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WO1996018406A2 - Ophthalmic formulations of substituted glycosides - Google Patents

Ophthalmic formulations of substituted glycosides Download PDF

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Publication number
WO1996018406A2
WO1996018406A2 PCT/US1995/015577 US9515577W WO9618406A2 WO 1996018406 A2 WO1996018406 A2 WO 1996018406A2 US 9515577 W US9515577 W US 9515577W WO 9618406 A2 WO9618406 A2 WO 9618406A2
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
ophthalmic
contact lens
lens care
saccharide
Prior art date
Application number
PCT/US1995/015577
Other languages
French (fr)
Other versions
WO1996018406A3 (en
Inventor
Tai-Lee Ke
Thomas Wernet
Diane S. Nelms
Ruth Ann Rosenthal
Original Assignee
Alcon Laboratories, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alcon Laboratories, Inc. filed Critical Alcon Laboratories, Inc.
Priority to AU43719/96A priority Critical patent/AU4371996A/en
Publication of WO1996018406A2 publication Critical patent/WO1996018406A2/en
Publication of WO1996018406A3 publication Critical patent/WO1996018406A3/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7008—Compounds having an amino group directly attached to a carbon atom of the saccharide radical, e.g. D-galactosamine, ranimustine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0048—Eye, e.g. artificial tears
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L12/00—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor
    • A61L12/08—Methods or apparatus for disinfecting or sterilising contact lenses; Accessories therefor using chemical substances
    • A61L12/14—Organic compounds not covered by groups A61L12/10 or A61L12/12

Definitions

  • the present invention is directed to the use of substituted glycosides, particularly alkyl glucamides, to potentiate the efficacy of antimicrobial agents in ophthalmic formulations.
  • substituted glycosides particularly alkyl glucamides
  • Some of the alkyl glucamides are effective antimicrobial agents themselves.
  • U.S. Patent No. 5,369,095 discloses the use of the compounds of the present invention as mucous membrane penetration enhancers.
  • An abstract for J 55102507-A discloses a fish preservative containing iodine, ethanol, and sucrose monolaurate.
  • An abstract for J 49054524-A discloses a food preservative containing a sucrose-fatty acid ester and /or polyoxyethylenesorbitol-fatty acid ester and a monoglyceride of six to eight carbon atoms.
  • EP 0422508 A2 discloses a liquid detergent useful for the skin and hair containing a nonionic saccharide surfactant, including a saccharide amide surfactant, and an antibacterial.
  • a cleanser composition containing a sugar based nonionic surfactant, including a sugar amide based surfactant, and an antiinflammatory.
  • the composition is useful for the skin and hair.
  • a translation of Japanese Patent Application No. 3-282925 describes a prophylactic for microbial infection.
  • the active component is a phosphate substituted alkyl glucamide.
  • Benzalkonium chloride although commonly used and quite effective, has been found to be toxic to the cornea at high concentrations (>.05%); chlorobutanol cannot be formulated above pH 6, and chlorhexidine readily precipitates with anions commonly used in ophthalmic formulations.
  • the compounds of the present invention potentiate the efficacy of known antimicrobials allowing for their use at lower, less potentially toxic levels.
  • the alkyl glucamides also produce significantly less corneal irritation than BAC; and they can be readily formulated in ophthalmic solutions at physiological pH.
  • the alkyl glucamides are useful to potentiate the efficacy of antimicrobial agents used as preservatives or disinfectants in ophthalmic formulations, such as contact lens care solutions, ophthalmic pharmaceutical compositions, and comfort or rehydrating eye drop formulations.
  • the invention is also directed to methods for preserving ophthalmic formulations and disinfecting contact lenses.
  • the substituted glycosides used in the present invention have the following structure:
  • R x is a hydrophobic group including saturated and unsaturated aliphatic hydrocarbon groups which range from 8 to 28 carbons in length with 1 to 5 double bonds.
  • the aliphatic hydrocarbon group can be a straight or branched chain and may be substituted by one or more aromatic, cycloaliphatic or hydrophilic (e.g. hydroxyl, thiol, ester or amino) groups.
  • 1 ⁇ is a group derived from any cyclic or acyclic saccharide containing 4 - 7 carbons and their isomers;
  • X is an integer from 1-10;
  • Z is an oxy (-0-), carbonyloxy (-0-C-), phosphoryl (-0-P-0-), thio (-S-), or O I
  • R 2 o- carboxamido
  • R 2 is covalently bound to such group.
  • R can be a straight 8-18 carbon alkyl chain in hemiacetal linkage (glycoside) to the saccharide;
  • the saccharide can be, for example, an aldehyde-containing saccharide (glucose, mannose, arabinose, galactose, xylose); a ketone-contair ng saccharide (fructose, xylulose, sorbose); a saccharide alcohol (sorbitol, inositol, xylitol, mannitol); a saccharide acid (glucuronic acid, neuramic acid, mannuronic acid); a deoxysaccharide (deoxy-ribose, rhamnose,); an aminosaccharide (glucosamine, galactosamine).
  • aldehyde-containing saccharide glucose, mannose, arabinose, galactose, xylose
  • a ketone-contair ng saccharide fructtose, xylulose, sorbose
  • a saccharide alcohol sorbi
  • Higher order saccharides being covalently linked in any of a number of ways to form different isomeric structures including for example, disaccharides such as maltose, cellobiose, sucrose, and lactose and trisaccharides, such as raffinose.
  • Preferred substituted glycosides are alkyl glucamides which have the following structure:
  • R t and Rj are as above defined and
  • R 3 is hydrogen, thiol, hydroxyl, amino, amine, C w alkyl, C]. 6 alkoxy or alkyl sulfide.
  • the substituted glycosides are useful as disinfectants or preservatives in all types of ophthalmic formulations, such as contact lens care solutions and pharmaceutical formulations.
  • the compounds are present in contact lens care formulations to potentiate the antimicrobial activity of a disinfectant or preservative at concentrations at or above about 0.01 weight/ volume percent (w/v%) to 10.0 w/v%; preferably 0.01-2 w/v%; most preferably 0.1-0.5 w/v%.
  • the compounds are useful in other ophthalmic formulations to potentiate the preservative efficacy of, for example, benzalkonium chloride (BAC), at concentrations at or above about 0.01 w/v%; preferably 0.01-2 w/v%; most preferably 0.1-0.5 w/v%.
  • BAC benzalkonium chloride
  • the BAC concentration can be reduced to about 75% of its usual concentration in ophthalmic formulations.
  • the preferred alkyl glucamides include compounds wherein Rj is C 10 , Rj is glucose, and R 3 is methyl (Glucamide C-10) and wherein Rj is , Rj is glucose, and R 3 is methyl (Glucamide C-9).
  • Most preferred is Glucamide C-10.
  • Glucamide C-10 is not only effective in potentiating the efficacy of BAC, but is useful alone as an ophthalmic preservative at concentrations of above 0.01 w/v%; preferably 0.05- 0.5 w/v%; most preferably 0.1-0.3 w/v%.
  • compositions can include other components known to those skilled in the art of formulating ophthalmic products.
  • the compounds of Structure I can be incorporated into various types of ophthalmic formulations for delivery to the eye.
  • the compounds may be combined with ophthalmologically acceptable preservatives, surfactants, viscosity enhancers, penetration enhancers, buffers, sodium chloride and water to form aqueous, sterile ophthalmic suspensions or solutions.
  • the compounds are combined with the active ingredient and a preservative in an appropriate vehicle, such as, mineral oil, liquid lanolin, or white petrolatum.
  • Sterile ophthalmic gel formulations may be prepared by suspending the active ingredient in a hydrophilic base prepared from the combination of, for example, carbopol-940 or the like according to the published formulations for analogous ophthalmic preparations; alkyl glucamides, preservatives, and tonicity agents can be incorporated.
  • Ophthalmic solution formulations may be prepared by dissolving the active ingredient in a physiologically acceptable isotonic aqueous buffer. Further, the ophthalmic solution may include an ophthalmologically acceptable surfactant to assist in dissolving the active ingredient and preservatives to preserve the solution.
  • the ophthalmic solution may contain a viscosity enhancing agent, such as, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylmethyl-cellulose, methylcellulose, polyvinylpyrrolidone, or the like to improve the retention of the medicament in the conjunctival sac or the comfort of a contact lens.
  • a viscosity enhancing agent such as, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylmethyl-cellulose, methylcellulose, polyvinylpyrrolidone, or the like to improve the retention of the medicament in the conjunctival sac or the comfort of a contact lens.
  • a viscosity enhancing agent such as, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylmethyl-cellulose, methylcellulose, polyvinylpyrrolidone, or the like to improve the retention of the medicament in the conjunctival sac or the comfort of a contact lens.
  • the following examples are representative of the type of ophthalmic formulation
  • Active ingredients can be added to the following formulations to provide preserved ophthalmic solutions. Active ingredients can include any medicament useful for treating the eye included at concentrations and made according to techniques known to those skilled in the art of making ophthalmic formulations. Examples 2-4 can also be used without the addition of a medicament as contact lens care solutions for disinfecting, rinsing, and storage of contact lenses. Examples 4-7 can be used without a medicament as ophthalmic comfort drop formulations.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Ophthalmology & Optometry (AREA)
  • Saccharide Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Ophthalmic formulations containing substituted glycosides useful as antimicrobial agents are disclosed. Methods for preserving ophthalmic formulations are also disclosed.

Description

OPHTHALMIC FORMULATIONS OF SUBSTITUTED GLYCOSIDES
The present invention is directed to the use of substituted glycosides, particularly alkyl glucamides, to potentiate the efficacy of antimicrobial agents in ophthalmic formulations. Some of the alkyl glucamides are effective antimicrobial agents themselves.
Background of the Invention
U.S. Patent No. 5,369,095 discloses the use of the compounds of the present invention as mucous membrane penetration enhancers. An abstract for J 55102507-A discloses a fish preservative containing iodine, ethanol, and sucrose monolaurate. An abstract for J 49054524-A discloses a food preservative containing a sucrose-fatty acid ester and /or polyoxyethylenesorbitol-fatty acid ester and a monoglyceride of six to eight carbon atoms. EP 0422508 A2 discloses a liquid detergent useful for the skin and hair containing a nonionic saccharide surfactant, including a saccharide amide surfactant, and an antibacterial. A translation of Japanese Patent Application No. 2-409899 describes a cleanser composition containing a sugar based nonionic surfactant, including a sugar amide based surfactant, and an antiinflammatory. The composition is useful for the skin and hair. A translation of Japanese Patent Application No. 3-282925 describes a prophylactic for microbial infection. The active component is a phosphate substituted alkyl glucamide.
None of the above references disclose the use of alkyl glucamides to potentiate the antimicrobial activity of antimicrobial agents in ophthalmic formulations, nor do they disclose them as useful as antimicrobial agents.
Benzalkonium chloride (BAC), although commonly used and quite effective, has been found to be toxic to the cornea at high concentrations (>.05%); chlorobutanol cannot be formulated above pH 6, and chlorhexidine readily precipitates with anions commonly used in ophthalmic formulations. The compounds of the present invention potentiate the efficacy of known antimicrobials allowing for their use at lower, less potentially toxic levels. The alkyl glucamides also produce significantly less corneal irritation than BAC; and they can be readily formulated in ophthalmic solutions at physiological pH.
Summary of the Invention
The alkyl glucamides are useful to potentiate the efficacy of antimicrobial agents used as preservatives or disinfectants in ophthalmic formulations, such as contact lens care solutions, ophthalmic pharmaceutical compositions, and comfort or rehydrating eye drop formulations. The invention is also directed to methods for preserving ophthalmic formulations and disinfecting contact lenses.
Detailed Description of the Preferred Embodiments
The substituted glycosides used in the present invention have the following structure:
(R2)x-Z-R,
wherein Rx is a hydrophobic group including saturated and unsaturated aliphatic hydrocarbon groups which range from 8 to 28 carbons in length with 1 to 5 double bonds. The aliphatic hydrocarbon group can be a straight or branched chain and may be substituted by one or more aromatic, cycloaliphatic or hydrophilic (e.g. hydroxyl, thiol, ester or amino) groups.
1^ is a group derived from any cyclic or acyclic saccharide containing 4 - 7 carbons and their isomers;
X is an integer from 1-10; and
O O
II II
Z is an oxy (-0-), carbonyloxy (-0-C-), phosphoryl (-0-P-0-), thio (-S-), or O I
II o- carboxamido (-N-C-) where R2 is covalently bound to such group. More specifically R, can be a straight 8-18 carbon alkyl chain in hemiacetal linkage (glycoside) to the saccharide; and
Ra a group derived from any of a variety of isomeric saccharides containing 5 or 6 carbons. The saccharide can be, for example, an aldehyde-containing saccharide (glucose, mannose, arabinose, galactose, xylose); a ketone-contair ng saccharide (fructose, xylulose, sorbose); a saccharide alcohol (sorbitol, inositol, xylitol, mannitol); a saccharide acid (glucuronic acid, neuramic acid, mannuronic acid); a deoxysaccharide (deoxy-ribose, rhamnose,); an aminosaccharide (glucosamine, galactosamine). Higher order saccharides being covalently linked in any of a number of ways to form different isomeric structures including for example, disaccharides such as maltose, cellobiose, sucrose, and lactose and trisaccharides, such as raffinose.
Preferred substituted glycosides are alkyl glucamides which have the following structure:
R3-N(R2)-C(=0)-R1
wherein Rt and Rj are as above defined and
R3 is hydrogen, thiol, hydroxyl, amino, amine, Cw alkyl, C].6 alkoxy or alkyl sulfide.
The substituted glycosides are useful as disinfectants or preservatives in all types of ophthalmic formulations, such as contact lens care solutions and pharmaceutical formulations. The compounds are present in contact lens care formulations to potentiate the antimicrobial activity of a disinfectant or preservative at concentrations at or above about 0.01 weight/ volume percent (w/v%) to 10.0 w/v%; preferably 0.01-2 w/v%; most preferably 0.1-0.5 w/v%. The compounds are useful in other ophthalmic formulations to potentiate the preservative efficacy of, for example, benzalkonium chloride (BAC), at concentrations at or above about 0.01 w/v%; preferably 0.01-2 w/v%; most preferably 0.1-0.5 w/v%. When used to potentiate the efficacy of BAC, the BAC concentration can be reduced to about 75% of its usual concentration in ophthalmic formulations.
The preferred alkyl glucamides include compounds wherein Rj is C10, Rj is glucose, and R3 is methyl (Glucamide C-10) and wherein Rj is , Rj is glucose, and R3 is methyl (Glucamide C-9). Most preferred is Glucamide C-10. Glucamide C-10 is not only effective in potentiating the efficacy of BAC, but is useful alone as an ophthalmic preservative at concentrations of above 0.01 w/v%; preferably 0.05- 0.5 w/v%; most preferably 0.1-0.3 w/v%.
The compositions can include other components known to those skilled in the art of formulating ophthalmic products. The compounds of Structure I can be incorporated into various types of ophthalmic formulations for delivery to the eye. The compounds may be combined with ophthalmologically acceptable preservatives, surfactants, viscosity enhancers, penetration enhancers, buffers, sodium chloride and water to form aqueous, sterile ophthalmic suspensions or solutions. In order to prepare sterile ophthalmic ointment formulations, the compounds are combined with the active ingredient and a preservative in an appropriate vehicle, such as, mineral oil, liquid lanolin, or white petrolatum. Sterile ophthalmic gel formulations may be prepared by suspending the active ingredient in a hydrophilic base prepared from the combination of, for example, carbopol-940 or the like according to the published formulations for analogous ophthalmic preparations; alkyl glucamides, preservatives, and tonicity agents can be incorporated. Ophthalmic solution formulations may be prepared by dissolving the active ingredient in a physiologically acceptable isotonic aqueous buffer. Further, the ophthalmic solution may include an ophthalmologically acceptable surfactant to assist in dissolving the active ingredient and preservatives to preserve the solution. Furthermore, the ophthalmic solution may contain a viscosity enhancing agent, such as, hydroxymethylcellulose, hydroxyethylcellulose, hydroxypropylmethyl-cellulose, methylcellulose, polyvinylpyrrolidone, or the like to improve the retention of the medicament in the conjunctival sac or the comfort of a contact lens. The following examples are representative of the type of ophthalmic formulations in which the substituted glycosides are useful. They are not meant to be limiting.
Active ingredients can be added to the following formulations to provide preserved ophthalmic solutions. Active ingredients can include any medicament useful for treating the eye included at concentrations and made according to techniques known to those skilled in the art of making ophthalmic formulations. Examples 2-4 can also be used without the addition of a medicament as contact lens care solutions for disinfecting, rinsing, and storage of contact lenses. Examples 4-7 can be used without a medicament as ophthalmic comfort drop formulations.
EXAMPLE 1
Component Concentration (w/v%)
Na2HP04 0.12
NaH2P04 0.18
NaCl 0.60
BAC 0.01
EDTA 0.01
Substituted Glycoside 0.20
Water qs
EXAMPLE 2
Component Concentration (w/v%)
Na2HP04 0.12
NaH2P04 0.18
Mannitol 3.31
Polyquad* 0.01
EDTA 0.01
Substituted Glycoside 0.05
Water qs EXAMPLE 3
Component Concentration w/γ%
Na2HP04 0.12
NaH2P04 0.18
NaCl 0.60
Polyquad* 0.01
EDTA 0.01
Glucamide C-10 0.20
Water qs
EXAMPLE 4
Component Concentration w/v%
Na2HP04 0.12
KH2P04 0.18
Mannitol 3.31
Polyquad® 0.001
EDTA 0.01
Substituted Glycoside 0.20
Water qs
EXAMPLE 5
Component Concentration w/v%
Na2HP04 0.12
NaH2P04 0.18
Mannitol 3.31
BAC 0.01
EDTA 0.01
Glucamide C-10 0.20
Water qs EXAMPLE 6
Component Concentration w/v%
Na2HP04 0.12
NaH2P04 0.18
Mannitol 3.31
BAC 0.0025
EDTA 0.01
Glucamide-9 0.20
Water qs
EXAMPLE 7
Component Concentration w/v%
NajHPO, 0.12
KH2P04 0.18
Mannitol 3.31
EDTA 0.01
Glucamide C-10 0.20
Water qs

Claims

We Claim:
1. An ophthalmic formulation comprising a substituted glycoside of the following structure:
(R^-Z-R,
wherein R is a hydrophobic group including saturated and unsaturated aliphatic hydrocarbon groups which range from 8 to 28 carbons in length with 1 to 5 double bonds. The aliphatic hydrocarbon group can be a straight or branched chain and may be substituted by one or more aromatic, cycloaliphatic or hydrophilic (e.g. hydroxyl, thiol, ester or amino) groups. R2 is a group derived from any cyclic or acyclic saccharide containing 4 - 7 carbons and their isomers; X is an integer from 1-10; and
O O
11 II
Z is an oxy (-0-), carbonyloxy (-0-C-), phosphoryl (-0-P-0-), thio (-S-), or O I
II r carboxamido (-N-C-) where R2 is covalently bound to such group.
2. The formulation of Claim 1 wherein R, is a straight 8-18 carbon alkyl chain in hemiacetal linkage (glycoside) to the saccharide; and
R2 is a group derived from any of a variety of isomeric saccharides containing 5 or 6 carbons selected from the group consisting of aldehyde-containing saccharides; ketone-containing saccharides; saccharide alcohols; saccharide acids; deoxysaccharides; and aminosaccharides; higher order saccharides being covalently linked in any of a number of ways to form different isomeric structures.
3. The formulation of Claim 1 wherein the substituted glycoside is an alkyl glucamide of the following structure:
R3-N(R2)-C(=Q)-R1 wherein Rt and Hr, are as above defined and g is hydrogen, thiol, hydroxyl, amino, amine, C^ alkyl, Cw alkoxy or alkyl sulfide.
4. The formulation of Claim 3 wherein R, is C10, , is glucose, and R3 is methyl.
5. The formulation of Claim 3 wherein Rj is , Rj is glucose, and R3 is methyl.
6. The formulation of Claim 1 wherein the ophthalmic formulation further comprises an ophthalmic medicament.
7. The formulation of Claim 3 wherein the ophthalmic formulation further comprises an ophthalmic medicament.
8. The formulation of Claim 4 wherein the ophthalmic formulation further comprises an ophthalmic medicament.
9. The formulation of Claim 5 wherein the ophthalmic formulation further comprises an ophthalmic medicament.
10. The formulation of Claim 1 wherein the ophthalmic formulation is a contact lens care formulation.
11. The formulation of Claim 3 wherein the ophthalmic formulation is a contact lens care formulation.
12. The formulation of Claim 4 wherein the ophthalmic formulation is a contact lens care formulation.
13. The formulation of Claim 5 wherein the ophthalmic formulation is a contact lens care formulation.
14. The formulation of Claim 10 wherein the contact lens care s formulation is a disinfecting formulation.
15. The formulation of Claim 10 wherein the contact lens care formulation is a rinsing formulation.
0 16. The formulation of Claim 10 wherein the contact lens care formulation is a storage formulation.
17. The formulation of Claim 1 wherein the ophthalmic formulation is a comfort drop formulation.
18. The formulation of Claim 3 wherein the ophthalmic formulation is a comfort drop formulation.
19. The formulation of Claim 4 wherein the ophthalmic formulation is a comfort drop formulation.
20. The formulation of Claim 5 wherein the ophthalmic formulation is a comfort drop formulation.
PCT/US1995/015577 1994-12-16 1995-11-30 Ophthalmic formulations of substituted glycosides WO1996018406A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU43719/96A AU4371996A (en) 1994-12-16 1995-11-30 Ophthalmic formulations of substituted glycosides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35924694A 1994-12-16 1994-12-16
US08/359,246 1994-12-16

Publications (2)

Publication Number Publication Date
WO1996018406A2 true WO1996018406A2 (en) 1996-06-20
WO1996018406A3 WO1996018406A3 (en) 1996-08-29

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0091645A1 (en) * 1982-04-14 1983-10-19 Bayer Ag Derivatives of amides of carboxylic acids in which the N atom is substituted by a glycosyl radical, method for their preparation and their use to influence the immunogenic system
EP0444778A1 (en) * 1990-02-14 1991-09-04 Alcon Laboratories, Inc. Use of alkyl saccharides to enhance the penetration of drugs
WO1995000151A1 (en) * 1993-06-24 1995-01-05 Uab Research Foundation Absorption enhancers for drug administration

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0091645A1 (en) * 1982-04-14 1983-10-19 Bayer Ag Derivatives of amides of carboxylic acids in which the N atom is substituted by a glycosyl radical, method for their preparation and their use to influence the immunogenic system
EP0444778A1 (en) * 1990-02-14 1991-09-04 Alcon Laboratories, Inc. Use of alkyl saccharides to enhance the penetration of drugs
WO1995000151A1 (en) * 1993-06-24 1995-01-05 Uab Research Foundation Absorption enhancers for drug administration

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
J PHARMACOL EXP THER, DEC 1994, 271 (3) P1274-80, UNITED STATES, XP002005626 PILLION DJ ET AL: "Alkylglycosides enhance systemic absorption of insulin applied topically to the rat eye." *
JOURNAL OF OCULAR PHARMACOLOGY, vol. 9, no. 4, 1993, pages 321-332, XP000570599 BUCOLO, C. ET AL: "Effects of Mipragoside on ocular allergic inflammation in the rabbit" *

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AU4371996A (en) 1996-07-03
WO1996018406A3 (en) 1996-08-29

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