SK161098A3 - Inhibitors of protein farnesyl transferase - Google Patents

Info

Publication number

SK161098A3

SK161098A3 SK1610-98A SK161098A SK161098A3 SK 161098 A3 SK161098 A3 SK 161098A3 SK 161098 A SK161098 A SK 161098A SK 161098 A3 SK161098 A3 SK 161098A3

Authority

SK

Slovakia

Prior art keywords

methyl

ethyl

imidazol

carbamoyl

phenylpropylcarbamoyl

Prior art date

1996-05-22

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• 108010054353 p21(ras) farnesyl-protein transferase Proteins 0.000 title abstract description 11
• 239000003112 inhibitor Substances 0.000 title abstract description 3
• 238000000034 method Methods 0.000 claims abstract description 80
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 38
• 201000011510 cancer Diseases 0.000 claims abstract description 27
• 208000037803 restenosis Diseases 0.000 claims abstract description 19
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 11
• 208000036142 Viral infection Diseases 0.000 claims abstract description 11
• 230000009385 viral infection Effects 0.000 claims abstract description 11
• -1 C 1 -C 6 alkyl Inorganic materials 0.000 claims description 342
• 150000001875 compounds Chemical class 0.000 claims description 232
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 159
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 123
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 117
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 114
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 87
• 229910052739 hydrogen Inorganic materials 0.000 claims description 55
• 239000001257 hydrogen Substances 0.000 claims description 55
• 239000000203 mixture Substances 0.000 claims description 50
• 125000000217 alkyl group Chemical group 0.000 claims description 34
• 150000002431 hydrogen Chemical class 0.000 claims description 30
• 150000002148 esters Chemical class 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• 150000003839 salts Chemical class 0.000 claims description 21
• 150000001408 amides Chemical class 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 229940002612 prodrug Drugs 0.000 claims description 16
• 239000000651 prodrug Substances 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 9
• 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
• PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 claims description 4
• 206010009944 Colon cancer Diseases 0.000 claims description 4
• KLNREZJWLLCYLH-RDFKHQOOSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-oxo-1-[[2-oxo-2-(2-phenylpropylamino)ethyl]-[(4-phenylmethoxyphenyl)methyl]amino]propan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 KLNREZJWLLCYLH-RDFKHQOOSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 125000001072 heteroaryl group Chemical group 0.000 claims description 4
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 3
• 125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 3
• 206010005003 Bladder cancer Diseases 0.000 claims description 3
• 208000026310 Breast neoplasm Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• DMGJRELNPSPIKC-IZCXSWDTSA-N benzyl n-[(2s)-1-[(3-chlorophenyl)methyl-[2-oxo-2-(2-phenylpropylamino)ethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC(Cl)=C1 DMGJRELNPSPIKC-IZCXSWDTSA-N 0.000 claims description 3
• NQVJXBFXQFGIHU-IZCXSWDTSA-N benzyl n-[(2s)-1-[(4-bromophenyl)methyl-[2-oxo-2-(2-phenylpropylamino)ethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=C(Br)C=C1 NQVJXBFXQFGIHU-IZCXSWDTSA-N 0.000 claims description 3
• SSXFUPUONWGRIP-IZCXSWDTSA-N benzyl n-[(2s)-1-[(4-chlorophenyl)methyl-[2-oxo-2-(2-phenylpropylamino)ethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=C(Cl)C=C1 SSXFUPUONWGRIP-IZCXSWDTSA-N 0.000 claims description 3
• NPVIMMQTVLPHKV-RWYGWLOXSA-N benzyl n-[(2s)-1-[[2-(2,2-diphenylethylamino)-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 NPVIMMQTVLPHKV-RWYGWLOXSA-N 0.000 claims description 3
• UYCQJDCAUDGFKR-DHUJRADRSA-N benzyl n-[(2s)-1-[[2-[2-(2-bromophenyl)ethylamino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound BrC1=CC=CC=C1CCNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 UYCQJDCAUDGFKR-DHUJRADRSA-N 0.000 claims description 3
• YDVQFZBNLASSIP-PQEJLDEPSA-N benzyl n-[(2s)-1-[[2-[[2-(2-chlorophenyl)-2-phenylethyl]amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound ClC1=CC=CC=C1C(C=1C=CC=CC=1)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 YDVQFZBNLASSIP-PQEJLDEPSA-N 0.000 claims description 3
• JOMJUWAAYRJJBC-DHUJRADRSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-oxo-1-[[2-oxo-2-(2-phenylethylamino)ethyl]-[(4-phenylmethoxyphenyl)methyl]amino]propan-2-yl]carbamate Chemical compound C=1C=CC=CC=1CCNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 JOMJUWAAYRJJBC-DHUJRADRSA-N 0.000 claims description 3
• QBYRWRXKLWORHI-DEGOBNMZSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-oxo-1-[[2-oxo-2-(2-phenylpropylamino)ethyl]-[(4-phenylphenyl)methyl]amino]propan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 QBYRWRXKLWORHI-DEGOBNMZSA-N 0.000 claims description 3
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
• KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 208000029742 colonic neoplasm Diseases 0.000 claims description 3
• 210000002966 serum Anatomy 0.000 claims description 3
• MWKXDVCRUBALLO-UHFFFAOYSA-N thiophen-3-ylmethyl carbamate Chemical compound NC(=O)OCC=1C=CSC=1 MWKXDVCRUBALLO-UHFFFAOYSA-N 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 3
• ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 2
• 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• 125000006483 4-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1I)C([H])([H])* 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
• MFVRMBXVDCCSLM-LJAQVGFWSA-N benzyl n-[(2s)-1-[(4-chlorophenyl)methyl-[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=C(Cl)C=C1 MFVRMBXVDCCSLM-LJAQVGFWSA-N 0.000 claims description 2
• MGAFFZTYMAFERW-HKBQPEDESA-N benzyl n-[(2s)-1-[(4-ethoxyphenyl)methyl-[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C1=CC(OCC)=CC=C1CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC(=O)NCC(C)(C)C1=CC=CC=C1 MGAFFZTYMAFERW-HKBQPEDESA-N 0.000 claims description 2
• ZYYZYRPGMHCHED-LJAQVGFWSA-N benzyl n-[(2s)-1-[(4-fluorophenyl)methyl-[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=C(F)C=C1 ZYYZYRPGMHCHED-LJAQVGFWSA-N 0.000 claims description 2
• SMBHALUVUUYXQI-CRGCAJGSSA-N benzyl n-[(2s)-1-[[2-[(2-cyano-2-phenylethyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C#N)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 SMBHALUVUUYXQI-CRGCAJGSSA-N 0.000 claims description 2
• YFOGKUOUUGQZPV-DHUJRADRSA-N benzyl n-[(2s)-1-[[2-[2-(2-aminophenyl)ethylamino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound NC1=CC=CC=C1CCNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 YFOGKUOUUGQZPV-DHUJRADRSA-N 0.000 claims description 2
• XSLKWQLVMQDCMX-LJAQVGFWSA-N benzyl n-[(2s)-1-[benzyl-[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]amino]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 XSLKWQLVMQDCMX-LJAQVGFWSA-N 0.000 claims description 2
• UKDHPFDMEXGIKI-HKBQPEDESA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[2-(4-methoxyphenyl)ethyl-[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C1=CC(OC)=CC=C1CCN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC(=O)NCC(C)(C)C1=CC=CC=C1 UKDHPFDMEXGIKI-HKBQPEDESA-N 0.000 claims description 2
• MYBBTGORNPKHDT-BHVANESWSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 MYBBTGORNPKHDT-BHVANESWSA-N 0.000 claims description 2
• VTDGRAHGAAMRGX-DHUJRADRSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylphenyl)methyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1C1=CC=CC=C1 VTDGRAHGAAMRGX-DHUJRADRSA-N 0.000 claims description 2
• HWLKYGTXYNWEPH-NYZBEGEVSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-oxo-1-[[2-oxo-2-(2-phenylbutylamino)ethyl]-[(4-phenylmethoxyphenyl)methyl]amino]propan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(CC)CNC(=O)CN(C(=O)[C@H](CC=1N=CNC=1)NC(=O)OCC=1C=CC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 HWLKYGTXYNWEPH-NYZBEGEVSA-N 0.000 claims description 2
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• BPJWSBYOKNFUGW-UMSFTDKQSA-N furan-2-ylmethyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1OC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 BPJWSBYOKNFUGW-UMSFTDKQSA-N 0.000 claims description 2
• 201000005202 lung cancer Diseases 0.000 claims description 2
• 208000020816 lung neoplasm Diseases 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• FDLIQPPVQBMJOV-DHUJRADRSA-N pyridin-3-ylmethyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1C=NC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 FDLIQPPVQBMJOV-DHUJRADRSA-N 0.000 claims description 2
• VKXMBBOHXRDTPM-UMSFTDKQSA-N thiophen-2-ylmethyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-1-oxopropan-2-yl]carbamate Chemical compound C=1C=CC=CC=1C(C)(C)CNC(=O)CN(C(=O)[C@H](CC=1NC=NC=1)NC(=O)OCC=1SC=CC=1)CC(C=C1)=CC=C1OCC1=CC=CC=C1 VKXMBBOHXRDTPM-UMSFTDKQSA-N 0.000 claims description 2
• 201000002510 thyroid cancer Diseases 0.000 claims description 2
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 1
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
• OZQYXZMRDXFVJM-XZMVMDBLSA-N CC(CNC(=O)CN(C(CC1=CC=C(C=C1)F)C2=CC=CC=C2)C(=O)[C@H](CC3=CN=CN3)NC(=O)OCC4=CC=CC=C4)C5=CC=CC=C5 Chemical compound CC(CNC(=O)CN(C(CC1=CC=C(C=C1)F)C2=CC=CC=C2)C(=O)[C@H](CC3=CN=CN3)NC(=O)OCC4=CC=CC=C4)C5=CC=CC=C5 OZQYXZMRDXFVJM-XZMVMDBLSA-N 0.000 claims 1
• 101000723968 Xenopus laevis Homeobox protein zampogna Proteins 0.000 claims 1
• MVURESJZKBGJAS-QNGWXLTQSA-N benzyl n-[(2s)-3-(1h-imidazol-5-yl)-1-[[2-[(2-methyl-2-phenylpropyl)amino]-2-oxoethyl]-[(4-phenylmethoxyphenyl)methyl]amino]-1-oxopropan-2-yl]-n-methylcarbamate Chemical compound C([C@H](N(C)C(=O)OCC=1C=CC=CC=1)C(=O)N(CC(=O)NCC(C)(C)C=1C=CC=CC=1)CC=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CN=CN1 MVURESJZKBGJAS-QNGWXLTQSA-N 0.000 claims 1
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
• 229940080818 propionamide Drugs 0.000 claims 1
• 125000004076 pyridyl group Chemical group 0.000 claims 1
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
• 201000001320 Atherosclerosis Diseases 0.000 abstract description 4
• 201000009273 Endometriosis Diseases 0.000 abstract description 3
• 238000002360 preparation method Methods 0.000 abstract description 2
• 239000008194 pharmaceutical composition Substances 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 140
• 239000000243 solution Substances 0.000 description 97
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 72
• 239000006260 foam Substances 0.000 description 70
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 61
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
• ZVTWZSXLLMNMQC-UHFFFAOYSA-N 4-phenylmethoxybenzaldehyde Chemical compound C1=CC(C=O)=CC=C1OCC1=CC=CC=C1 ZVTWZSXLLMNMQC-UHFFFAOYSA-N 0.000 description 41
• 108010014186 ras Proteins Proteins 0.000 description 41
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