ZA200603861B - Use of tricyclic compounds as glycine transport inhibitors - Google Patents
Use of tricyclic compounds as glycine transport inhibitors Download PDFInfo
- Publication number
- ZA200603861B ZA200603861B ZA200603861A ZA200603861A ZA200603861B ZA 200603861 B ZA200603861 B ZA 200603861B ZA 200603861 A ZA200603861 A ZA 200603861A ZA 200603861 A ZA200603861 A ZA 200603861A ZA 200603861 B ZA200603861 B ZA 200603861B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- phenyl
- oct
- azabicyclo
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title abstract 4
- 239000004471 Glycine Substances 0.000 title abstract 2
- 239000003112 inhibitor Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 16
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 10
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
- 239000012453 solvate Substances 0.000 claims abstract description 5
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract description 3
- 239000001961 anticonvulsive agent Substances 0.000 claims abstract 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- GEZMEIHVFSWOCA-UHFFFAOYSA-N (4-fluorophenyl)methanol Chemical compound OCC1=CC=C(F)C=C1 GEZMEIHVFSWOCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 239000003814 drug Substances 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
- 125000001424 substituent group Chemical group 0.000 claims description 4
- IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 claims description 3
- 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 claims description 3
- 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 claims description 3
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-L D-tartrate(2-) Chemical compound [O-]C(=O)[C@@H](O)[C@H](O)C([O-])=O FEWJPZIEWOKRBE-LWMBPPNESA-L 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 206010000117 Abnormal behaviour Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000002877 Epileptic Syndromes Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010033664 Panic attack Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000028017 Psychotic disease Diseases 0.000 claims 1
- 206010001584 alcohol abuse Diseases 0.000 claims 1
- 208000025746 alcohol use disease Diseases 0.000 claims 1
- 230000003556 anti-epileptic effect Effects 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000006111 contracture Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 235000012631 food intake Nutrition 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims 1
- 230000004112 neuroprotection Effects 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000019899 phobic disease Diseases 0.000 claims 1
- 230000009329 sexual behaviour Effects 0.000 claims 1
- 238000009097 single-agent therapy Methods 0.000 claims 1
- 201000002859 sleep apnea Diseases 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 abstract description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 3
- 102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 abstract description 2
- 108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 150000003936 benzamides Chemical class 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- 229940088352 Glycine transporter inhibitor Drugs 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000002075 anti-alcohol Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 230000002460 anti-migrenic effect Effects 0.000 abstract 1
- 230000000648 anti-parkinson Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 239000000939 antiparkinson agent Substances 0.000 abstract 1
- 239000002249 anxiolytic agent Substances 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000701 neuroleptic effect Effects 0.000 abstract 1
- 230000000324 neuroprotective effect Effects 0.000 abstract 1
- 230000001777 nootropic effect Effects 0.000 abstract 1
- 229940125725 tranquilizer Drugs 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
- 239000000203 mixture Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 19
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 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
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000003760 magnetic stirring Methods 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- NIMRADKLQRLIKO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-2-yl-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)C1N(CC2)CCC2C1 NIMRADKLQRLIKO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- GDYRVUKFWOCVKN-UHFFFAOYSA-N 2,6-dichloro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(Cl)=O)=C1Cl GDYRVUKFWOCVKN-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001559 benzoic acids Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- JCLQBOGMZQPCMD-UHFFFAOYSA-N n-(trifluoromethyl)benzamide;hydrochloride Chemical compound Cl.FC(F)(F)NC(=O)C1=CC=CC=C1 JCLQBOGMZQPCMD-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GFDFZTFQPIBNSQ-UHFFFAOYSA-N (+)-homo-18-epiormosanine Natural products C1C(C23)CCCN3CN3CCCCC3C32CN2CCCCC2C1C3 GFDFZTFQPIBNSQ-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- RWGDPJBUBMHJHS-LNVKXUELSA-N (z)-1-(1-azabicyclo[2.2.2]octan-2-yl)-1-(4-fluorophenyl)-n-phenylmethoxymethanimine Chemical compound C1=CC(F)=CC=C1C(\C1N2CCC(CC2)C1)=N\OCC1=CC=CC=C1 RWGDPJBUBMHJHS-LNVKXUELSA-N 0.000 description 1
- RTHCFCRUPYMVIW-VZXGSGAOSA-N (z)-1-(1-azabicyclo[2.2.2]octan-2-yl)-1-(4-fluorophenyl)-n-phenylmethoxymethanimine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C(\C1N2CCC(CC2)C1)=N\OCC1=CC=CC=C1 RTHCFCRUPYMVIW-VZXGSGAOSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- LIUAALCHBQSCCX-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane-2-carboxylate Chemical compound C1CN2C(C(=O)O)CC1CC2 LIUAALCHBQSCCX-UHFFFAOYSA-N 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
- PKEMXTIVOBWBNO-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1Cl PKEMXTIVOBWBNO-UHFFFAOYSA-N 0.000 description 1
- XZGNKKJDKWIOMY-UHFFFAOYSA-N 2-methyl-1-phenyl-n-phenylmethoxyoctan-1-imine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(C)CCCCCC)=NOCC1=CC=CC=C1 XZGNKKJDKWIOMY-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- YIYBPEDZAUFQLO-UHFFFAOYSA-N 4-amino-3-chlorobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1Cl YIYBPEDZAUFQLO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GFDFZTFQPIBNSQ-LDIYZUBKSA-N Homoormosanine Natural products N12[C@H]3[C@H](C[C@H]4[C@@H]5N(C[C@@]3([C@@H]3N(C1)CCCC3)C4)CCCC5)CCC2 GFDFZTFQPIBNSQ-LDIYZUBKSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- WXNXCEHXYPACJF-ZETCQYMHSA-N N-acetyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(C)=O WXNXCEHXYPACJF-ZETCQYMHSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 229960000669 acetylleucine Drugs 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000005957 chlorosulfonylation reaction Methods 0.000 description 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- GFDFZTFQPIBNSQ-WSBLSWJJSA-N jamine Chemical compound C([C@H]([C@H]12)C3)CCN2CN2CCCC[C@@H]2[C@]21CN1CCCC[C@@H]1[C@H]3C2 GFDFZTFQPIBNSQ-WSBLSWJJSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
- BDGDWWGTAFXEEW-UHFFFAOYSA-N methylsulfinylmethane;oxalyl dichloride Chemical compound CS(C)=O.ClC(=O)C(Cl)=O BDGDWWGTAFXEEW-UHFFFAOYSA-N 0.000 description 1
- QHEKTLMYNSGMRX-UHFFFAOYSA-N n-phenylmethoxyhydroxylamine;hydrochloride Chemical compound Cl.ONOCC1=CC=CC=C1 QHEKTLMYNSGMRX-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—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]
-
- 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
- C07D487/08—Bridged systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Anesthesiology (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (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 (1)
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200603861B true ZA200603861B (en) | 2007-12-27 |
Family
ID=34385252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200603861A ZA200603861B (en) | 2003-10-17 | 2004-10-15 | Use of tricyclic compounds as glycine transport inhibitors |
Country Status (33)
| Country | Link |
|---|---|
| US (3) | US7288656B2 (ru) |
| EP (1) | EP1680421B1 (ru) |
| JP (1) | JP4853918B2 (ru) |
| KR (1) | KR101125305B1 (ru) |
| CN (2) | CN101684118B (ru) |
| AT (1) | ATE386036T1 (ru) |
| AU (1) | AU2004281217B2 (ru) |
| BR (1) | BRPI0415489A (ru) |
| CA (1) | CA2542647C (ru) |
| CR (1) | CR8342A (ru) |
| CY (1) | CY1108925T1 (ru) |
| DE (1) | DE602004011806T2 (ru) |
| DK (1) | DK1680421T3 (ru) |
| EC (1) | ECSP066511A (ru) |
| ES (1) | ES2300837T3 (ru) |
| FR (1) | FR2861076B1 (ru) |
| HK (2) | HK1142887A1 (ru) |
| HR (1) | HRP20080186T3 (ru) |
| IL (1) | IL174940A (ru) |
| MA (1) | MA28099A1 (ru) |
| ME (1) | ME00111B (ru) |
| NO (1) | NO335462B1 (ru) |
| NZ (1) | NZ547163A (ru) |
| OA (1) | OA13317A (ru) |
| PL (1) | PL1680421T3 (ru) |
| PT (1) | PT1680421E (ru) |
| RS (2) | RS51587B (ru) |
| RU (1) | RU2346945C2 (ru) |
| SG (1) | SG147435A1 (ru) |
| TN (1) | TNSN06110A1 (ru) |
| UA (1) | UA81186C2 (ru) |
| WO (1) | WO2005037783A2 (ru) |
| ZA (1) | ZA200603861B (ru) |
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 |
| 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 |
| CA2561993A1 (en) * | 2004-03-30 | 2006-04-13 | Painceptor Pharma Corporation | Compositions and methods for modulating gated ion channels |
| FR2906251B1 (fr) | 2006-09-22 | 2008-11-07 | Sanofi Aventis Sa | Derives de pyrrolizine, indolizine et quinolizine, leur preparation et leur application en therapeutique |
| US11817637B2 (en) | 2006-11-18 | 2023-11-14 | Rfmicron, Inc. | Radio frequency identification (RFID) moisture tag(s) and sensors with extended sensing via capillaries |
| TW200911808A (en) * | 2007-07-23 | 2009-03-16 | Astrazeneca Ab | Novel compounds |
| JP5619609B2 (ja) | 2007-08-22 | 2014-11-05 | アボット ゲーエムベーハーウント カンパニー カーゲー | ４−ベンジルアミノキノリン類、これらを含む医薬組成物およびこれらの使用 |
| US8653100B2 (en) | 2008-04-01 | 2014-02-18 | Abbvie Inc. | Tetrahydroisoquinolines, pharmaceutical compositions containing them, and their use in therapy |
| EP2373651A1 (en) * | 2008-12-04 | 2011-10-12 | Sanofi | Novel polymorphic forms of an azabicyclo-trifluoromethyl benzamide derivative |
| AR075182A1 (es) * | 2009-01-28 | 2011-03-16 | Astrazeneca Ab | Compuestos 2-aza-biciclo (2.2.2) octano y sus usos |
| WO2010087762A1 (en) * | 2009-01-28 | 2010-08-05 | Astrazeneca Ab | 2-aza-bicyclo[2.2.1]heptane compounds and uses thereof |
| FR2941953B1 (fr) * | 2009-02-10 | 2011-04-08 | Sanofi Aventis | Derives de n-°(2-aza-bicyclo°2.1.1!hex-1-yl)-benzamide, leur preparation et leur application en therapeutique |
| FR2941954B1 (fr) * | 2009-02-10 | 2011-04-08 | Sanofi Aventis | Derives de n-°(6-aza-bicyclo°3.2.1!oct-1-yl)-aryl-methyl! benzamide, leur preparation et leur application en therapeutique |
| 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 |
| FR2943059A1 (fr) * | 2009-03-16 | 2010-09-17 | Sanofi Aventis | Derives de n-°6-aza-bicyclo°3.2.1!oct-5-yl)-aryl-methyl!- heterobenzamide,leur preparation et leur application en therapeutique |
| AU2010224720A1 (en) * | 2009-03-16 | 2011-10-06 | Sanofi | Derivatives of N-[(2-aza-bicyclo [2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, preparation thereof and application of same in therapeutics |
| FR2943056A1 (fr) * | 2009-03-16 | 2010-09-17 | Sanofi Aventis | Derives de n-°2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique |
| FR2944284A1 (fr) * | 2009-04-14 | 2010-10-15 | Sanofi Aventis | Derives de n-°7-aza-bicyclo°2.2.1!hept-1-yl)-aryl-methyl! -benzamide, leur preparation et leur application en therapeutique |
| US8153653B2 (en) * | 2010-06-22 | 2012-04-10 | Hoffmann-La Roche Inc. | Amido-tropane derivatives |
| US9045459B2 (en) * | 2010-08-13 | 2015-06-02 | AbbVie Deutschland GmbH & Co. KG | 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 |
| 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 |
| US9309200B2 (en) | 2011-05-12 | 2016-04-12 | AbbVie Deutschland GmbH & Co. KG | Benzazepine derivatives, pharmaceutical compositions containing them, and their use in therapy |
| US8853196B2 (en) | 2011-08-05 | 2014-10-07 | AbbVie Deutschland GmbH & Co. KG | Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy |
| CN104011028A (zh) | 2011-11-18 | 2014-08-27 | 艾伯维德国有限责任两合公司 | N-取代的氨基苯并环庚烯、氨基四氢化萘、氨基茚满和苯烷基胺衍生物、包含所述衍生物的药物组合物及其在治疗中的用途 |
| EP2786986B1 (en) * | 2011-11-29 | 2018-02-28 | Vivozon, Inc. | Novel benzamide derivative and use thereof |
| US9365512B2 (en) | 2012-02-13 | 2016-06-14 | AbbVie Deutschland GmbH & Co. KG | Isoindoline 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 |
| US9650334B2 (en) | 2013-03-15 | 2017-05-16 | Abbvie Inc. | Pyrrolidine 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 |
| JP2016533375A (ja) | 2013-10-17 | 2016-10-27 | 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 | アミノテトラリン誘導体およびアミノインダン誘導体、これらを含有する医薬組成物、および治療におけるこれらの使用 |
| 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 |
| WO2016060938A2 (en) | 2014-10-08 | 2016-04-21 | RF Micron, Inc. | Radio frequency identification (rfid) moisture tag(s) and sensors with extended sensing via capillaries |
| JP6906227B2 (ja) * | 2017-08-18 | 2021-07-21 | 国立大学法人千葉大学 | ハロゲン結合ドナー／有機塩基複合型化合物及び酸塩基複合触媒 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| NZ203861A (en) * | 1982-04-14 | 1986-07-11 | Beecham Group Plc | Bicyclic heterocyclic compounds and pharmaceutical compositions containing such |
| ES2051753T3 (es) * | 1986-12-16 | 1994-07-01 | Robins Co Inc A H | N-(1-azabiciclo(2.2.2)octo-3-il) benzamidas y tiobenzamidas ansioliticas. |
| GB8720805D0 (en) * | 1987-09-04 | 1987-10-14 | Naylor R J | 2-alkoxy-n-(1-azabicyclo(2 2 2)oct-3-yl)benzamides & thiobenzamides |
| CN1291984A (zh) * | 1998-03-06 | 2001-04-18 | 詹森药业有限公司 | 甘氨酸传输抑制剂 |
| FR2861076B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-heterocyclymethylbenzamide, leur preparation et leur application en therapeutique |
-
2003
- 2003-10-17 FR FR0312165A patent/FR2861076B1/fr not_active Expired - Lifetime
-
2004
- 2004-10-15 CN CN2009101638818A patent/CN101684118B/zh not_active Expired - Fee Related
- 2004-10-15 NZ NZ547163A patent/NZ547163A/en not_active IP Right Cessation
- 2004-10-15 ME MEP-2008-122A patent/ME00111B/me unknown
- 2004-10-15 ES ES04791554T patent/ES2300837T3/es active Active
- 2004-10-15 PL PL04791554T patent/PL1680421T3/pl unknown
- 2004-10-15 SG SG200807634-1A patent/SG147435A1/en unknown
- 2004-10-15 EP EP04791554A patent/EP1680421B1/fr active Active
- 2004-10-15 PT PT04791554T patent/PT1680421E/pt unknown
- 2004-10-15 UA UAA200605374A patent/UA81186C2/uk unknown
- 2004-10-15 WO PCT/FR2004/002643 patent/WO2005037783A2/fr active IP Right Grant
- 2004-10-15 RS RS20060314A patent/RS51587B/en unknown
- 2004-10-15 KR KR1020067007370A patent/KR101125305B1/ko not_active IP Right Cessation
- 2004-10-15 OA OA1200600127A patent/OA13317A/fr unknown
- 2004-10-15 AT AT04791554T patent/ATE386036T1/de active
- 2004-10-15 AU AU2004281217A patent/AU2004281217B2/en not_active Ceased
- 2004-10-15 BR BRPI0415489-4A patent/BRPI0415489A/pt not_active IP Right Cessation
- 2004-10-15 DE DE602004011806T patent/DE602004011806T2/de active Active
- 2004-10-15 RU RU2006116889/04A patent/RU2346945C2/ru not_active IP Right Cessation
- 2004-10-15 CN CN2004800335688A patent/CN1882587B/zh not_active Expired - Fee Related
- 2004-10-15 CA CA2542647A patent/CA2542647C/fr not_active Expired - Fee Related
- 2004-10-15 RS YUP-2006/0314A patent/RS20060314A/sr unknown
- 2004-10-15 JP JP2006534800A patent/JP4853918B2/ja not_active Expired - Fee Related
- 2004-10-15 ZA ZA200603861A patent/ZA200603861B/en unknown
- 2004-10-15 DK DK04791554T patent/DK1680421T3/da active
-
2006
- 2006-04-11 IL IL174940A patent/IL174940A/en not_active IP Right Cessation
- 2006-04-14 US US11/404,273 patent/US7288656B2/en active Active
- 2006-04-17 EC EC2006006511A patent/ECSP066511A/es unknown
- 2006-04-17 TN TNP2006000110A patent/TNSN06110A1/fr unknown
- 2006-04-17 MA MA28944A patent/MA28099A1/fr unknown
- 2006-04-18 CR CR8342A patent/CR8342A/es unknown
- 2006-05-05 NO NO20062030A patent/NO335462B1/no not_active IP Right Cessation
-
2007
- 2007-05-03 HK HK10109250.4A patent/HK1142887A1/xx not_active IP Right Cessation
- 2007-05-03 HK HK07104714.0A patent/HK1098465A1/xx not_active IP Right Cessation
- 2007-09-20 US US11/858,436 patent/US7619089B2/en active Active
-
2008
- 2008-04-23 HR HR20080186T patent/HRP20080186T3/xx unknown
- 2008-05-12 CY CY20081100494T patent/CY1108925T1/el unknown
-
2009
- 2009-10-05 US US12/573,470 patent/US8513246B2/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200603861B (en) | Use of tricyclic compounds as glycine transport inhibitors | |
| ES2282916T3 (es) | Derivados de n-(fenil(alquilpiperidin-2-il)metil)benzamida, su preparacion y su aplicacion en terapeutica. | |
| ZA200603941B (en) | Derivatives of N-[heteroaryl(piperidine-2-yl)methyl]benzamide, preparation method thereof and application of same in therapeutics | |
| CN102186826A (zh) | 制备双环5-三氟甲氧基-1h-3-吲唑甲酰胺合成中的吲唑中间体的非重氮化方法 | |
| Huang et al. | A facile approach to trans-4, 5-pyrrolidine lactam and application in the synthesis of nemonapride and streptopyrrolidine | |
| FR2943059A1 (fr) | Derives de n-°6-aza-bicyclo°3.2.1!oct-5-yl)-aryl-methyl!- heterobenzamide,leur preparation et leur application en therapeutique | |
| AU2007301880A1 (en) | Derivatives of pyrrolizine, indolizine and quinolizine, preparation thereof and therapeutic use thereof | |
| JP5698887B2 (ja) | （ｒ）−２−メチルピロリジンおよび（ｓ）−２−メチルピロリジンならびにその酒石酸塩を調製するための方法 | |
| Baraznenok et al. | 3-(2, 5-Dihydro-1H-pyrrol-2-ylmethoxy) pyridines: synthesis and analgesic activity | |
| WO1999002517A1 (fr) | Derives de 6-pyrrolidin-2-ylpyrindines, leur preparation et leur application en therapeutique | |
| Ruano et al. | Highly stereoselective reduction of acyclic α-sulfinyl ketimines: synthesis of enantiomerically pure β-aminosulfoxides | |
| MXPA06004270A (en) | Derivatives of n-heterocyclylmethylbenzamides, preparation method thereof and application of same in therapeutics | |
| FR2944283A1 (fr) | Derives de n-°(2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique | |
| FR2943056A1 (fr) | Derives de n-°2-aza-bicyclo°2.1.1!hex-1-yl)-aryl-methyl!- heterobenzamide, leur preparation et leur application en therapeutique | |
| CA2755526A1 (fr) | Derives de n-[(2-aza-bicyclo[2.1.1]hex-1-yl)-aryl-methyl]-heterobenzamide, leur preparation et leur application en therapeutique | |
| EP2396334A1 (fr) | Derives de n-[(2-aza-bicyclo[2.1.1]hex-1-yl]-aryl-methyl]-benzamide, leur preparation et leur application en therapeutique | |
| JP2012107006A (ja) | Ｎ−置換−環状アミノ誘導体の製造方法 |