DE69919580T2 - Verbindungen zur anwendung bei der behandlung entzündlicher erkrankungen - Google Patents

Info

Publication number

DE69919580T2

DE69919580T2 DE69919580T DE69919580T DE69919580T2 DE 69919580 T2 DE69919580 T2 DE 69919580T2 DE 69919580 T DE69919580 T DE 69919580T DE 69919580 T DE69919580 T DE 69919580T DE 69919580 T2 DE69919580 T2 DE 69919580T2

Authority

DE

Germany

Prior art keywords

amino

phenyl

oxy

acetyl

carbonyl

Prior art date

1998-12-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Lifetime

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• 150000001875 compounds Chemical class 0.000 title claims description 203
• 238000011282 treatment Methods 0.000 title claims description 16
• 208000027866 inflammatory disease Diseases 0.000 title claims description 6
• -1 nitro, hydroxy Chemical group 0.000 claims description 119
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 69
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
• 239000002253 acid Substances 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 28
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 27
• 235000019260 propionic acid Nutrition 0.000 claims description 26
• DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 125000003386 piperidinyl group Chemical group 0.000 claims description 19
• 125000004193 piperazinyl group Chemical group 0.000 claims description 18
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000002757 morpholinyl group Chemical group 0.000 claims description 14
• 229910052760 oxygen Inorganic materials 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 11
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• PGTAKIDUHHSBIG-NSOVKSMOSA-N (2s)-3-[4-(4-acetylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(C)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C PGTAKIDUHHSBIG-NSOVKSMOSA-N 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
• RZMCXMNNXGCFQG-DQEYMECFSA-N (2s)-3-[4-(4-carbamoylpiperidine-1-carbonyl)oxyphenyl]-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)C(N)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C RZMCXMNNXGCFQG-DQEYMECFSA-N 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
• 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 5
• 229920005990 polystyrene resin Polymers 0.000 claims description 5
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
• CKLKWCJTRNEBSS-UIOOFZCWSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C CKLKWCJTRNEBSS-UIOOFZCWSA-N 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 4
• 230000007062 hydrolysis Effects 0.000 claims description 4
• 238000006460 hydrolysis reaction Methods 0.000 claims description 4
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
• AZWCVTBCAZEECO-VMPREFPWSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-(furan-2-carbonyl)piperazine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(=O)C=2OC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C AZWCVTBCAZEECO-VMPREFPWSA-N 0.000 claims description 3
• PPSXZSXHLIIACO-HEVIKAOCSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(2-phenylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C PPSXZSXHLIIACO-HEVIKAOCSA-N 0.000 claims description 3
• FLJPNJMQUJHZIM-ZEQRLZLVSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C FLJPNJMQUJHZIM-ZEQRLZLVSA-N 0.000 claims description 3
• FSLIKVLFQCHCPY-VMPREFPWSA-N (2s)-3-[4-(4-acetylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1C=2OC3=CC=CC=C3C=2C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N1CCN(C(C)=O)CC1 FSLIKVLFQCHCPY-VMPREFPWSA-N 0.000 claims description 3
• ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
• 125000002785 azepinyl group Chemical group 0.000 claims description 3
• 239000000969 carrier Substances 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 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 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 3
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 3
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 3
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 3
• NKNFUWZGJLRHEF-SVBPBHIXSA-N (2s)-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1C=2OC3=CC=CC=C3C=2C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N1CCOCC1 NKNFUWZGJLRHEF-SVBPBHIXSA-N 0.000 claims description 2
• RXAZMQSANZTQIE-LQJZCPKCSA-N (2s)-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]-3-[4-[4-(piperidine-1-carbonyl)piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1C=2OC3=CC=CC=C3C=2C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N(CC1)CCC1C(=O)N1CCCCC1 RXAZMQSANZTQIE-LQJZCPKCSA-N 0.000 claims description 2
• OIJVNGXPZSGRQQ-UIOOFZCWSA-N (2s)-2-[[(2s)-2-[[2-(1-bromonaphthalen-2-yl)oxyacetyl]amino]-4-methylpentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C(=C2C=CC=CC2=CC=1)Br)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N1CCOCC1 OIJVNGXPZSGRQQ-UIOOFZCWSA-N 0.000 claims description 2
• HUHLSTSVAXPHTF-VMPREFPWSA-N (2s)-2-[[(2s)-2-[[2-(1-bromonaphthalen-2-yl)oxyacetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-(furan-2-carbonyl)piperazine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)COC=1C(=C2C=CC=CC2=CC=1)Br)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N(CC1)CCN1C(=O)C1=CC=CO1 HUHLSTSVAXPHTF-VMPREFPWSA-N 0.000 claims description 2
• VUUKBZDVYVDKTO-BCRBLDSWSA-N (2s)-2-[[(2s)-2-[[2-(2-benzoylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[[2-(4-chlorophenyl)acetyl]amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC=2C=CC(Cl)=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(=O)C1=CC=CC=C1 VUUKBZDVYVDKTO-BCRBLDSWSA-N 0.000 claims description 2
• PMOOREKUNZXHIM-ACHIHNKUSA-N (2s)-2-[[(2s)-2-[[2-(2-cyclohexylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-(furan-2-carbonyl)piperazine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(=O)C=2OC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C1CCCCC1 PMOOREKUNZXHIM-ACHIHNKUSA-N 0.000 claims description 2
• WBIZOZXBPMEAKK-BCRBLDSWSA-N (2s)-2-[[(2s)-2-[[2-(2-cyclohexylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(2-phenylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C1CCCCC1 WBIZOZXBPMEAKK-BCRBLDSWSA-N 0.000 claims description 2
• CNTMNVHPUBNDSY-CONSDPRKSA-N (2s)-2-[[(2s)-2-[[2-(2-iodophenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(2-phenylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1I CNTMNVHPUBNDSY-CONSDPRKSA-N 0.000 claims description 2
• GAMWEMQFIJRKSL-SVBPBHIXSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-(4-carbamoylpiperidine-1-carbonyl)oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)C(N)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C GAMWEMQFIJRKSL-SVBPBHIXSA-N 0.000 claims description 2
• WJESJYFVWLSEHU-YDAXCOIMSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(2,2-dicyclohexylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)C(C2CCCCC2)C2CCCCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C WJESJYFVWLSEHU-YDAXCOIMSA-N 0.000 claims description 2
• IBVIKWNMDVAQRX-HEVIKAOCSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(2-cyclohexylacetyl)amino]piperidine-1-carbonyl]oxyphenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC2CCCCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C IBVIKWNMDVAQRX-HEVIKAOCSA-N 0.000 claims description 2
• SBCVXKWLVINGKC-ZEQRLZLVSA-N (2s)-2-[[(2s)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)OCC1=CC=CC=C1 SBCVXKWLVINGKC-ZEQRLZLVSA-N 0.000 claims description 2
• HGSJTKUZEHRDMN-UIOOFZCWSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-(2-propylphenoxy)acetyl]amino]pentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound CCCC1=CC=CC=C1OCC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC(C=C1)=CC=C1OC(=O)N1CCOCC1 HGSJTKUZEHRDMN-UIOOFZCWSA-N 0.000 claims description 2
• VVZPENFOQVEKIV-VMPREFPWSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-[4-(piperidine-1-carbonyl)phenoxy]acetyl]amino]pentanoyl]amino]-3-[4-(morpholine-4-carbonyloxy)phenyl]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCOCC2)=CC=1)C(O)=O)C(=O)COC(C=C1)=CC=C1C(=O)N1CCCCC1 VVZPENFOQVEKIV-VMPREFPWSA-N 0.000 claims description 2
• VWZUYZXINJBNCA-DQEYMECFSA-N (2s)-3-[4-(4-acetylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-[[2-(2-iodophenoxy)acetyl]amino]-4-methylpentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(C)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1I VWZUYZXINJBNCA-DQEYMECFSA-N 0.000 claims description 2
• JPJAYGCKRULCOQ-UIOOFZCWSA-N (2s)-3-[4-(4-acetylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(C)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C JPJAYGCKRULCOQ-UIOOFZCWSA-N 0.000 claims description 2
• STUWBPZBJDJNLN-LQJZCPKCSA-N (2s)-3-[4-(4-benzoylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1C=2OC3=CC=CC=C3C=2C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N(CC1)CCN1C(=O)C1=CC=CC=C1 STUWBPZBJDJNLN-LQJZCPKCSA-N 0.000 claims description 2
• YNDIBNHBFJYOFE-ACHIHNKUSA-N (2s)-3-[4-(4-benzoylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(=O)C=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C YNDIBNHBFJYOFE-ACHIHNKUSA-N 0.000 claims description 2
• DYHCSOTYSDGRIJ-KYJUHHDHSA-N (2s)-3-[4-(4-benzoylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCN(CC2)C(=O)C=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C DYHCSOTYSDGRIJ-KYJUHHDHSA-N 0.000 claims description 2
• SKNQITACTVHHDP-NSOVKSMOSA-N (2s)-3-[4-(4-carbamoylpiperidine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]propanoic acid Chemical compound C([C@H](NC(=O)[C@@H](NC(=O)C=1C2=C(C3=CC=CC=C3O2)C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N1CCC(C(N)=O)CC1 SKNQITACTVHHDP-NSOVKSMOSA-N 0.000 claims description 2
• DCUOBFRTDYMALV-ZEQRLZLVSA-N (2s)-3-[4-(4-carbamoylpiperidine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-[[2-(2-iodophenoxy)acetyl]amino]-4-methylpentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)C(N)=O)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1I DCUOBFRTDYMALV-ZEQRLZLVSA-N 0.000 claims description 2
• BTPNIOFQMCTNHX-KYJUHHDHSA-N (2s)-3-[4-(4-carbamoylpiperidine-1-carbonyl)oxyphenyl]-2-[[(2s)-4-methyl-2-[[2-[4-(piperidine-1-carbonyl)phenoxy]acetyl]amino]pentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)C(N)=O)=CC=1)C(O)=O)C(=O)COC(C=C1)=CC=C1C(=O)N1CCCCC1 BTPNIOFQMCTNHX-KYJUHHDHSA-N 0.000 claims description 2
• SHNAAOJNYHBXJK-BCRBLDSWSA-N (2s)-3-[4-[4-[[2-(4-chlorophenyl)acetyl]amino]piperidine-1-carbonyl]oxyphenyl]-2-[[(2s)-2-[[2-(2-cyclohexylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]propanoic acid Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(OC(=O)N2CCC(CC2)NC(=O)CC=2C=CC(Cl)=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C1CCCCC1 SHNAAOJNYHBXJK-BCRBLDSWSA-N 0.000 claims description 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 239000000048 adrenergic agonist Substances 0.000 claims description 2
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
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