CA1055502A - Process for the preparation of 2,5-disubstituted benzamides - Google Patents
Process for the preparation of 2,5-disubstituted benzamidesInfo
- Publication number
- CA1055502A CA1055502A CA209,914A CA209914A CA1055502A CA 1055502 A CA1055502 A CA 1055502A CA 209914 A CA209914 A CA 209914A CA 1055502 A CA1055502 A CA 1055502A
- Authority
- CA
- Canada
- Prior art keywords
- methoxy
- ethyl
- reacted
- acid
- formula
- 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 abstract description 17
- 150000003936 benzamides Chemical class 0.000 title claims abstract description 8
- 229940054066 benzamide antipsychotics Drugs 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 4
- -1 heterocyclic radical Chemical class 0.000 claims description 12
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- BXWLVQXAFBWKSR-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoic acid Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(O)=O BXWLVQXAFBWKSR-UHFFFAOYSA-N 0.000 claims description 3
- JTVPZMFULRWINT-UHFFFAOYSA-N N-[2-(diethylamino)ethyl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(S(C)(=O)=O)=CC=C1OC JTVPZMFULRWINT-UHFFFAOYSA-N 0.000 claims description 3
- UNRHXEPDKXPRTM-UHFFFAOYSA-N Sultopride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=CC=C1OC UNRHXEPDKXPRTM-UHFFFAOYSA-N 0.000 claims description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
- UMFPWTPHSKBHSR-UHFFFAOYSA-N 2-methoxy-5-propylsulfonylbenzoic acid Chemical compound CCCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 UMFPWTPHSKBHSR-UHFFFAOYSA-N 0.000 claims description 2
- QCKAYJICSQJJCU-UHFFFAOYSA-N 2-methoxy-n-[(1-methylpyrrolidin-2-yl)methyl]-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(C)CCC1 QCKAYJICSQJJCU-UHFFFAOYSA-N 0.000 claims description 2
- NBFYWQQYIJTQQV-UHFFFAOYSA-N 5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 NBFYWQQYIJTQQV-UHFFFAOYSA-N 0.000 claims description 2
- GQDIQURYRXBQHH-UHFFFAOYSA-N N-[(1-ethylpiperidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound C(C)N1C(CCCC1)CNC(C1=C(C=CC(=C1)S(N)(=O)=O)OC)=O GQDIQURYRXBQHH-UHFFFAOYSA-N 0.000 claims description 2
- IJOVAPIWJRMZTB-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-5-(ethylsulfamoyl)-2-methoxybenzamide Chemical compound CCNS(=O)(=O)C1=CC=C(OC)C(C(=O)NCC2N(CCC2)CC)=C1 IJOVAPIWJRMZTB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- TZFATUOLQKYADA-UHFFFAOYSA-N (1-propylpyrrolidin-2-yl)methanamine Chemical compound CCCN1CCCC1CN TZFATUOLQKYADA-UHFFFAOYSA-N 0.000 claims 1
- JWEHBOYGKRBMBV-UHFFFAOYSA-N 1-ethyl-1-propylhydrazine Chemical compound CCCN(N)CC JWEHBOYGKRBMBV-UHFFFAOYSA-N 0.000 claims 1
- TWDGNKWWKCGFNH-UHFFFAOYSA-N 2-methoxy-5-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 TWDGNKWWKCGFNH-UHFFFAOYSA-N 0.000 claims 1
- NWTNGBCWLCHYLQ-UHFFFAOYSA-N 2-methoxy-N-[(1-propylpyrrolidin-2-yl)methyl]-5-propylsulfonylbenzamide Chemical compound C(CC)N1C(CCC1)CNC(C1=C(C=CC(=C1)S(=O)(=O)CCC)OC)=O NWTNGBCWLCHYLQ-UHFFFAOYSA-N 0.000 claims 1
- XKOQGSAPHHFILR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxybenzamide Chemical compound C(C)N1C(CCC1)CNC(C1=C(C=CC(=C1)S(N(C)C)(=O)=O)OC)=O XKOQGSAPHHFILR-UHFFFAOYSA-N 0.000 claims 1
- WCIDQZOQJOGWRO-UHFFFAOYSA-N 5-(ethylsulfamoyl)-2-methoxybenzoic acid Chemical compound CCNS(=O)(=O)C1=CC=C(OC)C(C(O)=O)=C1 WCIDQZOQJOGWRO-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- BYONKIGBXOVRHV-UHFFFAOYSA-N n-[(1-ethylpyrrolidin-2-yl)methyl]-2-methoxy-5-(methylsulfamoyl)benzamide Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)NC)=CC=C1OC BYONKIGBXOVRHV-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 4
- 208000008469 Peptic Ulcer Diseases 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 230000000949 anxiolytic effect Effects 0.000 abstract description 2
- 229940005530 anxiolytics Drugs 0.000 abstract description 2
- 125000002636 imidazolinyl group Chemical group 0.000 abstract description 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract description 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract description 2
- 125000001984 thiazolidinyl group Chemical group 0.000 abstract description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012074 organic phase Substances 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
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 229940073584 methylene chloride Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VRKXUSCKISXSIH-UHFFFAOYSA-N (1-butylpyrrolidin-2-yl)methanamine Chemical compound CCCCN1CCCC1CN VRKXUSCKISXSIH-UHFFFAOYSA-N 0.000 description 1
- RYDHRSXDITWYMH-UHFFFAOYSA-N 2-methoxy-N-[2-(propylamino)propyl]-5-sulfamoylbenzamide Chemical compound CC(CNC(C1=C(C=CC(=C1)S(N)(=O)=O)OC)=O)NCCC RYDHRSXDITWYMH-UHFFFAOYSA-N 0.000 description 1
- HJMBACRULXCTRQ-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methoxybenzoic acid Chemical compound COC1=CC=C(S(=O)(=O)N(C)C)C=C1C(O)=O HJMBACRULXCTRQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- CFNHVUGPXZUTRR-UHFFFAOYSA-N n'-propylethane-1,2-diamine Chemical compound CCCNCCN CFNHVUGPXZUTRR-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000725 suspension 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7335095A FR2245628B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-09-28 | 1973-09-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055502A true CA1055502A (en) | 1979-05-29 |
Family
ID=9125782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA209,914A Expired CA1055502A (en) | 1973-09-28 | 1974-09-24 | Process for the preparation of 2,5-disubstituted benzamides |
Country Status (11)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2418225A1 (fr) * | 1978-02-27 | 1979-09-21 | Synthelabo | Methoxy-2 benzamides et leur application en therapeutique |
| FR2418226A1 (fr) * | 1978-02-27 | 1979-09-21 | Synthelabo | Methoxy-2 alkylthio-5 benzamides et leur application en therapeutique |
| FR2447910A2 (fr) * | 1979-02-05 | 1980-08-29 | Synthelabo | Methoxy-2 alkylthio-5 benzamides et leur application en therapeutique |
| FR2478093A1 (fr) * | 1980-03-12 | 1981-09-18 | Ile De France | Nouveau procede de preparation de n-(1-alkyl (ou allyl) 2-pyrrolidinyl-methyl)2-methoxy (ou 2,3-dimethoxy) 5-sulfamoyl (ou sulfamoyl substitue) |
| AU2002364553A1 (en) * | 2001-12-28 | 2003-07-15 | Farmaceutsko-Hemijska Industrija "Zdravlje" | A process for synthesis of heterocyclic aminoalkyl benzamides |
-
1973
- 1973-09-28 FR FR7335095A patent/FR2245628B1/fr not_active Expired
-
1974
- 1974-01-01 AR AR255705A patent/AR205172A1/es active
- 1974-09-18 DE DE19742444587 patent/DE2444587A1/de not_active Withdrawn
- 1974-09-23 GB GB4131474A patent/GB1447329A/en not_active Expired
- 1974-09-23 CY CY974A patent/CY974A/xx unknown
- 1974-09-23 FI FI2762/74A patent/FI59087C/fi active
- 1974-09-24 ES ES430341A patent/ES430341A1/es not_active Expired
- 1974-09-24 CA CA209,914A patent/CA1055502A/en not_active Expired
- 1974-09-24 IE IE1971/74A patent/IE40402B1/xx unknown
- 1974-09-25 AT AT770474A patent/AT338235B/de not_active IP Right Cessation
- 1974-09-25 JP JP11039274A patent/JPS5715752B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1447329A (en) | 1976-08-25 |
| AR205172A1 (es) | 1976-04-12 |
| FI59087C (fi) | 1981-06-10 |
| IE40402B1 (en) | 1979-05-23 |
| CY974A (en) | 1978-12-22 |
| AT338235B (de) | 1977-08-10 |
| JPS5059350A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-22 |
| ES430341A1 (es) | 1977-05-01 |
| IE40402L (en) | 1975-03-28 |
| FR2245628A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-04-25 |
| ATA770474A (de) | 1976-12-15 |
| FI276274A7 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-03-29 |
| FR2245628B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-11 |
| FI59087B (fi) | 1981-02-27 |
| DE2444587A1 (de) | 1975-04-03 |
| JPS5715752B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-04-01 |
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