2-amino-1,3-propanediol compound and immunosuppressant

• US 5,604,229 A
• Filed: 06/17/1994
• Issued: 02/18/1997
• Est. Priority Date: 10/21/1992
• Status: Expired due to Term

• Current Assignee: Mitsubishi Tanabe Pharma Corporation (Mitsubishi Chemical Group Corp.)
• Original Assignee: Taito Co. Ltd. (Mitsui DM Sugar Holdings Company Limited), Yoshitomi Pharmaceutical Industries, Ltd. (UBE Corporation)
• Inventors: Adachi, Kunitomo, Chiba, Kenji, Sasaki, Shigeo, Mishina, Tadashi, Fujita, Tetsuro, Yoneta, Masahiko
• Primary Examiner(s): Ivy, C. Warren
• Assistant Examiner(s): COVINGTON, RAYMOND K
• Application Number:
  US08/244,942
• Time in Patent Office: 977 Days
• Field of Search: 546/210, 546/246, 546/247, 546/334, 560/172, 562/11, 558/169, 514/114, 514/119, 514/357, 514/255, 514/372, 514/403, 514/427, 514/438, 514/459, 514/471, 564/336, 564/340, 564/342, 564/346, 564/374, 564/383, 564/454, 564/123, 549/75, 549/426, 549/495, 548/214, 548/373.1, 548/516, 544/401
• US Class Current: 514/252.1
• CPC Class Codes: C07C 215/10 with one amino group and at least two hydroxy groups bound to the carbon skeleton
• CPC Class Codes: C07C 215/18 with hydroxy groups and at least two amino groups bound to the carbon skeleton
• CPC Class Codes: C07C 215/20 the carbon skeleton being saturated and containing rings
• CPC Class Codes: C07C 215/24 and acyclic
• CPC Class Codes: C07C 215/26 and containing rings other than six-membered aromatic rings
• CPC Class Codes: C07C 215/28 and containing six-membered aromatic rings
• CPC Class Codes: C07C 215/34 containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton and at least one hydroxy group bound to another carbon atom of the carbon skeleton
• CPC Class Codes: C07C 215/42 having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 215/54 linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 215/56 with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by hydroxy groups
• CPC Class Codes: C07C 215/68 having amino groups bound to carbon atoms of six-membered aromatic rings and hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 217/28 having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
• CPC Class Codes: C07C 217/30 having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
• CPC Class Codes: C07C 217/34 by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
• CPC Class Codes: C07C 217/48 the carbon skeleton being unsaturated and containing rings
• CPC Class Codes: C07C 217/52 having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 217/64 with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 217/72 linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 217/76 having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 219/06 having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 219/24 : having esterified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 219/30 : with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains further substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 225/04 : the carbon skeleton being saturated
• CPC Class Codes: C07C 225/06 : and acyclic
• CPC Class Codes: C07C 225/10 : with doubly-bound oxygen atoms bound to carbon atoms not being part of rings
• CPC Class Codes: C07C 225/14 : the carbon skeleton being unsaturated
• CPC Class Codes: C07C 225/16 : and containing six-membered aromatic rings
• CPC Class Codes: C07C 229/22 : the carbon skeleton being further substituted by oxygen atoms
• CPC Class Codes: C07C 229/38 : having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 229/46 : having amino or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
• CPC Class Codes: C07C 233/18 : having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 233/31 : with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 233/35 : with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 233/36 : having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 233/41 : with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 233/43 : having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
• CPC Class Codes: C07C 233/47 : having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 237/06 : having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 237/24 : having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 237/30 : having the nitrogen atom of the carboxamide group bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 251/38 : to carbon atoms of a saturated carbon skeleton
• CPC Class Codes: C07C 2601/08 : the ring being saturated
• CPC Class Codes: C07C 2601/14 : The ring being saturated
• CPC Class Codes: C07C 271/20 : to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 271/24 : with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
• CPC Class Codes: C07C 271/28 : to a carbon atom of a non-condensed six-membered aromatic ring
• CPC Class Codes: C07C 323/25 : the carbon skeleton being acyclic and saturated
• CPC Class Codes: C07C 323/30 : having the sulfur atom of at least one of the thio groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
• CPC Class Codes: C07C 323/32 : having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
• CPC Class Codes: C07C 323/34 : the thio group being a mercapto group
• CPC Class Codes: C07C 323/41 : Y being a hydrogen or an acyclic carbon atom
• CPC Class Codes: C07D 207/06 : with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 207/09 : Radicals substituted by nitrogen atoms, not forming part of a nitro radical
• CPC Class Codes: C07D 207/325 : with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
• CPC Class Codes: C07D 207/335 : Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 211/14 : with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
• CPC Class Codes: C07D 211/26 : with hydrocarbon radicals, substituted by nitrogen atoms
• CPC Class Codes: C07D 213/38 : having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
• CPC Class Codes: C07D 213/40 : Acylated substituent nitrogen atom
• CPC Class Codes: C07D 231/12 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 233/56 : with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• CPC Class Codes: C07D 233/64 : with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
• CPC Class Codes: C07D 237/08 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/26 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 241/12 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 249/08 : 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: C07D 261/08 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 263/32 : with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• CPC Class Codes: C07D 265/30 : not condensed with other rings
• CPC Class Codes: C07D 275/02 : not condensed with other rings
• CPC Class Codes: C07D 277/28 : Radicals substituted by nitrogen atoms
• CPC Class Codes: C07D 279/12 : not condensed with other rings
• CPC Class Codes: C07D 295/13 : to an acyclic saturated chain
• CPC Class Codes: C07D 295/135 : with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
• CPC Class Codes: C07D 307/52 : Radicals substituted by nitrogen atoms not forming part of a nitro radical
• CPC Class Codes: C07D 309/32 : having two double bonds between ring members or between ring members and non-ring members
• CPC Class Codes: C07D 317/28 : Radicals substituted by nitrogen atoms nitro radicals C07D317/16
• CPC Class Codes: C07D 333/20 : by nitrogen atoms nitro, nitroso radicals C07D333/12

Abstract

2-Amino-1,3-propanediol compounds of the formula (I) ##STR1## wherein R is an optionally substituted straight- or branched carbon chain, an optionally substituted aryl, an optionally substituted cycloalkyl or the like, and R², R³, R⁴ and R⁵ are the same or different and each is a hydrogen, an alkyl, an aralkyl, an acyl or an alkoxycarbonyl, pharmaceutically acceptable salts thereof and immunosuppressants comprising these compounds as active ingredients.

The 2-amino-1,3-propanediol compounds of the present invention show immunosuppressive action and are useful for suppressing rejection in organ or bone marrow tranplantation, prevention and treatment of autoimmune diseases or as reagents for use in medicinal and pharmaceutical fields.

Claims

1. A 2-amino-1,3-propanediol, having the formula ##STR437## wherein Re is a phenylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms;

a phenylalkyl which may be substituted by a straight- or branched chain C6-C20 alkyl optionally substituted by halogen, a straight- or branched chain C6-C20 alkoxy optionally substituted by halogen, a straight- or branched chain C6-C20 alkenyloxy, phenylalkoxy, halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl;

a cycloalkylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms;

a cycloalkylalkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

a heteroarylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms;

a heteroarylalkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

a heterocyclic alkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms, or a heterocyclic alkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

wherein the alkyl moiety may have, in the carbon chain, a bond or a hereto atom selected from the group consisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, and carbonyl, and may have, as a substituent, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino, hydroxy or carboxy;

or a pharmaceutically acceptable salt thereof.

2. A 2-amino-1,3-propanediol compound of claim 1, having the formula ##STR438## wherein Rf is a phenylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms which may have, in the carbon chain, one or two oxygen atoms;

a phenylalkyl which may be substituted by a straight- or branched chain C6-C20 alkyl optionally substituted by halogen, a straight- or branched chain C6-C20 alkoxy optionally substituted by halogen, a straight- or branched chain C6-C20 alkenyloxy, phenylalkoxy, halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl;

a cycloalkylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms which may have, in the carbon chain, one or two oxygen atoms;

a cycloalkylalkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

a heteroarylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms which may have, in the carbon chain, one or two oxygen atoms;

a heteroarylalkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

a heterocyclic alkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms which may have, in the carbon chain, one or two oxygen atoms, or a heterocyclic alkyl substituted by a straight- or branched chain alkyl having 6 to 20 carbon atoms;

wherein the alkyl moiety may have, in the carbon chain, a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino, hydroxy and carboxy;

or a pharmaceutically acceptable salt thereof.

