CH634822A5 - Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. - Google Patents
Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. Download PDFInfo
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- CH634822A5 CH634822A5 CH550481A CH550481A CH634822A5 CH 634822 A5 CH634822 A5 CH 634822A5 CH 550481 A CH550481 A CH 550481A CH 550481 A CH550481 A CH 550481A CH 634822 A5 CH634822 A5 CH 634822A5
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
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- 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
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
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- 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
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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Abstract
Description
Die Erfindung betrifft ein Verfahren zur Herstellung neuer l-(2-Phenyl-2-hydroxyäthylamino)-3-phenoxypropan-2-olen der Formel I The invention relates to a process for the preparation of new 1- (2-phenyl-2-hydroxyethylamino) -3-phenoxypropan-2-ols of the formula I.
60 60
ch-ch-nh-ch9-ch-cho-0 ch-ch-nh-ch9-ch-cho-0
I I ^ l 2 I I ^ l 2
OH k. OH OH k. OH
.(I) . (I)
3 3rd
634822 634822
und ihrer Säureadditionssalze, die sich zur Verwendung in Arzneimitteln und als Zwischenprodukte für die Herstellung von Arzneistoffen eignen. Die Basen der Formel I können dabei als Racemate, als Gemische von Racematen oder in Form einzelner optischer Antipoden vorliegen bzw. in den Salzen enthalten sein. and their acid addition salts, which are suitable for use in drugs and as intermediates for the manufacture of drugs. The bases of the formula I can be present as racemates, as mixtures of racemates or in the form of individual optical antipodes or can be present in the salts.
Die Reste R, bis R6 in der Formel I haben folgende Bedeutung: The radicals R 1 to R 6 in formula I have the following meaning:
Ri Wasserstoff, Halogen, Hydroxy, Amino, Alkyl, Alkoxy, Alkanoylamino oder Alkylsulfonylamino, Ri is hydrogen, halogen, hydroxy, amino, alkyl, alkoxy, alkanoylamino or alkylsulfonylamino,
R2 Wasserstoff, Hydroxy, Alkyl, Alkoxy oder Amino-carbonyl, R2 is hydrogen, hydroxy, alkyl, alkoxy or amino-carbonyl,
R3 Wasserstoff oder Halogen, Alkyl oder Alkoxy, R4 Wasserstoff, Methyl oder Äthyl, R3 is hydrogen or halogen, alkyl or alkoxy, R4 is hydrogen, methyl or ethyl,
R5 und R6 Wasserstoff, Halogen, Alkyl, Alkoxy, Hydroxy, Amino, Cyano, Carboxy, Carbalkoxy, Aminocarbo-nyl, Alkylenaminocarbonyl, Alkanoylamino oder Alkylsulfonylamino, R5 and R6 are hydrogen, halogen, alkyl, alkoxy, hydroxyl, amino, cyano, carboxy, carbalkoxy, aminocarbonyl, alkyleneaminocarbonyl, alkanoylamino or alkylsulfonylamino,
mit der Massgabe, dass falls with the proviso that if
Ri Wasserstoff, 4-Hydroxy oder 4-Chlor, Ri is hydrogen, 4-hydroxy or 4-chlorine,
R2 Wasserstoff, R2 hydrogen,
R3 Wasserstoff, R3 is hydrogen,
R4 Methyl und R4 is methyl and
R5 Wasserstoff oder 2-Halogen bedeutet, R5 represents hydrogen or 2-halogen,
R6 nicht für 4-Hydroxy steht. R6 does not represent 4-hydroxy.
Soweit in den obigen Definitionen Alkyl- oder Alkoxy-gruppen genannt sind bzw. andere Gruppen, die Alkyl- oder Alkoxygruppen enthalten, sind solche Alkyl- oder Alkoxy-gruppen gemeint, die 1 bis 4 Kohlenstoffatome aufweisen und geradkettig oder verzweigt sein können. Die Acylreste in den Alkanoylamino- oder Alkylsulfonylaminogruppen leiten sich von niederen aliphatischen Carbonsäuren oder Niederalkansulfonsäuren ab, die Alkylenaminocarbonyl-gruppen enthalten niedere Alkylengruppen. To the extent that alkyl or alkoxy groups are mentioned in the above definitions or other groups which contain alkyl or alkoxy groups, those alkyl or alkoxy groups are meant which have 1 to 4 carbon atoms and can be straight-chain or branched. The acyl radicals in the alkanoylamino or alkylsulfonylamino groups are derived from lower aliphatic carboxylic acids or lower alkanesulfonic acids, and the alkylene aminocarbonyl groups contain lower alkylene groups.
Hervorzuheben sind folgende Substituenten-Bedeutun-gen: The following substituent meanings should be emphasized:
R! Wasserstoff, Chlor oder Brom, Hydroxygruppe, Cj-oder C2-Alkyl, vor allem Methyl, Croder C2-Alkoxy, vor allem Methoxy, Acetylamino, Propionylamido oder Me-thansulfonamido; R! Hydrogen, chlorine or bromine, hydroxyl group, C 1 -C or C 2 -alkyl, especially methyl, Cr or C 2 -alkoxy, especially methoxy, acetylamino, propionylamido or methanesulfonamido;
R2 Wasserstoff, Hydroxygruppe, Methoxy; R3 Wasserstoff, Chlor oder Brom, Hydroxygruppe, Methyl oder Methoxy; R2 is hydrogen, hydroxy group, methoxy; R3 is hydrogen, chlorine or bromine, hydroxyl group, methyl or methoxy;
R4 Wasserstoff oder Methylgruppe; R4 is hydrogen or methyl group;
Rs Wasserstoff, Fluor, Chlor oder Brom, Methoxy, eine Hydroxy-, Cyano-, Carboxy-, Aminocarbonyl- oder Aminogruppe, eine Carbalkoxy-, Àlkylenaminocarbonyl- oder Acylaminogruppe, die jeweils bis zu 3 C-Atome enthalten. Rs is hydrogen, fluorine, chlorine or bromine, methoxy, a hydroxy, cyano, carboxy, aminocarbonyl or amino group, a carbalkoxy, alkylene aminocarbonyl or acylamino group, each of which contains up to 3 carbon atoms.
Das Verfahren ist dadurch gekennzeichnet, dass man ein Epoxyd der Formel IIa t The process is characterized in that an epoxide of the formula IIa t
t r2 t r2
r. r.
worin R'j, R'2 und R'3 die Bedeutung R,, R2 und R3 haben oder eine durch eine hydrogenolytisch abspaltbare Gruppe geschützte Hydroxy- oder Aminogruppe bedeuten, mit einem Phenoxypropanolamin der Formel III wherein R'j, R'2 and R'3 have the meaning R ,, R2 and R3 or a hydroxyl or amino group protected by a hydrogenolytically removable group, with a phenoxypropanolamine of the formula III
i r, i r,
"5 "5
i-CH«-CH0H-CHo-NH i-CH "-CH0H-CHo-NH
(III) (III)
worin R's und R'6 die Bedeutung von R5 und Re haben oder eine durch eine hydrogenolytisch abspaltbare Gruppe geschützte Hydroxy- oder Aminogruppe bedeuten, umsetzt, und eine gegebenenfalls vorhandene Schutzgruppe hydrogenolytisch abspaltet. in which R's and R'6 have the meaning of R5 and Re or a hydroxyl or amino group protected by a group that can be split off by hydrogenolysis, and a protective group which may be present is split off hydrogenolytically.
Statt von der Verbindung IIa kann man auch von dem Chlorhydrin der Formel ch0h-chr/.-c1 Instead of the compound IIa, one can also use the chlorohydrin of the formula ch0h-chr /.- c1
r. r.
(Hb) (Hb)
ausgehen, aus dem sich unter den Reaktionsbedingungen die Verbindung IIa bildet. start from which the compound IIa forms under the reaction conditions.
Die durch den Disclaimer ausgeschlossenen Verbindungen sind Gegenstand der DE-OS 2 502 993. The compounds excluded by the disclaimer are the subject of DE-OS 2 502 993.
Für das erfindungsgemässe Verfahren können auch optisch aktive Vorstufen eingesetzt und gegebenenfalls unmittelbar reine optische Isomere erhalten werden. Bei dem Verfahren anfallende Racemate können nach üblichen Methoden in die optisch aktiven Verbindungen aufgetrennt werden. Optically active precursors can also be used for the process according to the invention and, if appropriate, pure optical isomers can be obtained directly. Racemates obtained in the process can be separated into the optically active compounds by customary methods.
Die Basen der Formel I werden gegebenenfalls nach üblichen Methoden in Salze übergeführt oder, falls sie als Salze vorliegen, in Salze anderer Säuren oder in freie Basen. The bases of the formula I are optionally converted into salts by customary methods or, if they are present as salts, into salts of other acids or into free bases.
Alle Ausgangsstoffe können nach bekannten Methoden erhalten werden. All starting materials can be obtained by known methods.
Die Verbindungen der Formel I haben cardiovasculäre Wirkungen und sind ausserdem noch gefasserweiternd, antihypertensiv und antiarrhytmisch wirksam. Sie können beispielsweise als Wirkstoffe selektiv wirksamer Herzmittel verwendet werden, da sie eine positiv inotrope Wirkung mit nur geringer frequenzsteigernder Wirkung verbinden. The compounds of formula I have cardiovascular effects and are also vasodilatory, antihypertensive and antiarrhythmic. For example, they can be used as active ingredients in selectively active cardiac agents, since they combine a positive inotropic effect with only a slight frequency-increasing effect.
Dies zeigt sich beispielsweise in den Ergebnissen der Prüfung am isolierten Meerschweinchen-Herzvorhof. Die im üblichen Test mit ljig Wirkstoff/ml erhaltenen Werte der Amplitudenänderung (A) und der Frequenzänderung (F) betragen für l-[2-(4-Hydroxyphenyl)-2-hydroxyäthylamino]-4-cyanophenoxy)-propanol-(2) A: +37%, F: +7% und für 1-[2-(3,5-Dihydroxyphenyl)-2-hydroxyäthylaminol-3-(4-tolyl-oxy)-propanol-2 A: +36%, F: —3%. This can be seen, for example, in the results of the test on the isolated guinea pig atrium. The values of the amplitude change (A) and the frequency change (F) obtained in the usual test with ly active ingredient / ml for l- [2- (4-hydroxyphenyl) -2-hydroxyethylamino] -4-cyanophenoxy) propanol- (2) A: + 37%, F: + 7% and for 1- [2- (3,5-dihydroxyphenyl) -2-hydroxyethylaminol-3- (4-tolyloxy) propanol-2 A: + 36%, F : —3%.
Für die Anwendung werden die neuen Verbindungen mit den in der galenischen Pharmazie üblichen Hilfsstoffen zu gebräuchlichen Arzneimittelformen verarbeitet, z.B. zu Tabletten, Dragées, Kapseln, Tinkturen, Injektionslösungen, Suppositorien. For use, the new compounds are processed with the auxiliaries customary in pharmaceutical pharmacy to form common pharmaceutical forms, e.g. to tablets, dragées, capsules, tinctures, solutions for injection, suppositories.
Die Einzeldosis beträgt im allgemeinen zwischen etwa 1 und 100 mg, vorzugsweise 5 bis 50 mg, in Abhängigkeit von Applikationsform, Wirkstoff und Körpergewicht der zu behandelnden Personen. The single dose is generally between about 1 and 100 mg, preferably 5 to 50 mg, depending on the form of administration, active ingredient and body weight of the people to be treated.
5 5
10 10th
15 15
20 20th
25 25th
30 30th
35 35
40 40
45 45
50 50
55 55
60 60
65 65
634822 634822
4 4th
Das folgende Beispiel soll das Herstellungsverfahren der Wirkstoffe näher erläutern: The following example is intended to explain the manufacturing process of the active ingredients in more detail:
Die Bestandteile werden in üblicher Weise zu Tabletten von 600 mg Gewicht verarbeitet. Gewünschtenfalls kann der Wirkstoffgehalt erhöht oder vermindert und die Traubenzuckermenge entsprechend vermindert oder erhöht werden. The ingredients are processed in the usual way to tablets of 600 mg weight. If desired, the active substance content can be increased or decreased and the amount of glucose reduced or increased accordingly.
Suppositorien Zusammensetzung: Suppository composition:
Wirkstoff gemäss der Erfindung Laktose, gepulvert Kakao-Butter Active ingredient according to the invention lactose, powdered cocoa butter
50 Gew.-Teile 45 Gew.-Teile 1605 Gew.-Teile 50 parts by weight 45 parts by weight 1605 parts by weight
Die Bestandteile werden in üblicher Weise zu Suppositorien von 1,7 g Gewicht verarbeitet. The ingredients are processed in the usual way into suppositories weighing 1.7 g.
Kapseln Capsules
Zusammensetzung: Composition:
l-[2-(3,5-Dihydroxyphenyl)-2-hydroxyäthyl-amino]-3-(4-tolyloxy)-propanol-2 10 Gew.-Teile 1- [2- (3,5-Dihydroxyphenyl) -2-hydroxyethylamino] -3- (4-tolyloxy) propanol-2 10 parts by weight
Laktose 490 Gew.-Teile Lactose 490 parts by weight
Maisstärke 400 Gew.-Teile Corn starch 400 parts by weight
Je 1000 mg der fein pulverisierten Mischung werden in Hargelatinekapseln abgefüllt. 1000 mg each of the finely powdered mixture are filled into hargelatine capsules.
Die folgenden Beispiele sollen die Herstellungsverfahren der Wirkstoffe näher erläutern: The following examples are intended to explain the manufacturing processes for the active ingredients:
Beispiel s 1 -[2-(3-Hydroxyphenyl)-2-hydroxy-äthylamino]-3-(2-cyano-phenoxy)-propanol-2-fumarat a) 11,3 g2-(3-Benzyloxyphenyl)-äthylenoxyd (Kp0,! 152-155°C) und 16,8 g l-Benzylamino-3-(2-cyanophenoxy)-propanol-2- (Fp. 181-182 °C) in 50 ml Alkohol werden 8 Example s 1 - [2- (3-hydroxyphenyl) -2-hydroxyethylamino] -3- (2-cyano-phenoxy) propanol-2-fumarate a) 11.3 g2- (3-benzyloxyphenyl) ethylene oxide ( Kp0,! 152-155 ° C) and 16.8 g of l-benzylamino-3- (2-cyanophenoxy) propanol-2- (mp. 181-182 ° C) in 50 ml of alcohol are 8
io Stunden unter Rückfluss gekocht, Anschliessend wird der Alkohol im Vakuum abdestilliert, der Rückstand in Essigester aufgenommen und bis zur schwach sauren Reaktion mit ätherischer Salzsäure versetzt. Man lässt über Nacht stehen, saugt ab und trocknet. Das Hydrochlorid des l-[2-(3-Benzyl-is oxy-phenyl)-2-hydroxy-N-benzyl-äthylamino]-3-(2-cyano-phenoxy)-propanol-2 schmilzt bei 151—152 °C. Boiled under reflux for 10 hours, the alcohol is then distilled off in vacuo, the residue is taken up in ethyl acetate and ethereal hydrochloric acid is added until the reaction is weakly acidic. Allow to stand overnight, vacuum and dry. The hydrochloride of l- [2- (3-benzyl-is oxy-phenyl) -2-hydroxy-N-benzyl-ethylamino] -3- (2-cyano-phenoxy) -propanol-2 melts at 151-152 ° C .
b) Zur Entbenzylierung wird die in a) erhaltene Substanz in Methanol gelöst und nach Zugabe von Palladium/Kohle bis zur Aufnahme der berechneten Wasserstoffmenge bei b) For the debenzylation, the substance obtained in a) is dissolved in methanol and after addition of palladium / carbon until the calculated amount of hydrogen is added
20 Raumtemperatur geschüttelt. Anschliessend wird vom Katalysator abgesaugt, der Rückstand heiss in Alkohol gelöst und mit der berechneten Menge Fumarsäure versetzt. Man lässt langsam abkühlen, saugt ab und trocknet. Das Fumarat des l-[2-(3-Hydroxyphenyl)2-hydroxy-äthylamino]-3-[2-25 cyanophenoxy]-propanol-2 schmilzt bei 165-167 °C. 20 shaken room temperature. The catalyst is then suctioned off, the residue is dissolved hot in alcohol and the calculated amount of fumaric acid is added. Allow to cool slowly, suction and dry. The fumarate of l- [2- (3-hydroxyphenyl) 2-hydroxyethylamino] -3- [2-25 cyanophenoxy] propanol-2 melts at 165-167 ° C.
Entsprechend dem vorstehenden Beispiel werden auch die in der Tabelle aufgeführten Verbindungen hergestellt: The compounds listed in the table are also prepared in accordance with the example above:
Ri Ri
*2 R * 2 rows
Tabelle Verbindungen der Formel Table compounds of the formula
JL a choh-chra-nh-ch0-choh-ch0-o JL a choh-chra-nh-ch0-choh-ch0-o
Nr. No.
Rt Rt
Rz Margin
R3 R3
R* R *
Rs Rs
R6 R6
Salz* / Fp. [°C] Salt * / Mp. [° C]
1 1
H H
H H
H H
CH3(erythro) CH3 (erythro)
2-CN 2-CN
H H
Cl/169-170 Cl / 169-170
2 2nd
H H
H H
H H
CH3(threo) CH3 (threo)
2-CN 2-CN
H H
FU /177-179 FU / 177-179
3 3rd
4-OH 4-OH
3-OH 3-OH
2-CH3 2-CH3
H H
4-CH3 4-CH3
H H
Cl / 244 (Zers.) Cl / 244 (dec.)
