DE2322573A1 - Verfahren zur herstellung von n-aethyl2-(2-methoxy-5-sulfamoyl-benzoyl)-methylamino-pyrrolidin - Google Patents
Verfahren zur herstellung von n-aethyl2-(2-methoxy-5-sulfamoyl-benzoyl)-methylamino-pyrrolidinInfo
- Publication number
- DE2322573A1 DE2322573A1 DE2322573A DE2322573A DE2322573A1 DE 2322573 A1 DE2322573 A1 DE 2322573A1 DE 2322573 A DE2322573 A DE 2322573A DE 2322573 A DE2322573 A DE 2322573A DE 2322573 A1 DE2322573 A1 DE 2322573A1
- Authority
- DE
- Germany
- Prior art keywords
- ethyl
- sulfamoyl
- benzoyl
- methoxy
- pyrrolidine
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
- -1 5-sulfamoyl-benzoyl Chemical group 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- XFEJOGHZSITRAL-UHFFFAOYSA-N 3-chloro-1-ethylpiperidine Chemical compound CCN1CCCC(Cl)C1 XFEJOGHZSITRAL-UHFFFAOYSA-N 0.000 claims description 2
- OHLXXFUDMGUKCG-UHFFFAOYSA-N n-methylpyrrolidin-1-amine Chemical compound CNN1CCCC1 OHLXXFUDMGUKCG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010022714 Intestinal ulcer Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002888 effect on disease Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000008673 vomiting Effects 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES403003A ES403003A1 (es) | 1972-05-19 | 1972-05-19 | Nuevo procedimiento para la preparacion de la 2-metoxi 5- sulfamoil benzoil (n etil) 2-pirrolidinometilamina. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2322573A1 true DE2322573A1 (de) | 1973-11-22 |
Family
ID=8461225
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2322573A Pending DE2322573A1 (de) | 1972-05-19 | 1973-05-04 | Verfahren zur herstellung von n-aethyl2-(2-methoxy-5-sulfamoyl-benzoyl)-methylamino-pyrrolidin |
Country Status (13)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH584688A5 (enrdf_load_stackoverflow) * | 1972-06-23 | 1977-02-15 | Delmar Chem |
-
1972
- 1972-05-19 ES ES403003A patent/ES403003A1/es not_active Expired
-
1973
- 1973-04-06 LU LU67370A patent/LU67370A1/xx unknown
- 1973-04-09 AT AT309973A patent/AT332387B/de not_active IP Right Cessation
- 1973-04-16 BE BE2052692A patent/BE798252A/xx unknown
- 1973-05-01 CH CH620773A patent/CH585713A5/xx not_active IP Right Cessation
- 1973-05-04 DE DE2322573A patent/DE2322573A1/de active Pending
- 1973-05-11 NL NL7306580A patent/NL7306580A/xx not_active Application Discontinuation
- 1973-05-14 AR AR248013A patent/AR196765A1/es active
- 1973-05-16 BR BR3578/73A patent/BR7303578D0/pt unknown
- 1973-05-18 DD DD170921A patent/DD106372A5/xx unknown
- 1973-05-18 IL IL42308A patent/IL42308A0/xx unknown
- 1973-05-18 FR FR7318154A patent/FR2185621B1/fr not_active Expired
- 1973-05-21 GB GB2418973A patent/GB1393194A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2185621A1 (enrdf_load_stackoverflow) | 1974-01-04 |
| ES403003A1 (es) | 1973-06-16 |
| CH585713A5 (enrdf_load_stackoverflow) | 1977-03-15 |
| AT332387B (de) | 1976-09-27 |
| DD106372A5 (enrdf_load_stackoverflow) | 1974-06-12 |
| FR2185621B1 (enrdf_load_stackoverflow) | 1976-11-12 |
| AR196765A1 (es) | 1974-02-19 |
| NL7306580A (enrdf_load_stackoverflow) | 1973-11-21 |
| IL42308A0 (en) | 1973-07-30 |
| BR7303578D0 (pt) | 1974-08-29 |
| GB1393194A (en) | 1975-05-07 |
| BE798252A (fr) | 1973-08-16 |
| LU67370A1 (enrdf_load_stackoverflow) | 1973-06-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |