CH491873A - Process for the preparation of phenylalkylaminoguanidines - Google Patents
Process for the preparation of phenylalkylaminoguanidinesInfo
- Publication number
- CH491873A CH491873A CH801766A CH801766A CH491873A CH 491873 A CH491873 A CH 491873A CH 801766 A CH801766 A CH 801766A CH 801766 A CH801766 A CH 801766A CH 491873 A CH491873 A CH 491873A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen nitrate
- addition salts
- acid addition
- phenylalkylaminoguanidines
- formula
- Prior art date
Links
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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Verfahren zur Herstellung von Phenylalkylaminoguanidinen
Gegenstand der Erfindung ist ein Verfahren zur Herstellung von Phenylalkylaminoguanidinen der Formel: I
EMI1.1
sowie von Säure-Additionssalzen davon. In Formel I bedeutet A eine gerade oder verzweigte Alkylengruppe mit I bis 4 C-Atomen. Rr, R, und Rs sind gleich oder verschieden und stellen Wasserstoff, Halogen, Hydroxyl oder I bis 3 C-Atome enthaltendes Alkyl oder Alkoxy dar. Diese Verbindungen wirken hypotensiv und über- treffen in dieser Hinsicht bekannte Verbindungen dieser Wirkungsrichtung. Sie dienen somit der Bereicherung des Arzneimittelschatzes.
Die hypotensive Wirkung von Phenylalkylaminoguanidinen der Formel I und ihrer Säure-Additions- salze beruht auf einer Entspeicherung des Neurotransmitters Noradrenalin an den sympathischen Nervenendigungen, wodurch es zu einer Sympathicolyse kommt.
Pharmakologisch ist dies feststellbar an der Abnahme des Noradrenalingehaltes im Herzen der Maus und am Ausbleiben der Nickhautkontraktion bei prä-und postganglionärer Reizung des Halssympathicus der Katze.
Phenylalkylaminoguanidine gemäss Formel I bzw. deren Säure-Additionssalze werden erhalten, wenn man Phenylalkylhydrazine der Formel :
EMI1.2
worin A, Rl, R. und R3 die obengenannte Bedeutung haben bzw. deren Säure-Additionssalze mit Cyanamid umsetzt.
Soweit nach dem beschriebenen Verfahren freie Basen erhalten wurden, können diese gegebenenfalls nachträglich in ihre Säure-Additionssalze übergeführt werden.
Als Säure-Additionssalze von Phenylalkylaminoguanidinen der Formel I kommen diejenigen der gebräuchlichen anorganischen und organischen Säuren, wie Salzsäure, Bromwasserstoffsäure, Schwefelsäure, Salpetersäure, Phosphorsäure, Essigsäure, Kohlensäure, Oxalsäure, Weinsäure, Toluolsulfonsäure und dergleichen in Betracht.
Beispiel 1
Eine Lösung von 20,7 g (0,1 Mol) ss-(p-Chlor- phenyl) äthylhydrazin-Hydrochlorid und 17,9 g (0,425 Mol) Cyanamid in 100 ml Wasser wird während 8 Stunden auf dem Dampfbad erwärmt. Das Reaktionsprodukt wird durch Zusatz einer Lösung von 9,3 g (0,11 Mol) Natriumbicarbonat in 200 ml Wasser ausgefällt. Das entstandene Bicarbonat wird in 100 ml n-Propanol suspendiert und unter Rühren des Reaktionsgemisches mit einer Lösung von 1, 65 ml (0,03 Mol) Schwefelsäure in 25 ml n-Propanol behandelt. Wenn die Kohlen dioxyd-Entwicklung beendet ist, wird die Lösung mit Kohle behandelt und filtriert. Nach dem Abkühlen fallen 2,5 g #- äthylaminoguanidin-
Semidihydrogensulfat in Form von weissen Plättchen an.
