IL125061A - 4-substituted piperidine analogs and their use as subtype selective nmda receptors antagonists - Google Patents
4-substituted piperidine analogs and their use as subtype selective nmda receptors antagonistsInfo
- Publication number
- IL125061A IL125061A IL12506196A IL12506196A IL125061A IL 125061 A IL125061 A IL 125061A IL 12506196 A IL12506196 A IL 12506196A IL 12506196 A IL12506196 A IL 12506196A IL 125061 A IL125061 A IL 125061A
- Authority
- IL
- Israel
- Prior art keywords
- piperidine
- ethyl
- hydroxy
- hydrogen
- benzyl
- Prior art date
Links
- -1 4-substituted piperidine Chemical class 0.000 title claims abstract description 271
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 title claims description 69
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 title claims description 68
- 239000005557 antagonist Substances 0.000 title claims description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 293
- 239000001257 hydrogen Substances 0.000 claims abstract description 250
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 250
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 205
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 184
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 105
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 87
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 75
- 125000003118 aryl group Chemical group 0.000 claims abstract description 59
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 150000003839 salts Chemical class 0.000 claims abstract description 58
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 46
- 150000002367 halogens Chemical group 0.000 claims abstract description 46
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 36
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 30
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 29
- 125000005079 alkoxycarbonylmethyl group Chemical group 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 239000005977 Ethylene Substances 0.000 claims abstract description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 9
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims abstract 15
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims abstract 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 15
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 161
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 118
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 67
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 39
- 208000035475 disorder Diseases 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 35
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 27
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 25
- 241001465754 Metazoa Species 0.000 claims description 23
- 102000005962 receptors Human genes 0.000 claims description 19
- 108020003175 receptors Proteins 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 17
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 13
- 208000006011 Stroke Diseases 0.000 claims description 13
- 239000002552 dosage form Substances 0.000 claims description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims description 10
- QSDQBKUGYGVCCY-UHFFFAOYSA-N 6-[2-(4-benzylpiperidin-1-yl)ethoxy]-2-methyl-1h-benzimidazole Chemical compound C1=C2NC(C)=NC2=CC=C1OCCN(CC1)CCC1CC1=CC=CC=C1 QSDQBKUGYGVCCY-UHFFFAOYSA-N 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 9
