JPH0248028B2 - - Google Patents
Info
- Publication number
- JPH0248028B2 JPH0248028B2 JP57212045A JP21204582A JPH0248028B2 JP H0248028 B2 JPH0248028 B2 JP H0248028B2 JP 57212045 A JP57212045 A JP 57212045A JP 21204582 A JP21204582 A JP 21204582A JP H0248028 B2 JPH0248028 B2 JP H0248028B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pyrrolo
- imidazo
- alkyl
- hydrogen
- Prior art date
- 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.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 claims description 51
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 42
- 239000000463 material Substances 0.000 claims description 34
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000004715 keto acids Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical group C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 8
- GOHIXUOTOMMONS-UHFFFAOYSA-N 1h-pyrrolo[1,2-a]indole Chemical group C1=CC=C2N3CC=CC3=CC2=C1 GOHIXUOTOMMONS-UHFFFAOYSA-N 0.000 claims description 7
- IIOKDOJKJGCOEP-UHFFFAOYSA-N 3h-pyrrolo[1,2-a]imidazole Chemical group C1=CN2CC=NC2=C1 IIOKDOJKJGCOEP-UHFFFAOYSA-N 0.000 claims description 7
- CTTMASDELHSUQP-UHFFFAOYSA-N 4h-pyrrolo[1,2-a]benzimidazole Chemical group N1C2=CC=CC=C2N2C1=CC=C2 CTTMASDELHSUQP-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- BYLPZVAKOZYZPH-UHFFFAOYSA-N imidazo[2,1-a]isoquinoline Chemical group C1=CC=C2C3=NC=CN3C=CC2=C1 BYLPZVAKOZYZPH-UHFFFAOYSA-N 0.000 claims description 7
- UFBBWLWUIISIPW-UHFFFAOYSA-N imidazo[2,1-b][1,3]thiazole Chemical group C1=CSC2=NC=CN21 UFBBWLWUIISIPW-UHFFFAOYSA-N 0.000 claims description 7
- 150000002596 lactones Chemical class 0.000 claims description 7
- IEOUSWADWJLLCH-UHFFFAOYSA-N pyrrolo[1,2-a]quinoxaline Chemical group C1=NC2=CC=CC=C2N2C1=CC=C2 IEOUSWADWJLLCH-UHFFFAOYSA-N 0.000 claims description 7
- XUOAXCULCGCUDL-UHFFFAOYSA-N pyrrolo[2,1-b][1,3]benzothiazole Chemical group S1C2=CC=CC=C2N2C1=CC=C2 XUOAXCULCGCUDL-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000012024 dehydrating agents Substances 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- INSWZAQOISIYDT-UHFFFAOYSA-N imidazo[1,2-a]pyrimidine Chemical group C1=CC=NC2=NC=CN21 INSWZAQOISIYDT-UHFFFAOYSA-N 0.000 claims description 3
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 4
- 150000008065 acid anhydrides Chemical group 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- -1 4-morpholinophenyl Chemical group 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
- 239000000908 ammonium hydroxide Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- 239000004927 clay Substances 0.000 description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 8
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 5
- 239000012485 toluene extract Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- HGLISOFZJUBYPD-UHFFFAOYSA-N 2-(1-ethyl-2-methylindole-3-carbonyl)pyridine-3-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC=CC=C1C(O)=O HGLISOFZJUBYPD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000003094 microcapsule Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- BUZMJVBOGDBMGI-UHFFFAOYSA-N 1-phenylpropylbenzene Chemical compound C=1C=CC=CC=1C(CC)C1=CC=CC=C1 BUZMJVBOGDBMGI-UHFFFAOYSA-N 0.000 description 2
- ASRYMVLYDNUKPL-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(2-phenylpyrrolo[2,1-b][1,3]benzothiazol-1-yl)-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2SC3=C(N21)C=CC=C3)C1=CC=CC=C1)C ASRYMVLYDNUKPL-UHFFFAOYSA-N 0.000 description 2
