CA2487332C - Quaternised ammonium cyclodextrin compounds for use as antimicrobial agents, preservatives and penetration enhancers - Google Patents
Quaternised ammonium cyclodextrin compounds for use as antimicrobial agents, preservatives and penetration enhancers Download PDFInfo
- Publication number
- CA2487332C CA2487332C CA2487332A CA2487332A CA2487332C CA 2487332 C CA2487332 C CA 2487332C CA 2487332 A CA2487332 A CA 2487332A CA 2487332 A CA2487332 A CA 2487332A CA 2487332 C CA2487332 C CA 2487332C
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- Prior art keywords
- drugs
- composition according
- compound
- formula
- ophthalmic
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- -1 ammonium cyclodextrin compounds Chemical class 0.000 title claims abstract description 45
- 239000003755 preservative agent Substances 0.000 title claims abstract description 22
- 239000004599 antimicrobial Substances 0.000 title description 5
- 239000003623 enhancer Substances 0.000 title description 4
- 230000035515 penetration Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000003814 drug Substances 0.000 claims abstract description 57
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 52
- 230000002335 preservative effect Effects 0.000 claims abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 7
- 230000002924 anti-infective effect Effects 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 4
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 91
- 229940079593 drug Drugs 0.000 claims description 51
- 229960004853 betadex Drugs 0.000 claims description 13
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 8
- 208000010412 Glaucoma Diseases 0.000 claims description 7
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 7
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 7
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
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- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 claims description 4
- VYGQUTWHTHXGQB-FFHKNEKCSA-N Retinol Palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C VYGQUTWHTHXGQB-FFHKNEKCSA-N 0.000 claims description 4
- 239000003732 agents acting on the eye Substances 0.000 claims description 4
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
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- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
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- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
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- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 208000001491 myopia Diseases 0.000 claims description 3
- 230000004379 myopia Effects 0.000 claims description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 2
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- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 210000003786 sclera Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940010747 sodium hyaluronate Drugs 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
- JJICLMJFIKGAAU-UHFFFAOYSA-M sodium;2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)purin-6-olate Chemical compound [Na+].NC1=NC([O-])=C2N=CN(COC(CO)CO)C2=N1 JJICLMJFIKGAAU-UHFFFAOYSA-M 0.000 description 1
- RMLUKZWYIKEASN-UHFFFAOYSA-M sodium;2-amino-9-(2-hydroxyethoxymethyl)purin-6-olate Chemical compound [Na+].O=C1[N-]C(N)=NC2=C1N=CN2COCCO RMLUKZWYIKEASN-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical class OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
- 229940117013 triethanolamine oleate Drugs 0.000 description 1
- 229960003962 trifluridine Drugs 0.000 description 1
- VSQQQLOSPVPRAZ-RRKCRQDMSA-N trifluridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C(F)(F)F)=C1 VSQQQLOSPVPRAZ-RRKCRQDMSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
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
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/4535—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Virology (AREA)
- Dermatology (AREA)
- Ophthalmology & Optometry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02013074 | 2002-06-13 | ||
| EP02013074.6 | 2002-06-13 | ||
| EP02028554 | 2002-12-20 | ||
| EP02028554.0 | 2002-12-20 | ||
| PCT/EP2003/006192 WO2003105867A1 (en) | 2002-06-13 | 2003-06-12 | Quaternised ammonium cyclodextrin compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2487332A1 CA2487332A1 (en) | 2003-12-24 |
| CA2487332C true CA2487332C (en) | 2012-05-15 |
Family
ID=29737927
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2487332A Expired - Fee Related CA2487332C (en) | 2002-06-13 | 2003-06-12 | Quaternised ammonium cyclodextrin compounds for use as antimicrobial agents, preservatives and penetration enhancers |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US20050222085A1 (enExample) |
| EP (1) | EP1515729B1 (enExample) |
| JP (2) | JP4773721B2 (enExample) |
| CN (1) | CN100589809C (enExample) |
| AT (1) | ATE386532T1 (enExample) |
| AU (1) | AU2003276957A1 (enExample) |
| BR (1) | BR0311722A (enExample) |
| CA (1) | CA2487332C (enExample) |
| CY (1) | CY1108099T1 (enExample) |
| DE (1) | DE60319221T2 (enExample) |
| DK (1) | DK1515729T3 (enExample) |
| ES (1) | ES2301807T3 (enExample) |
| PT (1) | PT1515729E (enExample) |
| SI (1) | SI1515729T1 (enExample) |
| WO (1) | WO2003105867A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100678824B1 (ko) * | 2005-02-04 | 2007-02-05 | 한미약품 주식회사 | 용해성이 증가된 무정형 타크로리무스 고체분산체 및 이를포함하는 약제학적 조성물 |
| BRPI0709409A2 (pt) | 2006-03-28 | 2011-07-12 | Javelin Pharmaceuticals Inc | composição farmacêutica e método para tratar um mamìfero necessitando de analgesia |
| WO2008120249A1 (en) * | 2007-03-30 | 2008-10-09 | Sifi S.P.A. | Pharmaceutical formulations based on apolar and polar lipids for ophthalmic use |
| CN101757621B (zh) * | 2008-11-28 | 2012-07-04 | 天津金耀集团有限公司 | 一种眼部抗炎的环糊精包合药物组合物 |
| US9642920B2 (en) * | 2009-06-03 | 2017-05-09 | Case Western Reserve University | Therapeutic agent delivery system and method |
| CN102276761A (zh) * | 2010-06-11 | 2011-12-14 | 南京理工大学 | 单取代铵基正电型-β-环糊精及其制备方法 |
| GB201114459D0 (en) * | 2011-08-22 | 2011-10-05 | Isis Innovation | Anti-bacterial compounds |
| CN103497275B (zh) * | 2013-08-09 | 2015-12-23 | 华北电力大学（保定） | 一种抗菌、抗病毒胍盐星形聚合物及其制备方法和应用 |
| CZ307458B6 (cs) * | 2014-11-25 | 2018-09-12 | Spur A.S. | Vícevrstvý kryt rány s aktivní vrstvou a způsob jeho výroby |
| EP3227379B1 (en) * | 2014-12-02 | 2020-07-29 | B.G. Negev Technologies and Applications Ltd., at Ben-Gurion University | Quaternized starches for use as anti-microbial agents |
| CN109487588B (zh) * | 2018-11-19 | 2021-04-20 | 绍兴永通印花有限公司 | 一种印花用涤纶织物处理液及其使用方法 |
| BR112021014889A2 (pt) * | 2019-02-14 | 2021-10-05 | Cyclopure, Inc. | Materiais poliméricos de ciclodextrina com carga e métodos de fabricação e uso dos mesmos |
| CN109836512A (zh) * | 2019-03-04 | 2019-06-04 | 西南石油大学 | 一种新型β-CD双子表面活性剂为稠化剂的清洁压裂液 |
| CN112386710A (zh) * | 2020-12-09 | 2021-02-23 | 星拜(苏州)生物科技有限公司 | 一种利用包埋技术改善紫檀芪水溶性的方法 |
| CN116987213B (zh) * | 2022-04-26 | 2025-09-09 | 中国石油化工股份有限公司 | 一种具有表面活性剂功能的化合物、一种表面活性剂及其制备方法 |
| CN120435346A (zh) | 2023-01-12 | 2025-08-05 | 赛克洛珀股份有限公司 | 聚合环糊精吸附剂的再生 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453257A (en) * | 1967-02-13 | 1969-07-01 | Corn Products Co | Cyclodextrin with cationic properties |
| JPS58210901A (ja) * | 1982-06-01 | 1983-12-08 | Kao Corp | シクロデキストリン誘導体およびその製造方法 |
| IT1229133B (it) * | 1989-03-09 | 1991-07-22 | Farmhispania | Sali ammonici di policiclodestrine per l'impiego come agenti ipocolesterolemizzanti |
| KR927003645A (ko) * | 1990-05-21 | 1992-12-18 | 후지다 히로미찌 | 씨클로덱스트린 유도체 |
| JPH0481401A (ja) * | 1990-07-24 | 1992-03-16 | Toppan Printing Co Ltd | シクロデキストリン誘導体 |
| JPH0665307A (ja) * | 1992-06-17 | 1994-03-08 | Sankyo Co Ltd | シクロデキストリン誘導体 |
| US5891913A (en) * | 1994-10-10 | 1999-04-06 | Novartis Finance Corporation | Ophthalmic and aural compositions containing diclofenac potassium |
| JP3297969B2 (ja) * | 1994-12-26 | 2002-07-02 | ライオン株式会社 | 点眼剤 |
| US5869079A (en) * | 1995-06-02 | 1999-02-09 | Oculex Pharmaceuticals, Inc. | Formulation for controlled release of drugs by combining hydrophilic and hydrophobic agents |
| TW434023B (en) * | 1995-09-18 | 2001-05-16 | Novartis Ag | Preserved ophthalmic composition |
| NZ505951A (en) * | 1998-02-23 | 2003-02-28 | Cyclops Ehf | A method for enhancing the complexation efficiency of a heterocyclic drug with cyclodextrin, by subjecting the heterocycloc drug to chemically reversible ring-opening |
-
2003
- 2003-06-12 CN CN03813614A patent/CN100589809C/zh not_active Expired - Fee Related
- 2003-06-12 WO PCT/EP2003/006192 patent/WO2003105867A1/en not_active Ceased
- 2003-06-12 DK DK03740232T patent/DK1515729T3/da active
- 2003-06-12 JP JP2004512769A patent/JP4773721B2/ja not_active Expired - Fee Related
- 2003-06-12 DE DE60319221T patent/DE60319221T2/de not_active Expired - Lifetime
- 2003-06-12 AU AU2003276957A patent/AU2003276957A1/en not_active Abandoned
- 2003-06-12 US US10/516,247 patent/US20050222085A1/en not_active Abandoned
- 2003-06-12 EP EP03740232A patent/EP1515729B1/en not_active Expired - Lifetime
- 2003-06-12 CA CA2487332A patent/CA2487332C/en not_active Expired - Fee Related
- 2003-06-12 BR BR0311722-7A patent/BR0311722A/pt not_active IP Right Cessation
- 2003-06-12 AT AT03740232T patent/ATE386532T1/de active
- 2003-06-12 SI SI200331202T patent/SI1515729T1/sl unknown
- 2003-06-12 ES ES03740232T patent/ES2301807T3/es not_active Expired - Lifetime
- 2003-06-12 PT PT03740232T patent/PT1515729E/pt unknown
-
2008
- 2008-05-20 CY CY20081100523T patent/CY1108099T1/el unknown
- 2008-09-26 US US12/238,473 patent/US20090110734A1/en not_active Abandoned
-
2010
- 2010-08-20 JP JP2010185238A patent/JP2011006448A/ja active Pending
-
2011
- 2011-09-16 US US13/234,912 patent/US20120004158A1/en not_active Abandoned
-
2012
- 2012-12-21 US US13/723,257 patent/US20130137657A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN100589809C (zh) | 2010-02-17 |
| JP2005529175A (ja) | 2005-09-29 |
| US20050222085A1 (en) | 2005-10-06 |
| SI1515729T1 (sl) | 2008-08-31 |
| BR0311722A (pt) | 2005-03-01 |
| US20090110734A1 (en) | 2009-04-30 |
| ATE386532T1 (de) | 2008-03-15 |
| US20130137657A1 (en) | 2013-05-30 |
| CY1108099T1 (el) | 2014-02-12 |
| PT1515729E (pt) | 2008-05-30 |
| DK1515729T3 (da) | 2008-06-16 |
| AU2003276957A1 (en) | 2003-12-31 |
| WO2003105867A1 (en) | 2003-12-24 |
| JP4773721B2 (ja) | 2011-09-14 |
| EP1515729B1 (en) | 2008-02-20 |
| US20120004158A1 (en) | 2012-01-05 |
| DE60319221D1 (de) | 2008-04-03 |
| JP2011006448A (ja) | 2011-01-13 |
| CA2487332A1 (en) | 2003-12-24 |
| DE60319221T2 (de) | 2009-03-05 |
| ES2301807T3 (es) | 2008-07-01 |
| CN1658888A (zh) | 2005-08-24 |
| EP1515729A1 (en) | 2005-03-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140612 |