- 206010010904 Convulsion Diseases 0.000 claims description 9
- 208000010412 Glaucoma Diseases 0.000 claims description 9
- 208000019695 Migraine disease Diseases 0.000 claims description 9
- 208000018737 Parkinson disease Diseases 0.000 claims description 8
- 206010008118 cerebral infarction Diseases 0.000 claims description 8
- 208000014674 injury Diseases 0.000 claims description 8
- BHENPKJTLWGUQV-UHFFFAOYSA-N 4-[2-(4-benzylpiperidin-1-yl)ethoxy]aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 BHENPKJTLWGUQV-UHFFFAOYSA-N 0.000 claims description 7
- 201000006474 Brain Ischemia Diseases 0.000 claims description 7
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 7
- 208000000094 Chronic Pain Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 206010027599 migraine Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- UUIIJMFGMJHAJY-UHFFFAOYSA-N 4-[2-[4-[(4-ethylphenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(CC)=CC=C1CC1CCN(CCOC=2C=CC(O)=CC=2)CC1 UUIIJMFGMJHAJY-UHFFFAOYSA-N 0.000 claims description 6
- 208000013016 Hypoglycemia Diseases 0.000 claims description 6
- 206010046543 Urinary incontinence Diseases 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 6
- 208000016354 hearing loss disease Diseases 0.000 claims description 6
- 230000002218 hypoglycaemic effect Effects 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 230000008733 trauma Effects 0.000 claims description 6
- AXTILFAITMENGB-UHFFFAOYSA-N 1-(2-phenoxyethyl)-4-phenylpiperidine Chemical compound C=1C=CC=CC=1OCCN(CC1)CCC1C1=CC=CC=C1 AXTILFAITMENGB-UHFFFAOYSA-N 0.000 claims description 5
- QPYBWQAVWGJBQK-UHFFFAOYSA-N 2-[3-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]phenyl]ethanol Chemical compound OCCC1=CC=CC(OCCN2CCC(CC=3C=CC(Cl)=CC=3)CC2)=C1 QPYBWQAVWGJBQK-UHFFFAOYSA-N 0.000 claims description 5
- XJGIZSJFWHHEBW-UHFFFAOYSA-N 4-[(4-chlorophenyl)methyl]-1-[2-(2-nitrophenoxy)ethyl]piperidine Chemical compound [O-][N+](=O)C1=CC=CC=C1OCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 XJGIZSJFWHHEBW-UHFFFAOYSA-N 0.000 claims description 5
- DGFMEWURQCKDCI-UHFFFAOYSA-N 4-[2-(4-benzylpiperidin-1-yl)ethoxy]benzimidazol-2-one Chemical compound C12=NC(=O)N=C2C=CC=C1OCCN(CC1)CCC1CC1=CC=CC=C1 DGFMEWURQCKDCI-UHFFFAOYSA-N 0.000 claims description 5
- ABYUHJKPPSWBTJ-UHFFFAOYSA-N 4-benzyl-1-(2-phenylethyl)piperidin-4-ol Chemical compound C1CN(CCC=2C=CC=CC=2)CCC1(O)CC1=CC=CC=C1 ABYUHJKPPSWBTJ-UHFFFAOYSA-N 0.000 claims description 5
- VWUHMMQVNJLNKY-UHFFFAOYSA-N 4-benzyl-1-[2-[3-(trifluoromethyl)phenoxy]ethyl]piperidine Chemical compound FC(F)(F)C1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 VWUHMMQVNJLNKY-UHFFFAOYSA-N 0.000 claims description 5
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 5
- AJYHRDTZTAJIJN-UHFFFAOYSA-N 5-[2-(4-benzylpiperidin-1-yl)ethoxy]benzimidazol-2-imine Chemical compound C=1C2=NC(=N)N=C2C=CC=1OCCN(CC1)CCC1CC1=CC=CC=C1 AJYHRDTZTAJIJN-UHFFFAOYSA-N 0.000 claims description 5
- JZBMUBABCKVTIG-UHFFFAOYSA-N 5-[2-(4-benzylpiperidin-1-yl)ethoxy]benzimidazol-2-one Chemical compound C=1C2=NC(=O)N=C2C=CC=1OCCN(CC1)CCC1CC1=CC=CC=C1 JZBMUBABCKVTIG-UHFFFAOYSA-N 0.000 claims description 5
- IMHJOUGYGGCYGA-UHFFFAOYSA-N 5-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethoxy]benzimidazol-2-one Chemical compound C1=CC(F)=CC=C1CC1CCN(CCOC2=CC3=NC(=O)N=C3C=C2)CC1 IMHJOUGYGGCYGA-UHFFFAOYSA-N 0.000 claims description 5
