DE1939697C3 - Amino alcohol esters and agents containing them - Google Patents
Amino alcohol esters and agents containing themInfo
- Publication number
- DE1939697C3 DE1939697C3 DE1939697A DE1939697A DE1939697C3 DE 1939697 C3 DE1939697 C3 DE 1939697C3 DE 1939697 A DE1939697 A DE 1939697A DE 1939697 A DE1939697 A DE 1939697A DE 1939697 C3 DE1939697 C3 DE 1939697C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloride
- amino alcohol
- alcohol esters
- mol
- agents containing
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
R2 R 2
in der η = O oder 1 ist und R1 und R2 beide den Me- choleretische Wirkung haben, die um so überraschenthyl- oder Isopropylrest bedeuten oder zusammen 30 der ist, als kein bis heute bekanntes choleretischesin which η = O or 1 and R 1 and R 2 both have the choleretic effect, which is all the more surprisingly a thyl or isopropyl radical, or together 30 that, as no choleretic effect known to date
mit dem Stickstoffatom, an das sie gebunden sind, die Piperidino- oder Morpholinogruppe bilden sowie deren Säureadditionssalze.with the nitrogen atom to which they are attached, form the piperidino or morpholino group as well their acid addition salts.
Es hat sich gezeigt, daß die Verbindungen (I) eineIt has been found that the compounds (I) a
OCH3 CH,- CO- O— ■' OCH 3 CH, - CO- O— ■ '
Mittel von Aminoalkoholen abgeleitet ist.Agent derived from amino alcohols.
Die beanspruchten Verbindungen können durch Kondensation von Säurehalogeniden der FormelThe claimed compounds can be obtained by condensation of acid halides of the formula
(CH -CH)n -COX(CH -CH) n -COX
mit Aminoalkoholen der Formelwith amino alcohols of the formula
HO-CH2-CH2-NHO-CH 2 -CH 2 -N
hergestellt werden. In diesen Formeln ist X ein Halogen, wäKend die anderen Glieder die obengenannte Bedeutungen haben. Diese Kondensation wird vorteilhaft in einem nichtpolaren Lösungsmittel wie Benzol unter Bewegung und Ausschluß von Feuchtigkeit bei Umgebungstemperatur init stöchiometrischen Mengen der Reaktionsteilnehmer durchgeführt. Im allgemeinen wird die Reaktion 12 bis 24 Stunden bei Umgebungstemperatur oder einige Stunden am Rückfluß durchgeführt. Die Herstellung einiger Verbindungen der Formel (I) wird in folgenden Beispielen beschrieben.getting produced. In these formulas, X is a halogen, while the other terms are as mentioned above Have meanings. This condensation is advantageous in a non-polar solvent such as benzene with agitation and exclusion of moisture at ambient temperature in stoichiometric amounts the respondent carried out. Generally the reaction will take 12 to 24 hours at ambient temperature or carried out under reflux for a few hours. The preparation of some compounds of the formula (I) is described in the following examples.
Beispiel 1
Hydrochlorid von 2-Morpholinoäthyl-O-acetyl-example 1
Hydrochloride of 2-morpholinoethyl-O-acetyl-
vanillal
/I = O; NR1R2 = Morphotinovanilla
/ I = O; NR 1 R 2 = morphotino
In einen 250-ml-Dreihalsholben, der mit Rückflußkühler mit aufgesetztem Calciumchloridröhrchen, Tropftrichter und einem mechanischen Rührer versehen ist, wird eine Lösung von 13,7 g (0,06 Mol) O-Acetylvanilloylchlorid in 50 ml wasserfreiem Benzol gegeben. Durch den Tropftrichter wird allmählich unter Rühren eine Lösung von 7,9 g (0,06 Mol) 2-Morpholinoäthanol in 35 ml wasserfreiem Benzol zugesetzt. Anschließend wird 6 Stunden am Rückfluß erhitzt und die Lösung dann gekühlt. Die abgeschiedenen Kristalle werden abgenutscht und getrocknet. Hierbei werden 14 g unreines Hydrochlorid von 2-Morpholinoäthyl-O-acetylvanillat erhalten.In a 250 ml three-necked flask fitted with a reflux condenser with attached calcium chloride tube, dropping funnel and a mechanical stirrer is a solution of 13.7 g (0.06 mol) of O-acetylvanilloyl chloride in 50 ml of anhydrous benzene given. A solution of 7.9 g (0.06 mol) is gradually added through the dropping funnel with stirring. 2-morpholinoethanol in 35 ml of anhydrous benzene was added. The mixture is then refluxed for 6 hours and the solution is then cooled. The departed Crystals are suction filtered and dried. 14 g of impure hydrochloride of 2-morpholinoethyl-O-acetylvanillate are thereby obtained obtain.
Nach Auflösung in Wasser wird mit Natriumbicarbonat alkalisch gemacht und die Base mit Äther extrahiert. Das Lösungsmittel wird abgedampft, wobei 9,4 g der hellgelben^ öligen Base zurückbleiben, dieAfter dissolving in water, it is made alkaline with sodium bicarbonate and the base is extracted with ether. The solvent is evaporated off, with 9.4 g of the light yellow oily base remaining, the
durch Zusatz der in Äther gelösten berechneten Menge an wasserfreier Salzsäure in das Hydrochlorid umgewandelt wird. Nach Abnutschen, Waschen mit Äther und Trocknen werden 10,2 g des rohen Hydrochloride vom Schmelzpunkt 1600C erhalten. Nach Umkristalli-is converted into the hydrochloride by adding the calculated amount of anhydrous hydrochloric acid dissolved in ether. After filtering off with suction, washing with ether and drying, 10.2 g of the crude hydrochloride with a melting point of 160 ° C. are obtained. After recrystalline
sation aus 500 ml Aceton, dem 50 ml Äther zugesetzt worden sind, schmilzt das Hydrochlorid bei 1610C. Ausbeute 7,8 g entsprechend 36%. Die Verbindung ist leicht hygroskopisch und in etwa 5 Teilen Wasser löslich.sation of 500 ml of acetone, to which 50 ml of ether are added, the hydrochloride melts at 161 g corresponding to 36% yield 0 C. 7.8. The compound is slightly hygroscopic and soluble in about 5 parts of water.
Elementaranalyse für Ci,H2gClNOe:Elemental analysis for Ci, H 2 gClNO e :
Berechnet ... C 53,40, H 6,46, Cl 9,85, N 3,89%; gefunden ... C 53,27, H 6,20, C! 9,92, N 3,96%.Calculated ... C 53.40, H 6.46, Cl 9.85, N 3.89%; found ... C 53.27, H 6.20, C! 9.92, N 3.96%.
Hydrochlorid von 2-Dimethylaminoäthyl-O-acetylvanillat Hydrochloride of 2-dimethylaminoethyl-O-acetylvanillate
η = 0; R1 = R4 = Methyl η = 0; R 1 = R 4 = methyl
Der Versuch wird auf die in Beispiel 1 beschriebene Weise, jedoch unter Verwendung von 5,35 g (0,06 Mol) 2-Dimethylaminoäthanol an Stelle von 7,9 g 2-Morpholinoäthanol durchgeführt. Das rohe Hydrochlorid wird aus einem Aceton Äthylacetat-Gemisch (1: 2) »mkristallisiert. Hierbei werden 7,8 g (Ausbeute 41 %) eines stark hygroskopischen, leicht wasserlöslichen Produkts vom Schmelzpunkt 100 bis 1050C erhalten. Elementaranalyse für C14Hj0ClNO5:The experiment is carried out in the manner described in Example 1, but using 5.35 g (0.06 mol) of 2-dimethylaminoethanol instead of 7.9 g of 2-morpholinoethanol. The crude hydrochloride is crystallized from an acetone / ethyl acetate mixture (1: 2). 7.8 g (yield 41%) of a highly hygroscopic, easily water-soluble product with a melting point of 100 to 105 ° C. are obtained here. Elemental analysis for C 14 Hj 0 ClNO 5 :
Berechnet ... C 52,91, H 6,30, Cl 11,17, N 4,11 %; gefunden ... C 52,70, H 6,15, Cl 11,20, N 4,18%.Calculated ... C 52.91, H 6.30, Cl 11.17, N 4.11%; Found ... C 52.70, H 6.15, Cl 11.20, N 4.18%.
Hydrochlorid von 2-Piperidinoäthyl-O-acetylvanUlat Hydrochloride of 2-piperidinoethyl-O-acetylvanUlate
/J = O; NR1R* = Piperidino/ J = O; NR 1 R * = piperidino
Der Versuch wird auf die in Beispiel 1 beschriebene Weise, jedoch unter Verwendung von 7,75 g (0,06 Mol)
2-Piperidinoäthanol an Stelle von 7,9 g 2-Morpholinoäthanol _durchgeführt. Nach Umkristallisation aus
Aceton-Äther (8: 1) und einer zweiten Umkristallisation aus Aceton werden 9,2 g (Ausbeute 43 %) des
leicht hygroskopischen, in etwa 10 Teilen Wasser löslichen Hydrochlorids vom Schmelzpunkt 1690C erhalien.
Elementaranalyse für C17H84-ClNO5:The experiment is carried out in the manner described in Example 1, but using 7.75 g (0.06 mol) of 2-piperidinoethanol instead of 7.9 g of 2-morpholinoethanol. After recrystallization from acetone-ether (8: 1) and a second recrystallization from acetone 9.2 g (43% yield) of the slightly hygroscopic be erhalien, in about 10 parts water-soluble hydrochloride of melting point 169 0 C.
Elemental analysis for C 17 H 84 -ClNO 5 :
Berechnet... C 57,05, H 6,76 Cl 9,90, N 3,91%; gefunden ... C 56,99, H 6,82, Cl 9,88, N 4,25%.Calculated ... C 57.05, H 6.76, Cl 9.90, N 3.91%; Found ... C 56.99, H 6.82, Cl 9.88, N 4.25%.
Hydrochlorid von 2-Diisopropylaminoäthyl-O-acetylvanillat Hydrochloride of 2-diisopropylaminoethyl-O-acetylvanillate
η = 0; R1 ■·= R4 = Isopropyl η = 0; R 1 ■ · = R 4 = isopropyl
Der Versuch wird auf die in Beispiel 1 beschriebene Weise, jedoch unter Verwendung von 8,7 g (0,06 Mol) 2-Diisopropylaminoäthanol an Stelle von 7,9 g 2-Morpholinoäthanol durchgeführt. Nach Umkristallisation aus Äthylmethylketon werden 14,4 g (Ausbeute 64%) des leicht hygroskopischen, in etwa 4 Teilen Wasser löslichen Hydrochlorids vom Schmelzpunkt 1630C erhalten. The experiment is carried out in the manner described in Example 1, but using 8.7 g (0.06 mol) of 2-diisopropylaminoethanol instead of 7.9 g of 2-morpholinoethanol. After recrystallization from ethyl methyl ketone, 14.4 g (yield 64%) of the slightly hygroscopic hydrochloride, which is soluble in about 4 parts of water and has a melting point of 163 ° C., is obtained.
2-Morpholinoäthyl-O-acetylferulat-hydrc.jhlorid] « = 1; NR1R2 = Morpholino2-morpholinoethyl-O-acetylferulate-hydrc.jhlorid] «= 1; NR 1 R 2 = morpholino
In einen 1000-ml-DreihaIskolben, der mit einem Rückflußkühler mit aufgesetztem Calciumchloridröhrchen, einem Tropftrichter und einem mechanischen Rührer versehen ist, wird eine Lösung von 7,9 g (0,06 Mol) 2-Morpholinoäthanol in 25 ml wasserfreiem Benzol gegeben. Durch den Tropftrichter wird allmählich unter Rühren eine Lösung von 15,3 g (0,06 Mol) O-Acetylferuloylchlorid in 475 ml wasserfreiem Benzol zugesetzt. Das Gemisch wird noch 3 Stunden bei Raumtemperatur gerührt und eine Nacht stehengelassen. Nach Zugabe von 300 ml Petroläther wird 2 Stunden stehengelassen. Die Kristalle werden abgenutscht und im Exsiccator getrocknet. Hierbei werden 16,5 g iohes Hydrochlorid von 2-Morpholinoäthyl-O-acetylferulat erhalten. Nach Umkristallisaticn aus 600 ml Äthanol werden 13,3 g (Ausbeute 57 %) des nichthygroskopischen, in etwa 20 Teilen Wasser löslichen Hydrochlorids erhalten, das bei 2063C schmilzt. Eiementaranalyse für ClgHi4ClNOe: Berechnet ... Cl 9,19%;A solution of 7.9 g (0.06 mol) of 2-morpholinoethanol in 25 ml of anhydrous benzene is placed in a 1000 ml three-necked flask equipped with a reflux condenser with attached calcium chloride tube, a dropping funnel and a mechanical stirrer. A solution of 15.3 g (0.06 mol) of O-acetylferuloyl chloride in 475 ml of anhydrous benzene is gradually added through the dropping funnel with stirring. The mixture is stirred for a further 3 hours at room temperature and left to stand one night. After adding 300 ml of petroleum ether, the mixture is left to stand for 2 hours. The crystals are suction filtered and dried in a desiccator. This gives 16.5 g of iohes hydrochloride of 2-morpholinoethyl-O-acetylferulate. After Umkristallisaticn from 600 ml of ethanol (57% yield) of the non-hygroscopic, soluble in about 20 parts water hydrochloride 13.3 g are obtained, which melts at 206 3 C. Elementary analysis for C lg H i4 ClNO e : calculated ... Cl 9.19%;
gefunden ... Cl 9,03%.found ... Cl 9.03%.
Beispiel 6 Hydrochlorid von 2-Dimethylaminoäthyl-O-acetyl-Example 6 hydrochloride of 2-dimethylaminoethyl-O-acetyl-
η = η =
ferulat
= R* = Methylferulate
= R * = methyl
Der Versuch wird auf die in Beispiel 5 beschriebene Weise durchgeführt, jedoch unter Verwendung von
5,35 g (0,06 Mol) 2-Dimethylaminoäthanol an Stelle von 7,9 g 2-Morpholinoäthanol. Das rohe Hydrochlorid
wird aus Isopropanol, das dem Äther zugesetzt worden ist, umkristallisiert. Hierbei werden 14,8 g
(Ausbeute 72%) des hygroskopischen, in Wasser sehr 2$ leicht löslichen Hydrochlorids erhalten, das bei 136°C
augenblicklich schmilzt.
Elementaranalyse für C16H28ClNO5:
Berechnet ... N 4,07, Cl 10,3 %; gefunden ... N 3,81, Cl 10,35%.The experiment is carried out in the manner described in Example 5, but using 5.35 g (0.06 mol) of 2-dimethylaminoethanol instead of 7.9 g of 2-morpholinoethanol. The crude hydrochloride is recrystallized from isopropanol which has been added to the ether. In this case, can be obtained very easily soluble $ 2 hydrochloride in water 14.8 g (yield 72%) of the hygroscopic which melts instantly at 136 ° C.
Elemental analysis for C 16 H 28 ClNO 5 : Calculated ... N 4.07, Cl 10.3%; found ... N 3.81, Cl 10.35%.
B e i s ρ i e 1 7B e i s ρ i e 1 7
Hydrochlorid von 2-Piperidinoäthyl-O-acetylferulat « = 1; NR1R2 = PiperidinoHydrochloride of 2-piperidinoethyl-O-acetylferulate «= 1; NR 1 R 2 = piperidino
Der Versuch wird auf die in Beispiel 5 beschriebene Weise unter Verwendung von 7,75 g (0,06 Mol) 2-Piperidinoäthanol
an Stelle von 7,9 g 2-Morpholinoäthanol durchgeführt. Das rohe Hydrochlorid wird aus
1150 ml Aceton, dem 150 ml Äther zugesetzt worden sind, umkristallisiert. Hierbei werden 15,8 g (Ausbeute
68%) des nichthydroskopischen, in 5 Teilen Wasser löslichen Hydrochlorids vom Schmelzpunkt 168° C
erhalten.
