UA78025C2 - Derivatives of n-[phenyl(piperidine-2-yl)methyl]benzamide, method of synthesis and use in therapy - Google Patents
Derivatives of n-[phenyl(piperidine-2-yl)methyl]benzamide, method of synthesis and use in therapy Download PDFInfo
- Publication number
- UA78025C2 UA78025C2 UA20041008110A UA20041008110A UA78025C2 UA 78025 C2 UA78025 C2 UA 78025C2 UA 20041008110 A UA20041008110 A UA 20041008110A UA 20041008110 A UA20041008110 A UA 20041008110A UA 78025 C2 UA78025 C2 UA 78025C2
- Authority
- UA
- Ukraine
- Prior art keywords
- chloro
- group
- alkyl
- general formula
- phenyl
- Prior art date
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 15
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- 238000002560 therapeutic procedure Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 26
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 35
- -1 phenyl(piperidin-2-yl)methyl Chemical group 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001961 anticonvulsive agent Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 208000007848 Alcoholism Diseases 0.000 claims description 2
- 208000000094 Chronic Pain Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 208000002877 Epileptic Syndromes Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 208000005298 acute pain Diseases 0.000 claims description 2
- 206010001584 alcohol abuse Diseases 0.000 claims description 2
- 208000025746 alcohol use disease Diseases 0.000 claims description 2
- 230000003556 anti-epileptic effect Effects 0.000 claims description 2
- 230000003542 behavioural effect Effects 0.000 claims description 2
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 208000024714 major depressive disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 201000000980 schizophrenia Diseases 0.000 claims description 2
- 230000009329 sexual behaviour Effects 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 208000016153 withdrawal disease Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
- 239000000203 mixture Substances 0.000 description 56
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 230000008018 melting Effects 0.000 description 17
- 238000002844 melting Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 14
- 239000004471 Glycine Substances 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
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- 229910002027 silica gel Inorganic materials 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000872 buffer Substances 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
- 239000000126 substance Substances 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 241001465754 Metazoa Species 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 6
- 210000000278 spinal cord Anatomy 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 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
- 210000004027 cell Anatomy 0.000 description 5
- 238000003760 magnetic stirring Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920006395 saturated elastomer Polymers 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
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-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
- 108010078791 Carrier Proteins Proteins 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 4
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000007788 liquid Substances 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
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical class [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer 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
- 238000001665 trituration 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- 244000075850 Avena orientalis Species 0.000 description 3
- 235000007319 Avena orientalis Nutrition 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 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
- 150000001408 amides Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NPPPORJZPNJXNQ-UHFFFAOYSA-N 4-amino-3-(trifluoromethyl)benzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1C(F)(F)F NPPPORJZPNJXNQ-UHFFFAOYSA-N 0.000 description 2
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
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- 239000000164 antipsychotic agent Substances 0.000 description 2
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- 229910052786 argon Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- DMBUODUULYCPAK-UHFFFAOYSA-N 1,3-bis(docosanoyloxy)propan-2-yl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCCCCCC DMBUODUULYCPAK-UHFFFAOYSA-N 0.000 description 1
- VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
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- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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Landscapes
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- Rheumatology (AREA)
- Pulmonology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 (1)
| Publication Number | Publication Date |
|---|---|
| UA78025C2 true UA78025C2 (en) | 2007-02-15 |
Family
ID=28686193
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20041008110A UA78025C2 (en) | 2002-04-19 | 2003-04-17 | Derivatives of n-[phenyl(piperidine-2-yl)methyl]benzamide, method of synthesis and use in therapy |
Country Status (35)
| Country | Link |
|---|---|
| US (2) | US7326722B2 (zh) |
| EP (1) | EP1499589B1 (zh) |
| JP (1) | JP4597532B2 (zh) |
| KR (2) | KR20040103973A (zh) |
| CN (1) | CN100482646C (zh) |
| AR (1) | AR039413A1 (zh) |
| AT (1) | ATE361279T1 (zh) |
| AU (1) | AU2003262420B2 (zh) |
| BR (1) | BR0309397A (zh) |
| CA (1) | CA2481461C (zh) |
| CO (1) | CO5631432A2 (zh) |
| CY (1) | CY1108025T1 (zh) |
| DE (1) | DE60313602T2 (zh) |
| DK (1) | DK1499589T3 (zh) |
| EA (1) | EA007225B1 (zh) |
| EC (1) | ECSP045369A (zh) |
| ES (1) | ES2286444T3 (zh) |
| FR (1) | FR2838739B1 (zh) |
| HR (1) | HRP20040977B1 (zh) |
| IL (2) | IL164400A0 (zh) |
| IS (1) | IS2540B (zh) |
| MA (1) | MA27192A1 (zh) |
| ME (1) | MEP25608A (zh) |
| MX (1) | MXPA04010326A (zh) |
| NO (1) | NO329065B1 (zh) |
| NZ (1) | NZ536015A (zh) |
| PL (1) | PL373195A1 (zh) |
| PT (1) | PT1499589E (zh) |
| RS (1) | RS51888B (zh) |
| SI (1) | SI1499589T1 (zh) |
| TN (1) | TNSN04208A1 (zh) |
| TW (1) | TWI306402B (zh) |
| UA (1) | UA78025C2 (zh) |
| WO (1) | WO2003089411A1 (zh) |
| ZA (1) | ZA200408154B (zh) |
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 |
| 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 |
| 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 |
| US7202269B2 (en) | 2003-10-30 | 2007-04-10 | Janssen Pharmaceutica N.V. | GlyT2 modulators |
| WO2005092442A2 (en) | 2004-03-22 | 2005-10-06 | Apkarian Vania A | Method and compositions for treatment of chronic neuropathic pain |
| CN101189228A (zh) * | 2005-04-08 | 2008-05-28 | 辉瑞产品有限公司 | 用作i型甘氨酸转运抑制剂的二环[3.1.0]杂芳酰胺 |
| 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 |
| CN102083797B (zh) | 2008-04-01 | 2014-06-04 | Abbvie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 |
| AR075182A1 (es) * | 2009-01-28 | 2011-03-16 | Astrazeneca Ab | Compuestos 2-aza-biciclo (2.2.2) octano y sus usos |
| 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 |
| US9045459B2 (en) | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | Phenalkylamine 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 |
| 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 |
| 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 |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
| CA2839699A1 (en) | 2011-06-24 | 2012-12-27 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| JP2014521682A (ja) | 2011-08-05 | 2014-08-28 | アッヴィ・ドイチュラント・ゲー・エム・ベー・ハー・ウント・コー・カー・ゲー | アミノクロマン、アミノチオクロマンおよびアミノ−１，２，３，４−テトラヒドロキノリン誘導体、これらを含有する医薬組成物、ならびに治療におけるこれらの使用 |
| 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 |
| CA2924689A1 (en) | 2013-10-17 | 2015-04-23 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| EP3057958B1 (en) | 2013-10-17 | 2019-05-01 | AbbVie Deutschland GmbH & Co. KG | Aminotetraline and aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy |
| 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 |
| PL342818A1 (en) * | 1998-03-06 | 2001-07-02 | Janssen Pharmaceutica Nv | Glycin transport inhibitors |
| AU2001254546A1 (en) * | 2000-04-20 | 2001-11-07 | Nps Allelix Corp. | Aminopiperidines |
-
2002
- 2002-04-19 FR FR0204916A patent/FR2838739B1/fr not_active Expired - Fee Related
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2003
- 2003-04-15 AR ARP030101310A patent/AR039413A1/es unknown
- 2003-04-17 AT AT03740634T patent/ATE361279T1/de active
- 2003-04-17 WO PCT/FR2003/001232 patent/WO2003089411A1/fr active IP Right Grant
- 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 EA EA200401172A patent/EA007225B1/ru not_active IP Right Cessation
- 2003-04-17 KR KR1020087018794A patent/KR101019313B1/ko not_active IP Right Cessation
- 2003-04-17 DE DE60313602T patent/DE60313602T2/de not_active Expired - Lifetime
- 2003-04-17 CA CA002481461A patent/CA2481461C/en not_active Expired - Fee Related
- 2003-04-17 PT PT03740634T patent/PT1499589E/pt unknown
- 2003-04-17 ES ES03740634T patent/ES2286444T3/es not_active Expired - Lifetime
- 2003-04-17 JP JP2003586132A patent/JP4597532B2/ja not_active Expired - Fee Related
- 2003-04-17 PL PL03373195A patent/PL373195A1/xx not_active IP Right Cessation
- 2003-04-17 EP EP03740634A patent/EP1499589B1/fr not_active Expired - Lifetime
- 2003-04-17 AU AU2003262420A patent/AU2003262420B2/en not_active Ceased
- 2003-04-17 US US10/511,886 patent/US7326722B2/en not_active Expired - Fee Related
- 2003-04-17 BR BR0309397-2A patent/BR0309397A/pt not_active IP Right Cessation
- 2003-04-17 UA UA20041008110A patent/UA78025C2/uk unknown
- 2003-04-17 CN CNB038140063A patent/CN100482646C/zh not_active Expired - Fee Related
- 2003-04-17 RS YU91404A patent/RS51888B/en unknown
- 2003-04-17 ME MEP-256/08A patent/MEP25608A/xx unknown
- 2003-04-17 SI SI200330893T patent/SI1499589T1/sl unknown
- 2003-04-17 MX MXPA04010326A patent/MXPA04010326A/es active IP Right Grant
- 2003-04-17 IL IL16440003A patent/IL164400A0/xx unknown
- 2003-04-17 NZ NZ536015A patent/NZ536015A/en not_active IP Right Cessation
- 2003-04-18 TW TW092109074A patent/TWI306402B/zh not_active IP Right Cessation
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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 HR HR20040977A patent/HRP20040977B1/xx not_active IP Right Cessation
- 2004-10-18 TN TNP2004000208A patent/TNSN04208A1/fr unknown
- 2004-10-18 EC EC2004005369A patent/ECSP045369A/es unknown
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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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