KR960041154A - 플루오르 함유 벤조일구아니딘 유도체 - Google Patents
플루오르 함유 벤조일구아니딘 유도체 Download PDFInfo
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- KR960041154A KR960041154A KR1019960016096A KR19960016096A KR960041154A KR 960041154 A KR960041154 A KR 960041154A KR 1019960016096 A KR1019960016096 A KR 1019960016096A KR 19960016096 A KR19960016096 A KR 19960016096A KR 960041154 A KR960041154 A KR 960041154A
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- Prior art keywords
- general formula
- diaminomethylene
- compound
- physiologically acceptable
- trifluoromethylbenzamide
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- 229910052731 fluorine Inorganic materials 0.000 title claims 6
- AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical class NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 title claims 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title 1
- 239000011737 fluorine Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 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
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- ZPGGNWYEZUDURH-UHFFFAOYSA-N 2,4-dichloro-n-(diaminomethylidene)-5-(trifluoromethyl)benzamide Chemical compound NC(N)=NC(=O)C1=CC(C(F)(F)F)=C(Cl)C=C1Cl ZPGGNWYEZUDURH-UHFFFAOYSA-N 0.000 claims 1
- PNHHKAJKPVIHNZ-UHFFFAOYSA-N 4-bromo-n-(diaminomethylidene)-2,5-bis(trifluoromethyl)benzamide Chemical compound NC(N)=NC(=O)C1=CC(C(F)(F)F)=C(Br)C=C1C(F)(F)F PNHHKAJKPVIHNZ-UHFFFAOYSA-N 0.000 claims 1
- XNILGGNSCXXVGB-UHFFFAOYSA-N 4-bromo-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(Br)=C(C(F)(F)F)C=C1C(=O)N=C(N)N XNILGGNSCXXVGB-UHFFFAOYSA-N 0.000 claims 1
- MXCMNLNRFMEQPW-UHFFFAOYSA-N 4-chloro-n-(diaminomethylidene)-2-methyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(Cl)=C(C(F)(F)F)C=C1C(=O)N=C(N)N MXCMNLNRFMEQPW-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 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
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- -1 alkali metal cation Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000006793 arrhythmia Effects 0.000 claims 1
- 206010003119 arrhythmia Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000007574 infarction Effects 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- ZQSAQHGKLZBACJ-UHFFFAOYSA-N n-(diaminomethylidene)-2,4-dimethyl-5-(trifluoromethyl)benzamide Chemical compound CC1=CC(C)=C(C(F)(F)F)C=C1C(=O)N=C(N)N ZQSAQHGKLZBACJ-UHFFFAOYSA-N 0.000 claims 1
- XYEIQWWYUKARGX-UHFFFAOYSA-N n-(diaminomethylidene)-2-methyl-5-methylsulfonyl-4-(trifluoromethyl)benzamide Chemical compound CC1=CC(C(F)(F)F)=C(S(C)(=O)=O)C=C1C(=O)N=C(N)N XYEIQWWYUKARGX-UHFFFAOYSA-N 0.000 claims 1
- URBDIHSNGQFELA-UHFFFAOYSA-N n-(diaminomethylidene)-3-methylsulfonyl-4-(trifluoromethyl)benzamide Chemical compound CS(=O)(=O)C1=CC(C(=O)N=C(N)N)=CC=C1C(F)(F)F URBDIHSNGQFELA-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 229940121988 Antiporter inhibitor Drugs 0.000 abstract 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
- 230000003373 anti-fouling effect Effects 0.000 abstract 1
- 230000003834 intracellular effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (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)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
본 발명은 일반식(Ⅰ)의 헤테로시클릴옥시벤조일구아니딘
(단, 상기 식에서, R1, R2및 R3은 전기와 같은 의미이다.) 및 이의 생리학적으로 허용가능한 염에 관한 것으로, 본 발명의 화합물은 항부정맥 효과를 나타내며, 세포내 Na+/H+대향수송계(antiporter) 억제제로 작용한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (8)
- 일반식(Ⅰ)의 플루오르 함유 벤조일구아니딘 유도체 및 이의 생리학적으로 허용가능한 염.〔단, 상기 식에서, R1은 H, F, Cl, Br, I, A, CN, NO2, CnFmH2n+1-mOp, 탄소원자수 2 내지 4인 알키닐 또는 －X－R4이고, R2는 CnFmH2n+1-mOp이고, R3은 H, A, F, Cl, Br, I, CnFmH2n+1-mOp, SOq－R6, SO2NR4R5, Het, OR6, SR6, S－Het 또는 NR7－Het이고, R4및 R5는 각기 상호 독립적으로 H 또는 A거나, 또는 함께 탄소수 4 내지 5인 알킬렌(CH2기는 O, S, NH 또는 NA로 치환될 수도 있다)을 형성하고, R6는 Ph 또는 A이고, R7는 H 또는 A이고, A는 탄소원자수 1 내지 6인 알킬이고, X는 O, S 또는 NR7이고, Ph는 치환되지 않거나, A, OA, NR4R5, F, Cl, Br, I 또는 CnFmH2n+1-mOp로 일－, 이－ 또는 삼치환된 페닐이고, Het는 N, O 및/또는 S 원자수 1 내지 4인 일－ 또는 이핵의 포화, 불포화 또는 방향족 헤테로고리 라디칼(이들은 치환되지 않거나 F, Cl, Br, CnFmH2n+1-mOp, A, X－R4, NO2, CN 및/또는 카르보닐산소로 일－, 이－, 삼치환될 수 있다)이고, N 또는 C를 거쳐 벤조일계에 결합되며, m은 1,2,3,4,5,6 또는 7로, 2n+1 이하이고, n은 1,2 또는 3이고, p는 0 또는 1이고, q는 1 또는 2이다. 단, R3가 SOq－R6또는 SO2NR4R5인 경우, R1은 H이다.〕
- 제1항에 따른 하기 화합물 및 이의 생리학적으로 허용가능한 염. a) N－디아미노메틸렌－2－메틸－4－트리플루오로메틸－5－메틸술포닐－벤즈아미드; b) N－디아미노메틸렌－3－메틸술포닐－4－트리플루오로메틸벤즈아미드; c) N－디아미노메틸렌－2－메틸－4－브로모－5－트리플루오로메틸벤즈아미드; d) N－디아미노메틸렌－2,5－비스(트리플루오로메틸)－4－브로모벤즈아미드; e) N－디아미노메틸렌－2,4디클로로－5－트리플루오로메틸벤즈아미드 f) N－디아미노메틸렌－2－메틸－4－클로로－5－트리플루오로메틸벤즈아미드; g) N－디아미노메틸렌－2,4－디메틸－5－트리플루오로메틸벤즈아미드.
- 하기 일반식(Ⅱ)의 화합물(단, 상기 식에서, R1, R2및 R3는 전기에서 정의된 바와 같은 의미이고, Q는 F, Cl, Br, OA, O－CO－A, O－CO－Ph, OH 또는 기타의 에스테르화된 반응성 OH기 또는 친핵적으로 쉽게 치환될 수 있는 이탈기이다.)을 구아니딘과 반응시키거나; 하기 일반식(Ⅲ)의 벤조일구아니딘(단, 상기 식에서, R1및 R3는 전기에서 정의된 바와 같은 의미이고, R6는 Br, Cl, F, I 또는 기타의 친핵적으로 치환될 수 있는 기이다.)을 하기 일반식(Ⅳ)의 화합물CnFmH2n+1-mOp－L (Ⅳ)(단, 상기 식에서, n, m 및 p는 전기에서 정의된 바와 같은 의미이고, L은 H, (CH3)3－Si, CO2K 또는 CO2Na, 알칼리 금속 양이온, NH4 +, Ag+또는 Cu+이다.)과 반응시키거나; 일반식(Ⅰ)에 상응하되, 하나 이상의 수소 원자를 대신하여 하나 이상의 환원성기 및/또는 하나 이상의 추가의 C－C 및/또는 C－N 결합을 갖는 화합물을 환원제로 처리하거나; 일반식(Ⅰ)에 상응하되, 하나 이상의 수소 원자를 대신하여 하나 이상의 가용매분해성기를 갖는 화합물을 가용매분해제로 처리하거나; 및/또는 생성된 일반식(Ⅰ)의 염기를 산으로 처리함으로써 이의 염중 하나로 전환시키는 것을 특징으로 하는, 제1항에 따른 일반식(Ⅰ)의 플루오르함유 벤조일구아니딘 유도체와 이의 염의 제조방법.
- 제1항에 따른 일반식(Ⅰ)의 화합물 및/또는 이의 생리학적으로 허용가능한 염중 하나를 하나 이상의 고체, 액체 또는 반액체 부형제 또는 보조제와 함께 적당한 투여 형태로 만드는 것을 특징으로 하는 약제학적제형의 제조방법.
- 제1항에 따른 일반적인 일반식(Ⅰ)의 화합물 및/또는 이의 생리학적으로 허용가능한 염중 하나 이상을 함유하는 것을 특징으로 하는 약제학적 제형.
- 약물의 제조에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 또는 이의 생리학적으로 허용가능한 염.
- 질병의 제어에 사용되는 제1항에 따른 일반식(Ⅰ)의 화합물 또는 이의 생리학적으로 허용가능한 염.
- 부정맥, 협심증, 경색의 치료 및 예방용 약물제조에 사용되는, 제1항에 따른 일반식(Ⅰ)의 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19517848.3 | 1995-05-16 | ||
| DE19517848A DE19517848A1 (de) | 1995-05-16 | 1995-05-16 | Fluorhaltige Benzoylguanidine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR960041154A true KR960041154A (ko) | 1996-12-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960016096A KR960041154A (ko) | 1995-05-16 | 1996-05-15 | 플루오르 함유 벤조일구아니딘 유도체 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5747539A (ko) |
| EP (1) | EP0743301B1 (ko) |
| JP (1) | JPH08311011A (ko) |
| KR (1) | KR960041154A (ko) |
| CN (1) | CN1064955C (ko) |
| AT (1) | ATE204856T1 (ko) |
| AU (1) | AU713743B2 (ko) |
| CA (1) | CA2176553A1 (ko) |
| CZ (1) | CZ287750B6 (ko) |
| DE (2) | DE19517848A1 (ko) |
| DK (1) | DK0743301T3 (ko) |
| ES (1) | ES2161936T3 (ko) |
| GR (1) | GR3037033T3 (ko) |
| HU (1) | HU223046B1 (ko) |
| NO (1) | NO306157B1 (ko) |
| PL (1) | PL184192B1 (ko) |
| PT (1) | PT743301E (ko) |
| RU (1) | RU2159230C2 (ko) |
| SI (1) | SI0743301T1 (ko) |
| SK (1) | SK282052B6 (ko) |
| TW (1) | TW363052B (ko) |
| UA (1) | UA44260C2 (ko) |
| ZA (1) | ZA963870B (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 |
| DE19606509A1 (de) * | 1996-02-22 | 1997-08-28 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE19608161A1 (de) * | 1996-03-04 | 1997-09-11 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US5747639A (en) * | 1996-03-06 | 1998-05-05 | Amgen Boulder Inc. | Use of hydrophobic interaction chromatography to purify polyethylene glycols |
| DE19713427A1 (de) * | 1997-04-01 | 1998-10-08 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| WO2000030624A2 (en) * | 1998-11-26 | 2000-06-02 | Merck Patent Gmbh | Use of benzoylguanidines for the treatment of non-insulin-dependent diabetes mellitus |
| US7375138B2 (en) * | 2002-05-18 | 2008-05-20 | Sanofi-Aventis Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, processes for their preparation, their use as medicaments or diagnostic aids, and medicaments comprising them |
| DE10222192A1 (de) * | 2002-05-18 | 2003-11-27 | Aventis Pharma Gmbh | Pentafluorsulfuranyl-benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| US20050124666A1 (en) * | 2003-11-13 | 2005-06-09 | Aventis Pharma Deutschland Gmbh | Pentafluorosulfanylbenzoylguanidines, process for their preparation, use as a medicament or diagnostic aid, and medicament comprising same |
| DE10353204A1 (de) * | 2003-11-13 | 2005-06-16 | Aventis Pharma Deutschland Gmbh | Verfahren zur Herstellung von 4-Pentafluorsulfanyl-benzoylguanidinen |
| OA13285A (en) * | 2003-11-13 | 2007-01-31 | Sanofi Aventis Deutschland | Pentafluorosulfanyl benzoylguanidines, method for their production, their use as medicaments or diagnostic agents and medicament containing the same. |
Family Cites Families (10)
| 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 |
| EP0556673B1 (de) * | 1992-02-15 | 1997-09-17 | Hoechst Aktiengesellschaft | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE59302959D1 (de) * | 1992-02-15 | 1996-07-25 | Hoechst Ag | 3,5-Substituierte Benzoylguanidine, mit antiarrythmischer Wirkung und inhibierender Wirkung auf die Proliferationen von Zellen |
| ES2097409T3 (es) * | 1992-09-22 | 1997-04-01 | Hoechst Ag | Benzoilguanidinas, procedimiento para su preparacion, asi como su empleo como antiarritmicos. |
| TW250477B (ko) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| TW250479B (ko) * | 1992-12-15 | 1995-07-01 | Hoechst Ag | |
| DE4318756A1 (de) * | 1993-06-05 | 1994-12-08 | Hoechst Ag | Substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4328869A1 (de) * | 1993-08-27 | 1995-03-02 | Hoechst Ag | Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4417004A1 (de) * | 1994-05-13 | 1995-11-16 | Hoechst Ag | Perfluoralkyl-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| DE4430916A1 (de) * | 1994-08-31 | 1996-03-07 | Merck Patent Gmbh | Alkyl-benzoylguanidin-Derivate |
-
1995
- 1995-05-16 DE DE19517848A patent/DE19517848A1/de not_active Withdrawn
-
1996
- 1996-03-25 TW TW085103561A patent/TW363052B/zh active
- 1996-05-02 PT PT96106881T patent/PT743301E/pt unknown
- 1996-05-02 DK DK96106881T patent/DK0743301T3/da active
- 1996-05-02 EP EP96106881A patent/EP0743301B1/de not_active Expired - Lifetime
- 1996-05-02 DE DE59607559T patent/DE59607559D1/de not_active Expired - Fee Related
- 1996-05-02 ES ES96106881T patent/ES2161936T3/es not_active Expired - Lifetime
- 1996-05-02 AT AT96106881T patent/ATE204856T1/de not_active IP Right Cessation
- 1996-05-02 SI SI9630361T patent/SI0743301T1/xx unknown
- 1996-05-09 SK SK590-96A patent/SK282052B6/sk unknown
- 1996-05-13 AU AU52252/96A patent/AU713743B2/en not_active Ceased
- 1996-05-13 UA UA96051860A patent/UA44260C2/uk unknown
- 1996-05-13 CN CN961058854A patent/CN1064955C/zh not_active Expired - Fee Related
- 1996-05-14 CA CA002176553A patent/CA2176553A1/en not_active Abandoned
- 1996-05-15 RU RU96109204/04A patent/RU2159230C2/ru not_active IP Right Cessation
- 1996-05-15 ZA ZA963870A patent/ZA963870B/xx unknown
- 1996-05-15 NO NO961997A patent/NO306157B1/no not_active IP Right Cessation
- 1996-05-15 PL PL96314259A patent/PL184192B1/pl unknown
- 1996-05-15 CZ CZ19961408A patent/CZ287750B6/cs not_active IP Right Cessation
- 1996-05-15 KR KR1019960016096A patent/KR960041154A/ko active IP Right Grant
- 1996-05-15 HU HU9601305A patent/HU223046B1/hu not_active IP Right Cessation
- 1996-05-15 US US08/647,789 patent/US5747539A/en not_active Expired - Fee Related
- 1996-05-16 JP JP8144881A patent/JPH08311011A/ja active Pending
-
2001
- 2001-10-30 GR GR20010401903T patent/GR3037033T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1064955C (zh) | 2001-04-25 |
| RU2159230C2 (ru) | 2000-11-20 |
| EP0743301A2 (de) | 1996-11-20 |
| UA44260C2 (uk) | 2002-02-15 |
| ZA963870B (en) | 1996-11-21 |
| NO306157B1 (no) | 1999-09-27 |
| DE19517848A1 (de) | 1996-11-21 |
| DE59607559D1 (de) | 2001-10-04 |
| GR3037033T3 (en) | 2002-01-31 |
| NO961997L (no) | 1996-11-18 |
| AU713743B2 (en) | 1999-12-09 |
| ATE204856T1 (de) | 2001-09-15 |
| CZ140896A3 (en) | 1997-02-12 |
| HUP9601305A3 (en) | 1997-11-28 |
| EP0743301A3 (de) | 1997-06-11 |
| SK59096A3 (en) | 1996-12-04 |
| HU223046B1 (hu) | 2004-03-01 |
| CN1143632A (zh) | 1997-02-26 |
| CZ287750B6 (en) | 2001-01-17 |
| SI0743301T1 (en) | 2002-02-28 |
| SK282052B6 (sk) | 2001-10-08 |
| CA2176553A1 (en) | 1996-11-17 |
| PL184192B1 (pl) | 2002-09-30 |
| US5747539A (en) | 1998-05-05 |
| JPH08311011A (ja) | 1996-11-26 |
| EP0743301B1 (de) | 2001-08-29 |
| ES2161936T3 (es) | 2001-12-16 |
| DK0743301T3 (da) | 2001-11-26 |
| TW363052B (en) | 1999-07-01 |
| NO961997D0 (no) | 1996-05-15 |
| AU5225296A (en) | 1996-11-28 |
| HUP9601305A2 (en) | 1997-05-28 |
| PL314259A1 (en) | 1996-11-25 |
| PT743301E (pt) | 2002-01-30 |
| HU9601305D0 (en) | 1996-07-29 |
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