CH509273A - Verfahren zur Herstellung von Propionamidinen - Google Patents
Verfahren zur Herstellung von PropionamidinenInfo
- Publication number
- CH509273A CH509273A CH849767A CH849767A CH509273A CH 509273 A CH509273 A CH 509273A CH 849767 A CH849767 A CH 849767A CH 849767 A CH849767 A CH 849767A CH 509273 A CH509273 A CH 509273A
- Authority
- CH
- Switzerland
- Prior art keywords
- reaction
- hydrogen
- nitrile
- amidines
- phenoxyalkyl
- Prior art date
Links
- -1 Phenoxyalkyl amidines Chemical class 0.000 title claims abstract description 8
- 230000036772 blood pressure Effects 0.000 title abstract 2
- 230000001603 reducing effect Effects 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 150000002825 nitriles Chemical class 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- OEWPDZVHFDWAIH-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanenitrile Chemical compound N#CC(C)OC1=CC=CC(Cl)=C1 OEWPDZVHFDWAIH-UHFFFAOYSA-N 0.000 claims description 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 claims description 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical class CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000002585 base Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LSGPRLNRMANBIG-UHFFFAOYSA-N 2-(4-chlorophenoxy)ethanimidamide Chemical compound NC(=N)COC1=CC=C(Cl)C=C1 LSGPRLNRMANBIG-UHFFFAOYSA-N 0.000 description 2
- GGJZNRRFDCKJCD-UHFFFAOYSA-N 2-phenoxyethanimidamide Chemical class NC(=N)COC1=CC=CC=C1 GGJZNRRFDCKJCD-UHFFFAOYSA-N 0.000 description 2
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- KSVNOFHIFZIZHO-UHFFFAOYSA-N 2-(3-bromophenoxy)propanimidamide Chemical compound NC(=N)C(C)OC1=CC=CC(Br)=C1 KSVNOFHIFZIZHO-UHFFFAOYSA-N 0.000 description 1
- OJEXDCJEEJAVIA-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanimidamide Chemical compound NC(=N)C(C)OC1=CC=CC(Cl)=C1 OJEXDCJEEJAVIA-UHFFFAOYSA-N 0.000 description 1
- NFKBMFROTLXSLD-UHFFFAOYSA-N 2-(3-fluorophenoxy)propanimidamide Chemical compound NC(=N)C(C)OC1=CC=CC(F)=C1 NFKBMFROTLXSLD-UHFFFAOYSA-N 0.000 description 1
- CDMJMFMLDYNSFT-UHFFFAOYSA-N 2-(3-methoxyphenoxy)propanimidamide Chemical compound COC1=CC=CC(OC(C)C(N)=N)=C1 CDMJMFMLDYNSFT-UHFFFAOYSA-N 0.000 description 1
- UYCNOMSEXPUQTB-UHFFFAOYSA-N 2-(4-chlorophenoxy)propanimidamide Chemical compound NC(=N)C(C)OC1=CC=C(Cl)C=C1 UYCNOMSEXPUQTB-UHFFFAOYSA-N 0.000 description 1
- ZAVSPGJDAHKCPE-UHFFFAOYSA-N 2-(4-methoxyphenoxy)ethanimidamide Chemical class COC1=CC=C(OCC(N)=N)C=C1 ZAVSPGJDAHKCPE-UHFFFAOYSA-N 0.000 description 1
- PRBKNBDNRRUMRE-UHFFFAOYSA-N 2-phenoxypropanimidamide Chemical class NC(=N)C(C)OC1=CC=CC=C1 PRBKNBDNRRUMRE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- BEQAXQFDRFDRFN-UHFFFAOYSA-N C1(=CC=CC=C1)S(=O)(=O)O.ClC=1C=C(OC(C(=N)N)C)C=CC1 Chemical compound C1(=CC=CC=C1)S(=O)(=O)O.ClC=1C=C(OC(C(=N)N)C)C=CC1 BEQAXQFDRFDRFN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- WWLOCCUNZXBJFR-UHFFFAOYSA-N azanium;benzenesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC=CC=C1 WWLOCCUNZXBJFR-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH69970A CH489477A (de) | 1966-06-21 | 1967-06-15 | Verfahren zur Herstellung von Propionamidinen |
| CH69870A CH507212A (de) | 1966-06-21 | 1967-06-15 | Verfahren zur Herstellung von Propionamidinen |
| CH69770A CH521319A (de) | 1966-06-21 | 1967-06-15 | Verfahren zur Herstellung von Propionamidinen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27627/66A GB1194183A (en) | 1966-06-21 | 1966-06-21 | Biologically Active Propionamidines and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH509273A true CH509273A (de) | 1971-06-30 |
Family
ID=10262684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH849767A CH509273A (de) | 1966-06-21 | 1967-06-15 | Verfahren zur Herstellung von Propionamidinen |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53144676U (enrdf_load_stackoverflow) * | 1977-04-21 | 1978-11-15 |
-
1966
- 1966-06-21 GB GB27627/66A patent/GB1194183A/en not_active Expired
-
1967
- 1967-06-06 GR GR670134158A patent/GR34158B/el unknown
- 1967-06-07 CA CA992,470A patent/CA939385A/en not_active Expired
- 1967-06-09 IL IL28120A patent/IL28120A/xx unknown
- 1967-06-15 CH CH849767A patent/CH509273A/de not_active IP Right Cessation
- 1967-06-16 BE BE700096D patent/BE700096A/xx unknown
- 1967-06-16 AT AT560067A patent/AT291220B/de not_active IP Right Cessation
- 1967-06-19 SE SE08607/67A patent/SE339468B/xx unknown
- 1967-06-19 DK DK316667AA patent/DK126376B/da unknown
- 1967-06-20 LU LU53925D patent/LU53925A1/xx unknown
- 1967-06-20 NO NO168663A patent/NO120145B/no unknown
- 1967-06-20 ES ES342072A patent/ES342072A1/es not_active Expired
- 1967-06-20 NL NL6708561A patent/NL6708561A/xx unknown
- 1967-06-20 DE DE19671643216 patent/DE1643216A1/de active Pending
- 1967-06-20 FI FI671731A patent/FI48461C/fi active
- 1967-06-21 FR FR1572961D patent/FR1572961A/fr not_active Expired
- 1967-06-21 CS CS4552A patent/CS177802B2/cs unknown
- 1967-06-21 JP JP42039388A patent/JPS4927859B1/ja active Pending
- 1967-09-19 FR FR121436A patent/FR6910M/fr not_active Expired
-
1970
- 1970-06-01 JP JP45046452A patent/JPS4933941B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE1643216A1 (de) | 1971-07-29 |
| JPS4927859B1 (enrdf_load_stackoverflow) | 1974-07-22 |
| IL28120A (en) | 1971-03-24 |
| FI48461C (fi) | 1974-10-10 |
| BE700096A (enrdf_load_stackoverflow) | 1967-12-18 |
| FI48461B (enrdf_load_stackoverflow) | 1974-07-01 |
| FR1572961A (enrdf_load_stackoverflow) | 1969-07-04 |
| JPS4933941B1 (enrdf_load_stackoverflow) | 1974-09-11 |
| CS177802B2 (enrdf_load_stackoverflow) | 1977-08-31 |
| GB1194183A (en) | 1970-06-10 |
| AT291220B (de) | 1971-07-12 |
| NO120145B (enrdf_load_stackoverflow) | 1970-09-07 |
| SE339468B (enrdf_load_stackoverflow) | 1971-10-11 |
| ES342072A1 (es) | 1968-07-16 |
| CA939385A (en) | 1974-01-01 |
| FR6910M (enrdf_load_stackoverflow) | 1969-04-28 |
| DK126376B (da) | 1973-07-09 |
| NL6708561A (enrdf_load_stackoverflow) | 1967-12-22 |
| LU53925A1 (enrdf_load_stackoverflow) | 1968-03-11 |
| GR34158B (el) | 1968-03-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |