NZ587362A - 3-substituted-1,4-diazepan-2-one melanocortin-5 receptor antagonists - Google Patents

Info

Publication number

NZ587362A

NZ587362A NZ587362A NZ58736209A NZ587362A NZ 587362 A NZ587362 A NZ 587362A NZ 587362 A NZ587362 A NZ 587362A NZ 58736209 A NZ58736209 A NZ 58736209A NZ 587362 A NZ587362 A NZ 587362A

Authority

NZ

New Zealand

Prior art keywords

optionally substituted

group

methyl

oxo

diazepan

Prior art date

2008-02-29

Links

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• 108010088565 Melanocortin 5 receptor Proteins 0.000 title claims abstract description 75
• 102000030612 Melanocortin 5 receptor Human genes 0.000 title claims abstract description 74
• -1 3-substituted-1,4-diazepan-2-one Chemical class 0.000 title claims description 190
• 229940044551 receptor antagonist Drugs 0.000 title abstract description 4
• 239000002464 receptor antagonist Substances 0.000 title abstract description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 201
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
• 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 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 59
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 53
• 206010000496 acne Diseases 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 44
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
• 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 claims description 22
• 241000282414 Homo sapiens Species 0.000 claims description 21
• 229960005280 isotretinoin Drugs 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 21
• 125000003342 alkenyl group Chemical group 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 17
• 210000004378 sebocyte Anatomy 0.000 claims description 17
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 14
• 150000002367 halogens Chemical class 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 10
• 229910052794 bromium Inorganic materials 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 10
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 10
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
• 229910052740 iodine Inorganic materials 0.000 claims description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 230000004048 modification Effects 0.000 claims description 8
• 238000012986 modification Methods 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 7
• 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 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 239000003242 anti bacterial agent Substances 0.000 claims description 7
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000001188 haloalkyl group Chemical group 0.000 claims description 7
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 7
• 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 7
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 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 claims description 6
• 229910003827 NRaRb Inorganic materials 0.000 claims description 6
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 6
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
• 229940088710 antibiotic agent Drugs 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 5
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
• 125000004104 aryloxy group Chemical group 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 5
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
• 125000000623 heterocyclic group Chemical group 0.000 claims description 5
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
• 239000004342 Benzoyl peroxide Substances 0.000 claims description 4
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 4
• 108010069820 Pro-Opiomelanocortin Proteins 0.000 claims description 4
• 125000004442 acylamino group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
• 125000001769 aryl amino group Chemical group 0.000 claims description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
• 235000019400 benzoyl peroxide Nutrition 0.000 claims description 4
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
• 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• 230000004069 differentiation Effects 0.000 claims description 4
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 4
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 4
• 238000001794 hormone therapy Methods 0.000 claims description 4
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 4
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 3
• 239000004098 Tetracycline Substances 0.000 claims description 3
• 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 claims description 3
• 229960002916 adapalene Drugs 0.000 claims description 3
• 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 claims description 3
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
• 229960003328 benzoyl peroxide Drugs 0.000 claims description 3
• 230000033228 biological regulation Effects 0.000 claims description 3
• 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 claims description 3
• 229960002227 clindamycin Drugs 0.000 claims description 3
• 229960003276 erythromycin Drugs 0.000 claims description 3
• RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 claims description 3
• JVXXKQIRGQDWOJ-UHFFFAOYSA-N naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(=O)N)=CC=C21 JVXXKQIRGQDWOJ-UHFFFAOYSA-N 0.000 claims description 3
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
• 229960000565 tazarotene Drugs 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229960002180 tetracycline Drugs 0.000 claims description 3
• 229930101283 tetracycline Natural products 0.000 claims description 3
• 235000019364 tetracycline Nutrition 0.000 claims description 3
• 150000003522 tetracyclines Chemical class 0.000 claims description 3
• 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 claims description 2
• GXXJZWDJJIRYMP-IDLVSAJVSA-N (5s,9as)-5-[(2-aminophenyl)methyl]-2-[(e)-3-(4-chlorophenyl)prop-2-enoyl]-7-(2,2-diphenylethyl)-1,3,5,8,9,9a-hexahydroimidazo[1,5-d][1,4]diazepin-6-one Chemical compound NC1=CC=CC=C1C[C@H]1C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC[C@H]2CN(C(=O)\C=C\C=3C=CC(Cl)=CC=3)CN21 GXXJZWDJJIRYMP-IDLVSAJVSA-N 0.000 claims description 2
• TZSKJJAVKBXXPQ-RSPMAXTDSA-N (e)-3-(4-chlorophenyl)-n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(2-oxo-2-piperidin-1-ylethyl)-1,4-diazepan-5-yl]methyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)NC[C@H]1N[C@@H](CC(=O)N2CCCCC2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 TZSKJJAVKBXXPQ-RSPMAXTDSA-N 0.000 claims description 2
• RPHRMRGNTBZKER-UTSBYIISSA-N (e)-3-(4-chlorophenyl)-n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(2-phenylethyl)-1,4-diazepan-5-yl]methyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)NC[C@H]1N[C@@H](CCC=2C=CC=CC=2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RPHRMRGNTBZKER-UTSBYIISSA-N 0.000 claims description 2
• VCPOUCICPQBNHX-YZLBFCITSA-N (e)-3-(4-chlorophenyl)-n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(3-oxo-3-piperidin-1-ylpropyl)-1,4-diazepan-5-yl]methyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)NC[C@H]1N[C@@H](CCC(=O)N2CCCCC2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 VCPOUCICPQBNHX-YZLBFCITSA-N 0.000 claims description 2
• DQXVLHAVTHVSAU-RSPMAXTDSA-N (e)-3-(4-chlorophenyl)-n-[[(3s,5s)-1-(2,2-diphenylethyl)-2-oxo-3-(pyridin-2-ylmethyl)-1,4-diazepan-5-yl]methyl]prop-2-enamide Chemical compound C1=CC(Cl)=CC=C1\C=C\C(=O)NC[C@H]1N[C@@H](CC=2N=CC=CC=2)C(=O)N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 DQXVLHAVTHVSAU-RSPMAXTDSA-N 0.000 claims description 2
• YPJAUCSTGBVYRA-JZBGBCCGSA-N (e)-n-[[(3s,5s)-3-butyl-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]-3-(4-chlorophenyl)prop-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)CCCC)NC(=O)\C=C\C1=CC=C(Cl)C=C1 YPJAUCSTGBVYRA-JZBGBCCGSA-N 0.000 claims description 2
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 claims description 2
• GWVYLVYYSGEZAI-ATILKMQGSA-N 3,4-dichloro-n-[[(3s,5s)-2-oxo-3-(3-oxo-3-piperidin-1-ylpropyl)-1-[(2s)-2-phenylbutyl]-1,4-diazepan-5-yl]methyl]benzamide Chemical compound C([C@@H]1CCN(C([C@H](CCC(=O)N2CCCCC2)N1)=O)C[C@@H](CC)C=1C=CC=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 GWVYLVYYSGEZAI-ATILKMQGSA-N 0.000 claims description 2
• XMJIJOQAKOBWKZ-PXPNINDPSA-N 3-[(2s,7s)-7-[[[(e)-3-(4-chlorophenyl)prop-2-enoyl]amino]methyl]-4-(2,2-diphenylethyl)-3-oxo-1,4-diazepan-2-yl]propanamide Chemical compound C([C@H]1N[C@H](C(N(CC(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1)=O)CCC(=O)N)NC(=O)\C=C\C1=CC=C(Cl)C=C1 XMJIJOQAKOBWKZ-PXPNINDPSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 2
• 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 claims description 2
• 229960000978 cyproterone acetate Drugs 0.000 claims description 2
• METQSPRSQINEEU-UHFFFAOYSA-N dihydrospirorenone Natural products CC12CCC(C3(CCC(=O)C=C3C3CC33)C)C3C1C1CC1C21CCC(=O)O1 METQSPRSQINEEU-UHFFFAOYSA-N 0.000 claims description 2
• 229960004845 drospirenone Drugs 0.000 claims description 2
• 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 claims description 2
• 229960002568 ethinylestradiol Drugs 0.000 claims description 2
• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 2
• 229960004023 minocycline Drugs 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 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 claims description 2
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