RU2375356C2 - ПРОИЗВОДНЫЕ ИМИДАЗОЛА В КАЧЕСТВЕ ИНГИБИТОРОВ TAFIa - Google Patents

Info

Publication number

RU2375356C2

RU2375356C2 RU2006141246/04A RU2006141246A RU2375356C2 RU 2375356 C2 RU2375356 C2 RU 2375356C2 RU 2006141246/04 A RU2006141246/04 A RU 2006141246/04A RU 2006141246 A RU2006141246 A RU 2006141246A RU 2375356 C2 RU2375356 C2 RU 2375356C2

Authority

RU

Russia

Prior art keywords

phenyl

unsubstituted

independently

alkyl

imidazol

Prior art date

2004-04-22

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• 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract 2
• 239000003112 inhibitor Substances 0.000 title description 17
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 206
• -1 aminopyridyl Chemical group 0.000 claims abstract description 123
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 117
• 238000000034 method Methods 0.000 claims abstract description 100
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 69
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 38
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 32
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 28
• 150000003839 salts Chemical class 0.000 claims abstract description 19
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
• 150000002367 halogens Chemical class 0.000 claims abstract description 18
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 12
• 125000004419 alkynylene group Chemical group 0.000 claims abstract description 11
• 125000004429 atom Chemical group 0.000 claims abstract description 11
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 9
• 239000000126 substance Substances 0.000 claims abstract description 9
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims abstract description 8
• 239000003814 drug Substances 0.000 claims abstract description 7
• 125000001425 triazolyl group Chemical group 0.000 claims abstract description 7
• 108090000790 Enzymes Proteins 0.000 claims abstract description 5
• 102000004190 Enzymes Human genes 0.000 claims abstract description 5
• 150000002460 imidazoles Chemical class 0.000 claims abstract 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 30
• 125000006239 protecting group Chemical group 0.000 claims description 30
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 238000006243 chemical reaction Methods 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 22
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 20
• 235000019260 propionic acid Nutrition 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 230000015572 biosynthetic process Effects 0.000 claims description 13
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
• 238000004587 chromatography analysis Methods 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
• 229910052801 chlorine Inorganic materials 0.000 claims description 10
• 239000011737 fluorine Substances 0.000 claims description 10
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000003277 amino group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 7
• 238000000926 separation method Methods 0.000 claims description 7
• 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 6
• IQZKZQSOVLMDRA-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-cyclopentylimidazol-4-yl)propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C2CCCC2)C=N1 IQZKZQSOVLMDRA-UHFFFAOYSA-N 0.000 claims description 5
• QSHQJXGGJAQMDN-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[1-(2,2-diphenylacetyl)piperidin-4-yl]ethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CCC1CCN(C(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 QSHQJXGGJAQMDN-UHFFFAOYSA-N 0.000 claims description 5
• 230000005526 G1 to G0 transition Effects 0.000 claims description 5
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
• 230000003213 activating effect Effects 0.000 claims description 5
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
• GJRINXOSIZBUMP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynylimidazol-4-yl)propanoic acid Chemical compound CC#CCN1C=NC(C(CC=2C=NC(N)=CC=2)C(O)=O)=C1 GJRINXOSIZBUMP-UHFFFAOYSA-N 0.000 claims description 4
• OVRMEGOFIXQTHY-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-prop-2-ynylimidazol-4-yl)propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(CC#C)C=N1 OVRMEGOFIXQTHY-UHFFFAOYSA-N 0.000 claims description 4
• NPENPHRKLALGHB-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[4-(phenylcarbamoylamino)phenyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C=2C=CC(NC(=O)NC=3C=CC=CC=3)=CC=2)C=N1 NPENPHRKLALGHB-UHFFFAOYSA-N 0.000 claims description 4
• SQPQZHRORMHFGV-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[4-(propylcarbamoylamino)phenyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(NC(=O)NCCC)=CC=C1N1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 SQPQZHRORMHFGV-UHFFFAOYSA-N 0.000 claims description 4
• BMVIGUTXIDYQTP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[4-[(4-methylphenyl)sulfonylamino]phenyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(N2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)C=C1 BMVIGUTXIDYQTP-UHFFFAOYSA-N 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• UMNZFTZTLPYOTD-UHFFFAOYSA-N ethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C=1N(C2CCCCC2)C=NC=1C(C(=O)OCC)CC1=CC=C(N)N=C1 UMNZFTZTLPYOTD-UHFFFAOYSA-N 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• 230000003993 interaction Effects 0.000 claims description 4
• CRPVPLLSDAUWRU-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C=1C=C(N)N=CC=1CC(C=1N=CN(C=1)C1CCCCC1)C(=O)OC(C)OC(=O)OC1CCCCC1 CRPVPLLSDAUWRU-UHFFFAOYSA-N 0.000 claims description 3
• WJBQXBVLVFMKCZ-UHFFFAOYSA-N 2-hydroxyethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C1=NC(N)=CC=C1CC(C(=O)OCCO)C1=CN(C2CCCCC2)C=N1 WJBQXBVLVFMKCZ-UHFFFAOYSA-N 0.000 claims description 3
• RAMPTCMOFKZGMU-UHFFFAOYSA-N 3-(2-amino-1,3-thiazol-4-yl)-2-[1-[2-(benzhydrylamino)-2-oxoethyl]imidazol-4-yl]propanoic acid Chemical compound S1C(N)=NC(CC(C(O)=O)C=2N=CN(CC(=O)NC(C=3C=CC=CC=3)C=3C=CC=CC=3)C=2)=C1 RAMPTCMOFKZGMU-UHFFFAOYSA-N 0.000 claims description 3
• ACVDSSFNGUNMBR-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-benzhydrylimidazol-4-yl)propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C=N1 ACVDSSFNGUNMBR-UHFFFAOYSA-N 0.000 claims description 3
• XHKJBNCTUYFLDC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C2CCCCC2)C=N1 XHKJBNCTUYFLDC-UHFFFAOYSA-N 0.000 claims description 3
• ZPMPWZIJWOLMHZ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-(1-piperidin-4-ylimidazol-4-yl)propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C2CCNCC2)C=N1 ZPMPWZIJWOLMHZ-UHFFFAOYSA-N 0.000 claims description 3
• PZVHBTKXUXKQNV-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-(2-oxo-1-phenylpyrrolidin-3-yl)imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C2C(N(CC2)C=2C=CC=CC=2)=O)C=N1 PZVHBTKXUXKQNV-UHFFFAOYSA-N 0.000 claims description 3
• WEGXHKRQVOAGFJ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-(4,4-dimethylcyclohexyl)imidazol-4-yl]propanoic acid Chemical compound C1CC(C)(C)CCC1N1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 WEGXHKRQVOAGFJ-UHFFFAOYSA-N 0.000 claims description 3
• DXPCOTQKAXKFMI-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(1-benzoylpiperidin-2-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1N(C(=O)C=2C=CC=CC=2)CCCC1 DXPCOTQKAXKFMI-UHFFFAOYSA-N 0.000 claims description 3
• XKMXCWGVDVPCMG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(1-benzoylpiperidin-4-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1CCN(C(=O)C=2C=CC=CC=2)CC1 XKMXCWGVDVPCMG-UHFFFAOYSA-N 0.000 claims description 3
• QMRJCPJSDHBYFB-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(2-phenoxyphenyl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=CC=C1OC1=CC=CC=C1 QMRJCPJSDHBYFB-UHFFFAOYSA-N 0.000 claims description 3
• IGVKSGTWJAXFKC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(4-phenoxyphenyl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC(C=C1)=CC=C1OC1=CC=CC=C1 IGVKSGTWJAXFKC-UHFFFAOYSA-N 0.000 claims description 3
• OUEPOKZKQATUTC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[(5-chloro-1-benzothiophen-3-yl)methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CSC2=CC=C(Cl)C=C12 OUEPOKZKQATUTC-UHFFFAOYSA-N 0.000 claims description 3
• AOLAHILCSIUWTO-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-(1-benzoylpiperidin-4-yl)ethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CCC1CCN(C(=O)C=2C=CC=CC=2)CC1 AOLAHILCSIUWTO-UHFFFAOYSA-N 0.000 claims description 3
• URJJJWWMUNFNGO-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-(benzhydrylamino)-2-oxoethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC(=O)NC(C=1C=CC=CC=1)C1=CC=CC=C1 URJJJWWMUNFNGO-UHFFFAOYSA-N 0.000 claims description 3
• BJNWWXIWJGTHSF-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[1-(3-phenylpropanoyl)piperidin-3-yl]ethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CCC1CN(C(=O)CCC=2C=CC=CC=2)CCC1 BJNWWXIWJGTHSF-UHFFFAOYSA-N 0.000 claims description 3
• XYEGDLRCNCXMHF-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[1-(3-phenylpropanoyl)piperidin-4-yl]ethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CCC1CCN(C(=O)CCC=2C=CC=CC=2)CC1 XYEGDLRCNCXMHF-UHFFFAOYSA-N 0.000 claims description 3
• ZXEQDMODYQTMOP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[bis(4-methoxyphenyl)methylamino]-2-oxoethyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)NC(=O)CN1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 ZXEQDMODYQTMOP-UHFFFAOYSA-N 0.000 claims description 3
• FXZHWQIXDQMFSQ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[4-(benzylcarbamoylamino)phenyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C1=CN(C=2C=CC(NC(=O)NCC=3C=CC=CC=3)=CC=2)C=N1 FXZHWQIXDQMFSQ-UHFFFAOYSA-N 0.000 claims description 3
• COUCCQUHNMPVBC-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[4-(tert-butylcarbamoylamino)phenyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(NC(=O)NC(C)(C)C)=CC=C1N1C=C(C(CC=2C=NC(N)=CC=2)C(O)=O)N=C1 COUCCQUHNMPVBC-UHFFFAOYSA-N 0.000 claims description 3
• HXXCJSGIRMLZRA-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[1-(2,2-diphenylacetyl)piperidin-3-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1CN(C(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCC1 HXXCJSGIRMLZRA-UHFFFAOYSA-N 0.000 claims description 3
• MNEDSOSXIJHRPE-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[1-[3-(4-methylphenyl)benzoyl]piperidin-4-yl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=CC(C)=CC=C1C1=CC=CC(C(=O)N2CCC(CN3C=C(N=C3)C(CC=3C=NC(N)=CC=3)C(O)=O)CC2)=C1 MNEDSOSXIJHRPE-UHFFFAOYSA-N 0.000 claims description 3
• RBSVINXGWYQSOL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(2-phenylethylcarbamoylamino)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=CC(NC(=O)NCCC=2C=CC=CC=2)=C1 RBSVINXGWYQSOL-UHFFFAOYSA-N 0.000 claims description 3
• FTKURWJYNUMVKL-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(4-fluorophenoxy)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=CC(OC=2C=CC(F)=CC=2)=C1 FTKURWJYNUMVKL-UHFFFAOYSA-N 0.000 claims description 3
• DNWYCISHXTZYDG-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(benzylcarbamoylamino)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=CC(NC(=O)NCC=2C=CC=CC=2)=C1 DNWYCISHXTZYDG-UHFFFAOYSA-N 0.000 claims description 3
• CZPGSXRWHOZZMN-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(propylcarbamoylamino)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound CCCNC(=O)NC1=CC=CC(CN2C=C(N=C2)C(CC=2C=NC(N)=CC=2)C(O)=O)=C1 CZPGSXRWHOZZMN-UHFFFAOYSA-N 0.000 claims description 3
• XBSLXLYYKRRPIF-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[4-(1,2,4-triazol-1-yl)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=C(N2N=CN=C2)C=C1 XBSLXLYYKRRPIF-UHFFFAOYSA-N 0.000 claims description 3
• HGQDIZXJKHDJMJ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[4-(trifluoromethoxy)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=C(OC(F)(F)F)C=C1 HGQDIZXJKHDJMJ-UHFFFAOYSA-N 0.000 claims description 3
• 230000002378 acidificating effect Effects 0.000 claims description 3
• 239000000654 additive Substances 0.000 claims description 3
• MUHISURTDGVAGF-UHFFFAOYSA-N cyclopropylmethyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C1=NC(N)=CC=C1CC(C=1N=CN(C=1)C1CCCCC1)C(=O)OCC1CC1 MUHISURTDGVAGF-UHFFFAOYSA-N 0.000 claims description 3
• JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 3
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
• IRLIYIPUIDRSIO-UHFFFAOYSA-N methyl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C=1N(C2CCCCC2)C=NC=1C(C(=O)OC)CC1=CC=C(N)N=C1 IRLIYIPUIDRSIO-UHFFFAOYSA-N 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• WIQPBDWLVQXSNI-UHFFFAOYSA-N propan-2-yl 3-(6-aminopyridin-3-yl)-2-(1-cyclohexylimidazol-4-yl)propanoate Chemical compound C=1N(C2CCCCC2)C=NC=1C(C(=O)OC(C)C)CC1=CC=C(N)N=C1 WIQPBDWLVQXSNI-UHFFFAOYSA-N 0.000 claims description 3
• XTSVUWOVDVXUNJ-UHFFFAOYSA-N propan-2-yl 3-(6-aminopyridin-3-yl)-2-[1-[2-(benzhydrylamino)-2-oxoethyl]imidazol-4-yl]propanoate Chemical compound C=1N(CC(=O)NC(C=2C=CC=CC=2)C=2C=CC=CC=2)C=NC=1C(C(=O)OC(C)C)CC1=CC=C(N)N=C1 XTSVUWOVDVXUNJ-UHFFFAOYSA-N 0.000 claims description 3
• FBVNIMKXMMQQOJ-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[2-[[(4-chlorophenyl)-phenylmethyl]amino]-2-oxoethyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC(=O)NC(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 FBVNIMKXMMQQOJ-UHFFFAOYSA-N 0.000 claims description 2
• IBLOUCHJUQVAIP-UHFFFAOYSA-N 3-(6-aminopyridin-3-yl)-2-[1-[[3-(ethenylcarbamoylamino)phenyl]methyl]imidazol-4-yl]propanoic acid Chemical compound C1=NC(N)=CC=C1CC(C(O)=O)C(N=C1)=CN1CC1=CC=CC(NC(=O)NC=C)=C1 IBLOUCHJUQVAIP-UHFFFAOYSA-N 0.000 claims description 2
• 230000000996 additive effect Effects 0.000 claims description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
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