RU2555343C9 - Способы модулирования активности мс5 рецептора и лечение состояний, относящихся к данному рецептору - Google Patents

Info

Publication number

RU2555343C9

RU2555343C9 RU2010137030/15A RU2010137030A RU2555343C9 RU 2555343 C9 RU2555343 C9 RU 2555343C9 RU 2010137030/15 A RU2010137030/15 A RU 2010137030/15A RU 2010137030 A RU2010137030 A RU 2010137030A RU 2555343 C9 RU2555343 C9 RU 2555343C9

Authority

RU

Russia

Prior art keywords

methyl

oxo

diazepan

diphenylethyl

naphthamide

Prior art date

2008-02-29

Links

• Espacenet
• Global Dossier
• Discuss

• 230000000694 effects Effects 0.000 title claims abstract description 28
• 238000000034 method Methods 0.000 title claims description 74
• 238000011282 treatment Methods 0.000 title abstract description 27
• 150000001875 compounds Chemical class 0.000 claims abstract description 206
• 108010088565 Melanocortin 5 receptor Proteins 0.000 claims abstract description 66
• 102000030612 Melanocortin 5 receptor Human genes 0.000 claims abstract description 66
• -1 acrylamide - N - (((3S, 5S) -3- (2-aminoethyl) -2-oxo-1- (2-phenylbutyl) -1,4-diazepan-5-yl) methyl) -2-naphthamide Chemical compound 0.000 claims description 902
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 436
• 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 218
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 170
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 67
• 230000002829 reductive effect Effects 0.000 claims description 60
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 58
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
• 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 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 241000124008 Mammalia Species 0.000 claims description 14
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 8
• 239000010802 sludge Substances 0.000 claims description 7
• LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims description 6
• 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
• APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 6
• APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 claims description 5
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 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
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 4
• 230000002401 inhibitory effect Effects 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
• GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-UHFFFAOYSA-N 0.000 claims description 2
• DEPCHJKRPDKDGR-VMPREFPWSA-N 6-chloro-n-[[(3s,5s)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCCCC1)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)Cl)CN1CC1=CC(Cl)=CC(Cl)=C1 DEPCHJKRPDKDGR-VMPREFPWSA-N 0.000 claims description 2
• 125000005336 allyloxy group Chemical group 0.000 claims description 2
• 230000003247 decreasing effect Effects 0.000 claims description 2
• SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 claims description 2
• LVLRCGQAMVAAFS-QPQPGPPRSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]adamantane-1-carboxamide Chemical compound C([C@@H](CNC(=O)C12CC3CC(CC(C3)C1)C2)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 LVLRCGQAMVAAFS-QPQPGPPRSA-N 0.000 claims description 2
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 2
• GBRBKMXUVRDDFI-UHFFFAOYSA-N 4-(3,5-dimethylpyrazol-1-yl)benzamide Chemical compound N1=C(C)C=C(C)N1C1=CC=C(C(N)=O)C=C1 GBRBKMXUVRDDFI-UHFFFAOYSA-N 0.000 claims 1
• LUQVCHRDAGWYMG-UHFFFAOYSA-N 4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1 LUQVCHRDAGWYMG-UHFFFAOYSA-N 0.000 claims 1
• RUVGWFCTTWSCRR-UHFFFAOYSA-N 4-pyrrol-1-ylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1N1C=CC=C1 RUVGWFCTTWSCRR-UHFFFAOYSA-N 0.000 claims 1
• WBPYFGKGONNAFR-ZURQMKNRSA-N C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN=C(N)N)CN1CC(C(O)=O)C1=CC=CC=C1 Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN=C(N)N)CN1CC(C(O)=O)C1=CC=CC=C1 WBPYFGKGONNAFR-ZURQMKNRSA-N 0.000 claims 1
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
• 208000002874 Acne Vulgaris Diseases 0.000 abstract description 39
• 206010000496 acne Diseases 0.000 abstract description 39
• 239000003814 drug Substances 0.000 abstract description 15
• 208000008742 seborrheic dermatitis Diseases 0.000 abstract description 15
• 239000000126 substance Substances 0.000 abstract description 14
• 201000010099 disease Diseases 0.000 abstract description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
• 206010039792 Seborrhoea Diseases 0.000 abstract description 9
• 206010039793 Seborrhoeic dermatitis Diseases 0.000 abstract description 7
• 206010028980 Neoplasm Diseases 0.000 abstract description 5
• 230000009467 reduction Effects 0.000 abstract description 4
• 230000004071 biological effect Effects 0.000 abstract description 3
• 230000033228 biological regulation Effects 0.000 abstract description 3
• 201000011510 cancer Diseases 0.000 abstract 1
• 230000002349 favourable effect Effects 0.000 abstract 1
• 208000027866 inflammatory disease Diseases 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 429
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 158
• 125000006239 protecting group Chemical group 0.000 description 155
• 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 127
• 239000000203 mixture Substances 0.000 description 123
• 230000015572 biosynthetic process Effects 0.000 description 111
• 238000003786 synthesis reaction Methods 0.000 description 101
• 238000010511 deprotection reaction Methods 0.000 description 92
• 239000000243 solution Substances 0.000 description 88
• 125000000217 alkyl group Chemical group 0.000 description 86
• 238000006243 chemical reaction Methods 0.000 description 84
• 238000004128 high performance liquid chromatography Methods 0.000 description 73
• 125000003118 aryl group Chemical group 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 64
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
• 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 59
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 57
• 229940124280 l-arginine Drugs 0.000 description 56
• 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 47
• 125000001072 heteroaryl group Chemical group 0.000 description 46
• 125000002391 4-chlorocinnamoyl group Chemical group 0.000 description 44
• 229910052739 hydrogen Inorganic materials 0.000 description 42
• 239000000047 product Substances 0.000 description 39
• 239000012267 brine Substances 0.000 description 38
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 38
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 38
• 210000002374 sebum Anatomy 0.000 description 36
• 229920006395 saturated elastomer Polymers 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 125000000753 cycloalkyl group Chemical group 0.000 description 31
• 239000007787 solid Substances 0.000 description 30
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 238000003756 stirring Methods 0.000 description 26
• 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 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 238000002390 rotary evaporation Methods 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• 125000004404 heteroalkyl group Chemical group 0.000 description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 23
• 125000001424 substituent group Chemical group 0.000 description 23
• 239000012043 crude product Substances 0.000 description 22
• 150000002576 ketones Chemical class 0.000 description 22
• 229910052757 nitrogen Inorganic materials 0.000 description 22
• 239000003921 oil Substances 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
• 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 21
• 239000012074 organic phase Substances 0.000 description 21
• 238000002953 preparative HPLC Methods 0.000 description 21
• 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 20
• 230000014509 gene expression Effects 0.000 description 20
• 235000019198 oils Nutrition 0.000 description 20
• 239000011541 reaction mixture Substances 0.000 description 20
• 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 description 19
• 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 18
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 18
• 229910052799 carbon Inorganic materials 0.000 description 18
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 125000003342 alkenyl group Chemical group 0.000 description 17
• 150000001413 amino acids Chemical group 0.000 description 17
• 125000004429 atom Chemical group 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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
• 239000003153 chemical reaction reagent Substances 0.000 description 16
• 230000004048 modification Effects 0.000 description 16
• 238000012986 modification Methods 0.000 description 16
• 210000001732 sebaceous gland Anatomy 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 229960005280 isotretinoin Drugs 0.000 description 15
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
• 239000003995 emulsifying agent Substances 0.000 description 14
• 238000001704 evaporation Methods 0.000 description 14
• 230000008020 evaporation Effects 0.000 description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
• 238000004519 manufacturing process Methods 0.000 description 14
• 230000028327 secretion Effects 0.000 description 14
• 238000010898 silica gel chromatography Methods 0.000 description 14
• 238000007792 addition Methods 0.000 description 13
• 150000001408 amides Chemical group 0.000 description 13
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
• 125000003545 alkoxy group Chemical group 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 238000003818 flash chromatography Methods 0.000 description 12
• 239000012634 fragment Substances 0.000 description 12
• 125000002950 monocyclic group Chemical group 0.000 description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 description 12
• 239000000741 silica gel Substances 0.000 description 12
• 229910002027 silica gel Inorganic materials 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• BDHUTRNYBGWPBL-HNNXBMFYSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCCCNC(=O)OCC1=CC=CC=C1 BDHUTRNYBGWPBL-HNNXBMFYSA-N 0.000 description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• 241000282414 Homo sapiens Species 0.000 description 11
• 241000699670 Mus sp. Species 0.000 description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 239000000499 gel Substances 0.000 description 11
• 239000001257 hydrogen Substances 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 10
• 125000002619 bicyclic group Chemical group 0.000 description 10
• 230000003197 catalytic effect Effects 0.000 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 description 10
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
• 235000019197 fats Nutrition 0.000 description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
• 210000004378 sebocyte Anatomy 0.000 description 10
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 9
• RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 235000014113 dietary fatty acids Nutrition 0.000 description 9
• 230000003828 downregulation Effects 0.000 description 9
• 229930195729 fatty acid Natural products 0.000 description 9
• 239000000194 fatty acid Substances 0.000 description 9
• 229910052731 fluorine Inorganic materials 0.000 description 9
• 125000004430 oxygen atom Chemical group O* 0.000 description 9
• 102000005962 receptors Human genes 0.000 description 9
• 108020003175 receptors Proteins 0.000 description 9
• 241000282412 Homo Species 0.000 description 8
• 102000004378 Melanocortin Receptors Human genes 0.000 description 8
• 108090000950 Melanocortin Receptors Proteins 0.000 description 8
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
• 125000003710 aryl alkyl group Chemical group 0.000 description 8
• 229910052794 bromium Inorganic materials 0.000 description 8
• 239000012230 colorless oil Substances 0.000 description 8
• 125000004122 cyclic group Chemical group 0.000 description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 description 8
• 239000003480 eluent Substances 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 239000012467 final product Substances 0.000 description 8
• 229910052736 halogen Inorganic materials 0.000 description 8
• 150000002367 halogens Chemical class 0.000 description 8
• 230000001965 increasing effect Effects 0.000 description 8
• 239000010410 layer Substances 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• 229920001223 polyethylene glycol Polymers 0.000 description 8
• 238000005932 reductive alkylation reaction Methods 0.000 description 8
• 210000003491 skin Anatomy 0.000 description 8
• 239000001993 wax Substances 0.000 description 8
• 102400000740 Melanocyte-stimulating hormone alpha Human genes 0.000 description 7
• 101710200814 Melanotropin alpha Proteins 0.000 description 7
• 102100027467 Pro-opiomelanocortin Human genes 0.000 description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
• 230000007423 decrease Effects 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• 239000000839 emulsion Substances 0.000 description 7
• 150000002148 esters Chemical class 0.000 description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
• 125000000623 heterocyclic group Chemical group 0.000 description 7
• 125000004366 heterocycloalkenyl group Chemical group 0.000 description 7
• 125000001624 naphthyl group Chemical group 0.000 description 7
• 125000003367 polycyclic group Chemical group 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 238000004809 thin layer chromatography Methods 0.000 description 7
• 230000000699 topical effect Effects 0.000 description 7
• WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 7
• UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 6
• 125000002252 acyl group Chemical group 0.000 description 6
• 235000001014 amino acid Nutrition 0.000 description 6
• 239000012298 atmosphere Substances 0.000 description 6
• 210000004027 cell Anatomy 0.000 description 6
• 229920001577 copolymer Polymers 0.000 description 6
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 238000011161 development Methods 0.000 description 6
• 235000019441 ethanol Nutrition 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 125000005842 heteroatom Chemical group 0.000 description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
• USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 6
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 6
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
• 125000004434 sulfur atom Chemical group 0.000 description 6
• 239000002562 thickening agent Substances 0.000 description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• 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 5
• IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
• 125000005916 2-methylpentyl group Chemical group 0.000 description 5
• 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 5
• 239000007821 HATU Substances 0.000 description 5
• 239000002202 Polyethylene glycol Substances 0.000 description 5
• 241000700159 Rattus Species 0.000 description 5
• 229910004298 SiO 2 Inorganic materials 0.000 description 5
• 239000013543 active substance Substances 0.000 description 5
• 125000001931 aliphatic group Chemical group 0.000 description 5
• 125000000304 alkynyl group Chemical group 0.000 description 5
• 229940024606 amino acid Drugs 0.000 description 5
• 239000005557 antagonist Substances 0.000 description 5
• 239000003242 anti bacterial agent Substances 0.000 description 5
• 229940088710 antibiotic agent Drugs 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• 125000004104 aryloxy group Chemical group 0.000 description 5
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
• 239000004305 biphenyl Substances 0.000 description 5
• 235000010290 biphenyl Nutrition 0.000 description 5
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 239000003085 diluting agent Substances 0.000 description 5
• PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 5
• 239000003937 drug carrier Substances 0.000 description 5
• 125000001188 haloalkyl group Chemical group 0.000 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 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
• 239000011259 mixed solution Substances 0.000 description 5
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 5
• 229910052760 oxygen Inorganic materials 0.000 description 5
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
• 239000000546 pharmaceutical excipient Substances 0.000 description 5
• 108090000765 processed proteins & peptides Proteins 0.000 description 5
• 238000006268 reductive amination reaction Methods 0.000 description 5
• 238000007363 ring formation reaction Methods 0.000 description 5
• 125000006413 ring segment Chemical group 0.000 description 5
• 241000894007 species Species 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 229920002554 vinyl polymer Polymers 0.000 description 5
• JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 4
• AQTUACKQXJNHFQ-LURJTMIESA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanedioic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(O)=O AQTUACKQXJNHFQ-LURJTMIESA-N 0.000 description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
• VVSASNKOFCZVES-UHFFFAOYSA-N 1,3-dimethyl-1,3-diazinane-2,4,6-trione Chemical compound CN1C(=O)CC(=O)N(C)C1=O VVSASNKOFCZVES-UHFFFAOYSA-N 0.000 description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
• UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
• 238000010521 absorption reaction Methods 0.000 description 4
• 210000001789 adipocyte Anatomy 0.000 description 4
• 125000003302 alkenyloxy group Chemical group 0.000 description 4
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
• 125000005133 alkynyloxy group Chemical group 0.000 description 4
• 125000004103 aminoalkyl group Chemical group 0.000 description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
• 230000037396 body weight Effects 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 239000004359 castor oil Substances 0.000 description 4
• 230000001276 controlling effect Effects 0.000 description 4
• 239000013058 crude material Substances 0.000 description 4
• 125000000000 cycloalkoxy group Chemical group 0.000 description 4
• PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 4
• 238000001514 detection method Methods 0.000 description 4
• 239000006185 dispersion Substances 0.000 description 4
• 239000008298 dragée Substances 0.000 description 4
• 150000002191 fatty alcohols Chemical class 0.000 description 4
• 125000005456 glyceride group Chemical group 0.000 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 description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 description 4
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 4
• 230000007062 hydrolysis Effects 0.000 description 4
• 238000006460 hydrolysis reaction Methods 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 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 description 4
• 108090000629 orphan nuclear receptors Proteins 0.000 description 4
• 102000004164 orphan nuclear receptors Human genes 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 239000012188 paraffin wax Substances 0.000 description 4
• 239000008194 pharmaceutical composition Substances 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• 229920000728 polyester Polymers 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 229960004063 propylene glycol Drugs 0.000 description 4
• 239000011593 sulfur Substances 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• 238000002560 therapeutic procedure Methods 0.000 description 4
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
• VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 3
• YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 3
• YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 3
• 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 description 3
• PWXPFYVNYKVJBW-ZZXKWVIFSA-N (e)-3-(4-chlorophenyl)prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=C(Cl)C=C1 PWXPFYVNYKVJBW-ZZXKWVIFSA-N 0.000 description 3
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
• LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
• NPMCAVBMOTZUPD-UHFFFAOYSA-N 6-bromonaphthalene-2-carboxylic acid Chemical compound C1=C(Br)C=CC2=CC(C(=O)O)=CC=C21 NPMCAVBMOTZUPD-UHFFFAOYSA-N 0.000 description 3
• PLXBZRBLWZSFDH-LNMMVMNESA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-LNMMVMNESA-N 0.000 description 3
• 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 description 3
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
• 239000004342 Benzoyl peroxide Substances 0.000 description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
• 241000186427 Cutibacterium acnes Species 0.000 description 3
• 101001134060 Homo sapiens Melanocyte-stimulating hormone receptor Proteins 0.000 description 3
• 241000282560 Macaca mulatta Species 0.000 description 3
• 108010007013 Melanocyte-Stimulating Hormones Proteins 0.000 description 3
• 102100034216 Melanocyte-stimulating hormone receptor Human genes 0.000 description 3
• 241001494479 Pecora Species 0.000 description 3
• 108010069820 Pro-Opiomelanocortin Proteins 0.000 description 3
• 239000000683 Pro-Opiomelanocortin Substances 0.000 description 3
• 102000001708 Protein Isoforms Human genes 0.000 description 3
• 108010029485 Protein Isoforms Proteins 0.000 description 3
• BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 3
• SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
• 239000004480 active ingredient Substances 0.000 description 3
• 125000004442 acylamino group Chemical group 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 3
• 230000002280 anti-androgenic effect Effects 0.000 description 3
• 239000000051 antiandrogen Substances 0.000 description 3
• 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 3
• 125000005018 aryl alkenyl group Chemical group 0.000 description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
• 125000001769 aryl amino group Chemical group 0.000 description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 3
• XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
• 235000019400 benzoyl peroxide Nutrition 0.000 description 3
• 238000009835 boiling Methods 0.000 description 3
• 210000004556 brain Anatomy 0.000 description 3
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
• 239000002775 capsule Substances 0.000 description 3
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
• 235000019438 castor oil Nutrition 0.000 description 3
• 238000004113 cell culture Methods 0.000 description 3
• 230000008859 change Effects 0.000 description 3
• 238000000576 coating method Methods 0.000 description 3
• 238000004440 column chromatography Methods 0.000 description 3
• 229940125844 compound 46 Drugs 0.000 description 3
• 238000005859 coupling reaction Methods 0.000 description 3
• 239000006071 cream Substances 0.000 description 3
• 125000004465 cycloalkenyloxy group Chemical group 0.000 description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 3
• VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 3
• 239000002027 dichloromethane extract Substances 0.000 description 3
• 238000009826 distribution Methods 0.000 description 3
• 239000002552 dosage form Substances 0.000 description 3
• 230000002222 downregulating effect Effects 0.000 description 3
• 239000000284 extract Substances 0.000 description 3
• 150000004665 fatty acids Chemical class 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 235000011187 glycerol Nutrition 0.000 description 3
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
• 239000008187 granular material Substances 0.000 description 3
• 125000000262 haloalkenyl group Chemical group 0.000 description 3
• 125000000232 haloalkynyl group Chemical group 0.000 description 3
• 125000005843 halogen group Chemical group 0.000 description 3
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
• 208000015181 infectious disease Diseases 0.000 description 3
• 230000028709 inflammatory response Effects 0.000 description 3
• 239000007924 injection Substances 0.000 description 3
• 238000002347 injection Methods 0.000 description 3
• 150000002632 lipids Chemical class 0.000 description 3
• 239000002502 liposome Substances 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• 239000002609 medium Substances 0.000 description 3
• 108020004999 messenger RNA Proteins 0.000 description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
• 239000002480 mineral oil Substances 0.000 description 3
• 239000000178 monomer Substances 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 239000004006 olive oil Substances 0.000 description 3
• 150000007524 organic acids Chemical class 0.000 description 3
• 230000037361 pathway Effects 0.000 description 3
• 125000003386 piperidinyl group Chemical group 0.000 description 3
• 229920001296 polysiloxane Polymers 0.000 description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
• 230000035755 proliferation Effects 0.000 description 3
• CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 3
• 125000004742 propyloxycarbonyl group Chemical group 0.000 description 3
• 238000006722 reduction reaction Methods 0.000 description 3
• 230000001105 regulatory effect Effects 0.000 description 3
• 150000003335 secondary amines Chemical class 0.000 description 3
• 239000007909 solid dosage form Substances 0.000 description 3
• 229940031439 squalene Drugs 0.000 description 3
• TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 3
• 150000003431 steroids Chemical class 0.000 description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 229960003604 testosterone Drugs 0.000 description 3
• 239000012049 topical pharmaceutical composition Substances 0.000 description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
• PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
• UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
• IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
• CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 2
• ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 2
• PLWALTDUYKDGRF-SECBINFHSA-N (2s)-2-phenylbutan-1-amine Chemical compound CC[C@H](CN)C1=CC=CC=C1 PLWALTDUYKDGRF-SECBINFHSA-N 0.000 description 2
• MJZDTTZGQUEOBL-FQEVSTJZSA-N (2s)-4-(9h-fluoren-9-ylmethoxycarbonylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound C1=CC=C2C(COC(=O)NCC[C@H](NC(=O)OC(C)(C)C)C(O)=O)C3=CC=CC=C3C2=C1 MJZDTTZGQUEOBL-FQEVSTJZSA-N 0.000 description 2
• ZZDRDGKSMGGBDI-KRWDZBQOSA-N (2s)-4-azaniumyl-2-(9h-fluoren-9-ylmethoxycarbonylamino)butanoate Chemical compound C1=CC=C2C(COC(=O)N[C@@H](CCN)C(O)=O)C3=CC=CC=C3C2=C1 ZZDRDGKSMGGBDI-KRWDZBQOSA-N 0.000 description 2
• ICIJWOWQUHHETJ-UHFFFAOYSA-N (3,5-dichlorophenyl)methanamine Chemical compound NCC1=CC(Cl)=CC(Cl)=C1 ICIJWOWQUHHETJ-UHFFFAOYSA-N 0.000 description 2
• OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 2
• MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
• ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 2
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N 1,3-di(propan-2-yl)urea Chemical compound CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 2
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
• QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 2
• NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
• RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 2
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
• 108700034262 4-Nle-7-Phe-alpha- MSH Proteins 0.000 description 2
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
• 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 2
• PLXBZRBLWZSFDH-ZIIROOFJSA-N 6-chloro-n-[[(3r,5r)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H]1N[C@@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-ZIIROOFJSA-N 0.000 description 2
• PLXBZRBLWZSFDH-FWGANANOSA-N 6-chloro-n-[[(3r,5s)-2-oxo-1-[(2r)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-FWGANANOSA-N 0.000 description 2
• PLXBZRBLWZSFDH-FXZLDBAYSA-N 6-chloro-n-[[(3s,5r)-2-oxo-1-[(2r)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-FXZLDBAYSA-N 0.000 description 2
• PLXBZRBLWZSFDH-QHZFHHJPSA-N 6-chloro-n-[[(3s,5r)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-QHZFHHJPSA-N 0.000 description 2
• PLXBZRBLWZSFDH-OATBXSGESA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2r)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-OATBXSGESA-N 0.000 description 2
• YZMKIBCZAOOWRS-UHFFFAOYSA-N 6-chloronaphthalene-2-carboxamide Chemical compound C1=C(Cl)C=CC2=CC(C(=O)N)=CC=C21 YZMKIBCZAOOWRS-UHFFFAOYSA-N 0.000 description 2
• SRISHMVSUHENAI-UHFFFAOYSA-N 6-chloronaphthalene-2-carboxylic acid Chemical compound C1=C(Cl)C=CC2=CC(C(=O)O)=CC=C21 SRISHMVSUHENAI-UHFFFAOYSA-N 0.000 description 2
• CYKDCZRPLWJEKA-UHFFFAOYSA-N 6-fluoronaphthalene-2-carboxylic acid Chemical compound C1=C(F)C=CC2=CC(C(=O)O)=CC=C21 CYKDCZRPLWJEKA-UHFFFAOYSA-N 0.000 description 2
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• 102100022455 Adrenocorticotropic hormone receptor Human genes 0.000 description 2
• 102000054930 Agouti-Related Human genes 0.000 description 2
• 101710127426 Agouti-related protein Proteins 0.000 description 2
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
• 101100351303 Caenorhabditis elegans pdfr-1 gene Proteins 0.000 description 2
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
• 241000282472 Canis lupus familiaris Species 0.000 description 2
• 101800000414 Corticotropin Proteins 0.000 description 2
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
• 201000004624 Dermatitis Diseases 0.000 description 2
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
• 241001656095 Echinorhinus brucus Species 0.000 description 2
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 2
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 2
• 241000287828 Gallus gallus Species 0.000 description 2
• 108010010803 Gelatin Proteins 0.000 description 2
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• 239000004471 Glycine Substances 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 101000678419 Homo sapiens Adrenocorticotropic hormone receptor Proteins 0.000 description 2
• 101000978431 Homo sapiens Melanocortin receptor 3 Proteins 0.000 description 2
• 101000978418 Homo sapiens Melanocortin receptor 4 Proteins 0.000 description 2
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
• 206010061218 Inflammation Diseases 0.000 description 2
• 239000004166 Lanolin Substances 0.000 description 2
• 241000272168 Laridae Species 0.000 description 2
• 102100023726 Melanocortin receptor 3 Human genes 0.000 description 2
• 102100023724 Melanocortin receptor 4 Human genes 0.000 description 2
• 201000005979 Muir-Torre Syndrome Diseases 0.000 description 2
• AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
• QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 2
• 241000277275 Oncorhynchus mykiss Species 0.000 description 2
• AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 2
• 206010033733 Papule Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• 229920002472 Starch Polymers 0.000 description 2
• 235000021355 Stearic acid Nutrition 0.000 description 2
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
• 229930006000 Sucrose Natural products 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• 235000019486 Sunflower oil Nutrition 0.000 description 2
• 239000004098 Tetracycline Substances 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• 239000004164 Wax ester Substances 0.000 description 2
• OGQICQVSFDPSEI-UHFFFAOYSA-N Zorac Chemical compound N1=CC(C(=O)OCC)=CC=C1C#CC1=CC=C(SCCC2(C)C)C2=C1 OGQICQVSFDPSEI-UHFFFAOYSA-N 0.000 description 2
• LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• 230000004913 activation Effects 0.000 description 2
• 125000002015 acyclic group Chemical group 0.000 description 2
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
• 229960002916 adapalene Drugs 0.000 description 2
• LZCDAPDGXCYOEH-UHFFFAOYSA-N adapalene Chemical compound C1=C(C(O)=O)C=CC2=CC(C3=CC=C(C(=C3)C34CC5CC(CC(C5)C3)C4)OC)=CC=C21 LZCDAPDGXCYOEH-UHFFFAOYSA-N 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• UAHFGYDRQSXQEB-LEBBXHLNSA-N afamelanotide Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 UAHFGYDRQSXQEB-LEBBXHLNSA-N 0.000 description 2
• 235000010443 alginic acid Nutrition 0.000 description 2
• 229920000615 alginic acid Polymers 0.000 description 2
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
• 125000002947 alkylene group Chemical group 0.000 description 2
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
• 238000004458 analytical method Methods 0.000 description 2
• 239000003098 androgen Substances 0.000 description 2
• 230000008485 antagonism Effects 0.000 description 2
• 230000003255 anti-acne Effects 0.000 description 2
• 230000003110 anti-inflammatory effect Effects 0.000 description 2
• 239000008346 aqueous phase Substances 0.000 description 2
• BQMNFPBUAQPINY-UHFFFAOYSA-N azane;2-methyl-2-(prop-2-enoylamino)propane-1-sulfonic acid Chemical compound [NH4+].[O-]S(=O)(=O)CC(C)(C)NC(=O)C=C BQMNFPBUAQPINY-UHFFFAOYSA-N 0.000 description 2
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 235000013871 bee wax Nutrition 0.000 description 2
• 239000012166 beeswax Substances 0.000 description 2
• 230000009286 beneficial effect Effects 0.000 description 2
• 239000000440 bentonite Substances 0.000 description 2
• 229910000278 bentonite Inorganic materials 0.000 description 2
• 235000012216 bentonite Nutrition 0.000 description 2
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
• 229960003328 benzoyl peroxide Drugs 0.000 description 2
• SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
• 239000011230 binding agent Substances 0.000 description 2
• 230000031018 biological processes and functions Effects 0.000 description 2
• 125000001246 bromo group Chemical group Br* 0.000 description 2
• 239000006227 byproduct Substances 0.000 description 2
• 239000004204 candelilla wax Substances 0.000 description 2
• 235000013868 candelilla wax Nutrition 0.000 description 2
• 229940073532 candelilla wax Drugs 0.000 description 2
• GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
• 239000000969 carrier Substances 0.000 description 2
• 230000001413 cellular effect Effects 0.000 description 2
• 239000003610 charcoal Substances 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
• 230000001684 chronic effect Effects 0.000 description 2
• KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 2
• 229960002227 clindamycin Drugs 0.000 description 2
• 229940110456 cocoa butter Drugs 0.000 description 2
• 235000019868 cocoa butter Nutrition 0.000 description 2
• 229940125810 compound 20 Drugs 0.000 description 2
• 229940126086 compound 21 Drugs 0.000 description 2
• 229940125807 compound 37 Drugs 0.000 description 2
• 229940125898 compound 5 Drugs 0.000 description 2
• 238000001816 cooling Methods 0.000 description 2
• IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 2
• 229960000258 corticotropin Drugs 0.000 description 2
• 230000008878 coupling Effects 0.000 description 2
• 238000010168 coupling process Methods 0.000 description 2
• 238000002425 crystallisation Methods 0.000 description 2
• 230000008025 crystallization Effects 0.000 description 2
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 2
• NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
• 229910052805 deuterium Inorganic materials 0.000 description 2
• 206010012601 diabetes mellitus Diseases 0.000 description 2
• 125000004663 dialkyl amino group Chemical group 0.000 description 2
• 125000004986 diarylamino group Chemical group 0.000 description 2
• 235000005911 diet Nutrition 0.000 description 2
• 230000037213 diet Effects 0.000 description 2
• 230000004069 differentiation Effects 0.000 description 2
• 239000004205 dimethyl polysiloxane Substances 0.000 description 2
• 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
• 229960003276 erythromycin Drugs 0.000 description 2
• XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 description 2
• 230000029142 excretion Effects 0.000 description 2
• 239000000945 filler Substances 0.000 description 2
• 125000001153 fluoro group Chemical group F* 0.000 description 2
• 239000008273 gelatin Substances 0.000 description 2
• 229920000159 gelatin Polymers 0.000 description 2
• 235000019322 gelatine Nutrition 0.000 description 2
• 235000011852 gelatine desserts Nutrition 0.000 description 2
• 238000007429 general method Methods 0.000 description 2
• 239000008103 glucose Substances 0.000 description 2
• 238000010438 heat treatment Methods 0.000 description 2
• IUJAMGNYPWYUPM-UHFFFAOYSA-N hentriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IUJAMGNYPWYUPM-UHFFFAOYSA-N 0.000 description 2
• 125000004447 heteroarylalkenyl group Chemical group 0.000 description 2
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
• 229940088597 hormone Drugs 0.000 description 2
• 239000005556 hormone Substances 0.000 description 2
• 238000001794 hormone therapy Methods 0.000 description 2
• 239000003906 humectant Substances 0.000 description 2
• 206010020718 hyperplasia Diseases 0.000 description 2
• 239000003701 inert diluent Substances 0.000 description 2
• 230000004054 inflammatory process Effects 0.000 description 2
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
• 125000002346 iodo group Chemical group I* 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 238000001038 ionspray mass spectrometry Methods 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
• XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 2
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
• 229940119170 jojoba wax Drugs 0.000 description 2
• 239000008101 lactose Substances 0.000 description 2
• 235000019388 lanolin Nutrition 0.000 description 2
• 229940039717 lanolin Drugs 0.000 description 2
• 230000003902 lesion Effects 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 230000000670 limiting effect Effects 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 239000008297 liquid dosage form Substances 0.000 description 2
• 239000006210 lotion Substances 0.000 description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• 239000004005 microsphere Substances 0.000 description 2
• 235000010446 mineral oil Nutrition 0.000 description 2
• 150000007522 mineralic acids Chemical class 0.000 description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
• BQQWQJSSWRPXDB-IMKBVMFZSA-N n-[(1s)-1-[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]-2-naphthalen-2-ylethyl]acetamide Chemical compound C([C@H](N[C@@H](CCCNC(N)=N)C1=O)[C@H](CC=2C=C3C=CC=CC3=CC=2)NC(=O)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 BQQWQJSSWRPXDB-IMKBVMFZSA-N 0.000 description 2
• UGKNGKJOAUUJRL-UHFFFAOYSA-N n-[2-[methoxy(methyl)amino]-2-oxoethyl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)NCC(=O)N(C)OC)=CC=C21 UGKNGKJOAUUJRL-UHFFFAOYSA-N 0.000 description 2
• DKFQXTHTGAKMJQ-XLJNKUFUSA-N n-[[(3r,5r)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DKFQXTHTGAKMJQ-XLJNKUFUSA-N 0.000 description 2
• DKFQXTHTGAKMJQ-XDFJSJKPSA-N n-[[(3r,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DKFQXTHTGAKMJQ-XDFJSJKPSA-N 0.000 description 2
• DKFQXTHTGAKMJQ-BHYZAODMSA-N n-[[(3s,5r)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DKFQXTHTGAKMJQ-BHYZAODMSA-N 0.000 description 2
• KBNVEJCZPFDCIH-LRHLLKFHSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-[3-(propan-2-ylamino)propyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 KBNVEJCZPFDCIH-LRHLLKFHSA-N 0.000 description 2
• WUFPAWGDVHSNQX-WEZIJMHWSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-[3-[(n'-methylcarbamimidoyl)amino]propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)NC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 WUFPAWGDVHSNQX-WEZIJMHWSA-N 0.000 description 2
• FNOCAHWAWWALQQ-MALMBIFMSA-N n-[[(3s,5s)-2-oxo-1-[(2r)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@H](CC)C=1C=CC=CC=1)CN1CCCCC1 FNOCAHWAWWALQQ-MALMBIFMSA-N 0.000 description 2
• FNOCAHWAWWALQQ-GWTOPCPNSA-N n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 FNOCAHWAWWALQQ-GWTOPCPNSA-N 0.000 description 2
• IVQZHFPXELZMDW-SMCANUKXSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(F)=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 IVQZHFPXELZMDW-SMCANUKXSA-N 0.000 description 2
• JCDGDLIWBJJHQP-GOTSBHOMSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 JCDGDLIWBJJHQP-GOTSBHOMSA-N 0.000 description 2
• QHOCHQYTGSIOPC-ZEQRLZLVSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC1=CC(Cl)=CC(Cl)=C1 QHOCHQYTGSIOPC-ZEQRLZLVSA-N 0.000 description 2
• KIYXBNPDQRSXPO-PHXCCWLDSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCN)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 KIYXBNPDQRSXPO-PHXCCWLDSA-N 0.000 description 2
• WPCLPNAHZOHTIW-WEZIJMHWSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-bromo-n-methylnaphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCN)C1=O)CN(C)C(=O)C=2C=C3C=CC(Br)=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 WPCLPNAHZOHTIW-WEZIJMHWSA-N 0.000 description 2
• PWLOKCRKECNMCH-CDZUIXILSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 PWLOKCRKECNMCH-CDZUIXILSA-N 0.000 description 2
• OGICFAGGMUMKDU-LRHLLKFHSA-N n-[[(3s,5s)-3-[2-(diethylamino)ethyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(F)=CC2=CC=1)N[C@H](C1=O)CCN(CC)CC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 OGICFAGGMUMKDU-LRHLLKFHSA-N 0.000 description 2
• HFJKZDDMHRPINP-WNJJXGMVSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1h-indole-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1NC2=CC=CC=C2C=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HFJKZDDMHRPINP-WNJJXGMVSA-N 0.000 description 2
• WBKKFYBGSRVUDI-XCZPVHLTSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]benzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C1=CC=CC=C1 WBKKFYBGSRVUDI-XCZPVHLTSA-N 0.000 description 2
• DKFQXTHTGAKMJQ-CDZUIXILSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DKFQXTHTGAKMJQ-CDZUIXILSA-N 0.000 description 2
• JNPSAMRJNQMYOH-DQEYMECFSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1=CC(Cl)=CC(Cl)=C1 JNPSAMRJNQMYOH-DQEYMECFSA-N 0.000 description 2
• GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 235000015097 nutrients Nutrition 0.000 description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• 239000002674 ointment Substances 0.000 description 2
• 235000008390 olive oil Nutrition 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 125000000913 palmityl 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])C([H])([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 description 2
• 239000002245 particle Substances 0.000 description 2
• 239000002304 perfume Substances 0.000 description 2
• RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
• 229910052698 phosphorus Inorganic materials 0.000 description 2
• 230000035790 physiological processes and functions Effects 0.000 description 2
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 2
• 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920005862 polyol Polymers 0.000 description 2
• 150000003077 polyols Chemical class 0.000 description 2
• 229920000136 polysorbate Polymers 0.000 description 2
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 239000003755 preservative agent Substances 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• 235000018102 proteins Nutrition 0.000 description 2
• 102000004169 proteins and genes Human genes 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 239000001944 prunus armeniaca kernel oil Substances 0.000 description 2
• CRTBNOWPBHJICM-UHFFFAOYSA-N pyrazine Chemical compound C1=CN=CC=N1.C1=CN=CC=N1 CRTBNOWPBHJICM-UHFFFAOYSA-N 0.000 description 2
• 230000002285 radioactive effect Effects 0.000 description 2
• 210000004761 scalp Anatomy 0.000 description 2
• 235000011803 sesame oil Nutrition 0.000 description 2
• 239000008159 sesame oil Substances 0.000 description 2
• 230000019491 signal transduction Effects 0.000 description 2
• 229920002545 silicone oil Polymers 0.000 description 2
• 239000000344 soap Substances 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 239000008247 solid mixture Substances 0.000 description 2
• 239000000600 sorbitol Substances 0.000 description 2
• 235000012424 soybean oil Nutrition 0.000 description 2
• 239000003549 soybean oil Substances 0.000 description 2
• 238000010186 staining Methods 0.000 description 2
• 235000019698 starch Nutrition 0.000 description 2
• 239000000758 substrate Substances 0.000 description 2
• 239000005720 sucrose Substances 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
• 239000002600 sunflower oil Substances 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 229960000565 tazarotene Drugs 0.000 description 2
• XJVZHKXGDQXSNT-UHFFFAOYSA-N tert-butyl n-[2-[methoxy(methyl)amino]-2-oxoethyl]carbamate Chemical compound CON(C)C(=O)CNC(=O)OC(C)(C)C XJVZHKXGDQXSNT-UHFFFAOYSA-N 0.000 description 2
• 229960002180 tetracycline Drugs 0.000 description 2
• 229930101283 tetracycline Natural products 0.000 description 2
• 235000019364 tetracycline Nutrition 0.000 description 2
• 150000003522 tetracyclines Chemical class 0.000 description 2
• 210000001519 tissue Anatomy 0.000 description 2
• 238000010555 transalkylation reaction Methods 0.000 description 2
• 150000003626 triacylglycerols Chemical class 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 239000003643 water by type Substances 0.000 description 2
• 235000019386 wax ester Nutrition 0.000 description 2
• 239000000080 wetting agent Substances 0.000 description 2
• AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
• ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
• GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
• SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
• GCTFTMWXZFLTRR-GFCCVEGCSA-N (2r)-2-amino-n-[3-(difluoromethoxy)-4-(1,3-oxazol-5-yl)phenyl]-4-methylpentanamide Chemical compound FC(F)OC1=CC(NC(=O)[C@H](N)CC(C)C)=CC=C1C1=CN=CO1 GCTFTMWXZFLTRR-GFCCVEGCSA-N 0.000 description 1
• YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
• DSEKYWAQQVUQTP-XEWMWGOFSA-N (2r,4r,4as,6as,6as,6br,8ar,12ar,14as,14bs)-2-hydroxy-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1h-picen-3-one Chemical compound C([C@H]1[C@]2(C)CC[C@@]34C)C(C)(C)CC[C@]1(C)CC[C@]2(C)[C@H]4CC[C@@]1(C)[C@H]3C[C@@H](O)C(=O)[C@@H]1C DSEKYWAQQVUQTP-XEWMWGOFSA-N 0.000 description 1
• XYXYXSKSTZAEJW-VIFPVBQESA-N (2s)-2-(phenylmethoxycarbonylamino)butanedioic acid Chemical compound OC(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 XYXYXSKSTZAEJW-VIFPVBQESA-N 0.000 description 1
• WJMYMQGGFFEBPP-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxo-5-piperidin-1-ylpentanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CCC(=O)N1CCCCC1 WJMYMQGGFFEBPP-NSHDSACASA-N 0.000 description 1
• WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
• XDEHMKQLKPZERH-BYPYZUCNSA-N (2s)-2-amino-3-methylbutanamide Chemical compound CC(C)[C@H](N)C(N)=O XDEHMKQLKPZERH-BYPYZUCNSA-N 0.000 description 1
• ILYVXUGGBVATGA-DKWTVANSSA-N (2s)-2-aminopropanoic acid;hydrochloride Chemical compound Cl.C[C@H](N)C(O)=O ILYVXUGGBVATGA-DKWTVANSSA-N 0.000 description 1
• DNHNBMQCHKKDNI-SECBINFHSA-N (2s)-2-phenylbutan-1-ol Chemical compound CC[C@H](CO)C1=CC=CC=C1 DNHNBMQCHKKDNI-SECBINFHSA-N 0.000 description 1
• OFJWFSNDPCAWDK-VIFPVBQESA-N (2s)-2-phenylbutanoic acid Chemical compound CC[C@H](C(O)=O)C1=CC=CC=C1 OFJWFSNDPCAWDK-VIFPVBQESA-N 0.000 description 1
• FAXNZPTZQKITLW-NSHDSACASA-N (2s)-4-[methoxy(methyl)amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound CON(C)C(=O)C[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 FAXNZPTZQKITLW-NSHDSACASA-N 0.000 description 1
• STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
• UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
• XAEJSKLIFZIGGW-RUHGTMQNSA-N (3r)-n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-[3-[(n'-methylcarbamimidoyl)amino]propyl]-2-oxo-1,4-diazepan-5-yl]methyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@@H]1NCC2=CC=CC=C2C1)N[C@H](C1=O)CCCNC(=N)NC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 XAEJSKLIFZIGGW-RUHGTMQNSA-N 0.000 description 1
• VHRJTLUSJYUVEM-RUHGTMQNSA-N (3r)-n-[[(3s,5s)-3-(4-aminobutyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@@H]1NCC2=CC=CC=C2C1)N[C@H](C1=O)CCCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VHRJTLUSJYUVEM-RUHGTMQNSA-N 0.000 description 1
• QHDPVOTZDXQHFB-OGXMWTIWSA-N (3r)-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2,3-dihydro-1,4-benzodioxine-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@@H]1OC2=CC=CC=C2OC1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 QHDPVOTZDXQHFB-OGXMWTIWSA-N 0.000 description 1
• HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
• AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical class O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
• VHRJTLUSJYUVEM-GOBOWQCMSA-N (3s)-n-[[(3s,5s)-3-(4-aminobutyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@H]1NCC2=CC=CC=C2C1)N[C@H](C1=O)CCCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VHRJTLUSJYUVEM-GOBOWQCMSA-N 0.000 description 1
• SELTWCXBYXUAHF-ASVWTAOFSA-N (3s)-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@H]1NCC2=CC=CC=C2C1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 SELTWCXBYXUAHF-ASVWTAOFSA-N 0.000 description 1
• QHDPVOTZDXQHFB-XXJPWZBZSA-N (3s)-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2,3-dihydro-1,4-benzodioxine-3-carboxamide Chemical compound C([C@@H](CNC(=O)[C@H]1OC2=CC=CC=C2OC1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 QHDPVOTZDXQHFB-XXJPWZBZSA-N 0.000 description 1
• LAWBFOPWDRGSAA-ROUUACIJSA-N (3s,5s)-5-(aminomethyl)-1-(2-ethylbutyl)-3-(2-piperidin-1-ylethyl)-1,4-diazepan-2-one Chemical compound O=C1N(CC(CC)CC)CC[C@@H](CN)N[C@H]1CCN1CCCCC1 LAWBFOPWDRGSAA-ROUUACIJSA-N 0.000 description 1
• DXEIOFDUNMIKQD-ZQAZVOLISA-N (3s,5s)-5-[[(3,4-dichlorophenyl)methylamino]methyl]-1-(2,2-diphenylethyl)-3-(2-piperidin-1-ylethyl)-1,4-diazepan-2-one Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC[C@H]1N[C@@H](CCN2CCCCC2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 DXEIOFDUNMIKQD-ZQAZVOLISA-N 0.000 description 1
• FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 1
• VUEGYUOUAAVYAS-JGGQBBKZSA-N (6ar,9s,10ar)-9-(dimethylsulfamoylamino)-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline Chemical compound C1=CC([C@H]2C[C@@H](CN(C)[C@@H]2C2)NS(=O)(=O)N(C)C)=C3C2=CNC3=C1 VUEGYUOUAAVYAS-JGGQBBKZSA-N 0.000 description 1
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 description 1
• JSFIMWWDJRWMHJ-VOTSOKGWSA-N (e)-3-(4-methylphenyl)prop-2-enamide Chemical compound CC1=CC=C(\C=C\C(N)=O)C=C1 JSFIMWWDJRWMHJ-VOTSOKGWSA-N 0.000 description 1
• ZCVUMSAODQOJOW-BGMRFITDSA-N (e)-n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-(4-fluorophenyl)-n-methylprop-2-enamide Chemical compound C([C@H](N[C@@H](CCCN)C1=O)CN(C)C(=O)\C=C\C=2C=CC(F)=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ZCVUMSAODQOJOW-BGMRFITDSA-N 0.000 description 1
• PDMNGEJGQQMGAS-VQSCXVRDSA-N (e)-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-methyl-3-phenylprop-2-enamide Chemical compound C([C@H]1N[C@@H](CCCNC(N)=N)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)NC(=O)C(/C)=C/C1=CC=CC=C1 PDMNGEJGQQMGAS-VQSCXVRDSA-N 0.000 description 1
• DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
• HDDGFPOMMDMKBV-HCRUOQKOSA-N (z)-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-fluoro-3-phenylprop-2-enamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C(\F)=C\C1=CC=CC=C1 HDDGFPOMMDMKBV-HCRUOQKOSA-N 0.000 description 1
• ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
• YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical class C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
• CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• 229940058015 1,3-butylene glycol Drugs 0.000 description 1
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
• KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
• DRRVROVYLJHJIV-UHFFFAOYSA-N 1,4-diazepan-2-one Chemical class O=C1CNCCCN1 DRRVROVYLJHJIV-UHFFFAOYSA-N 0.000 description 1
• ZNGWEEUXTBNKFR-UHFFFAOYSA-N 1,4-oxazepane Chemical compound C1CNCCOC1 ZNGWEEUXTBNKFR-UHFFFAOYSA-N 0.000 description 1
• PKVNVXXWANAAFP-UHFFFAOYSA-N 1,7-dihydro-1,4-diazepin-6-one Chemical compound O=C1CNC=CN=C1 PKVNVXXWANAAFP-UHFFFAOYSA-N 0.000 description 1
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
• FZQXMGLQANXZRP-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-(3-imidazol-1-ylpropyl)thiourea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=S)NCCCN1C=NC=C1 FZQXMGLQANXZRP-UHFFFAOYSA-N 0.000 description 1
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
• WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
• KGVCCWDMPOPTEX-IGBKUBFESA-N 1-[(4-chlorophenyl)methyl]-3-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]urea Chemical compound C([C@@H]1CCN(C([C@H](CCN2CCCCC2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)NCC1=CC=C(Cl)C=C1 KGVCCWDMPOPTEX-IGBKUBFESA-N 0.000 description 1
• ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
• LLLWMXQKXWIRDZ-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one Chemical compound C=CN1CCCC1=O.C=CN1CCCC1=O LLLWMXQKXWIRDZ-UHFFFAOYSA-N 0.000 description 1
• WPHBEGTZYVDRQF-NUAIVLOPSA-N 1-methoxy-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C(=C3C=CC=CC3=CC=2)OC)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 WPHBEGTZYVDRQF-NUAIVLOPSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
• IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
• BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 1
• WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical class OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
• WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
• FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
• VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
• 125000003163 2-(2-naphthyl)ethyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(C([H])=C([H])C2=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
• RNAMYOYQYRYFQY-UHFFFAOYSA-N 2-(4,4-difluoropiperidin-1-yl)-6-methoxy-n-(1-propan-2-ylpiperidin-4-yl)-7-(3-pyrrolidin-1-ylpropoxy)quinazolin-4-amine Chemical compound N1=C(N2CCC(F)(F)CC2)N=C2C=C(OCCCN3CCCC3)C(OC)=CC2=C1NC1CCN(C(C)C)CC1 RNAMYOYQYRYFQY-UHFFFAOYSA-N 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 1
• UPRXEZSMODBTRU-UNMCSNQZSA-N 2-[(2s,7s)-7-(aminomethyl)-4-(2,2-diphenylethyl)-3-oxo-1,4-diazepan-2-yl]-n-methoxy-n-methylacetamide Chemical compound O=C1[C@H](CC(=O)N(C)OC)N[C@H](CN)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 UPRXEZSMODBTRU-UNMCSNQZSA-N 0.000 description 1
• OIQOAYVCKAHSEJ-UHFFFAOYSA-N 2-[2,3-bis(2-hydroxyethoxy)propoxy]ethanol;hexadecanoic acid;octadecanoic acid Chemical compound OCCOCC(OCCO)COCCO.CCCCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O OIQOAYVCKAHSEJ-UHFFFAOYSA-N 0.000 description 1
• PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
• VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
• YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
• TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
• YBGBTQXCWHOVIF-UHFFFAOYSA-N 2-amino-n-methoxy-n-methylacetamide Chemical compound CON(C)C(=O)CN YBGBTQXCWHOVIF-UHFFFAOYSA-N 0.000 description 1
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
• MGWAGIQQTULHGU-UHFFFAOYSA-N 2-ethylbutan-1-amine Chemical compound CCC(CC)CN MGWAGIQQTULHGU-UHFFFAOYSA-N 0.000 description 1
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
• 125000003934 2-norbornylethyl group Chemical group [H]C([H])(*)C([H])([H])C1([H])C([H])([H])C2([H])C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
• DNXZKXMSCFGWSA-UHFFFAOYSA-N 2-oxobut-3-enyl carbamate Chemical compound NC(=O)OCC(=O)C=C DNXZKXMSCFGWSA-UHFFFAOYSA-N 0.000 description 1
• YWUUAQSDHCZRNU-UHFFFAOYSA-N 2-phenylbutan-1-amine;hydrochloride Chemical compound Cl.CCC(CN)C1=CC=CC=C1 YWUUAQSDHCZRNU-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• XURBWYCGQQXTHJ-UHFFFAOYSA-N 3,4-dichlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C(Cl)=C1 XURBWYCGQQXTHJ-UHFFFAOYSA-N 0.000 description 1
• 125000006186 3,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C([H])=C1C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 description 1
• RMTFNDVZYPHUEF-XZBKPIIZSA-N 3-O-methyl-D-glucose Chemical class O=C[C@H](O)[C@@H](OC)[C@H](O)[C@H](O)CO RMTFNDVZYPHUEF-XZBKPIIZSA-N 0.000 description 1
• QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
• AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
• 125000002384 3-methylcinnamoyl group Chemical group 0.000 description 1
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
• WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
• 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 1
• SQTLUXJWUCHKMT-UHFFFAOYSA-N 4-bromo-n,n-diphenylaniline Chemical compound C1=CC(Br)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 SQTLUXJWUCHKMT-UHFFFAOYSA-N 0.000 description 1
• 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 description 1
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• NIIWETPFMGGCNJ-CPJSRVTESA-N 5,6-dichloro-2-[[(3s,5s)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]isoindole-1,3-dione Chemical compound ClC1=CC(Cl)=CC(CN2C([C@H](CCN3CCCCC3)N[C@H](CN3C(C4=CC(Cl)=C(Cl)C=C4C3=O)=O)CC2)=O)=C1 NIIWETPFMGGCNJ-CPJSRVTESA-N 0.000 description 1
• 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 1
• XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
• RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
• AHZLHBIQAMKSTD-CDZUIXILSA-N 6-amino-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(N)=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 AHZLHBIQAMKSTD-CDZUIXILSA-N 0.000 description 1
• PZZIFLZQVKUXJX-NSOVKSMOSA-N 6-bromo-n-[[(3s,5s)-1-(2-ethylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Br)=CC3=CC=2)CCN(C1=O)CC(CC)CC)CN1CCCCC1 PZZIFLZQVKUXJX-NSOVKSMOSA-N 0.000 description 1
• CKRUBELSJRPQAA-CDZUIXILSA-N 6-bromo-n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(Br)=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 CKRUBELSJRPQAA-CDZUIXILSA-N 0.000 description 1
• PLXBZRBLWZSFDH-JYJPFYCCSA-N 6-chloro-n-[[(3r,5r)-2-oxo-1-[(2r)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H]1N[C@@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-JYJPFYCCSA-N 0.000 description 1
• UNIUHTXBGLCPAQ-AWHRAJPHSA-N 6-chloro-n-[[(3r,5r)-3-(2-methyl-2-piperidin-1-ylpropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H]1N[C@@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)C(C)(C)N1CCCCC1 UNIUHTXBGLCPAQ-AWHRAJPHSA-N 0.000 description 1
• PLXBZRBLWZSFDH-JHIPEVQNSA-N 6-chloro-n-[[(3r,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 PLXBZRBLWZSFDH-JHIPEVQNSA-N 0.000 description 1
• CSDABATXCTVYHB-NGDHARACSA-N 6-chloro-n-[[(3s)-2-oxo-1-(2-phenylbutyl)-3-piperidin-4-yl-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H]2NC(CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CCN(C2=O)CC(CC)C=2C=CC=CC=2)CCNCC1 CSDABATXCTVYHB-NGDHARACSA-N 0.000 description 1
• RAYWGUBSGQJFLB-GIWKVKTRSA-N 6-chloro-n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCCCC1)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)Cl)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 RAYWGUBSGQJFLB-GIWKVKTRSA-N 0.000 description 1
• KTMMPQNVEBKYCG-LRHLLKFHSA-N 6-chloro-n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-(2-morpholin-4-ylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCOCC1)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)Cl)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 KTMMPQNVEBKYCG-LRHLLKFHSA-N 0.000 description 1
• IMOMRTFCBNFYET-OEJBOCFZSA-N 6-chloro-n-[[(3s,5s)-1-(2-cyclopropylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)CC(CC)C1CC1)CN1CCCCC1 IMOMRTFCBNFYET-OEJBOCFZSA-N 0.000 description 1
• CGGIHAUITVPBSD-NSOVKSMOSA-N 6-chloro-n-[[(3s,5s)-1-(2-ethyl-2-methylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)CC(C)(CC)CC)CN1CCCCC1 CGGIHAUITVPBSD-NSOVKSMOSA-N 0.000 description 1
• AZCPWHXJCFLILD-NSOVKSMOSA-N 6-chloro-n-[[(3s,5s)-1-(2-ethylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)CC(CC)CC)CN1CCCCC1 AZCPWHXJCFLILD-NSOVKSMOSA-N 0.000 description 1
• XITCVVZMRPNABW-YTMVLYRLSA-N 6-chloro-n-[[(3s,5s)-1-[(2,4-dichlorophenyl)methyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CN1C(=O)[C@H](CCN2CCCCC2)N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1 XITCVVZMRPNABW-YTMVLYRLSA-N 0.000 description 1
• QOKWAMNOBLWSAD-OIFPXGRLSA-N 6-chloro-n-[[(3s,5s)-1-[(2r)-2-ethyl-3-methylbut-3-enyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C(C)=C)CN1CCCCC1 QOKWAMNOBLWSAD-OIFPXGRLSA-N 0.000 description 1
• VECSQBGFYNJZBA-OIFPXGRLSA-N 6-chloro-n-[[(3s,5s)-1-[(2r)-2-ethyl-3-methylbutyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@H](CC)C(C)C)CN1CCCCC1 VECSQBGFYNJZBA-OIFPXGRLSA-N 0.000 description 1
• QOKWAMNOBLWSAD-MGONOCMRSA-N 6-chloro-n-[[(3s,5s)-1-[(2s)-2-ethyl-3-methylbut-3-enyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C(C)=C)CN1CCCCC1 QOKWAMNOBLWSAD-MGONOCMRSA-N 0.000 description 1
• VECSQBGFYNJZBA-MGONOCMRSA-N 6-chloro-n-[[(3s,5s)-1-[(2s)-2-ethyl-3-methylbutyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C(C)C)CN1CCCCC1 VECSQBGFYNJZBA-MGONOCMRSA-N 0.000 description 1
• KXPZUJMIXREJSZ-NSOVKSMOSA-N 6-chloro-n-[[(3s,5s)-1-[(3,5-dichlorophenyl)methyl]-3-(2-morpholin-4-ylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCOCC1)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)Cl)CN1CC1=CC(Cl)=CC(Cl)=C1 KXPZUJMIXREJSZ-NSOVKSMOSA-N 0.000 description 1
• QLTRQRZCYZZHLF-GTTXMTDLSA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-pyrrolidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCC1 QLTRQRZCYZZHLF-GTTXMTDLSA-N 0.000 description 1
• LKMBNIYBMMOPAD-DJDPXSJISA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CCN1CCCCC1 LKMBNIYBMMOPAD-DJDPXSJISA-N 0.000 description 1
• MKEKXEBBUBZRGU-GTTXMTDLSA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(piperidin-1-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)N1CCCCC1 MKEKXEBBUBZRGU-GTTXMTDLSA-N 0.000 description 1
• BUUJROZZGVHDFI-STQWGSIPSA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-[2-(propan-2-ylamino)ethyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCNC(C)C)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 BUUJROZZGVHDFI-STQWGSIPSA-N 0.000 description 1
• YEFKIQMFPUSTSU-STQWGSIPSA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-[2-(propan-2-ylcarbamoylamino)ethyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCNC(=O)NC(C)C)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 YEFKIQMFPUSTSU-STQWGSIPSA-N 0.000 description 1
• WQWHNZFYYOCLPK-XCZPVHLTSA-N 6-chloro-n-[[(3s,5s)-2-oxo-3-(2-piperidin-1-ylethyl)-1-[(2,3,5-trichlorophenyl)methyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCCCC1)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)Cl)CN1CC1=CC(Cl)=CC(Cl)=C1Cl WQWHNZFYYOCLPK-XCZPVHLTSA-N 0.000 description 1
• ONXNFKKPFDSIID-LNMMVMNESA-N 6-chloro-n-[[(3s,5s)-2-oxo-3-(3-oxo-3-piperidin-1-ylpropyl)-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CC(=O)N1CCCCC1 ONXNFKKPFDSIID-LNMMVMNESA-N 0.000 description 1
• QCWCXLLBEUYJPR-DJDPXSJISA-N 6-chloro-n-[[(3s,5s)-3-(2-cyclohexylethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CC1CCCCC1 QCWCXLLBEUYJPR-DJDPXSJISA-N 0.000 description 1
• GMVYBYJIVATXGS-MHWRTBLVSA-N 6-chloro-n-[[(3s,5s)-3-(2-methoxyethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCOC)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 GMVYBYJIVATXGS-MHWRTBLVSA-N 0.000 description 1
• UNIUHTXBGLCPAQ-DJDPXSJISA-N 6-chloro-n-[[(3s,5s)-3-(2-methyl-2-piperidin-1-ylpropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)C(C)(C)N1CCCCC1 UNIUHTXBGLCPAQ-DJDPXSJISA-N 0.000 description 1
• ZMSJRCXRXYIXPD-YDTRGFDASA-N 6-chloro-n-[[(3s,5s)-3-(2-methylpropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CC(C)C)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 ZMSJRCXRXYIXPD-YDTRGFDASA-N 0.000 description 1
• DIAZFFOHKUAJPX-GTTXMTDLSA-N 6-chloro-n-[[(3s,5s)-3-(2-morpholin-4-ylethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCOCC1 DIAZFFOHKUAJPX-GTTXMTDLSA-N 0.000 description 1
• KGURODXSJDZQFH-STQWGSIPSA-N 6-chloro-n-[[(3s,5s)-3-(3-methylbutyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCC(C)C)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 KGURODXSJDZQFH-STQWGSIPSA-N 0.000 description 1
• QHWSIXJXYXVLTI-YDTRGFDASA-N 6-chloro-n-[[(3s,5s)-3-(4-hydroxybutyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCCCO)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 QHWSIXJXYXVLTI-YDTRGFDASA-N 0.000 description 1
• MXQULUQGATWCNX-PBXQCXKZSA-N 6-chloro-n-[[(3s,5s)-3-[(diaminomethylideneamino)methyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CNC(N)=N)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 MXQULUQGATWCNX-PBXQCXKZSA-N 0.000 description 1
• GZBRXEXEFIIBOK-PHXCCWLDSA-N 6-chloro-n-[[(3s,5s)-3-[2-(diaminomethylideneamino)ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCNC(N)=N)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 GZBRXEXEFIIBOK-PHXCCWLDSA-N 0.000 description 1
• ZQSBKBHQNPDVKJ-MHWRTBLVSA-N 6-chloro-n-[[(3s,5s)-3-[2-[(n'-methylcarbamimidoyl)amino]ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCNC(=N)NC)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 ZQSBKBHQNPDVKJ-MHWRTBLVSA-N 0.000 description 1
• QKUWZBBGRJBZEA-GTTXMTDLSA-N 6-chloro-n-[[(3s,5s)-3-hexyl-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@H](CC)CN2CC[C@@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)N[C@H](C2=O)CCCCCC)=CC=CC=C1 QKUWZBBGRJBZEA-GTTXMTDLSA-N 0.000 description 1
• ILSJFQAVPNGFPA-COWIPBKQSA-N 6-chloro-n-[[3-(1-ethylpiperidin-4-yl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CC)C=1C=CC=CC=1)N(C1=O)CCC(CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)NC1C1CCN(CC)CC1 ILSJFQAVPNGFPA-COWIPBKQSA-N 0.000 description 1
• VMIUFLHAHCMJKL-WJHQPOGDSA-N 6-methoxy-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(OC)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCC1 VMIUFLHAHCMJKL-WJHQPOGDSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• XXSCONYSQQLHTH-UHFFFAOYSA-N 9h-fluoren-9-ylmethanol Chemical compound C1=CC=C2C(CO)C3=CC=CC=C3C2=C1 XXSCONYSQQLHTH-UHFFFAOYSA-N 0.000 description 1
• 208000030507 AIDS Diseases 0.000 description 1
• 244000215068 Acacia senegal Species 0.000 description 1
• 208000020154 Acnes Diseases 0.000 description 1
• 239000000275 Adrenocorticotropic Hormone Substances 0.000 description 1
• 229920001817 Agar Polymers 0.000 description 1
• 206010001488 Aggression Diseases 0.000 description 1
• 102000006822 Agouti Signaling Protein Human genes 0.000 description 1
• 108010072151 Agouti Signaling Protein Proteins 0.000 description 1
• 239000005995 Aluminium silicate Substances 0.000 description 1
• 244000144725 Amygdalus communis Species 0.000 description 1
• 235000011437 Amygdalus communis Nutrition 0.000 description 1
• 244000144730 Amygdalus persica Species 0.000 description 1
• 241000252073 Anguilliformes Species 0.000 description 1
• 235000017060 Arachis glabrata Nutrition 0.000 description 1
• 244000105624 Arachis hypogaea Species 0.000 description 1
• 235000010777 Arachis hypogaea Nutrition 0.000 description 1
• 235000018262 Arachis monticola Nutrition 0.000 description 1
• 239000004475 Arginine Substances 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 208000008035 Back Pain Diseases 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• 241000283690 Bos taurus Species 0.000 description 1
• 241000273930 Brevoortia tyrannus Species 0.000 description 1
• VOVNHCGKXKDUSO-CRUJJEGBSA-N C(=O)(OCC1=CC=CC=C1)N(C(NCCC[C@@H]1NC(CCN(C1=O)CC(C1=CC=CC=C1)C1=CC=CC=C1)[C@H](CC1=CC2=CC=CC=C2C=C1)N)=N)C(=O)OCC1=CC=CC=C1 Chemical compound C(=O)(OCC1=CC=CC=C1)N(C(NCCC[C@@H]1NC(CCN(C1=O)CC(C1=CC=CC=C1)C1=CC=CC=C1)[C@H](CC1=CC2=CC=CC=C2C=C1)N)=N)C(=O)OCC1=CC=CC=C1 VOVNHCGKXKDUSO-CRUJJEGBSA-N 0.000 description 1
• JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
• ZYUZLEUJKZZXNN-UHFFFAOYSA-N C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 Chemical group C1=CC(CC(N)C(O)=O)=CC=C1OS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 ZYUZLEUJKZZXNN-UHFFFAOYSA-N 0.000 description 1
• KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
• SOGRHEPKTOJIFD-DRWNPLCXSA-N CCC(CC)CN1CC[C@H](N[C@H](C1=O)CC(C)N)CNC(=O)C2=CC(=C(C=C2)Cl)Cl Chemical compound CCC(CC)CN1CC[C@H](N[C@H](C1=O)CC(C)N)CNC(=O)C2=CC(=C(C=C2)Cl)Cl SOGRHEPKTOJIFD-DRWNPLCXSA-N 0.000 description 1
• BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
• PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
• 241000282465 Canis Species 0.000 description 1
• 235000002566 Capsicum Nutrition 0.000 description 1
• 241000246211 Carassius auratus red var. Species 0.000 description 1
• 239000004215 Carbon black (E152) Substances 0.000 description 1
• OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• 201000002927 Cardiofaciocutaneous syndrome Diseases 0.000 description 1
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
• 102000009016 Cholera Toxin Human genes 0.000 description 1
• 108010049048 Cholera Toxin Proteins 0.000 description 1
• 108010066551 Cholestenone 5 alpha-Reductase Proteins 0.000 description 1
• 101150065749 Churc1 gene Proteins 0.000 description 1
• 206010010144 Completed suicide Diseases 0.000 description 1
• 229940126657 Compound 17 Drugs 0.000 description 1
• 229940126639 Compound 33 Drugs 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• OMFXVFTZEKFJBZ-UHFFFAOYSA-N Corticosterone Natural products O=C1CCC2(C)C3C(O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 OMFXVFTZEKFJBZ-UHFFFAOYSA-N 0.000 description 1
• 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• AHLPHDHHMVZTML-SCSAIBSYSA-N D-Ornithine Chemical compound NCCC[C@@H](N)C(O)=O AHLPHDHHMVZTML-SCSAIBSYSA-N 0.000 description 1
• 208000001840 Dandruff Diseases 0.000 description 1
• XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• 201000010374 Down Syndrome Diseases 0.000 description 1
• LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
• 208000004929 Facial Paralysis Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
• 241000206672 Gelidium Species 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 229920000084 Gum arabic Polymers 0.000 description 1
• 235000019487 Hazelnut oil Nutrition 0.000 description 1
• 241000711549 Hepacivirus C Species 0.000 description 1
• 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
• 101100005713 Homo sapiens CD4 gene Proteins 0.000 description 1
• 101001057504 Homo sapiens Interferon-stimulated gene 20 kDa protein Proteins 0.000 description 1
• 101001055144 Homo sapiens Interleukin-2 receptor subunit alpha Proteins 0.000 description 1
• 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 description 1
• 241000252234 Hypophthalmichthys nobilis Species 0.000 description 1
• 208000026350 Inborn Genetic disease Diseases 0.000 description 1
• 102000004877 Insulin Human genes 0.000 description 1
• 108090001061 Insulin Proteins 0.000 description 1
• 102100026878 Interleukin-2 receptor subunit alpha Human genes 0.000 description 1
• 241000721662 Juniperus Species 0.000 description 1
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
• 229910010082 LiAlH Inorganic materials 0.000 description 1
• 241000428198 Lutrinae Species 0.000 description 1
• 239000004472 Lysine Substances 0.000 description 1
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
• 101150048659 MC5R gene Proteins 0.000 description 1
• 240000003183 Manihot esculenta Species 0.000 description 1
• 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 241000283923 Marmota monax Species 0.000 description 1
• 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 1
• 102400000744 Melanotropin gamma Human genes 0.000 description 1
• 101800000520 Melanotropin gamma Proteins 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
• 102000014171 Milk Proteins Human genes 0.000 description 1
• 108010011756 Milk Proteins Proteins 0.000 description 1
• 239000004909 Moisturizer Substances 0.000 description 1
• 208000019022 Mood disease Diseases 0.000 description 1
• 241001529936 Murinae Species 0.000 description 1
• 235000021360 Myristic acid Nutrition 0.000 description 1
• LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
• MSTAOBRZXXUMJU-TXIPYEPDSA-N N-[[(3S,5S)-3-[3-(diaminomethylideneamino)propyl]-1-(2-oxo-1-phenylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound N(C(=N)N)CCC[C@H]1CN(CC[C@H](N1)CNC(=O)C1=CC2=CC=CC=C2C=C1)C(C=O)C1=CC=CC=C1 MSTAOBRZXXUMJU-TXIPYEPDSA-N 0.000 description 1
• CJUMAFVKTCBCJK-UHFFFAOYSA-N N-benzyloxycarbonylglycine Chemical compound OC(=O)CNC(=O)OCC1=CC=CC=C1 CJUMAFVKTCBCJK-UHFFFAOYSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
• FEZSMNOBCVMCBN-KXBFYZLASA-N NCC[C@H]1C(N(CC[C@H](N1)CNC(C1=CC(=C(C=C1)F)Cl)=O)CC1=C(C(=CC=C1)Cl)Cl)=O Chemical compound NCC[C@H]1C(N(CC[C@H](N1)CNC(C1=CC(=C(C=C1)F)Cl)=O)CC1=C(C(=CC=C1)Cl)Cl)=O FEZSMNOBCVMCBN-KXBFYZLASA-N 0.000 description 1
• 241000772415 Neovison vison Species 0.000 description 1
• 102000007399 Nuclear hormone receptor Human genes 0.000 description 1
• 108020005497 Nuclear hormone receptor Proteins 0.000 description 1
• 241001365789 Oenanthe crocata Species 0.000 description 1
• 240000007817 Olea europaea Species 0.000 description 1
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
• 235000019482 Palm oil Nutrition 0.000 description 1
• 235000021314 Palmitic acid Nutrition 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 206010034133 Pathogen resistance Diseases 0.000 description 1
• 235000019483 Peanut oil Nutrition 0.000 description 1
• 239000006002 Pepper Substances 0.000 description 1
• 241000530626 Percina Species 0.000 description 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
• 206010034972 Photosensitivity reaction Diseases 0.000 description 1
• 235000016761 Piper aduncum Nutrition 0.000 description 1
• 240000003889 Piper guineense Species 0.000 description 1
• 235000017804 Piper guineense Nutrition 0.000 description 1
• 235000008184 Piper nigrum Nutrition 0.000 description 1
• 235000019497 Pistachio oil Nutrition 0.000 description 1
• 208000000474 Poliomyelitis Diseases 0.000 description 1
• 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
• 102100038239 Protein Churchill Human genes 0.000 description 1
• 235000006040 Prunus persica var persica Nutrition 0.000 description 1
• 208000003251 Pruritus Diseases 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• 206010037714 Quadriplegia Diseases 0.000 description 1
• 235000004443 Ricinus communis Nutrition 0.000 description 1
• 235000019485 Safflower oil Nutrition 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 201000001880 Sexual dysfunction Diseases 0.000 description 1
• PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
• 206010040880 Skin irritation Diseases 0.000 description 1
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
• 235000002595 Solanum tuberosum Nutrition 0.000 description 1
• 244000061456 Solanum tuberosum Species 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• 206010042928 Syringomyelia Diseases 0.000 description 1
• 241000270666 Testudines Species 0.000 description 1
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
• 239000004473 Threonine Substances 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 1
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
• 235000004869 Tussilago farfara Nutrition 0.000 description 1
• 240000000377 Tussilago farfara Species 0.000 description 1
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 1
• 208000036826 VIIth nerve paralysis Diseases 0.000 description 1
• 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
• 241001135917 Vitellaria paradoxa Species 0.000 description 1
• 240000008042 Zea mays Species 0.000 description 1
• 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
• LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
• SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
• 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
• FRGAIZLZPOROJH-BKIJVIAGSA-N [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[2-hydroxy-3-[2-hydroxy-3-(2-hydroxy-3-octadecanoyloxypropoxy)propoxy]propoxy]oxan-2-yl]methyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COCC(O)COCC(O)CO[C@H]1O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)[C@@H](O)[C@H](O)[C@H]1O FRGAIZLZPOROJH-BKIJVIAGSA-N 0.000 description 1
• NWGKJDSIEKMTRX-BFWOXRRGSA-N [(2r)-2-[(3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)C1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-BFWOXRRGSA-N 0.000 description 1
• FNDUTDVAVGTYCL-SECBINFHSA-N [(2s)-1-azidobutan-2-yl]benzene Chemical compound [N-]=[N+]=NC[C@@H](CC)C1=CC=CC=C1 FNDUTDVAVGTYCL-SECBINFHSA-N 0.000 description 1
• RXGMLEVCVZWMSJ-SNVBAGLBSA-N [(2s)-2-phenylbutyl] methanesulfonate Chemical compound CS(=O)(=O)OC[C@@H](CC)C1=CC=CC=C1 RXGMLEVCVZWMSJ-SNVBAGLBSA-N 0.000 description 1
• PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
• GXJDMEXZCDYNHH-UHFFFAOYSA-N [2-[methoxy(methyl)amino]-2-oxoethyl] carbamate Chemical compound C(N)(OCC(=O)N(C)OC)=O GXJDMEXZCDYNHH-UHFFFAOYSA-N 0.000 description 1
• 230000005856 abnormality Effects 0.000 description 1
• 239000003082 abrasive agent Substances 0.000 description 1
• 239000002250 absorbent Substances 0.000 description 1
• 230000002745 absorbent Effects 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• 235000010489 acacia gum Nutrition 0.000 description 1
• 239000000205 acacia gum Substances 0.000 description 1
• IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
• 150000001242 acetic acid derivatives Chemical class 0.000 description 1
• 230000003213 activating effect Effects 0.000 description 1
• 239000008186 active pharmaceutical agent Substances 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 208000009956 adenocarcinoma Diseases 0.000 description 1
• 210000004100 adrenal gland Anatomy 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 235000010419 agar Nutrition 0.000 description 1
• 230000016571 aggressive behavior Effects 0.000 description 1
• 208000012761 aggressive behavior Diseases 0.000 description 1
• 230000008484 agonism Effects 0.000 description 1
• 239000000556 agonist Substances 0.000 description 1
• 235000004279 alanine Nutrition 0.000 description 1
• 206010056977 alcoholic pancreatitis Diseases 0.000 description 1
• 239000000783 alginic acid Substances 0.000 description 1
• 229960001126 alginic acid Drugs 0.000 description 1
• 150000004781 alginic acids Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000003973 alkyl amines Chemical group 0.000 description 1
• 125000005907 alkyl ester group Chemical group 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 1
• 239000008168 almond oil Substances 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• 229910052782 aluminium Inorganic materials 0.000 description 1
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 235000012211 aluminium silicate Nutrition 0.000 description 1
• 230000009435 amidation Effects 0.000 description 1
• 238000007112 amidation reaction Methods 0.000 description 1
• 238000010640 amide synthesis reaction Methods 0.000 description 1
• 125000006242 amine protecting group Chemical group 0.000 description 1
• 150000003862 amino acid derivatives Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 230000001548 androgenic effect Effects 0.000 description 1
• 229960003473 androstanolone Drugs 0.000 description 1
• 239000010775 animal oil Substances 0.000 description 1
• 125000000129 anionic group Chemical group 0.000 description 1
• 230000003042 antagnostic effect Effects 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 230000000843 anti-fungal effect Effects 0.000 description 1
• 229940121375 antifungal agent Drugs 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000006907 apoptotic process Effects 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000008135 aqueous vehicle Substances 0.000 description 1
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
• 229960003121 arginine Drugs 0.000 description 1
• 229910052786 argon Inorganic materials 0.000 description 1
• 206010003246 arthritis Diseases 0.000 description 1
• 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
• 235000009582 asparagine Nutrition 0.000 description 1
• 229960001230 asparagine Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
• 235000021302 avocado oil Nutrition 0.000 description 1
• 239000008163 avocado oil Substances 0.000 description 1
• 125000002393 azetidinyl group Chemical group 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 230000006399 behavior Effects 0.000 description 1
• 230000008901 benefit Effects 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical group CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
• CYKIHIBNSFRKQP-UHFFFAOYSA-N benzo[f][1]benzothiole Chemical compound C1=CC=C2C=C(SC=C3)C3=CC2=C1 CYKIHIBNSFRKQP-UHFFFAOYSA-N 0.000 description 1
• CGKYEIXJDLWFGW-MDXRQRRTSA-N benzyl 2-[(3s,5s)-1-(2,2-diphenylethyl)-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-2-oxo-1,4-diazepan-5-yl]-2-(methylamino)acetate Chemical compound C([C@H](N[C@@H](CC(C)NC(=O)OC(C)(C)C)C1=O)C(NC)C(=O)OCC=2C=CC=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 CGKYEIXJDLWFGW-MDXRQRRTSA-N 0.000 description 1
• 229960002903 benzyl benzoate Drugs 0.000 description 1
• TVRURNHJFQOAFC-UHFFFAOYSA-N benzyl n-(2-oxobut-3-enyl)carbamate Chemical compound C=CC(=O)CNC(=O)OCC1=CC=CC=C1 TVRURNHJFQOAFC-UHFFFAOYSA-N 0.000 description 1
• NWYPLKICSHBTAJ-UHFFFAOYSA-N benzyl n-[2-[methoxy(methyl)amino]-2-oxoethyl]carbamate Chemical compound CON(C)C(=O)CNC(=O)OCC1=CC=CC=C1 NWYPLKICSHBTAJ-UHFFFAOYSA-N 0.000 description 1
• HHJTZPGPTOVZMG-XLJNKUFUSA-N benzyl n-[3-[(2r,7r)-4-(2,2-diphenylethyl)-7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-oxo-1,4-diazepan-2-yl]propyl]carbamate Chemical compound C([C@@H](N[C@H](CCCNC(=O)OCC=1C=CC=CC=1)C1=O)CNC(=O)OC(C)(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HHJTZPGPTOVZMG-XLJNKUFUSA-N 0.000 description 1
• HHJTZPGPTOVZMG-XDFJSJKPSA-N benzyl n-[3-[(2r,7s)-4-(2,2-diphenylethyl)-7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-oxo-1,4-diazepan-2-yl]propyl]carbamate Chemical compound C([C@H](N[C@H](CCCNC(=O)OCC=1C=CC=CC=1)C1=O)CNC(=O)OC(C)(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HHJTZPGPTOVZMG-XDFJSJKPSA-N 0.000 description 1
• HHJTZPGPTOVZMG-BHYZAODMSA-N benzyl n-[3-[(2s,7r)-4-(2,2-diphenylethyl)-7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-oxo-1,4-diazepan-2-yl]propyl]carbamate Chemical compound C([C@@H](N[C@@H](CCCNC(=O)OCC=1C=CC=CC=1)C1=O)CNC(=O)OC(C)(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HHJTZPGPTOVZMG-BHYZAODMSA-N 0.000 description 1
• HHJTZPGPTOVZMG-CDZUIXILSA-N benzyl n-[3-[(2s,7s)-4-(2,2-diphenylethyl)-7-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-3-oxo-1,4-diazepan-2-yl]propyl]carbamate Chemical compound C([C@H](N[C@@H](CCCNC(=O)OCC=1C=CC=CC=1)C1=O)CNC(=O)OC(C)(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HHJTZPGPTOVZMG-CDZUIXILSA-N 0.000 description 1
• QGHMSBWCWODQPF-SMCANUKXSA-N benzyl n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-2-oxo-1,4-diazepan-5-yl]methyl]carbamate Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCNC(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 QGHMSBWCWODQPF-SMCANUKXSA-N 0.000 description 1
• LMNBZOIZCPFSJO-GOTSBHOMSA-N benzyl n-[[(3s,5s)-1-(2-ethylbutyl)-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-2-oxo-1,4-diazepan-5-yl]methyl]carbamate Chemical compound N1[C@@H](CCNC(=O)OC(C)(C)C)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)OCC1=CC=CC=C1 LMNBZOIZCPFSJO-GOTSBHOMSA-N 0.000 description 1
• PWOAEJAPBMWGKX-AXJMSPCVSA-N benzyl n-[[(3s,5s)-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-2-oxo-1-(2-phenylbutyl)-1,4-diazepan-5-yl]methyl]carbamate Chemical compound C([C@@H]1CCN(C([C@H](CCNC(=O)OC(C)(C)C)N1)=O)CC(CC)C=1C=CC=CC=1)NC(=O)OCC1=CC=CC=C1 PWOAEJAPBMWGKX-AXJMSPCVSA-N 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
• VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
• 230000027455 binding Effects 0.000 description 1
• OGODKNYCTJYXFF-UHFFFAOYSA-N bis(4-methylbenzoyl) 2,3-dihydroxybutanedioate Chemical class C1=CC(C)=CC=C1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=C(C)C=C1 OGODKNYCTJYXFF-UHFFFAOYSA-N 0.000 description 1
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
• 230000036760 body temperature Effects 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 239000006172 buffering agent Substances 0.000 description 1
• 235000019437 butane-1,3-diol Nutrition 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• DHAZIUXMHRHVMP-UHFFFAOYSA-N butyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCC DHAZIUXMHRHVMP-UHFFFAOYSA-N 0.000 description 1
• 229910000019 calcium carbonate Inorganic materials 0.000 description 1
• 235000010216 calcium carbonate Nutrition 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 235000013539 calcium stearate Nutrition 0.000 description 1
• 239000008116 calcium stearate Substances 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 238000004177 carbon cycle Methods 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000004203 carnauba wax Substances 0.000 description 1
• 235000013869 carnauba wax Nutrition 0.000 description 1
• 239000012876 carrier material Substances 0.000 description 1
• 238000005266 casting Methods 0.000 description 1
• 239000003054 catalyst Substances 0.000 description 1
• 230000022131 cell cycle Effects 0.000 description 1
• 230000004663 cell proliferation Effects 0.000 description 1
• 229940081733 cetearyl alcohol Drugs 0.000 description 1
• 229960000541 cetyl alcohol Drugs 0.000 description 1
• 229940085262 cetyl dimethicone Drugs 0.000 description 1
• 239000002738 chelating agent Substances 0.000 description 1
• 238000007385 chemical modification Methods 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 229960004926 chlorobutanol Drugs 0.000 description 1
• 235000012000 cholesterol Nutrition 0.000 description 1
• 150000001840 cholesterol esters Chemical class 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
• 150000001860 citric acid derivatives Chemical class 0.000 description 1
• 239000004927 clay Substances 0.000 description 1
• 239000011248 coating agent Substances 0.000 description 1
• 235000019864 coconut oil Nutrition 0.000 description 1
• 239000003240 coconut oil Substances 0.000 description 1
• 235000019516 cod Nutrition 0.000 description 1
• 235000012716 cod liver oil Nutrition 0.000 description 1
• 239000003026 cod liver oil Substances 0.000 description 1
• 210000001072 colon Anatomy 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000008139 complexing agent Substances 0.000 description 1
• 229940125797 compound 12 Drugs 0.000 description 1
• 229940126543 compound 14 Drugs 0.000 description 1
• 229940125758 compound 15 Drugs 0.000 description 1
• 229940126142 compound 16 Drugs 0.000 description 1
• 229940126208 compound 22 Drugs 0.000 description 1
• 229940125833 compound 23 Drugs 0.000 description 1
• 229940125961 compound 24 Drugs 0.000 description 1
• 229940125846 compound 25 Drugs 0.000 description 1
• 229940125851 compound 27 Drugs 0.000 description 1
• 229940127204 compound 29 Drugs 0.000 description 1
• 229940125877 compound 31 Drugs 0.000 description 1
• 229940125878 compound 36 Drugs 0.000 description 1
• 229940126540 compound 41 Drugs 0.000 description 1
• 229940125936 compound 42 Drugs 0.000 description 1
• 229940127271 compound 49 Drugs 0.000 description 1
• 229940126545 compound 53 Drugs 0.000 description 1
• 229940125900 compound 59 Drugs 0.000 description 1
• 229940126179 compound 72 Drugs 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 235000005822 corn Nutrition 0.000 description 1
• 235000005687 corn oil Nutrition 0.000 description 1
• 239000003246 corticosteroid Substances 0.000 description 1
• 229960001334 corticosteroids Drugs 0.000 description 1
• OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 1
• 239000002537 cosmetic Substances 0.000 description 1
• 235000012343 cottonseed oil Nutrition 0.000 description 1
• 239000002385 cottonseed oil Substances 0.000 description 1
• 239000012045 crude solution Substances 0.000 description 1
• 239000013078 crystal Substances 0.000 description 1
• MFNYBOWJWGPXFM-UHFFFAOYSA-N cyclobutanecarboxamide Chemical compound NC(=O)C1CCC1 MFNYBOWJWGPXFM-UHFFFAOYSA-N 0.000 description 1
• 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
• 125000006622 cycloheptylmethyl group Chemical group 0.000 description 1
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
• JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 229940086555 cyclomethicone Drugs 0.000 description 1
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
• UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
• 229960000978 cyproterone acetate Drugs 0.000 description 1
• 235000018417 cysteine Nutrition 0.000 description 1
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
• 230000006378 damage Effects 0.000 description 1
• BOUIEBMBWBCUPB-UHFFFAOYSA-N decyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OCCCCCCCCCC BOUIEBMBWBCUPB-UHFFFAOYSA-N 0.000 description 1
• 238000012217 deletion Methods 0.000 description 1
• 230000037430 deletion Effects 0.000 description 1
• 238000009795 derivation Methods 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• 231100000223 dermal penetration Toxicity 0.000 description 1
• 125000004431 deuterium atom Chemical group 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• METQSPRSQINEEU-UHFFFAOYSA-N dihydrospirorenone Natural products CC12CCC(C3(CCC(=O)C=C3C3CC33)C)C3C1C1CC1C21CCC(=O)O1 METQSPRSQINEEU-UHFFFAOYSA-N 0.000 description 1
• UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
• 229940008099 dimethicone Drugs 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• TVWTZAGVNBPXHU-FOCLMDBBSA-N dioctyl (e)-but-2-enedioate Chemical compound CCCCCCCCOC(=O)\C=C\C(=O)OCCCCCCCC TVWTZAGVNBPXHU-FOCLMDBBSA-N 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• 238000004090 dissolution Methods 0.000 description 1
• 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
• METQSPRSQINEEU-HXCATZOESA-N drospirenone Chemical compound C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 METQSPRSQINEEU-HXCATZOESA-N 0.000 description 1
• 229960004845 drospirenone Drugs 0.000 description 1
• 239000003974 emollient agent Substances 0.000 description 1
• 230000001804 emulsifying effect Effects 0.000 description 1
• 239000008387 emulsifying waxe Substances 0.000 description 1
• 239000003623 enhancer Substances 0.000 description 1
• 230000002708 enhancing effect Effects 0.000 description 1
• BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 210000002615 epidermis Anatomy 0.000 description 1
• 206010015037 epilepsy Diseases 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• 229960002568 ethinylestradiol Drugs 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
• 229940093499 ethyl acetate Drugs 0.000 description 1
• LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
• 229940093471 ethyl oleate Drugs 0.000 description 1
• 229940067592 ethyl palmitate Drugs 0.000 description 1
• 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 210000003499 exocrine gland Anatomy 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 230000001815 facial effect Effects 0.000 description 1
• 150000002194 fatty esters Chemical class 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000008098 formaldehyde solution Substances 0.000 description 1
• 239000003205 fragrance Substances 0.000 description 1
• VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
• 230000006870 function Effects 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• 230000001408 fungistatic effect Effects 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 239000003349 gelling agent Substances 0.000 description 1
• 208000016361 genetic disease Diseases 0.000 description 1
• 230000002068 genetic effect Effects 0.000 description 1
• 210000004907 gland Anatomy 0.000 description 1
• 235000001727 glucose Nutrition 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
• SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
• 239000003163 gonadal steroid hormone Substances 0.000 description 1
• 239000008169 grapeseed oil Substances 0.000 description 1
• 230000012010 growth Effects 0.000 description 1
• 229940069752 halibut liver oil Drugs 0.000 description 1
• 125000004438 haloalkoxy group Chemical group 0.000 description 1
• 239000010468 hazelnut oil Substances 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 125000006038 hexenyl group Chemical group 0.000 description 1
• SMWDEDPRQFUXNH-UHFFFAOYSA-N hexyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCC SMWDEDPRQFUXNH-UHFFFAOYSA-N 0.000 description 1
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
• 210000005260 human cell Anatomy 0.000 description 1
• 229930195733 hydrocarbon Natural products 0.000 description 1
• 150000002430 hydrocarbons Chemical class 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 229920006007 hydrogenated polyisobutylene Polymers 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
• 230000002519 immonomodulatory effect Effects 0.000 description 1
• 210000000987 immune system Anatomy 0.000 description 1
• 230000001506 immunosuppresive effect Effects 0.000 description 1
• 239000012535 impurity Substances 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 238000010348 incorporation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 description 1
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
• 230000006698 induction Effects 0.000 description 1
• 230000002757 inflammatory effect Effects 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 239000007972 injectable composition Substances 0.000 description 1
• 229940125396 insulin Drugs 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 210000003247 intermediate pituitary gland Anatomy 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 210000000936 intestine Anatomy 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 238000001990 intravenous administration Methods 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 229960000310 isoleucine Drugs 0.000 description 1
• AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
• 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
• 150000003903 lactic acid esters Chemical class 0.000 description 1
• 239000000787 lecithin Substances 0.000 description 1
• 235000010445 lecithin Nutrition 0.000 description 1
• 229940067606 lecithin Drugs 0.000 description 1
• 210000000265 leukocyte Anatomy 0.000 description 1
• 239000011981 lindlar catalyst Substances 0.000 description 1
• 235000021388 linseed oil Nutrition 0.000 description 1
• 239000000944 linseed oil Substances 0.000 description 1
• 229940057995 liquid paraffin Drugs 0.000 description 1
• 238000007449 liver function test Methods 0.000 description 1
• RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
• 238000011068 loading method Methods 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 210000005210 lymphoid organ Anatomy 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• 238000012423 maintenance Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000001819 mass spectrum Methods 0.000 description 1
• 230000010534 mechanism of action Effects 0.000 description 1
• 210000002752 melanocyte Anatomy 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
• HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• ZBELDPMWYXDLNY-UHFFFAOYSA-N methyl 9-(4-bromo-2-fluoroanilino)-[1,3]thiazolo[5,4-f]quinazoline-2-carboximidate Chemical compound C12=C3SC(C(=N)OC)=NC3=CC=C2N=CN=C1NC1=CC=C(Br)C=C1F ZBELDPMWYXDLNY-UHFFFAOYSA-N 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• ZMDGICHYDVYQDX-UHFFFAOYSA-N methylidenecarbamic acid Chemical compound OC(=O)N=C ZMDGICHYDVYQDX-UHFFFAOYSA-N 0.000 description 1
• 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• 239000004530 micro-emulsion Substances 0.000 description 1
• 244000005700 microbiome Species 0.000 description 1
• 229940016286 microcrystalline cellulose Drugs 0.000 description 1
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
• 239000008108 microcrystalline cellulose Substances 0.000 description 1
• 239000004200 microcrystalline wax Substances 0.000 description 1
• 235000019808 microcrystalline wax Nutrition 0.000 description 1
• 235000021239 milk protein Nutrition 0.000 description 1
• 229960004023 minocycline Drugs 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 230000001333 moisturizer Effects 0.000 description 1
• CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 210000003205 muscle Anatomy 0.000 description 1
• 230000035772 mutation Effects 0.000 description 1
• 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
• BQQWQJSSWRPXDB-PUPDPRJKSA-N n-[(1r)-1-[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]-2-naphthalen-2-ylethyl]acetamide Chemical compound C([C@H](N[C@@H](CCCNC(N)=N)C1=O)[C@@H](CC=2C=C3C=CC=CC3=CC=2)NC(=O)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 BQQWQJSSWRPXDB-PUPDPRJKSA-N 0.000 description 1
• WZZVZPAJKVCJKH-VTIYRKAUSA-N n-[2-[(3s,5r)-1-(2,2-diphenylethyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]ethyl]benzamide Chemical compound C([C@H](N[C@@H](CCN1CCCCC1)C1=O)CCNC(=O)C=2C=CC=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 WZZVZPAJKVCJKH-VTIYRKAUSA-N 0.000 description 1
• TXZSDUWGCSMZLE-BZFILIQBSA-N n-[2-[(3s,5r)-1-(2,2-diphenylethyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]ethyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCCCC1)C1=O)CCNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 TXZSDUWGCSMZLE-BZFILIQBSA-N 0.000 description 1
• FJJQFRFHGDPGKD-VHFKIGOXSA-N n-[2-[(3s,5r)-1-(2,2-diphenylethyl)-2-oxo-3-(2-pyrrolidin-1-ylethyl)-1,4-diazepan-5-yl]ethyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCN1CCCC1)C1=O)CCNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 FJJQFRFHGDPGKD-VHFKIGOXSA-N 0.000 description 1
• DAZFBUPSURRZJX-IAPPQJPRSA-N n-[2-[(3s,5r)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]ethyl]benzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCN)CNC(=O)C1=CC=CC=C1 DAZFBUPSURRZJX-IAPPQJPRSA-N 0.000 description 1
• PZKLIHADSFMOCW-BHYZAODMSA-N n-[2-[(3s,5r)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]ethyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CCNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 PZKLIHADSFMOCW-BHYZAODMSA-N 0.000 description 1
• LEFUZVHHQPSANP-HXUWFJFHSA-N n-[2-oxo-4-[[(2s)-2-phenylbutyl]amino]butyl]-3-phenylpropanamide Chemical compound C([C@@H](CC)C=1C=CC=CC=1)NCCC(=O)CNC(=O)CCC1=CC=CC=C1 LEFUZVHHQPSANP-HXUWFJFHSA-N 0.000 description 1
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
• LMLASWOOKOWICU-UHFFFAOYSA-N n-[4-[(3,5-dichlorophenyl)methylamino]-2-oxobutyl]naphthalene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC(CNCCC(=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)=C1 LMLASWOOKOWICU-UHFFFAOYSA-N 0.000 description 1
• JCQMVGHNRJRBCG-KPGYKUMBSA-N n-[[(3r,5r)-3-(2-amino-2-methylpropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@@H](CC(C)(C)N)N[C@@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 JCQMVGHNRJRBCG-KPGYKUMBSA-N 0.000 description 1
• QOIYHTMMIORSMO-PJJRWXIWSA-N n-[[(3s,5s)-1-(1-adamantylmethyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC23CC4CC(CC(C4)C2)C3)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 QOIYHTMMIORSMO-PJJRWXIWSA-N 0.000 description 1
• YDNYFVLZWYCBQI-SMCANUKXSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(2-oxoethyl)-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CC=O)C1=O)CNC(=O)C2=CC3=CC=C(C=C3C=C2)F)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 YDNYFVLZWYCBQI-SMCANUKXSA-N 0.000 description 1
• DXCWFDHGWWKHSM-JSXFGMRASA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(2-phenylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCC=1C=CC=CC=1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DXCWFDHGWWKHSM-JSXFGMRASA-N 0.000 description 1
• KDYBOQUPPNYUBG-GIWKVKTRSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(3-oxo-3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCC(=O)N2CCCCC2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 KDYBOQUPPNYUBG-GIWKVKTRSA-N 0.000 description 1
• IDXRWSTZYJEJCO-JSXFGMRASA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCN1CCCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 IDXRWSTZYJEJCO-JSXFGMRASA-N 0.000 description 1
• ANTSJPZYEYUKQW-LRHLLKFHSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(piperidin-1-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CN1CCCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ANTSJPZYEYUKQW-LRHLLKFHSA-N 0.000 description 1
• VNMYIZPJGNRHLF-LRHLLKFHSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(pyridin-3-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CC=1C=NC=CC=1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VNMYIZPJGNRHLF-LRHLLKFHSA-N 0.000 description 1
• BETPYZYCWAGILT-LRHLLKFHSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(pyridin-4-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CC=1C=CN=CC=1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 BETPYZYCWAGILT-LRHLLKFHSA-N 0.000 description 1
• CSVKOBXXZWQJFH-TWJUONSBSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-[2-(propan-2-ylamino)ethyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCNC(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 CSVKOBXXZWQJFH-TWJUONSBSA-N 0.000 description 1
• VLSQOCSIELJZCT-GIWKVKTRSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-[4-(propan-2-ylamino)butyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCCNC(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VLSQOCSIELJZCT-GIWKVKTRSA-N 0.000 description 1
• LWHDHUWSRWXMLJ-CDZUIXILSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-[2-[methoxy(methyl)amino]-2-oxoethyl]-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(F)=CC2=CC=1)N[C@H](C1=O)CC(=O)N(C)OC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 LWHDHUWSRWXMLJ-CDZUIXILSA-N 0.000 description 1
• FMQCPFGNUAWQSN-WEZIJMHWSA-N n-[[(3s,5s)-1-(2,2-diphenylethyl)-3-[3-(methylamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 FMQCPFGNUAWQSN-WEZIJMHWSA-N 0.000 description 1
• KHSZVGIVMCAAEX-UIOOFZCWSA-N n-[[(3s,5s)-1-(2-cyclohexylethyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CCC1CCCCC1 KHSZVGIVMCAAEX-UIOOFZCWSA-N 0.000 description 1
• BDLQPOKUIAQPOP-NSOVKSMOSA-N n-[[(3s,5s)-1-(2-ethylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(F)=CC3=CC=2)CCN(C1=O)CC(CC)CC)CN1CCCCC1 BDLQPOKUIAQPOP-NSOVKSMOSA-N 0.000 description 1
• DTOOUBDUVXWTKR-NSOVKSMOSA-N n-[[(3s,5s)-1-(2-ethylbutyl)-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)CC(CC)CC)CN1CCCCC1 DTOOUBDUVXWTKR-NSOVKSMOSA-N 0.000 description 1
• QLKOVWMYGSDFMS-GFMLHKOCSA-N n-[[(3s,5s)-1-(3-anilino-3-oxo-2-phenylpropyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C(=O)NC1=CC=CC=C1 QLKOVWMYGSDFMS-GFMLHKOCSA-N 0.000 description 1
• LXVAANGAZWTPKK-SVBPBHIXSA-N n-[[(3s,5s)-1-(cyclohexylmethyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]-4-phenylbenzamide Chemical compound C([C@H]1N[C@H](C(N(CC2CCCCC2)CC1)=O)CCCNC(=N)N)NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LXVAANGAZWTPKK-SVBPBHIXSA-N 0.000 description 1
• OHGAJPCQASYOGK-DQEYMECFSA-N n-[[(3s,5s)-1-(cyclohexylmethyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1CCCCC1 OHGAJPCQASYOGK-DQEYMECFSA-N 0.000 description 1
• ADKVQJADKHYOED-UPVQGACJSA-N n-[[(3s,5s)-1-(cyclohexylmethyl)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]quinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=NC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1CCCCC1 ADKVQJADKHYOED-UPVQGACJSA-N 0.000 description 1
• XPBDPPLRPHGTCD-AHCWXFLVSA-N n-[[(3s,5s)-1-[(2r)-2-(4-chlorophenyl)propyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@H](C)C=1C=CC(Cl)=CC=1)CN1CCCCC1 XPBDPPLRPHGTCD-AHCWXFLVSA-N 0.000 description 1
• CCWKJKIMXUBDRW-DSPMFFIESA-N n-[[(3s,5s)-1-[(2r)-3-methyl-2-phenylbutyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@H](C(C)C)C=1C=CC=CC=1)CN1CCCCC1 CCWKJKIMXUBDRW-DSPMFFIESA-N 0.000 description 1
• XPBDPPLRPHGTCD-GTTXMTDLSA-N n-[[(3s,5s)-1-[(2s)-2-(4-chlorophenyl)propyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@@H](C)C=1C=CC(Cl)=CC=1)CN1CCCCC1 XPBDPPLRPHGTCD-GTTXMTDLSA-N 0.000 description 1
• ITFIOTBKZZKPDD-HZFUHODCSA-N n-[[(3s,5s)-1-[(2s)-2-acetamido-2-phenylethyl]-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)NC(=O)C)=CC=CC=C1 ITFIOTBKZZKPDD-HZFUHODCSA-N 0.000 description 1
• CCWKJKIMXUBDRW-ZDCRTTOTSA-N n-[[(3s,5s)-1-[(2s)-3-methyl-2-phenylbutyl]-2-oxo-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@@H](C(C)C)C=1C=CC=CC=1)CN1CCCCC1 CCWKJKIMXUBDRW-ZDCRTTOTSA-N 0.000 description 1
• IZBHZOBLFBQQPY-SVBPBHIXSA-N n-[[(3s,5s)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-3-(pyrrolidin-1-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC(CN2C([C@H](CN3CCCC3)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)=C1 IZBHZOBLFBQQPY-SVBPBHIXSA-N 0.000 description 1
• VHKRXIDKQSHFJJ-DQEYMECFSA-N n-[[(3s,5s)-1-[(3-chloro-5-fluorophenyl)methyl]-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1=CC(F)=CC(Cl)=C1 VHKRXIDKQSHFJJ-DQEYMECFSA-N 0.000 description 1
• ZLZLPEBYLQRVNZ-CDZUIXILSA-N n-[[(3s,5s)-1-[2,2-bis(4-fluorophenyl)ethyl]-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ZLZLPEBYLQRVNZ-CDZUIXILSA-N 0.000 description 1
• UNHBDQDXOBLMTP-NHZFLZHXSA-N n-[[(3s,5s)-1-[2,2-bis(4-methoxyphenyl)ethyl]-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)CN1C(=O)[C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 UNHBDQDXOBLMTP-NHZFLZHXSA-N 0.000 description 1
• LLSPVLURZFRKQC-LIOFFLAUSA-N n-[[(3s,5s)-1-[2-(3-bicyclo[2.2.1]heptanyl)ethyl]-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CCC2C3CCC(C3)C2)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 LLSPVLURZFRKQC-LIOFFLAUSA-N 0.000 description 1
• WPCJZOUXSQEEEF-DQEYMECFSA-N n-[[(3s,5s)-1-benzyl-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1=CC=CC=C1 WPCJZOUXSQEEEF-DQEYMECFSA-N 0.000 description 1
• RQAUICUAVHREBS-UPVQGACJSA-N n-[[(3s,5s)-1-cyclohexyl-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1C1CCCCC1 RQAUICUAVHREBS-UPVQGACJSA-N 0.000 description 1
• MQVWWDKVLLEGKD-VLIDNHJSSA-N n-[[(3s,5s)-2-oxo-1-(2-phenylbutyl)-3-(3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)CC(CC)C=1C=CC=CC=1)CCN1CCCCC1 MQVWWDKVLLEGKD-VLIDNHJSSA-N 0.000 description 1
• SLIWKEWEOKKPCT-ZDCRTTOTSA-N n-[[(3s,5s)-2-oxo-1-[(2r)-2-phenylpentyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@H](CCC)C=1C=CC=CC=1)CN1CCCCC1 SLIWKEWEOKKPCT-ZDCRTTOTSA-N 0.000 description 1
• LPJIFZVWSJVIJR-IGBKUBFESA-N n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]-2-phenyl-1,3-thiazole-4-carboxamide Chemical compound C([C@@H]1CCN(C([C@H](CCN2CCCCC2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C(N=1)=CSC=1C1=CC=CC=C1 LPJIFZVWSJVIJR-IGBKUBFESA-N 0.000 description 1
• GRJDLJXFXZBQLM-AFAVSPFMSA-N n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]-4-phenylbenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN2CCCCC2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 GRJDLJXFXZBQLM-AFAVSPFMSA-N 0.000 description 1
• SLIWKEWEOKKPCT-CEUYOYMZSA-N n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylpentyl]-3-(2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@@H](CCC)C=1C=CC=CC=1)CN1CCCCC1 SLIWKEWEOKKPCT-CEUYOYMZSA-N 0.000 description 1
• JCQMVGHNRJRBCG-MHWRTBLVSA-N n-[[(3s,5s)-3-(2-amino-2-methylpropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CC(C)(C)N)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 JCQMVGHNRJRBCG-MHWRTBLVSA-N 0.000 description 1
• BWKKOIFSAZINTN-HOFKKMOUSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCN)NC(=O)C1=CC=C(Cl)C(Cl)=C1 BWKKOIFSAZINTN-HOFKKMOUSA-N 0.000 description 1
• BTIWBRIJMDPPKC-YTMVLYRLSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)NC[C@H]1N[C@@H](CCN)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 BTIWBRIJMDPPKC-YTMVLYRLSA-N 0.000 description 1
• HGIXWOZHCWCIOK-YTMVLYRLSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-(4-chlorophenyl)propanamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCN)NC(=O)CCC1=CC=C(Cl)C=C1 HGIXWOZHCWCIOK-YTMVLYRLSA-N 0.000 description 1
• QDLJXAZKKOTFNI-BDYUSTAISA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-(trifluoromethyl)benzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCN)NC(=O)C1=CC=CC(C(F)(F)F)=C1 QDLJXAZKKOTFNI-BDYUSTAISA-N 0.000 description 1
• CBFIYCZMOUVLSR-BDYUSTAISA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-(trifluoromethyl)benzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCN)NC(=O)C1=CC=C(C(F)(F)F)C=C1 CBFIYCZMOUVLSR-BDYUSTAISA-N 0.000 description 1
• HUOQZTHEUHMEDW-SMCANUKXSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 HUOQZTHEUHMEDW-SMCANUKXSA-N 0.000 description 1
• CSVQQMRXTKTVBN-LPHOPBHVSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethyl-2-methylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(C)(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(Cl)=C1 CSVQQMRXTKTVBN-LPHOPBHVSA-N 0.000 description 1
• VFXJBQANOFFTLE-GOTSBHOMSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethyl-2-methylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(C)(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 VFXJBQANOFFTLE-GOTSBHOMSA-N 0.000 description 1
• NCOYGPIFNDMXCO-LXKGCQHHSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethyl-3-methylbut-3-enyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)C(C)=C)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(Cl)=C1 NCOYGPIFNDMXCO-LXKGCQHHSA-N 0.000 description 1
• QJCVJUHQSMDVKK-JUQRWGLSSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethyl-3-methylbut-3-enyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)C(C)=C)CC[C@H]1CNC(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 QJCVJUHQSMDVKK-JUQRWGLSSA-N 0.000 description 1
• SFWBAROKYIEQQK-ICSRJNTNSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-chloro-4-methylbenzamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C)C(Cl)=C1 SFWBAROKYIEQQK-ICSRJNTNSA-N 0.000 description 1
• ZCQARZDWEORZBP-LPHOPBHVSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-chloro-3-fluorobenzamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(F)=C1 ZCQARZDWEORZBP-LPHOPBHVSA-N 0.000 description 1
• IZLQANWXAURBRV-ICSRJNTNSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-chloro-3-methylbenzamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(C)=C1 IZLQANWXAURBRV-ICSRJNTNSA-N 0.000 description 1
• IEKXJQVZGMJMCA-GOTSBHOMSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-bromonaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=C(Br)C=C2)C2=C1 IEKXJQVZGMJMCA-GOTSBHOMSA-N 0.000 description 1
• CUXGFAFNHPUFBW-GOTSBHOMSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 CUXGFAFNHPUFBW-GOTSBHOMSA-N 0.000 description 1
• VRPPVWOIMJSSEJ-GOTSBHOMSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=C(F)C=C2)C2=C1 VRPPVWOIMJSSEJ-GOTSBHOMSA-N 0.000 description 1
• HBKPZZFNAMXAOE-HSJPWVCISA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-(3-methyl-2-phenylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCN)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(C(C)C)C1=CC=CC=C1 HBKPZZFNAMXAOE-HSJPWVCISA-N 0.000 description 1
• ZLMMRMFQYXKUTG-JXFKEZNVSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2,4-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@H]1N[C@H](C(N(CC=2C(=CC(Cl)=CC=2)Cl)CC1)=O)CCN)NC(=O)C1=CC=C(Cl)C(Cl)=C1 ZLMMRMFQYXKUTG-JXFKEZNVSA-N 0.000 description 1
• VXNONGPPOZEGEO-UPVQGACJSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2,4-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(Cl)=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC1=CC=C(Cl)C=C1Cl VXNONGPPOZEGEO-UPVQGACJSA-N 0.000 description 1
• SSKMMZGAMAHEJL-KNBMTAEXSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2r)-2-ethyl-3-methylbutyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound N1[C@@H](CCN)C(=O)N(C[C@H](CC)C(C)C)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(Cl)=C1 SSKMMZGAMAHEJL-KNBMTAEXSA-N 0.000 description 1
• YNDUUKABKHQMSJ-NWVWQQAFSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2r)-2-ethyl-3-methylbutyl]-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(C[C@H](CC)C(C)C)CC[C@H]1CNC(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 YNDUUKABKHQMSJ-NWVWQQAFSA-N 0.000 description 1
• SSKMMZGAMAHEJL-SYNHAJSKSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2s)-2-ethyl-3-methylbutyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound N1[C@@H](CCN)C(=O)N(C[C@@H](CC)C(C)C)CC[C@H]1CNC(=O)C1=CC=C(Cl)C(Cl)=C1 SSKMMZGAMAHEJL-SYNHAJSKSA-N 0.000 description 1
• YNDUUKABKHQMSJ-DKLXNKCPSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(2s)-2-ethyl-3-methylbutyl]-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound N1[C@@H](CCN)C(=O)N(C[C@@H](CC)C(C)C)CC[C@H]1CNC(=O)C1=CC=C(C=C(Cl)C=C2)C2=C1 YNDUUKABKHQMSJ-DKLXNKCPSA-N 0.000 description 1
• LAOYIESGAAPHNK-PXNSSMCTSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@H]1N[C@H](C(N(CC=2C=C(Cl)C=C(Cl)C=2)CC1)=O)CCN)NC(=O)C1=CC=C(Cl)C(Cl)=C1 LAOYIESGAAPHNK-PXNSSMCTSA-N 0.000 description 1
• SAZDPTSZGYBNIO-ZEQRLZLVSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(Cl)=CC2=CC=1)N[C@H](C1=O)CCN)CN1CC1=CC(Cl)=CC(Cl)=C1 SAZDPTSZGYBNIO-ZEQRLZLVSA-N 0.000 description 1
• NKYAUCIDYPAKAP-ADNZQJBKSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(3,5-dimethylcyclohexyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C1C(C)CC(C)CC1CN1C(=O)[C@H](CCN)N[C@H](CNC(=O)C=2C=C(Cl)C(Cl)=CC=2)CC1 NKYAUCIDYPAKAP-ADNZQJBKSA-N 0.000 description 1
• GHTFXPGMMCNCPQ-OSTLVTSRSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[(3,5-dimethylcyclohexyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1C(C)CC(C)CC1CN1C(=O)[C@H](CCN)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 GHTFXPGMMCNCPQ-OSTLVTSRSA-N 0.000 description 1
• HKNGQTNXBWWWPO-AIKKUKTPSA-N n-[[(3s,5s)-3-(2-aminoethyl)-1-[2-(4-chlorophenyl)propyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCN)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(C)C1=CC=C(Cl)C=C1 HKNGQTNXBWWWPO-AIKKUKTPSA-N 0.000 description 1
• WICUPIKXMHXENI-FOLYQGEWSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-(2-phenylbutyl)-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN)N1)=O)CC(CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 WICUPIKXMHXENI-FOLYQGEWSA-N 0.000 description 1
• MPNJIEHJLOQRCL-KFTXQHHCSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-(2-phenylbutyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCN)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(CC)C1=CC=CC=C1 MPNJIEHJLOQRCL-KFTXQHHCSA-N 0.000 description 1
• FGZDTSSBZOVZFL-MQTLACETSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-(2-thiophen-3-ylbutyl)-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound O=C([C@H](CCN)N[C@H](CNC(=O)C=1C=C2C=CC(Cl)=CC2=CC=1)CC1)N1CC(CC)C=1C=CSC=1 FGZDTSSBZOVZFL-MQTLACETSA-N 0.000 description 1
• WICUPIKXMHXENI-MONBJTKQSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 WICUPIKXMHXENI-MONBJTKQSA-N 0.000 description 1
• MPNJIEHJLOQRCL-AIGMYPEUSA-N n-[[(3s,5s)-3-(2-aminoethyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCN)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 MPNJIEHJLOQRCL-AIGMYPEUSA-N 0.000 description 1
• IRRMHWXPTXBFMN-SMCANUKXSA-N n-[[(3s,5s)-3-(3-amino-3-oxopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCC(=O)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 IRRMHWXPTXBFMN-SMCANUKXSA-N 0.000 description 1
• ZOJZPJKDVGKPAL-WNJJXGMVSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1h-indole-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1NC2=CC=CC=C2C=1)N[C@H](C1=O)CCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ZOJZPJKDVGKPAL-WNJJXGMVSA-N 0.000 description 1
• FYYVLUVZEXACBD-WNJJXGMVSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-(4-fluorophenoxy)acetamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)COC1=CC=C(F)C=C1 FYYVLUVZEXACBD-WNJJXGMVSA-N 0.000 description 1
• QCBUQTAEJQXPDH-TXJYOHDVSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-ethylhexanamide Chemical compound O=C1[C@H](CCCN)N[C@H](CNC(=O)C(CC)CCCC)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 QCBUQTAEJQXPDH-TXJYOHDVSA-N 0.000 description 1
• XSOVPZBZTYQPSS-XTBGFXFQSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-oxo-1-phenylpyrrolidine-3-carboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)C(C1=O)CCN1C1=CC=CC=C1 XSOVPZBZTYQPSS-XTBGFXFQSA-N 0.000 description 1
• XAHFMULGPKQPNU-CUBQBAPOSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)C1=CC=C(Cl)C(Cl)=C1 XAHFMULGPKQPNU-CUBQBAPOSA-N 0.000 description 1
• YRIJEWGEWVSBMX-JDXGNMNLSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)NC[C@H]1N[C@@H](CCCN)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 YRIJEWGEWVSBMX-JDXGNMNLSA-N 0.000 description 1
• BETBALQOLRCOSP-YTMVLYRLSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)C(NN=1)=CC=1C1=CC=CC=C1 BETBALQOLRCOSP-YTMVLYRLSA-N 0.000 description 1
• RUDKYWWUECNFKN-TWJUONSBSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-phenylbenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 RUDKYWWUECNFKN-TWJUONSBSA-N 0.000 description 1
• LRHDGJCOTTVMKL-JDXGNMNLSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-5-(4-chlorophenyl)furan-2-carboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCN)NC(=O)C(O1)=CC=C1C1=CC=C(Cl)C=C1 LRHDGJCOTTVMKL-JDXGNMNLSA-N 0.000 description 1
• UOABSESNZXNJQO-IUDBTDONSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-5-methyl-1-phenylpyrazole-4-carboxamide Chemical compound CC1=C(C(=O)NC[C@H]2N[C@@H](CCCN)C(=O)N(CC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)C=NN1C1=CC=CC=C1 UOABSESNZXNJQO-IUDBTDONSA-N 0.000 description 1
• ZUIVKBAJDLMMDS-CDZUIXILSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-bromonaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(Br)=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ZUIVKBAJDLMMDS-CDZUIXILSA-N 0.000 description 1
• SBIOEJXYDUVYQR-CDZUIXILSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(F)=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 SBIOEJXYDUVYQR-CDZUIXILSA-N 0.000 description 1
• GJDBJWUKDCFAPT-WEZIJMHWSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-(2,2-diphenylethyl)-4-methyl-2-oxo-1,4-diazepan-5-yl]methyl]-6-bromonaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(Br)=CC2=CC=1)N([C@H](C1=O)CCCN)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 GJDBJWUKDCFAPT-WEZIJMHWSA-N 0.000 description 1
• XRTIRNHZVUVWOJ-UPVQGACJSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2,3-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=CC(Cl)=C1Cl XRTIRNHZVUVWOJ-UPVQGACJSA-N 0.000 description 1
• XTKNLEWVDDEEIW-ZCYQVOJMSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2,4-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=C(Cl)C=C1Cl XTKNLEWVDDEEIW-ZCYQVOJMSA-N 0.000 description 1
• GNYPKRMHSTUXSC-ZCYQVOJMSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC(Cl)=CC=C1Cl GNYPKRMHSTUXSC-ZCYQVOJMSA-N 0.000 description 1
• PJUVKKCZPWFZRM-OFVILXPXSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2,6-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=C(Cl)C=CC=C1Cl PJUVKKCZPWFZRM-OFVILXPXSA-N 0.000 description 1
• ALCHGVJBUISZGZ-ZAZPTELASA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2,6-dimethylcyclohexyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound CC1CCCC(C)C1CN1C(=O)[C@H](CCCN)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 ALCHGVJBUISZGZ-ZAZPTELASA-N 0.000 description 1
• GXINBEVXEUIFAY-ZCYQVOJMSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(2-chlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=CC=C1Cl GXINBEVXEUIFAY-ZCYQVOJMSA-N 0.000 description 1
• JKAROZVYTRWXET-DHLKQENFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(3,4-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=C(Cl)C(Cl)=C1 JKAROZVYTRWXET-DHLKQENFSA-N 0.000 description 1
• SDKHRVBEXCSFAH-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(3,5-difluorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC(F)=CC(F)=C1 SDKHRVBEXCSFAH-DQEYMECFSA-N 0.000 description 1
• CZZGONADCVJPNV-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(3-chloro-5-fluorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC(F)=CC(Cl)=C1 CZZGONADCVJPNV-DQEYMECFSA-N 0.000 description 1
• YFYIVHIAEHXMCH-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(3-chlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=CC(Cl)=C1 YFYIVHIAEHXMCH-DQEYMECFSA-N 0.000 description 1
• PXFWVGFTDAQGCB-UIOOFZCWSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(3-fluoro-5-methylphenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound CC1=CC(F)=CC(CN2C([C@H](CCCN)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)=C1 PXFWVGFTDAQGCB-UIOOFZCWSA-N 0.000 description 1
• FYYRJGXJJZHVBW-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[(4-chlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC=C(Cl)C=C1 FYYRJGXJJZHVBW-DQEYMECFSA-N 0.000 description 1
• NHAPQTWPUKDQDZ-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 NHAPQTWPUKDQDZ-DQEYMECFSA-N 0.000 description 1
• DPRPUEFBFUJOKZ-DQEYMECFSA-N n-[[(3s,5s)-3-(3-aminopropyl)-1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1=CC(F)=CC(C(F)(F)F)=C1 DPRPUEFBFUJOKZ-DQEYMECFSA-N 0.000 description 1
• HIXSQRVONZIWDI-WLHBAFDUSA-N n-[[(3s,5s)-3-(3-aminopropyl)-2-oxo-1-(2-phenylbutyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCCN)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(CC)C1=CC=CC=C1 HIXSQRVONZIWDI-WLHBAFDUSA-N 0.000 description 1
• BAKDCQAYDVMYLF-KYJUHHDHSA-N n-[[(3s,5s)-3-(3-aminopropyl)-2-oxo-1-[(1-phenylcyclohexyl)methyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCN)CN1CC1(C=2C=CC=CC=2)CCCCC1 BAKDCQAYDVMYLF-KYJUHHDHSA-N 0.000 description 1
• BQPYVCCPIGAKCW-PUUVEUEGSA-N n-[[(3s,5s)-3-(3-aminopropyl)-2-oxo-1-[(2r)-2-phenylpropyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@H](CN2C([C@H](CCCN)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)C)=CC=CC=C1 BQPYVCCPIGAKCW-PUUVEUEGSA-N 0.000 description 1
• HIXSQRVONZIWDI-WWEDSPNTSA-N n-[[(3s,5s)-3-(3-aminopropyl)-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCCN)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 HIXSQRVONZIWDI-WWEDSPNTSA-N 0.000 description 1
• BQPYVCCPIGAKCW-AIGMYPEUSA-N n-[[(3s,5s)-3-(3-aminopropyl)-2-oxo-1-[(2s)-2-phenylpropyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCCN)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)C)=CC=CC=C1 BQPYVCCPIGAKCW-AIGMYPEUSA-N 0.000 description 1
• NMLHHLNZWBDJJX-YTMVLYRLSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1OC2=CC=CC=C2C=1)N[C@H](C1=O)CCCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 NMLHHLNZWBDJJX-YTMVLYRLSA-N 0.000 description 1
• ZEMZLZWYFQYUMY-WEZIJMHWSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCCN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 ZEMZLZWYFQYUMY-WEZIJMHWSA-N 0.000 description 1
• YISLVKWGIZADMO-SVEHJYQDSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(naphthalen-1-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-(1h-indol-3-yl)acetamide Chemical compound C1CN(CC=2C3=CC=CC=C3C=CC=2)C(=O)[C@H](CCCCN)N[C@@H]1CNC(=O)CC1=CNC2=CC=CC=C12 YISLVKWGIZADMO-SVEHJYQDSA-N 0.000 description 1
• PDOBGZCNSXLOEM-YZNIXAGQSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(naphthalen-1-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-1-carboxamide Chemical compound C1CN(CC=2C3=CC=CC=C3C=CC=2)C(=O)[C@H](CCCCN)N[C@@H]1CNC(=O)C1=CC=CC2=CC=CC=C12 PDOBGZCNSXLOEM-YZNIXAGQSA-N 0.000 description 1
• MVRXLHCLTQPYTR-JDXGNMNLSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(naphthalen-1-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC=2C3=CC=CC=C3C=CC=2)C(=O)[C@H](CCCCN)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 MVRXLHCLTQPYTR-JDXGNMNLSA-N 0.000 description 1
• SDVSRNPMIZLVKX-FIBWVYCGSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(naphthalen-2-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-1-carboxamide Chemical compound C1CN(CC=2C=C3C=CC=CC3=CC=2)C(=O)[C@H](CCCCN)N[C@@H]1CNC(=O)C1=CC=CC2=CC=CC=C12 SDVSRNPMIZLVKX-FIBWVYCGSA-N 0.000 description 1
• VCMTYQKPHKCMBO-KYJUHHDHSA-N n-[[(3s,5s)-3-(4-aminobutyl)-1-(naphthalen-2-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC=2C=C3C=CC=CC3=CC=2)C(=O)[C@H](CCCCN)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 VCMTYQKPHKCMBO-KYJUHHDHSA-N 0.000 description 1
• SPIZUXNPIGYOQI-JDXGNMNLSA-N n-[[(3s,5s)-3-(aminomethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CN)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 SPIZUXNPIGYOQI-JDXGNMNLSA-N 0.000 description 1
• PCFLAUAVIGOSHR-LPHOPBHVSA-N n-[[(3s,5s)-3-(aminomethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@H]1N[C@H](C(N(CC=2C=C(Cl)C=C(Cl)C=2)CC1)=O)CN)NC(=O)C1=CC=C(Cl)C(Cl)=C1 PCFLAUAVIGOSHR-LPHOPBHVSA-N 0.000 description 1
• JOKUOPPJNZPFEZ-GOTSBHOMSA-N n-[[(3s,5s)-3-(aminomethyl)-1-[(3,5-dichlorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CN)CN1CC1=CC(Cl)=CC(Cl)=C1 JOKUOPPJNZPFEZ-GOTSBHOMSA-N 0.000 description 1
• SRVFWSOOORKLJH-GIWKVKTRSA-N n-[[(3s,5s)-3-(cyclohexylmethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CC1CCCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 SRVFWSOOORKLJH-GIWKVKTRSA-N 0.000 description 1
• PEDUKYVFLGCZSG-IXLXJOPFSA-N n-[[(3s,5s)-3-[2-(azepan-1-yl)ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN2CCCCCC2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 PEDUKYVFLGCZSG-IXLXJOPFSA-N 0.000 description 1
• LEXIOIJEBBDYFC-DJDPXSJISA-N n-[[(3s,5s)-3-[2-(azepan-1-yl)ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CN1CCCCCC1 LEXIOIJEBBDYFC-DJDPXSJISA-N 0.000 description 1
• DHCFNRRGYVCRJE-XWJWOQKWSA-N n-[[(3s,5s)-3-[2-(benzylamino)ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCNCC=2C=CC=CC=2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 DHCFNRRGYVCRJE-XWJWOQKWSA-N 0.000 description 1
• FUKQUWBYBLOIRV-SMCANUKXSA-N n-[[(3s,5s)-3-[2-(diaminomethylideneamino)oxyethyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCONC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 FUKQUWBYBLOIRV-SMCANUKXSA-N 0.000 description 1
• UWQQSOAJJGLAJJ-LRHLLKFHSA-N n-[[(3s,5s)-3-[2-(diethylamino)ethyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCN(CC)CC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 UWQQSOAJJGLAJJ-LRHLLKFHSA-N 0.000 description 1
• DIVJZDICYXIBKA-WEZIJMHWSA-N n-[[(3s,5s)-3-[2-(dimethylamino)ethyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCN(C)C)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DIVJZDICYXIBKA-WEZIJMHWSA-N 0.000 description 1
• YGGNBVSOSLCEBK-STQWGSIPSA-N n-[[(3s,5s)-3-[2-[[amino-(propan-2-ylamino)methylidene]amino]ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCNC(=N)NC(C)C)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 YGGNBVSOSLCEBK-STQWGSIPSA-N 0.000 description 1
• HFTHSMXFEPZROM-LNMMVMNESA-N n-[[(3s,5s)-3-[2-[acetyl(propan-2-yl)amino]ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@@H](CN2C([C@H](CCN(C(C)C)C(C)=O)N[C@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)CC2)=O)CC)=CC=CC=C1 HFTHSMXFEPZROM-LNMMVMNESA-N 0.000 description 1
• ZJQSFIJDEHYCSI-VUAYVDPTSA-N n-[[(3s,5s)-3-[2-[benzyl(methyl)amino]ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN(C)CC=2C=CC=CC=2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 ZJQSFIJDEHYCSI-VUAYVDPTSA-N 0.000 description 1
• LARCUJCRWYFCOJ-QURRFSBHSA-N n-[[(3s,5s)-3-[2-[tert-butyl(methyl)amino]ethyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-3,4-dichlorobenzamide Chemical compound C([C@@H]1CCN(C([C@H](CCN(C)C(C)(C)C)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 LARCUJCRWYFCOJ-QURRFSBHSA-N 0.000 description 1
• FVFAEOHHVAXJJV-QARUCVQPSA-N n-[[(3s,5s)-3-[3-(benzylamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCNCC=1C=CC=CC=1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 FVFAEOHHVAXJJV-QARUCVQPSA-N 0.000 description 1
• WBJLUKAHTWVGIC-GIWKVKTRSA-N n-[[(3s,5s)-3-[3-(cyclobutylamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCNC1CCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 WBJLUKAHTWVGIC-GIWKVKTRSA-N 0.000 description 1
• RAKGGYNKYIHQSI-DJDPXSJISA-N n-[[(3s,5s)-3-[3-(cyclohexylamino)-3-oxopropyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H]1N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN(C1=O)C[C@@H](CC)C=1C=CC=CC=1)CC(=O)NC1CCCCC1 RAKGGYNKYIHQSI-DJDPXSJISA-N 0.000 description 1
• IKEACBIJKWZQNF-BAEGBANDSA-N n-[[(3s,5s)-3-[3-(cyclohexylamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCNC1CCCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 IKEACBIJKWZQNF-BAEGBANDSA-N 0.000 description 1
• DOKVYAMBTPOVNF-JSXFGMRASA-N n-[[(3s,5s)-3-[3-(cyclopentylamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCNC1CCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DOKVYAMBTPOVNF-JSXFGMRASA-N 0.000 description 1
• XFTYVIHDMVCKHS-XMASUTJCSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,2,3,4-tetrahydronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C1CC2=CC=CC=C2CC1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 XFTYVIHDMVCKHS-XMASUTJCSA-N 0.000 description 1
• OIXMAOCJKIQWDP-BDYUSTAISA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,3-benzodioxole-5-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2OCOC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 OIXMAOCJKIQWDP-BDYUSTAISA-N 0.000 description 1
• OYYQWIXOFRMTOX-LSYYVWMOSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1,3-benzothiazole-6-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2SC=NC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 OYYQWIXOFRMTOX-LSYYVWMOSA-N 0.000 description 1
• RJGLNXBOEGFWTK-XCZPVHLTSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1-benzofuran-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1OC2=CC=CC=C2C=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 RJGLNXBOEGFWTK-XCZPVHLTSA-N 0.000 description 1
• QATWEZXRMWFGTE-XCZPVHLTSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1-benzothiophene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1SC2=CC=CC=C2C=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 QATWEZXRMWFGTE-XCZPVHLTSA-N 0.000 description 1
• LPMORJOHMZFEIK-YTMVLYRLSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-1-benzothiophene-5-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CSC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 LPMORJOHMZFEIK-YTMVLYRLSA-N 0.000 description 1
• BHYXUUNNKRKTBD-SMCANUKXSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2,3-dihydro-1h-indene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C1CC2=CC=CC=C2C1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 BHYXUUNNKRKTBD-SMCANUKXSA-N 0.000 description 1
• OJOHMJHTJUYUDU-SVEHJYQDSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2,4-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC=C1C(=O)NC[C@H]1N[C@@H](CCCNC(N)=N)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 OJOHMJHTJUYUDU-SVEHJYQDSA-N 0.000 description 1
• UFCYHRZLFHTIGL-TXJYOHDVSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-ethylhexanamide Chemical compound O=C1[C@H](CCCNC(N)=N)N[C@H](CNC(=O)C(CC)CCCC)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 UFCYHRZLFHTIGL-TXJYOHDVSA-N 0.000 description 1
• ICTHKJGARPGKGX-WNJJXGMVSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-phenoxyacetamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)COC1=CC=CC=C1 ICTHKJGARPGKGX-WNJJXGMVSA-N 0.000 description 1
• JPYWMTFCLCNPPY-RSNGWFSUSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2-phenylcyclopropane-1-carboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C1CC1C1=CC=CC=C1 JPYWMTFCLCNPPY-RSNGWFSUSA-N 0.000 description 1
• GPEJAIVLVVLFTF-IGKIAQTJSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-2h-benzotriazole-5-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2N=NNC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 GPEJAIVLVVLFTF-IGKIAQTJSA-N 0.000 description 1
• UYYDDRYFTZEDCZ-JDXGNMNLSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3,4-dimethylbenzamide Chemical compound C1=C(C)C(C)=CC=C1C(=O)NC[C@H]1N[C@@H](CCCNC(N)=N)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 UYYDDRYFTZEDCZ-JDXGNMNLSA-N 0.000 description 1
• BGYBDRQRKARBIH-NHZFLZHXSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-phenoxybenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 BGYBDRQRKARBIH-NHZFLZHXSA-N 0.000 description 1
• HSWYIFVAUMCGPT-JDXGNMNLSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-phenylpropanamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)CCC1=CC=CC=C1 HSWYIFVAUMCGPT-JDXGNMNLSA-N 0.000 description 1
• MGALBVBSAKGKNO-LSYYVWMOSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3h-benzimidazole-5-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2N=CNC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 MGALBVBSAKGKNO-LSYYVWMOSA-N 0.000 description 1
• JOPRNKCJFWPMKD-NHZFLZHXSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-phenoxybenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 JOPRNKCJFWPMKD-NHZFLZHXSA-N 0.000 description 1
• SEHSYULGJIALHX-TWJUONSBSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-4-phenylbenzamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 SEHSYULGJIALHX-TWJUONSBSA-N 0.000 description 1
• ZOFQWNXCEGKDES-IUDBTDONSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-5-methyl-1-phenylpyrazole-4-carboxamide Chemical compound CC1=C(C(=O)NC[C@H]2N[C@@H](CCCNC(N)=N)C(=O)N(CC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)C=NN1C1=CC=CC=C1 ZOFQWNXCEGKDES-IUDBTDONSA-N 0.000 description 1
• LUHXUGOQYLKEAQ-CDZUIXILSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-6-fluoronaphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC(F)=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 LUHXUGOQYLKEAQ-CDZUIXILSA-N 0.000 description 1
• SZIKENIAXDBLSZ-XCZPVHLTSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]cyclohexanecarboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C1CCCCC1 SZIKENIAXDBLSZ-XCZPVHLTSA-N 0.000 description 1
• IAFLAYKZFOVGIP-BDYUSTAISA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]cyclopentanecarboxamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCCNC(=N)N)NC(=O)C1CCCC1 IAFLAYKZFOVGIP-BDYUSTAISA-N 0.000 description 1
• XBQSFLUOEFLRMW-JDXGNMNLSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]isoquinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)C=1N=CC2=CC=CC=C2C=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 XBQSFLUOEFLRMW-JDXGNMNLSA-N 0.000 description 1
• JHNKBSKIHRSONS-DHIFEGFHSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]quinoline-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1N=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 JHNKBSKIHRSONS-DHIFEGFHSA-N 0.000 description 1
• DGSLZNRWLKTSPO-IZEXYCQBSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]quinoline-3-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=NC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DGSLZNRWLKTSPO-IZEXYCQBSA-N 0.000 description 1
• NLQZQYYRZWYWMJ-SVEHJYQDSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]quinoxaline-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1N=C2C=CC=CC2=NC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 NLQZQYYRZWYWMJ-SVEHJYQDSA-N 0.000 description 1
• ORGUBOVABKKYFO-ACHIHNKUSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylpropyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(C)(C=1C=CC=CC=1)C1=CC=CC=C1 ORGUBOVABKKYFO-ACHIHNKUSA-N 0.000 description 1
• MVQZRJYURGRTIW-ZEQRLZLVSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2-ethylbutyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound N1[C@@H](CCCNC(N)=N)C(=O)N(CC(CC)CC)CC[C@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 MVQZRJYURGRTIW-ZEQRLZLVSA-N 0.000 description 1
• CBJRTXOFLNIBPS-TXIPYEPDSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2-methoxy-2-phenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(OC)C1=CC=CC=C1 CBJRTXOFLNIBPS-TXIPYEPDSA-N 0.000 description 1
• WKXADWDUHHIJAQ-KYJUHHDHSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(2-naphthalen-2-ylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CCC=2C=C3C=CC=CC3=CC=2)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 WKXADWDUHHIJAQ-KYJUHHDHSA-N 0.000 description 1
• JKHAMWNJJHWPQL-IEWVHIKDSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(9h-fluoren-9-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC2C3=CC=CC=C3C3=CC=CC=C32)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 JKHAMWNJJHWPQL-IEWVHIKDSA-N 0.000 description 1
• RUAUGPCLNGSTAG-YTMVLYRLSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(naphthalen-1-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC=2C3=CC=CC=C3C=CC=2)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 RUAUGPCLNGSTAG-YTMVLYRLSA-N 0.000 description 1
• YUDDAXQRMZKAPF-VMPREFPWSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-(naphthalen-2-ylmethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(CC=2C=C3C=CC=CC3=CC=2)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 YUDDAXQRMZKAPF-VMPREFPWSA-N 0.000 description 1
• RADDCXSUXMLAEQ-LNMMVMNESA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(2r)-1,1-diphenylpropan-2-yl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C=1C=CC=CC=1C([C@@H](C)N1C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1)=O)C1=CC=CC=C1 RADDCXSUXMLAEQ-LNMMVMNESA-N 0.000 description 1
• OSNCOMUVMKIOFM-LNMMVMNESA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(2r)-1-fluoro-1,1-diphenylpropan-2-yl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C=1C=CC=CC=1C(F)([C@H](N1C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1)=O)C)C1=CC=CC=C1 OSNCOMUVMKIOFM-LNMMVMNESA-N 0.000 description 1
• RADDCXSUXMLAEQ-OATBXSGESA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(2s)-1,1-diphenylpropan-2-yl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C=1C=CC=CC=1C([C@H](C)N1C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1)=O)C1=CC=CC=C1 RADDCXSUXMLAEQ-OATBXSGESA-N 0.000 description 1
• SMUSSXMLUFUAPZ-DQEYMECFSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(3,5-difluorophenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC1=CC(F)=CC(F)=C1 SMUSSXMLUFUAPZ-DQEYMECFSA-N 0.000 description 1
• VCQJMRSDQYAODK-HDYFOKATSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(3,5-dimethylcyclohexyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1C(C)CC(C)CC1CN1C(=O)[C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=2C=C3C=CC=CC3=CC=2)CC1 VCQJMRSDQYAODK-HDYFOKATSA-N 0.000 description 1
• QUXFTJDVAXLSOB-SVBPBHIXSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[(3,5-dimethylphenyl)methyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound CC1=CC(C)=CC(CN2C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)CC2)=O)=C1 QUXFTJDVAXLSOB-SVBPBHIXSA-N 0.000 description 1
• DVRZIZBUPVOICY-AHWVRZQESA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[2-(2,4-dichlorophenyl)ethyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CCC1=CC=C(Cl)C=C1Cl DVRZIZBUPVOICY-AHWVRZQESA-N 0.000 description 1
• XEECERRNBOAODP-OZXSUGGESA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[2-(3,4-dichlorophenyl)ethyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CCC1=CC=C(Cl)C(Cl)=C1 XEECERRNBOAODP-OZXSUGGESA-N 0.000 description 1
• GQLFUOIDZYRUBH-HSJPWVCISA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-[3-(dimethylamino)-3-oxo-2-phenylpropyl]-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(C(=O)N(C)C)C1=CC=CC=C1 GQLFUOIDZYRUBH-HSJPWVCISA-N 0.000 description 1
• OGFAWJRTQSHKDV-XCZPVHLTSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-1-naphthalen-2-yl-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1CN(C=2C=C3C=CC=CC3=CC=2)C(=O)[C@H](CCCNC(=N)N)N[C@@H]1CNC(=O)C1=CC=C(C=CC=C2)C2=C1 OGFAWJRTQSHKDV-XCZPVHLTSA-N 0.000 description 1
• FQJPIRCJJADUTL-AQBAIUPUSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1-(2-phenoxy-2-phenylethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)OC1=CC=CC=C1 FQJPIRCJJADUTL-AQBAIUPUSA-N 0.000 description 1
• QSTKPYSOOVYKHW-KOPQTXDBSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1-(2-phenyl-2-phenylmethoxyethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)OCC1=CC=CC=C1 QSTKPYSOOVYKHW-KOPQTXDBSA-N 0.000 description 1
• YJVUOLOUFSCBHJ-ASYYUYISSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1-(2-phenyl-2-propoxyethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C([C@H](CCCNC(N)=N)N[C@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)CC1)N1CC(OCCC)C1=CC=CC=C1 YJVUOLOUFSCBHJ-ASYYUYISSA-N 0.000 description 1
• ZZGHTUOZQOCZOF-GAVYTZHXSA-N n-[[(3s,5s)-3-[3-(diaminomethylideneamino)propyl]-2-oxo-1-(3-oxo-2-phenyl-3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCNC(=N)N)CN1CC(C=1C=CC=CC=1)C(=O)N1CCCCC1 ZZGHTUOZQOCZOF-GAVYTZHXSA-N 0.000 description 1
• RBXZJSMWYMBTFP-GWTOPCPNSA-N n-[[(3s,5s)-3-[3-[butyl(methyl)amino]-3-oxopropyl]-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C1([C@H](CC)CN2CC[C@@H](CNC(=O)C=3C=C4C=CC=CC4=CC=3)N[C@H](C2=O)CCC(=O)N(C)CCCC)=CC=CC=C1 RBXZJSMWYMBTFP-GWTOPCPNSA-N 0.000 description 1
• XHLLZJNFKOIUFF-PUAPYOPTSA-N n-[[(3s,5s)-3-[3-[di(cyclobutyl)amino]propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCCN(C1CCC1)C1CCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 XHLLZJNFKOIUFF-PUAPYOPTSA-N 0.000 description 1
• JIUPIHOHJCKPTD-GIWKVKTRSA-N n-[[(3s,5s)-3-benzyl-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CC=1C=CC=CC=1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 JIUPIHOHJCKPTD-GIWKVKTRSA-N 0.000 description 1
• PEEXUKDMJXUJAG-WEZIJMHWSA-N n-[[(3s,5s)-3-butyl-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@@H](CNC(=O)C=1C=C2C=CC=CC2=CC=1)N[C@H](C1=O)CCCC)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 PEEXUKDMJXUJAG-WEZIJMHWSA-N 0.000 description 1
• IHEVWRFMSNWYFG-YDTRGFDASA-N n-[[(3s,5s)-3-butyl-2-oxo-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]-6-chloronaphthalene-2-carboxamide Chemical compound C1([C@H](CC)CN2CC[C@@H](CNC(=O)C=3C=C4C=CC(Cl)=CC4=CC=3)N[C@H](C2=O)CCCC)=CC=CC=C1 IHEVWRFMSNWYFG-YDTRGFDASA-N 0.000 description 1
• PNITVXIZXUWQET-UHFFFAOYSA-N n-[[1-(2,2-diphenylethyl)-2-oxo-3-(piperidin-4-ylmethyl)-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NCC(NC(CC1CCNCC1)C1=O)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 PNITVXIZXUWQET-UHFFFAOYSA-N 0.000 description 1
• YTNMWQMBKAZCMS-UHFFFAOYSA-N n-[[1-(2,2-diphenylethyl)-2-oxo-3-piperidin-4-yl-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)NCC(NC(C1=O)C2CCNCC2)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 YTNMWQMBKAZCMS-UHFFFAOYSA-N 0.000 description 1
• DKFQXTHTGAKMJQ-UHFFFAOYSA-N n-[[3-[3-(diaminomethylideneamino)propyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound O=C1C(CCCNC(=N)N)NC(CNC(=O)C=2C=C3C=CC=CC3=CC=2)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 DKFQXTHTGAKMJQ-UHFFFAOYSA-N 0.000 description 1
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• SWBLLSQMOMPTMC-UHFFFAOYSA-N naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)N)=CC=C21 SWBLLSQMOMPTMC-UHFFFAOYSA-N 0.000 description 1
• OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
• IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
• 238000006386 neutralization reaction Methods 0.000 description 1
• 231100000344 non-irritating Toxicity 0.000 description 1
• 239000012457 nonaqueous media Substances 0.000 description 1
• 239000002687 nonaqueous vehicle Substances 0.000 description 1
• 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
• KIQQMECNKUGGKA-NMYWJIRASA-N norgestimate Chemical compound O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 KIQQMECNKUGGKA-NMYWJIRASA-N 0.000 description 1
• 229960000417 norgestimate Drugs 0.000 description 1
• 235000019488 nut oil Nutrition 0.000 description 1
• 239000010466 nut oil Substances 0.000 description 1
• 230000035764 nutrition Effects 0.000 description 1
• 235000016709 nutrition Nutrition 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
• 229940127234 oral contraceptive Drugs 0.000 description 1
• 239000003539 oral contraceptive agent Substances 0.000 description 1
• 150000002895 organic esters Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• 150000003901 oxalic acid esters Chemical class 0.000 description 1
• 230000003647 oxidation Effects 0.000 description 1
• 238000007254 oxidation reaction Methods 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 239000002540 palm oil Substances 0.000 description 1
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
• 238000007911 parenteral administration Methods 0.000 description 1
• 239000006072 paste Substances 0.000 description 1
• 230000008506 pathogenesis Effects 0.000 description 1
• 235000020232 peanut Nutrition 0.000 description 1
• 239000000312 peanut oil Substances 0.000 description 1
• 230000035515 penetration Effects 0.000 description 1
• 210000003899 penis Anatomy 0.000 description 1
• UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical compound C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 210000005259 peripheral blood Anatomy 0.000 description 1
• 239000011886 peripheral blood Substances 0.000 description 1
• 230000002093 peripheral effect Effects 0.000 description 1
• 229950000688 phenothiazine Drugs 0.000 description 1
• WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
• 239000003016 pheromone Substances 0.000 description 1
• 239000011574 phosphorus Substances 0.000 description 1
• 230000036211 photosensitivity Effects 0.000 description 1
• LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
• IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
• 230000019612 pigmentation Effects 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 239000010665 pine oil Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000005936 piperidyl group Chemical group 0.000 description 1
• 239000010471 pistachio oil Substances 0.000 description 1
• 229940082415 pistachio oil Drugs 0.000 description 1
• 230000001817 pituitary effect Effects 0.000 description 1
• 239000000902 placebo Substances 0.000 description 1
• 229940068196 placebo Drugs 0.000 description 1
• 229920001451 polypropylene glycol Polymers 0.000 description 1
• 229950008882 polysorbate Drugs 0.000 description 1
• 239000010491 poppyseed oil Substances 0.000 description 1
• 235000020004 porter Nutrition 0.000 description 1
• 238000002600 positron emission tomography Methods 0.000 description 1
• 229940114930 potassium stearate Drugs 0.000 description 1
• ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000002243 precursor Substances 0.000 description 1
• 230000002335 preservative effect Effects 0.000 description 1
• 210000001948 pro-b lymphocyte Anatomy 0.000 description 1
• 230000008569 process Effects 0.000 description 1
• JDCXNNXRSROFIU-UHFFFAOYSA-N prop-2-enyl n-(2,2-diphenylethyl)-n-[4-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxobutyl]carbamate Chemical compound C=1C=CC=CC=1C(CN(CCC(=O)CNC(=O)OC(C)(C)C)C(=O)OCC=C)C1=CC=CC=C1 JDCXNNXRSROFIU-UHFFFAOYSA-N 0.000 description 1
• VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 1
• VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
• SJMCLWCCNYAWRQ-UHFFFAOYSA-N propane-2-sulfonamide Chemical compound CC(C)S(N)(=O)=O SJMCLWCCNYAWRQ-UHFFFAOYSA-N 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 210000002307 prostate Anatomy 0.000 description 1
• 239000012264 purified product Substances 0.000 description 1
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 239000010499 rapseed oil Substances 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 210000000664 rectum Anatomy 0.000 description 1
• 238000010992 reflux Methods 0.000 description 1
• 230000009892 regulation of energy homeostasis Effects 0.000 description 1
• 210000003289 regulatory T cell Anatomy 0.000 description 1
• 239000005871 repellent Substances 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229930002330 retinoic acid Natural products 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 235000005713 safflower oil Nutrition 0.000 description 1
• 239000003813 safflower oil Substances 0.000 description 1
• 150000003902 salicylic acid esters Chemical class 0.000 description 1
• 201000005218 sebaceous adenoma Diseases 0.000 description 1
• 230000035946 sexual desire Effects 0.000 description 1
• 231100000872 sexual dysfunction Toxicity 0.000 description 1
• 229940057910 shea butter Drugs 0.000 description 1
• 230000007781 signaling event Effects 0.000 description 1
• 150000004760 silicates Chemical class 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 208000017520 skin disease Diseases 0.000 description 1
• 230000036556 skin irritation Effects 0.000 description 1
• 231100000475 skin irritation Toxicity 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
• 235000017557 sodium bicarbonate Nutrition 0.000 description 1
• 239000012279 sodium borohydride Substances 0.000 description 1
• 229910000033 sodium borohydride Inorganic materials 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 229940046303 sodium cetostearyl sulfate Drugs 0.000 description 1
• 239000001509 sodium citrate Substances 0.000 description 1
• NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
• CLBALUNQCMWJSU-UHFFFAOYSA-L sodium;hexadecyl sulfate;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O CLBALUNQCMWJSU-UHFFFAOYSA-L 0.000 description 1
• 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
• 239000012177 spermaceti Substances 0.000 description 1
• 229940084106 spermaceti Drugs 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 230000000087 stabilizing effect Effects 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 239000003206 sterilizing agent Substances 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000005017 substituted alkenyl group Chemical group 0.000 description 1
• 125000005750 substituted cyclic group Chemical group 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 150000003900 succinic acid esters Chemical class 0.000 description 1
• 150000005846 sugar alcohols Chemical class 0.000 description 1
• 150000008163 sugars Chemical class 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 230000002195 synergetic effect Effects 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 230000008685 targeting Effects 0.000 description 1
• 150000003899 tartaric acid esters Chemical class 0.000 description 1
• 231100000462 teratogen Toxicity 0.000 description 1
• 239000003439 teratogenic agent Substances 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• MNQHBJNGAPHYNS-AWEZNQCLSA-N tert-butyl (2s)-4-[methoxy(methyl)amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoate Chemical compound CON(C)C(=O)C[C@@H](C(=O)OC(C)(C)C)NC(=O)OCC1=CC=CC=C1 MNQHBJNGAPHYNS-AWEZNQCLSA-N 0.000 description 1
• QDTBRYXNYPUARV-UHFFFAOYSA-N tert-butyl 2-oxobut-3-enoate Chemical compound CC(C)(C)OC(=O)C(=O)C=C QDTBRYXNYPUARV-UHFFFAOYSA-N 0.000 description 1
• VUMQRDCWJBJBHS-COAVLMKPSA-N tert-butyl N-[1-[(2S,7S)-4-(2,2-diphenylethyl)-2-methyl-7-(methylamino)-3-oxo-1,4-diazepan-2-yl]propan-2-yl]carbamate Chemical compound C(C)(C)(C)OC(=O)NC(C[C@]1(C(N(CC[C@H](N1)NC)CC(C1=CC=CC=C1)C1=CC=CC=C1)=O)C)C VUMQRDCWJBJBHS-COAVLMKPSA-N 0.000 description 1
• DLQDJBSUJNUBQX-UHFFFAOYSA-N tert-butyl n-(2-oxobut-3-enyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC(=O)C=C DLQDJBSUJNUBQX-UHFFFAOYSA-N 0.000 description 1
• PZOOCZCPCJCFIJ-MFUMQWNRSA-N tert-butyl n-[2-[(2s,7s)-7-(aminomethyl)-3-oxo-4-(2-phenylbutyl)-1,4-diazepan-2-yl]ethyl]carbamate Chemical compound C=1C=CC=CC=1C(CC)CN1CC[C@@H](CN)N[C@@H](CCNC(=O)OC(C)(C)C)C1=O PZOOCZCPCJCFIJ-MFUMQWNRSA-N 0.000 description 1
• VSEUTKFVGZBDSJ-UPVQGACJSA-N tert-butyl n-[2-[(2s,7s)-7-(aminomethyl)-4-(2,2-diphenylethyl)-3-oxo-1,4-diazepan-2-yl]ethyl]carbamate Chemical compound O=C1[C@H](CCNC(=O)OC(C)(C)C)N[C@H](CN)CCN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 VSEUTKFVGZBDSJ-UPVQGACJSA-N 0.000 description 1
• DBJCJZFIECOGNI-HOTGVXAUSA-N tert-butyl n-[2-[(2s,7s)-7-(aminomethyl)-4-(2-ethylbutyl)-3-oxo-1,4-diazepan-2-yl]ethyl]carbamate Chemical compound CCC(CC)CN1CC[C@@H](CN)N[C@@H](CCNC(=O)OC(C)(C)C)C1=O DBJCJZFIECOGNI-HOTGVXAUSA-N 0.000 description 1
• NQTYLHMVUDKHOK-IRXDYDNUSA-N tert-butyl n-[2-[(2s,7s)-7-(aminomethyl)-4-[(3,5-dichlorophenyl)methyl]-3-oxo-1,4-diazepan-2-yl]ethyl]carbamate Chemical compound O=C1[C@H](CCNC(=O)OC(C)(C)C)N[C@H](CN)CCN1CC1=CC(Cl)=CC(Cl)=C1 NQTYLHMVUDKHOK-IRXDYDNUSA-N 0.000 description 1
• HKITYPUMYQIWLX-UHFFFAOYSA-N tert-butyl n-[4-(2,2-diphenylethylamino)-2-oxobutyl]carbamate Chemical compound C=1C=CC=CC=1C(CNCCC(=O)CNC(=O)OC(C)(C)C)C1=CC=CC=C1 HKITYPUMYQIWLX-UHFFFAOYSA-N 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
• 238000011200 topical administration Methods 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• 230000037317 transdermal delivery Effects 0.000 description 1
• 230000009466 transformation Effects 0.000 description 1
• 238000000844 transformation Methods 0.000 description 1
• 229960001727 tretinoin Drugs 0.000 description 1
• 210000000427 trigeminal ganglion Anatomy 0.000 description 1
• 229910052722 tritium Inorganic materials 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 230000003827 upregulation Effects 0.000 description 1
• PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
• 239000007762 w/o emulsion Substances 0.000 description 1
• 239000010698 whale oil Substances 0.000 description 1
• 239000010497 wheat germ oil Substances 0.000 description 1
• WHNFPRLDDSXQCL-UHFFFAOYSA-N α-melanotropin Chemical compound C=1N=CNC=1CC(C(=O)NC(CC=1C=CC=CC=1)C(=O)NC(CCCNC(N)=N)C(=O)NC(CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)NC(CCCCN)C(=O)N1C(CCC1)C(=O)NC(C(C)C)C(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(CCSC)NC(=O)C(CO)NC(=O)C(NC(=O)C(CO)NC(C)=O)CC1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UHFFFAOYSA-N 0.000 description 1
• JPZXHKDZASGCLU-LBPRGKRZSA-N β-(2-naphthyl)-alanine Chemical compound C1=CC=CC2=CC(C[C@H](N)C(O)=O)=CC=C21 JPZXHKDZASGCLU-LBPRGKRZSA-N 0.000 description 1
• GZWUQPQBOGLSIM-VOOUCTBASA-N γ msh Chemical compound C([C@H](N)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1N=CNC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC(O)=O)C(C)C)C1=CC=C(O)C=C1 GZWUQPQBOGLSIM-VOOUCTBASA-N 0.000 description 1