GB1420890A - N-1-ethyl-2-pyrrolidinylmethyl-2-methoxy-5-sulphamoylbenzamide - Google Patents
N-1-ethyl-2-pyrrolidinylmethyl-2-methoxy-5-sulphamoylbenzamideInfo
- Publication number
- GB1420890A GB1420890A GB942574A GB942574A GB1420890A GB 1420890 A GB1420890 A GB 1420890A GB 942574 A GB942574 A GB 942574A GB 942574 A GB942574 A GB 942574A GB 1420890 A GB1420890 A GB 1420890A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- ethyl
- sulphamoylbenzamide
- pyrrolidylmethyl
- treating
- 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
- NWWDYCPAOHUKFF-UHFFFAOYSA-N N-ethyl-6-methoxy-6-(pyrrolidin-1-ylmethyl)-3-sulfamoylcyclohexa-2,4-diene-1-carboxamide Chemical compound C(C)NC(C1C(C=CC(=C1)S(N)(=O)=O)(OC)CN1CCCC1)=O NWWDYCPAOHUKFF-UHFFFAOYSA-N 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- BGRJTUBHPOOWDU-UHFFFAOYSA-N sulpiride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- MFBSRCLGOVIYSM-UHFFFAOYSA-N 3-cyano-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C#N MFBSRCLGOVIYSM-UHFFFAOYSA-N 0.000 abstract 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 1
- FOQGMMRMUFBONJ-UHFFFAOYSA-N N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzenecarbothioamide Chemical compound CCN1CCCC1CNC(=S)C1=C(OC)C=CC(=C1)S(N)(=O)=O FOQGMMRMUFBONJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 229940100198 alkylating agent Drugs 0.000 abstract 1
- 239000002168 alkylating agent Substances 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940046892 lead acetate Drugs 0.000 abstract 1
- 150000002681 magnesium compounds Chemical class 0.000 abstract 1
- IYFLWZQOYJVVPS-UHFFFAOYSA-N methyl 6-methoxy-3-sulfamoyliminocyclohexa-1,5-diene-1-carboxylate Chemical compound COC=1C(C(=O)OC)=CC(CC1)=NS(N)(=O)=O IYFLWZQOYJVVPS-UHFFFAOYSA-N 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- CWNMOSOZAFYNOE-UHFFFAOYSA-N o-methyl 2-methoxy-5-sulfamoylbenzenecarbothioate Chemical compound COC(=S)C1=CC(S(N)(=O)=O)=CC=C1OC CWNMOSOZAFYNOE-UHFFFAOYSA-N 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 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)
Abstract
1420890 Process for making N-(1-ethyl-2- pyrrolidylmethyl) - 2 - methoxy - 5 - sulphamoylbenzamide and intermediates therefor SOC D'ETUDES SCIENTIFIQUES ET INDUSTRIELLES DE L'ILE-DE-FRANCE 1 March 1974 [6 March 1973] 9425/74 Heading C2C The invention comprises a method of preparing N - (1 - ethyl - 2 - pyrrolidylmethyl) - 2- methoxy - 5 - sulphamoylbenzamide, its pharmaceutically acceptable addition salts with inorganic or organic acids, and quaternary ammonium salts obtained by reacting it with an aliphatic or aromatic alkylating agent, by treating 2 - methoxy - 5 - sulphamoylbenzoic acid with phosphorus pentachloride and ammonia to obtain 2-methoxy-5-sulphamoylbenzonitrile, treating this compound with methanol to give methyl 2-methoxy-5-sulphamoyliminobenzoate, treating the latter with hydrogen sulphide to produce methyl 2-methoxy-5-sulphamoylthiobenzoate, reacting this with the magnesium compound of N - ethyl - α - aminomethylpyrrolidine to give N - (1 - ethyl - 2 - pyrrolidylmethyl) - 2- methoxy - 5 - sulphamoylthiobenzamide, and treating this last product with lead acetate to produce N - (1 - ethyl - 2 - pyrrolidylmethyl)- 2-methoxy-5-sulphamoylbenzamide and optionally converting the product obtained into a salt thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7308033A FR2220522B1 (en) | 1973-03-06 | 1973-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1420890A true GB1420890A (en) | 1976-01-14 |
Family
ID=9115878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB942574A Expired GB1420890A (en) | 1973-03-06 | 1974-03-01 | N-1-ethyl-2-pyrrolidinylmethyl-2-methoxy-5-sulphamoylbenzamide |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5641631B2 (en) |
| AR (1) | AR200304A1 (en) |
| AT (1) | AT358567B (en) |
| CA (1) | CA1010046A (en) |
| DE (1) | DE2409891A1 (en) |
| ES (1) | ES423781A1 (en) |
| FI (1) | FI57931C (en) |
| FR (1) | FR2220522B1 (en) |
| GB (1) | GB1420890A (en) |
| IE (1) | IE38949B1 (en) |
-
1973
- 1973-03-06 FR FR7308033A patent/FR2220522B1/fr not_active Expired
-
1974
- 1974-02-25 CA CA193,458A patent/CA1010046A/en not_active Expired
- 1974-02-27 AT AT159074A patent/AT358567B/en not_active IP Right Cessation
- 1974-03-01 JP JP2411074A patent/JPS5641631B2/ja not_active Expired
- 1974-03-01 DE DE19742409891 patent/DE2409891A1/en active Pending
- 1974-03-01 ES ES423781A patent/ES423781A1/en not_active Expired
- 1974-03-01 GB GB942574A patent/GB1420890A/en not_active Expired
- 1974-03-04 FI FI62974A patent/FI57931C/en active
- 1974-03-04 AR AR25260474A patent/AR200304A1/en active
- 1974-03-04 IE IE44174A patent/IE38949B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE38949L (en) | 1974-09-06 |
| IE38949B1 (en) | 1978-07-05 |
| CA1010046A (en) | 1977-05-10 |
| FI57931C (en) | 1980-11-10 |
| AT358567B (en) | 1980-09-25 |
| JPS49124056A (en) | 1974-11-27 |
| FR2220522B1 (en) | 1977-02-04 |
| JPS5641631B2 (en) | 1981-09-29 |
| ATA159074A (en) | 1980-02-15 |
| ES423781A1 (en) | 1976-05-01 |
| FI57931B (en) | 1980-07-31 |
| DE2409891A1 (en) | 1974-09-12 |
| FR2220522A1 (en) | 1974-10-04 |
| AR200304A1 (en) | 1974-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19930301 |