RU2524245C2 - 3-замещенный-1,4-диазепан-2-оновые антагонисты меланокортин 5-рецептора - Google Patents

Info

Publication number

RU2524245C2

RU2524245C2 RU2010137033/04A RU2010137033A RU2524245C2 RU 2524245 C2 RU2524245 C2 RU 2524245C2 RU 2010137033/04 A RU2010137033/04 A RU 2010137033/04A RU 2010137033 A RU2010137033 A RU 2010137033A RU 2524245 C2 RU2524245 C2 RU 2524245C2

Authority

RU

Russia

Prior art keywords

group

methyl

oxo

diazepan

diphenylethyl

Prior art date

2008-02-29

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• 108010088565 Melanocortin 5 receptor Proteins 0.000 title claims abstract description 67
• 102000030612 Melanocortin 5 receptor Human genes 0.000 title claims abstract description 66
• -1 3-substituted-1,4-diazepan-2-one Chemical class 0.000 title claims description 187
• 239000005557 antagonist Substances 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 179
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 16
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
• 125000004429 atom Chemical group 0.000 claims abstract description 14
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000004122 cyclic group Chemical group 0.000 claims abstract description 11
• 239000003085 diluting agent Substances 0.000 claims abstract description 9
• 239000003937 drug carrier Substances 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
• 125000005843 halogen group Chemical group 0.000 claims abstract description 8
• 125000003277 amino group Chemical group 0.000 claims abstract description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract 2
• 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000001072 heteroaryl group Chemical group 0.000 claims description 45
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
• 125000000753 cycloalkyl 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 25
• 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 18
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 15
• HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 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
• 125000005916 2-methylpentyl group Chemical group 0.000 claims description 7
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 7
• 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
• 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
• 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
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• BILCCFIDWKMOQV-KUSJRIKGSA-N 6-chloro-n-[[(3s,5s)-2-oxo-1-[(2s)-2-phenylbutyl]-3-(2-phenylmethoxyethyl)-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)COCC1=CC=CC=C1 BILCCFIDWKMOQV-KUSJRIKGSA-N 0.000 claims description 2
• 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 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
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 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
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• UJHBYTZOMVVYLT-JSXFGMRASA-N n-[[(3s,5s)-3-(2-cyclohexylethyl)-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide Chemical compound C([C@H](N[C@@H](CCC1CCCCC1)C1=O)CNC(=O)C=2C=C3C=CC=CC3=CC=2)CN1CC(C=1C=CC=CC=1)C1=CC=CC=C1 UJHBYTZOMVVYLT-JSXFGMRASA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• LCZYDBODPLIUDE-JUKUECOXSA-N n-[[(3s,5s)-3-[(2-aminophenyl)methyl]-1-(2,2-diphenylethyl)-2-oxo-1,4-diazepan-5-yl]methyl]naphthalene-2-carboxamide 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](CNC(=O)C=2C=C3C=CC=CC3=CC=2)N1 LCZYDBODPLIUDE-JUKUECOXSA-N 0.000 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 claims description 2
• 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 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 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 claims 1
• 238000011282 treatment Methods 0.000 abstract description 25
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