NO309507B1 - Cyklodekstrininneholdende mucoadhesive emulsjoner - Google Patents

Cyklodekstrininneholdende mucoadhesive emulsjoner Download PDF

Info

Publication number: NO309507B1
Authority: NO; Norway
Prior art keywords: cyclodextrin; mixture; amount; acid; itraconazole
Prior art date: 1994-05-18

Application number

NO964853A

Other languages

English (en)

Norwegian (no)

Other versions

NO964853D0 (no

NO964853L (no

Inventor

Peter Putteman

Marc Karel Jozef Francois

Eric Carolus Leonarda Snoeckx

Original Assignee

Janssen Pharmaceutica Nv

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.)

1994-05-18

Filing date

1996-11-15

Publication date

2001-02-12

1996-11-15 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1996-11-15 Publication of NO964853D0 publication Critical patent/NO964853D0/no

1996-11-15 Publication of NO964853L publication Critical patent/NO964853L/no

2001-02-12 Publication of NO309507B1 publication Critical patent/NO309507B1/no

Links

229920000858 Cyclodextrin Polymers 0.000 title claims description 43
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims description 38
239000000839 emulsion Substances 0.000 title claims description 12
230000003232 mucoadhesive effect Effects 0.000 title claims description 12
239000000203 mixture Substances 0.000 claims description 60
229960004130 itraconazole Drugs 0.000 claims description 20
VHVPQPYKVGDNFY-DFMJLFEVSA-N 2-[(2r)-butan-2-yl]-4-[4-[4-[4-[[(2r,4s)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one Chemical compound O=C1N([C@H](C)CC)N=CN1C1=CC=C(N2CCN(CC2)C=2C=CC(OC[C@@H]3O[C@](CN4N=CN=C4)(OC3)C=3C(=CC(Cl)=CC=3)Cl)=CC=2)C=C1 VHVPQPYKVGDNFY-DFMJLFEVSA-N 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 11
229940079593 drug Drugs 0.000 claims description 10
239000003995 emulsifying agent Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
239000003381 stabilizer Substances 0.000 claims description 5
239000002562 thickening agent Substances 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 2
239000007762 w/o emulsion Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
239000012071 phase Substances 0.000 description 21
-1 itraconazole compound Chemical class 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
239000002253 acid Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
238000004566 IR spectroscopy Methods 0.000 description 7
AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
239000006071 cream Substances 0.000 description 7
239000003921 oil Substances 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 6
239000002585 base Substances 0.000 description 6
229940097362 cyclodextrins Drugs 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
OYZZJAQBPGMCDN-UHFFFAOYSA-N 18,18,18-trihydroxyoctadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)(O)O OYZZJAQBPGMCDN-UHFFFAOYSA-N 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
239000000872 buffer Substances 0.000 description 5
229940085262 cetyl dimethicone Drugs 0.000 description 5
210000004400 mucous membrane Anatomy 0.000 description 5
210000001215 vagina Anatomy 0.000 description 5
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
239000005662 Paraffin oil Substances 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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150000007513 acids Chemical class 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
229940121375 antifungal agent Drugs 0.000 description 4
239000003429 antifungal agent Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
238000004949 mass spectrometry Methods 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
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WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class 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 description 3
229960004853 betadex Drugs 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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238000002360 preparation method Methods 0.000 description 3
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KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000001116 FEMA 4028 Substances 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229920001214 Polysorbate 60 Polymers 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 2
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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230000037396 body weight Effects 0.000 description 2
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YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 2
SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
235000014655 lactic acid Nutrition 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
239000007764 o/w emulsion Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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208000013464 vaginal disease Diseases 0.000 description 2
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
BLSQLHNBWJLIBQ-OZXSUGGESA-N (2R,4S)-terconazole Chemical compound C1CN(C(C)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2N=CN=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 BLSQLHNBWJLIBQ-OZXSUGGESA-N 0.000 description 1
LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
LODHFNUFVRVKTH-ZHACJKMWSA-N 2-hydroxy-n'-[(e)-3-phenylprop-2-enoyl]benzohydrazide Chemical compound OC1=CC=CC=C1C(=O)NNC(=O)\C=C\C1=CC=CC=C1 LODHFNUFVRVKTH-ZHACJKMWSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
206010000117 Abnormal behaviour Diseases 0.000 description 1
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244000043261 Hevea brasiliensis Species 0.000 description 1
BYBLEWFAAKGYCD-UHFFFAOYSA-N Miconazole Chemical compound ClC1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 BYBLEWFAAKGYCD-UHFFFAOYSA-N 0.000 description 1
229920000881 Modified starch Polymers 0.000 description 1
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239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229960005137 succinic acid Drugs 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960000580 terconazole Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002110 toxicologic effect Effects 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
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
- A61K47/40—Cyclodextrins; Derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
- 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
- A61K9/0034—Urogenital system, e.g. vagina, uterus, cervix, penis, scrotum, urethra, bladder; Personal lubricants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nanotechnology (AREA)
Reproductive Health (AREA)
Inorganic Chemistry (AREA)
Gynecology & Obstetrics (AREA)
Molecular Biology (AREA)
Urology & Nephrology (AREA)
Medical Informatics (AREA)
General Engineering & Computer Science (AREA)
Biotechnology (AREA)
Biophysics (AREA)
Crystallography & Structural Chemistry (AREA)
Endocrinology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Cosmetics (AREA)
Materials For Medical Uses (AREA)
Adhesives Or Adhesive Processes (AREA)

NO964853A 1994-05-18 1996-11-15 Cyklodekstrininneholdende mucoadhesive emulsjoner NO309507B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP94201402		1994-05-18
PCT/EP1995/001760 WO1995031178A1 (en)	1994-05-18	1995-05-10	Mucoadhesive emulsions containing cyclodextrin

Publications (3)

Publication Number	Publication Date
NO964853D0 NO964853D0 (no)	1996-11-15
NO964853L NO964853L (no)	1996-11-15
NO309507B1 true NO309507B1 (no)	2001-02-12

Family

ID=8216883

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO964853A NO309507B1 (no)	1994-05-18	1996-11-15	Cyklodekstrininneholdende mucoadhesive emulsjoner

Country Status (30)

Country	Link
US (1)	US5814330A (zh)
EP (1)	EP0759741B1 (zh)
JP (1)	JP3862748B2 (zh)
KR (1)	KR100369703B1 (zh)
CN (1)	CN1091590C (zh)
AP (1)	AP731A (zh)
AT (1)	ATE174790T1 (zh)
AU (1)	AU680767B2 (zh)
BG (1)	BG62754B1 (zh)
BR (1)	BR9507873A (zh)
CZ (1)	CZ285606B6 (zh)
DE (1)	DE69506857T2 (zh)
DK (1)	DK0759741T3 (zh)
EE (1)	EE03304B1 (zh)
ES (1)	ES2127529T3 (zh)
FI (1)	FI964589A0 (zh)
HK (1)	HK1010688A1 (zh)
HU (1)	HU218082B (zh)
IL (1)	IL113742A (zh)
MY (1)	MY113846A (zh)
NO (1)	NO309507B1 (zh)
NZ (1)	NZ285761A (zh)
OA (1)	OA10321A (zh)
PL (1)	PL179619B1 (zh)
RO (1)	RO117145B1 (zh)
RU (1)	RU2164418C2 (zh)
SK (1)	SK282623B6 (zh)
TW (1)	TW438601B (zh)
WO (1)	WO1995031178A1 (zh)
ZA (1)	ZA954023B (zh)

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1995
- 1995-04-14 TW TW084103651A patent/TW438601B/zh not_active IP Right Cessation
- 1995-05-10 SK SK1469-96A patent/SK282623B6/sk unknown
- 1995-05-10 PL PL95317257A patent/PL179619B1/pl unknown
- 1995-05-10 BR BR9507873A patent/BR9507873A/pt not_active IP Right Cessation
- 1995-05-10 KR KR1019960706024A patent/KR100369703B1/ko not_active IP Right Cessation
- 1995-05-10 HU HU9603188A patent/HU218082B/hu not_active IP Right Cessation
- 1995-05-10 AP APAP/P/1996/000873A patent/AP731A/en active
- 1995-05-10 US US08/732,262 patent/US5814330A/en not_active Expired - Lifetime
- 1995-05-10 EE EE9600212A patent/EE03304B1/xx not_active IP Right Cessation
- 1995-05-10 RO RO96-02162A patent/RO117145B1/ro unknown
- 1995-05-10 WO PCT/EP1995/001760 patent/WO1995031178A1/en active IP Right Grant
- 1995-05-10 RU RU96123916/14A patent/RU2164418C2/ru active
- 1995-05-10 AT AT95919433T patent/ATE174790T1/de not_active IP Right Cessation
- 1995-05-10 DE DE69506857T patent/DE69506857T2/de not_active Expired - Lifetime
- 1995-05-10 CN CN95193083A patent/CN1091590C/zh not_active Expired - Lifetime
- 1995-05-10 NZ NZ285761A patent/NZ285761A/en unknown
- 1995-05-10 DK DK95919433T patent/DK0759741T3/da active
- 1995-05-10 ES ES95919433T patent/ES2127529T3/es not_active Expired - Lifetime
- 1995-05-10 CZ CZ963369A patent/CZ285606B6/cs not_active IP Right Cessation
- 1995-05-10 JP JP52933695A patent/JP3862748B2/ja not_active Expired - Lifetime
- 1995-05-10 AU AU25264/95A patent/AU680767B2/en not_active Expired
- 1995-05-10 EP EP95919433A patent/EP0759741B1/en not_active Expired - Lifetime
- 1995-05-16 IL IL11374295A patent/IL113742A/xx not_active IP Right Cessation
- 1995-05-17 ZA ZA954023A patent/ZA954023B/xx unknown
- 1995-05-18 MY MYPI95001311A patent/MY113846A/en unknown
1996
- 1996-11-04 BG BG100955A patent/BG62754B1/bg unknown
- 1996-11-08 OA OA60920A patent/OA10321A/en unknown
- 1996-11-15 FI FI964589A patent/FI964589A0/fi not_active Application Discontinuation
- 1996-11-15 NO NO964853A patent/NO309507B1/no unknown
1998
- 1998-10-27 HK HK98111557A patent/HK1010688A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0759741B1 (en)	1998-12-23
JP3862748B2 (ja)	2006-12-27
NO964853D0 (no)	1996-11-15
IL113742A (en)	1999-09-22
PL179619B1 (pl)	2000-10-31
TW438601B (en)	2001-06-07
AU680767B2 (en)	1997-08-07
DE69506857T2 (de)	1999-08-05
ZA954023B (en)	1996-11-18
KR970702719A (ko)	1997-06-10
CZ336996A3 (en)	1997-02-12
CN1148335A (zh)	1997-04-23
MY113846A (en)	2002-06-29
HUT76326A (en)	1997-08-28
FI964589A (fi)	1996-11-15
IL113742A0 (en)	1995-08-31
FI964589A0 (fi)	1996-11-15
US5814330A (en)	1998-09-29
SK146996A3 (en)	1997-05-07
SK282623B6 (sk)	2002-10-08
AP731A (en)	1999-02-08
ATE174790T1 (de)	1999-01-15
AU2526495A (en)	1995-12-05
HU9603188D0 (en)	1997-01-28
AP9600873A0 (en)	1996-10-31
EP0759741A1 (en)	1997-03-05
NZ285761A (en)	1997-05-26
CZ285606B6 (cs)	1999-09-15
JPH10500121A (ja)	1998-01-06
RU2164418C2 (ru)	2001-03-27
BG100955A (en)	1998-04-30
BR9507873A (pt)	1997-09-23
PL317257A1 (en)	1997-04-01
DE69506857D1 (de)	1999-02-04
DK0759741T3 (da)	1999-08-23
HU218082B (hu)	2000-05-28
KR100369703B1 (ko)	2003-04-16
ES2127529T3 (es)	1999-04-16
RO117145B1 (ro)	2001-11-30
WO1995031178A1 (en)	1995-11-23
NO964853L (no)	1996-11-15
EE03304B1 (et)	2000-12-15
OA10321A (en)	1997-10-07
BG62754B1 (bg)	2000-07-31
CN1091590C (zh)	2002-10-02
HK1010688A1 (en)	1999-06-25

Publication	Publication Date	Title
NO309507B1 (no)	2001-02-12	Cyklodekstrininneholdende mucoadhesive emulsjoner
US5538721A (en)	1996-07-23	Stabilization of aminosteroids for topical ophthalmic and other applications
KR930007386B1 (ko)	1993-08-09	γ-사이클로덱스트린 유도체의 제조방법
AU565966B2 (en)	1987-10-01	Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation
JP3034048B2 (ja)	2000-04-17	抗菌・抗カビ剤の経口製剤
EP1303541B1 (en)	2011-04-27	Compositions containing metronidazole
US8492538B1 (en)	2013-07-23	Cyclodextrin derivative salts
WO2001001955A1 (en)	2001-01-11	Nasal formulation of an antifungal
CA2189863C (en)	2006-03-21	Mucoadhesive emulsions containing cyclodextrin
EP2943224B1 (en)	2020-01-01	Voriconazole inclusion complexes
MXPA96005659A (en)	1998-02-01	Mucoadhesive emulsions containing ciclodextr
WO1996001558A1 (en)	1996-01-25	Anandamide analogue compositions and method of treating intraocular hypertention using same
JP2701029B2 (ja)	1998-01-21	低刺激性薬物担体