NZ511478A - Compounds useful in the treatment of inflammatory diseases - Google Patents

Info

Publication number

NZ511478A

NZ511478A NZ511478A NZ51147899A NZ511478A NZ 511478 A NZ511478 A NZ 511478A NZ 511478 A NZ511478 A NZ 511478A NZ 51147899 A NZ51147899 A NZ 51147899A NZ 511478 A NZ511478 A NZ 511478A

Authority

NZ

New Zealand

Prior art keywords

amino

oxy

phenyl

acetyl

propanoic acid

Prior art date

1998-12-18

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 212
• 238000011282 treatment Methods 0.000 title claims abstract description 19
• 208000027866 inflammatory disease Diseases 0.000 title claims abstract description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 53
• 239000001257 hydrogen Substances 0.000 claims abstract description 51
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
• 239000003814 drug Substances 0.000 claims abstract description 8
• 238000004519 manufacturing process Methods 0.000 claims abstract description 4
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims abstract 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 138
• -1 nitro, hydroxy Chemical group 0.000 claims description 101
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 100
• 235000019260 propionic acid Nutrition 0.000 claims description 95
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 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 53
• 239000002253 acid Substances 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 29
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 28
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 25
• 239000012453 solvate Substances 0.000 claims description 24
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 230000008569 process Effects 0.000 claims description 17
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 238000002360 preparation method Methods 0.000 claims description 12
• 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
• 125000002757 morpholinyl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 10
• UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 150000002431 hydrogen Chemical group 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
• GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 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
• 229960004017 salmeterol Drugs 0.000 claims description 3
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
• 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
• TWHFKICORXJNLC-VMPREFPWSA-N (2s)-3-[4-(4-benzoylpiperazine-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(=O)C=2C=CC=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC=CC=C1I TWHFKICORXJNLC-VMPREFPWSA-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
• 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
• 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
• 102100023170 Nuclear receptor subfamily 1 group D member 1 Human genes 0.000 claims description 2
• 239000013543 active substance Substances 0.000 claims description 2
• 125000000304 alkynyl group Chemical group 0.000 claims description 2
• 125000002785 azepinyl group Chemical group 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000000969 carrier Substances 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 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
• 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
• 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
• GSQDGGVMFJSFCY-KYJUHHDHSA-N (2s)-2-[[(2s)-2-(dibenzofuran-4-carbonylamino)-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)C=1C2=C(C3=CC=CC=C3O2)C=CC=1)CC(C)C)C(O)=O)C(C=C1)=CC=C1OC(=O)N(CC1)CCN1C(=O)C1=CC=CO1 GSQDGGVMFJSFCY-KYJUHHDHSA-N 0.000 claims 1
• 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 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
• 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
• 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 1
• 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 1
• 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 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
• 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
• 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
• 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 1
• 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 1
• 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 1
• YOBKQPYSHCFIGC-PXLJZGITSA-N (2s)-3-[4-[4-[[2-(4-chlorophenyl)acetyl]amino]piperidine-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)N(CC1)CCC1NC(=O)CC1=CC=C(Cl)C=C1 YOBKQPYSHCFIGC-PXLJZGITSA-N 0.000 claims 1
• 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 1
• RVYLHCXIFWMJSM-ZAQUEYBZSA-N (2s)-3-[4-[4-[[2-(4-chlorophenyl)acetyl]amino]piperidine-1-carbonyl]oxyphenyl]-2-[[(2s)-4-methyl-2-[[2-[3-(piperidine-1-carbonyl)naphthalen-2-yl]oxyacetyl]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)NC(=O)CC=2C=CC(Cl)=CC=2)=CC=1)C(O)=O)C(=O)COC1=CC2=CC=CC=C2C=C1C(=O)N1CCCCC1 RVYLHCXIFWMJSM-ZAQUEYBZSA-N 0.000 claims 1
• 230000007717 exclusion Effects 0.000 claims 1
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
• BWILYWWHXDGKQA-UHFFFAOYSA-M potassium propanoate Chemical compound [K+].CCC([O-])=O BWILYWWHXDGKQA-UHFFFAOYSA-M 0.000 claims 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
• 125000000623 heterocyclic group Chemical group 0.000 abstract 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 472
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 288
• 239000000543 intermediate Substances 0.000 description 214
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 155
• 239000000243 solution Substances 0.000 description 142
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 129
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 120
• 239000000203 mixture Substances 0.000 description 120
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 118
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 116
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 103
• 239000007787 solid Substances 0.000 description 101
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
• 238000003756 stirring Methods 0.000 description 98
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 84
• 239000011347 resin Substances 0.000 description 82
• 229920005989 resin Polymers 0.000 description 82
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 76
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 74
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