ES2530266T3 - Análogos de nitroimidazooxazina y sus usos - Google Patents

Info

Publication number

ES2530266T3

ES2530266T3 ES10740807.2T ES10740807T ES2530266T3 ES 2530266 T3 ES2530266 T3 ES 2530266T3 ES 10740807 T ES10740807 T ES 10740807T ES 2530266 T3 ES2530266 T3 ES 2530266T3

Authority

ES

Spain

Prior art keywords

methyl

nitro

oxazine

imidazo

dihydro

Prior art date

2009-07-31

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.)

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• YVMGQODAKAHLHB-UHFFFAOYSA-N 3-nitroimidazo[4,5-e]oxazine Chemical class O1N=C([N+](=O)[O-])C=C2N=CN=C21 YVMGQODAKAHLHB-UHFFFAOYSA-N 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 168
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 49
• 125000001424 substituent group Chemical group 0.000 claims abstract description 18
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 14
• 229910052740 iodine Inorganic materials 0.000 claims abstract description 8
• 239000000203 mixture Substances 0.000 claims description 105
• -1 {[4 ′ - (trifluoromethoxy) [1,1′-biphenyl] -3-yl] methoxy} methyl Chemical group 0.000 claims description 29
• 238000011282 treatment Methods 0.000 claims description 16
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
• 241000222727 Leishmania donovani Species 0.000 claims description 14
• 241000223109 Trypanosoma cruzi Species 0.000 claims description 11
• 208000015181 infectious disease Diseases 0.000 claims description 11
• 241000187479 Mycobacterium tuberculosis Species 0.000 claims description 10
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 230000000813 microbial effect Effects 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 239000003981 vehicle Substances 0.000 claims description 7
• 239000002671 adjuvant Substances 0.000 claims description 4
• 239000000872 buffer Substances 0.000 claims description 4
• 239000003381 stabilizer Substances 0.000 claims description 4
• YMBWFCMEEHOGSZ-SECBINFHSA-N (6r)-2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])OC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-SECBINFHSA-N 0.000 claims description 3
• YMBWFCMEEHOGSZ-VIFPVBQESA-N (6s)-2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C([C@@H]1CN2C=C(N=C2OC1)[N+](=O)[O-])OC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-VIFPVBQESA-N 0.000 claims description 3
• DKBRVRXAPWANPM-UHFFFAOYSA-N 2-nitro-6-[(4-phenylmethoxyphenyl)methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=C1)=CC=C1OCC1=CC=CC=C1 DKBRVRXAPWANPM-UHFFFAOYSA-N 0.000 claims description 3
• ZHRASUMKCIRTES-UHFFFAOYSA-N 2-nitro-6-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC1=CC=CC(OC(F)(F)F)=C1 ZHRASUMKCIRTES-UHFFFAOYSA-N 0.000 claims description 3
• YMBWFCMEEHOGSZ-UHFFFAOYSA-N 2-nitro-6-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC1=CC=C(OC(F)(F)F)C=C1 YMBWFCMEEHOGSZ-UHFFFAOYSA-N 0.000 claims description 3
• UIPIZMADAJJXSA-UHFFFAOYSA-N 2-nitro-6-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC1=CC=C(OC(F)(F)F)C=C1 UIPIZMADAJJXSA-UHFFFAOYSA-N 0.000 claims description 3
• DLBVAKLECIGBHD-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DLBVAKLECIGBHD-UHFFFAOYSA-N 0.000 claims description 3
• GYRYSVKOTZBBPG-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 GYRYSVKOTZBBPG-UHFFFAOYSA-N 0.000 claims description 3
• DIZRPICDSULNDS-UHFFFAOYSA-N 2-nitro-6-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DIZRPICDSULNDS-UHFFFAOYSA-N 0.000 claims description 3
• KKUKKUOZYLQOMW-UHFFFAOYSA-N 2-nitro-6-[[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 KKUKKUOZYLQOMW-UHFFFAOYSA-N 0.000 claims description 3
• QQLOFOVQUMKHPJ-UHFFFAOYSA-N 2-nitro-6-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 QQLOFOVQUMKHPJ-UHFFFAOYSA-N 0.000 claims description 3
• XIKLEESAKIVDNK-UHFFFAOYSA-N 2-nitro-6-[[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 XIKLEESAKIVDNK-UHFFFAOYSA-N 0.000 claims description 3
