AU6621600A

AU6621600A - Melanocortin-4 receptor binding compounds and methods of use thereof

Melanocortin-4 receptor binding compounds and methods of use thereof Download PDF

Info

Publication number: AU6621600A
Authority: AU; Australia
Prior art keywords: phenyl; tetrahydro; methoxy; pyrimidine; benzylsulfanyl
Prior art date: 1999-08-04
Legal status : Abandoned

Application number

AU66216/00A

Other languages

English (en)

Inventor

Mingshi Dai

Martin P. Maguire

Tricia J. Vos

Current Assignee

Millennium Pharmaceuticals Inc

Original Assignee

Millennium Pharmaceuticals Inc

Priority date

1999-08-04

Filing date

2000-08-04

Publication date

2001-03-05

2000-08-04 Application filed by Millennium Pharmaceuticals Inc filed Critical Millennium Pharmaceuticals Inc

2001-03-05 Publication of AU6621600A publication Critical patent/AU6621600A/en

2004-06-24 Priority to AU2004202804A priority Critical patent/AU2004202804B2/en

Status Abandoned legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 418
238000000034 method Methods 0.000 title claims description 213
230000027455 binding Effects 0.000 title claims description 180
108010021436 Type 4 Melanocortin Receptor Proteins 0.000 title description 249
102000001796 Melanocortin 4 receptors Human genes 0.000 title 1
-1 amino, amidino, guanidino Chemical group 0.000 claims description 324
125000000217 alkyl group Chemical group 0.000 claims description 265
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 116
125000000304 alkynyl group Chemical group 0.000 claims description 108
125000003545 alkoxy group Chemical group 0.000 claims description 97
229910052736 halogen Inorganic materials 0.000 claims description 97
150000002367 halogens Chemical class 0.000 claims description 97
102100023724 Melanocortin receptor 4 Human genes 0.000 claims description 94
239000001257 hydrogen Substances 0.000 claims description 94
229910052739 hydrogen Inorganic materials 0.000 claims description 94
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
125000004093 cyano group Chemical group *C#N 0.000 claims description 77
229910052799 carbon Inorganic materials 0.000 claims description 70
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 60
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 55
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 54
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 53
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 52
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
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
125000001072 heteroaryl group Chemical group 0.000 claims description 45
239000008194 pharmaceutical composition Substances 0.000 claims description 45
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 43
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 43
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
229910052757 nitrogen Inorganic materials 0.000 claims description 40
125000004122 cyclic group Chemical group 0.000 claims description 38
125000004433 nitrogen atom Chemical group N* 0.000 claims description 37
229910052717 sulfur Inorganic materials 0.000 claims description 37
229910052760 oxygen Inorganic materials 0.000 claims description 35
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
239000000460 chlorine Substances 0.000 claims description 32
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 31
125000003710 aryl alkyl group Chemical group 0.000 claims description 31
239000011593 sulfur Chemical group 0.000 claims description 31
229910052801 chlorine Inorganic materials 0.000 claims description 30
125000004663 dialkyl amino group Chemical group 0.000 claims description 30
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
229910052731 fluorine Inorganic materials 0.000 claims description 28
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
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 25
238000006467 substitution reaction Methods 0.000 claims description 25
150000005347 biaryls Chemical group 0.000 claims description 24
125000004430 oxygen atom Chemical group O* 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
150000003568 thioethers Chemical class 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 16
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
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
125000005647 linker group Chemical group 0.000 claims description 14