- OHXSPNCYEXAYMZ-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1)C OHXSPNCYEXAYMZ-UHFFFAOYSA-N 0.000 description 2
- SMCJMUGBZOBZMV-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)OC)C SMCJMUGBZOBZMV-UHFFFAOYSA-N 0.000 description 2
- RNZSCQZUPATAKS-UHFFFAOYSA-N 3-[4-(diethylamino)butan-2-yloxy]-3-(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)OC(C)CCN(CC)CC)=C(C)N(CC)C2=C1 RNZSCQZUPATAKS-UHFFFAOYSA-N 0.000 description 2
- DHZNOEONHMHDQZ-UHFFFAOYSA-N 6-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazole Chemical compound C1=CC(OC)=CC=C1C1=CN(C=CS2)C2=N1 DHZNOEONHMHDQZ-UHFFFAOYSA-N 0.000 description 2
- AHLNKXIKNJTQFJ-UHFFFAOYSA-N 7-(1-ethyl-2-methylindol-3-yl)-7-[6-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]furo[3,4-b]pyridin-5-one Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C1(C2=NC=CC=C2C(=O)O1)C(N1C=CSC1=N1)=C1C1=CC=C(OC)C=C1 AHLNKXIKNJTQFJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZKURGBYDCVNWKH-UHFFFAOYSA-N [3,7-bis(dimethylamino)phenothiazin-10-yl]-phenylmethanone Chemical compound C12=CC=C(N(C)C)C=C2SC2=CC(N(C)C)=CC=C2N1C(=O)C1=CC=CC=C1 ZKURGBYDCVNWKH-UHFFFAOYSA-N 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229920001568 phenolic resin Polymers 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZLFDMWVCAPSKJN-UHFFFAOYSA-N (1-propylcyclohexa-2,4-dien-1-yl)benzene Chemical group C(CC)C1(CC=CC=C1)C1=CC=CC=C1 ZLFDMWVCAPSKJN-UHFFFAOYSA-N 0.000 description 1
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 1
- DTCCVIYSGXONHU-CJHDCQNGSA-N (z)-2-(2-phenylethenyl)but-2-enedioic acid Chemical compound OC(=O)\C=C(C(O)=O)\C=CC1=CC=CC=C1 DTCCVIYSGXONHU-CJHDCQNGSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NAJSDBBBIPOIKV-UHFFFAOYSA-N 1h-benzimidazole;diphenylmethanone Chemical compound C1=CC=C2NC=NC2=C1.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 NAJSDBBBIPOIKV-UHFFFAOYSA-N 0.000 description 1
- OMVSWZDEEGIJJI-UHFFFAOYSA-N 2,2,4-Trimethyl-1,3-pentadienol diisobutyrate Chemical compound CC(C)C(=O)OC(C(C)C)C(C)(C)COC(=O)C(C)C OMVSWZDEEGIJJI-UHFFFAOYSA-N 0.000 description 1
- JCTXKRPTIMZBJT-UHFFFAOYSA-N 2,2,4-trimethylpentane-1,3-diol Chemical compound CC(C)C(O)C(C)(C)CO JCTXKRPTIMZBJT-UHFFFAOYSA-N 0.000 description 1
- OTLMQCNHFVYECA-UHFFFAOYSA-N 2-(2-carboxybenzoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1C(O)=O OTLMQCNHFVYECA-UHFFFAOYSA-N 0.000 description 1
- CPEQFJYBWAAQLE-UHFFFAOYSA-N 2-[4-(diethylamino)-2-ethoxybenzoyl]benzoic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O CPEQFJYBWAAQLE-UHFFFAOYSA-N 0.000 description 1
- QRBYEBPQYCYKFF-UHFFFAOYSA-N 2-[4-(diethylamino)-2-ethoxybenzoyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CC=C1C(O)=O QRBYEBPQYCYKFF-UHFFFAOYSA-N 0.000 description 1
- CONFUNYOPVYVDC-UHFFFAOYSA-N 3,3-bis(1-ethyl-2-methylindol-3-yl)-2-benzofuran-1-one Chemical compound C1=CC=C2C(C3(C4=CC=CC=C4C(=O)O3)C3=C(C)N(C4=CC=CC=C43)CC)=C(C)N(CC)C2=C1 CONFUNYOPVYVDC-UHFFFAOYSA-N 0.000 description 1
- ULBXMKVKEJWHAZ-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2)C1=CC=CC=C1)C ULBXMKVKEJWHAZ-UHFFFAOYSA-N 0.000 description 1
- RVSRYZXSKYCIRK-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(2-phenylimidazo[1,2-a]pyridin-3-yl)furo[3,4-b]quinolin-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(C=2C1=NC=1C=CC=CC=1C=2)=O)C1=C(N=C2N1C=CC=C2)C1=CC=CC=C1)C RVSRYZXSKYCIRK-UHFFFAOYSA-N 0.000 description 1
- PQXOBZKPEXKZMM-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2SC=CN21)C1=CC=CC=C1)C PQXOBZKPEXKZMM-UHFFFAOYSA-N 0.000 description 1
- DNKRRAKWDZQPPS-UHFFFAOYSA-N 3-(1-ethyl-2-methylindol-3-yl)-3-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)-2-benzofuran-1-one Chemical compound C(C)N1C(=C(C2=CC=CC=C12)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2C)C1=CC=CC=C1)C DNKRRAKWDZQPPS-UHFFFAOYSA-N 0.000 description 1
- ZVCFSCXUODRMKI-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)pyridine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=CC=CN=C1C(O)=O ZVCFSCXUODRMKI-UHFFFAOYSA-N 0.000 description 1
- ODEBUTRNSFVGRT-UHFFFAOYSA-N 3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-3-(4-morpholin-4-ylphenyl)-2-benzofuran-1-one Chemical compound O1CCN(CC1)C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1 ODEBUTRNSFVGRT-UHFFFAOYSA-N 0.000 description 1
- XPVSRXIKJFDZFV-UHFFFAOYSA-N 3-(4-ethyl-1-methyl-2-phenylpyrrolo[1,2-a]benzimidazol-3-yl)-3-(4-morpholin-4-ylphenyl)-2-benzofuran-1-one Chemical compound O1CCN(CC1)C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C=1C(=C(N2C=1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1 XPVSRXIKJFDZFV-UHFFFAOYSA-N 0.000 description 1
- BOYJNWSWUJMSKX-UHFFFAOYSA-N 3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-3-(4-morpholin-4-ylphenyl)-2-benzofuran-1-one Chemical compound O1CCN(CC1)C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1 BOYJNWSWUJMSKX-UHFFFAOYSA-N 0.000 description 1
- AUFACNFYIOJBBY-UHFFFAOYSA-N 3-[2-butoxy-4-(diethylamino)phenyl]-3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-2-benzofuran-1-one Chemical compound C(CCC)OC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1 AUFACNFYIOJBBY-UHFFFAOYSA-N 0.000 description 1
- HLKSLFDSPXCLGH-UHFFFAOYSA-N 3-[2-butoxy-4-(diethylamino)phenyl]-3-(4-ethyl-1-methyl-2-phenylpyrrolo[1,2-a]benzimidazol-3-yl)-2-benzofuran-1-one Chemical compound C(CCC)OC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C=1C(=C(N2C=1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1 HLKSLFDSPXCLGH-UHFFFAOYSA-N 0.000 description 1
- BBRNXZZTHPDLIQ-UHFFFAOYSA-N 3-[2-butoxy-4-(diethylamino)phenyl]-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound C(CCC)OC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1 BBRNXZZTHPDLIQ-UHFFFAOYSA-N 0.000 description 1
- ICQLWWINRCRUNX-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-2-methoxyphenyl]-3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)NC1CCCCC1)C1(OC(=O)C2=CC=CC=C12)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1 ICQLWWINRCRUNX-UHFFFAOYSA-N 0.000 description 1
- JJCBTAJQLJXEJT-UHFFFAOYSA-N 3-[4-(cyclohexylamino)-2-methoxyphenyl]-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)NC1CCCCC1)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1 JJCBTAJQLJXEJT-UHFFFAOYSA-N 0.000 description 1
- WDSFHHSUBDQIIY-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxybenzoyl]quinoxaline-2-carboxylic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC2=CC=CC=C2N=C1C(O)=O WDSFHHSUBDQIIY-UHFFFAOYSA-N 0.000 description 1
- MCSHTDYTMSHISE-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-(1-ethyl-6-phenylpyrrolo[1,2-a]imidazol-5-yl)-2-benzofuran-1-one Chemical compound C(C)OC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N1C=CN2CC)C1=CC=CC=C1 MCSHTDYTMSHISE-UHFFFAOYSA-N 0.000 description 1
- DFTFCQZCHHGLFZ-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound C(C)OC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1 DFTFCQZCHHGLFZ-UHFFFAOYSA-N 0.000 description 1
- MFPBSOKVCWEMBS-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)furo[3,4-b]quinoxalin-1-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2N3C=CC=C(C)C3=NC=2C=2C=CC=CC=2)C2=NC3=CC=CC=C3N=C2C(=O)O1 MFPBSOKVCWEMBS-UHFFFAOYSA-N 0.000 description 1
- WRPGXDPCGDRPMT-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxyphenyl]-3-[2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-yl]-2-benzofuran-1-one Chemical compound C(C)N(C1=CC(=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)N(C)C)OCC)CC WRPGXDPCGDRPMT-UHFFFAOYSA-N 0.000 description 1
- ZNMLIUFUSHRMES-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methoxyphenyl]-3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1 ZNMLIUFUSHRMES-UHFFFAOYSA-N 0.000 description 1
- MHXMRZFEESDFRO-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methoxyphenyl]-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1 MHXMRZFEESDFRO-UHFFFAOYSA-N 0.000 description 1
- BOPFGLBVHVYJJW-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methoxyphenyl]-3-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2SC=CN21)C1=CC=CC=C1 BOPFGLBVHVYJJW-UHFFFAOYSA-N 0.000 description 1
- UDZKABPMCQEKCX-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methoxyphenyl]-3-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2C)C1=CC=CC=C1 UDZKABPMCQEKCX-UHFFFAOYSA-N 0.000 description 1
- FOONUKVPCRTWED-UHFFFAOYSA-N 3-[4-(diethylamino)phenyl]-3-(4-ethyl-1-methyl-2-phenylpyrrolo[1,2-a]benzimidazol-3-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C=1C(=C(N2C=1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1)CC FOONUKVPCRTWED-UHFFFAOYSA-N 0.000 description 1
- BTXOBPDRILIJKK-UHFFFAOYSA-N 3-[4-(diethylamino)phenyl]-3-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2SC=CN21)C1=CC=CC=C1)CC BTXOBPDRILIJKK-UHFFFAOYSA-N 0.000 description 1
- YTWDRARDIBJWAM-UHFFFAOYSA-N 3-[4-(diethylamino)phenyl]-3-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=CC=CC=C12)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)OC)CC YTWDRARDIBJWAM-UHFFFAOYSA-N 0.000 description 1
- NMWKWBPNKPGATC-UHFFFAOYSA-N 4,5,6,7-tetrachloro-2-benzofuran-1(3H)-one Chemical compound ClC1=C(Cl)C(Cl)=C2COC(=O)C2=C1Cl NMWKWBPNKPGATC-UHFFFAOYSA-N 0.000 description 1
- NFJMJNFRPDEENH-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)-2-methoxyphenyl]-3-(4-ethyl-1-methyl-2-phenylpyrrolo[1,2-a]benzimidazol-3-yl)-2-benzofuran-1-one Chemical compound COC1=C(C=CC(=C1)N(CC)CC)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C=1C(=C(N2C=1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1 NFJMJNFRPDEENH-UHFFFAOYSA-N 0.000 description 1
- OFJIUQWAVXOXCJ-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1)CC OFJIUQWAVXOXCJ-UHFFFAOYSA-N 0.000 description 1
- VHLBHIGTVOBNCR-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(4-ethyl-1-methyl-2-phenylpyrrolo[1,2-a]benzimidazol-3-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C=1C(=C(N2C=1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1)CC VHLBHIGTVOBNCR-UHFFFAOYSA-N 0.000 description 1
- IBNUDWORCSDLMN-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(4-ethyl-2-phenylpyrrolo[1,2-a]benzimidazol-1-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C1=C(C=C2N(C3=C(N21)C=CC=C3)CC)C1=CC=CC=C1)CC IBNUDWORCSDLMN-UHFFFAOYSA-N 0.000 description 1
- OLILVNQSUGBEAW-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C1=C(N=C2SC=CN21)C1=CC=CC=C1)CC OLILVNQSUGBEAW-UHFFFAOYSA-N 0.000 description 1
- ZNJPAPIZIZVXRP-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C1=C(N=C2N1C=CC=C2C)C1=CC=CC=C1)CC ZNJPAPIZIZVXRP-UHFFFAOYSA-N 0.000 description 1
- WKYSLCSGQGVEEX-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3-[4-(diethylamino)phenyl]-3-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-2-benzofuran-1-one Chemical compound C(C)N(C1=CC=C(C=C1)C1(OC(=O)C2=C(C(=C(C(=C12)Cl)Cl)Cl)Cl)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)OC)CC WKYSLCSGQGVEEX-UHFFFAOYSA-N 0.000 description 1
- QOULJXYVKZMPDM-UHFFFAOYSA-N 4-imidazo[1,2-a]pyridin-2-yl-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1=CN(C=CC=C2)C2=N1 QOULJXYVKZMPDM-UHFFFAOYSA-N 0.000 description 1
- VVZZGSXQVGGQOR-UHFFFAOYSA-N 5-(1-methyl-3,4-dihydro-2H-quinolin-6-yl)-5-(2-phenylimidazo[1,2-a]pyridin-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CN1CCCC2=CC(=CC=C12)C1(OC(C2=NC=CC=C21)=O)C1=C(N=C2N1C=CC=C2)C1=CC=CC=C1 VVZZGSXQVGGQOR-UHFFFAOYSA-N 0.000 description 1
- LOMKTWZMPCISOR-UHFFFAOYSA-N 5-(1-methyl-3,4-dihydro-2H-quinolin-6-yl)-5-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CN1CCCC2=CC(=CC=C12)C1(OC(C2=NC=CC=C21)=O)C1=C(N=C2N1C=CC=C2C)C1=CC=CC=C1 LOMKTWZMPCISOR-UHFFFAOYSA-N 0.000 description 1
- GNXZFRHZNNCJIE-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)furo[3,4-b]pyridin-7-one Chemical compound C(C)N(C1=CC(=C(C=C1)C1(OC(C2=NC=CC=C21)=O)C1=C(N=C2SC=CN21)C1=CC=CC=C1)OCC)CC GNXZFRHZNNCJIE-UHFFFAOYSA-N 0.000 description 1
- DTFGHYOHVVPWAS-UHFFFAOYSA-N 5-[4-(diethylamino)-2-ethoxyphenyl]-5-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)furo[3,4-b]pyridin-7-one Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C1(C=2N3C=CC=C(C)C3=NC=2C=2C=CC=CC=2)C2=CC=CN=C2C(=O)O1 DTFGHYOHVVPWAS-UHFFFAOYSA-N 0.000 description 1
- VVJGYYIYWSWLRQ-UHFFFAOYSA-N 5-[6-(4-methoxyphenyl)imidazo[2,1-b][1,3]thiazol-5-yl]-5-(1-methyl-3,4-dihydro-2H-quinolin-6-yl)furo[3,4-b]pyridin-7-one Chemical compound CN1CCCC2=CC(=CC=C12)C1(OC(C2=NC=CC=C21)=O)C1=C(N=C2SC=CN21)C1=CC=C(C=C1)OC VVJGYYIYWSWLRQ-UHFFFAOYSA-N 0.000 description 1
- VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
- CLGWKWDAQBVGFJ-UHFFFAOYSA-N 6-(dimethylamino)-3,3-bis[2-(dimethylamino)phenyl]-2-benzofuran-1-one Chemical compound C=1C(N(C)C)=CC=C2C=1C(=O)OC2(C=1C(=CC=CC=1)N(C)C)C1=CC=CC=C1N(C)C CLGWKWDAQBVGFJ-UHFFFAOYSA-N 0.000 description 1
- QIZJCNXVHQWYGW-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(4,4-dimethyl-2-phenylpyrrolo[1,2-a]indol-3-yl)-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C=1C(=CN2C=1C(C=1C=CC=CC2=1)(C)C)C1=CC=CC=C1)C QIZJCNXVHQWYGW-UHFFFAOYSA-N 0.000 description 1
- NPEDOMPFRVJMTR-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(6-phenylimidazo[2,1-b][1,3]thiazol-5-yl)-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=C(N=C2SC=CN21)C1=CC=CC=C1)C NPEDOMPFRVJMTR-UHFFFAOYSA-N 0.000 description 1
- BMTUHIWGZCIIHR-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-(8-methyl-2-phenylimidazo[1,2-a]pyridin-3-yl)-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=C(N=C2N1C=CC=C2C)C1=CC=CC=C1)C BMTUHIWGZCIIHR-UHFFFAOYSA-N 0.000 description 1
