DE2327193C3 - N-(Diethylaminoethyl)-2-methoxy-5methylsulfonylbenzamid, seine Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Arzneimittel - Google Patents
N-(Diethylaminoethyl)-2-methoxy-5methylsulfonylbenzamid, seine Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2327193C3 DE2327193C3 DE2327193A DE2327193A DE2327193C3 DE 2327193 C3 DE2327193 C3 DE 2327193C3 DE 2327193 A DE2327193 A DE 2327193A DE 2327193 A DE2327193 A DE 2327193A DE 2327193 C3 DE2327193 C3 DE 2327193C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- methoxy
- diethylaminoethyl
- salts
- preparation
- 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
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 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 7
- 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
- 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
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 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
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 229960004503 metoclopramide Drugs 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
- 241001465754 Metazoa Species 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000002903 catalepsic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 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
- 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
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 230000036626 alertness Effects 0.000 description 1
- 230000003197 catalytic 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
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960004815 meprobamate Drugs 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
- 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)
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 (de) | 1974-01-03 |
| DE2327193B2 DE2327193B2 (de) | 1979-04-12 |
| DE2327193C3 true DE2327193C3 (de) | 1979-11-29 |
Family
ID=26217135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2327193A Expired DE2327193C3 (de) | 1972-06-01 | 1973-05-28 | N-(Diethylaminoethyl)-2-methoxy-5methylsulfonylbenzamid, seine Salze, Verfahren zur Herstellung dieser Verbindungen sowie diese Verbindungen enthaltende Arzneimittel |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS5112621B2 (hu) |
| AT (1) | AT330147B (hu) |
| AU (1) | AU468920B2 (hu) |
| BG (1) | BG21602A3 (hu) |
| CA (1) | CA991646A (hu) |
| CH (1) | CH567463A5 (hu) |
| CS (1) | CS168032B2 (hu) |
| DD (1) | DD107263A5 (hu) |
| DE (1) | DE2327193C3 (hu) |
| GB (1) | GB1394559A (hu) |
| HU (1) | HU166312B (hu) |
| IE (1) | IE37731B1 (hu) |
| IL (1) | IL42381A (hu) |
| LU (1) | LU67703A1 (hu) |
| MC (1) | MC969A1 (hu) |
| RO (1) | RO69230A (hu) |
| YU (1) | YU39068B (hu) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH614709A5 (hu) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag | |
| JPH06168042A (ja) * | 1993-08-06 | 1994-06-14 | Nippon Telegr & Teleph Corp <Ntt> | 定電流電源回路 |
-
1973
- 1973-05-28 DE DE2327193A patent/DE2327193C3/de not_active Expired
- 1973-05-28 MC MC1044A patent/MC969A1/xx unknown
- 1973-05-28 HU HUSO1080A patent/HU166312B/hu not_active IP Right Cessation
- 1973-05-28 CS CS3834A patent/CS168032B2/cs unknown
- 1973-05-28 BG BG023728A patent/BG21602A3/xx unknown
- 1973-05-29 IL IL42381A patent/IL42381A/xx unknown
- 1973-05-29 YU YU01419/73A patent/YU39068B/xx unknown
- 1973-05-29 GB GB2540173A patent/GB1394559A/en not_active Expired
- 1973-05-29 JP JP48060763A patent/JPS5112621B2/ja not_active Expired
- 1973-05-30 CH CH785773A patent/CH567463A5/xx 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
- 1973-05-30 AT AT474273A patent/AT330147B/de not_active IP Right Cessation
- 1973-05-31 CA CA172,910A patent/CA991646A/fr not_active Expired
- 1973-05-31 RO RO7374984A patent/RO69230A/ro unknown
- 1973-05-31 IE IE871/73A patent/IE37731B1/xx unknown
- 1973-05-31 DD DD171222A patent/DD107263A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4985043A (hu) | 1974-08-15 |
| RO69230A (ro) | 1980-12-30 |
| MC969A1 (fr) | 1974-02-01 |
| CH567463A5 (hu) | 1975-10-15 |
| AU468920B2 (en) | 1976-01-29 |
| DE2327193B2 (de) | 1979-04-12 |
| BG21602A3 (bg) | 1976-07-20 |
| AU5630573A (en) | 1974-12-05 |
| GB1394559A (en) | 1975-05-21 |
| IE37731B1 (en) | 1977-09-28 |
| YU39068B (en) | 1984-04-30 |
| DD107263A5 (hu) | 1974-07-20 |
| IL42381A (en) | 1976-04-30 |
| JPS5112621B2 (hu) | 1976-04-21 |
| AT330147B (de) | 1976-06-10 |
| LU67703A1 (hu) | 1974-07-05 |
| IL42381A0 (en) | 1973-07-30 |
| CA991646A (fr) | 1976-06-22 |
| ATA474273A (de) | 1975-09-15 |
| YU141973A (en) | 1982-02-28 |
| IE37731L (en) | 1973-12-01 |
| DE2327193A1 (de) | 1974-01-03 |
| CS168032B2 (hu) | 1976-05-28 |
| HU166312B (hu) | 1975-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) |