NO318788B1 - Adenosinderivater, samt fremgangsmate for fremstilling og anvendels derav og farmasoytisk preparat. - Google Patents

Info

Publication number

NO318788B1

NO318788B1 NO20006520A NO20006520A NO318788B1 NO 318788 B1 NO318788 B1 NO 318788B1 NO 20006520 A NO20006520 A NO 20006520A NO 20006520 A NO20006520 A NO 20006520A NO 318788 B1 NO318788 B1 NO 318788B1

Authority

NO

Norway

Prior art keywords

purin

diol

tetrahydrofuran

chloro

tetrahydro

Prior art date

1998-06-23

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• 238000000034 method Methods 0.000 title claims description 21
• 238000002360 preparation method Methods 0.000 title claims description 14
• 230000008569 process Effects 0.000 title claims description 9
• 150000003835 adenosine derivatives Chemical class 0.000 title description 4
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 194
• 239000000203 mixture Substances 0.000 claims description 172
• SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims description 42
• 229910052757 nitrogen Inorganic materials 0.000 claims description 36
• 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
• -1 N-phenylsulfonylamino Chemical group 0.000 claims description 15
• 238000006243 chemical reaction Methods 0.000 claims description 15
• 125000006239 protecting group Chemical group 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000000623 heterocyclic group Chemical group 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 208000002193 Pain Diseases 0.000 claims description 12
• DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 10
• 239000000556 agonist Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 7
• 125000001424 substituent group Chemical group 0.000 claims description 7
• 230000000694 effects Effects 0.000 claims description 6
• 208000031225 myocardial ischemia Diseases 0.000 claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 150000002431 hydrogen Chemical class 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• PQDWQMXDAMFTPA-WFXMFSGNSA-N (2r,3r,4s,5s)-2-[2-chloro-6-(2-chloroanilino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC=CC=4)Cl)=C3N=C2)O1 PQDWQMXDAMFTPA-WFXMFSGNSA-N 0.000 claims description 2
• KHQDLRSLCRTLGO-LUXYFRNMSA-N (2r,3r,4s,5s)-2-[2-chloro-6-(2-fluoroanilino)purin-9-yl]-5-[3-(hydroxymethyl)-1,2-oxazol-5-yl]oxolane-3,4-diol Chemical compound O1N=C(CO)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC=CC=4)F)=C3N=C2)O1 KHQDLRSLCRTLGO-LUXYFRNMSA-N 0.000 claims description 2
• AYJNASZSTCYQRC-LUXYFRNMSA-N (2r,3r,4s,5s)-2-[2-chloro-6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-[3-(hydroxymethyl)-1,2-oxazol-5-yl]oxolane-3,4-diol Chemical compound O1N=C(CO)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)O1 AYJNASZSTCYQRC-LUXYFRNMSA-N 0.000 claims description 2
• DQOMTAOIXFYYMS-WFXMFSGNSA-N (2r,3r,4s,5s)-2-[6-(2-chloroanilino)purin-9-yl]-5-[3-(hydroxymethyl)-1,2-oxazol-5-yl]oxolane-3,4-diol Chemical compound O1N=C(CO)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC=CC=4)Cl)=C3N=C2)O1 DQOMTAOIXFYYMS-WFXMFSGNSA-N 0.000 claims description 2
• IMAKIVMJONPAAR-LDNFRZNASA-N (2r,3r,4s,5s)-2-[6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound N=1OC([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)=NC=1C1CC1 IMAKIVMJONPAAR-LDNFRZNASA-N 0.000 claims description 2
• YBVMAERCFUQREI-WFXMFSGNSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[2-methoxy-6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(OC)=NC(NC4CCOCC4)=C3N=C2)O1 YBVMAERCFUQREI-WFXMFSGNSA-N 0.000 claims description 2
• AWCHZPJYODMTAD-TVKQPGBESA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[2-chloro-6-(2-chloro-4-fluoroanilino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(C(C)(C)C)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC(F)=CC=4)Cl)=C3N=C2)O1 AWCHZPJYODMTAD-TVKQPGBESA-N 0.000 claims description 2
• DRGGNPCPVZZQLR-DZCCDHAISA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[6-[(1-propan-2-ylsulfonylpiperidin-4-yl)amino]purin-9-yl]oxolane-3,4-diol Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2ON=C(C=2)C(C)(C)C)O1 DRGGNPCPVZZQLR-DZCCDHAISA-N 0.000 claims description 2