Elementaranalyse für C18H26CINO5:
Berechnet ... CI 9,23%;
gefunden ... CI9,20%.The experiment is carried out in the manner described in Example 5 using 7.75 g (0.06 mol) of 2-piperidinoethanol instead of 7.9 g of 2-morpholinoethanol. The crude hydrochloride is recrystallized from 1150 ml of acetone to which 150 ml of ether have been added. This gives 15.8 g (68% yield) of the non-hydroscopic hydrochloride, which is soluble in 5 parts of water and has a melting point of 168 ° C.
Elemental analysis for C 18 H 26 CINO 5 : Calculated ... CI 9.23%;
found ... CI9.20%.
Hydrochlorid von 2-Diisopropylaminoäthyl-O-acetylferulat Hydrochloride of 2-diisopropylaminoethyl-O-acetylferulate
η = 1; R1 = R* = Isopropylη = 1; R 1 = R * = isopropyl
Der Versuch wird auf die in Beispiel 6 beschriebene Weise unter Verwendung von 8,7 g (0,06 Mol) 2-Diisopropylaminoäthanol an Stelle von 7,9 g 2-MorphoIinoäthanol durchgeführt. Das rohe Hydrochlorid wird zweimal aus Äthylacetat umkristallisiert. Hierbei werden 8,6 g (Ausbeute 36%) des nichthygroskopischen, wasserlöslichen Hydrochlorids vom Schmelz-So punkt 14O0C erhalten.The experiment is carried out in the manner described in Example 6 using 8.7 g (0.06 mol) of 2-diisopropylaminoethanol instead of 7.9 g of 2-morpholinoethanol. The crude hydrochloride is recrystallized twice from ethyl acetate. Here, 8.6 g (yield 36%) of non-hygroscopic, water-soluble hydrochloride of melting-point So 14O 0 C was obtained.
Elementaranalyse für C20H30ClNO8:Elemental analysis for C 20 H 30 ClNO 8 :
Berechnet ... C 60,06, H 7,56, Cl 8,86%; gefunden ... C 60,53, H 7,58, CI 8,77%.Calculated ... C 60.06, H 7.56, Cl 8.86%; Found ... C 60.53, H 7.58, CI 8.77%.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR161993A FR7720M (en) | 1968-08-06 | 1968-08-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1939697A1 DE1939697A1 (en) | 1970-02-26 |
| DE1939697B2 DE1939697B2 (en) | 1974-08-22 |
| DE1939697C3 true DE1939697C3 (en) | 1975-04-24 |
Family
ID=8653490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1939697A Expired DE1939697C3 (en) | 1968-08-06 | 1969-08-05 | Amino alcohol esters and agents containing them |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE736675A (en) |
| DE (1) | DE1939697C3 (en) |
| ES (1) | ES370252A1 (en) |
| FR (1) | FR7720M (en) |
| GB (1) | GB1264339A (en) |
-
1968
- 1968-08-06 FR FR161993A patent/FR7720M/fr not_active Expired
-
1969
- 1969-07-28 BE BE736675D patent/BE736675A/xx unknown
- 1969-08-01 GB GB1264339D patent/GB1264339A/en not_active Expired
- 1969-08-05 ES ES370252A patent/ES370252A1/en not_active Expired
- 1969-08-05 DE DE1939697A patent/DE1939697C3/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR7720M (en) | 1970-03-02 |
| BE736675A (en) | 1969-12-31 |
| GB1264339A (en) | 1972-02-23 |
| DE1939697B2 (en) | 1974-08-22 |
| DE1939697A1 (en) | 1970-02-26 |
| ES370252A1 (en) | 1971-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| EGA | New person/name/address of the applicant | ||
| 8339 | Ceased/non-payment of the annual fee |