CA2322164A1 - Inhibiteurs du transport de la glycine - Google Patents
Inhibiteurs du transport de la glycine Download PDFInfo
- Publication number
- CA2322164A1 CA2322164A1 CA002322164A CA2322164A CA2322164A1 CA 2322164 A1 CA2322164 A1 CA 2322164A1 CA 002322164 A CA002322164 A CA 002322164A CA 2322164 A CA2322164 A CA 2322164A CA 2322164 A1 CA2322164 A1 CA 2322164A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- butyl
- bis
- fluorophenyl
- piperidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 239000004471 Glycine Substances 0.000 title claims abstract description 18
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 65
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 9
- 210000003169 central nervous system Anatomy 0.000 claims abstract description 7
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 7
- 210000001428 peripheral nervous system Anatomy 0.000 claims abstract description 7
- 206010019196 Head injury Diseases 0.000 claims abstract description 6
- 208000002193 Pain Diseases 0.000 claims abstract description 6
- 208000035475 disorder Diseases 0.000 claims abstract description 6
- 206010015037 epilepsy Diseases 0.000 claims abstract description 6
- 208000006011 Stroke Diseases 0.000 claims abstract description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 5
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 5
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 5
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 4
- -1 imidazo[1,2-a]pyridinyl Chemical group 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 150000003254 radicals Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- BGYYYLVRMYGCGR-UHFFFAOYSA-N 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1-(4-methoxyphenyl)-3-propan-2-ylurea Chemical compound C1=CC(OC)=CC=C1N(C(=O)NC(C)C)C1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BGYYYLVRMYGCGR-UHFFFAOYSA-N 0.000 claims description 2
- QVTQEMIJDHGPNP-UHFFFAOYSA-N 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1-(4-methoxyphenyl)-3-propylurea Chemical compound C=1C=C(OC)C=CC=1N(C(=O)NCCC)C(CC1)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 QVTQEMIJDHGPNP-UHFFFAOYSA-N 0.000 claims description 2
- KYXIMIWOAAGLJI-UHFFFAOYSA-N 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1-(4-methylphenyl)-3-propan-2-ylurea Chemical compound C=1C=C(C)C=CC=1N(C(=O)NC(C)C)C(CC1)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 KYXIMIWOAAGLJI-UHFFFAOYSA-N 0.000 claims description 2
- UEDJNQSCTRIKRF-UHFFFAOYSA-N 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-3-cyclohexyl-1-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1N(C(=O)NC1CCCCC1)C1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 UEDJNQSCTRIKRF-UHFFFAOYSA-N 0.000 claims description 2
- FPMKFEWMERVOQR-UHFFFAOYSA-N 3-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1-(4-chlorophenyl)-1-propan-2-ylurea Chemical compound C=1C=C(Cl)C=CC=1N(C(C)C)C(=O)NC(CC1)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 FPMKFEWMERVOQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- SQGPXLQVUBFEAE-UHFFFAOYSA-N n-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-1-(imidazo[1,2-a]pyridin-2-ylmethyl)benzimidazol-2-amine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(NC=2N(C3=CC=CC=C3N=2)CC=2N=C3C=CC=CN3C=2)CC1 SQGPXLQVUBFEAE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- VPDDKAHEMISYJT-UHFFFAOYSA-N 1-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]-3-ethyl-1-(4-methylphenyl)urea Chemical compound C=1C=C(C)C=CC=1N(C(=O)NCC)C(CC1)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VPDDKAHEMISYJT-UHFFFAOYSA-N 0.000 claims 1
