JP2005529923A5 - - Google Patents
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- Publication number
- JP2005529923A5 JP2005529923A5 JP2004505046A JP2004505046A JP2005529923A5 JP 2005529923 A5 JP2005529923 A5 JP 2005529923A5 JP 2004505046 A JP2004505046 A JP 2004505046A JP 2004505046 A JP2004505046 A JP 2004505046A JP 2005529923 A5 JP2005529923 A5 JP 2005529923A5
- Authority
- JP
- Japan
- Prior art keywords
- phenoxy
- ethylsulfanylmethyl
- phenyl
- oxadiazol
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 21
- 125000005647 linker group Chemical group 0.000 claims description 15
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- -1 -O- aryl Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 208000008589 Obesity Diseases 0.000 claims description 9
- 235000020824 obesity Nutrition 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- 150000001924 cycloalkanes Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 3
- 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 2
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 2
- 101800002739 Melanin-concentrating hormone Proteins 0.000 claims description 2
- UWAOJIWUVCMBAZ-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-dimethylazanium;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UWAOJIWUVCMBAZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000002830 appetite depressant Substances 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002466 imines Chemical class 0.000 claims description 2
- ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 claims description 2
- 102000047659 melanin-concentrating hormone Human genes 0.000 claims description 2
- 229940045623 meridia Drugs 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229940002552 xenical Drugs 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 15
- 101150065749 Churc1 gene Proteins 0.000 claims 15
- 102100038239 Protein Churchill Human genes 0.000 claims 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000002265 prevention Effects 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 4
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 3
- 208000024891 symptom Diseases 0.000 claims 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 2
- ZQFGMBMVBAUANY-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 ZQFGMBMVBAUANY-UHFFFAOYSA-N 0.000 claims 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 claims 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 2
- 201000001421 hyperglycemia Diseases 0.000 claims 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 2
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical group CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 claims 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical group CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical group CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 230000001568 sexual effect Effects 0.000 claims 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- NOBNOYZISXSMNC-UHFFFAOYSA-N 1-[2-(diethylamino)ethyl]-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(CC)CC)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 NOBNOYZISXSMNC-UHFFFAOYSA-N 0.000 claims 1
- VORMOLPPWUQLGJ-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-methyl-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)N(C)CCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 VORMOLPPWUQLGJ-UHFFFAOYSA-N 0.000 claims 1
- SYYBGPOTFZKZSU-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 SYYBGPOTFZKZSU-UHFFFAOYSA-N 0.000 claims 1
- NXQHAFFKQAKDKG-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 NXQHAFFKQAKDKG-UHFFFAOYSA-N 0.000 claims 1
- RUIWGKYCDZXWAA-UHFFFAOYSA-N 1-[3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]propyl]piperidin-4-one Chemical compound C1CC(=O)CCN1CCCOC1=CC=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=C1 RUIWGKYCDZXWAA-UHFFFAOYSA-N 0.000 claims 1
- CPBVAHJHYUDQLQ-UHFFFAOYSA-N 1-[4-[2-(1-benzofuran-2-ylmethoxymethyl)-1,3-oxazol-5-yl]phenyl]-3-(2-piperidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(COCC=3OC4=CC=CC=C4C=3)=NC=2)C=CC=1NC(=O)NCCN1CCCCC1 CPBVAHJHYUDQLQ-UHFFFAOYSA-N 0.000 claims 1
- QVWGXPSUJCXAJM-UHFFFAOYSA-N 1-[4-[2-(1-benzofuran-2-ylmethoxymethyl)-1,3-oxazol-5-yl]phenyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(COCC=3OC4=CC=CC=C4C=3)=NC=2)C=CC=1NC(=O)NCCN1CCCC1 QVWGXPSUJCXAJM-UHFFFAOYSA-N 0.000 claims 1
