CH343388A - Process for the preparation of new amides - Google Patents
Process for the preparation of new amidesInfo
- Publication number
- CH343388A CH343388A CH343388DA CH343388A CH 343388 A CH343388 A CH 343388A CH 343388D A CH343388D A CH 343388DA CH 343388 A CH343388 A CH 343388A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- alkylene
- radical
- preparation
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- DTGGNTMERRTPLR-UHFFFAOYSA-N 1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=CC=C1 DTGGNTMERRTPLR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- -1 1, 2-diphenylethylamide diethylaminoacetic acid Chemical compound 0.000 description 1
- LOBUEOHOZLKGHQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-phenylethanamine Chemical compound C=1C=C(Cl)C=CC=1C(N)CC1=CC=CC=C1 LOBUEOHOZLKGHQ-UHFFFAOYSA-N 0.000 description 1
- YIHSDPMXTWBNDR-UHFFFAOYSA-N 1-(4-methoxyphenyl)-2-phenylethanamine Chemical compound C1=CC(OC)=CC=C1C(N)CC1=CC=CC=C1 YIHSDPMXTWBNDR-UHFFFAOYSA-N 0.000 description 1
- DYPUFZGNHHLMAL-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-phenylethanamine Chemical compound C=1C=CC=CC=1C(N)CC1=CC=C(Cl)C=C1 DYPUFZGNHHLMAL-UHFFFAOYSA-N 0.000 description 1
- GEJJWYZZKKKSEV-UHFFFAOYSA-N 2-amino-1,2-diphenylethanol Chemical compound C=1C=CC=CC=1C(N)C(O)C1=CC=CC=C1 GEJJWYZZKKKSEV-UHFFFAOYSA-N 0.000 description 1
- JEQDSBVHLKBEIZ-UHFFFAOYSA-N 2-chloropropanoyl chloride Chemical compound CC(Cl)C(Cl)=O JEQDSBVHLKBEIZ-UHFFFAOYSA-N 0.000 description 1
- PCGSVMMXAQSTKX-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(OC)C(N)C1=CC=CC=C1 PCGSVMMXAQSTKX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HIPXPABRMMYVQD-UHFFFAOYSA-N n-benzylbutan-1-amine Chemical compound CCCCNCC1=CC=CC=C1 HIPXPABRMMYVQD-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung neuer Amide Es wurde gefunden, dass Amide der Formel
EMI1.1
<tb> Ar-C <SEP> H-N- <SEP> C <SEP> 0-Alkylen-Am
<tb> <SEP> R1
<tb> Ar-CH-R2
<tb> in welcher Ar gegebenenfalls durch niederes Alkyl, Alkoxy und/oder Halogen substituiertes Phenyl, R Wasserstoff, Alkyl, Alkenyl oder Aralkyl, R2 Wasserstoff, Hydroxy, Alkoxy, Alkenoxy, Alkinoxy oder Aralkoxy und Am eine sekundäre oder tertiäre Aminogruppe bedeutet, als Antikonvulsantia verwendbar sind.
Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung der in Formel I definierten Amide.
Das Verfahren ist dadurch gekennzeichnet, dass man ein Amin der Formel
EMI1.2
mit einer den Rest -CO-Alkylen-X abgebenden Verbindung, worin X einen durch eine sekundäre oder tertiäre Aminogruppe ersetzbaren Rest bedeutet. umsetzt und die erhaltene Verbindung der Formel
EMI1.3
mit einem primären oder sekundären Amin zur Reaktion bringt. Anschliessend können die so erhaltenen Amide, falls dies erwünscht, in ihre Säureadditionssalze überführt werden.
Als den Rest -CO-Alkylen-X abgebende Verbindung kann man verwenden: eine entsprechende Säure, ein Halogenid oder ein Anhydrid einer solchen Säure.
Der Rest X kann ein Halogenatom oder eine Alk-yl-SO,O- bzw. ArylO2O-Gruppe darstellen; durch Umsetzen eines Acylderivates der Formel III mit einem primären oder sekundären Amin erhält man ein Amid der Formel I.