3. A 2-amino-1,3-propanediol compound of any one of claims 1 or 2, having the formula ##STR439## wherein Rg is a phenylalkyl wherein the alkyl moiety is a straight- or branched chain having 6 to 20 carbon atoms which may have, in the carbon chain, one or two oxygen atoms;

a phenylalkyl which may be substituted by a straight- or branched chain C6-C14 alkyl optionally substituted by halogen, a straight- or branched chain C6-C14 alkoxy optionally substituted by halogen, a straight- or branched chain C6-C14 alkenyloxy, phenylalkoxy, halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl;

a cycloalkylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms;

a cycloalkylalkyl substituted by a straight- or branched chain alkyl having 6 to 14 carbon atoms;

a heteroarylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms;

a heteroarylalkyl substituted by a straight- or branched chain alkyl having 6 to 14 carbon atoms;

a heterocyclic alkyl wherein the alkyl moiety has 6 to 20 carbon atoms, or a heterocyclic alkyl substituted by a straight- or branched chain alkyl having 6 to 14 carbon atoms;

or a pharmaceutically acceptable salt thereof.

4. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR440## wherein Rh is a phenylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms, a phenylalkoxyalkyl wherein the alkyl moiety and alkoxy moiety have 6 to 20 carbon atoms in total, a phenoxyalkyl wherein the alkyl moiety has 6 to 20 carbon atoms or a phenoxyalkoxyalkyl wherein the alkyl moiety and alkoxy moiety have 6 to 20 carbon atoms in total, or a pharmaceutically acceptable salt thereof.

5. A 2-amino-1,3-propanediol compound of claim 4, which is selected from the group consisting of

2-amino-2-(8-phenyloctyl)-1,3-propanediol,

2-amino-2-(9-phenylnonyl)-1,3-propanediol,

2-amino-2-(10-phenyldecyl)-1,3-propanediol,

2-amino-2-(11-phenylundecyl)-1,3-propanediol,

2-amino-2-(12-phenyldodecyl)-1,3-propanediol,

2-amino-2-(13-phenyltridecyl)-1,3-propanediol,

2-amino-2-(14-phenyltetradecyl)-1,3-propanediol,

2-amino-2-(15-phenylpentadecyl)-1,3-propanediol,

2-amino-2-(16-phenylhexadecyl)-1,3-propanediol,

2-amino-2-[6-(8-phenyloctyloxy)hexyl]-1,3-propanediol,

2-amino-2-(8-phenylmethyloxyoctyl)-1,3-propanediol,

2-amino-2-(9-phenoxynonyl)-1,3-propanediol,

2-amino-2-(12-phenoxydodecyl)-1,3-propanediol and

2-amino-2-[6-(2-phenoxyethyloxy)hexyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

6. A 2-amino-1,3-propanediol compound of claim 4, which is selected from the group consisting of

2-amino-2-(10-phenyldecyl)-1,3-propanediol,

2-amino-2-(13-phenyltridecyl)-1,3-propanediol,

2-amino-2-[6-(8-phenyloctyloxy)hexyl]-1,3-propanediol,

2-amino-2-(8-phenylmethyloxyoctyl)-1,3-propanediol,

2-amino-2-(9-phenoxynonyl)-1,3-propanediol,

2-amino-2-(12-phenoxydodecyl)-1,3-propanediol and

2-amino-2-[6-(2-phenoxyethyloxy)hexyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

7. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR441## wherein Ri is a phenylalkyl substituted by a straight- or branched chain C6-C14 alkyl optionally substituted by halogen, a straight- or branched chain C6-C14 alkoxy optionally substituted by halogen or a straight- or branched chain C6-C14 alkenyloxy,

wherein the alkyl moiety of phenylalkyl may be substituted by hydroxy, or a pharmaceutically acceptable salt thereof.

8. A 2-amino-1,3-propanediol compound of claim 7, having the formula ##STR442## wherein Rj is a phenylalkyl substituted by a straight- or branched chain C6-C14 alkyl optionally substituted by halogen, a straight- or branched chain C6-C14 alkoxy optionally substituted by halogen or a straight- or branched chain C6-C14 alkenyloxy, wherein the alkyl moiety is a C2-C6 alkyl optionally substituted by hydroxy, or a pharmaceutically acceptable salt thereof.

