CA2542647C - Derives de n-heterocyclylmethylbenzamides, leur preparation et leur application en therapeutique - Google Patents
Derives de n-heterocyclylmethylbenzamides, leur preparation et leur application en therapeutique Download PDFInfo
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- CA2542647C CA2542647C CA2542647A CA2542647A CA2542647C CA 2542647 C CA2542647 C CA 2542647C CA 2542647 A CA2542647 A CA 2542647A CA 2542647 A CA2542647 A CA 2542647A CA 2542647 C CA2542647 C CA 2542647C
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- phenyl
- alkyl
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- 239000003814 drug Substances 0.000 title claims description 7
- 238000000034 method Methods 0.000 title description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 10
- 239000001961 anticonvulsive agent Substances 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 208000002193 Pain Diseases 0.000 claims description 5
- 208000006111 contracture Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
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- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims description 3
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract description 34
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- 125000001544 thienyl group Chemical group 0.000 abstract description 4
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- 125000002541 furyl group Chemical group 0.000 abstract description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
- 239000000243 solution Substances 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
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- 239000012074 organic phase Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
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- WRNSEKNHEIXBES-UHFFFAOYSA-N 2,6-dichloro-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC(C(F)(F)F)=C1Cl WRNSEKNHEIXBES-UHFFFAOYSA-N 0.000 description 1
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Landscapes
- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- General Health & Medical Sciences (AREA)
- Public Health (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Rheumatology (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0312165A FR2861076B1 (fr) | 2003-10-17 | 2003-10-17 | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
| FR0312165 | 2003-10-17 | ||
| PCT/FR2004/002643 WO2005037783A2 (fr) | 2003-10-17 | 2004-10-15 | Composes tricycliques comme inhibiteurs de transport de glycine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2542647A1 CA2542647A1 (fr) | 2005-04-28 |
| CA2542647C true CA2542647C (fr) | 2012-07-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2542647A Expired - Fee Related CA2542647C (fr) | 2003-10-17 | 2004-10-15 | Derives de n-heterocyclylmethylbenzamides, leur preparation et leur application en therapeutique |
Country Status (32)
| Country | Link |
|---|---|
| US (3) | US7288656B2 (OSRAM) |
| EP (1) | EP1680421B1 (OSRAM) |
| JP (1) | JP4853918B2 (OSRAM) |
| KR (1) | KR101125305B1 (OSRAM) |
| CN (2) | CN101684118B (OSRAM) |
| AT (1) | ATE386036T1 (OSRAM) |
| AU (1) | AU2004281217B2 (OSRAM) |
| BR (1) | BRPI0415489A (OSRAM) |
| CA (1) | CA2542647C (OSRAM) |
| CR (1) | CR8342A (OSRAM) |
| CY (1) | CY1108925T1 (OSRAM) |
| DE (1) | DE602004011806T2 (OSRAM) |
| DK (1) | DK1680421T3 (OSRAM) |
| EC (1) | ECSP066511A (OSRAM) |
| ES (1) | ES2300837T3 (OSRAM) |
| FR (1) | FR2861076B1 (OSRAM) |
| HR (1) | HRP20080186T3 (OSRAM) |
| IL (1) | IL174940A (OSRAM) |
| MA (1) | MA28099A1 (OSRAM) |
| ME (1) | ME00111B (OSRAM) |
| NO (1) | NO335462B1 (OSRAM) |
| NZ (1) | NZ547163A (OSRAM) |
| OA (1) | OA13317A (OSRAM) |
| PL (1) | PL1680421T3 (OSRAM) |
| PT (1) | PT1680421E (OSRAM) |
| RS (2) | RS20060314A (OSRAM) |
| RU (1) | RU2346945C2 (OSRAM) |
| SG (1) | SG147435A1 (OSRAM) |
| TN (1) | TNSN06110A1 (OSRAM) |
| UA (1) | UA81186C2 (OSRAM) |
| WO (1) | WO2005037783A2 (OSRAM) |
| ZA (1) | ZA200603861B (OSRAM) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2842804B1 (fr) | 2002-07-29 | 2004-09-03 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861076B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
| FR2861071B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(alkylpiperidin-2-yl) methyl]benzamide, leur prepartation et leur application en therapeutique |
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| US4066662A (en) | 1973-12-14 | 1978-01-03 | Science Union Et Cie., Societe Francaise De Recherche Medicale | N-substituted-2-aminomethyl-3-azabicyclo(3,3,0)octane compounds |
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