JP2003528810A5 - - Google Patents
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- JP2003528810A5 JP2003528810A5 JP2001515309A JP2001515309A JP2003528810A5 JP 2003528810 A5 JP2003528810 A5 JP 2003528810A5 JP 2001515309 A JP2001515309 A JP 2001515309A JP 2001515309 A JP2001515309 A JP 2001515309A JP 2003528810 A5 JP2003528810 A5 JP 2003528810A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- tetrahydro
- methoxy
- pyrimidine
- benzylsulfanyl
- 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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- 238000000034 method Methods 0.000 description 95
- 125000000217 alkyl group Chemical group 0.000 description 59
- 150000001875 compounds Chemical class 0.000 description 52
- 229910052739 hydrogen Inorganic materials 0.000 description 45
- 239000001257 hydrogen Substances 0.000 description 45
- 102100023724 Melanocortin receptor 4 Human genes 0.000 description 37
- 101710085775 Melanocortin receptor 4 Proteins 0.000 description 37
- 150000002431 hydrogen Chemical group 0.000 description 37
- 229910052736 halogen Inorganic materials 0.000 description 27
- 150000002367 halogens Chemical class 0.000 description 27
- -1 benzocarbonyl Chemical group 0.000 description 26
- 125000003342 alkenyl group Chemical group 0.000 description 25
- 125000003118 aryl group Chemical group 0.000 description 24
- 125000002252 acyl group Chemical group 0.000 description 21
- 125000004093 cyano group Chemical group *C#N 0.000 description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 19
- 125000000304 alkynyl group Chemical group 0.000 description 18
- 125000003545 alkoxy group Chemical group 0.000 description 14
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 241000124008 Mammalia Species 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 150000001721 carbon Chemical class 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- XWJXXXQFFDDHEK-UHFFFAOYSA-N 1-[[2-[(2-methoxynaphthalen-1-yl)methylsulfanyl]phenyl]methyl]pyrrolidin-3-amine Chemical compound COC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1CN1CCC(N)C1 XWJXXXQFFDDHEK-UHFFFAOYSA-N 0.000 description 4
- KWBJMDZAPHKDFB-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]piperidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CN1CCCCC1 KWBJMDZAPHKDFB-UHFFFAOYSA-N 0.000 description 4
- DYASGHCSJCHRAM-UHFFFAOYSA-N 1-[[3-fluoro-2-(2-naphthalen-1-ylethyl)phenyl]methyl]piperazine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC=1C(F)=CC=CC=1CN1CCNCC1 DYASGHCSJCHRAM-UHFFFAOYSA-N 0.000 description 4
- QRDFGAHATXGIBR-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-nitrophenyl)methoxy]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C([N+]([O-])=O)C=C1COC1=CC=CC=C1C1=NCCCN1 QRDFGAHATXGIBR-UHFFFAOYSA-N 0.000 description 4
- GLGIWLZTKPEBKS-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]-6-ethyl-1,4,5,6-tetrahydropyrimidine Chemical compound N1C(CC)CCN=C1C1=CC=CC=C1SCC1=CC(Br)=CC=C1OC GLGIWLZTKPEBKS-UHFFFAOYSA-N 0.000 description 4
- HMGGFEHSQUFZTI-UHFFFAOYSA-N 2-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methoxymethyl]pyrrolidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1COCC1NCCC1 HMGGFEHSQUFZTI-UHFFFAOYSA-N 0.000 description 4
- VBUILYKEAPKRKE-UHFFFAOYSA-N 2-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CC1=NCCCN1 VBUILYKEAPKRKE-UHFFFAOYSA-N 0.000 description 4
- OQQKRORCCALBOF-UHFFFAOYSA-N 3-(2-methylpiperidin-1-yl)-n-[[2-(2-naphthalen-1-ylethyl)phenyl]methyl]propan-1-amine Chemical compound CC1CCCCN1CCCNCC1=CC=CC=C1CCC1=CC=CC2=CC=CC=C12 OQQKRORCCALBOF-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- ZCBPTFJSXQSXMK-UHFFFAOYSA-N [1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]piperidin-2-yl]methanol Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1CN1C(CO)CCCC1 ZCBPTFJSXQSXMK-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- XYZDDOTYDXXWPM-UHFFFAOYSA-N n-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1SCC1=CC(Br)=CC=C1OC XYZDDOTYDXXWPM-UHFFFAOYSA-N 0.000 description 4
- 229910014033 C-OH Inorganic materials 0.000 description 3
- 229910014570 C—OH Inorganic materials 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052757 nitrogen Chemical group 0.000 description 3
- 208000016261 weight loss Diseases 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- DHMLFLUIIOQLOJ-UHFFFAOYSA-N 1,3-di(piperidin-1-yl)propan-2-yl n-(2-hexoxyphenyl)carbamate Chemical compound CCCCCCOC1=CC=CC=C1NC(=O)OC(CN1CCCCC1)CN1CCCCC1 DHMLFLUIIOQLOJ-UHFFFAOYSA-N 0.000 description 2
- RGFBAGOHQXOXRY-UHFFFAOYSA-N 1,3-di(piperidin-1-yl)propan-2-yl n-[2-(naphthalen-1-ylmethylsulfanyl)phenyl]carbamate Chemical compound C=1C=CC=C(SCC=2C3=CC=CC=C3C=CC=2)C=1NC(=O)OC(CN1CCCCC1)CN1CCCCC1 RGFBAGOHQXOXRY-UHFFFAOYSA-N 0.000 description 2
- GAZFMSFTOKVZQL-UHFFFAOYSA-N 1-(1-ethylpyrrolidin-2-yl)-n-(naphthalen-1-ylmethyl)-n-(naphthalen-2-ylmethyl)methanamine Chemical compound CCN1CCCC1CN(CC=1C2=CC=CC=C2C=CC=1)CC1=CC=C(C=CC=C2)C2=C1 GAZFMSFTOKVZQL-UHFFFAOYSA-N 0.000 description 2
- SHZPSAKOOSXLBB-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)-3-(2-phenylethyl)-1-(2-piperidin-1-ylethyl)thiourea Chemical compound C1CCCCN1CCN(CC=1C2=CC=CC=C2C=CC=1)C(=S)NCCC1=CC=CC=C1 SHZPSAKOOSXLBB-UHFFFAOYSA-N 0.000 description 2
- GIHQQJIHBAIGSO-UHFFFAOYSA-N 1-[2-(2-naphthalen-1-ylethyl)phenyl]ethane-1,2-diamine Chemical compound NCC(N)C1=CC=CC=C1CCC1=CC=CC2=CC=CC=C12 GIHQQJIHBAIGSO-UHFFFAOYSA-N 0.000 description 2
- ATZDPWOFOKHOFM-UHFFFAOYSA-N 1-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]-n,n-dimethylmethanamine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CN(C)C ATZDPWOFOKHOFM-UHFFFAOYSA-N 0.000 description 2
- HIZHZFLGIHIACW-UHFFFAOYSA-N 1-[2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]phenyl]-5,6-dihydro-4h-pyrimidin-1-yl]ethanone Chemical compound CC(=O)N1CCCN=C1C1=CC=CC=C1SCC1=C(F)C=CC=C1Cl HIZHZFLGIHIACW-UHFFFAOYSA-N 0.000 description 2
- OWTGZNSAINYLEJ-UHFFFAOYSA-N 1-[2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]-5,6-dihydro-4h-pyrimidin-1-yl]-2-phenylethanone Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NCCCN1C(=O)CC1=CC=CC=C1 OWTGZNSAINYLEJ-UHFFFAOYSA-N 0.000 description 2
- OJJQCZAOHMHZLQ-UHFFFAOYSA-N 1-[2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]-5,6-dihydro-4h-pyrimidin-1-yl]-3-methylbutan-1-one Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NCCCN1C(=O)CC(C)C OJJQCZAOHMHZLQ-UHFFFAOYSA-N 0.000 description 2
- QCIYTUBLCHCWKF-UHFFFAOYSA-N 1-[3-[(5-bromo-2-methoxyphenyl)methylsulfanyl]pyrazin-2-yl]pyrrolidin-3-amine Chemical compound COC1=CC=C(Br)C=C1CSC1=NC=CN=C1N1CC(N)CC1 QCIYTUBLCHCWKF-UHFFFAOYSA-N 0.000 description 2