9. A 2-amino-1,3-propanediol compound of claim 7, which is selected from the group consisting of

2-amino-2-[2-(4-heptylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tridecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tetradecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-hexyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-heptyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tridecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(8-fluorooctyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(12-fluorododecyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-fluoroheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(11-fluoroundecyloxy)phenyl)ethyl]-1,3propanediol and

2-amino-2-[2-(4-(7-octenyloxy)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

10. A 2-amino-1,3-propanediol compound of claim 7, which is selected from the group consisting of

2-amino-2-[2-(4-heptylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-heptyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecyloxyphenyl)ethyl]-1,3-propanediol and

2-amino-2-[2-(4-(7-octenyloxy)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

11. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR443## wherein Rk is a phenylalkyl substituted by phenylalkoxy, halophenylalkoxy, phenylalkoxyalkyl, phenoxyalkoxy or phenoxyalkyl, or a pharmaceutically acceptable salt thereof.

12. A 2-amino-1,3-propanediol compound of claim 11, having the formula ##STR444## wherein Rl is a phenylalkyl substituted by phenylalkoxy wherein the alkoxy moiety has 2 to 8 carbon atoms, halophenylalkoxy wherein the alkoxy moiety has 2 to 8 carbon atoms, phenylalkoxyalkyl wherein the alkoxy moiety and alkyl moiety have 2 to 8 carbon atoms in total, phenoxyalkoxy wherein the alkoxy moiety has 2 to 8 carbon atoms or phenoxyalkyl wherein the alkyl moiety has 2 to 8 carbon atoms, where the alkyl moiety has 2 to 6 carbon atoms, or a pharmaceutically acceptable salt thereof.

13. A 2-amino-1,3-propanediol compound of claim 11, which is selected from the group consisting of

2-amino-2-[2-(4-phenylmethyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(2-phenylethyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(3-phenylpropyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(4-phenylbutyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenylpentyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenylhexyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-phenylheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(8-phenyloctyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[4-(6-(4-fluorophenyl)hexyloxy)phenyl)ethyl]-1,3propanediol,

2-amino-2-[2-(4-(5-phenylpentyloxymethyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(4-phenoxybutyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenoxypentyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenoxyhexyloxy)phenyl) ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-phenoxyheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(4-phenoxybutyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenoxypentyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenoxyhexyl)phenyl)ethyl]-1,3-propanediol and

2-amino-2-[2-(4-(7-phenoxyheptyl)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

14. A 2-amino-1,3-propanediol compound of claim 11, which is selected from the group consisting of 2-amino-2-[2-(4-(6-phenylhexyloxy)phenyl)ethyl]-1,3-propanediol and 2-amino-2-[2(4-(5-phenylpentyloxymethyl)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

15. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR445## wherein Rm is an alkyl-substituted cycloalkylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms in total, or a pharmaceutically acceptable salt thereof.

16. A 2-amino-1,3-propanediol compound of claim 15, which selected from the group consisting of

2-amino-2-[3-(4-heptylcyclohexyl)propyl]-1,3-propanediol,

2-amino-2-[4-(4-butylcyclohexyl)butyl]-1,3-propanediol,

2-amino-2-[2-(4-octylcyclohexyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonylcyclohexyl)ethyl]-1,3-propanediol and

2-amino-2-[2-(4-dodecylcyclohexyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

17. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR446## wherein Rn is a 1-alkyl-substituted piperidin-4-ylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms in total, or a pharmaceutically acceptable salt thereof.

18. A 2-amino-1,3-propanediol compound of claim 17, which is selected from the group consisting of 2-amino-2-[2-(1-octylpiperidin-4-yl)ethyl]-1,3-propanediol and 2-amino-2-[2-(1-dodecylpiperidin-4-yl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

19. A 2-amino-1,3-propanediol compound of claim 3, having the formula ##STR447## wherein Ro is a thienylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms, an alkyl-substituted thienylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms in total, a pyridylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms or an alkyl-substituted pyridylalkyl wherein the alkyl moiety has 6 to 20 carbon atoms in total, or a pharmaceutically acceptable salt thereof.

20. A 2-amino-1,3-propanediol compound of claim 19, which is selected from the group consisting of

2-amino-2-[2-(5-octyl-2-thienyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(5-nonyl-2-thienyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(5-decyl-2-thienyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(5-dodecyl-2-thienyl)ethyl]-1,3-propanediol,

2-amino-2-[13-(2-thienyl)tridecyl]-1,3-propanediol,

2-amino-2-[2-(5-octyl-2-pyridyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(5-decyl-2-pyridyl)ethyl]-1,3-propanediol,

2-amino-2-[13-(2-pyridyl)tridecyl]-1,3-propanediol,

2-amino-2-[2-(2-octyl-5-pyridyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(2-decyl-5-pyridyl)ethyl]-1,3-propanediol and

2-amino-2-[13-(3-pyridyl)tridecyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

35. A 2-amino-1,3-propanediol compound of claim 8, which is selected from the group consisting of

2-amino-2-[2-(4-heptylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tridecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tetradecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-hexyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-heptyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-tridecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(8-fluorooctyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(12-fluorododecyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-fluoroheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(11-fluoroundecyloxy)phenyl)ethyl]-1,3propanediol and

2-amino-2-[2-(4-(7-octenyloxy)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

36. A 2-amino-1,3-propanediol compound of claim 8, which is selected from the group consisting of

2-amino-2-[2-(4-heptylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-decylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-heptyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-octyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-nonyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-undecyloxyphenyl)ethyl]-1,3-propanediol and

2-amino-2-[2-(4-(7-octenyloxy)phenyl)ethyl]-1,3-propanediol, a pharmaceutically acceptable salt thereof.

37. A 2-amino-1,3-propanediol compound of claim 12, which is selected from the group consisting of

2-amino-2-[2-(4-phenylmethyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(2-phenylethyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(3-phenylpropyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(4-phenylbutyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenylpentyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenylhexyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-phenylheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(8-phenyloctyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[4-(6-(4-fluorophenyl)hexyloxy)phenyl)ethyl]-1,3propanediol,

2-amino-2-[2-(4-(5-phenylpentyloxymethyl)phenyl)ethyl]-1,3 -propanediol,

2-amino-2-[2-(4-(4-phenoxybutyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenoxypentyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenoxyhexyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-phenoxyheptyloxy)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(4-phenoxybutyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(5-phenoxypentyl)phenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(6-phenoxyhexyl)phenyl)ethyl]-1,3-propanediol and

2-amino-2-[2-(4-(7-phenoxyheptyl)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

38. A 2-amino-1,3-propanediol compound of claim 12, which is selected from the group consisting of 2-amino-2-[2-(4-(6-phenylhexyloxy)phenyl)ethyl]-1,3-propanediol and 2-amino-2-[2-(4-(5-phenylpentyloxymethyl)phenyl)ethyl]-1,3-propanediol, or pharmaceutically acceptable salt thereof.

40. A method for immunosuppression of an immune system of a mammal, which comprises administering to a mammal an immunosuppressing effective amount of any one of the compounds claimed in claims 1, 21, 24, 29 and 32.

41. A method for suppression of rejection in an organ or bone marrow transplantation in a mammal, which comprises administering to a mammal a rejection suppressing effective amount of any one of the compounds claimed in claims 1, 21, 24, 29 or 32.

42. A method for prevention or treatment of autoimmune disease, which comprises administering to a mammal a therapeutically effective amount of any one of the compounds claimed in claims 1, 21, 24, 29 or 32.

43. The method according to claim 42, wherein the autoimmune disease is rheumatoid arthritis.

44. A method for prevention or treatment of psoriasis or atopic dermatitis, which comprises administering to a mammal a therapeutically effective amount of any one of the compounds claimed in claims 1, 21, 24, 29 or 32.

45. A method for prevention or treatment of bronchial asthma or pollinosis, which comprises administering to a mammal a therapeutically effective amount of any one of the compounds claimed in claims 1, 21, 24, 29 or 32.

46. The method according to claim 40, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

47. The method according to claim 41, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

48. The method according to claim 42, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

49. The method according to claim 43, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

50. The method according to claim 44, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

51. The method according to claim 45, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol or a pharmaceutically acceptable salt thereof.

52. The method according to any one of claims 40, 41, 42, 43, 44 or 45, wherein the compound is 2-amino-2-(2-(4-octylphenyl)ethyl)-1,3-propanediol hydrochloride.

21. A 2-amino-1,3-propanediol compound, having the formula ##STR448## wherein Rp is a phenyl substituted by C6-C18 alkyl, a cycloalkyl, heteroaryl or a heterocycle, or a pharmaceutically acceptable salt thereof.

22. A 2-amino-1,3-propanediol compound of claim 21, having the formula ##STR449## wherein Rq is a phenyl substituted by C6-C18 alkyl, or a pharmaceutically acceptable salt thereof.

23. A 2-amino-1,3-propanediol compound of claim 21 or 22, which is selected from the group consisting of

2-amino-2-(4-decylphenyl)-1,3-propanediol,

2-amino-2-(4-dodecylphenyl)-1,3-propanediol,

2-amino-2-(4-tetradecylphenyl)-1,3-propanediol and

2-amino-2-(4-hexadecylphenyl)-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

24. A 2-amino-1,3-propanediol compound, having the formula ##STR450## wherein R¹ is an optionally substituted straight- or branched carbon chain which may have, in the chain, a bond, a hetero atom or a group selected from the group consisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, and carbonyl, optionally substituted arylene, optionally substituted cycloalkylene, optionally substituted heteroarylene and an alicycle thereof, and which may be substituted, at the chain end (ω

-position) thereof, by a double bond, a triple bond, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heteroaryl or an alicycle thereof, an optionally substituted aryl, an optionally substituted cycloalkyl, an optionally substituted heteroaryl or an alicycle thereof, and

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is a hydrogen, an alkyl, an acyl or an alkoxycarbonyl;

wherein the optionally substituted straight- or branched carbon chain may have a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxyimino, hydroxy, carboxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted cycloalkyl, optionally substituted heteroaryl and an alicycle thereof; and

the aforementioned optionally substituted arylene, optionally substituted cycloalkylene, optionally substituted heteroarylene, an alicycle thereof, optionally substituted aryl, optionally substituted aryloxy, optionally substituted cycloalkyl, optionally substituted heteroaryl and an alicycle thereof may have a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkyl carbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy;

or a pharmaceutically acceptable salt thereof.

25. A 2-amino-1,3-propanediol compound of claim 24, having the formula ##STR451## wherein Rr is an alkyl optionally substituted by hydroxy and/or hydroxyimino which may have, in the chain, a double bond or carbonyl, or a pharmaceutically acceptable salt thereof.

26. A 2-amino-1,3-propanediol compound of claim 24 or 25, which is selected from the group consisting of

2-amino-2-(1,2,12-trihydroxy-4-octadecenyl)-1,3-propanediol,

2-amino-2-(1,2-dihydroxy-4-octadecenyl)-1,3-propanediol,

2-amino-2-(1,2-dihydroxyoctadecyl)-1,3-propanediol,

2-amino-2-(1,12-dihydroxy-4-octadecenyl)-1,3-propanediol,

2-amino-2-(1,2,4-trihydroxybutyl)-1,3-propanediol,

2-amino-2-(1,2,12-trihydroxyoctadecyl)-1,3-propanediol and

2-amino-2-(1,12-dihydroxyoctadecyl)-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

27. A 2-amino-1,3-propanediol compound of claim 24, having the formula ##STR452## wherein Rs is a phenylalkyl substituted by a straight- or branched chain C6-C14 alkyl optionally substituted by halogen, a straight- or branched chain C6-C14 alkoxy optionally substituted by halogen or a straight- or branched chain C6-C14 alkenyloxy, or a pharmaceutically acceptable salt thereof.

28. A 2-amino-1,3-propanediol compound of claim 27, which is selected from the group consisting of

2-amino-2-[1-hydroxy-2-(4-octylphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)-1-hydroxyethyl]-1,3-propanediol,

2-amino-2-[2-(4-heptyloxyphenyl)-1-hydroxyethyl]-1,3-propanediol,

2-amino-2-[1-hydroxy-2-(4-undecyloxyphenyl)ethyl]-1,3-propanediol,

2-amino-2-[2-(4-(8-fluorooctyl)phenyl)-1-hydroxyethyl]-1,3-propanediol,

2-amino-2-[2-(4-(12-fluorododecyl)phenyl)-1-hydroxyethyl]-1,3-propanediol,

2-amino-2-[2-(4-(7-fluoroheptyloxy)phenyl)-1-hydroxyethyl]-1,3-propanediol and

2-amino-2-[1-hydroxy-2-(4-(11-fluoroundecyloxy)phenyl)ethyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

29. A 2-amino-1,3-propanediol compound, having the formula ##STR453## wherein Rt is an optionally substituted straight- or branched carbon chain which may have, in the chain, a bond, a hetero atom or a group selected from the group consisting of a double bond, a triple bond, oxygen, sulfur, sulfinyl, sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl, carbonyl, optionally substituted arylene, optionally substituted cycloalkylene, optionally substituted heteroarylene and an alicycle thereof, an optionally substituted aryl, an optionally substituted cycloalkyl, an optionally substituted heteroaryl or an alicycle thereof, and