Als Amine der Formel III kann man beispielsweise verwenden: : l-Amino-1, 2-diphenyl-äthan, 1 -Hydroxy-2-amino- 1 ,2-diphenyl-äthan, 1-Methoxy- 2-amino-1 ,2-diphenyl-äthan, l-(4'-Methoxy-phenyl)- 2-phenyl-l-amino- äthan, 1-(4' -Chlor- phenyl)-2 phenyl- 1 -amino-äthan, 1 - (4'-Chlor-phenyl) 2-phenyl- 2-amino-äthan usw.
Diese Amine kann man beispielsweise mit Hilfe der folgenden Säurederivate in die Acylderivate der Formel III überführen: Chloressigsäurechlorid, a Chlor- propionsäurechlorid, fl - Chlor - propionsäure chlorid, a-Brom-buttersäurebromid usf.
Die so erhaltenen Acylderivate der Formel III kann man beispielsweise mit den folgenden Aminen umsetzen: Butylamin, Allylamin, Benzylamin, Dimethylamin, Diäthylamin, Dipropylamin, Dibutylamin, Methylbenzylamin, Methylpropylamin, Methylbutylamin, Butylbenzylamin, Morpholin, Piperidin, Pyrrolidin, C-alkylierte Piperidine oder Pyrrolidine, N-Alkyl-piperazine usf.
Beispiel
1 Mol 1,2-Diphenyl-äthylamin wird in der dreifachen Menge Aceton gelöst. Zu der Lösung gibt man 1 Mol fein pulverisiertes Kaliumcarbonat und lässt zu dem Ganzen unter Rühren 1,1 Mol Chloressigsäure- chlorid zutropfen. Nach 3 Stunden giesst man auf Eis, saugt das N-Chloressigsäure-(l 2-diphenyl-äthyl)- amid ab, löst dieses in der dreifachen Menge Methanol und versetzt mit 2 Mol Diäthylamin. Die Reaktionsmischung wird im Autoklaven 4 Stunden auf 1200 C erhitzt. Nach dem Aufarbeiten erhält man das Diäthylaminoessigsäure-1, ,2-diphenyl-äthylamid vom Smp. 940 C. Das Hydrochlorid der Base schmilzt bei 145 C, das N-Methylmethansulfonat bei 97" C.
In gleicher Weise, wie im vorstehenden Beispiel beschrieben, gewinnt man die folgenden Amide der Formel
EMI2.1
EMI2.2
<tb> <SEP> N-Methyl
<tb> <SEP> R1 <SEP> Am <SEP> Base <SEP> Smp. <SEP> oder <SEP> Sdp. <SEP> ! <SEP> Hydrochlorid <SEP> methansulfonat
<tb> <SEP> Smp. <SEP> Smp.
<tb>
<SEP> .CH3
<tb> <SEP> H <SEP> -N <SEP> 91"C <SEP> 171-172"C <SEP> 146-147"C
<tb> <SEP> CH3
<tb> <SEP> /CH3
<tb> CH3 <SEP> -N <SEP> 0,05: <SEP> 158-160"C <SEP> 187-188"C <SEP> 135-136"C
<tb> <SEP> CH3
<tb> <SEP> /C2H5
<tb> CH3 <SEP> -N <SEP> 0,15: <SEP> 1700C <SEP> 140"C <SEP> 133"C
<tb> <SEP> C2H5
<tb> <SEP> H-NS <SEP> 124-125"C <SEP> 1800C <SEP> 102-103"C
<tb> CH, <SEP> H <SEP> | <SEP> 0,07: <SEP> 175"C <SEP> 196"C <SEP> 80"C
<tb> <SEP> yCH5
<tb> <SEP> H <SEP> C2Hs <SEP> -N <SEP> 04 <SEP> : <SEP> 207 <SEP> C <SEP> 800 <SEP> c <SEP> 121 <SEP> 125 <SEP> C
<tb> <SEP> 0,04: <SEP> 2070 <SEP> C
<tb> <SEP> C2H0
<tb> <SEP> yCH3
<tb> <SEP> H <SEP> -N <SEP> 66-67"C <SEP> 113-114"C <SEP> 790C
<tb> <SEP> C3H7 <SEP> (n)
<tb> <SEP> CH5
<tb> <SEP> H <SEP> CH2 <SEP> (n) <SEP> 0, <SEP> 01 <SEP> 61-62"C <SEP> C <SEP> 136-137"C <SEP> 96-97"C
<tb> <SEP> 0,01:
<SEP> l971990 <SEP> C
<tb> <SEP> C4H9(n)
<tb>
Process for the preparation of new amides It has been found that amides of the formula
EMI1.1
<tb> Ar-C <SEP> H-N- <SEP> C <SEP> 0-alkylene-Am
<tb> <SEP> R1
<tb> Ar-CH-R2
<tb> in which Ar is phenyl optionally substituted by lower alkyl, alkoxy and / or halogen, R is hydrogen, alkyl, alkenyl or aralkyl, R2 is hydrogen, hydroxy, alkoxy, alkenoxy, alkynoxy or aralkoxy and Am is a secondary or tertiary amino group, as Anticonvulsants are usable.