- DWVZXZWVOVLLNB-UHFFFAOYSA-N 1-[3-[(5-bromo-2-methoxyphenyl)methylsulfanyl]quinoxalin-2-yl]pyrrolidin-3-amine Chemical compound COC1=CC=C(Br)C=C1CSC1=NC2=CC=CC=C2N=C1N1CC(N)CC1 DWVZXZWVOVLLNB-UHFFFAOYSA-N 0.000 description 2
- RCAPUOMCNFOSTP-UHFFFAOYSA-N 1-[4-methoxy-3-[[2-(1,4,5,6-tetrahydropyrimidin-2-yl)phenyl]sulfanylmethyl]phenyl]ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1CSC1=CC=CC=C1C1=NCCCN1 RCAPUOMCNFOSTP-UHFFFAOYSA-N 0.000 description 2
- UPUQOEPOWHSGPH-UHFFFAOYSA-N 1-[[2-(2-naphthalen-1-ylethyl)phenyl]methyl]piperazine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC1=CC=CC=C1CN1CCNCC1 UPUQOEPOWHSGPH-UHFFFAOYSA-N 0.000 description 2
- UWBWBCKISPTABJ-UHFFFAOYSA-N 1-[[2-(2-naphthalen-1-ylethyl)phenyl]methyl]pyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1=CC=CC=C1CCC1=CC=CC2=CC=CC=C12 UWBWBCKISPTABJ-UHFFFAOYSA-N 0.000 description 2
- BCQNKADIWADQCL-UHFFFAOYSA-N 1-[[2-(naphthalen-1-ylsulfanylmethyl)phenyl]methyl]piperazine Chemical compound C=1C=CC2=CC=CC=C2C=1SCC1=CC=CC=C1CN1CCNCC1 BCQNKADIWADQCL-UHFFFAOYSA-N 0.000 description 2
- WODPAVGRLDMTGA-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]-2-(methoxymethyl)pyrrolidine Chemical compound COCC1CCCN1CC1=CC=CC(Cl)=C1SCC1=CC(Br)=CC=C1OC WODPAVGRLDMTGA-UHFFFAOYSA-N 0.000 description 2
- JMUUYBCFUZIXOY-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]azetidine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1CN1CCC1 JMUUYBCFUZIXOY-UHFFFAOYSA-N 0.000 description 2
- NDPLIKQZAAIEAD-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]piperazine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1CN1CCNCC1 NDPLIKQZAAIEAD-UHFFFAOYSA-N 0.000 description 2
- AWVJYNDPVRJZQI-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]pyrrolidin-3-amine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1CN1CC(N)CC1 AWVJYNDPVRJZQI-UHFFFAOYSA-N 0.000 description 2
- IFCDMRMMCXRJEV-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]methyl]pyrrolidin-3-ol Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1CN1CC(O)CC1 IFCDMRMMCXRJEV-UHFFFAOYSA-N 0.000 description 2
- IILSKIZWMSVWAI-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]piperazine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CN1CCNCC1 IILSKIZWMSVWAI-UHFFFAOYSA-N 0.000 description 2
- IKYPYTQRZDPPLI-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]pyrrolidin-3-amine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CN1CC(N)CC1 IKYPYTQRZDPPLI-UHFFFAOYSA-N 0.000 description 2
- WOAQXXVCKUXXIM-UHFFFAOYSA-N 1-[[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]methyl]pyrrolidin-3-ol Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1CN1CC(O)CC1 WOAQXXVCKUXXIM-UHFFFAOYSA-N 0.000 description 2
- JLYBRUBFGATRBM-UHFFFAOYSA-N 1-[[3-chloro-2-(naphthalen-1-ylsulfanylmethyl)phenyl]methyl]piperazine Chemical compound C=1C=CC2=CC=CC=C2C=1SCC=1C(Cl)=CC=CC=1CN1CCNCC1 JLYBRUBFGATRBM-UHFFFAOYSA-N 0.000 description 2
- HVDWCFNXMDSFSR-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-[2-(naphthalen-1-ylmethylsulfanyl)phenyl]carbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=C1SCC1=CC=CC2=CC=CC=C12 HVDWCFNXMDSFSR-UHFFFAOYSA-N 0.000 description 2
- WSXOKTKQMKXUKK-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-yl n-[2-[(2-methylnaphthalen-1-yl)methylsulfanyl]phenyl]carbamate Chemical compound C1N(CC2)CCC2C1OC(=O)NC1=CC=CC=C1SCC1=C2C=CC=CC2=CC=C1C WSXOKTKQMKXUKK-UHFFFAOYSA-N 0.000 description 2
- JSSURDODLIXQJB-UHFFFAOYSA-N 1-methyl-2-[2-(naphthalen-1-ylmethylsulfanyl)phenyl]-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C1=CC=CC=C1SCC1=CC=CC2=CC=CC=C12 JSSURDODLIXQJB-UHFFFAOYSA-N 0.000 description 2
- WBODHADKZJNENR-UHFFFAOYSA-N 1-phenyl-3-piperazin-1-yl-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile Chemical compound N#CC1=C2CCCCC2=C(C=2C=CC=CC=2)N=C1N1CCNCC1 WBODHADKZJNENR-UHFFFAOYSA-N 0.000 description 2
- LPFIAUCSSYOSJI-UHFFFAOYSA-N 2-(2-benzhydrylsulfanylphenyl)-1,4,5,6-tetrahydropyrimidine Chemical compound C1CCNC(C=2C(=CC=CC=2)SC(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 LPFIAUCSSYOSJI-UHFFFAOYSA-N 0.000 description 2
- SYACJNJDWOFLPR-UHFFFAOYSA-N 2-(2-benzylsulfanylphenyl)-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=CC=1CSC1=CC=CC=C1C1=NCCCN1 SYACJNJDWOFLPR-UHFFFAOYSA-N 0.000 description 2
- VBGDTCBHSKWUHT-UHFFFAOYSA-N 2-(2-benzylsulfanylphenyl)-4,5-dihydro-1h-imidazole Chemical compound C=1C=CC=CC=1CSC1=CC=CC=C1C1=NCCN1 VBGDTCBHSKWUHT-UHFFFAOYSA-N 0.000 description 2
- ORVKGXPJZJAEEK-UHFFFAOYSA-N 2-(3-aminopropylamino)-6-[(5-bromo-2-methoxyphenyl)methylsulfanyl]benzonitrile Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC(NCCCN)=C1C#N ORVKGXPJZJAEEK-UHFFFAOYSA-N 0.000 description 2
- DJWODOBNDWFNTI-UHFFFAOYSA-N 2-(dimethylamino)ethyl n-[2-(naphthalen-1-ylmethylsulfanyl)phenyl]carbamate Chemical compound CN(C)CCOC(=O)NC1=CC=CC=C1SCC1=CC=CC2=CC=CC=C12 DJWODOBNDWFNTI-UHFFFAOYSA-N 0.000 description 2
- BPGGBTUYXDFQIR-UHFFFAOYSA-N 2-(naphthalen-1-ylmethylsulfanyl)-3-(1,4,5,6-tetrahydropyrimidin-2-yl)aniline Chemical compound C=1C=CC2=CC=CC=C2C=1CSC=1C(N)=CC=CC=1C1=NCCCN1 BPGGBTUYXDFQIR-UHFFFAOYSA-N 0.000 description 2
- KGUYGXACOPYBBV-UHFFFAOYSA-N 2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-(1,4,5,6-tetrahydropyrimidin-2-yl)pyrazine Chemical compound COC1=CC=C(Br)C=C1CSC1=NC=CN=C1C1=NCCCN1 KGUYGXACOPYBBV-UHFFFAOYSA-N 0.000 description 2
- SVPBPRSLWASWKI-UHFFFAOYSA-N 2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-piperazin-1-yl-6,7-dihydroquinoxaline Chemical compound COC1=CC=C(Br)C=C1CSC1=NC2=CCCC=C2N=C1N1CCNCC1 SVPBPRSLWASWKI-UHFFFAOYSA-N 0.000 description 2
- SCCAFPIBEOBGTQ-UHFFFAOYSA-N 2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]benzenecarboximidamide Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1C(N)=N SCCAFPIBEOBGTQ-UHFFFAOYSA-N 0.000 description 2
- VWLSDJQSNWMCNW-UHFFFAOYSA-N 2-[1-(2-naphthalen-1-ylethyl)pyrrol-2-yl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCN1C=CC=C1C1=NCCCN1 VWLSDJQSNWMCNW-UHFFFAOYSA-N 0.000 description 2
- XOTXXSNBMHVICF-UHFFFAOYSA-N 2-[2-(1-benzothiophen-3-ylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1SC2=CC=CC=C2C=1CSC1=CC=CC=C1C1=NCCCN1 XOTXXSNBMHVICF-UHFFFAOYSA-N 0.000 description 2
- DLZFOGIKAJESJI-UHFFFAOYSA-N 2-[2-(1-naphthalen-1-ylethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)SC1=CC=CC=C1C1=NCCCN1 DLZFOGIKAJESJI-UHFFFAOYSA-N 0.000 description 2
- FWPVLIBLPJCPKP-UHFFFAOYSA-N 2-[2-(2,3-dihydro-1,4-benzodioxin-5-ylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=2OCCOC=2C=1CSC1=CC=CC=C1C1=NCCCN1 FWPVLIBLPJCPKP-UHFFFAOYSA-N 0.000 description 2
