Claims
- 1. A glucopyranose compound of formula (I) or (IA): ##STR306## wherein R represents a hydrogen atom, a hydroxy group or an alkoxy group of from 1 to 4 carbon atom(s);
- R.sup.1 represents a single bond or an oxycarbonylalkylene group of from 2 to 20 carbon atoms;
- R.sup.2 and R.sup.6, independently, represent a hydrogen atom or a general formula: ##STR307## wherein R.sup.10 represents a hydrogen atom, an alkyl or alkoxy group of from 1 to 7 carbon atom(s) or a halogen atom, and s represents 1, 2 or 3, respectively;
- R.sup.3 represents an alkylene group of from 1 to 20 carbon atom(s);
- R.sup.4 represents a hydrogen atom or a formula: ##STR308## wherein R.sup.11 represents a hydrogen atom, an alkyl or alkoxy group of from 1 to 7 carbon atom(s) or a halogen atom, and t represents 1, 2 or 3;
- R.sup.5 represents an oxycarbonylalkylene group of from 2 to 20 carbon atoms;
- R.sup.7 represents a hydrogen atom or a hydroxy group;
- with the proviso that R.sup.2, R.sup.4 and R.sup.6 do not represent hydrogen atoms at the same time; or ##STR309## wherein W.sup.1 represents a hydrogen atom, a hydroxy group or an alkoxy group of from 1 to 4 carbon atom(s);
- W.sup.2 represents a group represented by A, B, D or E:
- A represents a formula: ##STR310## B represents a formula: ##STR311## D represents a formula: ##STR312## and E represents a formula: ##STR313## in each of A, B, D and E, l and q each represents an integer of 11.about.15, m and m' each represents an integer of 6.about.12, n represents an integer of 6-10, l' and n' each represents an integer of 9.about.13,
- G represents a single bond or an alkylene group of from 1 to 4 carbon atom(s);
- Y.sup.2 represents a hydrogen atom, an alkyl or alkoxy group of from 1 to 7 carbon atom(s) or a halogen atom;
- W.sup.3 represents a group represented by L, M or Q:
- L represents a formula: ##STR314## M represents a formula: ##STR315## and Q represents a formula: ##STR316## in each of L, M and Q, Z represents a single bond or an alkylene group of from 1 to 4 carbon atom(s), p and p' each represents an integer of 6.about.12, q' represents an integer of 11.about.15, r represents an integer of 6.about.10, Y.sup.3 represents a hydrogen atom, an alkyl or alkoxy group of from 1 to 7 carbon atom(s) or a halogen atom;
- W.sup.4 represents a hydrogen atom, hydroxymethyl group or sulfoxymethyl group;
- with the proviso that when W.sup.4 represents hydroxymethyl group, (A,M), (A,Q), (D,M), (D,Q) and (E,M) as the combination of (W.sup.2, W.sup.3) are excluded, and when W.sup.4 represents sulfoxymethyl group, (A,M) and (E,M) as the combination of (W.sup.2, W.sup.3) are excluded,
- or a non-toxic salt of the glucopyranose compound.
- 2. A compound according to claim 1, wherein R.sup.7 is a hydroxy group.
- 3. A compound according to claim 2, wherein R is a hydroxy group.
- 4. A compound according to claim 3, wherein R.sup.2 is a phenyl or phenoxy group, and R.sup.4 is a hydrogen atom.
- 5. A compound according to claim 4, which is selected from the group consisting of
- 2-deoxy-2-[3R-(4-phenylbutyryloxy)tetradecanoyl]amino-3-O-(4-phenylbutyryl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(5-phenylpentanoyloxy)tetradecanoyl]amino-3-O-(5-phenylpentanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(7-phenylheptanoyloxy)tetradecanoyl]amino-3-O-(7-phenylheptanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(9-phenylnonanoyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(10-phenyldecanoyloxy)tetradecanoyl]amino-3-O-(10-phenyldecanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3R-(10-phenyldecanoyloxy)tetradecanoyl]amino-3-O-(10-phenyldecanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(11-phenylundecanoyloxy)tetradecanoyl]amino-3-O-(11-phenylundecanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-(13-phenyltridecanoyloxy)tetradecanoyl]amino-3-O-(13-phenyltridecanoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3R-(9-phenylnonanoyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-D-glucopyranose and
- 2-deoxy-2-[3S-(8-phenoxyoctanoyloxy)tetradecanoyl]amino-3-O-(8-phenoxyoctanoyl)-4-O-sulfo-D-glucopyranose.
- 6. A compound according to claim 3, wherein both of R.sup.2 and R.sup.4 are phenyl groups.
- 7. A compound according to claim 6, which is selected from the group consisting of
- 2-deoxy-2-[3R-(9-phenylnonanoyloxy)-9-phenylnonanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-D-glucopyranose and
- 2-deoxy-2-[3S-(9-phenylnonanoyloxy)-9-phenylnonanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-D-glucopyranose.
- 8. A compound according to claim 3, wherein R.sup.2 is a phenyl or phenoxy group substituted by one to three alkyl or alkoxy group(s) of from 1 to 7 carbon atom(s) or halogen atom(s).
- 9. A compound according to claim 8, which is selected from the group consisting of
- 2-deoxy-2-[3S-[8-(4-methoxyphenyl)octanoyloxy]tetradecanoyl]amino-3-O-[8-(4-methoxyphenyl)octanoyl]-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-[9-(4-chlorophenyl)nonanoyloxy]tetradecanoyl]amino-3-O-[9-(4-chlorophenyl)nonanoyl]-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-[5-(4-pentylphenyl)pentanoyloxy]tetradecanoyl]amino-3-O-[5-(4-pentylphenyl)pentanoyl]-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3S-[8-(4-chlorophenoxy)octanoyloxy]tetradecanoyl]amino-3-O-[8-(4-chlorophenoxy)octanoyl]-4-O-sulfo-D-glucopyranose and
- 2-deoxy-2-[3S-[8-(3,5-dichlorophenoxy)octanoyloxy]tetradecanoyl]amino-3-O-[8-(3,5-dichlorophenoxy)octanoyl]-4-O-sulfo-D-glucopyranose.
- 10. A compound according to claim 3, wherein R.sup.2 is a naphthyl or naphthyloxy group.
- 11. A compound according to claim 10, which is selected from the group consisting of
- 2-deoxy-2-[3S-[9-(1-naphthyl)nonanoyloxy]tetradecanoyl]amino-3-O-[9-(1-naphthyl)nonanoyl]-4-O-sulfo-D-glucopyranose and
- 2-deoxy-2-[3S-[9-(2-naphthyl)nonanoyloxy]tetradecanoyl]amino-3-O-[9-(2-naphthyl)nonanoyl]-4-O-sulfo-D-glucopyranose.
- 12. A compound according to claim 3, wherein R.sup.1 is a single bond, R.sup.2 is a hydrogen atom and R.sup.4 is a naphthyl or naphthyloxy group.
- 13. A compound according to claim 12, which is selected from the group consisting of
- 2-deoxy-2-[9-(1-naphthyl)nonanoyl]amino-3-O-[9-(1-naphthyl)nonanoyl]-4-O-sulfo-D-glucopyranose and
- 2-deoxy-2-[9-(2-naphthyl)nonanoyl]amino-3-O-[9-(2-naphthyl)nonanoyl]-4-O-sulfo-D-glucopyranose.
- 14. A compound according to claim 2, wherein R is a hydrogen atom.
- 15. A compound according to claim 14, wherein R.sup.2 is a phenyl or phenoxy group, and R.sup.4 is a hydrogen atom.
- 16. A compound according to claim 15, which is selected from the group consisting of
- 2-deoxy-2-[3R-(9-phenylnonanoyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-1,5-anhydro-D-glucitol and
- 2-deoxy-2-[3R-(8-phenoxyoctanoyloxy)tetradecanoyl]amino-3-O-(8-phenoxyoctanoyl)-4-O-sulfo-1,5-anhydro-D-glucitol.
- 17. A compound according to claim 14, wherein R.sup.2 is a phenyl or phenoxy group substituted by one to three alkyl or alkoxy group(s) of from 1 to 7 carbon atom(s) or halogen atom(s).
- 18. A compound according to claim 17, which is selected from the group consisting of
- 2-deoxy-2-[3R-[8-(4-methoxyphenyl)octanoyloxy)tetradecanoyl]amino-3-O-[8-(4-methoxyphenyl)octanoyl]-4-O-sulfo-1,5-anhydro-D-glucitol,
- 2-deoxy-2-[3R-[8-(4-chlorophenoxy)octanoyloxy]tetradecanoyl]amino-3-O-[8-(4-chlorophenoxy)octanoyl]-4-O-sulfo-1,5-anhydro-D-glucitol and
- 2-deoxy-2-[3R-[5-(4-pentylphenyl)pentanoyloxy]tetradecanoyl]amino-3-O-[5-(4-pentylphenyl)pentanoyl]-4-O-sulfo-1,5-anhydro-D-glucitol.
- 19. A compound according to claim 14, wherein R.sup.2 is a naphthyl or naphthyloxy group.
- 20. A compound according to claim 19, which is
- 2-deoxy-2-[3R-[9-(1-naphthyl)nonanoyloxy]tetradecanoyl]amino-3-O-[9-(1-naphthyl)octanoyl]-4-O-sulfo-1,5-anhydro-D-glucitol.
- 21. A compound according to claim 2, wherein R is a methoxy group.
- 22. A compound according to claim 21, which is
- methyl 2-deoxy-2-[3R-(9-phenylnonanoyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-.beta.-D-glucopyranoside.
- 23. A compound according to claim 1, wherein both of R.sup.7 and R are hydrogen atoms.
- 24. A compound according to claim 23, which is
- 2,6-deoxy-2-[3S-(9-phenylnonanoyloxy)tetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-1,5-anhydro-D-glucitol.
- 25. A compound according to claim 1, wherein W.sup.4 is a hydrogen atom.
- 26. A compound according to claim 1 or claim 25, wherein R.sup.2 is the formula represented by B.
- 27. A compound according to claim 1 or claim 26, wherein W.sup.3 is the formula represented by L.
- 28. A compound according to claim 1 or claim 27, which is selected from the group consisting of
- 2-deoxy-2-(3-tetradecanoyloxytetradecanoyl)amino-3-O-tetradecanoyl-4-O-sulfo-1,5-anhydro-D-xylitol,
- 2-deoxy-2-[3-(9-phenylnonanoyl)oxytetradecanoyl]amino-3-O-(9-phenylnonanoyl)-4-O-sulfo-1,5-anhydro-D-xylitol,
- 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-tetradecanoyl-4-O-sulfo-1,5-anhydro-D-xylitol,
- methyl 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-tetradecanoyl-4-O-sulfo-5-anhydro-D-glucopyranoside,
- 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-tetradecanoyl-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-(3,4-didecyloxybenzoyl)-4-O-sulfo-D-glucopyranose,
- methyl 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-(3,4-didecyloxybenzoyl)-4,6-disulfo-.alpha.-D-glucopyranoside,
- methyl 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-(3,4-didecyloxybenzoyl)-4-O-sulfo-.alpha.-D-glucopyranoside,
- 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-tetradecanoyl-4,6-O-disulfo-D-glucopyranoside,
- methyl 2-deoxy-2-(3,4-didecyloxybenzoyl)amino-3-O-tetradecanoyl-4-O-sulfo-D-glucopyranoside,
- 2-deoxy-2-tetradecanoylamino-3-O-(3,4-didecyloxybenzoyl)-4-O-sulfo-D-glucopyranose,
- 2-deoxy-2-[3-(3,4-dioctyloxy)phenylpropionyl]amino-3-O-tetradecanoyl-4-O-sulfo-D-glucopyranose,
- methyl 2-deoxy-2-[3-(3,4-dioctyloxyphenyl)propanoyl]amino-3-O-[3-(3,4-dioctyloxyphenyl)propanoyl]-4,6-disulfo-.alpha.-D-glucopyranoside,
- methyl 2-deoxy-2-[3-(3,4-dioctyloxyphenyl)propanoyl]amino-3-O-tetradecanoyl-4,6-O-disulfo-.alpha.-D-glucopyranoside and
- methyl 2-deoxy-2-tetradecanoylamino-3-O-[3-(3,4-dioctyloxyphenyl)propanoyl]-4,5-O-disulfo-.alpha.-D-glucopyranoside.
- 29. A pharmaceutical composition for use in enhancing immunity, or in the treatment of a tumor comprising as active ingredient, a compound of the formula (I) or (IA) as set forth in claim 1, with a pharmaceutically acceptable carrier and/or coating.
Priority Claims (3)
Number |
Date |
Country |
Kind |
60-273440 |
Dec 1985 |
JPX |
|
61-210379 |
Sep 1986 |
JPX |
|
62-106298 |
May 1987 |
JPX |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a continuation in part, of U.S. application Ser. No. 938,308, filed Dec. 5, 1986, now abandoned and U.S. application Ser. No. 188,873 filed May 2, 1988, now abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
4304903 |
Nair et al. |
Dec 1981 |
|
4374831 |
Joseph et al. |
Feb 1983 |
|
4399126 |
Schaub et al. |
Aug 1983 |
|
4536572 |
Kim et al. |
Aug 1985 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
8404526 |
Nov 1984 |
WOX |
Non-Patent Literature Citations (2)
Entry |
Agricultural and Biological Chemistry, vol. 48, No. 1, Jan. 1984, pp. 251-252, "Synthesis of Biologically Active, Novel Monosaccharide Analogs of Lipid A". |
Chemical & Pharmaceutical Bulletin, vol. 33, No. 10, Oct. 1985, pp. 4621-4624, "Antitumor Activity and Biological Effects of Chemically Synthesized etc." |
Continuation in Parts (1)
|
Number |
Date |
Country |
Parent |
938308 |
Dec 1986 |
|