DE2327192C2 - Verfahren zur Herstellung von N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid und seinen Additionssalzen - Google Patents
Verfahren zur Herstellung von N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid und seinen AdditionssalzenInfo
- Publication number
- DE2327192C2 DE2327192C2 DE2327192A DE2327192A DE2327192C2 DE 2327192 C2 DE2327192 C2 DE 2327192C2 DE 2327192 A DE2327192 A DE 2327192A DE 2327192 A DE2327192 A DE 2327192A DE 2327192 C2 DE2327192 C2 DE 2327192C2
- Authority
- DE
- Germany
- Prior art keywords
- methoxy
- diethylaminoethyl
- preparation
- addition salts
- tia
- 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
- 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 5
- 238000000034 method Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 5
- 239000002253 acid Substances 0.000 claims description 6
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 230000002903 catalepsic effect Effects 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229960004503 metoclopramide Drugs 0.000 claims description 3
- 229960005344 tiapride Drugs 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 238000010171 animal model Methods 0.000 claims 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 2
- 239000011707 mineral Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 235000005985 organic acids Nutrition 0.000 claims 2
- 206010022998 Irritability Diseases 0.000 claims 1
- 230000003474 anti-emetic effect Effects 0.000 claims 1
- 239000002111 antiemetic agent Substances 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 claims 1
- 230000001079 digestive effect Effects 0.000 claims 1
- 231100001231 less toxic Toxicity 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 229940001470 psychoactive drug Drugs 0.000 claims 1
- 239000004089 psychotropic agent Substances 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 1
- XDMJPUGKVSMTJS-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound C(C)N(CC)CCC=1C(=C(C(=O)N)C=C(C=1)S(=O)(=O)C)OC XDMJPUGKVSMTJS-UHFFFAOYSA-N 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 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
- 239000002244 precipitate Substances 0.000 description 1
- 239000002904 solvent 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
- 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
- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- 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
-
- 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
- C07D211/18—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 with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—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 with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7219804A FR2193577A1 (en) | 1972-06-01 | 1972-06-01 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7219803A FR2187310A1 (en) | 1972-06-01 | 1972-06-01 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7221307A FR2187323A1 (en) | 1972-06-12 | 1972-06-12 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
| FR7312045A FR2224447A1 (en) | 1973-04-03 | 1973-04-03 | N-(substd alkyl)-2-alk(enyl)oxybenzamides - antiemetics digestion-regulators and psychotropics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2327192A1 DE2327192A1 (de) | 1973-12-13 |
| DE2327192C2 true DE2327192C2 (de) | 1983-02-17 |
Family
ID=27446178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2327192A Expired DE2327192C2 (de) | 1972-06-01 | 1973-05-28 | Verfahren zur Herstellung von N-(Diethylaminoethyl)-2-methoxy-5-methylsulfonylbenzamid und seinen Additionssalzen |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5648507B2 (en, 2012) |
| AU (1) | AU472570B2 (en, 2012) |
| BG (1) | BG21213A3 (en, 2012) |
| CA (1) | CA986927A (en, 2012) |
| CH (1) | CH585699A5 (en, 2012) |
| CS (1) | CS174885B2 (en, 2012) |
| DD (1) | DD107264A5 (en, 2012) |
| DE (1) | DE2327192C2 (en, 2012) |
| GB (1) | GB1394563A (en, 2012) |
| HU (1) | HU167379B (en, 2012) |
| IE (1) | IE38116B1 (en, 2012) |
| IL (1) | IL42380A (en, 2012) |
| LU (1) | LU67702A1 (en, 2012) |
| MC (1) | MC965A1 (en, 2012) |
| PH (2) | PH10249A (en, 2012) |
| YU (1) | YU39069B (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH605793A5 (fr) * | 1974-03-05 | 1978-10-13 | Soc Et Scient Et Ind | Procédé de préparation de nouveaux N-(1benzylpyrrollidinil 2-alkyl) benzamides substitués |
| GB1513631A (en) * | 1976-02-17 | 1978-06-07 | Gallardo Antonio Sa | Piperidine derivatives |
| US5721255A (en) * | 1992-08-19 | 1998-02-24 | Pfizer Inc. | Substituted benzylamino nitrogen containing non-aromatic heterocycles |
-
1973
- 1973-05-28 HU HUSO1079A patent/HU167379B/hu unknown
- 1973-05-28 CS CS3835A patent/CS174885B2/cs unknown
- 1973-05-28 DE DE2327192A patent/DE2327192C2/de not_active Expired
- 1973-05-28 MC MC1045A patent/MC965A1/xx unknown
- 1973-05-28 PH PH14660*A patent/PH10249A/en unknown
- 1973-05-28 BG BG023727A patent/BG21213A3/xx unknown
- 1973-05-29 JP JP6076473A patent/JPS5648507B2/ja not_active Expired
- 1973-05-29 IL IL42380A patent/IL42380A/en unknown
- 1973-05-29 GB GB2540273A patent/GB1394563A/en not_active Expired
- 1973-05-29 YU YU01420/73A patent/YU39069B/xx unknown
- 1973-05-30 AU AU56306/73A patent/AU472570B2/en not_active Expired
- 1973-05-30 CH CH785873A patent/CH585699A5/xx not_active IP Right Cessation
- 1973-05-30 LU LU67702A patent/LU67702A1/xx unknown
- 1973-05-31 DD DD171220A patent/DD107264A5/xx unknown
- 1973-05-31 CA CA172,906A patent/CA986927A/fr not_active Expired
- 1973-05-31 IE IE872/73A patent/IE38116B1/xx unknown
-
1975
- 1975-05-27 PH PH17195A patent/PH11617A/en unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| LU67702A1 (en, 2012) | 1974-07-05 |
| IE38116L (en) | 1973-12-01 |
| DD107264A5 (en, 2012) | 1974-07-20 |
| CH585699A5 (en, 2012) | 1977-03-15 |
| IE38116B1 (en) | 1978-01-04 |
| BG21213A3 (bg) | 1976-03-20 |
| AU472570B2 (en) | 1976-05-27 |
| PH11617A (en) | 1978-04-12 |
| CS174885B2 (en, 2012) | 1977-04-29 |
| HU167379B (en, 2012) | 1975-09-27 |
| YU39069B (en) | 1984-04-30 |
| IL42380A0 (en) | 1973-07-30 |
| CA986927A (fr) | 1976-04-06 |
| IL42380A (en) | 1976-12-31 |
| GB1394563A (en) | 1975-05-21 |
| YU142073A (en) | 1982-02-28 |
| JPS5648507B2 (en, 2012) | 1981-11-16 |
| AU5630673A (en) | 1974-12-05 |
| PH10249A (en) | 1976-10-14 |
| JPS4985037A (en, 2012) | 1974-08-15 |
| MC965A1 (fr) | 1974-02-01 |
| DE2327192A1 (de) | 1973-12-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8125 | Change of the main classification |
Ipc: C07C143/78 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |