DE2327193B2 - N- (Diethylaminoethyl) -2-methoxy-5methylsulfonylbenzamide, its salts, processes for the preparation of these compounds and medicaments containing these compounds - Google Patents
N- (Diethylaminoethyl) -2-methoxy-5methylsulfonylbenzamide, its salts, processes for the preparation of these compounds and medicaments containing these compoundsInfo
- Publication number
- DE2327193B2 DE2327193B2 DE2327193A DE2327193A DE2327193B2 DE 2327193 B2 DE2327193 B2 DE 2327193B2 DE 2327193 A DE2327193 A DE 2327193A DE 2327193 A DE2327193 A DE 2327193A DE 2327193 B2 DE2327193 B2 DE 2327193B2
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- compounds
- salts
- diethylaminoethyl
- male
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 14
- 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 title claims description 8
- 239000003814 drug Substances 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 5
- 229960004503 metoclopramide Drugs 0.000 claims description 4
- 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 claims description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 238000010171 animal model Methods 0.000 claims description 2
- 238000011065 in-situ storage Methods 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
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 231100001231 less toxic Toxicity 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002903 catalepsic effect Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229960005344 tiapride Drugs 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 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
- 239000002050 international nonproprietary name Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
Tabellen
Kataleptische WirkungTables
Cataleptic effect
VersuchstierLaboratory animal
Die Erfindung betrifft N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid sowie seine Salze mit pharmazeutisch verträglichen Mineral- oder organischen Säuren, ein Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Arzneimittel gemäß den vorstehenden Ansprüchen.The invention relates to N- (diethylaminoethyl) -2-methoxy-5-methylsulfonylbenzamide as well as its salts with pharmaceutically acceptable mineral or organic acids, a process for the preparation of these Compounds and medicaments containing these compounds according to the preceding claims.
Die Verbindung der Erfindung wird in an sich bekannter Weise erhalten, indem man Diethylaminoethylamin mit Phosphortrichlorid umsetzt und die in situ erhaltene Phosphazoverbindung der FormelThe compound of the invention is obtained in a manner known per se by adding diethylaminoethylamine Reacts with phosphorus trichloride and the phosphazo compound obtained in situ of the formula
(C2HS)2N-CH2-CH2-NH-P=N-CH2CH2-N(C2Hs)2 (C 2 HS) 2 N-CH 2 -CH 2 -NH-P = N-CH 2 CH 2 -N (C 2 Hs) 2
mit 2-Methoxy-5-methylsulfonylbenzoesäure reagieren läßt. Dabei wird ein Lösungsmittel, z. B. Pyridin, verwendet, wobei man bis zur Rückflußtemperatur erhitzt.can react with 2-methoxy-5-methylsulfonylbenzoic acid. A solvent, e.g. B. pyridine, used, heating to reflux temperature.
Die Verbindung der Erfindung, die inzwischen unter dem internationalen Freinamen Triaprid (TIA) geführt wird, weist interessante pharmakologische Eigenschaften auf. Im folgenden wird über die Ergebnisse von Vergleichsversuchen hinsichtlich der toxischen und kataleptischen Wirkung (vgl. Arzneimittel-Forsch. 12 [1962] S. 964-968) berichtet. Als Vergleichsverbindung wurde das strukturell verwandte N-(Diethylaminoethyl)-2-methoxy-4-amino-5-chlorbenzamid (Metoclopramid; MTC) herangezogen.The compound of the invention, which in the meantime led under the international non-proprietary name Triaprid (TIA) has interesting pharmacological properties. The following is about the results of Comparative tests with regard to the toxic and cataleptic effects (cf. Arzneimittel-Forsch. 12 [1962] pp. 964-968) reported. The structurally related N- (diethylaminoethyl) -2-methoxy-4-amino-5-chlorobenzamide was used as a comparison compound (Metoclopramide; MTC) used.
DE
TIADE
TIA
MTCMTC
Ratte (männl.)Rat (male)
30% bei 200 mg/kg30% at 200 mg / kg
3C3C
Die in Vergleich zu Metoclopramid erheblich herabgesetzte kataleptische Wirkung von Tiaprid läßt erkennen, daß die letztere Verbindung in der Humantherapie besonders gut vertragen wird. Tiaprid kann daher noch in Dosierungen verabreicht werden, die bei Metoclopramid wegen zu befürchtender pyramidaler Effekte nicht mehr möglich sind. Diese Ergebnisse konnten in umfangreichen klinischen Versuchen bestätigt werden.The significantly reduced cataleptic effect of tiapride compared to metoclopramide recognize that the latter compound is particularly well tolerated in human therapy. Tiapride can therefore still be administered in doses that are to be feared with metoclopramide because of pyramidal Effects are no longer possible. These results have been confirmed in extensive clinical trials will.
In klinischen Versuchen konnte weiterhin bestätigt werden, daß Tiaprid eine günstige sedativ-somatische Wirkung entfaltet, ohne daß dabei eine sedativ-psychische Wirkung, die in einer Schläfrigkeit und herabgesetzter Wachsamkeit zum Ausdruck kommt, auftritt. Diese Wirkung des Tiaprids erweist sich als besonders günstig für die therapeutische Behandlung des psychomotorischen Verhaltens von Alkoholikern, bei denen durch geeignete Dosierung ein günstiger sedativ-psychischer Effekt erhalten wird und die Patienten dennoch mit dem Pflegepersonal kooperieren können. Dieser Effekt kann beispielsweise mit einem bekannten, zentral wirkenden Muskelrelaxanz, dem Meprobamat, nicht erreicht werden.In clinical trials it could also be confirmed that tiapride has a favorable sedative-somatic Effect unfolds without thereby a sedative-psychic effect, resulting in a drowsiness and degraded Vigilance is expressed, occurs. This effect of the Tiaprids turns out to be special beneficial for the therapeutic treatment of psychomotor behavior in alcoholics in whom a favorable sedative-psychological effect is obtained through suitable dosing and the patient nonetheless be able to cooperate with the nursing staff. This effect can, for example, with a well-known, central effective muscle relaxant, the meprobamate, cannot be achieved.