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is a hydrogen, an alkyl, an acyl or an alkoxycarbonyl;

wherein the optionally substituted straight- or branched carbon chain may have a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy, carboxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted cycloalkyl, optionally substituted heteroaryl and an alicycle thereof; and

the aforementioned optionally substituted arylene, optionally substituted cycloalkylene, optionally substituted heteroarylene, an alicycle thereof, optionally substituted aryl, optionally substituted aryloxy, optionally substituted cycloalkyl, optionally substituted heteroaryl and an alicycle thereof may have a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy;

or a pharmaceutically acceptable salt thereof.

30. A 2-amino-1,3-propanediol compound of claim 29, having the formula ##STR454## wherein Ru is a phenyl substituted by alkyl having 4 to 16 carbon atoms, or a pharmaceutically acceptable salt thereof.

31. A 2-amino-1,3-propanediol compound of claim 29 or 30, which is selected from the group consisting of

2-amino-2-[2-(4-octylphenyl)ethenyl]-1,3-propanediol,

2-amino-2-[2-(4-decylphenyl)ethenyl]-1,3-propanediol,

2-amino-2-[2-(4-dodecylphenyl)ethenyl]-1,3-propanediol and

2-amino-2-[2-(4-tetradecylphenyl)ethenyl]-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

32. A 2-amino-1,3-propanediol compound, having the formula ##STR455## wherein Rv is an optionally substituted aryl, an optionally substituted cycloalkyl, an optionally substituted heteroaryl or an alicycle thereof;

R² a, R³ a, R⁴ a and R⁵ a are the same or different and each is a hydrogen, an alkyl, an acyl or an alkoxycarbonyl;

X is an oxygen, a sulfur, a sulfinyl, a sulfonyl, --N(R⁶)-- where R⁶ is hydrogen, alkyl, aralkyl, acyl or alkoxycarbonyl; and

α and

β

are 0 or an integer of 1-20 provided that α

+β

=5-20, wherein the optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted heteroaryl and an alicycle thereof may have a substituent selected from the group consisting of alkyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, alkylenedioxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, haloalkoxy, nitro, halogen, amino, hydroxy and carboxy;

or a pharmaceutically acceptable salt thereof.

33. A 2-amino-1,3-propanediol compound of claim 32, having the formula ##STR456## wherein Rw is a phenyl substituted by C4-C16 alkyl, or a pharmaceutically acceptable salt thereof.

34. A 2-amino-1,3-propanediol compound of claim 32 or 33, which is selected from the group consisting of

2-amino-2-(4-octylphenoxymethyl)-1,3-propanediol,

2-amino-2-(4-decylphenoxymethyl)-1,3-propanediol,

2-amino-2-(4-dodecylphenoxymethyl)-1,3-propanediol and

2-amino-2-(4-tetradecylphenoxymethyl)-1,3-propanediol, or a pharmaceutically acceptable salt thereof.

39. A 2-amino-1,3-propanediol compound of the formula ##STR457## wherein R¹ b is a substituted straight- or branched chain alkyl having 1 to 30 carbon atoms, a substituted straight- or branched chain alkenyl having 2 to 30 carbon atoms or a substituted straight- or branched chain alkynyl having 2 to 30 carbon atoms, and

R² b, R³ b, R⁴ b and R⁵ b are the same or different and each is a hydrogen, an alkyl or an acyl;

wherein the substituted straight- or branched chain alkyl having 1 to 30 carbon atoms, substituted straight- or branched chain alkenyl having 2 to 30 carbon atoms and substituted straight- or branched chain alkynyl having 2 to 30 carbon atoms have a substituent selected from the group consisting of alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, nitro, halogen, amino, hydroxy, carboxy, optionally substituted phenyl and optionally substituted cycloalkyl; and

the aforementioned optionally substituted phenyl and optionally substituted cycloalkyl may have 1 to 3 substituents selected from the group consisting of alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, aralkyloxy, acyl, alkylamino, alkylthio, acylamino, alkoxycarbonyl, alkoxycarbonylamino, acyloxy, alkylcarbamoyl, haloalkyl, nitro, halogen, amino, hydroxy and carboxy;

or a pharmaceutically acceptable salt thereof.