FR2503147A1 - Derives de 4-phenoxy-3-hydroxy-butyramidoxine, leur procede de preparation et leur utilisation en therapeutique - Google Patents
Derives de 4-phenoxy-3-hydroxy-butyramidoxine, leur procede de preparation et leur utilisation en therapeutique Download PDFInfo
- Publication number
- FR2503147A1 FR2503147A1 FR8106469A FR8106469A FR2503147A1 FR 2503147 A1 FR2503147 A1 FR 2503147A1 FR 8106469 A FR8106469 A FR 8106469A FR 8106469 A FR8106469 A FR 8106469A FR 2503147 A1 FR2503147 A1 FR 2503147A1
- Authority
- FR
- France
- Prior art keywords
- hydroxy
- formula
- allylphenoxy
- phenoxy
- butyramidoxime
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 7
- LDDFGSGAJBIUGA-UHFFFAOYSA-N n',3-dihydroxy-4-phenoxybutanimidamide Chemical class ON=C(N)CC(O)COC1=CC=CC=C1 LDDFGSGAJBIUGA-UHFFFAOYSA-N 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 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
- 230000033764 rhythmic process Effects 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 4
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 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
- 239000003416 antiarrhythmic agent Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- XVYAOTXJIUUBEB-UHFFFAOYSA-N 3-hydroxy-4-phenoxybutanimidamide Chemical class NC(=N)CC(O)COC1=CC=CC=C1 XVYAOTXJIUUBEB-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 210000000748 cardiovascular system Anatomy 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- ZQQFGDIJTQTKRO-UHFFFAOYSA-N n',3-dihydroxybutanimidamide Chemical compound CC(O)CC(=N)NO ZQQFGDIJTQTKRO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- YYTSGNJTASLUOY-UHFFFAOYSA-N 1-chloropropan-2-ol Chemical compound CC(O)CCl YYTSGNJTASLUOY-UHFFFAOYSA-N 0.000 description 1
- QIRNGVVZBINFMX-UHFFFAOYSA-N 2-allylphenol Chemical compound OC1=CC=CC=C1CC=C QIRNGVVZBINFMX-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- -1 4- (3,5-dimethylphenoxy) -3-hydroxy-butyramidoxime hydrochloride Chemical compound 0.000 description 1
- 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
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 102100038916 Caspase-5 Human genes 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 101100112336 Homo sapiens CASP5 gene Proteins 0.000 description 1
- 101100273286 Mus musculus Casp4 gene Proteins 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
- 239000013543 active substance Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 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
- 230000000059 bradycardiac effect Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 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
- 230000008034 disappearance Effects 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 235000011090 malic acid Nutrition 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
- 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
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
Priority Applications (11)
| 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 |
| GR67625A GR76039B (en:Method) | 1981-03-31 | 1982-03-17 | |
| US06/360,057 US4409242A (en) | 1981-03-31 | 1982-03-19 | 4-Phenoxy-3-hydroxy-butyramidoxime derivatives |
| EP82400521A EP0063508B1 (fr) | 1981-03-31 | 1982-03-23 | Dérivés de 4-phénoxy-3-hydroxy-butyramidoxime, leur procédé de préparation et leur utilisation en thérapeutique |
| DE8282400521T DE3260242D1 (en) | 1981-03-31 | 1982-03-23 | 4-phenoxy-3-hydroxy-butyramidoxime derivatives, preparation thereof and use thereof as medicaments |
| AT82400521T ATE7908T1 (de) | 1981-03-31 | 1982-03-23 | 4-phenoxy-3-hydroxy-butyramidoximderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel. |
| CA000399220A CA1177493A (en) | 1981-03-31 | 1982-03-24 | 4-phenoxy-3-hydroxy-butyramidoxime derivatives |
| 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 |
| ES510983A ES510983A0 (es) | 1981-03-31 | 1982-03-30 | Procedimiento de preparacion de un nuevo compuesto perteneciente a la familia de las 4-(alilfenoxi)-3-hidroxibutiramidoximas. |
| DK144082A DK144082A (da) | 1981-03-31 | 1982-03-30 | Fremgangsmaade til fremstilling af 4-phenoxy-3-hydroxy-butyramidoxim-derivater |
| JP57054761A JPS57176945A (en) | 1981-03-31 | 1982-03-31 | 4-phenoxy-3-hydroxybutylamidoxime derivative, manufacture and use |
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 |
|---|---|
| FR2503147A1 true FR2503147A1 (fr) | 1982-10-08 |
| FR2503147B1 FR2503147B1 (en:Method) | 1984-05-25 |
Family
ID=9256834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8106469A Granted FR2503147A1 (fr) | 1981-03-31 | 1981-03-31 | Derives de 4-phenoxy-3-hydroxy-butyramidoxine, leur procede de preparation et leur utilisation en therapeutique |
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) |
Citations (1)
| 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 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Patent Citations (1)
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0063508A1 (fr) | 1982-10-27 |
| FR2503147B1 (en:Method) | 1984-05-25 |
| JPS6358820B2 (en:Method) | 1988-11-17 |
| IE52792B1 (en) | 1988-03-02 |
| 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |