MXPA02001160A - Compuestos que se unen a los receptores para melanocortina-4, y metodo de uso de estos. - Google Patents

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Publication number

MXPA02001160A

MXPA02001160A MXPA02001160A MXPA02001160A MXPA02001160A MX PA02001160 A MXPA02001160 A MX PA02001160A MX PA02001160 A MXPA02001160 A MX PA02001160A MX PA02001160 A MXPA02001160 A MX PA02001160A MX PA02001160 A MXPA02001160 A MX PA02001160A

Authority

MX

Mexico

Prior art keywords

phenyl

methoxy

tetrahydro

benzylsulfanyl

bromo

Prior art date

1999-08-04

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 412
• 238000000034 method Methods 0.000 title claims abstract description 219
• 230000027455 binding Effects 0.000 title claims abstract description 128
• 108010021436 Type 4 Melanocortin Receptor Proteins 0.000 title description 250
• 102000001796 Melanocortin 4 receptors Human genes 0.000 title 1
• 230000004580 weight loss Effects 0.000 claims abstract description 15
• 102100023724 Melanocortin receptor 4 Human genes 0.000 claims abstract 91
• 101710085775 Melanocortin receptor 4 Proteins 0.000 claims abstract 91
• -1 amino, amidino, guanidino Chemical group 0.000 claims description 545
• 125000000217 alkyl group Chemical group 0.000 claims description 253
• 125000003118 aryl group Chemical group 0.000 claims description 142
• 125000003342 alkenyl group Chemical group 0.000 claims description 119
• 125000000623 heterocyclic group Chemical group 0.000 claims description 119
• 125000000304 alkynyl group Chemical group 0.000 claims description 104
• 229910052736 halogen Inorganic materials 0.000 claims description 95
• 150000002367 halogens Chemical class 0.000 claims description 95
• 125000003545 alkoxy group Chemical group 0.000 claims description 94
• 229910052739 hydrogen Inorganic materials 0.000 claims description 91
• 239000001257 hydrogen Substances 0.000 claims description 91
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 78
• 229910052799 carbon Inorganic materials 0.000 claims description 68
• 239000000460 chlorine Substances 0.000 claims description 59
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 58
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 52
• 150000001721 carbon Chemical group 0.000 claims description 52
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 51
• 241000124008 Mammalia Species 0.000 claims description 50
• 125000004432 carbon atom Chemical group C* 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 125000001072 heteroaryl group Chemical group 0.000 claims description 46
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
• 239000008194 pharmaceutical composition Substances 0.000 claims description 45
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 40
• 125000004122 cyclic group Chemical group 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 40
• 125000002252 acyl group Chemical group 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 125000001624 naphthyl group Chemical group 0.000 claims description 39
• 229910052717 sulfur Inorganic materials 0.000 claims description 39
• 229910052760 oxygen Inorganic materials 0.000 claims description 36
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
• 239000001301 oxygen Substances 0.000 claims description 32
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 30
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
• 239000011593 sulfur Substances 0.000 claims description 30
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
• 229910052794 bromium Inorganic materials 0.000 claims description 27
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 27
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
• 229910052731 fluorine Inorganic materials 0.000 claims description 25
• 238000006467 substitution reaction Methods 0.000 claims description 25
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
• 239000011737 fluorine Substances 0.000 claims description 24
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 23
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
• 150000005347 biaryls Chemical group 0.000 claims description 22
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
• 125000004429 atom Chemical group 0.000 claims description 20
• 230000003993 interaction Effects 0.000 claims description 19
• 150000003568 thioethers Chemical class 0.000 claims description 19
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 18
• 150000003573 thiols Chemical class 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 16
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
• 239000003937 drug carrier Substances 0.000 claims description 15
• SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical class NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 claims description 15
• 208000016261 weight loss Diseases 0.000 claims description 14
• 101100439662 Arabidopsis thaliana CHR5 gene Proteins 0.000 claims description 13
• 206010006895 Cachexia Diseases 0.000 claims description 13
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000003277 amino group Chemical group 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 125000000168 pyrrolyl 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
• 125000002837 carbocyclic group Chemical group 0.000 claims description 11
• RWRGOKPWZKWGMF-UHFFFAOYSA-N [2-(naphthalen-1-ylmethylsulfanyl)phenyl]carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1SCC1=CC=CC2=CC=CC=C12 RWRGOKPWZKWGMF-UHFFFAOYSA-N 0.000 claims description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
• 208000035475 disorder Diseases 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000004076 pyridyl group Chemical group 0.000 claims description 10
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
• 125000004434 sulfur atom Chemical group 0.000 claims description 10
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 9
• VBXZSFNZVNDOPB-UHFFFAOYSA-N 1,4,5,6-tetrahydropyrimidine Chemical compound C1CNC=NC1 VBXZSFNZVNDOPB-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
• 239000002253 acid Substances 0.000 claims description 8
• 239000000556 agonist Substances 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000002619 bicyclic group Chemical group 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 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 7
• CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical group C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 125000004103 aminoalkyl 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
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 7
• YXBXWTPGDOGXMJ-UHFFFAOYSA-N (2-hexoxyphenyl)carbamic acid Chemical compound CCCCCCOC1=CC=CC=C1NC(O)=O YXBXWTPGDOGXMJ-UHFFFAOYSA-N 0.000 claims description 6
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical group ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 6
• 229940126661 MC4 antagonist Drugs 0.000 claims description 6
• 239000005557 antagonist Substances 0.000 claims description 6
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000001153 fluoro group Chemical group F* 0.000 claims description 6
• MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 6
• 150000004702 methyl esters Chemical class 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 5
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 5
• 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 5
• 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 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
• 229910052744 lithium Inorganic materials 0.000 claims description 5
• 230000019612 pigmentation Effects 0.000 claims description 5
• JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical group C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 claims description 5
• MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical group C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 claims description 4
• JPBFKDIMIFKTGQ-UHFFFAOYSA-N 1-(2-naphthalen-1-ylethyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CCCCN1CCC1=CC=CC2=CC=CC=C12 JPBFKDIMIFKTGQ-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
• 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
• 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
• 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
• 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
• 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
• 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
• 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 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
• 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
• PTYYJYFKWLYTJJ-UHFFFAOYSA-N 2-[2-(naphthalen-1-ylsulfanylmethyl)phenyl]-4,5-dihydro-1h-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1SCC1=CC=CC=C1C1=NCCN1 PTYYJYFKWLYTJJ-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
• 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
• KEFSOJHGKGLWGI-UHFFFAOYSA-N 2-[2-[(2,6-dimethoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=CC(OC)=C1CSC1=CC=CC=C1C1=NCCCN1 KEFSOJHGKGLWGI-UHFFFAOYSA-N 0.000 claims description 4
• FGRRSCLWFFIDDZ-UHFFFAOYSA-N 2-[2-[(2-bromo-5-methoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C(CSC=2C(=CC=CC=2)C=2NCCCN=2)=C1 FGRRSCLWFFIDDZ-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
• 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
• JDLIHUYYNCQAES-UHFFFAOYSA-N 2-[2-[(2-methoxynaphthalen-1-yl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C2C=CC=CC2=C1CSC1=CC=CC=C1C1=NCCCN1 JDLIHUYYNCQAES-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
• 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
• 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
• 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
• AKAKMYRPGCQWGD-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)methylsulfanyl]-5-fluorophenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1CSC1=CC=C(F)C=C1C1=NCCCN1 AKAKMYRPGCQWGD-UHFFFAOYSA-N 0.000 claims description 4
• IGCCPAKERWHUNZ-UHFFFAOYSA-N 2-[2-[(5-bromo-2-methoxyphenyl)sulfanylmethyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(Br)C=C1SCC1=CC=CC=C1C1=NCCCN1 IGCCPAKERWHUNZ-UHFFFAOYSA-N 0.000 claims description 4
• HJWLUEOYGAIIGV-UHFFFAOYSA-N 2-[2-[(5-iodo-2-methoxyphenyl)methylsulfanyl]phenyl]-1,4,5,6-tetrahydropyrimidine Chemical compound COC1=CC=C(I)C=C1CSC1=CC=CC=C1C1=NCCCN1 HJWLUEOYGAIIGV-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
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