BG107530A - Нови съединения и тяхното използване като инхибитори на глициновия транспортер - Google Patents

Нови съединения и тяхното използване като инхибитори на глициновия транспортер Download PDF

Info

Publication number: BG107530A
Authority: BG; Bulgaria
Prior art keywords: alkyl; phenyl; dihydroisobenzofuran; chloro; halogen
Prior art date: 2000-07-21

Application number

BG107530A

Other languages

Bulgarian (bg)

English (en)

Inventor

Ejner Moltzen

Paul Smith

Christian Krog-Jensen

Klaus Bogeso

Original Assignee

H.Lundbeck A/S

Priority date (The priority date 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 date listed.)

2000-07-21

Filing date

2003-02-05

Publication date

2003-09-30

2003-02-05 Application filed by H.Lundbeck A/S filed Critical H.Lundbeck A/S

2003-09-30 Publication of BG107530A publication Critical patent/BG107530A/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 48
239000003112 inhibitor Substances 0.000 title abstract description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title description 29
239000004471 Glycine Substances 0.000 title description 20
201000010099 disease Diseases 0.000 claims abstract description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 claims abstract description 15
102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 claims abstract description 15
239000003814 drug Substances 0.000 claims abstract description 3
238000004519 manufacturing process Methods 0.000 claims abstract description 3
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 16
238000000034 method Methods 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 12
229920006395 saturated elastomer Polymers 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
206010012289 Dementia Diseases 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
201000000980 schizophrenia Diseases 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
208000002193 Pain Diseases 0.000 claims description 4
208000028017 Psychotic disease Diseases 0.000 claims description 4
230000019771 cognition Effects 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
208000030507 AIDS Diseases 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010019196 Head injury Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
208000024891 symptom Diseases 0.000 claims description 3
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims description 2
206010061216 Infarction Diseases 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
208000006011 Stroke Diseases 0.000 claims 2
230000008485 antagonism Effects 0.000 claims 2
208000005314 Multi-Infarct Dementia Diseases 0.000 claims 1
201000004810 Vascular dementia Diseases 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
239000003446 ligand Substances 0.000 abstract description 6
230000005764 inhibitory process Effects 0.000 abstract description 3
238000001819 mass spectrum Methods 0.000 description 60
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 43
-1 phencyclidine Chemical class 0.000 description 31
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
229960002449 glycine Drugs 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 11
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 7
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 7
239000000243 solution Substances 0.000 description 7
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000000203 mixture Substances 0.000 description 6
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000029936 alkylation Effects 0.000 description 4
238000005804 alkylation reaction Methods 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000011272 standard treatment Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XKOQVRLECUULHT-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-3,3-dimethyl-2-benzofuran-1-yl]ethyl-methylamino]acetic acid Chemical compound O1C(C)(C)C2=CC=CC=C2C1(CCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 XKOQVRLECUULHT-UHFFFAOYSA-N 0.000 description 3