Die Herstellung der Verbindung der Erfindung wird im folgenden anhand eines Ausführungsbeispiels näher erläutert.The production of the connection of the invention is explained in more detail below with the aid of an exemplary embodiment explained.
N-(Diethylaminoethyl)-2-methoxy-5-methyIsulfonylbenzamid N- (Diethylaminoethyl) -2-methoxy-5-methyl-sulfonylbenzamide
In einen 1-1-K.olben gibt man eine Lösung von 16,4 g N,N-Diethylethylendiamin in 376 ml Pyridin.A solution of 16.4 g is placed in a 1-1-K flask N, N-diethylethylenediamine in 376 ml of pyridine.
Dann fügt man bei Raumtemperatur eine Lösung von 3,76 g Phosphortrichlorid in 43 ml Pyridin hinzu. Nach 30minütigem Rühren fügt man 10 g 2-Methoxy-5-methylsulfonylbenzoesäure hinzu. Man erhitzt 4V2 Stunden am Rückfluß.A solution of 3.76 g of phosphorus trichloride in 43 ml of pyridine is then added at room temperature. After stirring for 30 minutes, 10 g of 2-methoxy-5-methylsulfonylbenzoic acid are added. The mixture is refluxed for 4V for 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%iger Salzsäure gelöst. Nach dem Filtrieren macht man das Filtrat mit Natronlauge alkalisch.After cooling, the solvent is evaporated off in vacuo. The residue is in a mixture dissolved by 130 ml of water and 6.5 ml of 36% hydrochloric acid. After filtering, make the filtrate with Caustic soda alkaline.
Der Niederschlag wird abfiltriert, gewaschen und im Trockenschrank bei 50° C getrocknet.The precipitate is filtered off, washed and dried at 50 ° C. in a drying cabinet.
Man erhält 7,5 g N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid. 7.5 g of N- (diethylaminoethyl) -2-methoxy-5-methylsulfonylbenzamide are obtained.
Smp. 122°CM.p. 122 ° C
S (%) berechnet: 9,76
b5 gefunden: 9,84S (%) calculated: 9.76
b5 found: 9.84
Claims (3)
reichungAppointment
reaching
TIA MTCDL 50 (mg / kg; base)
TIA MTC
13838
138
IPIV
IP
349157
349
13046
130
IPIV
IP
346240
346
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 DE2327193A1 (en) | 1974-01-03 |
| DE2327193B2 true 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) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH614709A5 (en) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag | |
| JPH06168042A (en) * | 1993-08-06 | 1994-06-14 | Nippon Telegr & Teleph Corp <Ntt> | Constant current power source circuit |
-
1973
- 1973-05-28 BG BG23728A patent/BG21602A3/xx unknown
- 1973-05-28 HU HUSO1080A patent/HU166312B/hu not_active IP Right Cessation
- 1973-05-28 DE DE2327193A patent/DE2327193C3/en not_active Expired
- 1973-05-28 MC MC1044A patent/MC969A1/en unknown
- 1973-05-28 CS CS3834A patent/CS168032B2/cs unknown
- 1973-05-29 GB GB2540173A patent/GB1394559A/en not_active Expired
- 1973-05-29 IL IL42381A patent/IL42381A/en unknown
- 1973-05-29 JP JP48060763A patent/JPS5112621B2/ja not_active Expired
- 1973-05-29 YU YU01419/73A patent/YU39068B/en unknown
- 1973-05-30 CH CH785773A patent/CH567463A5/xx not_active IP Right Cessation
- 1973-05-30 AT AT474273A patent/AT330147B/en not_active IP Right Cessation
- 1973-05-30 LU LU67703A patent/LU67703A1/xx unknown
- 1973-05-30 AU AU56305/73A patent/AU468920B2/en not_active Expired
- 1973-05-31 DD DD171222A patent/DD107263A5/xx unknown
- 1973-05-31 CA CA172,910A patent/CA991646A/en not_active Expired
- 1973-05-31 IE IE871/73A patent/IE37731B1/en unknown
- 1973-05-31 RO RO7374984A patent/RO69230A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH567463A5 (en) | 1975-10-15 |
| MC969A1 (en) | 1974-02-01 |
| AT330147B (en) | 1976-06-10 |
| DD107263A5 (en) | 1974-07-20 |
| YU39068B (en) | 1984-04-30 |
| AU468920B2 (en) | 1976-01-29 |
| IE37731L (en) | 1973-12-01 |
| GB1394559A (en) | 1975-05-21 |
| DE2327193C3 (en) | 1979-11-29 |
| HU166312B (en) | 1975-02-28 |
| YU141973A (en) | 1982-02-28 |
| RO69230A (en) | 1980-12-30 |
| IL42381A (en) | 1976-04-30 |
| IE37731B1 (en) | 1977-09-28 |
| JPS5112621B2 (en) | 1976-04-21 |
| BG21602A3 (en) | 1976-07-20 |
| DE2327193A1 (en) | 1974-01-03 |
| LU67703A1 (en) | 1974-07-05 |
| JPS4985043A (en) | 1974-08-15 |
| CS168032B2 (en) | 1976-05-28 |
| ATA474273A (en) | 1975-09-15 |
| CA991646A (en) | 1976-06-22 |
| IL42381A0 (en) | 1973-07-30 |
| AU5630573A (en) | 1974-12-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |