ES342072A1 - Biologically Active Propionamidines and their preparation - Google Patents
Biologically Active Propionamidines and their preparationInfo
- Publication number
- ES342072A1 ES342072A1 ES342072A ES342072A ES342072A1 ES 342072 A1 ES342072 A1 ES 342072A1 ES 342072 A ES342072 A ES 342072A ES 342072 A ES342072 A ES 342072A ES 342072 A1 ES342072 A1 ES 342072A1
- Authority
- ES
- Spain
- Prior art keywords
- prepared
- propionamidines
- preparation
- methoxyphenoxy
- chlorophenoxy
- 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.)
- Expired
Links
- GNFWGDKKNWGGJY-UHFFFAOYSA-N propanimidamide Chemical class CCC(N)=N GNFWGDKKNWGGJY-UHFFFAOYSA-N 0.000 title 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- -1 alkali metal amide Chemical class 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- WPZSAUFQHYFIPG-UHFFFAOYSA-N propanethioamide Chemical class CCC(N)=S WPZSAUFQHYFIPG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- OEWPDZVHFDWAIH-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanenitrile Chemical compound N#CC(C)OC1=CC=CC(Cl)=C1 OEWPDZVHFDWAIH-UHFFFAOYSA-N 0.000 abstract 1
- ABYGZZIGDUNFGL-UHFFFAOYSA-N 2-(3-chlorophenoxy)propanethioamide Chemical compound NC(=S)C(C)OC1=CC=CC(Cl)=C1 ABYGZZIGDUNFGL-UHFFFAOYSA-N 0.000 abstract 1
- BMPGGDBVJBYPRA-UHFFFAOYSA-N 2-(3-methoxyphenoxy)propanenitrile Chemical compound COC1=CC=CC(OC(C)C#N)=C1 BMPGGDBVJBYPRA-UHFFFAOYSA-N 0.000 abstract 1
- JNAYPRPPXRWGQO-UHFFFAOYSA-N 2-chloropropanenitrile Chemical compound CC(Cl)C#N JNAYPRPPXRWGQO-UHFFFAOYSA-N 0.000 abstract 1
- SSJVMRKIOZHZDX-UHFFFAOYSA-N Cl.COC=1C=C(OC(C(N)=NO)C)C=CC1 Chemical compound Cl.COC=1C=C(OC(C(N)=NO)C)C=CC1 SSJVMRKIOZHZDX-UHFFFAOYSA-N 0.000 abstract 1
- RCKYYKZMELQKRT-UHFFFAOYSA-N I.ClC=1C=C(OC(C(SC)=N)C)C=CC1 Chemical compound I.ClC=1C=C(OC(C(SC)=N)C)C=CC1 RCKYYKZMELQKRT-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 238000010171 animal model Methods 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 150000003943 catecholamines Chemical class 0.000 abstract 1
- RLZPCFQNZGINRP-UHFFFAOYSA-N n'-hydroxypropanimidamide Chemical class CCC(N)=NO RLZPCFQNZGINRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000002093 peripheral effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 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)
Abstract
The invention comprises compounds of formula wherein one of Z3 and Z4 is H and the other is H, halogen, C 1-4 alkoxy or CF 3 , their acid addition salts and their preparation (a) from the corresponding propionitriles and an aminonium salt, thiourea or alkali metal amide or (b) from the corresponding alkyl propionimidates or thiopropionimidates and ammonia, one or both of the reactants preferably being in the form of a salt or (c) from the corresponding thiopropionamides and ammonia or (d) from the corresponding propionamidoximes by reduction or (e) from appropriate alkali metal phenates and 2-substituted-propionamidines where the substituent is an alkali metalaccepting atom, e.g. halogen. 2 - Phenoxypropionitriles with substituents Z3 and Z4 as above are prepared from appropriate phenols and 2-chloropropionitrile. S - Methyl 2 - m - chlorophenoxy - thiopropionimidate hydriodide or p-toluenesulphonate is prepared from 2-m-chlorophenoxypropionitrile via 2-m-chlorophenoxy-thiopropionamide. 2 - m - Methoxyphenoxy - propionamidoxime hydrochloride is prepared from 2-m-methoxyphenoxy-propionitrile and hydroxylamine hydrochloride. The compounds of the invention are stated to produce peripheral and some central depletion of catecholamines in experimental animals, and may be made up with carriers into pharmaceutical compositions for oral administration.
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 |
|---|---|
| ES342072A1 true ES342072A1 (en) | 1968-07-16 |
Family
ID=10262684
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES342072A Expired ES342072A1 (en) | 1966-06-21 | 1967-06-20 | Biologically Active Propionamidines and their preparation |
Country Status (18)
| Country | Link |
|---|---|
| JP (2) | JPS4927859B1 (en) |
| AT (1) | AT291220B (en) |
| BE (1) | BE700096A (en) |
| CA (1) | CA939385A (en) |
| CH (1) | CH509273A (en) |
| CS (1) | CS177802B2 (en) |
| DE (1) | DE1643216A1 (en) |
| DK (1) | DK126376B (en) |
| ES (1) | ES342072A1 (en) |
| FI (1) | FI48461C (en) |
| FR (2) | FR1572961A (en) |
| GB (1) | GB1194183A (en) |
| GR (1) | GR34158B (en) |
| IL (1) | IL28120A (en) |
| LU (1) | LU53925A1 (en) |
| NL (1) | NL6708561A (en) |
| NO (1) | NO120145B (en) |
| SE (1) | SE339468B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53144676U (en) * | 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/en unknown
- 1967-06-07 CA CA992,470A patent/CA939385A/en not_active Expired
- 1967-06-09 IL IL28120A patent/IL28120A/en unknown
- 1967-06-15 CH CH849767A patent/CH509273A/en not_active IP Right Cessation
- 1967-06-16 AT AT560067A patent/AT291220B/en not_active IP Right Cessation
- 1967-06-16 BE BE700096D patent/BE700096A/xx unknown
- 1967-06-19 DK DK316667AA patent/DK126376B/en unknown
- 1967-06-19 SE SE08607/67A patent/SE339468B/xx unknown
- 1967-06-20 LU LU53925D patent/LU53925A1/xx unknown
- 1967-06-20 DE DE19671643216 patent/DE1643216A1/en active Pending
- 1967-06-20 NO NO168663A patent/NO120145B/no unknown
- 1967-06-20 NL NL6708561A patent/NL6708561A/xx unknown
- 1967-06-20 FI FI671731A patent/FI48461C/en active
- 1967-06-20 ES ES342072A patent/ES342072A1/en not_active Expired
- 1967-06-21 JP JP42039388A patent/JPS4927859B1/ja active Pending
- 1967-06-21 CS CS4552A patent/CS177802B2/cs unknown
- 1967-06-21 FR FR1572961D patent/FR1572961A/fr not_active Expired
- 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 |
|---|---|
| IL28120A (en) | 1971-03-24 |
| CH509273A (en) | 1971-06-30 |
| FR6910M (en) | 1969-04-28 |
| JPS4927859B1 (en) | 1974-07-22 |
| CS177802B2 (en) | 1977-08-31 |
| GB1194183A (en) | 1970-06-10 |
| GR34158B (en) | 1968-03-30 |
| LU53925A1 (en) | 1968-03-11 |
| FR1572961A (en) | 1969-07-04 |
| BE700096A (en) | 1967-12-18 |
| JPS4933941B1 (en) | 1974-09-11 |
| SE339468B (en) | 1971-10-11 |
| FI48461C (en) | 1974-10-10 |
| CA939385A (en) | 1974-01-01 |
| DK126376B (en) | 1973-07-09 |
| NO120145B (en) | 1970-09-07 |
| AT291220B (en) | 1971-07-12 |
| NL6708561A (en) | 1967-12-22 |
| FI48461B (en) | 1974-07-01 |
| DE1643216A1 (en) | 1971-07-29 |
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