- KJEOYXFPNLXFRC-UHFFFAOYSA-N 1-[4-[2-(1-benzofuran-2-ylmethoxymethyl)-1,3-oxazol-5-yl]phenyl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=CC(NC(=O)NCCN(C)C)=CC=C1C(O1)=CN=C1COCC1=CC2=CC=CC=C2O1 KJEOYXFPNLXFRC-UHFFFAOYSA-N 0.000 claims 1
- BRFZHDJIEUHNIA-UHFFFAOYSA-N 1-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenyl]-3-(2-piperidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NC=2)C=CC=1NC(=O)NCCN1CCCCC1 BRFZHDJIEUHNIA-UHFFFAOYSA-N 0.000 claims 1
- IBRRUVVATXUSGK-UHFFFAOYSA-N 1-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NC=2)C=CC=1NC(=O)NCCN1CCCC1 IBRRUVVATXUSGK-UHFFFAOYSA-N 0.000 claims 1
- FCIXWGXQJWSGDG-UHFFFAOYSA-N 1-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenyl]-3-(3-pyrrolidin-1-ylpropyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NC=2)C=CC=1NC(=O)NCCCN1CCCC1 FCIXWGXQJWSGDG-UHFFFAOYSA-N 0.000 claims 1
- DXBMLNGWAWQPAJ-UHFFFAOYSA-N 1-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]-3-(2-piperidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1NC(=O)NCCN1CCCCC1 DXBMLNGWAWQPAJ-UHFFFAOYSA-N 0.000 claims 1
- WTEMBRSLUATHAX-UHFFFAOYSA-N 1-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1NC(=O)NCCN1CCCC1 WTEMBRSLUATHAX-UHFFFAOYSA-N 0.000 claims 1
- OSFVOTFXYJVUPY-UHFFFAOYSA-N 1-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]-3-(3-pyrrolidin-1-ylpropyl)urea Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1NC(=O)NCCCN1CCCC1 OSFVOTFXYJVUPY-UHFFFAOYSA-N 0.000 claims 1
- CRXQXJBBEULVPF-UHFFFAOYSA-N 1-[5-(dimethylamino)pentyl]-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]urea Chemical compound C1=CC(NC(=O)NCCCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 CRXQXJBBEULVPF-UHFFFAOYSA-N 0.000 claims 1
- MWCQZISFODDCBB-UHFFFAOYSA-N 2-(1-benzofuran-2-ylmethylsulfanylmethyl)-5-[4-(3-piperidin-1-ylpropoxy)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=C(C=2OC(CSCC=3OC4=CC=CC=C4C=3)=NN=2)C=CC=1OCCCN1CCCCC1 MWCQZISFODDCBB-UHFFFAOYSA-N 0.000 claims 1
- LBCIHPFDTHADEK-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(2-piperidin-1-ylethoxy)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1)=CC=C1OCCN1CCCCC1 LBCIHPFDTHADEK-UHFFFAOYSA-N 0.000 claims 1
- LKNFOLRVASLWBO-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(2-piperidin-1-ylethoxy)phenyl]-1,3-oxazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NC=C1C(C=C1)=CC=C1OCCN1CCCCC1 LKNFOLRVASLWBO-UHFFFAOYSA-N 0.000 claims 1
- MUKSHRMCLVLWSW-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1)=CC=C1OCCN1CCCC1 MUKSHRMCLVLWSW-UHFFFAOYSA-N 0.000 claims 1
- QKLFDQIMIKMOHC-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,3-oxazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NC=C1C(C=C1)=CC=C1OCCN1CCCC1 QKLFDQIMIKMOHC-UHFFFAOYSA-N 0.000 claims 1
- FLRKUVKDVCRPIU-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-piperidin-1-ylpropoxy)phenyl]-1,3,4-oxadiazole Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 FLRKUVKDVCRPIU-UHFFFAOYSA-N 0.000 claims 1
- CZQLRFOIKRGPFY-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-piperidin-1-ylpropoxy)phenyl]-1,3-oxazole Chemical compound C1CCCCN1CCCOC(C=C1)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 CZQLRFOIKRGPFY-UHFFFAOYSA-N 0.000 claims 1
- AOVYQQZRAIMKCT-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-pyrrolidin-1-ylprop-1-enyl)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1)=CC=C1C=CCN1CCCC1 AOVYQQZRAIMKCT-UHFFFAOYSA-N 0.000 claims 1
- UPPLPXXCUVZKKS-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-pyrrolidin-1-ylprop-1-enyl)phenyl]-1,3-oxazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NC=C1C(C=C1)=CC=C1C=CCN1CCCC1 UPPLPXXCUVZKKS-UHFFFAOYSA-N 0.000 claims 1
- KODGODPHRAMNPH-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1,3,4-oxadiazole Chemical compound C1CCCN1CCCOC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 KODGODPHRAMNPH-UHFFFAOYSA-N 0.000 claims 1
- LOHATDVCIFLTAA-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]-1,3-oxazole Chemical compound C1CCCN1CCCOC(C=C1)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 LOHATDVCIFLTAA-UHFFFAOYSA-N 0.000 claims 1
- WRMXGNFJJFNDRZ-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(4-piperidin-1-ylbutoxy)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1OCCCCN1CCCCC1 WRMXGNFJJFNDRZ-UHFFFAOYSA-N 0.000 claims 1
- JRHDSZDDINSXKK-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(4-pyrrolidin-1-ylbutoxy)phenyl]-1,3,4-oxadiazole Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1OCCCCN1CCCC1 JRHDSZDDINSXKK-UHFFFAOYSA-N 0.000 claims 1
- WYRLGFNRKNSCQP-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(5-piperidin-1-ylpent-1-enyl)phenyl]-1,3,4-oxadiazole Chemical compound C1CCCCN1CCCC=CC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 WYRLGFNRKNSCQP-UHFFFAOYSA-N 0.000 claims 1
- JZIDIKMNTMIRMH-UHFFFAOYSA-N 2-(2-phenoxyethylsulfanylmethyl)-5-[4-(5-pyrrolidin-1-ylpent-1-enyl)phenyl]-1,3,4-oxadiazole Chemical compound C1CCCN1CCCC=CC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 JZIDIKMNTMIRMH-UHFFFAOYSA-N 0.000 claims 1
- XXWWMNADBZQFGR-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)COCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 XXWWMNADBZQFGR-UHFFFAOYSA-N 0.000 claims 1
- SMKNXGQNTADCGL-UHFFFAOYSA-N 2-[4-[(1-methylpiperidin-3-yl)methoxy]phenyl]-5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazole Chemical compound C1N(C)CCCC1COC1=CC=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=C1 SMKNXGQNTADCGL-UHFFFAOYSA-N 0.000 claims 1
- AJSPMLQIJMWNDO-UHFFFAOYSA-N 2-[4-[2-(azepan-1-yl)ethoxy]phenyl]-5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(O1)=NN=C1C(C=C1)=CC=C1OCCN1CCCCCC1 AJSPMLQIJMWNDO-UHFFFAOYSA-N 0.000 claims 1
- WUXSPYSSSUMUMB-UHFFFAOYSA-N 2-[4-[3-(azepan-1-yl)propoxy]phenyl]-5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazole Chemical compound C1CCCCCN1CCCOC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 WUXSPYSSSUMUMB-UHFFFAOYSA-N 0.000 claims 1
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| AU2004209505B2 (en) | 2003-02-10 | 2009-07-23 | Banyu Pharmaceutical Co., Ltd. | Melanin-concentrating hormone receptor antagonists containing piperidine derivatives as the active ingredient |
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| US7550602B1 (en) * | 2004-01-14 | 2009-06-23 | Palatin Technologies, Inc. | Small molecule compositions for sexual dysfunction |
| US7319108B2 (en) | 2004-01-25 | 2008-01-15 | Sanofi-Aventis Deutschland Gmbh | Aryl-substituted heterocycles, process for their preparation and their use as medicaments |
| US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
| DE102004003812A1 (de) * | 2004-01-25 | 2005-08-11 | Aventis Pharma Deutschland Gmbh | Arylsubstituierte Heterozyklen, Verfahren ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102004017932A1 (de) * | 2004-04-14 | 2005-11-03 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Alkin-Verbindungen mit MCH-antagonistischer Wirkung und diese Verbindungen enthaltende Arzneimittel |
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| CA2602336A1 (en) * | 2005-03-31 | 2006-10-05 | Ucb Pharma S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
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| CA2623327A1 (en) * | 2005-10-07 | 2007-04-19 | Kissei Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic compound and pharmaceutical composition comprising the same |
| ES2412007T3 (es) | 2005-12-21 | 2013-07-09 | Janssen Pharmaceutica, N.V. | Derivados de pirazinona sustituida novedosos para uso en enfermedades mediadas por MCH-1 |
| CA2636617A1 (en) | 2006-02-15 | 2007-08-23 | Lothar Schwink | Novel aminoalcohol-substituted aryldihydroisoquinolinones, process for their preparation and their use as medicaments |
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| US2641601A (en) * | 1950-11-24 | 1953-06-09 | Hoffmann La Roche | Furans and method of preparation |
| BE556801A (enExample) * | 1956-04-19 | |||
| US3708598A (en) * | 1970-07-10 | 1973-01-02 | Sandoz Ag | Substituted 2,4-(omega-aminoalkoxy)phenyl imidazoles as cholesterol reducing agents |
| US6034106A (en) * | 1996-06-07 | 2000-03-07 | Merck & Co., Inc. | Oxadiazole benzenesulfonamides as selective β3 Agonist for the treatment of Diabetes and Obesity |
| WO2000006556A1 (en) | 1998-07-27 | 2000-02-10 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
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| WO2002032897A1 (en) * | 2000-10-20 | 2002-04-25 | Pfizer Products Inc. | Alpha-aryl ethanolamines and their use as beta-3 adrenergic receptor agonists |
-
2003
- 2003-05-06 US US10/512,986 patent/US7229987B2/en not_active Expired - Fee Related
- 2003-05-06 WO PCT/US2003/012123 patent/WO2003097047A1/en not_active Ceased
- 2003-05-06 CA CA002484233A patent/CA2484233A1/en not_active Abandoned
- 2003-05-06 JP JP2004505046A patent/JP2005529923A/ja active Pending
- 2003-05-06 AU AU2003222648A patent/AU2003222648A1/en not_active Abandoned
- 2003-05-06 EP EP03719843A patent/EP1505968A1/en not_active Withdrawn
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