- ACJPYKJBCKVDIV-UHFFFAOYSA-N 2-[2-(2-naphthalen-1-ylethyl)-3-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC=1C(C(F)(F)F)=CC=CC=1C1=NCCCN1 ACJPYKJBCKVDIV-UHFFFAOYSA-N 0.000 description 2
- GPPWPYMVKYICCM-UHFFFAOYSA-N 2-[2-(2-naphthalen-1-ylethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC1=CC=CC=C1C1=NCCCN1 GPPWPYMVKYICCM-UHFFFAOYSA-N 0.000 description 2
- RTLGWGUKVAYFGQ-UHFFFAOYSA-N 2-[2-(2-naphthalen-1-ylethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC=C1CCC1=CC=CC2=CC=CC=C12 RTLGWGUKVAYFGQ-UHFFFAOYSA-N 0.000 description 2
- HQKSAFODQJVAMY-UHFFFAOYSA-N 2-[2-(9h-fluoren-9-ylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C1CCNC(C=2C(=CC=CC=2)SC2C3=CC=CC=C3C3=CC=CC=C32)=N1 HQKSAFODQJVAMY-UHFFFAOYSA-N 0.000 description 2
- HLXFXORVYDASPB-UHFFFAOYSA-N 2-[2-(cyclohexylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C1CCCCC1CSC1=CC=CC=C1C1=NCCCN1 HLXFXORVYDASPB-UHFFFAOYSA-N 0.000 description 2
- QDZMJIFWBKCDIU-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylmethoxy)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1COC1=CC=CC=C1C1=NCCCN1 QDZMJIFWBKCDIU-UHFFFAOYSA-N 0.000 description 2
- WUXIBNPXDCPMEH-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CSC1=CC=CC=C1C1=NCCCN1 WUXIBNPXDCPMEH-UHFFFAOYSA-N 0.000 description 2
- UWVOBSJHFFRYJU-UHFFFAOYSA-N 2-[2-(naphthalen-1-yloxymethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1=CC=CC=C1C1=NCCCN1 UWVOBSJHFFRYJU-UHFFFAOYSA-N 0.000 description 2
- FIZAQPWFWADZQW-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylsulfanylmethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1SCC1=CC=CC=C1C1=NCCCN1 FIZAQPWFWADZQW-UHFFFAOYSA-N 0.000 description 2
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| JPS63253073A (ja) * | 1987-04-08 | 1988-10-20 | Taisho Pharmaceut Co Ltd | ２−フエニルベンズイミダゾ−ル誘導体 |
| ZA923283B (en) * | 1991-05-29 | 1993-01-27 | Akzo Nv | Phenoxyphenyl derivatives |
| US5731408A (en) * | 1995-04-10 | 1998-03-24 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Peptides having potent antagonist and agonist bioactivities at melanocortin receptors |
| JPH09176871A (ja) * | 1995-12-25 | 1997-07-08 | Tamura Kaken Kk | 水溶性プリフラックス、プリント回路基板及びプリント回路基板の金属の表面処理方法 |
| US5932779A (en) * | 1996-06-10 | 1999-08-03 | Millennium Pharmaceuticals, Inc. | Screening methods for compounds useful in the regulation of body weight |
| YU52199A (sh) * | 1997-04-15 | 2003-02-28 | Csir Corporate Building | Farmaceutske kompozicije za suzbijanje apetita |
| ZA9811672B (en) * | 1997-12-19 | 2000-06-19 | Lilly Co Eli | Hypoglycemic imidazoline compounds. |
| JP2002517444A (ja) * | 1998-06-11 | 2002-06-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作動薬としてのスピロピペリジン誘導体 |
-
2000
- 2000-08-04 JP JP2001515309A patent/JP2003528810A/ja active Pending
- 2000-08-04 CA CA002381008A patent/CA2381008A1/en not_active Abandoned
- 2000-08-04 WO PCT/US2000/021327 patent/WO2001010842A2/en not_active Ceased
- 2000-08-04 BR BR0012984-4A patent/BR0012984A/pt not_active Application Discontinuation
- 2000-08-04 MX MXPA02001160A patent/MXPA02001160A/es active IP Right Grant
- 2000-08-04 EP EP00953837A patent/EP1204645A2/en not_active Withdrawn
- 2000-08-04 AU AU66216/00A patent/AU6621600A/en not_active Abandoned
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