Durch Konzentration der Mutterlauge werden weitere 7,1 g dieses Produktes erhalten ; die Gesamtausbeute beträgt somit 9,6 g (37 % der Theorie). Das aus wässrigem Athanol umkristallisierte Produkt zeigt den Schmelzpunkt 192-195 C.
Durch Aufnehmen dieses Produktes aus alkalischwässriger Lösung in Chloroform, Eindampfen, Aufnehmen des Rückstandes in wenig Wasser und Zufügen von etwas konzentrierter Salpetersäure erhält man das entsprechende Hydrogennitrat vom Schmelzpunkt 146 bis 147 C (unter Zersetzung ; aus Athanol).
Bei analogem Vorgehen wie im oben beschriebenen Beispiel erhält man weiterhin, z. B. die in der nachfol genden Tabelle II angeführten Verbindungen. In der Kolonne rechts sind in Klammer die Lösungsmittel bzw.
L¯sungsmittelgemische angegeben, aus welchen Kristallisation erfolgte; dabei bedeuten: Ae êther, Ael êthanol, D Diisopropyläther, I Isopropanol, M Methanol, P n-Propanol und W Wasser.
Tabelle 11 Beispiel A Ri R= Form Smp.
2 -(CH2)2- H H Hydrogennitrat 145 C (Ael/D)
Semidihydrogenoxalat 213-214 C Zers. (Ael/W) Hydrochlorid 114-121 C (P/D) Semidihydrogencarbonat 109-11 l-C Zers. (nach Waschen mit Ael, D)
Hydrobromid 119-120 C (P/D)
3 -(CH2)2- o-OCH3 H Hydrogennitrat129-132 C (W) 4- (CH ; r H H Hydrogennitrat81-84 C(AeI/D) 5- (CHl) r o-CH3 H Hydrogennitrat 126-129C C (I) 6- (CH) m-CH3 H Semidihydrogensulfat 171-174 C Zers. (Ael/D)
Hydrogennitrat 96-98 C (P/W) 7- (CH2) p-CH3 H Semidihydrogensulfat 178-184 C (Ael) Hydrogennitrat 118-119 C (W)
8 -(CH2)2- o-CH3 H Semidihydrogensulfat 171-176 Zers.
(Ael/I) Hydrogennitrat 150-151 C (W/I)
9 -(CH2)2- p-F H Semidihydrogensulfat 152-155 C (Ael/D) Hydrogennitrat 123-124C C (W)
10 -(CH2)2- o-F H Semidihydrogensulfat 170-173 C (Ael/W)
Hydrogennitrat 133-134 C (W)
11 -(CH2)2- p-OCH3 H Semidihydrogensulfat 207-215 C Zers.
(Ael W)
Hydrogennitrat 116-1189 C (Acl) 12- (CH2) 2-p-Br H Hydrogennitrat 160-162 C (W)
13 -(CH2)2- m-Cl H Hydrogennitrat117-120 C (W)
14 -(CH2)2- o-Cl H Hydrogennitrat 158-160 C (W)
15 -(CH2)2- o-Br H Hydrogennitrat] 58-1622 C (W)
16 -(CH2)2- 3-Cl 4-Cl Semidihydrogensulfat 230 C (M/D)
17 -(CH2)2- 2-Cl 4-Cl Hydrogennitrat 161-163 C (P)
18 -(CH2)3- o-F H Hydrogennitrat 783 C (I/D)
19 -(CH2)3- p-F H Hydrogennitrat 89-92 C (P/D)
20 -(CH2)3- o-Cl H Hydrogennitrat 127 C (Ael/D)
21 -(CH2)3- p-Cl H Hydrogennitrat 126-129 C (W) 22- (CHs) 3- p-CH :
! H Hydrogennitrat 105-107C C (I/D)
23 -(CH2)3- 2-Cl 4-Cl Hydrogennitrat 124-126 C (W)
24 -(CH2)3- 3-Cl 4-Cl Hydrogennitrat 140-142 C (Wi'I)
Process for the preparation of phenylalkylaminoguanidines
The invention relates to a process for the preparation of phenylalkylaminoguanidines of the formula: I
EMI1.1
as well as acid addition salts thereof. In formula I, A denotes a straight or branched alkylene group having 1 to 4 carbon atoms. Rr, R, and Rs are identical or different and represent hydrogen, halogen, hydroxyl or alkyl or alkoxy containing 1 to 3 carbon atoms. These compounds have a hypotensive effect and in this respect exceed compounds known in this regard. They thus serve to enrich the treasure trove of medicines.
The hypotensive effect of phenylalkylaminoguanidines of the formula I and their acid addition salts is based on the depletion of the neurotransmitter noradrenaline at the sympathetic nerve endings, which leads to sympathicolysis.
This can be determined pharmacologically from the decrease in the noradrenaline content in the heart of the mouse and the absence of nictitating membrane contraction in the case of pre- and postganglionic irritation of the cat's cervical sympathetic nerve.
Phenylalkylaminoguanidines according to formula I or their acid addition salts are obtained when phenylalkylhydrazines of the formula:
EMI1.2
wherein A, Rl, R. and R3 have the abovementioned meaning or their acid addition salts react with cyanamide.
If free bases were obtained by the process described, these can optionally be converted into their acid addition salts subsequently.
Suitable acid addition salts of phenylalkylaminoguanidines of the formula I are those of the customary inorganic and organic acids, such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, carbonic acid, oxalic acid, tartaric acid, toluenesulfonic acid and the like.
example 1
A solution of 20.7 g (0.1 mol) of ss- (p-chlorophenyl) ethyl hydrazine hydrochloride and 17.9 g (0.425 mol) of cyanamide in 100 ml of water is heated on the steam bath for 8 hours. The reaction product is precipitated by adding a solution of 9.3 g (0.11 mol) of sodium bicarbonate in 200 ml of water. The bicarbonate formed is suspended in 100 ml of n-propanol and treated with a solution of 1.65 ml (0.03 mol) of sulfuric acid in 25 ml of n-propanol while stirring the reaction mixture. When the development of carbon dioxide has ended, the solution is treated with charcoal and filtered. After cooling, 2.5 g of ethylaminoguanidine
Semi-dihydrogen sulfate in the form of white platelets.
Concentration of the mother liquor gives a further 7.1 g of this product; the total yield is thus 9.6 g (37% of theory). The product recrystallized from aqueous ethanol has a melting point of 192-195 C.
By taking up this product from an aqueous alkaline solution in chloroform, evaporating, taking up the residue in a little water and adding a little concentrated nitric acid, the corresponding hydrogen nitrate is obtained with a melting point of 146 to 147 ° C. (with decomposition; from ethanol).
With an analogous procedure as in the example described above, one still obtains, for. B. the compounds listed in the following Table II. In the column on the right, the solvents resp.
Solvent mixtures indicated from which crystallization took place; where: Ae êther, Ael êthanol, D diisopropyl ether, I isopropanol, M methanol, P n-propanol and W water.
Table 11 Example A Ri R = Form Smp.
2 - (CH2) 2- H H hydrogen nitrate 145 C (Ael / D)
Semidihydrogen oxalate 213-214 C dec. (Ael / W) hydrochloride 114-121 C (P / D) semidihydrogen carbonate 109-11 l-C dec. (after washing with Ael, D)
Hydrobromide 119-120 C (P / D)
3 - (CH2) 2- o-OCH3 H hydrogen nitrate 129-132 C (W) 4- (CH; r HH hydrogen nitrate 81-84 C (AeI / D) 5- (CHl) r o-CH3 H hydrogen nitrate 126-129C C ( I) 6- (CH) m-CH3 H semi-dihydrogen sulfate 171-174 C decomp. (Ael / D)
Hydrogen nitrate 96-98 C (P / W) 7- (CH2) p-CH3 H Semi-dihydrogen sulfate 178-184 C (Ael) Hydrogen nitrate 118-119 C (W)
8 - (CH2) 2- o-CH3 H semi-dihydrogen sulfate 171-176 dec.