- BDESPTXQJIAYQT-UHFFFAOYSA-N 6-(dimethylamino)-3-[4-(dimethylamino)phenyl]-3-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-2-benzofuran-1-one Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)OC)C BDESPTXQJIAYQT-UHFFFAOYSA-N 0.000 description 1
- SSLYXPCZDPVEMJ-UHFFFAOYSA-N 7-[2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-3-yl]-7-(2-methyl-1-pentylindol-3-yl)furo[3,4-b]pyridin-5-one Chemical compound C(CCCC)N1C(=C(C2=CC=CC=C12)C1(OC(C=2C1=NC=CC=2)=O)C1=C(N=C2N1C=CC=C2)C1=CC=C(C=C1)OC)C SSLYXPCZDPVEMJ-UHFFFAOYSA-N 0.000 description 1
- CZYPXIUACURBEQ-UHFFFAOYSA-N 8-methyl-2-phenylimidazo[1,2-a]pyridine Chemical compound N1=C2C(C)=CC=CN2C=C1C1=CC=CC=C1 CZYPXIUACURBEQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- XABKTVAKAYEZTR-UHFFFAOYSA-N CC1=NC2=CC=CC=C2N3C1=CC(=C3C4(C5=C(C(=O)O4)N=CC=C5)C6=CC7=C(C=C6)N(CCC7)C)C8=CC=CC=C8 Chemical compound CC1=NC2=CC=CC=C2N3C1=CC(=C3C4(C5=C(C(=O)O4)N=CC=C5)C6=CC7=C(C=C6)N(CCC7)C)C8=CC=CC=C8 XABKTVAKAYEZTR-UHFFFAOYSA-N 0.000 description 1
- MUYNLUAILSOBAI-UHFFFAOYSA-N CCN(CC)C1=CC(=C(C=C1)C2(C3=NC4=CC=CC=C4N=C3C(=O)O2)C5=C(N=C6N5C=CS6)C7=CC=CC=C7)OCC Chemical compound CCN(CC)C1=CC(=C(C=C1)C2(C3=NC4=CC=CC=C4N=C3C(=O)O2)C5=C(N=C6N5C=CS6)C7=CC=CC=C7)OCC MUYNLUAILSOBAI-UHFFFAOYSA-N 0.000 description 1
- QYBVJUNJGFUBKU-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(C=C7N6C8=CC=CC=C8S7)C9=CC=CC=C9)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(C=C7N6C8=CC=CC=C8S7)C9=CC=CC=C9)C QYBVJUNJGFUBKU-UHFFFAOYSA-N 0.000 description 1
- DIAVPRFGMDDEFB-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(N=C7N6C=CC=C7C)C8=CC=CC=C8)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(N=C7N6C=CC=C7C)C8=CC=CC=C8)C DIAVPRFGMDDEFB-UHFFFAOYSA-N 0.000 description 1
- BNCWDHXFYQPKFC-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(N=C7N6C=CS7)C8=CC=C(C=C8)OC)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5C=C4C(=O)O3)C6=C(N=C7N6C=CS7)C8=CC=C(C=C8)OC)C BNCWDHXFYQPKFC-UHFFFAOYSA-N 0.000 description 1
- QAUVDTCOWXWIOI-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CC=C7)C8=CC=CC=C8)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CC=C7)C8=CC=CC=C8)C QAUVDTCOWXWIOI-UHFFFAOYSA-N 0.000 description 1
- INLGMCNASHSOOC-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CC=C7C)C8=CC=CC=C8)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CC=C7C)C8=CC=CC=C8)C INLGMCNASHSOOC-UHFFFAOYSA-N 0.000 description 1
- PDRASDPRGHXIDU-UHFFFAOYSA-N CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CS7)C8=CC=C(C=C8)OC)C Chemical compound CCN1C(=C(C2=CC=CC=C21)C3(C4=NC5=CC=CC=C5N=C4C(=O)O3)C6=C(N=C7N6C=CS7)C8=CC=C(C=C8)OC)C PDRASDPRGHXIDU-UHFFFAOYSA-N 0.000 description 1
- HYIPUCVRHSEMAF-UHFFFAOYSA-N CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C1(C(C=C2N(C3=C(N21)C=CC=C3)CC)C3=CC=CC=C3)C)C Chemical compound CN(C1=CC=C(C=C1)C1(OC(=O)C2=CC(=CC=C12)N(C)C)C1(C(C=C2N(C3=C(N21)C=CC=C3)CC)C3=CC=CC=C3)C)C HYIPUCVRHSEMAF-UHFFFAOYSA-N 0.000 description 1
- RVQYDIGMKJPLSD-UHFFFAOYSA-N COC1=C(C=CC(=C1)NC1CCCCC1)C1(OC(=O)C2=CC=CC=C12)C=1C(=C(N2C1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1 Chemical compound COC1=C(C=CC(=C1)NC1CCCCC1)C1(OC(=O)C2=CC=CC=C12)C=1C(=C(N2C1N(C1=C2C=CC=C1)CC)C)C1=CC=CC=C1 RVQYDIGMKJPLSD-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- LCYXYLLJXMAEMT-SAXRGWBVSA-N Pyridinoline Chemical compound OC(=O)[C@@H](N)CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O LCYXYLLJXMAEMT-SAXRGWBVSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002174 