RU2530017C2 - Антагонисты 3-аминоалкил-1,4-диазепан-2-он меланокортина-5 рецептора - Google Patents

Info

Publication number

RU2530017C2

RU2530017C2 RU2010137034/04A RU2010137034A RU2530017C2 RU 2530017 C2 RU2530017 C2 RU 2530017C2 RU 2010137034/04 A RU2010137034/04 A RU 2010137034/04A RU 2010137034 A RU2010137034 A RU 2010137034A RU 2530017 C2 RU2530017 C2 RU 2530017C2

Authority

RU

Russia

Prior art keywords

methyl

oxo

diazepan

diphenylethyl

naphthamide

Prior art date

2008-02-29

Links

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• 108010088565 Melanocortin 5 receptor Proteins 0.000 title claims abstract description 47
• 102000030612 Melanocortin 5 receptor Human genes 0.000 title claims abstract description 47
• 239000002464 receptor antagonist Substances 0.000 title abstract 2
• 229940044551 receptor antagonist Drugs 0.000 title abstract 2
• -1 amino, phenoxy Chemical group 0.000 claims abstract description 875
• 150000001875 compounds Chemical class 0.000 claims abstract description 199
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
• 125000001424 substituent group Chemical group 0.000 claims abstract description 43
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 28
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
• 150000002367 halogens Chemical class 0.000 claims abstract description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 27
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 21
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 16
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 14
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 14
• 239000001257 hydrogen Substances 0.000 claims abstract description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
• 239000012634 fragment Substances 0.000 claims abstract description 8
• 239000004305 biphenyl Substances 0.000 claims abstract description 7
• 235000010290 biphenyl Nutrition 0.000 claims abstract description 7
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims abstract description 7
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 6
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 3
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 3
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 10
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract 4
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract 3
• 125000004950 trifluoroalkyl group Chemical group 0.000 claims abstract 3
• HPARLNRMYDSBNO-UHFFFAOYSA-N 1,4-benzodioxine Chemical compound C1=CC=C2OC=COC2=C1 HPARLNRMYDSBNO-UHFFFAOYSA-N 0.000 claims abstract 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims abstract 2
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 2
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract 2
• 239000012964 benzotriazole Substances 0.000 claims abstract 2
• 125000002541 furyl group Chemical group 0.000 claims abstract 2
• 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
• 125000001544 thienyl group Chemical group 0.000 claims abstract 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 394
• 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 203
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 146
• 125000000217 alkyl group Chemical group 0.000 claims description 103
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 54
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 49
• 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 13
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 8
• APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 239000010802 sludge Substances 0.000 claims description 7
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 6
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims description 5
• PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• 125000003974 3-carbamimidamidopropyl group Chemical group C(N)(=N)NCCC* 0.000 claims description 2
• 125000005336 allyloxy group Chemical group 0.000 claims description 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 2
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims 1
• 125000000842 isoxazolyl group Chemical group 0.000 claims 1
• JEPAGMKWFWQECH-UHFFFAOYSA-N n-(4-chlorophenyl)prop-2-enamide Chemical compound ClC1=CC=C(NC(=O)C=C)C=C1 JEPAGMKWFWQECH-UHFFFAOYSA-N 0.000 claims 1
• SJPFDTCYOWNRRA-QIZHTYKGSA-N n-[3-[(2s,7s)-4-(2,2-diphenylethyl)-7-[[[(e)-3-(4-methylphenyl)prop-2-enoyl]amino]methyl]-3-oxo-1,4-diazepan-2-yl]propyl]cyclohexanecarboxamide Chemical compound C1=CC(C)=CC=C1\C=C\C(=O)NC[C@H]1N[C@@H](CCCNC(=O)C2CCCCC2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 SJPFDTCYOWNRRA-QIZHTYKGSA-N 0.000 claims 1
• 230000000694 effects Effects 0.000 abstract description 15
• 239000000126 substance Substances 0.000 abstract description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 9
• 239000003814 drug Substances 0.000 abstract description 6
• DRRVROVYLJHJIV-UHFFFAOYSA-N 1,4-diazepan-2-one Chemical class O=C1CNCCCN1 DRRVROVYLJHJIV-UHFFFAOYSA-N 0.000 abstract description 3
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 441
• 125000006239 protecting group Chemical group 0.000 description 167
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 160
• 238000010511 deprotection reaction Methods 0.000 description 149
• 239000000203 mixture Substances 0.000 description 122
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 114
• 230000015572 biosynthetic process Effects 0.000 description 111
• 238000003786 synthesis reaction Methods 0.000 description 100
• 239000000243 solution Substances 0.000 description 95
• 238000006243 chemical reaction Methods 0.000 description 88
• 238000004128 high performance liquid chromatography Methods 0.000 description 73
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 62
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 60
• 229940124280 l-arginine Drugs 0.000 description 59
• 230000002829 reductive effect Effects 0.000 description 58
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 57
• 239000000047 product Substances 0.000 description 55
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 51
• 238000000746 purification Methods 0.000 description 50
• 150000001412 amines Chemical class 0.000 description 48
• 238000000034 method Methods 0.000 description 47
• LIWKOFAHRLBNMG-FQEVSTJZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-4-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCNC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 LIWKOFAHRLBNMG-FQEVSTJZSA-N 0.000 description 43
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
• 239000012267 brine Substances 0.000 description 40
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
• HNICLNKVURBTKV-NDEPHWFRSA-N (2s)-5-[[amino-[(2,2,4,6,7-pentamethyl-3h-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N[C@H](C(O)=O)CCCN=C(N)NS(=O)(=O)C1=C(C)C(C)=C2OC(C)(C)CC2=C1C HNICLNKVURBTKV-NDEPHWFRSA-N 0.000 description 38
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 36
• 208000002874 Acne Vulgaris Diseases 0.000 description 34
• 206010000496 acne Diseases 0.000 description 34
• 210000002374 sebum Anatomy 0.000 description 34
• 125000002391 4-chlorocinnamoyl group Chemical group 0.000 description 33
• 229920006395 saturated elastomer Polymers 0.000 description 33
• UTZVSIXTYYWUOB-USJZOSNVSA-N 2-[(1s,2s,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-n-methoxy-n-methylacetamide Chemical compound CC1(C)CCC[C@]2(C)[C@H](CC(=O)N(C)OC)[C@@](C)(O)CC[C@H]21 UTZVSIXTYYWUOB-USJZOSNVSA-N 0.000 description 31
• 239000007787 solid Substances 0.000 description 30
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
• 230000004048 modification Effects 0.000 description 29
• 238000012986 modification Methods 0.000 description 29
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• 125000000753 cycloalkyl group Chemical group 0.000 description 28
• 239000002904 solvent Substances 0.000 description 27
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• 238000002390 rotary evaporation Methods 0.000 description 26
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• 150000002576 ketones Chemical class 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• 238000011282 treatment Methods 0.000 description 22
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• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 18
• 125000003342 alkenyl group Chemical group 0.000 description 18
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 18
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 17
• SHGAZHPCJJPHSC-NUEINMDLSA-N Isotretinoin Chemical compound OC(=O)C=C(C)/C=C/C=C(C)C=CC1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-NUEINMDLSA-N 0.000 description 16
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• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
• 239000003995 emulsifying agent Substances 0.000 description 14
• 238000003818 flash chromatography Methods 0.000 description 14
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• PKAUMAVONPSDRW-IBGZPJMESA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CNC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 PKAUMAVONPSDRW-IBGZPJMESA-N 0.000 description 13
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• 125000003545 alkoxy group Chemical group 0.000 description 13
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• 230000014509 gene expression Effects 0.000 description 13
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• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• 125000002950 monocyclic group Chemical group 0.000 description 12
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