CHROMENE-2 DERIVATIVES AND USE THEREOF IN THE TREATMENT OF FIBROSIS
20170313673 · 2017-11-02
Inventors
Cpc classification
C07C409/02
CHEMISTRY; METALLURGY
C07C49/84
CHEMISTRY; METALLURGY
C07D311/04
CHEMISTRY; METALLURGY
International classification
C07D311/04
CHEMISTRY; METALLURGY
C07C43/20
CHEMISTRY; METALLURGY
Abstract
Disclosed are chromene-2 derivatives and the use thereof in the treatment of fibrosis. Specifically, disclosed are the derivatives of a compound having a main structure of 6,7-dimethoxy-chromenylium perchlorate (1) and pharmaceutical compositions, combinations and pharmaceutically suitable salts thereof for the treatment of fibrosis.
Claims
1. A compound containing Chromene derivatives of Formula (1); 6,7-dimethoxy-chromenylium perchlorate (1), its derivatives and pharmaceutical compositions containing these compounds wherein the structure is generated by removing carbonyl oxygen from Chromene structure to create a positive charge on Chromene ring thereby obtaining a new structure by alternating methyl (—CH3), ethyl (—C2H5) and hydroxyl (—OH) at position of R1 and R2 to generate 8 different molecules having the following formula: ##STR00010##
2. The compound as claimed in claim 1 wherein the compound is a “pyrylium salt” and is present in the reaction as a “perchlorate salt”.
3. The compound as claimed in claim 2 wherein said salt is substituted with PF6(Hexafluorophosphate—Lewis structure) or with BF4—(Tetrafluoroborate-Lewis structure).
4. The compound as claimed in claim 1 wherein main structure has the formula of ##STR00011## and when the compound is 6,7-dimethoxy-chromenylium perchlorate (4.1); R3, R4, R5, R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
5. The compound as claimed in claim 4 wherein when the compound is 6-ethoxy-7 methoxy 2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.2); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
6. The compound as claimed in claim 4 wherein when the compound is 7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.3) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
7. The compound as claimed in claim 4 wherein when the compound is 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.4); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
8. The compound as claimed in claim 4 wherein when the compound is 6-hydroperoxy-7-methoxy-2,3,4,5,8pentamethylnaphatehalen-1-ylium, (4.5); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
9. The compound as claimed in claim 4 wherein when the compound is 7-hydroperoxy-6-methoxy-2,3,4,5,8pentamethylnaphatehalen-1-ylium (4.6); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
10. The compound as claimed in claim 4 wherein when the compound is 6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (4.7) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
11. The compound as claimed in claim 4 wherein when the compound is 7-ethoxy-6˜hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (4.8) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
12. The compound as claimed in claim 4 wherein when the compound is 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.9); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
13. The compound as claimed in claim 1 wherein when the main structure is as shown in Figure (5.1) ##STR00012## And when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dimethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound(5.1); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
14. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-methoxy-3,4,5,8-tetra methyl-1λ.sup.3-chromen-(1:1) formaldehyde compound (5.2), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
15. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetra methyl-1λ.sup.3-chromen-(1:1) formaldehyde compound (5.3), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
16. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound (5.4), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
17. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1 formaldehyde compound (5.5), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
18. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-1Timethylphenyl)butan-2-yl)-7-hydroperoxy-6-methoxy-3,4,5, 8-tetramethyl-1λ<3>-chromen (1: 1) formaldehyde compound (5.6), R3, R4, R5, R6, R7, R8, R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
19. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dihydroperoxy-3,4,5,8-tetramethyl-1λ3-chromen (1:1) formaldehyde compound (5.7), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
20. The compound as claimed in claim 13 wherein the compound 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound (5.8); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
21. The compound as claimed in claim 13 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound (5.9); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
22. The compound as claimed in claim 1 wherein main structure is as shown in Figure (6.1) ##STR00013## and when the molecule is 7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.1); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
23. The compound as claimed in claim 22 wherein when the compound is 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.2); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
24. The compound as claimed in claim 22 wherein when the compound is 6-methoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (6.3); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
25. The compound as claimed in claim 22 wherein when the compound is 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (6.4); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
26. The compound as claimed in claim 22 wherein when the compound is 7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.5); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
27. The compound as claimed in claim 22 wherein when the compound is 7-(hydroxymethoxy)-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.6); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
28. The compound as claimed in claim 22 wherein when the compound is 6-hydroperoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.7); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
29. The compound as claimed in claim 22 wherein when the compound is 6-hydroperoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium(6.8); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
30. The compound as claimed in claim 22 wherein when the compound is 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (6.9); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
31. The compound as claimed in claim wherein main structure is as shown in Figure (7.1) ##STR00014## and when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetra methyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (4:1:1) formaldehyde compound(7.1); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
32. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.2); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
33. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.3); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
34. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.4); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
35. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.5); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
36. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.6); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
37. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.7); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
38. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.8); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
39. The compound as claimed in claim 31 wherein when the compound is 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(7.9); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
40. The compound a claimed in claim 1 wherein main structure is as shown in Figure (8.1) ##STR00015## and when the compound is 6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.1); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
41. The compound as claimed in claim 40 wherein when the compound is 7-methoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.2); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
42. The compound as claimed in claim 40 wherein when the compound is 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.3) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
43. The compound as claimed in claim 40 wherein when the compound is 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.4) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
44. The compound as claimed in claim 40 wherein when the compound is 6-(hydroxymethoxy)-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.5); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
45. The compound as claimed in claim 40 wherein when the compound is 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.6) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
46. The compound as claimed in claim 40 wherein when the compound is 7-hydroperoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-l-ylium (8.7); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
47. The compound as claimed in claim 40 wherein when the compound is 7-ethoxy-6-(-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.8); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
48. The compound as claimed in claim 40 wherein when the compound is 7-hydroperoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.9); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
49. The compound as claimed in claim 1 wherein main structure is as shown in Figure (9) ##STR00016## and when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.1); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
50. The compound as claimed in claim 49 wherein when the compound is 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.2); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
51. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8-tetramethyl-6-propoxy-1 λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.3); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
52. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.4); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
53. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-7-methoxy-3,4,5,8-tetra methyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.5); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
54. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.6); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
55. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.7); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
56. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.8); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
57. The compound as claimed in claim 49 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.9); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
58. The compound as claimed in claim 1 wherein main structure is as shown in Figure (10) ##STR00017## when the compound is 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.1); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.0 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
59. The compound as claimed in claim 58 wherein when the compound is 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (102) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
60. The compound as claimed in claim 58 wherein when the compound is 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (10.3) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
61. The compound as claimed in claim 58 wherein when the compound is 2,3,4,5,8-pentamethyl 6,7-dipropoxynaphatehalen-1-ylium (10.4); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
62. The compound as claimed in claim 58 wherein when the compound is 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.5); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
63. The compound as claimed in claim 58 wherein when the compound is 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.6); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
64. The compound as claimed in claim 58 wherein when the compound is 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.7); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
65. The compound as claimed in claim 58 wherein when the compound is 6-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (10.8); R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
66. The compound as claimed in claim 58 wherein when the compound is 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6,7-propoxynaphatehalen-1-ylium(10.9) R3,R4,R5,R6 and R7 can be hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
67. The compound as claimed in claim 1 wherein the main structure shown in Figure (11), ##STR00018## and when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound(11.1); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
68. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound(11.2); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
69. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound(11.3); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
70. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(3,4,5,8-tetramethyl-6,7-dipropoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(11.4); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
71. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound (11.5); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
72. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydroxymethoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.6), R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
73. The compound as claimed in claim 67 wherein when the compound is 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-1 λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6 trimethylphenyl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.7); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.1-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
74. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-(3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.8); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
75. The compound as claimed in claim 67 wherein when the compound is 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-(hydroxymethoxy)-(3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-1)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.9); R3,R4,R5,R6 R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxside, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
76. The use of the compound as described in claim 1 in the treatment of fibrosis diseases wherein the fibrosis is idiopathic pulmonary fibrosis, chronic obstructive pulmonary disease (COPD), sarcoidosis, kidney fibrosis, heart fibrosis, atherosclerosis, liver fibrosis, pancreas fibrosis, pancreatitis, liver cirrhosis, non-alcoholic steatohepatitis (NASH) and alcohol-dependent steatohepatitis.
Description
DESCRIPTION OF THE DRAWINGS
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EXPLANATION OF REFERENCES OF FIGURES
[0099] 1: 6,7-dimethoxy-2H-chromen-2-one [0100] 2: Main compound produced from 6,7-dimethoxy-2H-chromen-2-one [0101] 3: Side chain added to the compound described at
6: 3th structure produced from
6.1: 7-ethoxy-6methoxy-2,3,4,5,8-pentamethylnaphthalen-1-ylium
6.2: 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium
6.3: 6-methoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium
6.4: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium
6.5: 7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium
6.6: 7-(hydroxymethoxy)-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium
6.7: 6-hydroperoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl naphatehalen-1-ylium
6.8: 6-hydroperoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium
6.9: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
7: 4th structure produced from
7.1: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (4:1:1) formaldehyde compound
7.2: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
7.3: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
7.4: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound [0121] 7.5: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound [0122] 7.6: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
7.7: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
7.8: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
7.9: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
8: 5th structure produced from
8.1: 6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.2: 7-methoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium
8.3: 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.4: 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium
8.5: 6-(hydroxymethoxy)-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.6: 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.7: 7-hydroperoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.8: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
8.9: 7-hydroperoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium
9: 6th structure produced from
9.1: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.2: 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.3: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.4: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.5: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.6: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen-2-yl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.7: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.8: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
9.9: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
10: 7th structure produced from
10.1: 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
10.2: 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium
10.3: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium
10.4: 2,3,4,5,8-pentamethyl-6,7-dipropoxynaphatehalen-1-ylium
10.3: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
10.6: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
10.7: 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium
10.8: 6-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium
10.9: 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium
11: 8th structure produced from
11.2: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.3: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.4: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(0,3,4,5,8-tetramethyl-6,7-dipropoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.5: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound
11.6: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydroxymethoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.7: 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.8: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-(3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
11.9: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-(hydroxymethoxy)-(3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound
DESCRIPTION OF THE INVENTION
[0123] The present invention is about novel compounds which may offer alternative treatment options against IPF, which believed to develop as a consequences of smoking, pollution, allergens, toxins and seen in people who are older than 50 years old. The compounds mentioned in this application have been generated from “6,7-dimethoxy 2H-chromen-one (1), which was identified from local medicinal plants during our screening studies. The anti-fibrotic activity of this compound (“6,7-dimethoxy 2H-chromen-one (I) against TGF beta-induced collagen synthesis using 1.929 cells has been identified. For this, in 96-well plates, 1.929 cells were cultured in DMEM supplemented with % 10 serum, 10 μg/ml ascorbic acid and 20 μM prolin until they reached to confluency. Confluent cells were treated with 50 micromole of our compound (named as CP1) dissolved in DMSO for 1 hour, then 5 ng/ml of Mouse TGFβ2 was added and cells were further incubated for 72 hours at incubator supplied with 5% CO.sub.2 and 80% humidity. At the end of this incubation one of the plate was used to determine cell viability by using MTT test,
[0124] Structure of the above mentioned (CP1) compound is 6,7-dimethoxy 2H-chromen-2-one (1) and its chemical Formula is C.sub.11H.sub.10O.sub.4
##STR00009##
[0125] With this application, carbonyl oxygen is removed from Chromene structure, this yielded positively charged chromene ring, then from this structure, 8 different molecules (4,5,6,7,8,9,10,11) and their 9 different combinations were generated.
[0126] R1 and R2 positions of these 8 compound were chosen as site of modifications, and methyl(—CH3), ethyl(—C2H5), hydroxyl (—OH), and their combinations with one another were chosen to represent R and R2.
[0127] Eight different structure and their derivatives are explained below;
[0128] In the first compound (4), produced from main compound (2): when R1 and R2 are are methyl (—CH3), and in this compound (6,7-dimethoxy-chromenylium perchlorate(4.1) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0129] In the first compound (4), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is methyl(—CH3), and in this compound (6-ethoxy-7 methoxy 2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.2); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0130] In the first compound (4), produced from main compound (2); when R1 is methyl (—CH3) and R2 is ethyl(—C2H5), and in this compound (7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (4.3) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0131] In the first compound (4), produced from main compound (2); when R1 and R2 are ethyl(—C2H5), and in this compound (6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium) (4.4); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.1-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0132] In the first compound (4), produced from main compound (2): when R1 is hydroxyl (—OH) and R2 is methyl (—CH3), and in this compound (6-hydroperoxy-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium) (4.5); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0133] In the first compound (4), produced from main compound (2); when R1 is methyl (—CH3) and R2 is hydroxyl (—OH), and in this compound (7-hydroperoxy-6-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium) (4.6); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0134] In the first compound (4), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), and in this compound (6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium) (4.7); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0135] In the first compound (4), produced from main compound (2); when R1 is hydroxyl (—OH) and R2 is ethyl (—C2H5, and in this compound (7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium) (4.8); R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another in the first compound (4), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is hydroxyl (—OH), and in this compound (6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium) (4.9) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another
[0136] In the second compound (5), produced from main compound (2); when R1, R2, R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dimethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound (5.1) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0137] In the second compound (5), produced from main compound (2); when R1 is ethyl (—C2H5) R2 is methyl (—CH3), R11 and R12 are methyl (—CH3 and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound) (5.2) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0138] In the second compound (5), produced from main compound (2); when R1 is methyl (—CH3), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3) and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound) (5.2) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0139] In the second compound (5), produced from main compound (2); when R1 and R2 are ethyl (—C2H5), R11 and R12 are methyl (—CH3) and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-(1:1) formaldehyde compound) (5.4) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0140] In the second compound (5), produced from main compound (2); when R1 is hydroxyl(—OH) R2 is methyl (—CH3), R11 methyl (—CH3), R12 methyl (—CH3) and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound) (5.5) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0141] In the second compound (5), produced from main compound (2): when R1, methyl (—CH3) R2 hydroxyl (—OH), R11 methyl (—CH3), R12 methyl (—CH3) and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-7-methoxy-3,4,5,8-tetramethyl-1 λ.sup.3-chromen (1:1) formaldehyde compound) (5.6) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.1-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0142] In the second compound (5), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), R11 methyl (—CH3), R12 methyl (—CH3) and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dihydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound) (5.7) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0143] In the second compound (5), produced from main compound (2); when R1 is hydroxyl(—OH) and R2 is ethyl (—C2H5), R11 methyl (—CH3), R12 methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound) (5.8) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0144] In the second compound (5), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is hydroxyl (—OH), R11 methyl (—CH3), R12 methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen (1:1) formaldehyde compound) (5.9) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.1-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0145] In the third compound (6), produced from main compound (2); when R1 and R2 are methyl (—CH3), and in this compound (7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.1) R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0146] In the third compound (6), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is methyl (—CH3), and in this compound (6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.2) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0147] In the third compound (6), produced from main compound (2); when R1 is methyl (—CH3) and R2 is ethyl (—C2H5), and in this compound (6-methoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (6.3) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0148] In the third compound (6), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is ethyl (—C2H5), and in this compound (6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (6.4) R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0149] In the third compound (6), produced from main compound (2); when R1 is hydroxyl(—OH) and R2 is methyl (—CH3), and in this compound (7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.5) R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another
[0150] In the third compound (6), produced from main compound (2); when R1 is methyl (—CH3) and R2 is hydroxyl (—OH), and in this compound (7-(hydroxymethoxy)-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.6); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0151] In the third compound (6), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), and in this compound (6-hydroperoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl naphatehalen-1-ylium (6.7); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0152] In the third compound (6), produced from main compound (2); when R1 is hydroxyl (—OH) and R2 is ethyl (—C2H5), and in this compound (6-hydroperoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium(6.8) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0153] In the third compound (6), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is is hydroxyl (—OH), and in this compound (6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (6.9); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0154] In the fourth compound (7), produced from main compound (2); when R1,R2,R1 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (4:1:1) formaldehyde compound) (7.1); R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0155] In the fourth compound (7), produced from main compound (2); when R1 is ethyl(—C2H5), R2 is methyl (—CH3), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.2) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0156] In the fourth compound (7), produced from main compound (2); when R1 is methyl(—CH3), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.3) R3,R4,R5,R6, R7,R8,R9 and R10 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0157] In the fourth compound (7), produced from main compound (2); when R1 and R2 are ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.4) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0158] In the fourth compound (7), produced from main compound (2); when R1 is hydroxyl(—OH), R2 is methyl (—CH3), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.5) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0159] In the fourth compound (7), produced from main compound (2); when R1 is methyl (—CH3), R2 is hydroxyl (—OH), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.6) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0160] In the fourth compound (7), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1)) formaldehyde compound) (7.7) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.1-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0161] In the fourth compound (7), produced from main compound (2); when R1 is hydroxyl(—OH), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-7-propoxy-1 λ.sup.3-chromen and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.8) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0162] In the fourth compound (7), produced from main compound (2); when R1 is ethyl(—C2H5), R2 is hydroxyl (—OH), R11 and R12 are methyl (—CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-7-yl)oxy)methanol and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound) (7.9) R3,R4,R5,R6, R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0163] In the fifth compound (8), produced from main compound (2); when R1 and R2 are methyl and in this compound (6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.1); R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0164] In the fifth compound (8), produced from main compound (2); when R1 is ethyl(—C2H5) and R2 is methyl(—CH3), and in this compound (7-methoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.2); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0165] In the fifth compound (8), produced from main compound (2); when R1 is methyl(—CH3) and R2 is ethyl(—C2H5), and in this compound (6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.3) R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0166] In the fifth compound (8), produced from main compound (2); when R1 and R2 are ethyl (—C2H5), and in this compound (7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.4); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0167] In the fifth compound (8), produced from main compound (2); when R1 is hydroxyl (—OH), and R2 is methyl (—CH3) and in this compound (6-(hydroxymethoxy)-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.5); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0168] In the fifth compound (8), produced from main compound (2); when R1 is methyl (—CH3), and R2 is hydroxyl (—OH), and in this compound (6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.6), R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0169] In the fifth compound (8), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), and in this compound (7-hydroperoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.7), R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0170] In the fifth compound (8), produced from main compound (2); when R1 is hydroxyl (—OH), and R2 is ethyl (—C2H5), and in this compound (7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (8.8): R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0171] In the fifth compound (8), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is hydroxyl (—OH), and in this compound (7-hydroperoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (8.9); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0172] In the sixth compound (9), produced from main compound (2); when R1,R2,R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.1); R3,R4,R5,R6,R7,R8,R9 and R10 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0173] In the sixth compound (9), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is methyl (—CH3), R11 and R12 are methyl (—CH3), and in this compound (3-(6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.2); R3, R4, R5, R6, R7, R8, R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0174] In the sixth compound (9), produced from main compound (2); when R1 is methyl (—CH3), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(93); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0175] In the sixth compound (9), produced from main compound (2); when R1 and R2 are ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (I-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.4); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0176] In the sixth compound (9), produced from main compound (2); when R1 is hydroxyl (—OH), R2 is methyl (—CH3), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-7-methoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.5); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0177] In the sixth compound (9), produced from main compound (2); when R1 is methyl (—CH3), R2 is hydroxyl(—OH), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound(9.6); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0178] In the sixth compound (9), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound (9.7); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0179] In the sixth compound (9), produced from main compound (2); when R1 is hydroxyl (—OH), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound (9.8); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0180] In the sixth compound (9), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is hydroxyl (—OH), R11 and R12 are methyl (—CH3), and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound (9.9); R3,R4,R5,R6,R7,R5,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0181] In the seventh compound (10), produced from main compound (2); when R1 and R2 are methyl (—CH3), and in this compound (6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium(10.1); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0182] In the seventh compound (10), produced from main compound (2): when R1 is ethyl (—C2H5) and R2 is methyl (—CH3), and in this compound 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium (10.2); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0183] In the seventh compound (10), produced from main compound (2); when R1 is methyl (—CH3) and R2 is ethyl (—C2H5), and in this compound 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (10.3); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0184] In the seventh compound (10), produced from main compound (2); when R1 and R2 are ethyl (—C2H5), and in this compound 2,3,4,5,8-pentamethyl-6,7-dipropoxynaphatehalen-1-ylium (10.4); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H1-15), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0185] In the seventh compound (10), produced from main compound (2); when R1 is hydroxyl (—OH) and R2 is methyl (—CH3), and in this compound 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.5); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—CL), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0186] In the seventh compound (10), produced from main compound (2); when R1 is methyl (—CH3) and R2 is hydroxyl (—OH), and in this compound 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.6); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0187] In the seventh compound (10), produced from main compound (2): when R1 and R2 are hydroxyl (—OH), and in this compound 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium (10.7) R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0188] In the seventh compound (10), produced from main compound (2): when R1 is hydroxyl(—OH) and R2 is ethyl (—C2H5), and in this compound 6-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium (10.8); R3,R4,R5,R6 and R7 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0189] In the seventh compound (10), produced from main compound (2); when R1 is ethyl (—C2H5) and R2 is hydroxyl(—OH), and in this compound 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6,7-propoxynaphatehalen-1-ylium (10.9); R3,R4,R5,R6 and R7 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0190] In the eight compound (11), produced from main compound (2); when R1,R2,R11 and R12 are methyl (—CH3), and in this compound (3-(6,7-diethoxy-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound (11.1); R3,R4,R5,R6,R7,R8,R9 and R10 can be: hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6alkenyl, carboxyl (—COOH) and their combinations with one another.
[0191] In the eight compound (11), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is methyl (—CH3) R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.2); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0192] In the eight compound (11), produced from main compound (2): when R1 is methyl (—CH3), R2 is ethyl (—C2H5), R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane (3:1:1) formaldehyde compound (11.3); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0193] In the eight compound (11), produced from main compound (2); when R land R2 are ethyl (—C2H5), R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(0,3,4,5,8-tetramethyl-6,7-dipropoxy-1λ.sup.3-chromen-2-yl)butan-1-one-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.4); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0194] In the eight compound (11), produced from main compound (2); when R1 is hydroxyl (—OH), R2 is methyl (—CH3), R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one and methyl λ.sup.1-oxidane (3:1:1) formaldehyde compound (11.5); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0195] In the eight compound (11), produced from main compound (2); when R1 is methyl (—CH3), R2 is hydroxyl (—OH), R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydroxymethoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.6); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0196] In the eight compound (11), produced from main compound (2); when R1 and R2 are hydroxyl (—OH), R11 and R12 are methyl (—CH3) and in this compound (3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-1λ.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.7); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0197] In the eight compound (11), produced from main compound (2); when R1 is hydroxyl (—OH), R2 is ethyl (—C2H5), R1 and R12 are methyl (—CH3) and in this compound 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-(3,4,5,8-tetramethyl-7-propoxy-1λ.sup.3-chromen-2-yl)butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.8); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.
[0198] In the eight compound (11), produced from main compound (2); when R1 is ethyl (—C2H5), R2 is hydroxyl (—OH), R11 and R12 are methyl (—CH3) and in this compound (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-(hydroxymethoxy)-(3,4,5,8-tetramethyl-6-propoxy-1λ.sup.3-chromen-2-yl) butan-1-one-and-methyl-λ.sup.1-oxidane(3:1:1) formaldehyde compound (11.9); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (—H), hydroxyl, (—OH), fluoride (—F), chloride, (—CL), bromide (—Br), iodine (—I), methyl (—CH3), ethyl (—C2H5), amino (—NH2), nitro (—NO2), C.sub.3-C.sub.6 cycloalkenyl, C.sub.1-C.sub.6 alkoxide, C.sub.1-C.sub.6 alkyl, C.sub.1-C.sub.6 fluoroalkyl, C.sub.2-C.sub.6 alkenyl, carboxyl (—COOH) and their combinations with one another.