JP2005529923A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- QAXWPSTWSBJQAV-UHFFFAOYSA-N 2-[4-[3-(azetidin-1-yl)propoxy]phenyl]-5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazole Chemical compound C1CCN1CCCOC(C=C1)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 QAXWPSTWSBJQAV-UHFFFAOYSA-N 0.000 claims 1
- QTUDHTVBEVUINQ-UHFFFAOYSA-N 2-[4-[4-(azepan-1-yl)butoxy]phenyl]-5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazole Chemical compound C=1C=C(C=2OC(CSCCOC=3C=CC=CC=3)=NN=2)C=CC=1OCCCCN1CCCCCC1 QTUDHTVBEVUINQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- COBUEFWOFPRGFJ-UHFFFAOYSA-N 3-[2-chloro-4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=C(Cl)C(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 COBUEFWOFPRGFJ-UHFFFAOYSA-N 0.000 claims 1
- OKLYBVQCRORIII-UHFFFAOYSA-N 3-[2-fluoro-4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=C(F)C(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 OKLYBVQCRORIII-UHFFFAOYSA-N 0.000 claims 1
- ANZRQBNWYZGMKV-UHFFFAOYSA-N 3-[4-[5-(1-benzofuran-2-ylmethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCC1=CC2=CC=CC=C2O1 ANZRQBNWYZGMKV-UHFFFAOYSA-N 0.000 claims 1
- FPKBHVDTIBYEMY-UHFFFAOYSA-N 3-[4-[5-(1-benzothiophen-2-ylmethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]-n,n-dimethylpropan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCC1=CC2=CC=CC=C2S1 FPKBHVDTIBYEMY-UHFFFAOYSA-N 0.000 claims 1
- GVTGIXBRCDJEMP-UHFFFAOYSA-N 4-(dimethylamino)-n-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]butanamide Chemical compound C1=CC(NC(=O)CCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 GVTGIXBRCDJEMP-UHFFFAOYSA-N 0.000 claims 1
- FBIFJMUDQSKIHP-UHFFFAOYSA-N 5-(2-phenoxyethylsulfanylmethyl)-3-[4-(2-pyrrolidin-1-ylethoxy)phenyl]-1,2,4-oxadiazole Chemical compound C=1C=CC=CC=1OCCSCC(ON=1)=NC=1C(C=C1)=CC=C1OCCN1CCCC1 FBIFJMUDQSKIHP-UHFFFAOYSA-N 0.000 claims 1
- ZXGSNWSAMSRHSI-UHFFFAOYSA-N 5-[4-[3-(azepan-1-yl)propoxy]phenyl]-2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazole Chemical compound C1CCCCCN1CCCOC(C=C1)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 ZXGSNWSAMSRHSI-UHFFFAOYSA-N 0.000 claims 1
- NWAQMYSNSILJPY-UHFFFAOYSA-N 5-[4-[3-(azocan-1-yl)propoxy]phenyl]-2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazole Chemical compound C1CCCCCCN1CCCOC(C=C1)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 NWAQMYSNSILJPY-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 206010003210 Arteriosclerosis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 208000002249 Diabetes Complications Diseases 0.000 claims 1
- 206010012655 Diabetic complications Diseases 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010012735 Diarrhoea Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000007882 Gastritis Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 208000035150 Hypercholesterolemia Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 206010022714 Intestinal ulcer Diseases 0.000 claims 1
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims 1
- 206010029279 Neurogenic bladder Diseases 0.000 claims 1
- 206010030216 Oesophagitis Diseases 0.000 claims 1
- 206010036774 Proctitis Diseases 0.000 claims 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 1
- 208000025844 Prostatic disease Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 208000007107 Stomach Ulcer Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046543 Urinary incontinence Diseases 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000011775 arteriosclerosis disease Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 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 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 238000013016 damping Methods 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 235000014632 disordered eating Nutrition 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002183 duodenal effect Effects 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 230000004406 elevated intraocular pressure Effects 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 208000028329 epileptic seizure Diseases 0.000 claims 1
- 208000006881 esophagitis Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 201000005917 gastric ulcer Diseases 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Chemical group CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 1
- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical group CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 claims 1
- 230000004899 motility Effects 0.000 claims 1
- MMJIXDHGKDUZJF-UHFFFAOYSA-N n',n'-dimethyl-n-[5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]pyridin-2-yl]ethane-1,2-diamine Chemical compound C1=NC(NCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 MMJIXDHGKDUZJF-UHFFFAOYSA-N 0.000 claims 1
- XEOIELQFSLHQJZ-UHFFFAOYSA-N n',n'-dimethyl-n-[5-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]pyridin-2-yl]propane-1,3-diamine Chemical compound C1=NC(NCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 XEOIELQFSLHQJZ-UHFFFAOYSA-N 0.000 claims 1
- KBTNQTFYAXJMKZ-UHFFFAOYSA-N n,n-diethyl-2-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenoxy]ethanamine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 KBTNQTFYAXJMKZ-UHFFFAOYSA-N 0.000 claims 1
- VXTKGOGTBCLSAB-UHFFFAOYSA-N n,n-diethyl-2-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]ethanamine Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 VXTKGOGTBCLSAB-UHFFFAOYSA-N 0.000 claims 1
- HLIOSKOFXIHUFK-UHFFFAOYSA-N n,n-diethyl-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(CC)CC)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 HLIOSKOFXIHUFK-UHFFFAOYSA-N 0.000 claims 1
- DWZAWOZHCNOQRC-UHFFFAOYSA-N n,n-diethyl-4-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]butan-1-amine Chemical compound C1=CC(OCCCCN(CC)CC)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 DWZAWOZHCNOQRC-UHFFFAOYSA-N 0.000 claims 1
- BNPVPHRMMYHKHY-UHFFFAOYSA-N n,n-dimethyl-2-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenoxy]ethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 BNPVPHRMMYHKHY-UHFFFAOYSA-N 0.000 claims 1
- KAAOIQOCROJXCG-UHFFFAOYSA-N n,n-dimethyl-2-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,2,4-oxadiazol-3-yl]phenoxy]ethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C1=NOC(CSCCOC=2C=CC=CC=2)=N1 KAAOIQOCROJXCG-UHFFFAOYSA-N 0.000 claims 1
- PXGLOVSGDGKFPN-UHFFFAOYSA-N n,n-dimethyl-2-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]ethanamine Chemical compound C1=CC(OCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 PXGLOVSGDGKFPN-UHFFFAOYSA-N 0.000 claims 1
- MKIOEAGNHIITAW-UHFFFAOYSA-N n,n-dimethyl-3-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-4-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C1=COC(CSCCOC=2C=CC=CC=2)=N1 MKIOEAGNHIITAW-UHFFFAOYSA-N 0.000 claims 1
- REYCIVSSPSMWAL-UHFFFAOYSA-N n,n-dimethyl-3-[4-[2-(2-phenoxyethylsulfanylmethyl)-1,3-oxazol-5-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=CN=C1CSCCOC1=CC=CC=C1 REYCIVSSPSMWAL-UHFFFAOYSA-N 0.000 claims 1
- ZIVRLTKFQIPZFH-UHFFFAOYSA-N n,n-dimethyl-3-[4-[4-(2-phenoxyethylsulfanylmethyl)-1,3-thiazol-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C1=NC(CSCCOC=2C=CC=CC=2)=CS1 ZIVRLTKFQIPZFH-UHFFFAOYSA-N 0.000 claims 1
- UKZSXSPOAKBENX-UHFFFAOYSA-N n,n-dimethyl-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 UKZSXSPOAKBENX-UHFFFAOYSA-N 0.000 claims 1
- MRACXWKOBWZONH-UHFFFAOYSA-N n,n-dimethyl-3-[4-[5-(2-phenoxyethylsulfanylmethyl)furan-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=CC=C1CSCCOC1=CC=CC=C1 MRACXWKOBWZONH-UHFFFAOYSA-N 0.000 claims 1
- ICIVPPMCLWBVRG-UHFFFAOYSA-N n,n-dimethyl-3-[4-[5-(naphthalen-2-ylmethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCN(C)C)=CC=C1C(O1)=NN=C1CSCC1=CC=C(C=CC=C2)C2=C1 ICIVPPMCLWBVRG-UHFFFAOYSA-N 0.000 claims 1
- AIHUKDALKXAWMW-UHFFFAOYSA-N n,n-dimethyl-4-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]butan-1-amine Chemical compound C1=CC(OCCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 AIHUKDALKXAWMW-UHFFFAOYSA-N 0.000 claims 1
- KCSONBMYUUWGLH-UHFFFAOYSA-N n,n-dimethyl-4-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]but-3-en-1-amine Chemical compound C1=CC(C=CCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 KCSONBMYUUWGLH-UHFFFAOYSA-N 0.000 claims 1
- QJDPVBMRMRETTJ-UHFFFAOYSA-N n,n-dimethyl-5-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]pent-4-en-1-amine Chemical compound C1=CC(C=CCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 QJDPVBMRMRETTJ-UHFFFAOYSA-N 0.000 claims 1
- OGFSDDSLKXJBLI-UHFFFAOYSA-N n,n-dimethyl-6-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenyl]hex-5-en-1-amine Chemical compound C1=CC(C=CCCCCN(C)C)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 OGFSDDSLKXJBLI-UHFFFAOYSA-N 0.000 claims 1
- GQXSIISFOPTWNZ-UHFFFAOYSA-N n-methyl-3-[4-[5-(2-phenoxyethylsulfanylmethyl)-1,3,4-oxadiazol-2-yl]phenoxy]propan-1-amine Chemical compound C1=CC(OCCCNC)=CC=C1C(O1)=NN=C1CSCCOC1=CC=CC=C1 GQXSIISFOPTWNZ-UHFFFAOYSA-N 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000036269 ulceration Effects 0.000 claims 1
- 230000002792 vascular Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000006694 eating habits Nutrition 0.000 description 1
- 239000003667 hormone antagonist Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229960001243 orlistat Drugs 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38035102P | 2002-05-13 | 2002-05-13 | |
| PCT/US2003/012123 WO2003097047A1 (en) | 2002-05-13 | 2003-05-06 | Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005529923A JP2005529923A (ja) | 2005-10-06 |
| JP2005529923A5 true JP2005529923A5 (enExample) | 2006-06-29 |
Family
ID=29549955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004505046A Pending JP2005529923A (ja) | 2002-05-13 | 2003-05-06 | 肥満および糖尿病の治療におけるメラニン凝集ホルモンアンタゴニストとして使用するための多環式化合物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7229987B2 (enExample) |
| EP (1) | EP1505968A1 (enExample) |
| JP (1) | JP2005529923A (enExample) |
| AU (1) | AU2003222648A1 (enExample) |
| CA (1) | CA2484233A1 (enExample) |
| WO (1) | WO2003097047A1 (enExample) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1450801A4 (en) | 2001-11-27 | 2010-10-27 | Merck Sharp & Dohme | 2-aminoquinoline CONNECTIONS |
| US7727998B2 (en) | 2003-02-10 | 2010-06-01 | Banyu Pharmaceutical Co., Ltd. | Melanin-concentrating hormone receptor antagonists containing piperidine derivatives as the active ingredient |
| CA2542220A1 (en) * | 2003-10-22 | 2005-05-06 | Eli Lilly And Company | Novel mch receptor antagonists |
| WO2005066132A1 (en) * | 2004-01-07 | 2005-07-21 | Astrazeneca Ab | Therapeutic agents i |
| US7550602B1 (en) * | 2004-01-14 | 2009-06-23 | Palatin Technologies, Inc. | Small molecule compositions for sexual dysfunction |
| US7241787B2 (en) | 2004-01-25 | 2007-07-10 | Sanofi-Aventis Deutschland Gmbh | Substituted N-cycloexylimidazolinones, process for their preparation and their use as medicaments |
| US7319108B2 (en) | 2004-01-25 | 2008-01-15 | Sanofi-Aventis Deutschland Gmbh | Aryl-substituted heterocycles, 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 |
| DE102004039789A1 (de) | 2004-08-16 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Arylsubstituierte polycyclische Amine, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| WO2007050087A1 (en) | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
| ATE528001T1 (de) | 2004-08-25 | 2011-10-15 | Ardea Biosciences Inc | S-triazolyl-alpha-mercaptoacetanilide als inhibitoren von hiv-umkehrtranskriptase |
| EP2939674A1 (en) * | 2004-10-13 | 2015-11-04 | PTC Therapeutics, Inc. | Compounds for nonsense suppression, and methods for their use |
| MX2007011105A (es) | 2005-03-10 | 2007-10-08 | Pfizer | Compuestos de n-sulfonilaminofeniletil-2-fenoxiacetamida sustituidos. |
| EP1866293A1 (en) | 2005-03-31 | 2007-12-19 | UCB Pharma, S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| EP1717235A3 (en) * | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| KR20080066938A (ko) * | 2005-10-07 | 2008-07-17 | 깃세이 야쿠힌 고교 가부시키가이샤 | 질소 함유 복소환 화합물 및 그것을 함유하는 의약 조성물 |
| 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 |
| JP2009526795A (ja) | 2006-02-15 | 2009-07-23 | サノフィ−アベンティス | 新規なアミノアルコール置換アリールジヒドロイソキノリノン、それらの製造方法及び薬剤としてそれらの使用 |
| US8115005B2 (en) | 2006-08-04 | 2012-02-14 | Decode Genetics Ehf. | Pyrazolylphenyl and pyrrolylphenyl inhibitors of LTA4H for treating inflammation |
| ES2393412T3 (es) * | 2006-09-21 | 2012-12-21 | Actelion Pharmaceuticals Ltd. | Derivados de fenilo y su uso como inmunomoduladores |
| RU2461558C2 (ru) | 2006-12-05 | 2012-09-20 | Янссен Фармацевтика Н.В. | Новые замещенные диазаспиропиридиноновые производные для применения в лечении мсн-1-опосредованных заболеваний |
| EP2079694B1 (en) | 2006-12-28 | 2017-03-01 | Rigel Pharmaceuticals, Inc. | N-substituted-heterocycloalkyloxybenzamide compounds and methods of use |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| KR101669432B1 (ko) * | 2007-08-27 | 2016-10-26 | 다트 뉴로사이언스 (케이만) 엘티디. | 치료적 이속사졸 화합물 |
| TWI360535B (en) | 2007-08-30 | 2012-03-21 | Univ Nat Sun Yat Sen | Sulfur-containing compound, method of preparation |
| NZ595035A (en) | 2007-11-27 | 2012-11-30 | Ardea Biosciences Inc | Substituted diazole and triazole compounds and compositions and methods of use |
| TWI490214B (zh) * | 2008-05-30 | 2015-07-01 | 艾德克 上野股份有限公司 | 苯或噻吩衍生物及該等作為ｖａｐ－１抑制劑之用途 |
| WO2010068775A2 (en) | 2008-12-11 | 2010-06-17 | Amira Pharmaceuticals, Inc. | Alkyne antagonists of lysophosphatidic acid receptors |
| GB2466121B (en) | 2008-12-15 | 2010-12-08 | Amira Pharmaceuticals Inc | Antagonists of lysophosphatidic acid receptors |
| AR075402A1 (es) | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Derivados heterociclicos oxigenados y/o nitrogenados de tetrahidronaftaleno, medicamentos que los contienen y uso de los mismos en el tratamiento de trastornos metabolicos, tales como obesidad,entre otros. |
| AR075401A1 (es) | 2009-02-13 | 2011-03-30 | Sanofi Aventis | Indanos sustituidos, procesos para su preparacion y uso de los mismos como un medicamento |
| US8785468B2 (en) | 2009-02-13 | 2014-07-22 | Amgen Inc. | Phenylalanine amide derivatives useful for treating insulin-related diseases and conditions |
| GB2470833B (en) | 2009-06-03 | 2011-06-01 | Amira Pharmaceuticals Inc | Polycyclic antagonists of lysophosphatidic acid receptors |
| EP2462128B1 (en) | 2009-08-04 | 2016-09-21 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
| GB2474748B (en) | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| GB2474120B (en) | 2009-10-01 | 2011-12-21 | Amira Pharmaceuticals Inc | Compounds as Lysophosphatidic acid receptor antagonists |
| NZ600320A (en) * | 2009-11-17 | 2013-10-25 | Merial Ltd | Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| US9133123B2 (en) | 2010-04-23 | 2015-09-15 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| KR101250990B1 (ko) * | 2010-08-20 | 2013-04-04 | 한국화학연구원 | 신규 1,2,4-옥사다이아졸 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 유효성분으로 함유하는 ｍｃｈ 관련 질환의 예방 또는 치료용 약학적 조성물 |
| WO2012081563A1 (ja) * | 2010-12-14 | 2012-06-21 | 塩野義製薬株式会社 | 血管内皮リパーゼ阻害活性を有するベンゾチアゾールおよびアザベンゾチアゾール誘導体 |
| EP2694496A1 (en) | 2011-04-05 | 2014-02-12 | Amira Pharmaceuticals, Inc. | 3- or 5 - bi phenyl - 4 - ylisoxazole - based compounds useful for the treatment of fibrosis, pain, cancer and respiratory, allergic, nervous system or cardiovascular disorders |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| CN105492444B (zh) | 2013-07-02 | 2018-09-07 | 百时美施贵宝公司 | 作为rock抑制剂的三环吡啶-甲酰胺衍生物 |
| EP3016950B1 (en) | 2013-07-02 | 2017-06-07 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| CN106266963A (zh) * | 2016-08-31 | 2017-01-04 | 范佐刚 | 一种治疗脂肪肝及高血脂的中药组合物 |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| KR102847693B1 (ko) * | 2019-12-27 | 2025-08-18 | 서울대학교산학협력단 | 옥사디아졸 유도체를 포함하는 비만의 예방 또는 치료용 조성물 |
| WO2025176750A1 (en) * | 2024-02-23 | 2025-08-28 | Heinrich-Heine-Universität Düsseldorf | Dual targeting in a new class of active ingredients |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| AU5227999A (en) | 1998-07-27 | 2000-02-21 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| CN1444573A (zh) | 2000-07-31 | 2003-09-24 | 史密丝克莱恩比彻姆有限公司 | 甲酰胺化合物及其作为人11cby受体拮抗剂的用途 |
| EP1326861A1 (en) * | 2000-10-20 | 2003-07-16 | Pfizer Products Inc. | Alpha-aryl ethanolamines and their use as beta-3 adrenergic receptor agonists |
-
2003
- 2003-05-06 WO PCT/US2003/012123 patent/WO2003097047A1/en not_active Ceased
- 2003-05-06 EP EP03719843A patent/EP1505968A1/en not_active Withdrawn
- 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 US US10/512,986 patent/US7229987B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2005529923A5 (enExample) | ||
| CA2660201C (en) | Organic compounds | |
| JP2006509801A5 (enExample) | ||
| JP4958784B2 (ja) | ステアロイル−ＣｏＡデサチュラーゼ酵素によって媒介される疾患の処置のための複素環誘導体 | |
| AU2007318092B2 (en) | Calcium receptor modulating agents | |
| AU2010299114A1 (en) | Substituted amide compound | |
| RU2008116581A (ru) | Сульфонамидные производные, как активаторы гликокиназы, применимые для лечения диабета типа 2 | |
| KR20130084328A (ko) | 유기 화합물 | |
| JP2005529923A (ja) | 肥満および糖尿病の治療におけるメラニン凝集ホルモンアンタゴニストとして使用するための多環式化合物 | |
| RU2005117789A (ru) | Производные 4,5-диарилтиазола в качестве лигандов св-1 | |
| JP2010513283A5 (enExample) | ||
| JP2004509162A (ja) | アミノアルコール誘導体 | |
| CA2294293A1 (en) | Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents | |
| JP5782430B2 (ja) | 新規アミド誘導体およびその医薬としての用途 | |
| WO2007143597A9 (en) | Organic compounds | |
| KR20030016396A (ko) | 베타３ 아드레날린 효현제 | |
| AU2010362639A1 (en) | Processes for the preparation of Rivaroxaban and intermediates thereof | |
| JP2007510629A5 (enExample) | ||
| JP2007510629A (ja) | 新規ｍｃｈ受容体アンタゴニスト | |
| EP2483264A1 (en) | Pyrazole derivatives which modulate stearoyl-coa desaturase | |
| JP2009514899A5 (enExample) | ||
| WO2012038904A1 (fr) | Derives de nicotinamide, leur preparation et leur application en therapeutique | |
| KR20120047960A (ko) | 글루코키나아제(ｇｋ) 활성화제로서 치환된 벤즈아미드 유도체 | |
| RU2574409C2 (ru) | Новые амидные производные и их использование в качестве лекарственного средства | |
| AU2011246095B8 (en) | Novel amide derivative and use thereof as medicine |