• CSZAUOGTYXESGJ-MOROJQBDSA-N (2s,3s,4r,5r)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-[2-chloro-6-(4-chloro-2-fluoroanilino)purin-9-yl]oxolane-3,4-diol Chemical compound O1C(C(C)(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)O1 CSZAUOGTYXESGJ-MOROJQBDSA-N 0.000 claims description 2
• ZQHDCZIERLUDFZ-MOROJQBDSA-N (2s,3s,4r,5r)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-[6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1C(C(C)(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCOCC4)=C3N=C2)O1 ZQHDCZIERLUDFZ-MOROJQBDSA-N 0.000 claims description 2
• AJEOQIOYFCWGJB-MOROJQBDSA-N (2s,3s,4r,5r)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-[6-(piperidin-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1C(C(C)(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCNCC4)=C3N=C2)O1 AJEOQIOYFCWGJB-MOROJQBDSA-N 0.000 claims description 2
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 2
• 150000005072 1,3,4-oxadiazoles Chemical class 0.000 claims description 2
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 230000008901 benefit Effects 0.000 claims description 2
• 239000002775 capsule Substances 0.000 claims description 2
• 208000015114 central nervous system disease Diseases 0.000 claims description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
• 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 229940079593 drug Drugs 0.000 claims description 2
• QMGJRUZGPDDSAU-PFHKOEEOSA-N ethyl 4-[[9-[(2r,3r,4s,5s)-3,4-dihydroxy-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]oxolan-2-yl]purin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2OC(=NN=2)C(F)(F)F)O1 QMGJRUZGPDDSAU-PFHKOEEOSA-N 0.000 claims description 2
• 239000000194 fatty acid Substances 0.000 claims description 2
• 229930195729 fatty acid Natural products 0.000 claims description 2
• 150000004665 fatty acids Chemical class 0.000 claims description 2
• 125000005842 heteroatom Chemical group 0.000 claims description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
• 150000002545 isoxazoles Chemical class 0.000 claims description 2
• OFDYPFPWXVDAAP-DZCCDHAISA-N propan-2-yl 4-[[9-[(2r,3r,4s,5s)-5-(3-tert-butyl-1,2-oxazol-5-yl)-3,4-dihydroxyoxolan-2-yl]purin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2ON=C(C=2)C(C)(C)C)O1 OFDYPFPWXVDAAP-DZCCDHAISA-N 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 230000009467 reduction Effects 0.000 claims description 2
• 201000002859 sleep apnea Diseases 0.000 claims description 2
• 239000011593 sulfur Substances 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 2
• 125000000335 thiazolyl group Chemical group 0.000 claims description 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
• WWTYKHQSPLCZDS-LDNFRZNASA-N (2r,3r,4s,5r)-2-[6-(2-chloro-4-fluoroanilino)purin-9-yl]-5-(3-propan-2-yl-1h-1,2,4-triazol-5-yl)oxolane-3,4-diol Chemical compound N1C(C(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3N=C2)O1 WWTYKHQSPLCZDS-LDNFRZNASA-N 0.000 claims 1
• FBEVIUDXWACJHI-WFXMFSGNSA-N (2r,3r,4s,5s)-2-[6-(2-chloro-4-fluoroanilino)purin-9-yl]-5-[3-(hydroxymethyl)-1,2-oxazol-5-yl]oxolane-3,4-diol Chemical compound O1N=C(CO)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3N=C2)O1 FBEVIUDXWACJHI-WFXMFSGNSA-N 0.000 claims 1
• CCLNJQZNGVEFLE-TVKQPGBESA-N (2r,3r,4s,5s)-2-[6-(2-chloroanilino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC=CC=4)Cl)=C3N=C2)O1 CCLNJQZNGVEFLE-TVKQPGBESA-N 0.000 claims 1
• ITFVSCFLPGZLRD-LDNFRZNASA-N (2r,3r,4s,5s)-2-[6-(3,4-difluoroanilino)purin-9-yl]-5-(3-propan-2-yl-1,2,4-oxadiazol-5-yl)oxolane-3,4-diol Chemical compound CC(C)C1=NOC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(NC=4C=C(F)C(F)=CC=4)=C3N=C2)O)=N1 ITFVSCFLPGZLRD-LDNFRZNASA-N 0.000 claims 1
• JAAYQDHSCICGLX-XKGFGPFHSA-N (2r,3r,4s,5s)-2-[6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-(3-cyclopropyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound N=1OC([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)=CC=1C1CC1 JAAYQDHSCICGLX-XKGFGPFHSA-N 0.000 claims 1
• LVHVPCWNNCWYBN-DZCCDHAISA-N (2r,3r,4s,5s)-2-[6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-(3-pyridin-3-yl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound N=1OC([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)=CC=1C1=CC=CN=C1 LVHVPCWNNCWYBN-DZCCDHAISA-N 0.000 claims 1
• VPFSTFMWEFTGGR-MOROJQBDSA-N (2r,3r,4s,5s)-2-[6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-(5-methyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound O1C(C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)O1 VPFSTFMWEFTGGR-MOROJQBDSA-N 0.000 claims 1
• OQRRSDZKYMKLHA-LDNFRZNASA-N (2r,3r,4s,5s)-2-[6-(4-chloro-2-fluoroanilino)purin-9-yl]-5-(5-propan-2-yl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound O1C(C(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)O1 OQRRSDZKYMKLHA-LDNFRZNASA-N 0.000 claims 1
• FEGPIIQNLVLDBU-SSHHRWTQSA-N (2s,3s,4r,5r)-2-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1OC([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC=NC(NC4CCOCC4)=C3N=C2)=NC=1C1CC1 FEGPIIQNLVLDBU-SSHHRWTQSA-N 0.000 claims 1
• OSGNFKKRIOGRON-WFXMFSGNSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCOCC4)=C3N=C2)O1 OSGNFKKRIOGRON-WFXMFSGNSA-N 0.000 claims 1
• GYDXCUKNRHPYGU-TVKQPGBESA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[2-chloro-6-(4-chloro-2-fluoroanilino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(C(C)(C)C)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(Cl)=NC(NC=4C(=CC(Cl)=CC=4)F)=C3N=C2)O1 GYDXCUKNRHPYGU-TVKQPGBESA-N 0.000 claims 1
• VMXLHEWZESYBOS-TVKQPGBESA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(C(C)(C)C)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCOCC4)=C3N=C2)O1 VMXLHEWZESYBOS-TVKQPGBESA-N 0.000 claims 1
• PZFNFKCXHWGRKV-XKGFGPFHSA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[6-[(1-methylsulfonylpiperidin-4-yl)amino]purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(C(C)(C)C)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC4CCN(CC4)S(C)(=O)=O)=C3N=C2)O1 PZFNFKCXHWGRKV-XKGFGPFHSA-N 0.000 claims 1
• GWCWLLHLZSYIKP-DZCCDHAISA-N (2s,3s,4r,5r)-2-(3-tert-butyl-1,2-oxazol-5-yl)-5-[6-[(1-propylsulfonylpiperidin-4-yl)amino]purin-9-yl]oxolane-3,4-diol Chemical compound C1CN(S(=O)(=O)CCC)CCC1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2ON=C(C=2)C(C)(C)C)O1 GWCWLLHLZSYIKP-DZCCDHAISA-N 0.000 claims 1
• FTPXZPUMCDRAGL-SSHHRWTQSA-N (2s,3s,4r,5r)-2-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-[6-(oxan-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1C([C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C3=NC=NC(NC4CCOCC4)=C3N=C2)=NN=C1C1CC1 FTPXZPUMCDRAGL-SSHHRWTQSA-N 0.000 claims 1
• RHXPQNKDFQORGZ-QCUYGVNKSA-N (2s,3s,4r,5r)-2-(5-tert-butyl-1,3,4-oxadiazol-2-yl)-5-[6-(2-chloro-4-fluoroanilino)purin-9-yl]oxolane-3,4-diol Chemical compound O1C(C(C)(C)C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC=NC(NC=4C(=CC(F)=CC=4)Cl)=C3N=C2)O1 RHXPQNKDFQORGZ-QCUYGVNKSA-N 0.000 claims 1
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
• KNNRMJBGAZFUPQ-QCUYGVNKSA-N ethyl 4-[[9-[(2r,3r,4s,5s)-3,4-dihydroxy-5-(3-methyl-1,2,4-oxadiazol-5-yl)oxolan-2-yl]purin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2ON=C(C)N=2)O1 KNNRMJBGAZFUPQ-QCUYGVNKSA-N 0.000 claims 1
• ZLQLKNRZWVCJTB-XKGFGPFHSA-N ethyl 4-[[9-[(2r,3r,4s,5s)-5-(3-ethyl-1,2-oxazol-5-yl)-3,4-dihydroxyoxolan-2-yl]-2-methoxypurin-6-yl]amino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NC1=NC(OC)=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](C=2ON=C(CC)C=2)O1 ZLQLKNRZWVCJTB-XKGFGPFHSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 294
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 138
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
• 239000000243 solution Substances 0.000 description 100
• 235000019439 ethyl acetate Nutrition 0.000 description 98
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 84
• 239000000543 intermediate Substances 0.000 description 83
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 71
• 238000001819 mass spectrum Methods 0.000 description 70
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 63
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 58
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
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