The present patent relates to a process for the preparation of the amides defined in Formula I.
The process is characterized in that an amine of the formula
EMI1.2
with a compound releasing the radical -CO-alkylene-X, in which X is a radical which can be replaced by a secondary or tertiary amino group. and the resulting compound of the formula
EMI1.3
reacts with a primary or secondary amine. The amides thus obtained can then, if so desired, be converted into their acid addition salts.
As a compound donating the radical -CO-alkylene-X one can use: a corresponding acid, a halide or an anhydride of such an acid.
The radical X can represent a halogen atom or an alk-yl-SO, O or arylO2O group; by reacting an acyl derivative of the formula III with a primary or secondary amine, an amide of the formula I is obtained.
The following amines of the formula III can be used, for example: 1-amino-1, 2-diphenyl-ethane, 1-hydroxy-2-amino-1, 2-diphenyl-ethane, 1-methoxy-2-amino-1, 2 -diphenyl-ethane, 1- (4'-methoxyphenyl) -2-phenyl-1-amino-ethane, 1- (4 '-chlorophenyl) -2 phenyl- 1 -amino-ethane, 1- (4 '-Chloro-phenyl) 2-phenyl-2-amino-ethane etc.
These amines can be converted into the acyl derivatives of the formula III, for example, with the aid of the following acid derivatives: chloroacetic acid chloride, a chloropropionic acid chloride, fl-chloro-propionic acid chloride, a-bromobutyric acid bromide, etc.
The acyl derivatives of the formula III obtained in this way can, for example, be reacted with the following amines: butylamine, allylamine, benzylamine, dimethylamine, diethylamine, dipropylamine, dibutylamine, methylbenzylamine, methylpropylamine, methylbutylamine, butylbenzylamine, morpholine, piperidine, pyrrolidine, C-alkylated piperidines , N-alkyl-piperazines, etc.
example
1 mol of 1,2-diphenylethylamine is dissolved in three times the amount of acetone. 1 mol of finely powdered potassium carbonate is added to the solution and 1.1 mol of chloroacetic acid chloride is added dropwise to the whole with stirring. After 3 hours, the mixture is poured onto ice, the N-chloroacetic acid (l 2-diphenylethyl) amide is filtered off with suction, this is dissolved in three times the amount of methanol and 2 moles of diethylamine are added. The reaction mixture is heated to 1200 ° C. for 4 hours in an autoclave. After working up, 1, 2-diphenylethylamide diethylaminoacetic acid with a melting point of 940 ° C. is obtained. The hydrochloride of the base melts at 145 ° C., the N-methyl methanesulfonate at 97 ° C.
The following amides of the formula are obtained in the same way as described in the previous example
EMI2.1
EMI2.2
<tb> <SEP> N-methyl
<tb> <SEP> R1 <SEP> Am <SEP> Base <SEP> Smp. <SEP> or <SEP> Sdp. <SEP>! <SEP> hydrochloride <SEP> methanesulfonate
<tb> <SEP> Smp. <SEP> Smp.