YERIVNORZKQTBA-UHFFFAOYSA-N 2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]acetic acid Chemical compound C1CC2=CC(Cl)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 YERIVNORZKQTBA-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 description 3
102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
239000002671 adjuvant Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
KEIDEHNAVGKQCB-NVHKAFQKSA-N (2s)-2-[3-(3,3-dimethyl-1-phenyl-2-benzothiophen-1-yl)propyl-methylamino]propanoic acid Chemical compound S1C(C)(C)C2=CC=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=CC=C1 KEIDEHNAVGKQCB-NVHKAFQKSA-N 0.000 description 2
AQFYBBOVSHVEKK-CPFIQGLUSA-N (2s)-2-[3-[1-(4-chlorophenyl)-3,3-diethyl-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound C12=CC=CC=C2C(CC)(CC)OC1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 AQFYBBOVSHVEKK-CPFIQGLUSA-N 0.000 description 2
CDVLPBUKUVKVBA-UEDXYCIISA-N (2s)-2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]propanoic acid Chemical compound C1CC2=CC(Cl)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 CDVLPBUKUVKVBA-UEDXYCIISA-N 0.000 description 2
CIWXIAJJCJIWOE-UHFFFAOYSA-N 2-[2-[1-(4-chlorophenyl)-5-(5-chlorothiophen-2-yl)-3h-2-benzofuran-1-yl]ethyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(Cl)S1 CIWXIAJJCJIWOE-UHFFFAOYSA-N 0.000 description 2
SHIGDERHWRPXFW-UHFFFAOYSA-N 2-[3-[1,5-bis(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(Cl)C=C1 SHIGDERHWRPXFW-UHFFFAOYSA-N 0.000 description 2
JMZRXZUYTKWUCL-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(3,4-dichlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(Cl)C(Cl)=C1 JMZRXZUYTKWUCL-UHFFFAOYSA-N 0.000 description 2
KAPQYVCDDXBUIY-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-[2-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=CC=C1C(F)(F)F KAPQYVCDDXBUIY-UHFFFAOYSA-N 0.000 description 2
JUWVFZAPYCYAKO-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-[4-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(C(F)(F)F)C=C1 JUWVFZAPYCYAKO-UHFFFAOYSA-N 0.000 description 2
BYEFBPYBYKBWFR-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C=C1 BYEFBPYBYKBWFR-UHFFFAOYSA-N 0.000 description 2
IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 2
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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 2
238000005481 NMR spectroscopy Methods 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000004064 dysfunction Effects 0.000 description 2
239000003480 eluent Substances 0.000 description 2
OSVAYUPHKDNSKR-UHFFFAOYSA-N ethyl 2-[3-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetate Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(=O)OCC)C1=CC=C(F)C=C1 OSVAYUPHKDNSKR-UHFFFAOYSA-N 0.000 description 2
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
229960001269 glycine hydrochloride Drugs 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
WVKIFIROCHIWAY-UHFFFAOYSA-N hydron;2-(methylamino)acetic acid;chloride Chemical compound Cl.CNCC(O)=O WVKIFIROCHIWAY-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
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 2
239000002245 particle Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
KWDXGALCQUZREM-VKHMYHEASA-N (2s)-2-(methoxyamino)butanedioic acid Chemical compound CON[C@H](C(O)=O)CC(O)=O KWDXGALCQUZREM-VKHMYHEASA-N 0.000 description 1
UAUWLEHSOZBEQW-YXWRBFHGSA-N (2s)-2-[3-[1-(4-fluorophenyl)-5-(trifluoromethyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound O1CC2=CC(C(F)(F)F)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(F)C=C1 UAUWLEHSOZBEQW-YXWRBFHGSA-N 0.000 description 1
SXTQZBWYMOQNCU-VYTWEFSNSA-N (2s)-2-[3-[1-(4-fluorophenyl)-5-(trifluoromethyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid;hydrochloride Chemical compound Cl.O1CC2=CC(C(F)(F)F)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(F)C=C1 SXTQZBWYMOQNCU-VYTWEFSNSA-N 0.000 description 1
JSHPGKFTWNDYTC-JQVYNXHMSA-N (2s)-2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]propanoic acid;hydrochloride Chemical compound Cl.C1CC2=CC(Cl)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 JSHPGKFTWNDYTC-JQVYNXHMSA-N 0.000 description 1
BLRLFAJWSBAXFC-YXWRBFHGSA-N (2s)-2-[3-[5-chloro-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound O1CC2=CC(Cl)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 BLRLFAJWSBAXFC-YXWRBFHGSA-N 0.000 description 1
NNMDLTSDCPVATO-VYTWEFSNSA-N (2s)-2-[3-[5-chloro-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid;hydrochloride Chemical compound Cl.O1CC2=CC(Cl)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(Cl)C=C1 NNMDLTSDCPVATO-VYTWEFSNSA-N 0.000 description 1
AYMQVLIZSCJKJX-VIUMTJHJSA-N (2s)-2-[3-[5-cyano-1-(4-cyanophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]propanoic acid;hydrochloride Chemical compound Cl.C1CC2=CC(C#N)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(C#N)C=C1 AYMQVLIZSCJKJX-VIUMTJHJSA-N 0.000 description 1
QNZUEKRUUYXCNU-GZWBLTSWSA-N (2s)-2-[3-[5-cyano-1-(4-cyanophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]propanoic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=C(C#N)C=C1 QNZUEKRUUYXCNU-GZWBLTSWSA-N 0.000 description 1
KKNQZVJEWPHXIG-LBOXEOMUSA-N (2s)-2-[methyl-[3-(1-phenylinden-1-yl)propyl]amino]propanoic acid Chemical compound C1=CC2=CC=CC=C2C1(CCCN(C)[C@@H](C)C(O)=O)C1=CC=CC=C1 KKNQZVJEWPHXIG-LBOXEOMUSA-N 0.000 description 1
CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 1
UORHYDOYNNNDHW-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-(3-iodopropyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCI)C2=CC=C(C#N)C=C2CO1 UORHYDOYNNNDHW-UHFFFAOYSA-N 0.000 description 1
HCYFGRCYSCXKNQ-UHFFFAOYSA-N 2-(1,3-dimethyl-2,6-dioxo-7-purinyl)acetic acid Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)=O)C=N2 HCYFGRCYSCXKNQ-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
PXPLWZYFONHMMS-UHFFFAOYSA-N 2-[2-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]ethyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.O1CC2=CC(C#N)=CC=C2C1(CCN(C)CC(O)=O)C1=CC=C(F)C=C1 PXPLWZYFONHMMS-UHFFFAOYSA-N 0.000 description 1
HOKCJTQMQWEJBK-UHFFFAOYSA-N 2-[3-(3,3-dimethyl-1-phenyl-2-benzothiophen-1-yl)propyl-methylamino]acetic acid Chemical compound S1C(C)(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC=C1 HOKCJTQMQWEJBK-UHFFFAOYSA-N 0.000 description 1
JEAKOGHXLPESQX-UHFFFAOYSA-N 2-[3-(3,3-dimethyl-1-phenyl-2-benzothiophen-1-yl)propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.S1C(C)(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC=C1 JEAKOGHXLPESQX-UHFFFAOYSA-N 0.000 description 1
RQHGELJFTUQRGZ-UHFFFAOYSA-N 2-[3-(5-chloro-1-thiophen-2-yl-3h-2-benzofuran-1-yl)propyl-methylamino]butanoic acid Chemical compound O1CC2=CC(Cl)=CC=C2C1(CCCN(C)C(CC)C(O)=O)C1=CC=CS1 RQHGELJFTUQRGZ-UHFFFAOYSA-N 0.000 description 1
FVJLOLWSOFHASD-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-3,3-diethyl-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C12=CC=CC=C2C(CC)(CC)OC1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 FVJLOLWSOFHASD-UHFFFAOYSA-N 0.000 description 1
KGPQQENJOWEIII-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-3,3-dimethyl-2h-inden-1-yl]propyl-methylamino]acetic acid Chemical compound C1C(C)(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 KGPQQENJOWEIII-UHFFFAOYSA-N 0.000 description 1
SPHUZYRFLZYOHP-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(2,5-dichlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC(Cl)=CC=C1Cl SPHUZYRFLZYOHP-UHFFFAOYSA-N 0.000 description 1
OUFAHQPFGFOCCL-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=CC(C)=C1 OUFAHQPFGFOCCL-UHFFFAOYSA-N 0.000 description 1
RBAQCYGDDPOWCE-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=C(C)C=C1 RBAQCYGDDPOWCE-UHFFFAOYSA-N 0.000 description 1
