DE1793808C3 - 1 - (3-Hydroxymethyl-phenoxy) -2-hydroxy-3-sec-butylaminopropane, its acid addition salts, processes for their preparation and pharmaceuticals containing them - Google Patents
1 - (3-Hydroxymethyl-phenoxy) -2-hydroxy-3-sec-butylaminopropane, its acid addition salts, processes for their preparation and pharmaceuticals containing themInfo
- Publication number
- DE1793808C3 DE1793808C3 DE19671793808 DE1793808A DE1793808C3 DE 1793808 C3 DE1793808 C3 DE 1793808C3 DE 19671793808 DE19671793808 DE 19671793808 DE 1793808 A DE1793808 A DE 1793808A DE 1793808 C3 DE1793808 C3 DE 1793808C3
- Authority
- DE
- Germany
- Prior art keywords
- sec
- hydroxy
- hydroxymethyl
- phenoxy
- acid addition
- 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
- 239000002253 acid Substances 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 6
- 239000011780 sodium chloride Substances 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title description 3
- MSCNKABBKJRCLR-UHFFFAOYSA-N OCC=1C=C(OCC(CNC(C)CC)O)C=CC1 Chemical compound OCC=1C=C(OCC(CNC(C)CC)O)C=CC1 MSCNKABBKJRCLR-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- -1 3-hydroxymethyl - phenoxy Chemical group 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- VKMGSWIFEHZQRS-NSHDSACASA-N (1R)-1-(3,4-dichlorophenyl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NC[C@H](O)C1=CC=C(Cl)C(Cl)=C1 VKMGSWIFEHZQRS-NSHDSACASA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N (-)-tartaric acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- XTYWGSDRLPZAQF-UHFFFAOYSA-N 1-(butan-2-ylamino)propan-2-ol Chemical compound CCC(C)NCC(C)O XTYWGSDRLPZAQF-UHFFFAOYSA-N 0.000 description 1
- OKVJCVWFVRATSG-UHFFFAOYSA-N 3-hydroxybenzyl alcohol Chemical compound OCC1=CC=CC(O)=C1 OKVJCVWFVRATSG-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-Chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N Benzil Chemical group C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 206010007521 Cardiac arrhythmias Diseases 0.000 description 1
- 210000004351 Coronary Vessels Anatomy 0.000 description 1
- 229960001270 D- TARTARIC ACID Drugs 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N Sec-Butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- NXQMNKUGGYNLBY-UHFFFAOYSA-N Toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 description 1
- 229950000245 Toliprolol Drugs 0.000 description 1
- WOFJRZLKWHCFCL-UHFFFAOYSA-N [3-(oxiran-2-ylmethoxy)phenyl]methanol Chemical compound OCC1=CC=CC(OCC2OC2)=C1 WOFJRZLKWHCFCL-UHFFFAOYSA-N 0.000 description 1
- 230000002908 adrenolytic Effects 0.000 description 1
- 230000003276 anti-hypertensive Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 229940079593 drugs Drugs 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003287 optical Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 230000000069 prophylaxis Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
Description
oderor
-CH(OH)-CH2-HaI-CH (OH) -CH 2 -HaI
und Hai ein Halogenatom bedeutet, mit sek.-Butyiamin umsetzt und gewünschtenfalls die erhaltene Verbindung in ein physiologisch verträgliches Säureadditionssalz überführt.and Hai means a halogen atom, with sec-butyiamine converts and, if desired, the compound obtained into a physiologically compatible one Acid addition salt transferred.
3. Arzneimittel, enthaltend als Wirkstoff 1 -(3-Hydroxymethyl - phenoxy) - 2 - hydroxy - 3 - sek. - butylamino-propan bzw. dessen physiologisch verträgliche Säureadditionssalze.3. Medicines containing 1 - (3-hydroxymethyl - phenoxy) - 2 - hydroxy - 3 - sec. - butylamino propane or its physiologically acceptable acid addition salts.
Die Erfindung betrifft die in den Ansprüchen gekennzeichneten Gegenstände.The invention relates to the objects characterized in the claims.
Die Verbindung gemäß der Erfindung kann durch Umsetzung einer Verbindung der allgemeinen FormelThe compound according to the invention can be prepared by reacting a compound of the general formula
(D(D
* V-Q-CH2-Z * VQ-CH 2 -Z
CH2OH
in der Z die GruppeCH 2 OH
in the Z the group
-CH CH,-CH CH,
-CH(OH)-CH2-HaI-CH (OH) -CH 2 -HaI
Und Hai ein Halogenatom bedeutet, mit sek.-Butyltmin hergestellt werden.And Hai means a halogen atom, with sec-butyltmin getting produced.
Das Epoxid der Formel 1 läßt sich leicht durch Umsetzung von Epichlorhydrin mil 3-Hydroxymethylphenol bzw. -phenolat herstellen. Durch Umsetzung des Epoxids der Formel I mil Halogenwasserstoffsäuren sind die entsprechenden Halogenhydrine der Formel I darstellbar.The epoxide of formula 1 can easily be obtained by reacting epichlorohydrin with 3-hydroxymethylphenol or phenolate. By reacting the epoxide of formula I with hydrohalic acids the corresponding halohydrins of the formula I can be prepared.
Die erfindungsgemäße Verbindung besitzt ein asymmetrisches Kohlenstoffatom und kommt daher als Racemat wie auch in Form der optischen Antipoden vor. Letztere können außer durch Racematenlrennung mit Hilfe von üblichen Hilfssäuren wie Dibenzoyl-The compound according to the invention has an asymmetric one Carbon atom and therefore comes as a racemate as well as in the form of the optical antipodes before. The latter can, in addition to the resolution of racemates, with the aid of customary auxiliary acids such as dibenzoyl
D-weinsäure cdcr i>-3-Bromcampher-8-sulfonsüure auch durch Einsetzen von optisch aktivem Ausganusmaterial erhalten weiden. Das erfindungsgemiiüe 1 - (3 - Hydroxymethyl - phenoxy) - 2 - hydroxy - 3 - sekbutylamino-piopan kann in üblicher Weise in die physiologisch verträglichen Säureadditionssalze überführt werden. Geeignete Säuren sind beispielsweise Salz-, Bromwasserstoff-, Schwefel-, Mcthansulfon-, Malein-, Essig-, Oxal-, Milch-, Weinsäure oder 8-Chlortheophyllin.D-tartaric acid cdcr i> -3-bromocamphor-8-sulfonic acid also obtained by inserting optically active outlet material. The invention 1 - (3 - hydroxymethyl - phenoxy) - 2 - hydroxy - 3 - secbutylamino-piopane can be converted into the physiologically acceptable acid addition salts in the usual way will. Suitable acids are, for example, hydrochloric, hydrogen bromide, sulfur, methanesulfone, Maleic, acetic, oxalic, lactic, tartaric acid or 8-chlorotheophylline.
Die erfindungsgemäße Verbindung b?.«. deren physiologisch verträgliche Säureadditionssalze haben im Tierversuch an Meerschweinchen wertvolle therapeutische, insbesondere /.'-adrenolytische Eigenschaf-The compound according to the invention b ?. «. their physiological In animal experiments on guinea pigs, compatible acid addition salts have valuable therapeutic, especially /.'- adrenolytic properties
,5 ten gezeigt und können daher beispielsweise zur Behandlung oder Prophylaxe von Erkrankungen der Herzkranzgefäße und zur Behandlung von Herz- «rrythmien, insbesondere von Tachycardien. in der Humanmedizin eingesetzt werden. Auch die blutdrucksenkenden Eigenschaften der Verbindung sind therapeutisch interessant., 5 th and can therefore be used, for example, for the treatment or prophylaxis of diseases of the coronary arteries and for the treatment of cardiac arrhythmias, in particular of tachycardias. be used in human medicine. The antihypertensive properties of the compound are also of therapeutic interest.
VergleichsversuchComparative experiment
Die Prüfung auf isoprolerenol-antagonistische Wirkung erfolgte an lebenden Meerschweinchen. Als Standardsubstanz diente 3,4-Dichlorisoproterenol (DCI), dessen Wirkung gleich 1 gesetzt wurde.Testing for isoprolerenol-antagonistic effect took place on live guinea pigs. 3,4-dichloroisoproterenol was used as the standard substance (DCI), the effect of which was set equal to 1.
Verbindungconnection
A. Stand der TechnikA. State of the art
(belgische Patentschriften 6 41 133
und 6 52 336)(Belgian patents 6 41 133
and 6 52 336)
l-m-Tolyloxy^-hydroxy^-isopropylamino-propan
(Wirkstoff des Doberol*)lm-Tolyloxy ^ -hydroxy ^ -isopropylamino-propane
(Active ingredient of Doberol *)
B. Gemäß Erfindung
l-(3-Hydroxymethyl-phcnoxy)-B. According to the invention
l- (3-hydroxymethyl-phenoxy) -
Isoprolcrenol-Isoprolcrenol
antagun.antagun.
WirkuncEffect
5faeh DCl5faeh DCl
13,0lach DCI13.0 flat DCI
2-hydroxy-3-sek.-butylamino-propan2-hydroxy-3-sec-butylamino-propane
Die Einzeldosis der erfindungsgemäßen Substanz liegt bei 1 bis 300 mg; vorzugsweise 5 bis 100 mg (oral) bzw. 1 bis 20 mg (parenteral).The single dose of the substance according to the invention is 1 to 300 mg; preferably 5 to 100 mg (orally) or 1 to 20 mg (parenteral).
Die galenische Verarbeitung der erfindungsgemäßen Verbindung erfolgt in üblicher Weise. Die Formulierungen enthalten beispielsweise 9 oder 12.5% des Wirkstoffs.The galenic processing of the compound according to the invention is carried out in the customary manner. The formulations contain, for example, 9 or 12.5% of the active ingredient.
Die folgenden Beispiele crlüulern die Erfindung.The following examples illustrate the invention.
l-(3-Hydroxymethylphenoxy)-2-hydroxy-3-sek.-biityI-amino-propan 1- (3-hydroxymethylphenoxy) -2-hydroxy-3-sec-biityI-aminopropane
11,6 g (0.064MoI) l-(3-Hydroxymethylphenoxy)-2,3-epoxypropan werden in 100 ml Äthanol gelöst und nach Zugabe von 8.8 g (0,12MoI) sek.-Butylamin 3 Stunden unter Rückfluß gekocht. Nach Abdestillieren des Lösungsmittels im Vakuum verbleib! ein öliger Rückstand, der in wenig Äthanol gelöst und mit Äther versetzt wird. Die Base scheidet sich kristallin ab und wird noch zweimal aus Äthanol Äther umkristallisiert.11.6 g (0.064MoI) 1- (3-hydroxymethylphenoxy) -2,3-epoxypropane are dissolved in 100 ml of ethanol and after the addition of 8.8 g (0.12 mol) sec-butylamine Boiled under reflux for 3 hours. After the solvent has been distilled off, remain in vacuo! an oily one Residue, which is dissolved in a little ethanol and washed with ether is moved. The base separates out in crystalline form and is recrystallized twice more from ethanol ether.
Analyse:
Berechnet
ücfundcn .Analysis:
Calculated
find.
C 66,15. H 9.89. N 5.73"
C 66,3. H 9,76. N 5.81"C 66.15. H 9.89. N 5.73 "
C 66.3. H 9.76. N 5.81 "
Ausbeute: 11." g; Fp. 73 bis 75 C.Yield: 11 ″ g; m.p. 73 to 75 C.
3 ^ 43 ^ 4
FormulierunasbeispielFormulation example
2. Gelatine-Kapseln I. Tabletten2. Gelatin capsules I. Tablets
Der Inhalt der Kapseln setzt sich wie folsit !-(.-.-Hydroxymethyl-phenoxy)- zusammen'The contents of the capsules settle like folsit ! - (.-.- hydroxymethyl-phenoxy) - together '
2-hydroxy-3-sek.-butylamino- S2-hydroxy-3-sec-butylamino- S
propan - HCI 40 0 m» ' -(3-Hydroxymeihyl-phcnoxy)-propane - HCI 40 0 m »'- (3-Hydroxymethyl-phcnoxy) -
Maissiärke KS4() m» 2-hydroxy-3-sek.-bulyl-amino-Corn starch KS4 () m »2-hydroxy-3-sec.-bulyl-amino-
sek.-Calciumphosphat 240 0 m» propan ■ HCI 25,0 mgsecondary calcium phosphate 240 0 m »propane ■ HCl 25.0 mg
Magnesiumstearal 1^0 m» Maisstärke 175,0 mg Magnesium stearal 1 ^ 0 m »corn starch 175.0 mg
445^g~ 10 2l)0'OmS445 ^ g ~ 10 2l) 0 ' Om S.
HerstellungManufacturing
Die einzelnen Bestandsleile werden intensiv mit- HerstellungThe individual parts of the existing structure are intensively produced
einander vermischt und das Gemisch in üblicher Weise Die Bestandteile des Kapselinhalts werden intensivmixed together and the mixture in the usual way The components of the capsule contents are intense
granuliert. Das Granulat wird zu Tabletten von i5 vermischt, und 200-mg-Portionen des Gemischesgranulated. The granules are mixed into tablets of i 5 , and 200 mg servings of the mixture
445 mg Gewicht verpreßt, von denen jede 40 m» werden in Gelaiinc-Kapseln geeianeter Größe abge-445 mg weight, of which each 40 m »are compressed into gelinc capsules of a suitable size.
Wirkstoff enthält. PuH1 Jedc Kapsd enthält 25 ma des Wirkstoffs.Contains active ingredient. PuH 1 Jedc Kapsd contains 25 ma of the active ingredient.
Claims (2)
in der Z die GruppeCH 2 OH
in the Z the group
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671793808 DE1793808C3 (en) | 1967-12-22 | 1 - (3-Hydroxymethyl-phenoxy) -2-hydroxy-3-sec-butylaminopropane, its acid addition salts, processes for their preparation and pharmaceuticals containing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19671793808 DE1793808C3 (en) | 1967-12-22 | 1 - (3-Hydroxymethyl-phenoxy) -2-hydroxy-3-sec-butylaminopropane, its acid addition salts, processes for their preparation and pharmaceuticals containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1793808B2 DE1793808B2 (en) | 1975-08-14 |
| DE1793808A1 DE1793808A1 (en) | 1975-08-14 |
| DE1793808C3 true DE1793808C3 (en) | 1976-04-29 |
Family
ID=
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