<tb>
<SEP> .CH3
<tb> <SEP> H <SEP> -N <SEP> 91 "C <SEP> 171-172" C <SEP> 146-147 "C
<tb> <SEP> CH3
<tb> <SEP> / CH3
<tb> CH3 <SEP> -N <SEP> 0.05: <SEP> 158-160 "C <SEP> 187-188" C <SEP> 135-136 "C
<tb> <SEP> CH3
<tb> <SEP> / C2H5
<tb> CH3 <SEP> -N <SEP> 0.15: <SEP> 1700C <SEP> 140 "C <SEP> 133" C
<tb> <SEP> C2H5
<tb> <SEP> H-NS <SEP> 124-125 "C <SEP> 1800C <SEP> 102-103" C
<tb> CH, <SEP> H <SEP> | <SEP> 0.07: <SEP> 175 "C <SEP> 196" C <SEP> 80 "C
<tb> <SEP> yCH5
<tb> <SEP> H <SEP> C2Hs <SEP> -N <SEP> 04 <SEP>: <SEP> 207 <SEP> C <SEP> 800 <SEP> c <SEP> 121 <SEP> 125 <SEP > C
<tb> <SEP> 0.04: <SEP> 2070 <SEP> C
<tb> <SEP> C2H0
<tb> <SEP> yCH3
<tb> <SEP> H <SEP> -N <SEP> 66-67 "C <SEP> 113-114" C <SEP> 790C
<tb> <SEP> C3H7 <SEP> (n)
<tb> <SEP> CH5
<tb> <SEP> H <SEP> CH2 <SEP> (n) <SEP> 0, <SEP> 01 <SEP> 61-62 "C <SEP> C <SEP> 136-137" C <SEP> 96 -97 "C
<tb> <SEP> 0.01:
<SEP> l971990 <SEP> C
<tb> <SEP> C4H9 (n)
<tb>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH343388T | 1956-03-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH343388A true CH343388A (en) | 1959-12-31 |
Family
ID=4506513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH343388D CH343388A (en) | 1956-03-09 | 1956-03-09 | Process for the preparation of new amides |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH343388A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769466A (en) * | 1987-02-06 | 1988-09-06 | Pennwalt Corporation | 2-aminoacetamide pyridinyl derivatives |
| US4798687A (en) * | 1987-02-06 | 1989-01-17 | Pennwalt Corporation | 2-Amino-N-[1,2-Diphenyl-1-(thifluoromethyl)ethyl]acetamide derivatives |
| US4871872A (en) * | 1988-01-20 | 1989-10-03 | Fisons Corporation | 2-[(2-aminoacetyl)amino]acetamide derivatives |
| EP0356035A3 (en) * | 1988-08-12 | 1991-04-03 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5047541A (en) * | 1987-02-06 | 1991-09-10 | Fisons Corporation | 2-azacyclocarboxamide derivatives |
| US5093524A (en) * | 1990-10-15 | 1992-03-03 | Fisons Corporation | 2-(alkylamino)acetamide derivatives |
| US5331007A (en) * | 1987-02-06 | 1994-07-19 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5382683A (en) * | 1988-01-20 | 1995-01-17 | Fisons Corporation | 2-aminopropanamide derivatives |
| US5430044A (en) * | 1987-02-06 | 1995-07-04 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
-
1956
- 1956-03-09 CH CH343388D patent/CH343388A/en unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4769466A (en) * | 1987-02-06 | 1988-09-06 | Pennwalt Corporation | 2-aminoacetamide pyridinyl derivatives |
| US4798687A (en) * | 1987-02-06 | 1989-01-17 | Pennwalt Corporation | 2-Amino-N-[1,2-Diphenyl-1-(thifluoromethyl)ethyl]acetamide derivatives |
| US5047541A (en) * | 1987-02-06 | 1991-09-10 | Fisons Corporation | 2-azacyclocarboxamide derivatives |
| US5331007A (en) * | 1987-02-06 | 1994-07-19 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5430044A (en) * | 1987-02-06 | 1995-07-04 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5539120A (en) * | 1987-02-06 | 1996-07-23 | Griffith; Ronald C. | Arylalkyl-amines having anticonvulsant and neuroprotective properties |
| US5605916A (en) * | 1987-02-06 | 1997-02-25 | Astra Ab | Arylalkyl-amines having anticonvulsant and neuroprotective properties |
| US4871872A (en) * | 1988-01-20 | 1989-10-03 | Fisons Corporation | 2-[(2-aminoacetyl)amino]acetamide derivatives |
| US5382683A (en) * | 1988-01-20 | 1995-01-17 | Fisons Corporation | 2-aminopropanamide derivatives |
| EP0356035A3 (en) * | 1988-08-12 | 1991-04-03 | Astra Aktiebolag | Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| WO1991011995A1 (en) * | 1988-08-12 | 1991-08-22 | Fisons Corporation | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
| US5093524A (en) * | 1990-10-15 | 1992-03-03 | Fisons Corporation | 2-(alkylamino)acetamide derivatives |
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