CH437354A - Verfahren zur Herstellung von 1-(Acylphenyl)-2-amino-1,3-propandiolen - Google Patents
Verfahren zur Herstellung von 1-(Acylphenyl)-2-amino-1,3-propandiolenInfo
- Publication number
- CH437354A CH437354A CH1262963A CH1262963A CH437354A CH 437354 A CH437354 A CH 437354A CH 1262963 A CH1262963 A CH 1262963A CH 1262963 A CH1262963 A CH 1262963A CH 437354 A CH437354 A CH 437354A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- amino
- threo
- preparation
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- 229920000166 polytrimethylene carbonate Polymers 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- -1 p-acetylphenyl Chemical group 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical group O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005335 azido alkyl group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004966 cyanoalkyl group Chemical group 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004982 dihaloalkyl group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000005347 halocycloalkyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical class OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung von 1-(Acylphenyl)-2Wamino-1, 3-propandiolen
Die Erfindung betrifft ein Verfahren zur Herstellung von neuen Verbindungen der Formel:
EMI1.1
in denen Rt niederes Alkyl, wie Methyl, Äthyl, Propyl,
Isopropyl oder Isobutyl, Cycloalkyl, wie Cyclopentyl oder Cyclohexyl, substituiertes Cycloalkyl, wie Halogen cycloalkyl, Aryl, wie Phenyl, substituiertes Aryl, wie Tolyl oder Hydroxyphenyl, oder einen heterocyclischen Rest, wie Pyridyl oder Furyl, bedeutet.
Beispiele für die erfindungsgemäss herstellbaren neuen Verbindungen sind: D-threo- 1 -(p-Acetylphenyl)-2-amino- 1,3 -propandiol DL-threo-l -(p-Acetylphenyl)-2-amino-l 3-propandiol D-threo-l-(p-Benzoylphenyl)-2-amino-1, 3-propandiol, D-threo-1-(p-Cyclohexylcarbonylphenyl)-2-amino-1, 3- propandiol u. a.
Diese Verbindungen können zur Herstellung von neuen, substituierten 1,3-Propandiolen der Formel:
EMI1.2
verwendet werden, worin R2 niederes Alkyl, Aryl, Aralkyl, Cycloalkyl, Halogenalkyl, Dihalogenalkyl, einen heterocyclischen Rest, Azidoalkyl oder Cyanalkyl bedeutet und R3 Wasserstoff bedeutet, falls R4 Hydroxyl bedeutet, oder R3 und R. t zusammen =0, =NH oder
EMI1.3
bedeuten.
Das erfindungsgemässe Verfahren ist dadurch gekennzeichnet, dass man eine Verbindung der Formel
EMI1.4
bci seinem sauren pH-Wert hydrolysiert.
Die Ausgangsverbindungen können aus den ent sprechenden Cyanphenylverbindungen durch Umsetzung mit Verbindungen der Formel RtMgX, worin X Halogen bedeutet, oder der Formel R1Li unter wasserfreien Be dingungen und Hydrolisieren des Reaktionsproduktes in
Wasser erhalten werden.
Wie sich aus der Formel 1 ergibt, enthalten die neuen, erfindungsgemäss herstellbaren Verbindungen zwei asymmetrische Kohlenstoffatome und kommen daher sowohl als Strukturisomere als auch als optische Isomere vor, wobei sich der Ausdruck Strukturisomere auf die threo- und erythro-Form bezieht, die sich durch die Anordnung der an die beiden asymmetrischen Kohlenstoffatome gebundenen polaren Gruppen unterscheiden. So liegen in bezug auf eine durch die beiden asymmetrischen Kohlenstoffatome gelegte Ebene die am stärksten polaren Gruppen an den asymmetrischen Kohlenstoffatomen bei den Erythroverbindungen auf der gleichen Seite, bei den Threoverbindungen dagegen auf gegenüberliegenden Seiten. threo- wie auch erythro-Formen kommen als Racemate optisch aktiver Isomere vor, die in bekannter Weise in ihre rechtsdrehende (D-) und linksdrehende (L-) Form aufgespalten werden können.
