CHROMENE-2 DERIVATIVES AND USE THEREOF IN THE TREATMENT OF

FIBROSIS

FIELD OF THE INVENTION

The present invention is related to chromene-2 derivatives and use thereof in the treatment of fibrosis. The invention is related to 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.

The Rl and R2 positions are selected as main replacement positions and these points are combined with hydroxyl (-OH), methyl (-CH3), ethyl (-C2H5) and combinations thereof.

The compounds of this invention have the ability to affect the TGI signal transduction pathways for synthesis of collagen, elastin, fibronectin, COMP ( Cartilage Oligomeric Protein), Osteopontin etc , and inhibit epithelial mesenchimal cell transition. Thus, said compounds can be effectively used in the treatment of idiopathic pulmonary fibrosis-IPF, Chronic Obstmctive Pulmonary Disease(COPD) , sarcoidosis, kidney fibrosis, heart fibrosis, atherosclerosis, pancreatic fibrosis , pancreatitis, liver fibrosis and cirrhosis , non-alcoholic steatohepatitis- NASH) and alcoholic siteatohepatitis

Lung fibrosis is a disease with an unknown etiology. Although multiple factors have been blamed for development of IPF actual cause for development of IPF is unknown. . Since its cause is unknown it is named as idiopathic lung fibrosis. IPF is commonly accepted as a disease of elderly, and its prevalence is 20/100.000 for men and 13/100.000 for women. Currently, it is estimated that 5 million people are affected from this disease worldwide (Eric B Meitzer and Paul W Noble Idiopathic pulmonary fibrosis. Orphanet Journal of Rare Diseases 2008, 3:8: 1- 15). It is commonly accepted that growth factors and cytokine, which are secreted by macrophages accumulate in the lung as a response to inflammation, play significant role in development of IPF(Todd NW, Scheraga RG, Ga!vin JR, lacono AT, Britt EJ, Luzina 10, et al. Lymphocyte aggregates persist and accumulate in the lungs of patients with idiopathic pulmonary fibrosis. J Inflamm Res 2013: 6: 63-70.) Cytokines IL4, IL13 and TGI secreted by macrophages initiates EMT process and during which alveolar epithelia cells turn mesenchima fibroblasts, (Kim KK. Kugler MC Wolters PJ, Robillard L, Galvez MG, Brumwell AN, et al. Alveolar epithelial cell mesenchymal transition develops in vivo during pulmonary fibrosis and is regulated by the extracellular matrix. Proc Natl Acad Sci U S A 2006; 103 : 13180-131 8. onigshoff M. Lung cancer in pulmonary fibrosis: tales of epithelial cell plasticity. Respiration 201 1 ; 81 : 353-358). Among the secreted cytokines TGFb induces expression and deposition of collagen from alveolar epithelial cells. (Broekelmann TJ, Limper AH, Colby TV, McDonald JA. Transforming growth factor beta 1 is present at sites of extracellular matrix gene expression in human pulmonary fibrosis. Proc Nail Acad Sci USA 1991 ;88:6642- 646. Khalil N, O'Connor RN, Flanders KC, Unruh H. TGF-bl , but not TGF- b2 or TGF-b3, is differentially present in epithelial cells of advanced pulmonary fibrosis: an immunohistochemical study. Am J Respir Cell Mol Biol 1996; 14: 131-138). Structural proteins deposited at extracellular matrix reduces the size of alveolar space, limits diffusion of oxygen and make breathing impossible. (Zhang K, Rekhter MD, Gordon D, Phan SH. Myofibroblasts and their role in lung collagen gene expression during pulmonary fibrosis: a combined immunohistochemical and in situ hybridization study. Am J Pathol 1994; 145: 1 14-125. Turner- Warwick M, Burrows B, Johnson A: Cryptogenic fibrosing alveolitis: clinical features and their influence on survival. Thorax 1980, 35(3): 171 - 180. Agusti AG, Roca J, Gea J, Wagner PD, Xaubet A, Rodriguez-Roisin R: Mechanisms of gas-exchange impairment in idiopathic pulmonary fibrosis. Am Rev Respir Dis 1991 , 143(2):21 -225). Uncontrolled growth of lung cells and deposition of matrix proteins perturbs the structure of lung which can be visulized by computerised tomography (CT). According to the results obtained from CT scans, one of the hallmark of lung fibrosis is the formation of "honey comb" structures, and this is "gold standard" in defining this disease. (Parambil JG, Myers JL, Ryu JH: Histopathologic features and outcome of patients with acute exacerbation of idiopathic pulmonary fibrosis undergoing surgical lung biopsy. Chest 2005, 128(5):3310-3315. Akira M, Hamada H, Sakatani M, Kobavashi C, Nishioka M, Yamamoto S: CT findings during phase of accelerated deterioration in patients with idiopathic pulmonary fibrosis. AJR Am J Roentgenol 1997, 168(l ):79-83).

Since lung fibrosis was initialy thought to develop as a result of inflamation it was treated with anti-inflammator compounds such as prednisol, n-acetyl cystein, cyclophosphamide, and Cortisol. However, none of these treatment options produced significant survival benefit for IPF patients. (Collard HR, Ryu JH, Douglas WW, Schwarz Ml, Curran-Everett D, King TE Jr., Brown KK: Combined corticosteroid and cyclophosphamide therapy does not alter survival in idiopathic pulmonary fibrosis. Chest 2004, 125(6):2169-2174. Behr J, Maier K, Degenkolb B, Krombach F, Vogelmeier C: Antioxidative and clinical effects of high-dose N-acel lc steine in fibrosing alveolitis. Adjunctive therapy to maintenance immunosuppression. Am J Respir Crit Care Med 1997, 156(6): 1 897-1901. Zisman DA, Lynch JP 3rd, Toews GB, Kazerooni EA, Flint A, Martinez FJ: Cyclophosphamide in the treatment of idiopathic pulmonary fibrosis: a prospective study in patients who failed to respond to corticosteroids. Chest 2000, 1 17(6): 1619- 1626). Athe begining of 2000, small molecule named "Pirfenidone" was tested against IPF in USA and Japan. In 2008, a japanese company Shinogi completed a succesful phase III study and got approval fort he use Pirfenidone to treat IPF patients in Japan. (Azuma A, Nukiwa T, Tsuboi E, et al. Double-blind, placebo-controlled, trial of pirfenidone in patients with idiopathic pulmonary fibrosis. Am J Respir Crit Care Med 2005; 171 : 1040-1047). In addition to this, US company called InterMune conducted 3 independent phase 3 studies and showed the efficacy of this compound against IPF and got FDA approval in October of 2014, and began marketing Pirfenidone under the brand name Esbriest. Also, in October 2014, another novel drug " intedanib" produced by Boehringer Ingelheim (BI) got approval for IPF (Jason Potts, Dinesh Yogaratnam. Pirfenidone: A Novel Agent for the Treatment of Idiopathic Pulmonary Fibrosis The Annals of Pharmacotherapy n 2013 March, Volume 47 361 -367. and InterMune and BI Web sites).

Currently, the only treatment options for IPF are Pirfeinidone and Nintedanib and both drugs have limited efficacy. One of the main reasons for having difficulty to treat this disease is the fact that factor(s) causing the development of this disease are not fully understood. For this very reason, we believe that there is still need for development of new drug candidates to effective treatment of IPF.

In this respect, there are some patents or patent applications claiming the use of Chromene derivatives as an alternative treatment options. Some of these are shown below;

EP2295053A 1 discloses Chromene and some of its derivatives generated by changing Rl and R2 have been claimed for treatment of fibrosis.

US 8,048,912,B2 discloses the compound created from Chromene has been claimed to be used against fibrosis caused by TGF-beta.

US 2009/0088477 Al discloses the main structure shown below and its derivatives have been claimed to be used against asthma, COPD and atherosclerosis.

WO 2006 070984 discloses the main structure shown below and its derivatives have been claimed to be used against diseases which derive from collagen deposition.

US 2012/0196867 Al discloses the main structure shown below and its has been claimed to be used against COPD as phosphodiesterase inhibitor.

EP2620443A 1 discloses the main structure shown below and its derivatives have been claimed to be used against fibrosis as Galectin-3 inhibitor.

WO2006070984A 1 discloses the main structure shown below and its derivatives have been claimed to be used against fibroplasias and TGF-induced fibrosis.

Object of the invention

Although derivatives of 6,7-dimethoxy 2H-chromen-2-one ( l ) have been claimed to be used as anti-fibrotic agent, currently there is no chromene-derived anti-fibrotic drugs. In the present invention, carbonyl oxygen is removed from Chromene structure, this yielded positively charged chromene, then from this structure, 72 different molecules composed of 8 different molecule (4,5,6,7,8,9, 10, 1 1 ) with 9 different combinations were generated. Description of the Drawings

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

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

Figure 4: 6,7-dimethoxy-2H-chiOinen-2-one

Figure 5:Main compound produced from 6,7-dimethoxy-2H-chromen-2-one

Figure 6: Side chain added to the compound described at figure 5,

Figure 7: First structure produced from figure 5.

Figure 8: 6,7-dimethoxy-chromenyliiim perchlorate.

Figure 9: 6-ethoxy-7 methoxy 2,3,4,5, 8-pentamethyl naphatehalen-1 -ylium

Figure 10: 7-ethoxy-6-methoxy-2,3,4,5, 8-pentamethyl naphatehalen-l-ylium.

Figure 11 : 6,7-diethoxy-2,3,4,5, 8-pentamethyl naphatehalen-l -ylium.

Figure 12: 6-hydroperoxy-7-methoxy-2,3,4,5,8-pentamethylnaphatehalen-l -ylium

Figure 13: 7-hydroperoxy-6-methoxy-2,3,4,5,8-pentamethy1naphatehalen~1 -ylium

Figure 14: 6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-l-ylium

Figure 15: 7-ethoxy-6--hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-l -ylium

Figure 16: 6-ethoxy-7--hydroperoxy-2,3,4,5,8-pentamethylnaphatehalen- l -ylium

Figure 17: Second structure produced from figure 5.

Figure 18:2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7 -dimethoxy-3,4,5,8- tetramethyl- 1 λ' -chromen-( 1 : 1 ) formaldehyde compound

Figure 19: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-etho xy-7-methoxy- 3,4,5, 8-tetramethyl- 1 λ ^? -chromen-(1 : 1) formaldehyde compound

Figure 20: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-etho xy-6-methoxy-

3,4,5, 8-tetramethyl- 1 λ -chromen-(l : 1 ) formaldehyde compound

Figure 21 : 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-di ethoxy-3,4,5,8- tetramethyl-1 λ' -chromen-(l : l) formaldehyde compound

Figure 22: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydi Operoxy-7-methoxy-

3,4,5, 8-tetramethyl- 1 λ' -chromen (1 : 1) formaldehyde compound

Figure 23: 2-(4-(3,4-dimethoxy-2,5,6-trimethyiphenyl)butan-2-yl)-7-hydr operoxy-6-methoxy- 3,4,5, 8-tetramethyl- 1 λ ^'! -chromen (1 : 1) formaldehyde compound

Figure 24: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-di hydroperoxy-3,4,5,8- tetramethyl- 1 λ ³ -chromen ( 1 : 1) fornialdehyde compound Figure 25: 2-(4-(3,4-diinethoxy-2,5,6-trimethylphenyl)butan-2-yl )-7-ethoxy-6- hydroperoxy-3,4,5,8-tetramethyl- 1 λ ' -chromen ( 1 : 1 ) formaldehyde compound

Figure 26: 2-(4-(3,4-dimethoxy-2,5,6-trimethy phenyl)butan-2-yl)-6-ethoxy-7-hydroperoxy- 3,4,5, 8-tetramethyl-l λ ³ -chromen (1 : 1) formaldehyde compound

Figure 27: 3th structure produced from figure 5.

Figure 28: 7-ethoxy-6methoxy-2,3,4,5,8-pentamethylnaphthalen-l-ylium

Figure 29: 6,7-diethoxy- 2,3,4,5,8-pentamethyi naphatehalen-1 -ylium

Figure30:6-methoxy-2,3,4,5,8-pentamethyl-7-piOpoxynaphate halen- 1 -yl turn

Figure 31 : 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen- l -ylium

§ekil 32: 7-ethoxy-6-hydroperoxy- 2,3,4,5,8-pentamethyi naphatehalen-1 -ylium

Figure 33: 7-(hydroxymethoxy)- 6-methoxy- 2,3,4,5,8-pentamethyi naphatehalen- 1 - ylium Figure 34: 6-hydroperoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl naphatehalen-1 -ylium Figure 35: 6-hydropeiOxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen- 1. -ylium

Figure 36: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5.8-pentamethylnaphatehale n-l -ylium

Figure 37: 4th structure produced from figure 5.

Figure 38: 2-(4-(3,4-dimethoxy-2,5,6-triinethylphenyl)butan-2-yl)-7-eth oxy-6-methoxy-

3,4,5, 8-tetramethyl-l λ ^? -chromen and methyl- λ' -oxidane (4: 1 : 1) formaldehyde compound Figure 39: 2-(4-(3,4-dimethoxy-2,5,6-trimethylplienyl)butan-2-yl)-6,7-d iethoxy-3,4,5,8- tetramethyl-1 λ ³ -chromen and methyl- λ ^! -oxidane ( : 1 : 1 ) formaldehyde compound

Figure 40: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-meth oxy~3 ,4,5,8- tetramethyl-7-propoxy-l λ' -chromen and methyl- λ' -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 41 : 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2 -yl)-6-ethoxy-3 ,4,5,8- tetramethyl-7-propoxy- 1 λ' -chromen and methyl- λ' -oxidane (3: 1 : 1 ) tonnaldehyde compound

Figure 42: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-etho xy-6-hydroperoxy- 3,4,5, 8-tetramethyl-l λ ³ -chromen and methyl- λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound Figure 43: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-meth oxy-3,4,5,8- tetramethyl-1 λ ³ -chromen-7-yl)oxy)methanol and methyl- λ' -oxidane (3: 1 : 1 ) fomialdehyde compound

Figure 44: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydr opeiOxy -3,4,5,8- tetramethyl-l λ ^" ' -chromen-7-yl)oxy)methanol and methyl- λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 45: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydr operoxy -3,4,5,8- tetramethyl-7-propoxy-l λ ³ -chromen and methyl λ ¹ -oxidane (3 : 1 : 1 ) fomialdehyde compound Figure 46: 2-(4-(3,4-dimetlioxy-2,5,6-trimethylphenyl)butan-2-yl)-6-eth oxy-3,4,5,8- tetramethyl- 1 λ ³ -chromen-7-yl)oxy)methanol and methyl- λ' -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 47: 5th structure produced from figure 5.

Figure 48: 6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehaien- ! -ylium

Figure 49: 7-methoxy-2,3,4,5,8-pentamethyl- 6-propoxynaphatehalen- 1 -ylium

Figure 50: 6,7-diethoxy -2,3,4,5,8-pentamethylnaphatehalen- l -ylium

Figure 51 : 7-ethoxy-2,3,4,5,8-pentamethyi- 6-propoxynaphatehalen- 1 -ylium

Figure 52: 6-(hydroxymethoxy)- 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen- 1 -ylium Figure 53 : 6-ethoxy-7-hydroperoxy-2,3 ,4,5, 8-pentamethylnaphatehalen-l -ylium

Figure 54: 7-hydroperoxy-6-(hydroxymetoxy)-2,3,4,5,8-pentamethylnaphate halen- 1 -ylium Figure 55: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehale n-l -ylium Figure 56: 7-hydroperoxy -2,3,4,5, 8-pentamethyl-6-propoxynaphatehalen-l -ylium

Figure 57: 6th structure produced from figure 5.

Figure 58: l-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methox y-3 ,4,5,8- tetramethyl- 1 λ ³ -chromen~2-yl)butart-l -one and methyl λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 59: 3-(6,7-diethoxy-3,,4,5,8-tetramethyl--l ^J -chromen-2-yl)-l -(3,4-dimethoxy~2,5,6- trimethylpheny1)butan-l -one-and methyl- λ ^ι -oxidane (3: 1 : 1 ) formaldehyde compound Figure 60: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8- tetramethyl-6- propoxy-1 λ ^" -chromen-2-yl)butan-l-one and methyl λ ¹ -oxidane (3: 1 : 1) formaldehyde compound

Figure 61 : 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-3,4,5,8-t etramethy -6- propoxy-1 λ ³ -chromen-2-yl)butan- 1 -one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 62: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydiOxymethoxy) -7-methoxy- 3,4,5, 8-tetrainethyl- 1 λ ' -chromen-2-yl)butan- 1 -one and methyl λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 63: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydrope roxy-3 ,4,5,8- tetramethyl- 1 λ' -chromen-2-yl)butan-l-one-and methyl- λ ^! -oxidane (3: 1 : 1 ) formaldehyde compound

Figure 64: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(h ydroxyperoxy)- 3,4,5, 8-tetramethyl- 1 λ' -chromen-2-yl)butan- 1 -one and methyl- λ ^! -oxidane (3 : 1 : 1 ) formaldehyde compound

Figure 65: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydrox yperoxy)-3,4,5,8- tetramethyl- 1 λ ³ -chromen-2-yl)butan-l-one and methyl λ' -oxidane (3: 1: 1) formaldehyde compound Figure 66: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hy

propoxy-1 λ ³ -chromen-2-y )butan- 1 -one and methyl λ' -oxidane (3: 1 : 1) formaldehyde compound

Figure 67: 7th structure produced from figure 5.

Figure 68: 6,7-diethoxy-2,3,4,5,8-pentamethy naphatehalen-l -ylium

Figure 69: 7-ethoxy-2,3,4,5,8-pentamethyl-6-propoxynaphatehalen-l -ylium

Figure 70: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehaien- 1 -ylium

Figure 71 : 2,3,4,5,8-pentamethyl-6,7-dipropoxynaphatehalen-l -ylium

Figure 72: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehale n-l -ylium

Figure 73: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehaie n- l -ylium

Figure 74: 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-l -ylium

Figure 75: 6-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-7-propoxynaphatehal en-l -ylium Figure 76: 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6-propoxynaphatehal en- 1 -ylium Figure 77: 8th structure produced from figure 5.

Figure 78: 3-(6,7-dietoxy-3,4,5,8-tetramethyl-1 λ ^;! -chromen-2-yl)-l -(3,4-dimethoxy-2,5,6- trimethylphenyl)butan-l -one-and methyl- λ ^! -oxidane (3: 1 : 1) formaldehyde compound

Figure 79: l -(3,4-dimethoxy-2,5,6-tTimethylphenyl)-3-(7-ethoxy,3,4,5,8-t etramethyl-6-propoxy- 1 λ ³ -chromen-2-yl)butan-l-one-metliyl^ ^l -oxidane(3: l : l ) formaldehyde compound

Figure 80: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-t etramethyl-7- propoxy-1 λ ³ -chromen-2-yr)butan-l -one-methyl-?^-oxidane(3: l : l) formaldehyde compound Figure 81 : l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(,3,4,5,8-tetrameth yl-6,7-dipropoxy-l X ³ - chromen-2-yl)butan~l -one-methyl-X'-oxidane(3: 1 :1) formaldehyde compound

Figure 82: l -(3,4-dimethoxy-2,5,6-trimethylphenyi)-3-(7-ethoxy-6-(hydrox yperoxy)-3,4,5,8- tetramethyl- 1 ⁵ -chromen-2-yl)butan-l -one and methyl λ'-oxidane (3: 1 : 1 ) formaldehyde compound

Figure 83: 1 -(3,4-dimethoxy-2^,6-tnmeihylphenyl)-3-(6-ethoxy-7-(hydroxym ethoxy)-3,4,5,8- tetramethy1-- l λ ³ -chromen-2-yl)butan-l -one-and -methyl- λ'-οχΐάαηβ(3: 1 : 1) formaldehyde compound

Figure 84: 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethy1- l λ ³ -chromen-2-yl)-l-(3,4- dimethoxy~2,5,6-trimethylphenyl)butan- 1 -one-and-methyl-λ ¹ -oxidane(3 : 1 : 1 ) formaldehyde compound

Figure 85: l-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy )-(3,4,5,8- tetrainethyl-7-propoxy-l λ ³ -chromen-2-yl)butan-1 -one-and-methyl- λ '-oxidane(3: l :l ) formaldehyde compound

Figure 86: l -(3,4-dimethoxy-2,5,6-trimethyiphenyl)-3-(7-(hydroxymethoxy) -(3 ,4,5,8- tetramethyl-6-propoxy- 1 λ ^' -ch romen-2-yl)butan- 1 -one-and-methyl- λ '-oxidane(3 : 1 : 1 ) formaldehyde compound. EXPLANATION OF REFERENCES OF FIGURES

1 : 6,7-dimethoxy-2H-chromen-2-one

2: Main compound produced from 6,7-dimethoxy-2H-chiOmen-2-one

3: Side chain added to the compound described at figure 5

4: First structure produced from figure 5.

4.1: 6,7-dimethoxy-chromenylium perch lorate

4.2: 6-ethoxy-7 methoxy 2,3,4,5,8-pentamethyl naphatehalen- l -ylium

4.3: 7-ethoxy-6-methoxy-2, 3,4,5, 8-pentamethy I naphatehalen- 1 -ylium

4.4: 6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen- l -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-l -ylium

4.7: 6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen-l -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-l -ylium

5: Second structure produced from figure 5.

5.1: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan^

1 λ ³ -chromen-(l : 1 ) formaldehyde compound

5.2: 2-(4-(3,4-dimethoxy-2,5,6-trimethy1phenyl)butan-2-yl)-6-etho xy-7-methoxy-3,4,5,8- tetramethyl- 1 λ 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 λ ³ -chromen-(l : l) formaldehyde compound 5.4: 2-(4-(3,4-dimethoxy-2,5,6- irimethylphenyl)butan-2-yl)-6 ,7-diethoxy-3,4.5,8-tetramethyl-l λ' -chromen-(l : 1 )

formaldehyde compound

5.5: 2-(4-(3,4-dimethoxy-2,5,6-trimethy

tetramethyl- 1 λ ³ -chromen (1 : 1) formaldehyde compound

5.6: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-hydr operoxy-6-methoxy-3 ,4,5,8- tetramethyl- 1 λ ³ -chromen (1 : 1 ) formaldehyde compound

5.7: 2-(4 3,4-dimethoxy-2,5,6-trimethylphenyi)butan-2-yl)-6,7-dihydrop eroxy-3,4,5,8- tetramethyl- 1 λ ³ -chromen (1 : 1) formaldehyde compound

5.8: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-etho xy-6-hydroperoxy-3 ,4,5,8- tetramethyl-1 λ ³ -chromen ( 1 : 1 ) formaldehyde compound

5.9: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-etho xy-7-hydroperoxy-3,4,5,8- tetramethyl- 1 λ ³ -chromen (1 : 1 ) formaldehyde compound

6: 3th structure produced from figure 5.

6.1: 7-ethoxy-6 methoxy-2, 3 ,4, 5 , 8 -pen tamethy I n aph thalen- i -y Hum 6.2: 6,7-diethoxy- 2,3,4,5, 8-pentamethyl naphatehalen- 1 -ylium

6.3: 6-methoxy-2,3,4,5,8-pentamethyi-7-piOpoxynaphatehalen- 1 -ylium

6.4: 6-ethoxy-2,3,4,5,8-pentamethyl-7-propoxynaphatehalen- l -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-pentamethylnaphatehale n- 1 -ylium

7: 4th structure produced from figure 5

7.1: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yi)-7-etho xy-6-methoxy-3,4,5,8- tetramethyl-1 λ ^" ' -chromen and methyl- λ' -oxidane (4: 1 : 1) formaldehyde compound

7.2: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-di ethoxy-3,4,5,8-tetramethyl-l λ ³ -chromen and methyl - λ' -oxidane (3: 1 : 1 ) formaldehyde compound

7.3: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-meth oxy--3,4,5,8-tetramethyl-7- propoxy-1 λ ³ -chromen and methyl- λ' -oxidane (3: 1 : 1 ) fonnaldehyde compound

7.4: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-etho xy-3,4,5,8-tetramethyl-7- propoxy-1 λ ^' '-chromen and methyl- λ' -oxidane (3: 1 : 1 ) fonnaldehyde compound

7.5: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-etho xy-6-hydroperoxy-3,4,5,8- tetramethyl-1 X ^J -chromen and methyl- λ' -oxidane (3: 1 : 1) formaldehyde compound

7.6: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-meth oxy-3,4,5,8-tetramethyl-1 3-chromen-7-yl)oxy)methanol and methyl- λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound

7.7: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyi)butan-2-y )-6-hydropeiOxy -3,4,5,8- tetramethyl-1 ^'-chromen-7-yl)oxy)methanol and methyl- λ ¹ -oxidane (3: 1 : 1) formaldehyde compound

7.8: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydr operoxy -3,4,5,8- tetramethyl-7-propoxy-l ^-chromen and methyl λ'-oxidane (3: 1 : 1 ) formaldehyde compound 7.9: 2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-etho xy-3,4,5,8-tetramethyl- l λ ³ - chromen-7-yl)oxy)methanol and methyl-λ' -oxidane (3: 1 : 1 ) formaldehyde compound

8: 5 th structure produced from figure 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-propoxynaphatehaien- l -ylium

8.3: 6,7-diethoxy -2,3,4,5,8-pentamethylnaphatehalen-l -ylium

8.4: 7-ethoxy-2,3 ,4,5, 8-pentamethyl- 6-propoxynaphatehalen-l-ylium

8.5: 6-(hydroxymethoxy)- 7-methoxy-2,3 ,4,5,8-pentamethylnaphatehalen- 1 -ylium

8.6: 6-ethoxy-7-hydiOperoxy-2,3,4,5,8-pentamethylnaphatehalen-l -ylium

8.7: 7-hydropeiOxy-6-(hydroxymetoxy)-2,3,4,5,8-pentamethylnaphate halen-l -ylium

8.8: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehale n-l-ylium 8.9: 7-hydroperoxy -2,3,4,5, 8-pentamethyl-6-propoxynaphatehalen-l-ylium

9: 6th structure produced from figure 5.

9.1 : l-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-methox y-3,4,5,8-tetramethyl-l λ ³ - chromen-2-yl)butan- 1 -one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound

9.2: 3-(6,7-diethoxy-3,,4,5,8-tetramethyl--l -chromen-2-yl)-l -(3,4-dimemoxy-2,5,6- trimethylphenyl)butan-l -one-and methyl- λ' -oxidane (3: 1 : 1 ) formaldehyde compound

9.3: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8- tetramethyl-6-propoxy-l λ ³ -chromen-2-yl)butan- 1 -one and methyl λ ¹ -oxidane (3 : 1 : 1 ) formaldehyde compound

9.4: 1 ^3,4-dimethoxy-2,5,6-trimethylphenyl 3-(7-etboxy-3,4,5,8-tetrainethyl-6-propoxy-l λ ³ -chromen-2-yl)butan-l -one and methyl λ' -oxidane (3: 1 : 1) formaldehyde compound

9.5: l-(3,4-dimethoxy-2,5,6-trimethyiphenyl)-3-(6-(hydroxymethoxy )-7-methoxy-3,4,5,8- tetramethyl- 1 λ ³ -chromen-2-yl)butan-l -one and methyl λ' -oxidane (3: 1 : 1) formaldehyde compound

9.6: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-hydrope roxy-3,4,5,8-tetramethyl^ λ ³ -chromen-2-yl)butan- l -one-and methyl- λ' -oxidane (3 : 1 : 1 ) formaldehyde compound

9.7: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-6-(h ydroxyperoxy)-3 ,4,5,8- tetramethy -1 λ ³ -chromen-2-yl)butan- 1 -one and methyl- λ' -oxidane (3: 1 : 1) formaldehyde compound

9.8: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydrox yperoxy)-3 ,4,5,8- tetramethyl- 1 λ ³ -chromen-2-yl)butan-l-one and methyl λ' -oxidane (3: 1 : 1) formaldehyde compound

9.9: l-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-hydroperoxy-3,4 ,5,8-tetTamethyl-6-propoxy- 1 λ' -chromen-2-yl)butan-l -one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound

10: 7th structure produced from figure 5.

10.1: 6,7-diethoxy-2,3,4,5,8-pentamethylnaphatehalen-l -yliiim

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-l -ylium

10.5: 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehale n- l -ylium

10.6: 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehale n-l -ylium

10.7: 6,7-bis(hydroxymethoxy)-2,3,4,5,8-pentamethylnaphatehalen-l -ylium

10.8: 6-(hydroxymethoxy)-2,3,4,5,8-pentamethy1-7-propoxynaphatehal en-l -ylium

10.9: 7-(hydroxymethoxy)-2,3,4,5,8-pentamethyl-6-piOpoxynaphatehal en-l -yliuin

11 : 8th structure produced from figure 511.1: 3-(6,7-dietoxy-3,4,5,8-tetramethyl— 1 λ ³ - chromen-2-yl)- 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)butan- 1 -one-and methyl- λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound 11.2: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(7-eth^ λ ³ - chromen.-2-yl)butan-l -one-methyl- „'-oxidane(3: 1 : 1 ) formaldehyde compound

11.3: 1 -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-t etramethyl-7-propoxy- 1 λ'- chromen-2-yl)butan-l-one-methyl- λ ^l -oxidane(3 : 1 : 1 ) formaldehyde compound

11.4: l-(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(,3,4,5,8-tetramet hyl-6,7-dipiOpoxy- 1 λ - chromen-2-yl)butan- 1 -one-methyl- λ' -oxidane(3 : 1 : 1 ) formaldehyde compound

11.5: l-(3,4-dimethoxy-2,S,6-trimethylphenyl)-3-(7-ethoxy-6-(hydro xyperoxy)-3,4,5,8- tetramethy -1 λ ³ -chromen-2-yl)butan-l-one and methyl λ'-oxidane (3: 1 :1) formaldehyde compound

11.6: l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydrox ymethoxy)-3,4,5,8- tetramethyl— 1 ^-chromen-2-yl)butan~1 -one-and -methyl- '-oxidane(3: l : l) formaldehyde compound

11.7: 3-(6,7-bis(hydroxymethoxy)-3,4,5,8-tetramethyl-l ?^-chromen-2-yl)-l-(3,4-dimethoxy- 2,5,6-trimethylphenyl)butan- l -one-and-methyl- '-oxidane(3: 1 : 1 ) formaldehyde compound

11.8: l -(3,4-dimethoxy-2,5,6-tTimethylphenyl)-3-(6-(hydroxymethoxy) -(3,4.5,8-tetramethyl-7- propoxy-1 λ ^" ' -chromen-2-yl)butan-l~one-and-methyl- λ ¹ -oxidane(3: 1 : 1 ) formaldehyde compound

11.9: l -(3,4-dimethoxy-2,5,6-trimethylphem

propoxy- 1 -one-and-methyl- λ ¹ -oxidane(3 : 1 : 1 ) formaldehyde compound

Description of the invention

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 ( 1 ) against TGF beta-induced collagen synthesis using L929 cells has been identified. For this, in 96-well plates, L929 cells were cultured in DMEM supplemented with %10 serum, 10 μg/ml ascorbic acid and 20 μ prolin until they reached to confluency. Confluent cells were treated with 50 micromole of our compound (named as CP 1 ) dissolved in DMSO for 1 hour, then 5 ng/ml of Mouse ΤΟΡβ2 was added and cells were further incubated for 72 hours at incubator supplied with 5% CO? and 80% humidity. At the end of this incubation one of the plate was used to determine cell viability by using MTT test, figure 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 w ere fixed to bottom of the plated by adding % 0.5 gluteraldehyde prepared in I X PBS 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. T hen, "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 figure 1 , TGFP induced collagen level by %20 compared to control cells, however, in the presence of CPl TGFP induced collagen level by %10, in other words CPl inhibited TGFp-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 I X PBS) and blocked with %i BSA prepared in PBST for 2 hours, plate was washed with PBST and anti-collagen type 1 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 PBS T and ELISA was performed. As shown at figure 3, present compound (CP1 ) significantly inhibits TGFp-induced secreted collagen level. These results strongly indicate that the compounds derived from CPl may offer alternative treatment options to treat fibrosis patients.

Structure of the above mentioned (CPl ) compound is 6,7-dimethoxy 2H-chromen-2-one (1 ) and its chemical Formula is CnHj i

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, 10,1 1 ) and their 9 different combinations were generated.

Rl and R2 positions of these 8 compound were chosen as site of modifications, and methyl(- CH3), ethyl(-C2H5), hydroxy! (-011), and their combinations with one another were chosen to represent Rl and R2.

Eight different structure and their derivatives are explained below; In the first compound (4), produced from main compound (2); when R 1 and R2 are are methyl (-CH3), and in this compound (6,7-dimethoxy-chromenyliiim perchlorate(4.1)

R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C|-C ₆ afkoxide, C|-C ₆ alkyl, C|-C ₍ , fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (- COOH) and their combinations with one another.

In the first compound (4), produced from main compound (2); when Rl is ethyl (-C2H5) and R2 is methyl(-CH3), and in this compound (6-ethoxy-7 methoxy 2,3,4,5, 8-pentamethyi naphatehalen- 1 -ylium (4.2); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02). C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the first compound (4), produced from main compound (2); when Rl is methyl (-CH3) and R2 is et.hyl(-C2H5), and in this compound (7-ethoxy-6-methoxy-2,3,4,5,8-pentamethyl naphatehalen-l-ylium (4.3)R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C _r C ₆ alkyl, C,-C ₅ fluoroalkyl, C C _f , alkenyl, carboxyl (-COOFI) and their combinations with one another. In the first compound (4), produced from main compound (2); when R 1 and R2 are ethyl(- C2H5), and in this compound (6,7-diethoxy-2,3,4,5,8-pentamethyl naphatehalen-l-ylium) (4.4); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C3-C6 cycloalkenyl , C _r C ₆ alkoxide, C C ₆ alkyl, C C ₍ , fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (- COOH) and their combinations with one another. In the first compound (4), produced from main compound (2); when Rl is hydroxyl (-OH) and R2 is methyl (-CH3), and in this compound (6~hydroperoxy-7-methoxy-2,3,4,5,8- pentamethylnaphatehalen-l -ylium) (4.5); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2I J5), amino (-NH2), nitro (-N02). C C ₆ cycloalkenyl , C,-C ₆ alkoxide. C,-C ₆ alkyl, Ci- _f e fluoroalkyl, C?-C<, alkenyl, carboxyl (-COOH) and their combinations with one another.

In the first compound (4), produced from main compound (2); when Rl is methyl (-CH3) and R2 is hydroxy! (-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, (-011), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1). methyl (-CH3), ethyl (-C2H5). amino (-NH2), nitro (-N02), C,-C ₅ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, fluoroalkyl, C?-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the first compound (4), produced from main compound (2); when Rl and R2 are hydroxyl (-OH) , and in this compound (6,7-dihydroperoxy-2,3,4,5,8-pentamethylnaphatehalen- l-yh ^' um ) (4.7); R3,R4,R5,R6 and 7 can be; hydrogen, (-M), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) . bromide (-Br), iodine (-1), methy l (-CH3), ethyl (-C2H5), amino (- H2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Q-Q, alkoxide, C _r C ₆ alkyl, C Q fluoroalkyl, C?-Q alkenyl, carboxyl (-COOH) and their combinations with one another.

In the first compound (4), produced from main compound (2); when Rl is hydroxyl (-Oil) and R2 is ethyl (-C2H5 , and in this compound (7-ethoxy-6~hydroperoxy-2,3,4,5,8- pentamethylnaphatehalen-l -ylium) (4.8): R3,R4,R5,R6 and R7 can be: hydrogen, (-H), hydroxyl, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02). C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, Ci-C _f , fluoroalkyl, C^-C^ alkenyl, carboxyl (-COOH) and their combinations with one another

In the first compound (4), produced from main compound (2); when Rl is ethyl (-C2H5) and R2 is hydroxyl (-Oi l), and in this compound (6-ethoxy-7~hydroperoxy-2,3,4,5,8- pentamethyl naphatehalen-l -ylium) (4.9) R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C C ₆ alkoxide, C,-C ₆ alkyl, Cj-C _ft fluoroalkyl, C ₂ -Q, alkenyl, carboxyl (-COOH) and their combinations with one another

In the second compound (5), produced from main compound (2); when Rl , R2, Rl 1 and R12 are methyl (-CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6- trirnethylpheiiyl)butaii-2-yl)-6,7-dimethoxy-3,4.5,8-tetrame thyl- 1 λ ³ -chromen-( 1 : 1 ) formaldehyde compound (5.1) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen. (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) . bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NFI2), nitro (-N02), C _r C ₆ cycloalkenyl , C _r C ₆ alkoxide, C,-C ₆ alkyl, Cj -Ci fiuoroa!kyl, Cj-Q alkenyl, carboxy l (-COOH) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l is ethyl (- C2H5) R2 is methyl (-CH3), Rl 1 and R12 are methyl (-CH3 and in this compound (2-(4-(3,4- dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-ethoxy-7-metho xy-3,4,5,8-tetramethyI-l λ ^" ' - chromen-( l : l)fonnaldehyde compound) (5.2) R3,R4.R5,R6, R7.R8.R9 and RI O can be: hydrogen, (-H), hydroxyl, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-Q, alkoxide, Ci-C alkyl, C) -C<s fluoroalkyl, C?-C _f) alkenyl, carboxyl (-C001 I) and their combinations with one another. In the second compound (5), produced from main compound (2); when R i is methy l (-

CH3), R2 is ethyl (-C2H5), Rl 1 and R12 are methyl (-CH3) and in this compound (2-(4-(3,4- dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-metho xy--3,4,5,8 etramethyl- 1 λ ³ - chromen-( l : l) formaldehyde compound) (5.3) R3,R4,R5,R6, R7,R8,R9 and R I O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5 ), amino (-NH2), ηΐΐτο (-N02), C Q cycloalkenyl , C,-C ₆ alkoxide, C i-C ₆ alkyl, Ci -C ₆ fluoroalkyl, C?-C alkenyl, carboxyl (-COOH) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l and R2 are ethyl (-C2H5), Rl l and R12 are methyl (-CI 13) and in this compound (2-(4-(3,4-dimethoxy- 2,5,6-trimethylphenyl)butan-2-yl)-6,7-diethoxy-3,4,5,8-tetra methyl- l λ ³ -chromen-( 1 : 1 ) formaldehyde compound) (5.4) R3,R4,R5,R6, R7,R8,R9 and R 10 can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C,-C ₆ cycloalkenyl , C,-C ₆ alkoxide, C-Q, alkyl, C] -C6 fluoroalkyl, C2-C ₆ alkenyl, carboxyl (-COOM) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l is hydroxy 1(-

OH) R2 is methyl (-CH3), Rl 1 methyl (-CI 13), R 12 methyl (-CH3) and in this compound (2-(4-

(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6-hydrop eroxy-7-methoxy-3,4,5,8- tetramethyl-1 λ ³ -ehromen ( 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 (-1), methyl (-CH3), ethyl (-C2H5), amino (- H2), nitro (-N02), C C ₆ cycloalkenyl , C|-Ce alkoxide, CrQ alkyi, C{-C(, fluoroalkyl, C2-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l , methyl (-CH3) R2 hydroxyl ( -OH), R l 1 methyl (-CH3), R l 2 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- l λ ⁵ -chromen ( 1 : 1 ) formaldehyde compound) (5.6) R3,R4,R5.R6, R7,R8,R9 and R I O can be; hydrogen, (-H), hydroxyl, (-011), fluoride (-F). chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CTI3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, Ct-Ce alkyl, Ci-Ce fluoroalkyl, Ca-Q alkenyl, carboxyl (-COOH) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l and R2 are hydroxyl ( -OH), R l 1 methyl (-CH3), R 12 methyl (-CH3) and in this compound (2-(4-(3,4- dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-6,7-dihydroperox y-3,4,5,8-tetramethyl- 1 λ ³ - chromen ( 1 : 1 ) formaldehyde compound) (5.7) R3,R4,R5,R6, R7,R8,R9 and R I O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1). methyl (-CH3), ethyl (-C2H5), amino (-NH2 ), nitro (-N02), C _r C ₆ cycloalkenyl , C C ₆ alkoxide, C _r C ₆ alkyl, C i-C ₆ fluoroalkyl, C C _f , alkenyl, carboxyl (-COOH) and their combinations with one another.

In the second compound (5), produced from main compound (2); when R l is hyclroxyl(- OH) and R2 is ethyl ( -C2H5), Rl 1 methyl (-CH3), R 12 methyl (-CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-eth oxy-6-hydroperoxy-3,4,5,8- tetramethyl-1 λ ³ -chromen ( 1 : 1 ) formaldehyde compound) (5.8) R3,R4,R5,R6, R7,R8,R9 and R I O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2). nitro (-N02), C C _(l cycloalkenyl , Ct-Ce alkoxide, C |-C ₆ alkyl, C _t -C ₆ fluoroalkyl, Cj-Q alkenyl, carboxyl (-COOH) and their combinations with one another.

In the second compound (5 ), produced from main compound (2); when R l is ethyl (-

C2H5), R2 is hydroxy! ( -OH), R l 1 methyl (-CH3), Rl 2 methyl (-CH3), and in this compound

(2-(4-(3,4-dimethoxy-2,5,6-trimethylphenyi)butan-2-yl)-6- ethoxy-7-hydroperoxy-3,4,^ tetramethyl- 1 λ ^:ϊ -chromen ( 1 : 1 )formaldehyde compound) (5.9) R3,R4, 5,R6, R7,R8,R9 and R10 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C|-C _ti alkoxide, Ci-C ₆ alkyl, Ci-C ₆ fluoroalkyl, C C _¾ alkenyl, carboxyi (-COOH) and their combinations with one another.

In the third compound (6), produced from main compound (2); when R 1 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), hydroxy., (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2I I5), amino (-NH2), nitro (-N02), CVQ, cycloalkenyl , C _r C ₆ alkoxide, Cj-Q alkyl, C)-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyi (-COOH) and their combinations with one another.

In the third compound (6), produced from main compound (2); when Rl is ethyl (-C2H5) and R2 is methyl (-CH3), and in this compound (6,7-diefhoxy- 2,3,4,5, 8-pentamethyl naphateha!en-l -ylium (6.2) R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-Q, fluoroalkyl, C ₂ - Ce alkenyl, carboxyi (-COOII) and their combinations with one another.

In the third compound (6), produced from main compound (2); when Rl is methyl (-CH3) and R2 is ethyl (-C2H5), and in this compound (6-methoxy-2,3,4,5,8-pentamethyl-7- propoxynaphatehalen- l -ylium (6.3) R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (- C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyi (-COOH) and their combinations with one another. In the third compound (6), produced from main compound (2); when Rl is ethyl (-C2H5) and R2 is ethyl (-C2H5), and in this compound (6-ethoxy-2,3,4,5,8-pentamethyl-7- piOpoxynaphatehalen- l -ylium (6.4) R3,R4,R5,R6 and R7 can be; hydrogen, (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (- C2H5), amino (-NH2), nitro (-N02), C ₃ -Q, cycloalkenyl , C C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C C ₆ alkenyl, carboxyi (-COOH) and their combinations with one another.

In the third compound (6), produced from main compound (2);when Rl is hydroxyl(-OH) and R2 is methyl (-CH3), and in this compound (7-ethoxy-6-hydroperoxy- 2,3,4,5,8- pentamethyl naphatehalen-l-ylium (6.5) R3,R4,R5,R6 and R7 can be; hydrogen, (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (- 02), C ₃ -C ₆ cycloalkenyl , C _r C alkoxide, C C ₆ alkyi, Cj-Q fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one anot

In the third compound (6), produced from main compound (2); when Rl 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 (-1), methyl (-CF13), ethyl (-C2I I5), amino (-NH2), nitro (-N02). C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C C ₀ alkyi, C|-C(, fluoroalkyl, C2-Q aikenyl, carboxyl (-COOH) and their combinations with one another.

In the third compound (6), produced from main compound (2); when Rl and R2 are hydroxyl (-OH), and in this compound (6-hydroperoxy-7-(hydiOxymethoxy)-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 (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02). C,-C ₆ cycloalkenyl . C,-C ₆ alkoxide, C,-C ₆ alkyi, C ₁ -C fluoroalkyl, C Ce alkenyl, carboxyl (-COOII) and their combinations with one another.

In the third compound (6), produced from main compound (2); when R l is hydroxyl (-Oil) and R2 is ethyl (-C2H5), and in this compound ( 6-hydroperoxy-2,3,4,5,8-pentamethyl-7- propoxynaphatehalen- l -yliitm(6.8) R3,R4,R5,R6 and R7 can be; hydrogen, (-11), hydroxyl, (- OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C3-C ₀ cycloalkenyl , C _r C6 alkoxide, C]-C ₆ alkyi, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the third compound (6), produced from main compound (2); when R l is ethyl (-C2H5) and R2 is ishydroxvl (-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 (-1), methyl (-CH3), ethyl (-C2I I5), amino (-NH2 ), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C ,-C ₆ alky , Ci-C _f i fluoroalkyl, C2-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when R1 ,R2,R1 1 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-tetramethyi-l ³ -chromen and methyl- λ' -oxidane (4: 1 : 1) formaldehyde compound) (7.1); R3,R4,R5,R6. R7,R8,R9 and R 10 can be; hydrogen, (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, Ci-C-6 fluoroalkyl, C ₂ -C<; alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when R l is ethyl(-C2H5), R2 is methyl (-CH3),R1 1 and R 12 are methyl (-CH3), and in this compound (2-(4-(3,4- dimethoxy-2,5,6-tTimethylphenyl)buto λ' -chromen and methyl- λ ^! -oxidane (3 : 1 : 1 ) formaldehyde compound) (7.2) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxy I, ( -OH), fluoride (-F ), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Cj-Q alkoxide, CpQ, alkyl, C,-C6 fluoroalkyl, C?-C<j alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when Rl is methyl(-CH3), R2 is ethyl (-C2H5), Rl 1 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-l λ ³ - chromen and methyl- λ ¹ -oxidane (3 : 1 : 1) formaldehyde compound) (7.3) R3,R4,R5,R6,

R7,R8,R9 and R10 can be; hydrogen, (-H), hydroxy!, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CII3), ethyl (-C2I I5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C _r C ₆ alkoxide, C]~C<, alkyl, fluoroalkyl, Ci-Cf, alkenyl, carboxyl (- COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when R l and R2 are ethyl (-C2H5), R l 1 and R 12 are methyl (-CH3), and in this compound (2-(4-(3,4-dimethoxy-2,5,6- trimethylpheny )butan-2-yl)-6-ethoxy-3,4,5,8-tetramethyl-7-propoxy-l λ' -chromen and methyl- λ ^! -oxidane (3 : 1 : 1 ) formaldehyde compound) (7.4) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C |-C(, alkoxide, Ci-C ₆ alkyl, fluoroalkyl, Cj-Ce alkenyl, carboxyl (-COOI I) and their combinations with one another. In the fourth compound (7), produced from main compound (2); when R l is hydroxyl(- OH), R2 is methyl (-CH3), Rl 1 and R 12 are methyl (-CH3), and in this compound (2-(4-(3,4- dimethoxy-2,5,6-trimethylphenyl)butan-2-yl)-7-ethoxy-6-hydro peroxy-3,4,5,8-tetramethyl- l λ' -chromen and methyl- λ ^! -oxidane (3 : 1 : 1 ) formaldehyde compound) (7.5) R3,R4,R5,R6, R7.R8,R9 and Rl O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C]-C ₆ alkoxide, C,-C ₆ alkyl, C]-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (- COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when Rl is methyi (- CH3), R2 is hydroxy! (-OH), R l 1 and R12 are methyl (-CH3), and in this compound (2-(4- (3,4-dimethoxy-2,5,6-trimethylphenyl)butan-2-y )-6-methoxy-3,4,5,8-tetramethyl- 1 λ' chromen-7-yl)oxy)methanoi and methyl- λ ¹ -oxidane (3: 1 : 1 ) formaldehyde compound) (7.6) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , CrQ alkoxide, Cj-Cs alkyl, CrC ₆ fluoroalkyl, C:-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when Rl and R2 are hydroxyl (-OH), Rl 1 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-tetr amethyl-l ³ -chromen-7- yl)oxy)methanol and methyl- λ'-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 (-1), methy (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Ci-C ₆ alkoxide, Ci-C ₍ , alkyl, C _r C ₆ fluoroalkyl, CS-C alkenyl, carboxyl (- COOH) and their combinations with one another.

In the fourth compound (7), produced from main compound (2); when Rl is hydroxyl(- OH), R2 is ethyl (-C2H5), Rl 1 and R12 are methyl (-CI 13), 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-l λ'-chromen and methyl λ'-oxidane (3: 1 : 1 ) formaldehyde compound) (7.8) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen, (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NI I2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Ci-C ₆ alkoxide, C _r C ₆ alkyl, C C ₆ fluoroalkyl, C?-C ₆ alkenyl, carboxyl (- COOH) and their combinations with one another. In the fourth compound (7), produced from main compound (2); when Rl is ethyl(-C2H5), R2 is hydroxyl (-OH), Rl 1 and R 12 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- l λ' -chromen-7- yl)oxy)methanol and methyl- λ' -oxidane (3: 1 : 1 ) formaldehyde compound) (7.9) R3,R4,R5,R6, R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C3-Q cycloalkenyl , C _r C ₆ alkoxide, CyC ₆ alkyl, C _r C6 fluoroalkyl, C ₂ -C ₆ alkenyl, carbox l (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when Rl and R2 are methyl and in this compound (6-ethoxy 7-methoxy-2,3,4,5,8-pentamethylnaphatehalen- l -ylium (8.1); R3,R4,R5,R6 and R7 can be: hydrogen, (-H), hydroxyl, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C,-C ₆ cycloalkenyl , Cj-Q alkoxide, Cj-C ₆ alkyl, C -C ₆ fluoroalkyl, alkenyl, carboxyl (- COOH) and their combinations with one another. In the fifth compound (8), produced from main compound (2); when R l is ethyl(-C2H5) and R2 is methyl(-CH3), and in this compound (7-methoxy-2,3,4,5,8-pentamethyl- 6- propoxynaphatehalen- l -yliiim (8.2); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (- C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C _r C ₆ alkyl, C _r C ₆ fluoroalkyl, C C^ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when Rl is methyl(-CH3) and R2 is ethyl(-C2H5), and in this compound (6,7-diethoxy -2,3,4,5,8- pentamethy!naphatehalen-I-ylium (8.3) R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C,-C ₆ alkoxide, C, -C ₆ alkyl, Ci-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when Rl and R2 are ethyl (- C2H5), and in this compound (7-ethoxy-2,3,4,5,8-pentamethyl- 6-propoxynaphatehalen-l - y!ium (8.4); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C Q cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when R l is hydroxyl (-OH), and R2 is methyl (-CH3) and in this compound (6-(hydroxymethoxy)- 7-methoxy-2,3,4,5,8- pentamethylnaphatehalen- l-ylium (8.5); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C,-C ₆ alkyl, C ,-C ₆ fluoroalkyl, C ₂ -C _f , alkenyl, carboxyl (-COOH) and their combinations with one another. In the fifth compound (8), produced from main compound (2); when R l is methyl (-CH3), and R2 is hydroxyl (-OH), and in this compound (6-ethoxy-7-hydroperoxy-2,3,4,5,8- pentamethyinaphatehalen-l-ylium (8.6). R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F ), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2). nitro (-N02), C Q, cycloalkenyi . C,-C„ alkoxide, C,-C„ alkyl, C,-C ₍ , fluoroalkyl, CVC _f , alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when Rl and R2 are hydroxyl (-OH), and in this compound (7-hydroperoxy-6-(hydroxymetoxy)-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 (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyi , C C ₆ alkoxide, CrC ₆ alkyl, C C ₆ fluoroalkyl, CS-C _h alkenyl, carboxyl (-COOH) and their combinations with one another. In the fifth compound (8), produced from main compound (2); when Rl is hydroxyl (-OH), and R2 is ethyl (-C2H5), and in this compound (7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8- pentamethylnaphatehalen- l -ylium (8.8): R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-Ϊ), methyl (-CH3), ethyl (-C2H5), amino (-NFI2), nitro (-N02), C C _e , cycloalkenyi , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C2-C , alkenyl, carboxyl (-COOH) and their combinations with one another.

In the fifth compound (8), produced from main compound (2); when Rl is ethyl (-C2115), R2 is hydroxyl (-Oi l), and in this compound (7-hydroperoxy -2,3,4,5, 8-pentamethyl-6- propoxynaphatehalen-l-ylium (8.9); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (- OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CI I3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyi , C]-C ₆ alkoxide, C i -C ₆ alkyl, C _r C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when R1 ,R2,R1 1 and R12 are methyl (-CH3), and in this compound (l -(3,4-dimethoxy-2,5,6-trimethylphenyl)-3-(6- ethoxy-7-methoxy-3,4,5,8-tetramethyl-l λ ^" -chromen-2-yl)butan-l -one and methyl λ ¹ -oxidane (3: 1 : 1) formaldehyde compound(9.1); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NF12), nitro (-N02), C ₅ -Q cycloalkenyi , Cj-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOl I) and their combinations with one another. In the sixth compound (9), produced from main compound (2); when Rl is ethyl (-C2H5), R2 is methyl (-C113), Rl 1 and R12 are methyl (-CH3), and in this compound (3-(6,7-diethoxy- 3„4,5,8-tetramethyl--l '-chromen-2-yl)-l -(3,4-dimethoxy-2,5,6-trimethylphenyl)butan- l -one- and methyl- λ' -oxidane (3: l : l)formaldehyde compound(9.2); R3, R4, R5, R6, R7, R8, R9 and RIO can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-Γ), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , Ci-C _ft alkoxide, C,-C ₆ alkyl, Ci-C ₆ fluoroalky , C ₂ - ₆ alkenyl, carboxyl (-COOH) and their combinations with one another. in the sixth compound (9), produced from main compound (2); when Rl is methyl (-CH3), R2 is ethyl (-C2H5), Rl 1 and R12 are methyl (-CH3), and in this compound (l -(3,4-dimethoxy- 2,5,6-trimethylphenyl)-3-(7-methoxy-3,4,5,8-tetramethyl-6-pr opoxy-l λ' -chroinen-2-yJ)butan- 1-one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound(9.3); R3,R4,R5,R6,R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , Ci-C _f i alkoxide, Cj-C ₆ a!kyl, C _r C ₆ fluoroalkyi, C?-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when Rl and R2 are ethyl (-C2H5), Rl l and R12 are methyl (-CH3), and in this compound ( l-(3,4-dimethoxy-2,5,6- trimethylpheny!)-3-(7-ethoxy-3,4,5,8-tetramethyl-6-propoxy-l λ ³ -chromen-2-yl)butan-l -one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound(9.4); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (- 1), methyl (-CH3), ethyl (-C2H5), amino (-NF12), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C _r C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyi, C,-C _f , alkenyl. carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when Rl is hydroxyl (- OH), R2 is methyl (-CH3), Rl l and R12 are methyl (-CH3), and in this compound ( l -(3,4- dimethoxy-2,5,6-triniethylphenyl)-3-(6-(hy λ ³ -chromen-2-yl)butan-l -one and methyl λ' -oxidane (3: 1 : 1 ) formaldehyde compound(9.5): R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (-11), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Ci-C ₆ alkoxide, Ci-C ₆ alkyl, Ci-C ₆ fluoroalkyi, C?.-Ce alkenyl, carboxyl (-COOH) and their combinations with one another. In the sixth compound (9), produced from main compound (2); when Rl is methyl (-CH3), R2 is hydroxyl(-O I), Rll and R12 are methyl (-CH3), and in this compound (l-(3,4- dimethoxy-2,5,6 rimethylphenyl)-3-(6-ethoxy-7 iydroperoxy-3,4,5,8-tetramethyl-l λ ³ chromen-2-yl)butan-l-one-and methyl- λ ^! -oxidane (3:1:1) formaldehyde compound(9.6); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxy 1, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C C ₆ alkoxide, C _\ -C ₆ alkyl, C _r C ₆ fluoroalkyl, C ₂ -Q, alkenyl, carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when Rl and R2 are hydroxy! (-OH), Rll and R12 are methyl (-CH3), and in this compound (l-(3,4-dimethoxy- 2,5,6-trimetlvlphenyl)-3-(7-hydroperoxy-6-(hydroxyperoxy)-3, 4,5,8-tetramethyl-l ^J -chromen- 2-yl)butan-l-one and methyl- λ'-oxidane (3:1:1) formaldehyde compound (9.7); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxy 1, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Cj-Q alkoxide, C _\ -C(, alkyl, C _r C ₆ fluoroalkyl, C C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when R l is hydroxy! (- OH), R2 is ethyl (-C2H5), Rll and R12 are methyl (-CH3), and in this compound (l-(3,4- dimethoxy-2,5,6 rimethylphenyl)-3-(7-ethoxy-6-(hydroxyperoxy)-3,4,5,8-tetram ethyl-l λ' - chromen-2-yl butan-l-one and methyl λ' -oxidane (3:1:1) formaldehyde compound (9.8); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-11), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2I15), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Cj-C ₆ alkoxide, C _r C ₆ alkyl, C|-C ₆ fluoroalkyl, C C ₍ , alkenyl, carboxyl (-COOH) and their combinations with one another.

In the sixth compound (9), produced from main compound (2); when Rl is ethyl (-C2II5), R2 is hydroxy! (-OH), Rll and R12 are methyl (-CH3), and in this compound (l-(3,4- dimethoxy-2,5,6-trimethylphenyi)-3-(7-hydropeiOxy-3,4,5,8-te tramethyi-6-propoxy-l λ ³ chromen-2-yl)butan-l-one and methyl λ' -oxidane (3:1:1) formaldehyde compound (9.9); R3,R4,R5,R6,R7,R8,R9 and R10 can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₍₁ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another. In the seventh compound ( 10), produced from main compound (2); when R l and R2 are methyl (-CH3), and in this compound (6,7-diethoxy~2,3,4,5,8-pentamethylnaphatehalen- l - yiium( lO. l); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (- H2), nitro (-N02), QrQ _> cycloalkenyl , C C ₆ alkoxide, Cj-C ₆ alkyl, C |-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another. in the seventh compound ( 10), produced from main compound (2); when R l is ethyl (- C2H5) and R2 is methyl (-CH3), and in this compound 7-ethoxy-2,3,4,5,8-pentamethyl-6- propoxynaphatehalen- l -y lium ( 10.2); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (- OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-N.H2), nitro (-N02), (.. -( ^' ,, cycloalkenyl , CrQ, alkoxide, alkyl, C j-Q fluoroalkyl, C ₂ -C-6 alkenyl, carboxyl (-COOH) and their combinations with one another.

In the seventh compound ( 10), produced from main compound (2); when Rl is methyl (- CH3) and R2 is ethyl (-C2H5), and in this compound 6-ethoxy-2,3,4,5,8-pentamethyl-7- propoxynaphatehaien- l -ylium ( 10.3); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxy!, (- OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C _r C ₆ alkoxide, C _r C ₆ alkyl, C, -C ₆ fluoroalkyl, alkenyl, carboxyl (-COOI I) and their combinations with one another.

In the seventh compound ( 10), produced from main compound (2); when Rl and R2 are ethyl (-C2H5), and in this compound 2,3,4,5, 8-pentamethyl-6,7-dipropoxynaphatehalen- l - ylium ( 10.4); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OI L), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methy l (-CH3), ethyl (-C2115), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Ci-C^ alkoxide, C _r C ₆ alkyl, C]-C ₆ fluoroalkyl, j-Cf, alkenyl, carboxyl (-COOH) and their combinations with one another.

In the seventh compound ( 10), produced from main compound (2); when R l is hydroxyl (- OH) and R2 is methyl (-CH3), and in this compound 7-ethoxy-6-(hydroxymethoxy)-2,3,4,5,8- pentamethylnaphatehalen-l -ylium (10.5); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-Oi l), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide. C,-C ₆ alkyl, C ,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the seventh compound ( 10), produced from main compound (2); when Rl is methyl (- CH3) and R2 is hydroxyl (-OH), and in this compound 6-ethoxy-7-(hydroxymethoxy)-2,3,4,5,8- pentamethylnaphatehalen-l-ylium (10.6); 3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C,-C ₆ cycioalkenyi , C C ₆ alkoxide, C _r C ₆ alkyl, C _r C ₆ fluoroalkyl, CVCs alkenyl, carboxyl (-COOH) and their combinations with one another. In the seventh compound (10), produced from main compound (2); when Rl 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 (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycioalkenyi , C,-C ₆ alkoxide. C,-C ₆ alkyl, C _r C ₆ fluoroalkyl, C2-C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the seventh compound (10), produced from main compound (2); when Rl is hydroxyl(- OH) and R2 is ethyl (-C2H5), and in this compound 6-(hydroxymethoxy)-2,3,4,5,8- pentamethyl-7-propoxynaphatehalen- l-ylium (10.8); R3,R4,R5,R6 and R7 can be; hydrogen, (- I I), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2FI5), amino (-NH2), nitro (-N02), C C ₆ cycioalkenyi , C,-C ₆ alkoxide, C _r Q alkyl, C]-C ₆ fluoroalkyl, CVC _s alkenyl, carboxyl (-COOH) and their combinations with one another.

In the seventh compound (10), produced from main compound (2); when Rl is ethyl (- C2H5) and R2 is hydroxyl(-Ol l), and in this compound 7-(hydroxymethoxy)-2,3,4,5,8- pentamethyl-6,7-propoxynaphatehalen-l -ylium (10.9); R3,R4,R5,R6 and R7 can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycioalkenyi , C _r C ₆ alkoxide, C C ₆ alkyl, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the eight compound (1 1 ), produced from main compound (2); when RKR2.R1 1 and R12 are methyl (-CH3), and in this compound ( 3-(6,7-dietoxy-3,4,5,8-tetramethyl-l h ^* -chromen- 2-yl)-l-(3,4-dimethoxy-2,5,6-trimethylphenyl)butan-1 -one-and methyl- λ' -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 (-Γ), methyl (-CH3), ethyl (-C2H5), amino (-MH2), nitro (-N02), C ₃ -Q, cycioalkenyi , C,-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

I the eight compound ( 11 ), produced from main compound (2); when Rl is ethyl (-C2115), R2 is methyl (-CH3) Rl 1 and R12 are methyl (-CH3) and in this compound (l -(3,4-dimethoxy- 2,5,6-trimethylphenyl)-3-(7-ethoxy,3,4,5,8-tetramethyl-6-pro poxy- l λ ³ -chromen-2-yl)butan-l- one-methyl- λ' -oxidane(3: l : l ) formaldehyde compound (11.2); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , Cj- , alkoxide, Cj-Q alkyl, C _\ -C ₆ fluoroalkyl, C C aikenyl, carboxyl (-COOH) and their combinations with one another.

In the eight compound (1 1 ), produced from main compound (2); when Rl is methy l (- CH3), R2 is ethyl (-C2H5), Rl 1 and R12 are methyl (-CH3) and in this compound (l -(3,4- dirnethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-3,4,5,8-tetram ethyl-7-propoxy-l λ" -chromen- 2-yl)butan-l -one-methyl- λ' -oxidane (3: 1 : 1) formaldehyde compound (11.3); R3.R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxyl, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C C ₆ cycloalkenyl , C|-C ₍ , alkoxide, C _r C ₆ alkyl, C C<, fluoroalkyl, C?-C ₆ aikenyl, carboxyl (-COOH) and their combinations with one another. In the eight compound ( 11), produced from main compound (2); when R 1 and R2 are ethyl (-C2H5), Rl I and R12 are methyl (-CH3) and in this compound (l -(3,4-dimethoxy-2,5,6- trimethylphenyl)-3-(,3,4,5,8-tetramethyl-6,7-dipropoxy- 1 λ ³ -chromen-2-y l)butan- 1 -one- methyl- λ' -oxidane(3: l : i) formaldehyde compound (11.4); R3,R4,R5,R6,R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxyl, (-011), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (- 1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyl , C,-C ₆ alkoxide, C1-C6 alkyl, C]-C ₆ fluoroalkyl, C ₂ -C ₆ aikenyl, carboxyl (-COOH) and their combinations with one another.

In the eight compound (1 1 ), produced from main compound (2); when R l is hydroxyl (- OH), R2 is methyl (-CH3), R l 1 and R12 are methyl (-CH3) and in this compound (l -(3,4- dimethoxy-2,5,6-trimethylphenyl)-3-(7-ethoxy-6-(hydroxyperox y)-3,4,5,8-tetramethyl-l λ - chromen-2-yl)butan-l-one and methyl λ' -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 (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), Cj-C _f i cycloalkenyl , Ci-C ₆ alkoxide, C C ₆ alkyl, C(-C ₍ , fluoroalkyl, C2-Q, aikenyl, carboxyl (-COOH) and their combinations with one another.

In the eight compound (1 1), produced from main compound (2); when Rl is methyl (-CFI3), R2 is hydroxyl (-011), Rl l and R12 are methyl (-CF13) and in this compound ( l-(3,4- dimethoxy-2,5,6-trimethylphenyl)-3-(6-ethoxy-7-(hydroxymetho xy)-3,4,5,8-tetramethyl~ ³ - chromen-2-yl)butan-l -one-and-methyl- ¹ -oxidane(3: l : 1) formaldehyde compound (11.6); R3,R4,R5,R6,R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxy., (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C ₃ -C ₆ cycloalkenyi , Cj-C ₆ alkoxide, C,-C ₆ alkyl, C,-C ₆ fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOI I) and their combinations with one another. in the eight compound ( 1 1), produced from main compound (2); when Rl and R2 are hydroxy! (-OH), Rl l and R12 are methyl (-CH3) and in this compound (3-(6,7- bis(hydroxymethoxy)-3,4,5,8-tetramethyl-l „ ³ -chromen-2-yl)-l -(3,4-dimethoxy-2,5,6- trimethylphenyl)butan-l-one-and-methyl- λ' -oxidane(3 : 1 : 1 ) formaldehyde compound (11.7); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), ch!oride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (- 02), CrQ, cycloalkenyi , Cj- , alkoxide, C _r C ₆ alkyl, C _r Q, fluoroalkyl, C ₂ -C ₆ alkenyl, carboxy l (-COOH) and their combinations with one another.

In the eight compound (1 1 ), produced from main compound (2); when Rl is hydroxy! (- Oil), R2 is ethyl (-C2H5), Rl l and R12 are methyl (-CH3) and in this compound l-(3,4- dimethoxy-2,5,6-trimethylphenyl)-3-(6-(hydroxymethoxy)-(3,4, 5,8-tetramethyl-7-propoxy-l λ ^' ' -chromen-2-y l)butan- 1 -one-and-methyl- λ' -oxidane(3 : 1 : 1 )formaldehyde compound (11.8); R3,R4,R5,R6,R7,R8,R9 and RIO can be; hydrogen, (-H), hydroxy!, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2), nitro (-N02), C _. rQ cycloalkenyi , Ci-C ₆ alkoxide, Cj-Q alkyl, Q-Q fluoroalkyl, C ₂ -C ₆ alkenyl, carboxyl (-COOH) and their combinations with one another.

In the eight compound ( 1 1 ). produced from main compound (2); when Rl is ethyl (-C2H5), R2 is hydroxy! (-OH), R l l and R12 are methyl (-CH3) and in this compound (l-(3,4- dimethoxy-2,5,6 rimethylpheny!)-3-(7-(hydroxymethoxy)-(3,4,5,8-tetramethyl-6 -propoxy-l ^'1 - chromen-2-l) butan-l-one-and-methyl-/J-oxidane(3: l : l ) formaldehyde compound (11.9); R3,R4,R5,R6,R7,R8,R9 and RI O can be; hydrogen, (-H), hydroxy 1, (-OH), fluoride (-F), chloride, (-CL) , bromide (-Br), iodine (-1), methyl (-CH3), ethyl (-C2H5), amino (-NH2 ), nitro (-N02), C3-C ₆ cycloalkenyi , C ₅ -C ₆ alkoxide, C|-C ₆ alkyl, C)-C ₃ fluoroalkyl. C2-CV, alkenyl, carboxyl (-COOH) and their combinations with one another.