CH647504A5 - Procede de preparation de n-(1-alkyl (ou allyl)-2-pyrrolidinylmethyl)2-methoxy (ou 2,3-dimethoxy)-5-sulfamoyl (ou sulfamoyl substitue) benzamides. - Google Patents
Procede de preparation de n-(1-alkyl (ou allyl)-2-pyrrolidinylmethyl)2-methoxy (ou 2,3-dimethoxy)-5-sulfamoyl (ou sulfamoyl substitue) benzamides. Download PDFInfo
- Publication number
- CH647504A5 CH647504A5 CH1659/81A CH165981A CH647504A5 CH 647504 A5 CH647504 A5 CH 647504A5 CH 1659/81 A CH1659/81 A CH 1659/81A CH 165981 A CH165981 A CH 165981A CH 647504 A5 CH647504 A5 CH 647504A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- amine
- methoxy
- dimethoxy
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 6
- 229940054066 benzamide antipsychotics Drugs 0.000 title claims description 3
- 150000003936 benzamides Chemical class 0.000 title claims description 3
- -1 ALLYL Chemical class 0.000 title description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- TWHADRKVBHEANG-UHFFFAOYSA-N 5-chlorosulfonyl-2,3-dimethoxybenzoic acid Chemical compound COC1=CC(S(Cl)(=O)=O)=CC(C(O)=O)=C1OC TWHADRKVBHEANG-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- OUBZCDOQEMLMAB-UHFFFAOYSA-N 5-chlorosulfonyl-2-methoxybenzoic acid Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O OUBZCDOQEMLMAB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 2
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- HTGKTSVPJJNEMQ-QMMMGPOBSA-N [(2s)-1-prop-2-enylpyrrolidin-2-yl]methanamine Chemical compound NC[C@@H]1CCCN1CC=C HTGKTSVPJJNEMQ-QMMMGPOBSA-N 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims 10
- 239000002253 acid Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-UHFFFAOYSA-N 0.000 claims 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 239000002111 antiemetic agent Substances 0.000 claims 1
- 229940125683 antiemetic agent Drugs 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- 230000002936 tranquilizing effect Effects 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- GTKYLVJCMKDNTH-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(N)=O GTKYLVJCMKDNTH-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 6
- OFCFLGYUMQEVGO-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(N)=O)=C1OC OFCFLGYUMQEVGO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FODBVCSYJKNBLO-UHFFFAOYSA-N 2,3-dimethoxybenzoic acid Chemical compound COC1=CC=CC(C(O)=O)=C1OC FODBVCSYJKNBLO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003960 organic solvent Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/89—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing carboxyl groups bound to the carbon skeleton
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 |
|---|---|---|---|
| FR8005533A FR2478093A1 (fr) | 1980-03-12 | 1980-03-12 | Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH647504A5 true CH647504A5 (fr) | 1985-01-31 |
Family
ID=9239592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1659/81A CH647504A5 (fr) | 1980-03-12 | 1981-03-11 | Procede de preparation de n-(1-alkyl (ou allyl)-2-pyrrolidinylmethyl)2-methoxy (ou 2,3-dimethoxy)-5-sulfamoyl (ou sulfamoyl substitue) benzamides. |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE887797A (enExample) |
| CH (1) | CH647504A5 (enExample) |
| ES (1) | ES8201548A1 (enExample) |
| FR (1) | FR2478093A1 (enExample) |
| IT (1) | IT1170793B (enExample) |
| YU (1) | YU63981A (enExample) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5916M (enExample) * | 1966-01-21 | 1968-05-06 | ||
| FR2245628B1 (enExample) * | 1973-09-28 | 1977-03-11 | Ile De France | |
| FR2246545B1 (enExample) * | 1973-10-04 | 1978-09-15 | Ile De France | |
| FR2393794A2 (fr) * | 1977-06-06 | 1979-01-05 | Synthelabo | Preparation de methoxy-2 benzamides |
| FR2358892A1 (fr) * | 1976-07-19 | 1978-02-17 | Ile De France | N(1'-allyl 2'-pyrrolidylmethyl)2,3-dimethoxy 5-sulfamoyl benzamide, ses derives |
-
1980
- 1980-03-12 FR FR8005533A patent/FR2478093A1/fr active Granted
-
1981
- 1981-03-04 ES ES500052A patent/ES8201548A1/es not_active Expired
- 1981-03-05 BE BE1/10158A patent/BE887797A/fr not_active IP Right Cessation
- 1981-03-10 IT IT47985/81A patent/IT1170793B/it active
- 1981-03-11 CH CH1659/81A patent/CH647504A5/fr not_active IP Right Cessation
- 1981-03-12 YU YU00639/81A patent/YU63981A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478093B1 (enExample) | 1983-11-10 |
| IT8147985A0 (it) | 1981-03-10 |
| FR2478093A1 (fr) | 1981-09-18 |
| BE887797A (fr) | 1981-09-07 |
| ES500052A0 (es) | 1981-12-16 |
| YU63981A (en) | 1983-09-30 |
| ES8201548A1 (es) | 1981-12-16 |
| IT1170793B (it) | 1987-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |