KR860004029A - 이미다졸리움 염의 제조방법 - Google Patents
이미다졸리움 염의 제조방법 Download PDFInfo
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- KR860004029A KR860004029A KR1019850008349A KR850008349A KR860004029A KR 860004029 A KR860004029 A KR 860004029A KR 1019850008349 A KR1019850008349 A KR 1019850008349A KR 850008349 A KR850008349 A KR 850008349A KR 860004029 A KR860004029 A KR 860004029A
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- Prior art keywords
- methyl
- alkyl
- oxoethyl
- compound
- hydrogen
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- 238000004519 manufacturing process Methods 0.000 title claims 4
- 150000004693 imidazolium salts Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 21
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 6
- ASCIQIVNWKGROC-UHFFFAOYSA-N 1-(3-methoxyphenyl)-2-(3-methyl-1,2-dihydroimidazol-1-ium-1-yl)ethanone;bromide Chemical compound [Br-].COC1=CC=CC(C(=O)CN2C=C[NH+](C)C2)=C1 ASCIQIVNWKGROC-UHFFFAOYSA-N 0.000 claims 3
- ZTDPHAKYABZYBA-UHFFFAOYSA-N 1-(4-ethylphenyl)-2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)ethanone;bromide Chemical compound [Br-].C1=CC(CC)=CC=C1C(=O)CN1C=C[NH+](C)C1 ZTDPHAKYABZYBA-UHFFFAOYSA-N 0.000 claims 3
- XWTCJZBQURWTIB-UHFFFAOYSA-N 2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)-1-(3-methylphenyl)ethanone;bromide Chemical compound [Br-].C1=C[NH+](C)CN1CC(=O)C1=CC=CC(C)=C1 XWTCJZBQURWTIB-UHFFFAOYSA-N 0.000 claims 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 3
- 241000124008 Mammalia Species 0.000 claims 3
- 150000001450 anions Chemical class 0.000 claims 3
- 239000008280 blood Substances 0.000 claims 3
- 210000004369 blood Anatomy 0.000 claims 3
- 239000008103 glucose Substances 0.000 claims 3
- -1 phenacyl compound Chemical class 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- JSWBXVABBYOEOK-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)-2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)ethanone;bromide Chemical compound [Br-].C1=C[NH+](C)CN1CC(=O)C1=CC=C(C)C=C1C JSWBXVABBYOEOK-UHFFFAOYSA-N 0.000 claims 2
- JXYXHKUEFAMLCI-UHFFFAOYSA-N 1-(2,5-dimethoxyphenyl)-2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)ethanone;bromide Chemical compound [Br-].COC1=CC=C(OC)C(C(=O)CN2C=C[NH+](C)C2)=C1 JXYXHKUEFAMLCI-UHFFFAOYSA-N 0.000 claims 2
- RGUWRHYLMIWJDM-UHFFFAOYSA-N 1-(3-ethoxyphenyl)-2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)ethanone;bromide Chemical compound [Br-].CCOC1=CC=CC(C(=O)CN2C=C[NH+](C)C2)=C1 RGUWRHYLMIWJDM-UHFFFAOYSA-N 0.000 claims 2
- CONDXQDYTMAGTI-UHFFFAOYSA-N 2-(1-methyl-1,2-dihydroimidazol-1-ium-3-yl)-1-(2-methylphenyl)ethanone;bromide Chemical compound [Br-].C1=C[NH+](C)CN1CC(=O)C1=CC=CC=C1C CONDXQDYTMAGTI-UHFFFAOYSA-N 0.000 claims 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- SXFHGNOMYIJTOX-UHFFFAOYSA-M 2-(3-methylimidazol-3-ium-1-yl)-1-(4-methylphenyl)ethanone;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C(=O)C[N+]1=CN(C)C=C1 SXFHGNOMYIJTOX-UHFFFAOYSA-M 0.000 claims 1
- CVJNXVLQSKPUGP-UHFFFAOYSA-N 2-imidazol-1-yl-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)CN1C=CN=C1 CVJNXVLQSKPUGP-UHFFFAOYSA-N 0.000 claims 1
- IDAKXTKYNYKPIQ-UHFFFAOYSA-N [Br-].C(C)[NH+]1CN(C=C1)CC(=O)C1=C(C=CC=C1)C Chemical compound [Br-].C(C)[NH+]1CN(C=C1)CC(=O)C1=C(C=CC=C1)C IDAKXTKYNYKPIQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (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)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (15)
- 일반식(Ⅲ)의 1-알킬-이미다졸을 일반식 (Ⅳ)의 펜아실 화합물과 반응시키거나 ; 일반식(Ⅴ)의 1-펜아실 이미다졸을 일반식(Ⅵ)의 알킬화제와 반응시키거나 ; 일반식(Ⅶ)의 화합물을 일반식(Ⅱ)의 화합물로 산화시킴을 포함하여, 일반식(Ⅱ)의 화합물을 제조하는 방법.상기식에서, R1은 C1-C4알킬이고 ; R2및 R3는 독립적으로, 수소 또는 C1-C4알킬이며 ; R4는 각기 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시, 트리플루오로메틸 또는 C1-C4알킬티오이고 ; R5는 수소 또는이며 ; R6은 수소, C1-C4알킬, 또는이고 ; R7은 수소 또는 C1-C4알킬이며 ; R8은 각기 독립적으로, C1-C4알킬 또는 페닐이고 ; X는 치료적으로 허용되는 음이온이고 ; m은 0,1 또는 2이며 ; 단 R1이 메탈이고 R2및 R3가 수소이면 m은 0이 아니고 : R1이 메틸이고 R2및 R3가 수소이고 X가 브롬이며 m이 1이면, R4는 4-메톡시 또는 4-메틸이 아니다.
- 제1항에 있어서, 각각의 R4가 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오인 일반식(Ⅱ)의 화합물을 제조하는 방법.
- 제2항에 있어서, R1이 메틸이고 R2및 R3는 모두 수소인 일반식(Ⅱ)의 화합물을 제조하는 방법.
- 제2항에 있어서, R1및 R2가 메탈인 일반식(Ⅱ)의 화합물을 제조하는 방법.
- 제2항에 있어서, 1-메틸-3-[2-(3-메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-에톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(4-에틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-에틸-3-[2-(2-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(2,4-디메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 또는 1-메틸-3-[2-(2,5-디메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드를 제조하는 방법.
- 포유류의 혈당치를 저하시키는데 유용한 하기 일반식(Ⅰ)의 화합물.상기식에서, R1은 C1-C4알킬이고 ; R2및 R3는 독립적으로, 수소 또는 C1-C4알킬이며 ; R4는 각기 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시, 트리플루오로메틸 또는 C1-C4알킬티오이고 ; R5는 수소 또는이며 ; R6은 수소, C1-C4알킬, 또는이며 ; R7은 수소 또는 C1-C4알킬이며 ; R8은 각기 독립적으로, C1-C4알킬 또는 페닐이고 ; X는 치료적으로 허용되는 음이온이고 ; m은 0,1 또는 2이다.
- 제6항에 있어서, 각각의 R4가 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오인 혈당치를 저하시키는데 유용한 일반식(Ⅰ)의 화합물.
- 제7항에 있어서, R1이 메틸이고 R2및 R3는 모두 수소인 혈당치를 저하시키는데 유용한 일반식(Ⅰ)의 화합물.
- 제7항 또는 제8항에 있어서, 포유류의 혈당치를 저하시키는 유용한 화합물이 1-메틸-3-[2-(4-메틸페닐)-2-옥소에틸]이미다졸리움 브로마이드, 1-메틸-3-[2-(3-메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-에톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(4-에틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(2-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(2,4-디메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 또는 1-메틸-3-[2-(2,5-디메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드인 일반식(Ⅰ)의 화합물.
- 제7항에 있어서, R2및 R5중 하나가 수소이고 다른 하나는 메틸이며, R1은 메틸인 포유류의 혈당치를 저하시키는데 유용한 일반식(Ⅰ)의 화합물.
- 제7항에 있어서, R1, R2및 R3가 모두 메틸인 포유류의 혈당치를 저하시키는데 유용한 일반식(Ⅰ)의 화합물.
- 일반식(Ⅱ)의 화합물.상기식에서, R1은 C1-C4알킬이고 ; R2및 R3는 독립적으로, 수소 또는 C1-C4알킬이며 ; R4는 각기 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시, 트리플루오로메틸 또는 C1-C4알킬티오이고 ; R5는 수소 또는이며 ; R6은 수소, C1-C4알킬, 또는이고 ; R7은 수소 또는 C1-C4알킬이며 ; R8은 각기 독립적으로, C1-C4알킬 또는 페닐이고 : X는 치료적으로 허용되는 음이온이고 : m은 0,1 또는 2이며 : 단, R1이 메틸이고 R2및 R3가 수소이면, m은 0이 아니고 ; R1이 메틸이고 R2및 R3가 수소이며 X가 브롬이고 m이 1이면, R4는 4-메톡시 또는 4-메틸이 아니다.
- 제12항에 있어서, 각각의 R4가 독립적으로, -OR5, -NR6R7, C1-C4알킬, C1-C4알콕시 또는 C1-C4알킬티오인 일반식(Ⅱ)의 화합물.
- 제13항에 있어서, R1및 R2가 메틸인 일반식(Ⅱ)의 화합물.
- 제13항 또는 제14항에 있어서, 화합물이 1-메틸-3-[2-(3-메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-에톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(4-에틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(2-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(2,4-디메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 1-메틸-3-[2-(3-메틸페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드, 또는 1-메틸-3-[2-(2,5-디메톡시페닐)-2-옥소에틸]-1H-이미다졸리움 브로마이드인 일반식(Ⅱ)의 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US670776 | 1984-11-13 | ||
| US06/670,776 US4609670A (en) | 1984-11-13 | 1984-11-13 | Imidazolium hypoglycemic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR860004029A true KR860004029A (ko) | 1986-06-16 |
| KR880001231B1 KR880001231B1 (ko) | 1988-07-12 |
Family
ID=24691822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850008349A KR880001231B1 (ko) | 1984-11-13 | 1985-11-08 | 이미다졸리움 염의 제조방법 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4609670A (ko) |
| EP (1) | EP0182533B1 (ko) |
| JP (1) | JPH0647576B2 (ko) |
| KR (1) | KR880001231B1 (ko) |
| CN (1) | CN1013444B (ko) |
| AR (1) | AR244671A1 (ko) |
| AT (1) | ATE46505T1 (ko) |
| AU (1) | AU574532B2 (ko) |
| CA (1) | CA1266673A (ko) |
| DE (1) | DE3573114D1 (ko) |
| DK (1) | DK164547C (ko) |
| EG (1) | EG17707A (ko) |
| ES (1) | ES8702370A1 (ko) |
| GR (1) | GR852707B (ko) |
| HU (1) | HU195490B (ko) |
| IE (1) | IE59093B1 (ko) |
| NZ (1) | NZ214088A (ko) |
| PH (1) | PH21656A (ko) |
| PT (1) | PT81439B (ko) |
| SU (1) | SU1424733A3 (ko) |
| ZA (1) | ZA858499B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5656261A (en) * | 1995-01-18 | 1997-08-12 | The Picower Institute For Medical Research | Preventing and reversing advanced glycosylation endproducts |
| US5853703A (en) * | 1995-01-18 | 1998-12-29 | The Picower Institute For Medical Research | Preventing and reversing the formation of advanced glycosylation endproducts |
| FI119756B (fi) * | 1995-01-18 | 2009-03-13 | Alteon Inc | Tiatsoliumyhdisteiden käyttö pitkälle edenneen glykosylaation lopputuotteiden muodostumisen estossa ja suunnan muutoksessa |
| US20040198795A1 (en) * | 1996-05-08 | 2004-10-07 | Wagle Dilip R | Substituted imidazoliums and methods of use therefor |
| US6121300A (en) * | 1998-11-10 | 2000-09-19 | Wagle; Dilip R. | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
| US6781039B2 (en) * | 2002-05-07 | 2004-08-24 | Stine Seed Farm, Inc. | Soybean cultivar S010360 |
| DE102006028264B4 (de) * | 2006-01-10 | 2008-12-11 | Uwe Pisching | Sägebock |
| CN100460395C (zh) * | 2006-07-06 | 2009-02-11 | 云南大学 | 芳环和杂环酰甲基咪唑盐类化合物及其制备方法 |
| CN104592205A (zh) * | 2010-03-01 | 2015-05-06 | Gtx公司 | 用于治疗癌的化合物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3852301A (en) * | 1973-06-21 | 1974-12-03 | Squibb & Sons Inc | Enol betaines of imidazoles |
| US4017631A (en) * | 1974-11-19 | 1977-04-12 | Janssen Pharmaceutica N.V. | Imidazolium salts |
| GB1533706A (en) * | 1976-03-01 | 1978-11-29 | Ici Ltd | Fungicidal imidazoles and 1,2,4-triazoles |
