# US 5,763,413 A · Lewis-associated compound, process for producing the same, and anti-inflammatory

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- Number: US 5,763,413 A
- Document ID: US5763413A
- Status: Granted
- Kind: A
- Application number: 08/505,352
- Filed: 1995-08-30
- Granted: 1998-06-09
- Earliest claimed: 1993-03-04
- Assignees: Mect Corporation
- Inventors: Masaaki Numata; Shigeki Nunomura; Shuji Fujita; Masami Iida; Akira Endo; Takayuki Ishii; Tomoya Ogawa; Mamoru Sugimoto; Ryoichi Osawa; Masamichi Fujita
- Web page: https://patentgrep.com/patent/US5763413A

## CPC

- C07H 13/04: having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H 3/06: Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
- C07H 15/04: attached to an oxygen atom of the saccharide radical
- C07H 15/10: containing unsaturated carbon-to-carbon bonds
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

A Lewis-associated compound, represented by general formula (I), a process for producing the same, and an anti-inflammatory, wherein R.sup.1 and R.sup.3 represent each hydrogen, m SO.sub.3 H or CH.sub.2 COOH; R.sup.2 represents hydrogen, SO.sub.3 H, CH.sub.2 COOH or N-acetyl-neutraminic acid residue; R.sup.4 represents hydrogen; R.sup.5 represents O-lower alkyl, O-lower alkenyl, O-ceramide residue, O-mannose residue, O-galactose residue or O-lactose residue; R.sup.6 represents acetylamine; and R.sup.7 and R.sup.8 represent each hydrogen. ##STR1##

## Claims

### Claim 1

A Lewis-associated compound, represented by the formula (I), (II), (III), (IV), (V) or (VI): ##STR6## wherein R.sup.1 represents hydrogen atom, acetyl group, pivaloyl group, levulinoyl group, or SO.sub.3 M or CH.sub.2 COOM where M represents hydrogen atom, alkali metal or lower alkyl group;
R.sup.2 represents hydrogen atom, SO.sub.3 M, CH.sub.2 COOM, acetyl group, levulinoyl group or .alpha.-N-acetylneuraminic acid residue;
R.sup.3 represents hydrogen atom, SO.sub.3 M, CH.sub.2 COOM, acetyl group or levulinoyl group;
R.sup.2 and R.sup.3 may cooperate to form benzylidene group;
R.sup.4 represents hydrogen atom, acetyl group, benzyl group or pivaloyl group;
R.sup.5 represents O-1-imino-2,2,2-trichloro-etlhyl group or fluorine atom;
R.sup.6 represents acetylamino group, phthaloylamino group, hydroxyl group or O-pivaloyl group;
R7 represents hydrogen atom, acetyl group, benzyl group or pivaloyl group;
R.sup.8 represents hydrogen atom, acetyl group or benzyl group;
R.sup.10 represents hydrogen atom, acetyl group or benzyl group;
R.sup.30 represents hydrogen atom, acetyl group or benzyl group;
R.sup.40 represents hydrogen atom, acetyl group or benzyl group;
R.sup.50 represents O-lactose residue or O-lactosylceramide residue;
R.sup.60 represents acetylamino group or phthaloylamino group;
R.sup.70 represents hydrogen atom, acetyl group or benzyl group;
R.sup.80 represents hydrogen atom, acetyl group or benzyl group;
R.sup.11 represents hydrogen atom, acetyl group or benzyl group;
R.sup.12 represents hydrogen atom, acetyl group or benzyl group;
R.sup.13 represents hydrogen atom, acetyl group or benzyl group;
R.sup.12 and R.sup.13 may cooperate to form benzylidene group;
R.sup.14 represents acetylamino group or phthaloylamino group;
R.sup.15 represents hydrogen atom or pivaloyl group; and
R.sup.16 represents hydroxyl group, acetyloxy group, benzyloxy group or O-ceramide residue;
except that (a) when the compounds in which R.sup.1, R.sup.3, R4, R.sup.7 and R.sup.14 are all hydrogen atom, R.sup.2 is a-N-acetylneuraminic acid residue; (b) in formula (I), when R.sup.2 is not .alpha.-N-acetylneuraminic acid residue, at least one of R.sup.1, R.sup.2 and R.sup.3 is SO.sub.3 M or CH.sub.2 COOM; (c) in formula (II), when fucose residue is .alpha.-fucose, R.sup.2 is not .alpha.-N- acetylneuraminic acid residue; and (d) in formula (III), R.sup.2 is .alpha.-N-acetylneuraminic acid residue.

### Claim 2

A Lewis-associated compound, represented by formula (VII), (IX) or (X): ##STR7## wherein R.sup.1 represents hydrogen atom, acetyl group or benzyl group; and
R.sup.2 represents acetyl group or N-acetylneuraminic acid residue;
R.sup.3 represents hydrogen atom, acetyl group or benzyl group;
R.sup.4 represents benzyl group;
R.sup.5 represents acetyloxy group, alkylthio group, or fluorine atom;
R.sup.6 represents acetylamino group or phthaloylamino group;
R.sup.7 represents hydrogen atom, acetyl group or benzyl group;
R.sup.8 represents hydrogen atom, acetyl group or benzyl group;
R.sup.7 and R.sup.8 may cooperate to form benzylidene group.

### Claim 3

An anti-inflammatory agent comprising a Lewis-associated compound represented by general formula (III), (IV), (V) or (VI), or a pharmacologically acceptable salt thereof as an effective component: ##STR8## wherein R.sup.1 represents hydrogen atom, SO.sub.3 H OR CH.sub.2 COOH; R.sup.2 represents hydrogen atom, SO.sub.3 H, CH.sub.2 COOH or
N-acetylneuraminic acid residue;
R.sup.3 represents hydrogen atom, SO.sub.3 H or CH.sub.2 COOH;
R.sup.4 represents hydrogen atom;
R.sup.6 represents acetylamino group;
R.sup.7 represents hydrogen atom;
R.sup.8 represents hydrogen atom;
R.sup.10 represents hydrogen atom;
R.sup.30 represents hydrogen atom;
R.sup.40 represents hydrogen atom;
R.sup.50 represents O-lactose residue or O-lactosylceramide residue;
R.sup.60 represents acetylamino group;
R.sup.70 represents hydrogen atom;
R.sup.80 represents hydrogen atom;
R.sup.11 represents hydrogen atom;
R.sup.12 represents hydrogen atom;
R.sup.13 represents hydrogen atom;
R.sup.14 represents acetylamino group;
R.sup.15 represents hydrogen atom; and
R.sup.16 represents hydroxyl group or O-ceramide residue.

### Claim 4

A process for producing compound 86, comprising the steps of:
(a) reacting compound 42 and compound 65 with glycosylation catalyst to yield compound 79;
(b) acetylating compound 79 to yield compound 80;
(c) debenzylating and then acetylating compound 80 to yield compound 81;
(d) deacetylating anomeric acetate of compound 81 to yield compound 82;
(e) reacting compound 82 and trichloroacetonitrile to yield compound 83;
(f) reacting compound 83 and benzoyl ceramide to yield compound 84;
(g) converting compound 84 into its lithium salt 85; and
(h) then depriving the lithium salt 85 of protecting groups, wherein compounds 42, 65 and 79-86 have the following structures: ##STR9##

### Claim 5 (depends on 3)

The anti-inflammatory agent according to claim 3, wherein if R.sup.1 and R.sup.3 of the Lewis-associated compound are each hydrogen atom, R.sup.2 is .alpha.-N-acetylneuraminic acid residue.

### Claim 6 (depends on 3)

The anti-inflammatory agent according to claim 3, wherein the agent further comprises a carrier.