SU602116A3 - Способ получени замещенных (1-бензилпирролидинил-2-алкил)бензамидов или их кислых или аммонийных солей или их правовращающих или левовращающих изомеров - Google Patents
Способ получени замещенных (1-бензилпирролидинил-2-алкил)бензамидов или их кислых или аммонийных солей или их правовращающих или левовращающих изомеровInfo
- Publication number
- SU602116A3 SU602116A3 SU752109846A SU2109846A SU602116A3 SU 602116 A3 SU602116 A3 SU 602116A3 SU 752109846 A SU752109846 A SU 752109846A SU 2109846 A SU2109846 A SU 2109846A SU 602116 A3 SU602116 A3 SU 602116A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- alkyl
- hydrogen
- halogen
- alkenyl
- hand
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 5
- 150000003863 ammonium salts Chemical class 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 2
- 229940054066 benzamide antipsychotics Drugs 0.000 title 1
- 238000009835 boiling Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003277 amino group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005529 alkyleneoxy group Chemical group 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000896513 Kohautia tenuis Species 0.000 claims 1
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- OEYAFMGVIFWPQI-UHFFFAOYSA-N (1-benzylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1CC1=CC=CC=C1 OEYAFMGVIFWPQI-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- -1 pro-amine amine Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- RCFGFTLCCWRMTI-UHFFFAOYSA-N 2-methoxy-5-methylsulfonylbenzoyl chloride Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(Cl)=O RCFGFTLCCWRMTI-UHFFFAOYSA-N 0.000 description 1
- CLICAYDHIJRPTL-UHFFFAOYSA-N 3-sulfamoylbenzoyl chloride Chemical compound NS(=O)(=O)C1=CC=CC(C(Cl)=O)=C1 CLICAYDHIJRPTL-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SCSLYXQZQWKMEW-UHFFFAOYSA-N methyl 2,3-dimethoxy-5-(methylsulfamoyl)benzoate Chemical compound CNS(=O)(=O)C1=CC(OC)=C(OC)C(C(=O)OC)=C1 SCSLYXQZQWKMEW-UHFFFAOYSA-N 0.000 description 1
- OUEXNQRVYGYGIK-UHFFFAOYSA-N methyl 4-acetamido-5-chloro-2-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(NC(C)=O)C=C1OC OUEXNQRVYGYGIK-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940086542 triethylamine Drugs 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
-
- 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
- C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—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 one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7407535A FR2262966A1 (fr) | 1974-03-05 | 1974-03-05 | Nouveau benzamide hétérocyclique et son procédé de fabrication |
| FR7503799A FR2299862B1 (en) | 1975-02-07 | 1975-02-07 | Substd. N-(1-benzylpyrrolidinyl-2-alkyl)benzamides - used as antiemetics, anti-ulcer agents and CNS active |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU602116A3 true SU602116A3 (ru) | 1978-04-05 |
Family
ID=26218209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752109846A SU602116A3 (ru) | 1974-03-05 | 1975-03-04 | Способ получени замещенных (1-бензилпирролидинил-2-алкил)бензамидов или их кислых или аммонийных солей или их правовращающих или левовращающих изомеров |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4029673A (en, 2012) |
| JP (1) | JPS6058750B2 (en, 2012) |
| AR (1) | AR212960A1 (en, 2012) |
| AT (1) | AT350546B (en, 2012) |
| BG (1) | BG25072A3 (en, 2012) |
| CA (1) | CA1060029A (en, 2012) |
| CH (1) | CH605793A5 (en, 2012) |
| CS (1) | CS189691B2 (en, 2012) |
| DD (1) | DD117451A5 (en, 2012) |
| DE (1) | DE2508045C2 (en, 2012) |
| DK (1) | DK145376C (en, 2012) |
| EG (1) | EG11971A (en, 2012) |
| ES (1) | ES435273A1 (en, 2012) |
| FI (1) | FI58494C (en, 2012) |
| GB (1) | GB1466646A (en, 2012) |
| HK (1) | HK13978A (en, 2012) |
| HU (1) | HU172091B (en, 2012) |
| IE (1) | IE40860B1 (en, 2012) |
| IL (1) | IL46695A (en, 2012) |
| LU (1) | LU71948A1 (en, 2012) |
| NL (1) | NL184617C (en, 2012) |
| NO (1) | NO144740C (en, 2012) |
| OA (1) | OA04967A (en, 2012) |
| PH (1) | PH14207A (en, 2012) |
| PL (1) | PL96942B1 (en, 2012) |
| RO (1) | RO73247A (en, 2012) |
| SE (1) | SE411753B (en, 2012) |
| SU (1) | SU602116A3 (en, 2012) |
| YU (1) | YU51775A (en, 2012) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2392269C2 (ru) * | 2004-01-16 | 2010-06-20 | Санофи-Авентис | Производные арилоксиалкилкарбаматов, их получение и их применение в терапии |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4189495A (en) * | 1974-09-17 | 1980-02-19 | Synthelabo | 2-Methoxy-benzamide derivatives |
| US4172143A (en) * | 1974-12-18 | 1979-10-23 | Synthelabo | 2-Methoxy-benzamide derivatives |
| US4158060A (en) * | 1974-12-18 | 1979-06-12 | Synthelabo | 2-Methoxy-benzamide derivatives |
| US4163789A (en) * | 1976-02-17 | 1979-08-07 | Anphar, S.A. | Anti-psychotic (cycloalkenylalkylpiperidino) benzamides |
| NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
| FR2386524A1 (fr) * | 1977-04-05 | 1978-11-03 | Choay Sa | Amino-4 chloro-5 methoxy-2 n-(n-ethyl methyl-2 pyrrolidino)benzenesulfonamide, procede de preparation et medicaments le contenant |
| FR2387218A1 (fr) * | 1977-04-15 | 1978-11-10 | Ile De France | Nouveaux n-(1'-ethyl 2'-oxo 5'-pyrrolidinyl methyl) benzamides, leurs procedes de preparation et leur application comme modificateurs du comportement |
| FR2440946A2 (fr) * | 1978-01-20 | 1980-06-06 | Ile De France | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
| IT1095415B (it) * | 1978-02-16 | 1985-08-10 | Ravizza Spa | Processo per la produzione di una benzamide otticamente attiva,benzamide otticamente attiva cosi'ottenuta e composizioni |
| SE411118B (sv) * | 1978-03-23 | 1979-12-03 | Astra Laekemedel Ab | Ett forfarande for framstellning av 2,6-dialkoxibensamider med terapentiska egenskaper |
| FR2438650A1 (fr) * | 1978-10-11 | 1980-05-09 | Ile De France | N-(1-methyl 2-pyrrolidinyl methyl) 2,3-dimethoxy 5-methylsulfamoyl benzamide et ses derives, leurs methodes de preparation et leur application dans le traitement des troubles du bas appareil urinaire |
| US4263316A (en) * | 1978-10-11 | 1981-04-21 | Societe D'etudes Scientifiques Et Industrielles De L'ile De France | N-(1-Methyl-2-pyrrolidinylmethyl)-2,3-dimethoxy-5-methylsulfamoyl benzamide and its derivatives, methods of preparing them and their application to the treatment of troubles of the lower part of the body |
| US4210660A (en) * | 1978-12-20 | 1980-07-01 | Yamanouchi Pharmaceutical Co., Ltd. | Benzamide derivatives |
| FR2489327B1 (fr) * | 1980-08-28 | 1984-05-18 | Ile De France | N (1 allyl 2 pyrrolidinyl methyl) 2 methoxy 4 amino 5 methylsulfa moyl benzamide, son procede de preparation et son application comme medicament |
| SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
| JPS5970666A (ja) * | 1982-10-15 | 1984-04-21 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
| SE8503054D0 (sv) * | 1985-06-19 | 1985-06-19 | Astra Laekemedel Ab | Catecholcarboxamides |
| JPS62174017A (ja) * | 1986-08-29 | 1987-07-30 | Kyowa Hakko Kogyo Co Ltd | １，４−ジヒドロピリジン誘導体 |
| FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
| JP4113602B2 (ja) * | 1997-04-04 | 2008-07-09 | 株式会社資生堂 | ピロリジン誘導体及び抗潰瘍剤、抗菌剤 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
| US3891671A (en) * | 1968-08-01 | 1975-06-24 | Ile De France | N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides |
| DE1785124A1 (de) * | 1968-08-13 | 1971-11-11 | Prym Werke William | Reissverschluss |
| HU167379B (en, 2012) * | 1972-06-01 | 1975-09-27 | ||
| US3923829A (en) * | 1972-06-13 | 1975-12-02 | Fratmann Ag | Preparation of N-(1-ethyl-{60 -pyrrolidylmethyl)-2-methoxy-5-sulfonamidobenzamide |
| US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
-
1974
- 1974-03-05 CH CH279775A patent/CH605793A5/fr not_active IP Right Cessation
-
1975
- 1975-02-24 IL IL46695A patent/IL46695A/en unknown
- 1975-02-25 DE DE2508045A patent/DE2508045C2/de not_active Expired
- 1975-02-26 GB GB809475A patent/GB1466646A/en not_active Expired
- 1975-03-03 EG EG108/75A patent/EG11971A/ar active
- 1975-03-03 SE SE7502341A patent/SE411753B/sv not_active IP Right Cessation
- 1975-03-03 AT AT160675A patent/AT350546B/de not_active IP Right Cessation
- 1975-03-03 LU LU71948A patent/LU71948A1/fr unknown
- 1975-03-04 YU YU00517/75A patent/YU51775A/en unknown
- 1975-03-04 IE IE456/75A patent/IE40860B1/en unknown
- 1975-03-04 BG BG029147A patent/BG25072A3/bg unknown
- 1975-03-04 FI FI750619A patent/FI58494C/fi not_active IP Right Cessation
- 1975-03-04 NO NO750714A patent/NO144740C/no unknown
- 1975-03-04 CS CS751444A patent/CS189691B2/cs unknown
- 1975-03-04 ES ES435273A patent/ES435273A1/es not_active Expired
- 1975-03-04 CA CA221,237A patent/CA1060029A/en not_active Expired
- 1975-03-04 SU SU752109846A patent/SU602116A3/ru active
- 1975-03-04 OA OA55431A patent/OA04967A/fr unknown
- 1975-03-04 DK DK86875A patent/DK145376C/da active
- 1975-03-05 PL PL1975178532A patent/PL96942B1/pl unknown
- 1975-03-05 NL NLAANVRAGE7502607,A patent/NL184617C/nl not_active IP Right Cessation
- 1975-03-05 RO RO7581557A patent/RO73247A/ro unknown
- 1975-03-05 JP JP50027572A patent/JPS6058750B2/ja not_active Expired
- 1975-03-05 DD DD184578A patent/DD117451A5/de unknown
- 1975-03-05 US US05/555,376 patent/US4029673A/en not_active Expired - Lifetime
- 1975-03-05 HU HU75SO00001139A patent/HU172091B/hu not_active IP Right Cessation
- 1975-04-04 AR AR257836A patent/AR212960A1/es active
-
1978
- 1978-01-05 PH PH20622A patent/PH14207A/en unknown
- 1978-03-16 HK HK139/78A patent/HK13978A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2392269C2 (ru) * | 2004-01-16 | 2010-06-20 | Санофи-Авентис | Производные арилоксиалкилкарбаматов, их получение и их применение в терапии |
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