- KZAARFLXPDDLMI-UHFFFAOYSA-N 2-[[4-[4,4-bis(4-fluorophenyl)butyl]piperazin-1-yl]methyl]-3-(2-ethoxyethyl)imidazo[4,5-b]pyridine Chemical compound N=1C2=CC=CN=C2N(CCOCC)C=1CN(CC1)CCN1CCCC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 KZAARFLXPDDLMI-UHFFFAOYSA-N 0.000 claims 1
- SZILZUAXESPXJM-UHFFFAOYSA-N 4-[2-[1-[4,4-bis(4-fluorophenyl)butyl]piperidin-4-yl]acetyl]-3-phenyl-1,3-dihydroquinoxalin-2-one Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(CC(=O)N2C3=CC=CC=C3NC(=O)C2C=2C=CC=CC=2)CC1 SZILZUAXESPXJM-UHFFFAOYSA-N 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 abstract description 4
- 125000003386 piperidinyl group Chemical group 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 14
- 239000000543 intermediate Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 8
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 102000011714 Glycine Receptors Human genes 0.000 description 6
- 108010076533 Glycine Receptors Proteins 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 239000002858 neurotransmitter agent Substances 0.000 description 6
- 108010078791 Carrier Proteins Proteins 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
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- 230000001404 mediated effect Effects 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 210000000278 spinal cord Anatomy 0.000 description 4
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 210000000225 synapse Anatomy 0.000 description 4
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 3
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000002964 excitative effect Effects 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
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- GKRPRMLFFJTPKC-UHFFFAOYSA-N 4-chloro-1-thiophen-2-ylbutan-2-one Chemical compound ClCCC(=O)CC1=CC=CS1 GKRPRMLFFJTPKC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 206010012289 Dementia Diseases 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 208000008238 Muscle Spasticity Diseases 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241001279009 Strychnos toxifera Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
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- XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical group OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 2
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- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- 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
- A61P25/08—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
- A61P25/28—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
La présente invention concerne l'utilisation des dérivés [4,4-bis(4-fluorophényl)butyl]-1-(pipérazinyles et pipéridyniles), inhibiteurs du transport de la glycine, pour la préparation de médicaments destinés aux traitements des troubles du système nerveux périphérique et du système nerveux central, en particulier, des psychoses, de la douleur, de l'épilepsie, des maladies neurodégénératives (maladie d'Alzheimer), de l'ictus, du trauma crânien, de la sclérose multiple et des troubles de même genre. La présente invention concerne aussi de nouveaux composés, leur préparation et leurs formes galéniques.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98200701.5 | 1998-03-06 | ||
| EP98200701 | 1998-03-06 | ||
| PCT/EP1999/001309 WO1999044596A2 (fr) | 1998-03-06 | 1999-02-26 | Inhibiteurs du transport de la glycine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2322164A1 true CA2322164A1 (fr) | 1999-09-10 |
Family
ID=8233444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002322164A Abandoned CA2322164A1 (fr) | 1998-03-06 | 1999-02-26 | Inhibiteurs du transport de la glycine |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP1059922A2 (fr) |
| JP (1) | JP2002505277A (fr) |
| KR (1) | KR20010032968A (fr) |
