DE2327193A1 - PROCESS FOR THE PREPARATION OF 2-METHOXY-5-ALKYLSULFONYLBENZAMIDES - Google Patents
PROCESS FOR THE PREPARATION OF 2-METHOXY-5-ALKYLSULFONYLBENZAMIDESInfo
- Publication number
- DE2327193A1 DE2327193A1 DE2327193A DE2327193A DE2327193A1 DE 2327193 A1 DE2327193 A1 DE 2327193A1 DE 2327193 A DE2327193 A DE 2327193A DE 2327193 A DE2327193 A DE 2327193A DE 2327193 A1 DE2327193 A1 DE 2327193A1
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- benzamides
- general formula
- preparation
- alkylsulfonylbenzamides
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 5
- 150000003936 benzamides Chemical class 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004985 diamines Chemical class 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- BXWLVQXAFBWKSR-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(O)=O BXWLVQXAFBWKSR-UHFFFAOYSA-N 0.000 description 1
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- -1 N- (1-ethyl-2-pyrrolidinylmethyl) -2-methoxy-5-ethylsulfonylbenzamide chlorohydrate Chemical compound 0.000 description 1
- JTVPZMFULRWINT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC JTVPZMFULRWINT-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B44—DECORATIVE ARTS
- B44F—SPECIAL DESIGNS OR PICTURES
- B44F1/00—Designs or pictures characterised by special or unusual light effects
- B44F1/08—Designs or pictures characterised by special or unusual light effects characterised by colour effects
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Description
PATENTANWÄLTEPATENT LAWYERS
DR.-ING. RICHARD GLAWE · DIPL-ING. KLAUS DELFS · DIPL-PHYS. DR. WALTER MOLLDR.-ING. RICHARD GLAWE DIPL-ING. KLAUS DELFS DIPL-PHYS. DR. WALTER MOLL
MÜNCHEN HAMBURG MÜNCHENMUNICH HAMBURG MUNICH
POSTFACH 37PO Box 37
UEBHERRSTR. 20UEBHERRSTR. 20th
TEL. (0811) 22 65 48TEL. (0811) 22 65 48
WAITZSTR. 12WAITZSTR. 12th
TEL. (0411) 8? 22 55TEL. (0411) 8? 22 55
TELEX 212921 spezTELEX 212921 spec
UNSER ZEICHENOUR SIGN
SOCIETE D1ETUDES SCIEITTIPIQUES ET INDUSTRIELLES DE L·ILE-DE-PEANCE Paris / FrankreichSOCIETE D 1 ETUDES SCIEITTIPIQUES ET INDUSTRIELLES DE L · ILE-DE-PEANCE Paris / France
Verfahren zur Herstellung von 2-Methoxy-5-alkylsulfonyl"benzamidenProcess for the preparation of 2-methoxy-5-alkylsulfonyl "benzamides
Die Erfindung "betrifft ein Verfahren zur Herstellung von 2-Methoxy-5-alkylsulfonylbenzamiden der allgemeinen Formel (IV)The invention "relates to a process for the production of 2-methoxy-5-alkylsulfonylbenzamides of the general formula (IV)
C0-NH-(CH2)n-AC0-NH- (CH 2 ) n -A
XO2SXO 2 S
309881/1197309881/1197
sowie deren Salzen mit pharmazeutisch verträglichen Mineraloder organischen Säuren und bei der Reaktion dieser Benzamide mit einem aliphatischen oder aromatischen Alkylierungsmittel erhältlichen quartären Ammoniumderiväten.as well as their salts with pharmaceutically acceptable mineral or organic acids and in the reaction of these benzamides with an aliphatic or aromatic alkylating agent available quaternary ammonium derivatives.
Die allgemeinen Gruppen der obigen Formel können die folgenden Bedeutungen aufweisen:The general groups of the above formula can have the following meanings:
X eine Alkylgruppe mit 1 oder 2 Kohlenstoffatomen, η die Zahl 1 oder 2 undX is an alkyl group with 1 or 2 carbon atoms, η the number 1 or 2 and
A entweder eine Diäthylaminogruppe oder eine heterocyclische Gruppe der FormelA is either a diethylamino group or a heterocyclic group of the formula
C2H5 C 2 H 5
Das Verfahren der Erfindung umfaßt die Reaktion eines Diamine der allgemeinen Formel (II),The process of the invention comprises the reaction of a diamine of the general formula (II),
H2N-(CH2)n-A (II)H 2 N- (CH 2 ) n -A (II)
in der η und A wie oben definiert sind, mit Phosphortri-in which η and A are defined as above, with phosphorus tri-
309881/1197309881/1197
chlorid und die Kondensation des "in situ" erhaltenen
Phosphazoderivats (III) mit der 2-Methoxy-5-alkylsulfonylbenzoesäure
(I).chloride and the condensation of the "in situ" obtained
Phosphazo derivative (III) with 2-methoxy-5-alkylsulfonylbenzoic acid (I).
