DE19546736A1 - Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate - Google Patents
Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer PräparateInfo
- Publication number
- DE19546736A1 DE19546736A1 DE19546736A DE19546736A DE19546736A1 DE 19546736 A1 DE19546736 A1 DE 19546736A1 DE 19546736 A DE19546736 A DE 19546736A DE 19546736 A DE19546736 A DE 19546736A DE 19546736 A1 DE19546736 A1 DE 19546736A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- hydrogen
- alkyl
- substituted
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
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- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 235000013877 carbamide Nutrition 0.000 title claims description 7
- 150000003672 ureas Chemical class 0.000 title claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 title claims description 4
- 238000000034 method Methods 0.000 title description 16
- 239000000825 pharmaceutical preparation Substances 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 99
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 150000002431 hydrogen Chemical group 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical group 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000003951 lactams Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
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- 238000011282 treatment Methods 0.000 claims description 5
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- -1 aromatic sulfonamides Chemical class 0.000 description 56
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
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- 150000007513 acids Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 8
- 206010019280 Heart failures Diseases 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- 230000036982 action potential Effects 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
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- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
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- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- PVMBGVAQRSHDBB-UHFFFAOYSA-N benzenesulfonylthiourea Chemical compound NC(=S)NS(=O)(=O)C1=CC=CC=C1 PVMBGVAQRSHDBB-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 150000003456 sulfonamides Chemical class 0.000 description 5
- SSUQOCGURBMNOD-UHFFFAOYSA-N 5-chloro-2-methoxy-n-[(7-methoxy-6-sulfamoyl-3,4-dihydro-2h-chromen-4-yl)methyl]benzamide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCC1C2=CC(S(N)(=O)=O)=C(OC)C=C2OCC1 SSUQOCGURBMNOD-UHFFFAOYSA-N 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- 206010049993 Cardiac death Diseases 0.000 description 4
- 206010011906 Death Diseases 0.000 description 4
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 206010042600 Supraventricular arrhythmias Diseases 0.000 description 4
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- 125000003118 aryl group Chemical group 0.000 description 4
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- 150000002430 hydrocarbons Chemical group 0.000 description 4
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- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- XLTUPERVRFLGLJ-UHFFFAOYSA-N isothiocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=S XLTUPERVRFLGLJ-UHFFFAOYSA-N 0.000 description 1
- 150000002541 isothioureas Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 210000003205 muscle Anatomy 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
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- ZACBJJDJJBGIDC-UHFFFAOYSA-N n-(sulfanylidenemethylidene)benzenesulfonamide Chemical class S=C=NS(=O)(=O)C1=CC=CC=C1 ZACBJJDJJBGIDC-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical class ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000004036 potassium channel stimulating agent Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002336 repolarization Effects 0.000 description 1
- 229950011590 rilmakalim Drugs 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- XYMVZPOXZCDCNP-UHFFFAOYSA-N sulfamoyl cyanide Chemical class NS(=O)(=O)C#N XYMVZPOXZCDCNP-UHFFFAOYSA-N 0.000 description 1
- RISUTSCZAANJJQ-UHFFFAOYSA-N sulfinylurea Chemical compound NC(=O)N=S=O RISUTSCZAANJJQ-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- PMCLTINCHUUECN-UHFFFAOYSA-N sulfonylcarbamodithioic acid Chemical compound SC(=S)N=S(=O)=O PMCLTINCHUUECN-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 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
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UVVUGWBBCDFNSD-UHFFFAOYSA-N tetraisocyanatosilane Chemical compound O=C=N[Si](N=C=O)(N=C=O)N=C=O UVVUGWBBCDFNSD-UHFFFAOYSA-N 0.000 description 1
- NOGBKWXHNPDHFA-UHFFFAOYSA-N tetraisothiocyanatosilane Chemical compound S=C=N[Si](N=C=S)(N=C=S)N=C=S NOGBKWXHNPDHFA-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013343 vitamin Nutrition 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
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/42—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4
- C07D311/56—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms in positions 2 and 4 without hydrogen atoms in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/64—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with oxygen atoms directly attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19546736A DE19546736A1 (de) | 1995-12-14 | 1995-12-14 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate |
| AT96119262T ATE191212T1 (de) | 1995-12-14 | 1996-12-02 | Substituierte chromanylsulfonyl(thio)harnstoffe, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen präparaten sowie sie enthaltende pharmazeutische präparate |
| PT96119262T PT779288E (pt) | 1995-12-14 | 1996-12-02 | Cromanilsulfonil(tio)ureia substituida processo para a sua preparacao e sua utilizacao em composicoes farmaceuticas bem como composicoes farmaceuticas que os contem |
| ES96119262T ES2146348T3 (es) | 1995-12-14 | 1996-12-02 | Cromanilsulfonil(tio)ureas sustituidas, procedimiento para su preparacion y su utilizacion en preparados farmaceuticos, asi como preparados farmaceuticos que las contienen. |
| EP96119262A EP0779288B1 (de) | 1995-12-14 | 1996-12-02 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Präparaten sowie sie enthaltende pharmazeutische Präparate |
| SI9630206T SI0779288T1 (en) | 1995-12-14 | 1996-12-02 | Substituted chromanylsulfonyl(thio)ureas, process for their preparation, their use in pharmaceutical compositions and preparations containing them |
| DK96119262T DK0779288T3 (da) | 1995-12-14 | 1996-12-02 | Substituerede chromanylsulfonyl(thio)urinstoffer, fremgangsmåde til deres fremstilling, deres anvendelse i farmaceutiske sa |
| DE59604831T DE59604831D1 (de) | 1995-12-14 | 1996-12-02 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Präparaten sowie sie enthaltende pharmazeutische Präparate |
| US08/760,610 US5811448A (en) | 1995-12-14 | 1996-12-04 | Substituted chromanysulfonyl (thio) ureas, processing for their preparation and pharmaceutical uses thereof |
| PL96317397A PL186505B1 (pl) | 1995-12-14 | 1996-12-09 | Nowe podstawione pochodne chromanylosulfonylo(tio) mocznika, sposób ich wytwarzania i środek farmaceutyczny |
| RU96123576/04A RU2170733C2 (ru) | 1995-12-14 | 1996-12-11 | Замещенные хроманилсульфонил(тио)мочевины, способ их получения и фармацевтическая композиция |
| HR19546736.1 HRP960584B1 (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfonyl(thio)ureas, process for their preparation, their use in pharmaceutical compositions and pharmaceutical preparations containing them |
| SK1602-96A SK281739B6 (sk) | 1995-12-14 | 1996-12-12 | Substituované chromanylsulfonyl(tio)močoviny, spôsob ich prípravy, ich použitie a liečivo s ich obsahom |
| ZA9610461A ZA9610461B (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfony(thio)ureas processes of their preparation their use in pharmaceutical preparations and pharmaceutical preparations comprising them |
| TR96/00992A TR199600992A2 (tr) | 1995-12-14 | 1996-12-12 | Sübstitüe edilmis kromanilsulfonil(tio) üreler, bunlarin üretilmesine mahsus usul ve ispenciyari müstehzarlarin icinde kullanilmalari ile bunlari iceren müstahzarlar. |
| CNB961215348A CN1158272C (zh) | 1995-12-14 | 1996-12-12 | 取代的苯并二氢吡喃基磺酰(硫)脲、其制备方法、其在药剂中的应用及含其的药剂 |
| AU75312/96A AU707371B2 (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfonyl(thio)ureas, processes for their preparation, their use in pharmaceutical preparations, and pharmaceutical preparations comprising them |
| ARP960105642A AR005249A1 (es) | 1995-12-14 | 1996-12-12 | Cromanilsulfonil (tio) ureas sustituidas, procedimiento para prepararlas, su utilizacion para preparar medicamentos y medicamentos que las contienen |
| IL11982296A IL119822A (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfonyl (thio) ureas processes for their preparation their use in pharmaceutical preparations and pharmaceutical preparations comprising them |
| TW085115339A TW370528B (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfonyl(thio)ureas, the preparation processes and the pharmaceutical compositions for use as antiarrhythmics thereof |
| NZ299928A NZ299928A (en) | 1995-12-14 | 1996-12-12 | Chromanylsulphonyl(thio)urea derivatives, preparation and medicaments |
| CZ19963658A CZ291094B6 (cs) | 1995-12-14 | 1996-12-12 | Substituované chromanylsulfonyl(thio)močoviny, způsob jejich přípravy, jejich pouľití ve farmaceutických preparátech jakoľ i léčiva, která je obsahují |
| MYPI96005219A MY115229A (en) | 1995-12-14 | 1996-12-12 | Substituted chromanylsulfonyl(thio) ureas, processes for their preparation their use in pharmaceutical preparations, and pharmaceutical preparations comprising them. |
| JP33318096A JP4132115B2 (ja) | 1995-12-14 | 1996-12-13 | 置換されたクロマニルスルホニル（チオ）尿素、それらの製法、医薬製剤におけるそれらの使用およびそれらを含有する医薬製剤 |
| MXPA/A/1996/006397A MXPA96006397A (en) | 1995-12-14 | 1996-12-13 | Substituted chromanylsulphonyl(thio)ureas, processs for the preparation thereof and their utilization in pharmaceutical composiitons, as well as pharmaceutical composiitons containing the same |
| NO19965370A NO315159B1 (no) | 1995-12-14 | 1996-12-13 | Substituerte kromanylsulfonyl(tio)ureaer, fremgangsmåter til deres fremstilling, deres anvendelse i farmasöytiske preparater samtfarmasöytiske preparaterinneholdende forbindelsene |
| KR1019960065314A KR100460961B1 (ko) | 1995-12-14 | 1996-12-13 | 치환된크로마닐설포닐(티오)우레아및이를포함하는약제학적조성물 |
| HU9603450A HU222284B1 (hu) | 1995-12-14 | 1996-12-13 | Szubsztituált kromanil-szulfonil-tiokarbamidok, eljárás a vegyületek előállítására, gyógyszerkészítményekben történő alkalmazásuk, valamint a vegyületeket tartalmazó gyógyászati készítmények |
| CA002192916A CA2192916C (en) | 1995-12-14 | 1996-12-13 | Substituted chromanylsulfonyl(thio)ureas, processes for their preparation, their use in pharmaceutical preparations, and pharmaceutical preparations comprising them |
| BR9605989A BR9605989A (pt) | 1995-12-14 | 1996-12-13 | Cromanilsulfonil(tio)uréias substituídas processo para sua preparação e seu uso em preparados farmacêuticos bem como preparados farmacêuticos contendo as mesmas |
| GR20000400982T GR3033300T3 (en) | 1995-12-14 | 2000-04-21 | Substituted chromanylsulfonyl(thio)ureas, process for their preparation, their use in pharmaceutical compositions and preparations containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19546736A DE19546736A1 (de) | 1995-12-14 | 1995-12-14 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19546736A1 true DE19546736A1 (de) | 1997-06-19 |
Family
ID=7780152
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19546736A Withdrawn DE19546736A1 (de) | 1995-12-14 | 1995-12-14 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung pharmazeutischer Präparate |
| DE59604831T Expired - Lifetime DE59604831D1 (de) | 1995-12-14 | 1996-12-02 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Präparaten sowie sie enthaltende pharmazeutische Präparate |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59604831T Expired - Lifetime DE59604831D1 (de) | 1995-12-14 | 1996-12-02 | Substituierte Chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung in pharmazeutischen Präparaten sowie sie enthaltende pharmazeutische Präparate |
Country Status (29)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19647000A1 (de) * | 1996-11-14 | 1998-05-20 | Hoechst Ag | 3-Amido-chromanylsulfonyl(thio)harnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| FR2756284B1 (fr) * | 1996-11-26 | 2000-04-28 | Adir | Nouveaux derives du benzopyrane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| AU2830800A (en) * | 1999-03-25 | 2000-10-16 | Nissan Chemical Industries Ltd. | Chroman derivatives |
| DE10348298A1 (de) * | 2003-10-17 | 2005-05-19 | Solvay Pharmaceuticals Gmbh | Amidomethyl-substituierte 2-(4-Sulfonylamino)-3-hydroxy-3,4-dihydro-2H-chromen-6-ylderivade, Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US7368582B2 (en) * | 2003-10-17 | 2008-05-06 | Solvay Pharmaceuticals Gmbh | Amidomethyl-substituted 2-(4-sulfonylamino)-3-hydroxy-3,4-dihydro-2H-chromen-6-yl compounds, a process and intermediates for their production, and pharmaceutical compositions containing them |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE727417C (de) * | 1939-08-23 | 1942-11-03 | Paul Kretzschmar | Schwingbackenbrecher |
| DE1518874C3 (de) * | 1964-10-07 | 1975-03-13 | Farbwerke Hoechst Ag, Vormals Meister Lucius & Bruening, 6000 Frankfurt | Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung |
| US3803176A (en) * | 1969-05-09 | 1974-04-09 | Novo Terapeutisk Labor As | Sulfonylurea derivatives |
| GB1314325A (en) * | 1969-05-09 | 1973-04-18 | Novo Teapeutisk Lab As | Carboxylic acids |
| US3780027A (en) * | 1970-04-29 | 1973-12-18 | Merck & Co Inc | Anthranilic acid derivatives |
| JP2673024B2 (ja) | 1988-01-15 | 1997-11-05 | アボツト・ラボラトリーズ | アミノメチル‐クロマン及び‐チオクロマン化合物 |
| US5140039A (en) | 1988-01-15 | 1992-08-18 | Abbott Laboratories | Aminomethyl-thiochroman compounds |
| US5185364A (en) | 1988-01-15 | 1993-02-09 | Abbott Laboratories | Aminomethyl-chroman and -thiochroman compounds |
| DE3929582A1 (de) * | 1989-09-06 | 1991-03-07 | Hoechst Ag | Benzoylguanidine, verfahren zu ihrer herstellung, ihre verwendung als medikament sowie sie enthaltendes medikament |
| TW222637B (cg-RX-API-DMAC10.html) * | 1991-12-12 | 1994-04-21 | Hoechst Ag | |
| EP0556674B1 (de) * | 1992-02-15 | 1996-06-19 | Hoechst Aktiengesellschaft | 3,5-Substituierte Benzoylguanidine, mit antiarrythmischer Wirkung und inhibierender Wirkung auf die Proliferationen von Zellen |
| CZ284456B6 (cs) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje |
| 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 |
| RU2047614C1 (ru) * | 1992-06-15 | 1995-11-10 | Джон Вайс энд Бразер Лимитед | Гетероциклические соединения, или их фармацевтически приемлемые аддитивные соли кислоты, или n-оксид гетероциклического соединения, или его аддитивная соль кислоты |
| DK0577024T3 (cg-RX-API-DMAC10.html) * | 1992-07-01 | 1997-02-24 | Hoechst Ag | |
| EP0589336B1 (de) * | 1992-09-22 | 1997-01-08 | Hoechst Aktiengesellschaft | Benzoylguanidine, Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Antiarrhythmika |
| DK0590455T3 (da) * | 1992-09-28 | 2001-01-22 | Hoechst Ag | Antiarrytmiske og cardioprotektive substiuerede 1(2H)-isoquinoliner, fremgangsmåde til deres fremstilling, lægemiddel indeh |
| TW250477B (cg-RX-API-DMAC10.html) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| TW250479B (cg-RX-API-DMAC10.html) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| ES2100435T3 (es) * | 1992-12-16 | 1997-06-16 | Hoechst Ag | Aminobenzoilguanidinas 3,5-sustituidas, procedimiento para su preparacion, su empleo como medicamento o agente de diagnostico, asi como medicamento que las contiene. |
| 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 |
| DE59403818D1 (de) * | 1993-02-20 | 1997-10-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, als Inhibitoren des zellulären Na+/H+-Austauschs oder als Diagnostikum sowie sie enthaltendes Medikament |
| DE59401361D1 (de) * | 1993-02-23 | 1997-02-06 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe- Verfahren zu ihrer Herstellung und ihre Verwendung als Pharmazeutika |
| 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 |
| 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 |
| DE4325822A1 (de) * | 1993-07-31 | 1995-02-02 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| EP0639573A1 (de) * | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
| DE4327244A1 (de) * | 1993-08-13 | 1995-02-16 | Hoechst Ag | Harnstoffsubstituierte Benzoylguandine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| 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 |
| 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 |
| DE4344550A1 (de) * | 1993-12-24 | 1995-06-29 | Hoechst Ag | Substituierte 1-Oxo-1,2-dihydro-isochinolinoyl- und 1,1-Dioxo-2H-1,2-benzothiazinoylguanidine, Verfahrenzu ihrer Herstellung, ihre Verwendung als Medikamentt oder Diagnostikum sowie sie enthaltendes Medikamen |
| TW415937B (en) * | 1994-01-25 | 2000-12-21 | Hoechst Ag | Phenyl-substituted alkylcarboxylic acid guanidides bearing perfluoroalkyl groups, process for their preparation, their use as a medicament or diagnostic, and medicament containing them |
| DE4412334A1 (de) * | 1994-04-11 | 1995-10-19 | Hoechst Ag | Substituierte N-Heteroaroylguanidine, 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 |
| 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 |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4422685A1 (de) * | 1994-06-29 | 1996-01-04 | Hoechst Ag | Ortho-amino-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4432105A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Fluoro-alkyl/alkenyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4432106A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Mit Heterocyclen-N-Oxid-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum, sie enthaltendes Medikament sowie Zwischenprodukte zu ihrer Herstellung |
| DE4432101A1 (de) * | 1994-09-09 | 1996-03-14 | Hoechst Ag | Aminosäure-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4441880A1 (de) * | 1994-11-24 | 1996-05-30 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DK0723956T3 (da) * | 1995-01-30 | 2000-04-17 | Hoechst Ag | Basisk substituerede benzoylguanidiner, fremgangsmåde til fremstilling deraf, anvendelse deraf som lægemiddel eller diagnos |
| HU226462B1 (en) * | 1995-02-17 | 2008-12-29 | Hoechst Ag | Substituted benzol-sulfonyl-ureas and -thioureas, process for producing them, pharmaceutical compositions containing them, and their use |
| DE19505397A1 (de) * | 1995-02-17 | 1996-08-22 | Hoechst Ag | Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1995
- 1995-12-14 DE DE19546736A patent/DE19546736A1/de not_active Withdrawn
-
1996
- 1996-12-02 ES ES96119262T patent/ES2146348T3/es not_active Expired - Lifetime
- 1996-12-02 SI SI9630206T patent/SI0779288T1/xx unknown
- 1996-12-02 EP EP96119262A patent/EP0779288B1/de not_active Expired - Lifetime
- 1996-12-02 DK DK96119262T patent/DK0779288T3/da active
- 1996-12-02 AT AT96119262T patent/ATE191212T1/de active
- 1996-12-02 DE DE59604831T patent/DE59604831D1/de not_active Expired - Lifetime
- 1996-12-02 PT PT96119262T patent/PT779288E/pt unknown
- 1996-12-04 US US08/760,610 patent/US5811448A/en not_active Expired - Lifetime
- 1996-12-09 PL PL96317397A patent/PL186505B1/pl not_active IP Right Cessation
- 1996-12-11 RU RU96123576/04A patent/RU2170733C2/ru not_active IP Right Cessation
- 1996-12-12 AU AU75312/96A patent/AU707371B2/en not_active Ceased
- 1996-12-12 TW TW085115339A patent/TW370528B/zh not_active IP Right Cessation
- 1996-12-12 MY MYPI96005219A patent/MY115229A/en unknown
- 1996-12-12 CZ CZ19963658A patent/CZ291094B6/cs not_active IP Right Cessation
- 1996-12-12 AR ARP960105642A patent/AR005249A1/es active IP Right Grant
- 1996-12-12 NZ NZ299928A patent/NZ299928A/en not_active IP Right Cessation
- 1996-12-12 SK SK1602-96A patent/SK281739B6/sk not_active IP Right Cessation
- 1996-12-12 HR HR19546736.1 patent/HRP960584B1/xx not_active IP Right Cessation
- 1996-12-12 CN CNB961215348A patent/CN1158272C/zh not_active Expired - Fee Related
- 1996-12-12 ZA ZA9610461A patent/ZA9610461B/xx unknown
- 1996-12-12 TR TR96/00992A patent/TR199600992A2/xx unknown
- 1996-12-12 IL IL11982296A patent/IL119822A/xx not_active IP Right Cessation
- 1996-12-13 JP JP33318096A patent/JP4132115B2/ja not_active Expired - Fee Related
- 1996-12-13 NO NO19965370A patent/NO315159B1/no not_active IP Right Cessation
- 1996-12-13 KR KR1019960065314A patent/KR100460961B1/ko not_active Expired - Fee Related
- 1996-12-13 CA CA002192916A patent/CA2192916C/en not_active Expired - Fee Related
- 1996-12-13 BR BR9605989A patent/BR9605989A/pt not_active IP Right Cessation
- 1996-12-13 HU HU9603450A patent/HU222284B1/hu not_active IP Right Cessation
-
2000
- 2000-04-21 GR GR20000400982T patent/GR3033300T3/el unknown
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