TXGJKJXYOREALM-UHFFFAOYSA-N 2-[3-[1-(4-chlorophenyl)-5-[3-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C=1C=C2C(CCCN(C)CC(O)=O)(C=3C=CC(Cl)=CC=3)OCC2=CC=1C1=CC=CC(C(F)(F)F)=C1 TXGJKJXYOREALM-UHFFFAOYSA-N 0.000 description 1
HPGIDFCZZZSUNU-UHFFFAOYSA-N 2-[3-[1-(4-fluorophenyl)-5-(trifluoromethyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(C(F)(F)F)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C=C1 HPGIDFCZZZSUNU-UHFFFAOYSA-N 0.000 description 1
RTWGCBZBZKLFHN-UHFFFAOYSA-N 2-[3-[4-chloro-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC(C(=CC=C2)Cl)=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 RTWGCBZBZKLFHN-UHFFFAOYSA-N 0.000 description 1
PFUNWACYBDHFAL-UHFFFAOYSA-N 2-[3-[5-bromo-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(Br)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 PFUNWACYBDHFAL-UHFFFAOYSA-N 0.000 description 1
AZNVOIZXPGYOSB-UHFFFAOYSA-N 2-[3-[5-chloro-1-(4-chlorophenyl)-2,3-dihydroinden-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.C1CC2=CC(Cl)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 AZNVOIZXPGYOSB-UHFFFAOYSA-N 0.000 description 1
CYKZSTVLKQCCOE-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluoro-3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C(C)=C1 CYKZSTVLKQCCOE-UHFFFAOYSA-N 0.000 description 1
WKUPMDJWESAHCK-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluoro-3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C(C)=C1 WKUPMDJWESAHCK-UHFFFAOYSA-N 0.000 description 1
LKDQVWXBEMADHF-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.O1CC2=CC(C#N)=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C=C1 LKDQVWXBEMADHF-UHFFFAOYSA-N 0.000 description 1
DLIIPHVYOMLHBW-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-fluorophenyl)-3h-2-benzofuran-1-yl]propylamino]acetic acid;hydrochloride Chemical compound Cl.O1CC2=CC(C#N)=CC=C2C1(CCCNCC(=O)O)C1=CC=C(F)C=C1 DLIIPHVYOMLHBW-UHFFFAOYSA-N 0.000 description 1
ZFKXLIIUEFDRBB-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC=C(C#N)C=C2CO1 ZFKXLIIUEFDRBB-UHFFFAOYSA-N 0.000 description 1
VWFCLAZEBNWWKY-UHFFFAOYSA-N 2-[3-[5-cyano-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC=C(C#N)C=C2CO1 VWFCLAZEBNWWKY-UHFFFAOYSA-N 0.000 description 1
USZSGVSBDOXSIJ-UHFFFAOYSA-N 2-[3-[5-fluoro-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC=C(F)C=C2CO1 USZSGVSBDOXSIJ-UHFFFAOYSA-N 0.000 description 1
WINGQRZUAIJHKN-UHFFFAOYSA-N 2-[3-[5-fluoro-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC=C(F)C=C2CO1 WINGQRZUAIJHKN-UHFFFAOYSA-N 0.000 description 1
GIUHFAPURGBVFT-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-chlorophenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.O1CC2=CC=C(Cl)C=C2C1(CCCN(C)CC(O)=O)C1=CC=C(Cl)C=C1 GIUHFAPURGBVFT-UHFFFAOYSA-N 0.000 description 1
JVQZDCZIFSRDQU-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-fluoro-3-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC=C(Cl)C=C2C1(CCCN(C)CC(O)=O)C1=CC=C(F)C(C)=C1 JVQZDCZIFSRDQU-UHFFFAOYSA-N 0.000 description 1
ODHVKYXAEWWGCM-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-methoxyphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1(CCCN(C)CC(O)=O)C2=CC(Cl)=CC=C2CO1 ODHVKYXAEWWGCM-UHFFFAOYSA-N 0.000 description 1
FPZVLWDUJCYRDE-UHFFFAOYSA-N 2-[3-[6-chloro-1-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl-methylamino]acetic acid Chemical compound O1CC2=CC=C(Cl)C=C2C1(CCCN(C)CC(O)=O)C1=CC=C(C)C=C1 FPZVLWDUJCYRDE-UHFFFAOYSA-N 0.000 description 1
GXOOUMOOGHJCHS-UHFFFAOYSA-N 2-[methyl-[3-(3-methyl-1-phenylinden-1-yl)propyl]amino]acetic acid Chemical compound C1=C(C)C2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC=C1 GXOOUMOOGHJCHS-UHFFFAOYSA-N 0.000 description 1
HYHCUOXXBRKVIT-UHFFFAOYSA-N 2-[methyl-[3-[1-(4-methylphenyl)-3h-2-benzofuran-1-yl]propyl]amino]acetic acid Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=C(C)C=C1 HYHCUOXXBRKVIT-UHFFFAOYSA-N 0.000 description 1
