SK26095A3 - Benzolactame derivatives, method of their production and pharmaceutical agents containing them - Google Patents

Info

Publication number

SK26095A3

SK26095A3 SK260-95A SK26095A SK26095A3 SK 26095 A3 SK26095 A3 SK 26095A3 SK 26095 A SK26095 A SK 26095A SK 26095 A3 SK26095 A3 SK 26095A3

Authority

SK

Slovakia

Prior art keywords

methyl

amino

biphenyl

tetrahydro

oxo

Prior art date

1992-08-28

Links

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• 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
• 238000000034 method Methods 0.000 title claims description 113
• 239000008177 pharmaceutical agent Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 176
• 239000000122 growth hormone Substances 0.000 claims abstract description 51
• 102000018997 Growth Hormone Human genes 0.000 claims abstract description 50
• 108010051696 Growth Hormone Proteins 0.000 claims abstract description 50
• 241001465754 Metazoa Species 0.000 claims abstract description 13
• 239000004480 active ingredient Substances 0.000 claims abstract description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 668
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 406
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 265
• 238000002360 preparation method Methods 0.000 claims description 239
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 225
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 157
• -1 -S (O) m R 7a Chemical group 0.000 claims description 146
• 125000004432 carbon atom Chemical group C* 0.000 claims description 138
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 136
• 125000000217 alkyl group Chemical group 0.000 claims description 98
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
• 239000004305 biphenyl Substances 0.000 claims description 77
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 68
• 235000010290 biphenyl Nutrition 0.000 claims description 68
• LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 67
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 66
• 125000001424 substituent group Chemical group 0.000 claims description 62
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 54
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 47
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 45
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 40
• 229910052757 nitrogen Inorganic materials 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 38
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 30
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 27
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 27
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 25
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 25
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 22
• 150000002367 halogens Chemical class 0.000 claims description 22
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
• 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• XDEHMKQLKPZERH-UHFFFAOYSA-N 2-amino-3-methylbutanamide Chemical compound CC(C)C(N)C(N)=O XDEHMKQLKPZERH-UHFFFAOYSA-N 0.000 claims description 13
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
• 229910052717 sulfur Inorganic materials 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 11
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 11
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000001041 indolyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 7
• AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 102000004218 Insulin-Like Growth Factor I Human genes 0.000 claims description 6
• 108090000723 Insulin-Like Growth Factor I Proteins 0.000 claims description 6
• URINYHFMLIGJCL-UHFFFAOYSA-N NCSN Chemical compound NCSN URINYHFMLIGJCL-UHFFFAOYSA-N 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
• 208000008589 Obesity Diseases 0.000 claims description 5
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 125000001589 carboacyl group Chemical group 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 230000001925 catabolic effect Effects 0.000 claims description 5
• 125000005843 halogen group Chemical group 0.000 claims description 5
• 235000020824 obesity Nutrition 0.000 claims description 5
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 102000003982 Parathyroid hormone Human genes 0.000 claims description 3
• 108090000445 Parathyroid hormone Proteins 0.000 claims description 3
• UROSOAGIHCLPKT-HSZRJFAPSA-N [2-[4-[[(3r)-3-[(2-amino-2-methylpropanoyl)amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl] n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)C(C)(C)N)CCC2=CC=CC=C21 UROSOAGIHCLPKT-HSZRJFAPSA-N 0.000 claims description 3
• 239000000808 adrenergic beta-agonist Substances 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 239000003937 drug carrier Substances 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
• 239000000199 parathyroid hormone Substances 0.000 claims description 3
• 229960001319 parathyroid hormone Drugs 0.000 claims description 3
• 150000003254 radicals Chemical class 0.000 claims description 3
• NWQWNCILOXTTHF-HLCSKTDOSA-N (2s)-6-amino-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-aminopropanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@@H](N)C)C(=O)N[C@H](CC=1C=C2C=CC=CC2=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CNC=N1 NWQWNCILOXTTHF-HLCSKTDOSA-N 0.000 claims description 2
• WZHKXNSOCOQYQX-FUAFALNISA-N (2s)-6-amino-2-[[(2r)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2s)-2-amino-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](N)C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CN=CN1 WZHKXNSOCOQYQX-FUAFALNISA-N 0.000 claims description 2
• HRNLPPBUBKMZMT-SSSXJSFTSA-N (2s)-6-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-[[(2r)-2-aminopropanoyl]amino]-3-naphthalen-2-ylpropanoyl]amino]propanoyl]amino]-3-(1h-indol-3-yl)propanoyl]amino]-3-phenylpropanoyl]amino]hexanamide Chemical compound C([C@H](NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](C)NC(=O)[C@@H](CC=1C=C2C=CC=CC2=CC=1)NC(=O)[C@H](N)C)C(=O)N[C@@H](CCCCN)C(N)=O)C1=CC=CC=C1 HRNLPPBUBKMZMT-SSSXJSFTSA-N 0.000 claims description 2
• UEZOHQWPOBPNHU-RUZDIDTESA-N 2-amino-n-[(3r)-1-[[4-[2-(2-hydroxyethylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-2-methylpropanamide Chemical compound C([C@H](C1=O)NC(=O)C(C)(N)C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)NCCO UEZOHQWPOBPNHU-RUZDIDTESA-N 0.000 claims description 2
• AUFFEVJQULJDJJ-RUZDIDTESA-N 3-amino-3-methyl-n-[(3r)-1-[[4-[2-(methylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]butanamide Chemical compound CNC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 AUFFEVJQULJDJJ-RUZDIDTESA-N 0.000 claims description 2
• AZUINFTYYIHGPB-RUZDIDTESA-N 3-amino-3-methyl-n-[(3r)-1-[[4-[2-(methylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-7-(trifluoromethyl)-4,5-dihydro-3h-1-benzazepin-3-yl]butanamide Chemical compound CNC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC(C(F)(F)F)=CC=C21 AZUINFTYYIHGPB-RUZDIDTESA-N 0.000 claims description 2
• CXCJOGVDLBKKNN-GDLZYMKVSA-N 3-amino-3-methyl-n-[(3r)-1-[[4-[2-[2-(methylcarbamoylamino)phenoxy]phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]butanamide Chemical compound CNC(=O)NC1=CC=CC=C1OC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 CXCJOGVDLBKKNN-GDLZYMKVSA-N 0.000 claims description 2
• VGEZUROYNDUJQV-AREMUKBSSA-N 3-amino-n-[(3r)-1-[[4-[2-(2-hydroxyethylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound C([C@H](C1=O)NC(=O)CC(C)(N)C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)NCCO VGEZUROYNDUJQV-AREMUKBSSA-N 0.000 claims description 2
• ILHPFOPWLJMUOW-AREMUKBSSA-N 3-amino-n-[(3r)-1-[[4-[2-(2-hydroxyethylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-7-(trifluoromethyl)-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound C([C@H](C1=O)NC(=O)CC(C)(N)C)CC2=CC(C(F)(F)F)=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)NCCO ILHPFOPWLJMUOW-AREMUKBSSA-N 0.000 claims description 2
• SGOQHGJUBTWCSC-XMMPIXPASA-N 3-amino-n-[(3r)-1-[[4-[2-(carbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound C([C@H](C1=O)NC(=O)CC(C)(N)C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(N)=O SGOQHGJUBTWCSC-XMMPIXPASA-N 0.000 claims description 2
• 229920001774 Perfluoroether Polymers 0.000 claims description 2
• DPQAXNSOFFYKDS-UHFFFAOYSA-N Talipexole dihydrochloride Chemical compound Cl.Cl.C1CN(CC=C)CCC2=C1N=C(N)S2 DPQAXNSOFFYKDS-UHFFFAOYSA-N 0.000 claims description 2
• AUFBEVQCLQHDJE-XMMPIXPASA-N [2-[4-[[(3r)-3-[(3-amino-3-methylbutanoyl)amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl] n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 AUFBEVQCLQHDJE-XMMPIXPASA-N 0.000 claims description 2
• 108010083553 alanyl-histidyl-(2-naphthyl)alanyl-tryptophyl-phenylalanyl-lysinamide Proteins 0.000 claims description 2
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
• 108010015153 growth hormone releasing hexapeptide Proteins 0.000 claims description 2
• HEZQIHKSXBXJRH-RUZDIDTESA-N methyl 2-[[2-[4-[[(3r)-3-[(2-amino-2-methylpropanoyl)amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl]carbamoylamino]acetate Chemical compound COC(=O)CNC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)C(C)(C)N)CCC2=CC=CC=C21 HEZQIHKSXBXJRH-RUZDIDTESA-N 0.000 claims description 2
• SVORCIXGUBIZSS-RUZDIDTESA-N methyl n-[2-[4-[[(3r)-3-[(3-amino-3-methylbutanoyl)amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl]carbamate Chemical compound COC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 SVORCIXGUBIZSS-RUZDIDTESA-N 0.000 claims description 2
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• BQVGZFQLSSJSMW-UHFFFAOYSA-N 3-amino-3-methylbutanamide Chemical compound CC(C)(N)CC(N)=O BQVGZFQLSSJSMW-UHFFFAOYSA-N 0.000 claims 2
• 229940122361 Bisphosphonate Drugs 0.000 claims 2
• 239000000384 adrenergic alpha-2 receptor agonist Substances 0.000 claims 2
• 150000004663 bisphosphonates Chemical class 0.000 claims 2
• 125000001153 fluoro group Chemical group F* 0.000 claims 2
• IAOMOLWHQOVGIU-XMMPIXPASA-N 2-amino-2-methyl-n-[(3r)-1-[[4-[2-(methylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]propanamide Chemical compound CNC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)C(C)(C)N)CCC2=CC=CC=C21 IAOMOLWHQOVGIU-XMMPIXPASA-N 0.000 claims 1
• PQFKRKWOXGPALU-HSZRJFAPSA-N 2-amino-n-[(3r)-1-[[4-[2-(hydroxycarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-2-methylpropanamide Chemical compound C([C@H](C1=O)NC(=O)C(C)(N)C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)NO PQFKRKWOXGPALU-HSZRJFAPSA-N 0.000 claims 1
• DNCHAXGSIXXBPB-AREMUKBSSA-N 3-amino-n-[(3r)-1-[[4-[2-(dimethylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound CN(C)C(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 DNCHAXGSIXXBPB-AREMUKBSSA-N 0.000 claims 1
• KADJMKYUGUSZFG-JIPXPUAJSA-N 3-amino-n-[(3r)-1-[[4-[2-[[(2r)-2-hydroxypropyl]carbamoylamino]phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound C[C@@H](O)CNC(=O)NC1=CC=CC=C1C(C=C1)=CC=C1CN1C(=O)[C@H](NC(=O)CC(C)(C)N)CCC2=CC=CC=C21 KADJMKYUGUSZFG-JIPXPUAJSA-N 0.000 claims 1
• ACETZRBCYLZQPI-AREMUKBSSA-N 3-amino-n-[(3r)-7-fluoro-1-[[4-[2-(2-hydroxyethylcarbamoylamino)phenyl]phenyl]methyl]-2-oxo-4,5-dihydro-3h-1-benzazepin-3-yl]-3-methylbutanamide Chemical compound C([C@H](C1=O)NC(=O)CC(C)(N)C)CC2=CC(F)=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)NCCO ACETZRBCYLZQPI-AREMUKBSSA-N 0.000 claims 1
• 102100033367 Appetite-regulating hormone Human genes 0.000 claims 1
• 101710111255 Appetite-regulating hormone Proteins 0.000 claims 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
• 102000048143 Insulin-Like Growth Factor II Human genes 0.000 claims 1
• 108090001117 Insulin-Like Growth Factor II Proteins 0.000 claims 1
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
• 239000003324 growth hormone secretagogue Substances 0.000 claims 1
• 108010085742 growth hormone-releasing peptide-2 Proteins 0.000 claims 1
• VODXYXUYTFSXFK-HHHXNRCGSA-N n-[2-[4-[[(3r)-3-[(2-amino-2-methylpropanoyl)amino]-7-fluoro-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl]morpholine-4-carboxamide Chemical compound C([C@H](C1=O)NC(=O)C(C)(N)C)CC2=CC(F)=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)N1CCOCC1 VODXYXUYTFSXFK-HHHXNRCGSA-N 0.000 claims 1
• RGJHYPSPZYEZQK-MUUNZHRXSA-N n-[2-[4-[[(3r)-3-[(3-amino-3-methylbutanoyl)amino]-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]methyl]phenyl]phenyl]morpholine-4-carboxamide Chemical compound C([C@H](C1=O)NC(=O)CC(C)(N)C)CC2=CC=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1NC(=O)N1CCOCC1 RGJHYPSPZYEZQK-MUUNZHRXSA-N 0.000 claims 1
• 229960000208 pralmorelin Drugs 0.000 claims 1
• 230000000707 stereoselective effect Effects 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 68
• 230000012010 growth Effects 0.000 abstract description 10
• 150000003951 lactams Chemical class 0.000 abstract description 10
• 230000028327 secretion Effects 0.000 abstract description 8
• 235000013305 food Nutrition 0.000 abstract 1
• 235000013622 meat product Nutrition 0.000 abstract 1
• 230000001737 promoting effect Effects 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 282
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 228
• 239000000243 solution Substances 0.000 description 191
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 168
• 239000011541 reaction mixture Substances 0.000 description 140
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