Die erfindungs gemäss herstellbaren Verbindungen können also in vier verschiedenen isomeren Formen vorkommen.
Die folgenden Beispiele dienen zur näheren Erläuterung der Strukturbezeichnungen:
EMI2.1
<tb> <SEP> Hl <SEP> n
<tb> <SEP> ffi <SEP> (L <SEP> -G <SEP> -CH20H
<tb> R1 <SEP> H
<tb> <SEP> o <SEP> D-threo-Isomeres
<tb> <SEP> IFjil
<tb> <SEP> I
<tb> <SEP> vCIaSCH20H
<tb> <SEP> H
<tb> Ri-C
<tb> <SEP> 0 <SEP> D-erythro-Isomeres
<tb> <SEP> H <SEP> H
<tb> <SEP> c-CWOH
<tb> <SEP> INHsI
<tb> <SEP> o <SEP> L-erythro-Isomeres
<tb> <SEP> IHI
<tb> <SEP> ITI <SEP> H
<tb> <SEP> I <SEP> I
<tb> Ri-C
<tb> RtC
<tb> <SEP> II <SEP> L-threo-Isomeres
<tb> <SEP> 0
<tb>
Beispiel D-threo-1-(p-Isobutyrylphenyl)-2-amino-l, d-propandiol
Eine Lösung von 8,0 g D-threo-l-(p-Cyanphenyl) 2-acetamino-1,
3-propandiol in 100 ml wasserfreiem Tetrahydrofuran wird im Laufe von 15 Minuten unter Rühren zu 0,4 Mol Isopropylmagnesiumbromid in Tetrahydrofuran zugegeben. Die entstehende klare Lösung wird drei Stunden lang auf 50"C erhitzt, tropfenweise bei 0 C mit einer Lösung von 40 g Ammoniumchlorid in 80 ml Wasser versetzt und anschliessend 2 Stunden lang bei 250 C gerührt. Nach Trennung der beiden Phasen wird die wässrige Phase viermal mit je 150 ml Äthylacetat extrahiert.
Die vereinigten Extrakte werden über Natriumsulfat getrocknet und im Vakuum bei 450 C vom Lösungsmittel befreit, wobei 9,5 g orangegelbe, halbfeste Substanz erhalten werden. Dreiviertel (7,1 g) dieses Rückstandes werden in 100 ml 100!obige Schwefelsäure aufgenommen und in Stickstoffatmosphäre drei Stunden lang auf dem Dampfbad erhitzt. Nach Abkühlen auf 20-25 C wird die braune Lösung mit 75 ml Äther extrahiert. Der Extrakt, der weder Carbonyl noch Amidfunktion aufweist, wird verworfen. Die wässrige Phase wird mit konzentrierter Natronlauge bei 0 C alkalisch gemacht und fünfmal mit je 10 ml Äthylacetat extrahiert.
Die vereinigten Extrakte werden über Natriumsulfat getrocknet und im Vakuum vom Lösungsmittel befreit, wobei 5,4 g D-threo-l-(p-Isobutyryl phenyl)-2-amino-1,3-propandiol in Form einer lohfarbenen Festsubstanz vom Schmelzpunkt 98-99 C zurückbleiben, die nach zweimaligem Umkristallisieren aus Äthylacetat analysenreine, fast weisse Kristalle vom Schmelzpunkt 108-1090C, [a] = -22,0" (C = 1,05, Methanol) ergeben.
Claims (1)
- Analyse für Cl3Hl9NO3 Berechnet C 65,80 H 8,07 N 5,90 Gefunden C 66,01 H 7,96 N 5,66 PATENTANSPRUCH Verfahren zur Herstellung von Verbindungen der Formel EMI2.2 in der Rl einen niederen Alkyl-, Cycloalkyl-, substituierten Cycloalkyl-, Aryl- oder heterocyclischen Rest bedeutet, dadurch gekennzeichnet, dass man eine Verbindung der Formel EMI2.3 bei einem sauren pH-Wert hydrolysiert.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US231027A US3183265A (en) | 1962-10-16 | 1962-10-16 | Acylphenylacylamido-1, 3-propanediols and preparation therefor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH437354A true CH437354A (de) | 1967-06-15 |
Family
ID=22867493
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1262963A CH437354A (de) | 1962-10-16 | 1963-10-15 | Verfahren zur Herstellung von 1-(Acylphenyl)-2-amino-1,3-propandiolen |
| CH539267A CH460812A (de) | 1962-10-16 | 1963-10-15 | Verfahren zur Herstellung von Acylphenyldichloracetamino-1,3-propandiolen |
| CH539167A CH455838A (de) | 1962-10-16 | 1963-10-15 | Verfahren zur Herstellung von Acylphenylacetamino-1,3-propandiolen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH539267A CH460812A (de) | 1962-10-16 | 1963-10-15 | Verfahren zur Herstellung von Acylphenyldichloracetamino-1,3-propandiolen |
| CH539167A CH455838A (de) | 1962-10-16 | 1963-10-15 | Verfahren zur Herstellung von Acylphenylacetamino-1,3-propandiolen |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3183265A (de) |
| BE (1) | BE638755A (de) |
| BR (1) | BR6353747D0 (de) |
| CH (3) | CH437354A (de) |
| DE (1) | DE1518439A1 (de) |
| DK (1) | DK115265B (de) |
| ES (1) | ES292465A1 (de) |
| FR (1) | FR3897M (de) |
| GB (3) | GB1065124A (de) |
| SE (3) | SE301470B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0308289A (pt) * | 2002-03-08 | 2005-01-11 | Schering Plough Ltd | Antibióticos do tipo florfenicol |
| US8119667B2 (en) | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| EP2091909A1 (de) | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Wasserlösliche florfenicol-prodrugs und analoga |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2597248A (en) * | 1948-08-06 | 1952-05-20 | Smith Kline French Lab | Nu-substituted amino-ethanols |
| US2600077A (en) * | 1948-10-05 | 1952-06-10 | Schenley Lab Inc | Thiosemicarbazones |
| US2568571A (en) * | 1950-09-23 | 1951-09-18 | Parke Davis & Co | Haloacetylamidophenyl-halo-acetamidopropandiol |
| US2721207A (en) * | 1952-11-01 | 1955-10-18 | Parke Davis & Co | Process for the production of amino diols and intermediate products utilized in said process |
| US2921080A (en) * | 1956-11-21 | 1960-01-12 | Sterling Drug Inc | Process for making 5-cyano-2-allyl-pyrrolidines and products therefrom |
-
0
- BE BE638755D patent/BE638755A/xx unknown
-
1962
- 1962-10-16 US US231027A patent/US3183265A/en not_active Expired - Lifetime
-
1963
- 1963-10-11 GB GB12569/65A patent/GB1065124A/en not_active Expired
- 1963-10-11 GB GB40165/63A patent/GB1065123A/en not_active Expired
- 1963-10-11 GB GB4016/66A patent/GB1065125A/en not_active Expired
- 1963-10-14 ES ES292465A patent/ES292465A1/es not_active Expired
- 1963-10-14 FR FR950558A patent/FR3897M/fr not_active Expired
- 1963-10-15 DE DE19631518439 patent/DE1518439A1/de active Granted
- 1963-10-15 DK DK485763AA patent/DK115265B/da unknown
- 1963-10-15 CH CH1262963A patent/CH437354A/de unknown
- 1963-10-15 CH CH539267A patent/CH460812A/de unknown
- 1963-10-15 CH CH539167A patent/CH455838A/de unknown
- 1963-10-16 SE SE11347/63A patent/SE301470B/xx unknown
- 1963-10-16 BR BR153747/63A patent/BR6353747D0/pt unknown
-
1965
- 1965-04-01 SE SE420965A patent/SE315876B/xx unknown
- 1965-07-27 SE SE9857/65A patent/SE322237B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE322237B (de) | 1970-04-06 |
| GB1065125A (en) | 1967-04-12 |
| BR6353747D0 (pt) | 1973-07-12 |
| US3183265A (en) | 1965-05-11 |
| FR3897M (de) | 1966-02-07 |
| ES292465A1 (es) | 1964-03-01 |
| CH455838A (de) | 1968-05-15 |
| GB1065123A (en) | 1967-04-12 |
| GB1065124A (en) | 1967-04-12 |
| SE301470B (de) | 1968-06-10 |
| SE315876B (de) | 1969-10-13 |
| DE1518439A1 (de) | 1972-03-09 |
| DK115265B (da) | 1969-09-22 |
| BE638755A (de) | |
| CH460812A (de) | 1968-08-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH437354A (de) | Verfahren zur Herstellung von 1-(Acylphenyl)-2-amino-1,3-propandiolen | |
| DE3719488A1 (de) | Verfahren zur herstellung von 3,3-diarylacrylsaeureamiden | |
| CH395967A (de) | Verfahren zur Herstellung von racemischer und optisch aktiver 2,3-Dimercaptobernsteinsäure | |
| DE1212984B (de) | Verfahren zur Herstellung von basisch substituierten Cumaronen | |
| CH497367A (de) | Verfahren zur Herstellung von Zimtsäurederivaten und deren Verwendung | |
| DE716579C (de) | Verfahren zur Herstellung von Esteramiden der Mandelsaeure | |
| AT213884B (de) | Verfahren zur Herstellung von neuen 3-Phenyl-3-pyrrolidinol-Verbindungen | |
| DE437976C (de) | Verfahren zur Darstellung von Alkaminestern N-monoalkylierter und N-monoalkyloxyalkylierter Derivate der p-Aminobenzoesaeure | |
| AT146504B (de) | Verfahren zur Herstellung von Amiden der Pyrazinmonocarbonsäure. | |
| AT221508B (de) | Verfahren zur Herstellung von neuen Aniliden und deren Salzen | |
| AT203496B (de) | Verfahren zur Herstellung von neuen tertiären Aminen | |
| DE906572C (de) | Verfahren zur Herstellung von Oxazolinen | |
| DE875048C (de) | Verfahren zur Herstellung von 3-Pyrazolidonen | |
| AT202125B (de) | Verfahren zur Herstellung von neuen α-Mercapto-Säureamiden | |
| AT250334B (de) | Verfahren zur Herstellung von α-Carbalkoxy-β-arylamino-acrylsäureestern | |
| DE431166C (de) | Verfahren zur Darstellung von Alkaminestern N-monoalkylierter und N-monoalkyloxyalkylierter Derivate der p-Aminobenzoesaeure | |
| DE917424C (de) | Verfahren zur Herstellung von N-Acetyl-propargyl-arylaminen und ihrer p-staendigen Substitutionsprodukte | |
| AT203495B (de) | Verfahren zur Herstellung von neuen tertiären Aminen | |
| AT256825B (de) | Verfahren zur Herstellung von neuen heterocyclischen Benzamidoverbindungen und ihren Salzen | |
| DE723051C (de) | Verfahren zur Herstellung von Dialkylmalonamidsaeureestern | |
| AT163197B (de) | Verfahren zur Herstellung neuer Amine | |
| AT218509B (de) | Verfahren zur Herstellung von basisch substituierten Carbinolen, sowie von ihren sterisch einheitlichen Razematen und deren optisch aktiven Komponenten und/oder ihren Säureadditionssalzen | |
| DE1595903C (de) | 1-Substituierte 2,6-Dimethyl-4-phenylpiperazine | |
| AT217026B (de) | Verfahren zur Herstellung von neuen α-Aminoisobutyrophenonverbindungen und deren Säureadditionssalzen | |
| DE767146C (de) | Verfahren zur Herstellung basisch substituierter Phenylacetamide |