NO864337L - Dopamin-b-hydroksybeta-hydroksylase- inhibitorer. - Google Patents
Dopamin-b-hydroksybeta-hydroksylase- inhibitorer.Info
- Publication number
- NO864337L NO864337L NO864337A NO864337A NO864337L NO 864337 L NO864337 L NO 864337L NO 864337 A NO864337 A NO 864337A NO 864337 A NO864337 A NO 864337A NO 864337 L NO864337 L NO 864337L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- substituted
- imidazole
- thiol
- acid
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 150000003567 thiocyanates Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- -1 natriuretics Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
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- 229960003638 dopamine Drugs 0.000 description 10
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 238000006243 chemical reaction Methods 0.000 description 8
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 8
- 229960002748 norepinephrine Drugs 0.000 description 8
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 5
- YKFBBCYCBYMACS-UHFFFAOYSA-N 3-[(4-amino-3,5-difluorophenyl)methyl]-1h-imidazole-2-thione Chemical compound C1=C(F)C(N)=C(F)C=C1CN1C(S)=NC=C1 YKFBBCYCBYMACS-UHFFFAOYSA-N 0.000 description 5
- 150000003943 catecholamines Chemical class 0.000 description 5
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 4
- ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000002220 antihypertensive agent Substances 0.000 description 3
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 239000002934 diuretic Substances 0.000 description 3
- 229940030606 diuretics Drugs 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 3
- 229940116357 potassium thiocyanate Drugs 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 3
- QHGUCRYDKWKLMG-QMMMGPOBSA-N (R)-octopamine Chemical compound NC[C@H](O)C1=CC=C(O)C=C1 QHGUCRYDKWKLMG-QMMMGPOBSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- UCQCUJWREUJRPA-UHFFFAOYSA-N 3-[(3,5-difluoro-4-hydroxyphenyl)methyl]-1h-imidazole-2-thione Chemical compound C1=C(F)C(O)=C(F)C=C1CN1C(=S)NC=C1 UCQCUJWREUJRPA-UHFFFAOYSA-N 0.000 description 2
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- SKLUWKYNZNXSLX-UHFFFAOYSA-N 4-Acetamidobenzaldehyde Chemical class CC(=O)NC1=CC=C(C=O)C=C1 SKLUWKYNZNXSLX-UHFFFAOYSA-N 0.000 description 2
- COFNCCWGWXFACE-UHFFFAOYSA-N 4-amino-3,5-dichlorobenzonitrile Chemical compound NC1=C(Cl)C=C(C#N)C=C1Cl COFNCCWGWXFACE-UHFFFAOYSA-N 0.000 description 2
- KVHGANXAAWNSFM-UHFFFAOYSA-N 4-amino-3,5-difluorobenzonitrile Chemical compound NC1=C(F)C=C(C#N)C=C1F KVHGANXAAWNSFM-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical class CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
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- 241000700159 Rattus Species 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 235000021355 Stearic acid Nutrition 0.000 description 2
- 208000007107 Stomach Ulcer Diseases 0.000 description 2
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- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 229940127088 antihypertensive drug Drugs 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- 239000000496 cardiotonic agent Substances 0.000 description 2
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- QCVPUINEFOQBEP-UHFFFAOYSA-N n-(2,6-difluoro-4-formylphenyl)-2,2,2-trifluoroacetamide Chemical compound FC1=CC(C=O)=CC(F)=C1NC(=O)C(F)(F)F QCVPUINEFOQBEP-UHFFFAOYSA-N 0.000 description 2
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
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- XAAZZRBOUKPMHK-UHFFFAOYSA-N 3-[(4-amino-3-chloro-5-fluorophenyl)methyl]-1h-imidazole-2-thione Chemical compound C1=C(Cl)C(N)=C(F)C=C1CN1C(S)=NC=C1 XAAZZRBOUKPMHK-UHFFFAOYSA-N 0.000 description 1
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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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/42—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- A61P9/08—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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
-
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/793,512 US4719223A (en) | 1985-10-31 | 1985-10-31 | Imidazolethiol dopamine-beta-hydroxylase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO864337D0 NO864337D0 (no) | 1986-10-30 |
| NO864337L true NO864337L (no) | 1987-05-04 |
Family
ID=25160082
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO864337A NO864337L (no) | 1985-10-31 | 1986-10-30 | Dopamin-b-hydroksybeta-hydroksylase- inhibitorer. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4719223A (fi) |
| EP (1) | EP0221778A3 (fi) |
| JP (1) | JPS62108815A (fi) |
| KR (1) | KR870003994A (fi) |
| CN (1) | CN86107151A (fi) |