Die Benzamide der allgemeinen Formel (IV) weisen interessante pharmakologische Eigenschaften auf, welche in den
französischen Patentschriften ITr. 72 CAM, Hr. 4879 M und
Nr. 5916 M, eingereicht am 15. Oktober 1963, 1. April 1965
.bzw. 21. Jannuar 1966, beschrieben sind.The benzamides of the general formula (IV) have interesting pharmacological properties, which are described in the French patents ITr. 72 CAM, Mr. 4879 M and
No. 5916 M, filed October 15, 1963, April 1, 1965. January 21, 1966.
Das Verfahren der Erfindung ist aus dem folgenden Reaktionsschema ersichtlich:The process of the invention can be seen from the following reaction scheme:
+ 2 H2N-(CH2)n-A+ 2 H 2 N- (CH 2 ) n -A
(II)(II)
■* P■ * P
/,N-(CH2) -A/, N- (CH 2 ) -A
NH-(CH2)n-ANH- (CH 2 ) n -A
(III) "in situ»(III) "in situ"
+ 2+ 2
XO2SXO 2 S
CO,CO,
(D(D
XO2S'XO 2 S '
CO-NH-(CH2 )n-JCO-NH- (CH 2 ) n -J
irOCH3
(IV)ir OCH 3
(IV)
309881/1197309881/1197
Die 2-Methoxy-5-alkylsulfony!benzoesäure, die als Ausgangsmaterial verwendet wird, ist in der amerikanischen Patentschrift 3 342 826, veröffentlicht am 19- September 1967, beschrieben.The 2-methoxy-5-alkylsulfonylbenzoic acid, which is used as the starting material is used is in U.S. Patent 3,342,826, published September 19, 1967, described.
Die Reaktion wird in einem Lösungsmittel, z.B. Pyridin, durchgeführt, wobei man bis zur Rückflußtemperatur erhitzt.The reaction is carried out in a solvent such as pyridine while heating to reflux temperature.
Das Verfahren der Erfindung wird im folgenden anhand von Ausführungsbeispielen erläutert. Die Erfindung ist jedoch nicht auf diese Beispiele beschränkt.The method of the invention is described below with reference to FIG Embodiments explained. However, the invention is not limited to these examples.
B--(1-Äthyl-2-pyrrolidinylmethyl)-2-methoxy-5-äthylsulfonylbenzamid-Chlorhydrat B - - (1-Ethyl-2-pyrrolidinylmethyl) -2-methoxy-5-ethylsulfonylbenzamide hydrochloride
In einen 1 1-Kolben gibt man eine Lösung von 17*22 g N-Äthyl-oi- -aminomethylpyrrolidin in 36O ml Pyridin. Dazu fügt man bei Raumtemperatur eine Lösung von 3,51 g Phosphortrichlorid in 40 ml Pyridin-. Nach einstündigem Rühren setzt man 10 g 2-Methoxy-5-äthylsulfony!benzoesäure hinzu, Man erhitzt 4 1/2 Stunden am Rückfluß. Nach dem Abkühlen verdampft man das Lösungsmittel im Vakuum. Der Rückstand wird in 200 ml 20 folger Natronlauge gelöst. Die Lösung wird mit 200 mlA solution of 17 * 22 g of N-ethyl-oi- -aminomethylpyrrolidine in 36O ml of pyridine is placed in a 1 liter flask. A solution of 3.51 g of phosphorus trichloride in 40 ml of pyridine is added at room temperature. After stirring for one hour, 10 g of 2-methoxy-5-ethylsulfonylbenzoic acid are added and the mixture is refluxed for 41/2 hours. After cooling, the solvent is evaporated off in vacuo. The residue is dissolved in 200 ml of 20 % sodium hydroxide solution. The solution is with 200 ml
309881/1197309881/1197
Chloroform extrahiert.Chloroform extracted.
Die organische lösung wird getrocknet und filtriert. Das Lösungsmittel wird im Vakuum abdestilliert.The organic solution is dried and filtered. The solvent is distilled off in vacuo.
Der Rückstand wird in 150 ml Äthanol gelöst. Die Lösung wird mit Salzsäure angesäuert.The residue is dissolved in 150 ml of ethanol. The solution is acidified with hydrochloric acid.
Das Chlorhydrat wird abgesaugt und aus 100 ml absolutem Äthanol umkristallisiert.The hydrochloride is filtered off with suction and recrystallized from 100 ml of absolute ethanol.
Man erhält 7,2 g N-(1-Äthyl-2-pyrrolidinylmethyl)-2-methoxy-5-äthylsulfonylbenzamid-Chlorhydrat. Smp. 190 - 1930C.7.2 g of N- (1-ethyl-2-pyrrolidinylmethyl) -2-methoxy-5-ethylsulfonylbenzamide chlorohydrate are obtained. M.p. 190-193 0 C.
Reinheit (durch Dosierung von Perchlorsäure): 99,2 fi S (fo) berechnet: 8,19 gefunden: 8^20Purity (by adding perchloric acid): 99.2 fi S (fo) calculated: 8.19 found: 8 ^ 20
Beispiel II JT-(Diathylaminoathyl)-2-methoxy-5-methylsulfonylbenzamid Example II JT- (Diethylaminoethyl) -2-methoxy-5-methylsulfonylbenzamide
In einen 1 1-Kolben gibt man eine Lösung von 16,4 g Ν,Ν-Diäthyläthylendiamin in 376 ml Pyridin.A solution of 16.4 g is placed in a 1 l flask Ν, Ν-diethylethylenediamine in 376 ml of pyridine.
309881/1197309881/1197
Dann fügt man "bei Raumtemperatur eine Lösung von 3»76 g PhosphortriChlorid in 43 ml Pyridin hinzu. Nach 30-minütigem Rühren fügt man 10 g 2-Methoxy-5-methylsulfony!benzoesäure hinzu. Man erhitzt 4 1/2 Stunden am Rückfluß.A solution of 3 »76 g is then added at room temperature Add phosphorus trichloride in 43 ml of pyridine. After 30 minutes 10 g of 2-methoxy-5-methylsulfonylbenzoic acid are added with stirring added. The mixture is refluxed for 4 1/2 hours.
Nach dem Abkühlen verdampft man das Lösungsmittel im Vakuum. Der Rückstand wird in einer Mischung von 130 ml Wasser und 6,5 ml 36 folger Salzsäure gelöst. Nach dem Filtrieren macht man das FiItrat mit Natronlauge alkalisch.After cooling, the solvent is evaporated off in vacuo. The residue is dissolved in a mixture of 130 ml of water and 6.5 ml of 36 folger hydrochloric acid. After filtering, the filtrate is made alkaline with sodium hydroxide solution.
Der Niederschlag wird abfiltriert, gewaschen und im Trockenschrank bei 500C getrocknet.The precipitate is filtered off, washed and dried at 50 ° C. in a drying cabinet.
Man erhält 7,5 g N-(Diäthylaminoäthyl)-2-methoxy-5-methylsulfonylbenzamid.
Smp. 1220C7.5 g of N- (diethylaminoethyl) -2-methoxy-5-methylsulfonylbenzamide are obtained.
