Ethyleneglycol derivatives, their production and use

Claim 2

A compoud of the formula (I), inclusive of salts thereof, for use in inhibiting multiplication of tumor cells and prolonging the survival time of a tumor-bearing warm-blooded animal: wherein R 1 is C 8-26 aliphatic hydrocarbon residue which may be substituted; and R 2 , R 3 and R 4 are each hydrogen, C 1-5 alkyl which may be substituted, or - NR 2 R 3 R 4 represents cyclic ammonio.

Claim 3

The compound for the use according to Claim 1, wherein the aliphatic hydrocarbon residue is C 10-20 alkyl, C 10-20 alkenyl or C 14-24 aralkyl.

Claim 4

The compound for the use according to Claim 1, wherein - NR 2 R 3 R 4 represents cyclic ammonio.

Claim 5

The compound for the use according to Claim 3, wherein cyclic ammonio is pyridinio, oxazolio, thiazolio, pyridazinio, quinolinio or isoquinolinio.

Claim 6

The compound for the use according to Claim 1, wherein R 1 is C 10-15 aliphatic hydrocarbon residue, and R 2 , R 3 and R 4 are each hydrogen or C 1-5 alkyl which may be substituted.

Claim 7

The compound for the use according to Claim 1, wherein the compound is administered by injection at the dose level of about 0.1 to 100 mg per kilogram body weight daily.

Claim 8

A compound, inclusive of salts thereof, of the formula: wherein R 1 is C 8-26 aliphatic hydrocarbon residue, and A + is cyclic ammonio.

Claim 9

A compound, inclusive of salts thereof, of the formula: wherein R 1 is C 8-26 aliphatic hydrocarbon residue, and A + is cyclic ammonio.

Claim 10

The compound according to Claim 7, wherein the aliphatic hydrocarbon residue is C 10-20 alkyl, C 10-20 alkenyl or C 14-24 aralkyl.

Claim 11

The compound according to Claim 7, wherein A + is pyridinio, oxazolio, thiazolio, pyridazinio,-quinolinio or isoquinolinio.

Claim 12

The compound according to Claim 7, which is 2-octadecyloxyethyl 2-pyridinioethyl phosphate.

Claim 13

A compound, inclusive of salts thereof, of the formula: wherein is C 10-15 aliphatic hydrocarbon residue; and , and are each hydrogen or C 1-5 alkyl which may be substituted.

Claim 14

A compound, inclusive of salts thereof, of the formula: wherein is C 10-15 aliphatic hydrocarbon residue; and , and are each hydrogen or C 1-5 alkyl which may be substituted.

Claim 15

The compound according to Claim 11, wherein is C 10-15 alkyl.

Claim 16

The compound according to Claim 11, wherein , and are each unsubstituted C 1-5 alkyl.

Claim 17

The compound according to Claim 11, wherein is C 1-5 alkyl which is substituted with C 1-3 alkoxy- or hydroxy-carbonyl, and and are each unsubstitued C 1-5 alkyl.

Claim 18

The compound according to Claim 11, which is 2-tetradecyloxyethyl 2-trimethylammonioethyl phosphate.

Claim 19

The compound according to Claim 11, which is 2-tetradecyloxyethyl 2-[N,N-dimethyl-N-(3-methoxycarbonylpropyl)]ammonioethyl phosphate.

Claim 20

A pharmaceutical composition for inhibiting multiplication of tumor cells and prolonging the survival time of tumor-bearing warm-blooded animal which contains an effective amount of a compound (I), inclusive of salts thereof, as-defined in any one of claims 1 to 5 and 7 to 16 and a pharmaceutically acceptable carrier, vehicle or diluent therefor.

Claim 21

A process for producing a compound, inclusive of salts thereof, as claimed in any one of Claims 7 to 16, characterized by (a) reacting a compound of the formula: wherein R 1 is as defined in Claim 7 or is defined in Claim 11 and Y is halogen, with a compound of the formula: A wherein A is as defined in Claim 7, or with a compound of the formula: wherein , and are as defined in Claim 11, and if necessary, followed by treatment with water; or (b) reacting a compound of the formula: wherein R 1 is as defined above, with a compound of the formula: wherein A is as defined above, or with a compound of the formula: wherein , and are as defined above, or in case that R 3 and R are hydrogen, with a compound of the formula: wherein one of R' and R" is R 2 and another is a protective group, or R' and R", on cyclization with the adjacent N atom, form succinimido or phthalimido, followed by treatment with water and removal of the protective group, or ( c ) in case that and are hydrogen, reacting a compound of the formula: wherein is as defined above, with a compound of the formula: wherein X, R' and R" are as defined above, and if necessary, followed by treatment with water.