NO329065B1 - Derivater av N-[fenyl(piperidin-2yl)metyl]benzamid og anvendelse av de samme i terapeutika - Google Patents
Derivater av N-[fenyl(piperidin-2yl)metyl]benzamid og anvendelse av de samme i terapeutika Download PDFInfo
- Publication number
- NO329065B1 NO329065B1 NO20044388A NO20044388A NO329065B1 NO 329065 B1 NO329065 B1 NO 329065B1 NO 20044388 A NO20044388 A NO 20044388A NO 20044388 A NO20044388 A NO 20044388A NO 329065 B1 NO329065 B1 NO 329065B1
- Authority
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- Norway
- Prior art keywords
- group
- general formula
- compound
- chloro
- phenyl
- Prior art date
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- 239000003814 drug Substances 0.000 title claims description 5
- FYAFZECZBPTDGS-UHFFFAOYSA-N n-[phenyl(piperidin-2-yl)methyl]benzamide Chemical class C=1C=CC=CC=1C(=O)NC(C=1C=CC=CC=1)C1CCCCN1 FYAFZECZBPTDGS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 78
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- -1 1-ethylpiperidin-2-yl Chemical group 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 208000035475 disorder Diseases 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
- 208000007848 Alcoholism Diseases 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 206010012289 Dementia Diseases 0.000 claims description 3
- 208000002877 Epileptic Syndromes Diseases 0.000 claims description 3
- 208000019695 Migraine disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 206010001584 alcohol abuse Diseases 0.000 claims description 3
- 208000025746 alcohol use disease Diseases 0.000 claims description 3
- 208000029650 alcohol withdrawal Diseases 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000003556 anti-epileptic effect Effects 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 230000003542 behavioural effect Effects 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000037406 food intake Effects 0.000 claims description 3
- 235000012631 food intake Nutrition 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 208000024714 major depressive disease Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 230000009329 sexual behaviour Effects 0.000 claims description 3
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000013589 supplement Substances 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- 239000000203 mixture Substances 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 34
- 239000002904 solvent Substances 0.000 description 28
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- 239000004471 Glycine Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 16
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- 239000002585 base Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- 239000007995 HEPES buffer Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 108010078791 Carrier Proteins Proteins 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 5
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- 210000004027 cell Anatomy 0.000 description 5
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- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 210000000278 spinal cord Anatomy 0.000 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
- LZLSLGVFHCTZAH-UHFFFAOYSA-N 4-amino-3-chloro-5-(trifluoromethyl)benzoic acid Chemical compound NC1=C(Cl)C=C(C(O)=O)C=C1C(F)(F)F LZLSLGVFHCTZAH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229920003091 Methocel™ Polymers 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000007912 intraperitoneal administration Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000004570 mortar (masonry) Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920000136 polysorbate Polymers 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- AXOAWWUSRZCGKS-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C(F)(F)F)=C1Cl AXOAWWUSRZCGKS-UHFFFAOYSA-N 0.000 description 3
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 3
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- 150000001408 amides Chemical class 0.000 description 3
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- 239000007903 gelatin capsule Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SKOLQDLVAYRMCV-UHFFFAOYSA-M 1-(1-methylpyridin-1-ium-2-yl)-1-phenyl-n-phenylmethoxymethanimine;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C[N+]1=CC=CC=C1C(C=1C=CC=CC=1)=NOCC1=CC=CC=C1 SKOLQDLVAYRMCV-UHFFFAOYSA-M 0.000 description 2
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- KSEVEZSLOXSZLV-QQTWVUFVSA-N 2-chloro-n-[(s)-[(2s)-1-methylpiperidin-2-yl]-phenylmethyl]-3-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.CN1CCCC[C@H]1[C@H](C=1C=CC=CC=1)NC(=O)C1=CC=CC(C(F)(F)F)=C1Cl KSEVEZSLOXSZLV-QQTWVUFVSA-N 0.000 description 2
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- 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 2
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- 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
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Pulmonology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0204916A FR2838739B1 (fr) | 2002-04-19 | 2002-04-19 | Derives de n-[phenyl(piperidin-2-yl)methyl)benzamide, leur preparation et leur application en therapeutique |
| PCT/FR2003/001232 WO2003089411A1 (fr) | 2002-04-19 | 2003-04-17 | Derives de n-[phenyl(piperidin-2-yl)methyl] benzamide, leur preparation et leur application en therapeutique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20044388L NO20044388L (no) | 2005-01-19 |
| NO329065B1 true NO329065B1 (no) | 2010-08-09 |
Family
ID=28686193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20044388A NO329065B1 (no) | 2002-04-19 | 2004-10-15 | Derivater av N-[fenyl(piperidin-2yl)metyl]benzamid og anvendelse av de samme i terapeutika |
Country Status (35)
| Country | Link |
|---|---|
| US (2) | US7326722B2 (hu) |
| EP (1) | EP1499589B1 (hu) |
| JP (1) | JP4597532B2 (hu) |
| KR (2) | KR20040103973A (hu) |
| CN (1) | CN100482646C (hu) |
| AR (1) | AR039413A1 (hu) |
| AT (1) | ATE361279T1 (hu) |
| AU (1) | AU2003262420B2 (hu) |
| BR (1) | BR0309397A (hu) |
| CA (1) | CA2481461C (hu) |
| CO (1) | CO5631432A2 (hu) |
| CY (1) | CY1108025T1 (hu) |
| DE (1) | DE60313602T2 (hu) |
| DK (1) | DK1499589T3 (hu) |
| EA (1) | EA007225B1 (hu) |
| EC (1) | ECSP045369A (hu) |
| ES (1) | ES2286444T3 (hu) |
| FR (1) | FR2838739B1 (hu) |
| HR (1) | HRP20040977B1 (hu) |
| IL (2) | IL164400A0 (hu) |
| IS (1) | IS2540B (hu) |
| MA (1) | MA27192A1 (hu) |
| ME (1) | MEP25608A (hu) |
| MX (1) | MXPA04010326A (hu) |
| NO (1) | NO329065B1 (hu) |
| NZ (1) | NZ536015A (hu) |
| PL (1) | PL373195A1 (hu) |
| PT (1) | PT1499589E (hu) |
| RS (1) | RS51888B (hu) |
| SI (1) | SI1499589T1 (hu) |
| TN (1) | TNSN04208A1 (hu) |
| TW (1) | TWI306402B (hu) |
| UA (1) | UA78025C2 (hu) |
| WO (1) | WO2003089411A1 (hu) |
| ZA (1) | ZA200408154B (hu) |
Families Citing this family (37)
| 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 |
| FR2861070B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[phenyl(pyrrolidin-2-yl)methyl]benzamide et n-[(azepan-2-yl)phenylmethyl]benzamide, leur preparation et leur application en therapeutique |
| FR2861074B1 (fr) * | 2003-10-17 | 2006-04-07 | Sanofi Synthelabo | Derives de n-[phenyl(piperidin-2-yl)methyl]benzamide, 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 |
| FR2861073B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| US7202269B2 (en) | 2003-10-30 | 2007-04-10 | Janssen Pharmaceutica N.V. | GlyT2 modulators |
| US20050209317A1 (en) * | 2004-03-22 | 2005-09-22 | Apkarian A V | Method and compositions for treatment of chronic neuropathic pain |
| CA2603939C (en) * | 2005-04-08 | 2013-08-27 | Pfizer Products Inc. | Bicyclic [3.1.0] heteroaryl amides as type i glycine transport inhibitors |
| JP2009179562A (ja) * | 2006-08-11 | 2009-08-13 | Taisho Pharmaceutical Co Ltd | グリシントランスポーター阻害剤 |
| FR2917735B1 (fr) * | 2007-06-21 | 2009-09-04 | Sanofi Aventis Sa | Nouveaux indazoles substitutes, leur preparation et leur utilisation en therapeutique |
| WO2009013535A1 (en) * | 2007-07-23 | 2009-01-29 | Astrazeneca Ab | 2-azabicyclo(2.2.2)octane derivatives as modulators of the glycine transporter i receptor |
| US8420670B2 (en) * | 2007-08-22 | 2013-04-16 | Abbott Laboratories | 4-benzylaminoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| CN103224487A (zh) | 2008-04-01 | 2013-07-31 | 雅培股份有限两合公司 | 四氢异喹啉、含有它们的药物组合物和它们在治疗中的用途 |
| WO2010087761A1 (en) * | 2009-01-28 | 2010-08-05 | Astrazeneca Ab | 2-aza-bicyclo[2.2.2]octane compounds and uses thereof |
| AR075442A1 (es) | 2009-02-16 | 2011-03-30 | Abbott Gmbh & Co Kg | Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia |
| TW201038569A (en) | 2009-02-16 | 2010-11-01 | Abbott Gmbh & Co Kg | Heterocyclic compounds, pharmaceutical compositions containing them, and their use in therapy |
| JP5618047B2 (ja) * | 2010-01-29 | 2014-11-05 | 国立大学法人千葉大学 | ポジトロン断層撮影法およびポジトロン放出化合物 |
| US9051280B2 (en) | 2010-08-13 | 2015-06-09 | AbbVie Deutschland GmbH & Co. KG | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8883839B2 (en) | 2010-08-13 | 2014-11-11 | Abbott Laboratories | Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8877794B2 (en) | 2010-08-13 | 2014-11-04 | Abbott Laboratories | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8846743B2 (en) | 2010-08-13 | 2014-09-30 | Abbott Laboratories | Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| AU2012272898A1 (en) | 2011-06-24 | 2013-04-11 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| US8710043B2 (en) | 2011-06-24 | 2014-04-29 | Amgen Inc. | TRPM8 antagonists and their use in treatments |
| CA2844275A1 (en) | 2011-08-05 | 2013-02-14 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| WO2013072520A1 (en) | 2011-11-18 | 2013-05-23 | AbbVie Deutschland GmbH & Co. KG | N-substituted aminobenzocycloheptene, aminotetraline, aminoindane and phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| FR2983197B1 (fr) * | 2011-11-29 | 2014-07-25 | Assist Publ Hopitaux De Paris | Utilisation de phacetoperane pour traiter un trouble deficit de l'attention hyperactivite |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US9656955B2 (en) | 2013-03-15 | 2017-05-23 | Abbvie Inc. | Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| AU2014336154A1 (en) | 2013-10-17 | 2016-04-28 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN105992764A (zh) | 2013-10-17 | 2016-10-05 | 艾伯维德国有限责任两合公司 | 氨基色满、氨基硫代色满及氨基-1,2,3,4-四氢喹啉衍生物，包含其的药物组合物及其在治疗中的用途 |
| US9550754B2 (en) | 2014-09-11 | 2017-01-24 | AbbVie Deutschland GmbH & Co. KG | 4,5-dihydropyrazole derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US20170143681A1 (en) | 2015-11-02 | 2017-05-25 | Apkarian Technologies Llc | Methods and compositions for treating pain |
| FR3045044B1 (fr) * | 2015-12-11 | 2019-04-19 | Liphatech | Composition et appat rodonticide comprenant du flocoumafene, procede de lutte contre des rongeurs cibles nuisibles |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5254569A (en) * | 1991-01-14 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | (Amidomethyl)nitrogen heterocyclic analgesics |
| JP3026845B2 (ja) * | 1991-02-20 | 2000-03-27 | 日清製粉株式会社 | ピペリジン誘導体 |
| US5524569A (en) * | 1995-03-20 | 1996-06-11 | Rich; William A. | Anchor cover |
| CA2322136A1 (en) * | 1998-03-06 | 1999-09-10 | Ludo Edmond Josephine Kennis | Glycine transport inhibitors |
| CA2406652A1 (en) * | 2000-04-20 | 2001-11-01 | Nps Allelix Corp. | Aminopiperidines for use as glyt-1 inhibitors |
-
2002
- 2002-04-19 FR FR0204916A patent/FR2838739B1/fr not_active Expired - Fee Related
-
2003
- 2003-04-15 AR ARP030101310A patent/AR039413A1/es unknown
- 2003-04-17 PT PT03740634T patent/PT1499589E/pt unknown
- 2003-04-17 SI SI200330893T patent/SI1499589T1/sl unknown
- 2003-04-17 ES ES03740634T patent/ES2286444T3/es not_active Expired - Lifetime
- 2003-04-17 DE DE60313602T patent/DE60313602T2/de not_active Expired - Lifetime
- 2003-04-17 PL PL03373195A patent/PL373195A1/xx not_active IP Right Cessation
- 2003-04-17 US US10/511,886 patent/US7326722B2/en not_active Expired - Fee Related
- 2003-04-17 ME MEP-256/08A patent/MEP25608A/xx unknown
- 2003-04-17 AU AU2003262420A patent/AU2003262420B2/en not_active Ceased
- 2003-04-17 KR KR10-2004-7016718A patent/KR20040103973A/ko not_active Application Discontinuation
- 2003-04-17 DK DK03740634T patent/DK1499589T3/da active
- 2003-04-17 NZ NZ536015A patent/NZ536015A/en not_active IP Right Cessation
- 2003-04-17 EA EA200401172A patent/EA007225B1/ru not_active IP Right Cessation
- 2003-04-17 BR BR0309397-2A patent/BR0309397A/pt not_active IP Right Cessation
- 2003-04-17 EP EP03740634A patent/EP1499589B1/fr not_active Expired - Lifetime
- 2003-04-17 KR KR1020087018794A patent/KR101019313B1/ko not_active IP Right Cessation
- 2003-04-17 CN CNB038140063A patent/CN100482646C/zh not_active Expired - Fee Related
- 2003-04-17 AT AT03740634T patent/ATE361279T1/de active
- 2003-04-17 UA UA20041008110A patent/UA78025C2/uk unknown
- 2003-04-17 RS YU91404A patent/RS51888B/en unknown
- 2003-04-17 WO PCT/FR2003/001232 patent/WO2003089411A1/fr active IP Right Grant
- 2003-04-17 IL IL16440003A patent/IL164400A0/xx unknown
- 2003-04-17 JP JP2003586132A patent/JP4597532B2/ja not_active Expired - Fee Related
- 2003-04-17 MX MXPA04010326A patent/MXPA04010326A/es active IP Right Grant
- 2003-04-17 CA CA002481461A patent/CA2481461C/en not_active Expired - Fee Related
- 2003-04-18 TW TW092109074A patent/TWI306402B/zh not_active IP Right Cessation
-
2004
- 2004-09-30 IS IS7479A patent/IS2540B/is unknown
- 2004-10-04 IL IL164400A patent/IL164400A/en not_active IP Right Cessation
- 2004-10-07 MA MA27892A patent/MA27192A1/fr unknown
- 2004-10-08 ZA ZA200408154A patent/ZA200408154B/en unknown
- 2004-10-14 CO CO04103284A patent/CO5631432A2/es not_active Application Discontinuation
- 2004-10-15 NO NO20044388A patent/NO329065B1/no not_active IP Right Cessation
- 2004-10-18 TN TNP2004000208A patent/TNSN04208A1/fr unknown
- 2004-10-18 HR HR20040977A patent/HRP20040977B1/xx not_active IP Right Cessation
- 2004-10-18 EC EC2004005369A patent/ECSP045369A/es unknown
-
2007
- 2007-04-03 US US11/695,912 patent/US20070197601A1/en not_active Abandoned
- 2007-07-24 CY CY20071100988T patent/CY1108025T1/el unknown
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