| CN (1) | CN1292698A (fr) |
| AU (1) | AU3408999A (fr) |
| BG (1) | BG104685A (fr) |
| BR (1) | BR9907951A (fr) |
| CA (1) | CA2322164A1 (fr) |
| EE (1) | EE200000482A (fr) |
| HR (1) | HRP20000523A2 (fr) |
| HU (1) | HUP0101048A2 (fr) |
| IL (1) | IL138228A0 (fr) |
| NO (1) | NO20004431L (fr) |
| PL (1) | PL343435A1 (fr) |
| SK (1) | SK13082000A3 (fr) |
| TR (1) | TR200002567T2 (fr) |
| WO (1) | WO1999044596A2 (fr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ20014573A3 (cs) | 1999-06-28 | 2002-05-15 | Janssen Pharmaceutica N. V. | Inhibitory replikace respiračně syncyciálního viru |
| UA73749C2 (en) * | 1999-11-01 | 2005-09-15 | Diarylenines | |
| WO2001081308A2 (fr) * | 2000-04-20 | 2001-11-01 | Nps Allelix Corp. | Aminopiperidines |
| DE10040016A1 (de) * | 2000-08-16 | 2002-02-28 | Boehringer Ingelheim Pharma | Neue beta-Amyloid Inhibitoren, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| WO2002019967A2 (fr) | 2000-09-08 | 2002-03-14 | Gliatech, Inc. | Derives hydraziniques substitues |
| WO2002022581A1 (fr) * | 2000-09-14 | 2002-03-21 | Gliatech, Inc. | Composes azotes et leur utilisation comme inhibiteurs de transport de la glycine |
| AR032653A1 (es) | 2001-02-09 | 2003-11-19 | Telik Inc | Inhibidores heterociclicos del trasportador de glicina 2 composiciones farmaceuticas, uso y metodos. |
| US7030150B2 (en) | 2001-05-11 | 2006-04-18 | Trimeris, Inc. | Benzimidazole compounds and antiviral uses thereof |
| RU2355683C2 (ru) * | 2003-09-09 | 2009-05-20 | Ф.Хоффманн-Ля Рош Аг | Производные 1-бензоилпиперазина в качестве ингибиторов поглощения глицина для лечения психозов |
| EP1663232B1 (fr) * | 2003-09-09 | 2007-10-03 | F. Hoffmann-La Roche Ag | Derives de 1-(2-amino-benzol)-piperazine en tant qu'inhibiteurs de l'absorption du glycocolle pour traiter des psychoses |
| WO2005058885A2 (fr) * | 2003-12-18 | 2005-06-30 | Glaxo Group Limited | Composes |
| TW200630337A (en) | 2004-10-14 | 2006-09-01 | Euro Celtique Sa | Piperidinyl compounds and the use thereof |
| MX2007006429A (es) * | 2004-12-09 | 2007-07-19 | Hoffmann La Roche | Derivados de fenil-piperazin-metanona. |
| ES2338139T3 (es) * | 2004-12-15 | 2010-05-04 | F. Hoffmann-La Roche Ag | Fenil-metanonas bi- y triciclicas sustituidas como inhibidores del transportador de la glicina i (glyt-1) para el tratamiento de la enfermedad de alzheimer. |
| PE20061156A1 (es) | 2004-12-23 | 2006-12-16 | Glaxo Group Ltd | Derivados de benzamida como agentes inhibidores del transportador de glicina |
| GB0428233D0 (en) * | 2004-12-23 | 2005-01-26 | Glaxo Group Ltd | Compounds |
| US7485637B2 (en) | 2005-01-04 | 2009-02-03 | Hoffmann-La Roche Inc. | Benzoyl-tetrahydropiperidine derivatives |
| EP1836178A1 (fr) * | 2005-01-06 | 2007-09-26 | F. Hoffmann-Roche AG | Phenyl methanones sulfanyl substituees utilisees comme inhibiteurs du transporteur de glycine 1 (glyt-1) pour le traitement de troubles neurologiques et neuropsychiatriques |
| BRPI0519794A2 (pt) * | 2005-01-07 | 2009-03-17 | Hoffmann La Roche | derivados de [4-(heteroaril)piperazin-1-il]-(fenil 2,5-substituìdo)metanona como inibidores de transportador de glicina 1 (glyt-1) para o tratamento de distúrbios neurológicos e neuropsiquiátricos |
| AU2006207650B2 (en) * | 2005-01-18 | 2011-01-27 | F. Hoffmann-La Roche Ag | 2, 5-disubstituted phenyl methanone derivatives as glycine transporter 1 (GlyT-I) inhibitors for the treatment of neurological and neuropsychiatry disorders |
| AU2006208547B2 (en) | 2005-01-26 | 2011-02-10 | F. Hoffmann-La Roche Ag | Phenyl methanone derivatives and their use as glycine transporter 1 inhibitors |
| DK1848694T3 (da) * | 2005-02-07 | 2010-01-25 | Hoffmann La Roche | Heterocykliske substituerede phenylmethanoner som inhibitorer af glycintransporter |
| CN100341871C (zh) * | 2005-06-03 | 2007-10-10 | 复旦大学 | 含哌啶结构的有机硫化合物,制备方法和应用 |
| US8247442B2 (en) | 2006-03-29 | 2012-08-21 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use |
| US8791264B2 (en) | 2006-04-13 | 2014-07-29 | Purdue Pharma L.P. | Benzenesulfonamide compounds and their use as blockers of calcium channels |
| TW200812963A (en) | 2006-04-13 | 2008-03-16 | Euro Celtique Sa | Benzenesulfonamide compounds and the use thereof |
| KR20120031245A (ko) * | 2006-11-01 | 2012-03-30 | 퍼듀 퍼머 엘피 | 페닐프로피온아미드 화합물 및 그의 용도 |
| FR2910321B1 (fr) | 2006-12-21 | 2009-07-10 | Galderma Res & Dev S N C Snc | Gel creme comprenant au moins un retinoide et du peroxyde de benzole |
| FR2910320B1 (fr) * | 2006-12-21 | 2009-02-13 | Galderma Res & Dev S N C Snc | Emulsion comprenant au moins un retinoide et du peroxyde de benzole |
| WO2008124118A1 (fr) | 2007-04-09 | 2008-10-16 | Purdue Pharma L.P. | Composés benzènesulfonylés et leur utilisation |
| US8765736B2 (en) | 2007-09-28 | 2014-07-01 | Purdue Pharma L.P. | Benzenesulfonamide compounds and the use thereof |
| EP2231601B1 (fr) * | 2007-12-12 | 2014-06-18 | Amgen Inc. | Inhibiteurs du transporteur de glycine 1 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1140119A (fr) * | 1978-04-03 | 1983-01-25 | Joseph Torremans | Nouvelles n-heterocycle-4-piperidinamines |
| US4219559A (en) * | 1979-01-10 | 1980-08-26 | Janssen Pharmaceutica N.V. | N-Heterocyclyl-4-piperidinamines |
| US4695575A (en) * | 1984-11-13 | 1987-09-22 | Janssen Pharmaceutica, N.V. | 4-[(bicycle heterocyclyl)-methyl and -hetero]-piperidines |
| PH23995A (en) * | 1984-01-09 | 1990-02-09 | Janssen Pharmaceutica Nv | 4((bicycle heterocyclyl)-methyl and hetero)piperidines |
| WO1999025353A1 (fr) * | 1997-11-13 | 1999-05-27 | Merck Sharp & Dohme Limited | Utilisations therapeutiques de derives de triazolopyridazine |
-
1999
- 1999-02-26 TR TR2000/02567T patent/TR200002567T2/xx unknown
- 1999-02-26 AU AU34089/99A patent/AU3408999A/en not_active Abandoned
- 1999-02-26 PL PL99343435A patent/PL343435A1/xx not_active Application Discontinuation
- 1999-02-26 BR BR9907951-8A patent/BR9907951A/pt not_active Application Discontinuation
- 1999-02-26 IL IL13822899A patent/IL138228A0/xx unknown
- 1999-02-26 EE EEP200000482A patent/EE200000482A/xx unknown
- 1999-02-26 HU HU0101048A patent/HUP0101048A2/hu unknown
- 1999-02-26 HR HR20000523A patent/HRP20000523A2/hr not_active Application Discontinuation
- 1999-02-26 JP JP2000534198A patent/JP2002505277A/ja not_active Withdrawn
- 1999-02-26 WO PCT/EP1999/001309 patent/WO1999044596A2/fr not_active Ceased
- 1999-02-26 EP EP99915541A patent/EP1059922A2/fr not_active Withdrawn
- 1999-02-26 CA CA002322164A patent/CA2322164A1/fr not_active Abandoned
- 1999-02-26 SK SK1308-2000A patent/SK13082000A3/sk unknown
- 1999-02-26 KR KR1020007006315A patent/KR20010032968A/ko not_active Withdrawn
- 1999-02-26 CN CN998036471A patent/CN1292698A/zh active Pending
-
2000
- 2000-08-11 BG BG104685A patent/BG104685A/xx unknown
- 2000-09-05 NO NO20004431A patent/NO20004431L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20004431L (no) | 2000-10-30 |
| AU3408999A (en) | 1999-09-20 |
| BG104685A (en) | 2001-04-30 |
| HRP20000523A2 (en) | 2001-02-28 |
| PL343435A1 (en) | 2001-08-13 |
| SK13082000A3 (sk) | 2001-03-12 |
| NO20004431D0 (no) | 2000-09-05 |
| TR200002567T2 (tr) | 2000-11-21 |
| WO1999044596A2 (fr) | 1999-09-10 |
| CN1292698A (zh) | 2001-04-25 |
| BR9907951A (pt) | 2001-01-30 |
| HUP0101048A2 (hu) | 2001-10-28 |
| EP1059922A2 (fr) | 2000-12-20 |
| IL138228A0 (en) | 2001-10-31 |
| EE200000482A (et) | 2002-02-15 |
| KR20010032968A (ko) | 2001-04-25 |
| WO1999044596A3 (fr) | 2000-02-17 |
| JP2002505277A (ja) | 2002-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |