Isoprenoid derivatives and anti-ulcer agents containing the same

Claim 2

An anti-ulcer agent which comprises an isoprenoid derivative represented by the formula (I): Wherein: R represents a group of formula [in the above formula, R,, R 2 and R 3 may be the same or different each other and each represents a hydrogen atom, a hydroxy group, a lower alkanoyloxy group, a lower alkyl group or a lower alkoxy group, provided that two or more of them do not represent hydrogen atoms at the same time; R 4 and R s may be the same or different each other and each represents a hydrogen atom, a hydroxy group or a lower alkanoyloxy group; represents the single or the double bond between the carbon atoms; m represents 0 or 1; n represents 0 or an integer of from 1 to 9, provided that the sum of m and n is an integer of from 1 to 9].

Claim 3

An anti-ulcer agent as claimed in claim 1, wherein R represents a group of formula: [wherein Ri, R 2 and R 3 are as defined in claim 1].

Claim 4

An anti-ulcer agent as claimed in claim 2, wherein the isoprenoid derivative is a compound selected from the group consisting of: 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,4-hydroquinone, 2-Geranyl-1,4-hydroquinone, 2-Geranyl-1,3-hydroquinone, 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl]-1,4-hydroquinone, 2-Farnesyl-1,4-hydroquinone, 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl]-1,4-diacetoxybenzene, 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl]-1,4-dibutoxybenzene, 2-Geranylgeranyl-1,4-hydroquinone, 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,4-diacetoxybenzene, 2-(3,7,11,15,19-Pentamethyl-2,6,10,14,18-eicosapentaenyl)-1,4-hydroquinone, 2-(3,7,11,15,19,23-Hexamethyl-2,6,10,14,18,22-tetracosahexaethyl-1,4-hydroquinone, 2-(3,7,11,15,19,23,27-Heptamethyl-2,6,10,14,18,22,26-octacosaheptaenyl)-1,4-hydroquinone, 2-Solanesyl-1,4-hydroquinone, 2,6-Dimethyl-4-(3,7,11,15-tetramethyl-2-hexadecenyl)phenol, 2,6-Di-t-butyl-4-(3,7,11,15-tetramethyl-2-hexadecenyl)phenol, 2-Methyl-4-(3,7,11,15-tetramethyl-2-hexadecenyl)phenol, 3-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-benzenediol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-benzenediol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-dimethoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2,3-benzenetriol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3-diacetoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3-benzenediol, 2- (3,7,11,15-Tetramethyl-2-hexadecenyl)-1 , 3,5-triacetoxybenzene, 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3,5-benzenetriol, 4-(3,7 ,11 ,15-Tetramethyl-2-hexadecenyl)-1,3,5-triacetoxybenzene, 3-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-diacetoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-diacetoxybenzene, and 2-(3,7,11,15-Tetramethylhexadecyl)-1,4-hydroquinone, 4-(3,7,11,15-Tetramethylherxadecyl)-1,3-benzenediol.

Claim 5

An anti-ulcer agent as claimed in claim 1, wherein R represents a group of formula: [wherein Ra 4 , R 5 and are as defined in claim 1

Claim 6

An anti-ulcer agent as claimed in claim 4, wherein the isoprenoid derivative is a compound selected from the group consisting of: 2-Methyl-2-(4,8,12-trimethyltridecyl)-6-chromanol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-5-hydroxychromene, 2-Methyl-2-[4(R),8(R),12-trimethyltridecyl]-6-chromanol, 2-Methyl-2-[4(R),8(R),12-trimethyltridecyl]-6-chromanol acetate, 2-Methyl-2-[4(R),8(R),12-trimethyltridecyl]-5-acetoxychromene, 2-Methyl-2-[4(R),8(R),12-trimethyltridecyl]-6-t-butoxychromene, 2-Methyl-2-[4(R),8(R),12-trimethyltridecyl]-6-propionyloxychromene, 2-Methyl-2-(4-methyl-3-pentenyl)-6-chromenol, 2-Methyl-2-(4-methyl-3-pentenyl)-5-hydroxychromene, 2-Methyl-2-(4,8-dimethyl-3,7-nonadienyl)-6-chromenol, 2-Methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-6-chromenol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-7-chromanol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-7,8-dichromanol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-5,7-dichromanol and 2-Methyl-2-(4,8,12-trimethyltridecyl)-8-chromanol.