M.p. 122 ° C
S (#) berechnet: 9,76
gefunden: 9f84S (#) calculated: 9.76
found: 9 f 84
309881/1197309881/1197
Claims (1)
ι d. η CO-MH- (CH 9 ) -A
ι d. η
η die Zahl 1 oder 2 und A entweder eine Diäthylaminogruppe oder eine heterocyclische Gruppe der folgenden Formelin which X is an alkyl group with 1 or 2 carbon atoms,
η is the number 1 or 2 and A is either a diethylamino group or a heterocyclic group of the following formula
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7219802A FR2187309A1 (en) | 1972-06-01 | 1972-06-01 | 2-methoxy-5-alkylsulphonylbenzamides - pharmaceuticals |
| FR7220043A FR2188601A5 (en) | 1972-06-02 | 1972-06-02 | 2-methoxy-5-alkylsulphonylbenzamides - pharmaceuticals |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2327193A1 true DE2327193A1 (en) | 1974-01-03 |
| DE2327193B2 DE2327193B2 (en) | 1979-04-12 |
| DE2327193C3 DE2327193C3 (en) | 1979-11-29 |
Family
ID=26217135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2327193A Expired DE2327193C3 (en) | 1972-06-01 | 1973-05-28 | N- (Diethylaminoethyl) -2-methoxy-5methylsulfonylbenzamide, its salts, processes for the preparation of these compounds and medicaments containing these compounds |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5112621B2 (en) |
| AT (1) | AT330147B (en) |
| AU (1) | AU468920B2 (en) |
| BG (1) | BG21602A3 (en) |
| CA (1) | CA991646A (en) |
| CH (1) | CH567463A5 (en) |
| CS (1) | CS168032B2 (en) |
| DD (1) | DD107263A5 (en) |
| DE (1) | DE2327193C3 (en) |
| GB (1) | GB1394559A (en) |
| HU (1) | HU166312B (en) |
| IE (1) | IE37731B1 (en) |
| IL (1) | IL42381A (en) |
| LU (1) | LU67703A1 (en) |
| MC (1) | MC969A1 (en) |
| RO (1) | RO69230A (en) |
| YU (1) | YU39068B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089960A (en) * | 1975-09-25 | 1978-05-16 | Ciba-Geigy Corporation | Antiemetic, psychosomatic and antipsychotic heterocyclic pyridine carboxamides |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06168042A (en) * | 1993-08-06 | 1994-06-14 | Nippon Telegr & Teleph Corp <Ntt> | Constant current power source circuit |
-
1973
- 1973-05-28 BG BG023728A patent/BG21602A3/en unknown
- 1973-05-28 MC MC1044A patent/MC969A1/en unknown
- 1973-05-28 DE DE2327193A patent/DE2327193C3/en not_active Expired
- 1973-05-28 HU HUSO1080A patent/HU166312B/hu not_active IP Right Cessation
- 1973-05-28 CS CS3834A patent/CS168032B2/cs unknown
- 1973-05-29 GB GB2540173A patent/GB1394559A/en not_active Expired
- 1973-05-29 JP JP48060763A patent/JPS5112621B2/ja not_active Expired
- 1973-05-29 IL IL42381A patent/IL42381A/en unknown
- 1973-05-29 YU YU01419/73A patent/YU39068B/en unknown
- 1973-05-30 LU LU67703A patent/LU67703A1/xx unknown
- 1973-05-30 AT AT474273A patent/AT330147B/en not_active IP Right Cessation
- 1973-05-30 CH CH785773A patent/CH567463A5/xx not_active IP Right Cessation
- 1973-05-30 AU AU56305/73A patent/AU468920B2/en not_active Expired
- 1973-05-31 IE IE871/73A patent/IE37731B1/en unknown
- 1973-05-31 CA CA172,910A patent/CA991646A/en not_active Expired
- 1973-05-31 RO RO7374984A patent/RO69230A/en unknown
- 1973-05-31 DD DD171222A patent/DD107263A5/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089960A (en) * | 1975-09-25 | 1978-05-16 | Ciba-Geigy Corporation | Antiemetic, psychosomatic and antipsychotic heterocyclic pyridine carboxamides |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5630573A (en) | 1974-12-05 |
| YU39068B (en) | 1984-04-30 |
| CS168032B2 (en) | 1976-05-28 |
| RO69230A (en) | 1980-12-30 |
| IL42381A (en) | 1976-04-30 |
| JPS5112621B2 (en) | 1976-04-21 |
| CA991646A (en) | 1976-06-22 |
| AT330147B (en) | 1976-06-10 |
| YU141973A (en) | 1982-02-28 |
| IE37731B1 (en) | 1977-09-28 |
| DD107263A5 (en) | 1974-07-20 |
| DE2327193B2 (en) | 1979-04-12 |
| HU166312B (en) | 1975-02-28 |
| BG21602A3 (en) | 1976-07-20 |
| LU67703A1 (en) | 1974-07-05 |
| ATA474273A (en) | 1975-09-15 |
| AU468920B2 (en) | 1976-01-29 |
| MC969A1 (en) | 1974-02-01 |
| CH567463A5 (en) | 1975-10-15 |
| IE37731L (en) | 1973-12-01 |
| JPS4985043A (en) | 1974-08-15 |
| DE2327193C3 (en) | 1979-11-29 |
| IL42381A0 (en) | 1973-07-30 |
| GB1394559A (en) | 1975-05-21 |
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