| DE2643563A1 (de) * | 1976-09-28 | 1978-03-30 | Bayer Ag | Alpha-(4-biphenylyl)-benzyl-azolium- salze, verfahren zu ihrer herstellung sowie ihre verwendung zur bekaempfung von mikroorganismen |
| DE2714290A1 (de) * | 1977-03-31 | 1978-10-05 | Bayer Ag | Fungizide mittel |
| JPS5479278A (en) * | 1977-12-05 | 1979-06-25 | Nippon Soda Co Ltd | Imidazolium halide |
| JPS58150567A (ja) * | 1982-03-03 | 1983-09-07 | Kissei Pharmaceut Co Ltd | 新規な１，３−二置換イミダゾ−ル誘導体およびその製造方法 |
| US4581370A (en) * | 1983-07-12 | 1986-04-08 | Schering A.G. | Antiarrhythmic imidazoliums |
-
1984
- 1984-11-13 US US06/670,776 patent/US4609670A/en not_active Expired - Fee Related
-
1985
- 1985-11-05 CN CN85108115A patent/CN1013444B/zh not_active Expired
- 1985-11-05 DE DE8585308017T patent/DE3573114D1/de not_active Expired
- 1985-11-05 ZA ZA858499A patent/ZA858499B/xx unknown
- 1985-11-05 AT AT85308017T patent/ATE46505T1/de not_active IP Right Cessation
- 1985-11-05 EP EP85308017A patent/EP0182533B1/en not_active Expired
- 1985-11-05 AR AR85302178A patent/AR244671A1/es active
- 1985-11-06 PT PT81439A patent/PT81439B/pt not_active IP Right Cessation
- 1985-11-06 CA CA000494704A patent/CA1266673A/en not_active Expired - Lifetime
- 1985-11-06 NZ NZ214088A patent/NZ214088A/xx unknown
- 1985-11-08 DK DK515285A patent/DK164547C/da not_active IP Right Cessation
- 1985-11-08 PH PH33043A patent/PH21656A/en unknown
- 1985-11-08 GR GR852707A patent/GR852707B/el unknown
- 1985-11-08 KR KR1019850008349A patent/KR880001231B1/ko not_active IP Right Cessation
- 1985-11-11 AU AU49737/85A patent/AU574532B2/en not_active Ceased
- 1985-11-11 SU SU853972626A patent/SU1424733A3/ru active
- 1985-11-12 IE IE282285A patent/IE59093B1/en not_active IP Right Cessation
- 1985-11-12 EG EG722/85A patent/EG17707A/xx active
- 1985-11-12 JP JP60254599A patent/JPH0647576B2/ja not_active Expired - Lifetime
- 1985-11-12 ES ES548797A patent/ES8702370A1/es not_active Expired
- 1985-11-12 HU HU854325A patent/HU195490B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PT81439B (pt) | 1988-03-03 |
| DK515285A (da) | 1986-05-14 |
| EG17707A (en) | 1990-08-30 |
| CN85108115A (zh) | 1986-07-30 |
| HUT39164A (en) | 1986-08-28 |
| JPS61122212A (ja) | 1986-06-10 |
| CA1266673A (en) | 1990-03-13 |
| JPH0647576B2 (ja) | 1994-06-22 |
| PH21656A (en) | 1988-01-13 |
| CN1013444B (zh) | 1991-08-07 |
| ES8702370A1 (es) | 1987-01-01 |
| PT81439A (en) | 1985-12-01 |
| KR880001231B1 (ko) | 1988-07-12 |
| EP0182533A2 (en) | 1986-05-28 |
| IE59093B1 (en) | 1994-01-12 |
| NZ214088A (en) | 1988-09-29 |
| ATE46505T1 (de) | 1989-10-15 |
| DE3573114D1 (en) | 1989-10-26 |
| SU1424733A3 (ru) | 1988-09-15 |
| GR852707B (ko) | 1986-03-10 |
| US4609670A (en) | 1986-09-02 |
| EP0182533A3 (en) | 1987-06-03 |
| AU4973785A (en) | 1986-05-22 |
| DK164547C (da) | 1992-11-30 |
| DK164547B (da) | 1992-07-13 |
| ZA858499B (en) | 1987-06-24 |
| EP0182533B1 (en) | 1989-09-20 |
| IE852822L (en) | 1986-05-13 |
| ES548797A0 (es) | 1987-01-01 |
| HU195490B (en) | 1988-05-30 |
| AR244671A1 (es) | 1993-11-30 |
| DK515285D0 (da) | 1985-11-08 |
| AU574532B2 (en) | 1988-07-07 |
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