Chromene-2 derivatives and use thereof in the treatment of fibrosis

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 having the following formula: ##STR00010## wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, and hydroxypropyl; and X is a counter anion selected from the group consisting of perchlorate, hexafluorophosphate, and tetrafluoroborate.

2. The compound of claim 1, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, hydroxymethyl, and hydroxyethyl.

3. The compound of claim 1, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, and hydroxymethyl.

4. The compound of claim 1, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of methyl, ethyl, and propyl.

5. The compound of claim 1, wherein the counter anion X is perchlorate.

6. The compound of claim 1, which is selected from the group consisting of: ##STR00011##

7. A pharmaceutical composition comprising a compound having the following formula: ##STR00012## wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, and hydroxypropyl; and X is a counter anion selected from the group consisting of perchlorate, hexafluorophosphate, and tetrafluoroborate.

8. The pharmaceutical composition of claim 7, wherein the compound is selected from the group consisting of: ##STR00013##

9. The pharmaceutical composition of claim 7, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, hydroxymethyl, and hydroxyethyl.

10. The pharmaceutical composition of claim 7, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, and hydroxymethyl.

11. The pharmaceutical composition of claim 7, wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of methyl, ethyl, and propyl.

12. The pharmaceutical composition of claim 7, wherein the counter anion X is perchlorate.

13. A method for treating fibrosis comprising administering to a subject in need thereof a therapeutically effective amount of a compound having the following formula: ##STR00014## wherein each R.sub.1 and R.sub.2 are independently selected from the group consisting of H, methyl, ethyl, propyl, hydroxymethyl, hydroxyethyl, and hydroxypropyl; and X is a counter anion selected from the group consisting of perchlorate, hexafluorophosphate, and tetrafluoroborate.

14. The method of claim 13, wherein the fibrosis is lung fibrosis.

15. The method of claim 13, wherein the fibrosis is idiopathic pulmonary fibrosis (IPF).

16. The method of claim 13, wherein the fibrosis is liver fibrosis.

17. The method of claim 13, wherein the fibrosis is non-alcoholic steatohepatitis (NASH).

Description

DESCRIPTION OF THE DRAWINGS

(1) FIG. 1: Inhibitor effect of 6,7-dimethoxy 2H-chromen-one (1) on TGFbeta-induced collagen synthesis in L929 cells.

(2) FIG. 2: Inhibitor effect of 6,7-dimethoxy 2H-chromen-one (1) on proliferation of L929 cells.

(3) FIG. 3: Inhibitor effect of 6,7-dimethoxy 2H-chromen-one (1) on TGFbeta-induced secreted collagen synthesis in L929 cells

(4) FIG. 4: 6,7-dimethoxy-2H-chromen-2-one

(5) FIG. 5: Main compound produced from 6,7-dimethoxy-2H-chromen-2-one

(6) FIG. 6: Side chain added to the compound described at FIG. 5,

(7) FIG. 7: First structure produced from FIG. 5.

(8) FIG. 8: 6,7-dimethoxy-chromenylium perchlorate.

(9) FIG. 9: 6-ethoxy-7 methoxy 2,3,4,5,8-pentamethyl naphatehalen-1-ylium

(10) FIG. 10: 7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium.

(11) FIG. 11: 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium.

(12) FIG. 12: 6-hydroperoxy-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(13) FIG. 13: 7-hydroperoxy-6-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(14) FIG. 14: 6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(15) FIG. 15: 7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(16) FIG. 16: 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(17) FIG. 17: Second structure produced from FIG. 5.

(18) FIG. 18: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dimethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound

(19) FIG. 19: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound

(20) FIG. 20: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound

(21) FIG. 21: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound

(22) FIG. 22: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound

(23) FIG. 23: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-hydroperoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound

(24) FIG. 24: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dihydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound

(25) FIG. 25: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound

(26) FIG. 26: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound

(27) FIG. 27: 3th structure produced from FIG. 5.

(28) FIG. 28: 7-ethoxy-6methoxy-2,3,4,5,8-pentamethylnaphthalen-1-ylium

(29) FIG. 29: 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium

(30) FIG. 30: 6-methoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium

(31) FIG. 31: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium

(32) FIG. 32: 7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium

(33) FIG. 33: 7-(hydroxymethoxy)-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium

(34) FIG. 34: 6-hydroperoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl naphatehalen-1-ylium

(35) FIG. 35: 6-hydroperoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium

(36) FIG. 36: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(37) FIG. 37: 4th structure produced from FIG. 5.

(38) FIG. 38: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen and methyl-.sup.1-oxidane (4:1:1) formaldehyde compound

(39) FIG. 39: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(40) FIG. 40: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-7-propoxy-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(41) FIG. 41: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(42) FIG. 42: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(43) FIG. 43: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(44) FIG. 44: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(45) FIG. 45: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-3,4,5,8-tetramethyl-7-propoxy-1.sup.3-chromen and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(46) FIG. 46: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(47) FIG. 47: 5th structure produced from FIG. 5.

(48) FIG. 48: 6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(49) FIG. 49: 7-methoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium

(50) FIG. 50: 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(51) FIG. 51: 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium

(52) FIG. 52: 6-(hydroxymethoxy)-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(53) FIG. 53: 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(54) FIG. 54: 7-hydroperoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(55) FIG. 55: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(56) FIG. 56: 7-hydroperoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium

(57) FIG. 57: 6th structure produced from FIG. 5.

(58) FIG. 58: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(59) FIG. 59: 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(60) FIG. 60: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1 I-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(61) FIG. 61: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(62) FIG. 62: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(63) FIG. 63: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one- and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(64) FIG. 64: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(65) FIG. 65: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(66) FIG. 66: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(67) FIG. 67: 7th structure produced from FIG. 5.

(68) FIG. 68: 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(69) FIG. 69: 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium

(70) FIG. 70: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium

(71) FIG. 71: 2,3,4,5,8-pentamethyl-6,7-dipropoxynaphatehalen-1-ylium

(72) FIG. 72: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(73) FIG. 73: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-1-ylium

(74) FIG. 74: 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethynaphatehalen-1-ylium

(75) FIG. 75: 6-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen-1-ylium

(76) FIG. 76: 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-1-ylium

(77) FIG. 77: 8th structure produced from FIG. 5.

(78) FIG. 78: 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(79) FIG. 79: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(80) FIG. 80: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-1.sup.3-chromen-2-yl)butan-1-one-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(81) FIG. 81: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(3,4,5,8-tetramethyl-6,7-dipropoxy-1.sup.3-chromen-2-yl)butan-1-one-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(82) FIG. 82: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound

(83) FIG. 83: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydroxymethoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(84) FIG. 84: 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(85) FIG. 85: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-(3,4,5,8-tetramethyl-7-propoxy-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

(86) FIG. 86: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-(hydroxymethoxy)-(3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound.

EXPLANATION OF REFERENCES OF FIGURES

(87) 1: 6,7-dimethoxy-2H-chromen-2-one 2: Main compound produced from 6,7-dimethoxy-2H-chromen-2-one 3: Side chain added to the compound described at FIG. 5 4: First structure produced from FIG. 5. 4.1: 6,7-dimethoxy-chromenylium perchlorate 4.2: 6-ethoxy-7 methoxy 2,3,4,5,8-pentamethyl naphatehalen-1-ylium 4.3: 7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium 4.4: 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-1-ylium 4.5: 6-hydroperoxy-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium 4.6: 7-hydroperoxy-6-methoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium 4.7: 6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium 4.8: 7-ethoxy-6-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium 4.9: 6-ethoxy-7-hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-1-ylium 5: Second structure produced from FIG. 5. 5.1: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dimethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound 5.2: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound 5.3: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound 5.4: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-(1:1) formaldehyde compound 5.5: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydroperoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound 5.6: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-hydroperoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound 5.7: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dihydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound 5.8: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound 5.9: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen (1:1) formaldehyde compound
6: 3th structure produced from FIG. 5.
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 FIG. 5
7.1: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen and methyl-.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.sup.3-chromen and methyl-.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-1.sup.3-chromen and methyl-.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-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound 7.5: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydroperoxy-3,4,5,8-tetramethyl-1.sup.3-chromen and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound 7.6: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.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-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.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-1.sup.3-chromen and methyl .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-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound 8: 5th structure produced from FIG. 5. 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 FIG. 5. 9.1: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound 9.2: 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.sup.3-chromen-2-yl)butan-1-one- and methyl-.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-1.sup.3-chromen-2-yl)butan-1-one and methyl-.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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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-1.sup.3-chromen-2-yl)butan-1-one and methyl .sup.1-oxidane (3:1:1) formaldehyde compound 10: 7th structure produced from FIG. 5. 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 FIG. 5 11.1: 3-(6,7-diethoxy-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.sup.1-oxidane (3:1:1) formaldehyde compound 11.2: 1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound 11.7: 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and-methyl-.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-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.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-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.sup.1-oxidane (3:1:1) formaldehyde compound

DESCRIPTION OF THE INVENTION

(88) 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 g/ml ascorbic acid and 20 M 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 TGF2 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, FIG. 2. The second 96-well plate was used to determine the level of total collagen. To determine the level of total collagen medium was removed and cells were fixed to bottom of the plated by adding % 0.5 gluteraldehyde prepared in 1PBS for 30 minutes, then gluteraldehyde was removed, cells were washed with water and incubated with 100 microliter of 0.5 molar acetic acid for 30 minutes. At the end of 30 min, acetic acid was removed, cells were washed with water, air dried and 100 microliter sircol dye solution was added and further incubated for two hours at room temperature. Then, sircol dye solution was removed, plates was washed with water, air dried and 300 microliter of alkaline solution was added and shaken for 3 hours at room temperature to extract collagen-bound sircol. Absorbance of developed color was determined at 600 nm. As shown at FIG. 1, TGF induced collagen level by % 20 compared to control cells, however, in the presence of CP1 TGF induced collagen level by % 10, in other words CP1 inhibited TGF-induced collagen synthesis by % 50. In addition to total collagen, we also determined the level of secreted collagen by using ELISA. Briefly, supernatant (200 microliter) of cultured cells were transferred into high affinity binding ELISA plates and incubated this at 4 C. for 16 hours, then supernatant was removed, plate was washed with PBST (% 0.1 Tween-20 in 1PBS) and blocked with % 1 BSA prepared in PBST for 2 hours, plate was washed with PBST and anti-collagen type I antibody (1:2000 dilution) prepared in % 1 BSA was added and incubated for 1 hour at room temperature, this antibody was removed, plate was washed with PBST and relevant secondary antibody prepared in % 1 BSA was added at 1:2000 dilution and incubated at room temperature for 1 hour, then secondary antibody was removed, plate was washed with PBST and ELISA was performed. As shown at FIG. 3, present compound (CP1) significantly inhibits TGF-induced secreted collagen level. These results strongly indicate that the compounds derived from CP1 may offer alternative treatment options to treat fibrosis patients.

(89) 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

(90) ##STR00009##

(91) 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.

(92) 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.

(93) Eight different structure and their derivatives are explained below;

(94) In the first compound (4), produced from main compound (2): when R1 and R2 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.

(95) 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.

(96) 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.

(97) 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.

(98) 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.

(99) 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.

(100) 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.

(101) 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

(102) 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

(103) 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-1.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.

(104) 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-1.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.

(105) 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-1.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.

(106) 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-1.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.

(107) 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-1.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.

(108) 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.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.

(109) 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-1.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.

(110) 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-1.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.

(111) 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-1.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.

(112) 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.

(113) 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.

(114) 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.

(115) 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.

(116) 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

(117) 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.

(118) 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.

(119) 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.

(120) In the third compound (6), produced from main compound (2); when R1 is ethyl (C2H5) and R2 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.

(121) 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-1.sup.3-chromen and methyl-.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.

(122) 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-1.sup.3-chromen and methyl-.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.

(123) 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-1.sup.3-chromen and methyl-.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.

(124) 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-1.sup.3-chromen and methyl-.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.

(125) 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-1.sup.3-chromen and methyl-.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.

(126) 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-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.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.

(127) 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-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.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.

(128) 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.sup.3-chromen and methyl-.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.

(129) 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-1.sup.3-chromen-7-yl)oxy)methanol and methyl-.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.

(130) 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.

(131) 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.

(132) 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.

(133) 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.

(134) 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.

(135) 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.

(136) 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.

(137) 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.

(138) 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.

(139) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(140) 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-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.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.

(141) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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 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.

(142) 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 (1-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(143) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(144) 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-1.sup.3-chromen-2-yl)butan-1-one- and methyl-.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.

(145) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl-.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.

(146) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(147) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(148) 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.

(149) 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.

(150) 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.

(151) 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.

(152) 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.

(153) 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.

(154) 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.

(155) 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.

(156) 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.

(157) 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-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one- and methyl-.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.

(158) 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-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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.

(159) 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-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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.

(160) 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-1.sup.3-chromen-2-yl)butan-1-one-methyl-.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.

(161) 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-1.sup.3-chromen-2-yl)butan-1-one and methyl .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.

(162) 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-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.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.

(163) 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-1.sup.3-chromen-2-yl)-1-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1-one-and-methyl-.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.

(164) 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-1.sup.3-chromen-2-yl)butan-1-one-and-methyl-.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.

(165) 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-1.sup.3-chromen-2-yl) butan-1-one-and-methyl-.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.