SE452009B - 6-substituerade 6h-dibenso/b,d/pyranderivat, forfarande for deras framstellning samt farmaceutisk komposition innehallande nemnda derivat - Google Patents

Info

Publication number

SE452009B

SE452009B SE8106167A SE8106167A SE452009B SE 452009 B SE452009 B SE 452009B SE 8106167 A SE8106167 A SE 8106167A SE 8106167 A SE8106167 A SE 8106167A SE 452009 B SE452009 B SE 452009B

Authority

SE

Sweden

Prior art keywords

dibenzo

pyran

methyl

hydroxy

formula

Prior art date

1980-10-20

Links

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• 238000000034 method Methods 0.000 title claims description 38
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
• 238000002360 preparation method Methods 0.000 title claims description 3
• 150000001875 compounds Chemical class 0.000 claims description 230
• -1 ethyl-substituted piperidyl group Chemical group 0.000 claims description 168
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 120
• 229910052739 hydrogen Inorganic materials 0.000 claims description 75
• 239000001257 hydrogen Substances 0.000 claims description 73
• 239000000203 mixture Substances 0.000 claims description 42
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• 238000006243 chemical reaction Methods 0.000 claims description 40
• 150000002431 hydrogen Chemical class 0.000 claims description 38
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
• 238000011282 treatment Methods 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 20
• 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 17
• 239000000460 chlorine Substances 0.000 claims description 15
• 229910052783 alkali metal Inorganic materials 0.000 claims description 14
• 229910052705 radium Inorganic materials 0.000 claims description 14
• 229910052701 rubidium Inorganic materials 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 12
• 150000002367 halogens Chemical class 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 150000001412 amines Chemical class 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000006239 protecting group Chemical group 0.000 claims description 8
• 235000012000 cholesterol Nutrition 0.000 claims description 7
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
• 241001465754 Metazoa Species 0.000 claims description 6
• 230000015572 biosynthetic process Effects 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• 229910052731 fluorine Inorganic materials 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 238000007363 ring formation reaction Methods 0.000 claims description 6
• 238000002560 therapeutic procedure Methods 0.000 claims description 6
• ZQNSZNXHWQJCAK-UHFFFAOYSA-N (2-methoxy-4aH-benzo[c]chromen-6-yl)methanamine Chemical compound NCC1=C2C(=C3C(O1)C=CC(=C3)OC)C=CC=C2 ZQNSZNXHWQJCAK-UHFFFAOYSA-N 0.000 claims description 5
• AEGGBXJLMMKVEI-UHFFFAOYSA-N 2-chloro-6-methylbenzo[c]chromene-6-carboxylic acid Chemical compound C1=CC=C2C(C)(C(O)=O)OC3=CC=C(Cl)C=C3C2=C1 AEGGBXJLMMKVEI-UHFFFAOYSA-N 0.000 claims description 5
• YLGSBQPQENHHDS-UHFFFAOYSA-N 6-methylbenzo[c]chromene-6-carbonitrile Chemical compound C1=CC=C2C(C)(C#N)OC3=CC=CC=C3C2=C1 YLGSBQPQENHHDS-UHFFFAOYSA-N 0.000 claims description 5
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 210000002966 serum Anatomy 0.000 claims description 5
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• WDWLAWGHTXZJNS-UHFFFAOYSA-N ethyl 2-(4aH-benzo[c]chromen-6-yl)acetate Chemical compound C(C)OC(=O)CC1=C2C(=C3C(O1)C=CC=C3)C=CC=C2 WDWLAWGHTXZJNS-UHFFFAOYSA-N 0.000 claims description 4
• XLGFZPLLZBWTNP-UHFFFAOYSA-N ethyl 3-(2-fluoro-4aH-benzo[c]chromen-6-yl)propanoate Chemical compound C(C)OC(=O)CCC1=C2C(=C3C(O1)C=CC(=C3)F)C=CC=C2 XLGFZPLLZBWTNP-UHFFFAOYSA-N 0.000 claims description 4
• RADDJWUYJCISRB-UHFFFAOYSA-N ethyl 3-(8,9,10-trimethoxy-4aH-benzo[c]chromen-6-yl)propanoate Chemical compound C(C)OC(=O)CCC1=C2C(=C3C(O1)C=CC=C3)C(=C(C(=C2)OC)OC)OC RADDJWUYJCISRB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 150000003626 triacylglycerols Chemical class 0.000 claims description 4
• QULGJHLMOUBVQD-UHFFFAOYSA-N (8,9,10-trimethoxy-4aH-benzo[c]chromen-6-yl)methanamine Chemical compound NCC1=C2C(=C3C(O1)C=CC=C3)C(=C(C(=C2)OC)OC)OC QULGJHLMOUBVQD-UHFFFAOYSA-N 0.000 claims description 3
• MRQWUADQIMIYCZ-UHFFFAOYSA-N 1-methyl-4aH-benzo[c]chromen-6-amine Chemical compound NC1=C2C(=C3C(O1)C=CC=C3C)C=CC=C2 MRQWUADQIMIYCZ-UHFFFAOYSA-N 0.000 claims description 3
• QQLXHTCAMMRXCE-UHFFFAOYSA-N 2-(1-methoxy-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC=C3OC)C=CC=C2 QQLXHTCAMMRXCE-UHFFFAOYSA-N 0.000 claims description 3
• RSWULKOIAXFEBO-UHFFFAOYSA-N 2-(2-chloro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 RSWULKOIAXFEBO-UHFFFAOYSA-N 0.000 claims description 3
• DKMKBRUIEYBDBF-UHFFFAOYSA-N 2-(2-methoxy-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC(=C3)OC)C=CC=C2 DKMKBRUIEYBDBF-UHFFFAOYSA-N 0.000 claims description 3
• NAYXHONJVIWQTJ-UHFFFAOYSA-N 2-(2-nitro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC(=C3)[N+](=O)[O-])C=CC=C2 NAYXHONJVIWQTJ-UHFFFAOYSA-N 0.000 claims description 3
• OSLYOSBFYXMGCH-UHFFFAOYSA-N 2-(4ah-benzo[c]chromen-6-yl)acetic acid Chemical compound C1=CC=CC2OC(CC(=O)O)=C(C=CC=C3)C3=C21 OSLYOSBFYXMGCH-UHFFFAOYSA-N 0.000 claims description 3
• YLWZMRRIXRSMLG-UHFFFAOYSA-N 2-(8-chloro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC=C3)C=CC(=C2)Cl YLWZMRRIXRSMLG-UHFFFAOYSA-N 0.000 claims description 3
• ZLIVKHHDHFCBKG-UHFFFAOYSA-N 2-(8-fluoro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC=C3)C=CC(=C2)F ZLIVKHHDHFCBKG-UHFFFAOYSA-N 0.000 claims description 3
• KVNYCQKWTWETTI-UHFFFAOYSA-N 2-(8-methoxy-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC=C3)C=CC(=C2)OC KVNYCQKWTWETTI-UHFFFAOYSA-N 0.000 claims description 3
• RARZFNNGJNNUDK-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-amino-4aH-benzo[c]chromene-6-carboxylate Chemical compound CN(CCOC(=O)C1=C2C(=C3C(O1)C=CC(=C3)N)C=CC=C2)C RARZFNNGJNNUDK-UHFFFAOYSA-N 0.000 claims description 3
• SBOUATARNOBLKH-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-amino-6-methylbenzo[c]chromene-6-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCN(C)C)(C)OC3=CC=C(N)C=C3C2=C1 SBOUATARNOBLKH-UHFFFAOYSA-N 0.000 claims description 3
• VAJRCJHCRBQMFA-UHFFFAOYSA-N 2-(dimethylamino)ethyl 4aH-benzo[c]chromene-6-carboxylate Chemical compound CN(CCOC(=O)C1=C2C(=C3C(O1)C=CC=C3)C=CC=C2)C VAJRCJHCRBQMFA-UHFFFAOYSA-N 0.000 claims description 3
• WLLMAKBNRIDHGZ-UHFFFAOYSA-N 2-(dimethylamino)ethyl 6-methylbenzo[c]chromene-6-carboxylate Chemical compound C1=CC=C2C(C(=O)OCCN(C)C)(C)OC3=CC=CC=C3C2=C1 WLLMAKBNRIDHGZ-UHFFFAOYSA-N 0.000 claims description 3
• MBZHEZIRYJFAMC-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-chloro-4aH-benzo[c]chromen-6-yl)ethanol Chemical compound OC(CNC(C)(C)C)C1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 MBZHEZIRYJFAMC-UHFFFAOYSA-N 0.000 claims description 3
• FPKMNRCRAABLMG-UHFFFAOYSA-N 3-(2-chloro-4aH-benzo[c]chromen-6-yl)propanoic acid Chemical compound C(=O)(O)CCC1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 FPKMNRCRAABLMG-UHFFFAOYSA-N 0.000 claims description 3
• FBYYLFJDUPWLFR-UHFFFAOYSA-N 3-(4aH-benzo[c]chromen-6-yl)-N-methylpropan-1-amine Chemical compound CNCCCC1=C2C(=C3C(O1)C=CC=C3)C=CC=C2 FBYYLFJDUPWLFR-UHFFFAOYSA-N 0.000 claims description 3
• HQANBWUZTFFASO-UHFFFAOYSA-N 4-(4aH-benzo[c]chromen-6-yl)piperidine Chemical compound N1CCC(CC1)C1=C2C(=C3C(O1)C=CC=C3)C=CC=C2 HQANBWUZTFFASO-UHFFFAOYSA-N 0.000 claims description 3
• SEFMZHOARYMEQR-UHFFFAOYSA-N 6-(aminomethyl)-4aH-benzo[c]chromen-2-ol Chemical compound NCC1=C2C(=C3C(O1)C=CC(=C3)O)C=CC=C2 SEFMZHOARYMEQR-UHFFFAOYSA-N 0.000 claims description 3
• MFPHECWJSYZMRG-UHFFFAOYSA-N CCOC(=O)CC1=C2C=CC=CC2=C3C=C(C=CC3O1)O Chemical compound CCOC(=O)CC1=C2C=CC=CC2=C3C=C(C=CC3O1)O MFPHECWJSYZMRG-UHFFFAOYSA-N 0.000 claims description 3
• JSYKYPQFBMZXBT-UHFFFAOYSA-N CN(C)CCOC(=O)C1=C2C=CC=CC2=C3C=C(C=CC3O1)Cl Chemical compound CN(C)CCOC(=O)C1=C2C=CC=CC2=C3C=C(C=CC3O1)Cl JSYKYPQFBMZXBT-UHFFFAOYSA-N 0.000 claims description 3
• YMZUUWYQGIXQGK-UHFFFAOYSA-N CN(C)CCOC(=O)C1=C2C=CC=CC2=C3C=C(C=CC3O1)F Chemical compound CN(C)CCOC(=O)C1=C2C=CC=CC2=C3C=C(C=CC3O1)F YMZUUWYQGIXQGK-UHFFFAOYSA-N 0.000 claims description 3