- NPQTVQRRKPGNIM-UHFFFAOYSA-N 6-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethoxy]naphthalen-2-ol Chemical compound C1=CC2=CC(O)=CC=C2C=C1OCCN(CC1)CCC1CC1=CC=C(F)C=C1 NPQTVQRRKPGNIM-UHFFFAOYSA-N 0.000 claims description 5
- 206010011878 Deafness Diseases 0.000 claims description 5
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- HMWCELZHILBPJV-UHFFFAOYSA-N ethyl 2-[3-[2-(4-benzylpiperidin-1-yl)ethoxy]phenyl]acetate Chemical compound CCOC(=O)CC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 HMWCELZHILBPJV-UHFFFAOYSA-N 0.000 claims description 5
- 230000010370 hearing loss Effects 0.000 claims description 5
- 231100000888 hearing loss Toxicity 0.000 claims description 5
- AYMVHRIPVCZRBW-UHFFFAOYSA-N 1-(2-phenoxyethyl)-4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)C(O)CN1CCOC1=CC=CC=C1 AYMVHRIPVCZRBW-UHFFFAOYSA-N 0.000 claims description 4
- TVPVXKFRWMENMY-UHFFFAOYSA-N 1-(3-phenoxypropyl)-4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)C(O)CN1CCCOC1=CC=CC=C1 TVPVXKFRWMENMY-UHFFFAOYSA-N 0.000 claims description 4
- UNKJFGRGKFPFSV-UHFFFAOYSA-N 1-(3-phenoxypropyl)-4-phenylpiperidine Chemical compound C1CC(C=2C=CC=CC=2)CCN1CCCOC1=CC=CC=C1 UNKJFGRGKFPFSV-UHFFFAOYSA-N 0.000 claims description 4
- ORQNONHRFRGNJN-UHFFFAOYSA-N 1-(4-phenylbutyl)-4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound C1CC(C=2C=C(C=CC=2)C(F)(F)F)C(O)CN1CCCCC1=CC=CC=C1 ORQNONHRFRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- QRYBNQIMSKBBGH-UHFFFAOYSA-N 1-[2-(4-benzylpiperidin-1-yl)ethyl]-5H-pyrazolo[3,4-d]pyrimidin-4-one Chemical compound Oc1ncnc2n(CCN3CCC(Cc4ccccc4)CC3)ncc12 QRYBNQIMSKBBGH-UHFFFAOYSA-N 0.000 claims description 4
- JNARWPAFJLQYCY-UHFFFAOYSA-N 1-[2-(4-fluorophenoxy)ethyl]-4-[(3-fluorophenyl)methyl]piperidine Chemical compound C1=CC(F)=CC=C1OCCN1CCC(CC=2C=C(F)C=CC=2)CC1 JNARWPAFJLQYCY-UHFFFAOYSA-N 0.000 claims description 4
- PVARPKLXMNNXRN-UHFFFAOYSA-N 1-[2-(4-fluorophenoxy)ethyl]-4-[(4-fluorophenyl)methyl]piperidine Chemical compound C1=CC(F)=CC=C1CC1CCN(CCOC=2C=CC(F)=CC=2)CC1 PVARPKLXMNNXRN-UHFFFAOYSA-N 0.000 claims description 4
- WSIPXUYFJWCCRS-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-4-[(4-fluorophenyl)methyl]piperidin-4-ol Chemical compound C1CN(CCC=2C=CC(F)=CC=2)CCC1(O)CC1=CC=C(F)C=C1 WSIPXUYFJWCCRS-UHFFFAOYSA-N 0.000 claims description 4
- ACTLPYCXBIXVBA-UHFFFAOYSA-N 1-[3-(3-aminophenoxy)propyl]-4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound NC1=CC=CC(OCCCN2CC(O)C(CC2)C=2C=C(C=CC=2)C(F)(F)F)=C1 ACTLPYCXBIXVBA-UHFFFAOYSA-N 0.000 claims description 4
- OVYWGZXSPPWRCC-UHFFFAOYSA-N 1-[3-(4-fluorophenoxy)propyl]-4-phenoxypiperidine Chemical compound C1=CC(F)=CC=C1OCCCN1CCC(OC=2C=CC=CC=2)CC1 OVYWGZXSPPWRCC-UHFFFAOYSA-N 0.000 claims description 4
- ILZDHAOLOUIDFW-UHFFFAOYSA-N 2-[2-(4-benzylpiperidin-1-yl)ethoxy]-6-nitroaniline Chemical compound C1=CC=C([N+]([O-])=O)C(N)=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 ILZDHAOLOUIDFW-UHFFFAOYSA-N 0.000 claims description 4
- NBAWOUQRFLSHPU-UHFFFAOYSA-N 2-[2-(4-benzylpiperidin-1-yl)ethoxy]aniline Chemical compound NC1=CC=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 NBAWOUQRFLSHPU-UHFFFAOYSA-N 0.000 claims description 4
- PPBYIVNFLJYLRM-UHFFFAOYSA-N 2-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]aniline Chemical compound NC1=CC=CC=C1OCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 PPBYIVNFLJYLRM-UHFFFAOYSA-N 0.000 claims description 4
- VHAZVYIGBKHWNZ-UHFFFAOYSA-N 2-[3-[2-(4-benzylpiperidin-1-yl)ethoxy]phenyl]acetamide Chemical compound NC(=O)CC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 VHAZVYIGBKHWNZ-UHFFFAOYSA-N 0.000 claims description 4
- CKTQAMLYFPPLDF-UHFFFAOYSA-N 2-[3-chloro-4-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]phenyl]ethanol Chemical compound ClC1=CC(CCO)=CC=C1OCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 CKTQAMLYFPPLDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- MAIUUYCEZVWCCP-UHFFFAOYSA-N 3-[1-(3-phenoxypropyl)piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound O=C1NC2=CC=CC=C2N1C(CC1)CCN1CCCOC1=CC=CC=C1 MAIUUYCEZVWCCP-UHFFFAOYSA-N 0.000 claims description 4
- FCRHUHLYPYXAJG-UHFFFAOYSA-N 3-[2-(4-benzylpiperidin-1-yl)ethoxy]aniline Chemical compound NC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 FCRHUHLYPYXAJG-UHFFFAOYSA-N 0.000 claims description 4
- GUKRRWSCBWQAAA-UHFFFAOYSA-N 3-[2-(4-benzylpiperidin-1-yl)ethoxy]benzaldehyde Chemical compound O=CC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 GUKRRWSCBWQAAA-UHFFFAOYSA-N 0.000 claims description 4
- YPGDRJNNEGDQNT-UHFFFAOYSA-N 3-[2-(4-benzylpiperidin-1-yl)ethoxy]benzene-1,2-diamine Chemical compound NC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1N YPGDRJNNEGDQNT-UHFFFAOYSA-N 0.000 claims description 4
- NJMUPBHNJXOTOO-UHFFFAOYSA-N 3-[2-(4-benzylpiperidin-1-yl)ethoxy]phenol Chemical compound OC1=CC=CC(OCCN2CCC(CC=3C=CC=CC=3)CC2)=C1 NJMUPBHNJXOTOO-UHFFFAOYSA-N 0.000 claims description 4
- IVPJCBCTDJNWBG-UHFFFAOYSA-N 3-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]benzene-1,2-diamine Chemical compound NC1=CC=CC(OCCN2CCC(CC=3C=CC(Cl)=CC=3)CC2)=C1N IVPJCBCTDJNWBG-UHFFFAOYSA-N 0.000 claims description 4
- LWMQSZOHRRJZFV-UHFFFAOYSA-N 3-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound OC1=CC=CC(OCCN2CCC(CC=3C=CC(F)=CC=3)CC2)=C1 LWMQSZOHRRJZFV-UHFFFAOYSA-N 0.000 claims description 4
- DFOMDPKHTWXUPV-UHFFFAOYSA-N 4-[1-(4-phenylbutyl)piperidin-4-yl]phenol Chemical compound C1=CC(O)=CC=C1C1CCN(CCCCC=2C=CC=CC=2)CC1 DFOMDPKHTWXUPV-UHFFFAOYSA-N 0.000 claims description 4
- NUNYNXQLIBJISS-UHFFFAOYSA-N 4-[2-(4-benzylpiperidin-1-yl)ethoxy]-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 NUNYNXQLIBJISS-UHFFFAOYSA-N 0.000 claims description 4
- SACXHFNZXRLNSD-UHFFFAOYSA-N 4-[2-(4-benzylpiperidin-1-yl)ethoxy]benzene-1,2-diamine Chemical compound C1=C(N)C(N)=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 SACXHFNZXRLNSD-UHFFFAOYSA-N 0.000 claims description 4
- BXMUAGHJWZMQOK-UHFFFAOYSA-N 4-[2-[4-(naphthalen-2-ylmethyl)piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCN1CCC(CC=2C=C3C=CC=CC3=CC=2)CC1 BXMUAGHJWZMQOK-UHFFFAOYSA-N 0.000 claims description 4
- IWILKQYKKQYZDQ-UHFFFAOYSA-N 4-[2-[4-[(2-fluoro-4-methylphenyl)methyl]piperidin-1-yl]ethoxy]-2-methylphenol Chemical compound FC1=CC(C)=CC=C1CC1CCN(CCOC=2C=C(C)C(O)=CC=2)CC1 IWILKQYKKQYZDQ-UHFFFAOYSA-N 0.000 claims description 4
- CSUGDYBDZGUWGK-UHFFFAOYSA-N 4-[2-[4-[(3,4-difluorophenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCN1CCC(CC=2C=C(F)C(F)=CC=2)CC1 CSUGDYBDZGUWGK-UHFFFAOYSA-N 0.000 claims description 4
- KTAQQNPWECOTKZ-UHFFFAOYSA-N 4-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1OCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 KTAQQNPWECOTKZ-UHFFFAOYSA-N 0.000 claims description 4
- LGVUTMRBCLPYLN-UHFFFAOYSA-N 4-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]aniline Chemical compound C1=CC(N)=CC=C1OCCN1CCC(CC=2C=CC(Cl)=CC=2)CC1 LGVUTMRBCLPYLN-UHFFFAOYSA-N 0.000 claims description 4
- DMXNVOZCQAOVOF-UHFFFAOYSA-N 4-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]benzimidazol-2-one Chemical compound C1=CC(Cl)=CC=C1CC1CCN(CCOC=2C3=NC(=O)N=C3C=CC=2)CC1 DMXNVOZCQAOVOF-UHFFFAOYSA-N 0.000 claims description 4
- HVAIXAGEXCAFHX-UHFFFAOYSA-N 4-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(O)=CC=C1OCCN1CCC(CC=2C=CC(F)=CC=2)CC1 HVAIXAGEXCAFHX-UHFFFAOYSA-N 0.000 claims description 4
- HDDKNHXUXPDDDG-UHFFFAOYSA-N 4-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]ethylsulfanyl]phenol Chemical compound C1=CC(O)=CC=C1SCCN1CCC(CC=2C=CC(F)=CC=2)CC1 HDDKNHXUXPDDDG-UHFFFAOYSA-N 0.000 claims description 4
- ZWWLALNINLBQIQ-UHFFFAOYSA-N 4-[2-[4-[(4-propan-2-ylphenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(C(C)C)=CC=C1CC1CCN(CCOC=2C=CC(O)=CC=2)CC1 ZWWLALNINLBQIQ-UHFFFAOYSA-N 0.000 claims description 4
- BAOYJJJZDJVOOQ-UHFFFAOYSA-N 4-[2-[4-[(4-tert-butylphenyl)methyl]piperidin-1-yl]ethoxy]phenol Chemical compound C1=CC(C(C)(C)C)=CC=C1CC1CCN(CCOC=2C=CC(O)=CC=2)CC1 BAOYJJJZDJVOOQ-UHFFFAOYSA-N 0.000 claims description 4
- QASPJDSPYYZCHL-UHFFFAOYSA-N 4-benzyl-1-(4-phenoxybutan-2-yl)piperidine Chemical compound C1CC(CC=2C=CC=CC=2)CCN1C(C)CCOC1=CC=CC=C1 QASPJDSPYYZCHL-UHFFFAOYSA-N 0.000 claims description 4
- FPLHERVJOGBXHD-UHFFFAOYSA-N 4-benzyl-1-[2-(2-methoxyphenoxy)ethyl]piperidine Chemical compound COC1=CC=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 FPLHERVJOGBXHD-UHFFFAOYSA-N 0.000 claims description 4
- PNYSZPNUMVEFIO-UHFFFAOYSA-N 4-benzyl-1-[2-(4-methoxyphenoxy)ethyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCCN1CCC(CC=2C=CC=CC=2)CC1 PNYSZPNUMVEFIO-UHFFFAOYSA-N 0.000 claims description 4
- FJKYZHWHSYEJNH-UHFFFAOYSA-N 5-[2-(4-benzylpiperidin-1-yl)ethoxy]benzimidazole-2-thione Chemical compound C=1C2=NC(=S)N=C2C=CC=1OCCN(CC1)CCC1CC1=CC=CC=C1 FJKYZHWHSYEJNH-UHFFFAOYSA-N 0.000 claims description 4
- NAFAZYIKOZCZSR-UHFFFAOYSA-N 5-[2-[4-[(4-chlorophenyl)methyl]piperidin-1-yl]ethoxy]benzimidazol-2-one Chemical compound C1=CC(Cl)=CC=C1CC1CCN(CCOC2=CC3=NC(=O)N=C3C=C2)CC1 NAFAZYIKOZCZSR-UHFFFAOYSA-N 0.000 claims description 4
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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
- C07D211/10—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—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 radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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
- C07D211/20—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 singly bound oxygen or sulphur atoms
- C07D211/22—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 singly bound oxygen or sulphur atoms by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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
- C07D211/28—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 to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- 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
- C07D211/30—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 doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/36—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
- C07D487/04—Ortho-condensed systems
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US918495P | 1995-12-22 | 1995-12-22 | |
PCT/US1996/020872 WO1997023216A1 (en) | 1995-12-22 | 1996-12-20 | 4-substituted piperidine analogs and their use as subtype selective nmda receptor antagonists |
Publications (2)
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IL125061A0 IL125061A0 (en) | 1999-01-26 |
IL125061A true IL125061A (en) | 2004-05-12 |
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Application Number | Title | Priority Date | Filing Date |
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IL12506196A IL125061A (en) | 1995-12-22 | 1996-12-20 | 4-substituted piperidine analogs and their use as subtype selective nmda receptors antagonists |
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US (1) | US6124323A (bg) |
EP (1) | EP0869792B1 (bg) |
AT (1) | ATE290380T1 (bg) |
AU (1) | AU717185B2 (bg) |
BG (1) | BG63380B1 (bg) |
BR (1) | BR9612686A (bg) |
CA (1) | CA2240275A1 (bg) |
CZ (1) | CZ180298A3 (bg) |
DE (1) | DE69634447D1 (bg) |
EA (1) | EA001323B1 (bg) |
HU (1) | HUP9901296A3 (bg) |
IL (1) | IL125061A (bg) |
MX (1) | MX9805031A (bg) |
NO (1) | NO314580B1 (bg) |
NZ (1) | NZ330624A (bg) |
PL (1) | PL327493A1 (bg) |
SK (1) | SK82498A3 (bg) |
WO (1) | WO1997023216A1 (bg) |
ZA (1) | ZA9610745B (bg) |
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-
1996
- 1996-12-19 ZA ZA9610745A patent/ZA9610745B/xx unknown
- 1996-12-20 SK SK824-98A patent/SK82498A3/sk unknown
- 1996-12-20 DE DE69634447T patent/DE69634447D1/de not_active Expired - Lifetime
- 1996-12-20 EP EP96945682A patent/EP0869792B1/en not_active Expired - Lifetime
- 1996-12-20 NZ NZ330624A patent/NZ330624A/xx unknown
- 1996-12-20 WO PCT/US1996/020872 patent/WO1997023216A1/en not_active Application Discontinuation
- 1996-12-20 US US09/091,598 patent/US6124323A/en not_active Expired - Fee Related
- 1996-12-20 HU HU9901296A patent/HUP9901296A3/hu unknown
- 1996-12-20 CZ CZ981802A patent/CZ180298A3/cs unknown
- 1996-12-20 AT AT96945682T patent/ATE290380T1/de not_active IP Right Cessation
- 1996-12-20 PL PL96327493A patent/PL327493A1/xx unknown
- 1996-12-20 IL IL12506196A patent/IL125061A/en not_active IP Right Cessation
- 1996-12-20 BR BR9612686A patent/BR9612686A/pt not_active Application Discontinuation
- 1996-12-20 CA CA002240275A patent/CA2240275A1/en not_active Abandoned
- 1996-12-20 AU AU16899/97A patent/AU717185B2/en not_active Ceased
- 1996-12-20 EA EA199800592A patent/EA001323B1/ru not_active IP Right Cessation
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1998
- 1998-06-19 MX MX9805031A patent/MX9805031A/es not_active IP Right Cessation
- 1998-06-19 NO NO19982870A patent/NO314580B1/no unknown
- 1998-06-19 BG BG102562A patent/BG63380B1/bg unknown
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HUP9901296A3 (en) | 2001-01-29 |
SK82498A3 (en) | 1999-02-11 |
DE69634447D1 (de) | 2005-04-14 |
IL125061A0 (en) | 1999-01-26 |
AU717185B2 (en) | 2000-03-16 |
BR9612686A (pt) | 1999-07-20 |
MX9805031A (es) | 1998-11-30 |
EP0869792A4 (en) | 1999-09-22 |
WO1997023216A1 (en) | 1997-07-03 |
EA001323B1 (ru) | 2001-02-26 |
EA199800592A1 (ru) | 1999-02-25 |
US6124323A (en) | 2000-09-26 |
NO982870L (no) | 1998-08-24 |
BG63380B1 (bg) | 2001-12-29 |
CZ180298A3 (cs) | 1999-01-13 |
PL327493A1 (en) | 1998-12-21 |
HUP9901296A2 (hu) | 1999-08-30 |
CA2240275A1 (en) | 1997-07-03 |
BG102562A (bg) | 1999-04-30 |
EP0869792B1 (en) | 2005-03-09 |
ATE290380T1 (de) | 2005-03-15 |
NO314580B1 (no) | 2003-04-14 |
EP0869792A2 (en) | 1998-10-14 |
NZ330624A (en) | 2000-03-27 |
AU1689997A (en) | 1997-07-17 |
NO982870D0 (no) | 1998-06-19 |
ZA9610745B (en) | 1997-06-24 |
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