RU2190600C2 - Замещенные 2-нафтоилгуанидины и лекарственное средство на их основе - Google Patents
Замещенные 2-нафтоилгуанидины и лекарственное средство на их основе Download PDFInfo
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- RU2190600C2 RU2190600C2 RU97109003/04A RU97109003A RU2190600C2 RU 2190600 C2 RU2190600 C2 RU 2190600C2 RU 97109003/04 A RU97109003/04 A RU 97109003/04A RU 97109003 A RU97109003 A RU 97109003A RU 2190600 C2 RU2190600 C2 RU 2190600C2
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- OECMIBNCPUMKFU-UHFFFAOYSA-N n-(diaminomethylidene)naphthalene-2-carboxamide Chemical class C1=CC=CC2=CC(C(=O)N=C(N)N)=CC=C21 OECMIBNCPUMKFU-UHFFFAOYSA-N 0.000 title claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 91
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 23
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 21
- 229940079593 drug Drugs 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 201000010099 disease Diseases 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 239000013543 active substance Substances 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 17
- 230000002265 prevention Effects 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 208000010125 myocardial infarction Diseases 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 230000000302 ischemic effect Effects 0.000 claims description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 230000004663 cell proliferation Effects 0.000 claims description 3
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
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- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
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- 208000019425 cirrhosis of liver Diseases 0.000 claims description 2
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- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 241001168730 Simo Species 0.000 claims 1
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- 150000001875 compounds Chemical class 0.000 abstract description 42
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- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 32
- -1 2-pyridylthio group Chemical group 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
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- 229910052717 sulfur Inorganic materials 0.000 description 19
- 239000002244 precipitate Substances 0.000 description 18
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- 239000003112 inhibitor Substances 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- UKZOPQRTQJERQC-UHFFFAOYSA-N methyl 6-hydroxynaphthalene-2-carboxylate Chemical compound C1=C(O)C=CC2=CC(C(=O)OC)=CC=C21 UKZOPQRTQJERQC-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 5
- 206010048554 Endothelial dysfunction Diseases 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 3
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- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
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- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KZRRSHWRUTVRPI-UHFFFAOYSA-N 2-(6-methoxycarbonylnaphthalen-2-yl)oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=CC(C(=O)OC)=CC=C21 KZRRSHWRUTVRPI-UHFFFAOYSA-N 0.000 description 2
- KBOBQLJBYKKAPN-UHFFFAOYSA-N 2-chloro-2-methylhexane Chemical compound CCCCC(C)(C)Cl KBOBQLJBYKKAPN-UHFFFAOYSA-N 0.000 description 2
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- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P41/00—Drugs used in surgical methods, e.g. surgery adjuvants for preventing adhesion or for vitreum substitution
-
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19621483.1 | 1996-05-29 | ||
| DE19621483A DE19621483A1 (de) | 1996-05-29 | 1996-05-29 | Substituierte 2-Naphthoylguanidine, Verfahren zur ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU97109003A RU97109003A (ru) | 1999-04-27 |
| RU2190600C2 true RU2190600C2 (ru) | 2002-10-10 |
Family
ID=7795549
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU97109003/04A RU2190600C2 (ru) | 1996-05-29 | 1997-05-28 | Замещенные 2-нафтоилгуанидины и лекарственное средство на их основе |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6087304A (enExample) |
| EP (1) | EP0810206B1 (enExample) |
| JP (1) | JP4039588B2 (enExample) |
| KR (1) | KR970074776A (enExample) |
| CN (1) | CN1167759A (enExample) |
| AR (1) | AR008373A1 (enExample) |
| AT (1) | ATE198320T1 (enExample) |
| AU (1) | AU710065B2 (enExample) |
| BR (1) | BR9703338A (enExample) |
| CA (1) | CA2206366C (enExample) |
| CZ (1) | CZ163097A3 (enExample) |
| DE (2) | DE19621483A1 (enExample) |
| DK (1) | DK0810206T3 (enExample) |
| ES (1) | ES2154002T3 (enExample) |
| GR (1) | GR3035126T3 (enExample) |
| HR (1) | HRP970292B1 (enExample) |
| HU (1) | HUP9700955A3 (enExample) |
| ID (1) | ID16989A (enExample) |
| IL (1) | IL120924A (enExample) |
| NO (1) | NO308527B1 (enExample) |
| NZ (1) | NZ314915A (enExample) |
| PL (1) | PL185754B1 (enExample) |
| PT (1) | PT810206E (enExample) |
| RU (1) | RU2190600C2 (enExample) |
| SI (1) | SI0810206T1 (enExample) |
| SK (1) | SK282020B6 (enExample) |
| TR (1) | TR199700428A2 (enExample) |
| TW (1) | TW416944B (enExample) |
| ZA (1) | ZA974665B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19621482A1 (de) | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 1-Naphthoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JP2002538151A (ja) | 1999-03-02 | 2002-11-12 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | カテプシンの可逆的インヒビターとして有用な化合物 |
| US6420364B1 (en) | 1999-09-13 | 2002-07-16 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compound useful as reversible inhibitors of cysteine proteases |
| AR039156A1 (es) * | 2002-03-28 | 2005-02-09 | Novartis Ag | Amidas del acido piperidinilamino sulfamico o piperazinil sulfamico y su uso para la manufactura de un medicamento en enfermedades mediadas por la accion de la sulfatasa esteroide |
| DK1755593T3 (da) * | 2004-06-02 | 2008-05-19 | Hoffmann La Roche | Naphtalenderivater der er nyttige som histamin-3-receptorligander |
| TW200614995A (en) * | 2004-11-10 | 2006-05-16 | Nicholas Piramal India Ltd | Tricyclic guanidine derivatives as sodium-proton exchange inhibitors |
| AU2013205388B2 (en) * | 2005-06-24 | 2016-05-05 | Biotron Limited | Antiviral compounds and methods |
| DK2826770T3 (en) * | 2005-06-24 | 2019-01-07 | Biotron Ltd | Acylguanidine compounds with antiviral activity |
| ATE478847T1 (de) * | 2006-09-15 | 2010-09-15 | Pfizer | Substituierte pyridylmethylbicyclocarboxyamidverbindungen |
| WO2010090305A1 (ja) * | 2009-02-09 | 2010-08-12 | アステラス製薬株式会社 | 置換アシルグアニジン誘導体 |
| EP2394987A4 (en) * | 2009-02-09 | 2012-09-05 | Astellas Pharma Inc | ACYLGUANIDINDERIVAT |
| TW201116281A (en) * | 2009-08-06 | 2011-05-16 | Astellas Pharma Inc | N atom containing ring acylguanidine derivatives |
| CN103339109B (zh) | 2011-02-02 | 2015-04-29 | 安斯泰来制药有限公司 | 四氢异喹啉衍生物 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4251545A (en) * | 1979-09-19 | 1981-02-17 | Gaf Corporation | Fungicidal process using 1-(alkoxyaroyl)guanidines |
| IT1238227B (it) * | 1989-12-01 | 1993-07-12 | Modulo di smistamento per impianti di convogliamento a nastro e simili | |
| DE4035961A1 (de) * | 1990-11-02 | 1992-05-07 | Thomae Gmbh Dr K | Cyclische iminoderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| IL109570A0 (en) * | 1993-05-17 | 1994-08-26 | Fujisawa Pharmaceutical Co | Guanidine derivatives, pharmaceutical compositions containing the same and processes for the preparation thereof |
| DE4415873A1 (de) * | 1994-05-05 | 1995-11-09 | Hoechst Ag | Substituierte bizyklische Heteroaroylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| JPH08225513A (ja) * | 1994-12-21 | 1996-09-03 | Kanebo Ltd | ナフトイルグアニジン誘導体 |
| DE19621482A1 (de) * | 1996-05-29 | 1997-12-04 | Hoechst Ag | Substituierte 1-Naphthoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
-
1996
- 1996-05-29 DE DE19621483A patent/DE19621483A1/de not_active Withdrawn
-
1997
- 1997-02-28 PL PL97318723A patent/PL185754B1/pl not_active IP Right Cessation
- 1997-05-16 SI SI9730102T patent/SI0810206T1/xx unknown
- 1997-05-16 DE DE59702802T patent/DE59702802D1/de not_active Expired - Lifetime
- 1997-05-16 EP EP97108013A patent/EP0810206B1/de not_active Expired - Lifetime
- 1997-05-16 DK DK97108013T patent/DK0810206T3/da active
- 1997-05-16 PT PT97108013T patent/PT810206E/pt unknown
- 1997-05-16 AT AT97108013T patent/ATE198320T1/de not_active IP Right Cessation
- 1997-05-16 US US08/857,631 patent/US6087304A/en not_active Expired - Lifetime
- 1997-05-16 ES ES97108013T patent/ES2154002T3/es not_active Expired - Lifetime
- 1997-05-27 SK SK670-97A patent/SK282020B6/sk unknown
- 1997-05-27 HR HR970292A patent/HRP970292B1/xx not_active IP Right Cessation
- 1997-05-27 TR TR97/00428A patent/TR199700428A2/xx unknown
- 1997-05-27 AR ARP970102253A patent/AR008373A1/es unknown
- 1997-05-27 HU HU9700955A patent/HUP9700955A3/hu unknown
- 1997-05-27 TW TW086107120A patent/TW416944B/zh not_active IP Right Cessation
- 1997-05-27 IL IL12092497A patent/IL120924A/en not_active IP Right Cessation
- 1997-05-27 AU AU23645/97A patent/AU710065B2/en not_active Ceased
- 1997-05-27 NZ NZ314915A patent/NZ314915A/en unknown
- 1997-05-27 CN CN97113187A patent/CN1167759A/zh active Pending
- 1997-05-27 CZ CZ971630A patent/CZ163097A3/cs unknown
- 1997-05-28 CA CA002206366A patent/CA2206366C/en not_active Expired - Fee Related
- 1997-05-28 RU RU97109003/04A patent/RU2190600C2/ru not_active IP Right Cessation
- 1997-05-28 NO NO972433A patent/NO308527B1/no not_active IP Right Cessation
- 1997-05-28 ID IDP971814A patent/ID16989A/id unknown
- 1997-05-28 JP JP13822797A patent/JP4039588B2/ja not_active Expired - Fee Related
- 1997-05-28 ZA ZA9704665A patent/ZA974665B/xx unknown
- 1997-05-28 KR KR1019970021107A patent/KR970074776A/ko not_active Ceased
- 1997-05-30 BR BR9703338A patent/BR9703338A/pt not_active IP Right Cessation
-
2000
- 2000-12-28 GR GR20000402772T patent/GR3035126T3/el not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20040529 |