• GERCXGRNRCSOJG-UHFFFAOYSA-N CN(C)CCOC(=O)CC1=C2C=CC=CC2=C3C=CC=CC3O1 Chemical compound CN(C)CCOC(=O)CC1=C2C=CC=CC2=C3C=CC=CC3O1 GERCXGRNRCSOJG-UHFFFAOYSA-N 0.000 claims description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• RDWMLVIEHMPVOE-UHFFFAOYSA-N ethyl 2-chloro-6-methylbenzo[c]chromene-6-carboxylate Chemical compound C1=CC=C2C(C(=O)OCC)(C)OC3=CC=C(Cl)C=C3C2=C1 RDWMLVIEHMPVOE-UHFFFAOYSA-N 0.000 claims description 3
• YTTQOGOZQBPUOM-UHFFFAOYSA-N ethyl 3-(2-chloro-4aH-benzo[c]chromen-6-yl)propanoate Chemical compound C(C)OC(=O)CCC1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 YTTQOGOZQBPUOM-UHFFFAOYSA-N 0.000 claims description 3
• QFCZMYJZELGOCE-UHFFFAOYSA-N ethyl 3-(6-methylbenzo[c]chromen-6-yl)propanoate Chemical compound C1=CC=C2C(CCC(=O)OCC)(C)OC3=CC=CC=C3C2=C1 QFCZMYJZELGOCE-UHFFFAOYSA-N 0.000 claims description 3
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
• 230000002265 prevention Effects 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• XOPIRYPKEJPRLA-UHFFFAOYSA-N 1,10-dimethoxy-6-methylbenzo[c]chromene-6-carboxylic acid Chemical compound O1C(C)(C(O)=O)C2=CC=CC(OC)=C2C2=C1C=CC=C2OC XOPIRYPKEJPRLA-UHFFFAOYSA-N 0.000 claims description 2
• FOWDCBKFJNPSDG-UHFFFAOYSA-N 1-(1,10-dimethoxy-4aH-benzo[c]chromen-6-yl)piperazine Chemical compound N1(CCNCC1)C1=C2C(=C3C(O1)C=CC=C3OC)C(=CC=C2)OC FOWDCBKFJNPSDG-UHFFFAOYSA-N 0.000 claims description 2
• QIOIDCLMCBEBEI-UHFFFAOYSA-N 1-(2-chloro-4aH-benzo[c]chromen-6-yl)piperazine Chemical compound N1(CCNCC1)C1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 QIOIDCLMCBEBEI-UHFFFAOYSA-N 0.000 claims description 2
• HOPPSOGNVFCRAH-UHFFFAOYSA-N 1-(2-nitro-4aH-benzo[c]chromen-6-yl)piperazine Chemical compound N1(CCNCC1)C1=C2C(=C3C(O1)C=CC(=C3)[N+](=O)[O-])C=CC=C2 HOPPSOGNVFCRAH-UHFFFAOYSA-N 0.000 claims description 2
• GQYDQYFKLUPGDU-UHFFFAOYSA-N 1-(4aH-benzo[c]chromen-6-yl)-2-(tert-butylamino)ethanol Chemical compound OC(CNC(C)(C)C)C1=C2C(=C3C(O1)C=CC=C3)C=CC=C2 GQYDQYFKLUPGDU-UHFFFAOYSA-N 0.000 claims description 2
• QBVTWEZLAOCPQD-UHFFFAOYSA-N 1-methoxy-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC=C3OC)C=CC=C2 QBVTWEZLAOCPQD-UHFFFAOYSA-N 0.000 claims description 2
• WHWCHJDHCQDSPC-UHFFFAOYSA-N 2-(2-fluoro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC(=C3)F)C=CC=C2 WHWCHJDHCQDSPC-UHFFFAOYSA-N 0.000 claims description 2
• YPPHJKBBRWTSAF-UHFFFAOYSA-N 2-(8-nitro-4aH-benzo[c]chromen-6-yl)acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC=C3)C=CC(=C2)[N+](=O)[O-] YPPHJKBBRWTSAF-UHFFFAOYSA-N 0.000 claims description 2
• XSWBHGFPWPHCNM-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methoxy-4aH-benzo[c]chromene-6-carboxylate Chemical compound CN(CCOC(=O)C1=C2C(=C3C(O1)C=CC(=C3)OC)C=CC=C2)C XSWBHGFPWPHCNM-UHFFFAOYSA-N 0.000 claims description 2
• JHFHYTLSVGVYPA-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-nitro-4aH-benzo[c]chromene-6-carboxylate Chemical compound CN(CCOC(=O)C1=C2C(=C3C(O1)C=CC(=C3)[N+](=O)[O-])C=CC=C2)C JHFHYTLSVGVYPA-UHFFFAOYSA-N 0.000 claims description 2
• PNKNKZPWNPFZFL-UHFFFAOYSA-N 2-(dimethylamino)ethyl 6-ethylbenzo[c]chromene-6-carboxylate Chemical compound C1=CC=C2C(CC)(C(=O)OCCN(C)C)OC3=CC=CC=C3C2=C1 PNKNKZPWNPFZFL-UHFFFAOYSA-N 0.000 claims description 2
• PQDDMQPNFRIJQI-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-methoxy-4aH-benzo[c]chromen-6-yl)ethanol Chemical compound OC(CNC(C)(C)C)C1=C2C(=C3C(O1)C=CC(=C3)OC)C=CC=C2 PQDDMQPNFRIJQI-UHFFFAOYSA-N 0.000 claims description 2
• HVLQEMLOZQZNOJ-UHFFFAOYSA-N 2-[2-(trifluoromethyl)-4aH-benzo[c]chromen-6-yl]acetic acid Chemical compound C(=O)(O)CC1=C2C(=C3C(O1)C=CC(=C3)C(F)(F)F)C=CC=C2 HVLQEMLOZQZNOJ-UHFFFAOYSA-N 0.000 claims description 2
• YQCYLAFKFZPYMI-UHFFFAOYSA-N 2-chloro-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC(=C3)Cl)C=CC=C2 YQCYLAFKFZPYMI-UHFFFAOYSA-N 0.000 claims description 2
• LCVGSLUHRUEFQF-UHFFFAOYSA-N 2-chloro-6-methylbenzo[c]chromene-6-carbonitrile Chemical compound C1=CC=C2C(C)(C#N)OC3=CC=C(Cl)C=C3C2=C1 LCVGSLUHRUEFQF-UHFFFAOYSA-N 0.000 claims description 2
• FMJCLWACXVWTEV-UHFFFAOYSA-N 2-fluoro-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC(=C3)F)C=CC=C2 FMJCLWACXVWTEV-UHFFFAOYSA-N 0.000 claims description 2
• QRVIAYYVCKZNDL-UHFFFAOYSA-N 2-methoxy-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC(=C3)OC)C=CC=C2 QRVIAYYVCKZNDL-UHFFFAOYSA-N 0.000 claims description 2
• UXBZOIKFZKLKIP-UHFFFAOYSA-N 2-methoxy-6-methylbenzo[c]chromene-6-carboxylic acid Chemical compound C1=CC=C2C3=CC(OC)=CC=C3OC(C)(C(O)=O)C2=C1 UXBZOIKFZKLKIP-UHFFFAOYSA-N 0.000 claims description 2
• KNURFBBLRYWGPU-UHFFFAOYSA-N 2-nitro-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC(=C3)[N+](=O)[O-])C=CC=C2 KNURFBBLRYWGPU-UHFFFAOYSA-N 0.000 claims description 2
• VZVYWVAUYWGVHZ-UHFFFAOYSA-N 3-(2-nitro-4aH-benzo[c]chromen-6-yl)propanoic acid Chemical compound C(=O)(O)CCC1=C2C(=C3C(O1)C=CC(=C3)[N+](=O)[O-])C=CC=C2 VZVYWVAUYWGVHZ-UHFFFAOYSA-N 0.000 claims description 2
• OYDXACFITJOVNZ-UHFFFAOYSA-N 3-(8,9,10-trimethoxy-4aH-benzo[c]chromen-6-yl)propanoic acid Chemical compound C(=O)(O)CCC1=C2C(=C3C(O1)C=CC=C3)C(=C(C(=C2)OC)OC)OC OYDXACFITJOVNZ-UHFFFAOYSA-N 0.000 claims description 2
• YWSOVFGKQVPUIQ-UHFFFAOYSA-N 6-methyl-2-(trifluoromethyl)benzo[c]chromene-6-carboxylic acid Chemical compound C1=CC=C2C(C)(C(O)=O)OC3=CC=C(C(F)(F)F)C=C3C2=C1 YWSOVFGKQVPUIQ-UHFFFAOYSA-N 0.000 claims description 2
• JMIGYWBRQKIVES-UHFFFAOYSA-N 8,9,10-trimethoxy-4aH-benzo[c]chromene-6-carbonitrile Chemical compound C(#N)C1=C2C(=C3C(O1)C=CC=C3)C(=C(C(=C2)OC)OC)OC JMIGYWBRQKIVES-UHFFFAOYSA-N 0.000 claims description 2
• FJVKEZLUXBOCKN-UHFFFAOYSA-N 8,9,10-trimethoxy-4aH-benzo[c]chromene-6-carboxylic acid Chemical compound C(=O)(O)C1=C2C(=C3C(O1)C=CC=C3)C(=C(C(=C2)OC)OC)OC FJVKEZLUXBOCKN-UHFFFAOYSA-N 0.000 claims description 2
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