4 4th
4-OH 4-OH
H H
H H
H H
3-CN 3-CN
H H
Cl/154-156 Cl / 154-156
5 5
4-OH 4-OH
H H
H H
H H
2-CH3 2-CH3
H H
FU /123-125 FU / 123-125
6 6
4-OH 4-OH
H H
H H
H H
2-CN 2-CN
H H
Cl / 135-136 Cl / 135-136
7 7
4-OH 4-OH
H H
H H
H H
4-CN 4-CN
H H
Cl /157-159 Cl / 157-159
8 8th
3-OH 3-OH
H H
H H
H H
2-CH3 2-CH3
H H
FU/122 FU / 122
9 9
3-OH 3-OH
5-OH 5-OH
H H
H H
4-CN 4-CN
H H
FU/152-155 FU / 152-155
10 10th
4-OH 4-OH
H H
H H
H H
4-OCH3 4-OCH3
H H
Cl /142-143 Cl / 142-143
11 11
4-OH 4-OH
H H
H H
H H
3-OCH3 3-OCH3
4-OCH3 4-OCH3
Cl /177-179 Cl / 177-179
12 12
3-C1 3-C1
4-C1 4-C1
H H
H H
H H
H H
FO / 189-190 FO / 189-190
13 13
4-OH 4-OH
3-NH2 3-NH2
H H
H H
2-CH3 2-CH3
H H
Cl / 210 (Zers.) Cl / 210 (dec.)
14 14
4-OH 4-OH
3-NH-COCH3 3-NH-COCH3
H H
H H
2-CH3 2-CH3
H H
Cl/158-159 Cl / 158-159
15 15
4-OH 4-OH
H H
H H
H H
4-CH2-CONH2 4-CH2-CONH2
H H
FU /171-172 FU / 171-172
16 16
4-OH 4-OH
3-OCH3 3-OCH3
H H
H H
4-CH3 4-CH3
3-CH3 3-CH3
Cl /148-149 Cl / 148-149
17 17th
4-OH 4-OH
3-CONH2 3-CONH2
H H
H H
4-CH3 4-CH3
H H
Cl /195-196 Cl / 195-196
18 18th
4-OH 4-OH
H H
H H
CH3(erythro) CH3 (erythro)
4-CN 4-CN
H H
Cl/161-164 Cl / 161-164
19 19th
4-OH 4-OH
H H
H H
CH3(threo) CH3 (threo)
4-CN 4-CN
H H
Cl /169-171 Cl / 169-171
* Cl: Hydrochlorid; FU: Fumarat; FO: Formiat, * Cl: hydrochloride; FU: fumarate; FO: formate,
S S
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762606140 DE2606140A1 (en) | 1976-02-17 | 1976-02-17 | NEW DERIVATIVES OF 2-PHENYL-2-HYDROXYAETHYLAMINE |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634822A5 true CH634822A5 (en) | 1983-02-28 |
Family
ID=5970017
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184777A CH634820A5 (en) | 1976-02-17 | 1977-02-15 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH550481A CH634822A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH550381A CH634821A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH357282A CH635569A5 (en) | 1976-02-17 | 1982-06-09 | Process for preparing novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH184777A CH634820A5 (en) | 1976-02-17 | 1977-02-15 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH550381A CH634821A5 (en) | 1976-02-17 | 1981-08-26 | Process for the preparation of novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts. |
| CH357282A CH635569A5 (en) | 1976-02-17 | 1982-06-09 | Process for preparing novel 1-(2-phenyl-2-hydroxyethylamino)-3-phenoxypropan-2-ols and their acid addition salts |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS52100433A (en) |
| AT (1) | AT355008B (en) |
| AU (1) | AU512322B2 (en) |
| BE (1) | BE851503A (en) |
| CH (4) | CH634820A5 (en) |
| DE (1) | DE2606140A1 (en) |
| DK (1) | DK66177A (en) |
| ES (7) | ES455942A1 (en) |
| FI (1) | FI770170A (en) |
| FR (1) | FR2341557A1 (en) |
| GB (1) | GB1544883A (en) |
| IE (1) | IE45186B1 (en) |
| LU (1) | LU76774A1 (en) |
| NL (1) | NL7701613A (en) |
| NO (1) | NO143345C (en) |
| SE (1) | SE7701724L (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3062216D1 (en) * | 1979-09-06 | 1983-04-07 | Beecham Group Plc | Cinnamic acid derivatives, their preparation, and pharmaceutical compositions containing them |