208000016261 weight loss Diseases 0.000 claims description 14
230000004580 weight loss Effects 0.000 claims description 14
206010006895 Cachexia Diseases 0.000 claims description 13
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 12
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
125000003277 amino group Chemical group 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 12
208000035475 disorder Diseases 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
OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 claims description 10
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
150000001412 amines Chemical class 0.000 claims description 9
125000004104 aryloxy group Chemical group 0.000 claims description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
125000003373 pyrazinyl group Chemical group 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
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
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
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
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 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
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
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 7
VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-UHFFFAOYSA-N 0.000 claims description 7
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
239000005557 antagonist Substances 0.000 claims description 7
230000019612 pigmentation Effects 0.000 claims description 7
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 6
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
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 6
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 6
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 6
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
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 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
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
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
150000004985 diamines Chemical class 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
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
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
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
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
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
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
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 claims description 4
AFKXHBOKRSLWGJ-UHFFFAOYSA-N 2-(2-pentadecylsulfanylphenyl)-1,4,5,6-tetrahydropyrimidine Chemical compound CCCCCCCCCCCCCCCSC1=CC=CC=C1C1=NCCCN1 AFKXHBOKRSLWGJ-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
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
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 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
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
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
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 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
HLXFXORVYDASPB-UHFFFAOYSA-N 2-[2-(cyclohexylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C1CCCCC1CSC1=CC=CC=C1C1=NCCCN1 HLXFXORVYDASPB-UHFFFAOYSA-N 0.000 claims description 4
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
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 claims description 4
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 claims description 4
VJKACOCRHHQFEQ-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylsulfanylmethyl)phenyl]piperidine Chemical compound C=1C=CC2=CC=CC=C2C=1SCC1=CC=CC=C1C1CCCCN1 VJKACOCRHHQFEQ-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
LTWCBBRXEBVHTH-UHFFFAOYSA-N 2-[2-[(2,5-dichlorothiophen-3-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound S1C(Cl)=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1Cl LTWCBBRXEBVHTH-UHFFFAOYSA-N 0.000 claims description 4
WWNCZFPVXCKTNW-UHFFFAOYSA-N 2-[2-[(2,5-dimethoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(OC)C(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 WWNCZFPVXCKTNW-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
HGTPFVATRKNXIH-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound BrC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 HGTPFVATRKNXIH-UHFFFAOYSA-N 0.000 claims description 4
KEDBEJDOVCGYMS-UHFFFAOYSA-N 2-[2-[(2-bromophenyl)sulfanylmethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound BrC1=CC=CC=C1SCC1=CC=CC=C1C1=NCCCN1 KEDBEJDOVCGYMS-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
XUNKOLSVSAKVHQ-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound ClC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 XUNKOLSVSAKVHQ-UHFFFAOYSA-N 0.000 claims description 4
JCBIOHYTOHEEKN-UHFFFAOYSA-N 2-[2-[(2-chlorophenyl)sulfanylmethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound ClC1=CC=CC=C1SCC1=CC=CC=C1C1=NCCCN1 JCBIOHYTOHEEKN-UHFFFAOYSA-N 0.000 claims description 4
SMTXSQTYIZFVIR-UHFFFAOYSA-N 2-[2-[(2-cyclopentyloxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C1CCCC1OC=1C=CC2=CC=CC=C2C=1CSC1=CC=CC=C1C1=NCCCN1 SMTXSQTYIZFVIR-UHFFFAOYSA-N 0.000 claims description 4
VKOWVQSIVDKTFD-UHFFFAOYSA-N 2-[2-[(2-cyclopentyloxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=C(OC2CCCC2)C=1CSC1=CC=CC=C1C1=NCCCN1 VKOWVQSIVDKTFD-UHFFFAOYSA-N 0.000 claims description 4
RLQOQTQCFAZGSR-UHFFFAOYSA-N 2-[2-[(2-ethoxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CCOC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 RLQOQTQCFAZGSR-UHFFFAOYSA-N 0.000 claims description 4
UEYAWOPDBOWKEK-UHFFFAOYSA-N 2-[2-[(2-fluorophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound FC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 UEYAWOPDBOWKEK-UHFFFAOYSA-N 0.000 claims description 4
AMSWPHUXJQRFBP-UHFFFAOYSA-N 2-[2-[(2-iodophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound IC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 AMSWPHUXJQRFBP-UHFFFAOYSA-N 0.000 claims description 4
JQMKHYYNAWZZBX-UHFFFAOYSA-N 2-[2-[(2-iodophenyl)methylsulfanyl]phenyl]-4,5-dihydro-1h-imidazole Chemical compound IC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCN1 JQMKHYYNAWZZBX-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
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
JLIDYMPVMLNLGY-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-nitrophenyl)methylsulfanyl]pyridin-3-yl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C([N+]([O-])=O)C=C1CSC1=NC=CC=C1C1=NCCCN1 JLIDYMPVMLNLGY-UHFFFAOYSA-N 0.000 claims description 4
CGDASKIJYYWJSM-UHFFFAOYSA-N 2-[2-[(2-methoxy-5-phenylphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(C=2C=CC=CC=2)C=C1CSC1=CC=CC=C1C1=NCCCN1 CGDASKIJYYWJSM-UHFFFAOYSA-N 0.000 claims description 4
VUQUNQSDLBZMCT-UHFFFAOYSA-N 2-[2-[(2-methoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 VUQUNQSDLBZMCT-UHFFFAOYSA-N 0.000 claims description 4
QRISVWPWDXQJMG-UHFFFAOYSA-N 2-[2-[(2-methoxyphenyl)sulfanylmethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=CC=C1SCC1=CC=CC=C1C1=NCCCN1 QRISVWPWDXQJMG-UHFFFAOYSA-N 0.000 claims description 4
ZAZUDFGPICAKDI-UHFFFAOYSA-N 2-[2-[(2-methylnaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 ZAZUDFGPICAKDI-UHFFFAOYSA-N 0.000 claims description 4
MFWSRNUATFFCLO-UHFFFAOYSA-N 2-[2-[(2-methylphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC1=CC=CC=C1CSC1=CC=CC=C1C1=NCCCN1 MFWSRNUATFFCLO-UHFFFAOYSA-N 0.000 claims description 4
PHPOZVKYMNDMHX-UHFFFAOYSA-N 2-[2-[(2-phenylphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1CSC1=CC=CC=C1C1=NCCCN1 PHPOZVKYMNDMHX-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
MVFGKBOVQQMARR-UHFFFAOYSA-N 2-[2-[(2-propoxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CCCOC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 MVFGKBOVQQMARR-UHFFFAOYSA-N 0.000 claims description 4
YZQSLUVOBLBNMG-UHFFFAOYSA-N 2-[2-[(3,5-dimethoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC(OC)=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 YZQSLUVOBLBNMG-UHFFFAOYSA-N 0.000 claims description 4
COTASPQXFNVYQO-UHFFFAOYSA-N 2-[2-[(3-bromophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound BrC1=CC=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 COTASPQXFNVYQO-UHFFFAOYSA-N 0.000 claims description 4
QCHPOPXUCRMGCY-UHFFFAOYSA-N 2-[2-[(3-chlorophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound ClC1=CC=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 QCHPOPXUCRMGCY-UHFFFAOYSA-N 0.000 claims description 4
GMDPNUDGOALJPG-UHFFFAOYSA-N 2-[2-[(3-iodophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound IC1=CC=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 GMDPNUDGOALJPG-UHFFFAOYSA-N 0.000 claims description 4
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
IHIDTXABSJSEDM-UHFFFAOYSA-N 2-[2-[(3-nitrophenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound [O-][N+](=O)C1=CC=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 IHIDTXABSJSEDM-UHFFFAOYSA-N 0.000 claims description 4
OPPJDQNZBNINSH-UHFFFAOYSA-N 2-[2-[(3-phenylphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC(C=2C=CC=CC=2)=CC=1CSC1=CC=CC=C1C1=NCCCN1 OPPJDQNZBNINSH-UHFFFAOYSA-N 0.000 claims description 4
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
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
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
RTXJBQSGOVXPQR-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-3-fluorophenyl]-5,5-dimethyl-4,6-dihydro-1h-pyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=C(F)C=CC=C1C1=NCC(C)(C)CN1 RTXJBQSGOVXPQR-UHFFFAOYSA-N 0.000 claims description 4
ZECWULPQHNOWRR-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-5-fluorophenyl]-4,5-dihydro-1h-imidazole Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=C(F)C=C1C1=NCCN1 ZECWULPQHNOWRR-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
VJCWFTJNIJPWCW-UHFFFAOYSA-N 2-[2-[(5-bromo-2-propan-2-yloxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC(C)OC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NCCCN1 VJCWFTJNIJPWCW-UHFFFAOYSA-N 0.000 claims description 4
MUSSZQAYEUONGF-UHFFFAOYSA-N 2-[2-[(5-bromo-2-propoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CCCOC1=CC=C(Br)C=C1CSC1=CC=CC=C1C1=NCCCN1 MUSSZQAYEUONGF-UHFFFAOYSA-N 0.000 claims description 4
NHYCLGJOZNTBRB-UHFFFAOYSA-N 2-[2-[(5-ethynyl-2-methoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(C#C)C=C1CSC1=CC=CC=C1C1=NCCCN1 NHYCLGJOZNTBRB-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
TYHWUSYRUAHMBB-UHFFFAOYSA-N 2-[2-[(6-fluoronaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC(F)=CC=C2C=1CSC1=CC=CC=C1C1=NCCCN1 TYHWUSYRUAHMBB-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
GYJLBLSVLQVQOR-UHFFFAOYSA-N 2-[2-[2-(2-methoxynaphthalen-1-yl)ethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C2C=CC=CC2=C1CCC1=CC=CC=C1C1=NCCCN1 GYJLBLSVLQVQOR-UHFFFAOYSA-N 0.000 claims description 4
DSRUBXVCPSJSAX-UHFFFAOYSA-N 2-[2-[2-(2-methylnaphthalen-1-yl)ethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound CC1=CC=C2C=CC=CC2=C1CCC1=CC=CC=C1C1=NCCCN1 DSRUBXVCPSJSAX-UHFFFAOYSA-N 0.000 claims description 4
CCISHMCRIWHRTE-UHFFFAOYSA-N 2-[2-[[2,4-bis(trifluoromethyl)phenyl]methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC=C1CSC1=CC=CC=C1C1=NCCCN1 CCISHMCRIWHRTE-UHFFFAOYSA-N 0.000 claims description 4
RBUZILJRVMVRED-UHFFFAOYSA-N 2-[2-[[3,5-bis(trifluoromethyl)phenyl]methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 RBUZILJRVMVRED-UHFFFAOYSA-N 0.000 claims description 4
FSGARAUGNFHJCY-UHFFFAOYSA-N 2-[3-(naphthalen-1-ylsulfanylmethyl)thiophen-2-yl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1SCC=1C=CSC=1C1=NCCCN1 FSGARAUGNFHJCY-UHFFFAOYSA-N 0.000 claims description 4
HUQNTTQVZYURMS-UHFFFAOYSA-N 2-[3-[(5-bromo-2-methoxyphenyl)methylsulfanyl]pyridin-2-yl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=CN=C1C1=NCCCN1 HUQNTTQVZYURMS-UHFFFAOYSA-N 0.000 claims description 4
XFWBPYOQWBEJDY-UHFFFAOYSA-N 2-[3-chloro-2-(2-naphthalen-1-ylethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC=1C(Cl)=CC=CC=1C1=NCCCN1 XFWBPYOQWBEJDY-UHFFFAOYSA-N 0.000 claims description 4
VQPNUOOVVQVJAQ-UHFFFAOYSA-N 2-[3-fluoro-2-(2-naphthalen-1-ylethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC=1C(F)=CC=CC=1C1=NCCCN1 VQPNUOOVVQVJAQ-UHFFFAOYSA-N 0.000 claims description 4
VSLAWUJINZENSD-UHFFFAOYSA-N 2-[3-fluoro-2-(naphthalen-1-ylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CSC=1C(F)=CC=CC=1C1=NCCCN1 VSLAWUJINZENSD-UHFFFAOYSA-N 0.000 claims description 4
WWQPTDNNDBFOLF-UHFFFAOYSA-N 2-[3-methoxy-2-(2-naphthalen-1-ylethyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CCC=1C(OC)=CC=CC=1C1=NCCCN1 WWQPTDNNDBFOLF-UHFFFAOYSA-N 0.000 claims description 4
REYLZFXVSGOFRG-UHFFFAOYSA-N 2-[4-(naphthalen-1-ylmethylsulfanyl)phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound C=1C=CC2=CC=CC=C2C=1CSC(C=C1)=CC=C1C1=NCCCN1 REYLZFXVSGOFRG-UHFFFAOYSA-N 0.000 claims description 4
ZDCKTYHRUDDTRR-UHFFFAOYSA-N 2-amino-2-[2-(2-naphthalen-1-ylethyl)phenyl]acetonitrile Chemical compound N#CC(N)C1=CC=CC=C1CCC1=CC=CC2=CC=CC=C12 ZDCKTYHRUDDTRR-UHFFFAOYSA-N 0.000 claims description 4
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