| AU (1) | AU598485B2 (fi) |
| DK (1) | DK515786A (fi) |
| FI (1) | FI864431A (fi) |
| HU (1) | HU197563B (fi) |
| NO (1) | NO864337L (fi) |
| NZ (1) | NZ218098A (fi) |
| PH (1) | PH21776A (fi) |
| PT (1) | PT83628B (fi) |
| ZA (1) | ZA868269B (fi) |
| ZW (1) | ZW21586A1 (fi) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4743613A (en) * | 1986-04-08 | 1988-05-10 | Smithkline Beckman Corporation | Ester prodrugs of dopamine-β-hydroxylase, inhibitors, composition containing them, and method of using them to inhibit dopamine-β-hydroxylase activity |
| US5057613A (en) * | 1986-05-06 | 1991-10-15 | Merrell Dow Pharmaceuticals | Novel thione dopamine beta hydroxylase inhibitors |
| US4859779A (en) * | 1987-03-24 | 1989-08-22 | Smithkline Beckman Corporation | Dopamine-β-hydroxylase inhibitors |
| US4835154A (en) * | 1987-06-01 | 1989-05-30 | Smithkline Beckman Corporation | 1-aralykyl-5-piperazinylmethyl-2-mercaptoimidazoles and 2-alkylthioimidazoles and their use as dopamine-βhydroxylase inhibitors |
| US4882348A (en) * | 1987-12-29 | 1989-11-21 | Smithkline Beckman Corporation | 2-(aminoalkylthio)imidazoles as dopamine-β-hydroxylase inhibitors |
| DE19620408A1 (de) * | 1996-05-21 | 1997-11-27 | Bayer Ag | Mercapto-imidazolyl-Derivate |
| US20080002735A1 (en) * | 1997-04-01 | 2008-01-03 | Paradox Security Systems Ltd. | Device network |
| US7965734B2 (en) * | 2005-12-15 | 2011-06-21 | Paradox Security Systems Ltd. | Device network interface |
| EP3971178A1 (en) | 2012-03-07 | 2022-03-23 | The McLean Hospital Corporation | Aminoquinoline derivatives and uses thereof |
| CN103214421B (zh) * | 2012-12-11 | 2016-03-02 | 上海博康精细化工有限公司 | 2-巯基-1-甲基咪唑的工业化生产方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2180772A (en) * | 1935-10-25 | 1939-11-21 | Gen Aniline Works Inc | Trifluoromethyl benzaldehydes |
| FR1509975A (fr) * | 1965-10-21 | 1968-01-19 | Geigy Ag J R | Dérivés de l'imidazole et leur préparation |
| DE2259627A1 (de) * | 1972-12-06 | 1974-06-12 | Hoechst Ag | Imidazolyl-(2)-thio-alkansaeureester und verfahren zu ihrer herstellung |
| BR7708431A (pt) * | 1976-12-20 | 1978-08-15 | Wellcome Found | Processo para preparar imidazolinas e composicoes pesticidas que as contem |
| US4284641A (en) * | 1977-08-26 | 1981-08-18 | Burroughs Wellcome Co. | Pharmaceutically active imidazole derivatives |
| US4340738A (en) * | 1979-06-21 | 1982-07-20 | Janssen Pharmaceutica, N.V. | 2,3-Dihydro-imidazo[2,1-b]benzothiazoles |
| GB2096987B (en) * | 1981-04-22 | 1984-04-04 | Farmos Oy | Substituted imidazole and imidazole derivatives and their preparation and use |
| US4487761A (en) * | 1982-04-05 | 1984-12-11 | Merck & Co., Inc. | Dopamine β-hydroxylase inhibitors |
| US4532331A (en) * | 1983-04-12 | 1985-07-30 | Smithkline Beckman Corporation | 1-Benzyl-2-aminomethyl imidazole derivatives |
| PT78388B (en) * | 1983-04-12 | 1986-09-15 | Smithkline Beckman Corp | Dopamine-beta-hydroxylase inhibitors |
-
1985
- 1985-10-31 US US06/793,512 patent/US4719223A/en not_active Expired - Fee Related
-
1986
- 1986-10-27 ZW ZW215/86A patent/ZW21586A1/xx unknown
- 1986-10-27 PT PT83628A patent/PT83628B/pt unknown
- 1986-10-28 DK DK515786A patent/DK515786A/da not_active Application Discontinuation
- 1986-10-29 NZ NZ218098A patent/NZ218098A/xx unknown
- 1986-10-30 KR KR860009105A patent/KR870003994A/ko not_active Application Discontinuation
- 1986-10-30 ZA ZA868269A patent/ZA868269B/xx unknown
- 1986-10-30 JP JP61259600A patent/JPS62108815A/ja active Pending
- 1986-10-30 FI FI864431A patent/FI864431A/fi not_active Application Discontinuation
- 1986-10-30 AU AU64639/86A patent/AU598485B2/en not_active Ceased
- 1986-10-30 NO NO864337A patent/NO864337L/no unknown
- 1986-10-30 EP EP86308482A patent/EP0221778A3/en not_active Withdrawn
- 1986-10-30 PH PH34429A patent/PH21776A/en unknown
- 1986-10-31 CN CN198686107151A patent/CN86107151A/zh active Pending
- 1986-10-31 HU HU864574A patent/HU197563B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US4719223A (en) | 1988-01-12 |
| ZA868269B (en) | 1987-07-29 |
| EP0221778A3 (en) | 1988-03-23 |
| ZW21586A1 (en) | 1987-06-24 |
| NZ218098A (en) | 1989-07-27 |
| HUT43830A (en) | 1987-12-28 |
| NO864337D0 (no) | 1986-10-30 |
| PT83628A (en) | 1986-11-01 |
| PT83628B (en) | 1988-11-15 |
| CN86107151A (zh) | 1987-05-13 |
| FI864431A (fi) | 1987-05-01 |
| DK515786D0 (da) | 1986-10-28 |
| FI864431A0 (fi) | 1986-10-30 |
| EP0221778A2 (en) | 1987-05-13 |
| AU6463986A (en) | 1987-05-07 |
| JPS62108815A (ja) | 1987-05-20 |
| AU598485B2 (en) | 1990-06-28 |
| DK515786A (da) | 1987-05-01 |
| PH21776A (en) | 1988-02-24 |
| KR870003994A (ko) | 1987-05-06 |
| HU197563B (en) | 1989-04-28 |
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