(Ael / I) hydrogen nitrate 150-151 C (W / I)
9 - (CH2) 2- p-F H semi-dihydrogen sulfate 152-155 C (Ael / D) hydrogen nitrate 123-124C C (W)
10 - (CH2) 2- o-F H semi-dihydrogen sulfate 170-173 C (Ael / W)
Hydrogen Nitrate 133-134 C (W)
11 - (CH2) 2- p-OCH3 H semi-dihydrogen sulfate 207-215 C dec.
(Ael W)
Hydrogen nitrate 116-1189 C (Acl) 12- (CH2) 2-p-Br H Hydrogen nitrate 160-162 C (W)
13 - (CH2) 2- m-Cl H hydrogen nitrate 117-120 C (W)
14 - (CH2) 2- o-Cl H hydrogen nitrate 158-160 C (W)
15 - (CH2) 2- o-Br H hydrogen nitrate] 58-1622 C (W)
16 - (CH2) 2- 3-Cl 4-Cl semi-dihydrogen sulfate 230 C (M / D)
17 - (CH2) 2- 2-Cl 4-Cl hydrogen nitrate 161-163 C (P)
18 - (CH2) 3- o-F H hydrogen nitrate 783 C (I / D)
19 - (CH2) 3- p-F H hydrogen nitrate 89-92 C (P / D)
20 - (CH2) 3- o-Cl H hydrogen nitrate 127 C (Ael / D)
21 - (CH2) 3- p-Cl H hydrogen nitrate 126-129 C (W) 22- (CHs) 3- p-CH:
! H hydrogen nitrate 105-107C C (I / D)
23 - (CH2) 3- 2-Cl 4-Cl hydrogen nitrate 124-126 C (W)
24 - (CH2) 3- 3-Cl 4-Cl hydrogen nitrate 140-142 C (Wi'I)
Claims (1)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH801766A CH491873A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
CH898866A CH498097A (en) | 1964-05-05 | 1965-11-15 | 2 6-dihalophenylalkylamino guanidines useful as |
CH873466A CH497393A (en) | 1964-05-05 | 1966-06-16 | Phenylakylaminoguanidines used as hypoten - sives |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH585464A CH448057A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
CH801766A CH491873A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
Publications (1)
Publication Number | Publication Date |
---|---|
CH491873A true CH491873A (en) | 1970-06-15 |
Family
ID=4300408
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH801666A CH511216A (en) | 1964-05-05 | 1964-05-05 | Phenylalkylamino guanidines |
CH585464A CH448057A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
CH801766A CH491873A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH801666A CH511216A (en) | 1964-05-05 | 1964-05-05 | Phenylalkylamino guanidines |
CH585464A CH448057A (en) | 1964-05-05 | 1964-05-05 | Process for the preparation of phenylalkylaminoguanidines |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS4842627B1 (en) |
AT (3) | AT255433B (en) |
BE (1) | BE663481A (en) |
BR (1) | BR6569419D0 (en) |
CH (3) | CH511216A (en) |
CS (1) | CS151461B2 (en) |
DE (1) | DE1518222A1 (en) |
DK (2) | DK107288C (en) |
ES (1) | ES312384A1 (en) |
FI (1) | FI42316B (en) |
FR (1) | FR4399M (en) |
GB (1) | GB1096348A (en) |
IL (1) | IL23443A (en) |
NL (1) | NL6505684A (en) |
SE (2) | SE317057B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR200F (en) * | 1965-11-15 | |||
US3541218A (en) * | 1969-06-18 | 1970-11-17 | Lilly Co Eli | Omicron-fluorobenzylaminoguanidine for diabetes |
JPS5051717U (en) * | 1973-09-06 | 1975-05-19 | ||
JPS5391735U (en) * | 1976-12-27 | 1978-07-27 | ||
JPS54121027U (en) * | 1978-02-13 | 1979-08-24 | ||
