de l'echangeur sodium-proton et d'un derive amine de dihydro-1,3,5-triazine
RU2018131500A (ru)	2016-02-08	2020-03-10	Мерк Патент Гмбх	Кристаллические модификации гидрохлорида n-(4,5-бисметансульфонил-2-метилбензоил)гуанидина и солей n-(4,5-бисметансульфонил-2-метилбензоил)гуанидина
EP4230196A1 (en)	2022-02-21	2023-08-23	Som Innovation Biotech, S.A.	Compounds for use in the treatment of dystrophinopathies

Family Cites Families (4)

* 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
DE59305042D1 (de) *	1992-09-22	1997-02-20	Hoechst Ag	Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika
EP0604852A1 (de) *	1992-12-28	1994-07-06	Hoechst Aktiengesellschaft	2,4-Substituierte 5-(N-substituierte-Sulfamoyl)-Benzoylguanidine, als Antiarrythmika, Inhibitoren der Proliferationen von Zellen, und Inhibitoren des Natrium-Protonen-Antiporters
DE4430916A1 (de) *	1994-08-31	1996-03-07	Merck Patent Gmbh	Alkyl-benzoylguanidin-Derivate

1995
- 1995-08-11 DE DE19529612A patent/DE19529612A1/de not_active Withdrawn
1996
- 1996-07-16 TW TW085108613A patent/TW432039B/zh not_active IP Right Cessation
- 1996-08-02 AT AT96112498T patent/ATE252075T1/de active
- 1996-08-02 DE DE59610773T patent/DE59610773D1/de not_active Expired - Lifetime
- 1996-08-02 SI SI9630659T patent/SI0758644T1/xx unknown
- 1996-08-02 PT PT96112498T patent/PT758644E/pt unknown
- 1996-08-02 DK DK96112498T patent/DK0758644T3/da active
- 1996-08-02 ES ES96112498T patent/ES2206534T3/es not_active Expired - Lifetime
- 1996-08-02 EP EP96112498A patent/EP0758644B1/de not_active Expired - Lifetime
- 1996-08-05 CZ CZ19962312A patent/CZ292974B6/cs not_active IP Right Cessation
- 1996-08-05 AU AU61917/96A patent/AU709800B2/en not_active Expired
- 1996-08-07 SK SK1033-96A patent/SK281661B6/sk not_active IP Right Cessation
- 1996-08-08 ZA ZA9606773A patent/ZA966773B/xx unknown
- 1996-08-08 UA UA96083195A patent/UA45965C2/uk unknown
- 1996-08-08 JP JP22459596A patent/JP3901766B2/ja not_active Expired - Lifetime
- 1996-08-09 PL PL96315611A patent/PL184320B1/pl unknown
- 1996-08-09 CA CA002183050A patent/CA2183050C/en not_active Expired - Lifetime
- 1996-08-09 BR BRPI9603377-0A patent/BR9603377B1/pt not_active IP Right Cessation
- 1996-08-09 AR ARP960103933A patent/AR004677A1/es active IP Right Grant
- 1996-08-09 CN CN96109414A patent/CN1071743C/zh not_active Expired - Lifetime
- 1996-08-09 NO NO963340A patent/NO306858B1/no not_active IP Right Cessation
- 1996-08-09 MX MX9603300A patent/MX9603300A/es unknown
- 1996-08-09 KR KR1019960033207A patent/KR100447111B1/ko not_active IP Right Cessation
- 1996-08-09 US US08/699,053 patent/US5744641A/en not_active Expired - Lifetime
- 1996-08-09 RU RU96115459/04A patent/RU2159232C2/ru active
- 1996-08-09 HU HU9602196A patent/HU226134B1/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE252075T1 (de)	2003-11-15
DE59610773D1 (de)	2003-11-20
JPH0952876A (ja)	1997-02-25
TW432039B (en)	2001-05-01
EP0758644A1 (de)	1997-02-19
CZ292974B6 (cs)	2004-01-14
DK0758644T3 (da)	2003-12-22
AR004677A1 (es)	1999-03-10
CA2183050C (en)	2008-09-30
CN1071743C (zh)	2001-09-26
PL315611A1 (en)	1997-02-17
AU709800B2 (en)	1999-09-09
CN1148590A (zh)	1997-04-30
SK103396A3 (en)	1997-03-05
JP3901766B2 (ja)	2007-04-04
SI0758644T1 (en)	2004-04-30
NO963340L (no)	1997-02-12
KR970010740A (ko)	1997-03-27
BR9603377A (pt)	1998-05-12
CA2183050A1 (en)	1997-02-12
PT758644E (pt)	2004-02-27
BR9603377B1 (pt)	2009-01-13
HUP9602196A3 (en)	1998-07-28
CZ231296A3 (en)	1997-02-12
AU6191796A (en)	1997-02-13
EP0758644B1 (de)	2003-10-15
PL184320B1 (pl)	2002-10-31
UA45965C2 (uk)	2002-05-15
ZA966773B (en)	1997-02-19
MX9603300A (es)	1997-03-29
HU226134B1 (en)	2008-05-28
DE19529612A1 (de)	1997-02-13
HUP9602196A2 (en)	1997-05-28
RU2159232C2 (ru)	2000-11-20
KR100447111B1 (ko)	2004-12-08
NO306858B1 (no)	2000-01-03
NO963340D0 (no)	1996-08-09
HU9602196D0 (en)	1996-10-28
US5744641A (en)	1998-04-28
ES2206534T3 (es)	2004-05-16

Legal Events

Date	Code	Title	Description
2016-10-03	MK4A	Patent expired	Expiry date: 20160807

Publication	Publication Date	Title
PT667341E (pt)	2001-12-28	4-amino-1-peperidilbenzoilguanidinas como inibidores do antiporte na+/h+
SK281661B6 (sk)	2001-06-11	Derivát sulfonylbenzoylguanidínu alebo sulfinylbenzoylguanidínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
SK281446B6 (sk)	2001-03-12	Heterocyklylbenzoylguanidín, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
SK282202B6 (sk)	2001-12-03	Derivát kyseliny benzoovej substituovanej v orto polohe, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
RU2142940C1 (ru)	1999-12-20	Производные алкилбензоилгуанидинов, способ их получения и фармацевтическая композиция на их основе
US5807896A (en)	1998-09-15	Arylbenzoylguanidines
SK282052B6 (sk)	2001-10-08	Derivát benzoylguanidínu obsahujúceho fluór, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
SK281198B6 (sk)	2001-01-18	Derivát 4-aminobenzoylguanidínu, spôsob jeho prípravy a farmaceutický prostriedok, ktorý ho obsahuje
US5700839A (en)	1997-12-23	Alkyl-5-methylsulfonylbenzoylguanidine derivatives
US5731351A (en)	1998-03-24	Alkenyl-benzoylguanidine derivatives
AU706843B2 (en)	1999-06-24	4-mercaptobenzoylguanidine derivatives
SK78995A3 (en)	1996-01-10	Heterocyclyloxybenzoylguanidine their use, method of their production, pharmaceutical preparations on their base and method of their production