CA2381008A1 - Melanocortin-4 receptor binding compounds and methods of use thereof - Google Patents

Info

Publication number

CA2381008A1

CA2381008A1 CA002381008A CA2381008A CA2381008A1 CA 2381008 A1 CA2381008 A1 CA 2381008A1 CA 002381008 A CA002381008 A CA 002381008A CA 2381008 A CA2381008 A CA 2381008A CA 2381008 A1 CA2381008 A1 CA 2381008A1

Authority

CA

Canada

Prior art keywords

phenyl

tetrahydro

methoxy

pyrimidine

benzylsulfanyl

Prior art date

1999-08-04

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 423
• 238000000034 method Methods 0.000 title claims abstract description 213
• 230000027455 binding Effects 0.000 title claims abstract description 181
• 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 title description 246
• 102000001796 Melanocortin 4 receptors Human genes 0.000 title 1
• 102100023724 Melanocortin receptor 4 Human genes 0.000 claims abstract description 99
• 230000004580 weight loss Effects 0.000 claims abstract description 15
• 101710085775 Melanocortin receptor 4 Proteins 0.000 claims abstract 97
• -1 amino, amidino, guanidino Chemical group 0.000 claims description 319
• 125000000217 alkyl group Chemical group 0.000 claims description 257
• 125000003118 aryl group Chemical group 0.000 claims description 143
• 125000003342 alkenyl group Chemical group 0.000 claims description 121
• 125000000623 heterocyclic group Chemical group 0.000 claims description 115
• 125000000304 alkynyl group Chemical group 0.000 claims description 108
• 229910052736 halogen Inorganic materials 0.000 claims description 97
• 150000002367 halogens Chemical class 0.000 claims description 97
• 229910052739 hydrogen Inorganic materials 0.000 claims description 95
• 239000001257 hydrogen Substances 0.000 claims description 94
• 125000003545 alkoxy group Chemical group 0.000 claims description 92
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 83
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 77
• 229910052799 carbon Inorganic materials 0.000 claims description 71
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 60
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 53
• 241000124008 Mammalia Species 0.000 claims description 51
• 150000001721 carbon Chemical group 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 50
• 229910052717 sulfur Inorganic materials 0.000 claims description 50
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 45
• 239000008194 pharmaceutical composition Substances 0.000 claims description 45
• 229910052760 oxygen Inorganic materials 0.000 claims description 44
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 43
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 43
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
• 125000002252 acyl group Chemical group 0.000 claims description 42
• 125000001624 naphthyl group Chemical group 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000004122 cyclic group Chemical group 0.000 claims description 38
• 229910052757 nitrogen Inorganic materials 0.000 claims description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
• 239000001301 oxygen Substances 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 31
• 239000000460 chlorine Substances 0.000 claims description 31
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
• 229910052801 chlorine Inorganic materials 0.000 claims description 30
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 30
• 239000011593 sulfur Chemical group 0.000 claims description 30
• 229910052731 fluorine Inorganic materials 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• 239000011737 fluorine Substances 0.000 claims description 28
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 25
• 238000006467 substitution reaction Methods 0.000 claims description 25
• 150000005347 biaryls Chemical group 0.000 claims description 24
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 150000003568 thioethers Chemical class 0.000 claims description 19
• 125000004429 atom Chemical group 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 150000003573 thiols Chemical class 0.000 claims description 18
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 239000003937 drug carrier Substances 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
• SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000005647 linker group Chemical group 0.000 claims description 14
• 208000016261 weight loss Diseases 0.000 claims description 14
• 206010006895 Cachexia Diseases 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 13
• 229910014033 C-OH Inorganic materials 0.000 claims description 12
• 229910014570 C—OH Inorganic materials 0.000 claims description 12
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• 125000002837 carbocyclic group Chemical group 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• IIXSESNTPZDVOB-UHFFFAOYSA-N 2-[2-[(2,6-difluorophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound FC1=CC=CC(F)=C1CSC1=CC=CC=C1C1=NCCCN1 IIXSESNTPZDVOB-UHFFFAOYSA-N 0.000 claims description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
• 125000004434 sulfur atom Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 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 claims description 8
• 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 claims description 8
• 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 claims description 8
• CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 claims description 8
• 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 claims description 8
• 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 claims description 8
• 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 claims description 8
• 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 claims description 8
• 239000000556 agonist Substances 0.000 claims description 8
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• 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 claims description 8
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 8
• 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 claims description 7
• 239000005557 antagonist Substances 0.000 claims description 7
• 230000019612 pigmentation Effects 0.000 claims description 7
• 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 claims description 6
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
• JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 claims description 6
• MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims description 5
• ZACLFWISXHXZSS-UHFFFAOYSA-N 1-(6-bromo-2-chloroquinolin-4-yl)-3-[2-(diethylamino)ethyl]urea Chemical compound C1=C(Br)C=C2C(NC(=O)NCCN(CC)CC)=CC(Cl)=NC2=C1 ZACLFWISXHXZSS-UHFFFAOYSA-N 0.000 claims description 5
• BNMSJUIMZULLAS-UHFFFAOYSA-N 1-[5-(trifluoromethyl)pyridin-2-yl]piperazine Chemical compound N1=CC(C(F)(F)F)=CC=C1N1CCNCC1 BNMSJUIMZULLAS-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 5
• 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 claims description 5
• WBJVPAABGFBMJQ-UHFFFAOYSA-N 2-piperazin-1-yl-4-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC=NC(N2CCNCC2)=N1 WBJVPAABGFBMJQ-UHFFFAOYSA-N 0.000 claims description 5
• QLTXFTSBONWMPM-UHFFFAOYSA-N 4,6-dimethyl-2-piperazin-1-ylpyrimidine Chemical compound CC1=CC(C)=NC(N2CCNCC2)=N1 QLTXFTSBONWMPM-UHFFFAOYSA-N 0.000 claims description 5
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 5
• 229940126661 MC4 antagonist Drugs 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 5
• 235000010290 biphenyl Nutrition 0.000 claims description 5
• 239000004305 biphenyl Substances 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• ZXTWLUSWTSOFIV-UHFFFAOYSA-N methyl 6-piperazin-1-yl-7-(trifluoromethyl)thieno[3,2-b]pyridine-3-carboxylate Chemical compound C=1N=C2C(C(=O)OC)=CSC2=C(C(F)(F)F)C=1N1CCNCC1 ZXTWLUSWTSOFIV-UHFFFAOYSA-N 0.000 claims description 5
• GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 claims description 5
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
• 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 claims description 4
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• 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 claims description 4
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• 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 claims description 4
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• 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 claims description 4
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• 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 claims description 4
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• 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 claims description 4
• 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 claims description 4
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• YQXGBUCFRQYHMD-UHFFFAOYSA-N 2-[2-[(3-methoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 YQXGBUCFRQYHMD-UHFFFAOYSA-N 0.000 claims description 4
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• KWBUUMUFWHBVGS-UHFFFAOYSA-N 2-[2-[(4-fluorophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C1=CC(F)=CC=C1CSC1=CC=CC=C1C1=NCCCN1 KWBUUMUFWHBVGS-UHFFFAOYSA-N 0.000 claims description 4
• AWWMCYRTRDYSLP-UHFFFAOYSA-N 2-[2-[(4-methylnaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C12=CC=CC=C2C(C)=CC=C1CSC1=CC=CC=C1C1=NCCCN1 AWWMCYRTRDYSLP-UHFFFAOYSA-N 0.000 claims description 4
• DRCKIXIPSQZHTF-UHFFFAOYSA-N 2-[2-[(4-phenylmethoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1CSC1=CC=CC=C1C1=NCCCN1 DRCKIXIPSQZHTF-UHFFFAOYSA-N 0.000 claims description 4
• GPSOQGAPPIJCEG-UHFFFAOYSA-N 2-[2-[(5-bromo-2-ethoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CCOC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NCCCN1 GPSOQGAPPIJCEG-UHFFFAOYSA-N 0.000 claims description 4
• PXBUAHNXIUFNNY-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methoxy]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1COC1=CC=CC=C1C1=NCCCN1 PXBUAHNXIUFNNY-UHFFFAOYSA-N 0.000 claims description 4
• CPJWCFKQCQUQLI-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methoxymethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1COCC1=CC=CC=C1C1=NCCCN1 CPJWCFKQCQUQLI-UHFFFAOYSA-N 0.000 claims description 4
• RGMPFJUALNCLIZ-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3,4-difluorophenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(F)C(F)=CC=C1C1=NCCCN1 RGMPFJUALNCLIZ-UHFFFAOYSA-N 0.000 claims description 4
• BHRKIYVQKAPXBH-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3,5-difluorophenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(F)C=C(F)C=C1C1=NCCCN1 BHRKIYVQKAPXBH-UHFFFAOYSA-N 0.000 claims description 4
• FOVOETZPEDCAOZ-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3,5-difluorophenyl]-5,5-dimethyl-1,4-dihydroimidazole Chemical compound COC1=CC=C(Br)C=C1CSC1=C(F)C=C(F)C=C1C1=NCC(C)(C)N1 FOVOETZPEDCAOZ-UHFFFAOYSA-N 0.000 claims description 4
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