CA1064944A - Process for the preparation of n-(1-ethyl 2-pyrrolidyl methyl)-2-methoxy-5-sulfamoyl benzamide - Google Patents
Process for the preparation of n-(1-ethyl 2-pyrrolidyl methyl)-2-methoxy-5-sulfamoyl benzamideInfo
- Publication number
- CA1064944A CA1064944A CA254,479A CA254479A CA1064944A CA 1064944 A CA1064944 A CA 1064944A CA 254479 A CA254479 A CA 254479A CA 1064944 A CA1064944 A CA 1064944A
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- ethyl
- benzamide
- pyrrolidylmethyl
- sulphamoyl
- 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 description 6
- 125000003142 tertiary amide group Chemical group 0.000 claims abstract description 3
- 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000003474 anti-emetic effect Effects 0.000 abstract description 2
- 239000002111 antiemetic agent Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- UPWPDUACHOATKO-UHFFFAOYSA-K gallium trichloride Chemical compound Cl[Ga](Cl)Cl UPWPDUACHOATKO-UHFFFAOYSA-K 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 229960004503 metoclopramide Drugs 0.000 description 1
- FVLVBVSILSHUAF-UHFFFAOYSA-N n-benzyl-3,5-dimethyl-n-propan-2-ylbenzamide Chemical compound C=1C(C)=CC(C)=CC=1C(=O)N(C(C)C)CC1=CC=CC=C1 FVLVBVSILSHUAF-UHFFFAOYSA-N 0.000 description 1
- 125000003156 secondary amide group Chemical group 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7518180A FR2314178A1 (fr) | 1975-06-11 | 1975-06-11 | Nouveau procede de preparation du n-(1-ethyl-2-pyrrolidylmethyl) 2-methoxy 5-methoxy 5-sulfamoyl benzamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1064944A true CA1064944A (en) | 1979-10-23 |
Family
ID=9156330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,479A Expired CA1064944A (en) | 1975-06-11 | 1976-06-09 | Process for the preparation of n-(1-ethyl 2-pyrrolidyl methyl)-2-methoxy-5-sulfamoyl benzamide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5231068A (es) |
| AT (1) | AT349458B (es) |
| CA (1) | CA1064944A (es) |
| DE (1) | DE2623077A1 (es) |
| FI (1) | FI761680A7 (es) |
| FR (1) | FR2314178A1 (es) |
| GB (1) | GB1497005A (es) |
| IE (1) | IE43001B1 (es) |
| MX (1) | MX3519E (es) |
| PT (1) | PT65165B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1141095B (it) * | 1980-11-27 | 1986-10-01 | Ravizza Spa | Processo di risoluzione della sulpiride racema |
| ATE20881T1 (de) * | 1982-04-08 | 1986-08-15 | Ile De France | -n-(1-propyl-2-pyrrolidylmethyl-2-methoxy-5sulfamoyl-benzamide und heilverfahren gegen gewisse depressionen. |
| DE4425070A1 (de) * | 1994-07-15 | 1996-01-18 | Degussa | Verfahren zur Herstellung optisch aktiver l-substituierter 2-(Aminomethyl)pyrrolidine |
| JP7406897B2 (ja) * | 2018-12-07 | 2023-12-28 | キヤノン株式会社 | 搬送装置および物品の製造方法 |
-
1975
- 1975-06-11 FR FR7518180A patent/FR2314178A1/fr active Granted
-
1976
- 1976-05-22 DE DE19762623077 patent/DE2623077A1/de not_active Withdrawn
- 1976-06-01 PT PT65165A patent/PT65165B/pt unknown
- 1976-06-01 IE IE1167/76A patent/IE43001B1/en unknown
- 1976-06-01 AT AT400076A patent/AT349458B/de not_active IP Right Cessation
- 1976-06-08 JP JP51067551A patent/JPS5231068A/ja active Pending
- 1976-06-08 GB GB23696/76A patent/GB1497005A/en not_active Expired
- 1976-06-09 CA CA254,479A patent/CA1064944A/en not_active Expired
- 1976-06-09 MX MX76292U patent/MX3519E/es unknown
- 1976-06-11 FI FI761680A patent/FI761680A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2314178B1 (es) | 1979-04-27 |
| FR2314178A1 (fr) | 1977-01-07 |
| AT349458B (de) | 1979-04-10 |
| FI761680A7 (es) | 1976-12-12 |
| PT65165A (fr) | 1976-07-01 |
| IE43001L (en) | 1976-12-11 |
| MX3519E (es) | 1981-01-20 |
| DE2623077A1 (de) | 1976-12-30 |
| GB1497005A (en) | 1978-01-05 |
| IE43001B1 (en) | 1980-12-03 |
| JPS5231068A (en) | 1977-03-09 |
| ATA400076A (de) | 1978-09-15 |
| PT65165B (fr) | 1977-11-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3332950A (en) | 14-hydroxydihydronormorphinone derivatives | |
| KR100724170B1 (ko) | 1,2-다이아미노 화합물을 제조하기 위한 아자이드 비함유공정 | |
| US4535157A (en) | Process for making 6-desoxy-6-methylenenaloxone and 6-desoxy-6-methylenenaltrexone | |
| KR840005448A (ko) | 티에노〔3, 2-c〕 피리딘 유도체의 제조방법 | |
| CA1064944A (en) | Process for the preparation of n-(1-ethyl 2-pyrrolidyl methyl)-2-methoxy-5-sulfamoyl benzamide | |
| CA1171086A (en) | Substituted 2-phenyl-ethylamines and isosteric compounds, process for their production and use | |
| CN103459392A (zh) | 一种制备培美曲塞盐的方法 | |
| CA1116629A (en) | Troponyl-oxamic acid derivatives and process therefor | |
| US3111527A (en) | Amine compounds and methods for their production | |
| WO2005019199A1 (en) | Amorphous duloxetine hydrochloride | |
| US2793212A (en) | Substituted benzamidopiperidinopropanes | |
| US3795681A (en) | Aminothiophene-carboxylic acid esters | |
| US2855398A (en) | Amidines of the indole series | |
| Cruz-Almanza et al. | Deprotection of tetrahydropyranyl ethers with a Mexican bentonite: synthesis of farnesylhydroquinone | |
| DE69707639T2 (de) | Verfahren zur herstellung einer aktivierten aminosäure | |
| KR100829268B1 (ko) | 비정질 아토바스타틴 칼슘의 제조 방법 | |
| 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 | |
| US3821231A (en) | Method for preparation of n-substituted 4-aniline piperidines | |
| GB1565022A (en) | Methylamine derivatives and provesses for preparing the same | |
| US3842086A (en) | Process for the preparation of substituted or unsubstituted pyridines | |
| KR830000882B1 (ko) | N-(1-에틸-2-피롤리딜메틸)-2-메톡시-5-설파모일 벤즈아미드의 제법 | |
| US3089878A (en) | 3-alkyl-4-hydroxy-7-chlorocoumarin-6-sulfonamides | |
| US3410902A (en) | 3-oxo or oxy-1-phenyl-1-indanethylamines | |
| CA1078397A (en) | Process for the preparation of n-(1-ethyl-2-pyrrolidylmethyl)-2-methoxy-5-sulfamoyl benzamide | |
| US4010164A (en) | N-(furyl-methyl)-2-hydroxy-5,9,9-trimethyl-benzomorphans and salts thereof |