CA2355630A1 - Compounds useful in the treatment of inflammatory diseases - Google Patents

Info

Publication number

CA2355630A1

CA2355630A1 CA002355630A CA2355630A CA2355630A1 CA 2355630 A1 CA2355630 A1 CA 2355630A1 CA 002355630 A CA002355630 A CA 002355630A CA 2355630 A CA2355630 A CA 2355630A CA 2355630 A1 CA2355630 A1 CA 2355630A1

Authority

CA

Canada

Prior art keywords

amino

phenyl

oxy

acetyl

propanoic acid

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 208
• 238000011282 treatment Methods 0.000 title claims abstract description 20
• 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 8
• 238000000034 method Methods 0.000 claims abstract description 30
• 230000008569 process Effects 0.000 claims abstract description 17
• -1 nitro, hydroxy Chemical group 0.000 claims description 111
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 104
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 78
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 72
• 235000019260 propionic acid Nutrition 0.000 claims description 72
• 125000000217 alkyl group Chemical group 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 48
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000002253 acid Substances 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
• 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 37
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
• 125000003386 piperidinyl group Chemical group 0.000 claims description 15
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 9
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 208000006673 asthma Diseases 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 229920005990 polystyrene resin Polymers 0.000 claims description 5
• 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
• 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 4
• 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
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 238000011321 prophylaxis Methods 0.000 claims description 3
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
• JSTWZDLJUCKMAT-ACHIHNKUSA-N (2s)-2-[[(2s)-2-[[2-(1-bromonaphthalen-2-yl)oxyacetyl]amino]-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)COC=1C(=C2C=CC=CC2=CC=1)Br)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N(CC1)CCC1C(=O)N1CCCCC1 JSTWZDLJUCKMAT-ACHIHNKUSA-N 0.000 claims description 2
• PDIZNKWEIQNLRM-KYJUHHDHSA-N (2s)-2-[[(2s)-2-[[2-(2-benzoylphenoxy)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(=O)C1=CC=CC=C1 PDIZNKWEIQNLRM-KYJUHHDHSA-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
• 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
• UCZSIURMPKONTN-HEVIKAOCSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)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(C)(C)C UCZSIURMPKONTN-HEVIKAOCSA-N 0.000 claims description 2
• SBPBABMJZBJDSY-DQEYMECFSA-N (2s)-2-[[(2s)-2-[[2-(4-carbamoylphenoxy)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=C(C(N)=O)C=C1 SBPBABMJZBJDSY-DQEYMECFSA-N 0.000 claims description 2
• AHTKAFVUCFBDOD-VMPREFPWSA-N (2s)-3-[4-(4-benzoylpiperazine-1-carbonyl)oxyphenyl]-2-[[(2s)-2-[[2-(2,4-dichlorophenoxy)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=C(Cl)C=C1Cl AHTKAFVUCFBDOD-VMPREFPWSA-N 0.000 claims description 2
• 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 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
• OXRSFHYBIRFJSF-UHFFFAOYSA-N 3-phenyl-1,4-dihydropyrazol-5-one Chemical compound N1C(=O)CC(C=2C=CC=CC=2)=N1 OXRSFHYBIRFJSF-UHFFFAOYSA-N 0.000 claims description 2
• ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical group O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 claims description 2
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
• 239000000048 adrenergic agonist Substances 0.000 claims description 2
• 229940126157 adrenergic receptor agonist Drugs 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
• 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 claims description 2
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
• 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 6
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 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 1
• 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 1
• ODUJTJVQQFNWEX-PXLJZGITSA-N (2s)-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-4-methylpentanoyl]amino]-3-[4-[4-[(2-phenylacetyl)amino]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)CCC1NC(=O)CC1=CC=CC=C1 ODUJTJVQQFNWEX-PXLJZGITSA-N 0.000 claims 1
• 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 1
• 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 1
• CBMVWVGDWANVRN-GOTSBHOMSA-N (2s)-2-[[(2s)-2-[[2-(2,4-dichlorophenoxy)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=C(Cl)C=C1Cl CBMVWVGDWANVRN-GOTSBHOMSA-N 0.000 claims 1
• VGZIZPFNHCPKFY-VMPREFPWSA-N (2s)-2-[[(2s)-2-[[2-(2-benzoylphenoxy)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(=O)C1=CC=CC=C1 VGZIZPFNHCPKFY-VMPREFPWSA-N 0.000 claims 1
• MNASXWZLHZIIKC-BCRBLDSWSA-N (2s)-2-[[(2s)-2-[[2-(2-benzoylphenoxy)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(=O)C1=CC=CC=C1 MNASXWZLHZIIKC-BCRBLDSWSA-N 0.000 claims 1
• 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 1
• CNWGXOVQTHHLIP-VMPREFPWSA-N (2s)-2-[[(2s)-2-[[2-(2-cyclohexylphenoxy)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=C1C1CCCCC1 CNWGXOVQTHHLIP-VMPREFPWSA-N 0.000 claims 1
• WGIBNJMUDZATKD-GOTSBHOMSA-N (2s)-2-[[(2s)-2-[[2-(2-iodophenoxy)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=C1I WGIBNJMUDZATKD-GOTSBHOMSA-N 0.000 claims 1
• 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 1
• 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 1
• 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 1
• ILYWRYVNLPDLBT-HEVIKAOCSA-N (2s)-2-[[(2s)-2-[[2-(2-tert-butylphenoxy)acetyl]amino]-4-methylpentanoyl]amino]-3-[4-[4-[(4-fluorophenyl)methylcarbamoyl]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)C(=O)NCC=2C=CC(F)=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C(C)(C)C ILYWRYVNLPDLBT-HEVIKAOCSA-N 0.000 claims 1
• 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 1
• AHSAUCRZLMJPJJ-KYJUHHDHSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]amino]-3-[4-[4-(piperidine-1-carbonyl)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)C(=O)N2CCCCC2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1C AHSAUCRZLMJPJJ-KYJUHHDHSA-N 0.000 claims 1
• VTXMLKIDZLUPMQ-ACHIHNKUSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-(2-methylphenoxy)acetyl]amino]pentanoyl]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 VTXMLKIDZLUPMQ-ACHIHNKUSA-N 0.000 claims 1
• 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 1
• SKRVEEOVKDRPHA-ZAQUEYBZSA-N (2s)-2-[[(2s)-4-methyl-2-[[2-[3-(piperidine-1-carbonyl)naphthalen-2-yl]oxyacetyl]amino]pentanoyl]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=CC2=CC=CC=C2C=C1C(=O)N1CCCCC1 SKRVEEOVKDRPHA-ZAQUEYBZSA-N 0.000 claims 1
• 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 1
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