Styrene-butadiene Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 235000011132 calcium sulphate Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 150000001987 diarylethers Chemical class 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical group CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- YCZJVRCZIPDYHH-UHFFFAOYSA-N ditridecyl benzene-1,2-dicarboxylate Chemical compound CCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCCCCCCC YCZJVRCZIPDYHH-UHFFFAOYSA-N 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 125000005506 phthalide group Chemical group 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heat Sensitive Colour Forming Recording (AREA)
- Color Printing (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57212045A JPS58164642A (ja) | 1982-12-02 | 1982-12-02 | 発色性染料及びその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57212045A JPS58164642A (ja) | 1982-12-02 | 1982-12-02 | 発色性染料及びその製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58164642A JPS58164642A (ja) | 1983-09-29 |
| JPH0248028B2 true JPH0248028B2 (el) | 1990-10-23 |
Family
ID=16615953
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57212045A Granted JPS58164642A (ja) | 1982-12-02 | 1982-12-02 | 発色性染料及びその製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58164642A (el) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0373110B1 (de) * | 1988-12-02 | 1993-04-21 | Ciba-Geigy Ag | Druck- oder wärmeempfindliches Aufzeichnungsmaterial |
-
1982
- 1982-12-02 JP JP57212045A patent/JPS58164642A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58164642A (ja) | 1983-09-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3775424A (en) | Furo(3,4-b)pyridine-7(5h)-ones | |
| US4119776A (en) | Vinyl phthalide color formers | |
| CA1055943A (en) | Benzoindole phthalides | |
| US3916070A (en) | Pressure-sensitive copying paper containing lactone compound of pyridine carboxylic acid | |
| JPS6320868B2 (el) | ||
| US4275206A (en) | Lactone compounds containing an indolizine radical | |
| US4334072A (en) | Lactone compounds containing an indolizine radical | |
| JPH0248028B2 (el) | ||
| US4562449A (en) | Chromogenic dihydroquinazolines | |
| CA1307531C (en) | 3-(4-aminophenyl)-3-(1-substituted-3-indolyl) phthalides and their analogs, processes for their production and marking systems using the same | |
| US4506073A (en) | Chromenoazaindolizine compounds | |
| US4403791A (en) | Carbonless duplicating and marking systems | |
| US4232887A (en) | Lactone compounds containing an indolizine radical | |
| US4523018A (en) | Certain bis(benzoyl)pyridine compounds | |
| US4200751A (en) | Lactones of quinoline carboxylic acids | |
| US4211872A (en) | Substituted furopyridinones and furopyrazinones | |
| EP0430486B1 (en) | Divinyl carbinol or carbinol derivative chromogenic compounds and their use in record material | |
| US4732991A (en) | Substituted phthalides | |
| US4446321A (en) | 4-Aryl-bis 2,6-(aminophenyl)pyridines | |
| US4337340A (en) | Processes for preparing substituted furopyridinones and furopyrazinones | |
| US4736027A (en) | Indole-phthalide derivatives | |
| US4243250A (en) | Carbonless duplicating systems | |
| US4788285A (en) | Indole-phthalide derivatives | |
| US4558137A (en) | Bis phenyl (2 carboxylic acid or ester indol-3-yl)methanes | |
| IE49314B1 (en) | Substituted furopyridinones and furopyrazinones as color formers in pressure-sensitive and thermal imaging systems |