FWMFQNAGGJQHLP-UHFFFAOYSA-N 2-[methyl-[3-[1-[3-(trifluoromethyl)phenyl]-3h-2-benzofuran-1-yl]propyl]amino]acetic acid Chemical compound O1CC2=CC=CC=C2C1(CCCN(C)CC(O)=O)C1=CC=CC(C(F)(F)F)=C1 FWMFQNAGGJQHLP-UHFFFAOYSA-N 0.000 description 1
OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 description 1
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
244000223760 Cinnamomum zeylanicum Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
RKUKMUWCRLRPEJ-UHFFFAOYSA-N Didemethylcitalopram Chemical compound O1CC2=CC(C#N)=CC=C2C1(CCCN)C1=CC=C(F)C=C1 RKUKMUWCRLRPEJ-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
102000011714 Glycine Receptors Human genes 0.000 description 1
108010076533 Glycine Receptors Proteins 0.000 description 1
229940088352 Glycine transporter inhibitor Drugs 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
101000684936 Homo sapiens Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 description 1
102000006541 Ionotropic Glutamate Receptors Human genes 0.000 description 1
108010008812 Ionotropic Glutamate Receptors Proteins 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
208000016285 Movement disease Diseases 0.000 description 1
241001274216 Naso Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
101710083167 Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 1
102100028886 Sodium- and chloride-dependent glycine transporter 2 Human genes 0.000 description 1
238000006069 Suzuki reaction reaction Methods 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229950003769 acefylline Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000008186 active pharmaceutical agent Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
VLSMHEGGTFMBBZ-UHFFFAOYSA-N alpha-Kainic acid Natural products CC(=C)C1CNC(C(O)=O)C1CC(O)=O VLSMHEGGTFMBBZ-UHFFFAOYSA-N 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
150000001543 aryl boronic acids Chemical class 0.000 description 1
150000001499 aryl bromides Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
150000005347 biaryls Chemical class 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical class C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001793 charged compounds Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000017803 cinnamon Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000105 evaporative light scattering detection Methods 0.000 description 1
230000002461 excitatory amino acid Effects 0.000 description 1
239000003257 excitatory amino acid Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
150000002332 glycine derivatives Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
230000001057 ionotropic effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
VLSMHEGGTFMBBZ-OOZYFLPDSA-N kainic acid Chemical compound CC(=C)[C@H]1CN[C@H](C(O)=O)[C@H]1CC(O)=O VLSMHEGGTFMBBZ-OOZYFLPDSA-N 0.000 description 1
229950006874 kainic acid Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
102000006239 metabotropic receptors Human genes 0.000 description 1
108020004083 metabotropic receptors Proteins 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000010369 molecular cloning Methods 0.000 description 1
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
229950010883 phencyclidine Drugs 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011435 rock Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
210000003568 synaptosome Anatomy 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- 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
- A61P25/28—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
- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Public Health (AREA)
Psychology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Vascular Medicine (AREA)
Hospice & Palliative Care (AREA)
Heart & Thoracic Surgery (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Plural Heterocyclic Compounds (AREA)

BG107530A 2000-07-21 2003-02-05 Нови съединения и тяхното използване като инхибитори на глициновия транспортер BG107530A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200001124		2000-07-21
PCT/DK2001/000510 WO2002008216A1 (en)	2000-07-21	2001-07-19	Novel compounds and their use as glycine transport inhibitors

Publications (1)

Publication Number	Publication Date
BG107530A true BG107530A (bg)	2003-09-30

Family

ID=8159626

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG107530A BG107530A (bg)	2000-07-21	2003-02-05	Нови съединения и тяхното използване като инхибитори на глициновия транспортер

Country Status (28)

Country	Link
US (1)	US6921774B2 (de)
EP (1)	EP1301502B1 (de)
JP (1)	JP2004504393A (de)
KR (1)	KR20030015889A (de)
CN (1)	CN100509791C (de)
AR (1)	AR032358A1 (de)
AT (1)	ATE295844T1 (de)
AU (2)	AU8174001A (de)
BG (1)	BG107530A (de)
BR (1)	BR0113011A (de)
CA (1)	CA2416447A1 (de)
CZ (1)	CZ2003396A3 (de)
DE (1)	DE60110914T2 (de)
EA (1)	EA005621B1 (de)
ES (1)	ES2238466T3 (de)
HR (1)	HRP20030053A2 (de)
HU (1)	HUP0302778A3 (de)
IL (2)	IL153988A0 (de)
IS (1)	IS6693A (de)
MX (1)	MXPA03000642A (de)
NO (1)	NO20030243L (de)
NZ (1)	NZ523720A (de)
PL (1)	PL364439A1 (de)
PT (1)	PT1301502E (de)
SK (1)	SK2022003A3 (de)
UA (1)	UA75081C2 (de)
WO (1)	WO2002008216A1 (de)
ZA (1)	ZA200300514B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1622868A1 (de) *	2003-04-30	2006-02-08	H. Lundbeck A/S	Aromatische oxyphenyl- und aromatische sulfanylphenyl-derivate
BRPI0413587A (pt) *	2003-08-21	2006-10-17	Lundbeck & Co As H	usos de um composto e de um inibidor de glyt-1, composição farmacêutica, kit, e, método para o tratamento de doença
US7163954B2 (en) *	2003-09-25	2007-01-16	Wyeth	Substituted naphthyl benzothiophene acids
JP2007528879A (ja) *	2004-03-12	2007-10-18	ハー・ルンドベック・アクチエゼルスカベット	フェニルインダン誘導体
WO2005100301A1 (en) *	2004-03-31	2005-10-27	Eli Lilly And Company	2-aryloxyethyl glycine derivatives and their use as glycine transport inhibitors
WO2006000222A2 (en) *	2004-06-24	2006-01-05	H. Lundbeck A/S	The combination of an antipsychotic and a glycine transporter type i inhibitor for the treatment of schizophrenia
ES2412384T3 (es) *	2006-07-18	2013-07-11	Astellas Pharma Inc.	Derivado de aminoindano o sal del mismo
CA2661863A1 (en) *	2006-08-30	2008-03-06	F. Hoffmann-La Roche Ag	Inhibitors for glyt-1
US20100083581A1 (en) *	2007-06-18	2010-04-08	Mattice Douglas A	Environmental brush seal
EP2389187B1 (de)	2009-01-20	2016-11-16	Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center	Sorbin- und benzoesäure und derivate daraus zur verstärkung der wirkung eines neuropharmakons
EP2380595A1 (de)	2010-04-19	2011-10-26	Nlife Therapeutics S.L.	Zusammensetzungen und Verfahren zur selektiven Abgabe von Oligonukleotidmolekülen an spezifische Neuronentypen
US9700563B2 (en) *	2012-09-06	2017-07-11	MediSynergies, LLC	Kappa opioid receptor compounds

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1166711A (en) *	1966-03-28	1969-10-08	Kefalas As	Process for the Preparation of Phenyl-Indane and -Tetralin Derivatives
US3549656A (en) *	1967-12-28	1970-12-22	Kefalas As	Antidepressant 1 - aminoalkyl - thiophthalanes and acid addition salts thereof
GB1526331A (en) *	1976-01-14	1978-09-27	Kefalas As	Phthalanes
US5225323A (en)	1988-11-21	1993-07-06	Baylor College Of Medicine	Human high-affinity neurotransmitter uptake system
US5756348A (en)	1991-11-12	1998-05-26	Synaptic Pharmaceutical Corporation	DNA encoding a glycine transporter and uses thereof
US5824486A (en)	1996-05-31	1998-10-20	Allelix Neuroscience Inc.	Glycine transporter-transfected cells and uses thereof
US6008015A (en)	1997-04-11	1999-12-28	Allelix Neuroscience Inc.	Glycine transporter
AR021509A1 (es) *	1998-12-08	2002-07-24	Lundbeck & Co As H	Derivados de benzofurano, su preparacion y uso
AR021155A1 (es) *	1999-07-08	2002-06-12	Lundbeck & Co As H	Tratamiento de desordenes neuroticos
US6566550B2 (en) *	2001-06-21	2003-05-20	Pfizer Inc	Substituted aromatic ethers as inhibitors of glycine transport

2001
- 2001-07-19 AU AU8174001A patent/AU8174001A/xx active Pending
- 2001-07-19 AU AU2001281740A patent/AU2001281740B2/en not_active Ceased
- 2001-07-19 ES ES01960184T patent/ES2238466T3/es not_active Expired - Lifetime
- 2001-07-19 NZ NZ523720A patent/NZ523720A/en unknown
- 2001-07-19 MX MXPA03000642A patent/MXPA03000642A/es not_active Application Discontinuation
- 2001-07-19 HU HU0302778A patent/HUP0302778A3/hu unknown
- 2001-07-19 HR HR20030053A patent/HRP20030053A2/hr not_active Application Discontinuation
- 2001-07-19 CZ CZ2003396A patent/CZ2003396A3/cs unknown
- 2001-07-19 CA CA002416447A patent/CA2416447A1/en not_active Abandoned
- 2001-07-19 AT AT01960184T patent/ATE295844T1/de not_active IP Right Cessation
- 2001-07-19 PT PT01960184T patent/PT1301502E/pt unknown
- 2001-07-19 BR BR0113011-0A patent/BR0113011A/pt not_active IP Right Cessation
- 2001-07-19 CN CNB018158579A patent/CN100509791C/zh not_active Expired - Fee Related
- 2001-07-19 JP JP2002514122A patent/JP2004504393A/ja not_active Withdrawn
- 2001-07-19 EA EA200300180A patent/EA005621B1/ru not_active IP Right Cessation
- 2001-07-19 KR KR10-2003-7000851A patent/KR20030015889A/ko not_active Ceased
- 2001-07-19 EP EP01960184A patent/EP1301502B1/de not_active Expired - Lifetime
- 2001-07-19 PL PL01364439A patent/PL364439A1/xx not_active Application Discontinuation
- 2001-07-19 UA UA2003010452A patent/UA75081C2/uk unknown
- 2001-07-19 DE DE60110914T patent/DE60110914T2/de not_active Expired - Fee Related
- 2001-07-19 IL IL15398801A patent/IL153988A0/xx not_active IP Right Cessation
- 2001-07-19 WO PCT/DK2001/000510 patent/WO2002008216A1/en not_active Ceased
- 2001-07-19 SK SK202-2003A patent/SK2022003A3/sk unknown
- 2001-07-20 AR ARP010103460A patent/AR032358A1/es not_active Application Discontinuation
2003
- 2003-01-16 IL IL153988A patent/IL153988A/en unknown
- 2003-01-17 US US10/348,490 patent/US6921774B2/en not_active Expired - Fee Related
- 2003-01-17 NO NO20030243A patent/NO20030243L/no not_active Application Discontinuation
- 2003-01-20 IS IS6693A patent/IS6693A/is unknown
- 2003-01-20 ZA ZA200300514A patent/ZA200300514B/en unknown
- 2003-02-05 BG BG107530A patent/BG107530A/bg unknown

Also Published As

Publication number	Publication date
NO20030243D0 (no)	2003-01-17
EP1301502B1 (de)	2005-05-18
AU8174001A (en)	2002-02-05
EP1301502A1 (de)	2003-04-16
HRP20030053A2 (en)	2005-02-28
IL153988A (en)	2006-10-05
CZ2003396A3 (cs)	2003-05-14
ES2238466T3 (es)	2005-09-01
HUP0302778A3 (en)	2005-02-28
ATE295844T1 (de)	2005-06-15
DE60110914T2 (de)	2005-10-27
SK2022003A3 (en)	2003-06-03
EA005621B1 (ru)	2005-04-28
AR032358A1 (es)	2003-11-05
NZ523720A (en)	2004-07-30
US6921774B2 (en)	2005-07-26
HUP0302778A2 (hu)	2003-12-29
CA2416447A1 (en)	2002-01-31
CN1662519A (zh)	2005-08-31
BR0113011A (pt)	2003-07-01
ZA200300514B (en)	2004-08-20
WO2002008216A1 (en)	2002-01-31
AU2001281740B2 (en)	2006-02-16
PL364439A1 (en)	2004-12-13
JP2004504393A (ja)	2004-02-12
CN100509791C (zh)	2009-07-08
PT1301502E (pt)	2005-09-30
IL153988A0 (en)	2003-07-31
IS6693A (is)	2003-01-20
DE60110914D1 (de)	2005-06-23
KR20030015889A (ko)	2003-02-25
US20030181445A1 (en)	2003-09-25
MXPA03000642A (es)	2003-06-06
NO20030243L (no)	2003-03-06
EA200300180A1 (ru)	2003-06-26
UA75081C2 (en)	2006-03-15

Publication	Publication Date	Title
CN116589459B (zh)	2026-01-30	凋亡诱导剂
TWI543974B (zh)	2016-08-01	苯基－３－氮雜－雙環［３．１．０］己－３－基－甲酮及其作為藥物之用途
DE69608551T2 (de)	2001-01-18	Bicyclische amin-derivate und ihre verwendung als antipsychotische wirkstoffe
BG107530A (bg)	2003-09-30	Нови съединения и тяхното използване като инхибитори на глициновия транспортер
US10106523B2 (en)	2018-10-23	Amide compound
DE19952147A1 (de)	2001-05-03	Neue Cyclopropane, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
KR20120084771A (ko)	2012-07-30	브래디키닌 수용체 길항제로서 유용한 2-아릴-프로피온아미드 유도체 및 이를 함유하는 약학적 조성물
JP4937347B2 (ja)	2012-05-23	置換フェニルメタノン誘導体
AU2001281740A1 (en)	2002-05-02	Novel compounds and their use as glycine transport inhibitors
JP2003513970A (ja)	2003-04-15	中枢神経系障害の治療のための［（インドール−３−イル）−シクロアルキル］−３−置換アゼチジン
JP6401156B2 (ja)	2018-10-03	イミダゾ［２，１−ｂ］チアゾール誘導体、その製造方法、および医薬品としての使用
WO2022111473A1 (en)	2022-06-02	Compounds as mrgprx2 antagonists
AU3964393A (en)	1993-11-18	Novel amidoalkyl- and imidoalkyl-piperazines
JP2019516736A (ja)	2019-06-20	疼痛に対する多様な活性を有するテトラヒドロピラン誘導体およびチオピラン誘導体
KR20020084091A (ko)	2002-11-04	신규 이미다졸 유도체
JP6844822B2 (ja)	2021-03-17	疼痛に対して活性を有する置換モルホリン誘導体
JP3786983B2 (ja)	2006-06-21	ピロリジノン誘導体
JP2018531263A6 (ja)	2018-12-13	疼痛に対して活性を有するオキサジアザスピロ化合物
JP2018531263A (ja)	2018-10-25	疼痛に対して活性を有するオキサジアザスピロ化合物
KR101651994B1 (ko)	2016-08-30	아릴옥시 아제티딘 화합물, 및 이를 포함하는 약학 조성물
KR101837957B1 (ko)	2018-03-13	ｍＧｌｕＲ5 길항제로서의 활성을 가지는 티아졸-2-카르복사아마이드 유도체