IE52792B1 - 4-phenoxy-3-hydroxy-butyramidoxime derivatives, process for their preparation and their use in therapeutics - Google Patents
4-phenoxy-3-hydroxy-butyramidoxime derivatives, process for their preparation and their use in therapeuticsInfo
- Publication number
- IE52792B1 IE52792B1 IE760/82A IE76082A IE52792B1 IE 52792 B1 IE52792 B1 IE 52792B1 IE 760/82 A IE760/82 A IE 760/82A IE 76082 A IE76082 A IE 76082A IE 52792 B1 IE52792 B1 IE 52792B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxy
- formula
- allylphenoxy
- phenoxy
- butyramidoxime
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- LDDFGSGAJBIUGA-UHFFFAOYSA-N n',3-dihydroxy-4-phenoxybutanimidamide Chemical class ON=C(N)CC(O)COC1=CC=CC=C1 LDDFGSGAJBIUGA-UHFFFAOYSA-N 0.000 title claims 2
- 239000003814 drug Substances 0.000 title abstract description 3
- 238000002360 preparation method Methods 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 230000001225 therapeutic effect Effects 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- 230000000747 cardiac effect Effects 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000033764 rhythmic process Effects 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 3
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000003416 antiarrhythmic agent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QMIHLTWUCXXBQQ-UHFFFAOYSA-N n',3-dihydroxy-4-naphthalen-1-yloxybutanimidamide;hydrochloride Chemical compound [Cl-].C1=CC=C2C(OCC(O)CC(/[NH3+])=N/O)=CC=CC2=C1 QMIHLTWUCXXBQQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 230000001934 delay Effects 0.000 description 3
- USMXXSBPNFTBIA-PHFVEKHWSA-N v6d7xhx354 Chemical compound O[N+]([O-])=O.O([C@H]1[C@]2(O)C[C@H]3[C@@]45[C@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 USMXXSBPNFTBIA-PHFVEKHWSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000006218 bradycardia Diseases 0.000 description 1
- 230000036471 bradycardia Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OPENCMFJZQABIY-UHFFFAOYSA-N n'-hydroxybutanimidamide Chemical class CCCC(N)=NO OPENCMFJZQABIY-UHFFFAOYSA-N 0.000 description 1
- UPZVYDSBLFNMLK-UHFFFAOYSA-N nadoxolol Chemical compound C1=CC=C2C(OCC(O)CC(/N)=N/O)=CC=CC2=C1 UPZVYDSBLFNMLK-UHFFFAOYSA-N 0.000 description 1
- 229960004501 nadoxolol Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
Classifications
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/12—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines
- C07C259/14—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. N-hydroxyamidines having carbon atoms of hydroxamidine groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Materials For Medical Uses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8106469A FR2503147A1 (fr) | 1981-03-31 | 1981-03-31 | Derives de 4-phenoxy-3-hydroxy-butyramidoxine, leur procede de preparation et leur utilisation en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE820760L IE820760L (en) | 1982-09-30 |
| IE52792B1 true IE52792B1 (en) | 1988-03-02 |
Family
ID=9256834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE760/82A IE52792B1 (en) | 1981-03-31 | 1982-03-30 | 4-phenoxy-3-hydroxy-butyramidoxime derivatives, process for their preparation and their use in therapeutics |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4409242A (en:Method) |
| EP (1) | EP0063508B1 (en:Method) |
| JP (1) | JPS57176945A (en:Method) |
| AT (1) | ATE7908T1 (en:Method) |
| CA (1) | CA1177493A (en:Method) |
| DE (1) | DE3260242D1 (en:Method) |
| DK (1) | DK144082A (en:Method) |
| ES (1) | ES510983A0 (en:Method) |
| FR (1) | FR2503147A1 (en:Method) |
| GR (1) | GR76039B (en:Method) |
| IE (1) | IE52792B1 (en:Method) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2210388A1 (en) * | 1972-12-14 | 1974-07-12 | Lafon Labor | 4-Phenoxy-3-hydroxy-butyramidines - as agents for treating cardiac rhythm disorders |
| JPS517662A (ja) * | 1974-07-08 | 1976-01-22 | Toshin Giken Kk | Teiryokyokyusochi |
-
1981
- 1981-03-31 FR FR8106469A patent/FR2503147A1/fr active Granted
-
1982
- 1982-03-17 GR GR67625A patent/GR76039B/el unknown
- 1982-03-19 US US06/360,057 patent/US4409242A/en not_active Expired - Fee Related
- 1982-03-23 EP EP82400521A patent/EP0063508B1/fr not_active Expired
- 1982-03-23 AT AT82400521T patent/ATE7908T1/de not_active IP Right Cessation
- 1982-03-23 DE DE8282400521T patent/DE3260242D1/de not_active Expired
- 1982-03-24 CA CA000399220A patent/CA1177493A/en not_active Expired
- 1982-03-30 DK DK144082A patent/DK144082A/da not_active IP Right Cessation
- 1982-03-30 IE IE760/82A patent/IE52792B1/en unknown
- 1982-03-30 ES ES510983A patent/ES510983A0/es active Granted
- 1982-03-31 JP JP57054761A patent/JPS57176945A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2503147A1 (fr) | 1982-10-08 |
| EP0063508A1 (fr) | 1982-10-27 |
| FR2503147B1 (en:Method) | 1984-05-25 |
| JPS6358820B2 (en:Method) | 1988-11-17 |
| GR76039B (en:Method) | 1984-08-03 |
| ES8303311A1 (es) | 1983-02-01 |
| US4409242A (en) | 1983-10-11 |
| ES510983A0 (es) | 1983-02-01 |
| CA1177493A (en) | 1984-11-06 |
| DE3260242D1 (en) | 1984-07-19 |
| JPS57176945A (en) | 1982-10-30 |
| IE820760L (en) | 1982-09-30 |
| EP0063508B1 (fr) | 1984-06-13 |
| ATE7908T1 (de) | 1984-06-15 |
| DK144082A (da) | 1982-10-01 |
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