CA1078397A - Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide - Google Patents
Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamideInfo
- Publication number
- CA1078397A CA1078397A CA254,482A CA254482A CA1078397A CA 1078397 A CA1078397 A CA 1078397A CA 254482 A CA254482 A CA 254482A CA 1078397 A CA1078397 A CA 1078397A
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- ethyl
- pyrrolidylmethyl
- sulphamoyl
- salts
- 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
- 238000000034 method Methods 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000000962 organic group Chemical group 0.000 claims abstract description 4
- 150000002081 enamines Chemical class 0.000 claims abstract description 3
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 235000005985 organic acids Nutrition 0.000 claims abstract description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims abstract 2
- XFZMCFJADJFEBB-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(Cl)=O XFZMCFJADJFEBB-UHFFFAOYSA-N 0.000 claims 1
- GCLVFECQGYAYFG-KTKRTIGZSA-N CCN1C(CN/C(\C)=C(/C)\C(O)=O)CCC1 Chemical compound CCN1C(CN/C(\C)=C(/C)\C(O)=O)CCC1 GCLVFECQGYAYFG-KTKRTIGZSA-N 0.000 claims 1
- 230000003474 anti-emetic effect Effects 0.000 abstract description 2
- 239000002111 antiemetic agent Substances 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- XKORCTIIRYKLLG-ONEGZZNKSA-N methyl (e)-3-aminobut-2-enoate Chemical compound COC(=O)\C=C(/C)N XKORCTIIRYKLLG-ONEGZZNKSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- -1 pyrrolidylmethyl Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007787 solid Substances 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
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518824A FR2314918A1 (fr) | 1975-06-17 | 1975-06-17 | Nouveau procede de preparation du n-(1-ethyl-2-pyrrolidylmethyl) 2-methoxy 5-sulfamoyl benzamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078397A true CA1078397A (en) | 1980-05-27 |
Family
ID=9156603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,482A Expired CA1078397A (en) | 1975-06-17 | 1976-06-09 | Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS6016415B2 (ref) |
| AT (1) | AT349457B (ref) |
| CA (1) | CA1078397A (ref) |
| DE (1) | DE2622999A1 (ref) |
| FI (1) | FI761746A7 (ref) |
| FR (1) | FR2314918A1 (ref) |
| GB (1) | GB1501771A (ref) |
| IE (1) | IE43003B1 (ref) |
| MX (1) | MX3581E (ref) |
| PT (1) | PT65167B (ref) |
-
1975
- 1975-06-17 FR FR7518824A patent/FR2314918A1/fr active Granted
-
1976
- 1976-05-22 DE DE19762622999 patent/DE2622999A1/de not_active Withdrawn
- 1976-06-01 IE IE1169/76A patent/IE43003B1/en unknown
- 1976-06-01 AT AT399976A patent/AT349457B/de not_active IP Right Cessation
- 1976-06-01 PT PT65167A patent/PT65167B/pt unknown
- 1976-06-09 MX MX76294U patent/MX3581E/es unknown
- 1976-06-09 CA CA254,482A patent/CA1078397A/en not_active Expired
- 1976-06-10 GB GB24112/76A patent/GB1501771A/en not_active Expired
- 1976-06-14 JP JP51070315A patent/JPS6016415B2/ja not_active Expired
- 1976-06-16 FI FI761746A patent/FI761746A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6016415B2 (ja) | 1985-04-25 |
| MX3581E (es) | 1981-03-19 |
| FR2314918A1 (fr) | 1977-01-14 |
| ATA399976A (de) | 1978-09-15 |
| PT65167A (fr) | 1976-07-01 |
| IE43003L (en) | 1976-12-17 |
| JPS52262A (en) | 1977-01-05 |
| IE43003B1 (en) | 1980-12-03 |
| FI761746A7 (ref) | 1976-12-18 |
| GB1501771A (en) | 1978-02-22 |
| AT349457B (de) | 1979-04-10 |
| DE2622999A1 (de) | 1976-12-30 |
| FR2314918B1 (ref) | 1977-12-09 |
| PT65167B (fr) | 1977-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4329556A (en) | N-Azidosulfonylaryl-maleinimides | |
| US5221692A (en) | Ether linked and relatively nonpungent analogues of N-nonanoyl vanillylamide | |
| US4123530A (en) | N-cyclohexyl-piperazino acetamides and propionamides | |
| CA1078397A (en) | Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide | |
| US4117012A (en) | 2-aminomethyleneindanone analgesic agents | |
| CA1047504A (en) | N-(2-pyrrolidinyl alkyl) substitutes and derivatives thereof | |
| CA1055502A (en) | Process for the preparation of 2,5-disubstituted benzamides | |
| CH679856A5 (ref) | ||
| US3743647A (en) | Nicotinoylaminoethanesulfonylamino-thiazole and pharmaceutically acceptable acid addition salts thereof | |
| CA1069911A (en) | Enamines | |
| US4143143A (en) | Substituted imidazo[5,1-a]isoquinolines | |
| DE1518271A1 (de) | Verfahren zur Herstellung von substituierten Benzamiden | |
| IE861796L (en) | Imidazolines and intermediates thereof | |
| US4022830A (en) | Process for preparing polychlorobenzamide derivatives | |
| US4353914A (en) | Antitussive anilides | |
| US4161532A (en) | N-(1'-ethyl-2'-oxo-5'-pyrrolidinylmethyl) benzamide compounds and derivatives, method of preparation and pharmaceutical preparations | |
| GB2068963A (en) | Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents and relevant preparation processes | |
| JPS5555160A (en) | Preparation of substituted benzamide | |
| JP3892963B2 (ja) | Ｌ−バリンベンジルエステルｐ−トルエンスルホン酸塩の製造方法 | |
| US2674615A (en) | 1-arylcycloalkane 1-thiocar-boxylates | |
| KR970001536B1 (ko) | 트리요오도벤젠 유도체의 제조방법 | |
| AT368153B (de) | Verfahren zur herstellung des neuen n-(1'-allylpyrrolidin-2'-yl-methyl)-2-methoxy-4,5- azimidobenzamides und seiner saeureadditionssalze | |
| PT98184A (pt) | Processo de preparacao de derivados de 5-isotiazolamina e de composicoes farmaceuticas que os contem | |
| US3995037A (en) | Methods of treating a mammal afflicted with pain with dialkylaminoalkyl ethers of 2-alkoxy-3,5-dihalobenzene and salts thereof | |
| KR820000075B1 (ko) | 2,5-디치환 벤즈아미드의 제조 방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |