DD144665A5 - Verfahren zur herstellung von 1-phenoxy-3-aminopropan-2-olen - Google Patents

Verfahren zur herstellung von 1-phenoxy-3-aminopropan-2-olen Download PDF

Info

Publication number: DD144665A5
Authority: DD; German Democratic Republic
Prior art keywords: compound; propanol; general formula; methoxyethyl; phenoxy
Prior art date: 1978-06-30

Application number

DD79213965A

Other languages

German (de)

English (en)

Inventor

Eugene W Byrnes

Gustav B R Samuelsson

Axel K G Aberg

Original Assignee

Haessle Ab

Priority date (The priority date 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 date listed.)

1978-06-30

Filing date

1979-06-28

Publication date

1980-10-29

1979-06-28 Application filed by Haessle Ab filed Critical Haessle Ab

1980-10-29 Publication of DD144665A5 publication Critical patent/DD144665A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims description 99
-1 4- (2-methoxyethyl) -phenoxy Chemical group 0.000 claims description 98
238000000034 method Methods 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 27
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 25
239000007858 starting material Substances 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
239000002585 base Substances 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 6
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125000003277 amino group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
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XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims 1
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102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
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206010020772 Hypertension Diseases 0.000 description 1
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CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
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239000000853 adhesive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
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150000001340 alkali metals Chemical class 0.000 description 1
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125000002947 alkylene group Chemical group 0.000 description 1
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239000004202 carbamide Substances 0.000 description 1
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235000013355 food flavoring agent Nutrition 0.000 description 1
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238000001640 fractional crystallisation Methods 0.000 description 1
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230000003301 hydrolyzing effect Effects 0.000 description 1
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239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
208000028756 lack of coordination Diseases 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
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230000033001 locomotion Effects 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
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235000019341 magnesium sulphate Nutrition 0.000 description 1
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230000007246 mechanism Effects 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
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238000012986 modification Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960001412 pentobarbital Drugs 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000036581 peripheral resistance Effects 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
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239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
CPKXFZDVSRECFF-UHFFFAOYSA-M potassium;4-(3-hydroxypropyl)phenolate Chemical compound [K+].OCCCC1=CC=C([O-])C=C1 CPKXFZDVSRECFF-UHFFFAOYSA-M 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000003825 pressing Methods 0.000 description 1
239000002987 primer (paints) Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000004080 punching Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000003087 receptor blocking agent Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000020712 soy bean extract Nutrition 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229940124629 β-receptor antagonist Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Cardiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Pulmonology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)

DD79213965A 1978-06-30 1979-06-28 Verfahren zur herstellung von 1-phenoxy-3-aminopropan-2-olen DD144665A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SE7807408A SE7807408L (sv)	1978-06-30	1978-06-30	Hjertaktiva foreningar

Publications (1)

Publication Number	Publication Date
DD144665A5 true DD144665A5 (de)	1980-10-29

Family

ID=20335352

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213965A DD144665A5 (de)	1978-06-30	1979-06-28	Verfahren zur herstellung von 1-phenoxy-3-aminopropan-2-olen

Country Status (11)

Country	Link
EP (1)	EP0007294A3 (no)
JP (1)	JPS559084A (no)
AU (1)	AU4831779A (no)
DD (1)	DD144665A5 (no)
DK (1)	DK275179A (no)
FI (1)	FI792059A7 (no)
NO (1)	NO792113L (no)
NZ (1)	NZ190810A (no)
SE (1)	SE7807408L (no)
SU (3)	SU843733A3 (no)
ZA (1)	ZA792939B (no)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS55124742A (en) *	1979-03-20	1980-09-26	Kyowa Hakko Kogyo Co Ltd	Novel aminoalcohol derivative
JPS5746946A (en) *	1980-07-09	1982-03-17	Sandoz Ag	3-aminopropoxyphenyl derivative, manufacture and medicine containing same
US4410548A (en) *	1980-07-09	1983-10-18	Reckitt & Colman Products Limited	Propanolamine derivatives
DE3125870C2 (de) *	1980-07-09	1994-09-15	William John Louis	3-Aminopropoxyphenyl Derivate, ihre Herstellung und sie enthaltende Arzneimittel
FR2497194B1 (fr) *	1980-08-07	1985-06-14	Sandoz Sa	Nouveaux composes phenoliques
GB8519154D0 (en) *	1985-07-30	1985-09-04	Ici Plc	Aromatic ethers
DE3544172A1 (de) *	1985-12-13	1987-06-19	Lentia Gmbh	Neue kristalline salze von aryloxy-propanolaminen, verfahren zu ihrer herstellung und ihre verwendung
JPS6341451A (ja) *	1986-08-06	1988-02-22	Nippon Kayaku Co Ltd	エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物
DE3706585A1 (de) *	1987-02-25	1988-09-08	Schering Ag	Aryl- und aryloxy-substituierte tert.-alkylenamine, verfahren zu ihrer herstellung und ihre pharmazeutische verwendung
GB8925032D0 (en) *	1989-11-06	1989-12-28	Ici Plc	Chemical compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DD80923A (no) *
US3261829A (en) *	1964-08-12	1966-07-19	Searle & Co	Spiro(steroidal-6,3'-1-pyrazolines) and process
FR2119843B1 (no) *	1970-12-28	1974-03-22	Laroche Navarro Labo
FR2119844B1 (no) *	1970-12-28	1974-03-22	Laroche Navarro Labo
ZA754241B (en) *	1974-11-01	1976-06-30	Haessle Ab	New amines

1978
- 1978-06-30 SE SE7807408A patent/SE7807408L/xx unknown
1979
- 1979-06-13 ZA ZA792939A patent/ZA792939B/xx unknown
- 1979-06-22 AU AU48317/79A patent/AU4831779A/en not_active Abandoned
- 1979-06-22 NO NO792113A patent/NO792113L/no unknown
- 1979-06-25 NZ NZ190810A patent/NZ190810A/xx unknown
- 1979-06-26 EP EP79850061A patent/EP0007294A3/en not_active Withdrawn
- 1979-06-28 DD DD79213965A patent/DD144665A5/de unknown
- 1979-06-29 FI FI792059A patent/FI792059A7/fi not_active Application Discontinuation
- 1979-06-29 SU SU792784303A patent/SU843733A3/ru active
- 1979-06-29 DK DK275179A patent/DK275179A/da unknown
- 1979-06-30 JP JP8206379A patent/JPS559084A/ja active Pending
1980
- 1980-05-15 SU SU802921247A patent/SU873872A3/ru active
- 1980-05-15 SU SU802921298A patent/SU860692A1/ru active

Also Published As

Publication number	Publication date
AU4831779A (en)	1980-01-03
EP0007294A2 (en)	1980-01-23
ZA792939B (en)	1980-06-25
SE7807408L (sv)	1979-12-31
JPS559084A (en)	1980-01-22
SU873872A3 (ru)	1981-10-15
SU843733A3 (ru)	1981-06-30
FI792059A7 (fi)	1981-01-01
EP0007294A3 (en)	1980-03-19
NZ190810A (en)	1981-10-19
DK275179A (da)	1979-12-31
NO792113L (no)	1980-01-03
SU860692A1 (ru)	1981-08-30

Publication	Publication Date	Title
DE2558501C2 (no)	1987-07-16
DE1643262C3 (de)	1975-06-26	i-Phenoxy^-hydroxy-S-alklyaminopropane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2332837C2 (de)	1982-04-08	Amine, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2502993A1 (de)	1975-09-04	Amine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DD201305A5 (de)	1983-07-13	Verfahren zur herstellung von in 7-stellung substituierten benzopyranen
EP0074014A1 (de)	1983-03-16	2-(2'-Hydroxy-3'-(1,1-dimethylpropylamino)-propoxy)-beta-phenylpropiophenon, seine Säureadditionssalze, Verfahren zu seiner Herstellung und Arzneimittel
CH642066A5 (de)	1984-03-30	3-indolyl-tert.-butylaminopropanole, verfahren zu deren herstellung und sie enthaltende pharmazeutische mittel.
CH640227A5 (de)	1983-12-30	Aminoalkoxyphenyl-derivate.
DE2531312A1 (de)	1976-05-06	Aminderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE2418030A1 (de)	1974-11-07	Amine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0007294A2 (en)	1980-01-23	Membrane stabilizing compounds having beta-receptor blocking activity, their preparation, method for treatment of arrhythmic conditions, and pharmaceutical preparations containing same
EP0027928B1 (de)	1983-03-09	Piperidinderivate von 4,5-Dialkyl-3-hydroxy-pyrrol-2-carbonsäureestern, ihre Herstellung und diese enthaltende pharmazeutische Zubereitungen
EP0038936B1 (de)	1983-04-27	Neue 1-Aryloxy-3-alkylamino-2-propanole und Verfahren zu ihrer Herstellung
DE2530613A1 (de)	1976-05-06	Aminderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel
EP0000727B1 (de)	1980-08-20	3-(4-(1,3-Diazacycloalken-2-yl)-phenyl)-1,2-benzisothiazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel.
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
EP0035733B1 (de)	1983-09-14	Neue 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-aminopropane und Verfahren zu ihrer Herstellung
DE2743493A1 (de)	1978-04-13	Amine, verfahren zu deren herstellung und sie enthaltende arzneimittel
DE3014738C2 (no)	1989-08-03
DD213207A5 (de)	1984-09-05	Verfahren zur herstellung von phenoxy-1-alkylaminopropanolen-2
EP0086256B1 (de)	1985-08-21	1-(2,4-Dichlorphenoxy)-3-(3,4-dimethoxy-Beta-phenethylamino)-2-propanol, Verfahren zu seiner Herstellung und dieses enthaltende pharmazeutische Zusammensetzungen
EP0035734B1 (de)	1983-09-21	Neue 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-aminopropane und Verfahren zu ihrer Herstellung
DE2844353C2 (de)	1984-01-26	p-Isopropylthiophenoxypropanolamin-Derivate, Verfahren zu deren Herstellung und Arzneimittel
EP0073016B1 (de)	1985-11-27	Neue 1-Aryloxy-3-alkylamino-2-propanole und Verfahren zu ihrer Herstellung
EP0073011B1 (de)	1986-04-02	Neue 1-Aryloxy-3-alkinylamino-2-propanole und Verfahren zu ihrer Herstellung