JP2003528810A

JP2003528810A - メラノコルチン−４受容体結合化合物及びその使用方法

メラノコルチン−４受容体結合化合物及びその使用方法

Info

Publication number: JP2003528810A
Authority: JP; Japan
Prior art keywords: phenyl; methoxy; tetrahydro; pyrimidine; benzylsulfanyl
Prior art date: 1999-08-04
Legal status : Pending

Application number

JP2001515309A

Other languages

English (en)

Japanese (ja)

Other versions

JP2003528810A5 (enExample

Inventor

マーティンピーマグワイア

ミンシダイ

トリシアジェイヴォス

Original Assignee

ミレニアムファーマスーティカルズインク

Priority date

1999-08-04

Filing date

2000-08-04

Publication date

2003-09-30

2000-08-04 Application filed by ミレニアムファーマスーティカルズインク filed Critical ミレニアムファーマスーティカルズインク

2003-09-30 Publication of JP2003528810A publication Critical patent/JP2003528810A/ja

2007-09-20 Publication of JP2003528810A5 publication Critical patent/JP2003528810A5/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 436
238000000034 method Methods 0.000 title claims abstract description 292
108010021436 Type 4 Melanocortin Receptor Proteins 0.000 title description 242
102000001796 Melanocortin 4 receptors Human genes 0.000 title 1
102100023724 Melanocortin receptor 4 Human genes 0.000 claims abstract description 89
230000004580 weight loss Effects 0.000 claims abstract description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
101710085775 Melanocortin receptor 4 Proteins 0.000 claims abstract 88
-1 amino, amidino, guanidino Chemical group 0.000 claims description 718
125000000217 alkyl group Chemical group 0.000 claims description 257
125000003118 aryl group Chemical group 0.000 claims description 152
125000000623 heterocyclic group Chemical group 0.000 claims description 112
125000003342 alkenyl group Chemical group 0.000 claims description 109
125000000304 alkynyl group Chemical group 0.000 claims description 104
125000003545 alkoxy group Chemical group 0.000 claims description 92
239000001257 hydrogen Substances 0.000 claims description 92
229910052739 hydrogen Inorganic materials 0.000 claims description 92
229910052736 halogen Inorganic materials 0.000 claims description 90
150000002367 halogens Chemical class 0.000 claims description 84
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 76
229910052799 carbon Inorganic materials 0.000 claims description 71
125000004093 cyano group Chemical group *C#N 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 60
229910052757 nitrogen Inorganic materials 0.000 claims description 56
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 55
229910052717 sulfur Inorganic materials 0.000 claims description 52
125000000449 nitro group Chemical group [O-][N+](*)=O 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 50
241000124008 Mammalia Species 0.000 claims description 48
239000000203 mixture Substances 0.000 claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 47
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 46
150000001721 carbon Chemical group 0.000 claims description 46
125000001424 substituent group Chemical group 0.000 claims description 46
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
125000002252 acyl group Chemical group 0.000 claims description 42
229910052760 oxygen Inorganic materials 0.000 claims description 41
239000008194 pharmaceutical composition Substances 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 39
125000004122 cyclic group Chemical group 0.000 claims description 39
125000001624 naphthyl group Chemical group 0.000 claims description 39
125000001072 heteroaryl group Chemical group 0.000 claims description 36
125000004433 nitrogen atom Chemical group N* 0.000 claims description 34
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 32
239000001301 oxygen Substances 0.000 claims description 32
239000011593 sulfur Substances 0.000 claims description 32
125000003710 aryl alkyl group Chemical group 0.000 claims description 30
239000000460 chlorine Substances 0.000 claims description 30
229910052801 chlorine Inorganic materials 0.000 claims description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 29
239000011737 fluorine Substances 0.000 claims description 28
229910052731 fluorine Inorganic materials 0.000 claims description 28
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 26
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
229910052794 bromium Inorganic materials 0.000 claims description 26
125000004663 dialkyl amino group Chemical group 0.000 claims description 25
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
239000003814 drug Substances 0.000 claims description 21
150000005347 biaryls Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 18
125000005842 heteroatom Chemical group 0.000 claims description 18
239000003937 drug carrier Substances 0.000 claims description 16
125000005647 linker group Chemical group 0.000 claims description 16
SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
208000016261 weight loss Diseases 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
206010006895 Cachexia Diseases 0.000 claims description 12
125000003277 amino group Chemical group 0.000 claims description 12
229910014033 C-OH Inorganic materials 0.000 claims description 11
229910014570 C—OH Inorganic materials 0.000 claims description 11
125000003367 polycyclic group Chemical group 0.000 claims description 11
125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
150000003568 thioethers Chemical class 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 10
125000004076 pyridyl group Chemical group 0.000 claims description 10
125000000168 pyrrolyl group Chemical group 0.000 claims description 10
125000004434 sulfur atom Chemical group 0.000 claims description 10
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
125000003386 piperidinyl group Chemical group 0.000 claims description 9
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
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 8
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 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
239000005557 antagonist Substances 0.000 claims description 8
125000002837 carbocyclic group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 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 7
125000004103 aminoalkyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002619 bicyclic group Chemical group 0.000 claims description 7
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 7
125000004430 oxygen atom Chemical group O* 0.000 claims description 7
125000001544 thienyl group Chemical group 0.000 claims description 7
239000000556 agonist Substances 0.000 claims description 6
125000001207 fluorophenyl group Chemical group 0.000 claims description 6
230000019612 pigmentation Effects 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
125000002393 azetidinyl group Chemical group 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
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
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
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
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 claims description 4
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 claims description 4
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 claims description 4
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 claims description 4
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
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 claims description 4
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
ZLJUCWCUFIZEDW-UHFFFAOYSA-N 2-[2-[(2,5-dichlorophenyl)sulfanylmethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound ClC1=CC=C(Cl)C(SCC=2C(=CC=CC=2)C=2NCCCN=2)=C1 ZLJUCWCUFIZEDW-UHFFFAOYSA-N 0.000 claims description 4
USWIGGWFARNAIT-UHFFFAOYSA-N 2-[2-[(2,5-dimethylphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC1=CC=C(C)C(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 USWIGGWFARNAIT-UHFFFAOYSA-N 0.000 claims description 4
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 4
IKNWNXHMEIPMHN-UHFFFAOYSA-N 2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]phenyl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazole Chemical compound FC1=CC=CC(Cl)=C1CSC1=CC=CC=C1C(N1)=NC2C1CCCC2 IKNWNXHMEIPMHN-UHFFFAOYSA-N 0.000 claims description 4
HNKHRELQAZCOCP-UHFFFAOYSA-N 2-[2-[(2-chloro-6-fluorophenyl)methylsulfanyl]phenyl]-4,5-dihydro-1h-imidazole Chemical compound FC1=CC=CC(Cl)=C1CSC1=CC=CC=C1C1=NCCN1 HNKHRELQAZCOCP-UHFFFAOYSA-N 0.000 claims description 4
KTWWZGRWSAZNFV-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-nitrophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C([N+]([O-])=O)C=C1CSC1=CC=CC=C1C1=NCCCN1 KTWWZGRWSAZNFV-UHFFFAOYSA-N 0.000 claims description 4
YSKONJARCLBXRG-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-nitrophenyl)methylsulfanyl]phenyl]-3a,4,5,6,7,7a-hexahydro-1h-benzimidazole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1CSC1=CC=CC=C1C(N1)=NC2C1CCCC2 YSKONJARCLBXRG-UHFFFAOYSA-N 0.000 claims description 4
XROZEKFUKUQTAT-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-nitrophenyl)methylsulfanyl]phenyl]-4,5-dihydro-1h-imidazole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1CSC1=CC=CC=C1C1=NCCN1 XROZEKFUKUQTAT-UHFFFAOYSA-N 0.000 claims description 4
JURFLFGQSHDRQR-UHFFFAOYSA-N 2-[2-[(2-propan-2-yloxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)OC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 JURFLFGQSHDRQR-UHFFFAOYSA-N 0.000 claims description 4
PUDQPIKMLRFZPN-UHFFFAOYSA-N 2-[2-[(5-bromo-2-cyclopentyloxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=C(C=2NCCCN=2)C=1SCC1=CC(Br)=CC=C1OC1CCCC1 PUDQPIKMLRFZPN-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
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
BVRSBCUMISUFPR-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]-1,4,5,6-tetrahydropyrimidin-5-ol Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1C1=NCC(O)CN1 BVRSBCUMISUFPR-UHFFFAOYSA-N 0.000 claims description 4
ORJVHEZQRTWNPN-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-chlorophenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(Cl)C=CC=C1C1=NCCCN1 ORJVHEZQRTWNPN-UHFFFAOYSA-N 0.000 claims description 4
LNPRXFXPBRCTGB-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]-5-methyl-4,5-dihydro-1h-imidazole Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NC(C)CN1 LNPRXFXPBRCTGB-UHFFFAOYSA-N 0.000 claims description 4
VFXNWSNBKZPTTD-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]phenyl]guanidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CC=C1NC(N)=N VFXNWSNBKZPTTD-UHFFFAOYSA-N 0.000 claims description 4
DIHXBZVYCWIMIW-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)sulfanylmethyl]-3-chlorophenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1SCC1=C(Cl)C=CC=C1C1=NCCCN1 DIHXBZVYCWIMIW-UHFFFAOYSA-N 0.000 claims description 4
FYSBRELZWWDOLV-UHFFFAOYSA-N 2-[2-[(6-bromo-2-methoxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C2C=C(Br)C=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 FYSBRELZWWDOLV-UHFFFAOYSA-N 0.000 claims description 4
XZTTZBZEQYPTEC-UHFFFAOYSA-N 2-[2-[(6-methoxy-2,3-dihydro-1,4-benzodioxin-5-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C2OCCOC2=C1CSC1=CC=CC=C1C1=NCCCN1 XZTTZBZEQYPTEC-UHFFFAOYSA-N 0.000 claims description 4
UCANUPCLAHKJLU-UHFFFAOYSA-N 2-[2-[2-(2,3-dihydro-1,4-benzodioxin-5-yl)ethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=2OCCOC=2C=1CCC1=CC=CC=C1C1=NCCCN1 UCANUPCLAHKJLU-UHFFFAOYSA-N 0.000 claims description 4
WMSIKZDVBSROMD-UHFFFAOYSA-N 2-[2-[2-(5-bromo-2-methoxyphenyl)ethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CCC1=CC=CC=C1C1=NCCCN1 WMSIKZDVBSROMD-UHFFFAOYSA-N 0.000 claims description 4
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