• YFAXAFFUGBLZOP-UHFFFAOYSA-N 2-nitro-7-[(4-phenylmethoxyphenoxy)methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1OCC1=CC=CC=C1 YFAXAFFUGBLZOP-UHFFFAOYSA-N 0.000 claims description 3
• AFYYMFBWQPYVNA-UHFFFAOYSA-N 2-nitro-7-[(4-phenylmethoxyphenyl)methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC(C=C1)=CC=C1OCC1=CC=CC=C1 AFYYMFBWQPYVNA-UHFFFAOYSA-N 0.000 claims description 3
• KEPDMMNFWQRFEA-UHFFFAOYSA-N 2-nitro-7-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC1=CC=CC(OC(F)(F)F)=C1 KEPDMMNFWQRFEA-UHFFFAOYSA-N 0.000 claims description 3
• FJQBCEDWCKWTBL-UHFFFAOYSA-N 2-nitro-7-[[4-(trifluoromethoxy)phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC1=CC=C(OC(F)(F)F)C=C1 FJQBCEDWCKWTBL-UHFFFAOYSA-N 0.000 claims description 3
• AKYSJCGKQJLIEI-UHFFFAOYSA-N 2-nitro-7-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC1=CC=C(OC(F)(F)F)C=C1 AKYSJCGKQJLIEI-UHFFFAOYSA-N 0.000 claims description 3
• YRZTVAYXNMPEHK-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 YRZTVAYXNMPEHK-UHFFFAOYSA-N 0.000 claims description 3
• YXWALFWDXOZXLM-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 YXWALFWDXOZXLM-UHFFFAOYSA-N 0.000 claims description 3
• YHIHNLZSXHLZRO-UHFFFAOYSA-N 2-nitro-7-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 YHIHNLZSXHLZRO-UHFFFAOYSA-N 0.000 claims description 3
• HCEUKUYCMKEOMQ-UHFFFAOYSA-N 2-nitro-7-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 HCEUKUYCMKEOMQ-UHFFFAOYSA-N 0.000 claims description 3
• VCENEFJSXTYRJF-UHFFFAOYSA-N 6-[[4-(4-fluorophenyl)phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=C1)=CC=C1C1=CC=C(F)C=C1 VCENEFJSXTYRJF-UHFFFAOYSA-N 0.000 claims description 3
• YCDRNIZCGKVAJS-UHFFFAOYSA-N 6-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(N=C1)=CC=C1C1=CC=C(F)C=C1 YCDRNIZCGKVAJS-UHFFFAOYSA-N 0.000 claims description 3
• NBORUIOPRKKLHI-UHFFFAOYSA-N 6-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COC(C=N1)=CC=C1C1=CC=C(F)C=C1 NBORUIOPRKKLHI-UHFFFAOYSA-N 0.000 claims description 3
• QACAURHEZMYCGU-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)phenoxy]methyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=C1)=CC=C1C1=CC=C(F)C=C1 QACAURHEZMYCGU-UHFFFAOYSA-N 0.000 claims description 3
• IQJFYFAKNUOHAE-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)phenoxy]methyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(F)C=C1 IQJFYFAKNUOHAE-UHFFFAOYSA-N 0.000 claims description 3
• MCPRPFWJSZDYBF-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(N=C1)=CC=C1C1=CC=C(F)C=C1 MCPRPFWJSZDYBF-UHFFFAOYSA-N 0.000 claims description 3
• AGWAOZJROKGNRO-UHFFFAOYSA-N 7-[[5-(4-fluorophenyl)pyridin-2-yl]oxymethyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(F)C=C1 AGWAOZJROKGNRO-UHFFFAOYSA-N 0.000 claims description 3
• USIKCXQLXHGVDD-UHFFFAOYSA-N 7-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-2-nitro-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC(C=N1)=CC=C1C1=CC=C(F)C=C1 USIKCXQLXHGVDD-UHFFFAOYSA-N 0.000 claims description 3
• GQEZVYKTQWMCCO-UHFFFAOYSA-N 7-[[6-(4-fluorophenyl)pyridin-3-yl]oxymethyl]-7-methyl-2-nitro-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(F)C=C1 GQEZVYKTQWMCCO-UHFFFAOYSA-N 0.000 claims description 3
• YVHHDRCXDTWXRG-UHFFFAOYSA-N 7-methyl-2-nitro-7-[(4-phenylmethoxyphenoxy)methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1OCC1=CC=CC=C1 YVHHDRCXDTWXRG-UHFFFAOYSA-N 0.000 claims description 3
• VWGRTYXITWEZSS-UHFFFAOYSA-N 7-methyl-2-nitro-7-[(4-phenylmethoxyphenyl)methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=C1)=CC=C1OCC1=CC=CC=C1 VWGRTYXITWEZSS-UHFFFAOYSA-N 0.000 claims description 3
• SPAYDMYBDJTUPR-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[3-(trifluoromethoxy)phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC1=CC=CC(OC(F)(F)F)=C1 SPAYDMYBDJTUPR-UHFFFAOYSA-N 0.000 claims description 3
• PAYUNELULSPXRL-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-(trifluoromethoxy)phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC1=CC=C(OC(F)(F)F)C=C1 PAYUNELULSPXRL-UHFFFAOYSA-N 0.000 claims description 3
