HRP20020376A2 - Diaryl-enynes - Google Patents
Diaryl-enynes Download PDFInfo
- Publication number
- HRP20020376A2 HRP20020376A2 HR20020376A HRP20020376A HRP20020376A2 HR P20020376 A2 HRP20020376 A2 HR P20020376A2 HR 20020376 A HR20020376 A HR 20020376A HR P20020376 A HRP20020376 A HR P20020376A HR P20020376 A2 HRP20020376 A2 HR P20020376A2
- Authority
- HR
- Croatia
- Prior art keywords
- penten
- phenyl
- sarcosine
- compound according
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 124
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 70
- 229940043230 sarcosine Drugs 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- -1 heterocycloalkyloxy Chemical group 0.000 claims description 39
- 239000004471 Glycine Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims description 7
- VKSQEFQZQGQCCF-UHFFFAOYSA-N 2-[methyl-[5-(4-methylphenyl)-3-phenylpent-2-en-4-ynyl]amino]acetic acid Chemical compound C=1C=CC=CC=1C(=CCN(C)CC(O)=O)C#CC1=CC=C(C)C=C1 VKSQEFQZQGQCCF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- KIGCTKNPXSPYMQ-XKZIYDEJSA-N 2-[[(e)-5-[4-(furan-3-yl)phenyl]-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound C=1C=CC=CC=1C(=C/CN(C)CC(O)=O)\C#CC(C=C1)=CC=C1C=1C=COC=1 KIGCTKNPXSPYMQ-XKZIYDEJSA-N 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000005000 thioaryl group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- ZDUHEAHMELDYHK-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[5-(4-propan-2-ylphenyl)-3-[4-(trifluoromethyl)phenyl]pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)C(F)(F)F ZDUHEAHMELDYHK-UHFFFAOYSA-N 0.000 claims 1
- ZBUNUPLXGZUREY-UHFFFAOYSA-N 2-[[5-(1,3-benzodioxol-5-yl)-3-(3-fluorophenyl)pent-2-en-4-ynyl]-methylamino]acetic acid 2-[[3-(4-methoxyphenyl)-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound CN(CC=C(C#Cc1ccc2OCOc2c1)c1cccc(F)c1)CC(O)=O.COc1ccc(cc1)C(=CCN(C)CC(O)=O)C#Cc1ccc(cc1)C(C)C ZBUNUPLXGZUREY-UHFFFAOYSA-N 0.000 claims 1
- AUSKEXIWZLFQBZ-UHFFFAOYSA-N 2-[[5-(4-benzylphenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[[5-(4-ethylphenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[3-phenyl-5-[4-(trifluoromethyl)phenyl]pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C1=CC=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F AUSKEXIWZLFQBZ-UHFFFAOYSA-N 0.000 claims 1
- LTGNCFCEPVIRRQ-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[3-phenyl-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.ClC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 LTGNCFCEPVIRRQ-UHFFFAOYSA-N 0.000 claims 1
- BORJBSBRKQHWRL-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl BORJBSBRKQHWRL-UHFFFAOYSA-N 0.000 claims 1
- FWLUAHUEIQLNKL-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F FWLUAHUEIQLNKL-UHFFFAOYSA-N 0.000 claims 1
- WGMDIMQMNPJQHF-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl WGMDIMQMNPJQHF-UHFFFAOYSA-N 0.000 claims 1
- KZBRSMDVMITLTO-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CSC=C1.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC(=CC=C1)F Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CSC=C1.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC(=CC=C1)F KZBRSMDVMITLTO-UHFFFAOYSA-N 0.000 claims 1
- YGTRJOGPGUOVHV-UHFFFAOYSA-N C1(=CC=CC=C1)C(=CCN(C)CC(=O)O)C#CC1=CC=CC=C1.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F Chemical compound C1(=CC=CC=C1)C(=CCN(C)CC(=O)O)C#CC1=CC=CC=C1.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F YGTRJOGPGUOVHV-UHFFFAOYSA-N 0.000 claims 1
- MRAGRIYHJYUMQZ-UHFFFAOYSA-N CC=1C=C(C=CC1C)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1=C(C=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound CC=1C=C(C=CC1C)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1=C(C=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 MRAGRIYHJYUMQZ-UHFFFAOYSA-N 0.000 claims 1
- QGCVRYRLRVVMSF-UHFFFAOYSA-N COC=1C=C(C=CC1OC)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(OC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F Chemical compound COC=1C=C(C=CC1OC)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(OC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F QGCVRYRLRVVMSF-UHFFFAOYSA-N 0.000 claims 1
- XRFPOAAGUBVQEP-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound FC1=C(C=CC(=C1)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 XRFPOAAGUBVQEP-UHFFFAOYSA-N 0.000 claims 1
- SYBRNLPEAJXMNU-UHFFFAOYSA-N N1C(=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1OC=2C=C(C=CC2O1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound N1C(=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1OC=2C=C(C=CC2O1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 SYBRNLPEAJXMNU-UHFFFAOYSA-N 0.000 claims 1
- CWKQXDBGYZDSOO-UHFFFAOYSA-N [N+](=O)([O-])C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.[N+](=O)([O-])C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound [N+](=O)([O-])C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.[N+](=O)([O-])C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 CWKQXDBGYZDSOO-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 description 103
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 76
- 239000003921 oil Substances 0.000 description 75
- 235000019198 oils Nutrition 0.000 description 75
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 19
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 19
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 17
- 239000012230 colorless oil Substances 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- 239000006260 foam Substances 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 102000005962 receptors Human genes 0.000 description 12
- 108020003175 receptors Proteins 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [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 11
- 210000004027 cell Anatomy 0.000 description 11
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- PQJOSEVTIKYWLH-UHFFFAOYSA-N 1-iodo-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(I)C=C1 PQJOSEVTIKYWLH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 9
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 230000001404 mediated effect Effects 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 108010078791 Carrier Proteins Proteins 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- 102000011714 Glycine Receptors Human genes 0.000 description 6
- 108010076533 Glycine Receptors Proteins 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001503 aryl iodides Chemical class 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000002858 neurotransmitter agent Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 235000015320 potassium carbonate Nutrition 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 238000000159 protein binding assay Methods 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- 108010077895 Sarcosine Proteins 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000004327 boric acid Substances 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
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Classifications
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- 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
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- 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
- C07C229/34—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 containing six-membered aromatic rings
- C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Epidemiology (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)
- Plural Heterocyclic Compounds (AREA)
- Confectionery (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43102299A | 1999-11-01 | 1999-11-01 | |
| PCT/US2000/030074 WO2001032602A1 (en) | 1999-11-01 | 2000-11-01 | Diaryl-enynes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020376A2 true HRP20020376A2 (en) | 2004-02-29 |
Family
ID=23710104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020376A HRP20020376A2 (en) | 1999-11-01 | 2002-04-29 | Diaryl-enynes |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1226108A4 (xx) |
| JP (1) | JP2003513063A (xx) |
| KR (1) | KR100702717B1 (xx) |
| CN (1) | CN100357274C (xx) |
| AU (1) | AU780922C (xx) |
| BG (1) | BG65275B1 (xx) |
| BR (1) | BR0015199A (xx) |
| CA (1) | CA2387660A1 (xx) |
| CZ (1) | CZ20021545A3 (xx) |
| EA (1) | EA004602B1 (xx) |
| EE (1) | EE05031B1 (xx) |
| HR (1) | HRP20020376A2 (xx) |
| HU (1) | HUP0203182A3 (xx) |
| IL (1) | IL149347A0 (xx) |
| MX (1) | MXPA02004354A (xx) |
| NO (1) | NO20021936L (xx) |
| NZ (1) | NZ529245A (xx) |
| PL (1) | PL355425A1 (xx) |
| SK (1) | SK6202002A3 (xx) |
| UA (1) | UA73749C2 (xx) |
| WO (1) | WO2001032602A1 (xx) |
| ZA (1) | ZA200203458B (xx) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04225953A (ja) * | 1990-05-07 | 1992-08-14 | Shionogi & Co Ltd | スピロ ジベンゾスベラン誘導体 |
| ATE136461T1 (de) * | 1990-08-13 | 1996-04-15 | Searle & Co | Verwendung von heterozyklischen aminoalkoholverbindungen zur herstellung eines medikaments für die behandlung von erkrankungen des zns |
| ATE320804T1 (de) * | 1995-12-07 | 2006-04-15 | Daniel C Javitt | Behandlung negativer und kognitiver symptome der schizophrenie mit antagonisten der glycinaufnahme |
| UA52698C2 (uk) * | 1996-10-04 | 2003-01-15 | Х. Луннбек А/С | Похідні (3-алкоксіізоксазол-4-іл)заміщеної 2-амінокарбонової кислоти та їх сірковмісні аналоги, фармацевтична композиція на їх основі |
| BR9907951A (pt) * | 1998-03-06 | 2001-01-30 | Janssen Pharmaceutica Nv | Inibidores de transporte de glicina |
| CA2322136A1 (en) * | 1998-03-06 | 1999-09-10 | Ludo Edmond Josephine Kennis | Glycine transport inhibitors |
| PE20000728A1 (es) * | 1998-06-26 | 2000-08-21 | Cocensys Inc | Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda |
| US6103743A (en) * | 1999-08-06 | 2000-08-15 | Allelix Neuroscience, Inc. | Unsaturated amino acid derivatives |
-
2000
- 2000-01-11 UA UA2002043703A patent/UA73749C2/uk unknown
- 2000-11-01 CA CA002387660A patent/CA2387660A1/en not_active Abandoned
- 2000-11-01 AU AU14507/01A patent/AU780922C/en not_active Ceased
- 2000-11-01 HU HU0203182A patent/HUP0203182A3/hu unknown
- 2000-11-01 BR BR0015199-8A patent/BR0015199A/pt not_active Application Discontinuation
- 2000-11-01 JP JP2001534756A patent/JP2003513063A/ja active Pending
- 2000-11-01 SK SK620-2002A patent/SK6202002A3/sk unknown
- 2000-11-01 WO PCT/US2000/030074 patent/WO2001032602A1/en active IP Right Grant
- 2000-11-01 EP EP00976775A patent/EP1226108A4/en not_active Withdrawn
- 2000-11-01 MX MXPA02004354A patent/MXPA02004354A/es active IP Right Grant
- 2000-11-01 KR KR1020027005593A patent/KR100702717B1/ko not_active IP Right Cessation
- 2000-11-01 CZ CZ20021545A patent/CZ20021545A3/cs unknown
- 2000-11-01 EA EA200200521A patent/EA004602B1/ru not_active IP Right Cessation
- 2000-11-01 NZ NZ529245A patent/NZ529245A/en active Application Filing
- 2000-11-01 EE EEP200200229A patent/EE05031B1/xx not_active IP Right Cessation
- 2000-11-01 PL PL00355425A patent/PL355425A1/xx not_active IP Right Cessation
- 2000-11-01 CN CNB008151970A patent/CN100357274C/zh not_active Expired - Fee Related
- 2000-11-01 IL IL14934700A patent/IL149347A0/xx unknown
-
2002
- 2002-04-24 NO NO20021936A patent/NO20021936L/no not_active Application Discontinuation
- 2002-04-29 HR HR20020376A patent/HRP20020376A2/hr not_active Application Discontinuation
- 2002-04-30 ZA ZA200203458A patent/ZA200203458B/xx unknown
- 2002-04-30 BG BG106671A patent/BG65275B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU780922C (en) | 2005-10-20 |
| HUP0203182A2 (hu) | 2003-01-28 |
| KR100702717B1 (ko) | 2007-04-03 |
| HUP0203182A3 (en) | 2003-04-28 |
| IL149347A0 (en) | 2002-11-10 |
| MXPA02004354A (es) | 2003-10-06 |
| ZA200203458B (en) | 2003-10-29 |
| NO20021936L (no) | 2002-07-01 |
| EP1226108A4 (en) | 2004-06-16 |
| UA73749C2 (en) | 2005-09-15 |
| CA2387660A1 (en) | 2001-05-10 |
| WO2001032602A1 (en) | 2001-05-10 |
| PL355425A1 (en) | 2004-04-19 |
| NO20021936D0 (no) | 2002-04-24 |
| EA200200521A1 (ru) | 2002-10-31 |
| EA004602B1 (ru) | 2004-06-24 |
| EP1226108A1 (en) | 2002-07-31 |
| JP2003513063A (ja) | 2003-04-08 |
| BR0015199A (pt) | 2002-07-09 |
| SK6202002A3 (en) | 2002-10-08 |
| NZ529245A (en) | 2005-09-30 |
| EE05031B1 (et) | 2008-06-16 |
| CN100357274C (zh) | 2007-12-26 |
| AU1450701A (en) | 2001-05-14 |
| AU780922B2 (en) | 2005-04-28 |
| CZ20021545A3 (cs) | 2002-10-16 |
| BG65275B1 (bg) | 2007-11-30 |
| EE200200229A (et) | 2003-06-16 |
| KR20020060961A (ko) | 2002-07-19 |
| CN1387507A (zh) | 2002-12-25 |
| BG106671A (en) | 2003-02-28 |
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Owner name: NPS PHARMACEUTICALS, INC., US |
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| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20091026 Year of fee payment: 10 |
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