FR2478093A1 - Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) - Google Patents
Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) Download PDFInfo
- Publication number
- FR2478093A1 FR2478093A1 FR8005533A FR8005533A FR2478093A1 FR 2478093 A1 FR2478093 A1 FR 2478093A1 FR 8005533 A FR8005533 A FR 8005533A FR 8005533 A FR8005533 A FR 8005533A FR 2478093 A1 FR2478093 A1 FR 2478093A1
- Authority
- FR
- France
- Prior art keywords
- methoxy
- formula
- amine
- acid
- dimethoxy
- 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.)
- Granted
Links
- 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 title claims description 3
- -1 N-pyrrolidinyl Chemical group 0.000 title description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 229940054066 benzamide antipsychotics Drugs 0.000 claims abstract description 3
- 150000003936 benzamides Chemical class 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims 2
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- 239000002111 antiemetic agent Substances 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 230000003474 anti-emetic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 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 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 4
- 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
- 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 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
- LMRKXSDOAFUINK-UHFFFAOYSA-N 3-chlorosulfonylbenzoic acid Chemical compound OC(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 LMRKXSDOAFUINK-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
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect 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
-
- 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)
Priority Applications (6)
| 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) |
| ES500052A ES8201548A1 (es) | 1980-03-12 | 1981-03-04 | Un procedimiento de preparacion de n-(1-alcohil(o alil)-2- pirrolidinilmetil)-2-metoxi (o 2,3-dimetoxi)-5-sulfamoil (o sulfamoil sustituido)-benzamidas |
| BE1/10158A BE887797A (fr) | 1980-03-12 | 1981-03-05 | Nouveau procede de preparation de n-(1,alkyl (ou allyl)- 2-pyrrolidinylmethyl) 2-methoxy (ou 2,3-dimethoxy)-5-sulfamoyl (ou sulfamoyl substitue) benzamides |
| IT47985/81A IT1170793B (it) | 1980-03-12 | 1981-03-10 | Procedimento per preparare n-(1-alchil(oppure allil)-2-pirrolidinil-metil)-2-metossi (oppure 2,3-dimetossi)-5-solfammoil (oppure solfamoil sostituito)-benzammidi |
| 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. |
| YU00639/81A YU63981A (en) | 1980-03-12 | 1981-03-12 | Process for obtaining n-(1-alkyl(or allyl)-2-pyrrolidinyl-methyl)-2-methoxy(or 2,3-dimethoxy)-5-sulfamoyl(or substituted sulfamoyl)-benzamides |
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2478093A1 true FR2478093A1 (fr) | 1981-09-18 |
| FR2478093B1 FR2478093B1 (enExample) | 1983-11-10 |
Family
ID=9239592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8005533A Granted 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) |
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) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5916M (enExample) * | 1966-01-21 | 1968-05-06 | ||
| FR2245628A1 (enExample) * | 1973-09-28 | 1975-04-25 | Ile De France | |
| FR2246545A1 (enExample) * | 1973-10-04 | 1975-05-02 | Ile De France | |
| FR2358892A1 (fr) * | 1976-07-19 | 1978-02-17 | Ile De France | N(1'-allyl 2'-pyrrolidylmethyl)2,3-dimethoxy 5-sulfamoyl benzamide, ses derives |
| FR2393794A2 (fr) * | 1977-06-06 | 1979-01-05 | Synthelabo | Preparation de methoxy-2 benzamides |
-
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
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR5916M (enExample) * | 1966-01-21 | 1968-05-06 | ||
| FR2245628A1 (enExample) * | 1973-09-28 | 1975-04-25 | Ile De France | |
| FR2246545A1 (enExample) * | 1973-10-04 | 1975-05-02 | Ile De France | |
| FR2358892A1 (fr) * | 1976-07-19 | 1978-02-17 | Ile De France | N(1'-allyl 2'-pyrrolidylmethyl)2,3-dimethoxy 5-sulfamoyl benzamide, ses derives |
| FR2393794A2 (fr) * | 1977-06-06 | 1979-01-05 | Synthelabo | Preparation de methoxy-2 benzamides |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2478093B1 (enExample) | 1983-11-10 |
| IT8147985A0 (it) | 1981-03-10 |
| BE887797A (fr) | 1981-09-07 |
| ES500052A0 (es) | 1981-12-16 |
| YU63981A (en) | 1983-09-30 |
| CH647504A5 (fr) | 1985-01-31 |
| ES8201548A1 (es) | 1981-12-16 |
| IT1170793B (it) | 1987-06-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CL | Concession to grant licences | ||
| ST | Notification of lapse |