• UOHVERHTRSLFEH-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-(trifluoromethoxy)phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC1=CC=C(OC(F)(F)F)C=C1 UOHVERHTRSLFEH-UHFFFAOYSA-N 0.000 claims description 3
• 230000002924 anti-infective effect Effects 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• XDFSBIUYBLENFF-UHFFFAOYSA-N 2-nitro-6-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=1)=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 XDFSBIUYBLENFF-UHFFFAOYSA-N 0.000 claims description 2
• PICDIDORINAMBJ-UHFFFAOYSA-N 2-nitro-6-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound C1OC2=NC([N+](=O)[O-])=CN2CC1COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 PICDIDORINAMBJ-UHFFFAOYSA-N 0.000 claims description 2
• DJTARRPMUXHLQD-UHFFFAOYSA-N 2-nitro-7-[[1-[4-(trifluoromethoxy)phenyl]-2h-pyridin-2-yl]oxymethyl]-6,7-dihydro-5h-imidazo[2,1-b][1,3]oxazine Chemical compound O1C2=NC([N+](=O)[O-])=CN2CCC1COC1C=CC=CN1C1=CC=C(OC(F)(F)F)C=C1 DJTARRPMUXHLQD-UHFFFAOYSA-N 0.000 claims description 2
• ALHDHSLKVWVIHN-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[3-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=1)=CC=CC=1C1=CC=C(OC(F)(F)F)C=C1 ALHDHSLKVWVIHN-UHFFFAOYSA-N 0.000 claims description 2
• NUSXIGWKAHRZFJ-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NUSXIGWKAHRZFJ-UHFFFAOYSA-N 0.000 claims description 2
• NTTCBTHLOZNZJK-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethoxy)phenyl]phenyl]methoxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NTTCBTHLOZNZJK-UHFFFAOYSA-N 0.000 claims description 2
• JHWOUTVKJWPBQN-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[4-[4-(trifluoromethyl)phenyl]phenoxy]methyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 JHWOUTVKJWPBQN-UHFFFAOYSA-N 0.000 claims description 2
• DTEROJRFJGXHNX-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[5-[4-(trifluoromethoxy)phenyl]pyridin-2-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 DTEROJRFJGXHNX-UHFFFAOYSA-N 0.000 claims description 2
• VYTTWAYUURNVAL-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[5-[4-(trifluoromethyl)phenyl]pyridin-2-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(N=C1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 VYTTWAYUURNVAL-UHFFFAOYSA-N 0.000 claims description 2
• OMUSZRWPEMVKON-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[6-[4-(trifluoromethoxy)phenyl]pyridin-3-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 OMUSZRWPEMVKON-UHFFFAOYSA-N 0.000 claims description 2
• DSVKLHUIYADEGR-UHFFFAOYSA-N 7-methyl-2-nitro-7-[[6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]oxymethyl]-5,6-dihydroimidazo[2,1-b][1,3]oxazine Chemical compound C1CN2C=C([N+]([O-])=O)N=C2OC1(C)COC(C=N1)=CC=C1C1=CC=C(C(F)(F)F)C=C1 DSVKLHUIYADEGR-UHFFFAOYSA-N 0.000 claims description 2
• KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims 1
• 230000003287 optical effect Effects 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 490
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 330
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 315
• 239000000047 product Substances 0.000 description 272
• 235000019439 ethyl acetate Nutrition 0.000 description 245
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 238
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 225
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• 239000000741 silica gel Substances 0.000 description 174
• 229910002027 silica gel Inorganic materials 0.000 description 174
• 238000005160 1H NMR spectroscopy Methods 0.000 description 173
• 239000007787 solid Substances 0.000 description 159
• 238000010828 elution Methods 0.000 description 154
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 147
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 142
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