Novel sugar ureide and thioureide derivatives
AssigneeHaruo Ogura
InventorsHaruo Ogura, Hiroshi Takahashi
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Abstract
Novel sugar ureide and thioureide derivatives are provided by this invention, which exhibit certain antibacterial activity against a variety of gram-positive and gram-negative bacteria and useful in therapeutic treatment of bacterial infections. The compounds have the formula ##STR1## wherein R.sub.1 is a monovalent residue of aldose, aldonic acid and their 2-amino derivatives, R.sub.2 is an aralkyl, heterocyclic, sulfamoylaryl, R.sub.3 CONH or R.sub.4 NH-- where R.sub.3 is a heterocyclic and R.sub.4 is an aryl group and Y is oxygen or sulfur atom, which are prepared by reacting an isocyanate or isothiocyanate of the formula R.sub.1 NC=Y with an amino compound of the formula R.sub.2 NH.sub.2.
Claims18
Sugar ureide and thioureide derivatives of the formula:
- ##STR4## wherein R.sub.1 represents glucopyranosyl, arabinopyranosyl or gluconyl whose alcoholic hydroxyl groups have been protected by HO-protecting groups;
- R.sub.2 represents benzyl, .beta.-carboxy-phenethyl, p-sulfamoyl-benzyl, .alpha.-(3-carboxy-2,2-dimethylpenam-6-yl-aminocarbonyl)benzyl, .alpha.-(4-carboxy-3-methyl-3-cephem-7-yl-aminocarbonyl)benzyl, 2-pyridyl, 2-benzimidazolyl, 2-benzothiazolyl, 6-(1,3-dimethyl-2,4-dioxo)pyrimidinyl, 5-(4-carbamoyl-1-phenyl)pyrazolyl, 5-(4-ethoxycarbonyl-1-phenyl)pyrazolyl, 4-(2,3-dimethyl-5-oxo-1-phenyl)pyrazolinyl, 6-penicillanyl, 6-(3-phenacyl)penicillanyl, isonicotinoylamino, p-[N-3,4-dimethyl)-5-isoxazolyl]sulfamoylphenyl, p-[N-(2,6--dimethyl)-4-pyrimidinyl]sulfamoylphenyl, p-(N-2-pyrimidinyl)sulfamoylphenyl or p-(N-2-thiazolyl)sulfamoylphenyl;
- and Y represents an atom of oxygen or sulfur.
.alpha.-(2,3,4,6-Tetra-O-acetyl-D-glucopyranosylthioureido) benzylpenicillin and triethylammonium salt thereof.
.alpha.-(2,3,4-Tri-O-acetyl-D-arabinopyranosylthioureido) benzylpenicillin and triethylammonium salt thereof.
.alpha.-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido) benzylpenicillin and triethylammonium salt thereof.
7-[D-.alpha.-(2,3,4,5,6-penta-O -acetyl-D-gluconylthioureido)-phenylacetamido]-3-methyl-3-cephem-4-carboxyl ic acid.
Compounds selected from:
- 1-(2,3,4,6-Tetra-O-acetyl-.beta.-D-glucopyranosyl)-3-(benzimidazol-2-yl)-2- thiourea;
- 1-(2,3,4,6-Tetra-O-acetyl-.beta.-D-glucopyranosyl)-3-(benzothiazol-2-yl)-2- thiourea;
- 1-(4-Pyridylcarbonyl)-4-(2,3,4,6-tetra-O-acetyl-.beta.-D-glucopyranosyl)-se micarbazide;
- 1-(2,3,4,6-Tetra-O-acetyl-.beta.-D-glucopyranosyl)-3-(1,3-dimethylpyrimidin -2,4-dione-6-yl)-2-thiourea;
- 6-(2,3,4,6-Tetra-O-acetyl-.beta.-D-glucopyranosylthioureido) penicillanic acid and its triethylammonium salt;
- 1-(2,3,4-Tri-O-acetyl-.alpha.-D-arabinopyranosyl)-3-(benzothiazol-2-yl)-2-t hiourea;
- 6-(2,3,4-Tri-O-acetyl-.alpha.-D-arabinopyranosyl-thioureido) penicillanic acid and its triethylammonium salt;
- 1-(2,3,4,6-Tetra-O-acetyl-.beta.-D-glucopyranosyl)-3-(2,3-dimethyl-l-phenyl -3-pyrazolin-5-one-4-yl)-2-thiourea;
- 1-(2,3,4-Tri-O-acetyl-.alpha.-D-arabinopyranosyl)-3-(2,3-dimethyl-1-phenyl- 3-pyrazolin-5-one-4yl)-2-urea;
- 1-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl)-3-(benzothiazol)-2-yl)-2-thiourea;
- 6-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl-thioureido) penicillanic acid and its phenacyl ester;
- 1-(2,3,4,5,6-Penta-O-acetyl-D-gluconyl)-3-(.beta.-carboxy phenetyl)-2-thiourea;
- 1-Phenyl-4-ethoxycarbonyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole;
- 2-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido) pyridine;
- 1-Phenyl-4-carbamoyl-5-(2,3,4,5,6-penta-O-acetyl-D-gluconylthioureido) pyrazole;
- 1-(4-Pyridylcarbonyl)-4-(2,3,4,5,6-penta-O-acetyl-D-gluconyl)-thiosemicarba zide;
- 4-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido)-phenyl-N'-(3,4-dimethyl-5 -isoxazolyl)-sulfonamide;
- 4-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido)-phenyl-N'-(2,6-dimethyl-4 -pyrimidyl)-sulfonamide;
- 4-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido)-phenyl-N'-(2-pyrimidyl)-s ulfonamide;
- 4-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureido-phenyl-N'-(2-thiazolyl)-su lfonamide;
- and
- 4-(2,3,4,5,6-Penta-O-acetyl-D-gluconylthioureidomethyl)phenyl-sulfonamide.
Sugar ureide and thioureide derivatives of the formula:
- ##STR5## wherein R.sub.1 represents glucopyranosyl, arabinopyranosyl or gluconyl whose alcoholic hydroxyl groups have been protected by HO-protected groups;
- R.sub.2 represents p-sulfamoyl-benzyl, .alpha.-(3-carboxy-2,2-dimethylpenam-6-yl-aminocarbonyl)benzyl, .alpha.-(4-carboxy-3-methyl-3-cephem-7-yl-aminocarbonyl)benzyl, 2-benzimidazoyl, 2-benzothiazolyl, 6-(1,3-dimethyl-2,4-dioxo)pyrimidinyl, 5-(4-carbamoyl-1-phenyl)pyrazolyl, 5-(4-ethoxycarbonyl-1-phenyl)pyrazolyl, 4-(2,3-dimethyl-5-oxo-1-phenyl)pyrazolinyl, 6-penicillanyl, 6-(3-phenacyl) penicillanyl, isonicotinoylamino, p-[N-3,4-dimethyl)-5-isoxazolyl]sulfamoyl-phenyl, p-[N-(2,6-dimethyl)-4-pyrimidinyl]sulfamoylphenyl, p-(N-2-pyrimidinyl)sulfamoylphenyl or p-(N-2-thiazolyl)sulfamoylphenyl;
- and Y represents an atom of oxygen or sulfur.
Sugar ureide and thioureide derivatives of the formula:
- ##STR6## wherein R.sub.1 represents glucopyranosyl whose alcoholic hydroxyl groups have been protected by HO-protected groups;
- R.sub.2 represents .alpha.-(3-carboxy-2,2-dimethylpenam-6-yl-aminocarbonyl)benzyl, 2-benzimidazolyl, 2-benzothiazolyl, 6-(1,3-dimethyl-2,4-dioxo(pyrimidinyl, 4-(2,3-dimethyl-5-oxo-1-phenyl)pyrazolinyl, 6-penicillanyl or isonicotinoylamino, and Y represents an atom of oxygen or sulfur.
Sugar ureide and thioureide derivatives of the formula:
- ##STR7## wherein R.sub.1 represents arabinopyranosyl whose alcoholic hydroxyl groups have been protected by HO-protecting groups;
- R.sub.2 represents .alpha.-(3-carboxy-2-dimethylpenam-6-yl-aminocarbonyl)benzyl, 2-benzothiazolyl or 4-(2,3-dimethyl-5-oxo-1-phenyl)pyrazolinyl;
- and Y represents an atom of oxygen or sulfur.
As novel compounds sugar ureide and thioureide derivatives of the general formula:
- ##STR8## wherein R.sub.1 represents gluconyl group of which the alcoholic hydroxyl groups have been protected;
- R.sub.2 represents .beta.-carboxyphenetyl, p-sulfamoyl-benzyl, .alpha.-(3-carboxy-2,2-dimethyl-penam-6-yl-aminocarbonyl)benzyl, .alpha.-(4-carboxy-3-methyl-3-cephem-7-yl-aminocarbonyl)benzyl, 2-pyridyl, 2-benzothiazolyl, 5-(4-carbamoyl-1-phenyl)pyrazolyl, 5-(4-ethoxycarbonyl-1-phenyl)pyrazolyl, 6-penicillanyl, 6-(3-phenacyl)penicillanyl, isonicotinoylamino, p-[N-(3,4-dimethyl)-5-isoxazolyl]sulfamoylphenyl, p-[N-(2,6-dimethyl)4-pyrimidinyl]sulfamoylphenyl, p-(N-2-pyrimidinyl)sulfamoylphenyl or p-(N-2-thiazolyl) sulfamoylphenyl group;
- and Y represents an atom of oxygen or sulfur.
Dependencies are inferred from the claim text.