Claim 7

An anti-culcer agent as claimed in claim 1, wherein R represents a group of formula:

Claim 8

An anti-ulcer agent as claimed in claim 6, wherein the isoprenoid derivative is a compound selected from the group consisting of: 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,4-benzoquinone, and 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl)-1,4-benzoquinone.

Claim 9

An isoprenoid compound represented by the formula (la): wherein: R represents a group of formula [in the above formula, Ri, R 2 and R 3 may be the same or different each other and each represents a hydrogen atom, a hydroxy group, a lower alkanoyloxy group, a lower alkyl group or a lower alkoxy group, provided that two or more of them do not represent hydrogen atoms at the same time; R 4 ' and R s may be the same or different each other and each represents a hydrogen atom or a hydroxy group; represents the single or the double bond between the carbon atoms; m represents 0 or 1; n represents an integer of 3, 4 or 8, provided that - - - - - represents the single bond when n is 3 and represents the double bond when n is 8].

Claim 10

An isoprenoid compound represented by the formula (la): wherein: R represents a group of formula [in the above formula, Ri, R 2 and R 3 may be the same or different each other and each represents a hydrogen atom, a hydroxy group, a lower alkanoyloxy group, a lower alkyl group or a lower alkoxy group, provided that two or more of them do not represent hydrogen atoms at the same time; R 4 ' and R s may be the same or different each other and each represents a hydrogen atom or a hydroxy group; represents the single or the double bond between the carbon atoms; m represents 0 or 1; n represents an integer of 3, 4 or 8, provided that - - - - - represents the single bond when n is 3 and represents the double bond when n is 8].

Claim 11

An isoprenoid compound as claimed in claim 8, wherein R represents a group of formula: [wherein Ri, R 2 and R 3 are as defined in claim 8].

Claim 12

An isoprenoid compound as claimed in claim 9, which is selected from the group consisting of: 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1, 4-hydroquinone, 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl]-1,4-hydroquinone, 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl]-1,4-dibutoxybenzene, 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,4-diacetoxybenzene, 2-(3,7,11,15,19-Pentamethyl-2,6,10,14,18-eicosapentaenyl)-1,4-hydroquinone, 2,6-Di-t-butyl-4-(3,7,11,15-tetramethyl-2-hexadecenyl)phenol, 3-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-benzenediol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-benzenediol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-l,2-dimethoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2,3-benzenetriol, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1, 3-diacetoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3-benzenediol, 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3,5-triacetoxybenzene, 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,3,5-benzenetriol, 4-(3,7,11,15-Tetramethyl-2-hexadecenl)-1,2,3-triacetoxybenzene, 3-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-diacetoxybenzene, 4-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,2-diacetoxybenzene, and 4-(3,7,11,15-Tetramethylhexadecyl)-1,3-benzenediol.

Claim 13

An isoprenoid compound as claimed in claim 8, wherein R represents a group of formula:

Claim 14

An isoprenoid compound as claimed in claim 11, selected from the group consisting of: 2-(3,7,11,15-Tetramethyl-2-hexadecenyl)-1,4-benzoquinone, and 2-[3,7(R),11 (R),15-Tetramethyl-2-hexadecenyl)-1,4-benzoquinone.

Claim 15

An isoprenoid compound as claimed in claim 8, wherein R represents a group of formula: [wherein, R 4 ' and Rs are as defined in claim 8].

Claim 16

An isoprenoid compound as claimed in claim 13, selected from the group consisting of: 2-Methyl-2-(4,8,12-trimethyltridecyl)-7-chromanol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-7,8-dichromanol, 2-Methyl-2-(4,8,12-trimethyltridecyl)-5,7-dichromanol, and 2-Methyl-2-(4,8,12-trimethyltridecyl)-8-chromanol.