EP0021120B1 (en) * | 1979-06-01 | 1983-04-06 | The Wellcome Foundation Limited | 3,5-diamino-1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them |
GR68380B (en) * | 1979-06-01 | 1981-12-28 | Wellcome Found | |
FR2549049B1 (en) * | 1983-07-13 | 1986-06-20 | Chauvin Blache Lab | NEW AMIDINES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION |
HU190639B (en) * | 1983-12-12 | 1986-09-29 | Gyogyszerkutato Intezet Kv,Hu | Process for production of new aminoguanidin derivatives |
EP0325936A3 (en) * | 1988-01-16 | 1990-01-17 | Ono Pharmaceutical Co., Ltd. | Aminoguanidine derivatives and inhibitory agents on maillard reaction containing them as active ingredients |
US5891909A (en) * | 1996-03-29 | 1999-04-06 | 3-Dimensional Pharmaceuticals, Inc. | Amidinohydrazones as protease inhibitors |
TW499412B (en) * | 1996-11-26 | 2002-08-21 | Dimensional Pharm Inc | Aminoguanidines and alkoxyguanidines as protease inhibitors |
KR20030022353A (en) | 2000-08-04 | 2003-03-15 | 3-디멘져널 파마슈티칼즈 인코오포레이티드 | Cyclic oxyguanidine protease inhibitors |
-
0
- BE BE663481D patent/BE663481A/xx unknown
-
1964
- 1964-05-05 CH CH801666A patent/CH511216A/en not_active IP Right Cessation
- 1964-05-05 CH CH585464A patent/CH448057A/en unknown
- 1964-05-05 CH CH801766A patent/CH491873A/en not_active IP Right Cessation
-
1965
- 1965-04-26 SE SE5414/65A patent/SE317057B/xx unknown
- 1965-04-26 AT AT806266A patent/AT255433B/en active
- 1965-04-26 AT AT806366A patent/AT255434B/en active
- 1965-04-26 SE SE6816331A patent/SE371640B/xx unknown
- 1965-04-26 AT AT381265A patent/AT255432B/en active
- 1965-04-27 DE DE19651518222 patent/DE1518222A1/en active Pending
- 1965-04-28 IL IL23443A patent/IL23443A/en unknown
- 1965-04-29 ES ES0312384A patent/ES312384A1/en not_active Expired
- 1965-05-03 DK DK224365AA patent/DK107288C/en active
- 1965-05-03 GB GB18547/65A patent/GB1096348A/en not_active Expired
- 1965-05-04 FI FI1086/65A patent/FI42316B/fi active
- 1965-05-04 CS CS6249A patent/CS151461B2/cs unknown
- 1965-05-04 NL NL6505684A patent/NL6505684A/xx unknown
- 1965-05-05 FR FR15815A patent/FR4399M/fr not_active Expired
- 1965-05-05 BR BR169419/65A patent/BR6569419D0/en unknown
- 1965-05-06 JP JP40026185A patent/JPS4842627B1/ja active Pending
-
1966
- 1966-04-28 DK DK218666AA patent/DK111887B/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE663481A (en) | |
CH511216A (en) | 1971-08-15 |
GB1096348A (en) | 1967-12-29 |
CS151461B2 (en) | 1973-10-19 |
AT255433B (en) | 1967-07-10 |
JPS4842627B1 (en) | 1973-12-13 |
FI42316B (en) | 1970-03-31 |
DK107288C (en) | 1967-05-16 |
ES312384A1 (en) | 1966-03-01 |
DE1518222A1 (en) | 1969-06-12 |
CH448057A (en) | 1967-12-15 |
NL6505684A (en) | 1965-11-08 |
FR4399M (en) | 1966-09-05 |
SE371640B (en) | 1974-11-25 |
IL23443A (en) | 1968-09-26 |
SE317057B (en) | 1969-11-10 |
AT255432B (en) | 1967-07-10 |
AT255434B (en) | 1967-07-10 |
DK111887B (en) | 1968-10-21 |
BR6569419D0 (en) | 1973-08-02 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |