KR960007540A - 아릴벤조일구아니딘 유도체 - Google Patents
아릴벤조일구아니딘 유도체 Download PDFInfo
- Publication number
- KR960007540A KR960007540A KR1019950026799A KR19950026799A KR960007540A KR 960007540 A KR960007540 A KR 960007540A KR 1019950026799 A KR1019950026799 A KR 1019950026799A KR 19950026799 A KR19950026799 A KR 19950026799A KR 960007540 A KR960007540 A KR 960007540A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- carbon atoms
- compound
- diaminomethylene
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 125000002947 alkylene group Chemical group 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 4
- -1 biphenylyl Chemical group 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims abstract 2
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 238000011282 treatment Methods 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 206010061216 Infarction Diseases 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 150000007514 bases Chemical class 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- FJOOYRCQANEWMT-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-3-methylsulfonyl-4-phenylbenzamide Chemical compound CCC1=C(C(=O)N=C(N)N)C=CC(C=2C=CC=CC=2)=C1S(C)(=O)=O FJOOYRCQANEWMT-UHFFFAOYSA-N 0.000 claims 1
- RCKAWQCNULZGJE-UHFFFAOYSA-N n-(diaminomethylidene)-2-ethyl-4-(4-methylphenyl)-5-methylsulfonylbenzamide Chemical compound C1=C(C(=O)N=C(N)N)C(CC)=CC(C=2C=CC(C)=CC=2)=C1S(C)(=O)=O RCKAWQCNULZGJE-UHFFFAOYSA-N 0.000 claims 1
- XQYPJPSITWOGIY-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-4-(4-methylphenyl)-5-methylsulfonylbenzamide Chemical compound C1=CC(C)=CC=C1C1=CC(C)=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O XQYPJPSITWOGIY-UHFFFAOYSA-N 0.000 claims 1
- GGSMVRMJSSOOLO-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-(4-phenylphenyl)benzamide Chemical compound C1=C(C(=O)N=C(N)N)C(C)=CC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=C1S(C)(=O)=O GGSMVRMJSSOOLO-UHFFFAOYSA-N 0.000 claims 1
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 230000003834 intracellular effect Effects 0.000 abstract 1
Classifications
-
- 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
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C317/50—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
-
- 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
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Electroluminescent Light Sources (AREA)
- Photoreceptors In Electrophotography (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
본 발명은 하기 일반식(I)로 표시되는 아릴벤조일구아니딘 유도체 및 이의 생리학적으로 허요되는 염을 제공한다.
(단, 상기 식에서, R1은 A, CF3, CH2F, CHF2, C2F5, CN, NO2, Hal, C≡C 또는 -X-R4이고, R2및 R3는 H, Hal, A, -X-R4, CN, NO2, CF3, CH2F, CHF2, C2F5, CH2CF3, -SOn-R6, -SO2NR4R5, Ph 또는 OPh이며, R4는 H, A, 탄소수가 5~7인 시클로알킬, 탄소수가 6~8인 시클로알킬메틸, CF3, CH2F, CHF2, CH2CF3, Ph 또는 -CH2-Ph이고, R5는 H 또는 A이거나, 또는 R4및 R5는 함께 결합하여 탄소수가 4~5인 알킬렌이고, 여기에서 상기 알킬렌중의 하나의 CH2기는 O, S, NH, N-A 또는 N-CH2-Ph 로 대체할 수 있는 기이며, R6는 A 또는 Ph이고, A는 탄소수가 1~6인 알킬이며, X는 O, S 또는 NR5이고, Ph는 A, OA, NR4R5, F, Cl, Br, I 또는 CF3로 1회, 2회 또는 3회 치환되거나 또는 비치환된 페닐, 나프틸 또는 비페닐일이며, n은 1 또는 2이고, Hal은 F, Cl, Br 또는 I이다.) 본 발명의 화합물은 세포내 Na+/H+상호수송기의 억제제로서 작용하고 항부정맥 특성을 나타낸다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 일반식(I)로 표시되는 아릴벤조일구아니딘 유도체 및 이들의 생리학적으로 허용되는 염.(단, 상기 식에서, R1은 A, CF3, CH2F, CHF2, C2F5, CN, NO2, Hal, C≡C 또는 -X-R4이고, R2및 R3는 각기 독립적으로, H, Hal, A, -X-R4, CN, NO2, CF3, CH2F, CHF2, C2F5, CH2CF3, -SOn-R6, -SO2NR4R5, Ph 또는 OPh이며, R4는 H, A, 탄소수가 5~7인 시클로알킬, 탄소수가 6~8인 시클로알킬메틸, CF3, CH2F, CHF2, CH2CF3, Ph 또는 -CH2-Ph이고, R5는 H 또는 A이거나, 또는 R4및 R5는 함께 결합하여 탄소수가 4~5인 알킬렌이고, 여기에서 상기 알킬렌중의 하나의 CH2기는 O, S, NH, N-A 또는 N-CH2-Ph 로 대체할 수 있는 기이며, R6는 A 또는 Ph이고, A는 탄소수가 1~6인 알킬이며, X는 O, S 또는 NR5이고, Ph는 A, OA, NR4R5, F, Cl, Br, I 또는 CF3로 1회, 2회 또는 3회 치환되거나 또는 비치환된 페닐, 나프틸 또는 비페닐일이며, n은 1 또는 2이고, Hal은 F, Cl, Br 또는 I이다.)
- (a) N-디아미노메틸렌-2-메틸-4-(4-메틸페닐)-5-메틸술포닐벤즈아미드, (b) N-디아미노메틸렌-2-에틸-4-(4-메틸페닐)-5-메틸술포닐벤즈아미드, (c) N-디아미노메틸렌-2-메틸-3-메틸술포닐-4-(2-메틸페닐)벤즈아미드, (d) N-디아미노메틸렌-2-에틸-3-메틸술포닐-4-페닐벤즈아미드, (e) N-디아미노메틸렌-2-메틸-4-(4-비페닐일)-5-메틸술포닐벤즈아미드, (f) N-디아미노메틸렌-2-에틸-4-(2-나프틸)-5-메틸술포닐벤즈아미드.
- 제1항에 따른 일반식(I)의 표시되는 아릴벤조일구아니딘 유도체 및 이들의 염중 하나를 제조하는 방법에 있어서, 하기 일반식(Ⅱ)로 표시되는 화합물을 구아니딘과 반응시키거나, 또는 하기 일반식(Ⅲ)으로 표시되는 벤조일구아니딘을 하기 일반식(Ⅳ)로 표시되는 화합물과 반응시키거나, 또는 하나 이상의 수소원자 대신에 하나 이상의 환원성 기 및/또는 하나 이상의 추가의 C-C 및/또는 C-N 결합을 갖지만 그 밖에는 일반식(I)과 일치하는 화합물을 환원제로 처리하거나, 또는 하나 이상의 수소원자 대신에 하나 이상의 가용매분해성기를 갖지만 그밖에는 일반식(I)과 일치하는 화합물을 가용매분해제로 처리하거나 및/또는 생성된 일반식(I)의 염기성 화합물을 산으로 처리함으로써 이의 염중의 하나로 전환시키는 것을 특징으로 하는 제조방법.(단, 상기 식에서, R1, R2, R3및 Ph는 상기에서 정의된 바와 같고, Q는 Cl, Br, OA, O-CO-A, O-CO-Ph 또는 OH 또는 기타 반응적으로 에스테르화된 OH기 또는 친핵적으로 쉽게 치환될 수 있는 이탈기이고, R7은 Cl, Br, I 또는 O-SO2-R8이며, R8은 A, Ph 또는 CF3이고, R9는 각기 H, A이거나 함께 결합하여 탄소수가 2 내지 4인 알킬렌이다.)
- 제1항에 따른 일반식(I)로 표시되는 화합물 및/또는 이의 생리학적으로 허용되는 염중의 하나를 1종이상의 고체, 액체 또는 반고체 담체물질 또는 보조물질과 함께 적합한 투여형태로 만드는 것을 특징으로 하는 약제학적 제형의 제조방법.
- 제1항에 따른 일반식(I)로 표시되는 화합물 1종 이상 및/또는 이의 생리학적으로 허용되는 염중의 하나를 함유하는 것을 특징으로 하는 약제학적 제형.
- 제1항에 따른 일반식(I)로 표시되는 화합물 또는 이의 생리학적으로 허용되는 염을 질병의 치료를 위한 약물제조에 사용하는 용도.
- 제1항에 따른 일반식(I)로 표시되는 화합물 또는 이의 생리학적으로 허용되는 염을 질병의 치료에 사용하는 용도.
- 제1항에 따른 일반식(I)로 표시되는 화합물을 부정맥증, 협심증 및 경색증의 치료, 또는 상기 질병의 예방치료용 약물의 제조에 사용하는 용도.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4430213.4 | 1994-08-28 | ||
| DE4430213A DE4430213A1 (de) | 1994-08-28 | 1994-08-28 | Arylbenzoylguanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960007540A true KR960007540A (ko) | 1996-03-22 |
Family
ID=6526570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019950026799A KR960007540A (ko) | 1994-08-28 | 1995-08-28 | 아릴벤조일구아니딘 유도체 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US5807896A (ko) |
| EP (1) | EP0699660B1 (ko) |
| JP (1) | JPH0859598A (ko) |
| KR (1) | KR960007540A (ko) |
| CN (1) | CN1055919C (ko) |
| AT (1) | ATE172716T1 (ko) |
| AU (1) | AU704630B2 (ko) |
| BR (1) | BR9503810A (ko) |
| CA (1) | CA2156960A1 (ko) |
| CZ (1) | CZ289058B6 (ko) |
| DE (2) | DE4430213A1 (ko) |
| ES (1) | ES2125537T3 (ko) |
| HU (1) | HU216833B (ko) |
| NO (1) | NO305242B1 (ko) |
| PL (1) | PL180872B1 (ko) |
| RU (1) | RU2153490C2 (ko) |
| SK (1) | SK281135B6 (ko) |
| TW (1) | TW386988B (ko) |
| UA (1) | UA44237C2 (ko) |
| ZA (1) | ZA957163B (ko) |
Families Citing this family (11)
| 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 |
| NZ314105A (en) * | 1996-02-02 | 1997-12-19 | Sumitomo Pharma | Guanidine derivative substituted with a substituted indole which is peri condensed with a heterocyclic ring |
| DE19608161A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19624178A1 (de) * | 1996-06-18 | 1998-01-08 | Hoechst Ag | Ortho-substituierte 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 |
| GB0225548D0 (en) * | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| US7365070B2 (en) * | 2002-12-04 | 2008-04-29 | Ore Pharmaceuticals Inc. | Modulators of melanocortin receptor |
| GB0323584D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Compounds |
| GB0323585D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Compounds |
| GB0323581D0 (en) * | 2003-10-08 | 2003-11-12 | Glaxo Group Ltd | Novel compounds |
| GB0410121D0 (en) * | 2004-05-06 | 2004-06-09 | Glaxo Group Ltd | Compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3420874A (en) * | 1962-09-28 | 1969-01-07 | Standard Oil Co | Amine addition salts of nitro-carboxyalkali metal phenolates |
| ES2108144T3 (es) * | 1992-02-15 | 1997-12-16 | Hoechst Ag | Benzoilguanidinas sustituidas en orto, procedimiento para su preparacion, su utilizacion como medicamento o agente de diagnostico, asi como medicamento que las contiene. |
| CZ284456B6 (cs) * | 1992-02-15 | 1998-12-16 | Hoechst Aktiengesellschaft | Aminosubstituované benzoylguanidiny, způsob jejich přípravy, jejich použití jako léčiv a léčivo, které je obsahuje |
| DK0577024T3 (ko) * | 1992-07-01 | 1997-02-24 | Hoechst Ag | |
| DE59306029D1 (de) * | 1992-12-16 | 1997-05-07 | Hoechst Ag | 3,5-Substituierte Aminobenzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| 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 |
| 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 |
-
1994
- 1994-08-28 DE DE4430213A patent/DE4430213A1/de not_active Withdrawn
-
1995
- 1995-07-21 TW TW084107589A patent/TW386988B/zh active
- 1995-08-21 ES ES95113105T patent/ES2125537T3/es not_active Expired - Lifetime
- 1995-08-21 AT AT95113105T patent/ATE172716T1/de not_active IP Right Cessation
- 1995-08-21 AU AU30144/95A patent/AU704630B2/en not_active Ceased
- 1995-08-21 DE DE59504053T patent/DE59504053D1/de not_active Expired - Fee Related
- 1995-08-21 EP EP95113105A patent/EP0699660B1/de not_active Expired - Lifetime
- 1995-08-23 UA UA95083913A patent/UA44237C2/uk unknown
- 1995-08-25 CA CA002156960A patent/CA2156960A1/en not_active Abandoned
- 1995-08-25 RU RU95114440/04A patent/RU2153490C2/ru not_active IP Right Cessation
- 1995-08-25 PL PL95310193A patent/PL180872B1/pl not_active IP Right Cessation
- 1995-08-25 CN CN95116621A patent/CN1055919C/zh not_active Expired - Fee Related
- 1995-08-25 US US08/519,182 patent/US5807896A/en not_active Expired - Fee Related
- 1995-08-25 NO NO953351A patent/NO305242B1/no not_active IP Right Cessation
- 1995-08-25 ZA ZA957163A patent/ZA957163B/xx unknown
- 1995-08-25 CZ CZ19952182A patent/CZ289058B6/cs not_active IP Right Cessation
- 1995-08-25 SK SK1053-95A patent/SK281135B6/sk unknown
- 1995-08-25 BR BR9503810A patent/BR9503810A/pt not_active Application Discontinuation
- 1995-08-28 JP JP7240499A patent/JPH0859598A/ja active Pending
- 1995-08-28 HU HU9502516A patent/HU216833B/hu not_active IP Right Cessation
- 1995-08-28 KR KR1019950026799A patent/KR960007540A/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| SK281135B6 (sk) | 2000-12-11 |
| CZ218295A3 (en) | 1996-03-13 |
| UA44237C2 (uk) | 2002-02-15 |
| BR9503810A (pt) | 1996-04-16 |
| PL180872B1 (pl) | 2001-04-30 |
| HU9502516D0 (en) | 1995-10-30 |
| DE4430213A1 (de) | 1996-02-29 |
| CZ289058B6 (cs) | 2001-10-17 |
| HU216833B (hu) | 1999-09-28 |
| EP0699660B1 (de) | 1998-10-28 |
| US5807896A (en) | 1998-09-15 |
| HUT72303A (en) | 1996-04-29 |
| JPH0859598A (ja) | 1996-03-05 |
| RU2153490C2 (ru) | 2000-07-27 |
| TW386988B (en) | 2000-04-11 |
| ATE172716T1 (de) | 1998-11-15 |
| NO953351D0 (no) | 1995-08-25 |
| SK105395A3 (en) | 1996-03-06 |
| ES2125537T3 (es) | 1999-03-01 |
| CN1117962A (zh) | 1996-03-06 |
| CA2156960A1 (en) | 1996-03-01 |
| NO305242B1 (no) | 1999-04-26 |
| EP0699660A3 (ko) | 1996-03-20 |
| AU704630B2 (en) | 1999-04-29 |
| ZA957163B (en) | 1996-04-17 |
| PL310193A1 (en) | 1996-03-04 |
| DE59504053D1 (de) | 1998-12-03 |
| AU3014495A (en) | 1996-03-14 |
| EP0699660A2 (de) | 1996-03-06 |
| CN1055919C (zh) | 2000-08-30 |
| NO953351L (no) | 1996-02-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR960034164A (ko) | 스틸벤 유도체 및 이를 함유하는 약제학적 조성물 | |
| KR960007540A (ko) | 아릴벤조일구아니딘 유도체 | |
| KR950321212A (ko) | 4-아미노-1-피페리딜벤조일구아니딘 | |
| ES539658A0 (es) | Procedimiento de preparacion de nuevos derivados de la xan- tina y de sus sales de adicion con acidos apropiados | |
| CA2149285A1 (en) | Perfluoroalkyl-substituted benzoylguanidines, a process for their preparation, their use as a medicament or diagnostic agent, and a medicament containing them | |
| KR840007596A (ko) | 유기인 유도체의염의 제조방법 | |
| FR2800735B1 (fr) | Nouvelles aralkyle-1,2-diamines possedant une activite calcimimetique et leur mode de preparation | |
| KR890005035A (ko) | 벤조일아미노페녹시부탄산 유도체와 그의 제조방법 및 이를 포함하는 제약조성물 | |
| CA2221110A1 (en) | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents for the treatment of ocular hypertension | |
| KR960022542A (ko) | 광학 활성 벤조티에핀 유도체, 그의 제조방법 및 용도 | |
| JPS646243A (en) | Glycerin derivative | |
| ES551274A0 (es) | Un procedimiento para la sintesis de derivados de imidazol. | |
| BR9503536A (pt) | Composto processo para sua preparação seu uso e composição farmacêutica | |
| RU2218334C2 (ru) | Замещенные 1,2,3,4,5,6-гексагидро-2,6-метано-3-бензазоцин-10-олы и фармацевтическая композиция на их основе | |
| RU96115459A (ru) | Производные 4-сульфонил-или 4-сульфинил-бензоилгуанидина | |
| KR910000711A (ko) | 크로만 유도체 | |
| ES528561A0 (es) | Un procedimiento para la preparacion de compuestos nitro alifaticos | |
| CA2140989A1 (en) | Phenyl-substituted alkylcarboguanidides carrying perfluoroalkyl groups, a process for their preparation, their use as a medicament or diagnosticagent, and a medicament containing them | |
| KR960007538A (ko) | 알킬벤조일구아니딘 유도체 | |
| KR960029319A (ko) | 4-아미노벤조일구아니딘 유도체 | |
| KR890001965A (ko) | 스퍼구알린 관련 유도체 | |
| RU95114440A (ru) | Арил-бензоил-гуанидины, способ их получения, фармацевтическая композиция, способ ее получения | |
| KR900011724A (ko) | 특정 피롤릴페닐-치환된 하이드록삼산 유도체 | |
| ES2039719T3 (es) | Procedimiento para preparar un agente terapeutico para el tratamiento de la enfermedad de ulcera peptica. | |
| KR950011408A (ko) | 사이클릭 아민 유도체 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| NORF | Unpaid initial registration fee |