| DE3125870C2 (en) * | 1980-07-09 | 1994-09-15 | William John Louis | 3-aminopropoxyphenyl derivatives, their preparation and medicaments containing them |
| US7998992B2 (en) | 2007-03-30 | 2011-08-16 | Institute Of Medicinal Molecular Design, Inc. | Oxazolidinone derivative having inhibitory activity on 11β-hydroxysteroid dehydrogenase type 1 |
-
1976
- 1976-02-17 DE DE19762606140 patent/DE2606140A1/en not_active Withdrawn
-
1977
- 1977-01-20 FI FI770170A patent/FI770170A/fi not_active Application Discontinuation
- 1977-02-03 AT AT67677A patent/AT355008B/en not_active IP Right Cessation
- 1977-02-15 LU LU76774A patent/LU76774A1/xx unknown
- 1977-02-15 CH CH184777A patent/CH634820A5/en not_active IP Right Cessation
- 1977-02-16 ES ES455942A patent/ES455942A1/en not_active Expired
- 1977-02-16 JP JP1600477A patent/JPS52100433A/en active Pending
- 1977-02-16 SE SE7701724A patent/SE7701724L/en not_active Application Discontinuation
- 1977-02-16 NO NO770509A patent/NO143345C/en unknown
- 1977-02-16 GB GB6521/77A patent/GB1544883A/en not_active Expired
- 1977-02-16 BE BE174995A patent/BE851503A/en not_active IP Right Cessation
- 1977-02-16 NL NL7701613A patent/NL7701613A/en not_active Application Discontinuation
- 1977-02-16 DK DK66177A patent/DK66177A/en not_active Application Discontinuation
- 1977-02-16 AU AU22334/77A patent/AU512322B2/en not_active Expired
- 1977-02-17 IE IE341/77A patent/IE45186B1/en unknown
- 1977-02-17 FR FR7704568A patent/FR2341557A1/en active Granted
- 1977-12-02 ES ES464832A patent/ES464832A1/en not_active Expired
- 1977-12-07 ES ES464834A patent/ES464834A1/en not_active Expired
- 1977-12-07 ES ES464835A patent/ES464835A1/en not_active Expired
- 1977-12-07 ES ES464833A patent/ES464833A1/en not_active Expired
- 1977-12-07 ES ES464837A patent/ES464837A1/en not_active Expired
- 1977-12-07 ES ES464836A patent/ES464836A1/en not_active Expired
-
1981
- 1981-08-26 CH CH550481A patent/CH634822A5/en not_active IP Right Cessation
- 1981-08-26 CH CH550381A patent/CH634821A5/en not_active IP Right Cessation
-
1982
- 1982-06-09 CH CH357282A patent/CH635569A5/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI770170A (en) | 1977-08-18 |
| BE851503A (en) | 1977-08-16 |
| DE2606140A1 (en) | 1977-08-25 |
| ES464837A1 (en) | 1978-08-01 |
| CH635569A5 (en) | 1983-04-15 |
| IE45186L (en) | 1977-08-17 |
| NL7701613A (en) | 1977-08-19 |
| JPS52100433A (en) | 1977-08-23 |
| NO143345C (en) | 1981-01-21 |
| CH634820A5 (en) | 1983-02-28 |
| NO770509L (en) | 1977-08-18 |
| ATA67677A (en) | 1979-07-15 |
| NO143345B (en) | 1980-10-13 |
| LU76774A1 (en) | 1978-04-13 |
| AU512322B2 (en) | 1980-10-02 |
| SE7701724L (en) | 1977-08-18 |
| GB1544883A (en) | 1979-04-25 |
| IE45186B1 (en) | 1982-07-14 |
| FR2341557A1 (en) | 1977-09-16 |
| ES464834A1 (en) | 1978-09-01 |
| ES464832A1 (en) | 1978-09-01 |
| CH634821A5 (en) | 1983-02-28 |
| FR2341557B1 (en) | 1980-08-14 |
| AT355008B (en) | 1980-02-11 |
| ES464833A1 (en) | 1978-09-01 |
| ES464836A1 (en) | 1978-08-01 |
| ES464835A1 (en) | 1979-09-16 |
| AU2233477A (en) | 1978-08-24 |
| DK66177A (en) | 1977-08-18 |
| ES455942A1 (en) | 1978-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |